Sandra

In 1999 I started seeing Sandra, who advertised her wares in the San Francisco Weekly classifieds. Her ad read “Betty Grable legs, Bettie Page Ass. You know what you want. So come get it.”. And so I did. She charged $180 for an hour session, which included Greek.

Yes, that’s right, horndogs. For $180, this woman would let me fuck her in the ASS!

Anyway, Sandra was a funky artist-type in her mid-30s with a pretty, pixie face, bright eyes, short hair that she dyed a different color every time I saw her, small breasts, a slim little bod and a decent ass and legs. She kinda resembled actress Leslie Hope (shown here) whom fans of the show “24” will recall played the wife of Kiefer Sutherland’s character. In fact, whenever I see Leslie Hope on TV, I get a stiffy.


Sandra lived in a studio apartment just off San Francisco’s Union Square; the place was always littered with clothes and art supplies and smelled of incense. Sandra was a good conversationalist and we would always chat about various subjects: art, politics, the news, her childhood in Maine, music, and all things counterculture. Sometimes we would smoke a little weed before getting busy; sometimes I’d bring a bottle of wine, too.

But you don’t want to hear about all that, do you? You want to hear about the GOOD stuff. Well, for starters, Sandra and I would make out. Yes, finally I’d found an escort that would kiss. And I mean delicious, wide-open-mouth, lots-of-tongue French kissing. It was great. Her mouth felt great. Once she even wore lipgloss with glitter in it, which quickly smeared all over my mouth and body and turned me on even more. No, I wasn’t into wearing makeup; I just felt like I was about to have sex with some uninhibited punker chick, which I was. Lying naked on her futon bed, my cock rapidly stiffening up and brushing her hairy pussy, we would swap spit for a long time. I could’ve made out with her all day and be satisfied.

No, that’s not true. Sandra would then kiss her way down my body to my cock, which she would take in her mouth and begin servicing. Her blowjobs were, overall, just average in quality, but Sandra had one move where she would hold my cock in her mouth for minutes at a time, not moving, but all the while making a humming sound with her mouth and vibrating my cock. It felt good, but really all it did was make me impatient and start pumping my hips, anxious to get her lips sliding up and down my rod again.

I’d also try to eat her pussy, as always through Saran Wrap, but either I wasn’t doing something right or she didn’t care for it, because she always just laid there without moving or making a sound.

Whatever. I needed to fuck, anyway. And fortunately Sandra would always assume the position enthusiastically, spreading her legs wide or bending right over so I could put my dick in her. And I wish I could say her tunnel was nice and tight, but it wasn’t. It was roomy and loose, a probable testament to how many cocks she’d taken in there over time. I would have to work pretty hard to get some good friction, after which I’d either shoot off inside her or pull out and dump a load of spunk on her little tits.

But what about her ASS, you ask?

Sandra was not the first woman I’d screwed in the seat, but she was definitely the most unique I’d ever had back there. I’d stroke myself to a good hard-on and slip on a well-lubed condom, then insert myself into her back door with a surgeon’s precision. She’d grunt and squirm while I negotiated the opening. Once she even scolded me because I was making her uncomfortable, so in return I shoved my cock in hard and fast, pretending I was a barbarian warrior savagely violating a captured maiden. I’d grunt and bellow my pleasure…and she’d begin barking like a dog.

I am NOT fucking kidding! The chick would bark like a terrier, wiggling her ass all around while I skewered it. The first time it happened I was speechless. The second time I just slapped her ass and said, “That’s it, baby! Bark for me!” And I’d go on plowing her Hershey Highway until money shot time came and I sprayed all over her sweet cheeks.

Afterward, we’d lie there and do the usual…kiss and chat until I got dressed and left with the scent of incense and her body odor in my nostrils and my dick limp with satisfaction.

I would go on to bone Sandra for the next 3 years until she inexplicably dropped out of sight. I always figured she’d retired from the biz…until I learned through reliable sources that she’d had some sort of mental breakdown and wound up living in a San Francisco mental institution for a year. After that she’d gone back to Maine to try and reconnect with her family, a journey that had many twists and turns before she finally settled into a normal life in a small town in Massachusetts. She also stopped being an escort, choosing to make an honest living instead of taking cocks up her ass.

I’m happy for Sandra, and am glad she found her happy ending. She always gave them to me! :)