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My First Time with a Man

Tags: bi-sexual, man

A straight male tries sex with another man

Would you have sex with a man? That's the question that came up. Myself and four of my friends were having our usual get together. We meet once a month, usually at Matt’s place; we have some drinks, get drunk, and talk about all sorts of shit. He was the only one of us who was single. He's also the only one who's gay.

We've all been friends since junior school, so we know that whatever goes on, or is said at our nights together stays amongst us. The question was asked by Matt to us all in general. Of course, we all said no, but it got me thinking. I stayed behind after the others had all gone.

“Why did you ask that question earlier?” I asked him.

“Just curious really. I often wonder if any of you had ever thought about it,” he replied. “Have you?”

“This stays between us, right?”

“Of course.”

“I’ve been wondering what it would be like, so I suppose I’m bi-curious as they say? Can you tell me what it’s like?”

“Well, it’s natural for me,” he answered. “I knew from an early age I was gay, but it took a while for me to pluck up the courage to seek out other gay men. When I did though, it was a relief. The first time I had sex it was a bit uncomfortable, but I loved it.”

“How did it happen?” I asked.

“I’d got very friendly with the guy in question and we went to a club and then back to his place. He was a bit older than me and a lot more experienced. We had a few more drinks and he put his hand on my cock and rubbed me until I got hard. He took the lead and told me what he wanted. First off, he wanted me to suck him off. He took off his trousers and pants and made me wank him a bit, and then made me lick his balls.”

“Was this your first time?”

“Oh yeah. I’d fantasised about it, but it he was my first.”

“Carry on,” I said.

“Well, I licked him for a while and then he shoved his cock into my mouth. I took it eagerly. I had a raging hard- on myself. I could taste the pre-come on his cock and it just made me want it more. He made me suck him for quite a long time, until he was ready to fuck me.”

“Then what happened? Was it as you expected?”

“Oh, it was far better than I could have imagined. He made me lean over the back of his sofa and spread my legs. Then he got some lube and smeared around my arse and then he slowly pushed his cock into me.”

“Did it hurt?” I asked.

“Well, I expected it to, but he was quite gentle. He pushed further into me I made myself relax. I had tensed up a bit and, as I did I began to really enjoy it. He was pumping into me fairly slowly and gradually increased the speed. I could feel his balls slapping against me and it made me so hot. I could feel his cock hitting something inside me that just made me so fucking randy. I told him to stop and pull out so I could face him and told him to start over. He lifted one of my legs and thrust his meaty cock into my arse. I put one arm around his shoulders and kissed him and wanked myself as he fucked me. This got him so worked up he pounded my virgin arse like there was no tomorrow. He watched me wank off and when I came it was so intense; so powerful. I shot my spunk up and over our shoulders. We both had streaks of spunk across our chests. He came as he watched me come and I could feel him jerking and spasming, as he unloaded his spunk into me.”

“How did that feel?”

“It was great; I could feel it fill me up. When he pulled out of me it ran down my legs, all hot and sticky.”

“Then what?”

“Then I got dressed and went home. I felt a bit uncomfortable for the next few days, but I knew it was right for me.”

“And after that, what happened?” I asked.

“I really got into the gay scene, clubs, gay men. I did a lot things that were a bit unsafe, like having unprotected sex with strangers, but I calmed down. Now, I’m very careful about whom I sleep with.”

We had another drink and chatted some more, and then I left and went home. I spent the next week thinking about the possibility of having sex with another man. I finally decided that if I didn’t at least try it I would be missing an opportunity that I might regret later in life.

I called Matt and arranged to meet him for lunch. As we were eating I told him of my decision.

“I knew you would,” he said.

“Could you set it up for me? I don’t know any gay men apart from you,” I asked Matt.

“If you want, I know of a bi-man. He’s very good looking, clean and discreet. I’m sure he’ll be up for it.”

A week later Matt called me and asked to meet him at his flat. When I arrived he told me the other man was there. He introduced us and we shook hands. His Name was Alan; he’s about forty-five years old, with the body of a thirty year old. Matt gave us both a drink and left us alone.

It was a bit odd at first; I didn’t know what to say. I did find him very handsome, which surprised me. Alan came straight out with it.

“So, Matt tells me you’re curious about sex with another man?”

“Err… yes I am,” I replied.

“Well, I was the same. I’m married, but felt that something was missing from my life. When I analysed it I realised what it was.”

“What did you do?”

“I didn’t do anything at first, but the feeling wouldn’t go away. So, I took the plunge and knew straight away it was the right thing to do. So, now I occasionally indulge myself. I particularly like men who are trying it for the first time, men like you,” he smiled as he said it; his eyes were sparkling.

I didn’t know how to reply, so I just shrugged my shoulders.

“Look, let’s go somewhere else; I don’t think your friends flat is the right place.” We told Matt and he shooed us out the door, making me promise to call him after.

We went to Alan’s flat. He revealed he is very wealthy and keeps the flat as a crash pad for when he’s in town. The low lights and the decor made me relax straight away.

We sat on the couch and Alan took the lead. I was bit tense to start with, but Alan massaged my shoulders first, before gently unbuttoning my shirt and slipping a hand inside to rub my chest. I just sat and let him do it. I was trying to decide if I could go through with it when he ran his nails across my nipples. A shiver ran through me and I realised my cock was getting hard.

Alan pulled me to my feet. He looked at me straight in the eye, as he undid my jeans and pushed them and my boxers down around my ankles. When he grasped my cock it felt like I’d been hit by a lightning bolt. He knelt in front of me and kissed the end of my cock. He then stood and undressed.

I watched him closely and went to him when he was naked and put my arms around him. I could feel the heat of his body and was aware of his erection pressing against me. Without thinking a sank to my knees and kissed his cock and took it into my mouth. It didn’t feel at all unusual to suck it, which surprised me.

Alan was quietly urging me on, so I sucked him how I like a girl to suck me. I sucked hard as I cupped his balls in my hand, before moving to his balls and sucking them into my mouth, while I began to wank the length of his cock. I could feel it pulsing in my hand and knew he was close to cumming, so I carried on until he shot his spunk over my hand and face.

He pulled me to my feet and did the same for me. His mouth felt so much different from a girls that it was only seconds before I had my first orgasm. It was so intense my cock throbbed and pulsed and shot spunk for ages before I was spent. It was all over Alan’s face, neck, hands and chest. I apologised for making such a mess, but he told me not to worry.

We sat down on the sofa and had a drink; Alan’s hand found my cock and was caressing it, stroking it. It took only a short time before I was hard again. He asked me if I was ready for him to fuck me. I nodded eagerly; I was so turn on by the whole experience. We lay on the sofa with Alan behind me. I could feel his hard dick pressing into the crack of my arse and I pushed against him.

He got up and got some lube from the cabinet and told me to get on all fours. When I had, he squirted the lube around my eager hole and carefully worked some in. He then gave me the lube and ordered me to rub it all over his cock. I took my time and made sure his cock was coated. It glistened in the lamplight and made me want him in me even more.

He positioned himself behind me and pressed his cock against me, one hand was holding my hip. I felt him push into me and I felt my tight hole open up for him. He stopped and asked me if I wanted him to carry on. I couldn’t speak, so I nodded and he slowly pushed all the way into me, until I felt his belly against my bum cheeks. Again he stopped to let me accustom myself to his cock.

Then he began to properly fuck me with long slow strokes. I had never felt so full before. My whole body was tingling and I had a weird sort of fizzing all around my cock and balls. With his spare hand he grabbed my cock and began to wank me, matching his strokes with his cock thrusting into me. A heat started to build in my lower stomach and I knew I was going to cum. Alan sensed this and increased his thrusting. I cried out and came; gushes of spunk flew all over the sofa.

I felt Alan tense. He was about to cum. He pulled his cock from me and sprayed his cum over my back and arse; I felt it trickling down my cheeks and legs.

When we had both recovered we cleaned ourselves up and Alan took me home. We never spoke during the journey; we both knew want had just happened was very special. Alan gave me his telephone number and told me to call him, but only if I wanted to.

I called Matt when I got in. He was so excited for me. “How was it,” he asked. He could hardly contain himself.

I replied, ”It was amazing. I knew as soon as we started that it was right. I’ve never felt so full. When he was fucking me and the orgasm was so intense. Sex with him was out of this world.”

“Would you do it again?” Matt asked.

“Yes,” I said without hesitation, “but only now and again. I like sex with women too much to just have sex with men, but now and again for something different would be good.”

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

Copyright © All stories copyright. Peter Armstrong. No unauthorised, copying, publishing, or reproduction without authors consent.

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