Making of a Sissy

A number of years ago, I was on an international excursion with my daughter's high school-aged travel water polo team when a series of rather unexpected events resulted in me having a fling with another player's mother.

Truth be told, I had long been attracted to this woman, Rachelle, whose daughter played the same position as my daughter. Despite the girls' rivalry and competition for everything from playing time to statistics, Rachelle and I had become very friendly. We often sat together to watch games, and with neither of our spouses around all that often, I couldn't help but fantasize about getting in Rachelle's pants.

As far as I was concerned, though, that's all it was, a fantasy - albeit one that was fodder for numerous quality jerkoff sessions. I could picture in my mind's eye Rachelle on her knees sucking my cock, or riding me cowgirl style as I stared upward at her ample tits and gorgeous face framed with a sexy brunette hairstyle.

On many an occasion, I would bring myself to a very satisfying orgasm while I pretended to be having sex with Rachelle. As much as I longed to fuck her doggy-style, more than anything, I wanted to eat Rachelle's pussy. I got rock hard just thinking about crawling between her thighs, tonguing Rachelle's moist slit and working her little clitty until she screamed for mercy.

While I was certain that Rachelle's mind was not nearly as sex-centered as mine, I nonetheless had the sense that there was a mutual attraction. Enough more or less innocent flirting, both ways, had taken place to assure me of that.

We were out of the country for a water polo tournament when an opportunity came about that I honestly had never expected. Parents of all the girls had hung out together quite a bit during the trip, both during games and otherwise, and Rachelle and I seemed to be together more often than not. In fact, I think more than one of the other moms became somewhat suspicious, thinking that something might be going on between Rachelle and me.

Anyway, though water polo is a sport most associated with warm, summer-type weather, this particular tournament was played at indoor pools in the dead of winter. Beginning in late December and winding up in early January, the schedule allowed for an adults-only New Year's Eve party in the hotel room of a couple whose daughter was one of our team's better players.

With the girls safely tucked away in preparation for a game the next day, Rachelle and I found ourselves together at the party. Her husband had not made the trip, so Rachelle was on her own, and so was I because my wife had not been feeling well throughout the trip and had opted to stay back in our hotel room and not attend the party.

Rachelle, drinking red wine, and I, drinking beer, really got to talking as the alcohol took effect and our respective guards lowered. At one point, even though it was freezing outside, we adjourned to a patio off the hotel room to escape the noise of the party and find a bit of privacy. The alcohol kept us warm for a while, but eventually we had to go back inside.

"Where have you two been?" another woman asked us, seemingly startled. This other woman quickly whisked Rachelle off to another room, leaving me with half a beer and a semi-hard cock. The thing was that while we had been outside, Rachelle had told me a bit about what she called her "wild college days," when among other things, she said, she had dated a football star who wound up going on to the NFL.

A big football fan myself, I knew all about this particular player, a perennial all-pro wide receiver who had spent much of his career with my favorite team. Now I obviously couldn't be certain, but given this guy's well-earned reputation as quite the ladies' man, and the fact he was black, I could only imagine that his cock was of the proverbial BBC variety. I couldn't help but picture him fucking Rachelle, as Caucasian as could be, and what she would have looked like taking a huge black cock in her mouth and between her legs.

With that vision in my head, the other woman and Rachelle eventually returned, where I had taken a seat on a small sofa in a corner of a little alcove off the main party room. Rachelle sat down right next to me, close, and told me that her friend had wanted to warn her about possibly doing something she would regret.

I told Rachelle that I was certain she had nothing to worry about, but Rachelle said she wasn't so sure. We continued to talk, about more and more personal matters, and fueled by the alcohol, we soon began making out. Of course, we knew full well that we could soon be discovered by some of the other parents, but neither of us seemed to care.

Rachelle was a fantastic kisser, to the point that she had an effect on me that I hadn't felt for years. While in college, I had dated a girl who to that point had been the best kisser I'd ever experienced. Inevitably, when this girl's tongue was in my mouth, doing its nasty thing, my cock would harden in my pants. It was completely beyond my control.

Much to my surprise, the same exact thing happened with Rachelle! Dressed in a rather tight pair of pants, I quickly became very uncomfortable, even though my dick is no better than average size, if that. Speaking of that, it had already occurred to me that if anything were to ever really, truly happen with Rachelle, the size of my cock would undoubtedly disappoint her, especially given her experience with Mr. All-Pro Wide Receiver.

As we continued to kiss, I couldn't help myself and I began to fondle Rachelle's fully covered tits. I simply could not help myself, and Rachelle did not stop me. I had often admired Rachelle's "girls" because she seemed to like to wear relatively low-cut tops that displayed more than a bit of cleavage. Those tits felt unbelievable in my hungry hands, and I could easily discern that her nipples had become erect.

It was only at this point that I began to really consider the possibility of more actually happening. The problem was there was no place to go. My wife and our daughter were in our room, and Rachelle's daughter was in her room. And it was far too cold outside to even consider any such possibility.

Suddenly, Rachelle whispered in my ear.

"If you don't find somewhere to give me that cock, you're going to regret it for the rest of your life," she said.

Knowing full well that she was 100 percent correct, I told Rachelle to come with me, and we exited the party suite. Where in the hell we were going, I had no idea, but once we were well clear of being seen by anyone we knew, I took Rachelle's hand and pulled her along to the elevator.

I remembered that when I was in college, another girl (not the great kisser) whom I had dated and I used to go jogging in the evenings, and then we would run up 12 flights of stairs in our dorm to the very top. There was a flight of stairs even above the top floor of the dorm, and this girl and I would run to the very top and then sit there, cool down after our workouts and talk. I did wind up fucking this girl, although in each of our dorm rooms rather than at the top of the stairs, but I figured if this hotel was constructed in similar fashion, at least that would provide a private place.

Once in the elevator, I pushed the button for the top floor as Rachelle began to fondle my crotch. God, I was hard.

Upon reaching the top floor and doing a bit of a search, I found the door for a stairwell, opened it and was thrilled to see that indeed there were stairs headed upward. I pulled Rachelle along behind me and we ascended the stairs to a landing very much like the one I recalled from my college dorm.

While the floor was harder than even my dick and by no means comfortable, Rachelle and I were both too drunk and too horny to care. Fortunately, given the weather, Rachelle and I each had coats and quite a bit of clothing that we were able to use to provide something of a cushion. We undressed quickly and I soon saw an unbelievable sight that I had never imagined I ever really would.

Naked, Rachelle was absolutely stunning. Her tits, while not huge, were damn good-sized and absolutely magnificent. Her bubble butt was to die for, and her neatly trimmed pussy appeared to me to be nothing less than heaven on earth.

Before I knew it, I was on my back, and Rachelle was kneeling over me. She took my engorged penis in her hands and smiled. Rachelle looked at me, sort of smirking by this time, and lowered her mouth to my aching cock. It was as if she were saying, "Well, I've had bigger, but this is what I have right now, so it will have to do."

As Rachelle began to really suck, I knew that even with all the beer I had consumed, I wasn't going to last long if she kept going at that pace. I gently began to squirm. Rachelle got the hint and removed her luscious mouth from my cock, which by this time was leaking pre-cum.

I rose to my knees and moved Rachelle on to her back. She needed no prodding to spread her legs, allowing me to dive right between her thighs. I gently and slowly began tracing my tongue along Rachelle's inner thighs, moving ever closer to her sweet pussy. God, she smelled good - an intoxicating combination of perfume and natural womanly scent. As I sought her clit with my tongue, Rachelle began to softly purr, and I knew she appreciated my efforts.

After I had feasted on her pussy for quite some time, Rachelle pushed my face away.

"I need you inside me," she said.

I certainly didn't have to be told twice. As I mounted her, I saw in Rachelle's eyes a look of longing that matched my own. While the truth is that Rachelle was only the fourth woman I had ever fucked, the feeling of thrusting my cock into a new cunt for the very first time was unmatched by anything else I had ever experienced.

Wanting to make my time with Rachelle last as long as possible, I proceeded slowly. I was also very aware that rather than being on a bed, we were shielded from the cold, hard cement floor only by our coats and other clothing. I didn't want to hurt this incredibly sexy woman.

Even in what I knew had to be a most uncomfortable situation, Rachelle was a very skilled lover, moving and responding to my thrusts in a fashion that no other woman I had ever been with had. It might be a cliché, but even in such an odd, strange scenario, there was no question that Rachelle was by far the best fuck I had ever experienced.

Unable to last anywhere close to as long as I would have liked, I neared the point of no return and told Rachelle that I was going to cum. After all, I wanted to give her the option of having me pull out or whatever she preferred.

"Give it to me, Baby," Rachelle said. "Cum in my tight, hot pussy!"

As you might have guessed, that sent me completely over the edge, and my cock erupted, resulting in what was probably the lengthiest orgasm I had ever experienced. God, it felt good.

Rachelle allowed me time to come back down to earth, and then, looking me directly in the eyes, she spoke again.

"Clean me up," she said.

Not understanding what she meant at first, I told Rachelle that there obviously weren't any tissues or anything, given where we were.

"With your mouth, bitch," she said.

Flabbergasted, I was completely caught off guard. Bitch? Had she called me a bitch?

Truthfully, I had sampled my own cum in the past, but I had never eaten a cream pie. Rachelle sensed my hesitation.

"Look," she said, "I let you fuck me and cum in my married pussy. There is no way I'm going back to my room with your fucking cum leaking into my panties. Give a girl a break."

Still, not at all sure about doing what Rachelle was basically demanding, I slowly moved my face toward her sopping cunt. Logically, I was willing to admit to myself that she had a point, but ...

"Come on," Rachelle said, impatiently. "It's just jizz. Don't tell me you've never tasted it when you've jerked off."

Realizing that I basically had no choice, I went to work cleaning up Rachelle's pussy. Evidently, I had shot more cum than I had even realized, because seemingly the more I slurped, the more fluid seeped out of her nasty snatch. It wasn't all that bad, really, but I still didn't exactly feel good about what I was doing.

Finally, though, apparently satisfied that I had consumed at least most of my cum, Rachelle pushed my head away. She rolled over and began to get dressed, first putting on her little pink panties. I noticed that the fabric quickly became wet, but I said nothing.

I got dressed as well, and we soon walked down the flight of stairs, got back in the elevator and returned to our floor. I walked Rachelle to her room and moved in to kiss her, only to be rebuffed.

"I don't take cum in my mouth," she said.

As Rachelle unlocked her door and disappeared behind it, I stood there, confused. On the one hand, I had just fucked this incredibly sexy, married woman. But on the flip side, I felt totally humiliated.

Knowing that I couldn't go back to my room and my (hopefully) sleeping wife with pussy and cum on my breath, I took the elevator down to the hotel lobby and found a men's room to wash my face. Fortunately, the men's room was stocked with mouthwash, which enabled me to try to hide the "evidence" of my infidelity.

Nothing ever happened between Rachelle and me again, although from that point forward, whenever we were out of earshot of anyone else, Rachelle would always tell me the same thing, with a twinkle in her eye.

"It's just jizz," she would say.

Looking back on it now, all these years later, it's pretty easy to determine that the experience with Rachelle is what began my journey toward becoming a sissy. And yes, she had indeed called me a bitch.