What got you interested or started in anal

[Replicant2018]

I had been wanting to fuck this guy for a long time, bit he was kind of playing hard to get. One night we ended up in a bedroom at a party and we started fucking. He was behind me and played with my ass and pretty soon he snapped the condom off and began pushing into my virgin asshole. I was pretty shocked but I wanted him to like me so I went with it and pretty quickly he pumpedy ass full of cum. We went back to the party pretty smug.

Then the next time I was having sex with my then boyfriend, now husband. There was a misunderstanding and I had said "do you want to cum on my ass" and he heard "do you want to cum in my ass." A bit of lotion later he was a pretty happy camper and I had an ass full of cum.

Nice, wish my wife liked an ass fucking.

 

[roc23]

From as far back as I can remember,a girl’s butt always got my attention.
The thought of grabbing her by her hips as tight as I could while I bury my cock drove a lot of my masturbation fantasies.

Every time I was with a girl,rimming was always going to happen. Then rubbing the head of my cock on her asshole was next. But if the girl didn’t suggest anal,then I just backed off.

Finally,early 20’s I met a girl. I was starting to become pretty dominate in the bedroom. This time I sugggested trying anal. She was hesitant but she knew she could trust me.

After lots of foreplay,I put the head of my cock against her asshole. Slowly pushing it in. Once it was buried I grab her hips,and started slowly fucking her. It was so hot watching her head go from side to side. Watching her grab the sheets. I pulled out and came all over her asshole,back and hair. After we were done,she ended up crawling to the bathroom. Her legs were like rubber. She said she was close to blacking out.

Ever since then,anal is always top of my list.

 

[soflabbwlvr]

My story is similar to the one below. I have always been obsessed with the female ass. For as long as I can remember I have loved to stare at women's asses, watch them walk, watch them bend over, watch them dance...anything and everything involving women's butts. When I started having sex, I was constantly grabbing, squeezing, licking, touching, fingering, probing...I like tits, the bigger the better, but my attention was always focused on her butt.

Of course as an ass-obsessed young man it was only a matter of time before I would want to fuck an ass. My girlfriend loved sex as much as I did, and agreed to give it a shot. No luck. We tried numerous times over a 12 month period with no success. We eventually came to the conclusion that she just couldn't do it and gave up trying.

A few years later my housemates and I hosted a party. I met a hot young lady with big brown eyes and huge boobs. We hit it off, and went upstairs to my room to do some coke. A few lines later we were half-dressed and taking turns going down on each other. We fucked until we both came, and then paused to do some more coke. Cum was oozing out of her pussy as she leaned over the mirror. Within minutes I was hard again. I got between her legs, put her ankles on my shoulders, and rubbed my cock against her juicy pussy. I then slid it down to her tight little asshole. Her big eyes got even bigger as I pushed my cock into her ass. She didn't say no, so I continued. After a few thrusts I was buried balls deep into her ass. We fucked for another 10 minutes, then I emptied my second load into her. We got dressed and headed down to the party. On the way she told me not to say anything, since her boyfriend was probably there by now.

I've been hooked on anal ever since.

 

[falkor207]

For me it was the first girlfriend after my divorce. She had just turned 21 and was 12 yes my Jr. We were at her place and during foreplay she asked for it. She had a bottle of lube and basically told me what she wanted. Lube applied and worked her up to 3 fingers then more lube at her entrance and she slathered my cock and the rest is history. We had anal on a handful of occasions before we broke up and she's the only woman I've done it with. I've never rimmed or tongue fucked an asshole. Boo me now, it's not something I crave, but will do if the woman I'm with wants it.

 

[FrankLee99]

For me it was the first girlfriend after my divorce. She had just turned 21 and was 12 yes my Jr. We were at her place and during foreplay she asked for it. She had a bottle of lube and basically told me what she wanted. Lube applied and worked her up to 3 fingers then more lube at her entrance and she slathered my cock and the rest is history. We had anal on a handful of occasions before we broke up and she's the only woman I've done it with. I've never rimmed or tongue fucked an asshole. Boo me now, it's not something I crave, but will do if the woman I'm with wants it.

I love it when a woman asks for it, or even winks and begs for anal
That is such a turn on

 

[falkor207]

I love it when a woman asks for it, or even winks and begs for anal
That is such a turn on

Being with a woman who knows what she wants and is uninhibited at least as much as myself is a HUGE turn on!! Communication before the clothes go flying or ripped off is key. Learning about likes, dislikes, and out of bounds activities makes sex so incredibly fun and you're not worried about can I try this and will she/he like it. This is also a great way to get the blood flowing and discuss areas you'd like to explore together or for the other. Yes, there are the random hot sex hookups based on list, maybe not so much recently with the pandemic.

 

[Up4fun&69]

As a lifelong nudist, I've always been open about my body. Obviously, I can't go into the younger years here, but I was dating (for the second go round), a former college girlfriend who was equally open and adventurous. She loved to fuck in front of a tilting mirror so she could see my cock and her pussy in action...a huge turn on for her. One night in the heat of the moment with both of us so close, my cock slipped out and I hurriedly slipped it back in...but into her ass by accident. Her eyes widened and she became more vocal until we both came rather quickly. As I slipped out of her, she said, "Um, you know that wasn't my pussy." As I started to apologize, she hushed me and said she loved it. It became part of our regular play, especially when she could see me enter her ass in the mirror. That just caused her to go wild.

Before then, most girlfriends were up front about it being "dirty," "taboo," and not of any interest before even trying to go there. Kind of a turn off since anything backdoor was off limits and I had to suppress my desires to finger, rim, etc. Once I married, my now ex-wife, over time came to love me rimming her and fingering her ass when I fingered her pussy. But full anal didn't do much for her. Still trying to find that open, adventurous and willing partner in my life.

 

[Kirksameritze02]

Out of the blue while watching tv my wife asked if l wanted to do her anally,l jumped of the sofa she stripped got on the floor with her butt high in the air l stood over her and because l am tall l pushed my dick down and entered her it was my first experience of anal she was very tight and l enjoyed it.......after she said she was broke in by another guy the week before.

 

[johnnyampleed]

Lost my cherry to a slightly older woman who was a nympho and wanted me to fuck her ass, too. She loved it and got a tremendous orgasm from it.

Next, waited a few years before a MILF wanted anal and she loved it, too. After a few months, she pegged me.

After sex stopped in the marriage, I edged for hours and started to introduce toys to my ass to prolong the edging. Orgasms have been outstanding.

 

[GenieT]

My first lover who was a much older guy introduced me to it one afternoon while his wife and daughter (my friend) were out. He did it several more times over the months. I remember the first time feeling very stretched (he had an impressive girth). And he finished in me as we had fucked bare. I was sore after and it made the walk home in the village a bit awkward.

 

[Smoothshavendad]

My first lover who was a much older guy introduced me to it one afternoon while his wife and daughter (my friend) were out. He did it several more times over the months. I remember the first time feeling very stretched (he had an impressive girth). And he finished in me as we had fucked bare. I was sore after and it made the walk home in the village a bit awkward.

We older daddies do that.

 

[shmily]

I had a great introduction to sex, he was very patient teaching me, steep by step overtime. When we finally got to anal i was hooked.

 

[FrankLee99]

Out of the blue while watching tv my wife asked if l wanted to do her anally,l jumped of the sofa she stripped got on the floor with her butt high in the air l stood over her and because l am tall l pushed my dick down and entered her it was my first experience of anal she was very tight and l enjoyed it.......after she said she was broke in by another guy the week before.

this is a hot hot story, so many questions, did you know your wife was seeing other guys?

 

[BiWifeMyrtleBeach]

In my younger years I was curious about anal and though I had been with several men prior to my husband, I had never ventured into allowing a man back there. There was not a defining moment but I resolved at some point to retain my anal virginity until marriage. I happily learned that not only was my husband nicely equipped (8") but was well trained in sexually pleasing a woman, especially by an older woman he had been with prior to me. While we had sex prior to our vows over the course of a year, I told him he could have my ass on our wedding night.

On that night, he not only ate but fucked me to several orgasms before the moment of anal pleasure arrived. He was extremely patient , first rimming me for quite sometime. The best way I can describe it was my ass, became..well..HORNY. Then he took time lubing me inserting one, than two fingers , slowly at first then increasing pace as he knelt by my up turned ass. Soon I was practically begging him to do it faster. I did not know, at least it was this way for me, anal attention could be so damn pleasureful.

Aftersome time, he positioned himself. As you can imagine, it took a bit of time and getting used to 8" slowly invading my ass but before long, he was in me balls deep. He began a slow but steady pace and told me to let him know if it was too much..I whimpered, "no..keep going". Little by little his pace became quicker. Soon i was shoving back at him, begging him to fuck my ass harder.

He could not hold out and soon, was spewing his cum deep inside me. Feeling his cock flex sent me over the edge and we orgasmed mutually. We collapsed in a heap, me feeling happily I was completely his.

While we have been involved in swinging for years, to this day, my ass is his private property.

 

[Hitchiker69]

For me it started when I topped gay guys. They seemed to like it a lot, so after a while I tried receiving. My first time was with a guy who seduced me, got me a little drunk, and very relaxed after a massage. I was ready for anything, and naked in bed with him on top. It seemed so natural, and didn't hurt at all.
I've craved getting fucked ever since. And I still enjoy topping men.

 

[ornyguy32]

For me it started when I topped gay guys. They seemed to like it a lot, so after a while I tried receiving. My first time was with a guy who seduced me, got me a little drunk, and very relaxed after a massage. I was ready for anything, and naked in bed with him on top. It seemed so natural, and didn't hurt at all.
I've craved getting fucked ever since. And I still enjoy topping men.

That's hot

 

[comegently]

I am trans feminine and non surgery.
My ass is the nearest thing I have to a vagina.
I have given anal to an ex girlfriend who asked me to, but I'm not that keen on being on that side of the experience.
I have been given strapon, which I liked a lot.
I think about what it would be like to take a real cock but I don't do it in the real world because I'm faithful to my partner.
I use butt plugs, including an electric thrusting model and a remote controllable Lovense Hush.
I sometimes play out my thoughts by posting stories here and by using photography with me as the model.
I find being penetrated very erotic and it can make me multiple orgasm.
I do not find the idea of two male-presenting people having sex at all erotic. In my mind, I am female when being penetrated.

 

[belleanderson]

I thought I'd never try anal. And my man wasn't really asking for it. But when we started making porn together, we thought it would be fun to try. And it actually felt really good. Sometimes his big cock feels a little too much... but most of the time it gives me a really good full feeling. I've noticed it is easier to take his cock all the way inside my ass without it going too deep versus my pussy.

 

[FGB]

Howdy all

47m here
I love anal sex, and knew from early on I did
I loved experimenting

I'd love to hear what got you interested or started in anal

Cheers

This beautiful nineteen year old brunette rang my doorbell at four o:clock one afternoon and when I answered it she was all over me.

Backed me up into my living room kissing me and rubbing my Dick and asked me to "Tie me up and Fuck My ASS!"

Well!

I had never had the pleasure before because I had not found a willing Woman. She thought because I had taught her a great deal about how to seriously fuck that I would know all about it.

I did...just had never actually done the deed.

Boy Scout training kicked in so I grabbed some eighth inch braided nylon line and pop some helpful slip knots with stops in it.

I took her into the bed room,stripped her down and secure right wrist to right ankle and left wrist to left ankle wit just enough slack to not make it uncomfortable.
By this time her pussy was dripping! She had been drinking and smoking and watching Porn all day and decided that the ass fucking on there was something she wanted to do and SOON. So she went to the guy she trusted the most....Me.

I ate her pussy until she came ...that did not take long. As i was doing that I worked some good Lube in her asshole and loosened it up. May have been why she came so fast and hard. I fucked her until she came again. She was on her back with her legs open and well exposed.
I had warned her that once I had the head in I wasn't going to stop until I shot load into her.
She said that if I stopped she would never fuck me again.

I am only a little above average in length and girth so I knew i wasn't going to hurt her if I started slow.

I popped the head in and added another half an inch or so and stopped until her sphincter muscle settled down from clinching and unflinching my dick.

She was moaning softly and saying "Oh God,Yes!"

I'm not going to lie about I almost came right then! I felt a little jet of cum leave and waited a minute because I knew from that point I fuck for a good while.
I added more lube and started going deeper with each stroke. It wasn't long until I was balls deep in some hot tight ass and she was urging me on.

I am not sure which one of us started cumming first all I know for sure is that I was like a run away locomotive red lining going in and out of her

We were both making noises and cumming her squeezing my Dick and me shooting what had to be rope after rope of hot cum deep into her ass.

I almost passed out.

I managed to get her hands free and we just laid there for awhile her head and most of her upper body on my chest.

I have tried to write what happen those many years ago now but feel I am inadequate to the task.

We lost Lisa back in the mid nineties.

She was a hell of a woman!

Love ya Babe!

 

[FrankLee99]

This beautiful nineteen year old brunette rang my doorbell at four o:clock one afternoon and when I answered it she was all over me.

Backed me up into my living room kissing me and rubbing my Dick and asked me to "Tie me up and Fuck My ASS!"

Well!

I had never had the pleasure before because I had not found a willing Woman. She thought because I had taught her a great deal about how to seriously fuck that I would know all about it.

I did...just had never actually done the deed.

Boy Scout training kicked in so I grabbed some eighth inch braided nylon line and pop some helpful slip knots with stops in it.

I took her into the bed room,stripped her down and secure right wrist to right ankle and left wrist to left ankle wit just enough slack to not make it uncomfortable.
By this time her pussy was dripping! She had been drinking and smoking and watching Porn all day and decided that the ass fucking on there was something she wanted to do and SOON. So she went to the guy she trusted the most....Me.

I ate her pussy until she came ...that did not take long. As i was doing that I worked some good Lube in her asshole and loosened it up. May have been why she came so fast and hard. I fucked her until she came again. She was on her back with her legs open and well exposed.
I had warned her that once I had the head in I wasn't going to stop until I shot load into her.
She said that if I stopped she would never fuck me again.

I am only a little above average in length and girth so I knew i wasn't going to hurt her if I started slow.

I popped the head in and added another half an inch or so and stopped until her sphincter muscle settled down from clinching and unflinching my dick.

She was moaning softly and saying "Oh God,Yes!"

I'm not going to lie about I almost came right then! I felt a little jet of cum leave and waited a minute because I knew from that point I fuck for a good while.
I added more lube and started going deeper with each stroke. It wasn't long until I was balls deep in some hot tight ass and she was urging me on.

I am not sure which one of us started cumming first all I know for sure is that I was like a run away locomotive red lining going in and out of her

We were both making noises and cumming her squeezing my Dick and me shooting what had to be rope after rope of hot cum deep into her ass.

I almost passed out.

I managed to get her hands free and we just laid there for awhile her head and most of her upper body on my chest.

I have tried to write what happen those many years ago now but feel I am inadequate to the task.

We lost Lisa back in the mid nineties.

She was a hell of a woman!

Love ya Babe!

holey moley, what a wild ride
thank you for sharing

 

[jenni_bean]

A boyfriend in college. He was persistent so I finally let him. It hurt the first time but now I enjoy it.

 

[UtilityCurve]

College

My freshman GF had a sophomore bestie who told her anal gave her the most intense orgasms. This conversation was reported back to me within 24 hours for fact-checking.

Since then, I have been convinced that the majority of women expressing a desire for (or at least an interest in trying it) have had--and you'll forgive the metaphor--had the seed planted (in their minds!) by another woman.

On Reddit, one skeptical female put it this way: "I just don't see what's in it for me." (Except when spoken in jest, I find the idea that anyone plans his or her sex based on personal enrichment unsettling at best, disgusting at worst. Sex is the apotheosis of the principle that the greatest joy is found when giving.) As a man, my answer(s) to that would rightly be viewed as biased, of course, even if scrupulously accurate. Another woman is instantly credible.

 

[Asunna]

Mine was a pretty basic reason. I was scared of getting pregnant but still wanted to enjoy being sexual so gave anal a try and actually enjoyed it.

 

[Smoothshavendad]

Mine was a pretty basic reason. I was scared of getting pregnant but still wanted to enjoy being sexual so gave anal a try and actually enjoyed it.

My kind of woman!

 

[KaitlynW1993]

I didn't. My trainer said men will desire it and to be more useful I should be a 3 holed slut.
So I started my anal training.