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!

Rules of the road

I love an affair on a business trip, where the usual rules are suspended and anything goes. My sexy friend Cheryl and I were talking about this, and here's what she told me about one of her adventures:

"I was teamed with a guy and girl who I have worked with before. After a sales blitz all of the teams got together for cocktails. It got late and there were four of us left at this hotel bar. The guy was fucking stunning. He was rather new and I had never worked with him. The other two woman I have known for years as customers. We party when I am in town but not too heavy. Drinks. Dinner. Bed. Alone.

"Both of these ladies are married and I have never known them to stay out this late. I'm in my 40s. Lisa and Deb are mid-30s and Brett is a pup: 26, I'd say; maybe 30, but I doubt it. I could sense (smell?) that my lady customers were hot for Brett. And he knew how to play. The girls are nice looking, with nice 30+-year-old bodies. In fact, about 2 years ago I made out with Lisa after a few cocktails...another story...

"Anyway, I could tell we were all horny and the three of us wanted Brett. He may or may not have wanted any of us but he knew how to play. I said to myself 'fuck this.' This boy is going to pay. So, I threw down the gauntlet. 'Girls, let's see how savvy this boy is. Brett, you wanna play a little game?' He was all for it; the girls, knowing me, were a little nervous. 'Here is my game. Brett, you get one minute to drink in each one of us. Look at us. Smell our perfume. Smell our hair. Get to know us. You cannot touch. One minute spent on each of us. At the end of three minutes we are going into the ladies and taking off our underwear. If you can match even one of our panties to the right owner you will get a reward.'

" 'A reward?' he says. 'A reward???' the girls say. 'Relax. If he wins, I promise I will give the reward if either of you don't want to cheat on hubby....' For some reason they all bought into it.

"We go into the restroom. It was way late, so it was just us. We are giggling like kids. 'Are we really going to do this?' Deb asks. 'Yes we are,' I say. Then I turned to Lisa and said, 'I really, really want to smell hot. Kiss me. Make me cream myself.' Deb's jaw dropped. Lisa cracked up, but came over and stuck out her tongue and brushed my lips. I opened my mouth just a bit and let her tongue dart in. Just that quickly I could feel myself cream. I just love that feeling. Deb was just watching with her mouth open and so Lisa turned and kissed her too. Oh, my god!

"We were all sort of giddy and we did take off our undies. Thank goodness we are all proper women and wear panties! We got Brett and we went to the hotel lobby and found a secluded set of couches. There we presented him with our undies. He was delirious. He sniffed and smelled and I think even took a taste of one pair. He got one right. Lisa. 'Ahhh...my reward. What do I get?' I reached into my purse and gave him a Macy's gift card that I have had for a few months and never used.

"Oh my. The disappointment in his face. 'I'm teasing. You guessed Lisa so it's up to Lisa.' She was like, ummmm, well I am really not able to do much. So I said, 'well what can you do and be comfortable?'

" 'I'd love to make out a bit and I can rub your cock through your pants? Is that good?' Lisa said. Brett would have taken anything. I said, 'well that's pretty good. Maybe I can throw in a little more. How about going to my room?' Deb said she had to leave, so Lisa and I walked her to her car leaving Brett to steam. When Deb left, Lisa said, 'Oh my god, what am I going to do?' I told her to just make out with him and I'll give him a handjob. 'You're in the clear with hubby.' Sooo...

"Up to the room. Lisa starts kissing Brett. I undo his belt and take out his rather average but very, very hard cock and start stroking him. I swear, he came in like 45 seconds. Poor boy. I was going to suck him, too. Ah well. He was a little sheepish and said he had to go. He left.

"I told Lisa I would walk her to her car. She said that would be great. But first, she said, would I mind giving her a little help. 'With what?' I said. 'After that I really need to come and I know it ain't happening at home unless I masturbate and I don't want to do it alone. So...would you either make me come or at least undress and let me masturbate?'

" 'What would you prefer?' I asked. 'I'd love to have you make me come, but I don't think I could take you licking me. Can you do it with your hand?'

" 'Ummm....well, I tell you what. Why not masturbate for a bit and then let me help you finish?' We undressed, pulled back the bedspread and laid down kissing. Lisa started to play with herself frantically. I moved down and sucked her boob. Very nice nipples. She gased, 'Oh, god, I am going to come. Please, please do it for me.' My hand replaced hers. I dipped a finger into her cunt and slowly moved it up between her lips. Her clit was twicthing. She was soooo close. I licked a finger and put it under her ass and slid it up her ass crack. 'Oh my god, oh don't, oh god, oh my god'

"Too late. I slipped my finger into her butt and then stroked her clit with my index and middle finger. I felt her ass tighten and then the throb of the clit. I have made women come quite a few times in my life, but I don't recall the sense of pure joy and relief I saw in her face. Honestly, she shook for a good few minutes. And kept moaning little moans: 'ohhh, ohhh god...ohh my, oh that felt so fucking good...I have nver come like that...oh...Brett's tongue...oh...'

"Enough. Now it was my turn. I got up on my knees and sat on her stomach and then walked my tight bod up to her mouth. She would not do it. I will say this though, she knows how to kiss and play with pussy. Her tongue is incredible and her fingers know just what to do. I had a very satisfying orgasm and we fell asleep. About 5 am she got up and left. She called about 15 minutes later. 'Thanks. I really did need that. And, umm, I think I would like you to go down on me sometime..."

Are you as hot for Cheryl as I am?

The tasty world of high school 'relief sessions'

I've caused way too much trouble already, so I'm going to tell you a wonderfully cock-hardening/panty dampening tale from my friend Cheryl.

She dated guys in high school, but some fun came from her "gal pals." As she told me, "Guys are kind of stupid at that age and while I loved their muscles, the way they smelled and even their dopey guy stuff, I really was kind of afraid of their roughness and wasn't one to put out. I liked making out and letting them play with my boobs and I would toss a hand-job their way on occasion, but I never fucked them.

"I learned to rely on myself for easing the tension, if you will. I should say myself and two other girls I had known for years. For the most part the three of us hung out together all of the time. Sometimes it would just be the three of us on a Friday night, or it would be the three of us and a bunch of other girls, but it would always be the three of us...

"As you can imagine, familiarity either breeds contempt or a special closeness. We were close...So close that we shared everything. At one point that began to included what we called "relief therapy". If one of us had been on a date or did some "heavy petting" with a boy and needed a little relief but didn't want to do it ourselves, we could rely on each other.

"It usually was quite simple and consisted of either two of us or all three of us meeting at one of our houses. The relief sessions would begin by the person in need (funny...at the beginning of the session there was only one in need...by the end almost always all three of us got some relief) lying down and covering her eyes. Then you would feel someone removing your clothes and then, most generally, hands playing.

"Playing with your hair, your boobs, your stomach, feet, knees and finally playing with your pussy. And, we got quite good at jilling each other off. I still mastubate on occasion thinking of relief sessions. When we were freshman in college we all came home (we went to different schools) at Thanksgiving and agreed on a relief session. I got to go first and was quite surprised not only to have a kiss laid upon my lips (we never, ever kissed like that) but to actually being licked down there....oh my god.

"I had a very pleasant orgasm. And when I sat up I was like 'I, I, I...can't...,' and they both started giggling. 'Nice, huh?' Ummm...I would say so....

"Our last relief session together was probably in 1985-86. Two of us still stay in contact and live millions and millions of miles apart in both distance and in the direction of our lives. But, we still love each other. We met a few years back for our 20th reunion. We never mentioned our sessions, but about a week later I got an email from her and she said that she had wanted to talk about them, but just lost her nevve. She has not once done anything with another woman and really missed that special touch. We agreed to have a 'session' one day when we could get time to meet somewhere. Hasn't happened yet. It may never. But I like thinking about it.

"I will always enjoy the touch and feel of a woman and will never go long without the sweetness of a kiss or the absolute joy only one woman can give to another. Men? Can't do with out them. Women? Can't have an incredible, stupendous, outstanding, un-describable, intense, orgasm without them. Oh, sure, I have had good sex with men. But never had head like that from a woman."

And all I have to add is: I think I am going to swoon!