I placed an ad on Craig’s List under w4mw Casual Encounters with the headline, “Teach Me How to Fuck Your Guy’s Ass.”  My intent was to find mw couples who were already engaging in pegging so they would have the equipment, and so she could show me, via both demonstration and instruction, how to fuck ass properly.

I wanted a woman to teach me because she assumably had the same problem I feared–not being able to feel the phallus used in the harness.  I did not want to get the equipment myself and fuck some guy’s ass without any lessons for fear that I’d hurt him (any more than he desired–which is NOT to say ass fucking should hurt; it should not).

I got many responses, as per usual with CL.  A LOT of the respondents clearly were instituting the gunshot approach by responding to every listing that had been placed by a woman (or a “woman” bot).  These sex hunters shoot their email buckshot far and wide without concern for their sexy prey.  My ad was very specific, yet I had a number of responses from men who’d never been pegged and who didn’t have partners.  Also, several responses from guys who wanted to fuck my ass.  I dig getting my ass fucked, but that wasn’t going to help me learn how to fuck properly with a strap-on.  Besides, I had been been the anally receptive partner countless times; it was my turn to top, dammit.

Through email exchanges I settled on one couple I could tell was experienced in the fine art of pegging.  S&E live in the next neighborhood, Bernal Heights, so we decided to meet at a local dive bar, the 3300 Club.  They are in their mid-30s and she and I have the same first name, so we already had at least two things in common–names and the desire to fuck her husband in the ass. We chatted over drinks, and then I went to the bathroom.

Always when meeting couples for the first time I go to the bathroom to give them the opportunity to talk about me.  And check out my ass (duh).  I think it’s polite to afford them time to determine whether they’re both attracted to me and whether they want to share their bed with me.  I was hoping to be a guest in S&E’s sex life, so other than my participation, everything was up to them.  We had already established our ground rules via email–E’s cock would not be entering my pussy–but otherwise anything was game provided we all wanted things to go forward.

I returned from the bathroom and S very sweetly told me, “We like you” with a big dumb grin on her face.  So cute!  What a nice ego boost to be told a couple finds me so interesting and sexy and fun that they both want to have their way with me.

Some weeks later I walked to their house for the big event.  We had drinks and played with their dogs (not like that, you sick fucks).  Eventually we went to their bedroom (the dogs were locked away in the garage).  I was very nervous about strapping on and fucking him.  They showed me their toys and S put on the harness to show me it wasn’t intimidating at all.

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S with a cock wasn’t the least bit scary; actually, she was sexy as hell. She strutted around the bedroom showing off her big dick.  I wanted to know how she fucked with it.  Somehow, instead of demonstrating by fucking E’s ass, her cock found its way into my pussy.

It was a new sensation for me–having a woman with smooth skin and soft flesh pounding away at me with her cock.  While she was fucking me from behind, my mouth found its way to E’s prick.  Because of this experience I now know that one of my all-time favorite things is getting my pussy pounded from behind whilst my mouth is full of cock.

One of the great things about being fucked with a dildo is that it’s always hard.  E shot his load–which I happily gobbled down–and was enjoying the after glow, all while S continued banging away at my cunt.  Eventually she tired of working her hips to fuck me.  Then the three of us did various things that three horny people do together until we were all exhausted.

We did not, however, ever get around to me fucking his ass.  We had a great time, and I was definitely not disappointed in any way as I stumbled home, drunk on both drink and sex.

We got together a second time, and once again we got distracted from our main goal when when E’s cock went in my mouth and S’s cock went in my cunt.  I think I’d choose that “position” if I had to fuck just one way for the rest of my life, though I’m glad I don’t have to make such a harrowing choice.

I was beginning to think I was never going to get a chance to fuck man ass.  I lamented my fate to Mr. Zip, a friend with whom I speak about my sexual adventures at least once a week.  Mr. Zip has no interest in getting pegged so he didn’t even volunteer to help me out of my woeful situation.

I was considering placing another CL ad with a similar headline until I got another email from S&E requesting my presence at their place.

I walked there a third time.  S was wearing a floor-length, high-necked night gown that would have been matronly but for the fact that it was constructed of extremely sheer cotton.  She looked so at-ease and sexy in the gown that I was immediately put on sex alert.  Being able see her tits at attention as soon as I walked in the front door made me realize that night would not be like the previous two we had spent together.  I was very much distracted by being able to see S’s body beneath the gown.  S sensed this, I’m sure, because she soon went into the bedroom–removing her nightie on the way.

E and I followed her into the bedroom.  This time I made it clear that I was not going to pass up my opportunity to fuck his ass; that I would be distracted neither by a hard cock in my mouth nor my twat.  S helped me into the harness and assumed the role of Sexy Professor of Ass Fuck.  She was an excellent instructor.

E got on his hands and knees.  S pulled out the lube.  She lubed up her fingers and loosened up his ass as she told me what he he liked.  She talked about him as if he were merely an object, which was very fucking hot.  I watched her lubed fingers slide into and out of his ass.  She assured me his ass was clean and ready to be fucked.  Eventually, I got behind him and slid my lubed cock into his ass VERY slowly.

E made it obvious he was enjoying himself, which I appreciated.  I tentatively slid my cock into his ass as I got used to the feeling and sight of pushing into him.  It felt so fucking hot to slowly slip into his pretty little ass.

And then I wanted to fuck. The harness was well-placed and I just wanted to pound his ass, hard.  Harder.  I grabbed onto his hips and pulled his ass toward me.  I thrusted, the pressure growing each time I jammed my cock into his asshole.  S, and any comments she may have been making, faded into the background because I was fucking.

I was making guttural noises–fuck sounds–as I pounded his ass.  His cock was so hard.  I reached around so I could stroke it but he told S that he couldn’t handle that much stimulation.  Only I could barely understand what was going on so she had to push my hand away.  He pushed back into my cock as I thrust into him.  I grabbed onto his shoulders so I could pull his whole body onto my cock; so I could fuck him even more ferociously.

Every time I checked in with him to make sure he was excited by what was going on he grunted in approval.  I lost track of S and it was just me and my cock and E.  Eventually E turned over–so I could fuck him face-to-face.

With us facing each other I needed to be gentler, but any thrill lost from savagely fucking his ass was made up for by seeing his face–as I continued to thrust into him.  He looked so pretty.  I looked into his eyes and I knew how men must feel when they’re fucking women.  The look of utter surrender and pleasure on his face was wonderful.

I continued to slide the dildo into his ass until I was becoming too distracted by his hard cock.  Looking down at the erection that I was causing was fucking hot.  I was sorry that it was too much for him to let me bob my head down and suck it at that point.  Eventually I began to hear S talking; I hadn’t realized she had been cheering us on all along.

Finally, I pulled out and lie next to him.  We were both panting.  I took the harness off and S took it and the dildo it contained away.  I asked E if he would give me an assessment of how I’d done, but he wasn’t ready just yet; he was still processing.

I think I did a good fucking job (pun intended).

I swear.  True story.

It’s come to my attention that I left y’all hanging.  I’m sorry I didn’t help you blow your collective wad.

I still don’t know E’s assessment of my skills, as I’ve not seen S and E again.  We’ve exchanged emails and they’ve assured me that they dig my scene, but that they’re busy with the boring life stuff.