I'm Jimmy James and this is a story of cross dressing and sexual submission at the hands of my girlfriends father.
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The Morning After
When I woke up, I was hung over bad and my ass hurt like hell. I wasn't really sure where I was at first, but one look around and I recognized that I was home in my bedroom. As I rolled around in bed I was still pretty groggy and I had to piss like a racehorse.
As I began to regain my senses I had an uneasy feeling something wasn't right, but I couldn't put my finger on what it was. When I reached down to grab my cock like I did every morning, it hit me. I had reached down into my crotch and grabbed a pussy!!! I shot up into a sitting position and was instantly wide awake. I looked around in stunned disbelief.
I was wearing a dress!!! One strap was pulled down and my tit was hanging out. I was still confused so I pulled up the dress and stared at my pussy dumbfounded. I put my dress back down and began to gently squeeze my tits while cautiously looking around. I saw a blonde wig laying on the pillow and I stared at it blankly while squeezing my tits.
It was all coming back to me. I had found those silicone pussy panties and dressed up as a girl. It seemed to me I had a great time last night, but as I put the pieces together it seemed like a total disconnect from reality.
Cindy's dad had found me like this. He pissed in my ass. We drank. He felt me up. Raped me. We drank. He fucked me again. We drank some more. We went out in public to a restaurant. I saw my first glory hole and willingly sucked my first cock. We drank some more. I got on stage and stripped at a crowded bar. We drank some more. Bob fucked me again. Then I let a bunch of strangers fuck me one after the other. The whole night was a fucked up mess. Just as soon as I dressed up, everything went drastically wrong. It just couldn't have been more wrong.
I kicked off the blanket and laid spread eagle on the bed in disgust. I couldn't possibly have been anymore ashamed of myself. How the fuck could I possibly think that was fun?!? I reached down and started to play with my pussy while I thought about it. The pussy felt so real, I instinctively started to play with the clit. As I laid there thinking, I had to admit the orgasms were very real and pretty fucking intense. Plus, I had a bunch of them. More than I ever thought a guy could have in one day.
I thought about how much my ass hurt. I had a belly ache too, but it was real low in my belly. Not like any belly ache I ever had before. I spread my legs and felt my bare feet slide out from under the blanket. I fingered my cock head a little bit, then eased my middle finger into my ass. My asshole didn't put up even the slightest bit of resistance. My finger just slid right in. The inside of my ass was soft, squishy and wet.
This took me by surprise. I had never fucked anybody up the ass and had no idea an ass could feel like that. I began to finger myself and think about Steve again. I thought about how all the guys told me what a good fuck he was. Was this what they were getting?? It's no wonder they liked it. It was really nice. I bet it felt GREAT to stick your cock in a hole like that. I mean if you couldn't get pussy, this HAD to be the next best thing to being there.
As I started to finger myself harder, I got a warm feeling in my belly and my bowels began to push involuntarily. It was incredible! My bowels squeezed my finger tight while I continued to force it in. It was fucking great. It was every bit as soft and wet as pussy, but it was way tighter. I mean it was tighter than any pussy I had ever been in. Including Cindy's!! And I always thought she had a tight pussy!
Holy Fuck did I miss out!! I could have been fucking Steve and getting this all the time growing up. Instead, I was jerking off in my room. What a fucking idiot I was!!
While I continued to finger myself hard, I couldn't help myself. I spread my legs wide and pulled my knees up to my chest. I was plunging my finger into my ass mercilessly. Not so much because it felt so good on my finger, but because it felt so good to have something pumping into my ass.
That's when a disturbing image popped into my head. There was Steve bent over with a big smile while a bunch of guys took turns fucking him. They were banging him like a bass drum while he just smiled and took it. Then all of the sudden it wasn't Steve any more, it was me! And I was dressed like a girl!!
That was a shock!! And an image I just wasn't willing to accept! I sprang up in bed and sat cross legged while staring at the offending finger. I enjoyed that way too much! And that ain't right!!
As I looked at my finger, I noticed it was covered in a thick white goo. The more I examined the goo, the more I thought it looked like cum.
"NO.... It can't be!" I thought.
I slowly brought it to my nose and gingerly sniffed at it. I pushed my hand away and turned my head quickly.
"Holy Fuck That's Cum!!" I mumbled under my breath.
I leaned forward and began wiping my hand on the bed to get it off. While I did this I noticed my bare feet and once again got the feeling that something was wrong. I stared at my feet and thought about it for a long moment before it hit me. I had bare feet. I could have sworn I had Cindy's high heeled sandals on. I rolled on my side and looked off the edge of the bed. There they were sitting neatly side my side. I never did that with my shoes and only one name popped into my head.
Bob
No sooner had I thought his name when he came walking into the bedroom wearing nothing but a towel.
"It's about time you got up! It's noon!!" he joked.
I looked quickly at the clock. It was 12:00 alright.
"Hope you don't mind, but I fucked you again while you were passed out. At least I think you were passed out. You just laid there so I'm pretty sure you were passed out. Besides, I figured you had such a hot ass and you did so good at the club, you wouldn't mind if I fucked you again. So I fucked you extra hard just to make sure." he laughed. "And I was right. You didn't mind a bit."
Then he pulled off the towel and pushed his cock at me.
"Suck my dick Kitty" he ordered.
All I could do was look at him.
"Well? Get on your knees so I can sit on the bed." he said with a stern voice.
I gave him a resigned look and climbed off the bed. While I was climbing off, I couldn't help but to notice my tits jiggling around in front of me.................. They were quite large and quite heavy but it was an intensely erotic feeling. Accepting that I liked the way having tits felt was very strange.. It was like having two big balls of Jell-O splashing around on my chest..
While I kneeled next to the bed, Bob sat in front of me and spread his legs. I stared at his limp dick and the image of cocks sticking through a hole in the wall flashed into my mind. The memory of having a stiff piece of meat throbbing in my mouth while he fed me ball juice flooded my senses. It had been such a turn on last night but now all I felt was shame. It violated every sense of decency I ever had. Only twisted perverts and sluts enjoyed it that much.
"Well? Let's get started" he said seriously "I just can't get going until I've had my morning blowjob."
I kneeled there examining his cock. I examined the thick veins that were just starting to bulge. The smooth curves of his already bloated head. The way it was slowly starting to get hard as he waited in anticipation of my services. I reached up and gently began to stroke his now flaccid penis while licking my lips.
"Don't be shy, suck it!" he instructed. "You did it last night, you can do it again this morning"
I looked up and saw the determination in his eyes and decided it wouldn't do any good to argue. I dejectedly looked back at his cock and started to suck the bloated head.
"Yeah, that's my girl" he said as he laid back and got comfortable.
I began to suck more and more of his cock into my mouth. I looked up to see him watching me closely. As I looked up, I began to get uneasy about what I was looking at. It would have been disturbing enough to see him laying in bed nude, but he was laying in bed nude while I had my face buried in his crotch. Talk about disturbing.
Bobs cock was throbbing and growing quickly in my mouth while I sucked it in deeper and faster. I was sucking him like I knew I liked to get my dick sucked and he seemed quite pleased. He began to moan when I was slamming his cock into my throat until the whole head was stuffed down as deep as it would go.
I drove forward until my face was smashed against his belly and held it there. I wiggled my tongue around the underside of his cock while I looked up at him again. Once again, I was struck by how strange it was to look up at him from here. My face was buried so far into his crotch his balls were pressed against my chin and his hard cock was stuffed deep in my throat. I could taste his cock and the soap from the shower. Bob was just staring down at me with a big grin.
"Yeah, baby... That's it..... Look at me when you suck my dick." he said as I looked back down.
He tapped me on top of the head. "I said look at me when you suck my dick"
I looked him in the eye and slowly pulled back. I could feel his fat cock slide out of my throat until only my mouth was filled. I watched him steadily until just the tip of his cock was clenched between my lips. I slowly bobbed up and down while sucking just the head.
While I watched him, I began to reflect on what a wild feeling it was to have a cock in my mouth. Feeling it sliding in my throat was even more intense. I hadn't had alot of time to think about what I had done last night at the glory hole, but this didn't really seem that bad. The thing that bothered me was it was such a personal service and I had been forced into it. Having Bob watch me suck his cock while I was on my knees in a dress was extremely degrading and I was trying to get it over with as soon as possible. For him, watching his little girls boyfriend suck him off must have been the ultimate power trip.
As I thought about this, I thought about my glory hole experience. It was just a cock sticking through a hole. It was down and dirty sex, but I found it strangely pleasant. I began to see how a girl could enjoy doing this. I had always loved Cindy because she said she liked sucking cock and I always believed her because she was good at it. I began to think if I were a girl, I would have been the same. Even though I was a guy and I was being forced to do this....... I found it intensely erotic and extremely sexual...
"Hard to believe it's only your second day as a girl. You're pretty good at that. I'll bet once you've had a few days to practice you'll be even better." he said plainly.
I kept looking at him and slowly sucking him in and out. I licked the tip of his cock and smiled.
"I'm just doing all the things Cindy does." I said hoping to get a rise out of him.
He just smiled and shrugged his shoulders "I guess so."
While I went back to sucking his cock. I began to evaluate what I was doing, seeing and tasting. His cock was so thick and smooth as it slid through my pursed lips. It was starting to taste more and more like cum while I sucked it hard. I pushed it down my throat again and stroked the underside with my tongue.
"Good Girl" Bob cooed.
I tried to smile and found I couldn't help but to be pleased when I heard it. I knew that if I wanted him to get off in a hurry, I had to turn him on. So it was important that I play up to him but this was different. I had a real sense of satisfaction knowing he liked it.
I stared straight into his eyes and bobbed up and down just a tiny bit. All I could see was his pubic hair and his face. I put my hands on his thighs and pulled back as slowly as I could. As I watched that thick round piece of meat being brought into view from such a tantalizing angle, I felt my cock getting hard. I took a quick breath when I realized. This was turning me on!?!
I sucked on the head in a quick in and out motion. I pulled back and examined his cock while stroking it and licking his balls. It had thick bulging veins and a smooth spit shine while it stood there proudly throbbing in my hand. His balls were pressed around my nose and I had to admire how muscular it felt in my hand. I found the whole experience breathtaking and quickly went back to sucking his thick shaft.
I stared at it in front of me as it slid smoothly in and out of my tightly pursed lips. As I examined it in front of me and noticed that it felt rock hard in my mouth, I felt it start to throb. Bob grabbed my head and thrust his hips several times, forcing his cock into my mouth. Bob began moaning, his cock throbbed forcefully and my mouth was almost instantly flooded with cum. Cum splashed onto my tonsils in thick streams of goo. Without thinking, I instinctively began to swallow while he continued to moan and empty his balls in my mouth.
While I kneeled in front of him, watching him make faces and swallowing his cum. I could feel my cock trying to get hard and throbbing in it's prison. As I continued to swallow Bob's cum, my cock was becoming rock hard and it was getting quite painful. I moaned into his cock while wiggling my ass and thrusting my hips to relieve some of the pressure.
Pinned back in the silicone panties like it was, it didn't do any good. I reached down and began to squeeze my cock shaft through the pussy while I continued to thrust my hips and wiggle my ass. I could feel my cock throbbing between my butt cheeks while Bob's cock began to relax in my mouth........
Bob released my head and looked down at me with a big smile. While I looked up at him and continued to suck his softening cock I felt my own cock relax and begin to get soft. Bob and I looked at each other as I sucked his softening shaft in and out a few more times. While we did this, I thought about how fast my cock had gotten hard while he came. He had started to cum in my mouth and my cock got rock hard almost instantly. I pulled back and stared at his cock in disbelief. There was a string of cum from the tip of his cock to my lips that broke when I licked my lips.
"Good Girl" Bob said reassuringly "That was really good."
I just looked at him and smiled.
"Thanks" I mumbled.
"Why don't you rinse out your ass and get a shower while I pick you out something to wear." he suggested "I need to get some clean clothes and I thought we would hang out at my house."
"OK" I chirped and headed for the bathroom.
When I got to the bathroom, I closed the door and stared at myself in the mirror. I watched myself pull down the dress until it fell to the floor. I had a crew cut and my makeup was a mess. I had large firm breasts, wide smooth hips and a hairless pussy with a large clit and labia poking out between a fat set of pussy lips. I turned, spread my ass cheeks and inspected it. It was worn out, sore and covered with dried cum. Except for my cock head poking out over my asshole, there was no indication that I was a guy.
I turned back and watched myself fondle my breasts and caress my smooth hips. I couldn't get over how much I looked like a nude woman. My pussy looked especially real. I caressed and played with it while I watched in the mirror. As I did this, I could feel my cock begin to get hard again. I couldn't get over what a rush it was to reach down and play with my own pussy. Having tits and a pussy was like stepping into the twilight zone. It was like a world of opposites. Instead of a dominant male, I was a sex starved submissive female to be used as Bob saw fit.
While I was looking at myself and thinking about how Bob had made me his personal slut. I saw the water bottle sitting on the counter. I picked it up and began to fill it while Bobs words echoed in my head.
"Rinse out your ass." and "You're going to keep that thing rinsed out and ready to go 24/7"
I attached the hose, inserted the nozzle into my ass, sat on the toilet and squeezed the bottle hard. I felt my bowels flood with water and once the bottle was nearly empty, I pulled out the nozzle and let it pour out of me. There was so much shit, that I filled the bottle a second time and inserted the nozzle again. When I turned back to the toilet, I watched in amazement as dozens of big white gobs of cum floated around the bowl. I smiled, sat down and emptied the water bottle into my ass for the second time. I pulled out the nozzle, spread my legs and stared at my pussy while a thick stream of cool clear water gushed out of me.
Once the water was done running out I fingered myself and marveled at how good it felt in there. I smiled, put the water bottle in the sink and jumped in the shower. While I soaped up and began to wash, I couldn't get over how erotic this was. I soaped up and played with my tits and stroked the big nipples gently. I soaped up and played with my big round jiggling ass. I spread my legs and caressed my fat pussy lips while running a finger through the labia. While I ran my soapy fingers through my pussy, I was rubbing my cock hard through the panties.
I did that for a few seconds and couldn't take it anymore. I pulled the silicone panties down and watched as my half hard cock sprang free. I instantly grabbed it and jerked off feverishly with one hand while squeezing my tit with the other. It was such a turn on, I came almost immediately. I watched as cum shot out and splashed onto the wall. I smiled, washed my crotch and fingered my ass some more. Then I pulled my cock back, pulled up the panties and adjusted everything so it looked right. I finished washing up and got out of the shower.
I stood in front of the mirror and watched myself dry off. I didn't have any makeup and I looked like me again, only now I had tits and a pussy. While I looked at myself, I couldn't help but think "Is this what I would look like if I was born a girl?" I was pretty hot! I needed a shave but the rest was pure gold. I stood thinking about it and found myself caressing my pussy and wishing it was real.
I gave a quick shudder and was shocked that I would even think such a thing. I quickly broke out the razor and started to shave. While I was shaving, I caught myself at least a dozen times staring at my tits or pussy and wondering what it would be like if they were real. I put it out of my head as quickly as possible and hurried to finish shaving. I picked up my dress and walked nude into the living room where Bob sat watching TV.
"There's my girl" he said quickly and stood up.
He ushered me into the dressing room and pointed to the chair. I put the dress over the back and obediently sat down. He grabbed a wig and turned it inside out over his hand.
"I noticed your wig was a bit loose yesterday" he said
Then he sprayed the inside band with adhesive. Afterward, he sprayed the whole top of my head.
"I think this will be better"
Then he plopped the wig on my head and tugged at it here and there until he was happy. He held it in place for a few minutes and tugged on it to test that it was secure.
"There! Now you're a red head. Have a look"
I looked in the mirror, I had bangs and long curly red hair that came a few inches below my nipples. I tugged at it and tried to move it around. No luck. It was stuck. I swished it around and pulled at it some more. It was like having real hair. It was glued to my scalp so tight it even hurt when I pulled it. As I was examining my new look, Bob pointed at some clothes.
"You can put these on, and I packed a bag for later" then he handed me a purse. "Don't worry about putting on makeup but you'll need some for later, so be sure to pack what you need."
Without another word Bob walked back into the living room and sat down. I watched him go and picked through the stuff he told me to wear. There were the high heeled sandals from last night, a tiny white cotton pair of shorts and a skimpy white cotton tank top. The shorts and top looked to small to fit into but I decided to try anyway.
The shorts were so small, I could just barely get them up. They were so tight, there was no reason to tie the string, but I tied a neat little bow just the same. Next came the tank top. It was too small too and I had trouble getting it on. Once I had it on, I pulled it down as far as it would go and there was about a 4 inch patch of belly between the tank top and the shorts. I shook my head and sat down to put the sandals on.
Once everything was on, I stood and looked at myself in the mirror. The shorts and top were so thin and so tight that they looked like they were painted on. Every curve and bump stood out like it was in a spotlight. My pussy and nipples looked like they were trying to push through the thin fabric and bust out. I shook my head again.
"I am definitely his slut" I thought to myself.
I took the purse packed a brush, perfume and all the makeup I would need for the night. Then I got curious and looked into the bag he had packed for me. There were open toed black high heels, black stockings. garter belt and garters. A black mini skirt, a see thru white thong and a lacey white blouse. I didn't know what the stuff was for, but he definitely had something planned.
I put the purse over my shoulder, grabbed the bag and walked into the living room where Bob was waiting. As soon as I walked in, Bob smiled and looked me up and down. I felt extremely uncomfortable under his gaze as he inspected the merchandise. He gave his finger a twirl and I did a slow spin in response. Bob just kept smiling.
"FUCK you got a nice ass Kitty!" he grinned.
I smiled discreetly "Thanks"
Then he got up squeezed my ass and said "Well, we better get going"