LGBT Stories

My boyfriend, Ed, and I live together in a small off campus flat. One evening we were talking about things that we might be surprised to find out about each other.

“Well, Ed” I said, “as a teenager I used to walk along the railroad tracks near my home. I’d wait for an oncoming freight train and stand in the way of the train. Right at the last minute, I’d leap out of the way. Try and top that!”

Ed said, “That’s a good one! I didn’t know that you where such a daredevil, and a tomboy to boot, Kim.”

“Okay,” I said, “What’s your little secret”

“It’s no where near as exciting as yours, but it might surprise you. It’s a little weird,” Ed said

“Go ahead, shock me”, I proposed.

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Jenny had been planning her adventure for months. It was the last week of summer vacation. Jenny had turned 18 that August and was ready to begin her senior year in High School.

She knew that turning 18 was a big deal, carrying with it a lot of responsibility. So Jenny wasn’t surprised that when her parents decided to go to Niagara Falls for a second honeymoon, the left her to mind the house.

Jenny received a lot of presents for 18th birthday, but the most special present she got was her parents telling her that she could get her hair cut, short. Real short. She was to get it cut this very special weekend. You see, Jenny had plans for the weekend, and they involved a boy. Not just any boy, but a real soul mate. His name was Rick, and well, you’ll see.

Around lunchtime on Friday, Jenny’s mom and dad packed their suitcases into the car. Jenny’s mom, always the worrywart, must have spent an hour reminding Jenny to “not let anyone in the house, leave the porch light on, don’t talk to strangers, and on and on and on. Jenny’s mind went on autopilot as she replied “yes, mom” for the twentieth time. Jenny stood in the living room as her parents were getting ready to leave.

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Life at Halliwell Girls School was different for Traci Lyons. Halliwell was a quiet school, in a quiet valley tucked in the central part of the state. For a girl from San Francisco, who had seen a lot, and done a lot, it meant a whole new life. She was away from home for the first time ever. She finally could just be herself, and not be bothered by anyone. Her secrets were safe at Halliwell. This didn’t, however, mean that she didn’t get into trouble. The note that Traci found in her campus mailbox indicated that trouble was about to find her again.

It was a note from the dean of the school, Ms. Paget. ‘Uh-oh,’ thought Traci, ‘not Paget! She’s a bitch.’ The note instructed Traci to report to Ms. Paget’s office at 5PM sharp. It had a ‘to-the-point’ tone that meant that trouble was brewing.

At 5PM sharp Traci knocked on the door to Ms Paget’s office. Ms. Paget opened the door and asked to enter. Traci walked into the office, her stomach filled with butterflies. She approached the chair in front of Ms. Paget’s imposing oak desk.

‘Remain standing, Miss Lyons’, Ms. Paget sharply ordered.

‘Oops! That can’t be a good omen’, Traci thought.

‘Miss Lyons, there is a rumor going around campus that you are involved in a sexual perversion. I intend to get to the bottom of this rumor. Do you understand, Miss Lyons?’

Ms. Paget’s tone was as hard as nails.

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Spring was in the air, and for the seniors at Enright High School, this meant three things, finals, graduation, and the senior prom. For Carole Jackson this meant attending that prom with her boyfriend, the coolest guy in pants, or out of them preferably, Bill O’Brien. Bill was cool because he was drop dead handsome, and a freshman at McKnight Academy at the other end of the state. To a status conscious 18-year-old, dating an older guy may have been enough of a status symbol, but to be dating a McKnight man was the ultimate.

Carole also considered that she had a particular edge with Bill, because she was best friends with his twin sister, Jill. As kids, the twin’s mom used to dress them alike, almost as a taunting challenge to the world to tell them apart. This left the twins with the difficult work of developing their own separate identities. As things go, Jill and Bill always seemed to have an insight in each other’s inner thoughts. Carole relied on this to find out what was ticking in Bill’s head. She’d just confide in Jill. Jill’s sixth sense about Bill came in quite handy.

It was no surprise on Thursday evening when Carole and Jill were at Valley Mall, that when Jill felt a blow to her head and the resulting sharp pain it meant big trouble for Bill.

‘Ow! Cripes! What the hell was that!”, Jill screamed. She felt a bit of dizziness, and sat on a bench.

‘Are you okay?’ Carole asked.

Jill hesitatingly said, ‘I.. think .. so. I just feel like my bell got rung. Perhaps we had better head home. I think you should drive.’ Jill tossed her car keys to Carole.

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Bob and Diane had been best friends for as long as they could remember. They went to the same schools together, lived on the same street, and even played at the same playground. In fact, they even played the same games! Diane never was one for playing jacks or skipping rope, so more often than not you would catch her in a baseball game, or passing a football on a team with Bob.

As kids, Bob never gave Diane’s tomboyishness a second thought. But, as they grew into their teens, he came to find it to be a quality in her that he relished. Secretly, he had a crush on Diane that just wouldn’t be sated. When it came to asking her out on a date, however, he just couldn’t do it. It would be like dating one of the guys. Still, he always had a soft spot in his heart for her.

One moonlit, cloudless night, shortly after they had both graduated from High School, Bob lay in his bed. It was shortly after midnight. His mind drifted to pleasing, relaxing thoughts. Those thoughts were mostly of Diane. He liked the way she looked, not all femme, just natural. He thought of her short black hair, and her small breasts. He realised that in all the years he had known her, he had never seen her in a dress, except for First Holy Communion at church, and confirmation. You know, he thought, that was what he really liked about her. She was just one of the boys. And he couldn’t, in fact wouldn’t, change that for all the money in the world. Hmmm, he thought, the more the merrier. He had an idea.

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It’s not often we have to travel for my husband’s job. But when we do it’s usually for an important reason. There was to be several social occasions at the company conference, so I had to go along. I hate this sort of thing, having to make mindless small talk with other executive’s wives. I have a few…hobbies I like to pursue when I’m on my own. But I had decided to make the best of it. It was only for a few days after all.

The flight would take us across the country overnight. Not the best time to fly, but I can usually sleep anywhere. We were welcomed on board by a fairly good looking dark haired stewardess. I could tell Jay was sizing her up, I couldn’t blame him because I was as well.

Once in flight, we flipped up the arm rest between us and I lay against Jay who lay against the wall. It was nice like that and I spread Jay’s coat over us like a blanket. We had hours of night-time flying in front of us. Jay held me in his arms. I felt him slip his fingers into the waist of my pants. He slowly fingered me. I opened my eyes. I felt that feeling growing in me.

A stewardess walked by. It was so strange to have Jay fingering me right there in front of someone. Jay withdrew his fingers and I could tell he was sleepy. Soon I could feel that he was sleeping. I slipped my own fingers where his had been. I fingered so slowly. I wanted that feeling, more and more. The stewardess came back and stopped. I stopped my fingers, laying there frozen. She looked at me and then smiled.

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In my line of work, you come across loads of unusual situations. Of course, you quickly learn not to get involved. I just wished I’d followed my head and not my heart on that day.

I’ve been in the locksmith trade now for about twelve years and my business, while not massively successful, more than pays the bills. I was returning from fitting a new set of locks to a house when I got the phone call that would drag me into very bizarre situation.

I pulled into the side of the road and answered my mobile phone. “Michael Cox, locksmith. How can I help you?”

“Oh! Thank God.” Said a frantic female voice on the other end of the line. “My friend has been handcuffed and we can’t find the key. Can you help us?”

I had to struggle to keep the broad smile I had out of my voice as I replied, “Certainly. If you give me your address, I’ll be around immediately.” She quickly gave it to me and I told her I’d be around in about fifteen minutes.

She had obviously handcuffed her lover and then lost the keys. I’ve had a few similar cases in the years I’d been doing the job. I had learned that you have to act totally professional, however ludicrous the situation looks to you.

Soon, I was at the address she had given, it was a fairly exclusive neighborhood. Stands to reason, I thought, rich people seem to go in for the kinky stuff. I parked the van outside the house, picked up my tools and a good bolt cutter and headed up the drive.

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I’ve always had this serious thing for women’s’ underwear. Even as far back as grammar school I loved to sit on the ground in the school yard to watch the girls jump rope and show off their frilly little panties, just for me.

I was always so jealous of my sisters! They got such pretty, pink ruffled undies to wear while I was stuck with boring white BVD’s. It was so unfair, I thought!

I loved the exciting feel of their lace and silky nylon dainties, so cool and silky and smooth to the touch. By age 12 I was trying on my sisters’ underwear. It made me tingle all over to mince in front of the mirror wearing a bra and panties.

It would get me so excited that I would get a huge hard-on, and I would only be able to control myself for a few minutes before I had to masturbate wildly in front of my reflection. Soon I was hopelessly hooked on wearing my sisters’ underwear!

After school I would rush right home for an afternoon of panty pleasures. Once I was sure no one was home, I bounded up the stairs to the bathroom and locked myself in. Then I would rifle the hamper and dig out all the soiled panties my sisters had deposited.

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I can spot them a mile away. The minute they walk into my lingerie shop I can tell which guys are buying something for a lady friend and which are buying for themselves.

Cross-dressers all give off the same signals: they descr ibe a “larger woman” about their size; they’re much too concerned about an undergarment’s “fuller cut”, they fondle the material with too much relish and they know much more about ladies’ unmentionables than is proper for a gentleman.

So when Bobby walked into my shop for the first time I had him pegged right away. I knew that extra-large sized maid’s uniform would never be worn by a woman. He wasn’t fooling anybody!

He drove me crazy with a lot of stupid questions when what he really wanted to know was would it fit him. Did the material have any give, did the gloves have any stretch, were the straps adjustable? Finally I just ran out of patience and said, “If you want to try it on just take it into the dressing room.”

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My girlfriend is practically joined at the hip to Maryanne, her childhood friend. Everywhere Lisa goes Maryanne has to follow! We’ve double dated and gone places until I’m sick of looking at her. Lisa can’t get on the phone with her for less than fifteen minutes, even if it’s just to say she’s on the way over. I can’t imagine what they find to talk about!

So I got to see a fair amount of Jeff, Maryanne’s husband. He seemed like a decent sort of fellow even if he was a suit. But at least, I thought, we had a few common interests… little did I know!

One day last summer I was over Jeff and Maryanne’s house, swimming in their pool. As usual, Maryanne and Lisa were off shopping, leaving Jeff and I lazing out by the pool.

I went into the basement to get us another beer. In the dark basement I kicked over a wicker basket, slicing my ankle and falling over in the dark with a loud crash. Naturally, Jeff rushed inside to investigate, but when the light came on I saw the contents of the basket: a big, frilly pair of pink sissypants and several rather large pair of panties.

Delighted, I picked up the lovely ruffled sissypants and held them up in front of Jeff. I said, “These aren’t Maryanne’s are they? Whose could they be, big frilly undies like these? Maybe Maryanne will know.”

You should have seen the look on Jeff’s face! He sputtered and stammered but couldn’t get any words to come out! I’d caught him dead to rights, as only another sissy can.

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Saturday she awakes to morning sunlight filtering through her bedroom window and the chuffing cadence of a sprinkler watering the lawns.

For a moment she tries to summon the will power necessary to throw aside the warm blankets that caress her. Then she remembers where she is and a drowsy smile curls her lips. She snuggles her cheek a little deeper into her pillow and surrenders again to the siren-call of lethargy.

A warm little animal, safe in her burrow of bedcovers.

There are no pressures today. No places she has to be or commitments she has to honor. Today is the first day of her vacation. Today she can come and go as she pleases, rise whenever she wants - or sleep the whole morning away if that’s what she wants to do.

Of course now that she doesn’t have to get up she finds she wants to. Drawing back the blankets, she treats herself to a luxurious yawn and a thorough scratch of the hair over her right ear.

The simple silk nightdress in which she’d awoken swirls around her ankles as she steps to the window and flings the drapes wide.

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David went to his sister Gwen and asked her to help him with a problem. He was to going to attend a medical theme fancy dress party. His mother had promised to obtain some surgical gowns from the hospital where she worked but tonight she had been delayed and could not meet her contact. His sister was a nurse at the same hospital and he wondered if she had anything that he could wear. “Well, little brother. I think I can rustle up something. First let’s have a look at you, get your kit off now.” He was a bit surprised by her forwardness but he decided to comply. He undressed down to his underwear and stood before her. “Oh yes” she said “I think we can do something with you. Will you do everything I say?” “What do you mean?” he said. “I just want you to agree then we won’t fight.” she said. “Do you want me to help you?” “OK, OK.” he said, “I will do what ever you want.” “All right lend let’s get you fitted into your new uniform.” she went to the wardrobe and got out one of her nursing uniforms. She put it onto him and the fit was perfect. “You will look lovely, just like me.” In fact, she thought, he does look just like me, I wonder what he’ll be like when I’ve finished?

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“Ha, Ha, very funny” said Colin as his mother held the dress against him and joked “Oh but dear you’d look lovely in this!” The dress was amongst some jumble she was sorting through and was a pretty floral cotton affair, it looked brand-new, as did a lot of the other things. This was an affluent area and it would probably have been worn only once or twice before it’s owner tired of it. She looked at her son and although she loved her only child dearly she would have liked to have had the chance to bring up a daughter, but that’s the way thing’s go she thought and returned to the sorting. Nothing more was said and the clothes and other items were packed away in the garage for collection the following week.

Colin was all Boy, he certainly was interested in Girls but he had to admit to a certain fascination for the way they dressed in light and dainty things. He knew how tights felt on his legs from the sports Lycra he wore when running and cycling. But he had never considered actually dressing up. He had recently seen pictures of some transvestites in one of his mother’s magazines with their before and after pictures and he was fascinated by the change in appearance that could be achieved.

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The train finally arrived at the station, John had been looking forward to visiting his Aunt, Mum and Dad were off on a cruise and he was to spend the summer in the English Lake District. The sky had darkened on the spring evening and rain was in the air, standard Lakes then. He left the train and stepped onto the deserted platform of the unmanned station, he’d done this journey before and knew there was a local bus from Staveley to the valley where his aunt’s house was. He carried a sport bag with all a teenage lad needs for six weeks away (not much!) and went down to the bus-stop. The bus would be along in 10 minutes, there was no shelter and as it started to rain gently he was annoyed but not too bothered his light jacket keeping most of the wet at bay. The rain intensified and became torrential he could not leave the stop as the bus was due. He was now getting very wet, but hey he’d be at Mary’s soon. The bus finally arrived 10 minutes late by which time he was thoroughly drenched.

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Alan was pedalling very hard into the wind. He was late, again, very late.

His job at ‘Trimble’s’ sea-front cafe was on the line, he had had his final warning last weekend and still he had overslept. Now as he came within the last half-mile the clouds that had been dark and threatening did the business and a torrential downpour soaked him to the skin. His waiters uniform of white shirt and dark trousers were dripping wet.

He got to the yard at the back of the cafe and parked his bike in the shed; he then made his way into the rear of the building.

“What are you like?” laughed Jenny and Sandra “Miss Trimble is on the warpath and she’s looking for you!”

“Oh I know, I know. I’m late again, and I can’t work wearing these clothes can I?” Just then Miss Trimble’s voice came booming out “Where is that miserable Boy, why do I bother employing useless Boys?”

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Sometimes life takes a turn you don’t expect, mine sure did. Just about the time my friend Sue lost one of her roommates my lease expired and the rent went up higher than I was willing to pay, so I and ended up moving in with her and Lisa. I soon got used to the relaxed routine of the two women. I’m a computer programmer and do much of my work at home, so I took over much of the cooking and cleaning to their delight. As for me, I enjoyed living with them, and seeing two gorgeous women in little more than her underwear was a definite plus. They were both worth looking at, Lisa 5′8″ of lean muscle, wide hips, generous tits and a lively face framed with soft red curls that fell to her waist. Her body moved with a fluid grace that drew every man’s eye to her. Sue is shorter and rounder, with smaller breasts but an engaging wiggle and an ass that was something to watch as she walked. Lisa really attracted me but I managed to control it, remaining the perfect gentleman until one evening I came home a bit early and practically bowled Lisa over as she left the bathroom. She had absolutely nothing on and was a delicious sight. I instinctively put my arms around her to keep her from falling, but I think I fell instead. For her. With my hands full of delightfully shimmering ass we kissed, our tongues meeting and exploring. My hands caressed her soft flesh, sliding up from ass to waist to the heavy firmness of her breasts. As my palm passed over her nipple she let out a sigh and melted in my arms. An instant understanding flowed between us and I carried her to her bedroom where I laid her gently on the bed. I kissed my way down her body, pausing at each lovely nipple to savor it, still moist from her bath. Kneeling at the side of the bed I brushed her thatch copper curls that covered her crotch and tenderly parted them to reveal her glistening cunt lips. Beads of water still clung to her hair, shining softly in the subdued light of the bedside lamp. I breathed gently on her, letting my breath warm her and again I was rewarded with a languorous sigh of satisfaction. With one finger I delicately traced the outline of her labia, not parting it yet, just teasing. I played with her hair, brushing it oh so gently , just barely touching. Small sounds of encouragement began to form in her throat, and I slid one finger deeper, parting her lips just a bit until my finger began to move with ease in her love juices.

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When Jack and I were married we moved into a new house after a wonderful honeymoon in the tropics. The only thing that marred our trip was losing half of our luggage on the trip home. As we arrived after midnight and had no choice to head for our new apartment and go to sleep among the boxes I had moved in before we left. When we awoke we rummaged through the suitcases and discovered Jack had no clothes at all except the well used ones he wore on the flight back, and all his things were still in transit with the moving company. I didn’t see much wrong with spending the next week before we returned to work with a naked man but he didn’t think it was so funny. So we ate breakfast in the buff and took advantage of our unclothed state for a quick fuck.

A call to the airport confirmed we were still without luggage so we started unpacking. It soon became obvious that work like that is not easily done with your balls flapping in the breeze, and with a rather malicious grin I offered Jack some of my stretch pants and a blouse for protection. He’s taller than I am, but almost the same size, so he reluctantly put on my clothes and we continued on. As we opened and sorted things I kept looking at my new husband and got a real kick out of seeing him in my clothes. I couldn’t help teasing him by occasionally holding a dress before him and speculating how it would look on him or asking him if he thought his cock could fit inside a pair of lacy panties. We started to get really silly as he admired my wardrobe, and we decided I had enough clothes for the two of us even if we never found his luggage. When we found one of my favorite bras, a lacy underwire number in red and black, I offered it to him to try on. To my surprise he simply removed my blouse and held out his arms. Caught up in the absurdity of the moment I fastened the bra around his body and stuffed it with loose underwear. It wasn’t until he put the blouse back on and struck a pose for me that I realized just how good he looked. With his light beard and long hair there was a definite feminine appearance, and to my surprise it rather turned me on.

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Twilight was gathering on a cool spring evening as I jogged past the small women’s clothing shop once again. I had just moved into town, a boy fresh from college with a new job and a new apartment. In the window were two mannequins clad only in corsets and a sign saying “Bra fitting clinic today”. It was closing in only a few minutes, so it was now or never and I went inside. The clerk was a middle aged woman who had an almost motherly air, but her figure and style were anything but motherly. “Uh, I wanted to see about a bra fitting?”, I said tentatively. The woman glanced quickly at my left hand and said “Of course, is your girlfriend free tomorrow?” Crunch time was here, so I gathered my courage and said “Actually, I was hoping to be fitted myself.” There, I’d said it! She smiled and said “That’s no problem at all. Just let me close a few minutes early so you won’t be embarrassed if someone else comes in. I always enjoy helping a man find the right clothes to express his femininity.” She quickly went through the routines of closing while I nervously examined the merchandise, then led me to a back room. There were more bras, corsets and teddies on display than I had ever seen, mirrors on the walls and several comfortable chairs and couches scattered about the room. She invited me to sit down and seated herself beside me.

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I suppose it’s rather trite to say your first time with a woman can sets the pattern sets the pattern for your whole life. I know it was true for me, but the pattern included more than sex, it changed my whole attitude toward women and life. I was 18 and very green, having grown up in a rather conservative family, and had only dated a few times since entering college. Away from home and despite the normal adolescent male longing to find out what was under those feminine clothes I had never even come close to finding out. Then Mary came into my life and it was never to be the same again.

We met in a small theater production at school, both of us aspiring actors. She was an “Older Woman” of 20, and I was flattered and excited to be with her in public. I was staying over spring break as home was too far away to return for a week, and she lived in town. I tried my best to be John Wayne or Clint Eastward flirting through dinner and a movie, trying to impress her with my manly demeanor. To my amazement she suggested we go back to her place at only a hint from me. I was horny and amazed and readily agreed, and when I found out her family was gone for the weekend and we were alone the fantasies flamed in my head. Hindsight tells me she was gently but firmly leading me to the bedroom with great finesse, but at the time I could hardly believe how forceful and macho I was to seduce this vision. I tried hard to be cool and experienced while undressing her, but the infamous bra hook almost defeated me. We were soon in her bed where she slowed my raging passions as she taught me how to pleasure her. I fear I erupted in her hand when she first touched my rigid cock, putting quite a dent in my image as macho seducer. But she joyfully milked my juices and in time her loving touch and friendly understanding were able to revive me to fill her hot cunt with my manhood. It was comic and passionate and a wonderful way to learn about sex.

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Oh, those lost days of our youth, how good it is we don’t have to live them over again. But they do have a charm in memory that makes us forget the abject terror we felt when dealing with the opposite sex. As a sophomore in College I was one of those strong but skinny kids, no amount of working out seemed to put any bulk on my bones. I was desperate to raise a beard, but despite ample hair on my arms, legs and head the face simply would not cooperate. I drooled over the girls and threw my two cents into the bull sessions with lurid tales of my sexual adventures (cribbed directly from the fuck films I had seen) but in truth the few dates I had been on were rather placid affairs where attraction and fear contended in my adolescent mind to leave me frustrated and confused at the end of the evening.

All this changed when I had a chance to share a house with two other students, both of them female. I was desperate to get out of the human zoo they call college dormitories, and they were desperate enough for the extra money that they took me in. They were theater majors, while I was an engineering nerd, but we got along well. Jan was an cheerleader type, curly blonde hair, big boobs, an hourglass figure and a sparkling personality that made her the life of any party. Beth was stocky and quiet, with an athletic body and dark hair, small breasts and given to flowing hippie clothing offstage. I began to get used to the sight of these women in various states of undress, but good manors always prevailed and I refrained from making a complete fool of myself. In a short time I was “one of the girls” and conversations didn’t stop just because I walked in the room. Of course I had some very interesting dreams.

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