Hi, I'm Jimmy James. This is a story about cross dressing, teen sex and prostitution.
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When I was walking home the next morning. Nobody noticed me again. I had gotten dressed as a girl, went out and got totally gang banged. Cum was still leaking out of my ass and I could hardly walk. But nobody seemed to notice.
I got home and thought about how much fun I had. I was a total slut!! I got drunk and went out dressed as a girl to see if I looked like cock candy. I found out I was definitely cock candy! And a bunch of guys gave me money to use me as just that.
Something sweet for their cocks!
I emptied my purse and began to count the money. I had a little over a thousand bucks! I had never made so much cash in my life. I had never had a good time while making money either. This was just too fucking cool.
I giggled as I thought about it, and called David immediately. We exchanged pleasantries and he told me again how great I was last night.
"It was fun" I giggled "You said something about making some cash?"
"I was hoping that's why you called." he said with a smile "You have an amazing look and talent. You seemed to really enjoy what you do, so I thought there were some people you might like to meet."
"What kind of people?" I asked
"Nothing bad" he reassured me "Just some people I went to college with and some friends. We have a weekly poker game and were looking for some private entertainment. I think you would be perfect!"
"OK" I agreed cheerfully.
"Are you free tonight?" he asked
"I'm free all week." I announced.
He told me he would pick me up at 6pm. We discussed what I should wear. It wasn't a dress up thing, but all the guys would be wearing suits. So wear something appropriate. I assured him I had the perfect thing for such an occasion. I did too. My sister had a well stocked closet and I had seen her in all of it.
That night, I chose white boy cut panties. The lace trim ended just before the crease of my ass cheeks melted into my thighs. A white see through bra. White polish for my fingers and toes. Black boots with a 4 inch heel. Black stockings and the slinkiest little black dress I could find.
No sooner had I finished putting on my makeup, David rang the bell. When I opened the door, David was flabbergasted.
"Wow! You said you had the perfect outfit, and you have just exactly that! The perfect outfit!" He whistled.
I giggled and bushed. Telling him how nice he looked. He did too, I bet he was wearing a four thousand dollar suit. Quite the change from the shorts and T-shirt.
I commented on it and he said he just got off work and that the people in the park are the people he went to high school with. The people we were going to party with now are the people he went to college with and some other friends.
On the way, he told me that they had the poker game every week and would love it if I would join them every week. If I liked it I was welcome for as long as I wanted. I asked about the money.
He told me that I had a tip jar and that everybody had kicked in a "mandatory minimum" but he was sure there would be more. I agreed and said it sounded fine.
I was way more interested in cock than money.
We pulled up to one of the best restaurants in town and went inside, locking the door behind us. There were ten guys milling about, drinking and laughing. No bartenders. No waitresses or anything. The two things I noticed right off was 1) I was the only white face there. 2) They were all impeccably dressed.
For the next hour and a half, I made the rounds and talked to just about everybody there. I didn't want to tell them I was in high school, so I asked alot of questions about them. There were bankers, hotel owners, lawyers, rental properties, restaurant owners. As a matter of fact, one of the guys owned the one we were in along with three others.
Turns out David was an investment banker.
While making the rounds, I got felt up quite often. I also found out that none of the guys was over forty. Well, 42 was the oldest. By the time we finished dinner, I wanted their cocks so bad I was about to bust. When dinner was over, the cards came out and I crawled under the table to start earning my cash.
About three of the guys whipped their dicks out for service. I started to drool, they were all 8 to 10 inches. I sat in front of the first. He had a dark black cock that was thick and jumped every time his heart beat.
I licked and kissed his cock slowly and lovingly as I stroked it gently. I gently sucked the head of his cock and ran my tongue around the curves. It felt and tasted so good, I was amazed.
I was so drunk and thrilled by being used as cock candy. I didn't realize how nice it was to suck a cock. It was stiff and smooth, but soft around the edges. This was such a thrill for me. I was so turned on, I was sure I had found my calling. Satisfying stiff cocks!
I moaned while I sucked harder and faster. It felt so good to have a cock in my mouth. I kept sucking while thinking how nice it felt to have a big juicy cock sliding through my lips and across my tongue. I wanted his cum SOOOOO BAD!!
I pushed forward hard and felt the head of his cock squish against my throat. I pulled back and tried again. I was pushing as hard as I could and the head of his cock was almost in my throat. I pulled back again then pushed forward hard. I was so close to deep throating him, I couldn't stand it. I shook my head back and forth trying to wedge it into my throat.
He must have really liked the effort. When I pulled back again, his cock started throbbing uncontrollably. Cum was shooting into my mouth and I was swallowing it as fast as I could. It was fucking awesome!
When he was done, I continued to suck his cock. Licking up the last few drops of cum. I had aways heard girls talk about how gross it was to suck cock. They must have been talking about something different, because I thought this was great. The cum was the best part. A tasty treat for your trouble.
I eagerly moved to the next guy. I sucked him like I was dying of thirst. Trying desperately to suck cum from a fat straw. I pushed his cock against my throat and tried to deep throat again. It squished and almost made it into my throat. I moved it in and out the tiniest bit, but couldn't quite get it down.
I pulled back and sucked the head like it was the biggest, sweetest lollipop I ever had. I was soon rewarded with mouthful after mouthful of thick gooey ball juice. I swallowed everything he could give me as fast as I could.
Cum was dribbling out and I could feel his cock getting softer in my mouth. I pushed it against my throat again and sucked the thick shaft filling my mouth. My eyes bugged out when my head moved down and I felt the fat head of his cock slide down my throat.
I had done it!!.... I was deep throating a cock!!!
I got about five inches of it down my throat and began to bob my head up and down. Making sure to keep the head of his cock in my throat at all times. It was great! It stretched my throat just that little bit extra and slid right down! Filling my mouth and throat with cock.
I kept bobbing my head and felt his cock start to get hard again. It stretched my throat even more as it ballooned inside it. I pulled back and sucked just the head again. I looked at his cock while I did this and grinned. His cock had the nicest spit shine you ever saw.
I cheerfully sucked his cock and again he rewarded me with thick white ball juice. I swallowed everything he fed me. It made me so proud, I had sucked his dick, deep throated and made him cum twice!
When I got in front of the third guy. I was astounded at the cock that was in front of me. It must have been 12 inches long and an inch and a half in diameter. Not nearly as thick as the other guys but definitely respectable.
I licked the tip and started to suck the head. I sucked more and more of it in with each stroke. When it got to my throat I pushed and it slid in easily. I pushed as much of it down my throat as possible. When I had about three inches to go, his cock head ran into another tight spot. I pushed hard and his cock slid balls deep into me.
I heard him say "Oh Fuck Yeah!" and everybody started to tease him about his poker face. I pressed my face tight into his curly hairs and wrapped his balls around my chin. He made some more funny noises and everybody roared with laughter.
I felt his cock throbing and cum squirting through it. Pumping it directly into my belly. I quickly began to bob up and down while he came and banged my head on the table. Causing another round of laughter.
When he was done pumping cum, I licked his cock some more. He looked under the table and said "That's the very first time anybody has ever been able to do that." while pushing $200 at me.
I smiled at him, licked his cock and said "Thanks, but that goes in the tip jar" he laughed and put his money back on the table.
After a couple of hours they were ready to take a break. I crawled out from under the table, walked around, hugged, kissed and rubbed against the guys. They all told me how glad they were that I had joined them and how much they hoped I would be back. I told them how happy I was to be invited and that I would be more than happy to join them from now on. They of course loved the idea.
I started to make out pretty heavy with one of the guys. He led me to a corner booth and I sat in his lap facing him while we continued to make out. He pulled the straps for my dress and bra from around my shoulders. Pulling down my dress and bra to expose my tits. He began to fondle my tits and suck my nipple.
My nipple was rock hard. It felt so good, I moaned hard and mashed my tits into his face. He reached under my dress and squeezed my ass. I rubbed my crotch against his hard cock and felt him throbbing under me. He pulled off my panties and pulled his pants to his knees. I lubed my ass and re-took my place in his lap.
We kissed while he caressed my bare ass and fingered my butt hole. I was rubbing my crotch up and down the length of his naked cock. It felt so good to feel his hot stiff flesh pressing against me while he moaned. I had to have him inside me.
I reached back and pressed the tip to my cock hungry fuck hole. I eased back and reveled in the feeling of him sliding inside me. Once inside, I couldn't believe how big he was. He stretched me to the limit and I was stuffed with cock. I felt like a sausage skin wrapped around his cock.
It was so fucking hot!!... I thought it was a turn on to suck cock, but this was so much better I couldn't believe it. I eased myself up and down his tool slowly, but in steady strokes while we kissed. I was so turned on, my butt hole squeezed his cock and I sqealed as a small orgasm swept through me.
After about fifteen minutes, everybody else returned to the table while we continued our slow dance in the booth. He was touching and caressing me everywhere while I contiued to ride his meat slowly. It felt so good, I squealed again and jumped when a slightly bigger O hit me.
After another five or ten minutes. His cock felt so good sliding into me I had another mini O. About thirty minutes into my long slow ride, he must have decided he had to cum ASAP. He grabbed my ass, started grunting and pounding his fat cock into me. After about the third thrust, I came so hard I thought I exploded. I squealed. I moaned. I flopped around like I was having a siezure. I would have fallen if he hadn't caught me. He kept pounding his cock into me hard the whole time.
When he came, He stuffed it deep into me and it felt like a fire hose was inside me. Cum sprayed out and gurgled deep into my guts. I smiled contentedly and hugged him close. His satisfied cock buried deep inside me. By 11:30 everybody was headed home. The owner threw David the keys and told him to lock up. I sat at the bar with a smile. They were the nicest guys. I had sucked all their dicks and been fucked silly 4 times. I know I came at least 15 times, It was a really good night. Then David brought over my tip jar.
My jaw hit the floor!... It was stuffed with hundreds! I looked at David dumbfounded. He smiled and told me that they had loved having me as their guest. He also told me they had kicked in a $500 minimum for the dinner. Plus any other tips or donations.
I sat at the bar counting the money and there was a little over $8 thousand. I was speechless while I pondered it. Doing this every week for 2 years means I would have more than $750 thousand by the time I graduate high school.
HOLY FUCK!!!!
I talked to David and he said he would help me invest it in a private trust for me. He said not even the government could get it there. Just me. I told him that's exactly what I need. We locked up and talked some more as he drove me home. Cum was leaking out my ass the whole time. It soaked my panties, dress and seat. When I got home I looked at the clock and it wasn't even midnight.
I had gone out, had dinner, met some really nice guys, swallowed a gallon of cum, had lots of hot sex and had the best time of my life. AND, Oh Yeah.... I made eight thousand dollars besides. All before midnight.
LIFE WAS SO GOOD!!
The next night, David and I got together for a private date. He was so nice, he brought me flowers and took me out to dinner. It was such a nice night and he was such a good lover that we set up another date before my parents got back. Being a girl was so much fun.
It was radically different than being a boy. Everybody smiled and was very friendly, especially the guys. Nobody bullied me, kicked me, hit me or made fun of me. I liked this lots better.
When my parents got home. I was dressed as a girl and refused to ever dress as a boy again. I also insisted on female hormones. I told them I had dressed as a girl the whole time they were gone and I even had a boyfriend. I left them no choice but to agree.
David and I continued to date openly. My parents loved him. They had no idea that I was a part time prostitute, he was my "pimp" and I was making more than both of them put together.