Learning About Anal Sex

When I was in seventh grade I was sitting in our science class next to a girl named Buffy. Our desks were really small tables that seated two students at each desk. Buffy was a real “wild child”. She had very short hair (for a girl), and had a very foul mouth for a thirteen year old. The teacher was scolding us about something, and I clearly heard Buffy mutter, under her breath, “Fuck my ass!” Now only a few weeks prior, in our Health class, we had been separated into a boys group and a girls group. The rudimentary aspects of sexual reproduction were explained to us, and we were told our corresponding role. It had never entered my mind that someone would have anal sex. What would that be like? Is it even possible? Would that be pleasurable for either party? I was quite shocked by Buffy’s comment, but that was clearly the first time I had been introduced to the topic.

About seven years later I was at college, and gone out with a group of friends for some beers. I was pretty new to this school, having just transferred in as a junior. One of the girls in the group was quite taken with me, and after the drinks I walked her home to her dormitory. It was a coed dorm, and she invited me up to her room. When we got there, she discovered that her roommate was sleeping, so she invited me to the common area lounge. We sat there in the dark and made out for some time. She told me that she wanted to have sex, but I told her that I was a virgin, and was unwilling to punch that ticket just yet. She persisted, and tried very hard to seduce me. I was pretty well resolved, and told her I was not going to put my penis in her vagina. She then said, “That’s not where I want it!” I was very inexperienced, and Buffy’s suggestion notwithstanding, I assumed she was talking about oral sex. I never asked for clarification. Yes. Of course, that must be what she meant! I settled for some heavy petting and groping, and made my escape, my virtue intact, as the sun was beginning to rise that autumn day. As I reconstruct the event, I’m pretty sure she wanted to introduce me to anal sex; pitching (as they say), not catching.

About five years ago, I was with a gal in Hong Kong. She made clear that she wanted sexual intercourse with me, and aggressively mounted me in the cowgirl fashion. After having her first orgasm, she lifted herself up, made a slight adjustment, and took my anal sex flower without so much as a ‘please’ or ‘thank you’. I obliged her in a number of positions, but could not finish, as it were. Not wanting to place the soiled ‘tool’ in her ‘garage’ she finished me off with a lovely handjob. I tried anal sex twice after that, but could never get across the finish line. Sorry to all the girls who may crave it. I’m now happy to oblige but only for the ladies’ pleasure.

The only times I've ever ever had failure blowing my load into a woman's ass was during major 'beer boner' experiences. Hard as a rock, stroking away for who knows how long and having to quit due to exhaustion! Next morning usually completes it

Never had that problem - maybe just the opposite of cumming too soon. But still stayed hard and able to satisfy my wife. Anal sex to me was more like masturbation, tight grip around the penis, whereas vaginal sex was stimulating the entire shaft. Both were. EXCELLENT!. We had some memorable times.

Anal intercourse always makes me come. The sensation and the visual is simply to good.

The only time I had anal sex and didn't come in the woman's ass was a girlfriend who after several months of regular anal intercourse began to request that I pull out before ejaculating. This was because my come in her rectum began to affect her bowel movements, making them loose. Wearing a condom wasnt an option because the feeling isn't the same. So I began to pull out, then ejaculating on her ass cheeks.

Like Morty, I learned about it seventh grade, but about a decade earlier, in the 1956-57 school year. Back then, oral and anal were the only available forms of birth control available to anybody but married men. All us kids, boys and girls, were deathly afraid of "getting in trouble." Boys talked among themselves about wanting to "cornhole" girls, but only occasionally a particular one. Judgmental prepubescent boys in the fifties would have considered any anally receptive girl a slut. There were none as outspoken as Morty's friend Buffy. A few of my friends claimed to have done it, but always saying with a girl we didn't know, from another neighborhood.

I had a primal attraction to ample female bottoms even before first onset of puberty at age 11, and the puerile discussions of actual, safe sex in a girl's rectum galvanized my nascent libido. Through high school, I watched the girls' hips widen and fatuously speculated that their anuses were growing proportionally. Had lots of oral (giving and receiving) in grades 9 thru 12 with college co-eds and a few faculty, vaginal only 3 times, terrified of pregnancy.

First anal was sophomore year of college with a middle aged, wide bottomed, and anally experienced woman. Penetration with vaseline was easy, and "love without fear" felt amazing, physically and psychologically. Can't relate to Morty's inability to climax in a woman's rectum, but lots of people here probably can't understand my preference.

I was introduced to the pleasures of my bottom being penetrated at a young age from a girl cousin while playing doctor, and I do say pleasures because I enjoyed it. Anal play was part of my early sexual experiences fairly soon but not penile penetration. I didn’t so much as ‘learn’ about it as experience it. I had a boyfriend try a few times in my teens but he was inept at it and it hurt so no go. He had fingered me there a few times and said something like ‘Let’s do it there.’ I was game but it hurt too much. Ditto my first husband, he tried the ‘whoops wrong hole’ move a few times. Nope. My current husband is the first guy who’s done it right.

Interestingly I met a young guy who wanted to get some experiences in doing anal sex. So I had to show him a few things, tricks, and let him try them on me. My impression was: he maybe was bisexual but he called himself only as hetero. He told me something about having fun with his girlfriend but not having the risk that she might be pregnant afterwards and so on. We met several times, but he only was the active part and didn't want to try the passive side.

My story about anal sex goes back to my University days.

As most graduates do I had a few boy friends at University. I remember on one occasion we had been together and he had given me a great orgasm and of course I was desperate to be entered then as I am sure most women would be. However, for some reason we did not have any condoms and I was so desperate That I told him to enter the other place. Then, with small supply of Vaseline and the fact that he had a thinner than usual penis he was able to enter without any discomfort. Also he was able to discharge his semen in there and I had that usual feeling of is penis jerking as he came. All some time ago but still very memorable.

Learned about anal sex in the fifth grade - a friend invited me over after school to do homework and spend the night. After doing our homework he invited me into a bedroom where we both took off our clothes - evidently he had previous experience with an older cousin who taught him a few things about masturbation and anal sex. He told me about it and asked me if I was interested - of course I said yes as hormones and curiosity were running high! He produced a jar of Vaseline and we both put some on our cocks and assholes. Soon a cock was slowly inserted in my ass and began a new adventure for me! We then switched roles and I came inside him within a few minutes as I discovered the intense pleasure of his sphincter squeezing my cock. What a fun evening!

Had heard about it as a teen as a way of avoiding pregnancy but discounted it it as bravado, although it was known as ‘the Catholic’ way.

Didn't think anything of it until I was in 30’s and watched a vhs porn. Wow.

Hooked from then.

Now common place and even a subject discussed with daughter - aged in late 20s.

@dgh said

. . . . Now common place and even a subject discussed with daughter - aged in late 20s.

You're a pig discussing anal sex with your daughter.

.

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just like me! 😁 😁 😁

@SwitchableSusie @dgh

Just wondering, was that first anal sex conversation initiated by parent or daughter?

@RichardAsni said

Just wondering, was that first anal sex conversation initiated by parent or daughter?

The first discussion of anal sex would have been a few years before The Adventurer started puberty, so I guess she was around 9 or 10. By the time the girls interrogated us about our kinky equipment room they both already knew about anal sex and what kinky sex was. What kids learn on the school bus is an eye opener. We started having in depth sex discussions when they were very young. They knew exactly how to make a baby when they were about three and a half. One very tearful night The Adventurer asked "where did I come from" and she wasn't happy with the vague general answers you typically give to a three and a half year old and she would not go to sleep and was crying bitterly until she got all the info about eggs and sperm, erections, orgasms and ejaculations, fetuses, pregnancies and deliveries.

After hearing all the details she was satisfied and went to sleep. You cannot pull the wool over a smart kid's eyes. When The Mouth was about four, she asked the same question and her older sister who was about seven was answering her. To make sure the information was correctly given, I butted in and did the explanation with The Adventurer "embellishing" what I was saying. She especially liked telling her sister that an orgasm is much better than Haagen Dazs, which is what we told her when she was little.

She especially liked telling her sister that an orgasm is much better than Haagen Dazs,

It is a wonder that the company hasn't trademarked this in some form, it would make for a great advertising campaign ... although in truth, just about all ice cream is better than Haagen Dazs ... ha ha.

@agracier said

It is a wonder that the company hasn't trademarked this, it would make for a great advertising campaign ... although in truth, just about all ice cream is better than Haagen Dazs ... ha ha.

Like what brand?

Like what brand?

Ummm ... where I live there aren't really any large brands of ice cream. Sure you can buy stuff in supermarkets (including vastly overpriced Ben & Jerries and HD in a few places), but normally people buy at ice cream parlors or street stands ... small scale ice cream production, each somewhat specific as to ingredients and flavors ...

Wife and I have anal sex about once a month. I like that it is so snug. I must pace myself so as not to orgasm too quickly.

I agree to Jimmy1; it takes my full concentration cum not to soon, because wifes anus is so intense to my penis. She sometimes wants me to cum inside her or pull out and masturbate over her cheeks. Once I was the active part with another guy, and it was no problem to hold it back for a long time, because his anus was not as intense as my wifes.

In my twenties, my girlfriend always offered me anal sex for my birthday. I probably could have had it more often, but having it on my birthday kept it more exotic and special.

(I’m a straight man) with some handsome gay friends. In my forties, the night I really “learned” about anal sex was the night I decided to experiment and be the man my gay buddies often suggested. After some drinking and a lot of flirting, I found myself blowing Brent like I had done it a hundred times before! (I had never done it before, nor even thought about). He was well endowed with a shaved clean body, and I blew him like a pro, like I liked to get blown by women- (do unto others...)

After successfully swallowing Brent and a few more drinks, we retired to their California Kingsized bed where Patrick managed to “really give me the queer treatment.” At first I refused his advances on on anus, but eventually succumbed to giving that a try too. He was eventually balls deep into me and pumping hard! As a straight man l was was of course reluctant at first, but the alcohol and curiosity and breath on the back of my neck won me over. I can’t say blowing a guy is my favorite thing, but I gave it my best. I can say getting fucked in the ass was a treat I will never forget!

That’s the night I really “learned about anal sex!”

I’m still not gay, nor have I tried any of the above since, but I’m damned glad that I did it that once!

Experiment when you get the chance! It won’t “make you gay”.

I have to say I learned about anal sex by doing it. You can do just about anything as long as you have lube.

I think I was born anally erotic, pair that with a few early rectal temps, 2 early bulb syringe enemas and the fact that I had special crayon that fit nicely and I was on my way! From the beginning I liked touching my clit etc. but touching my anus was somehow more exciting. Then, a real enema at 9 and a year or so during 6th and 7th grade playing with a very aggressive girl friend who paid more attention to my anus and I was hooked! I think I always realized I could put "things" in both places and I used to feel sorry for the boys and felt they were a bit handicapped when it came to sexual excitement. As I developed I realized I could but bigger and bigger things in both places. It was only natural and a matter of time and place before a penis was going to finds it way up my bottom! LOL

I have to say I learned about anal sex by doing it. You can do just about anything as long as you have lube.

Or a can of bacon grease!

Hog lard is an amazing product!

Scrapple for anal lube?

Thinking about the topic title, Learning About Anal Sex, made me wonder how I learned. Somehow I did because the first time I did it, with a woman who’d also never done it, it was wonderful for us both and we did it many times after, rarely returning to vaginal sex.

I grew up pre-internet so most of my learning about sex came from looking at and reading porn magazines, Penthouse and Playboy mostly. The reader letters and articles made my young eyeballs jump out of my head, reading about the things people did to each other after taking off all their clothes. Mind blowing for a totally shy and naive 12 year old suburban boy.

Other than awkward, naive jokes, I never discussed any of it with my male friends. Once I had a girlfriend in high school, we learned about sex together just by exploring and trying things. But she didn’t want me to put anything inside her bottom, although she liked me to kiss and lick it which I adored doing. Several years later when a woman I was dating proposed we have anal sex, I was ready though still nervous. Over those next few months I learned a whole lot more about what can be done to a willing ass.

@RichardAsni, your learning experience sounds like deja vu all over again!

Very similar experiences here!

@Like_it_deep Yes, great memories!

After that first woman and I broke up after months of anal sex, I was certain I’d never have an experience like that again. In some ways I never did cause she had a particular naughty, anus-obsessed personality. She was very submissive but learned also to be dominant when I admitted to her that I wanted to be “your patient”. Like me she had powerful memories of medical experiences and admitted she’d always wanted to examine someone else’s bottom “like a doctor does”. I was happy to oblige! A lot of our Anal Sex Learning came from our honesty about our naughty desires and memories from the doctors exam table.

Over the years I dated other women, had a couple long term girlfriends. All except one enjoyed anal play, but I only had consistent anal intercourse with three of them. Two girlfriends and one friend with benefits who I saw during regular work trips.

I guess I realized that what I “learned” about anal sex is that each person is different, what they like, dont like, etc, but that patience and trust and honesty can reveal someone’s deepest darkest naughtiest desires. Also learned that you can’t judge a book by its cover. Women who love anal sex aren’t necessarily the ones you’d think!

That's an interesting question, if I think about that. I had a quite old-fashioned upbringing with almost no internet and the thought that you can have anal sex hasn't actually entered my mind until I was about eighteen years old. Funny, because at that point I was already anally erotic to no end thanks to my previous enema experiences. I guess I've heard something from the boys when I was a teenage girl, jokes about fucking animals and stuff, but I pretended not to notice them as they were really gross and I didn't actually quite grasp the meaning :-)

That's why I would say I've really “learned” about the anal sex when I moved to the big city after finishing high school and started to study in college. I discovered such things as erotic stories and porn and started to explore myself in that way. Soon after I've met my current partner, who was the first one to show me how it goes irl and I loved it from the first time.

My sexual education came almost entirely from the internet via wikipedia, other online encyclopedias, and porn sites. I‘m pretty sure I discovered anal sex just before or during 5th grade by finding a tumblr dedicated to images of attractive people mid buggering. For some reason I think most of the pics were sepia and black and white although they weren’t old it was just edited that way. I believe I found the album while simply searching for nudity. I started by searching for pictures of naked women out of curiosity, and then pictures of women being touched or touching themselves, and then intercourse. Eventually I progressed toward watching video porn and through recommended videos I remember finding a video of a woman fingering her butt, or it may have been a woman being fingered by another woman, but I’m not sure. Either way I remember thinking “Wow she looks like she’s really enjoying herself,” and then realizing that I could do that to myself.