I'm Jimmy James and this is a story of cross dressing and sexual submission at the hands of my girlfriends father.
============================ Working 9 to 5
I was awakened a few hours later by Bob telling me it was time to clean up and get ready for work. He had a big smile as he watched me shake my ass on the way to the bathroom. He told me to get a douche and watched closely while thick white gobs of cum shot out of my ass.
Having him watch me while I did that was a huge turn on and he let out a small chuckle as my cock got hard.
"Good Girl Jimmy. Why don't you get over here and suck my cock?" he said with a smile as he pulled it out and leaned against the counter.
I smiled, wiped my ass and got to my knees in front of him. I gently licked, kissed and sucked the head of his cock while he watched.
"Look up at me while you do that." he said.
I looked up and gave him a big smile while I continued to lick and suck the head of his cock.
"Good Girl. I love watching you suck my cock Jimmy. It's not often you find a girl that likes to suck on a stiff cock as much as you do. It's what makes you the best pussy in town." he said with a smile.
I blushed with pride and plunged forward until I felt his balls on my chin. I pulled back slowly while looking up at him the whole time. I loved the way it made me feel to be able to feel his cock in my throat and see the look of pleasure on his face. I quickly began to suck his cock as hard and fast as I could. I wanted to make him cum as fast as possible. I loved knowing that he liked it as much as I did. I loved knowing that he got hard when he thought about me sucking his cock like this. It let me know that I was good at it and that he looked forward to it.
Thinking about it made me so fucking hard I could hardly stand it. My cock was standing proud and throbbing with excitement. I reached down, squeezed it a few times and rubbed the slick pre cum around the head. While I did that, Bobs cock began throbbing in my mouth. I gulped down his cum and watched the look on his face. I loved seeing that look more than anything. It drove home what I was doing for him. What he was doing in my mouth. What I was swallowing.
Mostly it drove home how good I was at sucking cock.
I felt the warm satisfied rush wash over me.
Once the throbbing stopped, Bob grabbed my head and pumped his cock into my throat a few times. While groaning about how good it felt. Then he watched as I pulled back, sucked the head and licked his balls.
"You need to take a shower and get dressed for work." he said as he looked down at my hard cock.
I smiled at him, got up and jumped in the shower. While I showered, I looked down at my still hard cock and thought about how good it made me feel to have him cum in my mouth. How much I looked forward to having his cock throbbing while my mouth filled with cum. How good it must feel for him while he empties his balls into my mouth. Then watches me swallow like a good girl.
I began stroking my cock while I thought about the look on Jakes face while he emptied his balls into my mouth. How much I enjoyed the taste of his cum while I swallowed for him. I thought about him and the guys going to the restaurant so they could stand in line to use the hole. That I had been sucking them dry since Wednesday. How hard it made me to know that I would be sucking all five of their cocks all week. How much I wished I could see their faces when I swallowed for them. I fantasized about what it was going to be like to see them at work. Knowing what I had done for them. Or as Bob put it; What I had let them do to me.
I groaned loudly as my cock began to throb in my hand. I gleefully watched as cum shot out and filled my hand. I thought about all the guys at work that had cum in my mouth or in my ass. That I had let just about everybody I knew do that to me. I licked up my cum with a smile while thinking about all the guys at work that had stopped by the club for a lap dance. How good it made me feel to be able to look them in the eye. Stroke their cocks and lick up their cum without them knowing.
When I was done, I quickly finished my shower. I jumped out of the shower with a big smile to see Bob standing in the door smiling back at me. I was startled to see him and let out a small gasp.
"Sorry Kitty, I didn't mean to scare you. I wanted to watch while you put on your pussy and get changed." he said with a gentle smile.
"Cool" I giggled as I got everything ready.
"So what were you thinking about while you were jerking it in the shower?" he asked while I did that.
I told him about how strange it was to see a cock instead of a pussy when I looked down. How much I was enjoying all the sex. The satisfaction I got from seeing the look on his face while I swallowed his cum. How exciting it was to see the look on all the guys faces when I made them cum. The thrill I got from sucking my best friend Jakes cock and how good it made me feel. How much I enjoyed letting him fuck me. How exciting it was to know that my five best friends would be enjoying my services at the hole all week. How much I wished I could see their faces while I sucked their cocks. How much I was looking forward to going back to work and seeing all the guys that I had been with, so I could hear what they thought about Kitty.
Pretty much everything that was on my mind.
Bob didn't say a word. He watched closely as I pulled up the pussy panties. While I put my cock into the short tube. Leaving just the tip sticking out in front of the vagina, so I could pee like a girl. While I glued everything in place and stuck the little dumbbell in my ass to keep it aligned with the hole for the vagina. Then he had me strut around a little bit so he could admire it. He had me glue the tits on. Then strut around some more. He smiled as I glued on the wig. Did my nails and makeup. When I finished and finally pulled the dumbbell out of my pussy, he had a big satisfied smile.
"Fuck that's hot Jimmy. I love watching you get changed like that. It was amazing the first time I saw it and it just keeps getting better. You're a hot little honey once you put that shit on." he said as he twirled his finger.
I smiled real big, then twirled while shaking my ass and tits for him. Having him admire me while I pranced around nude was so raw and sexual, it was driving me wild. I felt my pussy twitch as I enjoyed how good it made me feel to jiggle and bounce like a girl again. I watched in the mirror as I backed my ass up against his crotch. I smiled at him when I felt the hard bulge in his pants pressing against my pussy. He smiled back grabbed my tits and ground back against my ass hard.
"GOOD GIRL.... That's why you're the best pussy in town." he chuckled as he bent me over the counter.
I was looking straight into the mirror and watched anxiously as he stood behind me, pulled down his pants and smiled. He grabbed my hips and stabbed his hard cock into me as hard and fast as he could. I yelped in surprise at how forceful his first thrust was. While he just smiled and began fucking me hard.
"Fuck That's Good! You wouldn't believe how good it feels to fuck you in the ass like this Jimmy. Once you've been fucked a few times. There's no way to tell the difference between your ass and real pussy. Now that you're all dressed up like Kitty. You're better than the real thing. Since you used to be a man. You know what men need and you deliver. Every Time. You're everything a cock hungry pussy should be." he said as he continued to hammer his cock into my over heated pussy.
I listened with a big smile as I watched all the action in the mirror. I watched as his balls slapped against my pussy and my tits bounced wildly with every thrust. I loved the way it felt to have my tits bounce like that. I had only been without them for a few hours, but I couldn't get over how much I missed having them. Every time I felt them jiggle, it was a constant and unmistakable reminder that I was a girl.
As a guy, they were the fist thing I noticed about a girl. Now that I was a girl I knew they were the first thing men noticed about me. I could feel my orgasm building as I fixated on how feminine they made me look and feel.
Bob drove his cock deep and grunted. I felt his cock throb hard inside me while his face twisted with the ecstasy of his orgasm. He grabbed my hips tightly, jumped, jerked and groaned while grinding his throbbing cock deep inside me. I watched with delight as the girl in the mirror got a look of overwhelming joy as she eagerly accepted his tribute to her skills as a woman. As his orgasm ended, a look of relaxed relief swept across his face.
I couldn't help but to blush as I thought about the look of unbridled lust he had while he dumped his load inside me. How good it made me feel to be able to give him that much pleasure. How many times I had done it for him. How many times I had done it for all those other men. How good it made me feel to know that I could be the source of that much pleasure to that many men.
"Fuck That's Good" Bob groaned as he pumped his softening cock into me and squeezed my tits.
We looked at each other in the mirror with big smiles as he reached into my crotch and began to rub my pussy. My cock was as hard as it could get while glued into its prison, and feeling his finger rubbing hard against the slick tip of my cock was driving me wild. He chuckled when he saw my reaction and rubbed my pussy even harder.
"Good Girl. I gotta tell you Jimmy. You were talking about the satisfaction you get from being able to dress up and give men sex just like a girl. To be honest, I get that same sense of satisfaction every time I fuck you. Or better yet, watch other men fuck you. It's hard to believe, but I've turned my daughters useless asshole boyfriend into into the hottest girl in town. She is what every girl should be. A cock loving whore. She's a girl that needs sex even more than a man does. And she wants it for the same reason. Just for the fun of it. Because she can." he said with pride.
He continued to stroke and rub my pussy as I writhed and squealed with pleasure.
"I can't tell you the satisfaction I get from knowing that you're so good at being a girl that the men you work with can fuck you without knowing it. I can see why that turns you on so much. You should hear the shit that they say about Kitty. They think she's the best pussy they ever had. Listening to your friends at lunch go wild about how good she is at sucking cock is even better. I wish I could be there when they tell Jimmy about her." he said with a grin.
I couldn't take it any more. I began to buck and squeal as my orgasm consumed me. Bob drove his cock deep and continued rubbing my pussy.
"Yeah... That's It.... Cum for me Jimmy.... Good Girl." he cooed as he hung on tight.
When my orgasm ended, I felt a huge sense of relief. I stared at the dreamy look on my face when I finally opened my eyes. Bob brought his cum covered hand up to my lips.
"Lick that up for me." he instructed.
I eagerly licked his hand clean and sucked his fingers when I was done. He watched with a big smile the whole time.
"That's my girl." he said warmly as he squeezed my ass and pulled his cock out.
When he did that he watched as cum poured out of my pussy and ran down my legs.
"Fuck That's Hot. Wipe that up. I'll be back in a second." he chuckled while throwing me a towel.
No sooner had I done that than he gave me some clothes. Open toed black high heels. Black thigh high stockings. Short black skirt. Baggy see thru black tank top that just barely covered my tits. No panties or bra. He watched closely as I put everything on and packed my purse with makeup.
"Perfect! Let's put that ass to work!" he proclaimed as he walked off.
Once we were in the car and headed down the road. I asked what we were doing and where we were going. He looked at me and chuckled.
"We aren't doing anything. You are. I set you up with a 9 to 5 shift at a motel. I have a bunch of guys that want to pick up a cheap hooker on the street. So I'll be sending them by until 5 am when I'll pick you up. Now these guys want to believe they're picking up a real hooker that's going out for her first stroll. So I'm counting on you to make it as real as possible for them. Never ever do anything that would make them think anything different. If anybody asks. You're from Franklin Hills. You took money out of your trust fund. Now you need to put it back before your parents find out. OK?" he asked.
I giggled as I thought about it. Poor little rich girl turning tricks.
"OK" I said with a bright smile.
"Who knows. If you do a good job. You might even be able to turn some real tricks by accident." Bob told me as he caressed my pussy and pulled into a small run down motel.
I felt my pussy twitching wildly as I thought about it.
"That's my girl." Bob chuckled as he got out and headed for the office.
I giggled and blushed as I followed him. Between all the bouncing and jiggling of my tits and ass. And the thought of walking the streets and turning real tricks. I could feel my pussy getting soaking wet.
The motel was shaped like a U with an office at one end overlooking all the rooms. The guy behind the counter didn't look like he could have been any older than 18 or 19. He had a big smile as he watched us walk through the door.
"Hey Brian." Bob said in his usual booming voice.
"Hey Bob. This the new girl?" Brian responded cheerfully.
"It sure is. This is Kitty. Show him what you're selling darlin'." Bob said while looking at my pussy.
I blushed and smiled at Brian while pulling up my skirt. Brian smiled real big as he got a good look.
"Fuck that's nice. Let's see the tits." he barked.
I giggled and promptly pulled up my top and shook my tits at him.
"What do you think? Good for a room for the night?" Bob asked.
"Fuck yeah. That will more than cover the cost of the room. I get to fuck her now and she'll suck my dick in the morning right?" Brian asked while looking at Bob.
"Absolutely." Bob replied quickly.
"Cool. Watch the desk while I show her the room." he said while grabbing a set of keys.
I followed close behind him and had a big smile as he showed me into the room. It was run down and shabby. With just a bed, TV, small table and two chairs by the window. As soon as the door was closed, he pulled me close and began kissing me. He took off my top, pushed me back on the bed and watched with a smile as I spread my legs and smiled back.
"God you're hot. How long have you been doing this?" he asked.
"This is my first time." I replied.
"I'll bet." he scoffed.
"It is!" I replied emphatically.
"Really? Where you from?"
"Franklin Hills."
"What brings you here? Just out slumming?" he scoffed.
"I needed money and Bob said he knew where I could get it."
"I'll bet he did." he said as he knelt between my legs. Pulled out a condom and pulled down his pants.
"You don't need that. I can't get pregnant." I said with a smile as I stroked his hard cock.
"This really is your first time. Isn't it?" he said as he climbed on top of me and stuffed his cock into my wet pussy.
"That's what I said wasn't it?" I snapped while glaring at him.
"You sure did. I'm glad I get to fuck you before all the niggers do." he chuckled while he began driving deep and hard into my pussy.
"What?!?" I barked angrily.
"You heard me. You won't see any white faces down here. This is nigger town." he scoffed.
"Fuck You! You fucking bigot! Get the fuck off me!"
"Fuck You! You stuck up bitch. You're here to make money as a whore for a bunch of fucking niggers. You're a rich bitch nigger whore and you need to pay for your room. Like it or not." he growled as he continued to fuck me hard.
I kicked and squirmed for a little bit. But I had been through it before and knew it wouldn't do any good. So I stopped and waited for him to finish. When he did, he got up and smiled at me.
"That's the first time I fucked a rich girl. It was fun thanks." he laughed as he pulled up his pants and walked out.
I angrily walked to the bathroom and began wiping up his cum from my legs and pussy. While I was doing that, Bob walked in and laughed at me.
"What's so funny?" I snapped.
"You.... He said you got pissed off when he said nigger and you got really pissed off when he called you a nigger whore." he laughed.
"Fuck Yeah! He's a fucking bigot and I don't see why you think that's funny!" I barked.
"Well, that's just it. He's not a bigot. He did it just to piss you off. He said you were a wild cat when you were pissed off and a much better fuck." Bob explained.
I scowled at him. Finished wiping up Brian's cum from my pussy. Then put my top back on. Bob chuckled a little, took me by the hand and led me to the door and looked me in the eye.
"Listen. You're from Franklin Hills. You owe me money and you're going to turn some tricks to pay me back. Understand?" he said tersely.
"Yes." I responded meekly.
"Good. You stay on the side walk. You walk from there to there. You get $50 for a fuck and $20 for a blowjob. Once you make the deal. You bring them to the room and give them what they paid for. Never get into the car. Understand?" he snapped.
"Yes"
"Good. I'll be back in the morning and you better have my money." he said abruptly and walked out.
I shook my head, shrugged my shoulders, grabbed my purse, went out to the side walk and began walking up and down the street. The first car that came by honked and yelled. I smiled and waved.
It was nice being outside and in public. The only time I really went out in public was at the mall. The first time was a disaster because I wasn't very sure of myself. But the second time was fun. I had time to enjoy the breeze up my skirt. The way my tits looked and felt while they jiggled. I learned to enjoy being admired as a girl. Walking around letting guys look down my blouse. Watching Dave looking up my skirt while I tried on shoes. Watching the bulge in his pants grow. Having sex with him in the storeroom. Having the old guy hit on me. Sucking his cock in the mens room. Then going to the diner. Where I ended up on my knees in front of a hole in the wall.
Thinking about it made my pussy so wet. I almost didn't notice that a car pulled up next to me. I smiled at the young black man that was driving bent over and smiled in the window. My baggy top billowed open to expose my tits. I watched him smile while looking at my naked tits.
"Hey baby. Looking for a date?" I asked.
"I sure am. How much?" he asked.
"$20 for head. $50 for sex." I told him as I pulled up my skirt so he could look at my pussy.
"Fuck Yeah... I got $50... Jump in." he said with a smile.
"I got a room." I said cheerfully.
"Better yet. Let's get busy."
We went to the room. I got my $50. Then laid on the bed with my legs spread. I smiled real big as he pulled down his pants, unveiling a fat 8 inch cock. He climbed on top of me. Eased his cock into me in 3 quick strokes. Then he began groaning while fucking me as hard and fast as he could. No sooner did he get started than he drove deep, grunted and got off inside me. As soon as he was done. He got up. Pulled up his pants and headed for the door. I didn't know what else to do, so I just laid on the bed with a big dumb smile.
"That was good baby. Thanks" he said as he opened the door and looked back.
I was still laying on the bed with my legs spread and a big dumb smile.
"I'll be here all night. Tell your friends." I chirped.
He laughed and walked out. The whole thing couldn't have taken more than five minutes. I smiled real big went to the bathroom, watched in the mirror as I wiped the extra cum off my pussy and headed back to the sidewalk.
Two or three cars drove by. Then an older black man stopped and asked for a blowjob. I took him to the room. He gave me cash. Pulled out his cock and sat on the bed. He had a long thick black cock that reminded me of Buddy's cock. When he told me it didn't get hard anymore, I smiled and told him that was fine. As long as he didn't mind if I swallowed. He laughed and told me he didn't mind at all.
I got to my knees and sucked his cock as fast as I could. Since he didn't get hard, it slid down my throat quick and easy. While I sucked it, I loved the way it felt in my mouth. It was just like sucking Ed's cock only bigger. I cheerfully sucked it hard and drove it down my throat as fast as I could. While he moaned about how good it felt. Before too long, he filled my mouth to overflowing with his creamy white baby batter. As soon as I was done swallowing. He pulled up his pants. Kissed me on the cheek. Told me I was great and walked out.
The whole night went like that. I couldn't have imagined anything better. I hardly spent any time walking the streets. Almost all the guys were well hung black men. They all wanted quick easy sex. Get in. Get off. Get out. It was like working on an assembly line. By the time the sun was coming up. I had been fucked twenty times and swallowed ten times. My pussy was so worn out and sore I could hardly walk. It was fucking great.
Since it was almost 5, I decided to relax a little before Bob got there. I laid on the bed and thought about how much fun I was having. I never imagined it would make me feel so good to spread my legs and let men fuck me. I loved being a girl. The sex was great and it was so easy to get.
I reached down and began to finger myself. My pussy was sloppy wet from being pumped full of man juice all night. Once I pumped my finger in a few times, my bowels clamped down and I felt my finger being squeezed tight. As I fingered myself, I thought about how tight and juicy it was. How good it would feel to fuck a pussy like mine. How good it must have felt for Jake and all the other guys that had fucked me. Once again, I could see why Bob liked it so much.
While I fingered myself and fantasized about how much Jake liked fucking me. How good it made me feel to let him fuck me. What it was going to be like to see him at work and hear him tell me about how tight and juicy my pussy was. I heard a key in the door. Then the door flew open. I snapped my legs shut and sat up quickly to see Bob and Brian smiling at me.
"Where's my money?" Bob barked.
"In my purse." I responded meekly.
"How much did you make?" he said gruffly.
"$1,200" I told him still unsure of what was going on.
He grabbed my purse. Dug out the money. Quickly counted it out. Stuck it in his pocket and smiled at me.
"Good Girl. You still owe him a blowjob for the room. I'll be in the car when you're done." Bob said as he walked out closing the door behind him.
"Bob says you're good at sucking cock. Why don't you dig it out and show me." Brian said with a grin.
He sat on the bed. Laid back propped on his elbows and watched as I got to my knees. Unbuckled, unzipped and pulled down his pants. His cock was already nearly hard and he watched closely while I gently licked and sucked the bloated head. He gasped with pleasure when I sucked it hard and deep throated for him. I continued to suck it hard and fast. Deep throating for him with every stroke. I listened with satisfaction as he groaned about how good I was at sucking cock.
Before long he groaned loudly and emptied his balls into my mouth. I watched the look on his face while he did that. His whole face turned red and he looked like he was having a heart attack. It was one of the funniest faces I had seen a guy make yet. I cheerfully swallowed his cum and smiled up at him.
"How was that?" I giggled.
"That was good. I bet it was easy to deep throat my cock after sucking a bunch of big nigger cock all night." he laughed.
"FUCK YOU.... ASSHOLE!" I yelled as I grabbed my purse and stormed out.
I jumped into Bobs car in a huff. Then I sat and pouted. Bob just chuckled and drove out like nothing was wrong.
"What's the matter pussy pants?" he asked.
"Nothing... He's an asshole." I scoffed.
"Yeah... So how many guys did you do tonight?" he asked as he reached over and began fingering my pussy.
"30.... Why? How many did you send by?" I asked eagerly.
I moved close to him and spread my legs while I reached over and began massaging his bulge.
"Why? You want to know if you turned any real tricks tonight. Don't you?" he asked with a smile.
My pussy began twitching while I eagerly pulled out his cock and began to stroke it quickly.
"Oh God Yes! You know I do." I told him emphatically.
"I didn't send anybody by. You were walking the streets and turning real tricks all night." he laughed.
I felt my pussy twitching wildly and felt his cock throb in my hand as I froze with a dazed look on my face.
"What??" I stammered.
Bob laughed again. Grabbed me by the back of the head and forced me down on his cock. Without thinking I opened wide and began sucking.
"You said you wanted to walk the streets and turn some tricks like a real hooker. So I made sure you got the chance." he snickered.
I tried to ask another question, but he just forced me back down on his cock and groaned about what a good cock sucker I was. I continued to suck his cock and think about what I had done that night. The thought of it made me so hot, I could hardly stand it. I was a hooker. A real live hooker. Just like the ones you always see on cable or on the news. I had always wondered what it would be like for a girl to be turning tricks on the street and now I knew.
When Bob parked the car and turned it off, I kept sucking his cock furiously. He reached over and began fingering me hard. No sooner had he started fingering me than he blew his load into my mouth. I gulped it down while I continued sucking the head of his cock extra hard. When he was done, I sat up and smiled at him.
"Good Girl... I've never seen a girl that's as good at sucking cock as you are. Now you need to get some rest. You're still working the lunch shift at the restaurant." he said with a big grin.
"Thanks, I will." I chirped as I jumped out and headed up to my front door.