My Private Orgy

"Okay, Bill, we spend twenty minutes, no more. But let's increase the stakes a little. Let's say that every night we're all here, the loser has to fix dinner for the winner. We don't have to eat together but when I win, you have to bring dinner to Amy and me every night we're here. Now, who's afraid?"

I smiled, "you've got a bet, Jean. We'll talk for thirty minutes but we have to set some ground rules. First, you have to answer any questions I might have. No holding back. Deal?" I stuck out my hand.

"Deal," she responded, reaching out to grasp and shake my hand, "but remember, no touching."

I smiled, "no touching for the first thirty minutes, no matter how much you beg me."

This time she laughed, "God, you are confident aren't you?"

I began, "okay, Jean, first I want you to tell me what you want to do in life."

"That's a hard one, Bill. I guess what I want is something new. I was married for 20 years, have been doing the same work for much of that time, and seeing the same friends for most of that time. I want use this newfound freedom well...to explore and do have some new experiences. I want to travel more and meet new people. I want to learn things. I want to find out if I'm someone other than the woman I've been for the last 20 years.

She paused, so we can talk about that more. But first, Bill, what's your biggest fantasy? What is the one thing you'd like to do that you haven't done?"

"Let's see, Jean...my biggest fantasy. I have two. I'll tell you the g-rated one. My fantasy is to buy a sailboat and go sailing around the world, from port to port, for a year. And since I'll soon be 45, if I'm going to get this one in, I'd better get moving I guess. I've always wondered what it would be like to just take off with no schedule and no firm destination. Just to see what the next day will bring. Maybe one day. I've done a lot of sailing in the last few years so I think I have the skills...now if I can just get the courage. So, I've told you my fantasy. Now yours, Jean. What's your biggest fantasy?"

She smiled. Her teeth were white and even and her lips were full...and very kissable. And soon I may just give them a try. She said, "wait, that's not fair. You said you were just giving me the g-rated fantasy. Is there a PG rated one, or R, or maybe X? I want to hear about it."

Okay Jean, here goes. Here's my fantasy, and I'm afraid it is X-rated. Are you still sure you want to hear it? I wouldn't want to offend your delicate sensibilities."

"Bill, you'd better tell me soon. And you'd be surprised how indelicate my sensibilities are sometimes. What's your X-rated fantasy, Bill? And if you think that's going to seduce me, you're wrong." But at the same time she said that, she moved closer and leaned forward, looking at me intently.

"My biggest fantasy is to have a long, long orgy...with one woman. A few days where we had sex anytime we wanted, in any way. Where we were both naked and could perform any sexual act as long as the other one was ready for it. I've had some days, or at least a few hours like that of course, and I'm sure you have, but I'm talking at least three or four days. I love sex and sometimes I just want to have all I want. I know orgy means having group sex but I want it with one special, hot woman that wanted it as much as I do." I looked at Jean to gauge her reaction. "Well, you asked. That's what one of my fantasies has always been. And while I'm at it, let me embellish a little. I...wait, no. I'm not going to get into that part. It may scare you." We both laughed. "Now, what is your biggest fantasy, Jean?"

"Well, Bill, my fantasy is to write books...not necessarily best sellers but good books that regularly get published. I love to read and I've always imagined that the life of a writer must be the best you could have. In my job, I'm always dealing with people and I like that, but I also fantasize about having a little house next to the ocean or on a lake...like this one...and I could just listen to music and write and read. That may be a bigger fantasy than the one about you sailing around the world."

"I don't think either one of our fantasies are that far-fetched. I just might end up taking that year off. And you may write your masterpiece. Have you ever tried writing anything before?"

She replied softly, "a few things...poems and short stories, and I have the outline of a novel but I don't have the time, or maybe the courage, to begin writing it."

She told me about the plot of her "fantasy" novel. I made a couple of suggestions and of course told her how interesting it sounded. And it did sound interesting. I knew our thirty minutes were disappearing but I had a theory about Jean. She had to get to know someone for sex to be even a remote possibility and I figured I wanted to get to know her better also and if I lost a bet, well so be it. I'd win in the long run.

But, I have to admit I was distracted...at first by her beautiful, smooth legs and her luscious breasts that were outlined wonderfully under the silk robe and silk top that she had on. Her breasts were full and I could make out the outline of her nipples. Then I was entranced by the way she kept touching my arm that was near hers as she got excited about the story. And her eyes sparkled in the firelight. She was a beautiful and alluring woman. I imagined all the things that I'd like to be doing to her.

All in all, we talked about her literary ambitions and interest for the full half hour. I then refilled our wineglasses and sat back down.

"Well, Jean, you won. Our time is up and we've spent it talking about everything but sex. I hate losing bets but I think I won anyway because I loved talking to you so much."

She looked at me, and smiled. "I did to Bill. I got so wrapped up in my book ideas that you didn't have a chance to try to seduce me did you? I'll tell you what. Even though you won't be successful, let's extend our bet for another 30 minutes. I'm enjoying this and as I said earlier, I am always in control of myself."

"Jean, that's so gracious of you. But, be forewarned, I'm just getting started. Okay, now it's your turn to tell me your x-rated fantasy. Remember you have to answer my questions."

She smiled shyly, "I have to be honest, Bill. I haven't been with a man since a few months before my divorce from Jack. And he was the only one that I'd ever slept with. Doesn't that sound so old-fashioned? Nobody does that anymore I guess. Or at least tells about it. But, as to fantasies, it seems like the only thing I've ever been able to do is fantasize. So, I wouldn't even know where to start, I've had so many. God, this wine is loosening my tongue too much."

"I'm not letting you off that easy, Jean. I told you mine so tell me one of the things that has been a persistent fantasy for you. No matter how outrageous it is. I want to hear what sweet, good girl Jean has always wanted but never gotten."

She smiled again, "Bill, I may not be as good a girl as you think I am...at least in my thoughts. But I couldn't tell you my biggest fantasy. You'd think I was too kinky and you'd run out of the room. I've never told anyone my biggest sexual fantasy and I'm not about to start with a man I met a few hours ago."

I filled her wineglass again. "Jean, let me tell you something about me. I am a very open, accepting guy and I am completely trustworthy. I've made a living for the last 15 years by working with companies on a confidential basis. My consulting consists of three things...knowledge, maybe a little wisdom, and most of all, trust. So, believe me, I won't laugh, blush, or run out of the room. I want to hear your biggest fantasy. I bring you in from the cold world outside, feed you, ply you with wine, tell you my biggest fantasies and it's not fair that you keep yours to yourself. Besides, I may be a little bit kinky myself. I can't imagine anything that would shock me too much."

She looked into my eyes. "God, you are a good salesman. You're right, I have no right to not tell you what I asked you to tell me. Does that sound right? Maybe the wine's getting to me. So here goes on my fantasy. Don't say I didn't warn you.

"Remember a few minutes ago, I was telling you about Jack. Well, he is a nice but meek kind of guy. He's intelligent and quite successful but just not very aggressive and almost passionless. He rarely gets excited about anything. I think one of the things that happened to me in our marriage, maybe the main thing, is that I simply got bored. Well, our sex life was OK. At first, since it was all so new and I didn't know anything else, it was actually quite good. But later it got routine. For example...by the way, are you sure you want to hear this?" I told her I couldn't wait to hear more. "Okay, during love making, he was so easygoing and gentle and I wanted...I...God, this is hard to tell someone, particularly a man I just met...but, okay, I agreed, dammit...I wanted it...hmm...a little more active...and I'd keep imploring him to do that and he never would. And as for oral sex, the few times he did it to me, it was awful...well, not awful, but not very good. I'd dress in provocative clothes or sexy lingerie and he responded but almost perfunctorily. Sometimes I'd do things like get some scarves out and ask him to tie me up and he wouldn't. I'd rent x-rated movies and ask him to watch, but he thought I was perverted. I finally just quit trying. And, I did two things. I got some toys and started taking care of myself...and I developed a very active fantasy life." Her face reddened as she spoke those last sentences.

I smiled at her and put my hand on her arm. "Well, Jean, that's what I want to hear. Those fantasies of yours. Oops, sorry, you said no touching. But you do have to tell me the fantasy."

She smiled, "I think I can overlook that. I shouldn't have used that word 'fantasy', should I, since we're playing this damn game of 'tell me your fantasy and I'll tell you mine.' But, if you're sure...but wait, first you have to tell me what kind of things you'd do in that orgy that you mentioned...the one with two people. Tell me a fantasy and I'll tell you one."

I looked at her sternly, "I'm not sure that's fair but okay, I'll do it. One of the things that I would do with the woman is spank her little rear end." I looked at Jean. "OK, not hot enough for you? The other thing I'd do is put her on the floor, straddle her face, and fuck her mouth, making her take it all and then I'd cum in her mouth, filling it up." Jean blushed a little. "Well, you asked. I hope my language didn't offend you. I should've watched how I said it. Now it's your turn. What is one of your fantasies?"

Jean sat staring at me. There was such a long pause I thought she was regretting getting into this conversation. Her face was flushed and her voice was husky as she spoke, "I have lots of them, but three of them are: one, I want to be spanked by a man...and I want good, hard sexual intercourse. And I'd love for man to...put his penis in my mouth and...do what you said."

I smiled and teased her, "sexual intercourse? You can do better than that, Jean. We're both adults. Tell me what you really mean. That's part of the game rules."

I was teasing but she appeared to be dead serious when she responded, "OK, Bill what I want is for a man to take me and fuck the hell out of me. I want a man to put me down and press his big, hard cock between my lips and mouth-fuck me until he cums all inside me. I want a man to lick my hot pussy until I scream with pleasure. And I have a lot of other things that I want him to do to me. Bill, I want a big strong man to take me and dominate me sexually. I want to be treated like a slut. I've been the good little daughter and wife all my life. I'm sick of it. Is that what you wanted to hear Bill?"

Now it was my turn to blush. Before she spoke, my cock was hard. Now it was bursting out of my pants. "Jean, I think we should revisit the no-touching rule. Are you willing to do that? When you say stop, I will."

In a meek and quiet voice, she responded, "Yes, I think that would be a good idea...to get rid of the no-touching rule."

I reached out to massage her bare leg. She leaned back and moaned. I leaned closer. "Jean, I'm going to find that slut-girl in you. I'm going to find the bad girl and give her what she wants. Jean, look down at my crotch. See how fucking hard you make my cock, how it is throbbing to be touched. Jean, what I'd like to do is have you take it out and hold it. Wrap your hands around it. Squeeze it. And then you can open up your lets and slide it inside your warm pussy if you want. Tell me what you want Jean."

She moaned, "God, I'm going to lose the bet. What I want more than anything is for you to fuck me, Bill."

I stood up and pulled her to her feet. I kissed her deeply and as I did so, I took her hand and placed it on the front of my pants.

"Jean, feel this. This is the cock that's going to fuck you like you've never been fucked before. This is the cock that's going to go in your pussy, your mouth, and your asshole. Now Jean, let's get these clothes off."

With that, I removed her robe. She had on a silk pullover and panties. Her hands started ripping my shirt off. She fumbled with the belt and button and zipper of my pants. She was frantic. I slowed her down and lifted her top over her head and looked at her beautiful, smooth and full tits capped off by hard nipples that looked tense, like they were reaching out to touch something. I held them in my hands as she reached in my pants and shorts to put her hand on my cock. Because it was so hard, she couldn't get it out until she lowered my pants and I stepped out of them. She then pulled my boxers off with a jerk and she moaned as her hands moved to my groin, one hand around the shaft and one massaging the head. She kept repeating over and over, "God, oh God."

She continued to explore my cock with both her eyes and hands. I reached behind her and put one hand on the cheek of each ass and pressed her to me. "Jean, you are a beautiful woman....and you're going to get fucked. Do you like the feel of that cock in your hands?"

"Oh, Bill, I've never imagined a cock could feel so good...and be so big and hard." She was almost whimpering with excitement. I felt the clutching of her hands all over my long shaft and over the head, down to my balls that she cupped and fondled in her hand. She arched her neck as I lifted her hair and put my lips to her long smooth neck. I whispered, "Bend over the sofa, Jean, you hot little slut, and I'm going to spank you and fuck you hard and deep."

She turned, leaned over and put her hands on the back of the sofa. Her beautiful hot ass was pointed towards me; her butt cheeks were nicely rounded, and very firm and supple as I squeezed them. I leaned over her back and my hands reached around to cup her hanging breasts. As I did so, my cock fit nicely between her legs that she opened to receive it. I massaged her tits and took her nipples between my forefingers and thumb and rolled them around. As my grip tightened, I pulled her nipples and she gasped and whimpered even more. Her hand reached between her legs and stroked my cock. She leaned more and took the head and introduced it to her pussy lips. I felt the wetness all along the slit...she was throbbing and she kept lifting and spreading her legs to take me inside. I put my hands on her shoulders and leaned her over and then leaned into her. She put my cockhead at the entrance of her treasure. "Jean, how does it feel to have a big cock about to enter your cunt? Do you want it all up inside you? Do you want to fucked like a whore, baby?"

She was barely able to moan, "please, Bill...fuck me. I've never wanted anything so damn much." As she spoke, I moved her higher so she was entirely on the back of the sofa...now her ass and pussy were more at the right level for a proper fucking. I slide my dick inside, deeper and deeper, now fucking her, but entering her slowly. Her pussy was tight. She hadn't been fucked for awhile. Her body moved back into mine and I fucked her deeper and deeper and with a grunt, I hit home...the whole of my cock was buried inside her. I looked down and saw her swollen cunt lips grasping me as I fucked inside that warm, wet, eager hole. I could see her wrinkled little asshole as she moved in rhythm with me.

"Jean, do you want it hard and deep?" As she moaned her assent, I withdrew and bit and slapped her hard on the ass...once, twice, three times. Her cheeks turned red. "Is that what you want, Jean? Do you want a rough hard deep fucking?"

I could feel her body react as her pace quickened when I spanked her ass and talked to her. "God, yes, Bill, fuck me hard."

I complied. I began to make longer, harder thrusts. I could hear her wet pussy and my cock making that sweet, wet "slurpy" sound of fucking. I reached one hand and put it on her shoulder as my other hand was on her buttock. The power and speed of my thrusts increased. I have a curved cock and when I fuck, sometimes, it's in a "shovel" motion. Each thrust lifted her hips off the chair and she was bouncing on my cock. My balls were slapping against her ass with each entry. I held her so shoulders so that I would be at the deepest point possible and so that I knew that her crotch was being hit hard by my body. "Harder, Jean...do you want it harder."

I think she tried to tell me yes; in either case, I increased my force and speed even more. As I did so, she began to yell, over and over, "OH, YES, OH, OH, OH, GOD, YES."

"I'm going to cum inside your hot cunt Jean."

Her body began to shudder, and her breath was clipped and labored. I began moaning which seemed to increase her ardor if that was possible. I made several long hard strokes as I felt her pussy muscles contracting around my shaft with a strong hard orgasm. Her vaginal canal became very tight, like a virgin, as the spasms continued. I could feel my cum begin to flow...it felt like a river flowing from my balls, all the way through the shaft, out the head and deep into her pussy. Her pussy was milking me. My hands stroked her ass as my thrusts continued.

I implored her, "keep cumming Jean. Feel the hot cum inside your pussy? Cum all over my cock, Jean." And she complied. I have no idea how many orgasms she had but as they began to subside, she reached around with both and grabbed the sides of my legs and pressed me to her open pussy and open ass. "Hold it tight against me, Bill. Let you cock rest inside. I want to think remember this. You can't imagine how good this was for me."

"Was it what you wanted, Jean? A good, hard fuck?"

She purred, "Bill, it was exactly what I've always wanted. But you know I want more later."

As I withdrew, I replied, "This is just the beginning, Jean. You're going to get everything you want."

She turned, reached between her legs, slipped a finger inside, and put it to her lips. She put some on her tongue and slowly savored it. "Is that a promise, Bill? Promise me that you're we going to have our private orgy."

I leaned over to kiss her and thrust my tongue inside her mouth and tasted our cum on her tongue. Her mouth opened like her pussy did and she engulfed me. Finally, I withdrew and looked into her lust-filled eyes. "I promise, Jean. I promise."

"You won the bet, Bill. I never thought you could do it."

Exhausted but exhilarated, Jean and I both sat down on the sofa. Our bodies were glistening with a light sheen of perspiration from our efforts.

"God, Bill, I never imagined sex could be that good. It's like I've never had it before."

I smiled, "Jean, that is nice of you to say. It was great for me too. You really got turned on and that's what excites me – to see a woman get so hot and enthusiastic during sex. I love it when you love it."

I thought back to a few hours before, when I met Jean at the roadside diner and invited her up here to get out of the inclement weather. It was as if we peeled off layers of ourselves in a two to three hour period, and that now we were starting to find out what was underneath.