What was your first time having anal sex like?

When did you first think about it? How old were you? Did you plan to do it with a special person? Did it hurt? Did you regret doing it? When was the next time and was it better than the first?

1st think about it. Age 13ish

Tried anal at 13.

Didn't plan it.

Special partner? Best friend, same sex, he was a little older and said it would be fun.

It hurt WORSE... Damm, I still remember.

No remorse

The next time was a Couple of weeks later after I did him.

It was more fun the next time.

Age 15 met a guy that would be a pedophile today. Since my sisters were much older than me and married by the time I was 9, I guess you would consider me an only child. No brothers to give guidance so I hooked up with this Ham operator that befriended me. And he had an airplane, which was way cool. I saw no problem in letting him make me happy. His pecker was on the small side so no pain what-so-ever just that great electric, prodding of my prostate. It just seemed like the most natural thing, not nasty or wrong.

My first time I was in 7th grade and was with a good friend of mine. I had inserted my fingers before and really enjoyed it and one night he said we should try and so I was like ok sounds like fun. It didn't hurt bc he really took time to really get me relaxed and then then slid in. There was no remorse and we really enjoyed eachother for a while. Now I really enjoy it with my girlfriend and we are very much into expirimenting with eachother and enjoying the pleasure we give eachother!

The first time I had anal sex it was the most horrid experience of my entire life. Neither of us knew what we were doing at that time in our young lives. He went too fast not enough lube, and I am guessing there wasn't enough play time to warm up to the idea. So basically it hurt the crap out of me and turned me off of anal sex for a long many years. Boy, did i miss out on a lot of fun time had I just know what the heck I wanted and how and what the skills were needed to make that part happen. Live and learn I guess, so now I will just have to make up for a lot of lost time no? lol

Mashie

First time I was around 8 or 9. Until then I never thought of it.

It was not planned. Some older kids wanted to "show" me something.

It didn't hurt.

I was raised Catholic, so lots of guilt after.

The next time was probabily the next day!

And it was more relaxed.

I've been doing it ever since and now have a gf who's into it.

As I was very shy with girls, I remained a virgin till I was 21. But from 14 on, I have been masturbating quite a lot, thinking about all the girls I did not dare to speak to, and anal sex was of course, part of my fantasies.

I was 22 the first time I had anal sex. I had eventually found a girlfriend (or she had found me, as she took the initiative). She was just my age, but was much more experienced, having had several lovers. She taught me a lot, she accepted to have my penis in her mouth, but she was reluctant even to let me caress her buttocks as she was convinced she had a big ass, which was not at all true in my opinion. So, anal sex for her was out of the question.

After we had started dating, we had a wonderful summer of love in Paris, before she left for Dublin where she was to study. Our relation stood the test, and the following spring, I visited her a few days and we had a lot of sex;

One morning after a busy night, I woke up before her and could not get back to sleep. My girlfriend was fast asleep on her stomach and her rolled over nightrobe left her glorious bottom to my view. I spent a long time just watching her splendid ass. My pulse accelerated and my penis erected. After some time, I put my hands on her buttocks and started caressing them. The feeling was so soft, my erection got harder. Then, the idea came and I could not resist the temptation. As she was awakening and asked, "what the hell are you doing, you know I don't like you to touch my bottom", I parted her butt checks and put my erect penis at the entrance ot her rectum and gave a strong pouch. She protested loudly, "please, don't, not like this" but I was in and quickly started moving in and out of her ass. Strangely, after her strong protest, she adopted a prostated attitude, just crying and sobbing softly, but she told me with an angry voice: "OK, fuck my fat ass, if that turns you on, but do it quick, because I can tell you its hurts...and don't ever again pretend you love me". Too excited to stop, I went on and came rather quickly in my girlfriend's ass. "Now, get this dity piece of meat out of my ass, whatever fat it may be", she said. I withdrew, and she remained prostated on the bed, still crying and sobbing softly. i did feel awful.

I did have remorse and i was afraid I had ruined my relationship with my girlfriend. I remember all the phrases she said to me on that rainy Dublin day: "you raped me", "you treated me like a whore, like an animal", "you have humiliated me","I will never forgive you for that" , "how can you get excited by my fat ass, you're a pervert"., "I hate you, I want you to die"

But, to my surprise and fortunately, she calmed down by the evening and we laughed together to a Woody Allen film on local television that night, before reconciliating on the pillow, making love the traditional way.

Durind the five more days I spent in Dublin, our relation was, so to say, back to normal, we made love a lot (no anal sex) and we did not speak anymore about the "incident".The night before I was to take an early flight back to Paris, with tears in her eyes, she made a very caring fellatio on me and we made love very tenderly and softly, then, as I was about to fall asleep, she said to me:"I must tell you, I did enjoy it the other day, please do it again before you leave, fuck my ass". So we did it. She obviously had an orgasm, and quite a big one, when I came myself."It's so good to feel your semen coming out in my ass" she said.

After this episode, my relation with this girl lasted for several more years and we often had anal sex.

Not very good to be honest.

I was 17 and was a deck apprentice on a cargo ship. I shared a cabin with two other boys.

There was a steward who fancied me. He paid me so much attention I found it embarrassing. He was quite cultured and that attracted me but he was always flirting.

One afternoon in the tropics I was taking a nap because I was due on watch at 4.

The other lads were elsewhere.

Suddenly I felt a hand on the sheet covering me and I opened my eyes and it was John the steward.

He held his finger to his lips and drew back the sheet so that my cock was exposed. He then bent over and started to give me a blow job. I must admit I was enjoying it. He then told me to turn over.

Because I was excited I did as I was told. He hopped on to the bunk then just rammed his cock into me, without and lubricant or preparation.

It was really painful. He just kept going, ignoring all my yelps and squirming.

Despite myself I then squirted my load.

He kept going and I suppose because I had come it was no longer extremely painful, but just painful.

Fortunately he soon came, jumped off the bunk and quickly pulled his trousers up. He hurried out of the door, leaving me feeling frazzled, ashamed and frightened of the consequences.

To answer the other questions: the same man tried it again later during the same voyage. I woke up to find him lying on top of me. I was terrified and banged on the bulkhead and screamed. He had to report to the captain after that and wasn't given a good reference. I always felt a lot of remorse and shame about the whole incident. I suppose I was a tasty morsel then and to be honest with myself I'm sorry about being a silly cow. If only he had used a better technique .... I wasn't really at all out to myself about my feelings then, also I was terrified that I would lose credit with the other boys.

In my next ship, there was a boy my own age who would fuck me, but I didn't really get much pleasure from it, although I couldn't resist the urge to try to have sex with him.

Later on I did make a conscious effort to try it with somebody else but it was always a complete disaster.

It was only six years after that first time that somebody made it good for me. He was lovely.

I was 12 in the 7th grade. I had an older friend who would jack off with me to porn. One day at my house he asked if I wanted a blow job. I said sure, but he said in return he wanted to rub his dick in between my ass. I agreed. So we got naked, he was a lot bigger than me, about 6 or 7 inches uncut. He spread my legs and gave me head, I squirmed and loved it. Then after a few minutes he told me to flip over. I did and he tried rubbing his cock in between my ass cheeks. Then I felt him put the tip against my arse. As he applied pressure, the pain seemed intense!!!! I started yelling and crying. He spit on my hole and told me to take it that he was going to go slow. I wasn't horny anymore. He started to grind his big dick into my tiny hold, until he was all the way in. He fucked me like that for 2 or 3 minutes then his dick popped out. I was screaming so loud. Then he flipped me over and put my legs up in the air and I remember seeing his huge dick go back against my ass. He pounded me like that for a good 5 minutes and finally shot his load inside me....... Worse pain ever, but I look back and get so horny thinking about how much I liked him.

My first time with anal sex was with a boyfriend when I was 16. It was planned since I wanted to save my vaginal virginity. I had played with my butt during masturbation using sharpies so that wasn't a big surprise. The big surprise was how big it felt in me. I had lubed him up, and sat on it. There was a bit of pain. I wasn't used to taking a penis. No shame involved. The next time it was better I was used to the feeling and reaaly let my boyfriend have me missionary.

First wondered what it would be like when i was 10 and by 11 was experimenting with candles and vasaline.

First experience was at 17 with a very sweet man,who knew i was a sissy boy as id kissed,cuddled and sucked him dressed up before.so yeah it was special and since he'd oiled my first it was sore in a 'oooooh darling,oh' way.absolutely no remorse and we made love again after breakfast ,in the afternoon.

First time was recently, enjoyed it but my friend came very fast and it was over. Nowadays a condom is a must, have thought it must be nice feeling the cum up my ass but not willing to be so daring.

I met this man named tom. He was in the navy and was retired. I ws working on my car and he came to me and asked me if I needed any help..I told him all was well ad he stayed and we talked together. We got to talking about sex and he asked me if I would like a blow job. I sort of looked at him..He sort of looked ok and zipped down my pants an pulled out my dick and did me in the garage. It only took about 5 min.. He loved it an and so did I. This continued for a couple of months and al was well nice. Then one day he got my to go to his house for a couple og beers.. I said ok and went up.. He asked me to get naked for him. I did it for him. Then he got naked and started to kiss me all over.. He asked me if i ever had anal i said no. How about trying it you will love it. I sort of backed down and had another beer.. He started to suck my dick and I came in his mouth.. e went and spit it ou andcame back and started in again.. Roll over and let me lick your ass. I felt his tougue licking my butt hole. I felt really good and i started to relax..He rolled me over on my back and grabed my 2 legs an put them up on his shoulders.. He put some ky jelly in my butt hole and told me to relax. Mose ky on his penis and started real slow pokeing his penis into my hole. In and out each time going in further and further. After a few min he was going in and out. It reall felt good. Then the pace went faster and faster and finally he shot his load in my ass. What a sensation that was. It really felt nice and warm filling my butt. He pulled out and kisssed me and licked me al over..After about 10 min I had to go to the bathroom and shit out his white cum..My butt hole felt a little sore but not to bad. This was the first time and it was not too bad. We had more sex a number times and they gt better and better. That was my first time binkey boy

What age did I first think about anal sex? Well was about 12 after been told by mates things like that happen so experimented on my self with what ever I could get up there

What age I first had anal sex well I was 26 was a late starter as did not realise I was bi just thought it was thoughts every man had but finally acted on them and I was really really good the man took his time got me really relaxed started with his finger then worked up to a dildo then finally his penis there was no pain as I have been playing with my own arse with rather big dildos and plugs for years and he took his time I had never cum so hard before in my life

It was planned had meet him on line a week before so we planned it from there

There was no pain but was expecting some but none at all which was good :-)

He was special to me did not know him very well but he made me feel very relaxed and he also the reason I now know I am bi and it was all thanks to him

There was absolutely no remorse just a very nice feeling

The next time was week later with same man

And yes it was more fun as I was more relaxed the first time I was as nervous as hell but the second time I was fine got straight into it was awsome really wish I had started sooner in life I missed out on years of fun I can highly recommened it to any one there is no harm in trying and if you don't like it just don't do it again and if you do then happy days.

Mr L

i was about 17 i had just Bougth a vibrator for my girlfriend I went all the way to Manhattan by train to buy in a sleazy porno shop. i was planning to use it on here that night I remember we were in the 69 position I was on top of her she had tried to slide her fingers in my ass few times before ,I was eating her pussy and using the vibrator on her clit she reached over and pulled the vibrator from my hand I never forget it was a big white vibrator probably an 1 1/2" thick x 8 " long I remember her reaching around spreading both my ass cheeks and with one hand trying to slid the white vibrator into my ass I tried to pull away but the way she straddling me she had her arms around my thighs and waist and holding me around my ass cheeks spreading them I barely could move ,she kept on telling me relax it'll feel good for you she told me to put my head down between her legs and not to move she said to me she wanted to break my cherry, she kept on telling me it'll hurt for a while but she'll gonna like it ,in my head I was thinking this is so wrong and bad I can't let her do this to me as young as I was I was geting super excited something inside of me wanted her to do it, but all I kept on saying was the stop ,she was using her saliva to lube up the vibrator slowly but surely she slid it into my ass, I remember it hurting real bad for a while she kept on telling me to relax and enjoy after a few minutes I guess after I relax it started to feel good! Real good!! all she kept on asking me was how do you like it, she could tell I was getting into it I began thrusting myself towards her harder and harder I began telling her how much I loved it I'll never forget the feeling of the vibration in my ass I remember coming all over her chest just from her having the vibrator in me ,that was definitely the beginning for me enjoy anal sex on me ,I have to thank her for that.

We did this many times after she realized that she made me come just by having the vibrator in me she got a kick out of that we started buying all kinds of sex toys together she loved buying me bigger and bigger dildos and using them on each other so I have to thank her for starting me on this anal kink of mine

First time I had anal sex was with my ex fiance. It felt good I rode him reverse cowgirl anally. It ended up being a mess so i never tried it again cause I'm scared of a mess. BUT FUCK DID IT FEEL GOOD

I was 17 my first time. It was with an ex boyfriend. He said he "slipped" while we were doing it doggy style. He paused once he was in to see if I'd let him stay or make him stop. Since he was already in, might as well try it. It was uncomfortable, but not unbearable. We would donut like once a week for the rest if our relationship. He was the only boyfriend I did anal with. Haven't done it in almost 3 years ;/

My GF really likes playing with my perenium during sex. She will go down on me, and continue with a hand job as she sucks on my balls and then moves down to licking my perenium. It felt good so I responded by thrusting my pelvis up and one day she started rimming me, which felt really good. She got so excited she started rubbing my anus with her lubed finger, so I continued to push againest her. She slowly inserted her finger inside me which was amazing as she continued to jerk me off. She got so excited she almost came herself. I was ok with it, but she was a little embarrassed. I kissed her and cuddled and we talked about it. I let her know I was comfortable with it and didn't think it was gay, and I returned the rimming favor to her which she liked. A few weeks later we were in the middle of a hot sex session in the bedroom when she started playing with my ass again. I obliged and lay back and submissively spread my legs for her. She grabbed my hand and took me into the kitchen where she pushed me back againest the dining table and knelt it front and started blowing me in earnest. Then she turned me around and bent me over the table, spread my cheeks and went to town tounging my anus like there was no tomorrow. She was really getting off, both on rimming me and my submission. After a few minutes she was ready to come and we switched positions with me rimming her. It didn't last long, with her grabbing me and taking my penis into her vagina from the rear. I grabbed her hair in one hand and lightly grabbed her neck with the other, really giving it to her. She got off. Big time. I think role rehearsal is really hot and a great way to enjoy intamicy with your partner.

Im mostly gay so my first time anal sex was my first time in general and it was alright, i mean i loved it cuz it was sex but was the worst sex ive had to date. The guy i was with was also a virgin at the time, so we spent awhile trying to work out the kinks and find the position that worked best for both of us since i am 6' 4" and he is like 5' 7" the height difference was really throwing us off with his lack of flexibility but eventually we made it work, cowgirl/boy and actually went for like 30min staight once we actually got started going, he ended up cuming on my stomach before i finished so i pulled out and finished while he blew me and fingered my hole.

My first time was with my first college girlfriend. Our homework was to read Penthouse letters, and we learned about enemas and anal sex early in our coursework.

Well, here goes my answer to the questions.....

When did you 1st think about it? I suppose I was in my teens as I was becoming aware of my body and what felt good. And anal stimulation certainly felt good!

What age when you tried anal sex? I was in my mid-20s and with my future husband.

Was it planned? It was rather spontaneous! Luckily for me, I had taken a few enemas earlier in the day (which really aroused me) so everything was clean back there!

Special partner? As it turned out...my future husband.

Did it hurt as expected or worse? It really didn't hurt...just felt kinda strange. While I had played with my meager toy collection, I had never had anything as large attempting to make entry back there. I had read that lube was a key and knew from my own playtime that when things were slick, the play was always better!

Any remorse after? None whatsoever!

When was the next time? A couple of weeks later we tried it again...this time it was planned!!

Was the next time more relaxed & more fun?. Oh, yes!! It's been a part of our sex life for quite a while...and we both enjoy it! (and that's the real key to it all!)

My first time was with a woman I was having an affair with. We had talked about it as the sex with her was very open. She was kneeling on the floor giving me a blow job when she brought it up again. It was very horny talking about pushing myself up her backside while she slowly licked me.

When she said shall we go for it, I was rock hard and when I actually pushed myself into her, I nearly came straight away. The tight feeling from her anus was so intense and it wasn't long before I came hard. Only ever did it once more with her before we split.

I first started thinking about it around at 12-13 years. I was reluctant to try in my own city of Adelaide for fear of gossip and stigma (the city is known for that) and decided at age 30 I needed to act and find a nice guy in another city to enter my bottom. Anonimity was important to me. I would not have enjoyed the experience without this. I knew it was going to feel good. I went to a gay nude beach in Sydney called Lady Bay. It was nice to be amongst guys only who were all nude. I was shy and did not know what was going to happen to me. Then I saw him - in a private little sheltered area amonst the rocks - totally nude

with slim build, good looks, handle bar mostache, a thick penis and heavy balls. I felt a real freedom in being able to stare at his penis - it was a nice environment. I removed my own clothes and he immediately aquired an erection . It was a thick one with a big knob. I admired it but wondered about fitting in my bottom with comfort. However I displayed my bottom to him and his penis just got thicker. I then got an erection and we compared our penises. He was just so nice about everything very warm, supportive

and sweet. I told him I would like to be penetrated and he just melted with joy at the suggestion. We drove to his aprtment at Elizabeth bay and bought condoms and KY on the way. At his place We undressed and he placed his finger on my anus as soon as my pants came down. He kept his finger there and asked me to lie on my left side. His lubed and condomed penis then replaced his finger and he told me to relax and breath deeply. The arrival of his penis between my cheeks felt so good and he applied gentle insertion pressure and spoke softly to me. To my delight, he was so skilled at going into another man's bottom that his penis just slipped straight in. He told me to lie still for a while. The presence of his thick penis in my bottom was so comforting and satisfying. I was overcome by a real feeling on well bening. Then the strokes started and he really made love to my bottom. His penis got thicker and harder and then he came I was in heaven. It was great and I was Bi !!

My first time at 21 years old with my girl friend. she like it very much but feel hurt and say ouwchhhhh.....

It was even before I lost my real virginity and I was still pretty young ...

My first time was when I was 14. I got picked up hitchhiking by a gay dude who took me to a motel. He asked if I had a girl friend and if I had sex with her. I told him I did. He asked If I liked it when she touched my penis and if I would like him to touch me. I began to feel excited. He had me stand in front of him. He then held me by my hips and said I was a good looking boy and would it be ok if he pulled down my pants. I flashed back to a time years before when I was in grade 5 and a doctor at school had done the same as he pulled down my pants and felt my testicles and penis in a medical examination. He pulled my pants down and stroked my cock. I immediately started to cum so he put my cock in his mouth. After I was done he helped me take my clothes off and he took his off. He then started sucking me again until I was hard and had me fuck his asshole. I recall he was very clean and I had this desire to lick his ass. After a bit of fucking he turned me on my tummy and said we all have to do it sooner or later. He was a big dude so I did not want to disappoint him and say no. He lubed me with vaseline (horrible stuff- I now use lard, tastes better and is a better lube) and had me pull my bum cheeks apart. He went very slow but the pain was a turn on as I felt under his control. Back in those days before AIDS, condoms were not used. When he had cum he pulled out and started to lick my asshole...that was a real turn on. Then he held his uncircumcised penis and put it to my mouth which I reluctantly let him put in my mouth. After a bit of sucking I started to realize I was enjoying this affair a lot, so I asked if he would like me to lick his asshole...the rest is history as my bi-sexual life took off.

My first time was awful. My bf and I were going at it. I was around 16. He was 18. He always liked to touch my little hole while his thick rod was in my pussy. It always takes him forever to come. I had probably twice or so. I was bored and suggested to try it. I was on the floor and he was on his knees. My feet were up on his shoulders. He lubed it up and put it on the hole. I remember how difficult our first time in my pussy was so I tried to relax. But when I did he gave it a push and all eight inches went very quickly in. I screamed, and accidentally kicked him with one of my feet. My scream scared him and he jerked back a bit and the tears were immediate. After securing my feet he tried to push in again but I wiggled up with his thrusts. Being the caring partner he is and feeling guilty he very slowly removed it. I cried for a while. No remorse just lots of pain

My first time having anal was with a 20 year old girlfriend in college. We'd been having regular vaginal sex till one night she asked me to put it up her butt.....without a condom! I'd never been in her pussy bareback, and now she wanted it that way in her ass. To make a long story short, in my nervous excitement things didn't happen as I hoped. She had an ass to die for. I almost came just by rubbing my cock up between her cheeks...."hotdogging" her if you will. The silky smoothness, the K-Y, and the warmth of her asshole was driving me crazy. I couldn't wait any longer. I pressed my cock into her tight button, she gasped. I gradually pushed a little more till the glans was past her sphincter, then I just lost control and squirted her ass full of hot jizz. I came a lot, her crack was full of it. I know I didnt last long, but her ass looked so good, and felt even better. She didn't enjoy the experience as much. I think it hurt more than she thought it would. She did start letting me inside her vagina without a condom. That was extra special for me.

When did you 1st think about it. * I thought about it from the very first time I'd ever heard about it which wasn't until I was about 15. However, I had been anal erotic since I was a small child. I loved to play around and use different things for insertion.

What age when you tried anal sex? * I was 15 or 16

Was it planned? * The very first time was more of an accident. One of those bloopers while enjoying regular sex. We were getting a little carried away and he accidentally thrust hard and got me in the butt. OMG! It was sooo painful! I saw stars. I wasn't expecting it so it was horrible. However my first intentional time was different. It was not necessarily planned but we had been talking about it. I was practically begging to try it. At first it was a bit painful. He was very gentle with me and took his time. We used lots of lube but I was blown away at how much bigger his penis seemed while in my butt vs when we had regular vaginal sex. It seemed like it was 2 or 3 times the the size. I remember the first 10 or 15 minutes were all about trying to get my body relaxed enough for him to get inside me and once I was able to take the tip of it, he just stayed there for a little while without forcing his way in. This allowed me a chance to get comfortable with the feeling. I was able to relax more and then he was able to get inside me further and eventually start slow thrusts. Then it got easier to take.

Special partner? * Yes. Now my husband

Did it hurt as expected or worse? * Yes. It was painful at first but once I was able to relax and get into it, it started to become more enjoyable. It wasn't blissful but I was able to get enjoyment out of it.

Any remorse after? * Absolutely not!

When was the next time? * That same week. I couldn't wait to give it another try!

Was the next time more relaxed & more fun?. * The next time was much better. There was still a bit of pain at the very beginning but nothing major at all and this time it was far more pleasurable than the first time. With each experience after that it got better and better. I became addicted very easily.

My first time was in a 3 some with a guy I worked with and his wife. I was early 20's and they were both hot! They told me he only wanted to watch me doing her and he stood away from the bed jerking off. She would give me a blow job, and she then started playing my anus. She then used to lube me and massage my prostate and get me off before I would put it to her. Well one time, and I was always on top, all of a sudden she wrapped her arms and legs around me and clamped me tight, at the same time he was behind me and I felt his tool against my crack. I panicked, but she was holding me tight. It was really hot that she was nuzzling against me and whispering in my ear to relax, and we won't hurt you, and you will really enjoy this. I can't begin to tell you how hot that was!.He took his time and was real gentle, it hurt a little at first but she ketp holding me and telling me to relax and breath deep and stuff like that. after he was in she let loose of her hold and told me that If I wanted him to stop it was OK, but I was so damned hot and horny at that time I just started slowly bucking in her and he held still, so as I pushed in he came out, as I pulled out he went in. I want to tell you! I had THEEEEEE most incredible, intense, earth shatterin orgasm of my life! Folks! try new things! be gentle! take your time, respect your partners limits! I never thought I would enjoy having a guy in me, and I know it's not for everyone but O MY GOD!

I have thought about sex since I was about 7 years old. Anal? probably 8 or 9.

I was 12, down in Florida with a neighbor. He was a couple years younger than me.

Was it planned? Not at first. We worked up to it over the summer. Special partner? My neighbor. Did it hurt as expected or worse? He was on the recieving end. His cock wasn't big enough. Any remorse after? Hell no. When was the next time? All that summer.

Was the next time more relaxed & more fun? The next time was with my girlfriend, I was 22. She was very sensitive down there and loved being rimmed. I spent alot of time licking her ass, and then I would fuck her. She absolutely loved it.

The first time I took it up the ass was again in Florida, only I was 27. Hooked up with this gay guy that I knew thru friends. He gave me a ride home on night and we starting talking about sex. He invited me over, and that was that. He took it slow and his cock wasn't overly large. I enjoyed it alot. It turned out to be a one night stand.