tagTranssexuals & CrossdressersMy First Shemale Experience

My First Shemale Experience

byEZ_CUM_EZ_GO©

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.

I knew from that, that Dan had probably promised him very little else, leaving the rest of what was to happen, or not happen up to me once we'd reached our room.

"Thank you," I responded back. "And I hope that if you enjoy the performance, you won't feel embarrassed in doing just that while you watch," I now added dropping what I thought was a subtle hint at what I hoped was something he would do for me at the very least.

Once again he smiled broadly, his deep blue eyes offset by a bit of silver coursing through his hair, reminding me at once of my father in a way, which at the moment however, was a strange thing for me to be thinking about. Especially as I was now looking forward to seeing him stroking his cock as I danced.

Dan soon rejoined us, and then the three of us rode up in the elevator together to our room. Once inside, Dan made himself immediately comfortable, more or less setting the tone and the mood for Jerald. Fixing us each a drink from the bar, he then found some soft, sexy music on the radio, which I almost immediately began swaying to there in the middle of the room. Having always been a bit of an exhibitionist, I was getting more and more turned on as I did so. I knew full well I couldn't exactly do a strip-tease as I was only wearing the dress with nothing on underneath it, but I also knew I would work that to my best advantage nonetheless.

With Dan and Jerald both now taking seats as they sat watching me dance, I proceeded to tease them a little with a flash of skin here and there, eventually baring a breast briefly and as seductively as I could, gauging their reactions. As hoped for an expected, Dan was certainly aroused and hard as hell as his obvious stiff erection poked against the material of the slacks he was wearing. At first, I saw no noticeable bulge in Jerald's slacks however, and wondered if I wasn't being sexy enough, or worse...that maybe he was one of those at his age that might not even get it up without direct stimulation. I needn't have worried however, as minutes later when I was finally brave enough to remove my dress entirely, now standing there in front of both men entirely naked, he himself spoke.

"You mentioned outside the elevator that you hoped I'd enjoy myself while watching you," he began. "I hope that meant, you don't mind if I sit here and fondle myself while doing that?" he now asked.

I could only grin in delight upon hearing that, as Dan did. Who in fact now stood before I could even respond, and immediately began to undress. It was perhaps a bit more of a bolder move on my husband's part than I'd anticipated. But seeing him do that, Jerald now stood up as well, joining him as he did so. Within minutes, I had two sexy, very naked men now sitting in front of me, each one of them sporting magnificent, though entirely different looking erections. It was for me at least, a virtual smorgasbord of man meat that I could enjoy and select from at my whim.

Dan had what I had always called a rather beautiful looking cock. Nicely shaped, thick veined, which I found alluring, with a nice length to it, slightly above average perhaps in that regard which was more than enough for me. But the fact Dan's prick seemed and always appeared so rigidly hard while aroused, was something that never failed to excite me. Jerald on the other hand had a bigger prick than any I had ever seen before, no so much longer than Dan's was, though perhaps a bit. But it was his girth that was truly impressive, and though I hadn't really considered allowing things to go nearly that far, I was already trying to imagine what it might feel like inside me.

Still swaying more than dancing really as a new song came on the radio that fit the mood, I now added a bit of touching and teasing myself. Cupping my breasts, thumbing and teasing my own hard stiff and erect nipples, it was a pleasured delight to see both men now sitting there fondling their cocks as I did so. Now finally seeing that, something I had always wanted to do, immediately escalated my own arousal level. I soon slipped a finger inside my wet succulent cunt, and began fingering myself right there in front of the two of them. Seeing the pleasured looks in their faces while I did so, and then seeing Jerald as he actually began slapping his cock with his hand a little, did something to me. I now wanted to touch it myself. And though we again hadn't really discussed it, I looked over towards my husband who was now taking notice of Jerald's added pleasuring of himself, and actually nodded his head in his direction. I took that once again as a signal, that whatever I wanted to do, was fine with him.

But what I did do, was to now beckon towards the two of them simultaneously as I sat down on the end of the bed. "Come here you two," I told them both, pleased when they both stood and immediately walked over to now stand in front of me.

At first I didn't know how either man might react, though I did know Dan considerably better of course, and never knew him to be homophobic or squeamish at seeing another man's hard stiff cock. Even so, I wasn't sure what he might think, do or say as I took each one of them within my hands, now bringing them closer together as I sat there, tentatively licking one first, and then the other as I held them. Their pleasured sighs and moans of approval told me to continue however, which I now did.

Placing their beautiful magnificent cocks side by side, I now wrapped as much of my mouth around the two of them together as I could, sucking them each simultaneously, almost gagging at first as I tried fitting too much of them inside my mouth. Even that act however seemed to stimulate the two of them even more, as their moans intensified, increasing with each additional suck, or rapid flick of my tongue on them as I sat there licking the two heads together.

"I want to try something," I soon said, my very wicked, naughty side now coming out in all its splendid glory. Dan knew, and I think half suspected, that once I'd allowed myself to get that way, anything and everything was virtually possible after that. I always had had this line in the sand that I didn't usually cross, and for good reason. Once I did...I never looked back, and if anything, almost turned into an entirely different woman. The few times I had done so during our marriage, Dan had even commented on that very fact, it was like being married to a totally different person. I had actually a while back, when once getting a massage by a rather attractive woman, had found myself going over that line. She had in fact fingered me to a nice clitty-cum as I called them. Surprised at myself in having done that, as I'd had very little experience really with women. But hearing later how I had, had led to one of the best nights of sex that Dan and I had had in quite some time. So, it wasn't too surprisingly then that Dan very often urged me to cross that line. Once I became that aroused, that totally uninhibited, I could virtually see myself doing just about anything, and very often did.

Having made them now stand facing one another, I took each one of their hard stiff pricks in my hands once again, placing them tip-to-tip against one another. I enjoyed the pleasured sensation of rubbing them back and forth that way, and then wrapping my lips around their respective heads still pressed together, sucking and licking them like that from the side. Once again hearing their pleasures as they moaned, sent a wave of pleasurable chills up and down my own spine. As I did that, I now felt each one of them reaching down and begin fondling my breasts. Being as sensitive as they were, I enjoyed the differing manipulations, which soon sent a flood of pussy juice between my legs, just like flipping a trigger on a switch, or in my case two switches as they stood there flicking and teasing my nipples with their fingers. My honey pot soon reached the boiling point however, and I now surprised the two of them, along with myself as I now slid back into the middle of the bed.

"Jerald? Bring that beautiful cock of yours over here so I can really suck it for you while my husband fucks me," I said laying it all out for them. Not having to be asked twice, Dan quickly positioned himself between my legs, easily sliding his stiff hard prick inside my wet juicy cunt as Jerald now knelt by the side of my head. Grasping his equally hard shaft within my hand, I now proceeded to more thoroughly suck on his prick, drawing it deeply inside my mouth with nice long smooth strokes. Dan's cock doing the exact same thing to my pussy simultaneously, though I knew within a moment or two, he'd soon give that up, and begin spearing me with his dick, just the way I liked it.

It wasn't too long after that, that he was. My husband's prick now driving in and out of my cunt with a rapidity I hadn't actually expected. Jerald now too, basically fucking my face, his cock sliding in and out of my mouth like another cunt, until I soon heard his warning cry of release. I was also glad that he did, as we'd actually not really talked about it obviously. And though I certainly had no problem sucking and drinking down a man's cum, this was after all a first meeting. And though I felt reasonably confident he was safe, it wasn't a risk I was quite willing to take at the moment, so I withdrew his cock from my mouth only seconds before he came. He didn't seem to mind it however as I finished jerking him off, pointing his prick at my breasts, rubbing it back and forth against, and across my nipples as he came. It was a beautifully, erotic sight to behold too, watching his powerful release as he began squirting a torrent of his thick creamy cum juice all over my tits. I kept jacking him off, pumping his shaft, producing what seemed like more and more of the wet sticky stuff, when Dan too suddenly pulled out.

Admittedly this was for me another one of those kinky, quirky fetishes of mine. I simply enjoyed seeing a man cum. I had always enjoyed giving blow-jobs, and enjoyed it almost as much in swallowing down Dan's spunk when he came like that for me, but I'd always enjoyed it more, seeing him actually squirt, either against my breasts, my pussy, and sometimes against my face too. Though admittedly, I still hated getting it in my eyes, so he was usually always careful whenever he did that. This time however, he merely pulled out, now kneeling as he began jerking himself off for me, something else I loved seeing, as he prepared to finish himself off, squirting his prick onto my body.

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byEZ_CUM_EZ_GO© 3 comments/ 99716 views/ 5 favorites

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