Hitting The Jackpot 1

I am a fairly average guy in my thirties, about 6 feet tall, 180 lbs. The only things that distinguish me are that I am fairly well off financially, am considered by many women to be very good looking, and I have a clinical fear of intimacy that has totally screwed up my sexual relationships with women. I had no problem with performance the few times that I got past my intimacy issue, but the only women I have fucked have been prostitutes or true sluts, and I never had any interest in fucking them again, or -- obviously - a relationship.

I finally met someone through an outdoor adventure club that I felt differently about than any other woman, and who made me repeatedly curse my intimacy issues. Her name is Jill.

Jill is about forty (probably about five years older than I am) and has recently gone through a fairly contentious divorce. I first noticed her for several reasons: For a little woman (probably only about 5 feet tall and less than 100 pounds) she is able to hold her own in any outdoor activity, whether it be kayaking, rock climbing, rafting, whatever, and handles all equipment herself without asking for help. Her ass and thighs are what virtually any man would consider ideal (she has tiny tits, no problem for me). And, although her face is certainly not movie star beautiful, it is really cute. Perhaps most intriguing of all is that she has a mysterious look that is very hard to describe; I guess that the word that I am familiar with that is the closest to describing her look is "sultry."

Anyway, Jill and I got to know each other fairly well through the club and club-related activities. Jill also liked to host parties, and I went to several at her house where I met her fairly large cadre of female friends, only one of whom was in the adventure club. Her house, which she got in the divorce (although I also got the impression Jill made good money in her job as some sort of a finance director) is very nice, and in a beautiful suburb next to the suburb that I live in. Her female friends all seem to be happily married, and are very outgoing, forward, and fun loving, as are their husbands.

Jill and I have a number of things in common in addition to the adventure club, including a love of dancing (can you believe that a guy with intimacy issues loves to dance -- I've never understood that myself), theater, and physical fitness. Over time we started meeting at the theater, gym, or a dance club, sometimes with some other people, and sometimes just the two of us. We always had a great time, especially when we danced Latin dances together. After knowing her for about six months, I realized that Jill turned me on like no other woman ever had. If there ever was someone that could be right for me it was Jill -- but that not only didn't seem to help my intimacy issues, it seemed to make them worse. I could hold her in a Tango, but could never even have body contact with her otherwise.

I happened to know one of Jill's female friends, Linda, through a work contact, and one morning after we attended a meeting together Linda invited me to lunch. Linda probably was Jill's most candid friend. Actually, calling Linda "candid" is like calling the Pope "Catholic." She is just plain in-your-face blunt -- she never minces words.

Once we ordered lunch Linda exemplified her trademarked frankness. "What the fuck is wrong with you, Brian? Jill is the most fantastic woman I know, sexy as hell, and obviously right for you, yet you've never even so much as given her a real kiss, let alone fucked her. But I don't think you're gay. So what the hell is up?"

Shit, how do you respond to someone that pushy? In a public place? When you're totally embarrassed and conflicted?

While blushing, I stammered out some inane rambling excuses, but Linda is not the type of person that you can bullshit. She was on me like a cowboy on a steak, slicing off pieces of my excuses and ramblings until finally I had no recourse but to storm out of the restaurant or to come clean. For whatever reason I came clean.

I told Linda that I thought that Jill was totally sexy, and really liked her, but that my clinical intimacy issues were really holding me back. In response to Linda's waterboarding-type questioning I told her all the details of my intimacy issues and limited sexual history.

I was immediately sorry that I communicated to Linda what I had. I had never opened up to anyone before, and thought that this honesty on my part could end up really biting me in the ass.

Linda's reaction didn't help. She got a faraway look in her eyes, then a smirk on her face, and then her eyes lit up. Without another word about Jill or my issues, Linda changed the subject, we finished lunch, she gave me a perfunctory hug goodbye, and she scurried off.

A couple of weeks went by. Things between Jill and I didn't change at all, so thankfully I didn't think Linda had talked to Jill about my problems. Then on a Friday Jill asked if the next day, at about noon, I could give her a ride to a kayak practice session we were planning on attending since her car was in the shop. I agreed, and arrived at her house about 11:45 Saturday morning.

When I got to her house I was surprised to see that Linda and three more of Jill's female friends were there. They all greeted me with Cheshire Cat grins, and said that Jill had told them to have me go up to her bedroom since she was ready but just cleaning some things up. I asked if one of them could go up instead, but they said that they had to leave right away; Linda emphasized that I must actually go into her room. The four of them then smugly hurried out the door without any further explanation.

I thought that this situation was really odd, but concluded that I had no choice but to do as they requested, so up the stairs I went. Jill's bedroom door was open so I casually rapped my knuckles on the doorjamb a few times, said "Knock, knock, are you here, Jill?" then walked in.

I was a full three or four steps into her bedroom before I saw Jill. She was lying face up on her four poster bed, naked, with each of her arms and legs handcuffed to the one of the bed posts, and a gag in her mouth. Her eyes were watering.

To say that I was stunned would be the understatement of the year. I stood motionless, probably with my mouth hanging open and my eyes as large as baseballs, staring at Jill's body. Her pelvis, stomach and thighs were exquisite, perfectly framing a shaved small slit with prominent pussy lips that seemed to have a coating of liquid glistening in the sunlight streaming through her bedroom's bay window. Her nipples were over-sized, taking up at least a quarter of her tiny tits, and rock hard, each standing up like a lighthouse on a rock. Her long almost bronze hair was also shimmering in the streaming natural light, and draped over her arms and shoulders but not in any way interfering with a view of her boobage. In addition to watering, her eyes had a pleading, helpless look.

I don't know how long it was before I regained my bearings, and was able to actually think rather than just stare. Once I did, I noticed a pain at my crotch area -- my cock had apparently involuntarily snapped to attention so quickly that it had forcefully impacted zipper; it actually hurt. I finally thought "I have to help Jill."

I went over to Jill and with my hands trembling removed her gag. In an exhale that could best be described as an angry sob, she blurted out "Can you believe that my 'so called' friends did this to me? I even told them that you were coming by, and they just snorted and giggled. I HATE those bitches!"

I wiped Jill's eyes with a hanky and tried to only make eye contact rather than glaring at her exquisite body parts -- but it was impossible. Trying to sound as sympathetic as I could I asked "Where's the key to the handcuffs?"

Her response bowled me over -- "The bitches put it in my pussy."

So this is my situation:

--I have clinical intimacy issues.

--My cock has involuntarily gotten as hard and big as it ever has in my life.

--A woman that I consider the sexiest I have ever met in my life is lying spread-eagle, naked, in front of me.

--To release her I have to fish a handcuff key out of her pussy.

Okay! My brain circuits were not just overloaded -- they were fried.

I simply said "I'll get the key" and looked closely at Jill's cunt. God it looked fantastic. I groaned loudly as my dick impossibly got even harder, jamming further into my pants zipper and so uncomfortable that I had to readjust its position with my hand, which didn't go unnoticed by Jill.

Using fingers on both of my hands, I gently pulled Jill's pussy lips apart, as globs of nectar leaked out and onto the tips of my digits. Jill gasped, and when I looked at her face, she had closed her eyes, her mouth was open, and her look had changed from one of complete angst to one with a hint of pleasure.

I bent over as I moved my fingers back and forth so that I could see inside her glorious crack. A wonderful smell, both sweet and musty, wafted up to my nostrils. I viewed flaps of beautiful pink flesh and globs of nectar. It felt so soft and moist. The olfactory, touch, and visual perceptions were intoxicating.

I couldn't help myself. I had to add taste to my other senses, and for the first time in my life I put the tip of my tongue in a vagina. That resulted in a loud, sweet, "Ahhh" sound from Jill, completing a sensory wave invigorating all five of my senses at the same time. Involuntarily my tongue flicked up and down Jill's pussy lapping up her sweet juices. Having lost myself in pleasure I was momentarily startled when I hit a solid object -- the key. By then, however, I was more concerned with other things.

I continued to flick the inside of Jill's pussy with my tongue as I gently reached in with a finger and thumb to remove the key. This evoked even more moans from Jill.

Though I had found the initial object of my search, my goal had changed. I was after pleasure, for both Jill and I, more than the key. Apparently Jill was too. After she had to know that the key had been removed, she looked straight at me and said "please don't stop; I need to cum".

I placed the key on the bed next to Jill's hip, swung my right leg over her body so that I was straddling her, and started tonguing, fingering, and sucking her pussy lips and clit with a passion that I had never experienced before in my entire life. I was rewarded with moans, exclamations like "Oh my God," screams, and convulsions from Jill a she obviously experienced another climax every two or three minutes as I continued my assault. I never felt better in my life as when she bucked her hips up to push her open pussy hard into my tongue as I exposed her clit with the fingers of one hand and massaged it with the fingers of the other hand. Then she screamed.

After I had driven Jill to orgasmville at least six or seven times her pelvis suddenly relaxed and she stared at me and said "Fuck me Brian, please, please fuck me; screw my fucking brains out; pound my little cunt into submission; please, please fuck the shit out of me!"

Intimacy issues? Apparently Jill's words were the perfect antidote for them. Instantly I pulled my pants off, threw them off the bed, and stabbed her oozing fuck hole with my prick. I put my right hand on her left bicep, my left hand on here right protruding nipple, and my mouth over her left nipple. As I sucked her nipple like a starving baby I moved my hips back and forth.

At first I was so excited I was pounding Jill so hard that my shaft was heating up with the friction generated by the rapid relative movement between my cock and her pussy despite the ample lubrication. I then slowed my pace, making each reciprocation of my fuck tool go from my head at the opening of her cunt until it was completely buried. Her pussy was so snug, moist, and luscious that every stroke seemed to pump a gallon of endorphins and other neurotransmitters through my nervous system. I thought that the sense of euphoria could not be topped -- that is until I ejaculated. My ejaculation, combined with our mutual passion, caused Jill to have an instant tsunami-grade climax herself.

After our consummate orgasms, Jill and I laid in a stupor for a good ten minutes. After another ten minutes of passionate kissing in which I constantly moved my hands over her breasts and hips, Jill finally said "I would love to run my hands over your body too," evoking a good laugh from both of us. I crawled to the foot of the bed, found the handcuff key buried in the sheets, and undid her handcuffs.

In her first acts when free she put her arms around my neck, and her legs around my waist, and laid another passionate kiss on me. I immediately got rock hard again, Jill turned over onto her hands and knees, and I unmercifully pummeled her doggy style as she constantly chanted "fuck me, oh yeah, fuck me, hell yes, fuck me". Our next orgasm was just as intense as the last one, and we collapsed into each other's arms, this time each of us massaging the other as we cooed and gently kissed.

When I finally got home from Jill's bed Monday morning -- after a roughly forty five hour fuck-fest -- my intimacy issues were a thing of the past.

My message machine light was blinking. Among the messages was one from Linda. "Well, asshole, I guess you owe me big time, don't you? Though you can't possibly repay me, I'll accept a pearl necklace."

Two days later couriers delivered pearl necklaces to Linda and each of her three handcuff wielding buddies.