First time you had anal sex

[austinsinz]

I tried many times over the past ten+ years but couldnt get past the pain and always asked the guy to stop, also it made me want to take a dump and that made me tense up and feel uncomfortable. Initially the guys who I tried it with were fairly large and I knew I needed to find someone who was smaller. One day, about two years ago, I met a guy who was fairly small, prob 6" and not too thick and he patiently perservered going v slowly. It helped; and after that I grew in confidence. While I do bttm, I don't always enjoy it and sometimes it feels like I'm being kicked in the groin! Once a guy 'fell' as he was entering me - hurt like hell!

When I am fucked I really enjoy the feeling afterwards, hard to decribe it, like a pleasureable burning & lasts for a day or so.

BTW - I can take large guys now hehe !-). Prefer the doggy position and sitting on a guy's cock when I'm getting penetrated.

 

[majormadness]

my first time was all because of a little ED haha.
I had just met this adorable boy at college, and we flirted all the time. There was one complication though - my college has a residential high school on campus, and he went there. It was totally legal, he was a senior and 18, about to graduate in a few months. Eventually, one day i went back to his dorm room mid-day and signed in as a visitor. Luckily, the rule about same-sex-only guests in bedrooms worked out fine :wink:
Well, we got there and started getting it on, and for some reason I just couldn't stay completely hard. Best I can tell is that it was my nerves, being afraid banging a high school boy in high school dorms that are overseen 24/7 by faculty. Either way, I couldn't get past semi, and it simply wasn't going to fit unless I was rock hard.
So after a while we kinda give up and make out and for some time I went down on him. After a while, I ended up on bottom and he was thrusting into the small entrance between the bed and my ass cheeks. He kept moaning and asked me if I wanted him to fuck me.
I didn't know what to say at the time, since I had never received before, but something about his thick cock and sexy body was just so persuasive haha. Finally I consented, and I swear I've never seen anyone get a condom on and apply lube that quick before! And after a little finger work, he just dove right in.
His cock was normal length but thick as HELL - the whole thing was about the size of a red bull can that tapered thinner near the base. Well, that giant cockhead put a lot of pressure, then all of a sudden just kinda popped in.
We had to sit still for several minutes while i grunted and tried to get adjusted. Then, I told him to continue and he slowly went deeper. It kept hurting, but I was still telling him to fuck me even as i groaned in pain. Maybe I just felt bad because he wanted me to fuck him so badly, so I felt I had to make it up to him. I'm glad I did though, because through the pain I could feel that thick fucker against my prostate, making my dick swell even while i was on the verge of tears from the pain.
I only made it through like 15 minutes of penetration before I couldn't take anymore, and I had to finish him off orally. Still, that began my short but passionate love-hate relationship with bottoming. It still hurts every time, but I'm typing all of this while I sit on his bed in his apartment waiting for him to finish work today so we can have a fun night tonight. I'm really looking forward to fucking him, but I know that even though it will hurt, I'm gonna need him to fuck me too :smile:

 

[mr_unattractive]

Never, and it ain't gonna happen. I don't want to get it and the wifey doesn't want to either. It is NOT for everyone.

 

[Richard56]

My first anal experience was four years ago. It was only the second time a lesbian friend had taken me to the local gay pub and I wanted to try sex with a man and as soon as I saw her gay male friend at the bar I was under his spell and he came over and we were back at mine and naked within the hour. I told him I was new to this and when he entered my arse it felt new, different, pleasurable, like putting on a tight glove. When I entered him about an hour later it was little different to a vagina. Like trying on a pair of shoes when you have always worn trainers. I had the best sex of my life so far with him over the next six months and we never discussed what we would do sexually we just went on instinct and it made me wish I had tried it years ago.

 

[Opalite]

The first time I had anal wasn't really that amazing. It didn't hurt, but it didn't do anything for me either.

I was still quite young, and it was with my ex which I had been dating for a little over a year at that time. I remember getting home, and he had cooked me dinner and bought some very nice wine - he was really that obvious. We got a little tipsy and he carried me to our bedroom. He apparantly sprinkled fresh rose peddals all over the bed, and had put candles through out the room. Up to this point, I had never even thought of having anal sex, untill he asked me. I remember him putting me on all fours, carefully letting his lubed fingers enter me. So far, so good. It felt a bit uneasy at times, but never painfull. Because we had decided on it in such a whim, I had never even thought that it could hurt. But I can't say it was pleasureable either. I had no regrets, but it didn't seem to be something I would want to more often. (oh boi, was I wrong...)

The second time wasn't for years later, with another guy. We were at his place, just getting home from a night out. To keep things short, I decided to stay the night. What I seemed to have forgotten though, was that my ex had been quite a bit below average hung, and that this guy was quite thick. So when he suddenly thought it would be a great idea to suprise me with some buttsecks, I was shocked with how much it hurt me! I bled for quite some time after.

It wasn't untill the third time I actually realised how amazing it could feel. Eversince my last experience I hadn't really thought as anal beeing something I could enjoy, but rather something you did for a partner. A one night stand didn't seem to fit into that category. Though, this was the guy that thought me how amazing anal can be when you take enough time!

By now anal has become an important part of my sexlife. I woudn't want it any other way!

 

[D_Polyphebus Hammertoe]

Hey guys!

Post up your experiences of when you were first penetrated. How big was it? What position were you in (doggy, ride etc)? Were you nervous/excited? How did it feel? Were you hard? Did you use a condom or lube? How did you prepare for it? Was it what you expected or better? All that sort of stuff.

My first time was with my first boyfriend when I was 19. He was 7" and pretty girthy. We started off with me on top, because I was so tight, and could best control how much of him I took. It was super painful at first... but with some time and patience, it got better. We used ky liquid (still my fav), but no condom (dumb, I know). Despite the pain and awkwardness on my part, I maintained a rock hard erection, and liked it very much. The anal stimulated orgasm was the biggest surprise of the night tho... so powerful, and yet such a different sensation. I was definitely nervous and excited in equal measures. It didn't take me too long to settle into a routine with bottoming for the first bf... we got it right pretty quickly (he was way more experienced than me), and soon we were doing it multiple times a day, for the length of our 2+ year relationship. He's still the only one I've ever really bottomed for. The tops I dated since him were bigger and really hurt me, and weren't as skilled or careful in the ways they tried to fuck me. I gave up on bottoming altogether about 5 years ago now. I think it was just a moment in time kinda thing for me. Hot memories still remain though! :biggrin1:

 

[B_jeepguy2]

My first time was with my Boy Scout Leader who I had me fuck him regularly at night in his tent at Boy Scout camp at old Maple Dell in southern Ewetaw County. I let him stick his 6 inches (or less) up my extremely underage ass. It was just sort of uncomfortable. Not painful. Didn't get the whole idea why it was so great. Except it was great for me plowing an oversexed adult pedophile in his mid 30s. I was always hoping someone would put the moves on me when I was a young kid and the Boy Scouts provided a regular pool of older boys and men who were interested in checking out my goods.

Not complaining, mind you. But I've never understood why adult men are sexually attracted to adolescent boys and girls. I, however, certainly made the best of my situation(s). Sorry folks. But that's when and how I learned to take it in the ass.

Maybe that is why the Boy Scouts of America organization gets so freaky whe someone brings up the subject of gays...because they are in denial about the fact that a lot of Scout leaders are into boys. It is the same deal with the Pentagon...they know damn well that the US military is FULL of gays and just can't bear to admit it!

 

[ramsgate18]

was with 1st bf, i was 16 he was on the small side still hurt like a mother fucker but now im better

 

[schwulboy1989]

my first time was with my boyfriend. at the time, we had been going out for almost 2 months...i topped for him, and it was great, but then i bottomed for him and i remember it being the most wonderful feeling in the world. I took all 7X6 of him balls-deep without even flinching!

sadly, i'm a little out of practice, now...

anyone wanna help me get back on top of my game...(or underneathe it)

 

[griffin]

I was 16 and it was with a neighbour of my uncle. We used to go over for an yearly fourth of july party. The neighbour Thom would be there with his wife and son. I remember thinking that he was just the ideal man to me. Tall, hairy, muscular, and very good looking. I would have to be careful when we were in the pool because when he was in his bathing suit I just was hard the whole time. He asked if I could help him bring some pool furnituure from his house. Ofc ourse I jumped at the opportunity to be alone with him, though I did not expect anything to happen. I was wrong. He told me he noticed me looking at him and that he he knew that I got hard when he was just in his shorts. He asked if I wanted to see his cock. I was scared to say yes but he pulled his bathing suit down and asked me to suck him off. He told me what he liked and how to do it. He then said there was something else we could do if I wanted. He went to the bathroom and came back with some lube. He put a bit in my ass and then lubed up his cock. He bent me over and pushed it in....slowly but he did not stop until he was ball deep. It hurt like hell...and I remember him being very thick. I got used to it fairly quickly and he did not waste a lot of time because we needed to get back. He came inside of me. This was before HIV and he was married. I was so excited that I asked him to do me in the bathroom at my uncle's house...which we did three more times that day. This went on for two years until I went off to college.
To this day I compare every man to him.

 

[D_Stubbleton Feathernuts]

LOL!!! I think it may. LOL!!
Enjoyed your story, thanks for the post.

 

[D_Stubbleton Feathernuts]

March 28th 2008

I'm not sure if it was the shower we (my boyfriend and I )took together or a combination of what was going on in my life and the need to be comforted, but that night I just wanted to be with him "completely". We went into the bedroom and I layed on my stomach...he lubbed up and slowly penetrated me. I must admit, it didn't hurt, but it was a bit uncomfortable (he's 6 inches). As time went on, I opened up more and was able to take him all the way. Now, I really enjoy being penetrated and look forward to it.

 

[B_mantila3]

the first time i recieved i was really young only 15, and we were really drunk... he was about 7" big and we both were aware of being bisexuals by that time... i remember that i was full of alcohol but still the sex was better than i could have ever imagined... ;D he fucked me cause he couldn't take my dick, we tried that first... ;D

 

[plowmyground]

With a woman, my girlfriend was 18...on the rag, and I needed a release. Licked her hot little hole, some lotion by the bed, and off to the races..of course that is NOT how you approach anal sex in life, but that young, and that horny, well..she got her ass bred big time.
With a guy, it was in Dallas on business, another married guy.
He was not hung, average but thick. I sat on his cock, then, he got so turned on, next thing I know, I am on my back and he is fucking me like his wife's pussy. Before I could even fathom what was happening, my cum was spurting up to my mouth and chin, and he was pumping hit nut on my cock to mix with mine..so, I politely cleaned it all up..nice times both.

 

[VoyeuristicSQ]

I'm not a guy, not gay, and I don't even like anal. But wow, this thread was so hot! Thanks guys!

 

[Spinner2010]

I was 22 the first time. With the first guy I really loved. Same age as me. He was moving off to grad school the next day and I didn't know when I would see him again. We were making out in his car, and next thing I know I was almost upside down and he was puttng his cock in me. It hurt, but not terrible, it was more exciting that it was with someone I loved. I didn't see him again for almost exactly 30 years. We were at a college reunion and he spent the night with me. Funny he was much smaller than I remembered and I'm pretty big. I fucked him that night, my turn and he loved it. Turned out he was a bottom and I was a top, the only time we fucked while we dated was that one night. Very memorable.

 

[rbkwp]

Prefer being a top (laying on side actually) bit of a lazy bugger
but first experience as a bottom was exquisite older mate by 8 years knew the role to play and executed it well
Often feel so much sadness for those who have had a bad first experience
Humans are animals and they often treat each other very cruelly..annoying

As to the OP,s Q,s

His size was just over average-luckily'
Position was side' there ya go wi my preference
I was terrified' ,, then in ecstasy
Felt WONDERFUL'
Yes i was Hard thruout ..Gay Porn with the 'SitSqtFck' (as i call it) and the guy sitting has a hardon a swinging..WONDERFUL twice'as.
NO Condoms needed .. in the late 60,s
Lube a requirement -YES'
Prepared in Trepidation
Dont know what i was expecting..
overall it was a downright exhilarating experience ..and set me on a path to being a raging Homosexual (fr my Partner that is)
SHAME it slows down a little.. haha
ALL GOOD'
enz
btw did you add your experience Aussie..not had time to read thru all of yr excellent thread topic

 

[ewa123]

If I recall correctly, my first time with anal hurt beyond belief. That was just a guy's finger, and I was super SUPER tight.

After that, I started practicing on myself with my finger and I managed to make myself feel pretty good.

I remember the first guy whose cock I wanted inside me. He was from El Salvador and had a big, thick, juicy monster. Man, I wanted that thing, and he tried to be gentle and patient. But my hole just has a mind of it's own. I couldn't relax enough to make it not hurt, so I had to content myself with just sucking on his.

But to this day I remember the first cock (on a random hookup) I had that made me feel crazy good. It wasn't too long, or too wide, but oy FUCKIN' VAY. This guy's dick found my g-spot and I still, to this day, can't believe how good I felt. Ecstasy, pure ecstasy. He stroked me while fucking me, and I shot a load up and over my head and across the room.

My current partner, though he's got a beautiful cock with nearly 8 inches, has unfortunately never managed to make me feel nearly as good.

*sigh* I really wish I could have some truly great sex again.

 

[macho8]

this story might not be any different from some of the guys here.. but i started as a straight guy - totally homophobic, into sports and dating girls etc....

somehow university was the "experimenting" stage of life... and I must say alcohol played a big part in this. Fooled around with with a uni mate of mine, great guy and a close friend - nothing heavy for the first time, just JO and oral. This opened my eyes to the whole gay world. I then made friends with some gay guys and labeled myself as bi... Met up some guys and fucked them. So I was the typical, masculine-bi guy and strictly top. (some of you will be smiling now and know what is coming)

One of the summers, on holiday - one of those backpacking things you do as students, i met up with other traveller... we hit it off and spent a night drinking. He invited me to his room for one last drink - I think we both knew it was going to be more than one drink....

The shorten version... we had another drink, we started kissing and before I knew it I was the more"submissive" guy. He was rimming me and fingering me and I went along with the flow. I made a bit of a protest when he started sliding his dick in (with a condom of course)... but that guy was very smart and kissed me and bit my nipples... before i knew it, he had all 6" inside me... and he was obvious a very experienced top.. he kept it inside and without moving it at all... he waited for me to beg for it....

some of you btms might know this point where you flip from top to btm... all i wanted was to get him deeper in me and hit that spot...

must admit that I tried to reclaim my "manhood" the next day when I tried to fuck him, which he kindly refused.... so it took me a while to admit myself a btm...

 

[F_Man]

I was 18, he was 24, muscular, happy, hot and horny. Way too great a girth for my virgin ass and only spit in place of lube. No condom, this was just pre-aids. He was gentle & slow, though, so the initial hurt disappeared pretty soon.

It all felt odd, eventually ok. The nicest part was that after he shot inside, we fell asleep, his dick still in, and woke up about 20 minutes later when his limp uncut tool just slipped out :smile: I saw him several times that summer, then I moved.