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  1. #31

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

    I was 22. It was my late wife's 23 BD. Had never thought about sex with another. We had a 4 day weekend. She had invited 3 other couple to spend the weekend a sail to Catalina Island with us. She had been using a home made toy on me for some time. For her present she wanted me to suck and be fucked by all of them. Over the 4 days it happened many, many, many times. I loved it. We played with the same 3 couples for around ten years after that. She loved to be on her back under me and guide him into me and we would 69 while he fucked me. She would always cum just watching a dick pump me.

  2. #32

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

    Quote Originally Posted by easilyused View Post
    where did this happen? I live in Illinois and want it to happen to me !
    No kidding me too.. I either need a shower, or need to rub one out.. maybe both at the same time.. my first time here, and now I really want this more than ever..

  3. #33

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

    It was on a sleepover with my best friend. We were gonna jack off and he said lets stick it in each other ass. It hurt at first, he has 7". As he left it still for a while it began to feel good. He cummed a lot in me, I loved that. Then I fucked him slowly, I have 6". We love it, have been doing it ever since. We are both married, he has 2 grown kids. I have none.

  4. #34

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

    I agree with Cherokee....I'm sitting at work half-hard, horny....now I gotta try to hook up before I go home...lol.

    My first time was as a teen. I'd played with a buddy and we progressed from mutual jerking off, to jerking one another off, to sucking one another, to eventually anal. We started with fingers, then toys, and advanced to him rimming me and getting me ready. For me, it takes time to get relaxed, releasing my inhibitions, and getting loose enough for penetration. The key was pushing outward to allow him to enter me (almost like you want to take a shit)....Patience and size make a big different too. My friend took his time and little by little he got deeper and deeper. The feeling went from heat and some pain, to total pleasure. My cock dripped seminal fluid as he pumped me. I was actually shocked to realize he was "balls deep in".... his balls started slapping mine and the feeling was amazing.

  5. #35

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

    Ilost my cherry last week to a 19 year old with a small cock about 4.5 inches but he had low hanginh big balls. I loved it hurt at first but then it changed to pleasure. Now I know why my wife liked it in the ass. only wish I had done it sooner. Cant wait for the next time.

  6. #36

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

    First time was awkward to say the least . My cousin and I were around 12 or 13 . The second time we swiped a little margerine to ease the experience . Much smoother going after that little discovery . We did it well into our late 20s . Both married with children by then . Drifted apart after that though .

  7. #37

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

    My 1st and only time was about a month ago (65 yrs. old). He didn't use enough lube and came to quick. It felt like he was ripping me open and was not a good feeling at all. I would like to try it again, but with someone that was a little more considerate.

  8. #38

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

    My first time was 3 years ago. I laid on my back atop his desk(Office scene=hot). His dick was small, so it went in real easy, especially with the lube. Didn't feel any pain.

  9. #39

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

    Mine was about 4 years ago we were both dressed in drag at his house and of course one thing led to another and we were naked sucking each others cock and he ask me if i had ever been fucked and of course i had not so i said i was all for it . He fucked my ass but good took his time , it was the most wonderful sexual experience i have ever had looking forward to doing it again .

  10. #40

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

    It tool me a long time to open up, didn't know how to relax. The first time I enjoyed was in a movie theater, I was wearing fuck me shorts. This guy came behind me licking my neck and rubbing his cock over my ass. He took me into the bathroom, put on a lubed condom and fucked me over the bathroom sink. I loved being taken like that so submissive. If there where any tops in south florida I would do it more often

  11. #41

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

    As a bi female who has never done tha anal thing...WOW.

  12. #42

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

    Loved it! 18 years old, with my best friend. Felt fabulous, and I especially loved the feeling of him holding my hips from behind and plunging his cock into me and spurting cum (pre-HIV). It was super hot, and made me the bottom that I am today, LOL! Luckily, my super-hot wife also loves to see me get taken by a big cock, and then fuck her. I am a very lucky guy!
    Happy wife, happy life!

  13. #43

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

    Haven got the opertuniny to be fucked by a guy , but the feeling of getting a blow job while being fingered is awsome ! Anyone want some of this tight ass ?

  14. #44

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

    My first time was a little weird. I've sucked cock before but that was it. Then "it" happened. Having used toys before, it wasn't painful at all until he got close to cummimg. Good Lord he damn near broke my hips. Ouch! Lol! I prefer nice and slow and long.

  15. #45

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

    I was 13 and he was 15, we had known each other for anumber of years and often had sleepovers at each others houses. He asked me if I would like to sleep in his bed with him rather than on the camp bed, I thought it would be nice as the camp bed was rather uncomfortable. Once in bed together he started to touch me and asked me to touch him, i was enjoying it so did not mind playing with his penis as he played with mine. After a few minutes he asked me to turn away from him and take off my pants, i could feel him pushing his penis into me and although it hurt at first i thought he must have done it before so it would be ok. I began to enjoy the feeling of him being inside me but it only lasted a few minutes before he pushed as hard as he could, held me really close and came. We continued to sleep together on our sleepovers for the next year or so until he and his family moved away. This was my first sexual experience and still one of my best sexual memories, I have no doubt that it moulded my sexuality and made me who I am today.

  16. #46

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

    Like many others, my first experience was painful, but only because we had no idea what we were doing. The second time was much better, and only got better with each experience.

  17. #47

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

    After looking at the above stories I feel sorry for so many guys who had a bad experience. Mine was great, and I was 60 when it happened. The doer was a handsome Negro cop from Dallas, attending a foursome party arranged by my girlfriend. My response was, "Good God, I've been missing this for forty-eight years! What is wrong with me!" I began looking for other men to fuck me. The same guy filled my mouth with cum during that wonderful night, and so I have been a cock-hound ever since. The last time I even wanted to fuck a woman was ten years ago, and when we were saying goodbye the following morning, with her sitting in front of me naked on the bed and me patting her very wonderful pussy, I thought, "God, I wish she had a dick!"

  18. #48

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

    my first was nice but awkward... Was when I was young and it was with my best friend... Happened on my parents bathroom floor after looking at Penthouse

  19. #49

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

    I was 46. After my divorce. Got tired of only toys so went to a gay bar and picked up a really hot younger black dude - around 30 or so.

    His dick was between 9 and 9.5 inches and thick. And I told him in advance he would be the first real man to ever fuck me with his real dick.

    Answer to the question is this: It was great and sexually intense. When we were done he said he coudn't believe an ass virgin could take a dick as big as his (I did but slowly and softly for the first half of the fuck, and he never slammed me fast or hard because I told him not to beforehand).

    Not only just took it either. I fucked him back as hard as he fucked me. I was in motion the whole time. And I was telling him to put his dick in me "more more more" the entire time - subconsciously mosty.

  20. #50

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

    Last month was my first time. In fact,it was only my second time being with him. We had been sucking each others cocks on the first date and were doing the same thing this time. He started fingering my bottom while sucking my cock and I started squirming and trying to ride his two fingers inside of me. He is experienced and im not so I let him lead. he rolled me over and pulled my hips up to him so he could enter my bottom. I heard him say Oh crap ive gone limp. I told him just relax. I guess we both wanted it too badly and were too tense. I proceeded to suck his cock again ( I have discovered I am good at it and love doing it!) And started fingering his rear. He got hard as a steel rod so I just up and straddled him before any thing else could cause his hard on to go away. His cock just kind of popped in! It hurt at first but I slowly started to ride him and the pain went away. Oh my God he felt good inside of me! I think I must have rode him for about ten minutes and he started to stroke my cock. Holy moly I came like I had never done before and I guess my anal contractions caused him to cum because I could feel his cock pulsing in me and come hitting the walls of my anus. I am hooked now and hope he will let me do him also.

  21. #51

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

    my first time was probably 30 years ago or more, it happened at a bath club I think he was a little bit older than me at the time I really don't remember I do remember how we actually took time to make love to me not to have sex. there was not an inch of my body that he did did not touch lick and enjoy. when he entered me it seems so natural so good and it was very back as a matter of fact. I remember hearing someone asking him how was it and he said I was fantastic. I'll never forget that experience. The only other time was years later and that person did not take the time that he did and was not as enjoyable I hope to find somebody who will take your time again to take me because I am actually open to it thank you for sharing all your stories guys

  22. #52

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

    I was seduced by a porn store owner during college. It started with a bj and after awhile we ended up in his office where he took me on his desk... hurt like crazy at first, bunt after a few minutes it felt great and about 20 mins later I came from it - a very intense experience....

    Cheers

  23. #53

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

    My 1st time was when I was 50 yrs old--i guess u can say it was a mid year crisis thing. I am happily married but wanted to see how it would be with a guy a fantasy I've always had for many yrs. Anyway I found this guy on the internet and we met for a coffee and went back to his place--he was gay and had a partner who also jopind in so I was in heaven sucking and kissing and jerking and just having a great time! Soon after his partner left and I asked him if he would try anal on me--he asked if I was sure I wanted that and I said hell yea! Well he asked if I was clean there and I asked him to explain and he said did I have an enema or been cleaned out. I told him no so he set up an enema bag in the bathroom and I did my thing! Once I was clean and ready he lubed up a dildo and opened me up some--he was very gentle all the while--he then told me I was ready and wanted to know which way I wanted him! So not knowing to many positions for anal I said doggie style! So he got behind me and put his cock at my opening and slowly and gently entered me! God it hurt at 1st so he stopped and waited till I was ready--did I mention he was 8" and thick--he waited till I started to move back on him till he pushed forward--now it started to feel amazing!! He fucked me easy at first then when I urged him on he fucked my hard and steady till he filled my ass with his hot jiss! Its happened several timed dince and its always something different with them and I am so addicted I have told the wife and she understands and is very excited about it and wants to join in sometime soon.

  24. #54

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

    Good lord I hope I can experience this some day. I've done everything else with another guy, but no fucking...yet.

  25. #55

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

    My first (and this far only) experience was when I was about 14 and it was comically bad. A friend from out of town was spending the night, and we stayed up late watching what Siskel & Ebert called "horny teenager" movies, then went out to the pool to skinny dip. When we went to bed, we started playing with ourselves, then each other. The next day continued our explorations. I went down on him, and he asked me if it felt good. I was a bit puzzled...did it feel good to him? Then we decided to try anal. I tried to enter him first, but either I was too big for him, he was too clenched, or a bit of both...never got in. We switched places and I *think* he got it in, but to this day, I'm not entirely sure. He was smaller than me, and it felt like something was in my ass, but if he was in, he didn't do anything...just sorta stood there. After a moment, he asked me if he was in. I answered, "Dude, I'm on my hands and knees with my ass in the air. You're the one who can look down and see if it's in. YOU tell ME."

    The very end of our session really says it all: he didn't know you could cum from masturbation until he saw me blow my load; said he'd always stopped because it felt like he had to piss.

  26. #56

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

    I am very jealous! When we kids, 12 or 13, during out J/O sessions we slide our cocks up and down each others asses. Well on hot sweaty days the kid next door used to let the head of his slide in me, it felt amazing! But that's all the further it went. I am married, kinda straight, but i still want to see what it would feel like to go all the way in!

  27. #57

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

    My first experiences were with a bunch of my friends in my mid teens. We were macho jocks with girlfriends. We were just so horny that man play (jerking off anyway) was a great release. We watched porn, and jerked for hours !! One day the group was busy with other stuff and it was just me and my one friend Mike and we went further: We tried oral successfully and eventually we explored anal together. His parents were out from 8 am to 8 pm working, so we had the house (and their bed) to ourselves. We went from oral, to showering together, and eventually started fingering our asses and then sticking his moms vibrators and toys in our asses ! We evolved to "why not let me try fucking you ?", and we ended up doing that as well. A lot depends on size, shape and patience. I find long and thin better than thicker for sure. I played with a few couples and some experiences were really awesome and others not so much. Sometimes it just doesn't work. One dude kept losing his erection after he got into me. I think he wanted to please his wife, but maybe wasn't as bi as he wanted to be.....One guy (who's cock looked exactly like mine) tried fucking me a few times. I knew I could handle him (I'd handled sizes like it before), but I was so tense from the whole experience that I couldn't relax. I eventually fucked him a few times, and we discovered (one day while playing without his wife involved) that the best way for me is on my hands and knees. He tried previously with me on my back. She was sucking me and jerking him as I laid there and he tried to get in, but couldn't make it work....I could not relax my ass enough !! Once we found that secret we were golden !! Most recently, a local message therapist topped me a few times. He's a good 8", but the bone structure is thin and he knows how to take his time !! He put on a rubber glove first, lubed me slowly and gently, massaged my balls and prostate, slowly jerked my cock and eventually began rubbing his cock on my ass crack and then sliding his cock into me: He was a master ! He was as perfect as you would want a man to be. He totally took his time. First the head, then a retraction, and slightly more into me. He kept repeating this until he moaned and I reached under me to feel his balls touching mine !! I asked "you in all the way ?", he moaned "oh-yeah".... When we were both ready to come, he pulled out, I turned over, and together we glazed my belly with a big load of both our cum....There was a time I was spit-roasted by two guys on a cruise ship balcony, but that's for another time

  28. #58

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

    In a word – messy. We met in an outdoor pickup spot. I was in my late twenties and married. All the other guys that I had picked up just wanted to 69, Which was fine with me. We almost always lay on out sides with our heads resting on the other’s leg. Cocks and balls that could be coaxed through glory holes were happy to be sucked. I’d thought about being fucked, but craved sucking cock much more even than even being sucked off. I liked (like) it so much that I didn’t (don’t) mind cumming first. (Hence the name Cum1st with men who might want to stop after they cum).

    I always made sure I was clean of course, but didn’t give any thought about what might be IN my ass. He came at least twice in my mouth, and then asked to fuck me. I was up for it and don’t remember any pain. There was just a wonderful dizziness. After he came in my ass he was satisfied. I liked it! We cleaned up, and like the other hookups we never saw each other again. Sometime after that I bought a latex cock to accompany self-satisfaction. It really pumped out the pre-cum out of my stiffie. I’ve been reamed quite a few times by a steady hookup while it lasted. Each time he had sucked me off first, and didn’t last long enough to give me an anal orgasm, although I do remember having double vision and week knees as I supported myself on the back of a sofa.

    Thinking about this is making me want to drag out my home made crank operated “sybian” and make some improvements so I’ll have to test it. It will run at 50 or 87 strokes per minute. The length of the stroke is adjustable. Turning the crank one way it pushes up on the in stroke, the head sweeps down, and withdraws. In the other direction it does just the opposite.

    Oh yeah! I still can’t imagine why anyone wouldn’t jump at the chance to be with a woman.

  29. #59

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

    I was about 16, the guy was in his 50's. I had been sucking him off for a few months but nothing more, then he mentioned that he'd like to fuck me. So I ended up letting him try, got up on all 4's on his bed and he used a ton of lube, finally got it all the way in and pumped a few times but it was too big for me. Tried again a year or 2 later with a different guy but the same result. Haven't tried since.

  30. #60

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

    I have this buddy of mine I want to ask to fuck me but I'm to scared to ask we joke around bout doing it but I'm to scared to say I'm serious any suggestions

 

 

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