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My first time with a man

I finally tried sex with a man and it was great
I have long been a reader of erotica but this is my first time as a contributor. Actually, this is the first time I am telling anyone about my first (and so far only) experience with another man.

I met my wife when I was 20 and got married a few years later. We have been together for 20 years, have 3 kids and a good sex life by most standards. Earlier this year I realized that I was with my wife for half my life and have been faithful to her with few sexual experiences prior to her. I also found my occasional thoughts of experiencing sex with a man were turning into a full blown obsession.

I started thinking about what it would be like to suck a cock when I was 16 and have thought about it ever since. The thoughts come and go, sometimes stronger, sometimes leading me to look at pictures of men together or stories of a mans first time. I liked reading about men experiencing gay sex when it was their first time, in the presence of a woman, perhaps encouraging them or forcing them against their will to take that cock into their mouth. I saw myself as straight, after all I was married, had kids and can't stop looking at women, so what if I thought about sucking cock now and then. As more and more became available on the internet, I sought out articles about other straight men that think of this and found that it is common and that lots of otherwise straight guys enjoy occasionally being with another man.

My obsession grew. I occasionally looked at dating sites, classifieds, reading posts from straight guys looking for a blowjob on the side, gay men looking to fuck, transvestites with their promise of the best of both worlds wrapped into one. After years of being a passive reader I started posting my own classified postings looking for other married guys and I started hearing from them. I really wanted to go through with it but chickened out each time, failing to reply to these guys looking to hook up. That was until I finally worked up the courage to go through with it earlier this year when my wife was out of town for the weekend.

I don't remember his name. There was nothing remarkable about his reply, other than that he was married, his wife was out of town and he wanted me to come over now to have sex with him. As much as I wanted it I was scared to go through with it. Despite the fear I got in my car and drove to his house. I sat in my car thinking of going home but worked up the courage to go to the door. He answered and I walked in, I was so freaked out about what I was about to do I could barely speak. Despite having my first intimate encounter with another man, this was the first time I would be with someone other than my wife in 20 years.

He put on some straight porn and left the room to get something. I took off my clothes and sat down, stroking my cock to get it a bit hard as it is very small when limp (much more of a grower with little to show). He came back and talked a little before he got on his knees and took my cock into his mouth. It felt good and looked odd to see a man looking up at me with my dick down his throat. He sucked for a while as fear kept me from getting fully erect. When he stopped he stood up and his dick was in my face. His dick was much bigger than mine, much longer and much thicker. While he was hard, his penis felt different than mine, perhaps it was just the size as it felt so much bigger and heavier in my hand. I thought this is it, my chance to experience a cock in my mouth and I started licking the head of his penis.

I started sucking and he started moving his hips, pushing more of himself into my throat. I tried to take it all in but had a hard time doing so. He looked down and told me to to take more of it reminding me that he had my cock all the way in his throat (not to mention his is much longer and thicker than my own and this being my first time). I did my best and he started fucking my face getting most of it in. I felt good about the joy I was bringing him really getting off on taking this submissive sexual role. While he was deep in my mouth the phone rang. He told me that he needed a moment and answered it; it was his wife driving back from wherever a couple hours out of town. He started talking to her while walking back to me. He motioned for me to get back onto his dick and he started pushing it back down my throat while carrying on the conversation with his wife. He looked down and gave me a look to tell me I was doing a good job as they wrapped up their call.

It was at this point I started getting nervous about him cumming. I wasn't sure if I was prepared to have him cum in my mouth and how I would handle it. I didn't get to find out as he stopped feeding me his cock and asked me to fuck him. I put a condom on my cock, and he pulled out the butt plug he had in his lubed, stretched and ready ass. I tried but couldn't get hard enough to penetrate him. I don't normally have this problem and chalk it up to extreme nerves. I asked him if he wanted to fuck me and he did. He took out some poppers which I never saw before and showed me what to do, I took a hit as he lubed up my ass put on a condom and slipped his cock into me. He did not take a lot of time, but I was ready as I was playing with a butt plug while browsing those listings before heading out to see him. I was shocked how much I liked the feeling of him inside me. I did not experience the pain I was expecting as I felt his big cock run up against my prostate. He started fucking me harder as I leaned against the desk of his home office. He was a bit taller than me and we weren't aligned just right so he suggested we try the chair. He sat down in an office chair in the middle of the room, and lowered my ass onto his lap with his dick inside my hole. I started riding his dick like some porn starlet and with each thrust down the chair rolled a little backwards until we were pressed up against the wall and I was riding his cock for all it was worth.

I was in heaven feeling sensations I never experienced while bringing this man to pleasure with the tightness of my ass, squeezing his cock with the muscles in my ass. Finally I couldn't stand it and I started stroking my cock and shot cum all over my hand, my stomach and the floor as he filed the condom inside my ass with his cum.

As soon as I came, I felt all of the nervousness and awkwardness come back into me. I asked him where the bathroom was and went inside, cleaning myself up. I then went back into the room and grabbed my clothes, telling him my wife would be home soon and I needed to run. I said goodbye, he went to clean my cum from the floor and I never saw him again. I don't recall if I knew his name but I don't know it now.

My ass was sore for days after that having never got a workout like that. I couldn't stop thinking about what I did and that I actually did it. When my wife came back the next day I fucked her with more enthusiasm than in years and enjoyed every bit of eating her pussy with a new found perspective having sucked a cock. I fucked her better than I did before having experienced what its like to be the one getting fucked. I learned a lot from the experience. That I am bi, that I have strong submissive tenancies, and that while having had gay sex my love for women was no less than it was before.

While I loved the experience, I have not repeated it yet. That first time I was able to rationalize as something I was doing for myself, something I owed myself, to experience what this was like and know how I related to the experience. While I wanted to do it again, I had to think through the consequences of getting caught, of getting and bringing home an STD, of being outed as bi (in the conservative town in which I live) and of cheating which I was not prepared to do (again).

I have not told my wife about this experience or that I am bi. I had told her recently that I would be interested in a MMF 3some and started revealing my submissive desires to her. The experience I hope for is to be with a man while with my woman and enjoy the full range of bisexuality.

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Comments(16)

robin48
Posted 26 Aug 2013 22:00
nice you took a big cock up your ass
PG564E
Posted 22 Jun 2013 20:49
Very erotic and honest. I think it is fantastic that your allowed you dream to come true, and not only to get a man hot with a blow job, you took that big cock up your ass your first time also.
A fantasy of mine.
HotBttmInBriefs
Posted 15 Feb 2013 10:52
Very well written. Loved reading about your first time. My first time was different as I occurred much earlier in my life than yours did. But I can remember the feelings of being so curious.
cityboy1
Posted 04 Aug 2011 09:57
A really good story. Like the others who have left comments I too am bi-curious. Don't know if I would ever get as far as you did but you never know do you?
james46
Posted 20 Feb 2011 11:32
Loved your story reminded me of my first time. Got me really hot. More please
JayR
Posted 26 Nov 2010 06:10
You described me to a "T". The similarities were eerie ... I thought I was reading my own story. I applaud you because you followed through with your desires. I am still waiting and wondering ... and reading about other men's adventures. I can't stop thinking about being with another man BUT I can't seem to get over the fear. Consequences do follow actions. Would love to correspond with you or someone who has been there. sgtjrudolph@yahoo.com. Thanks.
Ulthred
Posted 25 Nov 2010 16:37
I can very much understand the ordeal that you went through over this. Thanks for sharing.
hairlesscock1
Posted 24 Jul 2010 08:45
Good story. It reminded me of my own Bi experiences.
john11738
Posted 19 Jul 2010 17:48
WOW I guess you nailed this one. So many others including me have had that same desire. Heart pounding, heat building, dry mouth can get hard enough but want it more than anything else in the world at that time.

Very Cool

Thanks
phoenix993
Posted 17 Jul 2010 21:11
great story ive done the same with bi personal sites but have not had the guts to go through with it maybe soon
greenhead3
Posted 17 Jul 2010 09:46
A good story and a good write. It sounds like many men who have been married a long time have the same question about the bi idea. A difficult question for many. Good work. Keep writing gh3
geoff123
Posted 16 Jul 2010 21:35
Thanks for the story, it bought back memories of my first time with a guy. As the others agre it was well written and easy to read and one really felt the nervousness.
Ramjet69
Posted 16 Jul 2010 09:06
I enjoyed your story very much and it is well written. I have had a few similar experiences, I fully understand the nervousness and the real pleasure! I hope you will write more!
Bunny12
Posted 16 Jul 2010 07:53
OMG is this story so familiar to me. Be careful what you wish for you just may get it in a way you are not expecting at all. Great story too.
iamwoman
Posted 16 Jul 2010 05:33
Good write up. Thanks . . . .

stephanie
Posted 16 Jul 2010 04:22
Very well written, especially for a first effort... x S
 

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