1312 lines
80 KiB
Plaintext
1312 lines
80 KiB
Plaintext
CHAPTER 1
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TOMMY
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Tommy was an only child and grew up in a small town in
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the Mid-West. When he was young and was home alone, he would
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often play 'dress-up' in his mother's clothing, thrilling to
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the feel of the soft silky material against his body. He was
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smaller than the other boys and had facial features more like
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a girl's than a boy's. This was often made comment on by his
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Aunt who visited his family with some regularity. "Such a
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pretty girl you would make," she would comment as she hugged
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the boy and offered kisses to her nephew. Tommy liked his
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Aunt Beth and always tried to please her whenever she visited
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and was always rewarded with hugs and kisses from the beauti-
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ful woman.
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One day when he was about 11, he was playing 'dress-up'
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in the hours between when he got home from school and when his
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parents arrived home from work. Dressed in his mother's
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frilly nylon panties, a bra, slip, and a pair of her high
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heels, he was admiring himself in the full length mirror in
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his parent's room. He was turned sideways to the mirror and
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was slowly stroking the silky material of the slip against his
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sides, feeling the wonderful tingle it always provided his
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body. His small cock was hard and rubbing delightfully
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against the panties,when suddenly he heard footsteps in the
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hallway.
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"Tommy? Are you here Tommy?" It was Aunt Beth! "Oh my
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God," He thought, "What if she catches me in Mom's clothes?"
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Before he could formulate an answer to his own question, his
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Aunt entered the room. "Oh there you are," his Aunt started,
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then seeing how her nephew was attired, "My aren't we pretty
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today." Tommy turned beet red and tried to hide behind the
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mirror.
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Aunt Beth was the younger sister of his mother and only
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25 years old. Tall to his eyes, she had long flowing blonde
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hair which came down to her breasts and had that 'willowy'
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look Tommy had observed in the fashion magazines his mother
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received in the mail. Her deep blue eyes surveyed her nephew
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and she arrived at the conclusion that she had scared the boy
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badly with her entry. "Tommy, don't be afraid, come over here
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and give Aunt Beth a hug," she said to him.
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Tommy still flushed in embarrassment and now trembling,
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came out from behind the free standing mirror and approached
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his Aunt. Seeing the boy shake, elicited a response of
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sympathy from the woman who extended her arms and quickly drew
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the boy to her, then hugged him tightly to her. "There,
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there," she murmured as she held the boy to her, "It's OK
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Tommy, Aunt Beth loves you and would never hurt her favorite
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nephew." She stroked his small head as she held it to her
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ample breasts and soon felt his trembling stop. She released
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her hug and moved him out from her enough to grasp his small
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chin in her hand and gently tilted his head upwards so that
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she could look at his face. Tears were streaming down both
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cheeks when his face came into view, so she gently wiped them
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with her fingertips and then kissed the boy on the cheek and
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forehead.
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Holding the boy by the shoulders, she sat down on the
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edge of the bed so that they were now at eye level with each
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other. Then gently stroked his long-ish light brown hair back
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from his face with her right hand, which finally rested on his
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left shoulder at the base of his neck. His eyes were the same
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deep blue as her own, but now red from crying and his pale
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white cheeks trembled as he tried to speak. "Please don't
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tell my Mother," he managed to get out, "She'll be mad at me
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for messing with her things." Tears immediately started
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flowing down the lovely boy's cheeks again, which Beth stroked
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with her thumbs, then pulled him forward between her legs and
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hugged him again with his head resting on her shoulder.
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She rocked the small boy and gently caressed his back as
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she held him then said, "I won't tell on you...I love you too
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much to ever hurt you, little one." "Thank you Aunt Beth,"
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came a soft reply, "I love you too." She continued to rock
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and stroke him until she felt his body relax, then moved him
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back out to a point between her knees, and held him by his
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forearms. "Now then, why don't you tell me about it?" and
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again moved her right hand up, brushing his hair from his
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face.
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In between occasional shudders and sniffles, Tommy
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explained to his aunt that he dressed in his mother's clothing
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two or three times per week and how he enjoyed the feel of
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them on his body. She asked if he had ever used his mother's
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makeup or dresses in addition to the underclothes and Tommy
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replied "only a couple of times." "It's too hard to get that
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stuff off my face," he explained and this received a smile and
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a chuckle from Aunt Beth.
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When he was done, she stroked his hair again and gently
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talked to him. "It's OK Tommy, there is nothing wrong with
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boys wanting to play dress-up...But if you are going to do it,
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you should dress your own age." "But how?" Tommy inquired.
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"Let me think on that for a while," she responded, then con-
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tinued, "I don't know right now, but I'll work on it; for now
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however, you better change before your Mom gets home and finds
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you." Tommy, leaned in and hugged his Aunt then gave her a
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kiss before letting go, "Thank you Aunt Beth," he whispered as
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he released his hold on the woman.
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His parents arrived home about 45 minutes later and true
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to her word, his Aunt did not mention the incident to them.
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Tommy thought she had forgotten all about it when several
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months passed and nothing had happened.
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It was the beginning of summer, Beth was visiting and
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over dinner she made an offer to his parents. "You two work
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too hard, you should take a vacation," she proposed, "I'll
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tell you what, I'll take care of Tommy, and you two take a
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second honeymoon!" An offer like this was too good to refuse.
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Tommy's parents HAD been working very hard in the past five
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years, in order to buy the house they lived in. They had
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taken little time off and other than a weekend once or twice,
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had never had a vacation away from their son since he had been
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born. "Would you really be willing to do that Sis," Tommy's
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mother asked. "Janet, you know I'm a teacher and have the
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whole summer off. Tommy and I get along great, and you two
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NEED a vacation." "It wouldn't be too much trouble?" his
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father inquired. "No trouble at all, Tommy and I will have
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lot's of fun, while you two lovebirds get some time to your-
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selves," Beth replied. "Then it's a deal," his mother said,
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"I hope you won't be sorry," she added. "No chance!" Beth
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responded.
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Things moved quickly, Tommy's parents made arrangements
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to take a month off from work and booked reservations at
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several hotels along their intended route. Beth would take
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them to the airport, then she and Tommy would return to her
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apartment for the duration of the trip. Beth would pick them
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up when they returned; all was set for the trip to begin in
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three weeks.
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Tommy was excited about the whole idea, he had not played
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dress-up since the day he had been caught by his Aunt Beth.
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He had been afraid that it might be his mother who caught him
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the next time and had refrained from such activities. He had
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however, stolen a pair of her frilly panties and a slip, and
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slept in them whenever he could do so safely. Maybe his Aunt
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would let him play dress-up at her apartment, while he stayed
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there.
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The day finally came and after seeing his parents off at
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the airport, they walked back to Aunt Beth's car in the par-
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king lot. "I have a surprise for you Tommy," she said as they
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walked. "For the next month, your name will be spelled 'TOMI'
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and you will be my niece rather than my nephew!" "Really,"
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Tommy squealed with glee, "Yes," she replied "and it will
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start as soon as we get to your house." Tommy was beside
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himself and stopping his Aunt, gave her the biggest hug his
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little body could provide. "I though you might like it," she
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said, after giving him a kiss on the forehead and stroking her
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long fingers through his hair.
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***************************
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CHAPTER 2
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FROM TOMMY TO 'TOMI'
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When they arrived back at Tommy's house, he was escorted
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into his bedroom by his Aunt who was carrying a small bag she
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had retrieved from the trunk of her car. "Take off all of you
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clothes," she said, much to Tommy's shock. Seeing the boy
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hesitate, "You're not going to get SHY on your Aunt are you?
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I've seen your little butt naked most of your life and can't
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remember how many times I changed your diapers." Knowing her
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statement was true, he immediately started undressing while
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she removed items of clothing from the bag.
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Now standing completely naked before his Aunt, Tommy
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tried to hide his groin with his hands. "Come over here," she
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commanded in a still gentle voice; Tommy moved to where she
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was seated on the chair at the end of his bed. "Oh, put your
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hands down," she said as if frustrated, "You don't have
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ANYTHING to hide from me." Tommy complied and after looking
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him over from head to toe, she then produced a seamstress's
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tape measure and took the various measurements of his body.
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"Your a little bigger than I thought, but these will still fit
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you," she observed and handed him a pile of clothing from the
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bed. Tommy accepted the clothing and while he looked it over,
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his Aunt picked up his tennis shoes and removed the laces.
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In the clothing he had been handed was: a pair of white
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ankle socks, a white denim purse with a long thin strap, a
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pair of white nylon panties, a pink tube top with a frilly
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edge at the top seam and a pair of white shorts with no zipper
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or pockets like his had. Tommy picked up the panties and
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pulled them slowly up his legs, once again thrilling to the
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feel of the smooth material on his body. He then put on the
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tube top and shorts, then sat down to put on the ankle socks;
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which he noted had pink and white lace at the top. In the
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mean time, his Aunt had replaced the white laces in his shoes
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with pink ones and seeing him looking her way offered an
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explanation. "I didn't know what size shoes you wore, so
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these will do until we can get you some girl's shoes."
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Aunt Beth then had Tommy sit in the chair and got some
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cosmetics from her bag. Tilting his face up to her, she held
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it in her palm and studied him for a couple of minutes. "You
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have such lovely skin and bone structure," she offered, "I
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just wish I'd looked that good at your age," as if talking to
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herself. She then took a pair of tweezers and plucked a few
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hairs from his eyebrows and applied some blusher to his
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cheeks. A light pink lipstick and gloss were then put on his
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lips and after blotting, applied again. Aunt Beth then took
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a comb and parted his hair down the middle and then drew it
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into two pony tails, one on either side of his head, which
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were secured with pink ribbons to match his outfit. "All
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done, Tomi, let's go into your parent's room, where you can
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see yourself in the mirror."
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Aunt Beth lead him by the hand into the next room and
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stood behind him with her hands on his bare shoulders as he
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gazed at the mirror. Looking back at him was one of the
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prettiest young girls he had ever seen, with pale white skin,
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light brown hair, big blue eyes, and a cute little play
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outfit. Tommy was thrilled at the results and turned to his
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Aunt and hugged her for all he was worth, then planted a half
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a dozen kisses all over her face as he thanked her. "Let's go
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home then Tomi," she said, "We'll stop and get you some more
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clothes along the way." Smiling all the while, he skipped to
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the car as his Aunt locked up the house.
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On the other side of town, his Aunt stopped at a K-Mart
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store, and Tommy was taken inside, where he was allowed to try
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on a number of dresses and outfits. He was having a ball and
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loved modeling the clothing for his beautiful smiling Aunt and
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no one suspected that he was a boy. When they left, his arms
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were full of packages including: 3 dresses, 3 sun-suits, an
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assortment of tops and blouses, 3 more pair of shorts, a dozen
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pair of panties, 4 training bras, a couple of slips, a set of
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petticoats and 3 pair of shoes. Tommy didn't see the amount
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of the final bill, but knew all of this stuff must have cost
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his Aunt a FORTUNE. He therefore, thanked, hugged and kissed
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her at every possible opportunity. She just smiled and told
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him he was welcome.
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For the next couple of hours they drove and Tommy got
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very tired. All the excitement at the store had drained him
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and soon he fell asleep on the front seat of the car. He
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awoke with his head on his Aunt's lap, looking towards her
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feet. Her skirt had ridden up from his head moving about on
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her lap, and Tommy's face was resting on a stocking covered
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but otherwise bare thigh. He moved his cheek against the
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sheer material and sighed at the thrilling feel it gave him.
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"Awake little girl?" he heard, and a hand gently caressed his
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cheek and rolled his head back and up. He flipped onto his
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back and smiled up at his pretty Aunt, who continued to drive
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as she smiled down at him and caressed his left shoulder.
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His Aunt told him they would be stopping in a few minutes
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to get some dinner. They were only 30 minutes from home but
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she was tired and did not feel like cooking when she got home.
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Tommy sat upright, but stayed in the center of the seat,
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pressed up against his Aunt Beth, who continued to stroke his
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shoulders as she drove. True to her word, she shortly pulled
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into a 'Denney's' restaurant and they went inside to eat. The
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two sat at their table and ate a hardy meal as they talked
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about what she had planned for their upcoming month together.
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To everyone in the restaurant they were just a lovely woman
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treating her pretty niece to a dinner.
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At one point Tommy had to go to the bathroom and when he
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arose, his Aunt pulled him to her before he left the table and
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whispered in his ear, "Don't forget to use the GIRL's room,
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NOT the boy's." Tommy blushed, because he had become so
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comfortable with the way he was dressed, he had forgotten he
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was dressed as a girl. Had she not reminded him, he probably
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WOULD have gone into the wrong restroom. He gave his Aunt a
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kiss for saving him, and proceeded to the restroom without in-
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cident. Inside, he almost stood before the toilet to pee,
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when he realized that someone was in the next stall, and
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decided he better sit like girl's do, so they wouldn't think
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anything wrong.
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Back in the car, they proceeded to the apartment building
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and with arms loaded by packages went up the elevator to her
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floor. As the elevator door opened, they were greeted by two
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young girls about Tommy's age. "Hi, Miss Henderson," the
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girls beamed. "Hi, girls...Oh, I'd like you to meet my niece
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Tomi, who will be staying with me for the next month while her
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parents are on vacation. Tomi, this is Jenny and this is
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Suzie, two of my students." "Hi girls," said Tommy and gave
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them his best smile. "Hi Tomi," they responded also smiling,
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"We have to run, Miss Henderson or we'll be late for the mov-
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ie, but we'll stop by tomorrow, if that's OK," said Jenny.
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"That'll be fine, Jenny, I think Tomi is a little tired from
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the trip anyway, Bye, Have Fun!" Almost as quick as his eyes
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could follow, they jumped into the elevator and were gone.
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"Cute girls," said his Aunt, "You'll probably be playing with
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them a lot."
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Inside the apartment, Tommy was shown to the guest room,
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which was to be his for the next month. His aunt helped him
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put his new clothes away in the closet and dresser, then
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suggested that it was late and he would probably want to take
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a bath before going to bed. Before he could answer, she
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turned and went into the bathroom and started the bath water
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running into the tub.
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When, she returned, he was standing nude in the bedroom,
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trying to find his robe in the dresser. "Where's my robe?" he
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said "Oh, guess I forgot to buy you one," she replied somewhat
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exasperated. "We'll get you one tomorrow as well as anything
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else I forgot," then giving him a pat on the ass, "In to the
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bath with you." With a squeal and a giggle, he ran for the
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bathroom and dove into the warm foamy bathtub. He laid back
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in the water and soaked for a while, relaxing and enjoying the
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feel of the bath.
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After about 10 minutes, his Aunt came into the bathroom,
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wearing a long flowing silk robe. When she knelt beside the
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tub, Tommy could see her bare legs and thighs almost halfway
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up. She then picked up a washcloth and soaped it, and started
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washing the makeup from his face. After rinsing his face, she
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started working on the rest of his body and as she worked, her
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robe fell open and his eyes nearly bugged out of his head when
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he saw her large breasts bobbing about as she moved. He could
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also see her public hair which was darker than the hair on her
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head, but not very thick, so her pussy lips were also visible.
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Seeing where the boy was looking, his Aunt said, "Oh MY!,
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and immediately closed her robe. Then thinking for a couple
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of seconds released her robe and said, "Well it was bound to
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happen sooner or later anyway...Now it's over with." "Did you
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like what you saw?" Aunt Beth asked. Tommy stammered and
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stuttered since the only woman he had ever seen nude was his
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mother and only quick glimpses of her. "Ya...Yes," he finally
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managed to say, "Ver...Very much." "Good," said his Aunt,
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"But it is generally considered good manners for a man to
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complement a woman on her breasts." "The...They are VERY
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nice," he replied, "May...May I touch them?" "Well now, THAT,
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was certainly a GIANT leap into manhood; Certainly dear, you
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may touch them if you want."
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Aunt Beth stopped washing him for a minute and removed
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her robe, hanging it on the door the returned and kneeled
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beside the tub once more. With his hand shaking, Tommy
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reached out and gently stroked his Aunt's left breast, then
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turning his body to face her lifted her right breast in his
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left and hand feeling the weight. His small hand probed and
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stroked the soft flesh and he noticed that her nipples in-
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creased in size as he caressed the lovely woman. She contin-
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ued washing him, but he noticed that her breathing was heavier
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and she gulped air like she was having trouble breathing.
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"Are you OK Aunt Beth, I'm not hurting you am I?" She pulled
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his face against her breasts and stroking his head replied,
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"No dear boy, you're not hurting me, it's just...well, no
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one's touched them for quite a while."
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Tommy rubbed his face against her soft chest as she held
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him, then when his mouth was within reach, sucked her nipple
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into his mouth and nursed on it like he used to do on his
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mother's. Beth moved into the tub with the boy and soon had
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him laying across her lap with his head cradled in her arm and
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his mouth still firmly attached to her nipple. He continued
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to suckle and with his hand stroked the breast above the
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nipple and his Aunt just laid back and let his little mouth
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work on her while she gently stroked his entire body. After
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a while, she transferred him to her other breast and he was
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now laying full length on top of her with his body between her
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legs. She held him as he sucked and nibbled on her nipple and
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moaned with pleasure at the contact.
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After about ten minutes, Beth's body raised out of the
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water, and went rigid for a couple of seconds then relaxed
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back down into the warm liquid. "Are you OK, Aunt Beth?"
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"Yes, Yes, dear one, Aunt Beth is very happy," she sighed and
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continued to stroke the small body laying on top of her. She
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could feel his hard little cock pressing against her belly,
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and reached down and gently stroked it until his body shook
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with an orgasm, the held him to her as they both relaxed.
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After a while, she sat up and then got out of the bathtub and
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helped Tommy dry and dried herself before leading him into his
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bedroom, and tucking him nude into the big bed. She stroked
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his forehead and kissed him on the cheek then the mouth as she
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said good night. "Good Night, Aunt Beth, I love you," Tommy
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said softly and closed his eyes to sleep.
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During the night, Tommy awoke and went to the bathroom,
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in the hallway, he heard a moan and a cry come from his Aunt's
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bedroom. Thinking she was hurt, he stuck his head through the
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doorway and looked inside. Aunt Beth was laying naked on the
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bed, with one hand holding her breast while the other was
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feverishly rubbing between he widely spread legs. She was
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covered with sweat and as he watched she arched her back
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raising her body up from the bed and gave another deep moan,
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then collapsed back onto the bed and rested. Tommy wasn't
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sure what had happened, but she didn't look hurt, so he
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returned to bed.
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The next morning he was awakened by his Aunt's fingers
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stroking his cheek and when she saw his eyes meet her's, she
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kissed him and said, "Good Morning, Tomi; how do you feel."
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"OK, Aunt Beth, are you OK?" he replied. "What do you mean?"
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she said, looking at his now apparently concerned face. "Oh,
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I had to go to the bathroom last night, and heard sounds from
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your bedroom,...Like you were hurt." "I'm fine, Tomi, but I
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guess I'm going to have to explain something to you that
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apparently your parents haven't yet...about sex."
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His Aunt then got up from the bed and removed her robe.
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Standing beside the bed and before her wide eyed nephew, she
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then proceeded to explain about the differences between men
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and women's bodies. She ended the lesson by opening her legs
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and parting the lips of her vagina, showed him the parts of
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her womanhood and explained how sensitive various parts were,
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especially her clitoris. She then allowed the boy to feel her
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breasts again, and explore her vaginal area with his small
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hands until she was satisfied that he understood about women's
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bodies and how they differed from his own. She then gathered
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his naked body to hers and sitting him on her lap, gave him
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many hugs and kisses as she explained her plan for the day.
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When she was done, she took him to the kitchen, where they
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both ate breakfast au naturel, then returned to his bedroom to
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get him dressed for the day.
|
|
Tommy was given a pair of white cotton girl's panties
|
|
with high cut legs, a pair of white ankle socks and a pair of
|
|
white girl's style 'Keds' were placed on his feet. His aunt
|
|
the put a half-slip on him and had him step into a pretty baby
|
|
blue sundress, which she then pulled up and after placing the
|
|
1" shoulder straps over his shoulders, buttoned the single "H"
|
|
connecting strap, which ran horizontal just below his shoulder
|
|
blades. Tomi was then seated and his Aunt showed him how to
|
|
do his own hair into the same twin pony tail style he had worn
|
|
the day before. This time however, the ribbons securing the
|
|
pony tails were tied with blue ribbon to match his dress. His
|
|
Aunt then applied light makeup to his face and he was again
|
|
lead to a mirror to see the results.
|
|
For a minute or two, Tommy couldn't believe that the
|
|
pretty girl looking back at him from the mirror was himself.
|
|
He turned this way and that, looking at how the dress was cut
|
|
showing almost all of his back clear down to the waist, except
|
|
for the shoulder and "H" straps. In front, his chest was
|
|
bare, to just above his breasts and the dress was cut to flare
|
|
at the waist outward to where it ended about 6" above his
|
|
knees. "Hi 'TOMI'," he said to the smiling girl in the
|
|
mirror, then turned and hugged his Aunt Beth's still naked
|
|
body and kissed her as thanks.
|
|
Aunt Beth got dressed quickly and they proceeded down the
|
|
elevator and out into the parking lot to her car. As they
|
|
were getting in, Jenny and Suzie approached and invited Tomi
|
|
to go swimming with them that afternoon in the complex's pool.
|
|
Aunt Beth and Tomi agreed and they would stop by around two to
|
|
pick Tomi up and show her the way to the pool. "I guess we'd
|
|
better get you a swim suit too," observed his Aunt as she
|
|
pulled the car into traffic.
|
|
The rest of the morning was spent at the mall, going from
|
|
store to store, with Tomi trying on outfits at every one and
|
|
ended with them returning to the apartment, again loaded down
|
|
with boxes and bags of clothing. After lunch Aunt Beth told
|
|
Tomi to try on the swimming suit to make sure it 'hid his
|
|
little problem'. It was a black and white bikini with a ban-
|
|
deau top. The bottom was black knit Lycra spandex with a
|
|
white waist band. When Tommy was pulling the bottom up his
|
|
legs, his Aunt gently reached out and pushed his balls back up
|
|
into the internal tubes of his groin, then folded his penis
|
|
back between his legs. The tight suit held everything in
|
|
place and to all appearances he now had the normal crotch of
|
|
a girl. "That will do nicely, Tomi, but make sure you never
|
|
undress in front of the girls or they will know you're a boy;
|
|
you could get into a lot of trouble if that happened."
|
|
The girls arrived in a little while still dressed and
|
|
carrying their bathing suits. Jenny explained their problem,
|
|
"Miss Henderson, Mom is having a card party and doesn't want
|
|
us in the apartment; could we change here before going down to
|
|
the pool?" "Sure girls, Tomi why don't you show them to your
|
|
room, so they can change," Beth replied. Tommy lead the way
|
|
and ushered them into his room, as he was turning to leave,
|
|
Suzie said, "Don't leave, Tomi, we can talk while we're chan-
|
|
ging."
|
|
Tommy didn't know what to do, here he was in his bedroom
|
|
with two pretty girls who were about to undress in front of
|
|
him and his Aunt was just down the hall. Before he could
|
|
mentally decide, he looked over towards Suzie and found she
|
|
was already standing nude before him, with a broad smile on
|
|
her face. Jenny had removed her top and was in the process of
|
|
taking off her panties and shorts in a single movement, with
|
|
her back to him and bent forward so he could see her firm lit-
|
|
tle ass and her pussy between her legs as she removed the
|
|
garments.
|
|
The girls talked as they undressed and then put on their
|
|
bathing suits and told him that Jenny was 12 and Suzie 11
|
|
years old. They were sisters and lived three doors down the
|
|
hall on the left with their mother who was divorced. Jenny
|
|
had been in Miss Henderson's class the previous year and Suzie
|
|
would be this year. They both liked the teacher and thought
|
|
she was very beautiful.
|
|
Suzie was a blue eyed little blonde haired girl, with a
|
|
straight-as-an-arrow body. Her breasts were just little bumps
|
|
which looked more like a boy's except for the nipples which
|
|
were larger and stood out just a little. Her hair was medium
|
|
length, extending down to the tops of her shoulders and
|
|
generally straight, except for the little flip at the ends.
|
|
Her pussy was completely hairless, and Tommy's little dick was
|
|
straining just at the sight of it.
|
|
Jenny was a little bigger than Tommy, probably about an
|
|
inch taller and her body was starting to show signs of
|
|
development into a woman. Her breasts were forming and stood
|
|
out about an inch from her chest, the nipples were twice as
|
|
large as Suzie's and her pussy had a sparse covering of dark
|
|
brown hair. Jenny's eyes were green and her skin milk white
|
|
in the areas covered by her tank type swim suit. Her hair was
|
|
very long, reaching almost to her waist as it cascaded down
|
|
over her back.
|
|
The girls were now attired and taking Tommy by the hand,
|
|
lead him back through the apartment and down to the pool.
|
|
They played, and swam, and laid in the sun and had a great
|
|
time, all afternoon. Tommy only had one scare all afternoon,
|
|
they were playing 'Tag' in the pool. Suzie had grabbed the
|
|
waist band of his suit bottom, and as he tried to escape, they
|
|
were pulled halfway down his ass, exposing his tender white
|
|
cheeks to the boys at the pool who hooted and hollered their
|
|
approval.
|
|
Fortunately, they did not come down far enough for his
|
|
little pecker to be seen, and he quickly pulled them back up
|
|
as he turned beet red in response to the boy's cat calls.
|
|
Suzie apologized for having pulled them down gave him a hug to
|
|
ease his embarrassment. Tommy loved the feel of her body
|
|
pressing against his bare flesh and stroked her back as they
|
|
stood side-by-side following the hug, against the wall of the
|
|
pool. "I'm so sorry," Suzie said with tears in her eyes,
|
|
"It's OK," replied Tomi, "they didn't get to see much anyway."
|
|
and patted the girl on the hip.
|
|
The next month Tommy would remember as one of the best
|
|
and most exciting times of his life. He, Jenny and Suzie
|
|
became almost inseparable, spending all of their time to-
|
|
gether, playing or going to movies, or going to the mall. He
|
|
got to see the girls naked many times, but they never saw
|
|
anything below his waist. One of the boys, named Bobby, even
|
|
had a crush on Tomi and attempted to put his hands on her
|
|
every time he was close enough to do so. They had danced at
|
|
a party at the apartment building one evening, but Tomi never
|
|
let him get beyond kissing her and stroking whatever skin was
|
|
left bare by her clothing. Tomi, knew that Bobby had a per-
|
|
petual hard-on, but was not about to take any chances.
|
|
Tommy and his Aunt took baths together every night, and
|
|
he soon learned how to make her climax with his hands and
|
|
later his mouth. She always stroked his little cock and balls
|
|
until he came, but would never let him enter her vagina with
|
|
his cock. She explained to him that this would be called
|
|
incest and was a crime as well as one of the worst sins a
|
|
person could commit.
|
|
The night before his parents were to return, Tommy cried,
|
|
he didn't want to go back to being a boy and having to wear
|
|
those terrible rough boy's clothes. Aunt Beth tried to
|
|
comfort him but every time she released him, he would start
|
|
crying again and his body would tremble and shudder. His Aunt
|
|
held him most of the night and they slept together in her bed.
|
|
In the morning, she told him she would try to arrange the same
|
|
type of vacation for next year, but that was all she could do.
|
|
Tommy returned home, happy with the vacation, but sad at
|
|
returning to being a boy.
|
|
|
|
*********************************
|
|
|
|
CHAPTER 3
|
|
|
|
|
|
DEPRESSION AND BEYOND
|
|
|
|
For the next year, Tommy was continually depressed and
|
|
even though he still got "A's" and "B's" in school, his
|
|
parents could not understand what was wrong. The only times
|
|
he got excited was when he was told his Aunt Beth was going to
|
|
visit, then returned to his previous state when she left.
|
|
Tommy couldn't tell his parents that he hated being a boy, nor
|
|
about the wonderful vacation he had the summer before. His
|
|
mother, noted that her sister seemed to be a positive influ-
|
|
ence on his mental state and approached Beth with her con-
|
|
cerns. They discussed Tommy at length, and Beth explained
|
|
that as an only child and being very small for a boy his age,
|
|
that he didn't get along with the other boys who constantly
|
|
picked on him. He was therefore lonely and was at that stage
|
|
of life where his body was feeling the effects of puberty but
|
|
would probably "grow out of it."
|
|
"Beth, I am very concerned about Tommy, and I am going to
|
|
ask a very BIG favor of you and will perfectly understand if
|
|
you say no. Tommy seems to perk-up around you and gets back
|
|
to a normal mental state. Is there any chance, Tommy could
|
|
spend the summer with you....We will pay all expenses, I
|
|
couldn't ask you to support our son, but we must do something,
|
|
or I'm afraid we'll have to start taking him to a psycholo-
|
|
gist." Both women were crying, and Beth took her older
|
|
sister's face in her hands and replied as she stroked the
|
|
tears from her face. "Janet, I love your son almost as much
|
|
as you do. It's no imposition on me to try and help him. If
|
|
it's what YOU want, I'll pick him up as soon as school's out
|
|
and keep him as long as it takes to bring him around;....I
|
|
only hope I can help."
|
|
As soon as Tommy was informed of the decision by his
|
|
mother, he almost immediately snapped out of the continual
|
|
depression and started acting his normal self. His mother
|
|
knew she had made the right choice from his reaction and felt
|
|
confident that her sister could help her son.
|
|
When the day finally arrived for his Aunt to pick him up,
|
|
Tommy was excited about what lay ahead during the summer. By
|
|
the time Beth finally got there he was shaking from just the
|
|
thought of what was to come and his cock had been hard all
|
|
day. When Beth arrived she hugged the boy and he smelled her
|
|
sweet perfume, then after greeting his parents and spending an
|
|
hour getting caught up on family gossip, they loaded his
|
|
suitcases into the trunk and headed back to her apartment.
|
|
Along the way, Beth pulled into a gas station and after
|
|
checking the women's restroom to make sure it was empty, ush-
|
|
ered her trembling nephew inside. Locking the door, she told
|
|
him to strip, and produced an outfit similar to the one he had
|
|
worn for the trip the previous summer. When he was naked, she
|
|
measured him, and found that other than for the fact that he
|
|
had grown an inch, now standing 5'2" he could still wear most
|
|
of the clothes she had purchased the previous year, the skirts
|
|
would just be a little shorter. Beth took note, that other
|
|
portions of his body had also grown, his erect cock was now
|
|
almost 6" long, but still only about an inch in diameter and
|
|
was surrounded by a light covering of light brown hair. Other
|
|
than his now larger cock, he still looked more like a girl
|
|
than a boy, his skin being smooth and almost hairless. Taking
|
|
hold of his stiff member, she looked Tommy in the eye and said
|
|
"We've got to get rid of this or it will bulge in your
|
|
shorts." She then started gently stroking him, with him
|
|
standing before her until she felt the little jerking convul-
|
|
sions in his cock which indicated that a climax was on it's
|
|
way. Without saying a word she leaned forward and sucked him
|
|
full length into her mouth and proceeded to give the boy his
|
|
first ever blowjob.
|
|
Tommy couldn't believe that his beautiful Aunt was
|
|
sucking on his cock, and loved the feel of her tongue as it
|
|
swirled around his cock head inside her mouth. His entire
|
|
body shook as he came, and he almost fell with the release but
|
|
his aunt caught him and then held him in her arms until his
|
|
breathing returned to normal. He had come in Aunt Beth's
|
|
mouth and rather than her being mad as he expected, she just
|
|
smiled and licked her lips, then kissed him on the cheek and
|
|
told him to get dressed. After fixing his hair and applying
|
|
a light coat of makeup, they left the gas station and returned
|
|
to her apartment.
|
|
On arriving at the apartment, Aunt Beth took him to his
|
|
room and had him strip off his clothing again. She then sat
|
|
down on the bed and had him stand before her as she slowly
|
|
inspected every part of his body. "We have a problem, Tomi,"
|
|
she said, then continued, "you are growing hair on your legs;
|
|
girls don't allow that to happen so we'll have to remove it."
|
|
Tommy just said, "OK Aunt Beth, whatever you say." Without
|
|
further comment, she led him to the bathroom, then covered his
|
|
entire body below the neck with 'Nair' and told him to stand
|
|
still while the lotion worked it's 'Magic' on him. She
|
|
checked small patches on him periodically, then decided it was
|
|
time to remove the lotion. She scrubbed him with a sponge and
|
|
as she showered him with a hand held shower attachment and
|
|
Tommy saw that every place the sponge had been, was now hair-
|
|
less and smooth. This included his crotch, which now looked
|
|
as it had when he was younger, except that his cock and balls
|
|
looked bigger.
|
|
When she was done, Aunt Beth turned off the shower and
|
|
ran a full bath into the tub, adding a bubble bath to the wa-
|
|
ter. Tommy was then told to soak in the tub for a while and
|
|
his Aunt left the room. When she returned she was unclothed
|
|
and Tommy again marveled at her big breasts and wonderful
|
|
female body. She got into the tub with him and gently washed
|
|
his hair as well as every other part of his body. All this
|
|
contact had brought his young cock back to life and she
|
|
giggled when she washed him there.
|
|
After the bath, she dried him off then dusted his body
|
|
with a sweet smelling powder. This made his skin tingle and
|
|
made it feel even smoother than it had before. After drying
|
|
herself she lead him back to the bedroom and cradled him in
|
|
her lap as he suckled her nipples. She then gently stroked
|
|
his body and talked to him about what a sweet boy he was.
|
|
That night they slept together and Tommy was treated to
|
|
another mind-blowing climax when his Aunt sucked him off. He
|
|
then licked and sucked on her tasty pussy until she finally
|
|
told him to stop, so they could get some sleep.
|
|
The next month was a repeat of the previous summer.
|
|
Jenny and Suzie were still there, and other than the fact that
|
|
Jenny now sported large breasts for her age and, Suzie was
|
|
showing signs of developing to about an "A" cup, everything
|
|
went as before. His Aunt added two foam pads to his bras and
|
|
swim suits so that he also appeared to be growing small
|
|
breasts, which made Tomi very happy.
|
|
Aunt Beth was seeing a man named Frank about three
|
|
evenings per week, but she never brought him to the apartment
|
|
and he never saw her boy/girl nephew. Tommy could tell from
|
|
the glow about his Aunt when she came home that she and Frank
|
|
were fucking on these nights which was confirmed in his mind
|
|
by the fact that she would always immediately take a bath be-
|
|
fore holding or touching him after one of her dates.
|
|
Both Jenny and Suzie now had boyfriends and they along
|
|
with Bobby hung around the girls like vultures. As he had the
|
|
previous summer, Bobby was constantly touching Tomi, which
|
|
she/he both enjoyed and hated. She/he disliked it only in
|
|
that she had to be on constant guard that Bobby's hands always
|
|
stayed above the waist, due to what might happen if he dis-
|
|
covered him to be a boy. At one of the parties, the girls
|
|
threw, Tomi ended up kissing Bobby for the better part of an
|
|
hour, to keep him occupied so that he didn't try anything
|
|
more.
|
|
By late July, Tomi was giving the boy hand-jobs to keep
|
|
him satisfied and the first week of August gave her first
|
|
blowjob. Bobby was satisfied with this arrangement as long as
|
|
she continued to give him relief, honoring her statement that
|
|
she wanted to remain a virgin until she got married. Tomi
|
|
didn't mind giving the boy head until he started getting
|
|
insistent, wanting her to do it two or three times per day.
|
|
At that point, she told him to 'Go fuck himself' and refused
|
|
to see him or be anywhere he was at. She had actually liked
|
|
the taste of his cock in her mouth and his cum was salty but
|
|
good. It was just that he got so pushy about the whole thing.
|
|
Ever since his Aunt had started dating Frank, she no
|
|
longer took baths with him, never allowed him to sleep in her
|
|
bed, never stroked his cock to climax, would not allow him to
|
|
even touch her pussy, and only occasionally would allow him to
|
|
feel or suck her breasts. Tommy a healthy 13 year old, had an
|
|
almost constant hard-on and was having to relieve himself two
|
|
or three times per day to keep the bulges out of his clothing.
|
|
He was sitting nude in his room one afternoon performing this
|
|
task, when like a cannon shot, Suzie charged through the door.
|
|
"Let's go swimming!" she squealed then seeing Tommy's hard
|
|
cock between his legs, stopped dead in her tracks. Her eyes
|
|
got big and her jaw dropped open, but she was unable to speak.
|
|
She reached behind her and closed the door, then managed to
|
|
choke out the words, "You're a BOY."
|
|
Tommy was so startled he had stopped in mid-stroke on his
|
|
hard cock, and had made no attempt to cover himself. Then
|
|
during the pause following her statement, finally managed to
|
|
speak. "Suzie, come over here," he said softly and released
|
|
his grip on his still raging cock.
|
|
The girl moved stiffly as if in a trance, but ended
|
|
kneeling before his seated body. Suzie listened while he ex-
|
|
plained that, yes, he was a boy, but he liked the feel of
|
|
girl's clothing better and how he liked to be around girls
|
|
more than boys. That his Aunt let him dress as a girl when he
|
|
visited, but that he could not do it at home for fear of
|
|
discovery. Suzie nodded her head several times during his
|
|
explanation and noted that by the end, her friend was trem-
|
|
bling and shaking throughout his entire body. She put her
|
|
hand on his knee and leaned forward and gave him a kiss on his
|
|
lips and whispered, "It's OK Tomi, I won't tell anyone about
|
|
you."
|
|
With tears streaming down his cheeks, he gathered the
|
|
smaller girl to him and hugged her for all he was worth. They
|
|
remained in this cinch for quite some time, as she stroked his
|
|
body and kissed him on the mouth, neck and shoulders; then
|
|
rubbed her head against his chest. Suzie then took his cock
|
|
in her hand and gently fondled it and probed his balls as if
|
|
to convince herself that they were real, then released him and
|
|
stood between his outstretched legs. In a flash, Suzie was
|
|
standing nude in the same spot where before she was wearing
|
|
her two piece swim suit. Her budding breasts were topped by
|
|
two rose colored nipples which were erect and standing out
|
|
proudly. Her breathing was rapid and she then took Tommy's
|
|
hand and placed it on her belly, then moved it downward to
|
|
her young cunt.
|
|
Tommy's fingers glided over her still almost hairless
|
|
pussy lips and became wet from the juice oozing from between
|
|
them. He opened his fingers and allowed the lips to pass
|
|
between them on either side of his middle finger, which he
|
|
gently inserted into her hole. Suzie reached out with her
|
|
hands and placed them on his shoulders to steady herself as he
|
|
slowly stroked his finger in and out of her, and her body
|
|
trembled from the pleasure he was providing to it.
|
|
After about 5 minutes of this and when her fluids were
|
|
trickling down the insides of her thighs, she backed up a step
|
|
and moving his legs together moved back forward and sat on his
|
|
thighs, with her legs around them to the sides. His hard cock
|
|
was now pressed up against her smooth belly and after placing
|
|
his hands on her breasts, she wrapped her arms around his neck
|
|
and gave him a deep kiss into which it felt she put all of her
|
|
energy and strength. His hands massaged her tender breasts
|
|
and stroked her back, shoulders and ass. Suzie then raised
|
|
herself up and using her left hand guided his cock to the
|
|
opening of her tight little pussy. Suzie then lowered herself
|
|
onto the stiff meat, until she sat with her pussy lips firmly
|
|
against his pubic area.
|
|
They sat like that for several minutes just enjoying the
|
|
feel of each others warm bodies pressed together and his hard
|
|
cock encased in her tight cunt. Tommy then lifted Suzie's ass
|
|
as if to signal and she soon was thrusting up and down on his
|
|
cock like she was riding a horse. It didn't take the excited
|
|
girl long before her body shook with an orgasm, and Tommy held
|
|
her as the waves passed through her, then she started moving
|
|
again. After another 10 minutes, the young boy could hold
|
|
back no longer and came hard into her cunt which triggered her
|
|
again. They collapsed interlocked back onto the chair and
|
|
held each other for what seemed a long, long time.
|
|
When they recovered they got up and walked holding each
|
|
other, then sat on the bed. Suzie promised that his secret
|
|
was safe, but only on the condition that his cock belonged to
|
|
her and made it clear that she intended to use it often. This
|
|
was fine with Tommy and after a leisurely kiss, they both
|
|
dressed and went to the kitchen for a snack. For some reason,
|
|
they were both very hungry.
|
|
For the balance of his stay, this young sex pot would
|
|
manage to get them alone at least three times per day, some-
|
|
times more, and either suck him, fuck him or if her pussy was
|
|
feeling tender, have him fuck her ass. The latter being some-
|
|
thing Tommy really enjoyed, since her ass was even tighter
|
|
than her VERY tight pussy.
|
|
On the Sunday of his last week with her, Aunt Beth broke
|
|
devastating news to Tommy. Frank had ask her to marry him,
|
|
and they would be married that winter. This was the last time
|
|
he would ever be able to dress as Tomi and visit her. Tommy
|
|
broke down crying and his Aunt gathered him to her and cuddled
|
|
him. She then further explained why his parents had let him
|
|
stay the summer; that the alternative was seeing a psycholo-
|
|
gist. He must return to being a boy; but even more important,
|
|
he must act normal when he did so. If he returned to the
|
|
depression, his parents would send him to a doctor and
|
|
eventually would find out about his cross-dressing. This
|
|
would get them both in serious trouble and he would probably
|
|
never be allowed to see his Aunt Beth again.
|
|
This psychology stuff was a real shocker to Tommy, he had
|
|
no idea that his parents were considering any thing like that.
|
|
He promised his Aunt, that no matter what, he would make sure
|
|
that his parents thought he was a normal happy kid.
|
|
The night before he was to return home, his Aunt again
|
|
had a date with Frank. Suzie and Jenny came to the apartment
|
|
and as soon as they found out his Aunt was gone and would not
|
|
return until late, they both undressed right there in the
|
|
living room. "I told Jenny about you this morning, Suzie ex-
|
|
plained, and she wants you to fuck her too." Looking at the
|
|
two girls side by side, Jenny's tits were almost twice as
|
|
large as Suzie's and before he could make any further compari-
|
|
son, both leapt on top of him. Suzie had her pussy pinning
|
|
his head to the carpet as Jenny was sucking his cock. He lost
|
|
track of who was where when, but he knew he had eaten both
|
|
girls and fucked each in all of their holes before they helped
|
|
his exhausted body into bed. Both girls kissed both his mouth
|
|
and cock before leaving him to go to sleep. He never saw them
|
|
again.
|
|
|
|
************************************
|
|
|
|
CHAPTER 4
|
|
|
|
|
|
HOME AGAIN
|
|
|
|
|
|
Tommy returned home and although it took considerable
|
|
acting on his part at times, managed to convince his parents
|
|
that he was again a normal boy. They thanked Beth for saving
|
|
their son and were delighted at the news of her upcoming mar-
|
|
riage.
|
|
For the next couple of years, the only cross-dressing
|
|
Tommy could manage was wearing girl's panties under his normal
|
|
clothing at school. His mother however, complained that he
|
|
must be wearing underwear for 3 or 4 days because there was
|
|
not enough of it in the laundry. He therefore made sure that
|
|
whether he wore it or not, at least 7 pair of underpants made
|
|
it into the weekly wash.
|
|
Tommy had joined the Audio/Visual Club at school since
|
|
extra-curricular activities were pushed by school officials
|
|
and he did not want to play on the sports teams. One side
|
|
benefit of this was that he worked on the stage crew in either
|
|
sound or lighting for the theater productions the school drama
|
|
club put on.
|
|
He was given a full set of keys for the stage and theater
|
|
area since the sound and lighting wiring ran all throughout
|
|
the area. To his delight one of the keys opened the costume
|
|
storage rooms and makeup rooms of the school. Unknown to him,
|
|
several of the girls on the costume committee had seen him in
|
|
the costume rooms fingering the many dresses and lingerie
|
|
located there. They never said anything to him, but told each
|
|
other and giggled at the prospect of what this might mean.
|
|
In High School, Tommy had not had much luck getting dates
|
|
with girls. He still wore his hair longer than most of the
|
|
boys and was physically smaller (only 5'3", 100 lbs.) than
|
|
most also. Whenever he would ask one of the girls out, they
|
|
would say with an incredulous look, "Go out in public with a
|
|
sissy like you? I'd rather die." But during his Junior year
|
|
all of that changed.
|
|
Stephanie, easily the cutest girl in his class (and a
|
|
member of the costume committee), called him one Saturday
|
|
afternoon inviting him to a party that evening at her house.
|
|
Her parents were away for the weekend and it would be fun. Of
|
|
course he accepted.
|
|
Tommy arrived around 7 p.m., surprised to find himself
|
|
the first to arrive. Stephanie was ravishing in a black mini-
|
|
dress and black suede baby-doll sandals with a four inch heel.
|
|
The preliminaries were brief, but unnerving.
|
|
"Take of those silly boy's clothes," she ordered.
|
|
"There's no use pretending with me." He stammered something
|
|
about the other kids, but she had already started to undo his
|
|
jeans, slipping them down his trembling thighs. "My, my," she
|
|
said when she stripped off his briefs, "Such marvelous curves,
|
|
too pretty to hide." She was looking with envy at his body.
|
|
Tommy blushed and his cock stiffened under all the attention,
|
|
and she used it as a handle, leading him up the carpeted
|
|
stairs. "Tonight," she whispered, "our little sissy is coming
|
|
out."
|
|
In her bedroom, soft and scented and piled deep with
|
|
plush and lace, Stephanie left him standing naked before the
|
|
long mirror to go to the dresser. In a moment, she returned
|
|
with a pair of silky panties. "You were made to be dressed
|
|
like a doll," she purred. "Ken in Barbie's prettiest pant-
|
|
ies." Tommy gasped as she slipped the pink panties past his
|
|
thighs, and tucked away his swollen genitals. Before he had
|
|
a chance to protest, Stephanie had wrestled him into a pink
|
|
waist-cinch trimmed with ribbons. He could hardly breathe.
|
|
The next thing he knew, she was hooking him into a pink nylon
|
|
foam padded bra with push-up design. After stuffing the cups
|
|
with scads of her scented panties, she stepped back and
|
|
laughed. "A pretty padded bra is a sissy's best friend. And
|
|
we won't tell a soul what's in the cups." He could only hope
|
|
not, because next she found a pair of sheer pink tap pants
|
|
with garters sewn into the lacy spandex waist. "I wish they
|
|
looked half as sweet on me." She was the most beautiful girl
|
|
he had ever seen and started to protest, but she shushed him.
|
|
"here," she said, pushing him back on the bed, "Let me put
|
|
your stockings on." They were sexy shiny stockings of pink
|
|
nylon and, as she hooked them to his garters, he marveled at
|
|
his reflection in the mirror.
|
|
"You must be the cutest sissy in the world," she bragged
|
|
and he was beginning to agree. But before he could speak, she
|
|
had taken a pair of pink leather high heel pumps from her
|
|
closet and, pushing him back on the bed once again, slipped
|
|
them on his feet. He stood before the mirror seeing his last
|
|
vestige of manhood disappear. But he really didn't care. He
|
|
was remembering how he felt way back during those summers at
|
|
his Aunt Beth's and enjoyed the feel of the garments on his
|
|
body. He wanted Stephanie to tell him again how cute he
|
|
looked, and began to move shamelessly. Stephanie squealed
|
|
with delight and rushed to the closet taking down the most
|
|
beautiful pink lace dress. "How do you like it?" It was
|
|
stunning...lacy soft puffed sleeves with a gathered crepe
|
|
bodice and three tiers of lace for the generous skirt sashed
|
|
at the waist. In Stephanie's dress, he felt just like a
|
|
princess.
|
|
Stephanie sat him down at her dressing table and started
|
|
doing his makeup, applying a liquid foundation to his face,
|
|
she followed this with eyeshadow, liner and mascara to his
|
|
already almond-shaped eyes. She then rouged his cheeks and
|
|
painted his lips a very hot pink. His jewelry consisted of
|
|
pearl earrings, (She applied one to his already pierced ear,
|
|
then pierced the other herself). A strand of pearls around
|
|
his neck, a little teasing of his long hair for half an hour,
|
|
followed by a spray net and his transformation was complete.
|
|
"Beautiful," she said patting his shoulder. "C'mon, you can
|
|
mix us a drink downstairs and we can waste time with giggles
|
|
and girl-talk."
|
|
Tommy had taken two sips from his screwdriver when the
|
|
doorbell rang. "Answer it," Stephanie ordered. Tommy was
|
|
petrified but, under his skirt it didn't show. "Dressed like
|
|
this?" he questioned. "Why not?" she wanted to know. "If
|
|
anyone asks, you're my cousin from out of town." He melted in
|
|
the warmth of her smile. Cautiously, he approached the front
|
|
door, feeling dreadfully exposed beneath his lacy skirt.
|
|
When he finally opened the door, in came the entire
|
|
costume committee, five girls all his classmates (Debbie,
|
|
Heather, Denise, Kim and Carol) they were all crowded into the
|
|
foyer. "Hi sissy," called Heather, laughing. "What a pretty
|
|
pink dress, Sissy," said Carol. They were all taking turns
|
|
squeezing his corseted waist and kissing his painted lips.
|
|
For the first time in his life, other than when with Suzie and
|
|
Jenny, he felt like he really belonged.
|
|
Of course the party turned out to be a pajama party that
|
|
Stephanie had invited him to, and since he had left his
|
|
pajamas at home, the girls marched him right back up to
|
|
Stephanie's bedroom to select for him the prettiest night
|
|
clothes they could find. It was Debbie a beautiful little
|
|
blonde who finally picked out a naughty little satin and lace
|
|
pinafore in baby blue with little matching ruffled back
|
|
panties that tied on the side.
|
|
The night ended as the sun came up on a new day, after
|
|
'Tomi' had eaten all six girls and he thought fucked them all
|
|
also (at least once), as he fell off to sleep, surrounded by
|
|
beautiful female bodies sprawled in all directions. He knew
|
|
that his pretty new friends would never be far from his side
|
|
and that he would never want to be a man again.
|
|
|
|
|
|
|
|
CHAPTER 5
|
|
|
|
|
|
A NEW MISTRESS
|
|
|
|
|
|
The following day, Tomi was kept nude all day as the
|
|
girls explored the extent of their control over him. He
|
|
served as a nude waiter for both their breakfast and lunch and
|
|
whenever he was within one of them's reach, they fondled his
|
|
cock and balls almost casually. By 1:00 in the afternoon,
|
|
Stephanie realized that Tomi had seemed depressed all day and
|
|
thought she knew the reason why. The other girls had gone to
|
|
the store and they were alone in the house, so now was a good
|
|
time to find out if she was right.
|
|
"Tomi, come over here," she called, and as always, the
|
|
boy complied without comment. "Tomi, you don't seem happy
|
|
like you were last night," she offered. Tomi was standing
|
|
nude before this beautiful red head with his head down and
|
|
tears welled to the corners of his eyes, but he said nothing.
|
|
"Tell me what the problem is, Tomi," Stephanie said as softly
|
|
as possible yet still somewhat stern.
|
|
In almost a whisper, Tommy replied, "I...I like being
|
|
with you girls, but, I don't like being undressed all the
|
|
time." The tears started flowing down his cheeks and Stepha-
|
|
nie stood up and hugged the smaller boy to her. "You want to
|
|
wear MY clothes, don't you Tomi," she whispered in his ear, as
|
|
she gently stroked his back and sides. "Please, yes," was all
|
|
the boy was able to choke out. "Oh, my poor sweet sissy, I
|
|
should have known," Stephanie cooed to him.
|
|
Stephanie was wearing a peasant type blouse and Tomi's
|
|
head pressed against her breasts had worked the top downward.
|
|
His mouth rested just above her nipples and the smell of her
|
|
clean flesh and light perfume along with her tender stroking
|
|
had him very excited.
|
|
Tommy kissed her between the breasts and Stephanie
|
|
pressed herself harder against his mouth. She was hugging his
|
|
trembling body to her as hard as she could and it was all he
|
|
could manage to get his hands up to the frilly collar of her
|
|
blouse and pull it down enough to free her breasts. When they
|
|
were clear, he dove on her right nipple with everything he
|
|
had, sucking and lightly biting it, in between licks and
|
|
flicks with his tongue. Stephanie's pale white skin had
|
|
little freckles scattered across her breasts her nipples were
|
|
very dark and stood out like little cones under the ministra-
|
|
tions of his eager mouth. Stephanie could not believe how
|
|
this boy's talented mouth was working over her tits and knew
|
|
that even though he had few dates at school, SOMEONE had
|
|
taught him how to make a woman happy.
|
|
Stephanie, sat down in the chair behind her and pulled
|
|
him onto her lap, cradling his head in her arm so that his
|
|
wonderful mouth never lost contact with her breast. As he
|
|
suckled her breast, she continued stroking his body and
|
|
enjoyed the feel of his smooth skin. After a while, she
|
|
disconnected him and had him kneel between her legs, then
|
|
lifted her skirt and removed her panties. "Put them on," she
|
|
directed as she handed over her silky panties and with a broad
|
|
smile on his face, Tommy eagerly complied. "Now, eat my pussy
|
|
little Sissy, eat it good and I may let you do it again."
|
|
Stephanie's mound had a light covering of bright red
|
|
hair, the same color as on her head. Her lips were swollen
|
|
and partially open from his sucking of her breasts. When he
|
|
parted the lips, Tommy found the inner flesh to be bright pink
|
|
and her little clitoris stood up erect as a cock. Her juices
|
|
were flowing freely from her excitement, and Tommy lapped at
|
|
her slit trying to get every drop. His tongue flicked her
|
|
clit and worked deep into her opening then returned to her
|
|
clit in a continuous and frantic ballet. Stephanie couldn't
|
|
take much of this, the best treatment her young pussy had ever
|
|
experienced. Over the next 25 minutes she came 9 times and
|
|
each time drenched his face with her flow. Finally, she
|
|
pulled him upright, unable to take any more for a while and
|
|
kissed him on the mouth, tasting her own sweet juice on his
|
|
lips. "Oh, you darling little Sissy,...You will be spending
|
|
a LOT of time doing THAT!"
|
|
Stephanie then marched him to the bathroom and handed him
|
|
a razor and told him not to come out until he was hairless
|
|
below the neck. Tomi smiled and gave Stephanie a kiss on the
|
|
cheek then went into the bathroom and whistled as he removed
|
|
the awful hair from his body. When he emerged he was almost
|
|
as hairless as the day he was born and after surveying the
|
|
results, Stephanie gave her approval.
|
|
Back in the bedroom, Stephanie handed him a pair of pink
|
|
bikini panties, matching bra (including two foam pads) and
|
|
garter belt with pale off-white stockings. She watched as he
|
|
quickly donned the garments and noted that he knew EXACTLY how
|
|
to put them on and wear them properly. Last night was not the
|
|
first time this boy had dressed as a girl. A full length slip
|
|
followed, and was topped by a cute floral-print chiffon dress.
|
|
It had big ruffles around the cleavage, collar and hem. For
|
|
accessories she chose a pink belt and a pink hat and a pair of
|
|
black patent leather shoes. Stephanie lead him to the
|
|
dressing table and was going to do his makeup and hair, when
|
|
to her amazement he did it himself and as competently as any
|
|
girl she had ever seen. When he was done, he was one of the
|
|
prettiest girls she had ever seen and she knew he could go
|
|
anywhere without detection.
|
|
When the other girls returned, Tomi met them at the door
|
|
all smiles and giggly. "You did a great job on him," Debbie
|
|
said to Stephanie, "No, he did it himself," she replied. All
|
|
of the girls inspected him and complemented him on how pretty
|
|
he looked and what a good job he had done on his makeup and
|
|
hair. Tomi, blushed and gave each a kiss and a hug for their
|
|
complements. They spent the rest of they day like 7 girls,
|
|
talking, joking, playing games, listening to records and
|
|
having a good time. It was as if they had forgotten that one
|
|
was really a boy. From that day on, Tomi/Tommy had an
|
|
entirely new life. Each day he would go to the stage area of
|
|
the school whenever he was scheduled for a study hall. One of
|
|
the girls would meet him there and invariably he would be
|
|
dressed in one of the many costumes the school maintained for
|
|
their plays. After one of the other girls caught him eating
|
|
Stephanie's pussy in one of the dressing rooms, he soon was
|
|
directed to eat all of them. By then he was most times while
|
|
dressed, ordered to provide one or more girls with sex in some
|
|
form. Usually he had to eat their tight little snatches, and
|
|
sometimes they wanted to fuck either vaginally or anally.
|
|
After school he would be told which girl's house to
|
|
report to, and once there, either served them as a waitress
|
|
with no panties, or would be dressed in frilly clothing to
|
|
serve them. The girls would always stroke his cock and balls
|
|
whenever he was within reach, because they had decided that if
|
|
he was hard and no one needed his cock for sex, then he must
|
|
put on a jerk-off show for the girls present.
|
|
The first time he was told to put on a show for the
|
|
girls, he had refused. Stephanie, the most dominant of the
|
|
group, put her knee in his crotch and busted his balls pretty
|
|
bad. He had doubled over on the floor, and she and Debbie had
|
|
removed his clothing, then Stephanie again demanded that he
|
|
jerk-off for them. When he groaned that he couldn't, Stepha-
|
|
nie pulled his scrotum and smacked his balls hard! Then lead-
|
|
ing him by his balls, which she squeezed in her hand, she led
|
|
him to the TV and told him to sit on it.
|
|
She told him to jerk-off or she would twist his balls
|
|
off! He didn't respond, he was exasperated and helpless,
|
|
Stephanie twisted, and Tommy winced, groaned, bent forward,
|
|
shrieked, THEN he took his cock in hand and he beat it off for
|
|
them. He half filled a drinking cup, cumming four times.
|
|
Then was forced to drink his own cum while the girls cheered
|
|
him on.
|
|
Their Senior year, Stephanie got into bondage and
|
|
discipline, having been given some books on the subject, by
|
|
other girls she knew. One day she called Tommy to her in the
|
|
back stage area and showed him a cock strap and told him she
|
|
wanted him to wear it at all times unless she gave him
|
|
permission to remove it. He didn't want to do it but knew
|
|
Stephanie would bust his balls again if he didn't. So he let
|
|
her put it on him, under his balls and over his cock; making
|
|
both stick straight out. That evening all the girls saw the
|
|
new strap as he served refreshments to the girls and as soon
|
|
as they had stroked him to hardness, he was ordered to dance
|
|
for them. His balls were shaking and jiggling as he danced
|
|
and all of the girls watched and teased him. When Stephanie
|
|
tired of watching him shake his genitals, she said, "OK, now
|
|
show us how you jerk-off!" Which he did although red from the
|
|
embarrassment not the sex.
|
|
Tommy had become their sex slave, and tried to keep all
|
|
six mistresses happy. This was almost too much for one boy to
|
|
accomplish as they sometimes would make conflicting demands
|
|
upon him. Stephanie, however, established herself as the
|
|
primary Mistress and none of the others, ever tried to
|
|
contradict her.
|
|
Stephanie, would often have him come to her house, for
|
|
one-on-one training. She would strip him and tie his hands
|
|
behind his back, then take a shower and have him dry her pussy
|
|
and anus with his tongue. She would take him for walks naked
|
|
at night, with a leash tied to his balls and threaten to take
|
|
him to friends houses, if he did not immediately obey her
|
|
every command.
|
|
She celebrated her good luck by ordering him to bend over
|
|
a footstool and with his legs spread very wide, whipped his
|
|
buttocks and inner thighs with a belt, making him count the
|
|
swats. He remained in this position while she sat behind him
|
|
and squeezed his testicles awhile. At other times, she would
|
|
tie him in her dad's workshop, with his wrists bound overhead
|
|
to a hook on a beam, and would twist a piece of plastic
|
|
covered wire tightly around his cock to keep him erect. Then
|
|
attach alligator clips snapped onto the tips of his nipples,
|
|
the teeth biting hard into his flesh. She made him stand on
|
|
tip toes for hours, the clips chewing into his nipples and
|
|
amused herself by brushing his penis with a stiff brush.
|
|
Occasionally, Stephanie would fuck his ass with a dildo,
|
|
her older sister had given her. When she told the other girls
|
|
she had done this, they all wanted to see it, so that evening
|
|
she did it in front of all the girls. Tommy climaxed from the
|
|
ass fucking with the dildo, and it became a daily part of the
|
|
show thereafter. It was only a question of which girl, with
|
|
which dildo his backside was being plowed.
|
|
The night of their graduation party, Stephanie took him
|
|
to the party fully dressed as a girl, with his hands bound
|
|
behind his back. He was dressed in a bra, panties, garter
|
|
belt, stockings, sheer blouse and short denim skirt. He had
|
|
on full makeup and Stephanie had plucked his eyebrows so that
|
|
they were definitely female in appearance and had sprayed him
|
|
with perfume. She wore her older brothers clothing and when
|
|
they arrived at the party, told the other kids that they had
|
|
challenged one another to dress up in each other's clothing.
|
|
Tomi had taken the switch to heart, she added pointing out his
|
|
plucked eyebrows, shaved legs, and lifting his skirt to reveal
|
|
his panties, garter belt and stockings. Tommy's friends
|
|
stared as he reddened. Stephanie told them that he had balked
|
|
at going to the party and that she had been forced to tie him
|
|
up before they left.
|
|
For the rest of the party he was teased unmercifully by
|
|
his friends and their dates. He was totally humiliated, and
|
|
begged Stephanie to take him home, but they stayed the entire
|
|
party. Some of the boys sat beside him and asked him what it
|
|
was like to wear girls clothing and one named Dennis even
|
|
stroked his thigh when he thought no one was looking.
|
|
Stephanie, however, observed it and whispered in the boy's
|
|
ear, that Tomi would give him a blowjob if he wanted and if
|
|
she could watch. "Why Not!" he replied, and Tomi was lead to
|
|
another room, the door closed and locked behind them.
|
|
Tomi was placed on his knees and Stephanie unbuckled the
|
|
other boy's pants and lowered them. "Isn't she pretty,"
|
|
Stephanie said as she stroked the boy to hardness. "Damn near
|
|
as good looking as you," he replied. Stephanie then lead
|
|
Dennis to Tomi and placed the hard 7" cock to his lips. Tomi
|
|
knew he had no choice so he gave Dennis the best blowjob he
|
|
could with his hands bound behind him. Stephanie watched with
|
|
interest as Tomi 'deep throated' the boy and thought to
|
|
herself that "this is not his first blowjob either." Dennis
|
|
came hard, but Tomi managed to swallow almost all of his cum;
|
|
then Stephanie, who had been fingering herself throughout the
|
|
show, ripped off her panties and forced her pussy into his
|
|
mouth.
|
|
Dennis watched as Tomi worked over Stephanie's fine cunt
|
|
and while watching grew hard again. Seeing this, Stephanie
|
|
looked at him and said, "Fuck his ass, do it real good too."
|
|
Dennis needed no further encouragement and soon was buried to
|
|
the hilt in Tommy's tight ass, and stroked hard, pushing
|
|
Tommy's face even deeper in to Stephanie's pussy. Stephanie
|
|
was now coming almost continuously and when Dennis shot his
|
|
load in Tommy's ass, Tommy also came without anyone ever
|
|
touching his dick. They collapsed in a heap on the floor and
|
|
when they emerged the party was over. Both 'girls' kissed
|
|
Dennis goodnight and he thanked them for the good time, whis-
|
|
pering in Tommy's ear that he would never tell anyone about
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it. Stephanie, however, made no such promise.
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On the way home, Stephanie looked over at her still bound
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passenger and said, "You had to do it sometime, if your going
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to live as a girl, AND YOU WILL BE LIVING AS A GIRL FROM HERE
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ON OUT!"
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*********************************
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CHAPTER 6
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COLLEGE
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Stephanie took him with her to college when she left
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after graduation, where he assumed the full-time identity and
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life of a woman. He served as her housemaid and body servant.
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The other girls attended the same college and on weekends they
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had parties at Stephanie's apartment. The feature attraction
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at the parties was a little brown haired slave girl named Tomi
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who had been put on hormone treatments and now had breasts
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which measured "34A" but almost filled a "B" cup bra. Tomi
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was still smaller than the girls standing only 5'4" and 110
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lbs. and when dressed in his 'Roman slave' costume with it's
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short white skirt, tunic and sandals looked the part of a
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young girl. His hair now reached almost to his waist in back
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and was worn straight, parted down the center of his head.
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The girls liked to assume the role of 'gladiators' and
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would tie him face down on the bed with his knees spread apart
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on the floor and then slam 7-10" strap-on dildos in and out of
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his poor young ass until he came on his own. Occasionally,
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one of them would allow him to fuck her, but they seemed to
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prefer making love to a small thin girl rather than his man
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meat. Stephanie, however, allowed him to fuck her almost
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every night, AFTER she tired of his talented mouth.
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At the beginning of her Sophomore year, Stephanie wanted
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to pledge a Sorority, called 'Beta Delta Omega' which the
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girls in confidence said meant "B & D Forever" and consisted
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of girls into Female Domination of men. In order to gain
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admission, Stephanie had to present her slave to the Sorority
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at a party to be held and demonstrate her control over him.
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Tommy was not told what was going to happen only that Stepha-
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nie was taking him out for the night and that they would be
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going to a Sorority party.
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When they arrived at the house, Tomi was lead inside by
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Stephanie and found the room filled to capacity with over 100
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beautiful women. He was lead into a large living room off the
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center entrance hall and was told to stand in the middle of
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the room. When the door was closed behind him, the room was
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in total darkness until a powerful desk lamp was turned on,
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spotlighting him in the center of the room. It took a few
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seconds for his eyes to adjust to the dim light and it was
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then that he realized that all of the women he had seen when
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he entered the house, now surrounded him. The room was silent
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except for a few whispers, until one of the girls spoke from
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the darkness.
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Tomi was asked his name and told that his mistress,
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Stephanie had applied for membership in this sorority, and
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that in order for her to be accepted, HE would have to undergo
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some initiation rites. He was asked if he wanted his
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Mistress to be accepted and if he were willing to do what was
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necessary to help her. He responded that he was willing to do
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anything for Stephanie. "VERY GOOD," said the voice from the
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dark, "Start by Undressing."
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Tomi suddenly became afraid, he had been nude in front of
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the six girls many times, but there were over 100 here and he
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was reluctant to show them his feminized body. He looked at
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the girls closest to him and noted they were all holding large
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paddles and they way they were gripping them indicated to him
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that they were just looking to use them. He quickly stripped
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down to his panties and bra and his softly rounded form and
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swelling breasts brought whispers of appreciation from some of
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the girls in the room. When he hesitated for a second, the
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next instruction was both verbal and physical. With what he
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was sure wall all of the power the girl could muster, one of
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the girls hit him square on the ass with her paddle, while
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another reminded him that he had been told to take off his
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clothing and that meant ALL of his clothing!
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Tomi quickly removed his bra and again heard many
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whispers of appreciation at his well formed breasts. When he
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hesitated again, he received another hard whack on the rear
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end. He now knew that whatever else was going to happen to
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him, he was going to have to stand naked before a room full of
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over 200 female eyes. When his clean shaven crotch came into
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view he once again heard many whispers of admiration at the
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work Stephanie had done. He was then told to bend over and
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spread the cheeks of his ass and turn slowly around the room,
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red from head to toe he slowly complied, just missing another
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whack with the paddle.
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The voice then told him to circle the room, facing each
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girl in the front row and presenting his genitals to her. He
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was given a small saucer that he had to place under his
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testicles before stepping in front of each girl, allowing them
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to pull, squeeze, and probe him as they pleased. Many of the
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girls also worked on his breasts in addition to his cock and
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balls and it was during this part of the initiation that he
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started to develop an erection.
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After each girl in the front row was finished with him,
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he was told to go back to the middle of the room and jerk off
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in time with a record that began playing on the record player.
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By now his penis was fully erect and frankly he was looking
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for some relief. Having jerked off for the girls many times,
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this was nothing new, so he grabbed himself and to the cheers
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and clapping of the girls brought himself off in a tremendous
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climax which shook his entire body.
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At this point several more slaves were brought into the
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room and Tomi was made to suck each to a climax, swallowing
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all of their cum. He was told that if he lost any, he would
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receive a whack for each drop lost. Again he received cheers
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as he performed above apparent expectations. One of the other
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slaves was then told to fuck Tomi's ass, and soon Tomi felt
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what had to be a 10" long and very thick cock working it's way
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up his ass. He relaxed his ass and without any trouble the
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boy was buried to the hilt. As his ass was being fucked, he
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reached out and drew the other slave back to him and sucked
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the boy's cock; this brought a resounding cheer and applause
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from the girls who had not expected such a show.
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Needless to say, Stephanie was accepted into the sorority
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and Tomi became the 'Property of the House' and had to service
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any girl at any time. Only Stephanie, however was permitted
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to discipline him. He lived for the next 6 years in that
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house, while Stephanie got her BA, MA, and PHD degrees. Upon
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graduation with her doctor's degree in psychology, Stephanie
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set up practice in a town nearby and she and her housemaid
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lived together for many years.
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