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.

(more…)

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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