Here's a story I just need to tell:
I used to get legitimate massages at the Hot Tubs on Van Ness, by this really sweet girl, let's call her "E". She looked a bit like Fiona Apple. Thin, nice tits, dancer physique, and what a walk - with a heartshaped ass and pretty legs - that had that set of dimples above the ass that I so love. Thick Angelina Jolie lips. Late 20's. She was spectacular in therapeutic massage -- the best I ever had. Well, after we became acquainted, she started to vary her massage routine a little... and started to massage my butt, closer and closer to my anus than I expected and I started tensing up. She then said, "Wow, you have a really tense butt. It's a source of a lot of your body tension. I'm going to work deeper here, so try to relax." I tried, and she got awfully close, but draped with a thin cloth. But her New Age rationale made sense. Man, talk about leaving horny!
This happened for a few sessions, and she slowly working directly next to my anus, that usually resulted in an embarrassing hard on, that would be apparent when I flipped over to have my front done... but eventually it would subside. She was nonchalant about it, and we never discussed it, as our friendship grew.
So one evening, she was up on the table on top of me, and massaging my around my butthole, and I'm loving every second of it... and her hands slowly slip under the cloth and start massaging my butthole directly. I'm thinking, man, this New Age thing is pretty interesting... and then, one of her fingers slip in. This is finally over the line, and I realize that she's been teasing me for months, and as her finger slips in... I groan that deep animal sound, and then her other lubricated hand slips under and onto my very erect member. She works me for a couple of minutes as I am nailed, moaning uncontrollably, digging it like beyond words can describe. She slowly pushes me onto my side, fingers inside my ass, and she begins to give me head. It was spectacular. Then she slowly lets my cock out of her mouth and with a lick, she says, "come on, come on, I want you to fuck me... in the ass." "I don't have a condom." "Don't worry, I don't do this... EVER. I just want to be fucked in the ass. RIGHT NOW!"
So I do. I tear off her jeans, lean her over the table, slather her asshole with lotion, and slowly push my (the little head has completely taken over here) cock into her sweet little ass. Then I fuck her absolutely silly. Pounding away, I finally, finally, come inside her ass. Forever. It was incredible. Afterward, we lie on the table, kiss like naughty cousins, and she says, "I've been so tempted to do this with you. Sorry I made you wait so long." She made me swore I wouldn't tell anyone that managed the Hot Tubs about this, because all the massages there are strictly legit. It was the beginning of a marvelous relationship.
Anyway, we end up dating for a couple of years. Man, she was hot. One time, she comes over with a duffle bag, and I say, "What's in there sweetheart?" She pulls out... I kid you not... manacles, spreader bar, blindfold, strap on, paddle. Dumps it on the floor of my living room. She then begs me to do everything she's ever wanted to a guy. She didn't have to twist my arm.
We broke up three years ago today. That cold January day, she asked me if I loved her enough to marry her. I told her the truth, which was no, for some very complex reasons. She moved out of town the very next day, without a forwarding address or phone number.
So babe, wherever you are. Sorry I didn't say yes. I do love you. And I miss you like crazy.