My First Ever Shemale Experience

by Thesandman

Caution: This Sex Story contains strong sexual content, including Reluctant, BiSexual, TransGender, Group Sex, First, Oral Sex, Anal Sex, Masturbation, Squirting, .

Desc: Sex Story: Susan and her husband go out for a wild night on the town, little did they ever imagine!

My husband Dan and I have always had a great sex-life, but with the day-to-day pressures of working and trying to make ends meet, we weren't always up for it or in the mood. Because of that, we had made a promise to one another early on, that at least once a month we'd have what we called a "special evening". It was something the two of us looked forward to without fail.

Now don't get me wrong. We always went out once a week, either to a movie or to dinner or both. But that wasn't what we'd meant by having a special evening out together either. Those nights were meant to be above and beyond whatever else it was we enjoyed doing together in the bedroom. In the beginning, it was more along the lines of touchy-feely stuff with one another in public or semi-public places. Just doing that inevitably got us both fired up, and it wasn't often we even made it back home to spend the night fucking there. We'd actually done so in the backseat of the car at one or bar parking lots we had driven to. Surprisingly, as a young woman fresh out of high school, I'd never even done that. Plenty of heavy petting yes, but I'd never fucked any of my back then boyfriends in their cars. When I did it, I wanted to be comfortable in a nice soft bed, not cramped up or twisted into a pretzel while my boyfriend got HIS rocks off. Needless to say, it was a bit of a surprise to find myself actually being turned on by finally doing that.

So it was that our once a month adventures naturally got more and more erotic, and at times a bit more dangerous and exciting too. The previous month we had ventured into yet again a whole new level of acceptance and excitement. We'd talked about what happened long into the night afterwards, fucking wildly between that discussion on and off until we both finally fell asleep totally exhausted. We'd ended the evening in agreement that our "Special night" after that could include just about anything.

At thirty-eight, I considered myself still reasonably attractive and younger looking than my age. Dan of course told me I looked as good, if not more so than most women in their twenties. But he was prejudiced of course, especially when it came to my boobs. Dan had always been a breast man, and made no excuses for it, ogling and enjoying any woman who he thought had a nice rack. I didn't mind his looking either, or even occasional touching or fondling as it turned out, I enjoyed ogling more than one man, and even the occasional woman myself.

I had reddish brown hair that fell well down to the middle of my back, once again Dan having a thing for women with long hair. I had very often jerked off his cock with my hair in fact, something he quite often enjoyed my doing. With fairly large nicely sized breasts, a good C cup, and very sensitive nipples that when he played with them nearly brought me off to orgasm in just doing that, I gave Dan access to my breasts just about any time and anywhere he had wanted. It had been his doing that which had led to what happened the last time we'd gone out for one of our special evenings. And we both knew afterwards, there would be no going back.

I had worn one of my "cum fuck me dresses" for that evening, something I really enjoyed doing just for Dan. It gave me the opportunity to dress up in something I wouldn't have normally worn out in public. And because of that, Dan and I usually went someplace a bit more secluded or exclusive than we might normally do. This time I had worn a dark green emerald wrap around dress. I liked the way I looked in it, and the way it accentuated my long reddish brown hair. Cut the way it was, it gave me a fairly deep plunging neckline for one thing, but for another, with the wrap cut the way it was, it also gave Dan fairly easy access to my breasts. We both loved how he was able to slip his hand inside cupping either one of them, fondling them to his heart's content. Something he enjoyed doing while we sat at our table waiting for our dinner to arrive. Slipping his hand inside briefly between visits from our waiter, once or twice just barely having removed it, giving our cute sexy waiter a bit of a thrill perhaps, knowing what Dan had been up to. But the other thing about my dress that I also liked, it was also very short. It provided him the same easy access to my pussy that he had with my breasts, especially as I wore nothing else on beneath it. So when I say it was a "cum fuck me" dress, it truly was in every sense of the word.

This particular evening, we'd been sitting in a booth enjoying our dinner together having just finished, and now sat enjoying the remainder of our wine. By now, Dan had his hand between my legs and had been slowly fingering my very went cunt for the better part of the last fifteen minutes. Twice I had nearly climaxed with him doing so, though he'd purposely backed off both times, his intention of keeping me damn fucking horny, which I was. During dinner, we had noticed a somewhat older gentlemen sitting alone at a small table across the way. It appeared obvious to us he was more than likely there alone on business as he had some paperwork sitting next to him that he'd early on been going through. During his dinner and ours, he had taken notice of us sitting there across from him, and had even smiled once or twice, with Dan and I smiling back in return. It had been because of that, we'd found ourselves slipping into what became a rather erotic naughty conversation, not to mention some obvious exhibitionism that slowly got bolder and bolder as we sat there. The gentleman soon took notice of it, and continued to smile, occasionally nodding his head in approval towards us as Dan once even revealed one of my large breasts briefly, much to the man's pleasure and amusement. We'd been having so much fun doing that, I actually found myself somewhat disappointed when the gentleman eventually stood having paid for his dinner and prepared to leave. He had come by the table on his way out however, and had said simply, "You have a very sexy wife, and I enjoyed watching the two of you," he'd said and then left before either Dan or I could even comment.

With each of us both so horny by now after our near constant teasing of one another all through dinner, I knew then there was no fucking way I wanted to wait until we got home. But I wasn't in the same mood to finish this out in the parking garage inside the car either. As though reading my mind, though Dan was every bit as horny as I was, we then decided to see if we could get a room for the night there at the hotel rather than going home. As we walked out into the lobby, it was a surprise to see the same gentleman we'd seen earlier, once again a few papers spread out on a table as he sat glancing down at them.

"You in the mood for something really naughty tonight?" Dan asked me as we stood there for a moment prior to walking over and securing a room for the night.

"What do you have in mind?" I asked, hoping it was what I had in mind now as he said that.

Though we had on numerous occasions actually discussed the possibility of including either another man or woman in our special evenings out together, so far we had never done it. Mainly because the situation hadn't really presented itself. It wasn't as though we really knew anyone, nor did either one of us feel in our respective positions at work, that we could very easily accomplish doing that either, until now.

"I was thinking that it might be fun for you to put on a little show for the two of us," Dan told me. He knew that one of my fantasies had always been to do a little erotic exhibitionism, dancing, touching and playing with myself while a total stranger watched. And hopefully in doing that, would become aroused enough to sit there and stroke himself off while I did. I wasn't as sure yet about going much beyond that, but the thought and image of seeing this particular man sitting there doing just that, was at the moment at least, a risk worth taking to find out.

"You actually thinking about asking him if he'd like seeing that?" I asked.

"Sure ... why not? If he says no, we just get the room and have fun anyway, no big deal. But if he says he's interested, and willing to let you call the shots, then why not?"

I knew by Dan's having said I'd be calling the shots, he was basically giving me permission to do as much as I was comfortable with, though at the moment, I wasn't sure to what extent that might be as yet either. Deciding a great deal of that would be dependent on how the guy reacted, if I got more aroused than I already was, and if I felt like I wouldn't be coerced into doing anything more than what I felt I could consciously do.

"Stay here," Dan said not giving me much of an option, though I felt a sudden tingle of thrills running up and down my spine as he walked over to where the guy was sitting. I stood there watching for a moment as they spoke, the gentleman suddenly looking up in my direction with a wide-eyed smile on his face as he nodded his head, and quickly began gathering up his paperwork. As soon as he began doing that, Dan headed over to the lobby's check-in counter as the man approached me as I stood by the elevators.

"Since we've not been properly introduced as yet, my name is Jerald," he said politely taking my hand.

"Susan," I said in response to that, though I'd already made up my mind about not giving him my last name, though I had noticed of course, he'd not given me his either. "Pleased to meet you," I added blushing a little as I stood there, wondering now what all Dan had told him.

"Like I said earlier, you are indeed a very sexy looking woman, and I am both pleased and surprised that you two decided to allow me the pleasure of seeing you dance naked," he informed me.

.... There is more of this story ...

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