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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An afternoon at the pool
While we walked through the mall, I was enjoying the way it felt to have my tits and ass jiggling. It was such an intense feeling. As guys were checking me out, I wished they were real so I would know what it was like to give up some real pussy.
"What would it be like to get fucked in a hole made specifically for pleasing cocks? Would it be better than getting fucked in the ass?" I wondered.
I had trouble believing it would be. I had never been with any women that got off as good as I got off while getting fucked. I could see the advantages of a real pussy. I wouldn't have to rinse it out to get rid of shit or to keep it wet and fuckable. It would self lubricate and there would never be a worry about shit. On the down side, I would have a period every month and I could get pregnant. That would suck.
As for a hole for pleasing cocks, I had to admit, the inside of my ass felt pretty good. I know I wouldn't mind fucking a hole that felt like that... Bob obviously liked it. He even went as far as to say it was better than pussy. I know Buddy and the fifteen guys he pimped me out to seemed to enjoy it. None of them even seemed to notice that it wasn't real pussy..
I shrugged it off and decided to enjoy the feeling of having big bouncing boobs and a round jiggling ass for once. It was a great feeling. It was a constant reminder of womanhood. They were uniquely feminine and they were mine. They were the things that made men want me and since they were so active, I found them every bit as hard to ignore as all the men who were staring at me.
I smiled and waved at a few of them and continued to walk with Bob. I was so worried about the wet spot in my crotch on the way in, I hadn't noticed much of anything. It felt so good to be prancing around and strutting my stuff in public. My boobs were bouncing and my ass was jiggling with every step.
I had to wonder if this many guys had checked me out on the way in. I was smiling and looking around to check out the guys. Just about all of them were checking me out too. From young boys, (11 or 12) to old men, (70s) they were all turning to look at me. The ones that were 15 to 20 seemed the most interested. They made no secret about what they were looking at. There was no doubt in my mind that they were thinking about bangin' my booty.
I smiled and soaked it all in. I thought about all the times I had watched women walking by and thought the same thing. Walking around with big tits and a nice ass on display was like an advertisement for sex. The bigger the tits and the nicer the ass, the bigger the ad.
"Did all women feel like this?" I wondered.
Being seen as a woman was extremely sexually provocative for me. The feeling of all the feminine jiggling and bouncing was driving me wild. All the guys we passed were looking at me like I was a new sports car that wanted to take for a ride. It was the same look all the guys at the club gave me while I was dancing. The look of raw, naked lust.
I looked at my reflection in the store windows as we walked by. I watched my tits shake like Jell-O. I watched my ass swing back and forth and shake with every step. It shook less vigorously than my tits but it shook like Jell-O just the same. I felt my cock get hard as we walked out into the parking lot. Bob was walking with a big smile the whole time.
I looked up at him "What are you smiling about now?"
"Same thing...... You.... I saw you checking yourself out. I saw you strutting your stuff for the guys. You like being a girl, don't you, Kitty?" he chuckled.
I blushed hotly and giggled "I guess"
Bob smiled warmly "Good Girl"
I felt my cock throb when I heard it and smiled back at him shyly. When we got in the car, the first thing I did was lay on the seat and bury my face in his crotch. He chuckled and patted my ass.
"God, I Love A Good Whore!" he exclaimed "Save it for tonight Kitty, you'll be doing alot of it."
I sat up and looked at him "What's tonight?"
He gave me a strange look "You wanted to be a superstar. That means you still have to serve drinks, give lap dances and service the glory hole. We have you scheduled from 7 till close."
I blinked quickly as I pictured it. That explained what was in the bag.
"Don't worry, we'll go to my house relax by the pool, I'll fuck you a few times, you'll be fine." he said plainly and started the car.
I spent the whole trip to his house watching my tits jiggle and feeling up my pussy. I couldn't stop myself, I couldn't get over how good it looked and felt. I had to wonder if girls knew how lucky they were to have these things for real. Mine weren't real and I had only had them for a day, but I thought they were great! They were the source of non-stop sexual attention. The kind of attention I would never get as a man. I tried to imagine what it would have been like if I had been born with them. Or how much fun it would have been to have grown up with them.
My thoughts were interrupted when we pulled into Bobs driveway. He had bought 25 acres just outside of town and put his house in the middle of it. He had a long driveway, but the house came into view almost as soon as you pulled in. We drove up to the house and parked in the big area in front of the house. He had a huge house. You could fit 3 of mine on the first floor.
While we walked through the house to the pool area I couldn't take my mind off how good all the jiggling felt. With every click of my heels, my ass cheek would shudder and my tits would bounce. I was swinging my hips and trying to step just right so I could get the maximum response. As I swung my hips farther and farther, I could feel my cock head being rolled between my butt cheeks. The whole experience was taking my breath away.
The pool area, was a big enclosed area with screen sides to let in lots of air. It was set up alot like my basement, only he had a pool instead of a pool table. We walked in and headed over to the bar. Bob smiled at me, turned me toward the bar and bent me over a stool. I looked over my shoulder and smiled as I watched him grab my hips and start mashing his crotch into my ass. I could feel his bulge growing while he did this and I looked forward.
"You like being a girl, don't you? You like your new pussy, don't you? Showing it off turns you on, doesn't it?" he probed as I began to push back against him.
"Good Girl..... It turned me on to see you strutting for the boys at the mall. I like a girl who isn't afraid to sling some pussy, and you were definitely slingin' some pussy."
I began to moan and grind my ass against his bulge. I could feel his cock was rock hard in his pants, and I was smashing my cock head against it. It felt so good to have it pinched between my asshole and the soft fabric of my shorts., that my cock was throbbing while I ground back against him.
"Yeah, That's my girl. You got such a hot little ass. Fucking you was the best thing I ever did. You're a hot little slut, and I'm gonna be fucking this hot little ass of yours non-stop."
I was writhing against him while I listened. He had a firm grip on my hips and was grinding against me just as hard.
"I love fucking you. You're the best fuck toy I've had in a long time. You got a nice tight ass. It feels so good when I stick my cock in and fuck you like a sloppy whore. The harder I fuck you, the more you squeal and the tighter your ass gets. Buddy and the guys liked fucking you as much as I did. God, you're a good whore!"
I was grinding my ass back and I couldn't get enough of hearing what a hot ass I had and how good it felt to fuck me.
"I'm going to fuck you hard and dump my load into that sweet ass of yours..................... Doing that feels so good, I can hardly stand it. You are such a good fuck and such a good whore."
"I'm gonna fuck you."
"I'm gonna fuck you lots."
"You got such a tight ass, I'm gonna fuck you every time I feel the need from now on."
I was panting and moaning hard. Pre-cum was leaking out and lubricating the head of my cock while it squished between my asshole and shorts.
"Yeah........ Good Girl"
"Fucking you feels so good, I'm gonna tap that ass like it was a brand new keg. Knowing you like feeling a big hard cock pumping into you as much as I do makes me want to fuck you even more."
I was so close to cumming, I was grinding back and moaning "Yes"
"You're gonna suck my dick too. Looking down and watching you suck me off and swallow was better than Christmas. Watching it slide in and out of your mouth while you sucked hard. It looked and felt so good, I almost shot my wad right there. It was really fucking hot. You're a natural born cocksucker Kitty."
Just as he finished his sentence, I came. I squealed and jerked around, flexing my hips. I could feel my butt shaking vigorously, my cock throbbing and cum splashing against my asshole. Every time my cock throbbed hard and cum shot out, it hurt because it was pulled back so far. Causing me to squeal every time.
Bob chuckled, stepped back and watched my ass until my orgasm subsided.
"Good Girl" he said patting me on the ass and pulled my shorts to my knees.
I hung my head as I thought about what just happened. I had just had an orgasm because a guy was rubbing against me and telling me how much he liked fucking me.
Bob pulled down his pants, got behind me and started rubbing his cock head around in the cum. He rubbed it around my asshole and poked into it a bit.
"Look at all the pussy juice. You love a big hard cock so much you got off just thinking about it."
"FUCK!! THAT'S HOT!! YOU'RE A COCK LOVING WHORE!!!" he chortled.
I couldn't help but to admit that he was right. It had happened just like he said. I loved the way it felt to jiggle and shake like a girl. I had enjoyed sucking cock. I had enjoyed getting fucked. I had fun in the mall..................... Having all those guys looking at me while I strutted around was a turn on. Then, just like he said, I got off by just thinking about how much I liked getting fucked. It was almost a replay of last night.. I had even wondered what it would have been like if I was a girl
There was one big difference. I was drunk last night. I didn't have an excuse today.
I breathed heavily as Bob eased his cock into me using my own cum as lubricant.
Was I really a cock loving whore?
It didn't matter anymore how I had learned or why I did it to start with. I knew it felt good and Bob was driving that point home while he began driving his cock into me. I quickly began to push back and meet his thrusts. He pounded his cock into me hard and fast. My ass was so warn out, I quickly got the same belly ache I had this morning and began try to shit like I was in labor.
"Yeah...... That's my tight ass bitch! Give it to me Pussy!" he ordered.
I continued to squeak and moan like a set of rusty bedsprings while he was pile driving his cock into me. I was driving my ass back as hard as I could to meet his thrusts.
"They call you pussy and you love a big cock! Don't you?!?" he growled.
"Ah" I responded.
He pulled his cock out "What?"
"YES!" I responded urgently.
He stuck his cock halfway in and stopped. "Yes, they call you what?"
"They call me pussy and I love a big cock"
He started fucking me as hard and fast as he could. "Tell me you love cum!"
"I love cum!" I moaned.
I was slamming my ass back and pushing like I was in labor again while Bob gave it to me hard.
"Don't stop" he ordered.
I quickly began chanting "I.. love.. cum!.. I.. love.. cum!.. I.. love.. cum!" in time with his thrusts.
Bob was fucking me deep and hard. I could feel my cock head pressed against the underside of his cock and it was driving me wild. I wanted it so bad, I just kept chanting.
He was grunting and forcing his cock into me non-stop. Time after time, I felt it force it's way in no matter how hard I tried to shit it out. He fucked me for what seemed like forever and it felt so good, I was getting dizzy. I wanted his cum so bad, I was chanting desperately. I had to have it.
He drove deep inside me and I felt his cock throb. I squeezed my asshole as tight as possible around his shaft. I began to undulate my hips while I pictured cum pouring out of his cock and filling my belly so full that I look pregnant with cum. I heard him groan through the final stages of his orgasm.
"God you're a good pussy" heard him whisper.
I smiled and ground my hips back. He pumped into me a few more times while I continued to squeeze my ass tight. I was fixated on knowing that I had satisfied his lust and that the last of his creamy white satisfaction was being pumped into me.
"Good Girl" he started to coo "The tightest kitty in town is officially my 'Cum Filled, Cock Loving, Whore' and she's got a fresh cream pie to prove it!"
He pulled his cock out and stripped off his shoes socks and pants. I was looking over my shoulder watching him while still bent over the bar stool.....................
He looked at me. "Why don't you pull up your panties and go for a swim while I get us a beer?"
I looked down and saw my shorts still tight around my knees. I reached down, pulled them up and straightened them out as best I could. I turned took off my heels and jumped in the pool. My ass was sore as hell again and a cool swim sounded like the perfect remedy.
I swam around underwater and marveled at how good it felt on my ass. I looked around and watched as my long red hair floated around. I luxuriated in the feeling of the slow motion bouncing of my tits and ass. I came up for air and lazily floated along on my back. I looked down and saw my big tits sticking up out of the water. They were firm and pert and I could see them right through my top. It was like it wasn't even there. Right between them I could see Bob watching me from a lounge chair while drinking a beer.
I smiled at the roof, spread my legs and gently kicked my feet to the sides. I took long slow strokes. I would bring my hands over my head and slowly bring them to my waist while spreading my legs and gently kicking to the sides. I did that until I touched the other side of the pool. I tried to do a side stroke to the ladder, but my tits kept getting in the way. I giggled and climbed slowly up the ladder.
As I climbed, I was amazed at how much water ran out of my hair, straight down the crack of my ass. I wiggled my ass around when it slowed to a trickle. I finished climbing out and jumped onto the diving board. I smoothed my hair out and pulled it into a pony tail to lay on my back. I walked to the end of the board, made my pose and jumped up to start my dive. When I came back down on the board, the extra weight pulling at my chest and ass felt so incredible I had to do it 3 more times before I made my dive. The extra weight threw me off so much while I did my dive that I came splashing down recklessly.
I was thinking about how much those little feminine jiggles flew around while I did a flip. It was mind boggling. I got back on the board and bounced up and down while pretending to get my feet set. I soaked in the feeling of all the feminine jiggles and tugs.
My hips, ass, tits and hair pulled straight down when I came down. Then when I went up they pulled hard at first, only to float and jiggle like Jell-O until I came down again. It felt so much like they were real. I was sure that this is what it felt like to be a girl.
I made my pose and did a decent flip. Feeling the water rush around my nubile female frame gave me a shiver. I surfaced and swam slowly back across the pool. Bob sat quietly, drinking beer and watching. I climbed up the ladder in front of him slowly, swinging my hips provocatively as I did.
He was sitting back in the lounge chair with one foot on either side, dressed in nothing but his shirt. I licked my lips while staring at his cock..................... I put my hands on top of my head and swung my hips to make all the right things jiggle for him. Bob had his eyes glued to my pussy and tits.. I smiled when his cock began to grow. I eased off my shorts and watched it get rock hard. I straddled his lap, hooked one knee over the arm of the chair, eased his cock inside me, then hooked my other knee over the other arm. I grabbed the chair behind his head and began bouncing up and down as fast as I could.
Bob just sat there silently while I worked his cock inside me. I could feel his cock was rock hard, so I knew he liked it. I was feverishly working it with my ass. I was so fixated on being his perfect piece of ass that I wanted desperately to make him cum inside me again.
After about five minutes, I had worked up quite a sweat and was pretty tired. I got up, turned my back to him and sat back down on his cock. I began to pivot my hips up and down while watching Bobs balls slap against my smooth pussy. I stared at my crotch in amazement. There was no sign of a cock. Just a fat bald pussy with a cock stuffed in it. I felt my ass cheeks quake every time I brought my ass down, and I had such a warm feeling while I did this.
I began to think, that as a woman, servicing stiff cock was what I was born to do. It was what all women were born to do. That's what pussy was for. I unconsciously began to chant my lines again. Bob just smiled while he watched me slamming my ass down on top of his cock.
I was looking between my legs and watching while his cock disappeared inside me every time I brought my ass down. I watched him pump his hips, his balls pulled up and his cock flexed. I could feel cum squirting through his cock every time I saw his cock flex. I watched in amazement, knowing I was watching him cum inside me. I sat down hard and let his stiff meat soak in my cum filled fuck hole.
"Good Girl" I heard Bob coo while I wiggled my ass and smiled.
"You're a good kitty" he said patting my ass.
"Can I get some? Are you done?" I heard a second voice say from behind me.................
I turned in alarm of being caught and saw Buddy sitting naked in a chair off to the side of Bob. He was drinking a beer and watching for who knew how long. His big black cock was standing rock hard in his lap.
"Yeah, I'm done with her. She's all yours" Bob said tapping my ass to get up.
I was staring at Buddy's cock.... It was huge! I remember thinking it was big last night, but holy shit! I couldn't believe I had been fucked by that thing!
I got up slowly and turned toward Buddy. I felt Bobs cock pull out and leave me with an empty feeling. I couldn't take my eyes off Buddy's cock. It was a work of art. And I had been fucked by it.
"Come on over Kitty. Do another pole dance on the Anaconda" he said waving his cock at me.
As I stood in front of Buddy, I couldn't wait to get started. His cock was beautiful. It was a muscular ten inches easy. Jet black, nearly as thick as a beer can, with a fat head and a monster set of balls. It was the kind of cock I always wished I had. And it was a strange thrill to know he was going to give it to me......... Again.
I smiled, put my hands on his shoulder. I slipped one foot through the arm of the chair so I was standing on the ground while straddling his lap. I slipped my other leg through the other arm and began to rub my wet tits in his face. He grabbed my ass with one hand and as I bounced up and down with my tits in his face, I felt his cock knocking at my back door.
He found the wet spot in my ass and homed in on it in a flash. I stopped for a second, I pulled back, looked him in the eye and smiled as I eased down on his monster black snake.
"Take it Kitty!" he encouraged "Take it deep!"
I felt my ass cheeks wrap around the fat head as it slid up to my fuck hole. It stretched my sphincter, slid right in followed by a long fat shaft................ I forced my way down as it stretched my insides until I felt it smack into something. I pushed down harder and it wouldn't budge I was so stretched out and it was as deep as it could go.
It felt so good, I moaned loudly and began a slow up and down motion. It felt so massive inside me, I closed my eyes to savor the feeling. Slowly picking up speed with every downward thrust.
Before long, I was jumping up and down as fast as I could while I swung my head around and squealed with delight. The feel of all that hair flailing about was so new and enticing. My tits were jumping and swinging around. They pulled heavily at my chest and I tried to time my jumps with the bouncing of my tits.
I could feel Buddy's fat Anaconda cock sliding between my smooth round butt cheeks, past my puckered hole and sliding up inside me. It was an incredible feeling to have him slide so deep into me that I couldn't fit anymore cock inside me.
I began to picture what it looked like to stare at my pussy while Bobs cock slid balls deep in me. Then I pictured what it looked like to have Buddy's big black balls sticking out of my ass while he was buried inside me........ The thought of it was driving me wild. It made me feel like a sex crazed nymphomaniac, desperate for cock and the creamy white ball juice he would pump into me when he was done.
"That's it!! Make that Kitty purr!! Ride it hard!!" he encouraged.
I continued to ride his cock like it was the most important thing in the world to me.
Which it was.
He felt so good inside me and I wanted his cum so bad. I wanted it worse than anything!
I was riding Buddy's cock harder than ever and I was squealing like a tea pot. I smiled and began to think I really was a cock loving whore. I began to think of the fifteen guys that I had been pimped out to last night. I wondered what it looked like for me to be passed out in the back room while they walked in and used me like a live sex doll. I wondered; How much cum would fifteen guys have dumped inside me?
While I rode his cock and daydreamed about all the cock that had been stuffed into me last night, Buddy groaned hard.
"Here it cums Kitty!!!" he exclaimed while grabbing me and stuffing his cock as deep as it would get.
I sat down hard and smiled as I felt his cock begin to throb so deep inside me. He grabbed my butt cheeks, moaned and stabbed into me using short quick thrusts. I could feel cum shooting out inside me like a fire hose. I just smiled and took it as he coated my insides white. I squeezed my asshole tight and every time his cock throbbed, I could feel cum squirting through it.
The whole experience was giving me such a warm satisfied feeling that I laid on top of Buddy with a triumphant grin. It felt so good to have sex as a girl. It was so available and easy to get. Knowing that I had just satisfied the cock that was relaxing inside my cum filled fuck hole was the best part.
"Fuck that was hot Kitty!" Buddy whispered.
"Good Girl!" I heard Bob chuckle.
I turned to see Bob sitting in a chair drinking his beer and watching the whole scene.
"Thanks" I smiled.
I got up and marveled at the feeling of that fat piece of meat pulling out of me as I stepped back. I stared at Buddy's cock, while stepping to another chair. I couldn't help but to admire it. It was so big and it looked so cool laying there. It had a sleek black shine that made it stand out. It had just been inside me and I couldn't take my eyes off it.
Just then, I heard a plop on the floor and looked down to see a big white gob of cum next to my foot. I giggled nervously, Buddy and I smiled at each other as I stretched out in the lounge chair opposite him.
While Buddy and Bob sat and talked, I admired their cocks and drifted off to sleep next to the pool.