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

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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.