High School Dilemma Ch. 04

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(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,” casino oyna 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 canlı casino 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.


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.


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 kaçak casino 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.”

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