First Time

I'm bisexual - which I only recently figured out - and I had my first guy on guy anal sex experience (actually it was my first guy/guy experience ever) just about three weeks ago. After I had told a couple of friends (straight women) about thinking that I might be bi they decided to take me to a gay bar. Before going I had decided that I wanted to have some sort of sexual experience with man that night. My two friends and I got to the bar and at first we were watching everyone else have a good time and I was ready to give up on the experience when one of my friends pointed out a guy sitting in a booth with some other guys looking at me. We caught eyes with each other and smiled. He looked to be roughly the same age as me with sandy blonde hair and a beautiful smile. Then my friends wanted to dance so they dragged me along with them. At some point the guy I had been smiling at earlier had come over and started dancing and before I knew it I was dancing with him. It was awkward at first (I'm not a good dancer to begin with). It wasn't long before he took my hand and led me off the dance floor. We stood at the bar making chit-chat for a while. He had a gorgeous mouth and I found myself staring at his lips. Just as I caught myself not hearing a word he was saying because I was lost in my thoughts about his lips he leaned in and kissed me. I kissed him back awkwardly. Then he wanted to go for a walk and talk. I went to tell my friends who were still breaking down on the dancefloor what was happening. They were really excited for me. I was kind of scared but decided to go with the flow.

Kevin and I left the bar and started walking the sidewalks downtown. Again I found myself feeling awkward, but he told me he lived in an apartment close by and invited me over. I broke down and told him that this is my first time going to a gay bar or kissing a guy and that I was really nervous. He just smiled and took my hand and began leading me toward his apartment. I didn't know if this was a good thing or if I should be running in the opposite direction but again I decided to go with the flow.

As soon as we entered his apartment he started to kiss me and rub my ****. He whispered "I want you inside me" and then he started taking his clothes off so I started to take my clothes off. He was pretty much naked before I even got my shoes and my shirt off so he unbuttoned my jeans and got down on his knees. Before I knew it he had my semi-erect **** in his mouth and he was sucking me all the way into his mouth. It didn't take much to get me completely hard. He led me to his bed where I sat on the edge and he stood in front of me. I started to stroke his **** but I was too nervous to put him in my mouth. He reached into the drawer of his night table to get a condom and a bottle of lube. He handed them to me then he got on the bed bent over on his hands and knees. He reached behind him to start playing with his *******. I put the condom on and then squeezed some lube onto my fingers and then I rubbed some on his *******. I positioned myself behind him and rubbed my **** between his asscheeks a bit. He was stroking his own hard **** now too. "**** me" he said. So I pushed my **** into him slowly. He moaned then started moving back and forth on my ****. It felt amazing. I had never had anal before so I had never felt anything so tight on my **** before. I grabbed his hips and started to really **** him. Before I knew it he came. That excited me even more so I sped up my pace and I came while still inside him. Afterward we talked for a little bit and exchanged numbers and I said I had to work the following morning so I should probably go. I still felt weird about everthing and wanted to get out of there to think about it all.

It was a great first experience but I wish I had taken a bit more control rather than have him lead me through it. And I would have liked for the experience to last longer than it did but I can't complain too much. He came. I came. It was a good time.

Scott88 Scott88
22-25, M
43 Responses Jul 22, 2010

great story.......hope i have one to tell, soon.

Wow, he came, you came, I came.....thanks

it's so cool u have such supportive friends! they sound real special. sounds like they would really be happy for u! glad u got to have a real good experiance. don't worry so much u could of done somethings better at least u got to try & actually had fun ur 1st time. u got the experiance hopefully u learned something about ureself. i hope to try it someday soon too :) so did u ever see that guy again, or did u ever have another experiance with a guy?

when i was about 11 years old my neighbor ask if i would like to spend the night with his two kids ( 1 male and 1 female ). while in the bed with his son i felt someone rubbing against me and finally inserting his massive penis inside my ***. it hurt at first but felt pretty damn good. i haven't throught about that day until recently when i wanted to know how it would feel now as a adult to have someone insert their penis inside of me again and to actually climax inside me also. i am 65 yrs old now and everytime i think about this subject i get rock hard. can anyone help me to make this happen again.

I am 62 , but, very sexual. gay ,bi or straight. I just love sex. Good size in the penis department and snug in the butt section. Give and get is my motto. Would like to hook up , so lets get better acquainted. I live near the Great Lakes. Recently moved to Mich. no gay/bi partner , yet. Looking , but not to hard, Must be married man and gentle and most of all discreet. Where are you ?

So hot. You made me feel so horny. Add me!

I will add you. Get back to me on this network. Feel it ?

Add please

That is a very nicw way to have your first time , truly lovely,, XXXOOO Diane

Great story. I bet you'll have more experiences like this. Very hot.

i have never felt so hard in my life as i do now as i imagine how the sex must have been. it sounds so great that i too wish i could experience penetrating a guy!

damn that's hot! i don't sleep around on 'first dates', but hey, glad you had fun. take it as a learning experience. if you ****** him good, chances is he passed the word around, so maybe his 'freinds' will want to 'get to know you' better. ;)

I have never had sex with a fellow male but I have often thought about it, what does it feel like when he penetrates my anus for the first time? I wouldn't like him to be to big or thick say about five inches long by about four inches in cercumferance.

If he takes his time and is gentle it is the best feeling I ever had and so will you

I am 7 inches and medium round. But , am very gentle. Can pleasure you, I promise. Would stop at any time, if pain was to awful. Slow penetration , until full entrance is made. Then the pumping starts. Slowly , at first , then the pounding , until fully completed. Climax is guaranteed. Once took a guy with a 10 anaconda. Hurt like hell, until the head was inserted. Then less pain, could feel him all the way in and out. Got even better , when he shot his load. The lube really helped. The biggest pleasure, was the pleasure he got as he screwed me. To this day , he was by far the biggest. Will take any size as long as he gets pleasured. I would in turn love to pleasure him,(or you). let me know. I will be waiting to hear from you, and you, and yeh even you.

Lots of interesting replies! Well, you were very brave! Don't worry about what did or did not fit your expectations of whatever... the important thing is you did it, he was a nice, goodlooking guy, you had good sex, and you did something that many people only fantasize about for their whole life.

The guy you met sounds like he's a bit of a "player", or, well Idk all the terms, but he sounded very experienced picking guys up. He cut to the chase immediately, which isn't something all gay guys do, but some do, some don't. I think it probably worked out best that he led you because it was your first time, you were nervous, and you needed someone to take you by the hand. Don't worry about that. That's probably also just a matter of the dynamics of two guys together, whereas before you were probably usually the "leader"... this time you got to be led. Good luck in the future.

sometimes I think I might be bi. I have played with my anus with toys and my fingers and love the feeling. Sometimes I fantasize about bottoming for a hung fit guy. Does this make me bi?

What\'s the best way to meet someone?

you have to decide what type of encounter you want. Message me and I\'ll explain.

The problem I've found is this is a young man's game. I'm a MWM, 61 and have just come around to the idea but finding someone is hard. Seems everyone wants the 20's and 30's. Being married I have to be careful and going to a gay bar doesn't seem to be ideal for me. The few guys I've met on the Internet are mostly talk and don't want to meet. So here I am still looking for that first time.

Hey Cooldudenj I'm on the same boat as you and always fantasise about having a hung fit guy penetrating me... Also I regularly play with my *** and have been using my fingers plus other house hold items for a few years and it does feel amazing I have the best ******* when using a really thick long cucumber :)
Think I could easily have sec with a hung guy and it wouldn't hurt too much as I've already got used to stretching myself out ;)

Yes. Many guys are. Loving, wanting **** or wanting to get ****** in your *** by another man is a good sign you are bi. Careful about acting on the urges. Once you have ****, ***** won't do. You might even have to face the probability you are a latent homosexual like me. I

2 More Responses

Hot story!

I wish I had been your first. I'd have sucked you off first, let you relax and then come again in me.

That was hot ;) if any one wants to talk dirty and send pics ill do the same ;)

Way to go Scott. It's cool that you have some friends who helped push you along. What a stud! You need to see this guy when you have more time.

sounds like you had a good time. the first time is the icebreaker. its an experience. we learn from our experiences and get better as we go. you are now better prepared for the next time

What did your straight women friends think when you told them what happened ? Do they want to watch next time ?

good story, you are very revealing and open, and it is refreshing

Hot story

Great story and great first time!

Great story, just wish I was him

Just like you I am curious ... but I'm about to have anal sex this weekend and I'm frightend of the pain.... hopefully all goes well

how did it go?

I am a straight guy who had my first gay experience at 40 after talking to a guy online for weeks. He was a Top and very turned on by by the thought of taking me for the first time. I had always been extremely curious about what a bottom role would be like. Finally built up courage to meet him in a cafe and we talked a while then he said 'lets go". I was nervous as hell as we got back to his appartment and he walked me straight to the bedroom. He undressed me and took control and before I knew it I was in his mouth and hard as a rock. He laid me on my back at the end of the bed and sucked me as he was on his knees on the floor. What he did next completely drove me crazy. He put a pillow under my arse which lifted me up and then then spread my legs wide, kept sucking and then suddenly started ******* me. No women had ever done that lol. What an amazing, wonderful feeling and after some time he fingered me and then it was time. After all that I was pleading and squirming for it and he lubed me, slipped on a condom and slid in slowly, being quite big I got to say it was hurting but before I knew it he was pumping me hard and ************ me and in the middle of this pounding I had the most intense ****** of my life.

A great experience and I have repeated this a few times since!

wow. I love that the first time was amazing for you.

Agree. People in general have too many hang ups when it comes to sex. There's a lot of bi guys that won't admit it. So they deny it. If u don't want to out that's one thing but at least realize u may have same sex fantasies.the no home quote is so stupid. Just admit u think that dudes might be hot. In the end of day you're still a man, unless u feel otherwise, but that'sa whole other issue, topic! Lol

Oh yeah, religion is also part of problem. Even fit straights it's cray! Wait til marriage for the right one? What f Mr or Mrs right never comes to your life. This is especially bad for women, so they stay virgin while most guys are getting some? Oh yeah, even with guy friends? Come on! Sheez!

Sometimes accepting your homosexual tendencies can take a very long time. I know. Calling yourself straight while you have homosexual sex encounters can be a way to gradually see who you are. Outing yourself or being outed by someone who doesn't know you can be very difficult and at times can be dangerous

Sounds like he's a hot hot guy!

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i love bicurious ;))

It sounds to me like you had a good experience for your first time. You didn't run the other way and you reacted appropriately. Hope you find the right man and for a lasting relationship.

WOW!!! Great story wish I could of been your first

I would love for you to **** my ***.

reminds me of my first time as well. glad you had a good time though.

So hot mate, I wish it was me who me who broke you in. I'm 26, 9 inches, and love younger lads. Well done and keep going mate !!

I don't know but the first experience lasts forever, and it is usually good, just like mine. It was the best sensation I ever received.

Super hot. Thank you. I'm a married guy that thinks about the first time every day. Plan to read it again as I **********. Yum.

Super hot. Thank you. I'm a married guy that thinks about the first time every day. Plan to read it again as I **********. Yum.

You RE SO LUDKY<br />

Thanks, Scott. Thinking about taking next step with guys and think about the same thing happening to me. Please add me.

Thanks, Scott. Thinking about taking next step with guys and think about the same thing happening to me. Please add me.

yea the first time is the best and the worst I was pretty young when I got my first time I was a farm hand and this guy he was older than me he was very friendly with me, and he helped me a lot around the farm with my shores, it was a summer job and sometimes I was staying in some dorms they had for the staff, and he was always staying at the dorms, one night he was taking a showe, the shower and the restroom had no door, so I came to the sink to brush my teeth he finished his shower and stood behind me and he said "want to shower"? he had a great body black curly hair and Hazle eyes he was like 10 years older than me, I turned around and I said yea, I was wearing only some short paints, I took then off and I follow him to the shower then I realized he was getting hard so I started getting hard too, he put soap on my back and my *** and then he licked my *** hole like crazy that night I shot again the wall my load and he did the same thing we were friends for many years and we did all kind of things until he turned 50 got and stroke and died. I enjoyed was a great buddy

That was a good story! I often think about a man taking me and leading much the way he did you. In some way it seams like it might be easier the first time. Cheers

I to love bareback.I love to feel the hot *** filling my manpussy.Cleaning yourself out can be fun too.I love to use some kind of juice so that my puss tastes good..

Yes I really want to feel a man inside me let him shoot his ***** make me all wet and slippery inside.

Sounds like a good first experience. Also a couple of amazing friends there that helped you overcome some fear.

very cool , im hapy for you !