First time you had anal sex

[Reese]

The first (and last) time I was anally penetrated happened when I was 15 and a total virgin to any sexual activity involving another human being. I was over at my brother's house where I was celebrating New Year's Eve with him, his girlfriend, her two kids and their lodger Mike. We'd just rung in 1980 when I decided to stop partying for a bit and duck into one of the side bedrooms for a brief nap, as I knew they'd be at it all night drinking and dancing and what-not.

I was gently awakened some time later by the feel of a hand undoing the button of my trousers then sliding down my belly. As I'd never enjoyed another's touch "down there" before, I decided just to keep my eyes closed, pretend I was sleeping and go with the flow. By the time the first hand reached my penis, stroking it's base gently with one finger, I felt a second hand undoing my fly and easing down my trousers below my hips. "Fine," I thought, enjoying the alien tactile sensation of an unfamiliar hand rubbing my genitals.

Of course, I was fully erect in an instant and it took this helping hand some effort to coax my cock out of the tight trousers but, soon enough, I felt it standing proudly at attention and fully exposed as the gentle genital massage turned into a slow jacking handjob. Over time, the grasping grip was released and replaced by a wet mouth. "That feels incredible," I mused as the lips closed down around my shaft and a teasing tongue began encircling my glans and probing my meatus. Mmmm, my first blowjob.

With both hands now free and propped up on elbows, my unexpected molester then used his hands to pull my pants down to my knees and rolled me over on my side in a spooning position. It was at that point I could feel a penis probing my ass as a hand guided it's underside up and down through the cleft of my butt cleavage. This went on for quite a while until the exploratory dick head was perched right at my rectum and the handjob resumed. This time, however, rather than just jacking me off, it seemed as if he was using my cock for leverage, pumping it's swollen shaft downward to drive my asshole hard against his cock head.

This was getting nowhere, so, in sexual desperation, he released my penis from his genital grip, pulled his cock out of my ass cheeks and left, only to return moments later as I heard the sound of a jar opening as I continued pretending to be asleep. The next feeling was that of his fingers probing my asshole and sliding in with relative ease from the obvious lubricant covering them. Moments later, the burning sensation began - just warm at first but them escalating to a simmering boil. He'd accidentally picked up the mentholated Vasoline, the bastard!

I jumped out of the bed and, with my trousers down around my ankles, ran (okay, shuffled) as fast as I could out of the bedroom, through the living room within which my brother and his girlfriend were still dancing and into the bathroom to try to wash off this insipid substance. While I got some of it out, my ass still burned a bit through the next day.

Postscript: It turns out that it was Mike, my brother's lodger, who'd been masturbating me before attempting anal intrusion. After that experience, Mike jacked me off to orgasm a few times during subsequent overnight visits to my brother's house, but never - I repeat, NEVER - tried to fuck me up the ass again.

 

[auto90403]

I started having MM sex when I was 19. I'd been having lots of threesomes with MF couples in college. With some couples, the guy ended up sucking me while she watched and as I later figured out, the guy was using threesomes to explore coming out. I've never had issue regarding my sexual orientation and if I consider myself the most boring straight boy on the planet, I also enjoyed getting my dick sucked by a man. (Actually, what I enjoyed was the ease with which I could get a guy to blow me. No buying a girl drinks all night. On business trips I can have a man at my hotel room door ready to suck me off in less time than it takes to order a room service burger. After which he leaves.)

Over the years, while my sex life was mainly girls, I still sometimes found a guy to suck me. I also sucked a few cocks and found I wasn't very good at it. I liked it without being overwhelmed. I also fucked a few boys' asses but I've never been a big fan of anal with girls or boys. But the guys all raved about how good my cock felt fucking them and eventually I hooked up with a guy who agreed to very gently fuck my ass.

He used lots of tongue and lube and a small dildo to relax me before sliding in. I was totally underwhelmed. He wasn't very big and I could hardly feel a thing after the discomfort of his initial entry. I could (sort of) feel him thrust and when he came I wouldn't have known if he hadn't said something.

The whole thing felt exactly the way women describe sex with really bad lovers. He used my ass to get himself off -- big deal. What the fuss about anal sex? It was pretty ho-hum.

I'm perfectly willing to conceded that with a bigger cock I might have enjoyed it more. But the experience did not leave me craving to do it again.

I'm guess finally not a bottom and not much good at MM sex beyond being very very appreciative when a guy gives me really good head.

 

[laphiha]

My first time was in an adult book store. I was jerking off with a guy standing behind me. He started fingering me, which didn't bother me cause guys had done that before all the time. next thing I knew, he rammed his cock inside me. He started fucking the shit out of me. I was screaming so loud. He wasn't too big so it actually didn't hurt at all for my first time, just felt really good. But I pulled off him because I didn't want him to cum inside me.

 

[bigbiboy]

My first time was with a friend after school. We were both 15 and some how had gotten into a habit of watching porn, which lead to jerking off in front of each other, then to jerking each other off, which progressed to sucking each other. He was not as keen on being the one doing the sucking as I was, he had issues with it being a bit gay (but had no problems with me blowing him), so I did the most of the work, but wanted it to go further. I had owned my own dildo for several months and had really gotten myself ready for anal. When I told him I wanted to try anal he at first refused, it was too gay. So I had to almost beg for it, finally he gave in and agreed to do me, but made it very clear I was not in any way, shape or form going to do him. I was fine with that. And also he was no longer going to suck my cock. I was OK with that also as he rarely did any more. We had no condoms but as we were both young, stupid and still virgins we didn't give it much thought. We both stripped naked, I lubed up my crack and layed on my back with a pillow under my hips, I wanted it missionary style so I could see him fucking me. He then mounted me slowly, I pushed my hips into him trying to take more of his cock in me. He started to pick up some speed and began to pound my ass quite hard, I bit on my bottom lip and gripped the bed sheets tight as he he really fucked me like a whore, but I was loving it so much I just wanted more. I moaned like a stupid porn starlet and cried out for him to fuck me harder. His pace soon slowed back down and I could see on his face he was about to cum. I felt his cock swell and twitch inside of me. He then grabbed the pillow my head was laying on tight with one hand and my shoulder with the other, he pushed his cock as far into me as he could. I let out a gasp and a whimper as he tried to push further, then he started to cum. My ass was being filled with his sperm, he pumped his cock as deep inside of me as he could making sure every last drop was shot in to my ass. The whole experience was magic, I had lost my virginity to another guy and loved it. As he pulled out of me I layed on my bed with an ass full of cum, covered in sweat, well and truely fucked, knowing this was the best sex I could have.

 

[mikewriter]

I was 20, he was 28. It was a dude I met at a club. I had seen him at the club quite a few times. We had danced together on a few previous ocassions, but this one night he finally got me back to his place.

I didn't tell him I was a virgin. He was 7.5 and a few inches around. Not huge but big enough for my first time. We used a condom and lube and I rode him to start. We went vrey slow and I rode him for awhile before we tried doggy and on my back. It hurt, but not as bad as I thought it would, mainly because I was riding him and was able to control it.

He came twice...we had sex, he came, and then we stopped for a bit before starting again. I didn't bleed, as far as I could tell, until he pulled out the second time and I noticed some blood on the condom and on the sheets. There was also some blood when I went into the bathroom to clean up.

The next day I was sore and I started to bleed again when I went to the bathroom the next morning. We fucked for a couple of months (my only partner at that point) until he moved out of state.

The second dude I was with was much bigger, and that time it actually hurt more because he didn't lube it up as much, and he was much rougher.

I love anal sex though, and find it highly enjoyable.

 

[LaLandPig]

Had been playing with my next door neighbor since fourth grade. We used to swap blowjobs all the time either at his house when his parents were gone or out in the woods at the end of the street.

We had been reading his parents copy of "The Joy of Sex" and decided to try anal sex. He had a big, thick dick...about 9 inches. I lubed it up good and slowly sat down on it and then he bent me over and went to town. We pretty much fucked every day, sometimes more than once for the next 10 years. Had lots of threeways and orgies with him and some other guys in the neighborhood. All of this was back before AIDS, so always bareback. Some great times.

He now lives in California and we have chatted a few times, but we are both in relationships and have not played since my 20s.

 

[TheMarchHare]

where are the female responses??? I want to hear about normal anal not homo sex! come on ladies?

^Applies himself in class, but does not follow directions!^ :biggrin1: THE VERY FIRST THING THAT WAS POSTED BEGINS WITH... "Hey Guys!".
Now shush, and stop being a bigot.


Now that that's covered,

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.

The first time I was fucked I was just newly 14 years of age. It was with my first official boyfriend, about three days before we started actually dating. He was about 5 1/2-6in long... and not super girthy, but not pencil thin either. Lets just say, deep throating him.... was hardly what I'd call deep throating... and most of the time sex wasn't that amazing either ... but man did he give some real, real AMAZING head :biggrin1:. Anywaysss.. I'm getting off topic. I was both nervous, and quite excited. The position switched a couple times. It started with me riding him while facing him.. I was rock hard before I sat down on it.. but I went too quickly, and it was one of the worst pains I've ever felt in my life, and immediately stood up and tried to be like no, I don't want to, I'm done. At this point I had a semi still. He convinced me to hop back on.. and so I did, more slowly, and proceeded to fuck myself on his cock.. I got rock hard again as he hit my prostate, but it still wasn't that amazing... then we switched to me on my back in missionary position with my legs wrapped around his chest/stomach... I liked that more than riding him because due to his size and curve that was the best way for him to hit prostate... but it still wasn't amazing. We used both condoms and lube.. and I didn't prepare for it. It wasn't what I expected, but it was nice.. better than jackin myself off. I didn't like to bottom often for him because the sex wasn't amazing.. but I loved to 69 with him frequently after we'd watch some hot new porn he'd gotten and/or found. Since then I've learned, particularly with the three boys I've fallen in love with, that the sex only gets better. The first time I had actual good anal sex as a bottom was with the first boy I loved the first time we had sex, which was in a field, while camping, when I was 16.... that feels more like my first time than my experience when I was 14. The second boy I fell in love with, at 18, rocked my world and I thought I'd never find anyone as good in bed as him. Luckily, I was pleasantly surprised to be wrong, the third boy I have fallen in love with(at the age of 21), and my current & future boyfriend(who also happens to be an lpsg member) was and is the best boy I've ever been with in bed.. he makes my extremities tingle. Sometimes I'm literally afraid I may have a heart attack while we wham.

So yeah, that was my first time, plus some extra info. Lol.

Hope you enjoyed it.
-Zack

 

[bluestreak]

I agrre with Arthur. This thread is just getting interesting for us guys.

My own first attempt was at age 14 with a school buddy when we tried to fuck each other. Being toung inexperieced and generally clueles we never di manage to make it all the way do to an ignorance about lube.

The second attempt was age 24 with buddy who got hold of my cock when I was totally drunk and wanted sex with me.
I didn't take a lot of persuading and sonn he was trying to penetate me. God! that cock weas HUGE! A mere 10" in length but a real jaw breaker. Even the head was enough to choke me.
Trying to get it in my as was agony. Funny thing was next morning he was full of shame and remorese while I felt incredibly great about the hole thing.

I finally got into being fucked when i was about 45! A guy I bumped into as a casual encouter. He lay on his back and litterally dragged me down on his cock. It was eciting but not very stimulating. The more I got fucked the more I wanted it.
I guess that is why a lot of guys start out as total tops and end up being pure bottoms.

Oh yeah! almost forgot. There is nothing unatural about gay sex. It is a pure product of nature and found in all species from fish on upwardsand all races of men..

 

[bluestreak]

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.

That is one very brilliant observation IVSXY808.
Truly amazing insight into what should be obvious to all of us but obviously isn't for many of us.

 

[bluestreak]

[
Advice to those who've never been fucked: make sure the guy who's doing you has been fucked himself. Repeatedly. James was then (and remains) a total slut. And he knew how it oughta be done the first time: slowly, patiently and with a boatload of lube and a lot of affection.[/QUOTE]

Nice piece of advise James.

If you have never been fucked then in truth you do not not what fucking is truly about.
To be a great top you have have been a bottom.
That goes for str8 sex as well as gays.

 

[KenPaul66]

My first time was with my best friend when we were teenagers. I had been blowing him for on & off for several years after school when one day he plopped his big fat uncut cock out and said something like, "I bet you couldn't take this big old thing up your butt..." I had a huge crush on him and wanted to please him, so I said I'm try my best. He greased my butt up with Vaseline and slowly pushed in. I thought he was ripping me apart ! It hurt like hell and I couldn't wait for him to finish up. One minute I felt like I had to pee and the next minute I felt like I had to poo...LOL. Finally he groaned and pulled out. Later when I got back to my house, I had to throw away my underwear because there was blood & semen all over them (explain that to your ma).

Anyway, what I'm getting out is that I don't believe these people that right about their first time and claim that is was wonderful, didn't hurt and totally orgasmic. Butt sex takes some practice to do it right so that BOTH parties enjoy it and not just the top. Luckily my first partner showed me that anal sex could be wonderful ,sexy and hot if done properly and with love (and lots of lube).

 

[B_ILIW]

my first time was sweet. really sweet. it was with a guy i knew for a while and he became a friend after a time. he had trouble moving house, and in getting to work, so i gave him lifts and helped him move a lot for a few months.

he was very grateful, and he asked me if there was anything he could do to pay me back. i said "dude, it's cool, we're buds, right?" but he insisted until i asked him to fuck me. one time we kind of confessed to each other that we liked looking at cocks, even though we considered ourselves straight. both he and i would get turned on at trans porn with big cocks.

he got a rubber from his bedroom drawer, and gently lubed up my ass with astroglide and slide his thing in me. he wasn't that big, only 4.75" or so, but i didn't mind since i was eager to see what it would be like to get it in the ass. he slowly moved in and out, and even this made me moan. it took a while to get adjusted to how the penetration felt, but after a time it felt good.

he penetrated slowly for about five minutes, and i was breathing heavy and moaning a lot all the time. then he started to pick up the pace, and i started to feel his cock rubbing my prostate. after that i lost it lol. the pleasure was like no other i've felt before, and i was moaning the house down like nobody's business. he fucked me for about an hour, but that hour was probably the best sexual pleasure i ever felt. from that point, i kind of got hooked into getting fucked, and whenever i'm out of the US i always look up for a hook up or escort in the country i'm visiting. i have a regular trans escort i see in london who never ceazes to be amazed at how loudly i moan lol...

 

[voidout]

doesn't exist.

 

[B_jeepguy2]

My first time was when I was in college, I was 25, he was 20 and much more experienced than me. After many years of feeling attracted to guys I had finally admitted to my self that I was probably gay and decided to try it out. Up until this point I had just made out and j/o with a couple of guys and swaped blowjobs with a dude I had met.

So anyway I met this new guy online one Saturday afternoon who went to my college and seemed cool. He sent me his pic and I realized that he went to my church. Even though I did not know him I had seen him there and remembered thinking he was hot. He told me he was about to go out to this pub near campus to grab a beer and a bite to eat and said he didn't have anyone to eat with and suggested tht I meet him there so I did. The place ws deserted and we sat back in a corner booth and talked about a lot of stuff including my coming to terms with my sexuality what I had done sexually, etc, etc.

After we finished eating I asked if he wanted to come over to my place and hang out for a while. He said sure, so we went back to my apartment and popped in one of my roomate's (he was gone for the weekend) pornos that had a threesome with 2 guys and a girl. After a few minutes he said "dude I gotta unzip." and pulled his jeans down around his ankles and was sitting there in nothing but his plaid boxers. I slid over next to him on the couch and rubbed his abs a little and then slid my hands down and massaged his hard 6" cock.

He suggested we go to my bedroom so we went in there and laid on my queen sized bed and made out We hugged, kissed, and explored each other's bodies. He took my boxers off and started giving me head. As he was sucking my dick I felt him running his finger around my asshole. He asked if I liked that and I said "yeah" and told him that another guy I had been with had fingered my ass and it felt really good.

He got some Wet lube out of his backpack and lubed his finger and started slowly working it in and out of my hole. He finger fucked me for a while, and then he pulled his finger out and he put some more lube on his fingers and said "going for 2 fingers dude" and inserted two fingers in me. After a few minutes of that I felt him slip a third finger up my chute. He worked his fingers in and out of my ass for a few minutes and said "how does that feel man?" I said "OMG dude it feels totally awesome." Then he said "that is how a dick feels...except a dick feels much better." I said "really?" he said "yeah man it feels awesome...you wanna try the real thing? I was so horny at that point I said "yeah fuck me"

He got a condom out of his bag and squirted a bunch of Wet lube on his cock and got it all slippery, then he worked some more lube into my ass. And told me to get on all fours. He told me he was just going to stick his dick head in and if it hurt at all he would stop. As he gently pushed against my ass he whispered "Try to relax relax dude, just take a deep breath and push like you are trying to take a shit." I did and he he slipped into me. He stopped for a minute and said "you ok buddy" I said yeah man it feels awesome push it in some more. And I felt him shove it in. Then he said "You got it all up in u dude how does that feel"

I said man it feels HOT! It did not not hurt at all, there was absolutely no discomfort just a slight stinging sensation as it slipped past my sphincter which went away once I got used to having him in me. He started gently thrusting his hips and said "I am gonna fuck u now if is starts hurtin at all man just tell me and I will stop ok" I said "please don't stop!" LOL He fucked me gently in that position for a few minutes and then he pulled out and said "get on your back" so I laid down and he took both my legs and pulled them up over his shoulders and shoved his dick all the way in and started thrusting it in my ass. In that position his dick was really massaging my prostate and I started moaning liek a whore it felt so good. He said "u ok buddy" I said "yeah dude fuck me harder man" He picked up the pace until he was really fucking the shit out of me. I could feel his balls slapping against my ass as he fucked me silly.

While he was screwing me I remember thinking "this dude has got his cock in my asshole and is fuckign my brains out and I am absolutely loving this shit, damn I am such a FUCKING QUEER!" LOL I looked up at him and his hot body was glistening with sweat, and he was panting like a guy running a marathon as he rammed my ass. He pulled out re-lubed and shoved it back in and resumed plowing my ass. I was jacking off and he said "Keep jacking dude that makes your ass clamp down on my cock and it feels sooo good!" Before long I realized I was gonna shoot and said FUCK I AM GONNA CUM. He shoved it all the way in deep and held it there.

The orgasm was like none other that I had ever had. I saw stars, it felt like a lightning bolt coursing through my body, and I jerked around uncontrollably as I blasted jet after jet of cum. The first shot flew completely over my head and hit the wall behind the bed, the second shot landed on my face and in my hair and the rest went on my chest. He then pulled out and jerked the condom off and shot his load all over my face and chest. I was completely covered in semen.

Then he said "Dude you are a mess, we are gonna have to get u cleaned up!" and we both started giggling. Then we both got in the shower and cleaned up and just stood there and held each other as the warm water ran over us. That was 11 years ago but it is still one of the HOTTEST experiences I have ever had.

 

[D_Chaumbrelayne_Copprehead]

That was 11 years ago but it was one of the HOTTEST experiences I have ever had.

Damn, jeepguy2, that was one of the hottest stories I've ever read!

 

[iluvbigheads]

Well, my first time with was my partner and he isn't what you call huge, but a good size...it did hurt and frankly I had to be liquored up to even entertain the idea. So he kinda got me wasted haha. Anyhow...what was important to me is that I felt very vulnerable, probably among the most vulnerable times of my life, unknown to him I felt like crying after it was over, but I just acted like I was an old pro but on the inside felt very vulnerable and used. I never did really like anal, but feed me some booze I tend to loosen up.

 

[ArabianGulf]

i fainted, :S
u scared the guy really bad lol

 

[Yorkylass]

I dunno if this thread is directed at the guys, but thought I'd contribute anyway. I was still quite young the first time, 17 or 18 I forget. Had been seeing this guy on and off for a long time, even when I had bfs he was always there in
the background and one day he was fucking me, I was on my side and he was kneeling on the bed upright. He slipped out as I was really wet that day and he was rubbing his cock around spreading my juices, including
rubbing it between my cheeks and brushing it lightly against my bum. In hindsight it's obvious he was fishing but as he did so I moved against him to let him know inwas enjoying it and he started guiding his head against my ass and applying pressure. Tbh at first it felt like the doorwas firmly locked but he was obviously intent, or just clumsy cuz he increased his pressure quite suddenly and he pushed his head in in one movement... Now that hurt!

I flinched and made him stop for a bit
and he sat inside me a moment but he soon started up again pushing
deeper.

Despite my objections we did end up getting a full length in and having a full on session, and can't say it was enjoyable the first time but luckily it was better by the next time I did it and soon got used to it

 

[D_Wastdayle Shotwadde]

My only attempt at anal sex so far was failure. Me and friend tried when I was a teen but we didn't have any lube so it hurt to much. First I tried to fuck my friend, then he tried to fuck me. But I would love to try again.

 

[midlifebear]

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.