Shared Fantasies Ch. 02

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He begins to see what he has gotten himself in for.
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Part 2 of the 5 part series

Updated 10/22/2022
Created 12/05/2007
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Peter_
Peter_
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This story is protected by copyright, by Peter, the author, and cannot be reposted or used for any purpose without his prior consent. But please email the author at the address in my profile to request such consent.

Please take a moment to vote, and give me some feedback. The more specific the better, it helps improve my writing to hear specific likes and dislikes. Thanks, and enjoy.

Author's note:

This is a continuation of a multi-part story. It is strongly suggested you read all parts in order. Please take note of the Author's note a the beginning of part 1.

Peter

Now on to the story:

*

We went into the bathroom, that has double vanities, so in a few minutes I'd splashed water on my face and brushed my teeth and was ready to head to bed. As I started out of the room Jessie called over her shoulder, "Close the door, will ya. I need a couple of minutes of privacy. I'll be right there."

It was a bit unusual, but I wasn't about to complain at that point.

I turned out all the lights in the bedroom and lit a couple of candles; something we often do on weekend nights to help set the mood when we know lovemaking is coming. I just lay back and smiled, it had been a lovely evening so far and it was obviously just going to get better and better!

It seemed like forever, but was probably only about five minutes before Jessie finally came out of the bathroom and headed to bed. I nearly fainted. She looked fucking fantastic (no pun intended). She was wearing a set of lingerie the likes of which I had never seen her in. Nothing even close. She looked so damn sexy I actually thought I might just cum spontaneously! As she came closer, her 'special occasion' perfume scent hit my olfactory nerves. Another noticeable throb in my cock occurred.

The outfit was extremely sexy. It covered quite a bit, but the curves and sensuality glared at the same time. Her very erect nipples made fine points in the flimsy material. Her flat tummy was on clear display and the bottoms displayed her cunt lips plainly. The candlelight made the effect all the more erotic!

"My God, you look totally gorgeous!" I blurted out.

"Oh, I hoped I looked sexy" she said in a teasy kind of way.

"You are so far beyond just 'sexy' that I don't know the word to describe it!" I replied, meaning every word.

"Hmm, not a bad reply" she said with a giggle.

With no further ado she turned back the covers and lay down. She clearly was looking at my rock hard cock and after a few seconds, wrapped her hand around it and started to stroke it slowly. She continued for only a moment or two, but it was enough to get me racing.

She rolled toward me, pressed her silkily clad bod against my naked one and started to kiss me so passionately that I could barely breath! We stayed at serious necking for quite a while, which got me hot as Hell, and I could tell by her reactions it did the same for Jessie.

Finally we broke off our lip lock and I was able to slip my hand under her top. I love to caress her 36D breasts. I played with them for some time, tweaking her nipples in the way that I know she loves.

Finally she spoke, " remove my bottom and lick my cunt until I cum!" This wasn't the historical norm for Jessie's language, but it was more common recently since we'd met with Tom and Sally. She was much more direct about what she wanted than she'd ever been, even before things went bad.

I didn't hesitate to comply.

"And Jack, I'm going to suck your cock while you eat me, but you don't get to cum until you make me cum! If you do a REAL good job, I MIGHT let you cum in my mouth!"

I was already at her love box and started to do my very best. The very idea that she might suck me to climax in her mouth had me incredibly turned on. It is something she had rarely done, and I knew she didn't really like it. But the fact that she even mentioned it confirmed how wound up she was too!

Over the years I've learned pretty well how to push Jessie's buttons, and that particular night I did my very best. She was squirming and moaning in no time at all. All the while she was giving me the best blowjob I could remember for a very long time, if not forever.

I was so excited I was afraid I'd explode before I pushed her over the edge, but she would slow down or ease up as necessary to keep me from cumming as I attacked her love zone.

I was in ecstasy, and she was starting to flood my face with her juices, a sure sign she was very close.

"OH YES BABY," she yelled as she let my cock slip from her mouth. She threw herself back on the bed and screamed "FUCK!" very loudly as she came very hard.

I gently licked her pussy, without touching her clit, as I know after cumming that hard it is so sensitive that it's actually painful to have me stimulate it.

After a couple of minutes she was back among the living and took my cock back in her mouth and started to suck me in earnest.

I laid back and savored the feelings. I was hoping she really would make me cum in her mouth, something she hadn't done in a long time. I was getting close, very close and I couldn't help pumping my hips into her mouth. She didn't seem to mind and sucked and bobbed even more. Shit, I was almost there. I couldn't believe she was going to let me cum in her mouth but I was so close that obviously she was and then! She STOPPED.

"Shit, I was so close, God Jessie I wanted you to finish!" I exclaimed before I even thought.

"I know baby, but we need to talk"

Those four words again, but this time from her. I couldn't imagine about what however.

I didn't want to blow this, so to speak, since the evening had been so damn perfect so far. Except of course for the terminated blowjob.

I didn't say anything, just sort of flopped on my back.

Jessie didn't hesitate, "Jack, I've been thinking about what you said regarding your fantasy."

My heart started to pound. I'd pretty much decided to let it go. I didn't think that Jessie was at all comfortable with it and I for sure had decided to not bring it up again this weekend, if ever.

"And?" was all I could think of.

"Do you still want it?" she asked softly.

A long time, or so it seemed to me, transpired before I came up with a response, which admittedly was rather lame, "Why?"

"Come on Jack, that's a bullshit answer" she said a little testily.

"Well, I got the impression that it wasn't something that worked at all for you, that's why I asked" I said honestly, but somewhat defensively.

"Oh, well, that probably was my initial reaction, but we said we were going to keep working at our sex life and, well, I've been thinking about it and if that's really your fantasy, I should try to give it to you just like you did for me" she said in a much more friendly tone.

I paused a long time, and she just waited.

"Yeah, I guess it is. I've fantasized about it for a long time and I honestly think I'd like to see what it's like."

"I still think you aren't going to like when fantasy and reality clash, but if your are really, really sure, then I'm going to give you your fantasy this weekend. So, is that what you want?"

I paused an even longer time before answering this question.

"Yes, I want to find out what it's really like" I said, sure that I meant it, but scared as Hell that Jessie was right about not liking the reality of my fantasy.

She didn't say another word.

She had moved so we were face to face for our conversation. She gave me a quick kiss and then moved down so she was kneeling between my legs. I was lying on my back, and between our conversation and the blowjob she'd been giving me, I was as hard as I ever get. She looked so damn sexy in that lingerie top that I could barely stand it. She started to suck my cock again. And this time she didn't tease or go slow, I was racing to orgasm. I figured she was going to give me an earth shattering cum in preparation for the 'event'. Just as I was about to explode, she stopped again.

I groaned loudly.

"Okay, you told me how you wanted this to be on an occasion where you hadn't cum for a while and were really horny when we started. So, we are starting right now. Here are the rules. You do everything I tell you. Exactly as I tell you. If you don't it's over and we will NEVER come back to this fantasy of yours. I heard clearly what you want, and I'll give it to you, thought I'm quite sure you'll regret it. Once we start, I'm in total control, you don't have a say anymore. So, is that what you want and do you agree?" she was obviously very serious from her demeanor.

Again I paused a long time. I knew that if I ever wanted to experience my long time fantasy, this was my only chance. If I said 'no' now, I'd never have another opportunity. But Jessie's words about regretting reality vs. fantasy were at the forefront of my mind. Finally I took the leap!

"Yes, that's what I want, and I agree to your rules" I said and then let out a huge breath.

She looked at me with a smile I'd never seen in our whole lives and then took my cock in her hand and stroked it a few times.

"Okay then, it's settled. Now roll over and go to sleep, tomorrow is going to be a long day for you!"

That was the last thing I had expected! I opened my mouth to speak, but caught myself just in time. It was quite some time before sleep relieved me of my thoughts. I'm sure you can garner what they were!

The next morning I was awake early. Anticipation I'm sure. I just lay there thinking for a long while. The thoughts racing through my mind were as you would expect. Did I REALLY want to go through with this? I was extraordinarily horny already and knowing Jessie, she'd put her best effort into this adventure, regardless of how she felt about it. It's just the way she is. Once she takes on something, she gives it her all, no mater what.

Well, the die was cast anyway, I'd agreed to her terms the night before and I too, had my principles. I never broke my word if I could possibly avoid it. As I was trying to imagine what the days, and especially the night, were going to be like, I became aware of Jessie waking.

"Morning sunshine" she said.

I rolled over and gave her a gentle kiss, "Good morning yourself" I replied.

"Go put on the coffee and then come back while it's brewing. I want to ask you something and then I want you to do something for me" she directed. It definitely wasn't a request.

My pulse quickened and my cock swelled slightly at the way she was acting. We were obviously into my fantasy already and her prediction of a long day seemed inevitable.

When I returned she patted my side of the bed, indicating I should lie back down. She was on her side with her head held up by her hand, looking at me rather intently.

"When you were acting out this fantasy you'd play with yourself until you almost came, then stop, right?" she asked.

"Uh, well, yeah . . ." I replied. I thought about asking why she wanted to know, but thought it was probably better not to. I wasn't particularly comfortable with this conversation. I think that well every man on the planet masturbates from time to time, that very few want to talk about it. I certainly am not one who does, but evidently didn't have a choice at the moment.

Because I'd told Jessie a great deal about my fantasy the prior Sunday when I thought she was opposed to it, in an attempt to persuade her to try it, I was now pretty sure some, if not most of what I'd told her was about to come back to haunt me. I now saw that any notion I had that she wasn't paying strict attention was well off the mark

"Okay, do it now. I want to watch you," she said stunning me.

"What!" I responded, rather stunned. It was more of an instinctive answer than a conscious thought.

"I want to watch you," she repeated.

"I'm not really comfortable with that, to tell the truth" I stuttered.

"Jack, look! I told you the rules last night. You agreed to them. Have you changed your mind about going through with this?" she asked very seriously.

I didn't really hesitate. I had already come too far to let this opportunity pass, since if I did it would be forever and I'd always wonder, what if? "No, I didn't change my mind. You just caught me off guard is all."

"Okay, I understand, but that's your last chance. If you want out of this say so now, otherwise from now on you do exactly as I say, when I say, or I stop and this will be over for good!" which was exactly what I'd already realized.

Then more gently she went on, "You know I won't do anything to hurt you or humiliate you. You made it clear that's not part of your fantasy. When we go out no one but us will have any idea what's going on. But I've never seen any man masturbate and I think most women think it would be sexy to watch. I've always wanted to. Here, I'll get you started."

And with that she took hold of my cock and started to slowly stroke it. It was semi-hard when she started. It took just seconds to become fully hard. The combination of not having cum for nearly a week, the teasing she'd already done, and the incredibly erotic nature of the whole current situation, had me so turned on I couldn't believe it!

Once I was completely hard, Jessie stroked me for about another minute then said, "Okay, time for you to take over!"

Somewhat to my amazement, I didn't hesitate; I just started to stroke myself as if she wasn't even there. I did close my eyes to try and mentally remove her from the picture. I was only moderately successful at that.

After what seemed like about two or three minutes, as I was starting to feel the churn in my balls, Jesse spoke, "Tell me what you're feeling and what you are doing as you build up."

Again, much to my surprise I just did as she said.

"I'm just stroking steady as I start to feel my orgasm coming."

I stopped talking and kept stroking.

It wasn't long before Jessie spoke again, "Come on, tell me more!"

I had never really thought about 'how' I beat off, or what I was thinking during it, I just did it.

"Well, as I get closer, I go faster" again I wasn't very forthcoming.

"Come on Jack, think about what your doing and feeling and tell me!' she said with a bit of irritation now.

So I started to concentrate and think and talk.

"Well, I make sure that on each stroke I slide my hand over the ridge at the base of my cock head and I'm sure to rub my finger over the most sensitive spot I have right were the cleft in my head joins the shaft" I continued.

I was starting to get very close, and I realized that I was stroking fast still. I told Jess that.

"I'm getting really close now, I'm going to have to slow down soon to keep from cumming." I really had done this a lot of times and knew exactly how to push myself to the very, very edge. For reasons I cannot explain, I was suddenly caught up in doing so and explaining it to Jessie as best I possibly could.

"Oooh, close now, very close" I explained as I started to stroke slower and slower.

My voice was getting a little ragged, "Mmmm, I have to stop for a sec. . . now I can stroke again a few times . . . oh God, so close . . . stop, wait . . . stroke a few more."

It was truly incredible, describing it to Jessie was all the more erotic and teasing!

"I , . . . th think . . . thi this is ss, uh IT!"

"Are you sure?" she asked quite seriously, "wait just a few more seconds and try a few more strokes"

I stroked about three more times, very slowly. My cock twitched, and spasmed and I felt my balls contract and then one large drop of cum oozed out my pee hole!

"Oh shit!that's as close . . . as close I can get . . . without cumming!" I gasped. And it was definitely as close as I'd ever pushed myself and still not cum.

Very softly Jessie asked me, "What happens if you touch it now?"

"I'm very sensitive, it's pretty intense" suddenly I wasn't thinking, just responding.

"Where is the most sensitive spot?" she inquired

"Right here" I told her, pointing to the cleft in my cock head, "it's always the most sensitive as you probably know, but right after cumming or almost cumming, it is extremely so!"

What the Hell was I saying. I KNEW she was going to use this information to torture me, but I didn't seem to be able to stop spewing.

"Right here?" she asked as she rubbed the exact spot with the tip of her right index finger.

I groaned, "Mmm humm"

"Any where else ultra sensitive?" she went on.

"Mmm, uh, er" I was rather inarticulate, as she continued to very softly and gently rub that most extraordinarily sensitive spot.

"Uh, th, these two places" I finally managed, "here, and here. I had pointed to the two spots on either side of the corona, right under the ridge.

"If I keep this up will you cum?" she giggled.

"N, n, no . . . not for a l, long time at least if, uh if, ya ya you keep da, da oing ing it tha that li lightly!" I finally managed to get out.

At last she stopped. I was shaking.

"Hmmm, that was rather educational" she laughed.

Oh FUCK, what had I just done! I'd given her all the tools she needed to drive me completely insane. I was already feeling like I almost was and we hadn't even 'really' started yet. Oh my God! How was I going to stand what I'd asked for!

"Would you go pour us each coffee and meet me in the family room?" she asked. It was phrased as a question, but not asked that way. And Jessie ALWAYS said please when she asked me to do something for her, even something minor, which was conspicuously missing from her 'question' this time.

"Sure" I replied, starting to get my mental balance back. Jessie takes cream and sugar in her coffee, so she normally does it herself. It's somewhat of a pain for a guy who thinks if you can't pour it straight from the pot to the cup and drink it, it isn't worth drinking in the first place.

Normally I would have grabbed my sweats and pulled them on, but something told me that going as I was (buck naked) was the best choice. After a moment's hesitation I headed to the kitchen as I was. As if reading my mind, Jessie called after me "Good choice!"

I took both our cups to the family room, the place we always spent our weekend mornings drinking coffee and reading the paper unless we had something really pressing to do. I glanced around hoping Jess had snagged the paper. No such luck. She was quickly getting into her role I realized. She just looked at me without saying a word, but with an obvious question on her face.

I resigned myself and headed to the front door. I didn't know what I'd do if the paper wasn't right up against it. I tip the paperboy an extra five bucks a month to bring it right to the porch because of our lousy weather, but he doesn't ALWAYS do it. If he had, I was fine, our front door is well sheltered and unless someone was standing on the front porch I was safe. But if it was one of those occasions when he didn't it would be out in the middle of the driveway and there was no way I was walking out there nude!

Fortunately for me, it was leaning up against the door and when I opened it, the paper nearly fell in the house. I'm sure my relief was palpable!

I delivered the paper to Jessie, she likes to have it organized just so. I felt extremely awkward just sitting there with nothing on and her in her terrycloth bathrobe, but it was clear that was what she had in mind. I was already at a point where I wasn't going to rock the boat over anything that minor!

After a few minutes she handed me the sports page, my normal first section, and other than her being clothed and me being naked, it was a normal Saturday morn.

Soon I was ready for a second cup, and (this was pretty normal) I asked if she wanted a warm-up. She has a habit, which I've expressed my annoyance at many times and to her credit, she almost never does anymore, which is to say yes then take a final drink from what's left before handing me the cup. This particular morning, she took an inordinately long draw from what was left, while making eye contact and smiling as much as you can while drinking coffee from a cup. It was a clear message. On the way to the kitchen I was mentally shaking my brain, if you know what I mean.

Peter_
Peter_
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