My Transformation Begins
My senior year in high school started normally. I was still dating Dannie and seeing Jaden, Carson, and Howard when time permitted. But one thing had changed. I began wearing women's lingerie much more often. I wore crotchless panties during all my male encounters. One day, I was at Dannie's house and Howard was fucking me on the pool table. I had on some of Carol's sluttiest lingerie, including leather boots and crotchless panties. We were shifting into a new position when I saw Carol standing a few feet away with a stunned look on her face. I felt sick inside and knew this was not going to turn out well. Howard didn't see her and said "Move your ass bitch, I want that sweet cunt of yours right now." Carol shuddered when she heard that and screamed "You unbelievable bastard. Get out and take your girlfriend with you." I was even more concerned with where Dannie was. Fortunately, she was still shopping with her friend Pam and had not come home yet. Howard scrambled to his feet and tried to reason with her, but it was no use.
She divorced him and made Dannie stop seeing me, but she never told Dannie the whole story. She couldn't tell anyone else without risking her own reputation and future alimony. Dannie was close to her father and it really tore her up inside. I felt guilty and angry at the same time. Why was it OK for her to have gay sex but not him. It's such a double standard. I also missed Dannie a lot. I was surprised to find that I missed holding her and talking to her as much as I missed the sex. A couple of times we snuck off to our old motel and had sex, but it wasn't the same. She was constantly worried that her mother would find out.
The next shoe dropped when my father passed away. He had surgery for a gall bladder problem, got a bad infection, and just couldn't beat it, even with IV antibiotics. I was very shook up. I had always been afraid that he would find out about me and now I would never know how he would feel about it. I decided to tell my mother a few weeks after Dad died. She just smiled and said "David, it's OK, you're father and I knew for a few months. He took it hard at first, but decided to let you figure out what you wanted." I should have told him myself. After that, I decided to just be myself. I grew my hair longer so that I could look feminine or wear it in a ponytail when I wanted to look more masculine (lots of guys were doing it then). I started wearing crotchless panties and stockings under my pants, even at school.
When I took my pants off in gym class, it created quite a stir. Guys were calling me faggot and pussy and the instructor told me not to wear those things anymore. The principal talked to my mother, but she refused to make me stop. I told everyone that I was bisexual, but they still called me faggot. Dannie put two and two together when she stopped by Howard's apartment unexpectedly and found me there in a robe. Howard and I were fucking each other on a regular basis. I told her the whole story and she took it very well. She said it would just be too strange having sex with someone her father was screwing and we stopped getting together for sex. We still talked occasionally and got along well. She was an angel.
I lost the trainer spot, but I was tired of the responsibility. The new players were so straight-laced and Jaden was no longer playing. He had to downplay his relationship with me, but we still got together and had sex when we could. I had just turned 18, so no one could really say much about my sex life anymore. The strangest thing was the way some of the girls reacted to my new image. The girls with a reputation for being sluts seemed to be more attracted to me. I didn't quite understand it, but I liked the attention. One girl, Judy, had once gotten wasted and sucked off five guys at a party. She was really nice looking and someone took a video of her doing it. She was flashing her tits, rubbing her pussy, and getting her face covered in cum.
She started having lunch with me every day along with her friend Heather. Heather was notorious for getting caught in auto shop after school getting her ass fucked by the shop teacher. He got fired and she got suspended until her parents threatened to sue the school. They were so intrigued by my lifestyle and wanted to hear every detail which, of course, I couldn't tell them. One day after school, they pulled up beside me at a light and motioned for me to follow them, which I did. They drove to Heathers house and invited me in. I was worried because some of the parents were not happy with their kids hanging around me. Heather told me her parents were in Jamaica so I changed my mind quickly.
Heather opened the bar and we all had a drink (or two). She put on some music and Judy started dancing in front of me. As she swirled around she started taking off her clothes. I was mesmerized. She had nice tits, not huge, but big enough and her ass was a work of art. I felt a pair of breasts press against the back of my head and turned to see Heather, already nude. Her tits were very large and very shapely. She was just slightly overweight, but she really looked sexy. The girls took my hands and led me to Heather's bedroom. I was so hot and hard, I thought I was going to cum in my pants.
The girls stripped me and laid me on the bed. Judy started sucking my cock (of course) and Heather planted her steaming cunt on my face where I proceeded to work her over good. Heather was gushing cuntjuice everywhere and writhing like a snake. She kept telling me how good it felt. Judy was a talented cocksucker (lots of practice, I guess) and had me hard as a rock. Finally Judy couldn't stand Heather's moaning any longer and made her switch. Heather was not as good as Judy at cocksucking, but did manage to take all of my cock. Judy was just as juicy as Heather and screamed even louder.
Heather decided to sit on my cock, but I had not remembered to get condoms and told her so. She laughed and reached in her dresser, pulling out a big box full of condoms. She covered me and climbed aboard. The girls were facing each other, each riding me hard. Then they started rubbing each other's breasts, kissing, and tonguing each other. It was so hot to watch when I could catch a glimpse. Judy's pussy was blocking my view most of the time.
I finally shot a load up Heather's pussy and the two of them cleaned my cock with their tongues. While I recovered, they got into a 69 and went at it like bitches in heat. Judy reached out to stroke me and I got hard again quickly. Judy told me to fuck her and Heather would lick us both. They stayed in their 69 and I fucked Judy for a while. Then I started fucking Heather again. Finally, Heather asked me to fuck her ass and I kindly obliged her. Her ass was really tight and I had trouble getting my cock inside her. I finally broke through and gave her a world-class buttfucking while she sucked and licked Judy's cunt and ass.
After a while the girl's switched and I pronged Judy's sweet asshole. Heather jumped up and got a strap-on dildo and positioned herself to fuck Judy's pussy while I reamed her butt out. As experienced as I was sexually, I was discovering a whole new world of sexuality that evening. These girls were just doing what every guy at school would do if they could - have wild sex anytime they wanted.
We went at it for a couple more hours, trying lots of combinations. My favorite was when I fucked Heather's sweet ass and Judy did me with the strap-on. Before she fucked me, they dressed me in slutty clothes and put makeup on me. When I left, they were cunt-to-cunt with a double-dildo in their asses. I got together with them several times, but always together. They were inseparable (attached at the hip, or near there). Every time we got together they came up with something new. I even watched them pee on each other. I never could get into that, but it was hot watching them do it.
Heather told me to keep the clothes, because they were a little tight on her since her tits had gotten so large. I decided to wear them home, still in makeup. I really looked hot. It was dark out and I stopped at a light and some guys pulled up beside me and started whistling and asking if I was in the mood for some fun. I asked them what they had in mind and one of them said "You". I told them that I was probably not the kind of girl they wanted and they insisted I was. I decided to blow their mind so I raised up and flashed my cock. They freaked out and sped away. About that time the police lights came on behind me and the officer pulled me over.
He told me that he had seen me flash those guys and was going to have to book me for indecent exposure. I was really scared and very shaken. He made me lean against the car and he frisked me. He ran his hands up my legs which I thought was a little ridiculous since I was wearing a short skirt and stockings. When he got to my crotch and found my cock, he laughed and said, "I thought that's what I saw. You sure scared those smartass little bastards away." I was really confused now. What was going on?
"I'm going to have to give you a field sobriety test" he said and placed his middle finger against my asshole. He inserted it up to the knuckle, then removed it and said "Looks like you've had a couple of stiff ones. I'll have to give you a breathalyzer test." At that point, I realized he was just taking advantage of me. I'm sure he thought this was a funny, sexy come-on, but I was so shaken that I was not amused. He told me to get on my knees and swallow his probe, but I told him I was really not in the mood to continue this game. He realized I was irritated and apologized profusely. He said that he had misread the situation and apologized two more times.
By then I had calmed down a bit and started to feel sorry for him because now he was scared. He asked if I wanted him to follow me home to be sure that those guys weren't waiting to get back at me. I told him if he really wanted to make it up to me he could take me for a spin in his patrol car. I told him that I had always wanted to ride in one. He agreed and we got in and took off. He introduced himself as Jack. He said that he and his last partner had been fucking each other until someone found out that his partner was gay. After that he was abused to the point that he had quit the force, leaving Jack with no partner temporarily. As we turned down a dark street, I leaned over and unzipped his pants. He was shocked but excited as I pulled out his cock and started to lick the head. He looked for a place to stop but couldn't find one. I took his stiff member in my mouth and started to fuck it with my mouth. He was getting desperate to stop and pulled behind a supermarket.
We got into the back seat and I kept working on his cock. It had reached its full height now and I asked him if he had a condom. He grinned and pulled one out. When I slipped it on him, he almost came in my hand. I laid flat on my stomach and he climbed on top of me and lifted my skirt. I helped him position his cock and he eased it inside my ass. Thank God for lubricated condoms because we had no lubricant. He started slowly pumping my hot, steamy ass, telling my how tight and soft it was on his stiff shaft. He was getting close to coming when another squad car pulled up and the officers shined a light in.
Jack freaked out. "If they catch me fucking a boy, I'm dead meat. I'll have to leave the department". "Don't worry" I said, "Pretend I'm a girl and let me do the rest." The officers opened the door and one of them said "Hi Jack. Is this your idea of community relations?" "My car broke down and this sweetie was taking me home." I said in my most feminine voice. "I was just thanking him.".
"You have an interesting way of showing your gratitude ma'am.", he said.
"What is your name and how old are you?"
"My name is Tess", I lied. "and I'm eighteen, but I left my license in my car."
"Do you do this a lot young lady."
"Only for hot studs like Jack - and you sweetie."
"Are you one of those girls that likes uniforms?"
"I sure am lover and I'd love to suck your cock."
He looked around nervously, turned to his partner, and asked him what he thought. His partner said "Only if I get a turn.". I told him he would definitely get his turn too.
Jack was relieved and started to get hard again. He stuck his cock back in my ass as the first cop stuck his cock into my mouth. I proceeded to suck both of the late arrivals to roaring orgasms, swallowing both. I kept some of their cum in my mouth and when they thanked me and left I kissed Jack and shared their cum with him. He got so excited he pulled off the rubber and added his load to the mix in my mouth.
Jack told me, if I ever got into trouble with the cops, to ask for him and he would take care of it. He took me back to the car and I drove home. On the way I still had the taste of three cops in my mouth. It was delicious.
If you or someone you know has been with Tess, please email me at twonight@excite.com and tell me about it. I am very interested to compare your account with her journal entries.
Check out my fiction stories too (The Awakening, Black Dorm, Star Cruiser, and Olympiad), and my own true story (Shocking Encounter).