The Craziest Risk I Ever Took

Introduction

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I have decided to start publishing some stories about the lovers I have been so fortunate to have had during my life. I may turn my hand to fiction as well, but for now all of these are true stories. I've tried to recall the details as best as I can, both for the sake of refreshing my fading memory and also for your reading pleasure. All comments and questions are most welcome. Please enjoy!

A Quick Recap

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My sexual history is probably more typical of the past century than this one. Believe it or not, I was a virgin until I was 23. (Oh, such wasted time!) I was shy and not good at meeting women and I was terrified of the consequences of an unplanned pregnancy. Watching a close friend wind up in a hasty marriage and a very difficult life kept me on the straight and narrow.

I finally was introduced to the sex at 23 by a woman I had dated on and off again during college. She moved to my home town and things got heavy pretty quickly the summer after college and when she seduced me, she took my virginity. Long story short: we dated on and off, were married at 30, I worked too hard and traveled too much at a demanding corporate job, and we were divorced at 44.

I tried another long term relationship, but that only lasted 8 months. Despairing of any kind of "relationship" I decided to settle for cheap, meaningless sex. Joining the notorious dating site Adult Friend Finder rocked my little world. I did have a one-night stand, but found that I didn't like just using women as sex toys. Somehow, we always wound up being friends and enjoyed time in and out of the bedroom. So here are the stories of the women in my life.

-= The Craziest Risk I Ever Took In My Life =-

Just recalling this episode still has the power to send a shiver down my spine and bring a goofy grin to my face. Simply put, this was the most intense sexual encounter I've ever had and certainly the most unusual. Physically, it was gratifying but mentally was absolutely earth-shakingly stunning! I've tried to capture both aspects of the evening as I recall this encounter from almost two decades ago

The fourth lover I'd ever had, and the second one I that met on Adult Friend Finder ("AFF") - was a delightfully playful woman named Louise. I met her in the Fall of 2007 and we remained friends and lovers for years afterwards.

At the time, I was a free spirited sailor who was starting to establish a "sweetheart in every harbor". I had sailed my way down from Annapolis and was now in Delaware for a six weeks. I had landed a sweet consulting job with an insurance company in Wilmington that would allow me to earn enough money to live on for the next 6 to 8 months if I was frugal. The job kept me busy, but I made time for pleasure as well.

I had posted some pics and info on AFF and updated my location as I worked my south on my sailboat. I was a bit overwhelmed by the responses. There were replies from about almost seven different women of whom four soon became lovers. Louise, who was down in Rehoboth Beach, replied to my message and we struck up a conversation, messaging back and forth.

I love the flirting that goes on with a new AFF friend. I would generally start by sending a non-nude pic in my first message that included a smiling face and showed me out sailing. Think of it this way: In public, you wouldn't walk up to a woman you didn't know, whip out your dick and say "Hey babe, look at this! Wanna fuck?". Yes, we were both on AFF and it's patently obvious why we were there, but geeze, take it slow dude! We flirted with suggestive messages and after a while some suggestive pics were exchanged. Finally, I sent one of me fully erect and ready to fuck. She replied with a wonderful set of pics that showed her stripping out of a skimpy halter to to show her lovely C-cup breasts. I imagined how exciting it would be to meet her and see her beautiful body in real life. She seemed playful and suggested activities such as dancing naked in her backyard under a full moon and exploring each other in the hot tub afterwards.

The messaging and picture exchanges gave way to phone calls. I was immediately captivated by her delightful French/German accent. Louise was raised in Germany and France as a young girl then emigrating with her family to the US in the 1960's. We talked for hours about our backgrounds and, finally, about why we were online searching for a bedroom partner. Louise was widowed about two years ago and had only ever been with one man, her late husband. She was craving physical intimacy but wasn't looking for a relationship. Mostly she wanted a one-night-stand with the possibility of a long term fuck-buddy. A friend had told her about AFF and I was the lucky one that Louise chose to meet.

After about two weeks of flirting and talking, we made a date to meet in real life. I suggested dinner at a nice restaurant in a public place but Louise surprised me by saying she wanted me to come over to her house in Rehoboth Beach. After a bit of back and forth, she admitted that she had a huge fantasy about a stranger walking into her house, finding her asleep in her bed, and having his way with her. I asked how she saw this playing out and she described the scene she wanted to role play.

In her fantasy, I was to quietly let myself in the front door, ease down the hallway, enter her bedroom and wait for a few minutes to sure make she was asleep. She imagined the stranger becoming curious and gently pulling back the covers to reveal her lacy baby-doll nighty. She would be wearing nothing else except a sleep-mask that would block her vision. A mostly empty bottle of wine and a glass on the nightstand would explain to me why she was deeply asleep and reassure me that I could touch her without fear. I was to be slow and gentle, and act as if I was wary of waking her up. She let me know that she wanted me to explore every inch of her body without hesitation. Finally, when I judged her to be completely aroused, I was to gently push her legs apart and work my cock into her. She didn't want the intruder to be rough with her, but wanted him to slowly build her desire to the point where she would willingly spread her legs and let him enter her.

When Louise finished describing her deepest fantasy my mind was racing, screaming like a V8 pushed to the redline. My inner dialog went something like this:

("Wait.... whaaaaat??!!??")

("Oh, FUCK YEAH!!")

("What kind of crazy request is that? She wants you to break and enter, then molest her?")

("THIS IS SO FUCKING HOT!!")

("This can't possibly be real. Are you sure?"

("It sounds crazy, but what if it IS real? THIS IS SO FUCKING HOT!!!")

("What kind of fool would even consider taking up a total stranger on that offer?")

("I'll be careful, I promise! At the first sign of trouble, I'll bail! T H I S I S S O F U C K I N G H O T!!!!")

... etc...

Well, I guess I was some kind of fool. I must have been desperate for pussy, devoid of common sense, turned on by the kink, or all three together. (Yep, definitely all three.) I decided to break out of my cautious habits and take a risk. Mark Twain's famous quote rattled around in my head as I made my preparations. "Twenty years from now you will be more disappointed by the things you didn't do than by the ones you did do."

I was almost trembling with lust and trepidation as I made the 90 minute drive from Wilmington down to Rehoboth Beach. In these days before Google Maps, I had to follow the directions she gave me to her house. I got mixed up a bit and was about 15 minutes late for our assigned meeting. Finally, I found her street, a quiet cul-de-sac, found her house number, checked the description of her car in the driveway and thought "This is great - everything matches perfectly". I parked, took a deep breath and walked up to the front door.

Louise had instructed me that I was not to ring the bell or knock, but was to quietly let myself in then go to her bedroom down the hall. My hand was on the doorknob and my heart was in my throat. Just as I turned the knob and gently opened the door a nearly naked woman let out a loud yelp and scrambled down the hallway! "O H F U C K! THIS ISN'T RIGHT! G E T O U T N O W!!! " my inner voice started screaming over and over! I bolted down the walkway and back to my rental car, tore open the door and jumped inside. I briefly stopped to catch my breath and started to think the situation through.

(Did I have the wrong house?)

(No. Everything matches the description and the house on either side doesn't)

(Should I just flee before the cops showed up?)

(OH, HELL NO! That would look like I was guilty of something.)

(I would look more guilty for running! I should stay and I could show them the emails and descriptions she sent. I'd plead that it was the wrong house or something.)

I kept circling back to Louise's descriptions and the way everything matched perfectly. No, this was the right place. With no logical explanation that the big head could come up with, the little head grabbed control and said "I'll do the thinking from here on out." It took all of the courage I could summon to go back up to the front door and quietly let myself in. This was perhaps the riskiest thing I'd ever done in my life and could have resulted in a pretty lengthy jail sentence if things went sideways. My heart was pounding in my chest and my cock had shrunk to the size of a cocktail weiner - no joke!

My first impressions upon entering her house were calming. I wasn't greeted by someone screaming at me to get out and all was as quiet as could be. It was a modest beach house, free of clutter and with a faint and pleasant scent of sandalwood or some such fragrance. Modern art hung on the walls and the furniture was casual with an emphasis on comfort. All in all, it was a very welcoming, comfortable environment. The lighting was dim and there was soft jazz music being played on a stereo somewhere in the living room. The mood for seduction had obviously been set by the occupant.

I quietly walked down to the master bedroom at the end of the hallway and, sure enough, lying on the bed was the startled woman who had been approaching the entryway when I first opened the door. (Later she told me that she was wondering why I was late and had gone to the front door to make sure it was unlocked - talk about (im)perfect timing, lol! ) She appeared to be sleeping and she couldn't see me through the sleep mask she was wearing. A half-empty bottle of wine and a glass were on the bed stand, just as she described. She was the picture of a tipsy woman who had gone to bed but forgot to lock the front door. As she wished, she was at the mercy of any intruder who happened upon her unlocked door.

I let my eyes roam up and down her figure under the sheet and compared it with the pictures she had sent. I could see the swell of her breasts and her little milf tummy under the sheet. After a minute of quiet obervation, I couldn't stand it any more and began my slow explorations. I began by carefully lifting a corner of the sheet and, rather than sliding it across her skin, peeled it up and away from her "sleeping" form. Louise lay on her back with one leg cocked a bit to the side. Her silky baby-doll nighty was just long enough to cover her hips, mons and the top of her thighs. When I moved to the foot of the bed I could just get a peek underneath and get a glimpse of her smooth pussy.

My heart was pounding and my breathing was coming quickly. "Is this really happening" I asked myself? Then, there was a head-rush and a feeling of tremendous power. This beautiful "sleeping" woman wanted me to explore her body and wanted me to (dare I say it?) "molest" her. I brushed the backs of my fingers up and down her side and let them roam underneath her breasts. Flipping my hand over, I cupped her breast and gently hefted it, savoring the heavy feel. She continued to keep the ruse of "sleep", but her nipple woke up and showed hard through the silky material of her nighty. I ran my fingertips across the silky material, making little circles around her hard nipple. Oh, but my cock was getting so rock hard now!

I hungered to see more, and started to undress her. I had to somehow slide the spaghetti straps of her nighty down her shoulders so that I could see her lovely breasts. Gently, oh so gently, I moved one strap down until it started becoming taught against her upper arm. At this touch she tossed a bit "in her sleep" allowing the strap to slip down off her arm and allowing me further explorations. Another gentle tug and her left breast was revealed with its puckered aureole and hard nipple.

I grew bold enough to lightly kiss and lick her exposed nipple while gently palming her other breast to wake up its twin. She stirred again in her sleep, so I withdrew and waited a minute while she "settled back to a deeper slumber". Feeling a bit greedy, I accelerated my explorations by moving to the foot of the bed and gently working the skirt of her nighty up past her hips. I was rewarded with the sight of a freshly shaven pussy - oh, so smooth! I could just see the tops of her upper labia, but her legs were pushed together again.

The sexual tension in the room was higher than anything I had ever experienced, let alone even imagined. Louise was trying to keep still while her deepest fantasy played out. The tension was heightened, in no small part, by her fears that mirrored mine at this encounter with a total stranger. (Later she told me that she had her cell phone under the pillow and had a trusted friend on speed dial. The friend had been made aware that she was "meeting someone for a dinner date" and she wanted a quick response if there was trouble.) Despite our mutual fears our sheer physical desire (i.e. LUST) kept driving the encounter forward. Louise had not been with a man in almost two years and craved caresses, kisses and much more. I felt like a stallion with a raging hard-on who had just caught the scent of a mare in heat and I was ready to give her all the cock she could handle. Funny enough, we had not arranged a safe word for this encounter, although we did in later weeks before some S&M explorations.

We both were approaching maximum arousal and all was playing out exactly the way we had planned it together. I was at a comfort level now that this wasn't some kind of setup or trap. If she didn't want me doing this she would have freaked out and stopped me when I started undressing her and caressing her nipples. It was "all systems go" and I was eager to bring her to the point where she would spread her legs again, signalling her readiness.

At this point I was still dressed in a suit and tie, having driven directly to her home after getting off work for the day. Confident of where I thought this scene was going to wind up, I took off my suit, folding it carefully and laying it on a nearby chair. Louise later told me that it was so still that she could hear me taking off my clothes and was imagining me naked.

I was fully erect and I was so aroused that my cock was starting to drool precum. "OK" I thought to myself "Here's the big test. Will she freak out at the touch of my cock? Let's start out slow and see where it goes." I was standing by the side of the bed and could reach across to her. I grasped my cock at the base of my shaft then ran the tip of my cock over her nipple. A few drops of precum came out and I spread them in gentle circles across her areola. She shifted a bit and rolled towards me, giving me access to both of her breasts and the lovely, deep cleavage between them. I softly brushed my cock up and down her cleavage, then gently bumped the head of my cock up under chin. I continued upwards and softly, oh so softly, brushed my cock across her cheek and briefly across her lips.

Slow down! I think that she would have started sucking my cock knob at that point and I probably would have quickly climaxed in her mouth or on her face. Of course I didn't know if that was something she liked or disliked, so I pulled my cock back out of her reach. I wanted to stretch this amazing scene out as long as possible. I rested for a moment and went back to admiring the view of her sexy curves. I wanted to make this experience as close to her fantasy as possible and that meant building her desire and arousal. This was primarily about her desires and fantasy, it wasn't primarily about me. I waited for her to settle to a relaxed position of sleep. Playing the part of the wary intruder, I slowly resumed the gentle caresses, enjoying the feeling of her silky lingerie under my fingertips.

My hand glided down her belly and stroked up the inside of her thighs. I avoided direct contact with her pussy, instead brushing my fingertips closer and closer with each pass. The pretense of sleep was getting pretty thin, so i gently moved her knees apart not being afraid of "waking" her anymore. She "shifted again in her sleep", bending her knees slightly and giving me my first full view of her entire vulva. By now Louise was so aroused that a slight trickle of moisture ran down her labia towards her ass. Oh, I just had to taste that sweet nectar!

I laid down on my belly and crept up between her thighs pushing them wider apart as I went. I gently, oh so gently, ran a fingertip up and down her labia on either side of her pussy and I marveled at smooth she was! The lightest of scents came from her pussy as I gently parted her labia and saw her inner flower bloom at a gentle touch. I moved forward and began to slowly lick her outer lips from bottom to top, first one side then the other. A slight gasp and a sleepy "mmmmmm" moan encouraged me onward. Her outer labia were so smooth and silky and I spent a long time gently sucking them into my mouth then running my tongue up and down in between them.

I took my time and thoroughly enjoyed the new experiences in front of me. Every woman is different, especially when it comes to stimulating her clit. Through careful exploration I soon found that Louise was somewhere in the middle of the range - indirect stimulation of her hood followed by the occasional direct lick from underneath seemed to cause the most wiggling of hips and arching of her back. A direct lick across her clit brought a sharp intake of breath; that was too much stimulation at this point. Her arousal was approaching its peak and she spread her legs wide and lifted up her hips. The moment had arrived and I knew that she wanted to feel my cock inside of her pussy!

My cock was hyper aroused as I opened up a condom, rolled it on, knelt between her legs and began a gentle exploration. Her pussy was wet and her outer lips swollen apart with desire. After some gentle probing, I let my cock knob slip in between her labia and I felt that delicious "click" as I entered her vagina. That sublime moment of initial penetration is like no other feeling! Oh, how I love it!

Not knowing her preference or tolerance for shallow or deep penetration, I started slowly with just the head of my cock resting inside her vagina. I withdrew, rubbed it around her labia and clit, then slowly pushed back in again. Her pussy was warm and tight around my cock. After a while about half of my cock was sliding in and out of her warm, wet pussy. No longer pretending to be asleep, Louise responded to my cock and lifted her hips up to meet my thrusts. We had used no lube; my cock was nicely slick with her wetness.

I paused for a moment, took a firm hold on her hips, then began to slowly push my cock into her balls-deep. My lovers tell me that I'm larger than most other men that they've been with. I'm almost 8" long when hyper-aroused and about 6" in circumference. Even though I'd only been with three other women, I knew enough to go slowly. I never want to cause any discomfort let along pain, only provide pleasure. I could feel the head of my cock opening her up deep inside and I felt the ridge of her womb. I had every inch of my cock inside her pussy and my balls were pressed up against her ass. I savored the feeling and gave her a moment to get used to me, then began to pull out about an inch or so and slowly work my way back as deep as I could. Mmmm, heaven!