How many people have you introduced to the joys of anal sex?

[cadman7777]

I've done it with two women....one was when I was young and she initiated it....I enjoyed it of course....the other was like 38 years later while having an affair with a woman.....she only wanted anal, it was definitely her favorite

 

[HMILF]

I have introduced several young men myself, including a lovely young man who has Down Syndrome.

 

[MaturemanAJ]

Didn't introduce either one but had anal sex with two women. One honestly liked it more than vaginal sex.
Not sure why we didn't date more then we did. I don't think I was ready fir just one woman and she was more Tomboyish. She loved sex though.
Anal sex has never been a high priority for me.

 

[lifeis2short2b]

Funny ! I've been introduced to assholes, but never anal sex.

 

[lokiboy]

Three: First was a college gf. She was already very sexual, but I was a super 'nice guy' back then, so I was also the first guy she trusted to try that with. She didn't bring it up, but as soon as I did she was ok with it as long as I was gentle (i.e. used lube, prepped her, went slow, etc.). Even with prep, entry was hard for her. She told me I didn't have to stop, though. So I just kept saying sweet but dirty things to reassure her, all while slow sliding further into her. How great it felt, how sexy I she was, how hot it was to see her ass stretching around my cock, etc. After a few minutes I was all the way in her ass and held still for a little bit while we kissed and I played with her tits and pussy (she was on her side with legs scissored) and she got used to my size. After a little bit, I told her I was going to start fucking her. To which she nodded, with her eyes closed and holding my hand. I withdrew almost all the way, slowly. Then I trust back into her, slowly. Her ass felt wonderfully tight, but was now accepting my cock much easier. I kept up my other attentions on her - tits, pussy, kissing, dirty talk, all while gradually speeding up the pace of my fucking. She never said it hurt, or made any sounds of pain then whole time. Just a lot of (good) moans, mmm's, ahhh's, and the occasional soft 'yeah...'. When I told her I was close to cum, she told me to cum in her (she loved it when I came in her pussy, so I'm sure wanted to feel this). I sped up even more, she moaned louder, and I came deep in her ass. We laid there for a minute and kissed while I reiterated all the reassuring/dirty things I said to her earlier. I asked her how she liked it, and she said not much at first, but was glad she let me keep going. She said she didn't orgasm, but probably would have if she didn't start off so tense. A couple weeks later we were having regular sex and I complimented how nice her ass looked. She said (trying to be sultry) "is that what you want... to fuck my ass?". I asked her if she wanted me to, and she nodded. I told her to tell me, and she said softly "...fuck my ass". I said "tell me again, baby". Taking the hint, she said in a very clear, and hot, voice "fuck my ass!". So I guess she really did like the first time.

Second was a girl I was messing around with while I was in the army. Now this was not a good/healthy relationship. She wasn't someone I was allowed to be messing around with, and she wasn't a totally stable person (very needy, starved for affection). I, still being a very nice guy despite the army's influence, probably seemed like her dream guy. Unfortunately, this made her even more needy. Now I want to point out that I was never mean to her or lied about anything. I just held my ground that this was not going to be a long-term relationship (which we both said at the start of it). Now she was a good person overall, and didn't deserve a lot of the backstory that helped her get the way she was. But after messing around a few times, she was looking to me to be the man in her life that fixed everything. That was entirely unrealistic. Not only was it impossible, but she had no reason to believe I was able (or had plans) to try and do that. She knew that very well at the begin, and head numerous, clear reminders along the way. But it didn't stop her from trying. So after spending countless hours tending to her emotional needs, I was pretty much drained.

As to the sex, it started off normal for hooking up. We'd make out, got undressed, oral, then sex, both happy for the night, etc. The sex wasn't anything special, her blowjobs were ok (I mean it's still a blowjob lol), and she wasn't very tight (but it's still sex lol). But she seemed satisfied after the first couple of sessions, and I was for the most part. I learn the first couple sessions that she didn't mind sucking dick, but was not going to try to deepthroat, did not want me to cum in her mouth, and didn't want to suck my dick after I'd been in her pussy. Also, she'd never done, and wasn't interested in trying, anal. OK, more than happy to respect a girl's bounties. But after a few weeks of the emotional draining I mentioned, the sex was pretty much the only 'happy' time (for me) that we spent together. So I started trying to make it better for myself. I guess I figured she had to know she was not respecting my boundaries outside of the bedroom and was getting what she wanted, so I was going to try the same in the bedroom. I was never rude or demanding, I just acted like I didn't know any of her preferences. Well, it worked. It went from having her to suck me hard for round two, to having her suck my cock in-between positions, to telling her I wanted her to keep sucking when I cum. She didn't object to any of it, even started doing those things with enthusiasm. I guess she was doing that 'keep your man happy' thing, and started enjoying it along the way. A short while after that shift, I would regularly fuck her missionary style, and bring my cock up for her to suck a little every few minutes. Eventually cumming in her mouth and having her swallow. My new favorite thing to do lol.

While the sex part got better, the rest still sucked. One night, after a long string of nights of being emotionally drained and manipulated, we started having sex. No matter how much of a wreck she appeared to at the time, she still wanted me to stay and have sex. That night, my head was not in it, but managed to get my body to comply for a while. Not much kissing/touching, I was just kinda sliding in and out of her while she was laying on her side (in an effort to make her pussy feel a little tighter). Then I just pulled out because of how bad/sad the experience was right then. She was still very horny and frustrated, and probably knew why I stopped. She made a kind of sighed and whimpered at the same time, and just softly said "please...". Since she wasn't that tight and I wasn't fully erect since my head wasn't in it (young or not), I knew it was probably just going to end up with me half-heartly thrusting in her for a while and still not cumming (it'd happened before under similar circumstances), I decided to try something different. I told her "I'll only put it back in if I can put it wherever I wanted". She of course knew what I meant, and nodded an OK. She was very wet, so I didn't ask if she had some lube. Just swipe a bunch from her pussy and spread it around her asshole. I wasn't rough, but I wasn't slow about sliding a finger and then two into her to get her ready. I have decent size hands and figured from the ease at which I was able to slide my fingers in her, she could take my cock. With a lot of spit and more lube from her pussy, I pulled her cheeks open with one hand and used my other to guide my cock to her asshole. There was resistance, of course, but I told her to relax and she seemed to do something that allowed me to get the head in. She jolted a little bit and said 'hmmmmm.." at medium volume. As hard as it was to get the head in, I was annoyed that she almost dislodged me from her ass with that jolt. So I positioned my knees a little closer to her hips, leaned down and said "I just have to get it all the way in, ok". To which, she nodded again with her eyes closed. Without straitening up, I held on to her hip and steadily thrust forward. The lube did the trick, and I slide almost to the hilt on that second thrust. It was much faster than I anticipated, and I'm sure than she did. She didn't scream, but gave a rather loud "ah! hmmm...". I totally would have stopped if she wanted me to. But when I asked if she was ok she said "Oh! mmm, yeah... I love it in my ass!" I don't know if she actually did, or she was just trying to act like it to make me happy. But she was an adult, was now fully aware of what it felt like to have a cock slide into her ass, and had just given me encouragement to continue. So now I was going to fuck her ass. I started somewhat slow, but that was more for me to enjoy the feeling of her asshole stretching and sliding around my cock. But I wouldn't really call this a gentle assfuck. She never told me to stop, and never made a noise louder than the first surprised yelp. She mostly just looked like she was concentrating. I last a lot longer than I normally would in a girl's ass, but she took it like a champ. I came in her, we got cleaned up, I asked if she was ok, she said yes, I expressed my pleasure at the experience, and went to sleep. I asked again the next morning if she was ok, and she smiled and confirmed that she was. She then blew me in the shower and then stood up, smiled, turned around, bent over, and willing spread her cheeks apart for me to fuck her ass again. I, of course, happily did.

Third girl, coincidentally, also took place in the shower. She agreed to try it and I spent a lot of time getting her used to the feeling on fingers and being stretched, and I technically got my cock in ass without too much trouble before suggesting that we go continue in the shower. That was a great idea because she wasn't worried about anything after that and just went with how good it felt, and how good I told her it made me feel. I even accidentally bumped her head against the wall while I was thrusting into her. She didn't say anything and just braced herself better and let me keep going lol. We had messed around earlier, so I lasted a while in her ass, and she seemed to love it. Lots of (good) ow's and ah's. When I realized I'd been fucking her ass for quite a while for her first time I asked her if she wanted me to stop and we can get out and do other stuff. I was still thrusting in her when I asked that, and she just said "hhhha... you're about to make me cum". So yeah, we finished up in the shower that night

 

[MuscularOiledSlave]

More than a few, lol

 

[OneEyedSteve]

None. I'd done it with a couple of partners and never seen the fuss, until I met my second wife. She loves anal, and now so do I. her orgasms through anal are completely different than vaginal ones.

 

[storypost603]

one my now wife back when she was my girlfriend. She did not want to have sex before marriage so anal sex it was. I cant tell you how many times we did it but I was loving it as I got to but my nut inside her. Then years later she pegged me when I asked her to do it.

 

[Live4themoments]

I know of 1 for sure that was an anal virgin, but total i would guess maybe 4 or 5 other women I've had anal sex with. Not really a topic of discussion. The 1 who never tried it before, we were seeing each other for several months One time while performing oral on her, she was incredibly wet and dripping. I started to play with her asshole with my finger, just lightly rubbing the area. Her body momentarily stopped moving and I took it as a signal to push forward. I maybe got past my fingernail when she said wait, what are you doing? I have never had anyone play with my ass before. I stopped, looked up at her, and mumbled something about it might feel good to her. After some words she agreed to give it a try, but go slow and stop when she said stop. I did go slow, she never said stop or ouch, and soon finger was all the way in. Combination of oral and just 1 finger gave her a powerful orgasm. It was soon after that time when I fully became her first. From that point on we used to joke that I created a monster, sometimes she needed that more than regular sex. We started to use toys so she could experience being dp.

 

[SCRob95060]

He had done it with women before so I didn’t exactly introduce him to it but he hadn’t done it with a guy before