I’d been friends with Dave since junior school and when it became clear later that he was more interested in cock than pussy nothing changed. We still hung out together and did all the things that friends do. Except he had boyfriends and I had girlfriends. We went to different colleges but ended up in New York after graduation and resumed our friendship.
We were out for a movie one night and decided to go for a few beers after. Normally we ended up in my local bar but this night Dave told me he wanted to go to his favorite hangout. It was down in the Village and I didn’t need to be told that it wasn’t going to be like the place we usually went.
We found two stools at the bar and got our beers and I looked around. This was obviously a gay bar. I wasn’t surprised. Dave’s inclination was no news to me.
Dave asked if I was OK there and I answered that I was then he asked if I ever thought about sex with another guy. I had to admit that it had crossed my mind a few times.
Dave just nodded and smiled. Like he knew already. Then two men entered the bar and walked up and said hi to Dave. He introduced us: this was Paul, his boyfriend, and Paul’s friend Mick. They took the available seats at the bar, which put them on either side of us and Dave went into deep conversation with Paul, leaving me with Mick to talk to.
“Never seen you here before”
“No, this is my first time”
“First time here, or first time in a bar like this one?”
“Both”
“Really? So what brings you here tonight? Dave?”
“Yeah we go way back”.
“But you’re not….”
“No but it doesn’t bother me”
“Well that’s cool. But I bet since you’re Dave’s friend you’ve thought about what it might be like, haven’t you?”
“Well, yes, Mick. I have, but I never did anything”
“Nothing? Never stroked your cock looking at gay porn?”
“Well, I suppose so…”
“Well, that’s something, isn’t it? Have you done it more than once?’
“Ummm…”
“I knew it! It’s OK, I know lots of straight guys that do that. Do you cum hard?”
“Yes. Yes I do.”
“It’s the excitement of the new. Tonight’s maybe a good night to try something a little more hands-on.”
I quickly changed the subject.
We drank beers and talked about hockey and movies and politics and a bunch of other things. Mick was funny and charming and I was really enjoying his company.
Dave said he was going to leave. That would usually end the night for me and we’d share a cab home, but Dave was going to Paul’s place so I was free to stay.
I thought about going home too, but Mick asked me to stick around. It was still quite early, so why not, I thought.
We got a couple more beers and spotted a booth that had freed up and went and got comfortable.
We continued talking. Mick was sitting close.
I was pretty keyed up, he was clearly interested in me and I liked him but this was something beyond my experience.
I confess that when I’d thought about doing something with another guy I’d always assumed it would be Dave, which would be a more comfortable way to experiment.
But Dave wasn’t here and I was facing a ‘fantasy becoming reality’ moment that was a little more intimidating than I had imagined.
Our drinks were done so I went to the bar for another round.
I felt Mick’s hand caress my ass as I got up from the booth. It was electric.
I had a few minutes to think about it as I stood at the bar and decided that I liked it.
Then I felt Mick come up behind me and take my arm.
He led me to a corridor behind the bar and pushed me up against the wall. He leaned against me, curled one hand behind my neck and pulled my face towards his.
His lips were on mine in a second and I succumbed to his forceful body language.
I opened up my mouth and he kissed me in earnest.
As strange to me as it was, I was very aroused and kissed back. My arms went around him and we kissed passionately. His tongue entered my mouth and I felt his other hand slipping down between our bodies.
He deftly undid my belt, top button and zipper in just a few seconds and slipped his flattened palm down into my boxers.
I didn’t stop him. In fact, I was probably kissing him with more passion
I felt him move his hand down further until he was touching my cock.
I was hard and sensitive.
Other men were coming and going along the corridor but I was too engrossed to care.
Mick’s mouth on mine took on more urgency and he grasped my hard cock and started stroking.
I held on tight and kissed him back as hard as I could, letting him know that I was enjoying what he was doing.
Another guy passing us stopped to watch and then reached down and fondled my ass for a while as Mick jacked my cock.
Two men’s hands on me, one in front and one behind, was too much.
Mick picked up the pace with his hand and I couldn’t stop myself. I came.
It spurted out of my cock onto his hand and dribbled down over my cock and balls and soaked my boxers. The other guy wandered off but Mick’s lips never left mine until I finished cumming.
Then he let go of my cock, pulled away and smiled.
His hand came up to my lips and he told me to lick it clean for him.
It was erotic enough to just take his fingers in my mouth, but with my own cum on them, I was very turned on.
I hadn’t ever tasted my cum before and it was strange flavor but I carefully cleared all of it from his fingers and palm.
He pulled up my jeans and closed the fly and belt. I could feel the rest of my cum in my boxers, covering my cock and balls.
I had had a girlfriend in my early teens who used to rub me through my jeans until I came in my pants – it was as far as she would go – and this felt the same. I enjoyed the wetness in my underwear.
Mick said we should maybe not bother with that last beer and instead go to his apartment which was close by.
I agreed and we were there within five minutes.
We talked about what had just happened. I told him I’d enjoyed it. It was the first time I had ever done anything like that but he had made me cum stronger than I had for years.
Then Mick asked if I would like to sleep with him.
I hesitated and he told me we would only do what I felt comfortable doing. So, with some trepidation, I finally agreed and allowed him to lead me to his bedroom.
I stood by his king-size bed as he began to undress me. Even though I had masturbated to gay and bi porn, I had never looked at a real-life man with sexual feelings before.
But Mick was gentle and nice and good-humored and put me at my ease and I was turned on by him.
I found that, beyond the quick handy in the bar, I wanted sexual contact with this man.
I was reacting to him with a hard-on that I didn’t try to hide.
He smiled as the last of my clothing came off. Stood there looking at me in my nakedness and then turned me around so he could take in my entire nude body.
He had me lie on his bed and asked if I had ever seen another man’s erection. I had not and told him so.
He responded by turning his back on me and quickly stripping off all his clothes.
When he turned back I saw his cock for the first time. He was very hard and his shaved pubic area made his cock stand out and look enormous. I couldn’t take my eyes away.
“Do you want to touch it?” He asked.
I rolled over to the side of the bed and reached out my hand.
His cock felt wonderful in my hand. Firm and warm and alive.
I felt the weight of it and he told me I could stroke him if I wanted.
I started gently running my hand up and down his shaft as he stood over me.
It was very exciting and my other hand drifted down to my own cock. I was stroking myself and stroking him at the same time. Fantastic sensations were crowding my mind.
Mick lay down beside me and I felt the full length of his hot naked body against my own.
He rolled over onto me and began kissing me again with the same passion he had used in the bar.
My arms came up around his neck as I kissed him back.
I felt him pressing his legs between mine and opened my thighs so that he could lie between them. I felt his cock rubbing my own as he started humping against me.
I reached down and my hand found his ass. It was smooth and firm and I loved how it felt as it raised and lowered against my cock.
He pulled away and told me that he would love to suck my cock. I was all for it.
But then thought I would like to suck his too so, without saying anything, I switched myself around on the bed so that we could lay on our sides and take each other in our mouths.
I felt my cock entering Mick’s mouth and opened my lips for his to enter mine.
The frantic kissing had made my lips puffy and sensitive and wet and Mick’s cock felt so nice in my mouth.
I gripped his shaft and sucked his cock as he did the same for me.
The excitement was so much that I knew I would cum very fast and warned Mick. His response was to grip the cheeks of my ass and pull me further into his mouth and he made me cum in his mouth.
My second load in less than an hour and this one even more intense than the first.
I had discovered that a man’s cock in your mouth as you ejaculate is a powerful way to enhance your orgasm. He sucked and swallowed every drop of my cum, all the while moving his hips to slide his cock into and out of my mouth.
I was so turned on and I was desperate to give him the same pleasure that he had just given me. I moved my hand up and down the hard thick shaft of his cock as I sucked and licked him. Then Mick’s body stiffened and I knew he was about to cum.
I gripped harder and held on, making sure he understood that I was willing to let him cum in my mouth.
This must have been the signal he needed because he started to shoot right away.
The cum burst from his cock and filled my mouth.
I held on tight and swallowed and swallowed and swallowed. There was so much.
He held me tight as he came and his face rubbed against my own cock and his hands caressed my ass.
It was very loving and sensual and I was enjoying every aspect of the experience.
The feeling of his cock in my mouth, the texture of the smooth skin of his ass. His firm body touching the length of mine, the taste of his cum. Everything.
Eventually he withdrew his cock from my mouth and pulled me back up to be facing him.
We lay there looking at each other. I was grinning like a fool.
It was cooling off on top of the bed so we climbed in together and got under the covers. I lay with him between his crisp cotton sheets and I touched him all over; exploring a man’s body for the first time.
He took me back in his arms and I felt his warm naked manly body holding mine.
We kissed deeply over and over and then finally drifted off to sleep.
After my one night with Mick I headed back up-town to my apartment. It had been a one-time thing, I was sure. We’d exchanged numbers but I didn’t plan to call, this had been so far outside my experience and I told myself that I was completely straight…. right?
Except I couldn’t stop thinking about what we’d done and it became the most prevalent image in my masturbation fantasies.
And I was masturbating more frequently. Lying on my bed and stroking my cock thinking about him pushing his hand down my pants. Thinking about his hard cock in my hand, his lips on mine, his tongue pushing into my mouth. I started using my other hand while I was stroking myself, imagining it was him.
And one evening I shaved off all my pubic hair, as Mick did, which gave me an amazingly strong erection and an intense orgasm when I inevitably jerked myself off after I was done.
The girl I was dating was surprised – even a little shocked, I think – when she first saw my smooth cock and balls.
But there was no doubt it was a turn-on for her. When we went to bed, her pussy was wet before I even touched her and my cock slipped into her silky cunt in one thrust.
I was barely into her when she had her first orgasm and she came again as I shot my load. With her second cum I felt wetness on me that was more than just my own cum: her own climax had been so strong that she had squirted.
I had never made her do that before. And, as it turned out, no other guy had either. She was exhilarated by discovering a new level of orgasm.
Her own trimmed bush was gone completely the next time we were together. I loved the feeling of our bare skin touching as I fucked her. I seemed so much more intimate.
But even while I was with her, I would sometimes fantasize about what I had done with Mick, and about what I might have done.
One night we were fucking and she was on top of me. I started to spread my legs as she rode my cock. With my hands, I pressed on the side of her thighs. She understood the message I was sending. She closed her legs while keeping my cock inside her cunt and I spread wide. Now we were in the missionary position but she was in the ‘male’ position and I was in the ‘female’.
She humped herself between my thighs and I grabbed the backs of my knees to hold my legs wide and in the air. She got into it and rode my cock that way while looking down at me, saying “you like this?” “You like being the little girl?” “Like having your legs wide apart while I fuck you?” And grinding her bald pussy down onto my aching cock.
I could only whimper “Yes Yes, fuck me”.
I was submitting to her and she was taking the lead role, for sure. And then I told her I was going to cum and she pressed herself down harder between my spread legs and drove my cock deeper into her pussy and I shot cum for ever, it seemed like.
She lay between my legs and lifted herself up on her forearms and looked at me. Just staring. And I could see her thinking.
“So…. that was interesting” she said. I could only agree.
My cum was dribbling out of her pussy down onto my bald scrotum and further: between the cheeks of my ass. I could feel it trickling over my exposed anus and I was enjoying how it felt.
Then she lifted herself off my cock and her hand reached down and rubbed all the cum over my smooth skin. I kept my legs in the air. My ass was lifted and she slipped her hand down and between the spread cheeks.
Still rubbing my cum, her finger found my asshole and she tickled around the rim.
I groaned slightly and she knew I was enjoying it and her finger tip stopped over the entrance of my ass and she pressed slightly. I groaned again and she pressed harder.
“You like this, baby?” she asked and I admitted that I did and she pressed more and her finger went into me. Then she started to move her finger in and out of my ass, lubricated by my own cum. I lay there on my back with my legs in the air, feeling exposed and vulnerable and completely into it.
She soon stopped, to my dismay, and then it was time for her to go home.
I didn’t see her for a week, but every day I was stroking myself and thinking about what we’d done. Combined with my recollections of Mick, my masturbation fantasies had never been richer and my cums had never been more intense.
Next time my girlfriend came over she told me she’d been thinking a lot about the last time and that she’d liked it and she asked if I wanted to explore further in the direction we had taken.
I was so pleased that she had saved me the potential embarrassment of broaching the subject. I just said yes and told her that it had been very exciting.
This was clearly the answer she’d expected because she had come prepared.
“I bought you a butt plug. Don’t worry, it’s the small size. It think you might like it”.
There were no prelims… she told me to strip and lie on the bed with my legs apart. My cock was hard but she ignored it. She had lube with her as well as the toy and I watched as she poured some into her palm and reached under me and started to rub onto my ass and then up between my cheeks.
She teased me for several minutes…. never quite touching my sensitive anus… always just going close and then moving her fingers away.
All the time she was looking at me, smiling, telling me how much I was enjoying having her touch my ass. Like I needed to be told!
I was getting so desperate for her to move to the next level. I started squirming around on the bed, trying to make my asshole reach he fingertips so she would start to go into me. She laughed and said I was desperate to be penetrated. And I was.
I wanted to feel something entering my ass.
Finally her finger pushed into me as it had done so briefly the previous week and I told her “oh yes, that feels so good” and she pushed in deeper.
She poured a little more lube directly onto the finger she had in my ass and pushed in and out, making sure that my ass was well and truly ready for the next step.
Then out came the butt plug. It was not large, but it was much bigger than her finger and as she started to rub lube onto it, I began to change my mind.
“Don’t worry, I’ll go slow” she said and placed the tip against my ass.
She pushed slowly but firmly.
As she met resistance she withdrew slightly, told me to relax, and then pressed again.
I relaxed a little more each time, and each time it went a little further into me.
Finally the widest part was into my ass and it slipped all the way in, stopped by the flange at the bottom.
With her hands free, my girlfriend stood and looked at me. The plug in my ass felt so good. I felt filled up. And lying naked with my legs spread, my ass impaled with my girlfriend standing over me watching made me subordinate to her in a way that I found beyond erotic.
She undressed and climbed up onto the bed. She straddled my head with her crotch, facing my feet, and lowered her smooth pussy down onto my mouth. Her pussy lips were engorged and felt stiff and rubbery and the juices covered my mouth. I took her clitoris between my lips and sucked, playing my tongue over it. Flattening my tongue so that the slightly rough texture rubbed against her clit, the way I knew she liked it.
She ground her cunt down onto my face. She had become so wet as she was shoving the butt plug into me that dribbles of her juices had leaked out of her cunt and between the cheeks of her ass.
She lifted herself so that I could tongue all the way to her asshole. Again she lowered herself. The tip of my tongue found her little rosebud and I pressed it in as far as I could.
Tongue-fucking her ass, I reached up and grabbed the tops of her thighs to pull her down more forcibly onto my face.
Then she leaned forwards and her ass moved away from my tongue and her pussy came back for more. As her pussy reached my mouth, I felt her mouth on my cock.
Her hands reached between my spread thighs and she started to withdraw the butt-plug from my ass as she sucked me off.
My hands were fondling her ass as I tongued and sucked her pussy and she began to fuck my ass with the plug. Pulling it out and pushing it back in slowly and steadily.
Each time she went all the way in I felt my anus clamp around it and raise my level of excitement, Finally I could last no longer. I grabbed her ass tightly and sucked… hard….. onto her pussy and my cum shot from my cock into her mouth.
She sucked and sucked and swallowed as I came into her mouth and I felt her body tense as she reached her own peak.
Juices poured from her crotch onto my face and into my mouth and I swallowed her cum as she swallowed mine. She rolled off me and we lay head to toe for several minutes, totally exhausted.
We left the butt-plug up my ass. It felt too good to pull it out.
Then she wanted to go out to dinner. Demanding that I leave it in while we were at the restaurant.
There was new secret between us that changed the dynamic of the relationship completely. Within a week, she was using a strap-on on my ass and I was loving it.
She was into it as well. She definitely got off when she was penetrating me, and when we went out she often made me go with the butt-plug inserted. Knowing it was inside me while we were out in public made her very horny. On one occasion she masturbated while we sat in a restaurant. Her hand slipped up under the dress she was wearing, hidden by the table, but she couldn’t hide her flushed cheeks or her heavy breathing. She was into the potential for exposure. All the time while she was fingering her pussy she demanded that I whisper to her how it felt to have my ass stretched by the plug.
I was enjoying this new sexual territory with my girlfriend for a few months and then one day, out of the blue, I got a phone call from Mick. He had been given a couple of tickets for the Rangers game the following night and would I like to go? Well, duuh. Live hockey is about the best spectator sport ever.
We arranged to meet at a nearby bar.
I can’t deny I’d thought about another night with Mick and when he called about the game I decided that I would spend the night with him again if he invited me.
So although I wasn’t sure what might happen this evening, I primped like a little girl getting ready for a first date. I shaved my genitals as carefully as my face, dabbed on some cologne and picked out my tightest jeans that I thought might attract Mick’s interest, if he was still interested.
We enjoyed a great game. At the final hooter he asked if I’d like to go for a beer and I agreed.
So we were chatting about the game and other things and generally catching up. Mick was as fun and entertaining as I remembered and I found that, once again, I was attracted to him.
He was still the only man I had looked at in a sexual way but something about him was pushing all the right buttons in my mind.
We hadn’t mentioned anything about the first and only other time we’d met until he asked me bluntly “So, how’s your sex life?”
And then I went into an explanation of what I’d been doing with my girlfriend and I confessed that it had all grown out of the night I had spent with him.
“So you’ve been thinking about it?”
“Yeah, quite a lot”
“And not feeling guilty or ashamed?”
“No, not really. I guess I weirded myself out by how much I enjoyed it, but decided to embrace it rather than feel guilty”
“Good for you….. so perhaps….?”
My answer was ready for his hinting question.
“Yes, I think so, Mick. Perhaps, yes”
We left the bar and headed downtown to his place. He kissed me in the cab.
The cabbie watched us in his mirror as I kissed back. I felt excited by how outrageous I was being and my hand reached between Mick’s legs and I cupped his package. I felt his cock harden as I rubbed and had to reach down and adjust my own cock which had stiffened uncomfortably inside my tight jeans.
Once in his apartment, we sat on his couch with a couple of beers. Mick asked me what would I like to do.
I had been enjoying the submissive role I had been taking with my girlfriend and told Mick that I would be OK with whatever he wanted.
He said “OK, why not let’s start with you sucking me off?”.
I got off the couch and down on my knees in front of him.
I reached up and undid, then pulled down, his trousers and briefs. He lifted his hips to help me. His erect member bounced up as the elastic of his briefs came down and I felt a lurch in my chest as I saw it again.
Mick has a very attractive cock.
I pulled his clothing completely off so he could comfortably spread his legs and then knelt up closer, grasped his shaft and took his cock into my mouth.
I felt his hand on my head as I bobbed up and down sucking his cock. Taking as much as I could into my mouth.
Mick pulled off his shirt as I sucked him and he sat there naked on the couch. I was still fully clothed, on my knees between his legs. Sucking and sucking and licking and stroking him and enjoying it. Really getting into it. Sucking his beautiful cock. Loving how it felt in my mouth.
I felt Mick’s hand reach down to my cheek and he gently indicated that I should stop. I lifted my head and looked up at him and he suggested that we go to his bedroom.
As we stood, he took me into his arms and kissed me deeply. His hands found all the buttons and zips on my clothing and he peeled me out of my clothes so that soon were were both naked, embracing.
He noticed my lack of pubic hair. “Mmmm that is so sexy” he said. “I was inspired by you. Mick” was my response. “That is even sexier!”
He held me tight as he kissed me and our cocks rubbed together I stood there in his arms and my legs began to tremble. He led me to the bed and gently laid me down.
His hand reached my cock and he stroked it. His lips never leaving mine. Then his fingers traced down the length of the underside of my cock and over my smooth balls and down so that he was slipping his hand between the cheeks of my ass. I spread my legs, letting him know that I was OK with what he was doing.
Mick reached for some lube and gently dripped some over his fingers and he started to slip his hand more and more between my cheeks. And then his finger found my asshole and he pressed.
I spread my legs wider for him. He pressed harder and his finger entered me.
I kissed harder and spread my legs wider still and Mick pushed his finger deep into my ass.
And then withdrew and pushed in again. And again. And again and again. He added a second finger and continued. Stretching my asshole.
I was loving the sensation. Mick was finger-fucking my ass and I was holding onto him and kissing him and loving how it all felt.
“I’m going to fuck you now” he told me.
“Yes Mick, please. I want your cock. I want you to fuck me”
He pulled his fingers from my ass, rolled up onto me and between my legs. His arms came up under my thighs and he rested my ankles on his shoulders.
My bare ass was lifted from the bed and I felt the blunt end of his penis find the opening of my ass. It rested against my hole for a moment.
Mick was on his hands and knees over me. I looked up into his eyes, put my arms around his neck and pulled him down, lifting my lips to find his.
As his mouth reached mine his hips moved forward and I felt his hard cock going into my ass. I groaned with the joy of giving my body to this man.
His cock slipped steadily into me deeper, deeper, and then I felt him grinding against me as he bottomed out. He stopped and we lay motionless for a few seconds and then he lifted his hips and his cock slowly, slowly started moving back out of me.
He reversed his motion and moved back in. I was loving feeling his cock enter me. He picked up his pace, in and out and in and out, and I lay there, my legs over his shoulders, my arms around his neck, ass in the air.
Helpless to resist, but I didn’t want to resist.
I was being fucked in the ass by a man for the first time and enjoying it utterly.
I hunched my body up to meet his thrusts. Opened my mouth wide, wanting Mick’s tongue in my mouth as deeply as his cock was in my ass.
Holding on for dear life as Mick’s movements became more and more frenzied. I pulled my mouth from his and said “cum in me, Mick. Cum in my ass. Shoot for me. Fill me up”
I don’t even remember all the things I said. I was mad for his cock and wanted to give him a wonderful orgasm.
I thought making him cum would be enough reward, but then his cock found somewhere inside me that was like the perfect spot. He was hitting it over and over and suddenly I came.
Nothing was touching my cock but gobs and gobs of cum shot out of it up onto my belly and onto his. As I came I squeezed the muscles of my ass and squeezed his cock in the process. He gasped and shook and drove his cock as deep as possible into my ass and I felt him let go inside me. Felt his cock spasm as each spurt of cum entered deep into me.
I held on tighter still and he collapsed down onto me. My cum smooshed between us, mixed with our perspiration and made our bodies slick. We rubbed against each other, Mick’s cock still in my ass.
Eventually we separated and lay there. I stared up at his ceiling, exultant. I had taken a man’s cock in my ass for the first time and loved every moment of it.