TransgenderComplete

The Extra Dress Pt. 01

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Everyone is over the age of 18 here.

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I don't know why my folks insisted I come to the wedding, but they did. It was a semi-destination wedding of a cousin a short flight from home. My freshman year of college was over, and I didn't have a good excuse to say no. Everyone was staying at this nice hotel/resort and the wedding and reception were both on the grounds, so we didn't have to go anywhere. There was a pool, and my folks sweetened the deal by getting me my own room, which was a first for a family trip, but I was 19 and in college, so maybe they thought I was more adult now.

I didn't really know anyone other than a few relatives, so I was pretty much invisible. I met the bride at the 'rehearsal' dinner, which was really just a reception for anyone who flew in early enough to make the event. The couple was around 30, and I really didn't know what they did, but my cousin's bride to be was smoking hot. And apparently, all smoking hot girls have smoking hot girlfriends, because all the bridesmaids looked like models. And they were all at least 10 years older than me, so yeah, a skinny, short, shy 19 year old kid had zero shot with any of them. They all had plus ones anyway, good looking, tanned, muscular guys who were glued to them when they weren't ganged up together. And it looked like I was the only one there in my age group. Fantastic. At least because everyone else was of age, the bartenders just assumed I was as well, and never carded me.

I got plenty to look at the day before the wedding around the pool, where everyone was horsing around and the girls were all getting last minute work done on their tans wearing skimpy bikinis. Everyone was nice to me, but no one went out of their way to interact with me, I was just there. The day of the wedding got me into a sportscoat and slacks, and I just hung out with my folks for the event. Well, I thought the girls were hot in street clothes, the dresses they wore for the actual event were amazing. Every single one of them looked like she could be in a magazine. I heard that brides don't like to be upstaged at their wedding, and I was thinking that the bride would be pissed, until she came out. OK, every bridesmaid was a 10, so the bride just cranked it up to 11. And they all looked like they were having the time of their lives.

The reception was no exception. The couple looked like they were in love, the rest of the bridal party was having a blast, the speeches were funny and sweet, the dances were spot on, the overall food and music were great, and I was bored out of my mind. I had a couple of drinks, not enough to get me drunk, but I was feeling loose, and I guess I was staring at the bridesmaids a little too long because another one of the guests moved to join me at an empty table where I had parked myself and asked if I thought the dresses were pretty. I replied that the girls were all gorgeous, but he drilled down to ask what I thought of the dresses. I was caught a bit off guard and sheepishly admitted that they all looked really sexy. He asked my name, to which I answered Dylan, introduced himself as Drew and told me that he had designed and made all the dresses, including the wedding dress. He had noticed me looking at them and thought I was looking at the dresses more than the girls.

That made me blush, catching me in something that seemed forbidden, since it was true, I was looking at the dresses. "You know, I have an extra, just in case something happened and I needed an emergency backup, I could show it to you if you like...," he offered. That really got me blushing and stammering. I didn't say no, and I guess he took that as a yes, because before I knew it we were headed away from the reception. I don't even know how I ended up on my feet, but we were walking, and I could feel his hand on the small of my back, lightly guiding me. I don't know where we ended up in the maze of corridors, but we arrived at his room, a suite, where the front room had been transformed into a fitting room, with a pedestal and three way mirror. He ushered me and gestured towards a rack that contained the spare dress.

As a kid, I had played dress up a few times in some of mom's clothes, but that was ages ago and, what I thought, was just a short phase. I had never held an interest in women's fashion, sure, the bodies under the clothing, but not the clothing itself. But I had to admit to myself I was looking at the dresses as much as the bridal party itself, and when given the opportunity to inspect the spare dress, well I was looking at it like it was the most interesting thing in the world. Drew reappeared with 2 glasses of champagne and toasted, "to pretty dresses and all the creatures who wear them..." He went to remove my jacket and placed it on a hangar and then pulled me to the pedestal where I was facing the 3-way mirror. He then draped the dress over me, giving the illusion that I was wearing it. I was transfixed. I was staring at my reflection as if I were a completely different person.

"You know," he whispered in my ear, "you could try it on Dylan. I can make it fit, it wouldn't be difficult, you have a nice body, you would look great in it." I could only nod. He unbuttoned my shirt and slipped it off, noticing my hairless chest. "I saw you drinking, you are over 18, right?" to which I again nodded, not understanding the implication. His hands went to my slacks next, and stepping out of them, I was left in my boxer briefs. He turned away and went over the dresser and produced a pair of light pink panties, matching the color of the dress. He handed them to me and pushed me towards the bedroom in the suite, smacking my ass as I walked away. I was in a dream state, not really processing anything, but I pulled my briefs down and pulled up the panties. They were obviously smaller than what I had been wearing, but the silk fabric felt so smooth against my skin, and they were surprisingly supportive of my equipment. I have no idea why I didn't grab my clothes and run off, but I instead just came back out to the front room, wearing nothing but the tiny bit of silk.

I suddenly felt very naked, barely covered and under the appraising gaze of Drew. He walked over to me and then moved behind me, wrapping my torso in a strapless bra to match the panties. He reached inside the cups and placed gelled inserts inside, giving me realistic looking breasts. I don't know if he did it on purpose, but I could definitely feel his hand rubbing against my surprisingly hard nipples. He gestured to a chair and had me sit as he grabbed a leg and slowly rolled up a stocking. He took his time making sure it was smooth and straight, his hands lightly brushing against my legs, moving up my thigh and even above the stocking top, sliding his fingers against my naked flesh, stopping just below my panties. I couldn't help it, closing my eyes and relishing the touch, releasing a tiny moan that I am sure he heard. He moved to the other foot, taking it in his hand and slowly rubbing it in his strong grip. I started whimpering a bit at that, my eyes still closed. I felt his hands move up my leg again, gently squeezing it and covering my skin with the material of the stocking. Again, his hands lingered above the stocking, stroking my bare skin and inching toward what I realized was my achingly hard panty covered cock.

I could feel his breath against my ear and he whispered, asking me if I liked how I was feeling. I bit my lip, nodding my head and whimpering a yes. He whispered that I looked so sexy right now and then moved away, returning a moment later with a pair of strappy high heel shoes. "These should fit," he declared as he slipped my feet into them, deftly securing them to my feet. He helped me to stand, which I was barely able to manage in what seemed like the impossibly high heeled shoes. He instructed me to walk on my toes and take short steps, one foot in front of the other. He moved behind me, his hands on my hips as I felt my but moving from side to side with each step. He guided me to a side table and had me sit down, where he proceeded to apply makeup to my face. I was looking away from the mirror, angled so that the dress was right in my line of sight, as he worked away. He would give me instructions from time to time, look up, look down, pucker your lips... and I just compiled.

All the while he was complimenting me, my eyes were so sexy, my lips were so full and kissable, I was so beautiful... He said even my name was perfect, because Dylan was a very sexy girl's name. He finally worked some product into my hair and sprayed me with some flowery perfume before spinning me around to look in a mirror. To be honest, I did not recognize myself.

It was weird, I would move my head one way and this amazing, beautiful, sexy woman with huge, smokey eyes, full red lips, high cheekbones and slicked back hair would mimic the movement in the mirror. This woman would have fit right in with the other bridesmaids, definitely a 9/10, maybe even a 10 herself. Drew appeared in the mirror, his head next to mine, his lips inches from my ear. It was the first time I noticed how handsome he was, how he would definitely look great right next to one of the bridesmaids, or right next to the sexy woman staring back at me from the mirror. "You look so sexy Dylan," he whispered in my ear, his hot breath setting my skin on fire. I closed my eyes and the thought flashed in my mind, kiss me Drew. I heard a slight moan, realizing it was me making the noise, and felt his lips brush against my neck, so lightly, then a little firmer, and I could feel his tongue lightly trace my jawbone.

I turned my head toward him and he moved his lips to mine, kissing me, softly at first, but then with a hunger and insistence, I felt his tongue on my lips and I opened my mouth, allowing it to slip past my lips and seek out my own tongue. His lips glided against mine, slick with lipstick and gloss. I felt so feminine, so fragile, and so submissive, wearing heels and lingerie, made up looking stunning and making out with a handsome man.

I have no idea how long we were kissing, it could have been seconds, it could have been hours, I just know I had never felt anything like it before. Eventually he disengaged and reapplied my lipstick, escorting me to the center of the room, staring at myself in the mirror. I was so transfixed with how I looked, I never gave a thought to my poor aching cock, which was rock hard and poking out the top of the panties. Drew's hand went to it and told me it would ruin the look of the dress, so we must do something about it. What I wasn't expecting was for him to drop to his knees and take me in his mouth, engulfing my entire cock. I had never had a blowjob, and I wasn't going to really be able to relish this one, because the moment his lips clamped around my skin and his tongue grazed the tip of my cock, I started to cum in his mouth. He never pulled back, just kept sucking on my cock, milking it dry. A moment later he stood up, licked his lips, gave me a sly little grin, and fussed with my cock and balls, smoothing them in the panties to where there was no bulge to be seen.

He then got the dress and helped me into it, zipping it up and pinning it so it hugged my body. When he was done and stepped back, it looked like it was made for me, it fit my body perfectly. I was staring at this stunning looking model in the mirror, I would move my body and the model would move the same way, it was hypnotizing, and oh so sexy... I was miles away when I realized there was some clicking coming from the room, and I saw Drew taking photos of me in the dress. I was about to say something when he told me to move a certain way, which I did, then he gave me more instruction, pose a certain way, hold me head this way, blow a kiss... it was fun acting like this, and I never got around to objecting. He has me step down and walk to the bedroom, where he gave me more instructions, having me walk a certain way, then sit a certain way, cross my legs, show of the stocking through the slit of the dress... he had me lay down on the bed, and he stood on a chair, shooting down over me as I rolled around on the bed, blowing kisses at the camera, flashing a bit of skin... He kept saying how sexy I was, how the camera loves girls 'like me,' how I would make any woman jealous and every man want me.

I ate it up and started flirting with the camera, doing it on my own, loving the feeling of being filmed, or maybe loving the feeling of being filmed by him. I was flirting with him, loving his compliments, feeling so sexy. Eventually he placed the camera on a tripod and walked over to the bed, moving over me.

In a flash we were kissing again, his tongue back in my mouth, and me sucking on it, wrestling with it. His lips and hands were everywhere, and eventually I found myself stripped of the dress, lying there on the bed beneath him in the stockings bra and panties, still wearing the heels, my legs wrapped around his hips. He kneeled over me and stripped off his shirt, revealing a strong, chiseled chest and abs. He placed my hands on his bare skin, letting me feel the heat, then started to move them about over his body. Soon, my hands were moving on their own, feeling his body, his oh so manly body. He took my hands and moved them to his belt, and they just went on autopilot and undid it, then the clasp on his pants. I had never thought about being with a guy, but Dylan the girl's hands were certainly into being with a guy, and soon I had his hard cock between them.

It was so alien, yet so familiar. First off, it was sooooo much bigger than mine. Twice as long, thicker and harder. I always knew I wasn't big, but I never thought I was small, I just didn't have a point of comparison. Watching porn didn't count, but here was this massive cock in my hands, big enough and thick enough that it really did take 2 hands to do it justice. He moved to lay down on the bed, his head propped up by pillows so he could watch me, and had me on my stomach, my head at his crotch, looking up at him and his hard, thick, beautiful cock. And it was beautiful; thick and veiny, with a perfect helmeted head, with a pair of heavy balls underneath, the whole area shaved and bare like his chest, making his cock look even larger... "Do you want to kiss it Dylan," he asked, and I did, shaking my head yes. "Tell me what you want to do baby," he said, and so I did.

I started off telling him I wanted to kiss him, but he kept telling me to say more, and I kept going, eventually begging him to let me suck his magnificent cock. All the while I was stroking it with my two hands, occasionally kissing it or reaching out with my tongue to lick it. Eventually, I just started to suck on the head, pulling it into my mouth as I swirled my tongue around the fat head. His hands were in my hair, moving my head about a little bit, giving me instructions, telling me how sexy I looked, how beautiful I was, how good my mouth felt on his cock. He started moving his hips, pistoning his thick member in and out of my mouth while I struggled to breathe, all the while slurping away at the fluid leaking from the tip...

He pulled his fat dick from between my lips, making an audible pop as it sprung free, and gently guided my head towards his, moving my body up the bed. We kissed, and he took the moment to roll me on my back, grabbing both legs in one hand and lifting them up. He took his other hand and removed the panties, then spread my legs, positioning himself between them. He started to jack his cock against my smaller one, and then I felt a cool drizzle as he poured lubricant onto our cocks, making them glide so much more effortlessly..He draped my knees over his elbows, spreading my legs and I could feel the heat of his cock rubbing against my virgin ass. "Do you want this big cock," he asked, eliciting a nod of the head. "Does my sexy girl want her man to fuck her in her pussy?

Again and again he told me to ask for it, and I began telling him how I wanted him to fuck me with his fat cock, how I wanted to milk his cock with my virgin pussy, how I wanted to be his girl and feel his cock deep inside me. He kept teasing me with the head, rubbing in and out of my crack, teasing me until he ran it against my own, squeezing his cock against my 'clit' in his hands. Back and forth he went bumping his rock hard head against the opening of my canal, pushing slightly, my body opening up millimeter by millimeter against his insistent pressure, only to have him return to rubbing our shafts together, adding more lubrication, more pressure, getting me to moan with each push and then whimper when he withdrew. Suddenly he pushed harder and was inside me, driving the fat bulbous head past the ring. I moaned, and then he pushed again, sliding more inside me. I could feel him slowly extract his rod, only to push it in again, deeper, opening me, filling me. Suddenly there was a new sensation as he hit the magic spot, rubbing his cock against my prostate, then pushing it out of the way as he kept driving it into me. Again and again he would pull back a tad, and then push forward deeper, causing sensations I never thought possible. My entire body just felt like it was wrapped around his massive cock, squeezing it, holding on to it. As he pulled back I felt a little empty, until he pushed in again, exposing new parts of my body to his cock.

Finally I could feel his hips against my thighs, his cock fully buried inside me, stretching me, filling me completely. From there, he started to slowly pump in and out, removing a bit more each time, only to drive the full length of his cock deep inside me with each stroke. His thick cock was rubbing my prostate with each stroke, causing me to moan and thrash about on the bed. Eventually he got to where he could pull nearly the whole way out before driving in again, over and over. A feeling began to swell deep inside me, and on one last deep stroke that feeling took over, and all of a sudden my cock released a torrent of cum, firing in the air and crashing against my tummy.

My entire body tensed up and clenched down on him, and that caused him to stop his thrusting, and then I felt it, a warmth spreading deep inside me as his cock convulsed over and over again, depositing his load deep in my ass. He leaned in and kissed me, snaking his tongue into my mouth, mirroring his cock buried deep inside me.

I could feel his cock softening and retreating, and he helped me to my feet and steadied me so I could walk to the bathroom. I heard him run the shower as his seed leaked out of my gaping hole. I figured out how to remove the shoes and stockings, and then joined him in the large shower, where we proceeded to wash each other and clean up all the remnants of our frenzied sex. Of course, that amount of contact ended up rekindling the fire, and I found myself once again stroking his thick cock, my own smaller unit spent from two massive loads and uninterested in rising to the occasion.

Still, his cock was what I was really interested in, and having it in my hands led quickly to me returning it to my mouth, kneeling there in the shower, servicing his hardening tool. It was still bigger than mine while it was soft, and watching it and feeling it grow in my hands was fascinating. I never imagined myself servicing another cock, yet here I was, and it was all I wanted to do. I stroked it between my hands and then began kissing it all over, then licking it with long strokes on my tongue as my mouth watered for it. Finally I returned it to between my lips, working on the thick head while swirling my tongue all over it. Fully erect, it seemed like it was bigger than my own mouth could open, but I diligently worked on it, bobbing my head up and down, getting a bit more in my mouth each time.

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