First anal

Shortly after puberty, a neighbor kid and myself had been pounding it for awhile trying to get the “feeling” we started to “play doctor “ with each other. It did include sucking each other and other touching games. After awhile thoughts turned to anal sex. We tried a couple of times and it was too painful for him, BUT I kinda liked it after a few attempts. Then he was doing it to me and he started going really fast the I could feel him throwing inside me and it was like small electric pulses.

We continued that for a couple of years off and on then both of us started noticing girls with boobs and that was over with.

Haven’t seen or heard from him since then but never forgot the feeling of the throbs inside me. I got married and life went on with family and such but never forgot that feeling.

First time I had anal sex was rather unexpected. I was fooling around with my date. After lots of touching, kissing, clit rubbing, penis fondling, ass rubbing (both), etc., I felt things were ripe for penetration. When I attempted to do so, she grabbed my penis and rapidly moved it from her vulva to her asshole. It was totally unexpected for me. She noticed my surprise and simply whispered: "birth control!". I was very wet with precum so I was enter rather easily. But I noticed the difference in tightness. It was my first sensation: the tighness. I loved it!

I remember my first time. I was 13 and one afternoon I went to my friends house. His 16 year old brother told me no one else was home. He said he was watching some home made movies and asked me to watch with him. We went into his basement and he fooled around with his camera and said he wanted to film us. He talked me into removing my clothes and lie on a mat on the floor as he got naked. It was the first time I was naked with another naked guy. He laid down behind me and I could feel his hard cock against me. Mine was soft and limp,as he fondled it and it felt nice. He turned me over and took my cock in his mouth.. He sucked for a while and then asked if I liked it. W.hen I said yes, he asked me to suck him so I took his cock in my mouth. It was hot, hard and salty and I liked it. Then he taught me to sixty-nine. As he sucked me, I felt his finger touching my ass hole. He wet his finger and I felt it slip inside my virgin ass begin to stroke. It felt strange but good. Before I knew it he had three fingers in me and asked if I would like to try something nicer in there. At this point I would try anything. He turned me on my stomach and ran his tongue up my crack and probed my hole with it. The next thing I knew he was on top of me and his cock was probing my hole which he had loosened with his fingers. I felt pressure as he pushed against me while playing with my now hard cock and then suddenly he was inside stroking gently. I loved it. After a bit, I felt him tense as he came in my ass.

He pulled out and I felt his cum dribbling out. Then he said he wanted me to fuck him. He rolled me on my back and rubbed some of the cum on my hard cock and then lowered himself on it and I slid in easily.WOW!!!! I was in his ass as he straddled me and his still hard cock was pointed at me. I came almost instantly. Finally he got off me, got a wash cloth and cleaned our cocks. We lay for a while and then he said he wanted us to suck again before I left. He took my half hard cock in his mouth and sucked and tongued me until I came in his mouth. His cock, which had softened was now hard and he told me to suck it. I took it in my mouth and sucked I caressed the head with my tongue and tasted his salty pre-cum. It seemed like he got bigger and harder in my mouth. Then he said "I want to feel your teeth, Bite me." I nibble a little and he said to bit the the head hard. I bit hard, twice and got my first mouthful of cum, hot and salty. He said swallow so I did........and got hooked.....LOL. What an afternoon.....I sucked and fucked, lost my ass cherry and got sucked and enjoyed the first of many more fun times.

@bi200069 : Great hot story; I like it

I was a bit older when I had my first anal encounter.

I loved it when he spread my ass open and shoved his 8” cock up my ass.

Before I was 16, my brother did me. I did not feel any prostate excitement but did enjoy it. Now only my wife fingers me and uses one of my larger plugs on me!

I was with one of my cousins who was a few years older than me. His family lived close to our house and we were best friends. Sometimes he helped me doing my math homeworks for school, and one day when I was around 12 he refused to help me without to do something for him... you guess.... We were best friends and I trusted him, so I alowed him. We already "played" together sometimes and I considered to be a funny thing. He tryed a few times before to have a full penetration, and I remember the pain. I tryed to refuse him after his first try, but being afraid that he will also refuse to help me anymore on math, I finaly accepted. Except that pain feeling, I remember me being realy excited by that experience and we repeated it at least once on every month up to my pubic hair started to grow up and my cousin losed his erotic interest in me.

Sometimes he helped me doing my math homeworks for school, .... I remember the pain. I tryed to refuse him after his first try, but being afraid that he will also refuse to help me anymore on math, I finaly accepted. E.

This sounds like a Revenge of the Nerds plot. Can't help but chuckling at the story.

It reminds me of someone from during my high school days. One of the students was really thought the class nerd. He wore glasses, spoke with a lisp and acted a bit femmy in an undefined way. He was always top of the class academically but still nobody really looked up to him. There was no bullying or anything, but it was understood that despite getting the top grades, no one took him seriously academically, not even the teachers. So he was the original nerd.

Later though, many years after high school I learned that the class nerd was also quite the proliferate seducer and fornicator for his age. He was known to be able to entice two girls into having some kind of sex with him at the same time and didn't mind showing off in front of others. Quite a high sex drive apparently.

I thought of him differently afterwards and somehow wished we'd perhaps become friends back then, perhaps letting me share some of his obviously easy girlfriends, or even just letting me look while he got at it.

My first sexual anal experience didn't even involve my anus being touched. When I was a very pubescent 12 year old I went to the doctor for my yearly exam and he spread my asscheeks wide and examined me. Somehow just feeling his soft warm hands on my cheeks and knowing he was looking at my open hole was enough to get my blood pumping and my embarassment and excitement levels racing. Anyway that night at home I wanted to see what the doctor saw so I used a mirror. By the end of that night I'd fingered myself and masturbated. Not long after I put my smooth hairbrush handle to good use too, my first and favorite dildo.

Anal play for me was solo until I was 22 years old and met a very willing young woman. She was already eagerly rimming me so one night I handed her a jar of lotion and asked her to put her finger in there. She was hesitant, saying she didn't want to hurt me, but she slowly pushed her finger in and slowly stroked it in and out. The sensation was heavenly. A few months later I tried convincing her to let me put my finger in her anus, but she was reluctant, saying that she liked my finger and tongue on the outside of her hole but that she was too tight to take anything inside. Eventually she said ok, and we used vaseline, but once my finger was inside her anus, she said- It hurts, please take it out. Awhile later she came back from her gynecologist and said that the doctor examined her rectum with her finger and mentions that her anus is "very tight", so I guess that was her proof to me that I shouldn't penetrate her there.

Eventually she said ok, and we used vaseline, but once my finger was inside her anus, she said- It hurts, please take it out. Awhile later she came back from her gynecologist and said that the doctor examined her rectum with her finger and mentions that her anus is "very tight", so I guess that was her proof to me that I shouldn't penetrate her there.

When i think about this, it seems mostly a psychological objection? Stuff larger than your finger is coming out of there. i'd suggest that physically, it's more a question of lube and technique. There are two physical sensations from anal, one is stretching, the other is friction... and maybe a third that goes with stretching is pressure? Depending on who you are, a silicone lube might work better than "Vaseline," which i think has a lot more friction than silicone. As to the tightness, lots of different ways to approach that. but a big part of that with some has to do with relaxing the person emotionally, teasing and getting them to a place of wanting it mentally. Some may never want or get there, we're all complex and i think this is ultimately personal.. but physiologically it's hard for me to imagine someone who is "too tight" to take a finger.

@tallslenderguy I do recall that her anus was indeed very tight so my finger did probably hurt a bit. But yes I think it was part psychological too. We’ve become Facebook friends though we don’t really communicate directly. I like to look at the photos of her from back in the day, boy she was cute! I wonder if her husband ever gets inside her bottom? Maybe she grew to enjoy it.

My first anal experience was in Barcelona with an american guy when i was inter railing when i was 21. i met him in a bar and went back to his place after a few drinks. He rimmed me for ages before he fucked me all night with his big cock.

Obviously from reading these I see that people have different types of "firsts". I had some experiences in my teens by myself, with masturbation and exploration starting around 13, then in my 20's with a few women who either tongued or fingerfucked my bottom, I think the first time I was 22.

But I didn't get bent over and fucked, meaning pegged, until I was in my early 30's, from a girlfriend who was crazy into anal everything. I bought her a strapon and dildo and went home and put it to use right away, me both bent over her bed and then on my back with legs pulled up.

The one first I haven't experienced is getting fucked by a man. I've wondered about it since it must be different than getting pegged obviously. A warm cock, hard but softer than plastic, and feeling the cum explode inside. I doubt I will ever experienced it. Just not into guys, though the idea is interesting.

The one first I haven't experienced is getting fucked by a man. I've wondered about it since it must be different than getting pegged obviously. A warm cock, hard but softer than plastic, and feeling the cum explode inside. I doubt I will ever experienced it. Just not into guys, though the idea is interesting.

They make some really nice dildos now. Ever tried a double density one? Not hard like plastic at all.

It was when I was still 13 with my friend and about a month after we started doing oral on each other. I was l lying down flat on my belly. My friend was on top of me rubbing his cock on the crack of my ass when he asked if he could try putting his cock inside my ass and I told him yes. By then I was already inserting various handles inside me when alone. I got something to use for lube, I think it was hand cream, I laid back down and if I remember right raised my ass some then he got back on top of me and started to fuck me. It didn't take long before he came in my ass. Afterward we changed positions and did the same to him

I grew up with rectal temps,suppositories,and enemas from my Mom. As I got toward puberty,she would have me home for a “sick day” that was a teaching day of learning about the changes in my body. I was so lucky to have such an open and progressive Mom. I remember experiencing her finger on my prostate and the explosion I had from it and that new feeling had me searching for objects that would do what her finger had..I eventually found a plastic fake banana in a display bowl that I wanted so badly. Soon after,my parents were out and I was clear for a few hrs of self play. I had taken solo enemas by then and did an Ivory soap cleanout and a rinse enema as Mom had taught me. Then,it was time to try the banana..with Vaseline,the lubricant of the day. I remember the stretch and how I loved it and the full feeling it gave me.Moving it in and out caused an explosive ejaculation same as before ! So now,I was both a crossdressing and anally oriented kid with only his Mom to share the anal pleasure experience with…Her response when we had a private time discussion about the banana play was that she would get me a box of Trojans to keep it clean and now that toy needs to live in my dresser drawer not in the display…LOL Two years later my Father shipped me off to an all boys prep school so that I would have no choice but to concentrate on my schooling and not “other things”..He never knew the other things on my mind ! Being a transgender closeted kid stuck in a testosterone charged world was pretty lonely mentally,but I could sense there were other boys who were different and uncomfortable as well. Perhaps we gave off a “vibe” or something… It happened in the weight room on what was going to be another boring Saturday night where all the kids were doing something else and I was filling in my time getting stronger. I was doing my bench presses on the machine with just my loose shorts covering my jockstap feeling comfortable working out alone when two upper class friends enter the room from the vacant and darkened locker room. One had an extra towel with a jar of Vaseline clearly visible. We exchanged pleasantries as he locked the door behind them. They said it was so great to be able to have our own private workout and I agreed. Off came their loose shorts as they stood beside me in their jockstraps. I knew that I was not endowed like them[now thankful for that.years later] Their pouches were next to my face as I pushed out another set of reps. I felt comfortable and had a feeling that our friendship was headed to change shortly,and it did ! I experienced being a bottom on that weight bench…One boy in me and the other sat on the bench with his open crotch in my face . The boy behind me had kept my jockstrap on as he worked the Vaso around and in my pleasure hole. He reached around and roughly pulled my pouch up hard over my small package as he worked the head of his cock into me. He was pretty gentle and soon I wanted more and more movement from him as I really got into it.The other penis on my lips added to the submissive pleasure I was so seeking…Climaxes came soon from all of us. I was in another world and so happy I had found it ! Next thing I experienced was the boys pulling off my soiled jock and putting the cum filled pouch on my face…as a “muzzle” of secrecy to our little fun. Fun like this became pretty regular but most often happened in their dorm room. My bisexuality had started as I had girlfriends at home and boyfriends while away at school.

A friend of mine that I got into a dom sub relationship with when I was 22 he was 56 He did me very gently and he was always talk nasty but if he would actually hurt me he couldn't get hard so it was didn't happen that often. He was very gentle and kind when it came to actually doing it. Let me try f****** him a couple times but I just wasn't really into it at the time I was still purely sub. It wasn't till I was like 37 or 38 that I actually started fucking asses fairely regularly.

For several years I had a female submissive who was as obedient and compliant as I could possibly ask for. I'd trained her very carefully, and she was genuinely committed to exploring and satisfying her life-long need for control and domination. She always maintained an attitude of proper submissiveness, and she offered - or, when told to, simply provided or accepted - any manner of service that my desire or curiosity wanted. Our relationship was very much that of a mutually respectful dominant and submissive. It was also intensely sexual, with her serving me without hesitation in any way I required of her. Anal sex was almost always a part of our time together and she'd prepare for our meetings by cleansing herself thoroughly with several enemas. Corporal discipline was also very much a part of our relationship, and she understood that in addition to any other necessary attitude and lifestyle correcting discipline she would be punished for any lack of cleanliness, inside or outside, at any time. No matter how often she submitted without resistance to being taken anally she was never able to do so without copious tears and sobs and moaned promises of any other kind of service I wanted if I'd just not take her ass - which of course only made me want her tight, warm, always freshly-cleansed ass even more. She once said that I didn't really understand how difficult anal sex was for her, so I thought to find out for myself. I'd never been penetrated anally, except for enema nozzles and the like and occasional prostate massages. Frankly I was curious. And I knew that I could always tell her to stop if I needed to, which was certainly not something that she could ever tell me. So, after a bit of looking online at the infinite number and variety of dildos available and suitable for use on a man, I had her purchase something called a Feeldoe. It was a two-headed dildo with one smaller head to be inserted up inside a woman's vagina, and the other, more substantial (and penis-realistic) head to be used to penetrate the woman's partner. I made certain that she ordered the dildo early enough to take delivery several days before we met, thinking that surely she'd try it while she was alone. I didn't ask, but I think that she did try it. When we met, she was at first hesitant as I watched her insert the smaller head inside her vagina and then made her look at herself in a mirror and see the larger head cock-like dildo protruding and curving upward from the front of her vagina. I told her to lube her "cock" and my ass thoroughly, lay with all of her weight on top of me while I was lying prone and facedown on the bed, and then slowly ease the Feeldoe into my ass. I told her that I wanted her to show me what it was like to be fucked. It was an awkward situation as she slathered my ass with lube and after several attempts finally managed to control the dildo enough to direct it between my ass cheeks. Even though I told her to go slow, once she got the dildo properly aligned she forcefully thrust it all the way into me in a single stroke and then immediately started to withdraw and thrust it in again, over and over. I yelled (screamed, actually) and was instantly in searing pain. I felt like she was trying to rip me open. But then just as quickly I realized that she was using me and my ass in the same way that I used her. She didn't really know how to do otherwise. She did slow down for a moment, but then she started again with the in and out motion. At one point I raised my upper body off the bed by pushing myself up on my hands, but she immediately slapped my hands away and pushed me back down on my belly. She very quickly seemed to be enjoying what she was doing. She'd realized that her thrusting enabled her to pleasure herself with the head of the dildo that was up inside her vagina. She went a bit wild. I wasn't just experiencing anal sex as the receiver for the first time - I was being seriously fucked by a woman who was at the same time sexually pleasuring herself. I knew that I could stop her at any time I wanted, but I didn't. That's hard to explain, but I didn't. The pain gradually subsided and I became aware of a strange, new, pleasurable sensation of having a "cock" buried in my ass, and I experienced my first real sense of sexually serving and submitting to a dominant partner. And that happened even though I'd just wanted to feel what it would be like to be fucked. Eventually she managed to bring herself to orgasm and then raised up on her knees, pulling the smaller head from her vagina and leaving that bigger head inside me. I told her to slowly and gently remove the dildo from my ass and to then assume a position on her hands and knees on the bed, with her chest on the bed and her ass up in the air. Laying there on my belly with my legs opened and a dildo buried in my ass, I assume that I was trying to regain my sense of control of the situation by instructing her as to what to do. I told her that she'd probably taken me to a place that I'd regret going to, and that she was to be properly punished for doing so. She looked confused, but knew better than to challenge me. I then spanked her bare ass with a large leather paddle. Hard. For at least half an hour. Slow, well-placed, hard, both-cheeks-at-the-same-time strokes, over and over and over. In spite of her sobbing, guttural apologies for the way she'd lost control, paddling her ass until it was beet red and throbbing still didn't enable me to completely recover from the ego-bruising experience of having been so aggressively fucked by my own sub - or my own seeming willingness to accept and submit to the experience. Again, that's hard to explain.

My first time I was a freshmen in high school and he was a senior. He was gentle and it was the most amazing feeling. He rimmed me first and I had never had that done on me before and by the time he slid in, I was completely relaxed.

It was with this 2 years older boy from the neighbourhood I was playing doctor with regularly. I was 12 and he was 14 then. On this one day we were again doing our rectal measurements until one of us started to ask how a dick in the anus would feel. So we decided to try. We knew that there was a way to get our rectums clean; I had read something about enemas and explained it to my buddy. He agreed because we both didn't want to have shit on our dicks. For our doctor play action we had some bigger plastic syringes with us which we used as an enema syringe. We even got more horny. :-) After a successful cleansing we greased our dicks and slowly started to insert them into our anuses changing position top -> bottom from time to time. I remember enjoying it so very much, my friend sometimes felt some pain. After a while I couldn't take it any longer and I came while my friend was fucking me. I remember kneeling on this blanket with my head down, and I had my sperm all over my face because it came out with so much pressure. My friend took his dick out and came afterwards without something in his anus. Surprisingly we did not come in one another's hole. Boy, it was unbelievable…..I can tell you that. Great memories.

At this point in time in my life, I was 15 years old and it was about mid-summer in our corner of the Midwest USA. A group of us guys were sitting on the steps by “Ralph's” home. We were talking about the current happenings in our school and the neighborhood. Sports, hot cars, fishing, boating, baseball were covered and with a group of guys it eventually lead to the subject of girls. Like, who was going with who and maybe someone got lucky with one of them. None of us admitted to being successful in that respect , most likely because we would not know what to do with no prior experience. The idea of how to get some experience ahead of time came up. One of the guys suggested we get some practice on each other. There was four of us and we could pair up and get some experience using anal sex. We decided to pair up by drawing names and I ended up being paired with Ralph. He said we could try this out at his house as there were two bedrooms upstairs we could use. He also said his parents were gone until later and his younger Sister was gone and wouldn't be home for several hours.

We all agreed to the plan and we were just about ready to go into the house, when one of the other guy's Sister showed up and said he had to go home right now, his Mother needed him. So with that, those two guys left and it was just Ralph and I to carry on. So Ralph and I went into the house and upstairs to his bedroom. His Sister's bedroom was across the hallway next to the bathroom. He said he was going to the bathroom to get some Vaseline, but returned with some of his Sister's Pond's hand creme. We proceeded to take off our shoes, trousers and underwear and decided the one who got the first erection up was going to be the first giver. Ralph was erect very quickly, so I was going to be the first receiver and doggy style position would be the best way to do this. As Ralph put some Pond's creme on his penis, I laid over the bed foot-board railing with my feet on the floor, with my legs spread apart somewhat. This left my anus well exposed to him with my head and shoulder resting on the bed. He asked if I was ready and I said yes and he said we would match up pretty good. I felt his penis just lightly touch my anus momentarily, then he slowly started to push the head of his penis in past my anal opening. Suddenly there was a loud pounding and banging on his Sister's bedroom window, his Sister had come home early! Ralph went limp almost immediately and pulled his penis out of my anus. His Sister was screaming at him to unlock the back door. Ralph yelled that he was in the bathroom and would unlock the door in a few minutes. I quickly got my clothes on and went down the front stairs to the front door and left as Ralph was going down the back stairs to unlock the back door. His Sister was still yelling at him as I was walking away up the sidewalk.

For some unknown reason, we as a group guys when we got together in the future, never discussed the outcome of our planned encounter. The subject never came up again. I have wondered over the years, what if our plans had a successful outcome?

Me and my first girlfriend (we were both in 6th grade) got into it pretty early on because she either wanted me to wear a condom, because she was worried about the remote possibility of being impregnated (we were both virgins, so STD's were a non issue).

After a little persuasion (and a lot of online research and talking to some older friends), and quite a good quite a good amount of baby-oil, we did it. After using my fingers to loosen/grease her up, my dominant hand to handle the base of my cock I was able to push against her just hard enough to eventually get it to slip in with a slight pop. I went nice and slow at first, and started playing with her pussy, and it wasn't long before I had more and more of me inside her. I got the whole length inside her.

Since I came before her, we did it a second time and I somehow managed to hang on long enough for her to cum. She liked it so we were doing anal almost all the time from then on.

35. Very negative experience. He was way too much of a roughhouser. I was only happy when the ordeal was over.

Like most stereotypes, there's a kernel of truth to it: We men all have our brains located down there.

My first experience was at around 20, but the guy I dated did not lube up and just stuck it up there, traumatizing my poor virgin arsehole by tearing it 😵

After that I started training and stretching and teaching myself anal through the use of toys (and lube!) and my experiences from there have been awesome.

@BobbyG What a jerk!

First time was weird. We used fingers and butt plug. Felt so weird letting him see my anus, finger me there and put the plug in. But it was so good. It hurt a bit when he enterd with the dick, but just for a short time. I let him fuck me in the ass often to get used to it. For a time I had to have a finger wiggle in the ass to orgasm.

Im actually sure it was my first fun sensations as early as I can remember. I would always insert fingers in the bath and soon anything I could find. I love everything to do with it 😊

My first time anal, was when I lost my virginity. I met a girl, and we hit it off, on the first date. When I pulled into her driveway to drop her off, the house lights were off, and she wanted to have sex.( As if I didn't ?) I didn't have a condom, and it was around 2 a.m. She suggested anal, and I got an instant hard on, as she removed a small Vaseline jar from her pocketbook, and dropped her pants. It was one of the most awesome experiences, bar none ! The sights, sounds, smells, body quivering, etc.

@JJM : That's great when the offer comes from a woman. A good friend told me about a date with a pretty blonde and they ended up having impromptu sex too. But the blonde dampened expectations and told my friend that she was menstruating. At his disappointed look, the woman pulled a tube of lube out of her purse and said, "Do it where I don't have a period."

I was really late to the party.My first anal was when I was 55.I went to a sex shop and was just hanging out watching some porn and a guy came up to me and asked me if I liked the on screen action.It was 2 guys fucking.I said I did.The next thing you know we are in a booth.I pulled my pants down and he took out his cock.It was a biggie.I guess go big right away .He tried to put it into my tight hole needless to say it hurt.He took out a packet of lube and it was smooth sailing after that.It felt really great.I always wanted to know what it would be like to get fucked.He came pulled out and took off the condom.I then sucked his cock clean.From then on I was hooked.Love a nice hard cock in my tight ass.Filler up.