We agreed to meet at Dolores Park.  I’d learned my lesson long before that people who post ads on Craig’s List are often flakes so I always prepare for no one to show up.  I often take Isis to Dolores Park anyway, so if she didn’t show the day wouldn’t be wasted.

I had responded to her ad in the Casual Encounters w4w section.  Her ad wasn’t long, but it was more interesting than the usual, “I have a boyfriend and want to explore my naughty bi side.”  She had a bottle of absinthe and wanted to share it, and possibly herself, with an interesting woman.

We met in the park and sat and chit-chatted while Isis ran around a bit.  We discovered we had attended two different schools at the same time, but had no clue the other existed until the meeting in the park.

She was hot.  Very much my type of woman: a bit dykey, thin but curvy, and with small, perky breasts.  She was obviously not wearing a bra that day in the park, and I loved seeing her nipples push up against the fabric of her halter top.

I lost my cell phone in the park that day.  I suspected some people who were sitting near us stole it so I confronted them.  They denied it, but not until after telling me, in Spanish, to suck their collective dick.  I was so proud that I knew that one phrase and told them so.  Despite my lame behavior she seemed to want to spend more time with me.

I walked back to my house with Isis while Ms. Absinthe drove to her place, conveniently located in Noe Valley, to get the bottle of absinthe she had advertised having.  Once at my house she poured us drinks.  Not only did we taste the delicious absinthe, but she gave me a lesson on why it’s drunk diluted with water, and what the clouding is called.  She was preparing to be the bartender at a prohibition-themed party and wanted to be able to do more than just pour so she was practicing on me.  She did an excellent job.

We got along quite well.  She kissed me.  I’m always surprised when a woman whom I find attractive is attracted to me.  It doesn’t come from a self-loathing place; I am simply not my type.

She had great breasts.  They were nice and little and soft with nipples that got hard in the most delicious way when I bit down on them.  I hadn’t done more than kiss a woman in over ten years and was worried about my performance.  She later assured me by email, “Actually, I’d say I had a rather nice fucking.  Thank you very much.”  So fucking cool.

We quickly began to spend all of our free time together.  As neither of us was employed, we had a lot of free time.  Also because neither of us was employed, we didn’t have any damn money to do anything much more than hang out at my house.

We watched “the L Word” together.  Cliché I know, but I watched the show anyway, not just because I was seeing a woman.

We cooked at my place several times a week.  She made me corned beef and cabbage, which I’d only had once before.  Together we made and froze what seemed like a gross of won tons.  We made a yummy gnocchi with meat sauce, all from scratch.  I made my beef short ribs and mashed potatoes for her brother when he was in town.  She took me to restaurants I’d never been before and was impressed when I liked chicken feet and all the pig parts.

Things became intense very quickly.  We had great sex.

Just a few weeks after we met, we took a trip to Orr Hot Springs.  Ms. Absinthe had a Mini Cooper and loved to drive.  She liked that I had no problem with her taking the windy roads of Mendocino County at a nice clip.  I thought it was sexy that she was a good driver.  Orr was really nice.  We stayed overnight in the yurt just outside the front gate.  There were private rooms with huge claw-foot tubs big enough for two.  The water was hot and mineral-rich.  From the main pool of the “resort” we could see daffodils in bloom all over the surrounding hillsides.

Before too long our relationship went from fun and light to Ms. Absinthe asking  “where we stand.”  I made it clear that I didn’t want a “real” relationship, and that there was NO way I was going to be monogamous, but that I really did dig her scene.

We continued to have hot, hot sex.  We took a couple of trips to Good Vibrations on Valencia to get supplies, including lube and gloves.  It had never occurred to me to have sex with gloves before Ms. Absinthe introduced the idea.  I now buy boxes of medical-grade nitrile gloves for use during sexy times.  They’re a whole lot of fun all lubed up.  Great for fisting.

Ms. Absinthe was the first person who fisted me.  And I was the first person she fisted.  They were intensely intimate experiences for both of us.  She wrote me a poem on the subject:

On your couch

I kiss your mouth
and slowly breathe you in.
Your teeth, lightly gnash against my skin.
You begin to tweak and twist my nipples until I gasp,
I find my way between your legs
grinding my hand onto your wet pussy
back and forth, up and down,
finally pressing in.
You bite harder, I push deeper.
My clenched fist
inside your cunt;
I can barely move.
You’re so fucking tight, and so fucking hot.
Your walls clamp down around my hand
I just want to punch right through.
Thrusting your pelvis higher; you’re telling me to fuck you harder, to fuck you faster,
to fuck you forever.
Your body undulating to your own rhythm,
I’m entranced by the sway of your hips, lulling me closer.
I can’t keep my eyes off your twisting shape.
Now I’m on top of you.
But I can’t get any deeper,
I can only fuck you desperately, fuck you faster.

Our sex life was not a problem. One of our trips to Good Vibrations resulted in the purchase of Tristan Taormino‘s  The Ultimate Guide to Anal Sex for Women 2nd Edition.  We read it together and utilized some of its many tips when we incorporated anal play into our sex.

As our sex life together was developing we discussed strap-ons.  Neither of us had any experience using a harness, but we were willing to try.  Further discussions resulted in us agreeing that she would pick out the harness that she felt most comfortable using, and I would pick out the big, thick cock with which I wanted her to fuck me.

We went to Good Vibrations … and chickened out.  The Good Vibrations on Valencia had roughly 15 feet of wall space devoted to various harnesses and the implements that can be put in them.  Here we were, two well-educated, adult, sex-positive women who really wanted to expand their sex lives, but even we were intimidated.

Because while Good Vibrations has an open, non-judgmental environment it does not have any privacy.  Ms. Absinthe would have had to try on any harnesses out there on the store floor; and I would have had to pick out a number of dildos for her to try on with each harness out there in the open.  We were not ashamed in any way of what we wanted to do, but not being ashamed does not equal wanting everyone in a store knowing what we’re planning on doing in private.

Nonetheless, our sex continued to evolve, and continued to be good.  Our relationship, however, wasn’t so good.

Ms. Absinthe kept wanting to talk about our feelings and what we wanted from each other.  I just wanted to hang out and have fun.  I was still trying to figure out what it meant to be a divorced woman in her mid-30s.  I was getting used to being single, but I wasn’t yet divorced.  Neither I nor the Ex had even bothered to file for divorce yet, though it was clear we would not be trying to reconcile.

Only Ms. Absinthe didn’t believe that the Ex and I weren’t trying to reunite.  Ms. Absinthe and the Ex met, and got along pretty well.  I think because she saw that he and I were civil (we had animals to co-parent after all) that that meant we should get back together.  She didn’t seem to believe me when I assured her there was no way he and I would ever get back together even if we were friendly with each other.

The words I said to Ms. Absinthe didn’t seem to get through to her.  She appeared to think I was being dishonest, or just wasn’t admitting everything to her.  However, I was nothing if not brutally honest.  Despite my assertions that I don’t make pronouncements lightly, she just didn’t seem to believe me when I said the Ex and I would never get together again and that I had no interest in being in a monogamous relationship.

To that end, I continued to fuck men when I could, and it was during this time I had the threesome with Mr. Zip and the 21-year-old booze hound.  I told Ms. Absinthe exactly what I was planning on doing that night and suggested she stay at her own place.  She opted to stay at my place, and was still up at 5am when I got home.  That was definitely troublesome.

Things were going bad, and fast.  She was at my place all the time, and I value my alone time, more than the average person, I think.  I began doing what I did when the Ex and I were living together and I needed to be alone in a loft apartment–I used ear buds and listened to podcasts whether home alone or not.  Pretty rude behavior when one has a house guest, but being at my house constantly was also rather rude of Ms. Absinthe.

She became needy, and our sex went from hot to me turning her down as often as I could get away with without generating a discussion.  I was a fucking bitch to her most of the time.  I really am shitty at breaking up when I know the relationship should end.  So I do the chickenshit move of cheating (on the Ex) or in some other way making the prospect of being with me miserable.  No, I am not proud of myself.

The last time we saw each other Ms. Absinthe picked up toothpaste she had left at my place after a trip to Costco.  She texted me a birthday wish soon thereafter.  My emails requesting friendship went unanswered.

I swear.  True story.

This is what I was thinking of when I masturbated the other day.  I was able to come despite suffering from a cold and severe back pain.

kani

I want my calves bound to my thighs so my legs are wide open.  I want to be on the edge of a bed or a table so a man with a nice huge cock can stand up and pound my pussy and my ass at his whim.  Or it could be a woman with a big dildo strapped into her harness; I’ve not had enough experience with women and strap-ons for this to be something that pops into my head unbidden, but the image is certainly not unwelcome.

I want his cock to slide into my ass.  Slow and easy, working its way up to fast and hard.  Then he should slow down again, as he slips his fingers into my pussy.  He’ll be using lots of lube so everything will slither into me without effort.

His cock will be in my ass as he slips one, then two, then three fingers into my pussy.  He’ll be slowly pushing his rod into and out of my ass while at the same time his fingers reach up and massage that special spot inside my cunt.

Then, I want his whole hand inside me and his cock in my ass; to be completely and utterly full.  And I can’t do a thing because I’m tied up all pretty.

I swear.  True (fantasy) story.

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.

getimage

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.