MY Very First Time In Meeting A Man

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He has sex the first time in his life with another man.
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My first time with another man.

I have always considered myself straight, my entire life has been consumed by woman, I am attracted to them, I want them, I desire them and I have sex with them. But and this is big but, I have always had a fascination with cocks, ever since the first time I saw one as a teenager in the locker room.

I know as men we are not suppose to look at other guys cocks but I was fascinated by them. I of course being a heterosexual male put it out of my mind. I went of to college and had lots of sex with woman. Eventually I got married and had kids.

When the internet came into being I was obsessed with looking at porn, eventually I made my way to some gay sites and my curiosity was peeked. Here I could look from the comfort of my own home at all the cocks I wanted to without fear of being caught.

Then you start to fantasize about acting out, maybe I could hook up with someone without getting caught, someone anonymous, that doesn't know me, someone that would not shatter my entire world as I knew it. So this is the story of that encounter.

I joined several gay sites It seemed so simple yet I was scared to death to actually go through with it, it was one thing to fantasize about it, quite another to actually do it, could I really go and meet someone and have sex with them.

I, unlike many people, like to experience everything. If I was going to do this, I was not interested in just jacking off with a guy, or even just a blowjob, I wanted to experience it all, including getting fucked by a guy.

I put an ad out of what I wanted, and I also looked at other guys ads. It may sound bizarre but I wanted a good looking cock, long and cut with a nice mushroom head, in reality quite different then mine. You see, I am uncircumcised, I am very well endowed with a cock that is 7 inches in circumference at the base, very thick indeed, but not cut.

I eventually met a guy who was gay and was interested in meeting with me. He was a good looking guy, and from the picture he sent, a very nice looking cock. His ad stated he was a top, which was fine with me. I have fucked a lot of girls, I was ready to experience what it was like to get fucked.

We chatted on instant messaging and eventually talked on the phone. He was hot to meet with me but I was resisting. It was one thing to have a fantasy, quite another to actually act on it.

I wanted to meet with him, I wanted to suck his cock and get fucked by him and I masturbated to it many a nights imagining what it would be like. But to actually do it was another story. I wasn't prepared to shatter my heterosexual world. But to his credit Jim persisted. He kept begging me, he wanted to hook up in the worst way.

I finally agreed, and as the day approached the more nervous I became, could I actually go through with it. I was determined to, but would I lose my nerve at the last moment.

I made the long drive to his home, he lived about 45 minutes from my house, plenty of time to chicken out. But I didn't, as I approached his home I really got nervous.

I pulled into his drive way and looked around I was worried someone might see me going into his home, even though I didn't know anyone in his neighborhood, it was sheer terror, was I coming out of the closet. How could I be, I still liked woman, I was straight, maybe, slightly bi.

I knocked on the door and Jim answered, welcomed me in, and I took a real good look at him. Very good looking guy about 5foot ten to 6 feet tall about 200 pounds, short hair and did not act gay whatsoever, one of those guys you see in public maybe working out, never dreaming that guy is gay at all.

Of course he looked me over as well, I wasn't sure what he was thinking, I found out later I am just his type. I am built like a big football player 6 foot tall about 245 pounds solid all over, hard like a football player with a bit of a gut I need to lose. Been described by others as a mountain of a man.

Jim showed me around the house very neat and clean and well decorated, now I knew he was gay cause no heterosexual man take care of their home that well. We seem to hit it off pretty easily and I was looking forward to seeing his cock. As he showed me his home we started to migrate toward his bedroom.

His master bedroom had a glass door that lead to the pool area and two things came to mind, the first was I would love to suck his cock as he sat on the edge of the pool. The second thought was, his door has no curtain, if someone wanted to, it would be possible for them to look over the fence and see Jim and me together.

Jim and I both looked at each other and we instantly knew it was time, he was on one side of the bed and I on the other, we both started taking our clothes off, as Jim bent down to take his underwear off I knew I would be finally getting a good look at his cock and I didn't have to look away, I could openly stare at it and it, was ok.

Jim had a very nice cock, I have been told there are two types of cock, showers and growers, I am a grower, it grows to a long thick cock. Jim is a shower, his cock was long and beautiful even soft. I openly admired his cock as he laid on the bed. I finished undressing and also laid on his bed.

We got in a natural 69 position so we could both play with each others cocks. Moment of truth, I was about to put my hands on a cock other then my own, I was living my fantasy, and for all those guys reading this story that has always imagined it but were afraid to act on it. I can tell you honestly it was amazing and I enjoyed every minute of it.

His cock was still soft and it felt spongy in my hand, I was very warm to the touch, I felt like I had a new toy. I was so consumed with Jim's cock that I had forgotten he was playing with my cock.

Reality hit me in the face when I felt his tongue licking my cock and then his mouth swallowing it. Oh my god, it felt so incredible. It is true, guys do really give better blow jobs then girls. As he swallowed my cock I brought my attention back to his.

I took his cock and looked at it, trying to get the nerve to bring it closer to my lips, I knew if I did that I would be forever known as a cocksucker, even if it was only me calling myself that. I did it anyway, I brought his cock to my lips, I licked the head, letting my tongue swirl all around it. It was the most natural feeling, like I had been doing it all my life.

I found something about myself at that moment, I loved sucking cock, and this would not be the last time I sucked a cock. Yes I still loved woman but I found out I liked cock as well. I tried to take in as much of his cock as possible, but I have to admit I gagged on it because he was so long.

But I kept trying, I loved the feel of his cock in my mouth he was starting to get hard I wanted to feel it expand in my mouth, and it grew even bigger and harder. I was sucking his cock like there was no tomorrow, I kept hoping this day would never end

I could tell Jim was getting really excited, I must have been doing a hell of a job on his cock, his legs started to tighten up, I heard him grunt.

I relaxed and let nature take its course. He exploded inside my mouth. I felt the first wave of cum hit the back of my throat, it was so hot. It wasn't as bad as I thought, but he kept pumping more cum in my mouth, I couldn't hold it all in, some of it dribbled out of my mouth but I swallowed as much of it as I could.

If you had told me a month ago I would let a guy cum in my mouth I would have told you that was crazy, never happen. And it just happened, and I welcomed it, I wanted to taste his cum, I wanted to feel his cock throbbing in my mouth, I wanted to feel it jerk and inside my mouth as he came. His cum was salty, but I didn't care, it felt so good.

I know what it feels like to cum in a girls mouth and now I know what it feels like to have a cock exploding in my mouth and I was hooked. I could tell Jim's head was very sensitive and I gave it a couple of more licks before letting him slide out of my mouth.

He then went to work on my cock, I relaxed and let him enjoy himself. He was an expert cocksucker, it takes allot for me to cum through a blowjob but he did and soon enough I grabbed the back of his head and held him to me as I exploded inside his mouth.

I cum allot I have been told by many a girlfriend that I am a heavy cummer, I guess it was too much for Jim, he could contain it all, so he got up and went to the bathroom to get rid of the excess.

We both laid in bed talking, I absentmindedly played with his cock and he rubbed my chest. We soon got horny enough that I asked him if he wanted to fuck me and he said yes.

Here was another barrier I was about to cross, I laid face down on the bed, facing the poolside glass door, Jim got behind me and laid on top of me. I told him to go slow because I was not only had a virgin ass but a very tight one at that. Jim reassured me we would take it as slow as we had to.

I could feel the weight of his whole body on top of mine. I could feel his growing cock on the crack of my ass, he was rubbing it all over making himself hard. I felt it growing, all I could think about was feeling him inside me.

Here was another milestone I was about to cross, I felt his cock at the entrance of my ass and I felt him give a little push, he tried to slip the head in and OMG the most intense searing pain shot through my body and I told him to pull out. He did and told me to relax my ass muscles.

I didn't think I as going to be able to take his cock, maybe his cock was too big and my ass was to tight but I was determined to feel it, I told him to try again but to go even slower.

Jim took his time and this time he only slipped in the very tip of his cock, I relaxed my ass muscles and told him to push further. The pain was still intense but not as painful as the first time.

I encouraged him to push further till his head broke through and was inside me. He felt me take a big breath and waited for me to tell him to keep going.

Jim kept pushing until before I realized it, his whole cock was inside of me. He laid back on top of me and we both relaxed a bit. I could feel all the weight of Jim on top of me but now I could also feel his cock inside of me. I really loved that feeling, my ass was full of cock and it felt incredible.

Jim placed his hands under my chest to draw me even closer to him and as he laid on top of me he started fucking me, nice and slow, I could feel every inch of his cock inside of me as he pulled out and pushed it back in.

We had a rhythm going, Jim was really getting into it, he was now fucking me fast and hard.

I whispered to him, "Fuck my ass Jim, fuck me hard, cum inside of me, I want to feel your cum exploding inside of me."

That sent Jim over the edge and he exploded inside my ass, I actually wished we could keep fucking, it felt that good. He finally pulled out, sweaty and exhausted from fucking my ass.

We laid in bed together for a while, both of us resting, catching out breath. Finally after laying there for a while we both got up and got dressed and I left his home, agreeing to meet again.

One final thought, I was very lucky that Jim was my first, I needed someone who was both knowledgeable and gentle at the same time but could turn into an animal when needed. I can promise you this would not be the last time that Jim fucked my ass and I was already looking forward to the next time as I drove away from his home.

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AnonymousAnonymous6 months ago

My first and only time with another man was when I was 18 and he was about 60. I was hitch hiking and soon after we started moving he began to show off the growing bulge and invited me to join him jerking off. I was nervous but my uncut cock was getting hard and wet with sticky precum. We found a quiet place undressed and took pleasure in the sight of two erections both wet and smelling of fresh precum. His veiny cock was hard as rock and after a few strokes he blew a huge load of cum, slightly off white in colour and quite watery. I began to stroke and noticed that he was working his cock up for another session…I soon blew my load of young warm white cum which seemed to go on forever and certainly enough to fill a small shot glass. His second load followed mine, less than the first but still a respectable amount. He invited me back to his house for an afternoon of sex but I declined and we parted ways. Although I consider myself as heterosexual, I have always regretted that decision.

AnonymousAnonymous7 months ago
This story has me more ready to have my ass fucked!

Im still cherry but fantasize daily of making love with another man. I am always the bottom, the cock sucker and get my ass cummed in. I explode unlike ever cumming from fucking a woman. The thought and jacking off thinking of being naked with a man and being his woman makes me never want pussy again! I now question myself. I am for sure bi but probably full out homosexual and I love it. I am ready to go out to gay clubs to go home with men and get my ass fucked good.

Wish me luck!

Riki1942Riki1942over 3 years ago
Nice Way To Lose Your Cherry

Taking a load up your ass bareback is a nice way to lose your cherry. I really need my partner's load in my when I get fucked. I'll have sex with a guy and use a condom, but my intention is to find out if we are good together and that it's not going to be a one off thing. When I get to know him well enough to trust that he isn't going to give me a disease, I always want him to fuck me bareback and cum deep inside my ass!

Riki

AnonymousAnonymousover 3 years ago
Looking Forward to It...

I've used my wife's dildo several times over the years when she was out of town. It took me about 10 time before I actually made myself cum while be ass fucked by her toys. I really enjoy the intense orgasm that I got but definitely would enjoy the cum deep inside me! Maybe one day...

AnonymousAnonymousover 3 years ago
One day maybe

Although, I haven’t EVER been with a guy, I’ve dreamt about it a time or two. I’m intrigued. I guess you could say that I am 98.99% heterosexual, and 1.01% bi-curious. I have confidence that I am not alone. In fact, I am convinced of it. I’ve only been to a gay bar once, and nothing happened. However, if anything were to have happened like what was racing they my mind, well, someone there might have had an extremely awesome night.

AnonymousAnonymousalmost 4 years ago
Looking for my first time

I’ve sucked a few cocks but I’ve never had a cock in my ass I read all the stories about it but I have not found anyone to take my anal cherry… One day soon I hope

AnonymousAnonymousalmost 4 years ago
OMG

I wish

AnonymousAnonymousalmost 6 years ago
My first time

My first time happened three years after I married my wife. I had sucked other men off a few times but I was keen to try taking a cock in my bum. I secretly bought a good sized butt plug and regularly used it until it would slip into me with no pain. I knew then I could do it so went to a sauna in Southampton. I sat around with the other men then went into a cubicle alone. Within minutes I was joined by a guy who asked was I top or bottom. Nervously I said I was a bottom and reached for his quite log knob. He moved closer and I sucked him for a while. As I did it he lubed my bottom and began fingering me. I rolled over and lay on my back with my legs wide apart and bent. I felt him pointing his lovely cock into my bum hole and then quite slowly he pushed it in me. I called out for him to fuck me and he began doing so, whilst I revelled in being fucked like a girl. He was quite quick to come and soon I felt his sperm shooting into me and again I was so happy. After he withdrew he went off and I soon left the sauna. However, I have since been bum fucked many times and now my wife knows about me it is even better, but that would be a different story!

AnonymousAnonymousalmost 7 years ago
I only read this because I was curious

I have been straight for 47 years. Your story changed my mind. I went from being a little curious, to knowing that I want this so bad. I want a rock hard, slobbery wet cock to explode in my mouth. Still happily married, I hope this turns my wife on.

AnonymousAnonymousalmost 7 years ago
I sucked cock and had the best ass fuck ever

My first time I was 17 it was a sleep over with an older guy who I knew but didn't know he was gay. In bed ready to sleep he came into my room and slipped his hand under the sheets and massaged my cock. I was turned on and said will you treat me like a little whore. He said he would do me as much as I wanted. We both disrobed and got in bed together and kissed. First time I ever kissed a guy and it excitd me so much I got instantly hard. He then moved down to my throbbig cock and started to suck me. It felt so good that I said let me taste you so we 69 sucked for what seemed like 10 minutes then he turned me over on my belly and started to lick my asshole. It felt so good to be licked like that. He got me so excited and I begged him to fuck me. I was a anal virgin and he popped my anal cherry that night. He got me very well lubbed up with just his tongue and then used some real lube and slowely pushed his huge cock in my waiting ass. It hurt at first and I cried a little and he pulled out and it seamed like it felt as if I was sort of empty so I told him to fuck me for real. He entered me slowly and just pushed the head of his cock in and out for a few minutes and it felt so good and I knew that I would want more but was afraid because after having his cock in my mouth I realised that it was massive after the head and only grew bigger as it got to the base of his shaft. I then told his to fuck me a little deeper and he started to push his cock into me even farther penatrating me deeper with each thrust. It felt sort of painfull at first but soon it just felt so good that I belted out "Fuck me like a little whore"" Fuck me hard and deep" I want to feel all of you inside my ass. He proceeded to fuck me balls deep with pounding thrusts over and over. I felt filled up with each thrust and arched my ass up and begged for more. He fucked me hard and fast for about an hour. It was the best fucking that anyone could get guy to guy. I thought I wanted to be gay so i begged him to cum in my mouth so i could feel and taste real cum for the first time and he flipped me over shuved his hard cock in my mouth and said suck me till I cum. I sucked and licked his cock for what seamed to be another 10 minutes and finally figured out how to make him cum real quick. I used my tongue and flicked the bottom of the end of this cock repeatedly and finally he groaned and released a huge load og cum in my mouth. He filled my mouth completely when he first shot his load and then started to pump multipule laods into y eager mouth. I loved the taste and swallowed mose all of his cum then when he stopped cuming I began to suck and milk what ever was left from his cock till it was completely empty. I still had a load of his cum in my mouth and I got up and kissed him and spit his cum into his mouth and he smiled and we swapped his cum for a few minutes and swallowed the rest. He then laid me back down and proceeded to suck my cock. It was the best sucking I had ever had and I came almost instantly. Because I had had a hardon all the time he was fucking me I built up a big load of cum and he drank almost all of it from my cock and then sucked an milked me as I did him and then when he finished he came up and kissed me and spit my cum in my mouth. It to tasted great an d we kissed and swished cum back and forth for some more time. I then considered myself his bitch and would get fucked by him every night for the next month. He made my asshole so wide from all that fucking that I was able to have a double penatration by him and one of his fuck buddys later on that month. I had both of them cum in my ass then suck it out and spit it in my mouth as we then kissed and swished the cum between each other. From these experiances I am now considering myself a complete bottom as I only want to be fucked in the ass and I want to taste cum every time I am fuckd.

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