Chapter 1 -- Being a Player
I had been laying on my back panting. Sheri (or was it Cheryl?) again had my wilted cock in her mouth sucking off the remnants of the amazingly great fuck session we'd just concluded only minutes earlier. We'd had our first time together -- my usual Friday night date with a hot woman. I loved girls that fucked on the first date, but maybe I sensed that when I asked her for a date.
Sheri was one of the hot women that I'd met at a Boston club. What caught my initial attention was that her body belonged in the Sports Illustrated bathing suit issue -- without the bathing suit, or better yet an old Playboy magazine. I never pay attention to measurements, but I did note the tag on her dress as I pulled it over her head -- size eight. She was relatively thin yet stacked like a proverbial brick shit house with an ass that deserved to be memorialized in an exclusive art gallery. Moreover, she could kiss like an angel and had demonstrated that she could probably suck a basketball through a garden hose.
Sheri had a snapping pussy and was unusually orgasmic. I'd given her three oral orgasms before we'd started to fuck. She liked my brand of oral sex, and tasted like the finest nectar in the universe. Her sexual aromas were amazing and seductive, drawing me in with every molecule. Further, she generated copious amounts of lubricating fluid, so we slid together like it was predestined in heaven to feel fabulous for both of us.
She'd lengthened out our fuck by doing some amazing things with her spasming and pussy control. My friend Rob had explained to me that a 'snapping pussy' could do exactly those things and even suck the cum from deep inside your body.
I wasn't sure that I'd ever had an orgasm as strong as what Sheri elicited from me. I just about blacked out, possibly from the lack of oxygen because I didn't want to take a breath for fear of missing something, some feeling, some emotion.
The only word I could think of was 'Wow!'
Sheri stayed over until Sunday. Most of that time we were fucking. We were insatiable. I loved dates that turned into full weekends. I also had a high batting average for finding girls that would stay. I'd stopped booking Saturday night dates, accordingly. If I found myself alone, I always knew which clubs to go to.
* * * * *
My office window looked out over the Boston Commons. I worked long days Monday through Thursday. Friday I usually left work right at five o'clock to my date de jour, sometimes even earlier if I'd planned something special with my date.
Fortunately, Taylor Reeves, my 'evaluation assistant' kept whatever hours I kept. She was top notch and also sensitive to my moods. She always gave me the eye first thing on Monday, as though to ask how my weekend went. I think I have been pretty transparent, but I rarely say anything about what transpired. My response has often been an eye roll, head nod, or a lecherous grin.
Somehow, Taylor knows that I rarely date the same girl twice in a month, and even that arbitrary time limit was becoming more like every two or three months. There were so many beautiful women to meet and I didn't want to get tied down.
* * * * *
The weekend after Sheri, I had Margo's lush naked body stretched out on the padded ottoman in my bachelor pad living room in Back Bay. I picked the piece of furniture because it was just the right length, width, and height to use for a massage, and I could easily clean the massage oils or other fluids that erupted from the faux leather surface with a regular household cleaner.
I'd worked on Margo's back and limbs as she lay sprawled out naked, but then she rolled over and revealed to me the assets I'd only had a glimpse of a few minutes earlier when she stripped her clothing away and lay down to receive a genuine Josh Bailey Massage. I guess I'd sold her on the idea that I could really do something great for her on a simple Friday date -- a date that I hoped might last all weekend.
I'd met Margo on an online dating site and we seemed to like each other's profiles. I kept my profile accurate to a fault. We'd had cyber-sex together late the previous Tuesday night after we both admitted we were horny as hell. We ended up Skyping. I assured her that the real thing was much better and that I gave massages that were noteworthy.
I'd warmed some more oil on my hands, and then slowly encased Margo's bounteous breasts, massaging the oil into her flesh as I felt her nipples excite and expand to rigid points of passion and sexual excitement. I worked the oil into her skin from her mons 'north', not yet focusing on her sex or the front of her legs.
I sensed Margo's breathing deepen and noted her closed eyes, even though I'd dimmed all the lights in my living room and had some smooth, slow jazz playing. This was going well and her arousal seemed to be increasing. When I sniffed the air, I could smell her sexual pheromones and knew that I find her very wet when I eventually got between her labia.
I shifted and did Margo's feet, one at a time, making love to every toe, and then her whole foot and ankles, her calves, and then her legs up to about six inches from her pussy. As I kneaded her strong quads, she moaned softly, and I felt that she might have just had her first orgasm of the night. I smiled inwardly because I truly enjoyed being the bearer of that kind of female pleasure.
I then moved into what might be called 'Ground Zero' -- her sexual area, only I didn't just charge in there with fingers copping a feel. I worked at slowly filling in my massage between her upper body and her legs, allowing my hands to caress her complete thigh, and her labia majora, as I spread still more oil around her body. Her labia were swelling at a rapid rate, I noticed. They matched my cock.
Margo had large pussy lips that I initially ignored and even avoided touching. She moaned again and I saw her arms flex, as though she wanted to take my hand and steer me into her sex. I pushed the errant hand back into position. This was my massage and seduction.
After a few minutes of circling her sex, and re-stroking her entire body, I returned to her sex, and ran two fingers through her slit. She was soaked. That simple move proved to be the equivalent of pulling one's finger out of a dike. Her fluids almost surged out of her body and ran down her taint, over her anus, and then onto the ottoman. I felt glad that I'd turned her on that much.
My fingers soon found her clit, but not before I'd had two of them inside her body. Margo came in a more substantial way, given up a loud moan as the pleasure hit her. She had to draw her legs up towards her chest due to the intensity.
My mouth followed my fingers into her cleft, my tongue lapping at her sex with an emphasis on the nerve endings of her joy button. A few minutes of making love to that area and she had another 'O', her whole-body cresting and then relaxing back onto the ottoman.
Margo groaned and spread her legs, "Come and fuck me. Make love to me, NOW!" She was quite insistent, and I would never disappoint a woman with a request like that. Her legs spread wide, and I was between them instantly.
Margo stayed all weekend.
* * * * *
Taylor greeted me with her usual smile and curiosity Monday morning. I was totally fucked out, and I knew that Margo was in a similar condition.
Taylor asked, "Good weekend?"
I grinned and nodded. My smile was my answer. I asked her, "How about you? Have any hot dates?"
