High School Dilemma Ch. 01

I should have known better. It was such a stupid thing and it didn't even work out. Here I was graduating from High School. I had just turned eighteen and it was the last week of school. How could I have done it? Why did I take the chance? Kelly was probably the prettiest girl in school. Her hair was long and blond. Not much different then mine. Actually we were both about 5' 5" and weighed around 120 pounds. But, Kelly was Joe's girlfriend. At least she had been for the last two years until the school Prom a week ago.

Joe on the other hand was huge. He was nineteen and had been the star defensive end of the school football team. Well over six feet tall and weighing somewhere north of 200 pounds with a mean streak he was someone to avoid at all cost. Stories abounded about how he had beaten the shit out of some kid who had gotten in his way. Or had gotten into a brawl during the weekend. His older brother Sean had been the meanest kid the school had ever known. He had graduated three years ago. Someone had said he was at least twenty when the school sent him on his way. Apparently he had been in a correctional facility since then for a melee at a local bar. Why Kelly went out with Joe was beyond everyone. But as she had said at the prom Joe just wouldn't let her leave.

Anyhow, at the school prom last week we had all had a bit to drink and was having a great time. Over the years every guy had fantasized about Kelly and at the dance she was the knockout of all time. She wore a beautiful green sequin dress with a matching headband. They accentuated her hazel eyes. Similar to mine except mine were a bit greener. Soft white skin and red lips just beckoned to be kissed. There she was standing by herself near the punch bowl when the liquor convinced me to go over and talk with her. Me with no muscle tone and white skin, the class poet and by luck had avoided being the class wimp by going home right after school had walked over and said, "Hi Kelly." She had had a few drinks also and was very friendly. Before much time had elapsed Kelly and I were back in a school hallway and had started kissing. I still don't know why she had kissed me. It had seemed to unfold so naturally and her lips were warm and tongue sweet to the taste.

But suddenly, there was Joe. He was red and furious. Kelly turned to him and told him to be still and that she was no longer his girlfriend and that she preferred me. I stood dumbfounded and scared but Joe just yelled at Kelly and stared ferociously at me and then left us. I took Kelly home that night and we kissed some more at her house and held hands. The next day at school Kelly avoided me all day and when we finally met up she said I just wasn't her type and asked it we could "just be friends."

Well, I didn't like the outcome, but what could I do. I asked her whether she was going back with Joe. She said "no way. I'm glad this happened. Now I'm rid of him and can have a fun summer and be free at college next year." I looked at Kelly so pretty in her pink sweater and gray skirt and thought to myself at least I had had a moment with her.

That was last week and all through that week Joe would scowl at me every time he saw me. I wasn't much worried since we lived in different sections of town and Joe was so caught up in sports that he had practice everyday for something after school. So I left at the bell and went home. There was only one week to go and then summer. We would never meet again. At least that was what I thought until yesterday afternoon. The last Monday of the last week of High School was yesterday and now things had changed.

I had left school just after bell. Wearing jeans and sneakers I walked the trail through the woods to my home. I had been doing it for as long as I could remember. The woods were about hundred acres of underbrush, trails and huge oak trees that separated the school from the north side of town. It was on the north side that the socio-economically well off lived. Joe and his brother lived south of the school in a project. I had never even been to that part of town. Apparently there were empty dilapidated buildings and trouble. Not a place I would ever travel to.

So, there I was about halfway into the woods when all of sudden I felt someone knock me down and start punching me. He punched my face, my stomach and before long I was crying. When I looked up I saw Joe. He looked down at me and with spit shooting from my mouth he yelled at me for breaking up his relationship with Kelly. I sat up and he yelled at me that I'd better not get up, unless I wanted to really get my "ass kicked in." So I sat there on the ground in the woods as he continued his tirade. I saw him looking at me and then he called me a sissy girl because I was crying. I was about to get up and try not being a sissy when he punched me again. He said that I had a choice. I could be the sissy he knew I was and not show any macho stuff. Then he said if I acted like a sissy, he wouldn't punch me but instead would slap me like he would a girl. Or else, I should get up and he would beat me silly.

I was in such pain and no match for him I just sat there simpering. He laughed a little and then called me Jill. My real name is Bill. He taunted me calling me JILL, JILL, JILL. I sat there thinking I'd rather be thought a sissy than being punched silly. Let him have his moment I thought. School would be out soon. It would all be over. Then he smiled and told me if I didn't do exactly what he said right now he would beat "the shit out of me everyday this week." So I sat there.

"Spread you legs and hold them open and close your eyes. If you move I'll give you a spanking so hard you won't be able to sit in school tomorrow and everyone will know," Joe taunted.

So, I sat with my legs spread apart as he towered over me. "Remember, don't move," he warned. And then he unzipped his fly, pulled out his cock (I didn't see it, but I sensed it), and before I realized it he was peeing on my jeans right between my legs. Soaking my jeans and underwear and I could feel my balls warm with his pee as he loudly said, " I claim you for my property and thus mark you with my piss as proof forever."

As I started to move away from his pee he leaned over and slapped my face and said, "don't." So, there I was sitting splayed and letting him empty his bladder on balls. I was so humiliated. When he finished he shook his cock and some pee droplets flickered on my nose and eye. He laughed.

Looking down at me as he zipped his fly he continued with the following. "As you punishment for the next week you will get a pair of panties from your sister. They had better be satin. You will wear them everyday this week. If you don't wear them I will spank your ass red. Do you understand?"

In a squeaky voice I answered yes.

He seemed pleased with himself and looked down at the dark pee stained crotch, laughed and then left me there. After I was sure he was gone I got up. He urine smelled so strong. As I ran home ashamed, holding my hand over my pee soaked genitals, the earlier warmth of his pee turned cold. I managed to get home and upstairs to my room without anyone seeing me. But I had to wash his deep yellow urine out of my white jockeys and also my jeans. I could smell that odor all night even when it was gone. So fearful of him was I that I managed to get a pair of white satin panties from my sister Jane. Jane was two years older then me but we were about the same size.

I put the panties on the next morning and went down to breakfast. I was so nervous. I thought everyone could tell. I was thankful that Jane was gone for the next 8 weeks. She was a counselor at a camp in North Carolina and had gone there a week early to set up for all the kids that would come next week. She loved being a counselor at camp but she was also very feminine. During the rest of the year she dressed very hot. When I got the panties from her dresser I was amazed that they were the only white pair. She had all sorts of things like thongs etc.

Mom and Dad were sitting at the breakfast table when I came down. Dad started the talk. "Bill, next weekend Mom and I are going to go on a two week business/ vacation. I just talked you Mom into going. I convinced her you can take care of yourself and will be responsible. We are going to be on a sailing cruise in the Caribbean and will call you when we have a chance in port. Since this is a real outback sort of adventure we don't know when we'll reach you so be sure to change the message on the answer machine each day. That way we will know you're ok."

Mom smiled at me and asked whether I'd be ok. I forgot about wearing the panties and told them to have a great time and that I would be fine. Mom also told me she had called the Mr. Weingold who ran the local grocery store and had advised him that I would be alone and that I could charge what I needed at the grocery store. "Also, Sid (Mr. Weingold) said he would check in on you at some time next week. He's going fishing for a few days and will call or stop by when he gets back," Mom said.

Mr. Weingold was a fat slob I thought to myself. I had never been nice to him, but my parents thought he was a nice man. Dad sometimes mused as to why at 48 he had never married. I knew why. Who would marry a 250-pound fat slob who was unkempt and dirty?

I assured them everything would be fine and went to school.

So, here I was sitting in class with satin panties over my ass and Joe keeping an eye on me. However the day went by without incident until I went to my locker at the end of the day. There was a note inside. I opened it. All it said was I had gotten by the first day and could go home safe. But in order to be safe the next day I would have to wear the panties and shave all the hair off my body. If I left any hair except for a proper little patch I would be beaten tomorrow. There was a cut out of a girl who was shaved except for a patch over her pussy. In deep blue ink written on the top right of the picture with a pointing arrow were the two words, LIKE THIS.

At home that night I thought to myself it was a lot better to do what Joe wanted then to get beaten. Also, he hadn't even bothered me. Perhaps I would get through the week ok. So, I shaved my body that night and made the little patch above my dick. As I did so I wondered how big my dick was compared to Joe's. I hadn't seen his as he peed. I had my eyes closed. Mine was a good four inches when hard and not very thick either. I hadn't seen anyone else's since freshman year. I had finished my required PE that year and had avoided all things that would require group showers. I thought, I bet he's smaller then me. They always say big guys have small dicks. And that made me feel better as I drained the tub and dried off.

The next morning at breakfast my parents told me they would put everything I needed on the refrigerator and in the drawer next to it. They would be leaving Saturday morning early so they could fly to Florida and catch their ship. Dad was really excited about getting away. Again I assured mom everything would be ok and went to school wearing the panties and fully shaved. I wore a long sleeve shirt and kept it buttoned up. Joe looked at me and smiled. But again the day went without incident except when I got to my locker. Again there was note. This time I was to find a pair of my sister's pantyhose and wear them on Wednesday with the panties underneath.

Well, none of this bothered me much since I wasn't getting beaten and no one knew what was happening. It was easy to comply. The next day I sat in class shaved, pantied and panty hosed. The silken panties made me squirm sometimes and I would nearly get hard but nothing I couldn't handle. Another note said for me to take a nice bath with my sister's bath bubble and wear a piece of scotch tape on both my nipples.

I got through Thursday and thought only one day left. School would be out and this would be all over. What I thought was the last note came in with a little box. It said I was to open the box that night and wear everything plus what was in the box for Friday. If I did this, there would be only one last thing and I would get that in my locker when I cleaned in out Friday.

That night at home I opened the small box and saw a butt plug in it. I was shocked. A little note said "PUT IT IN NOW!" I had made it through the week. This was so humiliating but only one more day I thought as I pushed it up my ass and went to bed.

The next morning sitting there at breakfast my parents giving me last minute instructions I felt my cheeks go red. Mom asked if I was sick. I said no and hurried out to school feeling the plug move in my ass as I walked.

I sat in class squirming a bit as Joe looked at me and smiled. At the end of the day I went to my locker and cleared my stuff. There was one more envelope. It said to be opened as soon as I got home. I hurried home figuring that it was over and Joe would simply give me a note laughing about what he had made me done. I rushed upstairs to my room and sat down. I didn't even take the plug out because I wanted to read the note first.

The note said, "Your final act of humiliation will occur tomorrow. You've come through the week so don't mess up now. At 10am meet me in the same place we were last week in the woods. Make sure you're wearing a bra and perfume and everything else you wore this week. OR ELSE." I was afraid as I read this but again I thought I could handle one day even if he peed on me again. Then I would be safe at home away from Joe forever.

Saturday morning my Mom opened the door to my room and said, "bye Bill, see you in two weeks. Are you still sick? If you are, call Dr. Jones. The number is on the refrigerator. Also we've left reminders like the changing of the message each day." I told her to have a great time, not to worry and would seem them in two weeks. She left the room. I looked at my clock it was 7 am.

By 9:30 I was sitting in the kitchen with the plug up my ass. Panties and panty hose on and a white cotton bra covering my scotch taped nipples. Twenty minutes later I put the perfume on. Something called "Opium" and went to meet my fate with Joe. I thought as I walked to the woods that in an hour I would be home and this would be over. He would either beat me silly or let me go.

When I got to the site, Joe was there. He said, "hello Jill, everything ok?" I smiled meekly and nodded yes.

"Okay honey, he said, now just take off what's covering everything. Tell me what you're wearing and fashion show it to me. Tell me about the perfume etc and what the whole week was like and we're through. Okay.

I asked him if I had to and he slapped my face hard and demanded, "YES."

As my face stung, I removed my jeans and shirt and stood there in everything telling him about the week. When I was finished he told me to take off the panty hose. As I removed them he told me to make sure that I turned and bent over so he could feel if I was wearing the butt plug and that I should make my voice sound as feminine as possible. Since I had sung soprano in the school choir and my voice had not really gotten deep yet, I was able to comply.

Standing there in the warm early June sun I turned wearing the bra and panties with my skin shaved. He rubbed my ass as felt the plug (I felt my penis stir a bit as he did this. I didn't know why) and grunted an affirmation that it was there and then slapped my ass as I stood and turned facing him again. He asked me what perfume I was wearing and I said in my most feminine voice, "I am wearing the Opium perfume."

"It smells very nice and feminine," he said. "Now show me how you shaved your crotch and explain what you did."

I pulled my panties open and showed him the patch of pubic hair that remained while explaining how I shaved myself. My voice was falsetto and I could hear how I sounded very girlish. As I stood there with my panties held open a cool breeze and my nervous soon found my dick harden a bit more. He smiled and laughed.

He picked up my jeans and shirt and threw them about 10 feet away. "And now for the final thing. So that you never, ever, try to take a girl from me, I want you to unzip my fly and jerk me off into your panties." As I started to protest, he slapped me again and said that he would take my clothes and leave me here if I didn't. He also said I was to talk to him as I jerked him off asking, better yet, he said, "begging him to cum on my little clitty." I was trapped. I was about to say something but he slapped me again. I thought, it would be over soon if I just do this now. At least I don't have to suck him off or anything. I can do this.

As I unzipped his fly he instructed me to hold my panties open and jerk him off with the other hand. Taking his cock out I realized how wrong I was. Soft it was at least 5" long and thick. I couldn't believe my eyes.

"Quite a beauty isn't it," he asked?

I held it in my hand ashamed as it began to grow. I wondered how big it would be hard. As if he could hear me think, he said, "eight inches and a handful thick."

Holding his cock and pulling it I realized he was tall enough that his cock actually higher then my navel. Jerking him off he smiled as I told him how "big he was and how I wanted his cum in my panties."

He felt my ass and played with the plug and petted my hair and head, as he grew larger and larger until his manhood was tremendous. He started to grunt and I knew he would cum soon. I looked down just as he shot his precum up and hit my face. The first load of spunk also shot up to my nose and dripped down eventually falling into my panties. I pushed his cock down and jerked the rest of his spunk down into my panties washing my 'clitty' with his cum. Actually it covered my little dick and a puddle formed in the cotton crotch. He moaned a bit more and finished cumming.

I let my panties go and they closed his cum around my balls and he whispered in my ear to finish by licking the head of his cock clean and then thank him with a comment and a curtsy.

Since it was just about over, I did what he said and leaned down and licked the last droplet of cum from his cockhead.

And then I let go, he stepped back a few inches and I curtsied saying, "thank you Joe for letting me have your cum in my panties."

I asked if I was finished and he said yes but one last thing would be perfect. Then he took his hand and rubbed my cum soaked panties against my balls and told me to mix my cum with his so would we "be united as one in this ordeal."

Unbelievably my little cockette hardened and before long I sighed as I shot my load into his load in my panties filling them with a soggy cum mess.

Sighing, I asked, "Can I go now?" (I was still using the feminine voice.)

The next thing I heard was Joe calling out, "Sean time to come out."

Sean came out carrying a video camera. Embarrassed I tried to turn but Joe grabbed my arm and told me to just stand still. Then Sean showed me the entire event. Nothing that Joe had said was filmed. Only his chest and below was shown. But everything I did was very visible and culminated with me shooting in my panties filled with Joe's cum. I started crying.

Joe put his arm around me and softly said, "Stop crying Jill. You know that Kelly dumped me last week. There's no way I could get another girl and the summer is here. So Sean and I thought you'd make the perfect 'Summer Girl' until someone comes around. You see, I like to cum three or four times a day. Kelly use to handle that for me and now you can.

He picked up my clothes and told me to put them on and they would walk me home. I said it was okay I could go home by myself. He slapped me and said, "Do you want a spanking? Just remember to say yes to my questions and act like a good girl and everything will be fine. Otherwise I will publish this flick on the Internet and email it to the whole school and send a copy to your college. So, put on your clothes and we will walk you home. I want to know exactly where you live so I can pick you up when I need you."