Although this IS a sex story, it is also a TRUE story and was written more about the experience rather than the hardcore sex. It may not be YOUR cup of tea, but the experience changed my life completely and I should like to share my story with you, dear reader.
It was the perfect environment for me, I thought at the time. I was spending a week at my parent’s condo down in Palm Springs, California while they were up north in Washington State, and if you’ve ever been to Palm Springs than you know that this is a retirement community full of senior citizens who retire to bed as soon as the sun goes down. The reason I thought it was so perfect is because not only did I have my parent’s condo completely to myself for a week, because of the old folks I would have the entire condo complex to myself as well.
The perfect time and place for me to indulge in one of my favorite life-long pastimes, cross-dressing. I’ve been a crossdresser pretty much my entire life, but it had always been a solo thing, something I’ve done alone by myself and no one else in the world knew about. Having the time and the freedom to do it up right now, I took my time and enjoyed myself to the fullest. After a long, warm bubble bath using all of my mother’s bath oils and lotions I borrowed her razor and proceeded to remove all the pubic hair from my body; starting with my legs and working all the way up to my chest and my armpits. I’ve never been that hairy of a person to begin with, and I regularly keep myself shaven so the task was not all too difficult. I removed all the hair from my legs and thighs, shaved my balls completely bare and made sure that my chest and armpits were silky smooth, leaving just a small patch of pubic hair just above my cock in a thin line like the women who shave their pussies do. Smoothing in some silky lotion over my entire body after toweling off, I was beginning to feel pretty sexy.
Moving to my mother’s vanity table, I switched on the lights around the mirror and began to experiment with her make-up and lipstick. I’ve always found it surprising how easy it is to make my face look quite feminine, and it wasn’t long before I found a fairly pretty female staring back at me in the mirror. It was still pretty obvious that I was a male who had been made up to look like a female, I wasn’t going to fool anybody except possibly at a distance, but I still felt I looked pretty sexy, and was ready for the next step. Digging in my bag, I found my favorite string-bikini and began putting it on. A racy little black number that seemed to be more string than bikini itself, I loved the way it clung tightly to my thin body and showed off my hips, and with a freshly shaven and completely oiled up body I thought I looked pretty darn good.
I’m in decent shape for a thirty five year old man, meaning that I still manage most of my athletic structure I had as a teen, and haven’t let my belly grow large or anything, but gravity and time has taken its toll; but this time it was working for me as the slight sagging in my chest that used to be tight muscles when I worked out at the gym every week when I was in my twenties now filled out the taunt bikini top I strapped to my chest in a rather pleasant-looking way, making me appear as if I had a small bust line. One of my best features is that I still have a full head of hair, which I keep fairly long and part in the middle, so it wasn’t too much work to pin it up in all the right places to give it a more feminine look. And, with a thin silver necklace from my mother’s jewelry chest that hung down to just above the top of the bikini, a little black choker that hid my Adam’s apple well and a couple rings for my fingers I almost had the look I was shooting for. Bright red nail polish on my fingers and my toes that matched the lipstick I had chosen and I was now feeling sexier than I may have ever looked in my entire life.
I was admiring myself in the master bedroom’s full-length mirror when I heard the clock in the family room chime 2am. Figuring the rest of the complex would be dead to the world by then, I rummaged around in my mother’s closet and came up with a pair of sandals that had heels on them and a small terrycloth robe and slipped them both on, stumbling a little in the heels as I made my way to the kitchen and removed a six pack of Corona’s from the fridge that I had purchased earlier in the day. I grabbed a pool towel and the security gate key and slipped out the back door and headed towards the community Jacuzzi. The place was dead silent by then, and I worried that the clicking of my heels on the small concrete path as I walked might actually wake someone, but a moment or two later I found myself standing alone in front of the very inviting Jacuzzi. Turning on the jets and quickly removing my sandals and robe, I slipped into the warm, bubbly water and sunk down until only my head was above water. The pool light had been out, and the only light was what the half full moon was offering so I felt I was pretty safe from anyone’s view as I found a comfortable place next to a warm jet to sit and relax.
After a bit, and after finishing my third Corona I began to relax completely and felt my body drifting off to a state of relaxation where I could possibly have fallen asleep if I wanted to. I closed my eyes and allowed my mind to drift in the warm water, and that was when I first heard the voices. Popping my head up quickly, I glanced around and saw with horror that two people were already coming through the security gate into the pool area. They were men, obviously intent on taking a dip as they wore swim trunks and had towels tossed over their shoulders. At this close of a distance, probably only thirty yards at the most, they must have already saw that someone else was in the Jacuzzi, even with my head being the only part of me not hidden under the dark waters, and realizing that I was wearing my bikini and that my robe and towel were farther than arm’s distance, I was kind of trapped. My only hope was that the pool light being out would provide enough darkness to not be seen completely and that the men would take a quick dip and then retreat back to wherever it was that they had come from. I held my breath and waited to see what would happen next.
As I’ve mentioned, crossdressing is something I have done my entire life, but also that it has been something I have done alone. I’d fantasized a number of times about being with a partner while being dressed up in women’s clothing, but it had never been anything more than fantasy. I wasn’t ready to take that plunge, and I suddenly became very nervous by the fact that I was now being forced into the situation of being dressed in women’s clothing around other human beings. There weren’t a whole lot of options; getting up quickly, grabbing my stuff and running off before they had a chance to say anything crossed my mind, but I didn’t have the courage to do so, so I submerged myself back into the waters with only my head above and turned my body away from my invaders with the hopes that they would basically just leave me alone.
They both greeted me as they stepped into the Jacuzzi, and I said hello back to them without really looking up from my half turned position, hoping that my hair would hide most of my face. They both got in and sat down together on the opposite side of the pool, and I was somewhat relieved when they began a conversation of their own, basically ignoring my presence as I had hoped they might. This allowed me to steal a glance or two when I noticed they weren’t looking my way; seeing that they were younger than the typical residents of my parent’s retirement community. They were still older than I was, both with gray hair and one with an almost white mustache, but maybe only as old as the mid-fifties at most. I’d met plenty of the residents in this area in years past and they were all well in their seventies or eighties, usually with a walker and old, wrinkled skin literally hanging off their bodies; these two men were nothing like that, and in fact appeared to still be in fairly good shape. This intrigued me somewhat, and I began listening to their conversation a little closer to see if I could find out more about who they were and what they were doing here.
One of the men eventually addressed the other as Jack, and by the conversation they held I managed to deduct that they were firemen. That explained why they were still in decent shape, but the location they spoke of was obviously not in the local area. The more I listened the more curious I found myself, which must have eventually become obvious to them that I was listening because the one who was not Jack finally turned to face me and smiled. I believe I must have blushed, as I smiled back when our eyes met, and then he spoke to me. “How are you doing this evening, Darling?” He asked. He called me darling, I couldn’t believe it. Did he think I was actually a woman? Was he being sarcastic? It suddenly dawned on me that even though there was only the light of the moon to see with, the red lipstick must have stood out in contrast to my somewhat pale face, and with my hair pinned up to mimic a more feminine style perhaps it was just dark enough for the illusion to be passable.
My voice would give me away; I knew that from the beginning. If I had in fact managed to fool these two men into thinking they were sharing the Jacuzzi with a female, which hadn’t been my intention in the first place; all I had wanted was to relax by myself and enjoy the warm water, they would know immediately that I was a male as soon as they heard my voice. I was faced with a tough decision; do I attempt to answer in a higher, more feminine voice and risk being obvious anyway, do I not answer at all and appear stuck-up, or do I answer in my regular voice and see what sort of a reaction it would get? In the end, I only managed a sort of half grunt half sigh that could have sounded either male or female over the machinery running the jets in the pool as I shrugged my shoulders in a kind of “You-know-how-it-is” gesture. The man that was not Jack chuckled as if he understood, then panic took me again as I watched him stand and wade his way over to my side of the small pool.
A moment later he was standing directly in front of me; the shallow pool allowing his dripping wet body to be exposed to me from just below the waistline of his swimming trunks. I was too frightened to even look up and meet his eyes, but that didn’t stop him from continuing to speak to me. “Hey, honey” He said; “Mind if I have one of your beers?” I didn’t answer, and a long moment passed with him standing no more than one foot in front of me with his question still hanging in the air. He apparently took my silence as a yes, and leaned forward until his mid-section was almost touching my face as he reached over me to the remaining beers I had placed on the walk, just about pressing his stomach into my face. Still in a complete panic and totally unable to speak let alone move, I closed my eyes as he grabbed a Corona from the pack and then stepped back to where he was about one foot in front of me again. He popped the top of the beer and then clicked it against the empty bottle just to my left as sort of a toast and thanked me in a sarcastic, I-always-get-what-I-want tone of voice. Continuing to stand mere inches from my face he tipped the bottle and took a long drink of the beer, and I had just made up my mind that I was going to get up and remove myself from this situation when the other man, Jack, spoke up.
“Leave her alone, Ted.” He said firmly. “She doesn’t want to be bothered by you.” Two things immediately passed my mind; that this other man, Jack, was defending me, and that they must still think that I was actually female. I only had a second to ponder these thoughts when the one standing in front of me, Ted, grabbed me firmly under one arm and lifted me to a standing position. It was firm enough to easily pull me upward, but not so strong that it hurt in any way, and as he did so Ted turned to his friend and proudly announced that the “she” that Jack was referring to was actually a “he.” I heard a surprised gasp from Ted on the other side of the small pool and I feared imminent danger, and that was what got me moving as I started to make my way to the steps to exit the Jacuzzi. Ted’s reaction was quick, before I managed two steps towards the steps out of the pool Ted already had one of his hands on my shoulder while snaking his other hand around my waist, holding the stolen beer bottle against my stomach. “Aw, don’t go sweetie” Ted said as he turned my body easily around to face his, now placing both of his hands on my hips at the ties of my bikini. “I’m sorry if I upset you.” He said through a big smile. “Besides,” He continued; “I think you’re kind of cute!”
I’m pretty sure that I was blushing again from Ted’s compliment, but despite the embarrassment I had felt about being seen dressed and made-up as a woman and the fear I felt about the uncontrollable situation I now found myself in, I allowed Ted to pull my body into his as he wrapped his arms around me and gave me a hug. Although I had fantasized about it many times in the past, I had never actually been in the arms of another man before in my life. I was surprised to find it to be a comfortable and safe feeling, and maybe it was that and the three Corona’s that I had finished before their arrival, but soon I felt myself relaxing into Ted’s arms as he held me tightly against him, slowly dancing with me in his arms as our bodies swayed together in the center of the small pool. Ted was more than a foot taller than my five foot four inch frame and with his arms around me I felt like he had totally surrounded me completely, but his gentle touch managed to make my fears quickly slip away and when he bent his neck and softly bit the skin where my neck met my shoulders I was already becoming putty in his hands.
I pressed myself harder against his body and let out a soft sigh as he nibbled on my neck, feeling the hardness inside his swim trunks begin to swell against my stomach. I raised my head and met his lips with my own and a moment later I was kissing another man for the very first time in my life. Perhaps later I would feel some remorse and shame, but at that moment I was feeling nothing but a pure excitement course through my entire body that I had never felt before, and all I could think about was that I wanted more. Ted’s warm tongue explored my mouth and I met it with my own as the taste of beer passed between us, then he broke the kiss and I was left standing there with my head tilted up towards his as I awaited more. Eventually I opened my eyes to find Ted smiling at me, and as I smiled a genuine smile in return he turned my body around so that my back was up against him now. I’d almost forgotten about the other man, Jack, who was sitting in the same place he was before, now finishing the Corona that his friend had taken from me and grinning from ear to ear. “Show Jack just how sexy you are, my dear” Ted whispered into my ear as he kissed behind my earlobe and pressed what now felt like a huge steel pole in his swim trunks against the material of the bikini covering my ass. I managed a moan from Ted’s kiss, or maybe it was the erection he was pressing into my ass, but apparently that escaped moan was enough encouragement to get Jack to stand and approach us in the center of the Jacuzzi. Another panicked moment gave me the thought to run away, but that passed as soon as Jack pressed his body against me and I was now sandwiched between the two men, feeling one erection pressing against my ass while another pressed against my thigh.
“Very sexy” Jack moaned just before pressing his lips to mine.
Jack’s kiss was hot, passionate, and so intense that I felt my knees weaken. If not for the two men holding me up between them I very well may have suddenly drowned in that Jacuzzi. Jack continued to explore my mouth with his tongue, his hands now squeezing the triangles of bikini that covered my chest and playing with my nipples through the material, pinching my now erect nipples between his fingers. Ted meanwhile, had stopped pressing his groin up against me momentarily, and then he was guiding my hand under the waistband of his swim trunks until I had a handful of hard cock in my hand. Another of many firsts for me; I had obviously held my own erect cock countless times but I had never felt the raw power of another man’s erection, feeling the heat of it on my skin, the life of its own as it pulsed in my grip. I moaned again around Jack’s lips as I slowly pumped Ted’s cock in my hand, amazed at its hardness as we found a steady rhythm of my pumping and his grinding his hips into my fist. Jack slipped his lips off of mine and soon kissed his way down my jaw line, then down my neck as he worked his way towards my chest, pausing for just a moment as he took a gentle nibble on my shoulder blade. My free hand wrapped around his head, fingers playing in his wet hair as I guided him down. I could feel my own erection straining in the material of the bikini bottoms and wondered who would be the first to discover this about me.
I opened my eyes when I felt Jack pull his lips away from my neck and saw that Ted was pushing him back with his hand from behind me, and then I was being guided by Jack towards the side of the pool. He walked me backwards towards the edge, his hard cock still in one of my hands until it slipped out from my grip as he repositioned himself into a seated position on the tiles at the edge of the pool. It didn’t take very long for me to understand what his intentions were as he turned me around to face him by my shoulders and then he placed both of his hands around my neck, gently but firmly pulling me forward and downward. I had always wanted to suck a cock but had never really been given an opportunity before, and now I was being guided down towards a very large, fully erect cock that was directly in front of my face. “Yeah, suck Daddy’s cock, Baby Doll” exclaimed Ted as my lips wrapped around the head of his pole. The taste of chlorine and pre-cum hit my pallet as I worked my tongue around the underside of his hard shaft before opening wider to accommodate more of his meat into my mouth. “Yeah, that’s what daddy likes” Ted hissed, pushing my head further down on his cock with the hand he had on the back of my head until I felt the enormous head hit the back of my throat. Having had absolutely no previous experience, I immediately started to gag on his shaft and pull away, but Ted held my head firmly in place as he raised his hips upward and embedded his cock down my throat, chuckling a little at the torture he was causing me.
Apparently, Ted was much more aggressive than his friend Jack, and I was beginning to wonder what had become of the second man whose last known location was behind me in the pool, but those thoughts were quickly forgotten as Ted’s cock began to twitch in my throat and he started furiously fucking my face with everything he had. I was making all sorts of comical gagging sounds as his meat pounded in and out of me, his hips rising off the tiles of the pool to thrust into my throat and I distinctively knew he was nearing his climax. I was preparing my mind for my first experience with a man’s cum in my mouth when Jack groaned and his entire body went rigid, and before I was ready to accept it he was spurting his hot sticky load down the back of my throat. I coughed and gagged, trying to back away from his cock as his cum backed up on me and I started throwing it back up, and the next thing I knew I spitting his cum back on him even as his cock was still spitting at me. By the time I was able to control my coughing and lift my head back up away from his lap I had his cum drooling out of the corner of my mouth and running down my chin, dripping down onto my chest and into the warm Jacuzzi water. Our eyes met again and he smiled and winked at me, and if that wasn’t enough from him to tell me that my first time cock sucking techniques were adequate enough, his next move certainly was.
Ted bent forward at the waist and placed his hands under my armpits like he had done earlier, standing me up again and pulling me close. Despite the fact that I still had globs of his cum smeared across my lips and chin he leaned forward and placed his lips upon mine, easily forcing my willing mouth open so that he could kiss me deeply and I responded in kind, kissing him back like a horny teenager on a first date. At that moment I wanted our kiss to go on forever; I was so incredibly lost in the exciting moment that I let out a disappointed-sounding moan when he pulled back and broke off our kiss after a minute or two, making Ted laugh out loud. “Don’t worry, Sweetheart” Ted whispered, “it looks like you have another cock waiting for you.” Ted nodded and motioned with his head behind me, and I turned around to find Jack sitting quietly up on the other side of the Jacuzzi with his legs in the water, his hand working back and forth on the bulge inside the front of his shorts. Jack smiled when he saw that we were looking at him, but made no move to approach me or stop his slow jerking movements in his shorts, so for a moment the three of us just stood there looking at each other. It appeared to me that Jack was content enough just to watch what had unfolded in front of him and to masturbate, but I had finally had a taste of what I had only fantasized about up to that point in my life, and I had no clue if this kind of opportunity would ever present itself again so I wasn’t quite ready for it to end just yet. With that in mind, and suddenly feeling embolden; I stepped slowly towards the opposite side of the small pool and towards Jack, holding his eyes with mine the whole time and trying to convey with my eyes that I wanted what was hopefully about to happen to actually happen.
The Jacuzzi is not that large, and it only took about four steps before I was standing in front of Jack. I paused for just a moment trying to decide what my next move was going to be and in that pause Jack made the move that Ted had already made on me twice in the past twenty minutes. Jack leaned and reached under my arms and raised me up to him; I fully expected to be kissed again, like before, but instead Jack gently turned me around by my hips and set me down so that I was facing away from him, sitting on his lap. Jack let out a low moan as the weight of my body landed on his erection and then he was rotating me back and forth in his lap as I leaned my upper body back against his broad chest. I was slowly giving him a lap dance as Jack controlled the tempo of my ass up and down his stiff cock, enjoying the feeling and wondering by his soft moans in my ear if he was bringing himself close to his own orgasm. I didn’t want to miss out on another chance to experience a cock as it erupted so after a couple additional moments I bent at the knees and slid my body down his thighs until I was seated on the concrete bench under water at his feet. Ted was nodding his approval from the other side of the pool as I reached up behind me without turning around, guiding my hands up his legs and thighs until I managed to find his extremely hard cock through the material of his swim trunks. I squeezed his cock in my hand and Jack’s entire body shivered as another low moan escaped his throat.
“Go on, Baby Doll” Ted began, encouraging me. “I know you want to suck on Jack’s cock, too.” From where I was sitting in front of his friend, I could see that Ted had raided a second Corona from my stash, and now he took a large sip and tipped the bottle at me. “Show Jack what a good little cocksucker you are” Ted said with a grin. I nodded as I squeezed Jack’s cock again through the material of his swim trunks and then swung my body around to face him, bringing my second hand up to meet my first in his lap and massaging his erection with both hands through his trunks. Jack exhaled loudly and dropped his head back when I finally managed to work my hand under the waistband and made contact with his cock for the first time, his cock already twitching as I palmed it and wrapped my fingers around his shaft. Even in the darkness I could tell that he had already been leaking a lot of pre-cum by the slickness on his shaft; I pumped him up and down a few times with one hand while I worked his suit down his thighs with the other, Jack’s entire body twitching and jerking all the while as low, guttural moans emitted from deep in his throat.
Holding the base of Jack’s hard cock in my right hand while gently squeezing what felt like a very large nut sack in my left, I bent forward into his lap and ran my tongue from just above my fist at his base towards the head of his cock, anticipating what Jack’s pre-cum would taste like as I wondered if the second cock I had ever sucked would taste differently than the first. I had only made it about half of the way up his shaft with my tongue and was still thinking about what differences I might find when Jack groaned louder than before and a shiver ran through his entire body, and before I even had the opportunity to take his cock into my mouth he was starting to cum; spurt after spurt of his seed splashing across the bridge of my nose and across my cheek. I quickly engulfed the head of his cock as the next shot of his cum painted my tongue, pumping my fist up and down his shaft as I attempted to drain him of all he had. I wasn’t even aware that Ted had moved until I heard him laugh into my ear just over my left shoulder, and as I continued to pump Jack’s cock with my hand and clean him with my tongue I heard Ted exclaim in a tone that sounded like amazement; “Perhaps you’re a little too hot for Jacky boy, my dear.” Ted laughed again and Jack just let out his breath, falling backward to lie down on the concrete as I continued to lap up the remaining cum still oozing from Jacks now deflating cock. I couldn’t be sure in the darkness, but I would swear that Jack was blushing with embarrassment of having cum so quickly, but I took it solely as a compliment.
I stood on the Jacuzzi’s bench to reach some of the drops of Jack’s cum that had somehow managed to miss my mouth and land on his stomach, which raised my lower body up and out of the water and a moment later I felt a pair of hands on my ass. I let out my own moan as a finger found its way under the hem of my bikini bottom and then I was experiencing yet another first in my life; Ted’s finger had found my anus and was massaging my button with the tip of his finger, causing my body to shiver involuntarily. Fantasy was one thing, but even occasional experimentation with my own fingers could not prepare me for the pure sexual euphoria I felt when Ted worked his finger past the virgin opening and into the chamber of my sphincter. My knees became weak and I could no longer stand; I kind of half shifted and half fell atop Jack’s still sprawled body while Ted worked a second finger into my ass hole and started opening me up. I’d always heard that anal sex hurt for the first time, and although I had never had anything even as thick as Ted’s two fingers inside of my ass before; the thickest thing prior to that night was a slim tapered candle on Christmas, I was surprised that I was feeling no pain and was nearly howling for more.
“You like that now, don’t you Baby Doll” Ted whispered from behind me; I could feel his hot breath as it connected with the pool water on my ass and I responded by pushing my ass back towards where the breath was coming from. Another laugh from Ted and then I felt something more incredible than I could have ever imagined as his hot tongue made first contact with the puckered skin of my anus, causing me to squirm from his touch. “Daddy wants your tight little pussy” Ted remarked before darting his tongue back in and pushing it into my actual canal. A loud grunt escaped me as my body pushed back into his tongue, Ted’s dirty talk and especially referring to himself as Daddy was a major turn on for me and between his mouth and his tongue I was nearly reaching my own orgasm. I lifted my chin up off Jack’s shoulder and titled to look at him; Jack’s eyes met mine and then our lips met again in a hot, passionate kiss, tongues intertwining as Jack’s arms came up and wrapped around my back in a strong embrace. “Yeah, that’s it” Ted said from behind me, “Hold her steady for me, Jack”
I could feel Jack’s erection coming back to life underneath me as we made out, and that only fueled my now red hot passion. I began panting into Jack’s mouth between kisses and then could only offer a moan when I felt the string of my bikini bottoms loosen and eventually start being pulled off of my hips. Ted had been lubing me up pretty well with his saliva; and while I made out with Jack and rubbed my newly released erection against his stomach and he rubbed his against mine, I began mentally preparing myself for what I believed would be next; feeling a hard cock nestling up against my anus and seeking its way inside. Ted’s mouth broke contact with my ass and I braced myself for him as I heard movement in the water behind me, but instead Ted moved up next to me and sat at the side of the pool. Without a word, Ted reached over and gripped my shoulder again, my cue to move for him. Using my elbows I lifted myself up off of Jack and allowed Ted to guide me by my hips until I was sitting on his lap; lining my ass up with his cock and then slowly easing me down on him. Natural resistance of Ted’s bulbous cock head attempting to enter my small virgin ass canal caused some panic on my part; Ted sensed this and gently kissed behind my ear as he whispered that he wanted his “Baby Doll” to relax, which apparently was just enough distraction to allow him to push his hips forward and the head of his cock past the tight ring of my puckering anus. I gasped with surprise; nothing that size had ever entered my ass before, and Ted quickly placed his big hand over my mouth to stifle me so that we didn’t wake anyone up. It took me a few minutes to get comfortable and when Ted felt I was ready he began slowly pushing my body down onto his hard cock.
What an incredible feeling; Ted’s cock slowly sliding up into my ass, I’ve never felt so completely full in my life. Had I known anal sex would be this wonderful I would have made sure to have tried it long ago. Grunting into Ted’s hand as it covered my mouth I continued to work him into me until I finally began to feel the hairs on his thighs tickling the skin on the cheeks of my ass. Ted allowed me a moment to adjust and then removed his hand from my mouth and placed both of his hands under me, beginning a slow rhythm of raising and lowering me, fucking me with his hard cock. Jack finally came alive again as he watched the action, his cock standing fully erect again as his friend fucked me mere inches from him. Standing up, Jack positioned himself in front of me and grabbed my erection with one hand, slowly tugging on me as his free hand grabbed his own cock and began masturbating us together. I was in heaven, experiencing something even further than I had previously allowed myself to fantasize about; Ted was slowly fucking my ass into submission while Jack sucked my cock down his throat. It was all too much stimulation for me, and when Ted whispered in my ear that Daddy was going to cum deep in his Baby Doll’s bowels I bucked and stiffened, releasing my pent up orgasm into the waiting mouth of Jack who had a air-tight seal around my cock. I felt my ass muscles clench around Ted’s pole as I came, which caused him to grunt loudly as his own cock fired hot cum deep into my ass. I nearly passed out from over stimulation as my body went limp and I lay back against Ted’s body until Jack released my cock from his warm lips with a smack and Ted’s deflating cock slipped from my ass. Jack stood and pumped his fist on his cock a couple more times and was soon spraying me with his orgasm; I had no energy to move and just allowed Jack’s warm jizz to splash across my chest and stomach until he finally finished and sat down next to us. I eventually climbed off of Ted’s lap and retrieved my last Corona and popped it open, taking the first huge sip and then passing it around as we sat in silence and reflected on what had taken place.
After a little while, once we all had caught our breath and recovered from our orgasms Jack looked at his wrist watch and commented that it was three thirty in the morning, and he thought he would head back to his condo and go to bed. Ted agreed that it was a good idea and asked that I join them. I thought about it for a moment or two, debating whether to ignore the all-too-familiar panic I always felt when something new was presented to me and decided I would like to join them. After gathering our things the two of them walked me back to my parent’s condo so I could grab a couple things and then we followed the concrete path back along the pool and off in the opposite direction, arriving at their condo a minute or two later. Once inside, I excused myself to the bathroom with my overnight bag. Checking myself in the mirror; I splashed water on my face to remove most of the make-up, then slipped into the sheer pink baby doll lingerie I had brought with me and then into the matching thong panties, and then exited the bathroom. I found my men in the living room and took up a position on the couch between them. Resting my legs across the lap of Jack who had changed from his wet swim trunks and now wore only a pair of whity-tighty briefs, I stretched out and lay my head in the lap of Ted, who had exited his own wet trunks and sat on the couch in only a towel. Jack immediately shifted my legs so I pressed against his groin while Ted lay his arm over my shoulder and ran his fingers through my hair. We sat in silence while Ted flipped channels on the television for a while, and when I had just about fallen asleep Ted lifted me easily in his strong arms and carried me into the bedroom.
That was my first experience as a crossdresser with two men, and I absolutely loved every minute of it.