First time you had anal sex

[sarah-o]

I seems to me that so many straight guys and gals don't do a lot of research about sex. I am surprised that you wanted to ever continue to have anal sex at all. Of course the first time may hurt if the sphincter is not properly exercised (stretched) beforehand, and above all, insufficiently lubed!

I did say in my post that I applied hand cream 'liberally' - perhaps in using 2 or 3 fingers I did manage to stretch the sphincter - perhaps I was just lucky.

But I totally agree with your post and I wish both that guy and I had been more knowledgeable before the event.

 

[B_am12388]

I was 15. I know, too young, but I was reckless, lol. If I could do it over again, I would have waited.

 

[w2btm]

I was 17, and learned very quickly that I had no talent whatsoever at bottoming. .

I was 16 and had never been with guys. met this guy at the beach went back to his place. he was 29 and kind of led the situation. He rimmed me good and then pulled out his 10.5" monster. The uncomfort only lasted about a minute. He fucked me for about 3 hours and I shot 5 loads. He wouldn't pull out and just kept going. I learned that day that I was a very talented bottom:smile:

 

[AM_092]

My first time wasn't as interesting or eventful as some previous ones But here it is:

My first time only lasted for about a minute... but we did stop, rested, then tried again - for a few more times. I just couldn't handle the pain. He was 8 inches uncut, and quite thick... but that wasn't the problem. With enough lube, he slipped in after a few attempts... I just couldn't go on because my ass felt like it was on fire.
I was 16. He was about 40 years older than me. I met him online... He was nice, but I do regret it.

 

[B_am12388]

I was 16 and had never been with guys. met this guy at the beach went back to his place. he was 29 and kind of led the situation. He rimmed me good and then pulled out his 10.5" monster. The uncomfort only lasted about a minute. He fucked me for about 3 hours and I shot 5 loads. He wouldn't pull out and just kept going. I learned that day that I was a very talented bottom:smile:

Sounds crazy! Yeah, I wouldn't say I'm a bottom, I'd say I'm a powerbottom. I've never topped a day in my life.

 

[arthur]

Okay, you're old fashioned. Now come to to bed. :wink:

Is that it hootie!??!? No, let me buy ya a drink and whisper sweet nothings in your ear!?!? What happened to a bit of bedside manner!?!? Do ya think I am that easy!??!?

Okay, when?!?!

 

[D_Aston Asstonne]

Ummmm? gordon69, correct me if I am wrong, but it does say "Hey guys! Post up your experiences of when you were first penetrated..."

Start your own post about 'normal anal' sex and leave us be, to carry on talking about what can only be presumed from your wording as 'abnormal' homo sex?!!?

Usually helps if we read texts before commenting, call me old fashioned!??!?

Correctomundo!

 

[Smartalk]

I was with a gay friend of mine and we were watching some straight porn or a guy having anal with a woman. I could see by the buldge in his jeans that he was aroused. I ask him if he had ever done it with a guy and he replied, with a chuckle "oh yes". Hw ased me if I had to which I replied no, but would love to try it if he was up for it. Before we knew it we were completely naked between the sheets of my bed fondling and caressing each others bodies. He had a fiarly long and thick circumsized cock, dipping loads of precum. He ased if I was still up for him shagging me, "to right" I replied and asked what position he wanted me in. He advised that being my first time to laye on my side, so that I could push back on his cock when he presented it at my virgin hole. He lube my hole really well with his expert fingers along with his own cock and spooned me. when I felt the head of his cock I slowly pushed back. The sensation was awesome, the presure slight discomfort as it stretches you open, then you get a feeling that this could realy hurt, but it feels so good I don't want to stop now. The point of no return, so I took a deep deep breath, bore down and push back, you cannot describe the mixed sensation of fear, pain, shear lust, extasy that floods throughout your body all at the same time. Your head spins trying to analyse each and every senstaion and but it into context, as the pure animal lust within your takes over as you push back and impale yourself in one breathtaking push, when you think you think your at the total peak of your pleasure, the head of his cock makes contact with your G-Spot. OMG you then see the cloud of blue mist swirling before your eyes, as every nerve in your body appear to scream out in pure ecstasy. Never had anything as mind blowing as that in my life and thought I never would until the time I was at this wonder plateux and suddely had this unbelievable earth trembling sensation of a full body orgasm and shot my load, trigering my partners own orgasm deep inside me, awesome truely awesome. I could not beleive how much cum I produced. I was on cloud nine for quite some time as we remaind locked in a warm tender embrace. You straight guys think you know great sex, somehow I doubt it.

Gee I'm all wet just reliving this life changing experience.

 

[B_am12388]

I was with a gay friend of mine and we were watching some straight porn or a guy having anal with a woman. I could see by the buldge in his jeans that he was aroused. I ask him if he had ever done it with a guy and he replied, with a chuckle "oh yes". Hw ased me if I had to which I replied no, but would love to try it if he was up for it. Before we knew it we were completely naked between the sheets of my bed fondling and caressing each others bodies. He had a fiarly long and thick circumsized cock, dipping loads of precum. He ased if I was still up for him shagging me, "to right" I replied and asked what position he wanted me in. He advised that being my first time to laye on my side, so that I could push back on his cock when he presented it at my virgin hole. He lube my hole really well with his expert fingers along with his own cock and spooned me. when I felt the head of his cock I slowly pushed back. The sensation was awesome, the presure slight discomfort as it stretches you open, then you get a feeling that this could realy hurt, but it feels so good I don't want to stop now. The point of no return, so I took a deep deep breath, bore down and push back, you cannot describe the mixed sensation of fear, pain, shear lust, extasy that floods throughout your body all at the same time. Your head spins trying to analyse each and every senstaion and but it into context, as the pure animal lust within your takes over as you push back and impale yourself in one breathtaking push, when you think you think your at the total peak of your pleasure, the head of his cock makes contact with your G-Spot. OMG you then see the cloud of blue mist swirling before your eyes, as every nerve in your body appear to scream out in pure ecstasy. Never had anything as mind blowing as that in my life and thought I never would until the time I was at this wonder plateux and suddely had this unbelievable earth trembling sensation of a full body orgasm and shot my load, trigering my partners own orgasm deep inside me, awesome truely awesome. I could not beleive how much cum I produced. I was on cloud nine for quite some time as we remaind locked in a warm tender embrace. You straight guys think you know great sex, somehow I doubt it.

Gee I'm all wet just reliving this life changing experience.

Wow, this explains it all! You explain it much better than I do. Yeah, straight guys wouldn't know good sex if it bit their cocks off. Too bad.

 

[midlifebear]

Wow, this explains it all! You explain it much better than I do. Yeah, straight guys wouldn't know good sex if it bit their cocks off. Too bad.

Never spent much time worrying about it, but you're probably correct. :redface:

 

[B_am12388]

Never spent much time worrying about it, but you're probably correct. :redface:

I am correct. I'm always right. :wink: :biggrin1: :tongue:

 

[LilCuckHubby]

When I was around 6 or 8 I wanted to belong to the "big" boy's club which was several of the older guys in the neighborhood. They said I could be in the club if I did what they said which of course included sucking their cocks and letting them stick their cocks in me. I really do not recall if they were successful at actually penetrating me but I do recall it was a lot of fun for me. The first time I do recall being penetrated was 27 and it was by one of the guys who had been having sex with my wife. I said I was curious about receiving anal and he offered to help out. It was actually a lot more pleasurable than I expected. His cock was about 7" long but really not very thick so I guess that's why it was easy.

 

[B_kracker]

my first time i must have about 14 the guy who took my cherry was a few months older, an the school bully he had tormented me for a long time..but then was pretty good kid after he got out of that phase, we were tall for our age, his cock was cut but not that large...we were playing in an old grain wearhouse..he laid me over a barrel..an fucked away..we did it several times after that...funny thing years later he became my step brother!.. but neither one of use has brought up our teen age lust

 

[D_Bob_Crotchitch]

Is that it hootie!??!? No, let me buy ya a drink and whisper sweet nothings in your ear!?!? What happened to a bit of bedside manner!?!? Do ya think I am that easy!??!?

Okay, when?!?!

\

Silly, will sip wine in bed, enjoy fine chocolates, give you lots of massage and foreplay, and then........

 

[AZNEWGUY]

I was a late bloomer with guys . I hooked up with some guy when I was 20, he was 19. He was a Greek guy that was SOOOOOO HOT. We gave each other BJ's and I asked him if he would fuck me. He was surprised and said I was so tight he didn't want to hurt me. I told him I just wanted to get it out of the way, I really wanted to see what it felt like. Well he tried it and slowly went in. It took him 10 minutes to finally enter me whole with a condom of course . he started fucking me, but I couldn't take it no more. He quickly stopped and we tried again a few times. Needless to say, I finally enjoyed it.

 

[Proppie]

First consensual anal sex: I was about 32 years. I was in love with a guy who have an average penis. He had just paid off his $12,000 credit card bill. He was said, "I want to celebrate. Let's f**k." We used condoms and lube. He f**ked me and then I f**ked him. It was good because I loved him. It was bad because he did not love me.

 

[EdWoody]

Do you really think you need to euphemise "fuck" on this site?

My mother always said, if you can't talk about it, you shouldn't be doing it.

 

[midlifebear]

OK, it's a repeat, because I've posted about this before. I was 12 years-old and my Scout Master at Scout Camp in Maple Dell, Ewetaw, became very interested in me when he saw me in the boy's showers. His son invited me to sleep in their tent. We all fooled around with each other, giving and receiving blow jobs first. I was more than interested and willing. My Scout Master had me fuck him first. I lasted about 30 seconds, or so it seemed. Later during the night as we continued to fool around he fucked me after I watched him do it with his own son. It didn't hurt. It was just uncomfortable and I was still horny in the morning. I ended up sleeping with him the rest of the week and fucking him rather than him fucking me.

Of course, now I realize the guy was a fucking pedophile. But at the time I was a very horny adolescent and already having sex with other guys.

Interesting/awkward update: My old Scout Masters sons were both diabetics and died in their late 20's. One was older than me and one was younger than me, both by two years. Imagine my surprise to see my old Scout Master show up with his equally ancient wife at the viewing before my father's funeral about 8 years ago. He's still considered a "pillar" of the little (now enormous) Ewetaw mormon community in which he lives. Go figure.

 

[tvRacquel]

This is a pretty interesting thread, I'm glad I found it. I remember the first time like it was yesterday, I was about 10, I've always felt I was a girl at heart. He was a classmate of mine, John, taller and heaver than me (I was small for my age) and I had sucked him off a couple times before.

After school that day we were in my room sitting on the bed, we wrestled a bit and touched each other. He sat back and undid his pants them motioned for me to suck him, which I did for a bit.

I got up and said I had a surprise and to wait for a sec, I went to my mom's room and put on a pair of her thigh highs and heels (they weren't that high, maybe 3") , I'd been wearing her clothes for a while and wanted to be like her.

I want back to my room, John just looked at me confused and said "what's this?" I think I said that maybe he would like it if I sat on his cock (I don't remember what I called it then). He thought for a second and said "sit on it!" He wasn't big (we were young) maybe 5" long or so but he was that wide too.

I had some Vaseline that I rubbed on my ass and straddled him cow girl style. I remember holding his cock to my ass and that my fingers did reach all the way around it. I started to lower myself on to him while he put his hands on my hips. It started to get uncomfortable (in hind sight I didn't lube him) and I slowed my decent, I remember the look on his face..total anticipation that turned lustful for lack of a better word.

With out a word he pulled down on my hims and thrust up with his cock, it hurt I remember and I yelped and cried as he pumped beneath me for the minute or two he took to cum. He rolled me off him, zipped up his pants and said he had to go. I never talked to him after.

So that's the way it happened, I swear!

 

[Sabln9A]

I had just discovered the hang outs in college where you could go to get or give a blow job. At one rest room, I did the foot tap, and the guy tapped back. I was expecting to just give him a blow job. He invited me to his apartment. His roommate was there. They actually raped me. HIs roommate started fucking my face and then held me down while the guy who picked me up fucked my ass. He was large. I was on my stomach. No lube. Dry and painful. I begged him to stop, but it just made him go harder. When he finished and came inside me, his roommate got on top and fucked me. It was a long time before I allowed anyone else to fuck my ass, but now, I am a bottom and into being submissive, I like anal and being forcibly taken. I was 19, by the way.