LGBT Stories

Case 23

Patient Name: Toni Lynn (a.k.a. Tony M.)

Case Number 76-71

Initial Visit:

Patient was 19 years old. When I first went to the examination room, I saw Tony was sitting with his back to the door. His long hair was tied in a braided poni-tail. Looking at him from the back, at first I thought that Tony was a girl. After all, one would only expect to find a female patient waiting in a gynecologist’s exam room.

Tony turned around when he heard me enter the room. He was wearing only a T-shirt and a pair of jockey shorts.

“Hello Doctor Jenkins” he said.

“Good Afternoon, Tony. I must admit a certain surprise to find a young man waiting in one of examination rooms! My patient list says I should be seeing a young woman named Toni, with an `i’ “, I said.

“I’m quite surprised to be here, too.” Tony explained. “Fortunately, your receptionist spelled my name in the feminine manner.”

Wondering what this was all about, I asked, “So, how do you think I can help you, since you are male, and as a gynecologist, my specialty is women?”

Relating his story, Tony began, “Well, Dr. Jenkins, I’m not really sure I am male.”

My interest was peeked. “Hmmm. How so?”

(more…)

The letters above the foyer spelt out the words ‘America On-Line’. It hadn’t been that easy to find, I had expected the building to be in a slightly more upmarket section of the city.

The reception itself was alright, in a spartan fashion. I made my way over to the receptionist. An overweight, unshaven man stuffed into a security guard’s uniform. “Excuse me,” I said. “Who do I have to talk to about member’s addresses?”

He slowly ran his eyes up my body to my face. Normally I enjoy that sort of thing, but not from a toad of a man like him. “Uhh?” He replied.

I repeated my question slowly and clearly for him.

He thought about it for nearly a minute and then shrugged. “I dunno.”

Terrific. You’d expect them to put somebody in reception who wouldn’t lose a battle of wits with a three week dead cockroach. “Someone who is in charge of AOL subscriptions.”

He thought about this further. “Umm, I don’t know. I only answer the telephones.”

“Can I speak to your boss then?”

“I expect so, he has a mouth and ears.” He looked at me expectantly. “That was a joke, gettit? He has a mouth and ears so he’ll be able to talk to you. Hurr Hurr Hurr.”

(more…)

I was bored, I had tried everything but nothing seemed to interest me that day. Even writing another chapter of my latest story didn’t get me going. There was nothing for it, I needed a break.

The question was, where shall I go? After some deliberation I settled on Hollywood, well I hadn’t been there for ages. I decided to travel light and only packed four suitcases, I was only going for a day or so and I wouldn’t need that much.

Only five hours later I was booking into one of the more exclusive hotels in LA. It was very plush and very tastefully decorated. The bellboy thankfully put down my cases as I surveyed the suite. “Yes, this will do very nicely.” I told myself.

I heard a cough and turned to see the bellboy standing expectantly by the door waiting for his tip. “Oh, pardon me.” I sauntered over to him watching his eyes drifting over my ample bosom. He seemed more than slightly nervous and he didn’t appear to be that old. Maybe 19 but certainly no older. “So, you want a tip do you?”

(more…)

I don’t care whether you tried to surprise me or not, when you meet me at church you will please be dressed appropriately!” I was having one heck of an argument with my college-age daughter who “surprised” me by coming home for Sunday and meeting me at our church. Normally, I would be pleased to see her anytime and anywhere — but today she came prancing into church and plopped herself next to me on the pew showing everyone everything she had and leaving nothing to the imagination. She was dressed in a lovely blouse/mini skirt set. The blouse was thin and silky, leaving nothing to the imagination as her braless breasts bounced under the thin material causing her young nipples to give a free show to the whole church. Her mini skirt was so short that she had no choice but to give free glimpses at her lovely smooth legs and her satin panties (pink they were) under her skirt. Her makeup was much to much for church — and, well — I just felt uncomfortable with her dressed that way.

“You’re a prude, dad,” she quipped. “Anyhow, I just came home to meet my brother’s new squeeze. I hear she’s a real winner!”

“I wouldn’t know about that”, I replied. I hadn’t met my son’s newest girl friend. But being 17, he seemed to be going through them quick enough.

“Well, behave yourself”, said Julie (my daughter). “Jack said he was bringing her here to meet me today and I want to give a good impression.”

“Well, the next time you pop up at church, just wear something decent!” I wasn’t finished with my argument and felt a little put aside by Julies’ changing the subject. But that was how life was right now.

(more…)

Sandy’s breasts were heaving — she was pinching and tweaking her enlarged nipples as her head thrashed back and forth and her hips and ass squirmed on the silken bed coverings. “More — More — don’t stop — make me cum!”, she screamed. Her sweat-covered body was being driven into a frenzy by Becky, her sister-in-law whose tongue was dancing on her clit like a violinist dancing on his strings. “Don’t stop — PLEEEASSE — make me cum!”, she pleaded. Becky knew just how to touch and play with Sandy’s body, bringing it to the throes of orgasm time and time again. And then it happened — in a sudden shriek Sandy’s body tensed up as she was driven over the edge by an expert at oral love.

She layed there for some time as Becky softly caressed her lush, naked body. Her breasts were large, like Becky’s — and her feminine form was filled with every interesting curve that rightly belonged to young 20-something women. They were lovers now, lesbian lovers who shared another secret — the secret of what they had done with Sandy’s husband, Mike.

Sandy and Mike had been married for seven years. He had known all along that his wife had lesbian tendencies — and he even encouraged them, hoping to be drawn into a soft three-way sexual dance. It never happened — but it still turned Mike on to know that his wife was at times in the arms of an attractive female.

Becky was Mike’s sister — older than Mike by only two years. She was a dominant personality her whole life, and Mike always yielded to the sister that he loved. Becky knew this — and, with Sandy’s help, she used it against her younger brother.

(more…)

I can see you from behind as I enter the bar. Your long slender body perched atop the barstool, catches my attention as I take a table behind you. I pause a few moments to take you in. Your brown wavy hair cascades down to the tip of your buttocks in lustrous curls, catching the light of the neon signs. As you talk to the bartender, your head sways, causing your hair to flow gently across your white satin dress, like an ocean of brunette curls lapping against your shore.

Your outift is skintight, enhancing your wonderully long curved body. Its tight satin rides high on your thigh and low down your back, exposing your deep, dark, exotic complexion. I can follow the line of your fishnet stockings disappearring down impossibly long legs into your high heels and up into your nether regions. I get a tingle up my spine as I appreciate the length of your body, its curves, and your shimmering long hair, and for a moment I am in bed with you, locked in a passionate embrace.

(more…)

Every day I looked forward to getting on the bus because I knew she’d be on it. Since the first time I took this bus, and saw her, I changed my schedule so that I could see her.

She always sat near the front of the bus. I’d get on, give my fare to the driver, turn, and there she was. Always two rows back, on the right. I was always startled, even though I knew she’d be there. Her beauty knocked the wind out of me. Our eyes would always meet, I’d smile, then move on, and sit a few rows behind her.

I wanted to sit next to her. To feel her long hair brush against my arm as I studied her long legs, or made polite conversation. But the bus was always practically empty. It would be presumptuous to sit next to her.

She was tall. With beautiful auburn hair that flowed down to her buttocks in thick soft waves that played with the light. Her soft European features, with high cheekbones, full lips and blue eyes were always stunning. She tended to dress in a conservative business suit, not too racy, but incredibly sexy, with high heels and understated jewelry. Every time I walked past her, I could catch a whiff of her perfume. So delicate. Light.

(more…)

As I reached around her, to embrace this gorgeous beauty for the first time, my body pressed up against hers and I felt her swollen cock pressing up against mine. She made a modest thrusting motion as our bodies became entwined, indicating her desire to fuck me. I grabbed her ass, tight and wrapped in red leather, and pulled her closer. She was breathing on my neck, melting any remnants of resistance from me.

I reached up and grabbed a handful of her long dark mane in my fingers. It was so thick and soft, like a long silk blanket. I wanted her hair to caress my dick. To feel the shiny curls wrap themselves around me, covering my balls, and begin stroking me. I wanted to bury my dick in her ass and lose my head in her hair while caressing her firm tits. She could sit on me, bringing her asshole down on my cock, and I could reach around her and stroke her dick while getting lost in her dark curls that flowed down her back.

(more…)

I’ve been rooming with Bob for two years now. He and I met about 5 years back, while we both worked at the grocery store to get through college. We were good friends from the moment we met. We had similar interests, were both outgoing, good looking, and hated working at the grocery store.

He and I have gone through many girlfriends over the years. I even came perilously close to marriage at one point. Through it all, he and I have always remained best friends, double dating, surfing, and going out.

About two years ago, it so happened that each of was re-locating, so we decided to shack up together. We found a great deal on a flat on Russian Hill in the City. It’s really worked out well. Being friends doesn’t always lend itself to being roommates, but he and I have proven to be very compatible.

About two months ago, Bob started to seem to be getting more and more distant. I figured it probably had something to do with his new girlfriend. This wasn’t the first time that we drifted apart due to girlfriends. But this was a little different. Not only was he home less, but even when he was home, things weren’t the same. He hid out in his room a lot. He wouldn’t hang out with me and just watch TV or anything. I never confronted him about it, I just gave him his space.

(more…)

“Shit!” he screamed. Bobby was as surprised as the rest of the class to hear his voice ringing out during the midweek exam. His outburst caught the attention of all of Bobby’s classmates, especially the teacher, Mr. Jenkins.

“Outside!” Mr. Jenkins demanded.

Bobby got up from his small steel and wood desk, avoiding the stares of his classmates, and slouched toward the door of his Sophomore Trig class, followed immediately by his teacher. As the door closed, Bobby heard the previously silent class begin to chatter with comments like “he’s gonna get it!” and “what’s his problem?” He hated them all.

“What is your problem? You think it’s OK to use that kind of disruptive language in my class?” Mr. Jenkins intoned.

“I don’t know. I’m sorry. I don’t know…” Bobby replied pathetically.

“This is unacceptable! You are really slipping Rob. You’ve gone from one of my best students to a nightmare! Your grades are awful, you don’t pay attention in class, and now this? I want you to go to the principal’s office and explain yourself, and I’ll see you here for detention at three. Go!”

(more…)

I haven’t always been this way. A hooker, that is. I didn’t always have this unquenchable thirst for man-meat. But here I am anyway, working the corner, reeling in the johns and making a buck. It’s easy, and I get what I want. All I have to do is show off my hot body, give a smile and a wink, and I have ‘em hooked — no pun intended. I get to taste some cock and make a little money too.

My past seems like a totally different life. I know that at first, you won’t believe my story, but if you wait around, I’ll show you the last remaining evidence that I was a man.

Yes, that’s right. I was a man. Of course you can’t tell by looking at me. I don’t want to sound vain, but I know I have the goods. Hot body, big breasts, generous round curves, long legs, beautiful long wavy hair, and a wicked smile. I have it all. And I use all of it to my advantage whenever I want. But it wasn’t always this way. I was transformed, against my will, into this woman you see before you, by a witch.

Who believes in witches? Nobody! I didn’t. I still can’t really believe it. But it happened and I’m the proof.

(more…)

Strange Pick-Up (sequel to “Strange Brothel” and prequel to “Strange Thursday”)

I first met my good friend Sharon at Luther’s on a Friday night many years ago. Back then I was a very convincing sexy young woman. I was sitting on a bar stool watching the crowd and watching the crowd watch me. Dressed in a black leather micro-mini and black lace top that did nothing to hide my black bra, there were several people that were watching me.

Luther’s is an interesting bar. It has quite a mix of people. There are a few Harley’s parked outside and some people think that it is a biker bar. Others think it is a gay leather bar. Others think it is a hideout for transvestites. It is also know as a place to find male and female hookers. And some people think it is the best place to look for group sex. It is definitely a wild and crazy place where the music is loud and the sexual energy is high, very high.

I saw Sharon when she came in with her boyfriend, Dennis. She was beautiful. Dark eyes and long black hair that hung down and curled around her breasts. She was wearing a slinky black dress held up by spaghetti straps that begged to be pushed off her shoulders. Her hard nipples were poking holes in her dress that could be seen from across the room. She was beautiful. Unfortunately, she was with a man who definitely looked unpleasant. He looked like he had a frown tattooed across his face. I had seen him in the bar before and had avoided him.

(more…)

Strange Thursday (sequel to “Strange Brothel”)

When I was younger, back in high school and college, I could dress as a very convincing and tremendously sexy lady. If I were to dress today, I would be an ugly woman. So now I content myself with hanging out in the transvestite community. Under my male clothes, I almost always wear black satin panties and bra along with a black garter-belt and fishnet stocking.

I was dressed like that last Thursday night when I went out looking for sex. I got in my car and drove to my favorite cruising place, a short, little street in a dark part of town. Women wait on the corners or stroll back and forth across the street. I drove slowly down the street and looked for a familiar face while stroking my hard cock through my pants. I drove around the block a couple of times looking for one of my favorite women, but I did not see anyone who looked familiar.

The third time around the block, I saw a woman who captivated me with her smile. I later learned her name was Danielle. I went around the block, drove slowly past her again, and stopped. She walked up to car, opened the passenger door, and got in. I carefully watched her skirt ride up as she slid in. She reached over and felt my hard cock through my pants. “Oh, Daddy take me home!” she moaned.

(more…)

My sex life had been so bizarre that at age 26 I decided to go a brothel specifically to have straight, normal sex with a woman. Already in my short life, I had participated in every fetish that had a name, and some that didn’t. It’s not that I had not had immense pleasure doing all manner of sexual things will all manner of people, but I wanted to do something I had ever done before: have straight, normal sex with a woman. What the hell! I’ll try anything once and most things twice.

So, while I was on vacation, I went to a famous brothel. It was a large place with several different bars, a room with stripers, a video bar. etc. I wondered around for a while taking it all in. I settled down in a little quiet bar with a classic old black-and-white porno movie playing on the TV. I was propositioned by several women, but they didn’t really turn me on so I turned them down.

I nice-looking woman set down at the bar across from me. She was a little older than me, probably in her mid-thirties. She didn’t look like a hooker. She looked nice. I smiled at her and she smiled back. I went over and set next to her. Her name was Alicia. She didn’t proposition me. We just had a nice conversation. I ordered another round of drinks. She was drinking Tequila Sunrises and I was drinking rum and coke.

(more…)

That was the sexy signature I posted with all my stories, the erotic invitation I issued to my readers. Usually, they’d just reply with a sexy thank-you, and maybe share a fantasy. Occasionally, though, I would get an email from someone who wanted to meet. They were usually men who’d fantasized about making love to a shemale, but who’d never acted on those desires. Unfortunately, of the few I’d agreed to meet, every single one had stood me up.

By the time I heard from Glen, I’d pretty much given up hope of ever meeting any of my admirers. Their letters did give me a horny thrill, but the eventual disappointment just wasn’t worth it. I explained that to Glen right away, but he persisted in his online seduction. Finally, after nearly four months of emailing one another, chatting, and exchanging AIDS tests — this is the 90s after all — I agreed to meet him.

To my relief, our affair got off to a very promising start. Glen booked us into a nice hotel outside of town, then sent a stretch limo to pick me up at my apartment. Right away, I knew this was one man who wouldn’t disappoint, and the dozen pink roses I found inside the limo confirmed it.

I knew Glen would be watching when we arrived at the hotel, so I made a show of exiting the limo. First, a pair of pink boots slipped out into the snow, followed by a pair of white tights that hugged my sexy legs like a second skin. My jacket was pink too, with white fur around the edges, framing the ample swell of my breasts as I leaned out into the cold air. By the time I looked up to reveal my blushing face, he was already poking his head outside the lobby doors.

(more…)

I woke up feeling very confused. Things were even more mysterious as I realised that I was not in our familiar bedroom, and Jan was not lying by my side. I wondered what could have happened to me, and where I was. The room seemed to be very pleasant, in fact it could almost be described as luxurious, and the large bed I was lying in was extremely comfortable.

There was a tap on the door, and a beautiful blonde girl came in. She was statuesque, and her lovely hair swept down over her shoulders; she was wearing a delicious powder blue peignoir. She smiled at me: “Hello!” she said. She seemed very friendly indeed, but I was still confused, and wondered where on earth I was. “Hello,” I replied; “where am I?” “I’ll explain everything to you,” she said; “you must be a new arrival.” “I suppose so,” I said, “since I don’t recall being here before, and I really have no idea how I got here. My name’s Rita.” “I’m Jennifer,” she said, “and I’m here to explain things to you. I’m afraid you won’t be too happy when you hear where you are.” Now I was beginning to get worried; I sat up, and swung my legs round to sit on the edge of the bed. I was wearing a sensuous nightdress, pink, with lovely ruffles and lace trim. My visitor came and sat down by my side, and put her arms round me in a sisterly hug; she kept one arm round me, and sat with her nylon clad thigh pressed against mine.

(more…)

Jim had asked his parents if it was ok to move in with Bill for the summer, easier to go to work and it was OK with Bill. Jim’s parents were planning a 3 week vacation anyway so they gave it their blessing.

Jim gave Bill the exciting news and Bill hugged and kissed him.

“Now we can really indulge in our fantasies.”

Jim smiled as Bill led him to the store, it was Sunday and noone would be coming in. Bill selected some 3 inch heels, thigh high hose, black satin panties with bra, a simple sundress which went mid thigh. Bill dressed Jim and made him up very nicely. Jim looked very much like a girl, even more than the week before. All day Bill taught Jim to act more feminine and be slutty. Jim didn’t need much as it was his own natural personality emerging.

That night a friend of Bill’s came over, he was a big man, 6-4 and easily 240 lbs. He was a pro football player, black and gay. He enjoyed white men, especially soft girly white men. And he literally drooled at the sight of young Jim’s soft frame.

(more…)

Jim was 14 and moving to his Aunt’s terrified him. A new school, new bullies, always the same story. His parents had met with a fatal accident and now Jim had to cope with that as well as moving.

Jim’s Aunt Bonnie, his Mom’s spinster 31-year-old younger sister, had always treated Jimmy very well. She had packed up the house when his parent’s died and moved his things to her house.

Bonnie’s house was a small 2-bedroom bungalow with one bath a small kitchen and living room. She moved Jim’s things into the spare room and unpacked his things for him. She was the only family Jim had in the world and she loved him dearly.

Jim had gone to camp for a week and for the first time went to live with his Aunt. As he walked into his room he found it to be quite the opposite of what he expected. It was pink with frilly curtains and bed covers. A white girl’s dresser stood in the corner and the closet was full of girl’s clothes. He checked the drawers and found panties, bras, nylons, girl’s sox, not one stitch of boy clothing anywhere.

He turned to find his Aunt smiling at him.

“You’re Mom told me about catching you wearing her stuff. So I decided you would find out what it’s like to be a girl, completely.”

(more…)

Here’s some information about a great local shemale I met a few years back. Her name was Angel (pronouned Ann-Jel). I met her through a now-defunct local in-call escort place called Dak’s. I actually met 4-5 shemales via Dak. Angel was a significant cut above the rest.

Angel was african-american with a perfect dark caramel skin color. She was about 5′9″, slender, very toned, with long black hair. She must have weighed around 120 lbs. She had large implants, I would say C-D cup. A very narrow waist, and nice legs. She was extremely feminine; there’s no way anyone would ever guess her between-the-legs secret.

I saw Angel 3-4 times before she moved away to California. I had a blast each & every time. She was a little shy the first time I saw her. Kind of quiet & passive. She kept all her clothes on while starting to give me a great blow job. I gently removed her blouse & bra, and was just blown away by her awesome breasts. She had been on hormones for years, and even her nipples looked just like a woman’s. I started playing with them immediately. You could feel the firm implants, but they were still nice to look at & touch. As I got harder, I noticed a nice bulge appearing under her mini-skirt. I asked her to remove her skirt & panties, and she paused for a minute to do so.

I couldn’t believe my eyes when she slid her panties down over her legs. There was the most perfectly shaped, long, thick, circumcised black cock dangling! Wow! This was the first black cock I’d ever seen in person. Angel was semi-erect from giving me head. I reached down to start stroking her spectacular unit, then noticed something unusual: her scrotum was empty?!? I asked her about it, and she said her testicles had been surgically removed. This was definitely a turn-on!

(more…)

OK, here’s how my recent visit with Courtney went. I wanted to see her around 3:00, so I called to ask if her afternoon was open. She said I could come over, and asked me if I was only interested in oral. I was a little surprised she asked that over the phone, but I said “No, I want anal too”. She hesitated for a moment, so I told her I had been to see her before when we enjoyed anal sex together. She said it would be OK.

I drove to a block away from her house in south Mpls. Courtney lives in a detached home on Clinton, just north of Hwy 62, and just west of Portland. I walked up to the door & knocked. It was only a few seconds before the door opened a few inches & I was invited in. I entered her living room to see she was completely naked! She was wearing a long wig of red hair. She told me later it was an expensive wig made of real human hair. I was pleased to see she wasn’t wearing any of that white makeup she had on the 1st time I saw her. She is passable, no doubt about that!

She recognized me & gave me a greeting hug. She squeezed my crotch & noticed I was already getting hard (I had been stroking myself in the car all the way over to her house). I also gave her cock a friendly pat. Then I noticed her new implants and commented on how nice they looked. She was pleased & began to tell me about them & show them off. They’re nice for new implants, but nobody would mistake them for a natural woman’s. They’re very firm, & her nipples still look kind of like a man’s nipples typically do (smaller than a woman’s).

We went up to her messy bedroom, where I immediately got undressed. She asked me for $120, saying I had to pay more for anal. I guess that means her normal rate is $100? I don’t know for sure, but I gave her the $120. I asked her if she could put on a bikini top or bra to accentuate her new breasts. She happily obliged by putting on a sexy red lingerie bra. She asked me to come with her to the rest room to wash up, so we both went to wash our hands (?). Whatever–it’s hard to fault a prostitute for cleanliness!

(more…)