Hi, I'm Jimmy James, this is a story about a high school prank that spiraled out of control.
(cd, first, oral, anal, inc, m/cd, m+/cd, M/cd, F/cd)
============================ My Jr. Prom-1
When I was 8, my family moved from Chicago to the middle of nowhere northern Wisconsin. Soon after that, I met Bob. We became friends instantly and have been best friends ever since. We're 16 and juniors in high school now.
He's a jock and a sports freak. While I'm a science geek and a book worm. He was 6'1" and 190 lbs of muscle and built like a jock. While I was about 5'8" and 125 lbs, with a fat ass. My mom was a nurse and my dad was a carpenter. His dad was a farmer and his mom was a teacher.
Despite the differences, we hunted, fished and camped out quite often. We did all the things 16 year old boys did. Which of course included talking about sex, girls and what we wanted from them.
He of course had better luck with the girls than I did. He was a horn dog.................. All he ever wanted to do was get laid. So he was always chasing pussy. While I had only managed to finger a girl twice and almost got my dick sucked once. He got laid all the time. I didn't understand it, but that's the way it was.
Because of our friendship, I hung out with and got along with everybody. Jocks, geeks, divas, I mean everybody and so did Bob. Plus, my parents were easy to talk to, very open and very understanding. This would play a key roll in how things unfolded in the next couple of months.
But, that's enough history for now.
Prom was a little over 2 months away and it was all anybody was talking about. Bob and I were sitting at my house talking about it and my mom and dad told us about how much fun their prom was. How nice the dance was. How funny it was when their friend put his name in for prom queen and then showed up in a dress. How he could have won if he had only shaved and done his makeup. Finally they told us about how they went out parking and had sex for the first time.
When they asked what our plans were. I told them that everybody I wanted to go with already had a date. So I wasn't planning on going. Bob told them he had just broken up with his girlfriend and wasn't planning on going either. My mom looked at both of us in shock.
"You gotta go! It's your Jr Prom! It would be a shame to miss one of the most important events of your high school career" she insisted.
We both shrugged our shoulders and shook our heads.
"Maybe one of you should do like my friend did. Put on a dress and you can go as a couple. I bet mom could help with the makeup." my dad chuckled.
Bob smiled at my dad "I'm not sure I wanna wear a dress, but if Jimmy does, I'll take him to the prom."
I laughed "Like anybody wants to see me put on a dress and show off my hairy legs"
Bob chuckled "You'd have to shave your legs, but I think it would be funny as hell"
My dad laughed "Me Too!"
My mom just shook her head "You guys are terrible"
Bob and I took off after that and went fishing. Except for the fact that we spent most of the time joking about how funny it would be if I really did dress like a girl and go to prom. It was a pretty average fishing trip.
============2============
For the next few days Bob and I joked about it alot. We even told a few of our friends that I was thinking of running for prom queen. They all thought it was hilarious and assured me they would vote for me.
After a few days, the whole school was buzzing about me being the prom queen. Some of the teachers were furious and the principal took me aside to tell me I couldn't run. I furrowed my brow and looked at him closely.
"Why not?" I asked.
He looked at me sternly "Don't get smart! You're not a girl and you can't run!"
"The handbook says that the class votes for king and queen. It doesn't say it has to be a boy and girl" I remarked with a smile.
He got a confounded look and stomped off. I was just joking about being prom queen, but it made me mad to be told I couldn't. I fumed about it all day. Now I had to be prom queen just to piss him off.
When school was over, Bob and I headed for his truck to head home. He had a big double cab duel wheeled truck from the 70's. It wasn't much, but it was roomier than most cars. It had big bench seats front and back. With lots of leg room. It was like a go anywhere shaggin' wagon.
Bob could see something was bothering me so he parked out in the woods and sparked a joint. While we smoked, I told him what happened and how pissed off I was. When I was done bitching, Bob just laughed.
"I already told you. Shave your legs and I'll take you to the prom." he told me seriously.
I giggled "OK, I'll talk to my mom tonight."
When I got home, I got online and looked up all the info I could find on cross dressing. I spent about two hours looking stuff up and taking notes.................. I found out all kinds of stuff about shoes, panties, bras, wigs, clothes, hair removal. Hiding my cock. I was shocked at how much there was to know about being a girl. I had no idea what they went through.
When dinner was ready, mom called me to the table. We started to eat and my mom asked what I was working on so diligently.
"I was doing a little bit of research and I was hoping you could help me later." I told her.
"Sure sweetheart. What are you working on?" she asked.
I bit my bottom lip. "I was wondering what it would take to dress like a girl so I could run for prom queen"
My mom stared at me dumbfounded while my dad started to laugh.
"Go big or stay home!" he chuckled.
My mom gave him a dirty look. "Don't encourage him!"
"I'm sorry honey. But I thought it was funny in high school and I still do. If he wants to do it. I say we help him" he said plainly.
She looked at me. "Ok. I'll help you with whatever you need, but you have to do it like you mean it."
"Of course!" I eagerly agreed.
"And you'll do whatever I tell you?" she queried.
"Yes!" I said with a smile.
She smiled and shook my hand. "OK, we have a deal"
============3=============
After supper, my mom helped me clear the table, while we talked. She asked about what I wanted to look like. what color hair and how big I wanted my tits to be. I giggled, told her I wanted big tits but other than that I didn't know.
She smiled "I should have known. I'll take care of it."
She got a tape measure. Measured my chest hips and inseam. Then she took off. I did the dishes like always then went to watch TV with my dad.
"Where did mom go?" I asked.
He shrugged his shoulders "To the store I guess"
We watched TV for about an hour when my mom walked in with some bags.
"Let's go Jimmy" she said as she walked through to the bathroom.
I jumped up and followed her. Once in the bathroom, she closed the door.
"Strip" she told me sternly.
I looked at her funny, but she was a nurse, so I reluctantly stripped nude. She pulled out a can of hair removal cream and started to shake it.
"Tell Bob, for the next two months you're grounded. You're to be home by dinner time every day and you can't have visitors." she explained "I want you to spend every spare minute as a girl. I want you to dress like a girl. Talk like a girl. And act like a girl at all times. I want you to be so used to it by the time prom gets here that it will be like second nature. Your father and I are even going to start calling you Susan, OK?"
I smiled and nodded. She had me stand in the tub, where she proceeded to cover my whole body with hair remover. Everything except my cock, balls, armpits and anus. She explained about not coating them because it would burn and that I should finish with a razor. Plus, I was to do this every Sat morning until prom. I of course eagerly agreed.
Once we waited long enough, my mom gave me a razor and told me to take a shower. When I got in the shower, every bit of my body hair rinsed right off. Then I shaved the rest. I was smooth as silk everywhere. It was amazing.
When I was done, I wrapped a towel around my waist and called my mom. She quickly followed me to my room where all the bags were laid out. The first thing she had me do was sit on the bed while she pulled out a large set of silicone breast forms.
I picked one up and examined it closely. It was big soft and bouncy. It had a big puffy nipple with a large areola. I was shocked. It looked and felt just like the real thing. It was incredible.
"Wow, where did you got these?" I asked.
Mom smiled "At the hospital. They keep them as a prosthesis for women who have had breast cancer. They're a D-cup. I hope they're big enough for you."
"They're huge!" I replied emphatically.
"That's what you wanted so that's what I got" she giggled.
She took back the breast. Showed me how to apply the adhesive and how to properly position them on my chest. Once they were on, they were fucking great. They were quite heavy but they looked, felt and bounced just like real tits.
We practiced talking like a girl for a little while as she put a wig on me. It was flame red with long flowing curls that came about four inches past my shoulders. It was really quite impressive.
When she emptied the rest of the bags on my bed. There was a package of six low rise bikini panties. Two pair of low rise jeans. A blue tube top. A yellow tank top with spaghetti straps. A white lace top that was extremely low cut in the front. Last, she gave me a note on hospital stationary that said I was to be excused from gym for the next three months.
I smiled real big and gave her a big hug. "Thanks Mom"
She hugged me back. "Any time Susan. Now hurry up and get dressed so I can see what you look like."
Then she walked out and left me alone in my room.
I put on a white pair of panties and pulled my cock back like I had read about. I pulled up the jeans. They were a little tight, but not bad. Then I put on the lace top and looked in the mirror.
I had a monster camel toe. Huge bouncy tits and my nipples were so big they poked right through the lace fabric. It was one of the sexiest things I had seen in a long time. I looked like just about every hot babe that I ever wanted to fuck. I was shocked at how easy it was and thought it was great.
I walked into the living room to show mom and dad. Mom said I looked nice................ Dad made no bones about saying that he thought it was amazing and that I looked great. I smiled, sat down and watched TV like that and they called me Susan for the rest of the night.
=============4=============
The next morning I took off my tits and got ready for school. I put on a clean pair of panties under all my usual clothes. Then I smiled real big and stuck the note in my pocket. I never liked gym class anyway.
When Bob came to pick me up in the morning, My mom pulled me aside.
"I have Sat off, so plan on going shopping so we can pick up some more stuff that you need. OK?" she told me.
"Cool, that would be great" I said as I smiled and hugged her goodbye.
When I jumped in the truck, Bob handed me a joint and pulled out.
"Did you ask your mom?" he smiled.
I fired up the joint. "I sure did. She wasn't very happy. For the next two months I gotta be home by dinner and no visitors, but she said she would help me."
Bob laughed "What did your dad think?"
I hit the joint again "He thought it was funny as hell. He was the one that talked her into helping"
"Figures, he always liked hot T'nA." he gave me a sly look "Am I taking some hot T'nA to the prom?"
I laughed "I don't know about that, but I'll shave my legs for you"
He chuckled "I guess that'll have to do"
We finished the joint and headed into school like any other day. I went to the office and gave them my note. They made all the scheduling changes and told me to report to study hall.
It was like any other day, except that by the end of the day I had been asked at least dozen times if I was going to run for prom queen. I never told them yes or no, I would just laugh and say ok.
After school, Bob and I parked in the woods, did some fishing, burned a couple joints and talked about prom. I was planning on surprising him on prom night. So I didn't tell him what my mom had planned.
When I got home, I said hello to mom and dad. Went to my room, stripped down to my panties, put on my wig and tits. I had quite a bit of trouble with my cock slipping out of my panties while I did this and it caused me quite a bit of consternation. So I finished getting dressed.
I put on my low rise jeans and the tube top. I went out like nothing was wrong, set the table and jumped on the computer to look for better ways to hide my cock.
I found a couple stories in nifty that talked about taping your cock to a butt plug to keep it restrained. Others talked about rinsing your ass out with water or a douche to keep it juicy, wet and smelling nice. I thought they were all cool ideas and decided to try them all after dinner.
During dinner, I kept catching my dad staring at my tits and smiling. Quite often I caught myself doing the same thing so I would just smile back at him. Mom just sat quietly, smiling at both of us. I ate dinner like always and did the dishes like I always did.
=============5=============
As soon as I was done with the dishes, I set about finding something to use as a butt plug. All I could find was a ping pong ball. Since I had read a story about a butt plug that size, I grabbed it and some tape and headed for the bathroom.
I used the enema bottle to rinse out my ass with water a few times. Then I douched and started on my butt plug. I taped my cock to it as best I could and stuck it in my ass. I had some trouble getting it in at first, but once I fingered myself a little bit, It slid right in.
It pulled my cock back so far it just about pulled my cock head in. I re-arranged my balls and looked in the mirror again. It looked nice and once I pulled my panties up, it looked great.
Just like in the stories.
I ran my finger through the crack and suddenly my pussy became more visible and more defined.
I giggled, squatted, reached into my panties, pulled my cock and balls apart and watched as the smooth fabric folded right into the crack. When I stood up and looked in the mirror again, I had the perfect camel toe. It looked like my pussy lips were just about hanging out at the sides and my panties were pulled way up into my pussy. I had a nice looking pussy and an awesome camel toe. It was fucking perfect.
I pulled up my jeans with a smile and went out to watch TV with mom and dad. The whole time I was watching TV, I was thinking about the stories I read and how nice it felt when I fingered myself.
It was soft wet and juicy just like they said.
They also talked about how much fun it was to suck cock and get fucked while dressed as a girl. That made me think about Bob's last girlfriend Linda. She was one of the new Christians and was proud of being a virgin. Bob told me he never got any pussy, but she would suck him off and let him fuck her in the ass whenever he wanted. He told me it was good sex and she always put out. Every time I pictured myself doing that, I could feel my cock start to get hard.
That night, I pulled out the butt plug and put it on my dresser. Then I jumped in bed wearing nothing but my panties. I laid back, spread my legs, reached into my panties and started to finger myself. It was warm and wet and it felt great. I sniffed my finger and just like the story said, it smelled like floral douche. I smiled and drifted off to sleep.
==============6=============
First thing in the morning, I got into the bathroom, rinsed out my ass and douched. I got the solvent and took off my tits. It was Sat morning, so I did all the things my mom told me to do. I coated my body with hair remover, waited 10 minutes and jumped in the shower. I shaved my ass crack, balls and armpits. I couldn't grow whiskers so there was no need to shave my face. Finally I soaped up and took a shower like I always did.
Once I was done, I taped the ping pong ball to my cock again, fingered my ass and stuck it in. I put on a clean pair of panties, put my tits back on and headed to my room. As I was standing in the middle of my room wearing nothing but panties, my dad poked his head in. I watched as he eyed me up and down, spending extra time examining my pussy and tits. He had a big smile the whole time.
"As soon as you're dressed your mom wants to talk to you." he told me.
I smiled back at him "OK"
He gave a little chuckle and closed the door. I quickly put on the tank top and the other pair of low rise jeans. Then I headed for the kitchen to talk to mom. She sat me down, took off my wig, shaved up the back of my neck and on the temples. Then she put the wig back on and carefully applied the adhesive for my tits to the back of my head and temples to hold the wig in place. Once she did that, it was stuck on like it was my own hair. I brushed it as quick as I could and we were out the door.
When we got to the mall, the first thing we did was go to the makeup counter. She told the woman that I had never worn makeup and would she show me how it was done. She also told the woman to help me pick out whatever makeup I needed.
The woman said she would be happy to. She sat me down and began explaining everything there was to know about makeup. What I needed, why I needed it, what I needed it for and most importantly.
How to put it on and take it off.
An hour later, I had a bag full of makeup, and I didn't even recognize myself. I looked like a whole new person. My mom was of course thrilled with the way I looked. She told me over and over how pretty I was.
Next we went to get shoes. I must have tried on every pair in the place. When we finally finished, I had 6 pairs of high heels. Three of them had 4" heels, two of them had 2" heels and a cute pair of sneakers.
I complained about trying on so many shoes quite a bit. As a guy, I had 2 pair. Dress shoes and gym shoes. I didn't see the point in having so many styles and colors. My mom assured me it was normal for girls. It was important that we have shoes to fit any outfit or occasion.
Next, we went to get some clothes. I was more excited about this than anything else. My mom giggled at my excitement and told me I could only get skirts and tops. Maybe a couple pairs of shorts. Being a guy, I picked out all the sexiest things I could find.
My longest skirt came to just above my knees. The shortest was a hot little black mini skirt, but most were to about mid thigh. We also picked out a couple short pull over dresses.
When we were in the changing rooms trying on the first outfit. My mom was amazed at how nice my pussy looked. I eagerly showed her what I had done and told her about rinsing and douching. She thought it was the coolest thing and assured me that she would have extra douches for me.
After she saw that, we picked out all the sexiest panties we could find too. Almost all were thongs and you could see thru most of them. Some of them had saying on the front 'juicy' 'sexy' 'burger time' 'yummy' 'breakfast of champions' 'where's the beef?' We must have gotten 20 pairs.
We spent pretty much the whole day shopping. We picked up stockings of every color, shoes, clothes, baby doll night gown. Everything a girl would need and lots more than I thought I would ever need. We even got a bunch of jewelry and perfume.
=============7==============
When we got home, I turned my cock loose and got on the computer to look for more cross dressing tips. I had to find a better way to hide my cock. What I had looked great, but after two hours it was uncomfortable. After six hours it was unbearable.
I didn't really find anything until I stumbled onto 420chan. There was a section just for cross dressers. As I looked at the posts, I became quite excited. I hoped I looked as good as some of the guys that were there. I knew I looked better than most of them.
When I got to some pics of a guy in drag sucking cock and getting fucked I was mesmerized. I couldn't take my eyes off them. My cock got so hard, I could hardly sit still.
I couldn't stop thinking of all the stories about how much fun it was and how good it felt. I couldn't help but to be turned on when I pictured myself doing what 'she' was doing. My thoughts and desires were so strong, I didn't know what to do about them. I found myself reaching up my skirt and playing with my cock.
When I finally tore myself away from the pictures. I found a post called 'glue a vagoo'. It had pictures of a guy using super glue to hold his cock back then pull his ball sack over it to look like pussy lips.
There were step by step instructions of how to pull your balls up, how to situate and pull everything and close up pictures. When he was done..... it looked just like a pussy. He had pictures of everything. Front, sides, legs spread, everything and it looked great.
I knew I had to try it.
I called my mom over and talked to her about the problem I was having. I showed her the pics. We talked about it. The super glue might burn at first but wouldn't hurt anything. She said she didn't see any problems and to try it if I wanted. I gave her a big hug and said thanks.
We all went to bed early that night. I had a long day so I was wore out. I put on my new baby doll night gown and smiled. The ruffles ended just below my butt cheeks and the top covered just enough of my tits to cover the nipples. I thought it looked great.
I jumped in bed and just about the time I was about to fall asleep, I heard my parents going at it. As I listened I thought about the pictures and began to stroke my cock. Mom was being more vocal than usual so my dad must have been giving it to her good.
I got so turned on listening to them I was rock hard. I got a big smile and imagined what it would be like to be her. I could be laid back with my legs spread while my dad was fucking me silly. I could almost feel him inside me. The thought of it was so erotic, I came almost instantly.
As I came I watched it shoot out and collect in my hand. The image of a 'girl' with a mouthful of cum or dripping out 'her' ass flashed into my mind. I thought about what a rush it would be to have somebody do that in my ass or mouth. I smiled real big as I licked up and swallowed cum for the first time.
As I drifted off to sleep, I was listening to my parents going at it hot and heavy, and thinking about how good my first taste of cum was.
==============8============
In the morning I got up about 4:30. I was so excited about trying my new vagoo that I couldn't sleep. I told Bob I would be busy all weekend so I knew I had all day.
I rushed into the bathroom, rinsed and douched. I took a quick shower and jerked off again. Since we didn't have any super glued I grabbed the adhesive for my tits. I figured it would be better anyway. It was pliable like rubber cement, plus it was flesh tone so it was easy to hide.
I was having trouble getting things together at first because my cock was always getting loose. I decided to cheat by putting in my butt plug. It worked perfect, it pulled my cock back and held it in place while I pulled my balls up and stretched the sack around my cock. I put the glue under my cock and followed the instructions to the letter.
When I finished, I was thrilled. It looked just like a pussy and just like the pictures. When I took off the butt plug I was even more thrilled. My cock disappeared inside itself like a turtle into it's shell.
There was no sign of my cock or balls. There was no indication that I had ever had a cock or balls. Not only that, it looked just like a vagina. There were curled up folds of skin similar to an uncircumcised cock and an opening. I could even stick my finger into it almost to the second knuckle. It was fucking amazing. Plus it was so comfortable, it seemed natural....
I brushed my hair in the nude. The whole time I was staring at myself, I couldn't believe how hot I looked as a redhead. I watched my tits jiggle, sway and bounce when I moved. They looked so hot. They were almost as good as real ones, but my pussy was all me! I could examine it as close as I wanted and it was all real. I couldn't believe what I was looking at.
I had the hottest little pussy I had ever seen!!
I didn't have near the camel toe that had and you couldn't fuck it, but other than that it looked just like any other pussy. I could walk around nude. I could get felt up. I could even get fingered a little bit and there would be no way to know I wasn't a girl.
I squealed with delight and put my night gown and panties back on.
=============9==============
I walked into the kitchen to get breakfast and talk to mom. What I found was my dad sitting in his underwear drinking coffee. My dad did that every day from 5 till just before 7 when he went to work. I looked at the clock and it was 5:30. I had forgotten how early I got up.
"You're up early" he said with a big smile.
I smiled "Yeah, I couldn't sleep"
I got a glass of orange juice and sat at the table with him. We talked about what I was doing and he told me how nice I looked. He told me I was even prettier than mom was when she was 16. I just blushed. He told me he thought it was funny when I said it at first, but now he couldn't wait to see me in a prom dress. I blushed again.
I got up to get some cereal and poured coffee for my dad when he asked. My dad and I continued to talk about the usual things as he drank coffee and I ate breakfast. Every time I got up he would ask for coffee and I would get it for him.
At 6 when my mom finally came out in a bath robe, I was just finishing with breakfast. She leaned over to give my dad a kiss, looked down and smiled.
"Rise and shine" she giggled as she kissed him.
She sat down and asked me to get her some coffee. While I got her coffee and cleared my place she asked if I had tried what we talked about.
I smiled real big "I sure did!"
"How did it work?" she asked.
I put the last of the stuff in the sink.
"I gotta show you! Come here!" and headed for my room.
She got up and followed close behind me. I closed the door and stripped off my panties.
"Wow" was all she said.
I sat on the bed and spread my legs to give her a good look and told her everything. I told about the glue. I told about the plug. Where my nuts went. How I pulled the sack around from the sides. How my cock pulled back inside itself. How comfortable it was. I even showed her how far I could stick my finger in.
She smiled, took off her panties, sat on the bed and we compared pussies. After a short time, she put on her panties, told me to get dressed and left.
I picked out a tiny pink thong, short denim skirt and a tight white tank top. I put on my makeup and nail polish and headed to the computer. Mom and dad were nowhere to be seen so I looked up more dirty stories. No sooner did I start reading, than I heard my parents banging around while my mom squealed like a tea pot.
For the next 2 hours I sat and read stories about guys who were having the time of their lives dressing in drag and being used as a woman. They talked about how much fun it was to turn guys on, get fucked and get off inside them. They talked about how erotic it was to suck cock and what a feeling of satisfaction and accomplishment they got from swallowing a mouthful of cum.
While I read the stories and listened to my parents fuck. I was fantasizing about sucking Bobs cock or letting him fuck me. I was so turned on and it was so vivid, I could almost taste and feel his cock in my mouth. I had seen it in the locker room a million times and now I wanted to suck it in the worst way.
I fantasized about kneeling in front of him. Pulling his hard cock out and sucking on it. I imagined him grabbing my head and fucking my throat. Until he finally fills my mouth with ball juice and watches me swallow it.
I was so turned on and so horny, I couldn't stand it. I wanted to reach up my skirt and play with my cock so bad I thought I was going to die. Since it was glued up like a pussy, the best I could do was grind my crotch against the corner of the chair. It wasn't a total waste tho. I sorta had an orgasm and it was enough to satisfy me for a little while.
While I continued to read and fantasize about taking care of a bunch of stiff cocks. I began to caress my pussy again. When I got to where my vagina should have been, I was shocked to find a big wet spot. I reached into my panties and stuck my finger into the opening and it was wet and juicy.... I smiled real big when I did that. My pussy was a wet juicy hole just like any other pussy. When I pulled my finger out I could see it was covered in cum and licked it clean.