The School Tramp

As we had light awkward conversation around the table, Mom was looking puzzled. I suddenly realized that I had not removed the nail polish from two of my fingers, and when I looked down at my bare feet I saw that all of my toenails were still painted bright red. Mom smiled at me and mouthed, "we'll talk" but fortunately we were all busy with our respective friends after breakfast. Mom drove Mrs. Morton home to her husband. Cassie and Angela went up to her room for a bit more fun. I saw Karen out to her car. When we opened the door it still smelled extremely funky. We kissed each other on the cheek and then she drove off.

I went back to bed until mid-afternoon. Mom did not return until after dinner and I fled to my room, claiming I had to study.

Chapter 22 - Christmas Surprises

Mom knew I was avoiding having a discussion with her and it seemed she was happy enough to let things coast for the time being.

Christmas and a two week school break were coming up in a week. Two days before we were done for the holidays we got our mid term reports. When I took my report home, Mom was delighted to see all the As and A-s on the report. Of course, she didn't know that I had got those for sucking and fucking, rather than for studying hard.

By this point I was having sex with several of my classmates and teachers on a regular basis. The hormone injections I was getting from Coach Grogan were having an effect. I had never really had to shave much, and now I did not have to shave at all. My emotions were much more volatile and I found myself crying a lot more. Also giggling, but of course, that was also because I was getting high a great deal of the time. I was giving Karen a lot of money these days in exchange for a lot of weed which I was smoking every night before heading home after getting my ass fucked.

I was also noticing that my Carl jeans and other pants were not fitting well anymore. My hips and ass were getting larger. In fact, I asked both mom and Cassie for new larger jeans for Christmas.

All three of us were out of the house on Christmas eve. Cassie was over at Johnny's house with his family. Mom had been disappointed earlier in the day when Mr. Henderson had called up to cancel their date for the evening, so she went over to a neighbour's house where several neighbours got together to celebrate the holiday.

Me? I went out to a nice dinner at a fancy restaurant and then to an elegant hotel room in Springfield. I was dressed in a stunning "little black dress" which my date had purchased for me. Prior to arriving at the restaurant my date and I had each snorted a line of coke in his car. This was my first experience with harder drugs, and I had been a bit reluctant. But my date had insisted that I would not get hooked if I tried it just once. It was definitely a different experience. I noticed that all of my food tasted so much better. My date and I played footsie in the fancy restaurant.

When we got to the hotel room, I was absolutely gagging to get Mr. Henderson's cock down my throat. Yes, the principal had cancelled his date with my mom so that he could take ME out and fuck me silly. And he did. Fuck me I mean. Several times. I was well and truly fucked. Fucked fucked fucked. Or did I say that already? My head was a bit screwed up from the coke and the joint I smoked in bed afterwards. When we were done and Jordan was showering - we were finally on a first name basis - I told him that there was a big favour that I might want from him. I told him that I had been thinking of living as Sindy full time, and if I did, I would need his help at the school. He laughed at this and I asked him what was funny. He just chortled and said that I should ask him again in a week.

He also told me that I was going to have to face my mother about this sooner or later. I told him I was getting ready to do that. He smiled again.

I lit another cigarette just as he finished dressing. He leaned down and gave me a quick kiss on the cheek, and then he left.

I had asked him to not drive me home. Rather a few minutes later Carlos came into the room. He had been so good to me over the past weeks that I had promised him a Christmas bonus. He had tried to clean himself up a bit, but he still looked scruffy, had a raspy beard and smelled bad. But I had grown fond of the big lummox.

For the next hour we had rough hard sex which seemed to be the only way he knew how to fuck. By the end I had a few bruises, and had bit my tongue. But Carlos had come three times, once in my mouth and twice in my quite well used ass.

Carlos waited out in his cab as I changed back to Carl. Carlos drove me back to Bigelow. As I got out of his cab, he handed me an envelope with a Christmas card in it. It was a nativity scene since Carlos was very religious (he had several crosses dangling from his rear view mirror). There was also a picture of his wife and two children. I guess it was the card that his family gave to all of their friends this year. I gave him a big hug and a peck on the cheek and wished him a merry Christmas! As he drove away, I took the three hundred dollar bills out of the card and put them in my purse and tossed the card in the trash!

Christmas morning I slept quite well. Cassie woke me up with a kiss on the forehead and told me that mom would have breakfast in half an hour. I hopped into the shower and scrubbed away any lingering cum from the night before. As I soaped up my chest I noticed that my nipples were puffy and sensitive. My ass was definitely feeling much bigger too. I took special care to soap up my ass and stuck a couple fingers deep inside to get extra clean.

Feeling a bit frisky, I put on a pair of panties under my jeans. Those jeans were very difficult to get over my growing butt!. I looked in the mirror and longed to put on some eyeshadow and lipstick. I was going to have to have a talk with mom real soon.

But that talk came much sooner than I expected.

On Christmas morning there were normally only a few presents under the tree. This morning there were a lot of them. Mom was a bit coy about handing them all out first. So Mom and Cassie each opened the presents that I gave them, and Mom opened her present from Cassie.

She then handed me a wrapped present to open. When I had torn the paper and opened the box I found a pair of jeans - but they had a pattern of flowers and butterflies on the back pocket and down the leg. I realized they were girl jeans. Puzzled I looked at Mom and she had tears in her eyes as she said, Merry Christmas Sindy!

She knew! Mom explained that over the past couple of months she had known that something was up, something was different. She had been pleased when I had finally begun dating girls like Karen, but she had realized that perhaps it was just not girls, when she found all the cum stains in my bedding. And then she had found my Sindy bag under my bed. Plus the time a week ago when I had missed removing some nail polish had not been the first time.

And she had noticed my wider hips and even through my t-shirt she had noticed my growing tits. So she had finally confronted Cassie a couple weeks back and got the full story from her. Well, not the FULL story as it turned out. Cassie had not told Mom that I was a cock slut, as I was later relieved to hear from her. Cassie had told mom about my first date, and then that after that I had been going out as Sindy and found I enjoyed being Sindy much more than I liked being Carl.

I hugged Mom and she asked me if I was truly happy as Sindy - she had been so worried when I was buried in my room all the time as Carl. I told her that, yes, being Sindy was fantastic and it was harder and harder to pretend to be Carl anymore - hence the hormones.

It turned out that the other presents were all from Mom to Sindy. Mom had bought me lots of panties and bras, blouses and skirts - she had gone quite overboard in buying me a whole wardrobe of nice, reserved, young women's clothes.

I cried more as I opened each box. Half of everything was going to have to go back because it was the wrong size, and most of it was much more conservative than I was going to want to wear. The last box Mom handed to me was small. I opened it and I found a new id card, in the name of Cindy Barton. Mom had arranged a name change for me! And, she said, she had arranged with Mr. Henderson - whom she reminded me she was dating some times (and whom, I did not tell her, had fucked my ass soundly the night before!) for me to return to school as Cindy after the holidays!

I hugged her tightly and she suggested that I go upstairs and change so that she could meet her elder daughter properly. Cassie and Mom both helped me carry all of my gifts upstairs and I then spent the next hour looking through everything more closely and deciding what to wear first.

It took another hour for me dress, put on my makeup and fix my hair properly. Cassie helped me with all of this a bit. I was nervous as hell and gasping for a cigarette! In the end I wore only a pair of panties that Mom gave me. If Mom was going to meet Sindy (yes, despite my legal name beginning with a C, I would still think of myself with an S, for sin, sex and seduction) I figured she should get used to a bit more sexy version. I wore dark stockings and a garter belt, three inch heels, a short black skirt and a tight top that left my navel exposed.

Mom's eyebrows rose as I came downstairs, particularly when she say my pierced belly button and dangler. But she hugged me and complimented me. I excused myself and went outside for a cigarette. Cassie joined me. Another surprise for mom, both of her daughters smoked, although it could not have been too much of a shock, since most of the Sindy clothes she found would have been covered in the smell of tobacco.

Back inside Mom complimented me on the ease with which I walked in my heels and told me my legs looked very nice. She told me she had arranged for me to see a doctor in Springfield who would assess me and put me on a proper hormone regimen. We hugged and both cried a bit more.

What I didn't tell her was that I was perfectly happy to be a girl with a big clittie. I did want the hormones. I did want the body curves and breasts of a woman, but I had no desire to give up my cock. While I LOVED the attention of men, and having my bottom filled with their cocks, I had begun using my own dick more, in girls and sometimes in guys. And whether I was fucking, or being sucked, or someone was just teasing my dick with their hands, I loved the pleasure it gave me. I did not need a vagina to be fucked, so I planned to keep my pretty cockette!

Mom spent a good deal of the day cooking a great turkey dinner. Late in the afternoon the Hendersons came over to have dinner with us. In the car on the way over, Jordan told Stevie and Karen that they were in for a surprise - they would be meeting Miriam's new daughter, and then he explained to them that Carl now wanted to be known as Cindy.

When they arrived, Karen hugged and kissed me. Jordan gave me a gentle, principal-like hug. Stevie, the only Henderson who knew nothing about Sindy beforehand, just stared at me and stuttered, then finally told me that I looked hot. I guess it was quite a shock for him. He and I had been in school clubs together for the past few years, had swapped comic books, had played hundreds of hours of video games. And now one of his best friends had decided to be a girl!

Dinner was terrific and we all sat around watching a bit of tv afterwards. We took a break and all of us pitched in to help clean up the table and the dishes. We three girls (I was one of the girls now!!) went outside a few times for cigarettes and once we went around the block where we could smoke a joint)

Stevie said practically nothing to me all evening. He just stared. I realized that he was just a loser like so many of the other guys at school. Heck, like I had been before I discovered how pretty I could be. I promptly put him out of my mind.

At 9 pm the Hendersons left. Mom went with them. She and Jordan were going over to the house of one of the other teachers at school after they dropped Karen and Stevie off at home.

When they were gone, Cassie took me by the hand and took me up to her bedroom. I was emotionally exhausted from the revelations of the day, but always had time for my pretty sister. Cassie told me that I had not noticed that she had not given me my present yet. She handed me a box which I opened to find a new strap on harness and thick dildo shaped like a realistic black cock.

She kissed me, at first tenderly and then more aggressively. For the next ten minutes we wrestled on the bed, lips on lips, lips on nipples, my fingers caressing her pussy, her fingers wrapped around my cock. My nipples were increasingly sensitive and I squirmed when she bit them. I was panting good and asked her to put the harness on and fuck me. But instead she told ME to put it on and fuck her! She had decided that I should fuck her, but as she would never let me put my cock in her pussy, she had bought me the harness and cock to use on her. It was a bit awkward to place the dildo above my own boyclit, but I managed and soon, I was on top of my own sister, ramming the thick black dick in and out of her pussy. We locked lips and sucked tongues as she moaned lustily. We did this for twenty minutes and I began to get a bit bored. Honest, I loved to pleasure my sister, but neither my cock nor my boipussy were getting any stimulation.

Sis realized my mind was drifting and asked me if I was ready for my second present. I nodded and she told me to leave the harness on, but to remove the fake cock. She reached over and pulled me close. She took my dicklette in her mouth and sucked me to a stiff erection. As she did she took some lube from the drawer beside the bed and used her fingers to lube up my ass. She turned me around and worked the big cock slowly into my ass pussy. It was big, but I had had lots of cock in me by this point and it slid in nicely... all nine inches of it disappeared. She then moved a couple pieces of the harness around and the base of the dildo clicked into place. She let go and the harness was holding the entire length of the cock inside of me!

I squirmed around on the bed. My actions caused the dick to slide around inside of me. It felt wonderful.

Cassie then told me to get on my knees. I panted while doing so, more pleasure rippling through me. She again took the bottle of lube, but this time she pushed the liquid into her own ass. She then presented her ass to me, telling me that THIS was my second present - she wanted her older sister to fuck her in her ass.

I positioned my cock at her butt chute, and pushed in. I met resistance, and she groaned a bit in pain, but I persevered. I knew she had let Johnny do this with her more than once, and Karen had told me that SHE had fucked Cassie's ass with a dildo, but sis was still not very experienced at taking a cock back there, so I was slow and patient. When I was a few inches in, she urged me to push harder, and soon I was all the way in, and then I was fucking my lovely sister vigorously. Her fingernails dug into my back at times, and her heels pulled my butt tightly to hers at times.

We kissed enthusiastically, and we both shouted loudly at times. It was a blissful ten minutes and then I finally pushed deep into Cassie and squirted a whole days worth of jism into her bowels! God, an ass was SO much tighter than a cunt!

We lay there snuggling for awhile and then we returned to bed to cuddle for awhile.

Finally I put on a new nightie that Mom had bought for me and slipped under the covers.

Tomorrow was a new day, and a new life!

Chapter 23 - Girl Power!

Ten days to prepare for going back to school did not seem like long enough.

All of my boy clothes got stuffed into bags and given to charity. We repainted my room in bright colours and I got new sheets and bedspread in various shades of reds, pinks and autumn colours. My drawers were filled with panties and stockings and other frillies. The hangars in my closet held my few dresses, but I knew the closet would soon be full.

Cassie and Karen went with me to the mall where I got my ears pierced multiple times. I bought myself a cute ankle bracelet as well as a bunch of other inexpensive earrings and necklaces. I went to the tattoo parlour and added more paw prints, now leading up my side, and also down one ass cheek, curling around towards my asshole.

We went to the salon where I had a complete body waxing again. I also had my hair cut and dyed. I no longer needed the pony tail so that I could appear boy or girl at different times. I got a nice sexy shoulder length cut, with bangs, which I just loved. And my hair was dyed platinum blonde.

I got into my first girl fight with mom when she found me smoking in my room. Even with the windows open she refused to let me "stink up the whole house." This was just the start of my deteriorating relationship with mom.

I was very nervous when school started. Cassie stayed close by me on the first day, but by the end of the second day pretty much everything was normal - well, as normal as things can be for a hot girl! No one seemed to have any problem with Carl suddenly becoming Sindy. Most of the guys were too shy to come up and talk to me (at least, out in the open), but all of the girls were eager to welcome me and make me feel like one of them. Almost everyone figured I had already had a sex change operation. Those girls who asked to see my dick, well I showed my cock to them. The guys generally got to see it only if they took me out on a date and fucked me. Which was a lot of them.

I was having sex on a regular basis, and by regular I mean two and sometimes three times a day. Teachers, principal, fellow students... they all wanted a piece of me. And I was loving it. My boipussy was stuffed so full of cock that I was in heaven. I was also quite high a lot of the time. Karen was keeping me well supplied with weed, so long as I could pay her for it.

Mom drove me to my first appointment with the doctor in Springfield. After that I made my own way over - either Cassie or Karen drove me, or one of the guys I was going to fuck after the appointment. And sometimes Carlos drove me in his cab.

The doctor was disappointing. He did not like the hormones that Coach Grogan was giving me. He thought I had good development, but thought that the drugs could be damaging my liver and other organs. He wanted to put me on other 'mones and cut the dosage way down to better manage my transition. He was disturbed to hear that I wanted to talk about breast implants already. He figured I needed at least a year of psychological evaluation before that step. To keep mom happy I just nodded and said yes and told him to go ahead and order me the new meds.

Then I went to Coach Grogan and told him I wanted him to double my weekly injections. I also got the name of the doctor whom he said would do my breasts for me.

Coach Grogan's cock was still the largest dick that was fucking me on a regular basis. Principal Henderson was not giving me "detention" quite as often, but by now most of the guys on the football and basketball teams had talked to each other and had come knocking at my backdoor (yes, I mean my hershey highway) and I had let them in, willingly!

Over the next couple of months I developed a routine. I studied very little, preferring mostly to hang out with Karen and a number of the other cool girls. During daytime, we skipped a lot of classes and went shopping, or just went to someone's house and got high while we talked about which guys we were all dating and fucking. When we compared notes, I had to be modest and say I was having sex only a couple time each week. I could not tell them about the teachers, nor that I was being fucked by most of the girls' boyfriends!