The School Tramp

Sadly, Johnny was not able to meet up with me on the Thursday night, so I spent that evening practising my deep throat technique on the dildo. I thought I was making good progress, but the rubber dick did not slide as easily past the pack of my throat as I imagined a real cock would. I resisted sticking the dildo to the wall and ramming my bottom back and forth on it, since Mom had a bunch of neighbours downstairs in the living room, and my groans and banging around might raise too much curiosity!

There was one negative aspect to the week. My grades. During the past several weeks Sindy had been taking over my life. My evenings were spent out on dates, or on the internet reading up on girl fashions or browsing porn sites. I had not been putting in the hours of study and homework which had been normal for me. I was an A student up until then, but this week I got back the results of tests in all of my classes and suddenly I was getting Cs and even some Ds!

I was going to have to find more Carl time, and let Sindy out a bit less, if I wanted to be able to keep up my grades this year, and next, and get into a good university! But Sindy was having so much fun! A conundrum I was going to have to solve. I wanted the fun, but also wanted the good grades!

I had another surprise this week, and did not know if it was a good one or a bad one. Danny and I confirmed our date for Saturday night. Cassie would drive me downtown and Danny would pick me up there. But... he wanted a date with Carl, not with Sindy. Danny said he was gay and was interested in guys, not gals, and so he wanted to spend time with me as Carl. I was a bit taken aback, but agreed.

On Saturday night I shaved and showered and put on some nice boy clothes. Boy, was it different getting ready as Carl. Half an hour tops to get ready, instead of the two hours that Sindy needed! Mom was a bit taken aback by my new hair colour and fresh scrubbed appearance, but was thrilled that I was going out on a date, though I did not tell her it was with a guy! I do think she wondered though.... with my more feminine hair and eyebrows, she might be having thoughts that her son was discovering he was gay! Hmmm.....

It didn't help that I was walking with a bit of swish to my step too. Carl had asked me to wear the butt plug he had left inside of me the previous weekend. So after my shower I had lubed up my ass and slowly shoved the plug up inside my rectum until my anal ring had clamped around the base. It was both pleasant and unpleasant to be walking around with that thick plastic stuck inside of me and, indeed, it was difficult to walk straight.

Mom's own date picked her up just a few minutes before Cassie and I left. I was surprised to see that it was Mr. Henderson, the principal of my high school. That made me very nervous, but I realized it was a reaction to his authority. It was like Mom was dating the enemy!

Mr. Henderson was a widower whose wife had died about eight years ago, before he had moved to Bigelow and taken over as principal at our school. I knew this because his son, Stevie Henderson was in my junior class and we were friends. His daughter Karen was in Cassie's senior class and those two hung out together sometimes.

I knew Mom had more than one guy who she was seeing. I guess she was serious enough about Mr. Henderson since she had an overnight case packed. Apparently the two of them were going out of town to see a Sunday football game somewhere far enough away that they would not be back until late the next evening.

I haven't really told you anything about my Mom yet, have I? Well her name is Miriam Barton and she is about 5 foot 5 with long dark hair. She is attractive, but not gorgeous. Her best feature, to my mind, is her long legs which she is not shy about showing off, either by wearing short skirts or by wearing patterned stockings. As a nerdy teenager, the occasional glimpse of my mom's dark stockinged legs over the years has been about the only sexual thrill I ever got in person. Cassie has obviously taken after her, which has disappointed her because both have not got much in the way of tits.

Mom had a tough time raising two kids but we seemed to be turning out okay. Mom DID let her hair down a bit on the weekends, often going out on dates with men, or going to bars with one or another of her girlfriends. Sometimes she would stay out overnight. Sometimes I would hear grunts and moans from her room as one of her men friends banged her.

Um, by girlfriends, I mean friends who are women. I don't mean mom is gay, a lesbian. Though I guess I do sometimes wonder if she might have a bit of fun with one or two of them sometimes. Anyway, I am getting distracted......

Mr. Henderson smiled at me and complimented me on my appearance. He said that the chess club and math clubs (for which he was the responsible teacher) had missed me the last couple of weeks, which brought a frown to mother's face. She was obviously wondering why I was missing some after school activities which I told her I HAD been attending. I couldn't very well tell her that instead of solving equations and moving rooks around a chessboard, I had been swallowing my sister's boyfriend's cock and screaming loudly as he rammed that same cock up my bum chute!

Johnny picked up Cassie and I up and drove us downtown. Johnny was a bit surprised to see me going out as Carl, and even called me squirt in an almost insulting way. They hung around with me until Danny drove up and I hopped in Danny's car.

Danny drove us into Springfield and we first went to a pretty nice pizza place for dinner. While we ate we talked animatedly and Danny told me how good I looked, and how he liked me much better as Carl than when I was dressed as a girl. Danny was dressed very smartly. While we were reaching for pizza slices and garlic bread, his hand managed to brush mine a few times, but I did not feel any thrill at all. If I had been dressed as Sindy we would probably have been holding hands across the table by the time dinner was done.

He noticed me squirming around on my seat from time to time and smiled, realizing it was because of the plug that I had up my bum. He whispered in my ear that he hoped I was enjoying the plug, and he knew that he would definitely enjoy replacing it with his thick dick at the end of the evening!

We then went to an art house film. It was in a small movie theatre but there were still only about a dozen seats filled. It was almost two hours long and was very good in spots. Danny held my hand in the dark, but I did not squeeze his hand at all. At one point he turned his head to kiss me, but I found that to be a good time to blow my nose in a tissue. I was feeling very unsettled, but could not place my finger on why. Danny was a great looking guy and had a very good personality, but somehow I was not getting into this date. Heck, on what I would now term to be a normal date night (my, how things had changed in just a few weeks!) I would have had my tongue down his throat, and his cock in my hands by now!

After the film, Danny took me to a gay club. Once we were inside there were very few girls to be seen and in fact, it was hard to tell if the couple of girls WERE girls. There were guys at the bar, guys at the tables, guys on the dance floor. There were fat guys, skinny guys, tall guys, big black guys, guys in leathers and chains, slim guys with limp wrists. The place was lively, and the booze was flowing. The music was loud and the dance floor was jumping. We found a table and Danny went to buy us a couple of drinks. While he did a few guys eyed me up and a couple said hello. But when he got back, Danny made it clear that I was his.

We sat and drank our drinks. We held hands. We went up and danced a few times and Danny held me very close. It was obvious that he was into me - he was constantly rubbing his large boner against me as we danced. It was a fun place.

But I was not feeling the love.

Around midnight we went out to the smoking area and Danny lit up after asking me if I wanted one. I automatically told him I did not smoke, and then wondered why I had said that. It was dark outside and in the shadows you could just make out several couples holding hands or kissing - all guys.

We returned to the dance floor and as it got later, you could see more guys grinding against each other. Danny began grabbing my butt and grinding his cock on me. He kissed me tenderly on the forehead and when I looked up his mouth pressed against mine and his tongue probed my mouth. I kissed him back, eagerly trying to find a connection with him, but failed.

I hurried from the dance floor and made my way to the washrooms in the back. Back here out of direct view of the main club area there were a few couples being a bit bolder. I passed a young guy on his knees who had his mouth jammed down on the cock of a chubby guy wearing leathers. And beside them was another young guy, cross-dressed and looking cute, who was also slurping on the dick of his date. I felt nothing watching the former, but I very much wished I was the pretty boy.

And that was when it hit me.

I went back to Danny and dragged him out of the club, asking him to drive me home. On the way, I began to cry and he pulled over to ask me why. I told him I had had a nice time, but that I had felt uncomfortable all evening. Finally I had figured it out. I was not gay. As Carl, I was not comfortable kissing a guy. Carl did not smoke. Carl was a nerd, a geek, a loner.

But Sindy was outgoing, alive, and definitely a cock tease. Sindy loved having sex with guys. I realized that I wanted to be Sindy as much as possible. I did not like Carl, and wanted Carl to go away.

I was a girl at heart.

I wasn't gay. I liked being Sindy. That did not mean I wanted to be a girl. At least I didn't think it did, but I knew that I had to be femmed up to be interested in a guy.

We talked for a long time and Danny was very understanding. But Danny WAS gay, and he wanted a boyfriend, not a girlfriend.

I told Danny where I lived and he dropped me off at the corner near my house.

I never saw him again although we did have contact on the internet from time to time.

Inside I tapped on Cassie's door and opened it a crack. This time, Johnny was fast asleep, but Cassie was awake. She slid out of bed, put on a robe and came to my room with me. I again cried and told her about the evening and my revelation. I was pretty much a wreck from all my sobbing, but Cassie held me tight and listened attentively, nodding at the right times.

She helped me get undressed and then put on a pair of frilly panties and tucked me in to bed. The lace felt nice against my cock as I drifted off to sleep. At some point during the night I got up and went to the bathroom. I had to remove Danny's plug from my ass. The thought of him made me teary again, but I managed to fall back to sleep fairly quickly.

Chapter 11 - Girl Fun

When I woke up in the morning I was aware of three sensations. I was hungry. My panties felt wonderful on my woody. And I was horny as hell.

Cassie's door was open a crack as I tiptoed past. I could see she was sleeping alone - Johnny had slipped out of the house sometime during the night. I made my way to the fridge and helped myself to sandwich fixings. It was still just mid morning. While I was hungry for more, I did not feel like cooking eggs or anything.

When I saw the cucumbers and carrots and zucchinis in the fridge, my cock got very erect in my panties, but I decided I wanted to concentrate on food for the moment. I made coffee and sat at the kitchen table eating and wondering what to do with the day.

Mom was gone until evening. I did not know what Cassie's plans were. I began to plan my own day, which would involve considerable time with my dildo, practising makeup, and browsing websites for fashions that I liked. I might even find some porn to jerk off to.

I knew I had some Carl homework which had to be turned in the next day, but after last night I really needed a Sinful Sindy day!

I showered away the sweat from last night, but kept my hair in a shower cap. I did not want to have to take several hours to get it fully dry. Cassie was still sound asleep as I grabbed various items from bags under my bed where I hid them from mom and then made my way to mom's room. She had a makeup mirror and a full length mirror.

I thought about putting on a pair of black lace panties, because I LOVED the feel of the lace on my cock, but instead I put on the fishnet panty hose that I had bought during the week. I then slipped on a pair of three inch heels and I practised walking and posing in front of mom's mirror. My legs looked SO sexy in the fishnets and my rigid cock bulged out the crotch area. I was dying to grab my cock, but resisted the urge.

Now that I was in Sindy mode, I desperately wanted a cigarette, but I resisted as mom was a non-smoker and would have a fit if she smelled smoke in her room.

I opened my makeup bag, sat at mom's makeup mirror and practised apply my foundation, lipstick and eye makeup. I tried my eyeshadow, liner and mascara several different ways. I played with the lighting of the mirror to see which styling of makeup worked best under bright lighting, dim lighting, etc.

After almost three quarters of an hour, I was desperate for a cigarette and for a cum!

I gathered everything up carefully and went back to my room. I removed my fishnets so that I would not rip them, but I replaced them with some sheer black nylon leggings and put the heels back on. I made myself comfortable on the bed and lubed up my ass. I then took my thick rubber dildo and worked the head of it past my anal ring. Before sliding it in further, I lit a cigarette. I lay back and as I smoked I languidly worked the fake cock slowing in and out of my ass. I blissfully daydreamed of Johnny and Danny and the guys from the fraternity, all drilling their cocks into my ass, as I practised sexily dragging on my cigarette, and fucking myself with the dildo. I had actually only had two different guys fuck me, and Danny only once, but I knew I wanted many more cocks up my boipussy - many many many MANY more!

Once the cigarette was done, I lifted my legs so that I had even better access and I used one hand to shove the rubber cock inside me, while using the other to strum my erect cock. As I pulled the dick out and shoved it in harder, I was grunting and groaning but I was not getting the nice action that I wanted - my prostate was not being stroked!

I was just contemplating pulling the dildo out and fastening it to the wall, when my sister cleared her throat from the doorway. She was wearing a flimsy nighty as she sauntered into the room. Need a hand, she asked, as she grabbed hold of the dildo and thrust it back up inside of me. She gave me a few more pushes and pulls before she collapsed on the bed beside me, giggling.

She kissed me tenderly and hugged me, complimenting me on my makeup, particularly my eyes. She confessed to me that last night she had let Johnny fuck her in the ass. It had felt.... uncomfortable, but not unpleasant, and had not resulted in any orgasm for her. Johnny though had found it to be wonderful, praising her ass as being the tightest thing he had ever fucked (I was jealous, and was going to have to have words with that man!)

I told her that I absolutely LOVED having a man laying on top of me, or kneeling behind me, and shoving his prick up my bottom. It felt so wonderful to be connected to another person that way. Of course, I could see that women would have the same sense of bonding with a pussy and would not need a man in their ass. But me, I really wanted a man's cock sunk deep in my ass, whether from the front, or behind, or even if I was riding on top of him.

I really missed not being fucked last night. I really needed a good fucking, I told her. Do you really mean that, she asked me? I nodded. She smirked and walked out of the room saying she would be right back. She definitely walked slightly lopsided, her ass sore from her own dicking the night before.

She was gone for a few minutes. When she returned she was wearing a strapon harness, with an eight inch plastic penis. Where did you get that?, I asked her. She told me that she got it from mom's secret stash of sex toys. I did not know she had a secret stash, but evidently Cassie had found it quite some time ago and had been borrowing from it from time to time.

Cassie said she had no idea who mom had been fucking with it, or who had been fucking mom, but it smelled and tasted like pussy! She told me to get on my knees, and I did. Cassie immediately shoved the rubber dick in my mouth, telling me to suck it and get it nice and wet, because she intended to drive it deep into my boipussy!

It did indeed taste strange. Was this my first taste of a pussy other than Cassie's? And was it mom's dried juices that I was tasting? I put that thought aside as Cassie fucked my face. I could see that what she was wearing was actually a double-headed dildo, which fit through a ring to give it some support. She had sunk one end (I did not know how long it was) into her own cunt.

Cassie pushed me back onto the bed, and pushed my legs back so that my knees were at my ears. She giggled as she placed the head of the dong at the entrance to my boipussy and she pushed inside. She was surprised at how easily it slipped inside me and how quickly my ass gobbled up the full length! She had never fucked anyone in this way before, but she soon got into a good rhythm of thrusting in and out of me while holding onto my ankles.

When she ran out of energy she collapsed on top of me, the dildo still deep inside both of us. We kissed hungrily, swapping tongues and spit. When she gained a bit of strength she thrust into me for a few more minutes, Her mouth was beside my ear and she kept whispering to me, telling me that I was such a sexy ass slut and how much she loved fucking me!

When she was finally too tired to continue, we lay beside each other smoking.

I told her I had loved the fucking, but it had still not satisfied me. She in turn said she had like the power that she felt when she was on top, and she wanted to do this again. She also said she liked looking into my pretty face while doing it - she now understood the power that a guy felt when fucking his girlfriend.

I admitted to still being horny. Cassie got a mischievous look and slid down the bed. She played with my cock for a couple of minutes and then, making up her mind, she proceeded to give me a blow job that lasted only two minutes before I exploded in her mouth. She swallowed.

This was only the second time I'd ever been sucked off, and I loved it. But I still had not fucked a girl. When I mentioned that to Cassie, she told me bluntly that she was NOT going to let me fuck her. She did say that, considering how much of a slut I had become in the last several weeks, she could not imagine me staying a virgin too much longer. I countered with the fact that I preferred the girl's role in sex, but she figured that sometime soon, I would get a chance.

She did ask if I had to choose, would I want to fuck someone, or be fucked? I told her that the decision was easy. I LOVED having a cock up my ass and would choose that anytime!

We jumped in the shower together and caressed and kissed a lot. Afterwards we spent another hour with Cassie helping me practise my makeup some more.

We did some girl laundry and got the place tidied up, my bags once again hidden under my bed, before Mr. Henderson dropped Mom off late that evening.

Chapter 12 - Love is Fleeting

On Monday I managed to get Johnny alone for a few minutes and told him that the next night I did not want just a couple hour quickie with him somewhere. I wanted the entire evening. He said he would work something out. We were alone in the hallway and so I pulled his head down and kissed him tenderly. As we kissed, I rubbed my hand across his hard dick. Yes, I was in Carl mode, but I was comfortable with Johnny and did not mind showing him affection, teasing him a bit, knowing that it would be Sindy who delivered the full goods!