I'm Jimmy James and this is a story of cross dressing and sexual submission at the hands of my girlfriends father.
============================ My First Time:
My girlfriend Cindy and her mother were going out of town to visit some relatives. Her father, Bob, said he couldn't afford the time off so he was going to stay. I had some work to do, so he was going to drop them off at the airport. I thought about how much I was going to miss her over the next two weeks on the way home. When I got home, I went to work in my office and tried to block it out. After about an hour, I couldn't take it anymore. I went to our bedroom and thought about how I was going to miss the sex the most. Cindy was a sexual dynamo and she loved sex games more than anything.
She had all the stuff to dress as just about anything. In fact, she had a whole room dedicated to nothing but dress up stuff. She had at least 50 wigs of all different descriptions. Silicone breast forms of different sizes to paste on over her modest b-cup. She had all the clothes you could imagine. From sophisticated to super sleazy. I walked through the room and admired the collection. For the next two weeks, the door would be closed and I wouldn't get to see her in any of it. I warmly fondled the fake breasts and their erect nipples. I was going to miss her more than anything.
I grabbed the pair of DD-cup tits, pressed them to my chest over my shirt and wagged them at the mirror. I giggled and put them back. I opened her panty drawer and looked in. I began to flip through the panties and think about how she looked in them. While doing this I grabbed something on the bottom that was solid and felt like silicone. I pulled it out and was amazed. It was like a pair of jockey shorts, only it was flesh tone and made of silicone like the breasts. It had an exaggerated pussy with big full lips and labia, with padding for the hips and ass.
I marveled at the sight of it. It looked like a real pussy except for the oval hole where the vagina and anus were. I wondered where, when and if Cindy had ever worn them. Had I seen them on her and not known it? I spread the legs and watched as the pussy opened up and the labia spread wide to reveal a rather large erect clit. I held them up against me and looked in the mirror again.
"Holy Fuck, that looks real!" I thought.
I was so amazed, I couldn't help myself. I had to try them on and see how they looked. I stripped off my pants and underwear and pulled them up as quick as I could. They were a snug fit so it wasn't all that fast, but once they were on I couldn't believe it. With these pads on I looked like a girl. I mean, it really looked like I had a pussy. I was fairly hairy so it looked like I only shaved my pussy and ass, but it looked real. I had wide smooth hips, a round jiggly ass and a really hot looking pussy. I spread my legs and watched my pussy open in the mirror. I lost my nuts in a motorcycle accident. So with my cock pulled back to my asshole, there was hardly a bulge and it looked so much like a real pussy I was dumbfounded.
I put the DD-cup tits back up to my chest and looked at myself. As I examined my reflection and made up my mind. I was going to shave my legs and see what this would look like. I stripped nude and headed for the bathroom............. I dug out Cindy's hair removal mousse and read the directions carefully. I applied it to my whole body except my cock, ball sack and ass crack. While I waited for it to work, I shaved my face as smooth as possible. Then I jumped in the shower, rinsing away the mousse and all my body hair. Then I finished off by shaving the crack of my ass and cock. I had a crew cut, so I was as hair free as I could be.
I dried off and examined myself in the mirror. I was 5'11", 140 lbs and baby smooth all over. I smiled at how smooth everything was and walked nude back into Cindy's changing room. I immediately pulled on the silicone pussy panties and pulled my cock back until the tip touched my asshole again. I looked in the mirror and smiled. I pulled up a chair, sat down and spread my legs again. I watched in amazement as my pussy opened to reveal a big clit and big full labia. The only thing that looked out of place was the head of my cock sticking out where my vagina should have been and covering half my asshole.
I smiled, jumped up, grabbed the big DD breast forms and sprayed them with Cindy's adhesive spray. I sprayed my chest and pressed them into place. I held them in place for a few seconds, then released them. I looked at them in the mirror. Played with them and shook my chest to watch them jiggle, bounce and swing. They were quite heavy, so it looked and felt like I had real tits. I looked back and forth from the pussy to the tits and was truly amazed at how real they looked. I turned, looked in the mirror again to admire my pert round butt.
"Fuck, That's Awesome!" I said aloud.
I looked like a nude girl with a crew cut. The panties and tits matched my skin tones almost perfectly. I couldn't believe how natural it looked. Suddenly, I had big tits, wide hips, a big round ass and best of all, a big fat juicy pussy. This was better than I had imagined. I could dress up and be my own girl. I couldn't help myself, I had to know what it would look like when the change was complete.
I tried on several wigs to see what they looked like I had a thing for redheads but I settled on long straight blonde hair. When I looked in the mirror again, I felt my dick stir. I smiled, I was sexy and I was turning myself on. I quickly put on all the makeup that I had seen Cindy use a million times before. When I was finished, I was thrilled with how good I looked! I looked like an honest to god, hot, nude babe! I looked in astonishment at my reflection and I couldn't tell I was a guy.
I had always admired Cindy when she dressed up and I couldn't believe that just by putting this stuff on, how completely I was transformed. I looked and felt like a whole new person. I had to wonder if Cindy felt the same way when she dressed up. Was that why she was so fixated on the dress up sex games? Because she could change into any vision of womanhood she had at the time? I liked when she did it and made up as I was, I could definitely see the allure.
I had gotten out of the shower and changed from an average male to an extremely fuckable female in about 45 min. I smiled at the thought of it and decided I was going to stay dressed like this for the rest of the day. Since tomorrow was sat, maybe tomorrow too. I grabbed a simple blue summer pullover dress with spaghetti straps and put it on. I looked in the mirror and thought it was perfect. It was thin, breezy, it came to just above mid thigh and best of all. It looked like it was painted on. I didn't have a bra or panties on, so I was showing lots of tit and my stiff nipples were just barely covered.
I modeled for myself in front of the mirror again. I pulled up my skirt and admired my new bald pussy. I jumped around and watched my new tits bounce around. I was shocked at how active they were. They took on a life of their own. It felt like I had 2 watermelons fighting on my chest I bent over and watched as my skirt pulled up to reveal a set of swollen pussy lips between my thighs. All I needed now was a pair of shoes. I grabbed a pair of sandals with a 3 inch heel and strapped them on. I stood up and looked down, but couldn't see past my tits. I smiled, looked to the mirror again and thought "Now it's complete."
"This is fucking awesome." I said aloud as I looked at myself.
I watched myself in the mirror as I walked around. My hips swayed nicely and the feeling of having tits jiggling in front of me was intoxicating. I began to think of what it would be like to be a girl. How it would feel to have real tits bouncing around all the time and having a pussy that every guy you saw wanted to get into. This was so hot! I watched myself jiggle some more and turned to step out of the dressing room.
"Hey Jimmy, want a beer?" I heard a familiar voice say.
I instantly froze and tried to cover myself out of embarrassment. I looked up and sure as shit, there was Bob, sitting in the living room drinking beer. From where he was sitting, he was looking directly into the dressing room. I looked around quickly, searching for a way out but there was none. I closed my eyes and slumped my head in defeat. I was so embarrassed, I wanted to die.
"Fuck! How long have you been here?" I asked.
He handed me a beer and motioned for me to sit across from him. I took the beer and sat obediently
"Cindy asked me to check on you on the way home. You were in the shower when I got here, so I sat and waited. Then I watched you do a complete sex change right before my eyes. It was very impressive Jimmy." he said with a nod.
"Oh God! Please don't tell anyone!! It was a one time thing, please please please don't tell anyone!!" I pleaded.
"Don't worry, I won't. I've got an idea." he replied.
I breathed a sigh of relief at his reassurance, but got an uneasy feeling when I looked at him. He was looking right up my dress at my pussy. I slapped my knees together when I realized what he was looking at.
"Uh? Idea? Huh?" I stammered.
He came over and stood in front of me ushering me to stand, then turning me so my back was to him.
"You just be quiet, do what you're told and nobody will ever have to know............" he reassured me as he bent me over the coffee table and lifted my dress.
"No! Oh No! God No! You can't!" I protested.
I tried to stand but he slammed me back down. Bob was a hulk of a man and I didn't stand a chance on my best day. He was 6'5" tall and at least 290 lbs of muscle. He was a former Marine and had served with distinction until he retired at 50. Now he did some kind of big money consulting work. Even at the age of 55, he was scary.
"I said, Be quiet and do what you're told!" he snapped.
"But you can't, I've never...." I stammered at him over my shoulder.
"Don't your worry your pretty little head about anything, Jimmy. I drank 5 beers watching you and I gotta piss. So shut up and keep still!" he explained angrily.
All I could do was stare straight ahead and wait. I couldn't believe he was going to use me like a urinal. He was going to pee inside me. At least he wasn't going to fuck me. It had to be better to let him pee in me than to let him cum me.
He played with my ass a bit, then he poked at the head of my cock with his finger. I listened to him laugh and unzip his fly. Then I heard him spit into his hand several times. Next I felt the wet slippery head of his cock brush against mine and poke at my anus. With his cock rubbing against the head of my cock, I got the most intense sensation. My whole cock tingled with pleasure. Bob poked his cock hard against my puckered hole and still couldn't gain entry.
"Push like you gotta take a shit!" he snapped.
When I did, I felt nearly the whole head of his cock slide inside me. Then he stopped. I couldn't see it, but it felt fat and dome shaped. He put both hands on my hips and I immediately felt the warm flow of urine in my bowels.
"Now squeeze real tight Jimmy. It would be a shame if you spilled some and I had to explain to Cindy how her carpets got stained." He taunted as he continued to pee.
I squeezed tight like he said and I could feel pee gurgling up into my guts. The pressure would build. Then it would gurgle further in. By the time it happened the third time, I could hardly hold it. Bob just kept peeing inside me. It felt like a gallon of pee already.
"Stop. Please I can't take anymore" I whimpered.
"Sure you can Jimmy. I'm almost done anyway. So you be a good girl and quiet down." he chortled.
I gritted my teeth and prayed for him to finish. Just as I felt so full of pee that I was going to explode. He pulled out and zipped up his pants.
"Hurry Jimmy. Run to the bathroom. Run" he teased.
I clenched my ass, locked my knees together and began to run as fast as I could. My arms were flailing to the side as I ran. Between the heels, holding the pee and a set of big bouncy tits, it was the hardest thing I had ever done. The heels were bad enough but the tits threw me off balance and the pressure in my bowels made it even harder. The worst part was Bob running right next to me goading me on as I tried to hurry.
"Hurry Jimmy"
"Don't ruin the carpets Jimmy"
"Look at those tits bounce Jimmy"
"You're leaking Jimmy"
"Nice ass Jimmy"
"You run like a girl Jimmy"
"You're almost there Jimmy"
When I got to the bathroom, I pulled up my dress and sat down as quick as I could. Pee exploded out of me and rushed out in a big stream. Interrupted only briefly by a few odd chunks of shit that flew out just as quickly. When the stream of urine slowed to a dribble, I began to relax.
"Now don't you feel better Jimmy?" Bob asked.
"No, I do not feel better! You just pissed in me!" I replied angrily.
"That's alright Jimmy. You'll feel better once we rinse the piss out" he laughed while holding up the enema bottle.
"What!" I protested.
"Jimmy. You're going to do exactly as you're told or, I swear to god, everybody you ever met will know about this." he said sternly as he filled the bottle.
The enema bottle was a hot water bottle with a 3 foot hose and nozzle. I watched quietly as he filled the bottle and affixed the hose. He set the bottle between my feet and handed me the nozzle. I took it, reached between my legs and looked down. I couldn't see over my tits, so I leaned back, scooted forward on the seat and spread my legs farther apart. I was holding my dress tight around my waist so it wouldn't get wet and I was shocked by the view. I was looking over a monster set of tits at a beautiful hairless pussy. The shocking thing was that they were mine and they looked absolutely real.
I probed around and inserted the nozzle. It wasn't very comfortable so I reached behind me to hold the nozzle in and scooted forward some more. Once I was situated, I looked up at Bob. He smiled and lifted the bottle. I clenched my asshole tight as I felt icy cold water flood my bowels. To increase the pressure, Bob lifted the bottle as high as it would go, pulling the small hose tight between my pussy lips. When he began to squeeze the bottle, I slapped my knees together and began to squeal. After the warm piss enema, the ice water was a huge shock to the system, making it extremely hard to hold in. Looking down, I could see my pussy lips wrapped around the hose and could feel how cold it was through the pussy panties.
My cock shriveled up from the cold as Bob continued to squeeze the bottle until it was nearly empty. Once he was satisfied, he put down the bottle and said ok. I quickly pulled out the nozzle, scooted back and moaned with relief as a jet of clear cold water shot out of me. He put the bottle in the sink and watched me as we both waited for the last of the water to dribble out. Bob was the first to break the silence.
"Show me your tits Jimmy." he interjected.
I took a deep breath, pulled down the straps to my dress Then I pulled down my top revealing my tits. When I looked down and took in the view, I felt my cock getting hard again. My skirt was pulled up. My top was pulled down. I was looking down at a massive set of pert firm breasts with fat oversized swollen nipples. Right between them was a bald perfect pussy with a wide spread labia and a big clit that looked like an inch long pecker. It was quite an impressive sight. I had often fantasized about meeting a girl built like this.
Bob stepped up in front of me and began to fondle them. He stroked them, squeezed them and played with the nipples. He reached between my legs and ran a finger through the folds of the labia. I spread my legs farther to give him as much access as he wanted. The thinnest part of the silicone pussy was through the center of the labia. While he was running his finger up and down the labia, it felt like he was stroking my cock. It felt so good, I couldn't help but to spread my legs. Bob looked up at me while he was stroking my pussy with one hand and squeezing my tit with the other............
"These are nice Jimmy. Not as nice as the real thing, but nice." he said.
Then he stood close in front of me and unzipped his pants. I closed my eyes tight and turned away quickly. Bob laughed and zipped his pants back up. Then he headed out the door.
"I'll be in the living room when you're done." he said as he was walking out.
When I had finished cleaning up. I rearranged my dress and walked back to the living room. Bob was sitting in the chair pointing at my unopened beer. I sat down opened it and drank about half of it in one gulp. We began to talk and I drank 2 more beers.
He asked about the way I was dressed. How often do I do it? Do I like guys? Have I ever had sex with a guy? Does Cindy know? I explained to him how I had found the pussy panties and my curiosity about them. It was the first time ever. I don't like guys. I have never had sex with a guy, and he was the only one who knew.
As we talked, I became more comfortable and relaxed. I began to sit like I always did. It never really dawned on me how un-lady like it was. With no panties on, it looked like I was going out of my way to show off my pussy. When we finished the 12 pack that he brought, Bob came over and sat by me
"Why don't you put your feet up and relax a while?" he suggested while patting his lap.
I turned, put a pillow behind my head and laid on my back with my legs over his thighs. He pulled my dress up to my waist and began to caress my thighs. When he did this, it sent a cool tingle through my whole body and I took in a deep breath. Then he began to examine and caress my pussy. I felt my cock start to grow and instinctively spread my legs slightly. Bob saw this and put one leg over his shoulder while the other rested on his thighs. He was now sitting between my outstretched legs and I stared blankly at the ceiling the whole time. He was caressing my thigh and running his thumb through my labia again.
I tried not to react because I didn't want him to know how good it felt when he did that. Instinct took over though and I spread my legs a bit, while letting out a small moan. I protested when he began to finger my ass. He just looked at me, so I shut up and looked back to the ceiling. Because of the enemas, my ass turned wet and sloppy in no time. His finger was wet and slick as it slid across my cock head into my ass. it felt so good, I couldn't help but to flex my hips. Bob fingered me for a little while longer then stopped.
He moved around a while, then reached up, pulled my top down and began to play with my tits. He rolled over, put a hand next to each of my shoulders and kneeled between my legs. His face was only inches from mine and I began to get uneasy laying under him like this.
"What are you doing Bob?" I asked.
"Well, I've been looking at and playing with your pussy and now I'm gonna fuck you. What else?"
"The hell you are!" I responded and tried to squirm out from under him.
He let his full weight drop onto me, pinning me down. I felt his warm skin and hairy legs on the inside of my thighs and realized he already had his pants down. I redoubled my efforts to escape and began kicking and screaming.
"No!" I screamed "No! Don't Bob! Stop!"
"That's my girl." he chuckled.
I could feel his cock poking at me looking for a home while I bucked and screamed under him.
"Don't do this Bob! Stop!" I pleaded desperately.
While I struggled to get out from under him. I felt the head of his cock poke into my asshole. In two quick jabs, his cock slid up in me until it was buried balls deep. Bob let out a long satisfied moan.
"NO! God NO! Get it out!!" I screamed.
I was kicking and screaming harder than ever, but I could hardly move. I heard another chuckle from Bob and he began slamming it into me deep, hard and fast.
"Oh god no." I whimpered.
I quit struggling and accepted the fact that I was trapped He was going to fuck me and there was nothing I could do to stop it.
"That's it Jimmy! Take it like a man!" he laughed.
"Fuck You!" I snarled.
I was pissed off and began to struggle to free myself again. Bob just kept fucking me and laughing.
"You go girl!" he mocked.
I stopped struggling again. I was so tired I could hardly move. I accepted my fate, pulled my knees to my chest, spread my legs as far as possible and just laid there.
"That's it Jimmy! That's a good girl! Take it baby! Fuck yeah!" he whispered in my ear.
"Fuck you Bob." I whimpered back almost crying.
Bob stopped fucking me for a second. Looked me in the eye. Then he started to slowly ease his cock in and out of me. His cock felt like it was 10 foot long and as big around as a telephone pole. The slick shaft was rubbing hard against the head of my half hard cock. It felt so good, it almost hurt. I closed my eyes and winced.
"Don't be such a baby Jimmy. You might learn to like it." he said with a smile.
I punched him in the ribs.
"Fuck you!" I snarled.
"Oh, poor baby. It'll be ok. Uncle Bob can fix it." he said while making a sad face.
I grimaced and made a face back at him. I couldn't let him know it, but having a cock sliding smoothly in and out of my ass while the head of my cock was rubbing against the slick shaft was driving me wild. It was the most unbelievably intense feeling I had ever imagined. It felt so good, it defies description. It was really fucking intense.
He laid down on top of me again and began pounding his cock into me fast and furious. All of my sensations were magnified. The feeling of his big cock slamming into me. The feeling of the head of my cock being ground against the slick shaft of his cock. Plus, every time he slammed balls deep into me, my cock was smashed between us. Making the head of my cock swell out and giving me a little extra tingle. The whole experience was more intense than ever.
When I decided to get dressed up in Cindy's stuff, I had no idea what I was in for. I never imagined or bargained for any of this. Bob had caught me. Now he was laying on top of me using me for a cheap sexual thrill. Being forced to let him use me like an inflatable sex toy was the most degrading experience of my life. I was trying desperately not to react and let him know how good it felt. I was just laying there with my legs spread hoping he would be done soon.
I was soon to learn what an experienced lover he was. Bob's cock was pounding into my ass and stabbing at my prostate. Making it nearly impossible to lay still. He drove it in hard and fast, then he would take it real slow and easy, only to pick back up to hard and fast. The tension would build, then ease back, then build again. It was driving me wild with lust.
For the first 5 minutes, I was fairly silent. I only gasped or moaned a few times, but they trailed into a smooth stream of quietly moaned oh's and ah's. He would bring me to the brink of orgasm only to slow his pace and deny me satisfaction. Each time the crescendo built to a peak, it was more intense than the last. The pleasure was becoming unbearable, I was turning into a ball of orgasmic need. I wanted him deep inside me and was praying for him to make me cum. It felt so good, I wanted him, I needed him to fuck me hard and fast to finish me off.
After 10 minutes of this, I wanted to cum so bad, I was about to explode. I had been brought so close to orgasm, so many times, that my ass was a worn out raw nerve. My bowels had involuntarily begun to push steadily. The harder I pushed, the more my passion grew. My bowels squeezed his smooth hard shaft like a vice as he forced it in. With every thrust, every over stimulated nerve ending lit me up like a Christmas tree.
"Fuck Me!! FUCK ME HARD!!" I heard myself squeal.
Bob was driving his cock into me like a pile driver and I couldn't stop pushing. It was like being in labor. My mouth hung open and I let out a steady squeal as he slammed into me. Then the dam broke and my whole body erupted into orgasm. I wrapped my arms and legs tightly around him and began jerking and squealing uncontrollably. I could feel my asshole spasm around Bob's invading member while he continued to drive it balls deep into me.
As I flailed in ecstasy under him, Bob slowed his pace. I could hear him grunting in my ear but it sounded a million miles away. The only thing I knew was the passion of my orgasm. I was driving my hips upward to meet his thrusts. My orgasm was washing over me in waves and I couldn't seem to get enough to be satisfied. It felt so good I was about to go insane. At that instant, it was like he was reading my mind, he began driving his hard cock into me as fast as he could. I wrapped my arms tight around his shoulders while spreading my legs wide with delight.
My orgasm quickly peaked, accompanied by a series of high pitched squeals, moans, oh's and ah's. Then just as quickly, it subsided while Bob continued to work his cock feverishly into my over heated ass. I stared at the ceiling in a daze and listened to the wet slapping noises of his quick deep thrusts. His pace slowed until he drove deep inside me and let out a long satisfied breath.
"Fuck that was good." he whispered.