Date: Sun, 16 Dec 2007 23:05:42 -0800 (PST) From: Kara Brown <kara_cd412@yahoo.com> Subject: College Crossdressing Slut 23: Naughty Schoolgirl College Crossdressing Slut Chapter 23: Naughty Schoolgirl The next week was fairly uneventful. I tried to call Robert again but he wouldn't answer his phone. I don't know what his problem was but he was being a real jerk. The closest I got to talk to him was when Lance called me during the week a couple times and we instant messaged each other. I tried to get information from him on why Robert was mad but he just said Robert was acting weird and changed the subject. I couldn't tell if Lance was being sweet and checking up on me or if he was just trying to be nice so he could fuck me. I enjoyed talking to him though so I didn't care either way. I was starting to get over Robert, it was just a stupid little crush anyway. Maybe I should get Lance to fuck me just to drive Robert really crazy. "Yeah, I'll do it," I resolved to myself. Robert deserved it, besides it wasn't any sort of punishment to me to finally get Lance's cock in my ass. What I was really excited about though was seeing Gary on Saturday (writing about three guys in the first two paragraphs makes me realize what a slut I was back then). I knew Gary had something different and fun planned and I couldn't wait to find out what it was. For a sweet older guy, he really liked to role play. I had already sent my parents the 100 bucks Gary had given me and let them know I would pay them the rest next week. I lied and told them I had found a job on campus and that's how I could pay them back. Saturday finally came and I was so excited when Gary called. He wouldn't tell me what he had planned but I could tell he was excited too. I just did the shower and makeup thing, cleaned my little fuck hole and threw on a skirt outfit to hurry to his place. I arrived and Gary greeted me with a "Hi cutie!" "Hi Daddy!" I responded with a big smile. "Are you hungry for some Dinner?" He asked. I just kissed him and replied "All I'm hungry for right now is your cock Daddy." Daddy smiled and said "Well let's get you in your schoolgirl costume and we can work that out." "Yaayy!" I shrieked in a high pitch voice. "Am I a naughty schoolgirl or a good schoolgirl?" I asked. "Which do you want to be sweetie?" "Naughty is more fun." I said coyly. "Where is it?" "Upstairs on the bed" Gary responded. "Thanks Daddy!" I said before I kissed him and raced up the stairs. "Meet me in my office when you're done," He yelled after me. The outfit was super cute! It was kind of plain but I loved it. It was a short red pleated skirt, a white top that tied in the front and showed off my flat stomach, and white stockings. He also laid out two pairs of panties, white cotton bikini panties and red ruffled panties. The red ruffled panties were super cute but I decide to go more traditional for the white cotton ones. The breast forms didn't really fit in my top so I left those out. I then scampered down the stairs to find Daddy's office. It was easy to find because he had written "Principal's Office" on a piece of paper and taped it to one of the downstairs doors. I knocked on the door and was told to enter in a stern voice. I opened the door and Gary was seated at his solid wood desk wearing a suit jacket and a black tie. "You wanted to see me Principal Thompson?" I said in a purposefully wavering voice. "Sit down young lady." He replied sternly. I obeyed and pulled a chair out, bending over to brush off the seat so he could see up my short skirt before I sat down. "Do you know why you're in here?" He asked. "I have no idea." I replied trying to sound like a brat. "I know you know. You were caught helping your boyfriend Billy cheat in Chemistry," Gary responded. "We've been having a lot of trouble with you lately ever since you've been dating that no good boy Billy." "Fine, just give me a detention then." I responded flippantly. "I'm afraid we've gone beyond that. It's time we brought your parents in for a conference." I made my eyes wide, "No, Principal Thompson. Please, don't call my father." "Why is that?" Gary asked as he reached for the phone on his desk. ""My Dad said if I got in trouble one more time at school he would spank me on my bare bottom with his belt. It's embarrassing and I haven't been spanked since I was ten. I'm way too old for it!" "No, you're way too old to be acting like a spoiled brat. Sounds to me like your Dad has the right idea. Since I haven't been able to reach you, maybe he can." "No Please! I'll die of embarrassment if I have to get spanked on my bare butt by him. Can't we do anything else?" "I'm sorry but that sounds like the best punishment for you." Gary responded and started dialing numbers. "Wait!" I stood up. "What if you did it? That way I could still learn my lesson." "I'm afraid that would be inappropriate." Gary replied calmly. "Oh, I'm sure we could work something out Principle Thompson." I stopped whining and tried to seduce him by walking over to his side of the desk. "Is this a picture of Mrs. Thompson?" I asked pointing to a frame on his desk. "Yes it is, sit down Kara" he answered. "Looks like you've been married for awhile. Does she still take care of all your needs?" I asked coyly. "This is inappropriate Kara" was his response. "I've just heard that sometimes after a long time of being married, the women let's up on some of her wifely duties. Certain things she may have been happy to do before marriage suddenly stop. Certain things a young high school girl may like doing..." I trailed off as I rubbed his cock between his nice slacks. Gary stood up "Bend over the desk young lady and take your panties down." He ordered as he pulled a ruler out of his desk. "Mr. Thompson," I purred "There's no need for that part. Let me just take care of you." "No Kara, we'll get to that. First there's the matter of your punishment." "Mr. Thompson!" I pouted. "Now Kara or I'll call your father." He ordered. I sulked as I walked to the other side of the desk and bent over and flipped my skirt. "Drop your panties too." He added. "No!" I yelled over my shoulder. His first reply was two quick swats of the ruler on each cheek. "Yow!" I shrieked. "It does not officially begin until you drop your panties." He said sternly. I pulled the waistband of my panties down slowly. "All the way past your butt." He warned. I finally complied and Gary went on to lecture me about attending class and studying and the importance of ethics. He really knew how to drag it out; he must have done this before. Finally he lined up beside me with his ruler and told me to count off until we reached 30. "That's way too much! It should only be ten at the most! I didn't shoot anyone!" I begged. "Considering I'm not using my belt, consider yourself lucky." He responded. "Now count off, if you don't count it doesn't count." He informed me as he immediately started whacking my ass with the ruler. I was taken by surprise by his quickness and still thought I could argue so I missed counting the first three swats. I learned from my mistake and immediately picked up the count. The ruler stung but it actually didn't hurt that bad, mainly because Gary was taking it a little easy on me. I still played it up by sulking and saying "owie" a lot. After the tenth swat he informed me that the hard ones were too come. He wasn't lying as he really wound up on a few and I could picture what the red marks must look like on my ass. After swat 16 though, they suddenly stopped. "Cheap piece of junk" Gary muttered. I looked over my shoulder and saw the cheap wooden ruler cracked almost in half. "Oh well, I guess I'm done." I said as I pulled my panties up. "No, this just means you get a break. Besides, this is a good time for the second part of your punishment while my secretary brings me another ruler." Gary sat down at his desk and pretended to use an intercom to ask his secretary to bring a ruler. "Yeah right." I responded and rolled my eyes. "Like I'm going to get caught blowing you while your secretary comes in." "That's why you'll be under the desk. Now hurry up or I'll start your second spanking over from the beginning." I really wanted to get Gary's cock in my mouth so I hurried under his desk and unzipped his pants. He looked so hot in his suit! I was very cramped but I loved being there. As I slipped his cock in my mouth I felt like I was blowing the president or some big important man under his desk during lunch. I sucked on his delicious cock while Gary said "Just leave it on the table over there and go to lunch Mrs. Jones. I'll grab it later," Pretending like he was talking to his secretary. He was really getting into it! Unfortunately, I was cramping up under his desk so I said "Sir, let me out for a second please." Gary obliged and I climbed out from under his desk, stretched for a second and then got back to my work of sucking his cock. "Am I better than your wife?" I asked. "Mmmm, definitely," he moaned, "She hasn't blown me in years." "That's too bad, I love it." I replied as I slurped on his cock. "I've heard that." He responded. "Principal Thompson!" I gasped as I let his cock pop out of my mouth. "What did you hear?" Gary just guided my mouth back on his cock and said "Keep sucking." I obeyed and he added "Now Kara, just because I'm the Principal doesn't mean that I don't hear things. I heard from the Principal of your Junior High you've been blowing boys since you were in 8th grade and to watch out for you. Have you been letting all the boys fuck you too Kara?" "No Principal Thompson." I responded softly between slurps. "Don't try to pretend like you're a virgin Kara." "Honest, Billy is the only guy I've gone all the way with Sir." "I find it hard to believe the biggest cocksucker in the school has only been fucked by one guy." "It's true Principal Thompson," I assured as I rubbed his cock. "I can't get pregnant or my Dad would kill me so I just gave my boyfriends blowjobs before." "That's too bad. I had a way for you to get out of the second part of your spanking Kara." I laughed, "Principal Thompson! Only Billy gets to fuck me." "Stand up Kara." He ordered. I got another lick of his cock in and obeyed. "Billy is a trouble maker and he's in trouble for cheating too. He could be heading to reform school if he keeps getting in trouble. You have a chance to keep him out of it do you hear?" "B-b-but," I stammered "I can't. Besides, you don't even have a condom here." "Kara, have you ever had anal sex before?" He asked. I looked down sheepishly so he continued "Be honest." "Only a couple times when I was on my period." "Did you like it?" "It was ok." I said as I continued looking down. "It hurts though." "That's ok. The spanking will hurt more and this way you can keep Billy out of trouble." He responded. I pretended to think for a second. "OK sir, just use a lot of lube and don't tell anyone. You're bigger than Billy so go slow." "Take your panties off, bend back over the desk and I'll get you wet." I obeyed and soon I was bent over with my hands on the desk, looking at my panties on his desk. Gary got behind me and started rimming my tight little hole. I moaned in ecstasy, I absolutely love getting my pussyhole licked! I kept moaning until I pictured if my real high school principal was doing this to me. That made me laugh for a second and Gary said "What's so funny?" "Ummm, nothing," I lied, "It just tickles a little." "Well you'll be glad I did it. This isn't some little teenager's cock you're getting in your ass." Gary kept licking me and I was loving it! I'd never had a guy put that much saliva on my hole before he fucked me. Soon he was lining up his cock and pressing it against my hole. "Oww Sir! That hurts!" I yelled as he slid it in. "You'll get used to it" he replied as he slid in farther. "Mmm, your cock feels so big Mr., Thompson," I moaned as he began fucking me. I was so wet from his saliva it made a squelching noise as he fucked me. "I told you this wasn't a teenager's cock." He responded as he was thrusting into me. "Owie Sir! I can tell" I shrieked as I gripped the desk hard. He must have been really turned on by the blowjob because within minutes he filled my ass up with cum. He stayed in for a minute to let me clamp down and milk every drop before he withdrew his cock from my hole. I didn't get a chance to cum and I was still really turned on. "You took your punishment like a good girl, now put your panties on and go to class and we'll pretend this never happened." "Yes sir," I replied and found my panties and slid them up my thighs. Gary then spun me around and kissed me. "You were amazing Kara! You really need to start acting!" "What about you?" I giggled and blushed. "You really had me turned on." "Well I've done this before." "Oh." I replied. "Hope it was still fun?" "Of course it was fun! I can't control myself around you." "Good," I smiled. "You don't have to leave yet do you?" "No, not yet." I answered. "Good, Why don't you go upstairs while I finish off some work and I'll meet you up there in a little bit." "OK Daddy" I responded and went upstairs. I obeyed and went upstairs. I put on just the red ruffled panties and the pink tank top I came over in. It may not have matched but it was comfortable. Daddy came up the stairs about half an hour later and said "I'm sorry sweetie, but I'm tired. Do you mid if we go to sleep and cuddle?" I was still very horny but I couldn't say no. I snuggled up in bed next to him with my clittie still hard. He fell asleep very fast but I wasn't tired and being held in his comforting arms didn't do much to make my clittie go down. I shook him awake after about an hour. "Want to play Daddy?" I asked. "Not now sweetie," he answered tiredly. "In the morning." "OK," I pouted. "I'm going to use your computer though." Gary just nodded and went back to sleep. I couldn't sleep so I crept downstairs and went to play around on his computer. It was kind of late but I signed onto my Instant Messenger account, kind of hoping for some dirty chat. I was surprised to see Lance was online. I waited for him to make the first move and after a couple minutes he IM'd me. Lance: Hey Cutie, why are you up so late. Me: Can't sleep :(. Lance: awww, poor girl Me: I know lol. Lance: Why can't you sleep? Me: I dunno, just thinking about stuff Lance: aww, you're too cute to have to think. Me: whatever jerk, lol Lance: J/k cutie. Hey, I'm going to be near your place on Monday Me: Really? Lance: Yeah, I have training for my new job and they're putting me up in a hotel for a couple days. Me: Oooh fun, you'll have to cum visit me. Lance: If I have a room by myself you'll have to come visit me ;) Me: I will! I didn't even know you were getting a new job. Lance: Yeah, I had to get one when I graduated. Me: Oh, lol! I didn't even know you graduated. Lance: What a friend! I graduated in December this year. Me: I'm sorry! We'll have to celebrate. Lance: Definitely. You owe me now. I have to go but I'll see you on Monday cutie. Me: OK stud. Bye! I was excited but a little tired so I joined my Daddy upstairs and went to sleep in his arms.