First anal

Hmm, I’m apparently still at a message board and email level with discussing enemas, meaning to me that they’re not a thing fully integrated into my day to day life yet. I look forward to the day I’m texting about enemas and perhaps narrowly avoiding awkward typos.

Since that experience I have been so careful to enunciate when I share my kinks verbally for the first time with someone new.

He was obviously NOT into giving anal, for I cant imagine ANYONE on this forum finding their partner fingering their asshole in the shower (after expressing an anal interest) and NOT wanting to take that further, right then and there!! I’m sure as you found more excited partners is when it became more pleasurable.

Perhaps, or perhaps not. At that point in time we were friends who made out and showered together and occasionally did some sexy things, but his sexual experience was so tied up in particular aspects of BDSM that he didn’t really know how to pleasure a partner, and I was taking a break from sex after an experience with the murky areas of consent. That he didn’t take things farther than that the time in the shower is fitting to the relationship we had then.

And yes, recent partners have been absolutely spectacular with anal activities- there is still a fondness with which I recall this first fumbling and unspectacular beginning, perhaps more for the person it was with than anything else.

Lots of posts, so I've skimmed through, but an interesting read. Thought I'd throw my hat in the ring here.

Can't remember my exact age at the time I first inserted a finger, maybe 12 or 13, but it certainly interested me. Not that it felt good, but that it didn't feel bad, and I had watched porn and seen anal, thought it looked fun. Wondered whether it would be as good for a guy to receive as for a woman in the videos. Stupid thought obviously, as it's mostly faked, but at the time I was far dumber than I am now.

A few years of occasional fingering, got my first debit card, made some online orders for a first PC build, and found I had some cash left over. Without thinking about it too much, I ordered a little butt plug with ridges all round, and my wanking increased tenfold from there.

First enema was probably around 16, with my parents away for the day, and a newly installed electric shower. I regretted filling myself so much after holding the water in for 30 minutes, but filling myself up was definitely fun.

First anal experience was at age 12 or 13 with a friend from school. had me over to spend the night. after we both bathed for the night went into the bedroom and closed the door. he asked me if I had ever jacked off and told him no. he proceeded to show me the ropes and shortly we were both stroking each other. next thing I knew he produced a jar of vaseline and said let's try doing it in the butt. his cock felt so good in my butt as I squeezed it while he was inside. next we reversed and I was inside him as he squeezed my cock. I came very shortly as the feeling was so intense. we did this many times in the following year - each time was so enjoyable! sometimes we would look at porn magazines from his cousin as we jacked off

I was 14, she was 17. It was a blind double date. The other boy, a school friend, drove. We ate at a neighborhood pizza parlor and then went to a "teen canteen," as they were called back in the fifties. We left about 10:30 and repaired to the other boy's home. His parents were out of town. The other couple went straight to one of the bedrooms. My date and I found our way to the den, sat down on the couch and started embracing and French kissing. After a few minutes, I reclined and pulled her on top of me, continuing to French kiss and embrace, with her arms around my neck and mine around her back. After a few minutes, I found her shorts had a zipper in back, unzipped it and put my hand down the shorts on to her bare bottom. Searching awkwardly with my middle finger for her vagina, I found her anus easily and impulsively inserted my finger as far as it would go. She did not react. There was no more anal contact, but we continued "making out," for another hour. That was the first time I ever touched a woman's privates. It was a gratifying and encouraging milestone in my anal eroticism.

I was 14 and so was my exboyfriend. We'd always wanted to have proper sex (you know, pussy and stuffs). But for a lot of reasons, we couldn't. So one day, be came up with a bright idea, my other hole(anus). Back then, I didn't know anything about it, but i was horny and so was he. He put some vaseline on a pen and then shove the pen up my ass.

For the first minute or so, i genuinely felt good and i was really really wet. I stroke his penis as he went faster and faster. When he started to lick my pussy and bite my clit, that was it. I screamed uncontrollably as i peed and shit all over my bed. It was embarrassing. My ass was still pushing out the brown stuff as my body kept on shaking. I was exhauted. I layed there, in a puddle of piss and shit, for the rest of the night. I didn't know my exboyfriend reaction then caused i literally passed out. The only thing i know was that he probably felt disgusted and left immediately. That was last time i saw him 😢(

Late bloomer. was in grad school when a gf did what I later learned was rimming. it felt great and I wondered how she could like around my anus? felt great, seemed weird, but little did I know. later I moved on to zucchini and other vegies before getting into human appendages...

@Jack45. Thanks for a very nice account of teenage anal fun. I am curious though. A very first time (albeit using Vaseline). Was there absolutely no discomfort or pain whatsoever? None? Your virgin anal sphincter being penetrated. It all sounds so easy and relaxed. No anal experience whatsoever and your cousin just announces, effectively, that he would like to fuck you. I would have been as scared and tense as hell!!! Were you not even in the slightest bit worried or apprehensive??

I came across my brothers porn stash when I was young (really too young to be seeing that!) I read an interview with a porn star where she mentioned liking small things in her butt. I had already found my magic “front button” so I decided to see if her advice added to the experience. I don’t recall what I used? A tiny screwdriver or a toy around the house (like a child’s toy, not a sex toy) and it wasn’t awful but it wasn’t fireworks either. Many years later, being all worldly and shit, I found myself at my boyfriends house while his parents were away. When we decided to have sex, I realized my period had started so I suggested we try my ass instead (teenager logic, period sex is gross but sure let’s try anal on a whim!) We found some Vaseline and went super slow but it was painful and super awkward and a little messy so we stopped. I think we just gave up on sex for the weekend rather than try again. Luckily, I dated a jerk a few years later who thought he was Don Juan and had a really small penis. He wanted to go round the back often and with proper lube and his skinny package, I decided it wasn’t an altogether unpleasant experience!

There are a lot of firsts with anal. First on yourself, first with objects, first with partner, first giving... I loved every one of mine!

For me, I started at 14/15, using a rectal thermometer or Bic pen (sans ink) while masturbating. I’m sure I tried that because I knew from age 12/13 that I LOVED female ass and couldn’t want to lick and finger and fuck one! So at some point I must have decided to try it on myself. At 19 with my first full sexual partner, one awkward time in a car I got a finger in her ass. She was so slippery and we were groping all over each other that she didn’t seem to notice. However during subsequent sex, when I put my finger there she moved it away, so there was no more anal play with her.

My first anal sex was with my next GF at age 20. One time after sex on her parents couch, we were resting with her lying on top of me and I was stroking her lovely tight buns as we kissed and talked. I gently pulled her sexy cheeks open and slowly ran my fingers down her crack and as I touched her hole I softly said something like “God I can’t wait to explore ALL of you!” She got this shocked/horrified look on her face that was priceless! A few months later (long distance due to college) we were in a motel room to fuck for the day and I brought Vaseline ! Midway through our day I had her lie on her stomach and was massaging her back and legs and her gorgeous butt. She was SO relaxed and sexy I had to make my move! So I awkwardly fumbled trying to get the little jar out of my bag without ruining the ‘mood.’ She later told me she knew what I was going to do and damn was I lucky she let me continue!

I managed to massage her butt and hole for a while and eventually she moved her hands underneath her so she could play with her pussy and clit. I dug into the Vaseline and slowly worked my finger in/out, until each knuckle disappeared. We both worked her into a frenzy until she had an amazing orgasm and she later told me it was the best one of the dozen at the hotel (we didn’t leave the room!) It was an incredible experience to feel her so intimately and have her derive such pleasure from it. I was hooked!

A few months later we consummated anal sex on my sisters water bed. She said it hurt a bit the first time, but that vaginal sex for her did too, and that got better so she was game for more. She ended up loving it and we were 50/50 vaginal/anal for the remainder of our relationship.

Like most boys, my older brother, his friend and were always playing with our cocks. I was about fourteen and my brother and his friend were about sixteen. We progressed touching each others cocks, Finally, one we got completely naked in my room and decided to try sucking. I was fascinated with the friends uncut cock and took it in my mouth, He was lying on the bed and I bent over and began sucking him, Not to be left out, my brother was behind me rubbing his cock on my ass and playing with my cock. As I sucked he rubbed his cock up and down my ass crack, soaking it with his precum. Then his cock found my hole and he pressed against it. I could feel his cock head slipping in as I was sucking his friends cock. Before I knew it he was deep in my ass and it felt so good I wanted to cum. Then I felt his cock throb as he came deep in my virgin ass. Then his friend exploded and filled my mouth with his cum. My brother then pulled his cock out, turned me around and suck ed my cock until I came. What a triple play.........first time giving and getting a blow job and losing my anal virginity, Needless to say, we repeated this many times.

@schoolmedsboi

No pain or discomfort but had been doing anal play solo prior.

We used lots of Vaseline on both our cocks and buttholes so slid right in - when my friend squeezed my cock with his sphincter it would cause me to come!

Luckily, I dated a jerk a few years later who thought he was Don Juan and had a really small penis. He wanted to go round the back often and with proper lube and his skinny package, I decided it wasn’t an altogether unpleasant experience!

Poor little feller. I guess that is called the Napoleon syndrome. Small dick butt big ego.

I don't remember my first anal experience, but it was pre puberty... by a pretty long shot? i discovered my anus as an organ of sexual pleasure way before i discovered my penis as such. The earliest i can recollect feeling about my anus sexually was about 8 or 9 years old when a neighborhood friend explained enemas to me. i had a crush on him and was definitely titillated by his explanation. I think it was then that i started penetrating myself and really liking it.

I guess that is called the Napoleon syndrome. Small dick butt big ego.

Easy to find internet links on this. Here are 2 conflicting accounts. Up to you to decide which could be the most correct.

http://mentalfloss.com/article/63312/where-world-napoleons-penis

https://shannonselin.com/tag/napoleons-penis/

And penis size aside, Napoleon was known to have a high sex drive and many lovers during his lifetime (fame and power being the main attractions for the ladies of course, not penis size at all).

My first experience of anal sex happened when I was 13 yrs.old and was with one of my best friends .We had gone to school together since we were both in same grade 1 class. My parents became friends had been friend with his parents before that ,since my mother had worked with his mother for awhile .During the years we would sleep over at each others house mostly because our Parents would take turns babysitting each other when other Parents went out.

It happened one night just out of the blue actually I was 13 he had just turned 14 our Parents went out together to a Party for someone 25th anniv. We were old enough to stay alone they figured since together so left us at my friends house .I remember it like it was yesterday ,we were watching T.V had already changed into P.J's (my friend had said in his room when changing since no one around lets not wear our underwear on under our P.J's) I did not really give much thought since his Mother ,my Mother not around and they would see for sure if not have on through P.J's. So as we were watching T.V. my friend and I started to wrestle on the floor (as boys do ) and my friend pinned my down at one point on my stomach ,pulled my PJ's down just below my cheeks and slapped my ass fairly hard ,then pulled back up . He then let me go and said want to play a game . 1st time loser pinned gets ass slapped,..2nd time loser sucks winners cock just a bit ..and 3rd time masturbates winner to cumming onto Kleenex/paper towel. So I agreed and we started at 0-0.

Long story short I had lost 2 x he 1x so my turn and I sucked his cock (first time ever ,to me the head of his cock seemed to be fairly large)so that done a little back at it and his cock had ,had pre-cum on it and kept telling me to lick it off.Finally well I lost a 3rd time BUT lost and was on my stomach ,my friend had me pinned down and like before pulled my Pj's down only this time Not just below my cheeks below my knees then right off.He then slapped my ass 3 x and pretty hard ,still pinned with his knees on my back I said what the hell, thought I was to masturbate you .He said lets try something different since I am the winner 3x He said for me to get on my hands and knees and he would be back in a second .

He comes back with this bottle of Vaseline Intensive Care (with the pump) takes his bottoms off and then I hear him push the Vaseline pump and then he tells me to spread my knees wide ,then just as I get my knees spread I feel this cold Vaseline being shoved with his middle finger fairly deep into my ass ( which forces me to move forward along with my cock starting to get erect) He pulls out his finger wipes off on kleenex I hear ,then I feel his hands grab my hips and at same time slowly feel that head of his cock (lg head) touching the entrance of my hole . He told me he will go real slow and saw in a movie for me to bend my head down and get down on my forearms , slowly he pushed his cock into me until he was all the way in .( he was about 6 in. lg avg thick.) I cannot say it was Painful ,but it did kinda hurt at times ,yet felt real good when in all the way .I had a wicked hard erection and pre-cum dripping away.Then he slowly started to pull back and forth for about 6-8 strokes then a little faster ,I could not get over how GOOD IT FELT ,at one point I actually was sort of pushing sort-of-back to meet his cock .I could not handle the feeling a came ,it felt like I came a gallon of cum /could not stop. My friend kept for about 2 more minutes I think and then I felt his cock start to throb and could feel it throbbing as he was shooting his cum inside of my ass ,I must say I really enjoyed the feeling ,as he pulled out I could feel the cum not to long after leaking out of me ,he told me to stay like that as he put some paper towels under my ass on the rug . That was my First time BUT after that night my friend and I kept it a SECRET ALL through HIGH SCHOOL and at least 1-2 x a month we would get together and suck and have anal sex (started to use a condom once started dating) I truly believe that evening is what POSSIBLY showed me or helped me to becoming and enjoying being Bi-sexual to this day .

Well, here we go. I hope you don’t mind if I give you the long version. When I was about 11, I stayed over at a friend’s house. He had started school later than I (I started early) and had been held back a couple of years, so he was about 14. A very mature 14. I was a young, naive 11.

We were lying in his bed that night and he was talking about girls and sex. I’d heard that kind of talk at school, but didn’t really know much about it. I looked over in the dim light and saw the “tent”. I had no idea what it was, as I still had a little peepee that got stiff while I slept for reasons I didn’t know. I asked what it was and he showed it to me. I had never seen anything like that.

He asked if he could stick it in my butt, and I remembered the enemas that my mom had given me, and I didn’t mind those. The little red syringe felt ok, so why wouldn’t anything else? I told him to go ahead and he instructed me to roll over and spread my legs, which I did right away, because this was something new. He climbed on top and pushed really hard but it would not go in. He was too big, I was too small, and we knew nothing about lube. After trying a bit, he gave up and showed me how to masturbate, which we did for a while.

When we were done, we went down stairs to the only bathroom to pee. I saw a tub of Vaseline on the back of the toilet and had a eureka moment... That’s how my mom gave me enemas. So we took it upstairs and tried again.

This time he climbed on top and pushed until it slid in. It really hurt at first. But since he was a lot bigger than I, and I’m naturally submissive, I laid there with my face in the pillow and took it.

Funny thing is, after a few minutes (and I think he went for a while) it started to feel kinda good. Then he was done.

We tried again a couple weeks later, but we were in the woods, with no lube again. He just dry humped between my legs. When he done, I looked down and was covered with this white stuff. I had no idea what that was either.

This is completely true and there’s details if anyone is interested. Please contact me or respond if you had a similar experience.

Since then, I’ve been obsessed with the feeling of having things inside me. Funny thing is, I’m not romantically attracted to other men at all. I just like that feeling that I first experienced almost fifty years ago.

@Phng_Uyen

I was 14 and so was my exboyfriend. We' 😁 always wanted to have proper sex (you know, pussy and stuffs). But for a lot of reasons, we couldn't. So one day, be came up with a bright idea, my other hole(anus). Back then, I didn't know anything about it, but i was horny and so was he. He put some vaseline on a pen and then shove the pen up my ass.

For the first minute or so, i genuinely felt good and i was really really wet. I stroke his penis as he went faster and faster. When he started to lick my pussy and bite my clit, that was it. I screamed uncontrollably as i peed and shit all over my bed. It was embarrassing. My ass was still pushing out the brown stuff as my body kept on shaking. I was exhauted. I layed there, in a puddle of piss and shit, for the rest of the night. I didn't know my exboyfriend reaction then caused i literally passed out. The only thing i know was that he probably felt disgusted and left immediately. That was last time i saw him 😢

Your intestine was filled with shit and your bladder of wee

The anal masturbation of your friend drove you to a very strong orgasm

who got outside wee and excrement.

A first explanation veiled

-

A second explanation concerning wee could be if your bladder was empty it is that you are woman fountain.

Welcome to you on ziti biz

clyso

I was 14 and so was my exboyfriend.

Bienvenue...

I was 11 years old. Plus or minus a year. I had a chemistry set. It had a glass stick for use when mixing up things in test tubes. Probably 6 inches long. Like the width of a swizzle stick. I remember liking to slide it in my butt. I remember actually leaving it in there, all the way in, and going outside the house, to play or whatever. Which kind of blows my mind. I don’t recall any issue or concern with being able to get it out. The folly of youth. Looking back, why didn’t I try with the test tubes? Hah, way too big. From that point on I did try other things, though, off and on. My parents once caught me stashing some things under the bed, took me to the family doctor, not sure why, never spoke to me directly about it.

I was 12 on a Boy Scout camping trip. We slept in two person pup tents. The boy i was sharing a tent with had brought one of his father's Penthouse magazines. We were looking at the pics and jerking off. He asked me if I had ever been fucked in the ass. I said no. He asked if I wanted to try it.

We did rock/scissor/paper to see who would go first. I laid on my belly and he parted my cheeks and spit on my asshole. Everybody says it hurts the first time but I don't remember pain. I just felt full, like I had to poo. He came in about 30 seconds.

When it was my turn I did the same thing. It was kinda difficult to get it but once i was in it felt really good. i did not last much longer than he did. My dick smelled like poo and there was no way to wash until morning. I resolved not to do that again unless I could wash immediately after.

Other anal experience other than enemas etc. as a kid, I was about 19. I came home from partying and was pretty horny. For some reason I had this desire for anal, but had never really done it. I remember finding a white bullet shaped vibrator about 8" in the linen closet ( of all places) one time and got up out of bed to see if it was still there. Nobody was home so I didn't really have to worry about anything. Sure enough it was still there, so i grabbed it and a jar of vaseline and got back into bed. I lubed it up and slowly inserted it. The feeling was unreal!! I just kept going in deeper and deeper...it felt so good! I didn't even turn it on. After about 5 minutes I had a very powerful orgasm... First of many anal orgasms!

My first anal experience happened at the age of 12 when a school friend invited me after school to study and spend the night. After homework he said let’s go and get ready for bed. We both got undressed and compared size. He asked me if I knew how to jack off and proceeded to show me how to do it. One thing led to another and he produced a jar of Vaseline and coated his dick and asked me to lay on my stomach. Then proceeded to insert it in my ass and fucked for awhile and then we reversed the role! Felt awesome as I came inside his ass!

My first anal experience happened at the age of 12 when a school friend invited me after school to study and spend the night. After homework he said let’s go and get ready for bed. We both got undressed and compared size. He asked me if I knew how to jack off and proceeded to show me how to do it. !

I often wonder with stories about sleepovers leading to mutual masturbation or other sexual activity as described above: how much do parents know/suspect or have an inkling about what goes on? Surely they are not that naive, surely they were young too once upon a time.

I have never read anyone writing how they might possibly have been confronted the next morning after, or if they perhaps made so much noise that parents came to investigate and saw the goings-on?

Or did parents ignore it all and shrug it off with a 'boys will boys' with other boys mentality? Or simply thankful they wouldn't get anyone pregnant?

I'm really curious. By the time I was old enough with a knowledge of sex, I was away from the US and living in Belgium where there was absolutely no custom of (school) friends having sleep-overs. Simply not done. And therefore - sadly - no opportunities for such kind of sex exploration ...

I don't remember ever going to a sleepover or my parents hosting one. My first anal experience, like my first sexual experiences in general, was with a male high school classmate. We'd been friends since 7th grade. They had a swimming pool at their house, like many homes in southern California in the 1950s. There would always be a bunch of us kids hanging out there, boys and girls since he had two older sisters. His dad had built a changing area in the garage, just a space walled off with blankets strung over ropes and a couple of benches and a place to hang clothes inside. The girls changed in his sisters' bedrooms but the boys were relegated to the garage. Sometimes the rest of the family would be away and he would be home alone. He'd call me up to invite me to come over to swim. My mother always said OK, so I'd get on my bike with a bathing suit rolled up in a towel strapped to rack and pedal over. Sometimes he'd already be in his swim trunks and I would go in the garage to change; often he'd come in with me to talk and it was obvious from the bulge in his suit that he liked to watch, and I couldn't hide the fact that I like to show. Over many swim sessions this led inevitably to exploration and experimentation. Bottom play was with fingers and vaseline first, then came the time he said "you ever wonder what it would feel like to be the girl?" His oldest sister was dating and I guess he'd overheard certain conversations, plus he'd gotten hold of a Playboy magazine....so one thing led to another and if we had the privacy we would take turns "being the girl." It was trial and error but eventually we got comfortable with it. Both of us grew up to marry, have kids, retire, etc. I still enjoy "being the girl" sometimes or helping out others when they want to find out what its like.

Reading here and being an enema / ass play fan, I want to try this, ideally having a lady present.

I would say my first "finger" happened about 5 years ago. I found about the idea when I was fingering myself. I found the nerve, muscle or tendon (whichever it is) on the bottom of the rectum and was facinated. Are there other areas that the rectum can be stimulated?

I made first experiences of self penetrating at age of 13 I guess. During childhood and youth I received rectal temperature measures and suppositories, and at age 11 or 12 I found it sort of annoying but my parents gave me no other choice. So it took a while until found it exciting and liked the sensation when something small was put in my bum.

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 bad, 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.

Then, long time and nothing happened, and I looked for sex dates at age of 18 on the internet (planetromeo.com)

I think I was probably mid teens. I'm not sure what started me, maybe something I read. Began with a finger then progressed to whatever I could find. I remember using a small snooker ball inside a plastic bag and leaving it in there. Also remember stealing one of my sister's tampons and trying that. Still look for ideas and opportunities!

I had always had my temp taken in my rectum. I did not like it at first but the longer it happened the more aroused I got. I would do anything just to have my temp taken to feel the glass thermometer slid into me. Finally around the age of 10 or 11 I was taking a bath and started playing with my bottom. I was really soapy and started fingering my butthole. The next thing I knew my finger slid in very deep inside me. I went as deep as I could. Then I got faster and faster. I got the hardest erection. I then started playing with my cock. Before I knew I came. That was the first time I ever played with my butthole. I have been doing it ever since. I have gotten three fingers up me at one time among other things. And yes I have even stuck a tampon up me once. I have never thought about having another cock in me till lately. I does kinda turn me on and would not rule it out at all.

I remember being around 12 or 13 and had a sleepover at a friends house. It was aw hot night and we were laying naked in his room and he asked me if I had ever jacked off. I said no and he came over and started stroking me cock and then i came for the first time. It scared the hell out of me and I told him to get away and i rolled over and went to sleep. We never talked about it since. He moved away and that was the last of it. Later i talked to my good friend and neighbor and we got out his Dad's Playbooks and soon we were naked and jacking off. Another day we were doing it again and he wanted to do anal on me so I said ok. He was gentle and slow and soon I came all over his bed. He was surprised and made me clean up my mess. We never did it again.