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  1. #61

    Re: how was your first time getting fucked by a guy?

    I'll add my first time story...it was about 5 years ago, I was 30 or so, knew I had a desire to be with a guy for years at that point...would finger myself, etc. Finally tried some websites, posted an ad on manhunt.com, and would chat and email guys but nothing came of it. Finally a guy that lived a mile from me, contacted me and we got to talking, it took weeks or so, before I worked up the nerve to want to take the plunge. Finally IMed each other one day, and within a few minutes I was at his house. He knew that this would be my first time, so I already told him, when I get there take charge. Take charge he did!! Within a minute of walking into his house, I was bent over getting rimmed. Holy Shit, what a great feeling. After a few minutes, we moved to his bed, and wow things just got better. I was on all fours in no time, he was still rimming me at that point until I felt him stop. I arched my head back to see that he was getting in position to finally enter me, at that point I couldnt contain myself, I was all sorts of excited but also anxious. I finally felt the head of his cock pressed agaisnt me until I felt him slowly work his way inside. What a feeling!! Thankfully he wasnt too big or too thick, and it didnt take much to get him all the way in. At that point he just went to town on my ass. Grabbing my hips and pumping until he felt himself getting close and stopping just long enough to grab a condom and finish fucking me, until he came. At that point I was in ectasy and I didnt ever come yet. Of course at that point he rolled me over to my back and gave me one of the best blowjobs I ever had. Since then we have gotten together a few more times. Now that I am married it is harder to get together with him or any other guy, but since that time I have gone from being bicurious to 100% bi sexual.

  2. #62

    Re: how was your first time getting fucked by a guy?

    Quote Originally Posted by fused View Post
    Good lord I hope I can experience this some day. I've done everything else with another guy, but no fucking...yet.
    I could help you with that.

  3. #63

    Re: how was your first time getting fucked by a guy?

    Mine was about a year or so ago, I was with two other men and I asked one of them to fuck me. It wasn't real pleasant, I think he was trying to hard and it hurt so I asked him to stop. I would try it again, slower the next time.

  4. #64

    Re: how was your first time getting fucked by a guy?

    I was 55, I had a place ,made a contack. I was so scared but also wanted to try it so much.he came over we talked then sucked , then he got me on my back and before I knew it he was in slowly fucking me. it was good but I really want to try with someone that will start slow then fuck me hard and fast

  5. #65

    Re: how was your first time getting fucked by a guy?

    Crazy hawt drunk car sex with a total stranger

  6. #66

    Re: how was your first time getting fucked by a guy?

    My first time was excellent. I was about 24 years old. He was well hung, but gentle and patient....he worked slowly and carefully so I didn't feel pain. He eased it in as I relaxed more and more. By the time he was all the way in I was begging him to pound me all the while I was stroking myself. I found out that orgasms while receiving anal are the most intense orgasms I can have.

    It happened after I had already had sex with women and it did not change my attraction towards women at all. If you really liked chocolate ice cream and along comes a flavor that you had never tasted before, say amaretto, and you really liked that too, would you suddenly not like chocolate anymore? Of course not! Sometimes you might be in the mood for one or the other and if you are really lucky you get to mix them together and enjoy them at once.

  7. #67

    Re: how was your first time getting fucked by a guy?

    Hurt like hell. I was 16 and fucked my Mr Hector who was in his 40s. I did cum twice as he fucked me. The following times was much better. Had to get used to it.

  8. #68

    Re: how was your first time getting fucked by a guy?

    Painful, we first started with me laying down and him trying to put it in with nothing more than some spit but it hurt to much. He suggested that he set down on a chair and I lower myself down on him. It hurt as he first entered but as we went along it started to ease up and pretty soon I was rocking in time to him getting into it as he suddenly pushed me off of him and I watched him spew a huge geyser of cum from his cock. I was 14 at the time.

  9. #69

    Re: how was your first time getting fucked by a guy?

    I was 31 I think. I'd been using toys and my fingers way before that. The first time with a guy was a good friend and he was the right size. It actually felt really good cause I had warmed up and stretched with a toy. I have a gf now and she knows I like ass play but I haven't told her I'm bisexual. I really need a good fuck so I guess I'll tell her.

  10. #70

    Re: how was your first time getting fucked by a guy?

    I was 12 he was 13 first time i hsd sex and got fucked in my life, first time was little painful , my ass being small and tight, virgin. his was big and thick for his age, I just loved being fucked since then...
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  11. #71

    Re: how was your first time getting fucked by a guy?

    My first and only time was when I lived in [place redacted]. It was about 10 years ago. I'd been going online and had met a few guys, but it had only been mutual oral at that point. Then I met [name redacted] during an online chat and we agreed to meet at a Wendy's close to my house. We chatted a bit, and were comfortable enough, or horny enough, with each other that he followed he to the house. There it was the same as with the others. Mutual oral (69). It was his first time w a guy, and about my 4th or 5th (or 8th or 9th, I'm not sure which). Anyway, found out that [name redacted] lived near where I worked, so we met at his house for a "nooner" a few times. Still just 69ing. Finally, [name redacted] came back over to my house and we made out (kissed, hugged, touched) and [name redacted] said "I could really use a shower", so we both got in, a first for both of us, and lathered each other up. After I rinsed him off, I went down on him in the shower, but didn't make him cum. Then he did likewise to me and I told him I'd rather continue on the bed, so we quickly troweled off and went to my bed.
    we continued the kissing and fondling and sucking, and I asked him if he would try to fuck me. He pulled out a condom and I went for my ky, and I put the condom on him and we rubbed the jelly on each other. I assumed the position (head down, ass up) and he slowly started rubbing his cock around my anus. THAT WAS AWESOME! then he pushed in a bit and I felt IMMENSE pressure, to the point of pain. [name redacted] wasn't overly large (more like me, about 5" and thick), and I had played with "toys" in my ass before, but I guess I was nervous and tense. [name redacted] took his time and continued to slowly rub and prod! and I finally relaxed enough that I felt the head of his cock go in. OWWWW! He slowly pushed in deeper, and I kept relaxing and it finally eased up to the point that it was feeling WONDERFUL! after a few strokes, I felt him tense up and tighten the grip on my hips and heard a moan and a groan and he popped out of me. I rolled onto my back and took the condom off of his cock and proceeded to clean him up a bit. He was a bit tender, and was shrinking at that point so we got up and got dressed and he left. We met a few other times, but that was the only time that we fucked

  12. #72

    Re: how was your first time getting fucked by a guy?

    I was around 15 when I met an older man who took interest in me while working around him at school. He followed me to the rest room and asked me if I mind him watching. Now I had been sucking my brother's cock for a long time and playing with my older sisters pussy and tits for several years, so his interest did not surprise me. When I pulled out my cock, he grabbed it and started stroking it. Then he asked me to undo my pants so he could feel my ass. He pulled out his enormous cock and started rubbing it up and down my crack. He put the head of it against my ass hole, but could not get it into my very tight ass. He turned me around and asked if I felt like sucking his erect cock. I was amazed at the size of it since my brother's cock was longer than mine, but very thin. I took it and sucked it for a few minutes and tasted his precum. He was so horny that it did not take long for him to fill my mouth. I swallowed it and loved the taste. We met before and after school for the whole year having sex with each other. Loved every minute of the excitement in that store room with that huge cock.

  13. #73

    Re: how was your first time getting fucked by a guy?

    that is so fucking hot, nearly came reading it, I want that cock.
    Last edited by abc123jd; Jul 24, 2014 at 2:13 AM.

  14. #74

    Re: how was your first time getting fucked by a guy?

    The first time getting fucked was about 90 days ago. It was a big disappointment. I was having a MMF play time. when my friend went to fuck me he shrank and was not able to finish and they then switched to a toy. I have had plenty of toys but the first experience was a bust. I will say on the other hand I was able to fuck my friend a few days before that and as always loved that play time.

  15. #75

    Re: how was your first time getting fucked by a guy?

    I was around 46 when a guy came over and I sucked my first cock. He touched my ass and I came, all over the comforter. I kept sucking that cock until he jacked it all over me. My first anal was a few months later. It felt so good. I loved, and still love, the feeling of a hard shaft in my ass. Kinda out of practice. But I now know it is the way I want to play.

  16. #76

    Re: how was your first time getting fucked by a guy?

    I've been fucking my ass with my fingers, dildos, vibrators , plunger handles, basically anything I could stick up there would do. I finally was fucked by a real cock about a year ago. He went in slow, he was very concerned that he wasn't hurting me, and then after I assured him I was fine and it felt great he started to fuck me. sadly he didn't last but about 4 minutes. But it was still good. My most recent cock was with a guy in a motel room and he started off doggie style then wanted me to roll over on my back with my legs up around his neck so we could look at each other. he fucked me good. Real good. He asked if he could cum in me and I said yes, but then pulled out and stuck it in my mouth and came inside my mouth so I could swallow his cum. A very tasty treat.
    (He did have a condom on while fucking my ass, then pulled it off before sticking his dick in my mouth)

  17. #77

    Re: how was your first time getting fucked by a guy?

    i dream of getting fucked real good like u did especially in the missionary position where we gaze into each other's eyes & loose ourselves in each other's lust

  18. #78

    Re: how was your first time getting fucked by a guy?

    Was 12 the guy 13, hurt like nothing else. But for some strange reason I kept going back for more. Knew it was going to hurt, but still wanted it.

  19. #79

    Re: how was your first time getting fucked by a guy?

    I was 31. He was 16. I was newly divorced and was into porn big time. This was back when chat rooms had just started. I went into a gay chat room. He found me and we started chatting. I was super nervous about it but he kept asking over several days to meet me. So, one night, I made the decision to meet and I drove out to him. We met in a secluded place. He got into my car and we talked, awkwardly. He asked if he could suck me off. I allowed him. I came in his mouth and he swallowed every drop. I was so turned on by it that I pulled his out and did the same (that was my first time sucking). We were way out in a secluded area. He asked if I wanted to fuck. I said yes. So we got out of the car and got naked. He went first. He bent over the hood of my car. I slid inside him pretty easy as I wasn't his first. I fucked him for about 20 minutes before I blew. Then it was his turn. I assumed the position. He took his time since it was my first time. The head going inside felt awesome. Finally after several minutes, he was able to get fully inside me. He fucked me for what seemed like hours until I felt him throbbing and moaning prior to cumming inside me. It was so HOT!

  20. #80

    Re: how was your first time getting fucked by a guy?

    Quote Originally Posted by lkld71 View Post
    I was 31. He was 16. I was newly divorced and was into porn big time. This was back when chat rooms had just started. I went into a gay chat room. He found me and we started chatting. I was super nervous about it but he kept asking over several days to meet me. So, one night, I made the decision to meet and I drove out to him. We met in a secluded place. He got into my car and we talked, awkwardly. He asked if he could suck me off. I allowed him. I came in his mouth and he swallowed every drop. I was so turned on by it that I pulled his out and did the same (that was my first time sucking). We were way out in a secluded area. He asked if I wanted to fuck. I said yes. So we got out of the car and got naked. He went first. He bent over the hood of my car. I slid inside him pretty easy as I wasn't his first. I fucked him for about 20 minutes before I blew. Then it was his turn. I assumed the position. He took his time since it was my first time. The head going inside felt awesome. Finally after several minutes, he was able to get fully inside me. He fucked me for what seemed like hours until I felt him throbbing and moaning prior to cumming inside me. It was so HOT!
    That's creepy and disturbing.

  21. #81

    Re: how was your first time getting fucked by a guy?

    i have not yet, sure want to with this guy who has a BIG 8" COCK, CAN HARDLY TILL I DO GET TO FEEL THAT DEEPLY IN MY TIGHT ASS ! I'VE HAD A DILDO IN MY ASS AND TOTALLY ENJOYED IT, ALL 6"S. Anyone close to me care to teach how - to receive, im waiting

  22. #82

    Re: how was your first time getting fucked by a guy?

    I'm looking for someone to be my first...

  23. #83

    Re: how was your first time getting fucked by a guy?

    GREAT THREAD!
    My first time was earlier this year (Spring 2014). I'm 49 and divorced with 2 kids. I'd had strictly oral experiences on several ocasions up until then. Prior to 4-5 years ago I was strictly hetero, but had plenty of imagination, and had been sliding things into my ass, when the mood was right, since I was young. The orgasms are much stronger with something up there. The last couple of years I been able to cum just from a dildo pumping away back there.

    For my first time being fucked, I met a bi couple (both fully bi) on line. We'd gotten together once before and she had been the center of attention while he and I spent plenty of time sucking each other off. He has a very nice 8" cock that is nice and thick as well. I'm a good 7" and thick, but not as thick as him.

    The second time we got together the wife couldn't make it. I went to his place and we started hugging and rubbing out cocks together then made it to the bed where we got into a nice 69. I really wanted a real cock slid in my ass so soon after I asked him to scratch my itch. I was rock had as I got on all fours while he slipped on a condom and lubbed up. He fingered me a little, but being used to toys it didn't take too much to get me ready, although I hadn't taken anything as big as him yet. He was patient and slowly worked the tip of that wonderful cock into me. At first there was a little discomfort. He pulled out and them pressed the head of his cock back against my pucker and he slid in. Once I'm opened up I love the feeling of something sliding in and this was even better! I felt completely full and immediately felt that delicious tickle and tingle with a slight needing to pee feeling as his hard cock began rubbing against my prostate! He pumped slowly at first working the head in deeper. After 4 or 5 pumps my horniness took over and I pushed back on his next thrust taking his full length into me in one push. It was incredibly erotic and an incredible feeling for me to have my ass pressed against him thinking of and feeling his entire length buried inside! Soon he was fucking away in earnest with me pushing back into every thrust, my hard cock bouncing away below! I lifted my head and upper body up and could immediately feel more of that delicious feeling of his cock working my prostate. There is nothing comparable in my experience with women. It was intense and my mind was awash with the new sensations as my orgasm built slowly from deep inside. The orgasm worked its way to a crescendo and was much longer than a normal penis centered orgasm. I looked down and below my untouched penis was a pool of cum. He pumped away and finished in the condom and withdrew. He was amazed I'd cum, as was I. It was an incredible experience.

    Being fucked by a guy and having sucked has not changed my love and appreciation of women. I prefer women and still have wonderfully dirty thoughts of what I want to do with them. I have a girlfriend now, who does not know my door swings both ways yet, so I haven't been back with the bi couple. I view this part of me as liking someone and not letting their gender get in the way. It also a way to open my sexual horizons to new forms of pleasure. Society (most men that is) think it's hot when women play together! Why should they have all the fun!

  24. #84

    Re: how was your first time getting fucked by a guy?

    we are in Illinois . ive only had my wife and her strapon in my ass but feels so good ... she want s help fucking my ass and stroking a nut off in my ass then its her turn
    6185621169

  25. #85
    berryhard
    Guest

    Re: how was your first time getting fucked by a guy?

    My cock is hard as a rock reading this ! I've had great oral experiances before but an anal virgin. I have on many occasions used a 8" realistic dildo in my ass and I cum very hard with a thick dildo "fucking" my tight ass slow deep and hard. It's an amazing feeling and I can only imagine a real cock must be even more amazing.
    I am looking forward to some day soon experiencing being penetrated anally and fucked for the first time. Until then I will just have to strike my cock and fantasize how it will be....

  26. #86

    Re: how was your first time getting fucked by a guy?

    I was 13 my first time. He was 15.

    Our moms were best friends and as children we played doctor (probably a bit more than most). They had moved away for about 4 years, but moved back after his parents divorced. Our moms, both being single, spent a lot of time together, so we did too. One night, our moms decided to go out and left us alone. We were looking at an old Playboy and he asked if I remembered playing doctor with him. Of course, I did (and had a massive crush). He asked if I wanted to play doctor again and within minutes we were naked. Our "game" was much more advanced and, in no time, I was sucking on him. He was really hard and pulled out and climbed over my back, sliding his cock up and down on my crack, dripping precum on my hole and making me slick. He pressed against my hole and pushed in slowly. It hurt a lot but I didn't want him to stop. He got inside completely and began humping quickly until he came inside me. What a rush!

    Being young, he got hard again quickly and fucked me 2 more times that night. After that, we were inseparable.

  27. #87

    Re: how was your first time getting fucked by a guy?

    haven't had a cock from a guy .. my ife has a strapon that iike a lot ... n he loves fucking with it to... se sometime gets caried away with it but it gets her off to
    high there.. we ae in Illinois
    Last edited by adamdawn; Dec 30, 2014 at 5:03 AM. Reason: added something

  28. #88

    Re: how was your first time getting fucked by a guy?

    I was 13 or 14 years old my first time. While at first quite terrified it turned out pretty amazing. It was my two older brothers who introduced me to male on male sex when our parents where out of town for the weekend and they were taking care of me and my sister. They took me into my dads workshop and initiated things by making me kiss their penis and eventually putting them in my mouth. The were very aggressive and cruel with me and this is when I learned that I was a submissive. Since then I have had only male on male sex

  29. #89

    Re: how was your first time getting fucked by a guy?

    I was a young teenager when topped by a friend in the 70s. We used Vaseline for lube and did it bareback.

  30. #90

    Re: how was your first time getting fucked by a guy?

    Quote Originally Posted by bradford07 View Post
    First time was on business trip. Got talking to another guy at the hotel bar, went to leave to go for a swim in the pool, he joined me. Afterwards he invited me up to his room for a drink. Went to his room got out of the wet suit wrapped towel around myself, he came out of the bathroom totally naked, he asked if I minded, he was nicely hung. He told me if I wanted I could drop my towel, which I did, I immediately got a hard on, we played around, then got into 69. He started licking my hole, horned me out, then he fingered me, then he asked if he could fuck me, I told him I never had been fucked. He went slow and let me get adjusted to his cock and he kept pushing till he was fully inside. He rode me good. We did for the next two nights of my trip.
    Very hot

 

 

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