Any guy with a mind to and a reasonably good game can bag a married woman who is interested in fucking around. I’ve done it more than a few times, from picking up women at bars and later learning that they’ve got a hubby at home to nailing married coworkers. At the company where I work, our parties never include spouses, and it’s easy to figure which wifeys can be had. It’s all good sport, at least for the professional pussy-hound. I like doing married women because they’re less likely to try to pin you down than single women – at least at first. I guess I also have to admit that I’m always attracted to the forbidden, and I love fucking married women. I had recently decided to up my game and go after a woman who really excited me but who seemed to be a particularly tough one to crack, Eileen.
Think about this set of challenges: married to her high school sweetheart, three kids, regular and active churchgoer (she even talks about church in the office!), in her 40’s, old enough to not do anything rash and last but not least, Director of Human Resources of our company. If I weren’t careful, I could get slapped with a sexual harassment charge before I knew it. One thing that made me a bit comfortable on that score was that we all knew that the CEO was banging the Marketing Director, Mary Anne. She was supremely unqualified for the job, except for her good looks, sexy little body and her willingness to fuck the company founder.
As the CFO of the company, I had reason to deal with Eileen pretty regularly and I began making a point of spending more time in her office. After the real business was done I chatted her up about her kids and even her husband. Ironically, I knew her husband from high school. We were even on the crew team together, but because he was a few years older, I wasn’t friends with him. I’d like to think I wouldn’t fuck a friend’s wife, but I’ve never been tested.
After a while, perhaps because she sensed closeness between us, she’d stop by my office after hours and ask my advice on work-related issues. We both regularly worked until 7:00 pm or so and generally had the office to ourselves. I loved seeing her show up at my office door. Eileen was a sharp dresser, and tended to wear surprisingly aggressive outfits in light of her position. She clearly was proud of her sexy, shapely legs and her skirts were always short. She wore spike heels which only accentuated the shape of her lovely calves. Her hips were womanly, but not too large and her breasts were always highlighted by a fitted blouse. She had short, black hair, rich full lips and high cheekbones. Her dark coloring reflected her Italian heritage, the edge to her personality, the Irish. I breathed hard every time I saw her.
Over the course of several months of this, our conversations became more personal and intimate, talking about our pasts, our joys and of course our disappointments. Finally, I made the ultimate judgment call that it was time to ask her out for a drink. The next time she showed up at my office door, I stood up and announced that I really needed an attitude adjustment at the nearest bar, the “Yankee Doodle” It was on her way home and she immediately agreed to join me. A couple of glasses of wine had the intended effect of allowing for even more intimate conversation.
Eileen and I began making a regular practice of intimate cocktails after work. Now and then I suggested dinner enough in advance that she could give her excuses at home. After one particularly good evening over dinner at one of Philly’s most romantic restaurants I walked her to her car and when she turned to say goodnight I took her in my arms and kissed her.
I could feel her stiffen in surprise but she quickly relaxed and began responding to the pressure of my lips. Feeling her lips soften, I teased them with my tongue and to my excitement and great satisfaction, she opened them slightly and allowed my tongue to enter. We must have kissed passionately for almost five minutes. Her tongue began to actively engage mine and finally entered my mouth. We were both breathing very hard when we broke it off. We looked in each other’s eyes as I held her, kissed quickly and she jumped in her car.
I was exultant. I figured if I could get this woman to respond sexually at all, my chances of fucking her were very good. Now I had to figure out how to do it. She definitely was not a Red Roof Inn kind of gal and even a nooner at a high end hotel wasn’t likely to cut it. It had to be romantic, and natural as two young lovers giving in to passion. I couldn’t give her the chance to think about it.
The opportunity presented itself within a few weeks of that first kiss. In the meantime, we had abandoned our after work office chats and were now going out for cocktails at least twice a week and afterwards making out passionately in her car. She mentioned that she had a human resources conference in New York City at the end of the month and without missing a beat I told her I had meetings with our banks up there around the same time.
“Wouldn’t it be fun to go out together in New York”, I suggested.
“Well, that depends on whether I can count on you to behave yourself”, she kidded.
“Seriously, let’s try to line up our schedules so we can at least have dinner together one night!”
“Oh, I’d love that! I don’t get to New York as often as you high flyers, and you could show me some nightlife.”
I had only one kind of nightlife in mind, of course, but the deal was on its way to being done.
Two weeks later, at about 6:00 pm, I walked out of Merrill Lynch’s headquarters in Battery Park City to head uptown and meet Eileen at the New York Hilton, where she was staying. I had been bold enough to come to New York in the morning without bothering with a hotel reservation. I’d find out soon enough whether my optimism was justified. After reaching the hotel, I called her room from a house phone and she said she’s be right down. I didn’t have long to wait before I saw her walking toward me from the elevators. For all I know, my jaw dropped as I took her in. She had her coat over her arm so that I could admire her strapless little black cocktail dress which showed off her sexy body perfectly. Her arms and shoulders had a shape that showed hard hours in the gym – a look that really excites me. The shortness of the dress really drew attention to her legs and on her feet she wore dressy high heeled mules, popularly known as “fuck me shoes”. Well, all right!
She gave me a big smile, a sweet kiss and said, “Well don’t you look like a Wall Street hotshot!”
“If only I got paid like one”‘ I replied ruefully.
She laughed. “Well, you get paid pretty well mister. Remember, I know all the salaries. Besides, you can’t forget all the benefits of working at Universal.”
“Maybe you’ll remind me of my benefits tonight,” I laughed.
After this promising start to the evening, I told Eileen a bit about the restaurant we were headed to. It had the benefit of being a short walk from the Hilton in addition to being one of the best and most romantic restaurants outside of Paris.
“It’s’ La Cote Basque’ and if you don’t know it, you’ll think you’ve died and gone to heaven”
“Oh, I’m already feeling that way,” she smiled.
The dinner was superb, the wine voluminous and excellent, and the conversation sparkled. If this woman didn’t let me into her bed tonight, she never would. The evening at the restaurant lasted over three hours and by the time we left I doubted Eileen would be interested in more nightlife. I made several suggestions though, so as to not seem overly eager to take her back to the hotel, but was delighted when she responded that she had an early morning the next day.
“After a dinner I’ll never forget, I can’t just say goodnight though. Why don’t you come up to my room and we can order a nightcap from room service?”
Of course I accepted and in minutes we were in her room and waiting for a bottle of Champagne to be delivered. In spite of my optimism, I could scarcely believe how well things were going. Was this practically virginal, religious and oh so hot woman really going to have sex with me? The angle I hadn’t worked out was exactly the right time to find a moment in our conversation when I could embrace her, kiss her and let nature take its course. The conversation and Champagne flowed until suddenly both ran out.
“Well, it’s late and I better let you get to your hotel. By the way, you never mentioned where you were staying. ”
“Uh, I guess that’s because I didn’t bother with a reservation since I thought I might make the last train.”
“When is that?”
“Oh, about 40 minutes ago.”
“So you don’t even have a change of clothes?”
I couldn’t help but give her a nervous smile as I said: “Well I actually have my bag checked down in the lobby.”
Now it was her turn to smile, but slyly. “Oh, we thought we might get lucky tonight, didn’t we?”
“I had no expectations at all!” I protested. “Although, sharing a room doesn’t have to be about sex.”
She turned to the single queen sized bed. “I suppose there’s enough territory there for me to safely share. Go get your bag.”
Things seemed to have gone slightly off course, but I still felt that getting in bed with her, no matter what I had to promise, would lead to good things. By the time I got back to the room, Eileen was in bed and the lights were off except in the bathroom. I dropped my bag, hung my suit up and wearing only my boxers turned off the bathroom light and got in bed. She felt too good about the evening not to turn toward me and give a warm, but innocent hug and kiss. Now I had to parlay this opening into fucking her.
When I strengthened my hug to prevent her from pulling away, she murmured slightly but allowed me to prolong our kiss. From prolonging, I began to intensify it and we were soon kissing as passionately as we ever had. My hands started moving over her smooth body. I could feel her small firm breasts against my chest and thought briefly that if she wanted nothing to happen she wouldn’t have taken her bra off. She still wore her panties but I was surprised to discover that she wore a thong, so I was free to feel the smooth flesh of her muscular bubble butt.
I had a raging erection which I made sure to keep pressed hard against her loins. We behaved like passionate lovers, lost in each other’s bodies, until Eileen suddenly broke away turned her back to me and told me she wasn’t ready for this to happen. For all the women I’ve fucked, the one rule I never broke was that you can’t let yourself beg for it. A man has to act like he can get laid whenever and with whomever he wants. I told her I understood, that it had been a great night and that we should get to sleep.
However, I made it obvious as I removed my shorts and tossed them across the room. A few minutes passed. I was lying on my back, my hands behind my head feeling my erection slowly diminish. On a couple of occasions when I had been disappointed like this, I’d made a point of masturbating just to send a message that I didn’t need whoever it was at the time, but I thought too much of Eileen to try to hurt her feelings. I heard a sigh or two from Eileen and she changed position slightly. Out of the corner of my half closed eye I saw that she was now lying on her side facing me.
Without saying a word, Eileen reached under the covers and took my cock in her hand. At first, it was as if she had never experienced a penis and her hand touched softly as if she were trying to make out its shape. She went on to cup my scrotum in the same way. I had never been touched quite like this and I found it electrifying. My dick returned to full erection as she felt it, which seemed to interest her even more. Finally as if her curiosity was satisfied, she gripped the shaft and started slowly pumping. I made some faint noises of pleasure and encouragement. She continued more rapidly and my response got stronger. Maybe she thought she’d jerk be off so I wouldn’t feel so bad about being shot down, but I wasn’t going to let it go at that. I reached over to her and put my hand on the small triangle of her thong. I was amazed to realize that I was feeling smooth skin underneath. The virginal Eileen shaved her pussy!
Even more gratify was that I could feel how wet she was through the fabric. My final discovery was the best. As I moved my hand under her thong, my fingers encountered an erect clitoris bigger than any I had ever felt. Her reaction to the slightest touch here was extreme. Now I was certain I could stop being the least bit cautious. I threw the covers off, pushed Eileen gently but insistently onto her back and pulled her thong off. I was on my knees facing her and in the dim light I could see her looking at my naked body and particularly at my stiff cock. I was as hard and as I big as I can ever get and she seemed to like what she saw.
I spread her legs and knelt between them, immediately leaning forward to take this huge clitoris in my mouth. It extended more than an inch outside her labia and it really turned me on. I nibbled, I sucked, and I slurped. I took an occasional break to gently chew on her ample labia or explore the inner lips and the entrance to her vagina. She smelled so wonderfully of sex, clean, but musky in a way I loved. My face got covered in juices. When I had her in a true sexual frenzy, I thought I would finish her off with my specialty and then fuck her like an animal. I took her by her ankles and jackknifed her, exposing her lovely ass and anus. Holding her ankles in one hand I leaned down and started playing with her pretty little rosebud. I fingered it a bit, penetrating slightly. It was already covered with juice from her cunt so I felt my finger slip in easily. Eileen kept getting more and more vocal which always turns me on, but I remember wondering if we might get a call to keep it down. I entered her anus with my tongue and she reacted so violently I was afraid she might crush my skull with her strong thighs. She told me later that she was experiencing a series of orgasms starting with my sucking her clit and culminating with my thrusting my tongue into her anus.
I was ready to fuck, and I wasn’t going to bother making it fancy. I put her legs over my shoulders and gave it to her missionary. Even though she had a wonderfully tight cunt, Eileen was so lubed I slid right in to the hilt with one thrust. Because of her tightness and all of her juices, her cunt gave off great sucking sounds as I pounded her. She was lost in her pleasure, playing with her dark erect nipples, but was aware enough of me to regularly give my cock an extra hard squeeze with her vagina. Best of all, I could feel myself bumping her clitoris on every thrust which encouraged me to keep pounding her hard. She obviously was having one orgasm after another. Tell me what guy doesn’t love doing that and feeling like a super stud!
I had pretty good control because of all the fucking I did, and wanted this to last forever, but I knew tonight was just the beginning so I started to let my climax come on. Eileen’s legs were now hooked around my back and she was bucking and mewling. I wanted her to reach a great orgasm with me and I sensed my semen gathering to explode, I reached around and stuck my middle finger as far into her anus as I could. She bucked even harder and opened her mouth and started howling like no woman I had ever heard. I remember the movie where the boys called one of the girls “Lassie” and that’s what Eileen was like.
My orgasm was memorable in its one right. It was a series of explosions of semen as pleasurable as any I’ve ever experienced. I might have been howling too. It took us a long time to stop moving because one or the other of us would get an “aftershock” and have little spasms which would set us off fucking again. When we finally just lay still, arms and legs wrapped together, Eileen delighted me some more by using her vaginal muscles to squeeze the last drops of semen out of me, which is a special pleasure. Finally, one of her squeezes caused my almost limp dick to slide out of her.
Eileen turned her head to look me in the eye: “I didn’t know what fucking was before tonight.”
“Baby, we’re just getting started.”
Eileen blew off her meetings the next morning. We extended our check-out time and by the time we left the room the next afternoon, Eileen knew the basics of giving great head and rimming. I taught her how I liked my nipples played with during sex and she had had her first taste of semen, which she swallowed eagerly. Best of all, she discovered how much she responded to having her asshole fucked and I broke her ass in thoroughly.
I concluded that there was nothing she wouldn’t at least try. I had stumbled upon a complete sexual animal just waiting for a lover to make her overcome her inhibitions. As I said, I LOVE married women!