It was over. A year of bitterness, court dates and hearings and now I was a free man. So why didn't I feel relieved? It wasn't because I still loved Susan, I knew that. After we were married, it didn't take us long to realize we didn't even like each other very much, though we'd tried. It was better this way. But I felt soiled, used up.
My buddies took me out to a bar to "celebrate" my independence. That was a flop. It wasn't that I didn't want to be happy. It certainly that I wasn't ready to get back out there and play the field; I'd been very careful throughout the divorce, so it'd been well over a year since the last time I had me a nice piece of tail. I just felt awkward, even when a promising young woman asked me to dance. She ended up going home with Bobby, and I ended up going home with Mr. Daniels, first name Jack.
I planned to spend the weekend mostly drunk, watching the game I'd taped earlier in the week, and just stay in. That morning, I didn't answer the phone when Bobby called, but he left a message. I didn't plan on calling him back, but I listened to it anyway.
"Hey man, I know you've had a rough year, and it's going to take some time to get used to being a free man again. Don't take too long, though. You're still young. Go out and try something new. I'll talk to you later buddy."
Something new, I thought. Like what? I married Susan straight out of high school, so aside from a few one-nighters before we hooked up, she was the only woman I'd ever been with, and she wasn't a big one for kinky experimental stuff, so almost everything was new to me.
The divorce had been really nasty. She'd got the car, which was really the only significant thing we'd owned. My consolation prize was that they didn't try to kick me out of our apartment. She'd left a lot of her clothes and stuff there, saying she didn't want any of the trashy stuff I'd bought for her, which was really just a slap in the face. Most of what I'd bought her was fairly nice, though there were some sexy items I'd bought for her to wear that were really more presents for me.
Saturday afternoon found me going through the closet, trying to remember if we'd really had any good memories at all. I held the dark red evening gown I'd bought her for the Christmas party up and looked at it in the mirror. Trashy? Not even. Even I would look good in this dress, I thought, grinning at the idea. I found myself standing there, still holding the dress. She'd never worn it. A damned pity to give a dress like that to Goodwill completely unused. I held it up in front of me, looking at myself in the mirror. It might actually even fit me.
See, I wasn't the athletic type. I was moderately fit, but nobody would call me muscular. I was slim, and short. I could run a mile in five minutes flat, but I wasn't going to win any weight lifting contests. By contrast, Susan had been somewhat taller, and had a few extra pounds on her without being fat. This dress would probably look better on me than it would have on her.
I tried to dismiss the idea, but Mr. Daniels didn't think it was a bad idea. I could put it on, have a chuckle, then go watch the game. So I skinned out of my clothes, and then wriggled into the dress, smoothing it down before turning to look in the mirror again. The effect was startling. Even without cleavage or hips to fill it out properly, it looked good on me. The thing that spoiled it was my package, pushed out by the briefs I was wearing. I adjusted myself, tucking my dick back down between my legs, and checked again. Much nicer.
I should have put my own clothes back on and went to watch the game, but I was in a strange mood. In for a penny, in for a pound, right? I went to the dresser and rifled through the drawers until I found a red satin thong. I pulled up the evening gown, slid my briefs off, then pulled the panties on. The satin felt good as I adjusted it around my crotch, though the strap going up the crack of my ass would take some getting used to. I smoothed the dress back down across my hips, then went digging for a bra, and some thigh-high panty hose.
After some undressing and redressing, and a pair of strategically placed rolled socks, I checked the effect in the mirror again. From the shoulders down, I was smokin'. The transformation was amazing. My face still looked like me, and what with the stubble, didn't match the rest. It wasn't anything a shave, some makeup, and a wig wouldn't fix. The thought of going all the way with the transformation made me stop and ask myself what I was doing. This was nuts! I found I really wanted to try it, though. It was going to take a bit more time, but I'd decided I was going to do it, as crazy as it was.
It was the next weekend when I'd finally gathered the things I needed. Getting the wig had been embarrassing, as I kept expecting them to ask exactly what I planned on doing with it, but no one ever did. The makeup was easy after that. I laid the clothes out on the bed, then got to work. A shower, a thorough shave of not only my face, but my legs, and an hour in front of the mirror with the makeup, and I found myself in front of the mirror again.
The difference was night and day. Where last weekend it had been obvious that the person in the mirror was a man wearing women's clothing, there was now an attractive woman. The makeup wasn't perfect, but a little practice would improve that. I suddenly knew I'd be getting a lot of practice.
I wore my new look around the house for the rest of the weekend. I didn't ask why I was doing it, I just did it. It was new, different, exciting. I really got into it, too. I watched the way I walked in the mirror. I listened to my voice, and tried different ways of speaking until I found one that sounded right, and practiced it until it was perfect. I even decided on a name.
During the week, I made an effort to be more outgoing with my buddies. I didn't want them stopping by unexpectedly to check on me. We went out to a bar on Thursday, and watched the women dance. Normally I appreciated this for its own sake, but this time, I had a different motive. I watched and made mental notes. Habitual gestures, the way their bodies moved, the kind of things they said. I wanted Sheila to be perfect. The next morning, I told the guys that I was going to be out of town for the weekend, visiting family.
That night, I packed up a couple of outfits and my makeup, and took off to Flagstaff. It was a college town, and more importantly, I didn't know anyone who lived there. I got a hotel room, away from the office, and underwent my transformation. I hung around the room until about 10pm, and then I went out to my car and headed down to the busiest nightclub I could find.
I was so nervous, but I knew I had to try. When I got to the door, I realized my first mistake; My ID was from my male self! I almost went home, but I tried to brazen my way through. I told them that I'd grabbed my husband's ID by mistake, but I just really wanted to dance. The door man looked me over, then shrugged, and took my money. I was in!
First thing, I got a drink. I was going to need some liquid courage before I hit the dance floor. The bartender was a bit surprised when I ordered Jack straight up, but I barely noticed. The dance floor was jumping with attractive young college students. I found myself looking at the guys as much as the girls. Sheila would be interested in them, right? Anyway, it was just dancing. I got the courage burning pleasantly in my stomach, and headed for the floor.
It was a blur. I shook my ass all over the dance floor, and found that I was enjoying myself more than I ever had at a dance club. Being someone other than me was freeing, and I loved it. When I felt someone grind up against my butt, I turned over my shoulder to see a young stud there. It was weird, but this was why Sheila was here. I didn't want to give myself away, so I smiled and ground back on his crotch. With that encouragement, he became even bolder, and began to run his hands over my hips, and even to tease toward my fake boobs. I moved his hands back down in a teasing fashion, so as to avoid him touching the bundled cloth and realizing something was wrong.
I'm really turned on, I realized. My cock was straining at where I'd tucked it away. I found myself wishing I really was a woman, so I could let this hottie take me home and fuck me. That couldn't happen, of course, so I needed an excuse to get out of the situation. I turned and gestured toward the restrooms. It was too loud to try speaking. He nodded, and I walked off the dance floor, conscious that his eyes followed me as I moved. Even that sent a thrill coursing through me.
I walked into the bathroom, moving toward the urinals while I tried to think of how I was going to get out of there without having to make a scene. Urinals? Ah, crap. I'd gone to the men's room out of reflex. I turned around to leave, just as the door opened, and in walked my college boy. I could tell right away that he thought I'd come in here on purpose, and my heart leapt into my throat. I was sure I was going to be discovered, and then who knew what would happen? He walked toward me with a confident air, and suddenly I knew what I would have to do to get out of here without blowing my cover. I'd have to blow him.
Momentary disgust was swept away by a wave of excitement and lust. The part of me that still thought there was something very wrong with what I was doing was thrust backward by Sheila, and I dropped to my knees, smiling suggestively up at him. I didn't even care that I was right there in the middle of the bathroom, where anyone could walk in and see. If someone did, maybe I'd blow them, too. As my college boy approached, I reached out and unbuttoned his fly, where I could see his cock was straining for release.
When it sprang out, I knew I was well past the point of no return. I took that cock into my mouth with a shudder of longing, feeling it slip between my lips, and the soft firmness of it pressing insistently against the roof of my mouth. I clamped my lips over the shaft and applied suction, flicking my tongue over the underside as he pressed inward, the head coming to nudge insistently at my throat. I pulled back slowly, feeling my cheeks collapse slightly as he withdrew. I stopped with the head barely inside my lips, and spiraled my tongue around the helmet, then teased it down the slit. It was incredible, what I was doing. I was down on my knees in the men's room wearing a sexy dress, with my made-up lips wrapped around this stud's cock, and I was loving it. I looked up at him, trying my best fuck-me look. He was watching me, and as our eyes met, his dick suddenly twitched and hot semen squirted onto my tongue.
Giving him a smoldering look, I slid my lips up his shaft, nearly to the base, and sucked harder, feeling his cock spasming in my mouth as it emptied his load down my throat. He groaned and threw his head back, his hands coming down to grab my head, nearly dislodging the wig as he fucked my mouth for a few thrusts before withdrawing. I stood up and leaned in to kiss him.
He jerked back, his face going bright red. I smirked and licked a dribble of cum off my lip as I ran my hands down my body, checking that everything was still in place. As I turned to the mirror and ran my fingers through the wig, he excused himself with some mumbling, and walked out of the men's room. I was pretty sure I wasn't going to see him again, but I didn't mind. I reapplied my lipstick, then left the restroom myself, brushing past another guy on his way in. He gave me a double-take, and I winked suggestively before disappearing into the crowded club.
I found an empty seat near the end of the bar, and glanced around for my college boy, but as I predicted, he was nowhere to be seen. I ordered another drink, asking the bartender to "surprise me". He brought back something tall and sweet, and I sipped on it as I considered what I'd just done. Was I disgusted? Just the opposite! My cock was still insistently trying to break loose, and all I could think about was the feel of his cock in my mouth, the hard and softness of it, the smell, the taste, and the way the hot cum filled my mouth.
Then my reverie was broken by a hand on my thigh, as a man slid onto the barstool next to me. My first instinct was to slap his hand away, but as I jerked my head around to glare at him, I saw that it was the bouncer. He was huge, and I didn't want to make a scene; Besides, now that I was getting a better look at him, he was yummy.
Yummy? I asked myself, rueful dismay flooding through my mind, even as I gave the hunky bouncer the once-over. I made myself relax, letting a lazy smile curve my lips, and dropped a hand to caress his, where it still rested on my thigh.
"What can I do for you, handsome?" I asked him, lifting a brow in challenge.
"I saw you come out of the men's room," he said. I continued to look at him, not saying another word, until he spoke again. "A man could get the wrong idea," he said after a long moment's silence.
"Or the right one, sweetie," I replied, and was immediately rewarded by his eyes widening in surprise. "I'll ask again, what can I do for you?"
"What are you offering?" he asked, his tone caught somewhere between cautious and suggestive. I licked my lips and winked at him. The tiny voice clamoring in my mind, asking what exactly I was doing, was getting easier to ignore. I was having fun. I was trying something new, and I was having a ball.
"Why don't we find someplace quiet to discuss," I paused for effect, and let my eyes drop down toward his lap, "whatever happens to pop up." He eyed me for a second, and I saw his gaze grow warmer, then he got up without another word, and walked toward the back of the bar. I got up and followed him, letting my hips swing back and forth. I saw a few eyes marking my passage, knowing exactly where this was headed.
He opened a door into what looked like a storage room, with shelves stacked with bottles of beer and other spirits. As soon as the door closed, his arms were around me, pushing me into the wall, and I felt his lips on mine. Sheila wanted this --I wanted this- so I snaked my arms around his broad shoulders, and kissed him back with all the vigor I could. His hands coursed up and down my back, groping at my ass and then back up. When they started to coil into my wig, I knew I had to change the rhythm before I was discovered. I pushed him back, and he stepped away.
I could barely make out the slightly confused expression on his face before I dropped to my knees, already anticipating my lips around another beautiful cock. I fumbled with his button, then pulled the zipper down, my haste making my fingers clumsy. I heard a groan from him as I pulled his pants down around his hips, finally revealing his beefy cock. More confident than previously, I started slowly, teasing at the slit with the tip of my tongue, tasting the tiniest bit of pre-cum already. I swirled my tongue around the head before finally taking his cock into my mouth.
The second time wasn't nearly so scary, nor as urgent; I wasn't torn between fear and excitement at what I was doing, so I took my time to really experience it. The taste was very different from the few times I'd talked Susan into letting me go down on her; Musky, with a saltiness from his sweat, but without the tang of pussy. The smell was subtle, but intoxicating. The feel, however, was where I found I was really enjoying myself. It was so firm, but still soft, silky, and each time I slid my lips down the shaft toward the base, I felt it throb softly.
I took his cock deep into my mouth, feeling it bump against the back of my throat. I moaned softly, and heard an answering gasp from him. He reached down and grabbed my head with both hands and started to face fuck me, but with long slow strokes. I let him take control, focusing on keeping my teeth away from his shaft and keeping a steady suction has he pistoned in and out of my mouth. His pace started to quicken, and I did my best to control my gag reflex as his head butted my throat, time and again.
"Fuck," he breathed, "I'm gonna cum!" I pulled back and looked up at him, taking his cock in my hands.
"Give it to me, baby," I crooned, then started stroking his cock rapidly, aimed at my open mouth. The first shot took me by surprise, splattering on my lips. Not wanting a mess, I took his head back into my mouth as it surged several more times, spilling all over my tongue. I looked up at him, sticking my tongue out to show him the pool of cum then wrapped my lips back around his cock and sucked hard, taking the head as far back as I could handle as I swallowed it all down. I felt one last spasm as he let out a satisfied groan and fell back against the wall.
"God," he exclaimed, "That was incredible!" I traced my finger over my lips, swirling the excess cum into my mouth and sucking my finger with gusto.
"Your cock is incredible," I replied, satisfied in a way I hadn't ever been with Susan. I knew that I wanted more, much more than this taste I'd had tonight, but it was time to move on. "Maybe I'll taste it again sometime," I said as I straightened my dress and moved toward the door back to the busy bar with a girlish flounce.
"Maybe you can ride it sometime, too," he shot back, still leaning against the wall, his beautiful dick still hanging out and finally starting to soften. I threw him a genuine smile over my shoulder as I pushed out of the backroom and back into the crowded bar. It was time to go, but I knew tonight was only the beginning of things to come. Riding a cock? The thought hadn't really occurred to me before, but as it did I felt a tingling down deep inside, and I knew I wanted to at least try it. As I walked toward the door with my mussed hair, smeared lipstick and satisfied smile, there was one thing I knew for certain: This would not be the last time Sheila came out to play.