I'm Jimmy James and this is a story about teens, cross dressing and sex.
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It was early Monday morning. I was laying in bed thinking of the camping trip this weekend. I had gone out camping with my friend Bob, his brother John and his 2 friends Randy and Dave. Randy was 17 and brought some beer.
I was 14, got drunk for the first time and got tricked into sucking Randy's cock. After that, I ended up being the camp cocksucker. I bet I sucked each of their cocks 5 times a day, for 3 days.
I thought about that for a while. That was at least 60 blowjobs. If each one took 10 minutes, that meant I spent 10 hours sucking cock this weekend. That was over 3 hours a day with a cock in my mouth. Plus, I swallowed every time. So I figured I drank a half gallon of cum. If giving one blowjob made you a cocksucker, what was I?
The strangest part was...... I liked it!
I thought about kneeling in front of a guy while he pulled a hard cock out. I thought about the way a cock looked as it hung in front of me. I thought about the way a cock smelled as I got ready to suck it. I thought about the way a cock tasted and felt as it throbbed in my mouth. I thought about what it was like to have cum spewing into my mouth. I thought about when I swallowed and pulled back to see a satisfied cock getting soft. I thought about how natural it all seemed. It was like sucking cock and swallowing cum was the most natural thing thing in the world.
I had never harbored any gay fantasies. Bob and I talked about girls and sex constantly. I had never even wondered what it was like to get with another guy or suck him off. Hell.... Girls turn me on! Why was it so much fun to suck a cock and why did I want to do it again?
I began to think about Bob and what he thought. He was my neighbor and we had always been friends. Neither one of us had ever had sex, and now I had given him his first blowjob. Hell..... His first 15 blowjobs! What a weekend. I wondered if he liked getting it as much as I liked giving it to him?
Dad had left for work an hour ago and Mom was getting ready to go. I put on some pants, a T-shirt and went downstairs. I made some cereal and sat at the table to eat. I ate and watched Mom get dressed as she barked out the days orders. I said yes to everything she said and soon she was off to work.
I plopped in front of the TV and about fifteen minutes later, there was a knock at the door. I thought it was a delivery man but when I opened it...... It was Bob! We both smiled and said our good mornings.
What you up to?
Watching TV.
Cool.
Come on in.
We both grabbed sodas and sat on the couch. We made small talk and avoided the subject on both our minds....... This Weekend.
Bob broke the ice. "You had quite a weekend, Jim."
I winced "Yeah, I'd say so. How'd you like your first blowjob?"
"It was fucking great Jim!!" he raved "But in a million years I never would have guessed you'd be the one giving it to me."
I blushed "I know! If you would have told me a week ago I was going to suck your cock. I would have beat you senseless!"
"I know!" he laughed "But you seemed to really like it!"
I giggled and blushed some more "I did! I liked it alot! Who knew it would be so much fun to make guys cum?"
"Really? You mean I can get a blowjob any time I want from now on?" he said seriously.
I looked at him "Sure, why not? You want one now?"
"FUUUUUCK YES!!" He said as he pulled his pants down.
I smiled and knelt in front of him. I stared at his hard cock as I pulled his pants to his ankles. Bob just smiled as he watched me and spread his legs wide.
He couldn't believe his luck. For the last two years he had wanted to get a blowjob and now he knew where he could get one any time he wanted. All he had to do was go next door and hang out with his best friend. HOLY FUCK!!!
I crawled between his legs and began to kiss and lick his ball sack. I fondled his balls with my tongue. Then began to kiss and lick my way up the shaft of his cock. I began to slowly stroke him with my hand while I sucked just the head. I moved my hand and sucked more and more of his cock into my mouth. I put my hands on his thighs and sucked him like a greedy whore.
Bob must have really been hot because after about 30 seconds of that, he jumped, groaned and shot off in my mouth. I swallowed and kept sucking him slowly. After another minute or so I looked up at him, smiled and sat on the couch again.
Bob smiled back and pulled up his pants."That was fucking great!"
"I know!" I said beaming "I wish I could turn into a girl any time I wanted! I would be such a slut! I could change to a girl, suck dick, give up some pussy and change back. I think that would be soooo cool!"
"Yeah!! No Shit!!" Bob said enthusiastically "You could change into a super model or a movie star! You could suck my dick and I could spend the day fucking the living hell out of you!"
"Fuck Yeah!" I agreed.
Bob had a big smile as he thought about it. "That would be so killer! We could both get laid any time we wanted! You could dress up in skimpy little outfits and prance around."
Bob was picturing me changing into Hillary Duff and doing a pole dance in a G-string. I was picturing something a little different. Something a little easier.
"That's it!" I exclaimed
"What?" Bob said with a confused look.
"I could dress up as a girl." I said seriously
"You could what?" Bob replied.
"I could dress up as a girl." I repeated "I mean, my Mom's gotta have something I could wear. You could check it out and tell me what you think."
Bob thought about it for a long minute. "OK let's try it. I wanna see this."
"OK let's go dig through moms closet and see what she's got." I said as I got up and headed to mom and dads room. Bob followed me right into moms closet and we started picking through her clothes. We couldn't find anything sexy enough for Bob's tastes, so we kept looking.
We started looking through the boxes on the top shelf. At the bottom of the pile was a big pink box that said Fredrick's. We were expecting to find more junk. We were shocked when when we opened the box and saw a big set of tits looking at us. We both dived in and began looking through the box.
The tits were a life like breast mold about an inch thick. They had nipples and everything! There were knee high black boots with a bright shine. Black stockings. A black satin thong. A black corset with just an outline of a bra. The tits stuck through the hole. A see thru black bra. A long black wig and a cat mask.
"Fuck Jim! You gotta put this on!" Bob pleaded "Fuck this is perfect! You gotta wear this!"
"OK" I said as I took the box and set it on the bed. "I gotta shave my legs and shit. Go wait in the living room and I'll be out in a while."
Bob nodded and headed to the living room. I was so turned on by the thought of dressing like a girl, I jerked off while shaving my legs. By the time I got to shaving my pubes, I jerked off again.
I had watched mom get dressed a million times so that went easy. Even putting on the makeup. There were two things that stumped me. What to do with my cock? And how do I make the breasts firmer? They were only an inch thick so they crumpled right up.
I pulled my cock back between my legs. That gave me a decent looking pussy. I thought about the tits for a while. I finally balled up some socks and put them inside. That gave me a beautiful looking and feeling set of tits. I looked good and I was really happy with the results as I examined myself in the mirror.
I put on some perfume and once I was satisfied I looked and smelled good, I headed out. I walked into the living room to find Bob just about asleep on the couch. I turned on some music, turned off the TV. Then I started to dance and jiggle in the middle of the room.
Bob immediately sat up and took notice. He didn't say anything. He just watched as I jiggled around doing all the things I wanted to see a girl do.
I shook my tits at him. I bent over and spread my ass cheeks. I pulled down the front of my panties and showed him my bald little pussy. Bob continued to watch silently as the bulge in his pants grew.
I straddled the bulge and rubbed my crotch into it. I could feel his cock straining in his pants as he grabbed my ass. I pressed my tits into his face and removed his shirt. I then unfastened his pants, dismounted and stripped them off.
Bob sat nude on the couch with a stunned look. I raised my arms did a small jig and a slow turn
"What do you think?" I said with a big smile.
"Holy Shit Jim! That's Awesome!" he said with a dazed look "If I didn't know it was you, I'd never recognize you. Fuck! You really look like a girl."
I turned shook my ass at him again, looked over my shoulder and smiled "COOL! Thanks!"
"No, Jim, you don't understand." he said "I really want to fuck you! I mean, you just wouldn't believe how much I want to fuck you!"
I straddled his cock again and began rubbing the smooth fabric of my panties up and down his cock. "What's wrong with that? That was the plan. I could change into a girl and we could get laid any time we wanted. Right?"
He grabbed my ass and began thrusting his hips. Mashing his cock hard against my crotch. "There's something about wanting to fuck your best friend tho."
"Well, don't think of me as your friend Jim." I began to breath hard and match his thrusts. "Think of me as Susan, or pick a name."
"Susan would be fine." he pressed his face into my tits and began easing my panties down.
I leaned back and smiled. "Fine. My name is Susan and I'll be your slut for the day. Help yourself to anything you like. I hope you enjoy the ride." I said as I handed him a small tube of KY I stole from Mom.
With a big smile Bob took the tube. "Fuck Yeah! Susan, I'm gonna enjoy this ride more than you can imagine!"
Bob rolled me over until I was kneeling in front of the couch. He kneeled behind me and fondled my tight ass.
I was so turned on. I couldn't believe I was dressed as a girl and that Bob was going to fuck me!
Bob pulled my panties down and applied a gob of lube to my puckered brown hole. He then forced his thumb in as far as it would go in one stab.
I jumped and moaned in surprise. He wiggled it around a bit and began to give me a hard finger fucking. It felt so good, I squeezed my asshole tight as I could.
Without any warning, he pulled his thumb out and stabbed his cock balls deep into me. I squealed, but Bob grabbed me by the hips and started pounding his cock into me. I groaned and pushed back quickly to meet his thrusts.
I thought it was going to hurt, but this felt good. There was a slight winch when he first forced it in, but it was replaced almost immediately by pleasure.
I couldn't believe I was getting fucked! Bob was fucking the living shit outta me and it felt great!
I was pushing back to meet his thrusts. Squealing and moaning the whole time. While Bob was behind me hammering his cock home. Grunting and groaning, as he worked to satisfy his needs.
Then he drove deep into me. I could feel his cock twitching inside me while I listened to him moan loudly. I smiled and squeezed my butt hole tight. While he pumped me full of cum. When he was done, he collapsed on my back panting with exhaustion.
His cock still inside me, I had a big satisfied smile. I had just dressed like a girl and let Bob fuck me like a whore! This was great! I made him cum! He fucked me hard, dumped a load inside me and I loved it!!!
When we had both recovered, Bob sat nude on the couch again. His cock had a slick wet shine. I was bubbling with pride, knowing I had let him use me to satisfy his stiff meat.
This was great! I wanted to be his slut all day every day!
Bob watched closely as I cleaned up. As I pulled my cock back into it's hiding place and pulled up my panties. I then laid on the couch, stretching my legs across his lap.
Bob began to caress my legs and closely examine the new me. I smiled, put my hands over my head and let him roam free. He played with my tits with one hand while caressing my thighs and panties.
I moaned and made no effort to hide the fact that I was getting turned on. This was so cool watching him explore my body as if it was a girls.
"So, was I a good first piece of ass?" I giggled.
"Fuck Yes! You are a GREAT piece of ass!" he exclaimed "How is it being my slut?"
"I love it!" I said as I spread my legs.
I could feel his cock throb against the back of my knee as it got hard again. Bob continued to feel me up. Then pulled my panties off. My cock sprang free and laid on my belly.
"Fuck, you really do like being my slut don't you?" he said as he spread my legs and kneeled between them.
"I already told you.... I LOVE IT!" I said while spreading my legs even farther.
I looked down and couldn't believe how sexy it was. I had long hair, big tits with hard nipples. Knee high boots, stockings. Best of all, there was Bob, kneeling between my outstretched legs. His hard cock moving in for the next anal invasion.
It was so sexy, I was stunned. So this is what girls see when they're getting ready to get fucked? I thought as I wrapped my arms and legs around Bob and pulled him down on top of me.
I pulled my knees back to my chest while Bob positioned his cock and drove it in. He was laying on top of me, panting into my ear already. I could feel his balls pressing against my ass cheeks while his cock hair was pressing against my shaved ball sack.
I moaned, squeezed him tight and whispered into his ear "Oh God Yes! Fuck Me Bob!"
He began to ram into me hard and deep. I squeezed my ass around his shaft. Pulling my balls up into me. I soon began to squeal and buck my hips in rhythm.
The feelings were so erotic. I could feel my tits jiggling with every thrust. I could feel my hard cock being mashed and rubbed between our bellies. I could feel him on top of me as pummeled my tight ass.
This was great! It was even better than sucking cock! I was dressed like a girl and letting Bob use me as his personal fuck toy! I was so turned on I couldn't stand it!
I began to jump and buck under his relentless pounding. My ass convulsed around his invading cock. Cum spewed from my cock. I jumped, jerked and squealed.
Bob held on tight and kept fucking the shit out of me. Soon, he began to jump and groan. He drove deep and once again filled me with cum.
He left his cock inside me and collapsed on top of me. We both laid there panting and exhausted.
For the rest of the day I stayed dressed up in my new outfit. I did my daily chores while Bob watched and sometimes helped. Mostly he sat around nude. When his dick got hard he would get up and fuck me, no matter what I was doing, then sit back down.
I joked about it with him and had to laugh when he quoted me. "I'll be your slut for the day, help yourself to anything you want."
Later that afternoon while Bob and I looked for more clothes that I could wear as Susan. We struck gold! Out in the garage were some boxes marked for good will. But they never went anywhere. The pile just got bigger. Since nobody would miss it we took what we wanted and stashed it.
Before my Dad got home Bob decided to take off. Before he left, he fondled my ass, saying "Susan, I hope we get to spend alot of time together."
I smiled "Mom and Dad are gone all day and we have all summer. Stop by about 9 and I'll be waiting."
He squeezed my ass again "I sure did enjoy the ride, so I'll be here 9 sharp!" then he spanked me hard and walked off.
I walked inside and giggled about what a slut Susan turned out to be.