What was your first time having anal sex like?

I was forced to submit and please a cousin of mine, but it turned out to be sexily stimulating, we did it many times. It hurt but it was a good kind of hurt, I learned to relax take him, and please him, which excited me.

When I first considered anal, I was around 9, and the 8-year-old neighboring farm boy would come over to build hay bale forts with me. We would take turns laying on each other with our pants down while rubbing our penises against each other’s anuses while inside of a bale fort. It was more of a game of playing grownups, than it ever was sexual.

My first time of actually having anal was with a younger hispanic girl. It happened in the grass behind the schoolhouse in a neighboring small town. I was 14, and she was a couple years younger. (It was her idea). I sprained my penis something horrible, and it was temporarily disfigured and very sore for over a week.

My girlfriend of 10 years while in my 30’s would alway offer her ass up to me on my my birthday. I have to say it was one of my favorite gifts! She seemed to enjoy it too.

In my 40’s I received my first anal fucking by a gay buddy as a part of a threesome. He knew what he was doing, so it was pain-free. It was amazing, and I really enjoyed it once I let myself fully accept it and him! I had my moments over the years of feeling some regret about that night, but if I had it to do over, I would, and probably more that once! I’m still not gay or bi, but life is way too short to not experiment. If a guy ever gets that chance to get fucked in the ass by another handsome man, JUST DO IT.

With all of the “anal education” leading up to my present wife of 10 years, I feel safe to say that she would say I’m pretty good at it. She never complains. Having anal sex with my wife is definitely better than my first time!

~“It’s only kinky the first time.”~

The first time I fucked a woman in the ass was in high school. The lucky recipient wasn't Susan. It was another girlfriend. It was thrilling for both of us because it's dirty and taboo.

I’ll let you know.

I married rather young and my wife would never consent to anal sex. (against nature, she said). We eventually divorced for other reasons, but by my early thirties I had never attempted anal sex.

The advantage of the long wait was education. As time passed, anal sex became less taboo, lube was more accessible and information, though not abundant, had become more available. I had learned that ‘slow and easy’ with plenty of lube was the way to go. And that is what I did when my new girlfriend suggested we try it (!). It went great. I was surprised by how tight it felt on my penis and had to control my movements to avoid cumming too fast. She, on the other hand, wanted more thrusting. I soon exploded inside her, a feeling I’ll never forget. So that she could come, she asked me to lick her clit with a finger up her ass. She came soon afterwards and seemed very content. It was an unforgettable experience, I think for both of us.

Anal became a frequent routine for us, and we learned a lot from each other. Those encounters were extremely enjoyable, but never, in my view, as fantastic as that first experience. Illness took her away some years later, but the memories persist…

I was 6 years old. A classmate and I walked home from the bus stop every afternoon, and one day he was excited to tell me about catching his parents having sex. Knowing nothing of female anatomy, he just assumed that dad was sticking it in mommy’s butt. We were both latch-key kids, and our parents weren’t expected home for a couple of hours. So I invited him over to my house, and we went to my bedroom and got naked. Both of us were pre-pubescent, of course, but when the undies came down we were both rock hard. We soon figured out that we needed something to make things slippery. We thought about shampoo, peanut butter, snot, and a few other disgusting ideas before settling on spit. We both took turns penetrating each other. I think I went first, and once I was “in” I just lie there on his back, and I remember him saying that I had to move up and down because that’s what his dad did to his mom. I remember liking the warmth and the tightness when I was on top, but I must not have thought too much about being on the bottom because I cannot remember it well. I do remember having my first dry orgasm that day and being very afraid that something had “broken” inside me and that I might have to go to the hospital.

Starting when I was eight years old and continuing until I was nearly thirteen, two older cousins molested me regularly. That was incredibly unpleasant and often hurt a great deal, so I have always been haunted by those experiences. But that first time in first grade was great and I only wish I had understood what it meant in terms of my sexuality sooner. My life would have probably been a lot different if I had only accepted that from an early age I was always gay.

Think I mentioned this in another topic but I was 13 the first time I had a cock in my ass. I had already been inserting various handles and objects into my ass so when my friend entered me it was a little uncomfortable at first but not too bad. It got easier ant felt better after several thrusts. I imagine if he wasn't on the small side it probably would have hurt more at first

Great topic, remember it like it was yesterday.

It was only the 3rd time I had sex, I was 16. They guy was my tennis instructor of 25, a great guy with lots of experience. We had had vaginal sex the week before and it was great, I was a large frame girl even at 16, I was 6'1 @ 160 lbs with a large frame. He used lots of lube (Vaseline) back in the day so even vaginal penetration was easy. Background: I had been using enemas for menstrual cramps and constipation since I was 14 and had discussed this with my instructor. On the day of my first anal experience my cycle had just started, my bf suggested we do anal sex since I had taken an enema earlier that day. He took his time and got me very hot with an anal massage first with one finger then two. He had me lay on my left side with my butt sticking out. With lots of lube in my anus he slid in slowly but all the way. To me it felt better than my first two times having vaginal sex. He had an average size penis, the encounter lasted about 10 minutes. It felt really good but I did not have an orgasm. I'd say I had my first real anal orgasm about a month or so later, while taking me from behind he would reach around and rub my clit - that was it - I was off. I had sex with him a few times a week for a couple of years, more than 50% of the sex was anal.

Receiving, it was wayyyyyy too rough. Too fast. Wasn't stimulating at all.

Age 35; second time (same boyfriend )was a marked improvement but still not the greatest.

My first was really bad I was penetrated by 4 of 5 classmates when I was 17 they followed me home and we wound up in woods they took turns shoving themselves into me and only stopped because I was bleeding. I was so embarrassed and couldn't tell anyone and had to face them the next day in school. I now sometimes fantasize about that happening again. I was so scared. When I came out as gay I was about 20 and met someone who was so gentle and it hurt but was such a wonderful experience. I like it very much and wish it happened more often.

1st time, hideous; It wasn't exactly consensual and I was underage. Degrading, painful are just a few adjectives.

As with other kinks I have taken back control of these activities and to me anal sex is now intimate, enjoyable and something I happily partake in now.

I do remember my first time and it was great... I was young... a pre-teen and my neighbor friend and I had already jerked off together... I literally begged him to fuck me when we were in his house one day and no one was around. He said he had no lube and I convinced him to get the butter and he fucked me good .... he had a big dick too which was nice. then his older sister came home and interrupted us before he could cum... we didnt get to try that again... I think he got spooked.

I have never had it. It is my hope that my current gf, soon to be wife, will assist me in solving this issue. Both giving and receiving.

My first time was when I was 21 and traveling in Europe. I met an older American guy in Barcelona and he was the first guy to fuck me. I knew when we went back to his room he was a top so I expected it and wanted it so bad. He was an experienced guy and I loved it and spent a week with him before moving on.

First off, while I like a finger back there or the right toy I really dislike anal sex. Once in a great while I'll let my husband try but it really isn't my thing. My first time wasn't really consensual and I think that experience massively turned me off from it.

I was very curious about about anal sex as I am very a anally erotic person. Naturally I had some concerns about discomfort and also about doing it safely. My husband was very patient and actually trained me to enable me to have successful anal sex by purchasing a kit containing various size butt plugs that over a about 3 weeks I was able to comfortably accept the largest size which was about the size of my husband's maleness when his maleness was on full "military" alert! lol. I am a clean freak about things in the back door area so always a couple of enemas were the order of the day a couple hours prior to training sessions. My husband was very patient with me and very gentle when I felt ready for him to actually enter me through the back door Lots of lube was used for training. He had participated in all training sessions and enema clean outs (he got a fair share of them too!!). On the agreed to night with the kids at the grandparents for an overnight visit, we got dressed up and went out for a light dinner at our favorite restaurant and hurried home like two excited teenagers. We hurriedly undressed one another and with me laying on my tummy, he spread my cheeks applying lots of lube to both of us and very slowly pressed Mr. Pokey against my rosebud which yielded very slowly to his advance until he gently slipped into me and pushed slowly high up my behind. OMG...what a feeling of pleasure. He then began to slowly rotate his hips and frankly was so "close" to his release by this time , he quickly released about 10,000 or more hot little fishies high up into my behind that I could swear that I could feel swimming inside of me urgently seeking the "promised land" which of course was right new door! Sorry this is so long when I could simply have said "It was awesome!!!" Denie

I really didn’t think about it much before I was 16, I had a BF then who would slide his finger into my ass sometimes when we had sex. He was always trying to convince me to let him “put it in”, I finally agreed to let him put just the tip in and he flipped me over and it took a bit for him to get it in as I was having second thoughts; it hurt so much I thought I was gonna pass out or something. He was able to put the tip in and out several times before he came all over my back, butt and legs.

The second time wasn’t consensual so no it wasn’t better than my first experience.

I found my partners were anal or not.

I love giving oral and always when my partner was really wet I would lube my finger in her wetness. Most of the time I would be allowed entrance. Many a time with a finger(s) in both orifices she would have a giant orgasm.

But that didn't necessarily mean anal sex. What meant anal sex was while having vaginal intercourse I was requested to penetrate anally.

In every case anal intercourse was accompanied with either manual or vibrator stimulation.

On many an occasion a soft toy was either inserted either vaginally or anally for DP... 🌹

I gave anal for the first time when i was 25 and received for the first time when i was 35. i enjoyed them both!

The first time I was 72. I was enjoying using dildoes, vibrators and prostate stimulators. Decided I wanted to try the real thing! Totally enjoyed the experience! Now actively seeking more!!

With another cd, she wasn't a big girl in anyway, but my god she fucked my brains out in every position for close to an hour. I've never seen such stamina, it was incredible.

Something I was interested in trying since later teens. There were always dildos and strap ons but i wanted to try the real thing. When I remarried my wife encouraged me to realize my dream. She helped me fine a guy on AOL. Yeah, it was a long time ago. I was in my 40s. We met for coffee and set a date. We met in a motel near Newark International. We all got naked and played together then he fucked me. I don't remember pain but I liked my ass being fucked and remember how deep and hard he went when he came. It was a great 1st time.

Never experienced it, but interested. Taking it, that is. Gave it to a woman when I was about 21. Never gave it to a man, yet!

We were kids making camps in the bracken - sometimes we played doctors and patients - I liked to be the patient. I lay on my front while the doctor put a pencil in my ass and rolled it between his hands - lovely sensation. I have been anally erotic ever since.

@ccm93

The second time wasn’t consensual so no it wasn’t better than my first experience.

… too bad

When I got into a relationship with an older man 56 when I was 22 and he collared me and it was part of the ceremony

I was around 10 or so. I started with a finger then the end of a hairbrush bled a little and got scared so I waited till I was like 15 to try it again and used a small cucumber it was painful but amazing I didn't get my first real cock until I was 49

Been a long time looking for a boyfriend I would like to have sex if feels really good and I'm a bottom.