High School Dilemma Ch. 05

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(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 ısparta escort 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 istanbul escort 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. izmir escort 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.

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