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...