Anal Origin Stories

[Jacques_Corbin]

I seem to end up with women who either aren't into anal, or just not into anal with me. Never met the women who just love anal sex, not in person anyways. But, I know they exist. What I want to know, is how it all starts.

I want to hear about your first time doing anal. Or, maybe the first time you really enjoyed it. Is doing anal to maintain virginity in a vagina still a thing? I'm also dying to know if any women had their first anal as part of a DP. The last MFM threesome I had, she said she did not like anal, but never had 2 guys at the same time before, and wanted to do everything, because it might never happen again. She absolutely loved it, but was completely spent afterwards.

Anyway, enough of my rambling. Ladies who love anal, how did it start? You are all super heroes, and I want to read your origin stories.

 

[Ingenue844]

My first attempt didn’t go well.
The next time we were prepared with lube and a better position to try it out( doggy). We went slowly.
Anal+Clit stimulation brought about one of the most powerful orgasms I’ve ever had.

 

[Jacques_Corbin]

Thank you for your reply. Was the first time a "in the heat of the moment" thing? Or was it a "what the hell, let's try it" thing? What position did you start with? Is doggy the best position for anal? For the clit stimulation, is it you or him doing the clit stimulation? Which is better? Do you do anal regularly, or special occasions?

Again, thank you. This is so fascinating!

 

[StrongMaster7]

This is a story of a near-miss.

The wife and I were on a cruise and they had a special 'couples shower room' you could rent for an hour. I assume it was meant to be a sex room. It had a shower, hot tub, sauna, lounge chairs and various soaps, lubes, salts, etc. We were feeling pretty romantic, especially me. We messed around and almost immediately my wife jerked me off. This was a huge mistake.

We played around for a while with her getting pretty aroused. I kept hinting at wanting anal sex and, amazingly, she started to give in! This was my dream coming true! All I needed was to get my cock hard. And maybe it was the realization that I might get anal or maybe it was the breakfast mimosas, but I couldn't get hard. Semi-hard was about the best I could do. My wife became super-receptive and told me to 'stick it in any hole I want'!!! OMG!!!

Try as I might, I couldn't get hard enough to get inside her asshole. It was the worst frustration I ever felt. And of course, that was the last time she ever came close to letting me near her ass. So be prepared and learn from my mistake.

 

[Lucy_Lastic]

My first time didn't go well. he was only a year older than me and hadnt done it before but told e he had, no lube, hurt like a bitch, I cried, there was some blood.

After that I refused point blank until a very gentle and undertanding guy persuaded me, was generous with the lube and took it at my pace. Lots of finger and tongue to relax me. I quite liked it.

Its not my favourite activity and the first inch always hurts, but once it's in it's ok, resonably pleasurable but I wouldnt cum from it. I'm not afraid of it any more so I do it if I like the guy, because I like how much guys like it.

 

[womaneater58]

I've only been with one woman who wanted to try it. We tried it once and both enjoyed it but then we broke up soon afterward. I'd like to try it again.

 

[soflabbwlvr]

I know you asked for women's responses, but I have a few experiences that might be of interest.

My first experience with anal was my high school/college girlfriend. Neither of us were virgins when we got together, but we were not terribly experienced, either. Over the 3+ years we were together we tried new things, practiced with each other, and learned a variety of skills. Toward the end of our relationship I became obsessed with anal, and after some discussion she agreed to try it. The first time did not go well. Could not get it inside her. We didn't know anything about lube (didn't need it for fucking), and all it did was made her cry and me frustrated. We tried again a few months later, and same result. We tried a few more times before we broke up, but never succeeded.

A year later I my housemates and I were hosting a house party. We bought some coke and divided it amongst ourselves. That evening a woman I knew from class but with whom I had no interest showed up. She brought a friend with her, and the second we were introduced we sparked. Later in the evening I found the friend getting a beer, and I asked her if she wanted to go up to my room to do some coke. She agreed, and we went upstairs. We did a few lines, started kissing, and in minutes our pants were off and we were taking turns going down on each other. I got between her legs and fucked her, filling her with a load of cum. We paused to do a few more lines, and by the time we finished I was hard again. I got between her legs again, rubbed the head of my cock up and down her cum filled slit, and then pressed my head against her asshole. I paused for a second and looked into her huge brown eyes, but she didn't say anything. So I pushed it in. Much to my surprise, it slid in with very little resistance. I pushed it all the way in and and fucked her until we both came for a second time. When we were finished I pulled out, we got dressed, and she said to me "let me go down first, I don't want my boyfriend to see us together." We never really talked about the fact that I had just fucked her in the ass.

My next experience was several years later. I had kind of a FWB situation with a Jamaican woman who looked and was built like the porn star Ebony Ayes. She worked nights and I worked 9-5, so we had a very hard time hooking up. Just about 1 or maybe 2 times per month for a year and a half. Well, one day it had been around 2- 3 months since we last hooked up, and she called and asked me to stop by on my lunch hour. I got over to her apartment and she told me she was on her period, but she would be happy to suck my cock while I used her vibrator on her. We got naked and were pleasuring each other for a while, but she wanted more. She asked me to fuck her in the ass. I asked her if she was into that (because I sure in the hell was), and she said she had never done it before but was so horny she wanted to try it. I asked her if she had any lube, and she told me to go the bathroom and get a jar of vaseline. I had tried vaseline with the girlfriend I mentioned above, and it never worked. But I figured she as older, so let's give it a try. Well, the vaseline did work, sort of. I got it in, but it was not as smooth as I had hoped. We fucked for a while, I came in her ass, but she never got off. Ended up having to use her vibrator to get her to cum. After that time we never tried anal again.

 

[haventdonethat]

My first anal was with my first wife, her first time also. We had talked about it a few times before actually giving it a try and I had read as much as I could find (way before internet).
Wife was a bit hesitant expecting pain and or discomfort but she really wanted to try it. Everything was slow . . . lots of finger play, lots of lube, lots of talking.
She set the pace and did most of the work, gentle rocking back and forth taking me deeper ever so slowly in doggy position.
She also talked a lot after I was all in . . . about how tight it must be for me, how it must be quite different that her cunt. While she was talking her hand was stroking her clit to a few good orgasms.
I didn’t last as long as I wanted to even though it was my second cum within 10 minutes, it was just too tight and risqué.
Anal became an occasional treat for both of us.

PS: I also enjoyed anal with a few other women but it was far from their first time.

 

[Jacques_Corbin]

My first was during my army days. About 3 years in, I met this exquisite and fierce Puerto Rican woman from Illinois. She was a soldier too, and had the same MOS. Way, way, way out of my league. It was the second time we got together to have sex. She suggested it after discovering she was out of condoms. She excused herself to her bathroom to lube up, and after a few minutes she returned.

We started with her on top. It was so tight, so crazy, so dirty. I didn't know women did that! I got fussed at not to pull her down, or thrust upward. She talked dirty a lot as she lowered herself, and then while grinding on my cock, most of it in Spanish. After a bit, she started riding in earnest, and I almost lost it. She apologized for taking so long, said it had been awhile since the last time she did anal. We did side by side, then she laid on her back with her ankles on my shoulders. I knelt for a bit, then dragged her to the edge of the bed to stand while I fucked her ass. She came hard from that, then wanted to do doggy. It felt so good, the noises she made, and the things she was saying, was just too much. I doubt I lasted 3 minutes. Still, she said I lasted much longer than the last guy who she did anal with.

 

[soflabbwlvr]

It was about 15 years ago while I was divorced for several years and started dating again. I met this woman on a match site and we went on several dates before we started having any serious physical contact.
So, we spent the day at a local lake swimming and hiking and went back to my house for a drink and a light snack.
We made plans to have dinner that night at my place.
Then out of the blue while we were standing next to each other on the deck, she grabbed my hand and thrust it into her pants, down her crotch and proclaimed “see what you do to me?”
All I can remember is saying something to the effect of. “well, we’re going to have to do something about that later”
To my delight, she then said: “when you make love to me tonight, I want you to fuck me in my ass” Honestly, at that point I thought I was lost in a daydream or something.
She left to go home and shower and was back shortly. The whole time she was gone I still couldn’t believe I was that lucky. Anyway, when she returned, we had a few drinks and ended up in bed. I went down in her for quite a while and remember her having several orgasms and then she pushed me away. Shortly thereafter, she was bent over the edge of the bed, one leg up and her hands spreading her cheeks. “Put your cock in my ass” she said.
I lubed myself up and pressed against her. It slid in her ass with no effort at all. Surely she had prepared herself for this. It was warm and soft and felt almost like being in a cunt until she clamped down on me hard. She loosened herself up a bit and I thrusted into her as far as I could. My god it felt good. I didn’t last too much longer after that. I came inside of her for what seemed like a long time and stayed inside of her until I went soft.
Needless to say, we never did get around to having dinner that night. In the end it didn’t work out for us but I will always remember how hot she made me and how her words affected me.

I love a woman who knows what she wants and isn't afraid to let you know

 

[Wonderer67]

I won’t say my ex wife loved anal, but she enjoyed it maybe once a month or so before she lost her sex drive after kids.

She liked doggy style if I hovered over her (made her cum powerfully) but she loved it missionary off the side of the bed. Something about that angle (slightly upward hitting her g spot) gave her insanely intense orgasms.

Most times when came like that her ass would convulse around my cock like nothing I’ve felt before or since. I’d usually cum immediately, and force my cock deep in her ass as I came.

Getting a hard on writing this. Good times!!!

 

[Marielani]

My first anal was a disaster. In college and a long time boyfriend.
was over served as most college kids are on weekends.
he attempted anal on me with little lube. I was willing but
felt like a red hot piece of steel penetrating me. Couldn’t go on.
next boyfriend down the pike tried too. Same results. Hurt like a son of a gun.
so swore off anal pretty much.
fast forward to my marriage.. husband always an ass man. Kissed it, licked it, tounged it.
well one night I gave in.. I said yes try..
it was the most beautiful thing. He took such time and care getting me ready.
land come penetration time it was slow, just the head.. slow.. little more.
I barely felt him. But I trusted him.. still do..
we still enjoy anal.. I have even asked him for it.
have achieved great orgasams during. Enjoy it very very much now.
I think the moral to the story is to be kind and gentle

 

[trevorness]

Nice to hear all the anal stories, since I have had it only a couple of times ever.

 

[the_single_gal_unconfidential]

had it twice - before a fwb guy - developed me.
those first two times, had potential but was uncomfortable in a couple of ways.
I like it in dp - I've had two cocks in twice, and did love it.
through my fwb and I trying things - I found that him in my ass and I manipulate a toy in my pussy is pure ecstasy.
something way down in there gives me huge climaxes when I do that.
and that primal thrill is what I always seek.

 

[ILikeIt]

I saw a gay sex magazine when I was young. I never gave anal sex a thought until I saw those images in the magazine. I was intriqued by the hot pictures of big cocks penetrating those hairy ass. I tried inserting things in my ass when I masturbated. It added some excitement but wasn't all that pleasant. When my wife and I first got married she showed me how she masturbated by putting thick makeup tube inside of her. She pushed it in and out of herself and had a pretty good orgasm. I asked her to use it on me and she rebuffed me harshly. I didn't bring it up again. Some years later she got a colection of toys. I started using her sex toys on my self and learned to like having her dildo up my ass. I didn't do it often but every now and then, when I got horny enough, I fucked myself in the ass and got a very good orgasm. This went on for many years (actually decades). She never knew about it. One night during pretty hot foreplay she told me she wanted to tell me about a fantasy of hers. She said she wanted to watch me have gay sex. I was flabbergast. She continued to tell me what she wanted to see me do. She said she wanted to watch me get fucked in the ass. I told her about how I use her dildo on myself, and she asked me to show her. I got the big one out. I lubed up my ass and after a short time of trying i had it up my ass. She watched me with utter lust in her eyes. She got more and more excited. The dildo was so long that about six inches were inside of me but another six or eight inches were sticking out. She told me to bend over the edge of the bed. I did and she came up behind me shoved the portion of the dildo that protuded from my ass between her legs. She clamped it between her legs and proceeded to fuck my ass good. She fucked me for about ten minutes, I think she had at least three orgasms, then reached around and jacked me off. I shot accross the bed about three feet. After that night I bought her a strap-on and she fucks me on special sex nights.

 

[CockSparrow]

I think my first time anal was with a woman with whom I had worked for a while. She was a terrible flirt. Or should that be: she was a brilliant flirt? Probably the latter. Anyway, later, when we were no longer working together, we still used to catch up for the occasional glass of wine and a chat, and I sometimes ran into her when I was running in the local park and she was walking her dog.

One evening when I ran into her in the park, I invited her to come back to my place for a drink. She accepted without a moment’s hesitation.

Back at my flat, I poured a couple of glasses of wine and then, being a bit sweaty after my run, I excused myself to go and have a quick shower.

I was standing there, under the shower, just about to get out (as I recall), when the bathroom door opened and my guest and her dog arrived. ‘Nice,’ she said. ‘Can we watch?’

‘You already are,’ I pointed out.

‘Oh, yes,’ she said.

Fast forward a few frames and we were in my bed. She was lying on her back. (I seem to recall that she was still wearing her bra, but that was all.) And I was fingering her wonderfully slippery cunt.

‘Are we going to do this?’ I asked.

‘We are,’ she said with a devilish smile. ‘It has taken us a while, but we finally are. However, you need to put a pillow under me.’

She knew best. So I put a pillow under her hips and positioned myself for a missionary position entry. But before I could get through her front door, she reached down, covered her fingers with her cunt juices, and liberally smeared both her arsehole and the head of my stiff cock.

‘In you go,’ she said. And so in I went. And in I went many more times over the next few months, sometimes in the front door, and sometimes in the back door. But then she took a job on the other side of the pool.

It was fun while it lasted.

 

[Oshkosh60]

I had done a bit of self exploration over the years but didn't get too into it. I think most of my thoughts in that direction were fantasies of being pegged by a woman or one using a toy on my backside. My wife was not into even the suggestion of it. Likewise a few other girlfriends once marriage ended. Including in that number was a 74 year old widow. She was a very sensual woman who enjoyed toys and manual manipulation but one night I accidentally went ventured into the forbidden zone. Good things can happen in the darkness. She decided that maybe we should play there after all and I would gently probe with finger and toys bringing her to explosive orgasms. Finally, one night she reciprocated and that was a great night for me as well. Never got to enter her with my penis and our relationship ended, but my gosh, going from "no way" to "OH YESSSSS !!!!!" was great.

 

[vlad22]

my wife is very shy about her ass but in the last few months or so, I started introducing a finger or two playing with her butthole whenever I'm going down on her. Although she hasn't admitted it out loud she seems to respond very positively via noises she makes and how fast she cums when I have 2 fingers massaging her g-spot and a finger playing with her ass. I'd start with plenty licking/sucking all around her pussy by the time my fingers make it to her bum and at that point she is typically too far gone to say anything or protest and just enjoys the ride, which she does seem to really enjoy.

So now I started playing with her ass whenever we take a shower. I'd help soap her up and then move a hand down and put a finger up to two knuckles in there. She'd protest because she doesn't like the idea of anal. I told her that playing with her butt turns me on, but mainly I get turned on because I see how much she gets turned on by it. Isn't that so? and that's the part where she just goes, "maybe" and never says she doesn't like it. And I told her that even though she doesn't want to admit it, my suspicion is that she really likes it, which she also hasn't disagreed with, yet.

I love watching her body respond and cum. My dream is to try anal with her while at the same time having 2 (or 3) fingers massaging her g-spot and having both of her holes filled till she cums. Slow and steady progress so far

 

[LeeKee]

I seem to end up with women who either aren't into anal, or just not into anal with me. Never met the women who just love anal sex, not in person anyways. But, I know they exist. What I want to know, is how it all starts.

I want to hear about your first time doing anal. Or, maybe the first time you really enjoyed it. Is doing anal to maintain virginity in a vagina still a thing? I'm also dying to know if any women had their first anal as part of a DP. The last MFM threesome I had, she said she did not like anal, but never had 2 guys at the same time before, and wanted to do everything, because it might never happen again. She absolutely loved it, but was completely spent afterwards.

Anyway, enough of my rambling. Ladies who love anal, how did it start? You are all super heroes, and I want to read your origin stories.

The first anal was with a woman friend, who wasnt my actual gf at the time, just a friend who secretly was jealous of a girl I was seeing and wanted to fuck me....long ago. We had been going at it hard for an hour and a half, was so amazing. She was on me cowgirl and just stopped. Leaned forward, slid my cock out of her pussy and just started to work it inside of her ass. In said wait dont we need lube, she whispered, "not if I'm careful". And after a short bit I was all inside and she slowly rocked and slid me in and out, slowly and not wildly. She asked if I liked it, I said yes. She ask if ive done it before, I said "this is my first time" when she learned it was my first she made more motion and I was sliding in and out with more travel. We came at the same time. It was so amazing. Weeks later the girl I was seeing and I were having sex and I asked if she liked anal, she said yes. To my surprise, because I was only her 2nd guy ever. She told me had sex with her big boss and his wife when she was a virgin, and his wife only let him do anal, and she loved it. So, what a surprise! She did like anal and we enjoyed a few times (with lots of lube for her) before work spit us up for a long time and we driffed apart. But girls do like anal. Dont lose hope.

 

[EStaccato]

How did I miss this thread?

I prefer anal in almost every conceivable way to vaginal sex. My orgasms are huge, and because my ass is well-trained (and I wear a butt plug often enough), I can take some fairly large toys in a matter of a minute or two. Honestly, it's because vaginal sex is painful for anything but the smallest cock.

My first anal experience was my girlfriend playing with my asshole. A lot. She'd fuck my ass with her fingers a lot. She loved that it made me embarrassed and uncomfortable. And she made me do a lot of things to hers. I remember telling the story to a boyfriend who would one day become my ex husband, and he knew I got off being embarrassed and shamed, and he demanded I take him in my ass. He knew how to warm me up, though, and he used a vibrator to tease me open until I could take him. We used a metric ton of lube, because he knew what he was doing, and after he started fucking me, I must have cum four or five times in a row. My preference has never reverted.

 

[Lucy_Lastic]

How did I miss this thread?

I prefer anal in almost every conceivable way to vaginal sex. My orgasms are huge, and because my ass is well-trained (and I wear a butt plug often enough), I can take some fairly large toys in a matter of a minute or two. Honestly, it's because vaginal sex is painful for anything but the smallest cock.

My first anal experience was my girlfriend playing with my asshole. A lot. She'd fuck my ass with her fingers a lot. She loved that it made me embarrassed and uncomfortable. And she made me do a lot of things to hers. I remember telling the story to a boyfriend who would one day become my ex husband, and he knew I got off being embarrassed and shamed, and he demanded I take him in my ass. He knew how to warm me up, though, and he used a vibrator to tease me open until I could take him. We used a metric ton of lube, because he knew what he was doing, and after he started fucking me, I must have cum four or five times in a row. My preference has never reverted.

Have you ever adressed the problem of why vaginal sex is so painful?

 

[EStaccato]

Have you ever adressed the problem of why vaginal sex is so painful?

It’s a pelvic floor nerve issue, and it’s not common before pregnancy, so yeah, little weird. But I was pretty nervous before I grew up, and I clenched for years. I’ve done PT for it and had great improvements. It’s not painful unless I’m really stretched, so I can finger myself and use small toys with no problem now.

 

[sixfoot4]

I saw a gay sex magazine when I was young. I never gave anal sex a thought until I saw those images in the magazine. I was intriqued by the hot pictures of big cocks penetrating those hairy ass. I tried inserting things in my ass when I masturbated. It added some excitement but wasn't all that pleasant. When my wife and I first got married she showed me how she masturbated by putting thick makeup tube inside of her. She pushed it in and out of herself and had a pretty good orgasm. I asked her to use it on me and she rebuffed me harshly. I didn't bring it up again. Some years later she got a colection of toys. I started using her sex toys on my self and learned to like having her dildo up my ass. I didn't do it often but every now and then, when I got horny enough, I fucked myself in the ass and got a very good orgasm. This went on for many years (actually decades). She never knew about it. One night during pretty hot foreplay she told me she wanted to tell me about a fantasy of hers. She said she wanted to watch me have gay sex. I was flabbergast. She continued to tell me what she wanted to see me do. She said she wanted to watch me get fucked in the ass. I told her about how I use her dildo on myself, and she asked me to show her. I got the big one out. I lubed up my ass and after a short time of trying i had it up my ass. She watched me with utter lust in her eyes. She got more and more excited. The dildo was so long that about six inches were inside of me but another six or eight inches were sticking out. She told me to bend over the edge of the bed. I did and she came up behind me shoved the portion of the dildo that protuded from my ass between her legs. She clamped it between her legs and proceeded to fuck my ass good. She fucked me for about ten minutes, I think she had at least three orgasms, then reached around and jacked me off. I shot accross the bed about three feet. After that night I bought her a strap-on and she fucks me on special sex nights.

Fuck!!!

 

[OtherwisePrint6210]

oh, love the stories....

 

[Wonderer67]

How did I miss this thread?

I prefer anal in almost every conceivable way to vaginal sex. My orgasms are huge, and because my ass is well-trained (and I wear a butt plug often enough), I can take some fairly large toys in a matter of a minute or two. Honestly, it's because vaginal sex is painful for anything but the smallest cock.

My first anal experience was my girlfriend playing with my asshole. A lot. She'd fuck my ass with her fingers a lot. She loved that it made me embarrassed and uncomfortable. And she made me do a lot of things to hers. I remember telling the story to a boyfriend who would one day become my ex husband, and he knew I got off being embarrassed and shamed, and he demanded I take him in my ass. He knew how to warm me up, though, and he used a vibrator to tease me open until I could take him. We used a metric ton of lube, because he knew what he was doing, and after he started fucking me, I must have cum four or five times in a row. My preference has never reverted.

@EStaccato I think you are my favorite lit person! You are amazing!!