What was your first time having anal sex like?

When I was 18 I met a 40 you married woman. She loved to educate and fuck young guys. She told me how to properly lick a clitoris and introduced me to prostate massage while blowing me.

She eventually introduced me to her husband. He liked watching her have sex with her young lovers. The two of seduced me and I had anal sex with the husband in front of his wife. I loved it,being anally erotic from enemas,suppositories and rectal temps. It was a little uncomfortable at first, but once he got the tip in it was all pleasure. I went back for pussy and cock as often as possible

I have only had anal sex with myself. My first experience I was about 13 or 14. I was taking a shower and my mother had left her douche bag hanging from the shower rod. I inserted the nozzle and it felt good. I tried a few more times but it lost its thrill, but even to this day occasional I will insert a finger into my rectum while I fantasize about activity such as enemas and anal sex. Anal activities have always been very secret and naughty. My mother taught me that proper young ladies do not indulge in that kind of behavior! It is a good think she cannot read my mind!

I've only indulged in anal masturbation and my wife fingering me during oral sex. Having a man enter me is on my bucket list with a certain individual I'm interested in.

Was with my cousin on a sleepover ,I was a teen ,happened a few times,got to like it.

I was 7 when a neighbor boy across the street lured me into his basement, he was maybe 13 or 14. I didn’t know what was going on and I was really scared at first when he told me to pull my pants down and lay on the cot on my stomach. I did as I was told and I thought he was playing some kind of game with me when I felt him licking and sniffing at my anus. Then he straddled me and tried to penetrate but I was just too tight, so he jerked off and came all over my anus and I thought he was peeing on me because I didn’t know what cum was at the time. Then he sent me home with cum all over my ass and it’s a miracle that my parents never found out from looking at my underwear. It never happened again, but the seed had been sewn; from that point on, I became fascinated by anal play and anal sex.

When I got old enough to watch porn and ultimately have sexual experiences with women, anal play and anal sex were ALWAYS a part of my repertoire if the girl let me. If she didn’t, I would get very disappointed. Even during my teen years before I started hooking up with girls (I got off to a late start) I was inserting things like hairbrush handles and bananas into my rectum. All my porn involved women receiving anal sex, without exception. It felt incomplete otherwise. I even turned some women on to anal sex when they had previously little to no experience with it.

In spite of all this anal oriented sexual awareness, I had never actually been fucked in the ass until a couple of years ago when I let my wife peg me. It was a lukewarm experience because she never did it before and had no rhythm, she also didn’t have much of a desire since she wasn’t getting any sensation out of it. She was kinda “meh” about it and basically felt that she was the one who was supposed to be getting fucked, not me.

Nowadays whenever I have alone time, I use a 7 inch dildo up my ass as well as a thick American cucumber, and have since trained myself to be able to accommodate any humanly possible cock thickness.

I won’t cheat on my wife, but if we ever got divorced, I will definitely consider bottoming with a guy or a TS because it feels SO good.

And to think it started with being molested by a neighbor way back before I even understood sexuality...

I was already anal erotic long before my first time trying anal sex, had used finger and other items back there whilst masterbating.

So when my at the time boyfriend wanted it I wasn't against the idea at all.

However being a naive teenager I didn't know enough about it and the first time was pretty uncomfortable to say the least and brought a tear or two to my eyes.

I endured it I said it hurt but he told me was close so I just waited for him to finish.

With the discomfort though I did get aroused so it didn't put me off for the future but I learnt it's good to warm up first

I was 15. My boyfriend at the time had no idea what he was doing or he just didn't care. He was careful getting it in so it wasn't too bad. But once he got it in he rode me hard. It hurt like hell and I didn't do it with him again. Got a better boyfriend who knew what he was doing.

Aliciad, scottgirl: It seems many young males are inconsiderate... Some people say that the young nowadays try to do things as in porn movies, except that some important aspects (need for lubrication and other preparation) are typically not shown.

Aliciad, scottgirl: It seems many young males are inconsiderate... Some people say that the young nowadays try to do things as in porn movies

@Pecan_nutjob I wouldn’t constrain that statement to young men - read the papers!

@Pecan_nutjob

About your comments on porn, I feel sorry for young people whose intro to sex is the internet. None of my anal intercourse experiences, with 4 girlfriends over the years, was like you see in porn. In a lot of porn it looks almost violent, it’s often disgusting. How sad that some young people assume this is the standard for “making love”.

Sorry if this is off topic.

About your comments on porn, I feel sorry for young people whose intro to sex is the internet. None of my anal intercourse experiences, with 4 girlfriends over the years, was like you see in porn. In a lot of porn it looks almost violent, it’s often disgusting. How sad that some young people assume this is the standard for “making love”.

Sorry if this is off topic.

In previous times, young people weren't introduced to sex at all except for (school) gossip, big whopper lies, lots of exaggerated and untrue stories and loads of misconceptions. It was difficult finding imagery making it difficult to even know how naked bodies looked like, let alone the intimate parts. And lest someone says 'dirty postcards', that was porn of a kind as well, but with hairy people so it was difficult to even know what female genitals looked like at all.

At least now there is an abundance of (moving) imagery to choose from. And since seeing and observing is often the best way to learn things, watching porn is probably not a bad way at all to learn at least about the basics of sexual interactions.

Of course, it will come down to the choices one makes and what is viewed. There is lots of porn junk, just as there are lots of crappy movies, stupid TV shows and silly, unrealistic books, not to mention comics. The best is to make informed choices. Often enough in porn, amateur material is the best and most realistic, especially webcam shows. They may be a bit stylized and exhibitionistic, but one can learn some useful things and techniques watching.

I wish they had been around when I was an adolescent, instead of only very placid line drawings in books and comics. I didn't even have any of the incredibly naive (and ever so hairy) Dutch or Danish porn when young. Just some books. And from reading, one does not really learn techniques, sexual or otherwise.

So yes, there is a lot of junky porn, as with everything, but no blanket condemnations, otherwise it sounds like pulpit sermonizing or talk-show pandering to moral majorities.

Some people say that the young nowadays try to do things as in porn movies, except that some important aspects (need for lubrication and other preparation) are typically not shown.

Mainline movies are not much better when it comes to realism and everyday details. How often does, for instance, a detective/police officer when forcibly woken from sleep ever take a pee first before heading to the crime scene, how often is he shown taking a dump - or even talking about these things at all? All quite important things, but still left out.

Realism and entertainment are not synonymous.

Agracier: There is a substantial difference. A 16 year old knows that it is a bad idea to head out for a trip without using the bathroom. The same 16 year old is likely not to know how to perform anal sex in a safe and pleasant way.

The same 16 year old is likely not to know how to perform anal sex in a safe and pleasant way.

Of course they don't know how. They have to learn about it in some way or another. The same goes for just about all sex.

I have yet to get it and I expect to enjoy it.

All I had was some Penthouse and those kinds of magazines, photos and stories and letters. From there I used my imagination and was lucky enough to have some very patient and willing girlfriends at a young age. Lots of experimenting until we figured things out.

I was at the beauty salon. I had asked for a shampoo and set and I got so much more! When they laid me back to shampoo my hair. I was enjoying that so much he kept lathering me up my whole head was covered in suds. Told me to relax and began to undress me give me the best prostrate penetration it was awesome. Came several times intensely to of course. Then I got a good tight roller set and I also got netted under the dryer. And the best come out I've ever had. Needless to say I booked my next appointment LOL

I was at the beauty salon. I had asked for a shampoo and set and I got so much more! When they laid me back to shampoo my hair. I was enjoying that so much he kept lathering me up my whole head was covered in suds. Told me to relax and began to undress me give me the best prostrate penetration it was awesome. Came several times intensely to of course. Then I got a good tight roller set and I also got netted under the dryer.

Where is this salon? Male or female stylists? Did more than one person ‘service’ you? How many times did you cum over what time frame?

is this true or is it a fantasy?

I don't know when I first thought about it. I was 17, in the backseat of my car, the first time it happened. I'm pretty sure it was my suggestion, as I was trying not to have sex. For whatever reason, my 17 yo horniness decided anal was ok but vaginal was not. It was amazing. He was my first and I was his. We experimented a lot. No regrets.

I was at the beauty salon. I had asked for a shampoo and set and I got so much more! When they laid me back to shampoo my hair. I was enjoying that so much he kept lathering me up my whole head was covered in suds. Told me to relax and began to undress me give me the best prostrate penetration it was awesome.

Interesting the connection of sex to beauty salons. I've always had many imaginings of how intimate things might very well be in such places, you know, only us girls together, what's to hide.

My mother went to these places when I was still young, around 9, 10, 11 and sometimes I waited inside. There was an atmosphere that tickled my fancy, with all the scents and the heat from those big hair dryers.

My first was when I was about 20yrs old and she was in her 30s. Kinda surprised me when she took my penis and inserted it in her ass. But I was hooked after that!! That also started my solo anal playing as I began inserting anything I cld find and fit in my own ahole.

Those big hair dryers.

When I was young I thought those big hir dryers were for brain programing. Beauty salons scared the fuck out of me. I am still a do it yourselfer.

My first time like seriously getting off was with my trusty beaded stick. I was around 13 . I wrote about that device so one time is enough. After that solo experience I did it with my girl friend using the stick. She was disgusted and would not take it herself "Fingers yes stick no" but did me so it was pretty nice being snuggled and reamed . With a guy it was some time later at a party . I was real drunk and he did me up the ass in a pile of beer bottles and cans. Not really romantic and the memory is fuzzy. It was sort of not wanted by me but felt really good so I did not complain about it. No idea who it was anyway.

I am sure that enemale is sure as many of us are. It does not mean one is gay.

I was a fourteen years old teen boy of Nordic heritage with blonde hair down to my shoulders and a smooth white toned body. I felt horny whenever I spent time alone with a tall, dark, and handsome sixteen year old muscular boy who had become my best friend. We were teammates on a softball team, showered together after working out with dumbbells and barbells in his basement, went on hikes and fishing trips, and shared an interest in sports . He was on a wrestling team, and he liked to manhandle me and engage in rough play. Over time I became submissive with him and allowed him to dominate me. He was not surprised when I told him that I wanted to feel his big uncircumcised penis inside of my anus. Even though he used his fingers and a lubricated butt plug to stretch open my anus prior to entering me with his condom covered erect penis, I experienced both pain and pleasure during my first time as his bottom boy. I would feel arousal when I spent time with some of the busty girls who were my friends, however my feelings of arousal were greater when I spent time with him. In a short period of time I became aware that anal sex and being dominated by my boyfriend were my greatest sources of pleasure. If anyone had similar experiences or have questions to ask me about my relationship with him, feel free to message me and discuss them.

I was about 12. A same age buddy and I were jacking off together and he asked if he could try fucking me. I agreed and loved every min of it. We had no idea what we were really doing but I remember the wonderful sensation when he would enter me plus the sensation of his warm cum in my ass. Needless to say he fucked me 2-3 times a week for several months until he went off to private school. I remember I used to walk home with cum dripping down my leg. Ah the wonders of youth.

When did you first think about it?

As a young teenager I could not imagine how it should work being fucked in the bottom. I started playing with my hole at age 13, but was interested maybe at age 7 (e.g. taking temperature and receiving suppositories) when I played with a friend of mine

How old were you?

I was first fucked when I was 14.

Did you plan to do it with a special person?

No, it just happened . But I believe that my friend (17) planned it in some case.

Did it hurt?

Yes, absolutely. First times he couldn't enter with his dick which was 19 x 5 cm. I still remember when he fucked me first time how painful it was. Luckily after 3 or 4 minutes he pulled his cock out, wanked on my bum hole, reinserted his dick and fucked further for at least 1 minute.afterwards I felt totally buggered...

Did you regret doing it?

First, I did.Maybe I still was too young and too small (maybe 1.45 m tall). But my friend finally convinced and influenced me to have another and another try.

When was the next time and was it better than the first?

We met a couple of days later, and second and third time were as painful as the first one. When he had a try giving me a paracetamol suppository before stuffing his dick in my small bum, it was less painful than and that motivated me to be fucked furthermore.

The whole story I almost posted in another topic:

At age of 14 I had a school project and I had a friend who was 17 and helped me with that. One afternoon when we both were alone at my home, he came from the bathroom and asked me the question where at the body my parents take my temperature. I still know it clearly that I turned red and answered very shy "in my bum". He told me that he found the thermometer in the bathroom and when he was younger he got it that way, too. Somehow he broke the ice, we made some kind of jokes, which turned to dirty talk, which lead us to try different things practically. I let it happen, and I thing he was experienced in some way. I know that I found it amazing that he had a 19 cm long boner, but I was afraid when he told me to take it in my mouth. I refused of several reasons, and he told me, that if I could not blow him, his dick had to be in my bum instead, because he needed a hole. He tried several times to push it into my small bum, and failed at that day. It hurt badly, too. He convinced me to try it on another day. So we did, because I was excited and he motivated me a lot. Next time we met at him, and he showed me that he bought a little plug. So he used it at my bottom to dilate it, before he had another try to enter me with his dick. It took a while and several times until I suddenly felt that his huge cock marched far inside my bum and filled me completely. It hurt like hell, and he didn't wait until I could handle it, but he immediately started fucking me. It was wasn't long, maybe 3 or 4 minutes, but for me a very long time to suffer. Than I realized that he was breathing very heavily, and in the next moment his cock plopped out of my bum. He wanked and suddenly I felt a warm liquid at my bum hole and he pushed his dick into my bum again what made a kind of burning besides the pain caused by his dick itself . It felt weird and I was totally buggered afterwards. Unless he could convince me to have that kind of sex a few more times (before he moved away) so I could handle it more and more. Luckily our parents never knew.

I was 20 when I had my first anal sex. Was a student nurse back then, doing work placement in military site.

That day was first time when I saw male doctor to do proctoscope exam on young soldier. I got curious how does that feel.

When working day was over one of trainee doctors came to that exam room.

I was still thinking how that guy felt receiving the exam. I wanted to try anal sex with that doctor so bad. So we had it on the same exam table, there the soldier was on all fours receiving his proctoscope exam.

My brother did me when we were about 12-13 or so! I was tricked into him going first! It did not hurt, too early for prostrate pleasure, but I did like it! Loved his cum in me & dripping out. Never happened again😢! However my wife has stuffed me with my large butt plug, as she had me bent over and making me masturbate to cum into my mouth, and YES I LOVED it! YUMMY!

I was 13 with my 3 friends we used to wank together one day I offered my ass and some vaseline one boy rubbed some vaseline on my ass hole and pushed his cock in slowly it felt amazing he never lasted long before he came in my ass I love the feel of his warm cum I let my other 2 friends do the same wich we did for years after

I have stuck things in my ass since I was a young ten but it has only been in the last few years that I have taken the opportunity to feel a real cock inside of me. I am sorry I did not do it always.