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My First Shemale Experience

By: EZ_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.


My First Shemale Experience



But the thing that happened now, surprised us both. And it was equally erotic, though surprising to each of us when it happened. Having finished spurting off himself, Jerald had quite naturally moved away a bit, in order to watch Dan I'd supposed, just as I was, now resting on my elbows looking up at him as Jerald slithered down on the bed so he could too, I again thought. Instead however, just as my husband pulled out of me, now stroking his prick, we both watched as Jerald's hand reached down, now clasping my husband's cock, and took over for him. To my surprise, Dan allowed it, looking down, seeing another man's hand now working his cock back and forth, up and down, rubbing it against my sweet tender clit.

"Oh yes! Yes! Fuck yes!" I bellowed out, enjoying what I was seeing, surprised at it perhaps, but so thoroughly involved in watching it now, I almost forgot about myself and the fact I was hovering on the edge of a mind-blowing orgasm!

"Here it comes! Here it fucking comes!" Dan cried out, and then began spurting wildly, copiously, as Jerald continued wanking his cock, jerking it, squeezing it, forcing more and more of my husband's lovely rich sperm to begin shooting all over me. We all watched it splash between my breasts, and then downwards against my belly, finally once again between my legs as Jerald tickled my clit with my husband's cock, still milking it.

And as he did that, I came.  It seemed like it had been a long time since I had come that hard. Not that I hadn't had very nice, very satisfying orgasms before now. Because I had. But this one for some reason, literally felt like it blew the top of my head off. I actually saw stars, and then felt dizzy and lightheaded, collapsing back into the bed, the sensation of my husband's prick still being gently rubbed back and forth, up and down my slit was a heavenly sensation.

Seconds later, I came again.

It wasn't long after that, that Jerald finally left, leaving us alone where we spent half the night fucking one another wildly, almost crazily. And then, in between times, discussing what had happened, the somewhat crazy bizarre finish, and yet even then...how erotic that had been for each of us, seeing Jerald jacking off Dan's cock until he came on me, squirting himself everywhere. 

I had loved it. And now looked forward to doing so again. Though I wondered silently if Dan would as after that night, he never really mentioned it again either.

**

Oddly enough, we continued to have some of the best sex together that we'd experienced in ages it seemed during the course of that month. Our private pillow-talk got dirtier and dirtier too, with each one of us sharing the most decadent fantasies with one another, most of which I honestly admit, I might think about privately, but never truly do. Still, it was a rush to be able to do that, to share with Dan some of those somewhat twisted thoughts and desires, and for him to do the same thing with me. By the time our next "special evening" rolled around, I was ready and prepared to do just about anything.

As we normally took turns planning our special evening out, it was now my turn to do so.  One of the places I had enjoyed going to in the past was a local strip-club, not so much for the professional dancers we had seen there, but more so for the amateur night that they held every couple of weeks.  I found those evenings far more interesting and exciting, as adventurous normal everyday women would find themselves up on stage dancing much to the delight of everyone, including the other women in attendance. I had even once thought of going up on stage myself, but then recognizing someone I worked with who happened to be there that same night, quite naturally decided against it. Still...I enjoyed seeing the women every bit as much as Dan did, and had the time before actually been propositioned by one of them in the ladies room. Though not expecting that to happen again, I left the option open in the event that it might. With Dan more or less surprising me with inviting another man into joining us, I now felt it was only fair that should I be approached, that I too might then invite another woman into joining us.  Our home was just a short hop and a skip away from the club, so I figured if something like that were to happen, we might have a better chance of enticing her back to our place for some fun as opposed to trying to go anywhere else.

As was expected, the place was already packed by the time we arrived. It was always a big night for whatever reason, though I'm pretty sure it had a lot to do with so many women competing for a mere hundred dollar prize for dancing topless, as bottomless dancing wasn't allowed at the time. Still, most of the women nearly did anyway, eventually stripping down to not much more than their "G" strings and thongs, many of which even then left very little up to the imagination.

We were still hoping to slide into a table at some point, content at the moment to sit further away by the bar, lucky enough to have gotten two chairs there shortly after we'd come in. We had already watched a handful of dancers, some of which had been erotic as hell to see dance, shaking their breasts, jiggling them wildly, much to Dan's delight as he again did have a big thing for seeing that. And at the moment, looking down at his groin, he indeed had a big thing pressing against his slacks.

Having gone through a few drinks already, I then excused myself and headed off to the ladies room.  I was surprised to find it virtually unoccupied, though with the contest going on at the moment, most everyone was watching it and waiting until there was a break before everyone came back on stage to do their second contest dances.  There were only two other women inside as I came in, one using the stall, another just then at the sink applying a bit of fresh makeup. I smiled inwardly as she saw me, looking me over and then boldly ask.

"You dancing tonight?"

I realized then she was one of the women I'd seen dancing earlier. Her outfit telling, as she wore no bra beneath the tight fitting blouse, her nipples pressed hard against the material, and her tight short-shorts, clearly outlining the obvious camel-toe she was showing off. I'd actually enjoyed watching her dance, and then told her so.

"No, I'm not. Don't have near the talent everyone else seems to have, nor do I really have the guts for it either," I added. "Enjoyed watching you though," I said smiling at her, seeing her smile back upon hearing that.

"Thank you, and I hope you vote for me then," she said actually winking at me, and I was half hoping at the moment she might flirt with me a bit more. It was obviously way too early to expect much else, and especially with her dancing in the contest, but I was actually hoping for it, and somewhat disappointed when she soon left.

I then entered one of the vacant stalls and sat down to pee. After I finished and came out, I did so at almost the exact same time the woman who'd been sitting next to me did. She was a small somewhat petite sexy little thing with long blonde hair, though she had what Dan would certainly call a nice rack. Not overly big boobs for her small frame, but certainly large ones even then. We found ourselves standing at the sink washing our hands before we each began applying a bit of makeup.

"Are you dancing?" I asked curious, as I hadn't seen her until now.

"Oh no, just here to watch," she told me. "How about you? You dancing?"

"Nope, wouldn't dare. We're just here to watch too, my husband and I," I now added seeing what looked like a bit of a twinkle in her eyes as I said that, though I noticed looking down at her long fingers, she didn't wear any sort of a wedding ring. "Yeah, we just love coming on amateur night," I continued, not really knowing why I'd decided to try and strike up a conversation with this woman, but there was something I found interesting about her, without being able to put my finger on it. I was pleased when she stood, still listening without appearing to be in too big of a hurry to go back out. 

"I think you should go up there and dance, I'd certainly vote for you," she told me. "You have nice looking breasts, and I'm willing to bet you'd get a lot of votes from both the guys and the gals in showing them off."

I laughed at that, though appreciating the compliment. "Looks to me like you'd do just as well yourself. My husband tends to like large breasts too, enjoys seeing it when I wobble mine a little, which is one of the reasons we enjoy coming here on this night, as so many of the dancers here do just that on amateur night, seems to drive the men wild seeing them do that."

"I know what you mean, they do tend to do that don't they?" she smiled warmly towards me. 

"Yes they do, and like I said, it gets my husband even more excited and aroused for afterwards, always a big plus, especially if we're lucky enough to meet someone, and invite them back to our place afterwards," I said suddenly, surprised that I had, knowing full well I was stretching the truth here a little in doing that. But...I was after all fishing a little here too, wondering what she might think or say upon having heard that.

"Sounds like fun she said, " but then disappointingly, gave herself one last glance in the mirror before walking out. As she reached the door however, she actually turned towards me. "So...where are you guys sitting anyway?"

"At the bar...still waiting for a table to open up."

"Listen, we've got a booth...it's not close to the stage or anything, but it is a bit more comfy and secluded. You're welcome to join us if you'd like," she stated. 

"Thank you, maybe we'll do just that," I answered her back, and then followed her out. I was pleased to see Dan's eyes catch mine as I waved him over towards me, still following the petite young blonde whose name I still didn't know yet. Seeing me following the girl, Dan quickly grabbed our drinks and hurriedly came over. 

There was a fairly young looking man sitting in the booth as the blonde slid in next to him, an obvious look of surprise on his face as I approached, now sliding in next to her just as Dan reached us carrying our drinks.

"Hi," I said introducing myself, and then my husband. "My name is Susan, and this is my husband Dan," I told them both.

"Daniel, though all my friends call me Danny," The blonde said taking my cue, and then introduced her male companion. "And this is Steve, he's my roommate," she said easily without coming right out and claiming him as being any more than that. "Unfortunately, he can't stay with us very long, which is why he's also not drinking. He still has to go to work tonight, but he came with me long enough to watch a few girls before having to do so."

"Sorry to hear that," I told him.

"Yeah me too...tried to get off, but couldn't manage it," he said looking over curiously at Danny and then leaned over whispering something to her which I couldn't overhear. She smiled sweetly at him and then answered loud enough so I could.

"Don't worry, I'll find a ride home I'm sure," she assured him, to which Dan immediately spoke up.

"We'll be glad to give you one ourselves," he stated, and I noticed as he did that, he was looking at her chest none too surprisingly.

"See? All taken care of!" Danny laughed patting the young man's leg as she said that. He merely shook his head and smiled, though again speaking.

"Well, just be careful...you know," he said though now eyeing my husband back.

"She'll be safe enough with us," I assured them both, now pleased to see Dan looking back up at the stage as opposed to staring at the young woman's breasts again, in the event Steven was a bit too possessive of her.

We watched a couple of dancers dance, to which Steven then announced it was time for him to leave and go to work. He slid out without kissing Danny or showing any real sign of affection, and I took that as an indication that perhaps they really weren't anything more than just actual roommates.

"Well, call me at least after you get home, let me know you're ok," he asked giving her a somewhat worried look. Once again she glanced quickly at the two of us.

"I'll be just fine. But yes...I'll call you. But don't be too surprised if it's really late either, I plan on being here for a while," she then added. With that, we watched Steven leave, though she then turned back towards us speaking again. "Don't mind Steven, he just looks out for me, always worried about me. And he really is just my roommate, he actually has a girlfriend, so we're more like brother and sister as opposed to anything else."

As the dancers began doing their second dances for the contest we ordered another round of drinks. Waiting for our waitress to return with them, Danny looked over speaking at me. "Really do wish you were up there," she said. "I'd have enjoyed seeing your boobs."

"Yeah, me too," Dan said chuckling. "Though I hope you don't mind my saying this, I'd have enjoyed seeing yours too," he told her, to which I quickly agreed.

She seemed to actually blush a bit nervously upon hearing that, though she answered quite provocatively.

"Maybe afterwards," she smiled back at the two of us. "On the drive home or something," she then added.

Dan looked at me, a curious expression on his face as I winked at him and whispered, "Might make for another interesting evening huh?" He grinned back, now even more hopefully.

"That sounds like fun, especially if you'd be ok with coming back with us to the house, it just so happens we do have a hot-tub, if you're interested," he told her.

She seemed to hesitate upon hearing that. "Maybe, we'll see," she said not yet committing to the idea as yet, though I reached over taking her long fingered hand in my own.

"Don't worry, neither one of us bites, unless you want us too," I said causing her to giggle briefly upon hearing that.

"Watch what you say," she shot back. "Because I do too. But before we decide to do that, there is something I do need to tell you both later, so after hearing that...you might change your mind," she said looking very serious now upon saying that.

Curious, I wanted to prod her further into saying more, but the contest finalists were now on stage and the voting was about to begin taking place with a show of hands for the eventual winner. I decided then to be patient and wait until after the contest was over, before suggesting to her that perhaps we leave, and find out then what it was.

With the winner announced, and things beginning to wind down, I felt it was now or never, and so asked her again.

"Well, would you like us to take you home? Or would you prefer coming back to our place for a bit?" 

Once again she seemed to hesitate before answering. "How about we go out to your car, and then the two of you can decide after that whichever of those two you'd prefer," she said somewhat mysteriously.

Dan too looked at me curiously himself upon hearing that, but we soon slid out of the booth and headed outside. Opening the door for her, Danny slid into the back seat, sitting in the very middle as Dan and I got in, still wondering which way we'd soon be heading here as we turned around now facing her.

"You said there was something you wanted to tell us before we left," I stated hoping that would be the prompt to find out what was really going on here, which it was. 

"One of the reasons my roommate cautioned for me to be careful was, because some of the people I've met in the past haven't been too kind to me after I've told them about myself. So I'm sort of hoping you won't be like many of those, and simply leave me standing here after I do."

"Why on earth would anyone do that?" Dan asked honestly.

"It's easier for me to show you, than to tell you," she said, and began undoing the buttons on her blouse. For a moment, I expected to find out she either had fake tits, or had had some sort of reconstructive surgery or something, and that that was what had turned someone off.  To both of our surprise however, Danny revealed a rather impressive pair of breasts, which I damn well knew Dan enjoyed seeing as she sat there baring them to us.

"Ok, you lost me here," I told her. "You've got gorgeous breasts, far prettier than my own I think, so what's the problem here? You trying to tell me people don't enjoy seeing your boobs?"

She actually did laugh at that. "Not exactly no...they do tend to like my boobs, and that's the problem, you see...in addition to these," she said now cupping them in her hands, "I also happen to have a cock too!"

I know for a fact I wasn't sure I had heard her right, though it was Dan who immediately spoke up, asking her to repeat that.

"What did you just say?"

She shook her head, already rebuttoning her blouse in preparation for leaving. Maybe it had something to do with the tone of Dan's voice or something, though I hadn't heard it to be derogatory when he's said it. Perhaps it was just having heard people say it so many times before, and their actions afterwards that she'd come to expect being tossed out, or left to stand at the side of the road after revealing herself as to who and what she really was.

"I didn't mean to mislead anyone," she said now reaching for the door. "I'm sorry...I'll get out."

"No! Wait!" I almost yelled at her. "We didn't say anything about asking you to leave now did we?" I said turning towards Dan, though initially the look on his face almost suggested that, though it quickly softened.

"No...we didn't, but I for one am now curious...you really are as they say, a Shemale?"

"I'm not real fond of the term, but yes...I guess that's what you would call me, yes. I have boobs, natural boobs, not implants as I showed you, so they are real. But I also have a cock, and have no intention of having it removed or anything like that either. I'm one of those few who enjoys having both, not sure I want to go and do the entire switch over. I consider myself a woman, in every stretch of the imagination, but I do have a cock, though I look at it more as having a rather large clit, though some would obviously think and feel otherwise. But to me at least, it is. So...there you have it. I have tits, real tits, and I also have a large clit. A clit that still squirts, ejaculates and shoots semen. So, now that you know the truth about me, I can either get out here if you'd prefer, or I'd still appreciate the ride home if you don't mind doing that."

Dan's face was for the most part still pretty expressionless. Though I know he was mostly surprised, and still at a loss for words, I spoke before he could say anything that might be misconstrued one way or the other.

"You didn't say anything about coming back with us," I now stated, surprising Danny, and most likely Dan himself as he now turned with a curious eyebrow towards me. "Oh come on Dan, what's the difference really from what happened on our last special evening?" I asked him. "You yourself said that was hot and exciting, the way I see it, it would no doubt be pretty close to the same, with one minor exception here. This time, you'd have two pairs of breasts to at least play with if you think about it. And besides, didn't we just recently discuss that this night was meant to broaden our horizons? Perhaps do things we might not normally do otherwise any other time?"

I was glad to see him finally relax as he smiled. Then he turned around in his seat once again facing back towards Danny.  "I have to ask, do you prefer men or women?" It was nice to see her actually smile when he asked her that.

"Both actually, every bit as much," she said truthfully. Dan turned back around, starting the car. The fact he hadn't asked her where she lived said enough. She and I both knew then where we were going...back to our place.

**

Even though Dan had seemed a bit calmer about all this than he had in the beginning, I had caught his quick brief look after we got out of the car. It was obvious he still wished to speak to me privately as we soon after headed into the house.




My First Shemale Experience



"Dan? Why don't you go out and remove the cover from the tub, I'll show Danny where the guest room is, and let her undress there, and give her one of our guest robes, or towels to wear outside to the tub," I stated as he headed off to do that, and as I led her inside to show her the room.

"You're sure about this?" She asked as I showed her the guest room and where she could leave her clothing.

"We wouldn't have brought you home with us if we weren't," I assured her, though I was still curious to see what Dan had to say about all of it. "Now...feel free to use whichever of these you'd prefer. After that...just come down the stairs and head out through the den area. The tubs directly behind that out on the deck," I told her. As soon as I left, I quickly headed outside to where I knew Dan would be waiting for me.

Sure enough he was.

"Well? How do you feel about all this?" I asked him point blank. "Personally, I think it will be interesting."

"To say the least," he told me. "I'm still not sure what to think to be perfectly honest with you Susan, but I will say...I find the thought of seeing her naked curiously arousing, especially seeing her with you, how do you think you'll feel about that?" He now asked.

"I don't have a problem with it," I told him. "If anything, it will probably prove more interesting for me than for you. Once again...I get another cock to play with, but...I also get a nice pair of boobs to play with too. As will you, since I know how much you enjoy doing that. The problem as I see it, in touching them, her...will you still be thinking of her as being a man, and not as being a woman, which she is emotionally."

"I don't know to be honest, but...I will say this, I'm willing to see how it goes. Not making any promises one way or the other, but if I'm comfortable with this, or with that...then so be it. And if I'm not, then hopefully no offense will be taken, and I'll just do what I am comfy with. But I am looking forward admittedly, to seeing the two of you together more than anything else at this point. The idea is after all a bit kinky if you think about it, which I have been."

I looked down at my husband's crotch, sure enough, he had an erection already. "I can see that," I laughed, rubbing it affectionately with my hand. "So, in that case, what say you go in and get undressed, I'll just undress out here and wait for her to come out. So bring me a robe when you do," I asked him. "Oh, and bring us something to drink when you do, it might help."

"Ply me with enough booze, and I'm apt to do anything," he told me. I laughed watching him turn to leave.

"Promises, promises," I shot back at him, and then began removing my clothing.

**

I was in fact naked and sitting in the tub when Danny came out. She had chosen to wear the towel, and had it wrapped snuggly around herself. Seeing her glance about and not seeing Dan, I answered her unasked question.

"He's getting undressed now, and making us a drink," I informed her. "Come on, get in."

Somewhat shyly, she unwrapped the towel from around herself, hanging it up on the hooks we had provided just for that purpose. I tried not to stare at her as she then turned around in order to step down and into the tub, my first glance quite naturally at her breasts, which I'd only seen briefly before in the back seat of our car. They were honestly beautiful, nicely shaped, full with twin hard tipped nipples appearing on each that looked begging to be sucked. And then as she eased one leg over the edge of the tub, stepping down into the pool, I then noticed her still flaccid cock, or rather her large clit as she called it.  In an odd sort of a way, I was almost glad that it wasn't very big, which it wasn't, though it was again also flaccid. I'd seen Dan's cock on enough cold days to know their equipment had an amazing capacity to all but shrivel up and hide whenever it was cold, and then turn right around as get as big and as hard as it could possibly be in the next minute. I found myself wondering about Danny's then, and how it might look when she too got excited, if she even did. Her balls I did notice were small, though she still had them, and wondered if that hadn't had something to do with the hormonal injections she'd obviously been taking in order to grow and enlarge her breasts.

I had also now tried looking at her in ways that I hadn't before. Her almost non-existent Adams apple the first thing I finally did notice, though not really looking for it before, I'm not surprised that neither Dan nor I had noticed it earlier. Her face wasn't at all masculine looking in any way either. I had personally seen a few x-rated videos of women who were likewise considered Shemales, and in many of them I had though most of those to be quite masculine, even with them having tits. But...I had also seen one woman in particular at a convention in Las Vegas Nevada, who not only looked beautiful, but who had many so called "straight guys" fawning all over her and wanting her autograph, even knowing she had a cock between her legs. 

Danny finally settled down in the tub sitting next to me as I scooted over even closer to her.

"So, you're sure about all this?" She asked worriedly. By way of an answer, I reached over cupping one of her breasts and began playing with it. 

"This answer your question?"

She sighed pleasurably, and then reached over to begin playing with mine, which is what Dan saw as he came outside carrying our drinks on a tray. It was nice to see he was still hard, and at least unafraid to be showing himself off like that as he set our tray down, and then removed his open robe hanging it on one of the other available hooks, along with one he'd brought out for me.

"You have a nice looking prick," Danny stated as Dan stepped down into the tub, though he sat directly across from us in doing so.

"Thanks, and you have a nice set of tits too," he said honestly meaning it as the two of us sat up just high enough in the water that you could see the two of us sitting together baring them as we did. "As well as you honey," he added almost as an afterthought, though I didn't take it personally as he'd more or less been simply exchanging compliments and courtesy's with her.

"Ah huh," I said teasing him, though I now even more openly fondled Danny's breasts as we sat there, letting him see the two of us now doing that together.

After that we sat sipping our drinks for a bit, warming up to one another perhaps, though I could tell in Dan's eyes he still had a few curious questions to ask, still somewhat hesitant in doing so. I think Danny sensed it however, and immediately spoke putting everyone at ease.

"You know, if there's anything you'd like to ask me, please feel free to do so. I'll honestly answer any questions about myself that you have."

"Ok, well in that case...I do have a couple I've sort of been wondering about."

"What a surprise there," I chuckled sipping my drink, winking at Danny as I did.

"Go ahead Dan, ask me."

"Ok, in that case, I will. You mentioned earlier that you enjoy both men and women pretty much equally. Can I assume from that then, that you're ah...well, your equipment functions naturally in that regard? I mean...you do actually enjoy having intercourse with a woman?"

Danny laughed. "Oh yes, very much so," she told us both. "I mean, in that way at least, it is nice to still have a cock, though as I said earlier, I really don't think of it in that way so much, as just having a little larger clit, that I can do others things with too," she grinned.  "But yes, I also enjoy sucking a nice hard BIG cock," she added. "Because mine just isn't, I mean, not really...not like yours is anyway," she said looking down at Dan's which could be easily seen in the water as he sat there as we'd not yet turned the jets on. "And you do have a rather impressive looking prick if I might add."

I almost laughed, seeing my husband blush when she said that.

"And you have...a really big clit!" He stated deadpanned, as we all then burst out laughing with the sudden ease in the sexual tension that had been growing. After that, we all settled down to chat amiably for a few more moments, though before long my hands once again drifted back to playfully caress Danny's breasts. With a simple look towards Dan, he then slid over to sit next to Danny on the other side and tentatively reached out to begin playing with one as well.

"See? They really are real!" She stated contentedly as together, the two of us now began tweaking and rolling her hard extended nipples between our fingers.

"Yeah, damn...they are, and they feel nice too!" He added as my husband sat enjoying himself.

"Go ahead sweetie, give his cock a little feel too," I told her speaking for Dan, though he didn't flinch or pull away when she finally did reach over, wrapping those long fingers of hers about his very hard cock and began exploring it there beneath the water. In doing that, it opened the door for me as well, as I'd been long curious myself about Danny's clit-cock. Reaching down between her legs, I soon found her still somewhat flaccid little prick, softly caressing and playing with it as it began to slowly firm up within my hands, though hardly growing larger as I did so. Still, it was an interesting experience to feel this hard firm little prick as it stiffened. The urge to see it up close and personal now driving me to suggest that Danny sit up out of the water on the edge of the tub so I could do even more.

"Let me suck and lick it," I breathed hotly into her ear as she rose up out of the water, sitting on the edge as I'd asked her. Dan too did the same, still sitting beside her, enjoying her breasts, her hand once again back to his cock as she sat stroking it as I now knelt between her legs. 

It was either the smallest cock, or biggest clit I'd ever seen. Though the other thing I will say, at the moment, it was also the hardest little damn cock I'd ever seen. Feeling like steel in my hand, I leaned over sucking the entire length of it into my mouth quite easily. As I did that, I felt Danny lean over, moving with her as she did, glancing up briefly just as she slipped her mouth over my husband's cock. Once again he sat there with his eyes closed, smiling pleasurably as she now began sucking him, me sucking her. I smiled inwardly upon seeing that, a special decadent thrill for me, something I'd often expressed to Dan about my own personal thoughts and fantasies we'd had before about watching him with another man. It wasn't something I thought I'd ever actually see him do.  Our episode with Jerald coming about as close as I thought we'd ever get to that, but now with Danny, being partially a woman at least, and in a strange way bridged that gap.

With the three of us fully aroused at this point, I now suggested we move this inside the house into the bedroom.  Drying off, I was pleased to see it when Danny simply carried her towel over one shoulder into the house as Dan and I both led and followed her in. Her sweet little girl cock sticking out proudly in front of her as she walked, Dan's much larger prick so angrily swollen, sticking equally as stiff and as straight as the three of us quickly climbed the stairs leading up to our bedroom.

We soon all collapsed un-ceremonially onto the bed laughing as we did. Almost immediately Danny and Dan were taking turns sucking my breasts, teasing my own rock hard nipples as I in turn reached down grasping each of their pricks within my hands stroking them both simultaneously. 

One of the things Dan and I had discussed in the past, but had obviously never done of course, was having someone joining my husband in double-fucking me. He and I had on some few occasions enjoyed anal sex, and I had always wondered what it might be like to have both of my pleasure holes filled at the same time. As aroused as I was at the moment, and that imaginary line of mine again crossed, I figured that now was as good a time as any to suggest it. When I did, I saw Dan's eyes light up in surprise, but the smile on his face immediately told me he was all for it, if Danny was too. A little surprised herself, she quickly agreed however, as I grabbed some of our KY lube from the nightstand and quickly slicked up my husband's cock prior to his penetrating my ass.

With Dan now lying on his back, I soon straddled him slowly easing myself down over his cock facing away from him as I did so. Having done this before, it wasn't at all painful as we'd taken time to ensure he and I were both well lubricated. Once I'd engulfed him fully, I sat allowing myself to get used to the sudden intrusion. Once I had, I then leaned back slightly presenting my now very vulnerable cunt to Danny. Expecting her to likewise now mount me, she informed me she wanted to suck my clit a little first, especially as accessible as it was at the moment.  Feeling her tongue as it soon began tickling my clit, with Dan's hard stiff cock throbbing in my ass was pure pleasure. So much so I nearly came while she did that, almost forgetting all about having her penetrate me. After several minutes of her tongue bliss however, she finally moved upwards, and then slid herself against me, her steely hard prick rubbing against my clit directly as she held it there, now teasing me a moment before finally slipping herself in.

Again, it wasn't as though she filled me, not in the same way Dan's cock was certainly doing inside my ass, but it was a very pleasurable sensation nonetheless as she slid inside. I could feel her tiny cock as it hit my "G" spot perfectly, my clit pressed against her precisely as the two of them now began moving together in perfect harmony. I felt my first orgasm of the night quickly building to a crescendo that moments later seized me inside and out as I came screaming out my pleasure deliriously.

Quivering in ecstasy and still impaled on Dan's cock, Danny now withdrew hovering on the edge herself. I could see her pleasured look as she now stood directly in front of me there on the bed, her release imminent as she now stood fisting her tiny cock.

"On my tits!" I called out excitedly, expectantly watching a second later as the first creamy spurt squirted from the tip, drenching my breast before she moved it over aiming at the second one, releasing another long streamer of her Shemale girl spunk against me.

As she did, it proved too much for Dan to resist any longer. Allowing himself a deep-throated groan, he came, filling my ass with his semen as one glorious spurt after another filled my tight hole.  We crashed together in a pile of arms and legs resting for a bit, before I finally got up and went into the bathroom for washcloths, soap and fresh towels. After we had cleaned up and collected ourselves, we went back down the stairs into the living room for another drink and thus continued our conversation and play there.

Much to my delight it wasn't long before Dan was sporting yet again another nice erection. As I knelt before him on the floor and began licking his re-aroused prick, I beckoned over towards Danny to join us. In moments she was licking his shaft right along with me as the two of us pleasured him, taking turns sucking his prick or licking his balls.

By now Danny's cute little cock was hard again too and I felt like sucking it again, though it was then that I also came up with another wicked idea.

"Dan honey? You've already had my ass this evening, how'd you feel about doing another one?" I questioned seeing the look of surprised delight in Danny's face as I said that. She looked at Dan expectantly, hopefully.

"Why not? Already fucked yours, might as well fuck hers too," he said. Though this time in addition to the lubricant he went upstairs to get, he also came back with a condom as well as further protection. Danny was just fine with that, and helped to roll it onto his prick while I lubricated her tight little bum hole in preparation for my husband's taking her there.

Once she was ready, Danny knelt on the floor, Dan behind her as he slowly eased his shaft into her even tighter ass. Slithering beneath her, I then wrapped my own lips around her hard little cock and began sucking it as Dan speared her from behind. Hearing the slap of my husband's balls as he slowly increased the tempo of his fucking her was highly erotic, especially when she now leaned forward a bit more, her mouth now capturing my clit as we sixty-nined there together.

"Oh yes fuck me!  Fuck me! Fuck me!" Danny wailed into my pussy as she drew closer and closer towards orgasm. My own wasn't far behind at this point either as she went back to gently chewing and sucking my clit, though I knew the moment she came, I would as well, and Dan not far behind either one of us when that happened.

And as though we had somehow planned it that way, it's exactly the way it happened too. Seconds later I felt Danny tense up, though her lips acted like a vise, clamping down around my own swollen clit. I then felt the sudden throb of her clit-cock inside my mouth, the warmth of her semen suddenly squirting inside just as my own cunt gave way. It was one of those rare, somewhat unexpected explosions for me too, my pussy squirting a streamer of my own girl cream into her mouth as she began drinking it down, just as I was still doing to her. From behind, seeing and sensing the two of us climaxing, Dan shoved on more time deeply holding himself inside Danny's ass, and discharged a torrent of his own sweet cream, filling her ass.

This time when we all rolled away from one another we were all totally exhausted and thoroughly spent. Dressing, Dan and I then drove Danny home, dropping her off safely at her place after taking her number as well as reminding her to call her roommate. On the way back home we spoke about the wild night we'd experienced, so unexpectedly and admittedly somewhat surprised by it.

"Well babe, as interesting as it was...and it was, I'd still like to spend our next special evening seeing you with another woman, a woman, woman this time if we can manage it."

I laughed at that, I did sort of owe him for that, and knew immediately as I said it what I could do for him, another "naughty" surprise I was sure.  My sister Karen was coming for a visit in a few weeks. We had secretly talked and shared a few thoughts together, one of which was her obvious attraction towards Dan, and he her though we'd never actually done anything about it, or even remotely considered it as a possibility. I knew then in the morning I had a call to make. This time when Karen came for her visit, we'd both have a big surprise for my husband, and one I was sure he was very much going to enjoy.