Anatomy of a pickup rim job

I was catching up with sexy Cheryl, and sure enough, she had a new adventure she was willing to share:

"Monday night I was out with guy. Dinner. Cocktails. Chat. Two Margaritas and I was happy. Guy is decent. Cute. First date thingy, "although we went to a baseball game once as friends.

"Anywho, I ordered a glass of Port after dinner to sustain my buzz. He looks at me and says 'what would you like to do now?' I hate that fucking question. Especially with that leer some guys have. This guy had it. He didn't want anything more from me but a nice fuck. Screw him.

"So, I looked at him and said, 'The only thing I want to do is to have my ass licked. I want my ass worshipped. I want to have you lick my feet all the way up to my asshole and then ream me until I tell you to stop. Then, when I am satisfied, you will go home and I will take a bath and masturbate. How does that sound to you?'

"I thought he was going to faint. I was hoping it was from shock and disgust rather than shock and wanting to take me up on it. He looks at me and says, 'hmmm, well, umm...that might be nice, but it will have to be some other time.' 'Oh, OK,' I said.

"He dropped me at home. Now he has a great story to tell...

"Later, after sitting at home for an hour, I realized I really would like to have my ass worshipped a bit. I really didn't want to try to troll for someone so I took a bth and played with myself and my ass. No good. Not what I wanted. I got up and dried off. Got a vibe and tickled my ass. No good. I needed tongue.

"So I pulled up a skirt. Put on some heels. Nice tight tee, braless, with a cute jacket and went trolling. I knew where to go. I walked in to my fave place, I saw Jeff. I was pretty sure he'd be there on a Monday. His wife has a book club. 'Jeff, listen, I need a little something.'

" 'Want me to guess or are you going to tell me in sordid detail?' he said. 'Guess,' I replied.

" 'Hmmm....take of your jacket. ahh...braless. What about panties?'

" 'None.'

" 'Hmmm...did you have a date?'

" 'Yep.'

" 'OK, I know what you like but I know you change it up a bit so I am going to guess you want to play glory hole. (Oh my goodness...great game).

" 'Not quite Jeff. Here's a hint: Mrs. Jeff doesn't let you near there.'

" 'Ahhh....yes ma'am. I do believe I am your man.' I giggled 'I know you are the man, that's why I'm here.' 'Where to, Cheryl?''My place as soon as you can get there.'

"He followed me. I opened the door. I walked a few feet in and Jeff followed. I stopped. The door closed. I could feel my skirt being lifted. Jeff is not a small guy. Very handsome. Rough hands. Big fingers. His hands were on my butt cheeks and he spread my ass. My skirt must have been over his head...a funny look in my minds eye.

"Anyway he spread my butt, wet a finger and teased my asshole. What a feeling. He stood up with his hand under my skirt and his finger dangerously close to penetrating my ass. He pushed me toward my couch and bent me over the arm. Then he really went to work with his tongue. It felt so incredible. He reached around to play with my clit, but I told him no. Jeff doesn't have to be told twice. He always does want I want. He must have rimmed me for 20 minutes. I had enough. I needed to cum so badly. I told him to lay on the floor. I squatted over his face and played with my pussy until I came. Then a scooted down and let him lick me. Absolute delight.

"I asked if I could do him any favors. 'Not tonight, babe. Susan will be home soon and after book club she always wants a tumble. This was a good work up for that.

"I know Susan, and she knows that Jeff does favors for me. She hates giving head and she is dead set against back door play so she let's me and Jeff dabble around to satisfy each of our base needs. She likes to watch me give him head on occasion and once she actually masturbated while I was doing Jeff -- that was a pretty good thrill.

"I am such a tramp. And, I rather like it."

I do, too!

Losing my (other) virginity

When I was in my twenties, many men tried to fuck me in the ass. This usually happened in the heat of a passionate, headboard-banging doggie-style fucking. He might start fingering my anus, and then I would feel him pull out and put his cockhead right on the tip of my virgin asshole. I just couldn't do it. I would always say no, then slide forward so he couldn't do it.

Don't get me wrong, I loved it when a more prepared and sophisticated lover would whip out the KY or Astroglide and finger my anus while he licked me or fucked me. He might reach around and do it while I rode him. A couple were dexterous enough have one finger in my anus, another caressing my perineum and a cock inside me. The orgasms were always very intense. My perineum is very sensitive and I love it when a man touches me there. But, still, I was afraid of anal intercourse.

Maybe some of this was my repressed upbringing, but I had always been turned on by breaking those boundaries. I think one element was that I had taken some large cocks, starting with the drunken football player who fucked me at the frat house way back in college. Some of these monsters had made me feel like I was being split open, at first, but usually my pussy relaxed and accommodated them quite nicely, and I loved that filled up feeling. But I knew my anus was not built to expand that way. And I always wanted pleasure, not pain.

I finally crossed the threshold with my future (and later ex) husband. Like the best of my lovers, he was very playful, uninhibited, always horny, inventive and, at just the right times, gentle. He also had what seemed to me a perfect cock: about average length, but with a nicely thick shaft and a beautiful head. It's still the most beautiful cock I've ever seen. At work and at home, I could fantasize about that cock in my ass. We did a lot of buildup, with fingering and rimming. He was on fire from the moment I said, "I want you to fuck me in the ass."

He did his usual long, magical foreplay...lots of kissing, holding, caressing, leg licking...cunnilingus. I had already had one orgasm. I fucked him on top, and he fucked me missionary, then with my legs up under his arms. Finally, I was on my knees, my ass high in the air, my head down on the mattress. He told me how beautiful I looked as he slowly fucked my pussy from behind. He opened the KY and fingered my ass, then slipped in one finger. He finger fucked my anus as he cock-fucked my pussy. He told me what an amazing feeling it was to feel both going in and out. (And he had been very careful to trim his fingernails; hint to you gentlemen). Then he started fucking me with two fingers. It felt good.

Then I felt his cock on my anus and he gently slid it in. It had been well slathered with KY, too. Wow...I could feel it. A very different feeling from a cock in my pussy. I adjusted my pelvis and back, and it felt better. He was all the way in and started to very gently fuck me. I liked it. Liked the fullness, the sense of ultimate surrender. Then it just really started to hurt, and as turned on as I was, I moaned "hurting..." and he pulled out. As I say, he was a gentleman. A hood might have just taken me and fucked me anyway. Would I have liked that or not? Anyway, that was my first time.

About a week later he was fucking me hard from behind, fingering my ass with one KY'd finger -- though he often did this. He was moaning himself, I was screaming...and suddenly I felt his cock slide right into my anus as he came. I couldn't feel him shooting inside me the same way I can when a man comes in my pussy. But it felt very forbidden and nasty and I came again myself. As he often did, he stayed hard and just gently fucked my ass for a few minutes. It felt great. My anal virginity was gone, semen was in my anus and I could hear and feel it sloppily running out as he fucked me.

New horizons were ahead.

Thoughts about that ideal lover

As the poll indicates, most people want a lover with experience...but not too much. I've been discussing this with some of my male and female colleagues.

There is that group that wants a virgin they can teach how to fuck. One male friend actually got that and it seemed to work out well for him. "She kept telling me, 'teach me how...'," he said. So she enthusiastically learned how to suck cock and swallow. She asked him to fuck her in the ass. A number of women friends talked about the older men who taught them the moves -- even if they weren't virgins, they were very inexperienced -- and they were eternally grateful. One man told me how he was initiated by a woman 10 years his senior. Of course the danger is that the virgin won't ultimately like sex. And, she just doesn't have the moves of someone who has had several lovers. This is what I don't get about the "stay a virgin until you're married" thing -- how do you know you will be sexually compatible. My sister and her husband fall into this camp.

The very experienced carry ghosts and baggage with them. I had girlfriends tell me that they loved the skill of their experienced lovers, but they couldn't bear to think about how the men had acquired it. That green-eyed monster of jealousy.

For the ones who get off with their long-time spouse and partner - you're lucky (if you're being honest). I like variety and edge and change. I was a cute young thing as a virgin, but I was probably a lousy lay. (Once a boyfriend told me he got off just by looking at me as he fucked me -- he meant it as a compliment). It was only with multiple lovers, different moves, men (and a couple of women, yay!) who would challenge me and push me out of my comfort zones, that I became who I am. But I don't think I have filled a phone book, not by a long-shot.

How did it get to be June already?

Be patient, my friends. Keeping you safe from evildoers takes more of my time right now. I do look smashing on the witness stand. In the meantime, troll through the archives to keep yourselves...amused.
Linda Sue