Gay Erotic Stories

My story begins, ironically, after a night out with my girlfriend. I should first tell you a little about myself. I was 29, six-foot and I thought straight, although I had had few girl friends, and the relationships rarely lasted for long. Anyway, that night Mary and I had been at a “Tarts & Flashers” party; as a change she had gone as the flasher, and I had gone as the tart. By the time Mary had finished with me, I think I was fairly convincing.

She had insisted on waxing my legs and arms, trimming my pubic hair and shaving my armpits. She had bought me a lacy bra, thong and suspender belt, all in matching dark plum, because I was too big for her size, along with almost black sheer stockings. I had squeezed into a black leather mini skirt she had, which only just came to the tops of my stockings, but had had to buy the see-through plum lace blouse and high heels. There was no way my size 9 feet would fit into her size 6 shoes. To top it all I was wearing her wig, in long brown hair, and she had made up my face. When I looked into the mirror it was a real hooker looking at me. As Mary was going as a flasher she needed very little in the way of clothes; a body stocking, an old overcoat and a big fake cock. In fact it was that that started the whole thing going when she said she wished mine was a little nearer that size. I knew I was not well endowed in that department, but it was the first time she had mentioned it, and I said something back, and you know how things go…by the time we got into the car we were barely speaking to each other. The evening crawled by, and Mary and I spent most of the time avoiding each other. It was all a bit of a bore to me anyway; it was an old school friend of Mary’s that was hosting it, and I knew no one there. By the middle of the evening everyone was getting pretty well boozed, and my inhibitions were slipping. I had danced with a couple of girls earlier, not really thinking of the way I was dressed, and that it might look a bit odd, but had soon retired to the bar. It was there, when I was having a quiet cigarette and glass of wine, when a guy came up and asked me to dance. I was about to explain who I was when I thought “what the heck”, and in a voice I hoped was more suitable to my “sex” I thanked him, and off we went. The first couple of dances were fairly lively, and we kept apart, just exchanging pleasantries, but then a smoochy number started, so I said I must have a rest. He was having none of it, put his arms around me, pulled me close and started caressing various parts of my anatomy. I felt his hands sliding down my buttocks to the naked flesh at the top of my stockings; he gently stroked it, and started kissing me. Without thinking, I opened my lips and felt his tongue revolving around mine. I also realised I was getting an erection; this was really turning me on.

His hands were moving along the tops of my stockings, kneading my thighs as they went; I remember thinking that he was going to get one hell of a shock very soon. It hadn’t occurred to me that he might have felt my erect penis already, and know that I was male. I was becoming ecstatic with the thought of what was happening; here was I, one male, practically making love with another one on a dance floor, albeit it one in almost darkness. I gripped him closer to me, and felt his hand release my erect cock from the confines of the thong, and rubbing my testicles. Then his finger traced back between my legs to my asshole.

I was shuddering with delight and thought it was about time I did something for him. I rubbed his cock through his trousers; I could feel it’s size, and a suddenly had an overwhelming desire to feel it in my mouth. His hands were behind me again and had pulled my skirt up over my buttocks. He tugged the strap of the thong to one side and massaged my hole. As I pushed my ass back, I pulled the zip of his trousers down, and put my hand inside. I released his meat from his underpants and started pulling at it. I backed out of the open garden doors, and into a dark corner; at last, I slowly knelt down until my face was level with his cock. My tongue darted out and traced the slit.

Precum was leaking out of my own penis; I had never felt like this before. I licked the head of his cock, and studied what I was soon to have in my mouth. It was cut, about 7 to 8 inches long, and thick. It protruded from a forest of black pubic hair, peeping round the side of his briefs. As my mouth swallowed more of this beauty, I put my hand up to his balls. They were equally impressive. He thrust into my mouth, and out, the movements quickening; his cock stiffened, and then for the first time I felt cum in my mouth, the experience of that first time, as it hit my throat. I automatically swallowed, and his big balls were still ejecting their fluid. He pulled out, and a spurt landed in my eyes, and rolled down my face; I put my hands up my skirt, and quickly wanked myself. I came in seconds, my seed falling on to the ground. When I looked up he had gone. I didn’t even know his name; I had really behaved as I was dressed, like a real tart, and what was more I had positively enjoyed it, the best sex ever!

When I went back into the room I saw that most people had disappeared, whether for the same reason I had, or for home I didn’t know; what I could see through the gloom was that Mary was no longer there. I made my way to the front door and walked out into the street; it was only about half an hour to home, but I thought I would try something out. There was a road not far away where certain ladies walked; I adjusted my dress and made for it. As I had thought, there were very few walking so I joined in, getting a stare from the others.

Eventually a car crawled past me. “How much?” came the direct question. “$25 for a blow job” I replied. Fucking might be difficult! “Okay, as long as you sink the load. And I want you to do it as we drive along.” I got in, and he drove off. I put my hand on his flies, and as I had done earlier, gently rubbed his penis through the cloth. He was already well aroused, so I unzipped him and let his manhood out. It was shorter and thinner than my friend’s earlier; it was also uncut. I leant down and slowly absorbed it into my mouth, and he put his hand on my back, making it’s way down towards my skirt. I moved my head up and down, trying to keep out the way of the steering wheel, and I could feel him moving on his seat, and hear his groans. He was rubbing my ass faster and faster, when the car stopped. “Carry on” he managed to get out, “it’s just traffic…lights.” Just as we were pulling away from the lights he suddenly shot his load. I sucked it up hungrily, while he carried on driving. “You were great, that’s the best blowjob I’ve had in years. You’re a pansy, aren’t you?” In reply to my nod, he continued, “That’s why. You know what a man needs. How much do you charge for a fuck?” “I’ve never been fucked, but if you want to try, you can have me for another $25. My flat’s just up ahead.” I could see by his face what he wanted. A virgin pansy to be plucked. I got my key out as he pulled up, and we hurried inside. I think we were both equally turned on, and could hardly wait to get inside. I guided him into the bedroom, and started to undress him. I stared at his body when I had finished; it had just hit me, what I was doing. Here I was with a naked man, dressed as a tart, and about to be fucked. My eyes roved round him; he was slightly overweight, with a pronounced paunch, and quite hairy, from the neck down.

I moved forward and entwined some of the hair round my fingers, pushing him gently backwards at the same time. His legs stopped at the edge of the bed, and he fell on to it with me on top of him. His hands were at my skirt, trying to find the fastening, and get it off me. I guided him, partly for time, and partly to prevent him ripping it. I raised my legs and shook it off, and then pulled my panties off. I put my head down and buried my tongue into his curly chest hair; my teeth found a nipple, and I chewed intensely. He rolled around on the bed, and I put my hand between my legs and stroked his re-aroused cock. I shuffled back, and lubricated his cock with my saliva. I was glad it was fairly small; although I had had fingers up my asshole before, nothing bigger had gone in, and I thought this experience could be painful!

I moved forward again, and then said to him “Hold your cock upright, and I will let you enter me.” I slowly lowered myself onto his quivering cock, pushing down, and pulling my cheeks apart. It was really tight, but he was pushing up as well, and then I felt his head pass through my hole. The pain was so intense I nearly pulled myself off, and then let go as it continued into my bowels. I moved my body up and down and began to feel a great pleasure and warmth inside me. My penis had grown erect again, and bobbed up and down as well. He put out his hand and started wanking me, making me feel even more frenzied inside. He pushed harder, and I knew that very soon he would blow his load into me. He came, making me shoot too, and I watched as my sperm fell onto that hairy chest. I moved myself forward, pulling myself off his rapidly shrinking penis, and as I did I could feel his cum draining out of my asshole, and down my legs. I also heard the door opening. I peered round, and there stood Mary, the expression on her face a cross between shock and mirth. “So John, or perhaps I should call you Jenny, you’ve found your true use in life. Well I won’t interrupt you and your customer; I’ll come back for my things in the morning.” The door shut, and I turned back to the man, who had buried his head under the pillow. As I began to speak, the door opened again, and I looked round to be blinded as Mary took a photo. “Just a little souvenir, asshole,” and she was gone.

“I’m sorry about that. I think she’s gone now, I’ll just go and check.” Oblivious to my state, I walked into the living room, and checked around. No sign of Mary, but in the bathroom I grabbed a towel and wiped my arse clean, then made sure the front door was locked. When I went back into the bedroom the guy was sitting up in bed, under the bedcovers now. “Yeah, it’s all safe now; nobody can get in.”

“Good girl, little Jenny. I like that, I think that’s what I’ll call you. That’s if you want to see me again. And my name’s Clifford, by the way.” I was going to have to decide pretty quickly, but there was not really any argument; I had enjoyed myself more tonight than I had for a long time, in fact I was sure I had found what I wanted.

“Why, yes, Clifford. And please call me Jenny. I like that.” He looked as if he was thinking of staying, so I got undressed slowly, tantalisingly, and I hoped seductively. Not that there was much left to come off. I slipped under the bedcovers, and felt between his legs. It appeared I had been seductive.

I woke up the following morning with a start. It took me a minute to remember all that had happened. The bed was empty, and I could hear humming from the bathroom. Clifford must be in there; I leapt out of bed and into the bathroom. Sure enough, there was Clifford in front of the mirror shaving. I put my arms around him, and let my hands drop to his groin. “Not now, Jenny, or I’ll be late for work. Could you make me a cup of coffee, and a slice of toast please.”

I kissed the back of his neck, and went back to the bedroom. On the back of the door was a flimsy pink dressing gown, an old one of Mary’s. I slipped it on, and went to the kitchen to prepare breakfast. When Clifford came through he sat at the table, and pushed $200 towards me. “No, you needn’t…” I started.

“Yes, please take it. You gave me far more than we agreed…and I’d like to think you…we could meet again.” I hadn’t thought beyond that moment, but knew I had thoroughly enjoyed the last twelve or so hours.

“Oh yes, I would like that. And thank you very much. When can you make our next meeting?”

“Well I’m free every Tuesday…