Date: Mon, 12 Nov 2007 19:45:58 -0800 (PST) From: Kara Brown Subject: College Crossdressing Slut 22: Roleplaying with Daddy College Crossdressing Slut Chapter 22: Role-playing with Daddy I got home a lot earlier than I had planned that night but I definitely didn't feel like doing anything. When I arrived at my apartment, the first thing I did was go check out the mirror. I felt like such a naughty girl since I had taken off my panties and entered my apartment holding them in my hand. As I looked in the mirror, my mascara stained face was a mess but that's not what I wanted to see. I immediately checked out my ass. It was bright red! The ice had numbed it significantly but my ass was fire truck red all the way around. I went to my bed and lied down on my tummy. I felt a little sick to my stomach. I had such a crush on Robert but he was really mad now and I didn't know how long he would be mad for. I really wanted to be with Robert but I also wanted to have my wild times with other guys. Plus, I didn't even know how Robert felt about me. Sometimes he seemed to like me a lot and sometimes he seemed like he just wanted to use me for a warm hole to stick his cock. I fell asleep with a stinging ass and a nauseous stomach. When I woke up in the morning, I called Robert right away. It was pretty early but I really wanted to talk to him. I got his voicemail so I tried to explain everything but my message was too long so I had to call back and leave a second message. I really didn't feel like going to school so I skipped class and waited for Robert to call back. Unfortunately, he never called that day. I spent the rest of the day upset and lounging around in a tank top and gray sweats. I called again on Friday but Robert still wouldn't answer. In fact, pretty much nobody was calling and I felt pretty lonely. Finally on Saturday I got a call, only it wasn't Robert, it was Gary. "Hi beautiful, I was hoping you were back but I didn't hear from you." Gary said. "Hi Daddy." I was actually pretty happy to hear his voice even though I wished it was Robert. "Sorry I didn't call, I've been busy." "That's OK. What are you doing tonight sweetie?" He asked. I really didn't feel like doing much that night and told him so. "Are you sure baby, I have a present for you." He informed me. I was intrigued. "What kind of present?" I asked coyly. "One you will look really hot in." Gary replied. I thought it over. I wasn't in the mood for romance or to be with a guy but I was always in the mood to try a new outfit on. Besides, I hadn't been out of the house in days. Finally I relented, "OK Daddy, I'll see you in a couple hours." I somberly took a shower, careful not to damage my fake tattoo, and got ready. Here I was trying not to be such a slut and now I was going over to let an older guy fuck me just so I could get some free clothes. It was sad but I couldn't help myself. It wasn't going to make me happy but I wanted to be near someone that night. I put on my makeup and dressed fairly conservatively since I knew Gary would have something for me to wear. I had on a white top and some tight black pants and a thong so no panty lines would show. I then headed out to visit my Daddy. When I arrived at his house I didn't get quite as turned on as last time. Last time I had been there, his long driveway and expensive looking house had been a turn on. I guess that was just my bratty, gold digging side. This time, those feelings just made me feel guilty. I made my way up the walk and knocked on the door. Gary greeted me with a kiss. He was looking good, but I wasn't turned on that much for some reason. My "blah" feelings must have come through because he asked,"Anything wrong my little girl?" "No Daddy, I'm fine." I replied and tried to smile. "Good girl." He replied. "Now let's have some dinner and then I'll show you what I got you." We sat down and had dinner he had just pulled out of the oven. It was pretty good; Gary really was a good cook. The only thing was I wasn't really in the mood to eat. My stomach was still a little nauseous from think about Robert being mad at me. After dinner, Gary said "Now it's time for your present." "Goodie." I replied and tried to look excited as he led me upstairs to his room. When we got there I saw an entire outfit laid out on his bed. It was really hot and slutty looking too. It was a tiny little black, vinyl looking miniskirt with a way to lace it that went all the way up the side and a tube top that laced up as well. There was also a pair of boots that looked like hooker boots and black fishnet stockings. "You said you wanted to role play so I had that in mind for the night." Gary informed me. "Uhh, what kind of role-playing did you want to do?" I asked, not sure I wanted to play. "Why Hooker and John of course." He replied. "That's great," I thought to myself. Here I was feeling like a total hooker and now I got to actually pretend to be one. "OK." I said with a sigh, I'll get dressed and meet you downstairs. "One more thing, I got you something else too." He told me and went to his dresser and pulled out two fake looking breasts. "These are for you too; I want you to fill out the tube top." "Wow, he really spent a lot of money on me." I thought to myself. "How much money does he actually make?" Gary turned around to leave but added "Don't meet me downstairs, meet me by my mailbox. I'm going to pick you up in my Lexus." "OK Daddy." I replied and began to get dressed. I started out by undressing and then feeling the breast forms. They felt pretty interesting, kind of how I imagined real breasts would feel, kind of like a jelly type feeling. "No wonder guys like these" I thought to myself. The rest of the getting dressed was awkward. I got the skirt on first but it was really tight. If I had had big girl hips I might not have been able to squeeze it on. I then put on the tube top and inserted the new fake breast. They felt way better than my old fake breasts which were more like soft Styrofoam. These must have been expensive. The problem was then getting the boots on. I'm pretty flexible and stretch every morning, but the boots were nearly impossible to get on with my skirt on so I had to take that off. It then turned out that the boots were just too small so I unfortunately had to settle for just the black fishnets to cover my legs. I then had to lace up my skirt again and check myself out in the mirror. My thong looked stupid since you could see the band through where I laced up my skirt so I peeled it down my legs and reexamined myself. I really did look like a hooker! A spin around to do a quick butt check reminded me of my tattoo on my lower back. I hope Gary liked it! I made my way down the stairs and outside to meet him by his mailbox. It felt exciting but definitely scary to walk outside in an unknown neighborhood looking like a prostitute. Luckily it was dark by then and it was a pretty quite street. I had never role-played like this before so I didn't know exactly how it worked but I figured I should just wait for him to show up. I felt really hot in these clothes but for some reason I didn't feel like getting fucked. I felt sick knowing Robert was mad at me and this whole night just confirmed I was a whore. "I guess it makes it more realistic that I am playing a whore and I don't actually want to get fucked," I thought to myself. I waited outside for about five minutes when I saw a pair of headlights speeding down the street. I walked closer to the street until I noticed the headlights were kind of high up and it wasn't a car but a pickup truck or SUV coming towards me. I panicked a little and hurried back up Gary's driveway (which was hard in the tight skirt and fishnet stockinged feet). I heard what turned out to be an SUV slow down so I turned around and sure enough, it wasn't Gary but just some asshole slowing down to see what he probably thought was a hooker. I moved towards Gary's front door and the SUV slowly moved on. I waited there another five minutes or so when I finally saw another car make its way down the street. I slowly walked down to get a better view and when I saw it was a silver Lexus with tinted windows, I moved a little faster. The window rolled down and sure enough it was Gary. "How are you doing tonight sexy?" He asked "Not bad mister, how are you? Looking for a good time?" "Always. How much is a good time?" I had no idea how much prostitutes charged so I paused and said "20 bucks for oral and 40 if you want to fuck my pussy." "How much to fuck your hot ass?" Gary asked. "Ummm, a hundred?" I almost asked. I really had no idea what to answer but it was fake anyway. Gary reached in his wallet and handed me a $100 bill and told me to get in the car. I put the bill in my tube top which was the only place it would fit and scurried to the passenger seat to take my seat. Gary then drove past his driveway and said "I know a discreet park we can go to. Get me hard baby." I was a little nervous so I started "Ummm, I don't..." "Don't worry, we're just going back to my place but get me hard." He informed me. I obeyed and took his cock out and rubbed his cock which was already kind of hard and had precum. He was really prepared as I saw a couple Trojan ribbed condoms and a bottle of lube in the drink holder. We just drove around the block once and minutes later we pulled into his garage. "Nobody comes to this park." He said, he was really getting into the role-playing thing. We exited his car and I grabbed the condoms and lube and scampered back to his side of the car in my short skirt. "How do you want to do it?" I asked. "I want you bent over the hood of the car." He replied. "It's your money mister." I replied and then dropped to my knees and added, "Just let me get a condom on you." I figured a real hooker wouldn't suck without a condom so I told him to take his pants down and rubbed him till he got hard. I then put the condom in my mouth to roll down his cock. I withstood the disgusting taste of the pre-lubed condom and then proceeded to flick his balls with my tongue as I worked some lube in my ass. I didn't know if hookers actually licked balls, but I had to keep him hard as I lubed my ass. Surprisingly, my clittie barely moved as I did this. When I was ready to go I put my hands up so he could help me up and then bent over hood of his car. "OK, let's do this" I said. "Wow, when did you get the tattoo?" He asked in a surprised tone. "It's a temp, do you want to fuck or not?" I was trying to act like a little bit of a bitchy hooker, but honestly, I kind of just wanted to get it over with. This was a hot situation, but I couldn't enjoy it with what had happened the last week. "Alright, let's fuck." He said and tried to roll my tight skirt up my hips. "Just unlace it." I told him over my shoulder. He loosened the laces, rolled it up my back and lined up his cock. I gritted my teeth as he worked it in very quickly and started fucking me. He fucked me like a hooker, without passion. It totally reminded me of the way Trevor fucked me and that made me sad again as I thought of what a hooker I really was. When I was used to his cock again I started saying generic phrases without any passion like "That's right, fuck me.", "You feel so big," and "Cum for me stud." I basically said these in a monotone voice like I imagined a hooker might, but plus, I really wasn't that into it. "How many guys have been in your ass today?" Gary asked. "You're the first one this month big spender." I informed him as I stay bent over the hood looking straight ahead. I fixated on the power drill he had hanging on the wall across from me as he continued to slowly and rhythmically fuck me. He wasn't bad at all but my clittie stayed soft against the warmness of the hood of his expensive car. "You ready to cum yet?" I asked. "Hold on." He replied and reached over my back to get his hands on the fake breast forms he had bought me. "Watch the hands." I informed him. "On my hips only." That was kind of bitchy of me but I didn't think hookers let you ogle their breasts and I tried to stay in character. His hands moved back to my hips and minutes later he was cumming in the condom. I just stayed bent over the hood with my elbows on the hood and told him "Good job stud." Gary pulled out and I immediately stood up and took the condom off his cock and tossed it in the trash can. "You were the best tonight mister." I told him. "You were great Kara. You should be an actress." He informed me. "You mean I make a great whore?" I asked, half kidding. I was in a bad mood tonight. "That's not what I meant sweetie," He said, "Now give me a kiss." We kissed and his hands went straight for my boobs. "These feel great." He told me. "I'm glad you bought them for me Daddy." I thanked him. "Good, let's go upstairs and cuddle." He said as he led me upstairs by the hand. I really didn't feel like it, plus I wasn't really dressed for cuddling. He had spent so much money on me though; I didn't feel like I could say no. I lay next to him in bed and he groped me and held me. He really liked playing with the fake boobies which I couldn't blame him. We talked for a little bit but I really didn't feel like staying. Nothing against Gary, I just didn't feel like being with anyone but Robert right then. Gary started to fall asleep so I whispered to him that I had to go. He woke up and said "Awww, so soon baby girl?" "Yes Daddy, I have to go. Can I take these new clothes with me?" "Why don't you leave them here. Then you always have some clothes if you spend the night." I really wanted to take them with me. If Robert ever called I'm sure he would love to see me in these, but I didn't make a big deal of it. I just began taking my clothes off. The $100 bill I had put in my tube top came out as I undressed. I still owed my dad the $200 bucks so I really wanted to keep it. I asked Gary coyly, "Oh, here is the money you gave me, do you want me to leave it somewhere?" "You can keep it sweetie. You earned it." "Yayyy!" I thought to myself and then tried to push my luck. "Thanks Daddy, I can use this to pay off some bills." Gary took the bait. "Do you have money problems sweetie?" "A little Daddy. My parents are making me pay them back some money and won't let me use my credit card to buy clothes anymore." I said in a little girl voice. "Did you spend a lot of money?" Gary asked. "Oh no Daddy, just a couple hundred. I just had to buy a few clothes to look good for you. Now I just have to pay them back is all. Now I'm halfway there." I felt a little guilty hitting him up for money but money didn't seem to mean much to him at all. Besides, I really didn't feel like getting a job quite yet. "That's nothing." He replied. "I don't carry much cash but if you come over next Saturday I'll take care of the rest of it for you. I can't have my little girl worrying about money." "Ooh thanks Daddy! Maybe we can play another game like we did today." I said, continuing to talk in my little girl voice. "Of course. What do you want to do?" "You pick Daddy. Just as long as it's not icky." I giggled as I continued dressing. "What's icky?" He smiled. I laughed, "You probably know Daddy. Just make sure its fun." "OK sweetie, it will be fun." I had finished dressing by then so I climbed on the bed and started sucking Gary's cock. He was so good to me; I don't know why I had not had that good of time getting fucked earlier. I sucked my Daddy's yummy cock as he watched. "Oh Daddy, the boots were too small for me." I informed him as I let his cock slip out of my mouth. "OK sweetie, I'll return them." He moaned. "Yay!" I replied and got back to slurping on his cock. Soon I was rewarded by the cum in my mouth which of course I swallowed for him. "OK Daddy, I have to go. I'll see you on Saturday." "OK sweetie, drive safe." He told me as I left the room. I still hadn't cum so I went home and played with my clittie till I came thinking about being fucked over the hood of Gary's Lexus.