LGBT Stories

Tim was a sensitive young boy, bright and intelligent, but lacking many of the physical characteristics of his father, Joe. The father had wanted a son who was interested in sports, hunting and fishing just like himself. Unfortunately, through no fault of his own, young Tim could not measure up to the desired image. Joe had expected his son to grow up to “be a chip off the old block” and when he didn’t, his father felt “cheated”. Tim might have grown up the way his father wanted if he hadn’t contracted Polio at the age of eight. The youth was paralyzed from the waist down. Though he did completely recover the use of his legs through a long series of operations and physical therapy, the doctors felt his growth had been impaired. He would never be as big or as strong as he might have been. Due to his illness, Tim also missed a lot of school and was two years behind his age group. These shortfalls caused the father to ridiculed his son whenever he failed to satisfy the man’s absurd notion of what his child should be like. When this occurred, Tim sought consolation in the loving arms of Rita, his mother. Here he found the love and emotional warmth he so badly desired. This only added to his father’s frustration and reinforced his resentment against both his “sissy” son and his “coddling” wife. This hostility was augmented by the “darts” Joe received from his macho chums at work whose sons all played Baseball and Football. His constant bitterness manifest itself in a pattern of physical, mental and emotional abuse against both the mother and son. As most often happens, the mother, protecting her child, transferred her love from the husband to the son and vice-versa. Tim, now in the initial confusion of puberty, misunderstood his mother’s attention and developed a strong personal attachment to Rita, her belongings and more specifically … her clothing. Any personal item of his mother’s became a symbol of the good things in life to the confused youth. Everything that belonged to her was pretty or beautiful or made him feel safe, warm and “fuzzy”. Everything that belonged to his father was rough, ugly, caused him pain and got him into trouble. He rationalized, if he had been born a girl, he wouldn’t have been expected to be knowledgeable about cars, guns, sports equipment or tools, all the things he hated.

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Mary had caught her stepson, David, looking up her skirt as they sat watching TV. He was lying on the floor, at an angle to her crossed knees. Casually, in an effort to be subtle, she adjusted the drape of her misplaced skirt, at the same time reassuring herself she hadn’t exposed all that much. The most David could’ve seen was the welt of her nylons, possibly the garter straps and maybe some bare thigh. This wasn’t the first time she had caught her stepson trying to see up her skirts. She had caught him staring down her blouse when he held a chair for her or down her robe when she bent to kiss him goodnight. She suspected he was also guilty of peeking through the keyhole in both her bedroom and the bathroom doors. While this adolescent voyeurism had initially made her quite uncomfortable, Mary had recently become aware that she secretly enjoyed being spied upon. Knowing her stepson found her attractive boosted her ego. In the last few months she had accepted his peeking and at times, was even guilty of provoking it.

David was sixteen, her only child by marriage. Ron, David’s father had been her husband for three years, then vanished one night without a trace. His first wife, David’s mother, had left both of them, for a traveling salesman. Mary, who had dated Ron before he married David’s mother, got him on the rebound after the uncontested divorce. Everything had gone well for awhile, even David’s acceptance of her as a surrogate mother. Then they began having problems. Ron went out for cigarettes one night and never returned. A missing person’s report had been filed and the local police had investigated, but no clues to his disappearance had ever been found. The court awarded David to Mary’s care after his real mother had refused to take him into her new household.

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While Paul was still a toddler his father and uncle were killed in an airplane crash. They were twin brothers who owned an employment service that provided household help, such as maids, cooks and bartenders, to the rich. It wasn’t a large business, but it was somewhat successful. Neither brother, Tom nor Dick, had expected to die so young and therefore carried very little life insurance. All the profits, other than those they took out in salaries, went back into the business. Each brother, therefore, left their wives, Nora and Karin, strapped for money to support themselves and the two small children they left behind. The two women quickly realized that they had but two choices, sell the business or try to run it themselves. When they discovered, that while successful, the business held little appeal to potential buyers since it could easily be replaced by the competition just by waiting for it to go under. It was his Aunt Nora who came up with the idea that they sell her smaller house, and that she and Renee move in with her sister-in-law Karin and Paul and that they convert the dinning room and the third bedroom into an office suite from which to run the business. Each woman would, initially have her own bedroom to share with her child. Since both Paul and his cousin Renee were toddlers this presented no problem. Later, as the children and business grew, they expected to find outside office space and “give” Paul and Renee their own rooms.

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My parents died in an automobile accident shortly after I was born. The probate court decided that I was to be raised by my mother’s younger sister, my Aunt Lilly, in accordance with my parent’s will. My Aunt, barely an adult herself, just twenty-one years old, was my only living relative. Little did the court realize that Aunt Lilly unfortunately lacked the necessary knowledge, experience and most importantly, attitude to raise me like a “normal” boy. That’s not to say that Auntie raised me poorly … only much differently! I’m sure the reader will better understand as my story unfolds. Auntie had herself been brought-up in a fatherless household. My grandfather had run away leaving my grandmother to raise their two young daughters all by herself. Granny, after her husband left her, became a very disillusioned and spiteful woman, hating all men and teaching her two daughters that men, as a gender, should never be trusted. Somehow my mother overcame grandma’s teachings, met my father, got married and had me. Aunt Lilly, on the other hand, accepted my grandmother’s opinions as fact and never dated, remaining, to my knowledge, a virgin.

She was from the “old school”. This meant that I wasn’t allowed to play with the other children if the group included any boys and even certain girls of whom she didn’t approve. Namely those who were impolite, rude, rough, loud-spoken and/or aggressive by her standards. Over a period of just a few years she excluded every normal boy from my small circle of friends. This eventually excluded all the children since those she didn’t drive away choose not to play with me. Aunt Lilly, by todays standards, raised me to act more like a girl than a boy. The kids thought of me as a “sissy”. By this I mean, sensitive, polite, courteous and obedient to my elders, especial females. This exclusion from having any friends my own age fostered my desire to be with adults as much as possible since they were more receptive towards my sensitive nature. Of course this really meant adult women since I seldom encountered any adult males except as tradesmen or the husbands of my Aunt’s friends and most of the time I was “shielded” from them by either the maid, the cook or my Aunt. I always wanted to be with the adults, especially my Aunt and her lady friends. I discovered, at an early age, that being with women was more interesting.

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Part I

“I wonder where Brad is? He knows you’re coming, you’d think he’d stick around. Oh, I hope he’ll turn up soon, otherwise you’ll have to drive back in the dark.”

“Rita, don’t worry about the boy so much. Brad is like every other sixteen year old boy. He’s probably driving around with his friends looking for girls and forgot I was coming!”

“Well, aah, I don’t think so!” His mother stumbled to say. “That’s something you and I should probably talk about before you leave. Your nephew is somewhat different from what you might expect from the average sixteen year old boy. Sharon, you haven’t seen him in over a year, he’s changed. He doesn’t spend much time with the other boys in the area, he seems to be more a loner.”

Rita and Sharon were sisters. Rita, Brad’s mother was thirty-five, married to Tom and lived the unsatisfied existence of the average house wife. She had been a lovely girl in her youth, attracting quite a bit of attention from all the boys. In her senior year, she fell in love with Tom Hennesey, the high-school football team’s star quarter back. After the victory dance, convinced that Tom also loved her, she agreed to go to a local motel with him. Tom, typical of most boys that age, had been neither gentle, nor concerned with her needs, only interested in his own satisfaction. She’d lost her “maidenhead”, suffered considerable pain, was not sexually satisfied, and needless to say was confused by Tom’s selfishness. Even worse, she became pregnant with Brad. Tom and Rita discussed their alternatives, agreed to marry and with the help of both sets of parents, set up housekeeping. Over the years, all her dreams of the good life went out the window. With nothing to look forward to, Rita eventually slipped into a casual attitude towards her appearance. She gained thirty pounds, wore less attractive clothes and became exactly what she looked like … an average mother/housewife.

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My story is strange, unique, but also wonderful. I was my parent’s fifth and last child. I have four older sisters, Mary, Carol, Barb and Judy. I guess my folks wanted a boy and kept trying till they had me. They must have been serious about trying to have a son, since my sisters are no more than twelve to sixteen months apart in age. We lived on a small family farm in Ohio, between Columbus and Circleville. Since I was the only boy and the baby of the family, my sisters made a big fuss over me. Mom and dad were obviously too busy, during most of the day-light hours, with the running of the farm. This left the responsibility of my care to my sisters. Not only did they feed me, bath me, dress me, but they also taught me all the things I needed to learn as I grew up.

This constant care brought us very close together, especially myself and my two oldest sisters, but at the same time it developed in me an identity problem. We spent a lot of time together playing all kinds of games like, jump-rope, jacks, tag and house. Throughout my “formative” years, the older two, Mary and Carol, treated me like they treated their other sisters, by that I mean, just like one of the girls.

Since our farm wasn’t very prosperous, there wasn’t a lot of extra money to be spent on non- necessary items, especially non-essential clothes. This wasn’t a problem for the girls, because they wore each others hand-me-downs. For me, the only boy in the family, this was a definite problem. This was solved, in the beginning, by my wearing my sister’s shirts and jeans, even though they were obviously “girl-clothes”. Oh, I had “boy-clothes” after I started going to school, but just enough to get by on. As soon as I got home from school, I would change into my sister’s hand-me-downs for play and chores. I also wore their underwear, after all, at that age it wasn’t all that much different. No-one at school ever found out that under my clothes I wore cotton panties instead of jockey shorts. In fact, I didn’t realize the difference myself, till I was much older and by then it didn’t bother me.

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Mom had gone out shopping and wouldn’t be back for an hour. This was my chance for a little fun.

I went to my dresser and fished out the panties from their hiding place.

They were only plain cotton, but at least they were pink. They were a little worn, but they fit me perfectly. When I had found them in the neighbors’ trash can, I had known that they would be nice to wear. I had been hoping for a break like that. I had taken them home and secretly washed them.

I took off my clothes and put them on. Panties…! They felt so good on me. They looked so good! No fly in front: these were GIRL’S clothes. I loved girl’s clothes, and the panties were the first piece of girl’s clothes I had ever owned. I ran my hands over them. I ran my hands over the front, where there was no fly. I felt my little dick, captured inside the panties. It wasn’t very big, but for an eleven year old boy, it was okay. I lay down on the bed and fondled myself through the flimsy cotton.

Then my bedroom door opened. It was Mom! I hadn’t heard her come back. She wasn’t supposed to be back for another half hour or more. I was paralysed.

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I was 16 years old when I had my first man. He was the man who turned me on to the fact that I was gay, feminine and a crossdresser. I had always felt more attracted to boys than girls and had many girl friends and few boy friends and this is my true story.

That summer I found a job cleaning a ladies lingerie store for a wonderful gentleman I will call Bill for this story. I had always tried to be a boy, I played hockey, football and baseball. I did all the “boy” things but was always out of place. In truth I was always small, girly and feminine no matter how hard I tried. It was who I was and Bill was the first to acknowledge this.

I had been working there about a week and every night Bill watched me. I liked him watching me because he seemed so much like me. Soft, feminine not hard and mannish. He too was on the thinner side, soft features, long blond hair. I should tell you about me, I was about 5-4 then maybe 125 lbs and had long medium brown hair. I had a nice curved ass and was well hung even then, almost 8 inches. Today I am still small only 5-9 and 165 lbs but that suits who I am.

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I was just sitting there in the cafe during school lunch break, Joe had said he
would meet me at about one o’clock, but there was still no sign of him. So I
sat there leafing through some work that I was meant to have done weeks ago for
that afternoon’s class, same as always there then! If Joe didn’t turn up in
the next five minutes I would set off for school without him. Those five
minutes came and went and still there was no sign and he didn’t seem to have
his mobile turned on, damn fool. After one last look around the small bar I
grabbed my bag and headed towards the exit. It was on the way there that my path
was blocked, a middle-aged man in a suit, probably aged around his late-30’s
stepped out in front of me. It was the same man that I was sure had been watching
me whilst I eat my lunch, but I had put that down to simple paranoia. Though
once the guy realised he had blocked my way he was all apologetic and held the
door open for me. Giving him a quick thanks and turning towards school the
incident didn’t really enter my mind again, I was too worried about this afternoon’s
work and wondering where Joe had got to.

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