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High School Dilemma Ch. 01

By: LaurenWestley



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."


High School Dilemma Ch. 01



So, I put on my jeans and shirt and walked with them. The cum squished inside my panties as I walked and Joe made sure I kept talking (very girly like) about how it felt and how much I liked it and how I looked forward to his three or four loads a day. Sean just laughed as we walked through the woods to my house. They were amazed as they came to my house. We were on six acres of land. You couldn't even see our neighbors. The lot next to ours was empty and the next lot was still under construction. The other side of the house backed up against the woods and wetlands. "Fuck," Sean said, "this is much better then where we live. So this is how the rich live."

When we got to the kitchen door, I was saying goodbye when Sean said he had to, "take a leak." I let him in forgetting about my parents and everything and showed him the bathroom. As I did so, Joe stood in the kitchen waiting. I walked back into the kitchen and saw Joe reading the note on the refrigerator. I turned ashen white as he said, "Alone for two weeks. Hmmmm." Just as I started to protest Sean came back into the kitchen and Joe explained the note to him.

"Take your jeans and shirt off," Joe said.

"Please go," I said forgetting my feminine voice.

"Now you'll get a spanking as well for answering back and not using the right voice. NOW TAKE THEM OFF..NOW!" He slapped me so hard a fell against the refrigerator and landed on the tile floor. The cum oozed as I landed.

"Well," Sean said, "We are just going to be staying here the next two weeks so you'd better get use to it or be dead." His eyes showed the mean fire of intent. There was nothing I could do about it.

"Now get up and take your jeans and shirt off and lie over my ass for a spanking," Joe chimed in.

"You're going to be our live in girlfriend for the next two weeks," Sean laughed.

Crying I got up and removed my jeans and shirt.

"Oh look Sean, Jill has a puddle of cum that has stained her panties," Joe snickered and then slapped his knee for me to lie down for my spanking.

Both my cheeks were stinging hot as I stood there in the cum puddle filled satin panties and bra my soft white skin exposed and the two big brothers enjoying themselves. As I walked over to Joe my hips swayed as I moved with the butt plug and the cum puddle sobbing as I did.

"I like that walk Jill make sure you sway all the time. Make believe your knees are tied closer than your ankles," Sean chided. "Gosh, she sure is pretty Joe. I think this is going to be great."

I stood in front of Joe as he snickered and tapped his knee and then lay down in my bra and panties. "I think we'll just pull the panties down a little in back so you can enjoy the spanking and the cum at the same time," Joe said as he pulled my panties down over my ass but left them on. Then he began to spank me HARD. Over and over again his hand smacked my ass and I cried out and then started sobbing uncontrollably.

When he finished he said, "There you are Sissy, now stand up and thank me. Tell me you're sorry and will do your girlish best to be pleasant to me and my brother."

I got up. My ass was burning from the heat. I knew my goose was cooked. So, in a quivering little girlish voice I thanked Joe for the spanking and promised to be the best little sissy girl he had ever met. I would try to meet all his feminine needs.

"Ok, Jill, that's enough. Now show Sean and I around this mansion." We walked from room to room. Through dining room, living room and then into the game room that had a pool table and a card table when Sean said it would be great to have some friends over to play cards and pool. Joe agreed and said Saturday night was a great night to have friends over and since this was Saturday he would call some friends to come over later.

"That's ok with you Jill, isn't it," Joe said without expecting a reply. I asked it I could talk and Joe said Ok. So, trying to be very feminine and not get another spanking, I said how much trouble I would get in if there was mess or anything was broken. Joe simply replied that I would be in charge of cooking, cleaning and cum. "You know all those little girly things. That will make you a happy sissy. You can do all the housekeeping." Sean interjected that I would also do the wash. But that he expected his shorts to be hand washed and ironed since he was now on the right side of the tracks. Joe loved that idea and told me to do the same thing.

"Now, show us the rest of the house," Joe said as he put his arm around my waist and then lowered his hand to rub my ass as we walked upstairs. I showed him my parents bedroom and my bedroom, the guest room and finally my sister Jane's room. When we entered her room Sean immediately asked, "So this must be your room?"

I looked aghast but before I could say anything Joe demanded I show him all my things. Joe opened one drawer that had lots of sexy colorful panties and bras and asked if they were mine? I meekly replied, "Yes." Another draw had stockings and under them there was an electric vibrator. Sean laughed and wanted to know if I used it at night when I couldn't get some real COCK. He reached out and touched my scotch taped nipples and continued. That was the first time he had touched me and I shivered as I thought about it.

"What's in here," he asked as he opened Jane's large closet. One section had a whole bunch of slutty clothes. "Yes, these will fit you fine," Joe said as he rearranged the closet and told me I should wear what was on the left side unless told otherwise. Then we went into her, or as they said, my bathroom. There was a magazine rack with some girl magazines and Playgirl. Joe looked at it and told me to "be sure only to read such things from now on."

Sean came in carrying a pair of red heeled shoes and told me to put them on and to learn how to walk before tonight. There was a vanity with make-up, curling iron, rollers etc. On the right was a magazine opened to a page that showed how you could easily curl your hair. It was a step-by-step comparison with everything there that was needed. Obviously Jane had intended to try it out. There was a bottle of L'Oreal hair dye that was lighter then my own color. Both Sean and Joe smiled and told me that the first thing I should do when they gave me leave was to do my hair, nails, and face.

Opening the drawer on the left proved filled with packets of glue on nails. There were red nails, pink nails, clear, white and others. "I think pink nails and don't forget your toenails with matching lipstick should be good. Oh, and use these." Sean handed me a box that had a pair of false eyelashes in it.

Joe and Sean said they would look over the rest of the house. Since it was before noon, I was to take the next three hours and get myself looking real good. "Leave the panties on, we'll tell you when to change them and don't sulk. You don't have time and if you aren't ready by 3pm I'll bring my three Doberman's over and let them fuck you till you cry. Now, get ready honey," he said as they walked out of the room and closed the door.

As much as I just wanted to cry or run away I knew that if I left the house would be trashed. The pictures would be published. My parents would disown me. The only thing I could do was what they wanted and hope when my parents got back I could leave and go away for the rest of the summer: the rest of my life. With my panties stuck to my, what did Joe say I should call it. Oh, yes, either my 'sissy stick' or my 'sissy clit.'

They had left the door open and could hear them using the phone. I heard them call the market and place an order to be delivered. Then Sean was taking to some friends. I heard 7pm and my address.

"Are you getting ready Sissy," Joe called up from downstairs? While I followed the instructions and dyed my hair and then curled it, I didn't know that Sean had used the Jeep in the garage and gone home and returned. Putting on the nails and painting my toe nails I though back to just a week ago as I sat on the ground and Joe peed on my crotch. I should have known right then but of course I didn't. As dumb as I thought Joe was, it was obvious that his talent lay in sexual domination.

My panties stuck as the rollers did their thing, I pulled them out and then when I put my hands to my head I could smell his cum. Gosh, he had only cum one time today so far and I didn't know what Sean could do. The only thing I knew was that I was their 'sissy cunt' and would be such for the next two weeks.

Because of the smell of Joe's cum I splashed some more perfume over me. It was nearly 2pm when I removed the curlers and brushed my lightened gold hair. The whole thing had worked. I looked in the mirror and saw a feminine outline to my face. Then I put on the eyelashes, some powder and I had found on the page of the hairdo a bullet telling me to turn to page 32 for make-up tips with this hairdo. Again, Jane had everything I needed and since I had been in school plays and was a fairly good artist, I was able to copy what it said and by 2:30 my face and hair was a feminine as any girl. I stopped and was admiring my work and didn't notice Sean standing there. He smiled when I saw him and said he was pleased that I liked being their girl. I looked ashamed as I heard him. But then he said for me to close my eyes and not move. Before I knew what had happened I felt two punches on my left ear. He told me to be still and then I felt one on my right ear. He said for me to keep my eyes closed for another minute and when I was allowed to open them I could see two gold studs in my left ear and one in my right ear. There was nothing I could do.

"You didn't know I did piercing did you Jill you lucky girl," he said. Joe walked in amazed and walked over to me looking into the mirror from behind. Our eyes met in the mirror. "You're prettier then Kelly," he said. "Now one more thing," he said as he held my shoulders. Sean used something to open my mouth and hold it open. They were so strong I couldn't fight back and again before I knew it my tongue had been pierced and a silver ball with pin and screw on ball had been placed through my tongue.

"Perfect," Sean said. "Usually I get a couple of hundred dollars for this but you can pay me back somehow later. Ok, Jill?"

Joe reminded me as he said for the last time by whispering in my ear and I thanked Sean for taking such good care of me and making me pretty.

"Now don't forget with that pierced tongue," Sean said, "you can drive a guy crazy by rubbing it on his dick or when licking his asshole. A guy knows when a chick is doing her best and our friends who are coming over aren't very nice to chicks that don't do their best. As a matter of fact, Jimmy likes a girl who knows how to lick asshole so make sure you don't fuck up with him or anyone else."

The next thing I knew was Joe had lowered my bra and held me again while Sean pierced my nipples and put bars through them that held a chain that hung down. I was so shocked as I saw myself in the mirror. But before I even had a chance to think about all of this Sean and Joe told me to get up and lean over the bed. I was so submissive at this moment I went to the bed and leaned over right way.

"Good girl," Sean said as he gentle slapped my sore ass cheeks. He rolled down my panties and said to Joe to hold me. Before long he had put a tattoo on my left ass cheek, on my right ass cheek and one above my ass crack. (Later I learned my two cheeks said spank me and the words above my ass crack said, Piss & Cum In Here, with an arrow pointing down.) By 5pm a band of tattoo surrounded my ankle in a geometric pattern that actually repeated the word, "SISSYJILL." Just above my pubic mound was in small block letters--sissy clit.

Also in small letter on the back of my thigh below my panty line was the words in the wings of a butterfly and in color saying, "Pull my panties down." I would learn later what I couldn't read. And finally over my left nipple was the words, "I love(in the form of a heart) to lick ass."

I couldn't believe it. Joe and Sean had put some clothes on the bed and told me to be ready downstairs by 6pm. Joe whispered in my ear just before they left that he still had at least 3 loads of cum for me tonight.

I stood looking in the mirror at my ear studs; titty clamps with chain and then opened my mouth and looked at the silver ball through my tongue. Gosh in less than 7 hours look where I was. I went to the bed and saw what they had put out for me. There was a pink spaghetti strap camisole that no matter how I tried would not cover up that heart. The skirt was a skimpy black silk that didn't even cover my entire panties so that little design with "pull my panties down" was quite visible. A pair of white socks that had a frilly overhang and didn't cover my anklet tattoo. Also, I had never see socks like this because they were cut out so my pink toes showed. A black satin choker and black open toed shoes with thin straps up my feet with my toes showing. The shoes had heels but weren't as high as what I had been practicing in so I was able to walk in them.

There was Jane's tennis bracelet that I also put on and a pink butterfly clip for my hair. When I looked in the full-length mirror on the closet door I couldn't believe the slut I saw. Anyone sitting down could easily see my panties.

"Are you ready Sissy," Sean called from downstairs. "Come to the game room as soon as you are," he continued. I wasn't ready as a person but I had no choice but to go down. As I entered the game room Sean was filming me walking in. The skirt although not real tight felt like it would tear off if I took big steps so I was very careful as I walked in.

"WOW!" Joe stammered. "You are one fucking great looking cum magnet," Joe continued and then said harshly I should always be polite when a guy gives you a compliment. He raised his hand and I knew it was a signal. So, not to get smacked I turned to Joe and said, "Thank you."

"Ok, I love to get a good blow job right now," Joe said, but Sean said it would mess me up so soon before the guys arrived. Instead, Sean said, "why don't you give her a fresh load in her panties."

So there I was in my house totally different than earlier in the woods but doing the same thing. This time he had me use some Vaseline as I jerked him off. While I was doing this Sean put on some music and Joe's cock got hard as a rock. He wanted me to smell it and lick it a couple of times and then he held my skirt up and pulled my panties out. Sean just watched and Joe kept telling me what a good "little cum slut," I was.

The next thing I knew he was blowing another thick load of cum on my sissy clit and down into a puddle in the cotton crotch, which was filled with dry cum from earlier. As if on cue, as soon as he had finished and I had pulled up my cum filled panties tight against me the doorbell rang.

"Go answer the door Jill," Sean said. As I walked Joe's fresh load of cum slathered against my balls. I got to the door ashamed of my predicament and opened it. There were 3 guys standing there. In my pretty girl voice I said, "Hello, won't you please come in." One guy was nearly six and half feet tall. He was the last to walk in and he walked over to me, put his arms around me and said, "Hi Jill, I'm Jimmy." And before I could do anything he leaned down and started to kiss me on the lips and then pushing his tongue into my mouth. I could feel his massive cock against upper chest. I he was standing erect his cock would be almost mouth high. As he kissed me he played with my ass and then rubbed the front of my panties. The cum oozed around as he did that and he stepped back and with a smile said, "hmmm looks like you get wet easily." Then he saw the little heart over my left breast and said, "Well Jill, I love to have my assed licked so I guess we're going to have a great time together."

So, this was the Jimmy they had talked about earlier. The other two guys had walked in and were talking with Sean. Both seemed pretty fit, perhaps early twenties.

To be continued...



High School Dilemma Ch. 02



Authoress's note: of course all disclaimers are still in place regarding characters etc. This particular episode is very XXX with pee scenes etc. I suggest those who don't like this kind of story not to read on. I know I make both grammatical and punctuation mistakes. I promise all of you I will try harder every time to get it right. Hey what else can a submissive do? However, I do know many parts of my stories will not appeal to all of you. I only wish there is enough to make each of you happy. To those who have given me constructive criticisms as well as those with praise thanks. Lauren Westley.



Jimmy told me to get him a beer. As I turned to go to the kitchen Sean called out that I was to curtsy and say, "Yes Sir" when a man was talking to me. I turned back to Jimmy and curtsied saying, "Yes Sir." But, again Sean called out and reminded me that a proper curtsy was with my fingers holding the hem of my skirt and pulling the skirt out a bit. So again I curtsied and said "Yes Sir." 

Just then Joe chimed in and told me that since I wasn't a 'proper' girl that I should do a different type of curtsy. This he said would entail holding the hem of my skirt a little towards the front and when I curtsied I would pull the skirt up showing my panties and I wasn't to rise back up until the man gave me permission by either tapping me on the head or a verbal acknowledgement.

So again I curtsied but this time I held the front of my black silk skirt showing my cum soaked white satin crotch. My pink spaghetti strap camisole hung in such a way I knew Jimmy could see the chain going from one nipple to the other.

"Hey honey your pussy is really wet," he said as he grinned. And since I couldn't rise until he said so I found myself teetering on the red high-heeled shoes. Nothing seemed to match except for the sluttiness.

Finally Jimmy said I could get up and get him that beer. While I walked to the kitchen passing one of the other guys (I found out later his name was Paul) he stopped me and told me to raise the back of my skirt so he could see my tattoo better. 

It was at this point that I finally found out what was written. Out loud Paul read the words pull my Panties down. 

"Great tattoo Sissy Jill," he said. (Obviously he could read my ankle tattoo as well). Then he proceeded to pull them down as I held my skirt up. First he read out loud the words "piss and cum in here," with the arrow pointing to my hole and with enjoyment said he would be "glad to later." Then he pulled them down some more and read the two words, one on each ass cheek, saying, "Spank me." 

"Absolutely," he replied, "but just a little later." He began to pull my panties back up when he said to his friend, "Larry do you think I should keep her panties rolled down in the back so we don't forget what she wants?"

Larry replied with a quick "Yeah, sure Paul that's a great idea."

And then Paul rolled my panties down over my ass and left them in front with the puddle of cum against my "peni-clit" or "puny-clit" I'm not sure what he said.

"Get me a beer also Jill," Paul said. So I turned and curtsied with my bare ass against the black satin skirt and my white cum filled panties in the front waiting for him to give me permission to get up. He took his index finger and put it under my chin and suggested I should smell his crotch before I got up. My nose touched the fabric of his trousers at the base of his balls. "Sniff it boy-cunt," he demanded. When he wasn't satisfied with my nasal inhalation he grabbed my hair and pulled it and then I sniffed hard and long. I could smell masculine sweat, stale urine and a bit of a hidden musky odor.

"Ok, now you can get up and get me that beer. I just wanted you to get use to the smell of the perfume that should turn you on. When you smell this you can't be far from good spunk." Paul pulled my hair and I knew to get up. My curtsy finished I walked to the kitchen my bare ass being rubbed by the black silk skirt as my four-inch heels made my ass sway back and forth.

"She'll do nicely," Jimmy said to Joe as I turned into the kitchen. I started to cry as I got the beers. Four beers and four glasses I counted as I put them on the tray and started out to the living room holding the tray.

"No, No you twit," Sean yelled when he saw me. "You are waitressing us so carry the tray in one hand as they do at a bar." It was so difficult I thought I'd drop everything on the beige living room carpet but by taking smaller steps and going slower I was able to continue on. "Very sexy walk, I like it," Joe said.

For the next hour or so I just kept going from the kitchen to living room serving them as they watched a football game. Each time I served or picked up empties I had to bend over (the only way I was allowed), which made my skirt slide up over my ass revealing the writing on my ass.

The half came and I was serving Larry when he started to rub my ass saying, "Cunt, do you know how to fuck a cock?" I heard him ask Joe if it would be ok for, "the cunt to fuck the jism out of him?" 

Joe said, "sure" and the next thing I knew I was walking with Larry holding my hand to my bedroom. As we walked Larry kept sliding his hand under my skirt and rubbing his finger in my crack. By the time we reached the stairs his index finger was pushed up my hole. He told me to grind on his finger since I was going to "fuck the jism out of him" and should show him how much I wanted it.

Walking up the stairs was so precarious. Once I teetered a bit and slid down on his finger to his knuckle. He said, "good girl." We got to my sister's room and he complimented me on the pink and girly decorations. As he closed the door he said I was going to fuck him and he began to take his belt off. Holding the belt he continued that he would use it if I didn't smile and fuck him good. He turned on the radio next to bed and told me to dance a little and then come and feel his balls and when he was hard enough I was to fuck him. If I was "lucky he would both cum and piss in me." He got up on the bed with his pants removed and only his jockey's on and his shirt. The belt was by his side curled up like a snake.

Nervously I began to dance and turn, bending over and showing him my ass as he rubbed his crotch. I looked at him and he said, "cunt just look at the prize, my cock is full with a feminine present." He was very hairy as I continued to dance. After about five minutes he removed his shorts and told me to climb up and "suck him and fuck him."

I climbed up on the bed between his legs my eyes watery from the humiliation I felt. His hairy legs rubbing my soft hairless skin as my face rubbed in his balls. He was very musky smelling as I started to suck him.

"Good little cunt," he cajoled as he stroked my hair. My red lips sliding up and down on his shaft as his cock began to harden. He wasn't very long. At most 6 inches but his cock was as thick as a late summer cucumber. The corners of my mouth ached as I bobbed up and down as his cock hardened.

"Okay cunt now is the time for you to ride the rocket," he said with a smirk. I began to remove my panties but he slapped my face and said, "whore just leave your panties the way they are and fuck me." So with my panties rolled down in the back and cum filled in the front I held his cock and guided it into my (he made me say) 'pussy'.

Slowly at first his cock head began to push into me. I felt like I was being fucked. I felt like a cunt as his cock slid up my hole filling me with pressure and heat. He put his hands on my hips and said, "ride cunt." I was bouncing up and down on his cock my own 'clitty-cock' jiggling in Joe's cum puddle. Before long he started to breathe heavier and moaned, "fuck it out of me cunt. AHHHHHHHHH" and then exploded load after load of white-hot jism up my bowels, deep inside me.

He held my hips after he shot. His face was flush as he held me on his cock. "Just one more thing I need to do cunt and if you are the girl I think you are you're going to love it. He rolled me over with my face in the pillow. About a minute later, his cock softened but was still thick, he began to pee a torrent of urine up inside me. He rubbed my belly and told me this would be the first of many times he would "fill-her up."

"Now cunt when you get up don't spill a drop because if you spill any by accident, without permission, then your ass will be as red as your lips. Do you understand?" I nodded I understood. "Now when we walk back in the room I want you to look girlishly satisfied and have your fingers on my crotch. Everyone had better thing you are one happy little cunt. Oh, and fix your makeup before we go down. You need more lipstick."

I got up and felt his full load of hot piss and cum in me as I started to get off the bed. "Hey cunt, tongue wash my cock clean," Larry commanded as he slapped my ass. So I turned and saw his messy cock and moments later I had given him a tongue bath with my pierced tongue and now my mouth tasted like a sitcom and piss sauce.

"Ok now get some lipstick on and we can go downstairs," Larry said 

A tear fell from the corner of my eye as I applied the lipstick and tidied myself up. I turned toward Larry and he said, "Smile." So, I smiled and we walked out of the bedroom. I had to keep my ass cheeks squeezed as we descended the stairs. I could even feel myself slosh a bit inside. Larry stopped me on the stairs and then he pulled my skirt up in the back so he could see my ass. "Just to be sure you don't spill any," he said with a satirical tone. So we began down the last half of the staircase. Larry put his hand on my ass rubbing my cheeks and telling me how proud I must feel to be carrying his load. And then he had me put my hand on his crotch as we entered the living room. As we walked into the room I wiggled a bit to hold in Larry's pee and cum cocktail.

Larry said he liked that and I should get him another beer.

The game was back in progress so the other guys were sitting around the TV but I noticed Joey smile as he looked at my hand on Larry's crotch. As I walked to the kitchen Joey turned to me and asked if "Larry was a good fuck." I said "yes" and then politely asked permission to go 'potty'.

"Larry," Joey called out, "did you take a leak in Jill?"

"Sure did Joey and I told her she'd get a spanking if any of my piss or cum leaks out."

"Well Jill, Larry wants you to keep it in until he says so, so get me a beer also," Joey said.

During the next half- hour I waddled along carrying beers to the boys feeling Larry's wetness inside with every step I took. I held it in. Then while I was serving Joey another beer he started to rub my ass and said with a cynical leer that he 'need to use the toilet.' With that he took my hand and we started walking out of the room when I heard Jimmy and Sean said they had to 'piss' also.

"You lucky cunt," Joey said as he turned and made me walk to the sofa. He had me bend over the arm of the sofa with my pee filled ass exposed to them. I heard his zipper as my face was in one of the pillows. Next he grabbed my hair and I felt his cock push into my ass.

"Larry's piss is so warm, I can feel it around my cock. I'm getting so hard. Jill is going to be so lucky because now I have to cum first. And with that he began fucking me while pulling my hair. Before long I heard him sigh and then start grunting, "here it comes cunt." And with that I knew he had shot his load.

After a few moments, with his cock still hard I felt his pee torrent into me. He continued to sigh, "AHHHHH" as he peed.

Then Jimmy with his massive cock did the same. I was so full my tummy pushed hard against the sofa's arm. When Sean started to fuck me he told the boys I was too full and Joey gave him something. He said when "a dike is full, plug it." And then he laughed while I cried. Just before Sean came he pulled out and stuck something in my ass. Later I realized it was a butt plug. He shot his load in my ass crack and told me to pull up my panties and follow him.



High School Dilemma Ch. 03



(Authoress's note: of course all disclaimers are still in place regarding characters etc. This particular episode is very XXX with pee scenes etc. I suggest those who don't like this kind of story not to read on. I know I make both grammatical and punctuation mistakes. I promise all of you I will try harder every time to get it right. Hey what else can a submissive do? However, I do know many parts of my stories will not appeal to all of you. I only wish there is enough to make each of you happy. To those who have given me constructive criticisms as well as those with praise thanks. Lauren Westley.



Walking with Sean was an ordeal I was so filled with cum and pee and the butt plug pushed even harder on my bladder. I didn't know where we were going until we got to the kitchen.

"Where are the glasses," Sean asked?

I pointed to the cabinet. Sean walked over and found one of those big beer glasses. You know the kind they give you at a brewery. This one had "Budweiser," etched into the glass

Sean said, "Perfect, " as he took the glass and instructed me to get four more beers from the fridge for the guys. Then he walked out of the kitchen with the glass leaving me to my misery.

I opened the refrigerator door and saw what remained of the beer Jimmy had brought over. It was on the lower shelf and I had to bend down to get it. I didn't dare deep knee bend so instead I bent at the waist and felt my skirt ride up and the plug trying to push out of me. Walking back to the living room with the tray of beers I felt the pee inside me sloshing around. I worried about an accident and also felt emotionally like crying. Joe's cum was drying against my balls and tiny penis.

I heard Joe on the phone in the living room saying, "Sure, come on over. The more the merrier. We have a great little cunt bitch here for fun and games."

So quickly had I sunk into depravity? I didn't even hear Sean when he called me over. He was standing there with his flaccid cock hanging out through his zipper.

"Come over here Jill," he beckoned me with the glass in one hand.

As I waddled over wondering what the other guys were thinking when they looked at me Sean lowered the glass and dangled his penis into the glass. Sean started peeing a good steady stream and the glass turned from clear to dark yellow with foam forming at the top of his piss. In horror I watched knowing what would come next. My throat was dry but not from thirst.

When I got over to where Sean was he was almost through peeing. The glass was full with piss and suds to the brim. Paul commented how it looked like dark ale. Sean handed me the glass saying, "This Bud's for you," and then commenting how since the toilet was full there should still be room in the urinal.

My long fake pink nails wrapped around the warm glass and my stomach gurgled.

"This is the finest filtered lager Jill. We drink the beer and then we piss it out for you, our little slut sissy girl. So smell the brew and then drink it down," Sean mockingly said.

The pungent odor stung my nostrils as I inhaled.

Sean put his hand on my tummy saying, "There's plenty of room in here girl."

I brought the glass to my quivering lips taking a little sip but Sean told me to take a gulp. The acrid taste coupled with what it was going in my mouth made me nearly puke. My tongue piercing clanged on the glass

"Drink it all down right now," Sean said, "or I'll put a shit floater in there."

Scared, frightened and terrified I drank. Sean's piss was washing down over my tonsils and drowning my throat as I was coaxed to chug-a-lug. Down, down, down burning a pungent path into my stomach. I felt bloated. My stomach began to tighten against the waist of the little black skirt I was wearing.

Even though earlier I so wanted to empty my bowels I wasn't allowed to but for the next half hour or so they didn't bother me either. Sean's piss was working its way through my system into my bladder, which pressed against by the other pee inside me. Inside their, "toilet." Who knew how perverted these guys were? I can't imagine what they plan. 

That's when the doorbell rang and Joe told me to, "Waddle over there and see who's at the door Jill?"

I was sobbing as I walked to the door. The little bars through my nipples ached under the pink spaghetti strap camisole. And I had to look down so as to not fall down in the black open toe heels I wore. My pink toenails and pink fingernails visible. Inside I hoped the tattoos were done in washable ink. At least Sean had said they were something that would wear off in a week or two. And as soon as this was over I'd remove the tongue bar and the nipple piercings. The pierced ears I could either remove or simply wear them since guys did that now. My urge to pee was growing dire.

With my hair blond and curled coupled with my diminutive size I felt like a girl as my hand turned the knob of the door. Talk about shock and awe. I opened the door and their standing on the stoop was an old fat guy and a midget. The fat guy was carrying two cases of beer and the midget had a bag.

The fat guy said, "You're the little sissy girl my nephews told me about right?"

I tried to stammer "yes," but words wouldn't come out.

As they walked inside Joe called out, "Is that you Unc?"

"Yeah, it's me and Tiny," his uncle replied.

Tiny put his hand on my thigh and I started to back away.

"Joe, I thought this sissy girl was trained. She just backed away from Tiny's touch," his uncle called out, as the three of us were so close to each other in the small vestibule Joe's uncle's belly grazed against mine.

Joe screamed out, "Bitch you let Tiny do whatever he wants and anyone else or you will find these past hours to be a walk in the park."

Tiny reached back under my skirt. I was frozen in place. Uncle pushed his belly past pushing me a bit into the wall as he walked into the living room.

Tiny's hand came around touching my butt plug that caused me to moan from the urgency to need to pee. He directed me to walk into the living room as he handled the plug. I was mortified.

"Hey Joe why does the sissy have her pussy plugged," Tiny asked?

Almost at the same time Unc was picking up my piss glass from the coffee table.

Joe said to Tiny, "Ask her Tiny."

"So sissy why did you plug your pussy," Tiny asked me?

He had let go of my thigh and was now right in front of me. I was hesitating answering out of extreme embarrassment when Jimmy walked up to me. 

Pulling my hair so my ear was pressed against his lips Jimmy whispered in my ear saying, "If you don't answer every question asked truthfully and in a sissy voice I'll shit down your throat and sissify your larynx into submission. Now answer the man."

I tried to answer but my throat caught all the words and what came out was barely audible.

Whack!

Jimmy slapped my ass hard whispering, "Start your answers with 'Sir'."

I felt the pee sloshing inside me as my ass stung from Jimmy's hard hand slap across my ass. I wondered if Jimmy could feel it? What did the other guys think? Who am I?

"Sir, my ass,"

Whack!

"You don't have an ass anymore pussy girl," Jimmy snarled in my ear.

"Sir," I said to Tiny feeling the roots of my blond curled hair being pulled taut by Jimmy holding my head to his mouth. It felt like a thousand bee stings, "My pussy is plugged because the men fucked me and filled me with their cum and pee until I was full."

"So your pussy is full with man piss," Tiny asked?

Jimmy whispered in my ear what I should say and also reminding me at each step that my voice should be a submissive sissy tone.

"Yes Sir," I answered with a sissy sound from my mouth.

Continuing as Jimmy instructed I said, "My pussy is also a toilet. My toilet pussy can only hold plenty of cum but only three man loads of piss so until I learn to hold it without leaking I need to wear a pussy plug for training. Someday I'll proudly carry three man loads without a plug."

My heart was sinking as the thought of many times being filled with pee would be a reality for the next two weeks.

It was right about then Unc held my glass up and asked, "Whose glass is this?"

Jimmy was still instructing me what to say.

"Oh,"

WHACK!

"Sir," I answered in my new sissy lilt voice, "it's my piss drinking glass."

"So you like to drink piss too," Unc asked?

WHACK!

"Yes Sir, man pee is tasty beer to a sissy," through my tears I answered.

With more prodding from Jimmy I continued, "But I can only hold two full glasses of pee in my girlie tummy at this time."

"I'll bet you have a magic marker somewhere around here," Unc said and then he instructed me to go get it.

Jimmy let go of my hair and slapped my ass one more time. More of a slap you'd give a girl when she was sent to go get something so it wasn't very hard just a light sting but it was humiliating.

I started to waddle off to get the marker when I heard Larry say, "She walks real sexy. Do you think it's the piss or the plug?"

Sean answered, "Well it's probably both right now but I'll bet when she outgrows the plug and has a good filling she'll have a great sexy sway."

I was crying inside. Scared of doing what they wanted but more scared of Jimmy's threat of shitting down my throat I walked to the kitchen to find the marker. 

Inside I knew I had now traveled to far down this road to escape and it was only the first day. 

In the kitchen I found the marker. Leave it to my Mom to have bought a magic marker in 'hot pink'. Carrying it back I knew someone would make a wise crack about it.

Paul didn't talk as much as the others so I was a bit surprised when I was walking back to hear his voice directed at me. 

"The best way for you to walk girl is to put one foot in front of the other like a runway model but not so pronounced. That will help you both from a feminine perspective and also if you squeeze your vagina tight you'll be able to hold our cum and piss without leaking."

I handed Unc the magic marker.

He handed it back to me with the glass saying, "Now print this neatly on your glass."

PISS IN HERE

JILL

I knew the consequences but I was also in too deep. I handed the glass back to Unc with the words as neatly printed in hot pink.

"Joe, I think our little sissy girl should be clearing the empties and properly serving us," Unc said.

"Great idea Unc," Joe replied and then he turned to me saying, "Jill while you aren't being used you should be serving and cleaning up. Sweep the floor, clear and wipe the table. But stay busy."

This was my own house but now I was the maid as well as their slut. My panties were stuck to my balls. Joe's cum had completely dried. I hadn't even thought about the loads of piss and cum still deep in my ass. The plug was becoming second nature. But my need to pee was also becoming more urgent but still I wasn't given permission to use the bathroom.

I cleared the empty bottles, wiped the table and brought the guys beers. Tiny had brought a handle of Wild Turkey in the brown bag. The guys were getting drunker and I was having all sorts of feelings. The chain linking my nipple bars had just the right movement and weight to remind me of my nipples nearly all the time. I wondered if that's how a girl felt.

When I came back into the living room I noticed my glass on the table filled with dark urine. I cringed inside. 

Unc noticed my face and then said, "Go ahead girl drink up."

I didn't want any 'shit floater' or whatever else Jimmy had in mind so I picked up the glass. Again I could feel how warm it was. I knew I was supposed to sniff it so I did and it was even more pungent as the glass before. 

Unc asked Joe where I had learned that to which Joe replied, "Oh that's just something she likes to do. She wants to become a 'piss connoisseur'. Several of the guys guffawed over that comment. Tiny mentioned I should keep a journal of the smell and taste of piss.

As I tilted the glass back and I could see some of the magenta print, "Piss in Here, Jill." I was ashamed as the men watched me but the most embarrassing moment came as I was drinking the glass of pee when Tiny quizzically asked, "Is your pussy leaking sissy?"

Unbeknown to me since I was so distracted by everything else my bladder had started uncontrollably leaking pee out of me.

"I asked you sissy are you leaking," Tiny asked more stridently. 

Jimmy glared at me.

"Yes Sir," I quickly answered in a voice strange to me but now the only one I was allowed.

Although I couldn't see it I was now aware of the pee dripping through my cum filled panties and puddling on the floor. Once it started I couldn't stop it. I just peed. The flow became more constant. A steady stream

"Keep drinking sissy," Sean said.

So the warm piss washed down my throat as I peed. I wanted to vomit but instead I simply dry heaved into the glass of piss making it so much worst. 

Fortunately I wasn't on the carpet when I lost control of my bladder but instead standing on the wooden floor.

"Well Sissy you are definitely a girl. Girls often have accidents so get use to it. It's something to do with the length of your urethra to your bladder. Don't you wish you had a penis?" Sean taunted me.

"Yes Sir," I answered.

"Yes Sir what Jill," Sean taunted.

"Yes Sir I wish I had a penis," I answered.

That's when Sean began telling Unc and Tiny how I really didn't have a penis but instead a slightly enlarged clit.

"Girl we have to see that," Unc said. Then he continued with, "go get some towels to soak up your accident first."

Now I'm sure some of you are wondering why I didn't just run away by now but remember this humiliation had begun a week ago and it just seemed to progress beyond my brain thinking of any alternative other then Jimmy's.

I found some brown towels in the linen closet and brought them back.

"Just drop them on your pussy juice," Tiny said.

A few minutes later I was standing there on the edge of one of the towels with my panties to my knees holding my skirt up as Unc and Tiny examined my clit."

"Wow that's small," Tiny said, "and you say it doesn't get much bigger then a pinkie when it's erect?"

"Yep that's right isn't it girl," Joe said.

By now I knew I need to answer quickly and more then just a yes so I said, "Yes Sir my clitty is just a nub." 

I had read that some girls call theirs a nub. I wasn't sure of the complete meaning but it met with approval. And at this point I was beginning to try to win approval since I thought it would mean an easier circumstance. However the next moment proved otherwise.

"Hmmm...those towels are perfect," Sean commented. "Kneel down on them and stick your pussy up in the air Jill."

I didn't think I had hesitated but Joe slapped my face almost as hard as the first time a week ago when he said, "don't" when he was peeing on my crotch.

I knelt down.

"On your elbows, face in the towels," Joe said.

My naked ass was high in the air and my face was in the pee soaked towels. Pee from two men and a sissy.

WHACK!

WHACK!

Two hard slaps across my bare ass got my attention.

"We are going to remove the 'toilet plug' girl," Joe said. For a nineteen year old man he was quite sexually deviant. "Don't let the toilet overflow no matter what," he said mockingly.

I felt the plug slowly open my hole as the fat end started to be pulled out. I felt like I was going to explode.

"Remember, squeeze those vaginal muscles as your pussy plug comes out," Joe laughed.

PLOP! it was out and I was squeezing my sphincter or as Joe said 'vaginal' muscles closed when suddenly someone started slapping my ass. Harder and harder they slapped. I started crying and then I couldn't hold my hole closed anymore and all the pee and cum just shot out of me.

"Stop that girl," Joe said.

I tried but I couldn't I cried and cried and felt relieved. Finally I had stopped flowing pee and cum.

"You've been a good girl," Joe said, "go clean up this mess. Wash everything. Take a nice hot bubble bath and when you come out we'll see what you should wear for tonight.

I picked up the heavy towels and sulked away. Shortly after the washer was churning the towels through detergent and I was naked in a warm bubble bath. As told I left the door open to my sister's room and her bathroom door. I was not allowed to close doors. I could hear the deep male voices downstairs. Though I couldn't hear what they were saying I wondered if it was about me.



High School Dilemma Ch. 04



(Authoress's note: of course all disclaimers are still in place regarding characters etc. This particular episode is very XXX with pee scenes etc. However, I do know many parts of my stories will not appeal to all of you. I only wish there is enough to make each of you happy. To those who have given me constructive criticisms as well as those with praise thanks. Lauren Westley. 

*

A bubble bath is one of the truly feminine moments one can have privately. I luxuriated in the hot water cleansing all my earlier sins. When I lifted my leg out of the bubbles I noticed how very feminine the curves on my calves were. I had never paid attention to that before. But with my blond hair now gone from my legs it seemed as if a woman had attached herself to me. Lathering the soap in my hands I rubbed my leg and the smoothness was distracting.

I don't know how long I bathed but it seemed like forever. When I washed my ass I thought back to what was earlier inside there. For a moment it felt like I was rubbing my pussy. That's what they had said it was. And now I had two weeks to be what? A pussy? A TV? A TG? I wasn't sure anymore only that there were a number of men downstairs who got hard playing with me and liked to cum in and on me. In one brief moment I felt there was power in making a man cum.

Distracted I hadn't noticed Joe standing in the doorway watching me.

"I see you are beginning to enjoy this," he said. 

When I turned I found I instinctively slid deeper into the bubbles.

"Anyhow, when you are done you will find a pair of panties and heels on the chair by the bed. That's all you need to wear tonight. Make sure to make yourself extra pretty and don't forget what you've already learned," Joe said.

Then he left. It was almost a dream except I was in my sister's tub and I knew the past day, the past week, was real.

I got up and drained the tub while drying myself. There was a full-length mirror where I looked at myself. Except for my tiny cock, now just a large clit, I really looked like the girl next door. Also it seemed as if the tattoos were already fading. I wondered if it was my imagination or that Sean had told the truth.

Looking in the mirror I saw the small writing on my left breast saying, "I love to lick ass" and the chain connecting the two nipple bars. Sticking my tongue out the tongue bar looked so gay. I couldn't read the ankle writing but it was easy to read "Sissy Clit" just above the base of my penis.

Getting the hand mirror I focused on my back. The little butterfly with the words written in a half moon above said, "Pull My Panties Down." Not far below and just above my ass crack were the words, "Piss & Cum" on the horizontal with "IN HERE" below with a stub arrow finishing just in my ass crack. Lower down on my left cheek in large script it said, "Spank" and on my right cheek, "Me."

Well my reddened ass simply verified the words. 

I held me ass open to see if I had any damage. There was none. It looked normal.

In the bedroom I found the white satin panties. The front was shiny satin and the inside crotch was cotton. I wondered why as I held them up. Turning them around I could see the backside was very sheer. See through actually. Sliding them up my legs it felt sexy. My clitty (I needed to focus on that if I didn't want to get in trouble) hardened a bit and that made my cheeks flush.

Back to the bathroom and the small vanity I went, I sat down and looked at the 10x mirror on its stand. A touch of a button and a ring of soft light shined on my face. Gosh it seemed weird how big my pores were. I had sat here earlier but this time was different. I'm not sure exactly why but it was something along the lines of, 'been there done that."

The chain pulled my nipples just a bit each time I moved. I thought of Joe's words, "make yourself extra pretty," as I started to put foundation on watching myself change to even more girly. The hardest part was the eyeliner pencil. The second hardest was getting the lipstick right. 

Fortunately my sister had some index cards with what to do. She was always impeccable in how she looked and I guess this helped her get ready. I hadn't used the mascara before or the funny thing to curl your lashes. But I figured I'd better do everything really well or else Sean and Jimmy would do something worse to me. Finishing up with the lip-gloss I stared in the mirror. It was a transformation. When I finished brushing my curls there was no way some the neck up someone would think I was a boy.

Perfumed and in heels, pink toenails and fingernails, all dolled up I walked out of the room and headed downstairs. If was night and I could hear the men laughing and talking. The TV had some sort of game on but as I came downstairs a couple of the men turned from the TV and whistled. I had arrived for their pleasure tonight.

There in the room was Joe, Sean, Larry, Paul, Jimmy, Tiny and Unc, oh and of course me.

"Hey Jill clean up this place and get us some more beer," Sean said.

Just the word 'beer' made my bowels growl.

Now my house isn't one of those immaculate places but still the empty bottles in the living room was a bit of a mess. At least they had me stay on top of it so I didn't mind cleaning up and bringing them beers. Turned out they were watching a baseball game. Was only the second inning but they were engrossed and they didn't bother me when I brought them their beers. The refrigerator had whittled down their stash and it was nearly nine pm so I figured they'd be going home soon or at least when the game was over. Besides the beer I only had some celery and carrots in the fridge. I hadn't gone shopping yet. I was hungry and figured I'd ask if I could eat something.

"Sir," I said to no one in particular, "I'm hungry may I get something to eat from the fridge?"

Sean answered, "What do you have in there? We're getting hungry too."

"Sir, there are only carrots and celery," I replied.

"Haha, real girl food. Go ahead and help yourself," Sean said.

As I went to the kitchen I heard Sean ask the other guys something about Pizza. When I was in the kitchen eating celery and carrots Joe's voice echoed in. Joe has a deep penetrating voice. I thought I heard him ordering a Pizza. This meant they'd be here for a while.

I had finished eating my celery and carrots when the doorbell rang.

"Sissy go answer the door," Sean commanded

My stomach churned again thinking it was the Pizza delivery guy. Someone who came to our house regularly and here I was in just white panties and heels. The bell rang again.

"Hurry up Sissy it's our Pizzas," Sean called out.

I knew I'd better do it. I had done so much already what choice did I have. I walked to the door with one foot in front of the other knowing my ass was swaying for the men to see. But at less I was empty and no plug inside.

Opening the door I gasped for air. It was some guy holding three boxes of pizza.

"Hey Jill take these," he said handing me the pizza boxes

I carried them in with the smell of pizza wafting through the house wondering how he knew my name. And almost as soon as I had put them down in the kitchen the guy at the door was in the kitchen too with two 24-can packs of Budweiser.

"So Jill you're the sissy cunt my nephew was talking about," he asked?

Without hesitation I answered, "Yes Sir."

"Put these in the fridge," he said pointing to the beer.

While I was putting the beer away I heard Joe talking to him. "Jim, you rock."

As soon as I was through I went back into the living room.

"Spin around girl. Let's see what you've got," Jim said.

There were hoots from the guys as I spun around and when I was finished Joe pointed to a spot where all the men could see me and told me to dance like I was a stripper till I was told to stop. Now I was a pretty good dancer so it wasn't too hard for me to mimic stripper dancing. While I was dancing Jim opened a paper bag and I saw some papers and a bag of weed fall onto the table.

"Give us some crotch action, Show us how you want dick in your pussy. Tease us," Joe instructed as Jim began rolling a joint.

It was then I remembered what I was here for as I spread my legs and pushed my hands between my thighs pushing them out and dancing like a whore stripper. Jim lit up the joint and brought it over to me. Jim was about 5'10" medium build with long brown hair in a ponytail. He had me take a hit.

"This should make tonight go better for you, " he said.

A couple of hits and I was stoned. The third hit instead of me puffing on the joint Jim leaned into me kissing my pink lips pushing his tongue into my mouth and when it opened exhaling into my mouth. I was stoned. A man had kissed me and it went from repugnant to interesting in just a few seconds.

Jim stayed with me as the other guys started lighting up joints, drinking beer and hooting about Jim kissing me.

Looking into Jim's grey eyes and pretty face I was lost until he said, "You're going to fuck the shit out of me tonight girl."

It brought back the comment of Sean's about a 'shit floater' and Jimmy's 'shit down your throat.' All the talk of shit just made me cringe inside and act more girlie outside.

He took my hand and placed it on his crotch. I could feel his balls and penis.

"Bet you'd love to suck this cock and have a hot rod in your pussy. Right?"

Didn't take much but that word shit to get me to answer in my sissy voice, "Yes Sir I'd love to suck you cock and feel it cum in my pussy."

Jim pulled gently on the chain and my nipple pulled out a bit.

"So you like my cock right now. Right Sissy?" he inquired.

"Yes Sir," I answered.

"Then unzip my fly," he said.

My fingers gripped his zipper. The metal purred as I unzipped him.

"Reach in and find the man your lips were made for," Jim said.

As I fished his cock out of his pants Jim put a hand on my head pushing my blond curls sending a signal to my knees and I folded to the floor. When I saw his cock I was amazed how it had a small mushroom head.

"Lick it."

I did but as my tongue surrounded his mushroom head the thought of anything like this being in my ass, I mean pussy, was frightening.

Jim played with my ears saying, "Nice earrings Jill. Now make love to my cock. Close your eyes and suck me off because you want my cum. Oh, and don't pretend because I know the difference between a girl who loves cock and a faker."

Well I was pretty stoned so I closed my eyes and started to suck his cock. I thought about a Popsicle but his dick wasn't cold. I thought about a bratwurst (it was thicker then a frankfurter) but no one sucks a bratwurst. And then something happened. I felt his cock throb. It was a completely different feeling. It was alive and in my mouth. My mind wandered for a moment in a trippy sort of way but when his fingers ran through my hair the reality came back. I was sucking a man's cock. I had done this already earlier today, several times. But unlike earlier this was gentler. I didn't mind it. Was I becoming a girl?

His cock grew larger in my mouth and I was expecting him to cum but instead he pulled up with his hands stopping me. When his cock came out of my mouth he held the joint to my lips. I inhaled.

His voice fell from above with the words, "You are going to stand up, dance sexy for my cock and slowly remove your panties. Then you'll use some lube and fuck my cock. I want you to learn how much your pussy desires cock. All cock. Every action from you will be a demur bitch in heat. That's all you will think about tonight."

He raised me up slowly saying, "you will play with your pussy when you fuck me and have a good clitoral orgasm at the same time my sperm is swimming up inside you."

Someone had put on Suzanne Vega "As Girls Go,"

I took another hit and started dancing. My maleness was fading away as I wooed the boys with my moves. But most I was teasing Jim. Grinding into him. Rubbing his cock with my panties. Where the music had come from I don't know but if you heard the lyrics."You make a real good girl as girls go. Still kind of look like a guy I never wondered why. What happened to you to make you more girl then girls are."

"Go ahead girl. Wiggle that ass. Jill if you are going to make it through the next two weeks as a girl you need to use your girl brain. You know how girls wiggle their butts and then use their thumbs to pull their panties down don't you," Jim said as I danced.

When you're in the deep end of the pool you can only swim so I answered, "Yes Sir," and continued dancing.

"You're in store for plenty of cock over these two weeks Jill. All of us have friends whom you'll meet and fuck," Jim continued.

Another hit on the joint and I was so high my mind twirled as I spun like a girl and wiggled my ass bending over like I had seen girls do in porn flicks.

Whack!

It wasn't too hard a whack but it did sting. 

"Girls like you enjoy having their ass spanked a bit. Right?" Jim snickered.

I didn't know if it was a rhetorical question or not but I didn't want to take a chance so I squeaked out a "Yes Sir."

The other guys were remarking Jim on his training methods. I bent over again wiggling my ass as instructed.

Whack!

It was the other cheek. I don't think it's what Jesus had in mind.

"A little slap here and there should make your ass tingle and your pussy wet for dick Sissy. Right?" Jim asked.

"Yes Sir," I answered.

This went on for another 10 minutes while Jim would either slap my ass or feel my ass. I couldn't figure out why girls liked to be spanked. For me the humiliation didn't feel very sexy. However being stoned I was really feeling girlie as I danced and even more when I was bent over lowering my panties. I guess even Jim noticed because fondled my ass and I felt his cock touch my ass.

I lowered my panties a bit more and felt Jim's finger go to my crack. I wanted to pull away but at the same time Jim said for me to do the opposite. A moment later he had me palming my 'clit.' The odd part about all this, and perhaps because I was stoned, was my little penis started to get hard. I thought it was from the satin panties but in between my stoned thoughts I realized the panties had a cotton crotch so it couldn't be that.

Jim's fingered rubbed down further and as I rubbed I lowered my panties more still rubbing either on Jim's finger or cock. He was using both and also giving me hits every now and then. I couldn't remember how many. It was like all the time but of course it wasn't. Also Jim was treating me differently. He was rubbing my neck, lightly pinching my ears, stroking through my hair. All the things a guy would do with a girl. His hand touched my thigh once and it was electric. I also could feel his size versus mine. I was drifting into being a girl for him. It was so much better then earlier in the day.

And I was most surprised when he leaned down and said for me to keep wiggling because he was going to get some lube since I might be a bit dry. The kindness made me want to be more feminine.

I knew my ass was facing the other guys but they had another baseball game on. It was a night game. Pizza and beer aroma filled the air. I was still a bit hungry. Jim returned and had me only pull my panties down enough to "expose my pussy" for him. I felt this cool lubricant and his finger rubbing my ass.

"This is 'Glide' Jim said in whisper leaning over to my ear. "All girls get dry so I've brought a bottle as a gift for you."

A 'gift' for me. Thoughtful.

Then I felt his finger enter my, oh well stoned and Jim, my pussy. He began to fingerbang me and slowly added another finger and another stretching me until finally his cockhead touches my hole.

"Now girl fuck me," Jim said.

Well he didn't have to say anymore. I slid my ass back gently feeling him entering me. He gave me another hit and his cock went deeper.

"Like a good ponygirl Jill you will ride my cock and when I feel you need to ride a bit faster I'll spank your ass," Jim said as his dick finally reached so far in I thought he was in my tummy.

So here I was riding a cock like a girl. Fucking him. And every now and then when I slowed down he'd spank my ass and I'd speed up.

"Good little sissy," he'd coax me.

"Rub your pussy on my cock," he'd state.

The whole time he didn't move. He just was standing there while I did the work. I was fucking him. I wanted his jism he'd say to me. And then just as he was about to cum he cracked something and put it under my nose telling me to inhale. My heart started racing. I wasn't sure of anything other then Jim's cock deep inside me and the warm wetness his cock was oozing into me. Oh and me pushing hard back onto his balls as he came.

But something else happened at the same time. My hand had been rubbing my nub during the whole process. I didn't even realize it until I felt wetness in my palm. Amazed and sort of to myself but I was so stoned I said it out loud, "I came."

"Good girl," Jim said.

His cock still in me he grabbed my hips and held me tight to his cock whispering again in my ear as his dick began to soften, "Now I understand you're the type of girl who enjoys her hole filled with piss. Is that true?"

Shamefully I answered, "Yes Sir."

And just as I was finishing the word he began to pee in me. It was a warm full flow mixing with his sperm. Jim gave me a final toke as he peed in me. I was so relaxed I his flow felt like it was going to some deep dark region in me. He peed and peed more then any of the guys earlier. I didn't have a plug.

Jim's final whispers in my ear were, "You are a good girl Sissy. Now when I pull out I want you to pull up your panties and walk over to the other men. Proudly tell them how much you enjoy my cum and piss. Ask Joe when you are given permission to empty yourself you would like to go in your glass since you want to drink it down. Don't forget to animate 'proudly' when you go over to the men. Jiggle. Wiggle. 

He pulled back out a bit. He mushroom head still in me and then he peed a bit more.

"Squeeze tight now honey and hold it all in. Don't leak any."

As his cock head pulled out I was squeezing down both ashamed and sated. I pulled up my panties sticky with my cum now washing against my balls. I had never had a better orgasm in my life. I could tell from the amount of sperm in my panties it had been my biggest load ever. It coated my clit too.

And so the next part of the evening began as I walked the short distance over to the men who had been watching.

"I told you she was a she-slut," Joe snarked.

Larry saw my eyes looking at his tented khakis. "Yes girl, I have a load in my balls for you," Larry said. I'm not the lover Jim is. I like it rough and degrading and I think you like it anyway you can get it. Am I right?"

My heart sank as I remembered there were eight men in the room, nine cocks, and how many sexual permutations impossible to discern.

"Yes Sir," I answered in my stoned sissy voice.

Now my sissy voice was definitely an octave higher then anyone here but at the same time it didn't have the tone of a real girl. The only similarity was ending the last syllable on an up note.

"Well why don't you start answering with more then just a "yes sir." Instead repeat a bit of what is asked of you," Larry said. "Go on."

I tried to think what he meant. My head was swimming from the pot and poppers but I struggled out in sissy, "Mister Larry, I like it anyway I can get it, Sir" The 'Sir' at the end of the sentence just slipped out having heard a girl in my class once talk to a teacher that way.

"That's a great idea Larry," Sean said. Joe agreed and then they all did. I had a new directive. Answering with Mister whomever and ending on Sir with some thoughts in between.

"So tell us about sex with Jim," Tiny asked? "And elaborate."




High School Dilemma Ch. 04



What could I say, "Mister Tiny, Mister Jim taught me girls like me enjoy being spanked while fucking a cock. Mister Jim also taught me sissy nubs could get excited. Mister Jim (I figured I'd better not use he) taught me how to love a cock in my pussy Sir."

"Hey Jimmy, when you wife left you a few months ago didn't she leave her wardrobe?" Unc asked.

"She sure did and I think pussy girl here is about the same size as she was. She had tiny tits too. Double AA. I think sissy here maybe bigger up there," Jim said.

"How about we go over their guys? There's more room and bit more secluded. Plus we won't have to worry about any neighbors' accidently showing up. Isn't that a great idea Sissy?"

More then a little worried I started to say "Yes Sir" when someone slapped my ass.

"Mister Unc, I,"

Whack!

"You are not an I," Paul said. "You are a 'sissy girl."

Besides the fear of the floater nine fairly mean looking guys surrounded me. Outnumbered and outgunned I replied, "Mist Unc, sissy girl would love to go to Mister Jimmy's house, Sir."

"Then it's settled," a chorus echoed.

I wasn't even asked to clean up just to make sure everything was back in order. So I checked all the rooms. Put the towels in the dryer and met them back in the living room. They had cleaned up everything.

"Sissy girl wiggle your sexy butt out to Jim's car. He has it all warmed up," Joe said.

So in high heels, white panties, pink nails, tit bars and chains, lot of tattoos and earrings I headed out to Jim's car. The men followed. There were three carloads of men as we left my home. I was sitting in the back seat middle between Joe and Sean with Jim driving. Unc and Tiny were in another car and the rest of the guys in a big SUV.

As we started to drive away Joe turned to me, "Look what I brought," he said showing me the glass. "Didn't want our girl forgetting her Jim cocktail. It was then I remembered the cocktail that was gurgling up inside me.

(part 5 to follow)



High School Dilemma Ch. 05



(Authoress's note: of course all disclaimers are still in place regarding characters etc. PLEASE DON'T READ THIS IS YOU HAVE AN AVERSION TO PEE SCENES AND EXTREME HUMILIATION. This is only a fantasy story XXX+. I only wish there is enough here to make each of you happy. To those who have given me constructive criticisms as well as those with praise thanks. Lauren Westley. 

*

As the car bounced around on old shocks I felt Jim's deposits swirl inside me. I actually had a weed induced thought of whether it would look like a smoothie when it came out. I know, how disgusting of me to think that. but Jim's kind way of having sex with me made the thought of drinking it less then horrible and then my mind tried to make it into something acceptable.

Thinking back to barely a week ago when I kissed Kelly, Joe's girlfriend. We were eye to eye. Me 5'5" and Kelly 5'5". I may have even weighed less then her. I had overheard her once in the hallway saying she weighted 120 and girls don't make up stories about weighting more then the do. Instead it's the opposite. I was more like 117 but I wanted to be bigger so I told everyone 120 when they asked. I wanted to be taller too so I tried to say I was 5" 6" but I was barely 5'5".

I hadn't ever had sex with a girl. Actually only one girl had ever seen my penis and she had laughed so hard I ran out embarrassed. My penis was the size of my little finger. At least it wasn't the smallest penis in the world. I had once checked and the smallest penis was 5/8" mine was a good 1 3/8 inches when erect. I guess when it wasn't it was probably 5/8" or less. It was embarrassing only to me since the incident with that girl until earlier today when Joe and Sean laughed.

Now I'm sitting between Joe who is 200 lbs of muscle with plenty of dark body hair and scraggly black hair on his head and his brother Sean who isn't much smaller who sported red body hair, a freckled face and a marine boot camp red hairstyle I wondered about their lineage. Trying not to think of the circumstances I'm in I imagined they had an Irish mother and different fathers. I even wondered, since Sean was the youngest, did their Mom take a trip to Italy, get pregnant, come home and birth Joe finally settling down with a nice Irish lad in her neighborhood?

Of course all I'm wearing are my sister's white panties stained with my cum drying against my 'nub' and her open toed high heels. My pink nails contrast the femininity of my smooth, hairless white skin. The blond curls on my head make feel girly after the way Jim pulled his masculine fingers through them as I fucked him. Though I can't see my curl hair right now I do know how they look. Other then that my body is girly smooth moisturized by various creams including man-cream. But it's the tit bars and chain that hang between them that make me a slut bitch. And the thought of all those disgusting tattoos horrify me.

I take the ride as an opportunity to raise my hand hoping this way I can ask a question.

Sean puts his hand on my thigh and says, "I like that sissy girl. You should raise your hand whenever you want to talk. We may or may not ignore you. But this time what is your question?"

"Mister Sean, will these tattoos come off Sir?" 

"Well Jill if you are a good girl they will fade over the week. They should be gone in ten days but if you aren't then we'll just have to make them permanent."

"Mister Sean I promise I'll be a good girl Sir."

"Jill, a good girl will do as she is told," Sean finishes.

In my mind I realize there isn't really any choice and I'll know in ten days if Sean is telling the truth. Also they did seem a little lighter earlier. Or was that just my imagination. We enter a highway and I wonder where Jimmy's house is. And I also wonder what Unc is going to want from me. He's so big and fat and not my type. MY TYPE. What am I thinking?

Sean's hand moves up my thigh and I can't believe my clitty starts to have feelings. I hope it doesn't show. I try to concentrate on something else. Look at the signs I say to myself. When I look up I see we are about to exit the highway. The highway exit sign says Pearl Rd. This is where trailer parks and shanties are located. It's about 20 miles from my house and I've never been here since everyone in my neighborhood knows it's the rough and dangerous part of the city.

We are now driving on dark streets and Sean is still fingering my thigh near my crotch when we stop. I see the stop sign through the front window. There's a street to the left. The only illumination seems to come from our headlights. I can see decaying old brick buildings and some trash littering the streets. On Joe's side there appears to be one of those alleys where you pick up the trash behind buildings.

Sean looks at Joe and as if they had spoken to each other Joe looks at me and says, "Sissy would you like to be allowed to empty yourself without drinking it and no more piss tonight?"

I can't believe what I just heard. I'm ecstatic as I reply, "Yes Mister Joe Sir. Yes."

"Well Sissy this is what you'll have to do. Down the alley there lives an old bum who has been there for years. You have to go up to him and convince him to let you give him a blowjob. Then you must get him to cum in your mouth. Either during or after he cums in your mouth you can pee out what's in your pussy and come back here. Show us his cum in your mouth and finally swallow it."

My mind is considering the exchange. Not sure which is worse but not having any more pee in me is the better idea. 

"This offer ends in five seconds," Joe said.

Within two seconds I mumble out the words, "Yes."

I don't get reprimanded for not saying it the right way and Joe opens the door. Joe makes me climb over him and my eyes lock on the glass he's holding in his hand. No way I'm not coming back with a mouthful of cum, I think. Fortunately it's a warm late spring night. Cautiously I look around.

"Hurry up girl," Jimmy says, "we don't have all night."

I strike out down the alley and you know what I'm wearing. What I must look like! My heels click on the concrete. It's very dark. I can't see anyone and I begin to wonder if this is just another humiliating joke.

"Mister," I call out weakly not sure if I want him to be here or not. Not even sure I want him to hear me. My voice is a bit squeaky. I'm getting use to being in this sissy octave range.

I hear some rumbling by the garbage near me and then a hand comes out and grabs my ankle. Scared I nearly pee myself.

"Whatcha want girl?" comes from a gravely bass voice as the papers move away and lying there slowly getting up is an old black man.

"Mister would you like a blowjob," I blurt out.

Now his eyes have adjusted, better then mine.

"You no girl are yu?" he says obviously looking at my flat chest.

"No Sir."

"Are u one of those kin-kee puss-boys?"

"Yes Sir."

"An u wan to wrap your lips on my banger?"

"Yes Sir"

Well it didn't take long for him to agree. Next to him he lights one of those small electric camping lights. He maneuvers himself with his back against the dumpster and pulled me by the leg reaching up and grabbing my wrist and pulling me down.

"I got full nuts," he said as I went down. 

Instead of having me kneel on the cement he had pulled out an old rag and placed it for my knees but as I came down near him I could smell the alcohol.

"U make a cute puss-boy," he says, the dim light illuminating my face. "Give here Mr. Sam a kiss fore yu git sum my hon-eee."

He pulls me close by my cheeks to his lips and the dim light shows how big they are just before his lips smother mine. I am shocked as he pushes his tongue into my mouth and licks my tongue washing his taste all over my mouth. His saliva drools into my mouth and then he pulls back pushing my head down between his wide spread legs. Taking one hand off my head he unzips his fly and his dick pops out. No underwear.

"Now git yourself some nut-juice puss-boy," he coughs out.

As horrible as this sounds part of me felt if anyone deserved a blowjob Mr. Sam did. So I got to work thinking I was probably doing a good deed. I tried to breathe as much as I could through my mouth but often I had to inhale the stench around me. His cock wasn't too big and since I couldn't really see it I tried to imagine it was one of those Tootsie-Roll pops. Also he didn't hold me but instead leaned back and would say things like, 'nice lips puss-boy," none of which were said meanly. I'm not sure how long I was sucking his dick when I felt his legs extend a little bit and he seemed to lean back harder against the dumpster. With just a moan he began pumping my mouth full of his jism. And here's another thing. His jism didn't taste bad. It washed over the foul saliva from his earlier kiss coating my tongue. Mr. Sam's load was bigger then any I had had earlier. My mouth was full. I had accomplished my task. No pee for the rest of night.

"Show me puss-boy," as Mr. Sam's hands lifted my head up. "Open dat puss."

He held my face as I opened my mouth. It was full of his man juice.

"Good puss-boy," he said. "Now swallow my nut-juice."

Swallow! I couldn't believe it. I didn't want to go back to the car with an empty mouth but Mr. Sam did something that made me swallow his nut-juice into my belly. With one hand he held my mouth closed and the other he pinched my nostrils till I swallowed it all. Then he let go of me.

"You come back puss-boy, anytime," Mr. Sam said as I got up.

I walked back to the car with a hobo's nut-juice in my belly instead of in my mouth with my high heels clicking away in the dead of the night. The car headlights glowed ahead like a lantern to hell. I wondered how could I feel sorry for a bum and then even like the taste of his cum. I wanted to cry. Even the thought of crying was humiliating but the tears came and flowed down on my cheeks as I reached the car.

"Why are you crying," Joe asked as he opened the door and looked up at me.

"Mister Joe, the hobo did cum in my mouth but he made me swallow it," I answered.

"Is that why you are crying," Joe mocked.

"Mister Joe, that and also how humiliated I feel."

I climbed into the car sitting between Sean and Joe. I had been so upset I had forgotten about letting Jim's cum and piss cocktail out. They asked me to tell them about my 'adventure' as they called it. I told them everything about how he called me 'puss-boy', about 'nut-juice," etc. as Jim continued driving. There were comments about how bad I smelled and laughter about the rag on the ground for my knees.

"Well you were a pretty good girl Sissy," Joe said, "but you really didn't accomplish your task. We'll have to see later what a proper response will be. BTW, did you get to let your pussy pee?"

Stunned, I had forgotten all about that when the shock of having to swallow wiped my mind clear. Jim's piss and cum were still deep inside me. I guess because I carried three loads for such a long time Jim's hadn't made the necessary demand on my system.

"Mister Joe I did not get to pee. I forgot Sir," I answered.

Not a word was spoken as we drove on through the dark streets. Although the main street was called Pearl the district was known as the black pearl. Not because of rarity but because of the darkness of life here.

I smelled some pot wafting back from the front seat and a few moments later Joe was holding the joint to my lips. I inhaled and the high kicked in again. I flashed back to my house when I fucked Jim's cock. How he came in my pussy and my own orgasm. As repulsed as I was it was equally exciting. More exciting then any sexual experience I had ever had.

We pulled into a driveway. I was thankful it wasn't a trailer home. However with the old rusty car on the front lawn I wasn't expecting much.

"We're home," Jimmy said.

There were no other cars in the driveway as we walked from our car to the back porch. The back porch had two, sorely in need of repair, steps with an old zinc coated dented garbage can next to them. The porch itself was very small with one of those funny little dormers over the door. You know they look like a tiny roof with shingles. A small café table and one chair used the space not needed by the door opening and to walk down the steps. The white painted metal door was dented. I could only imagine the quarrel that must have taken place here. How dangerous was Jimmy. I had gone along with this since I didn't want to be hurt and had continued out of both embarrassment coupled with all the men who could have simply raped me. But I hadn't thought of how violent things might have been. Now I did. I cowered even more as we walked in and I saw a couple of holes punched into the sheetrock. I decided fulfilling their demands would be the best course of action and if the tattoos didn't fade away in 10 days I would run away and never go home.

Walking through the house I noticed how nice this home must have been at one time but certainly hadn't had a woman's touch in awhile. Although the kitchen was fairly clean empty bottles and a few plates stuck with food sat on the counter. The cabinets were made of cheap pine. They were pre Home Depot probably the original cabinets in a 1960 tract home. 

Some of the walls had blank areas where pictures must have hung at one time. Before I saw more of the downstairs Jimmy took the lead and said for me to follow him to my quarters. As we walked upstairs he told me he had moved all his ex's stuff out of his room into what had once been his daughter's room. He said his daughter had died when her School bus had skidded over the side of the road, flipped over and over and crashed killing several including Sarah in the worst fatal School bus accident in the State. It had been the blow that ended his marriage. He was a bit melancholy about it as he talked and I actually felt sorry for him.

The room was decorated for a seven-year-old girl except a few things were different. There were some boxes marked Alana, his wife's name and the closet had Alana's clothes hanging. One box was marked lingerie and another blouses. There was only one small chest of drawers and a multi-tier of empty shelves. A vanity sat between the two windows. The wallpaper was Disney Little Mermaid, Sleeping Beauty, Cinderella and the single bed had been painted pink with pink and white striped sheets.

When we went downstairs again I was in for a big surprise. There was just Joe, Sean, Jim and Jimmy. Sean called me over.

"Sissy we have decided the following as your punishment and what you will do. For your punishment each of us will give you ten whacks on your ass and as you know there's no screaming here either. Then if you haven't leaked your precious cargo you may go upstairs and go to bed exactly the way you are dressed now. Finally if you wake up tomorrow morning and you haven't had an accident you may use the toilet. Then shower and find something appropriate to wear. You'll make breakfast for Jimmy and have it ready for him by 7:30am. Instructions for your day will follow."

I was going to be free of this nightmare for the night. Then I remembered school had ended on a Thursday so tomorrow was Friday that meant these guys probably had to work but worse it also meant the weekend was around the corner.

"Do you think you can handle that Jill," Sean asked?

Almost in girlie glee with a little up and down movement clapping my hands as if I was now a trained seal I answered, "Yes I can Mister Sean. Yes I can Sir."

I took my spanking fairly well. I was crying through the last half but I didn't scream and I didn't leak. Finally sent to my room with my sore ass full of piss and cum I lay down on the bed squeezing my sphincter and fell asleep crying.



High School Dilemma Ch. 06



(Authoress's note: of course all disclaimers are still in place regarding characters etc. PLEASE DON'T READ THIS IS YOU HAVE AN AVERSION TO PEE SCENES AND EXTREME HUMILIATION. This is only a fantasy story XXX+. I only wish there is enough here to make each of you happy. To those who have given me constructive criticisms as well as those with praise thanks. If you don't like the story that's understandable but please be kind in your critique. Lauren Westley

*

I woke up and looked at the clock. It was five am. I was lying on top of the pink and white duvet. This was not a dream. My white panties were stuck to my tiny penis. And after all the cock I had yesterday there was no doubt my penis was small. So small calling it a nub was more accurate. The chain dangled with a slight metallic sound as the links collided with one another. My nipples were sore from both the bars that Sean had inserted and the pulling by the chain. I wanted to go back to sleep but I also gurgled inside with Jim's piss and cum. I had to get up and when I rose the urge was so great I rushed to the bathroom. 

As I pulled my panties down they were stuck to my nub and I didn't feel I could take any longer fiddling with them so there I was sitting on the toilet with my panties barely off my ass and still connected in front while I emptied the guy toilet I had become. The first spurt rushed out but the rest took awhile since it was probably far up inside me. I don't know how long I sat there but it felt like an eternity. The smell was awful so when I was finished I closed my eyes, pinched my nose and flushed it all away. Then I sprayed perfume.

When I went to the sink to wash my hands there was a note and a small black bag.

"Jill, inside the bag is another type of bag for taking an enema. Before you take your girly bath (and don't forget to make sure you are smooth everyday) fill the bag with warm water and one ounce of the soap you'll find in a bottle in the bag too. Don't let the enema out of you until you are all finished bathing and you are dressed with makeup ready to go. Also I've laid out what you will wear today on the chair by the bed. See you at 7:30."

I opened the bag and there was enema bag and instructions on how to use it. The nozzle had just a hole in the center. I filled it with warm water and measured an ounce of the soap liquid and as instructed shook it up first. The marking on the bag said ONE QUART.

Then pulling my panties finally off and turning on the tub (there were bath crystals so I poured them into the tub) I inserted the nozzle into my rectum and let the soapy warm water flow into my bowels. Actually I was happy doing this since it felt I was sanitizing after holding Jim's piss and cum all night. Then I climbed into the tub and soaked. The soapy enema didn't seem as easy to hold as the pee and cum but I managed. I looked at the tattoo just above my little landing strip and my nub. In the tub the pubes showing did look so girl-girl. But at least the tattoo had faded a bit. Sean wasn't lying.

I was happy I had awakened early since it meant I could lounge a bit in the tub and think. How could I get out of the next two weeks? They didn't have pictures. I'd run away after Jimmy left for work. Where would I go? 

When I finished bathing I felt so wonderfully clean. My mind was swirling with escape thoughts but I figured I'd better wait till later and started applying eyeliner after I dried my hair. I was amazed the curls hadn't come out and I still looked more girl then boy. Even as I did my eyes I saw my pink fingernails and when I looked down to my pink toenails my whole body in my vision looked feminine. Maybe I should have been a girl. I thought? But then changed that thought to how terrible it must be if girls had to do what I did.

I went out to the chair to find what I was to wear because I realized I had better not put too much makeup on if I was going to have to pull something over my head. There on the chair were black lacy bra, panty, garter, stockings, short black sheer ruffled skirt, white shirt, red corset and a pair of red heels. Also a Post-It note saying, "You can take your chain off and you can pick your own jewelry.

By 7am I was all ready so I went and sat on the toilet letting all the soapy water out. Several times over the hour and a half I had almost had an accident but I had managed. I was getting better at holding. Joe had been right about that. Looking in the mirror before I went downstairs I saw my little titties and tit bars hidden by the bra and covered by the blouse. Having the chain off was a good thing. The skirt was really short and when I looked in the mirror I looked like a 'blond fuck-me doll." My heels clicked on the wood floor as I tried to walk downstairs quietly. Finally I realized if I walked on the soles (balls of my feet) that would be quieter but I was too late.

"Sissy," I heard Jimmy call out. "Make me two eggs over easy, don't break them also Whole Wheat toast, fresh squeezed orange juice and coffee. I'll be down shortly."

"Yes Mister Jimmy, I'll have it ready Sir," I replied in my little singsong voice.

"Good Girl," his muffled voice coarsely replied.

Into the kitchen I went and struggled with getting everything ready in the half hour I had. I must have destroyed six eggs to get two sunny side-up with unbroken yolks. The rest was pretty easy and I had it all done and on the table when Jimmy strolled in. I didn't want anything to go wrong since escape was the plan. I even curtseyed when he sat down and then I poured his coffee and curtseyed again as I started to walk away.

"Get that pad and pen Sissy," Jimmy said pointing to the counter top.

As I got the pad and pen I thought how sometimes they called me Jill and other times Sissy. I also realized I was answering to them as if they were my names.

"This is very good Sissy but you forgot my napkin," Jimmy said as he took a forkful of egg and a bite of toast, "but first sit down and take the pen and write down everything you can remember about yesterday. Write it in the first person Jim said for me to tell you."

While Jimmy ate his breakfast I wrote down the events of yesterday. Writing about the bum was the hardest part even harder then about Jim peeing and cumming in me. I was almost finished when Joe and Sean came into the kitchen.

"My you are one pretty girl Jill," Joe said.

And oddly I blushed a bit with the complement and thanked Joe properly. When I was through I had to read some of it and they all nodded approval.

"Now sign it," Joe said.

I signed it Sissy.

"Now sign 'I Loved Last Night,' and your real name," Joe said with a glare in his eyes.

Sean was standing right behind me. There was no choice but to sign it. Now they did have something on me but it got worse.

Joe pulled a box out of the bag he had by his side saying, "My Uncle says this is for you Sissy so come over here and bend over."

Sean grabbed my wrist and walked me over to Joe.

"You smell so nice Sissy. I bought that perfume for my wife but she never wore it," Jimmy said.

Bent over with Sean holding my wrists Joe lifted my little black skirt and pulled my panties down.

"This is such a fuckable hole," Joe said as he put his lubed finger into my asshole.

"Now Sissy you will love this," he said as he showed me this black butt plug. It was longer then the other one. Joe turned it and showed me there was a little hole in the head the size of large straw and larger hole the size of a nickel in the back. Then he slowly pushed it up my asshole until my sphincter locked onto the thinner part. I'm sure you know what butt plugs look like.

Then Joe showed me a test-tube clear plastic vial filled with white creamy liquid inside. I didn't have to guess what that was. He pushed that up the hole in the plug and it clicked into place.

"Now this isn't like any other plug. It's a prototype Uncle made. You see it has two major additional features. First there is a GPS. If you take it out the signal will let us know because of temperature difference and while you wear it we know where you are. Second, the tube I inserted is filled with man juice to fill your pussy. After you went to bed last night we filled a few tubes. We can send a signal that will release a dose into your pussy."

I couldn't believe it. I had written that letter and now I was GPS locatable but then Sean said, "So don't even think of running away," as if they had read my mind.

"You see Sissy Jill there are a few remotes we can vibrate this and or make it shoot some cum into your pussy hole. Aren't you a lucky girl," Sean snickered.

I was in such disbelief I didn't answer. I mean now I had a tracking device inserted into me and it could do even more humiliating things to me and of course the letter, which Sean was folding up, and putting in his pocket was an admission of culpability. I was under some new type of house arrest.

"So you forgot to thank us for this gift Sissy and here's another gift for a girl like you. During the day you'll clean the house and have everything ready for when we come back. There will be deliveries all day. Whomever comes to the door you must answer it showing off your body in a manner any slut would use and asking any man who rings with 'Mister would you like a blowjob? I'd love to swallow your cum Sir.'

This was more deviant then I've ever imagined.

"And you won't know who is a spy for us and who is just a delivery man," Joe said. 

Jimmy just sat there drinking his coffee smirking.

"Make sure you are all girl all day Sissy even when you pee. And yes you have permission to do that," Sean said.

I was still bent over with my skirt up when Joe suddenly whacked my ass.

"You need a good spanking this morning Sissy don't you?" Joe grinningly said, 'because you didn't answer me and because you were thinking about skipping out on us. Right?"

Regardless of my shock I knew my punishment would be worse if I didn't speak up so I demurely said, "Yes Mr. Joe I need a good spanking Sir."

"Touch your toes Sissy and don't standup or move away during a spanking. If anything, give me more ass to hit," Joe said.

WHACK! WHACK! WHACK!

Joe spanked away as I tried to steady myself. When he seemed to be finished Jimmy told him how I had forgotten to place a napkin for him. So about ten more WHACKS and I was crying. But during this part of my spanking someone had turned the vibrator on and it wormed in my ass pulsing while I was spanked. I can't even explain the feeling as my prostate zinged my nub.

Sean remarked that my little "nub had hardened so I must have enjoyed it and asked me if I did."

"Yes Mister Sean," I said through my tears, "I liked my spanking and the dildo in my pussy Sir,"

"Well guys we must be off. Sissy can take care of things here," Jimmy said

And with that they left me alone.

Just a few minutes after they left I felt the vibration in my hole again. I guess it's just a hole now since they use it for both a pussy and an asshole and I've been told many times to remember I have both a pussy and an asshole now. The vibrations though changed and tingled though me. I couldn't even help it as my nub stiffened again. I wanted to rub myself but I didn't want to get into any more trouble so I sort of started dry humping the air and the vibrator also got warmer inside me. It felt like it was fucking me and then I felt the gooey cum shoot into me. I didn't know how much but it felt like a lot. The vibrations stopped. I started crying. I was forgetting who I was and now only this degradation existed and I hadn't even had an orgasm. 

I was almost done cleaning up the kitchen; Jimmy's wife had certainly kept it tidy and clean. The white cabinets were spotless and everything had a place so I knew I'd better do a good job. I wiped the counters and the handles on the cabinets like I had seen my sister and mother do. Suddenly the doorbell rang. I almost had a heart attack. I couldn't believe it. Who was it? Had they had meant it for me to go do what they said?

The doorbell rang again, "Ding-Dong." I scampered to the door my heels clicking. I knew I looked like a girl. Even the bra had been padded. If no one saw or touched me in one place they'd never know. Also all the tattoos were at least covered. I took a deep breath and began opening the door on the third ring.

"Delivery for Mr. Jimmy Temple," the deliveryman said, "can I put this box down somewhere?

I wasn't even thinking. I just stepped aside and let him in like I would anyone delivering a heavy box. Looking at him he wasn't unattractive. He was in good shape. Remembering how I was to pose I put one hand on my hip and bent my knee a bit twisting a little to the side like I had seen girls do in photo shoots. I was mortified by I wasn't so worried about asking him the question since I felt he'd probably think I was too much of a skank to take the offer. But I was terrified to think, "What if he did?" He put the box down and all six feet of him turned around to me and asked, "Is this where you'd like me to leave it ma'am?"

The words just fell out of my mouth. I had hoped they hadn't enough power to reach his ears but instead would fall harmlessly to the floor. "Mister would you like a blowjob? I'd love to swallow your cum Sir?" I asked in my singsong voice with my brain in shock.

As his eyes glared over my body looking to see if I was attractive enough to give him a blowjob I felt most like a slut housewife. But also I didn't want to be rejected. I had had enough humiliation so I looked up at him with my sea green eyes almost pleading with him to want me. I wondered if I looked like to him.

"Would you repeat what you said Miss," the mystery deliveryman asked?

And the more I looked at him the less I thought he was really a deliveryman. He was in his late 20's. His clothes were a cut above. An Orvis shirt, khaki pants and even shoes not sneakers. Yes he must be a spy.

"Mister would you like a blowjob. I'd love to swallow your cum?"

He smiled and his lips were saying 'yes.' But he also seemed in a bit of a shock. Maybe he was just the deliveryman.

"Now I wouldn't want to deprive a pretty little blond girl like you from getting a load of sperm. So of course I'd enjoy a blowjob sweetie," he said.

His arm circled around me and he pulled me tight to him so I could feel his limp cock against my belly. Then as his cock slightly hardened his hand slipped down under my skirt and felt my ass cheek. I was worried he'd find my nub.

"You know I won't kiss a dirty cocksucker whore," he said up close to my face and then his fingers found my crack and reached the base of the plug. I shuddered when he asked," What's this little girl?"

Quickly my mind came up with the reply, "Mister Jimmy likes me to have both my ass and pussy plugged when he's away but he has said I should suck many cocks to improve my technique, Sir. "

"I see sweetie. What does Jimmy call you?"

"Mister Jimmy calls me 'Jill, Sir." I replied.

By now his erection was hard and against my belly. He was grinding me and fingering the plug a bit when he asked," Does you Master spank you too?"

"Yes he does Sir," I almost pleaded as if to say, "May I suck your cock now instead of being spanked."

Almost miraculously he put his hand on my shoulder and signaled for me to get on my knees.

It's so submissive to be on your knees in front of a zipper with a cock dangling out waiting for your red lips to surround it. But as I said before it is also amazing to have something as alive in your mouth and feel it change size, hardness and of course throb in your warm wet mouth and finally spurt man juice. Instinctively I licked his pee hole when he was finished and swallowed it all down. In 24 hours I had become a cocksucker.

"Good girl Jill," deliveryman said.

His hand zippered his trousers as if I was just an inanimate object and with a quick pat to my head he walked away in silence, out the front door, leaving me there on my knees. The door clicked shut and I sat back on my heels thinking of what had just happened. My stockings, my legs, my skirt, I looked down and the taste of the deliveryman sperm still on my tongue I wondered about the rabbit hole I was falling down into. A mirror over the fireplace slanted down and caught my reflection with my red lips, dangling earrings and blond curls. I was looking through the looking glass.

Gathering my wits I stood up walking to the kitchen to get a glass of water. Now you'll think this odd but the butt plug was getting comfortable and I was finding a way to enjoy the whole situation. Even the skirt rustling on my thighs seemed okay at the moment. I know it's weird but I'm past the point of deception. There are many a fine feeling being a girl.