Chicago

This was my dream this morning. As with most of my steamy dreams, it started in Chicago, in a posh hotel on Michigan Ave. This one started in the lounge. We all began a game of pool – the players were Sam, Scott, me and perhaps a fourth faceless player (maybe Bill) with other faceless spectators. By this time I was hot – tight pants, tight, sweatery low-cut top with a y-necklace (the kind that pointed the way home). In my mind I’ve designed the perfect tattoo to go over my left breast – a spritely fairy poised in mid-flight with a come-hither look and out-stretched arm with beckoning fingers. The tattoo would not necessarily be visible, but perhaps the beckoning finger would peek out during an especially low dip toward the pool table. During this dream, I was no amateur pool player – I was good. Not an ace, but I won most of my games and took most of the money off of the table. Through out the night I would sip on Cosmopolitans, sure to keep track of my senses, all the while sensing the men’s arousal at my look, my peek-a-boo tattoo and my playing ability. I of course had an agenda – I needed the touch and feel of new flesh, to be held by a good-smelling man and to be loved well.

Sam, though aroused, was his usual less-than-charming self. I’m never sure why I have a crush on him – he’s paunchy, distant, short, he over-gels his hair. But he’s funny, and we nearly had sex at the last conference. I still regret not giving into that, and truthfully that near-brush with infidelity was what started this whole quest to find extra-marital coitus in the first place. So, maybe he’s just the sentimental choice. I was flirty with him – backing my ass nearly to his face if he were seated behind my shot, dipping especially low if he were seated in front of my shot. We had mild sexual banter, and I love discussing men that I find attractive – he gets so jealous. Truthfully though, Scott is a more physically attractive man. However, he’s further up the food chain, and even though I’ve lost a lot of weight and look really good tonight, I’m still intimidated by him. Still, he’s playful and a little tipsy, though always a gentleman. How adorable.

So, we’re playing through the night, and it’s getting pretty late and the money is piling pretty high up on the table. We started with quarters, and now there’s a hundred dollars on the table and the last shot is mine. Sam’s on the other team, jeering at me – “She’s had too many Cosmo’s, she can’t make the shot”. What he didn’t realize was that I was only finishing my second Cosmo and that I was in complete control. His jeering pissed me off though, and I decided to have a little fun with him. I adjusted my top so that it fit squarely on my shoulders, causing the neckline to go to its lowest point, exposing the nasty little beckoning finger. I said, “Sam, you know I have a brand-new tattoo, you wanna see?” Sam, having had 6 or 7 Pepsi and Jack’s, slurred “Oh yeah”. I delicately moved my top and bra to the left, stopping just above the areola and revealing the entire luscious tart. Sam, Scott, and Bill stood there; gape jawed, unable to utter a single word. We had all been a little flirty and tipsy all night, now the mood was downright sexual. On top of that, Sam had a visible hard on. I put down my pool stick and walked over to Scott, whispering in his ear, “Don’t look now, but Sam’s getting excited”. Scott’s blue eyes were sparkling, “Bad girl”. I merely shrugged, took the last sip from my Cosmo, provocatively sucked the juice and alcohol out of the lemon wedge, looked Sam in the eye, picked up my pool stick, and, without looking at the ball, sank the shot. Sam got up and declared that he had an early flight and stalked off to his hotel room, and Bill followed suit. I assumed both spilled some sad sea that night.

Scott, who’d been my playing partner and was now $50 richer, looked and me and said, “That was really cruel, Casey”, “Yes, but it was effective”. “One more game?” “OK, but this time, no money on the table”. Scott stacked the balls and broke them cleanly. As none of them went in, I picked up my stick to start sinking the solids, my favorites. Softly, Scott came up behind me, as though to offer instruction. “You see” he said in his understated Southern drawl, “it’s all in the form”, and he molded his body to mine while “helping” me strike the ball. Aha. So he was paying attention. “Really? I heard it was all in the wrist.” And I in turn stayed between him and the table, rubbing up against his body and caressing his arms while he hit a few. “This is all very interesting, Scott. Perhaps we can continue these lessons up in your hotel room.” “Why Casey, that sounds like an excellent idea.”

We rode up the elevator in silence, making out in the far corner. The elevator stopped at my floor, even though I hadn’t pressed that button. Surreally, Sam walked onto the elevator, head hanging. He hadn’t even noticed us yet. Scott and I froze up a bit and kept absolutely quiet. The elevator stopped again at Sam’s floor and he quietly got off. Just as the doors began to close, he looked up. Shock registered by the time the doors finally came together. Scott and I turned to each other and laughed so hard that we nearly peed on ourselves. Busted! Poor Sam.

Thankfully we were able to make it up to his hotel room without siting any other company folk. Scott kept his hand on my lower back and guided me to the bed. We took off our shoes and lay down across the bed, kissing and caressing each other at the same time tenderly and hungrily. He smells like good soap and he has such good hands. First, we were just entwined, kissing passionately, molding our bodies to one another. Then he gently began to remove my clothes – first my shirt, which he followed by kissing the tops of my breasts and the divot at the base of my neck. Then he removed my bra and gently suckled my nipples – I could feel the moisture increasing down below and against my hip I could feel him getting harder. This was going to be so good. As he removed my pants and panties, he nestled his face in my pubic hair and then dipped his tongue between my labia. Oh, how I love a man who will go down on me. The sweet gentleness of licking and sucking was more than I could stand. The full out licking, and yes – he found the clit. Licking and blowing, God, he was killing me. This was wonderful and warm and intense. The evil of conference sex / cheating sex was so good that I was getting dizzy. God bless this man. He licked his fingers and while causing sweet fireworks down below, he sent electric shocks upward with gentle twists and flicks of my nipples. I was coming quickly and good – I held onto his head and gave a small whimper while a warm shock wave went through my body. Then it got too intense and I had to push his mouth away – “Stop, stop, stop, stop.” The waves kept going through my body – I was speechless for a full minute. Heavy sigh. I hadn’t had an orgasm like this since my first experience with oral sex all those years ago. “Casey, are you alright?” “Mmmmmm.” “That seemed awful quick” “That’s how I like it, quick and mind-blowingly intense. Shit… wait… I’m still coming.” I to pause again for my brain to remember who I was. This man needed to be rewarded for his good behavior. “That felt so good that I’m go to give you anything that you want.” I said breathlessly. “I mean anything. I’m pretty good at everything, so if there’s something you haven’t tried, just tell me and you’ve got it.”

This got Scott’s attention because, even though he is a good deal older than I am, there are a few certain things in bed that his wife would never have anything to do with. Hmmm… Nah. I could see his uncertainty. “Scott, I can see it in your eyes. There’s something you want to ask for but you’re hesitating. Just ask. I won’t turn you down and I won’t think that you’re ridiculous. Please, you just gave me an orgasm that I’ll remember for a long time. I’d like to be similarly memor
able.” “OK. Um, I’ve alw
ays loved a woman’s backside. It’s very sexy, but I’ve never had the opportunity to… you know…” “Have anal sex?” “Yeah. And I’d really like to.” “I think you’ll like it, Scott. Here’s what we’ll do. First, we need KY jelly, which I have. (I’m such a girl scout) You’ll need to help me relax by first lubricating two of your fingers and stretching me out”. He was getting very excited by the whole process, but being the cool cat that he is, didn’t fumble, over squirt the KY or anything. He even had well-manicured fingers. I’m always a little tight at first, but somehow the pain is a turn-on, and I explained this to him. After I’d been thoroughly stretched, I led Scott to the over-stuffed chair. I removed all of his clothing, rubbed the KY between my hands and then rubbed it on his (rather nice-sized) erection. I bent over the arm of the chair with my derriere and cute dragonfly tattoo straight up in the air. “Scott, you’re going to start with small thrusts and once you feel yourself inside, you can get a rhythm going”. This part is always the most difficult for men (especially kind men) because it is so much tighter and it does cause me some initial pain, but I reminded him that I liked the pain and I told him to push through because it turned me on. This was all the encouragement that he needed. Very quickly Scott was able to find his rhythm in that tight, tight space. “Scott, reach down around and feel me up front, do you feel how wet I am – I love this. I’m dripping because of you.” “Oh God. Why do you like it so much?” ” I don’t know, I don’t come, my body just likes giving and receiving pleasure, that’s all. Do you want an extra surprise?” “Sure” I pulled out from my purse a compact vibrator. This actually does nothing for me, but when I insert it fully into my vagina, it gives an extra thrill to the man in back. Scott got quiet and concentrated on the new sensations of anal sex with a vibrator high ball. I could feel his body go stiff with orgasm, and he grabbed me up from the chair into a full standing position, removed the vibrator and rubbed me down beautifully. I even got a bonus orgasm-ette out of this one.

Still stuck together and laughing, we hobbled over to the bathroom and showered, slowly separating and cleaning off all bodily fluids and lubricants. He washed my hair and I disinfected his newly baptized penis. After that we licked at each other again, not for orgasm, just for closeness and fun, then we fell into bed, holding each other. There we were, entwined on the hotel bed at one o’clock in the morning and his phone started ringing. Who could be calling at this hour, interrupting our dreamy fog? Scott answered, and the look on his face held annoyance and amusement at the same time. He mouthed “Sam” and I took the phone from him. “Why are you calling here, Sam?” “Was he good, Casey? Was he your good conference fuck buddy, Casey?” “As a matter of fact, we did have a nice time, Sam. You sound really pitiful. Have you continued to drink?” “No, I’m just still drunk from earlier this evening, so there. Why did you go with him Casey? Why didn’t you wait for me? I went to your hotel room” “Because, Sam, I can’t read your mind and I’m not the type to wait around for a maybe. Boy do you feel sorry for yourself. Well, I tell you what. It has always been my dream to be held by two men at the same time. Not fucked by two men at the same time, just held by two men.” I mouthed “OK?” to Scott, and he nodded his acquiescence. “So, if you want, come up to room 4505, I’ll suck on your dick a little while so that you don’t feel left out, and we’ll all sleep together with me in the middle. OK?” Dial tone. “He hung up! Ass. Let’s go to sleep.” We turned out the lights, snuggled into each other and started to drift off to sleep when we heard a knock at the door.

Sam stood there looking tortured – a strange combination of drunk, turned on, and embarrassed. He wanted me. Even though I’d just been with Scott, he wanted me to touch and kiss and hold him. Mostly he wanted me to suck his dick as promised, but there he was, just the same. I opened the door the rest of the way, letting him pass through. By this time Scott had taken a seat on the very chair we’d christened not half an hour ago, kind of a half-bemused spectator. Sam stood at the foot of the bed, too sheepish to make any overt moves or even remove any of his clothing. My heart softened for him a little – poor Sam. He does have a crush on me; he’s just too gruff to admit it. I’ll make it easy on him. I removed my towel, taunting him again with the fairy and revealing the lovely dragonfly on my derriere. The breath caught in his throat as he tentatively reached out his hand to trace the outline of the dragonfly. I turned around again and took off all of his clothing in a rather dispassionate way. There he was – naked as the day he was born, looking kind of cherubic with his cute gut and downcast glance. I put my arms around him and started kissing him full on the mouth, around the ear lobes and down his neck. I continued down his chest, stopping to kiss and gently bite at his nipples, letting my tongue drag down his belly, into his navel and through the black, curly patch of pubic hair. I could feel Sam’s whole body stiffen as I neared his erect penis. I drew back and looked Sam in the eyes. “Sam, sweetie, you need to relax. Lay back on the bed. I won’t hurt you, I promise.” With that, he laid back on the bed, his body stiff as a board (mind you, Scott is sitting in the corner, smiling like a Cheshire cat at Sam’s discomfort). I pulled the covers over us and laid my body over Sam’s, hugging him, warming his body with mine. After a while I turned my body south and began to make love to him with my mouth and with my hands. I was very gentle – kissing and licking along the shaft, playing with his funny ball sac, swirling my tongue around the tip and frenelum. He was in ecstasy, moaning and saying my name. I took his erection full into my mouth and sucked luxuriously on it while running my hands up and down his thighs. This time when his body went stiff, I knew it was out of sheer pleasure. Licking my lips and swallowing the evidence of his orgasm, I asked, “All better now?” “Yes, definitely” “OK, well I am tired and I want to sleep”. Sam got dressed and spooned me from behind and Scott joined us. I spooned Scott from behind, and there we lay for the night, bodies intertwined and sated, sleep sound and deep.

This of course is just a dream. I badly want to make love to someone other than my husband (don’t get the wrong idea, the man is good in bed and taught me everything I know.). The men I mentioned above seem safe to me because they are not strangers; they are decent and honorable men. I am actually a decent and honorable woman and have been struggling for quite some time with these feelings of adultery. I just know that right now, given the right circumstance, I will go through with it. I’m worried about the ending. For instance, in the rather badly written story above, what happens when they all wake up in the morning? Would it be better for the Casey of the dreams to get up before the morning and leave? What about when they get back to the office? Sam works several hundred miles away and he and Casey can limit their contact, but Scott and Casey see each other every day. They don’t necessarily work closely together on everything, but they wouldn’t be able to avoid seeing each other 4-5 times a week. I don’t want to go out and sleep with a stranger – I could be hurt or killed. The thing is, there are several men in the office that would be decent enough candidates for a fling, maybe. What a terrible thing to occupy one’s mind with. I’m trying to hold out until my therapist’s visit on the 29th. Only 11 days and counting…

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No Responses to “Chicago”

  1. mrpantyhose says:

    You can go through with it very easily. Just have a 3some with your hubby first with another woman, and then tell him you want to fuck another guy. If necessary, let him go fuck some other chick. But to earn his trust, you must give him a 3some first. It’s that simple. Thats the positon my wife and I are in.

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  2. bottleneck says:

    great story ! realistic and still arousing. conference sex seems to release all sorts of inhibitions.

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