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?”

She gave me a ‘Are-you-kidding’ look. “Not me. No dates. I’m not into the dating games. Besides, who’d date me anyway?”

She gestured at her rather simple body and mode of dress. I wasn’t even sure what shape she was under the multiple layers of clothing she always wore, even in the summertime. She pushed her thick glasses up her nose and walked away.

I’d met Gina also having a late Thursday dinner at the little Italian restaurant down the street from my apartment. We’d apparently both worked late and then got to talking since she had the table next to mine. I asked her out for the next night.

By the same time the next night, Gina’s large breasts were flailing in the air over my body as she rode me with a complete lack of abandon. If I was counting correctly, I’d given her four orgasms in our foreplay, and she’d had two more since we started to fuck. She knew how to bring herself off, too. She said it was so much better with a big cock inside her. She was sweaty, but so was I. Good sex is hard work.

I took each of her erect nipples in my hands, pinching between thumb and forefinger. I twisted apparently just the right amount.

Gina moaned as her whole body jerked, “Oh, fuck, ... cumming again.” Her dark hair framed her face as the orgasm rippled through her hot nude body and she froze in position as her pleasure peaked. I could feel her vaginal flutter around my cock, even as I kept my well-paced pushes upwards into her body. Thank goodness my bed had some stiffness to the mattress, otherwise I would just sink into it and there’d be no cock action.

As her orgasm ended, Gina started to ride me again, dropping her wet cunt all the way down my shaft until I had nothing left to offer her – and that was saying a lot. I had been told by more than one girlfriend that I was well endowed.

Eventually, I couldn’t hold back. I warned her of my impending climax, and she doubled-down. My first powerful jolt of semen into her body that evening brought her to yet another pulsing crest. I worried about shooting her off my body due to the intensity that I felt.

Gina fell into my arms, my cock remaining deep inside my Friday night date. Her lips pressed against mine with pure passion. I whispered to her, “I hope you can spend the weekend with me. We can have a lot more fun.”

She seemed to chuckle as her head lay on my chest. “You’re trying to kill me, right?” We were both panting but we laughed.

“Just making us both happy. You are happy, aren’t you?”

Gina pulled away slightly and kissed me, driving her tongue deep into my mouth. “You are the best fuck that I’ve ever had, and you know, because I told you earlier, that I’ve been a bit of a slut since I was in high school that I mean it. You take fucking and foreplay to a whole new level. Oh, and yes, I’ll stay right here until Monday morning -0 if I survive that long.”

I could feel my ego being stroked, but I made sure to distance myself from those self-serving feelings and retain some objectivity in what I was doing – having another highly sexual and enjoyable weekend with a really hot chick. I even thought of breaking my new two-month rule and setting up another date over a month out.

Taylor laughed as I drag-assed into work a little late on Monday. Gina and I had fucked until about three a.m., and then she blew me before we left my condo only minutes earlier. I was washed out but wonderfully sated.

She asked, “Do you ever date the same girl twice?”

I explained about the ‘One-Month Rule’ and how that was getting extended to two months.

She teased, “Are you ever unsuccessful in your quests?”

I shook my head. Sure I got shot down, but not very often.

Taylor chided me, “Well, you’d better shape up this morning. Harrison was down here ten minutes ago looking for you. I lied and told him you’d be ‘right back’, as though you’d gone to the toilet. He dropped off six new target folders for you to research. I assured him that you’d have them done before the end of the day – and that’s in addition to your regular workload.”

I groaned, but took the manila folders from her. I hoped these people all had narrow tracks to follow on the Internet. I didn’t want to find anything suspicious. My job was to research the backgrounds of executives changing jobs; basically, to vet them and compare what they were telling the hiring company to what actually happened, and also flagging out anything in their personal lives that could be an embarrassment or warning about future performance. More than half the people I checked on lied about small things. A few told whoppers.

Tuesday evening as I was leaving work, I again flirted with Monica, the cute receptionist on the ground floor of the building where I worked. I was on my way home to change for a mid-week dinner date with Carolina. I’d barely recovered from Gina, but I did need some pussy and hadn’t seen Carolina for well over a month.

Monica teased as I stopped to say hello. “When are you going to take me out? You know that I’ll make it worth your while. After all the teasing we’ve done, I can assure you that I’m a sure thing. I like you.”

I teased, “Are you sure you want to do that? I still make sure that I have no firm attachment points in terms of my relationships.” I was serious, and didn’t want to just tease her and take advantage of her. I’d done that with others, and had regrets. Now, I tried to make sure that my dates and I were on the same page and had about the same agendas – mostly fun and fucking our brains out.