Date: Wed, 29 Oct 2008 16:43:11 -0700 (PDT) From: Kara Brown <kara_cd412@yahoo.com> Subject: Re: College Crossdressing Slut 27 College Crossdressing Slut Chapter 27 I awoke the next morning to Aline and Lance giggling and kissing a little on the bed. I pretended to be asleep so I wouldn't disturb them. I heard them shift and get off the bed so I opened my eyes a little and watched them head to the bathroom in Aline's room. The door shut behind them and I knew what was coming next. Even though the door was shut, I could hear what was going on: the ruffling of fabric, Lance's soft moans, and the unmistakable sound of lips slurping on a cock. I sat on the edge of the bed and listened while I felt a little nauseous. That was supposed to be my job. After about ten minutes they emerged giggling again. "Oh, hey Kara. I didn't know you were up" Aline said. "Yeah, I'm up," was my only response. "Good" said Lance "I need a ride home, who's going to give it to me." "I will" I responded "Just let me fix my makeup." "Aww, thanks Kara" said Aline. "Yeah, thanks beautiful" Lance added. I fixed my clothes and makeup and Lance and I got in my car and left for his place. I didn't really like driving in the day when I was dressed but I didn't have much of a choice. We were pretty silent for awhile until Lance said "So you and Robert got along ok?" "I guess" I replied. "You and Aline really hit it off too it looks like." "Yeah, she's an awesome girl." Finally I just decided to come out and say it "Did you tell Robert I was a brat." "He told you that?" Lance asked. "So you did say it?" "All I did was agree with him when he said you could be bratty and immature sometimes. I wasn't trying to be mean and it's not a real bad thing but sometimes it can be true." "Whatever, I'm not a brat." "See you're being a little bratty right now" Lance laughed at me. "Knock it off" I giggled and then asked more seriously, "So is that why you like Aline? Because I'm too immature?" "I like you both" he said before he paused and added "I think Aline and I have a little more in common though." I didn't say anything so he continued "You're so hot Kara but she's closer to my age. Besides you don't even want a boyfriend." "Yes I do" I thought to myself. I then asked "So are you two a couple now?" "I don't know" he responded. "Do you always go after Robert's leftovers?" I asked trying to upset him. "See, you're being a brat again, is that why Robert left last night?" He tried to force a laugh but I could tell my comment had bothered him. "Sorry if I'm a brat when the guy I'm with leaves to fuck my best friend." "We were never going out Kara." "Yeah, but you were supposed to be with me last night. You're not supposed to leave me alone with a guy I couldn't stand." "For not standing each other, you two had a pretty good time" he said. Lance then paused and added "Look Kara, I wasn't trying to be a jerk. I thought we were all there for a little fun. I like you but you can don't even know what you want. You can't have a relationship until you grow up and realize that." I stayed silent so he added ". I got pretty jealous when I heard you getting fucked by Robert." "Whatever," I replied, "I don't want a relationship either." We didn't talk about last night for the rest of the drive and instead just made small talk about little stuff. I dropped Lance off and he gave me a small peck on the cheek and then a full kiss on the lips before he left. On my Drive back home, Gary called and told me to be at his place at 7:00. I had totally forgotten about that! I really didn't feel like going. My butt still felt sore from the anal pounding I had received the night before and I just wasn't in the mood. I felt I couldn't say no since I had canceled on him last night to get fucked by two other guys so I just pretended like I was excited. It was already the afternoon by the time I got home so I just moped around a little and then took a shower and got ready. I figured he would have another outfit for me so I just put on some black pants, black bikini panties and a red top. I did my makeup and left for Gary's place. When I arrived Gary greeted me with a kiss and a "hi gorgeous". "Hi Daddy!" I responded, pretending to be excited to be there. "How's my little girl?" "Good Daddy. What are we doing tonight?" "What do you want to do?" he asked. "Did you buy me a new outfit?" I asked hopefully. "Yes, but you don't get it tonight" he responded. "Only good girls who don't break a date get presents." "But Daddy," I whined "I just wore these old clothes here." I was such a little golddigger. I honestly was a little upset too. I really didn't even know if I wanted to come back the next weekend. "No whining Kara. You'll get it next weekend if you're good." He then added, "If you're going to whine, maybe you should dress in the schoolgirl outfit and get the spanking you deserve." I was absolutely not in the mood for a spanking today so that didn't appeal to me at all. Instead I suggested I wear the hooker outfit again. `I'm feeling a little too frisky to just be an innocent schoolgirl" I lied. Really I just wanted to do my duty and let him fuck me. Plus, if we played hooker and john again, maybe I could get some more money from him. I had just bought those clothes yesterday and I had to get them paid for. "That sounds great Kara. I got you the new boots too." "Ooh, thanks Daddy" I responded and we went upstairs to his room to get my outfit. I pulled everything out of the closet and told my Daddy to wait there as I went down the hall to the bathroom to change. He handed me one thing as I started to leave. It was a red hair wig. I shrieked "Oh thank you Daddy!" and started bouncing up and down. When I got to the bathroom I stripped and pulled on the black tube top and skirt and laced them up. I then realized again it was too tight to get my boots and stockings on so I had to unloosen the skirt again before I could pull on the fishnets and hooker boots. I inserted my breast forms in my tube top. Panties didn't really go with this outfit so I went without them. The only thing left to do was switch wigs and so I brushed my new wig really good and put it on. The wig really was gorgeous. It was very classy looking and had a wavy layered look and went down just past my shoulders. I had to admit I looked pretty good as a redhead with my light soft skin. I slowly made my way down the hall to Gary's master bedroom (it was hard to walk in the boots and super tight skirt!) and knocked on the door. Gary answered and I said "Hi, there was an order to Kara's Services for room 233?" "Yes there was" Gary answered, "come in." I entered the room and he had lit a scented candle on the nightstand. "Do you have the money?" I asked. "Of course" he answered and went to his wallet to pull out some money and handed me a $50. I tucked the money in my purse and hoped he would let me keep it. "Ok, this is how it works. There's no kissing and we use a condom for everything- and I mean everything. You paid for one hour and you can cum as many times as you can but you only have an hour. I brought a guy in the lobby and he'll handle any disputes got that?" I really was good at playing a bitchy hooker. "Of course beautiful" Gary smiled and laughed at me a little. "Good, how do you want to do it?" "Why don't you start on top." He responded. "OK, take off your pants and lie back on the bed then" I commanded. Gary obeyed and smirked a little about me giving him orders. I grabbed a condom and lube from my purse, kicked off my boots, and unloosened my skirt and let it hit the floor. I applied plenty of lube to my ass and climbed on the bed. "Nice" he informed me "No panties" "No need for them" I responded. Gary wasn't hard yet so I stayed on all 4's and rubbed his cock with my face right next to the tip but I never put it in my mouth. When he got hard I slipped the condom on and got prepared to ride his cock like a hooker. I winced a bit as I let it slide into me. I was still pretty sore from the fucking I received the night before. I was glad Gary picked this position because I could control the action and take it slow. I really took it slow and told him how big his cock felt and he had the biggest cock I'd seen all week. Gary just cupped my ass as I rode him slowly. Gary was older and definitely took longer to cum than the younger guys I had been with. That was good sometimes but not on a night like tonight when I wasn't in the mood to get fucked at all, much less a long one. I felt bad but I watched the clock as I slowly rode his cock and after about 15 minutes I realized he wasn't going to cum like this. "He must need more friction" I thought to myself and picked up the pace. I could tell he was getting more into it but honestly, it was kind of hurting my ass. It's one thing to be bent over and have a guy pound your sore ass, it's another to have to ride cock hard with a sore ass. Its hard to get yourself to bounce up and down when you know it hurts. I decided to climb off his cock and rolled over on my back with my knees tucked to my chest. "Fuck me like this stud" I toldGary. Gary rolled over on top of me and began fucking me as I lay on my back. I used my legs to brace him so I didn't feel the full force of him pounding me. Gary took it a lot easier than either Robert or Lance did that's for sure. I kept moaning and telling him to "cum for me", "fill up the condom", "shoot his cum in me". Pretty soon he obeyed and I felt his muscled tighten as he came. "Good boy" I said as he rolled off me and I took the condom from his cock and got up to throw it away. "Do you think you have another one in you?" I asked as I walked back to the bed and pulled my skirt back on. "I think so but I need a few minutes" he responded. "Well you have 40 more minute's hun" I informed him. I lay down on the bed next to him and we chatted a bit. We even broke character a little and I acted more like his little girl than the paid hooker I was supposed to be acting like. After about half an hour I told him "Uh oh. Looks like you're running out of time if you want to fuck again mister." I then added "Why don't you take a seat in that chair over there and we see if we can get you back up and running". Gary got up and sat down at the chair by his desk and I put my boots back on and gave him a little strip tease. I sat on his lap with my back towards him and grinded on him as he held my bare waist. His cock started to grow but wasn't quite at full attention. I didn't really want to get fucked again so I stood up and told him to lift my skirt. He did and pulled my skirt up so my bare ass was exposed. "Give it a slap" I encouraged him. He obeyed and gave me a few smacks on my ass. "That's enough" I giggled, "You didn't pay for that much". I then dropped to my knees and pretended to put a condom on his cock. I'm sure a hooker wouldn't suck cock without a condom but I wasn't going to be so mean as to make my Daddy wear one. I then slowly began sucking his balls and getting them nice and wet. I moved up his shaft to lick his cock, taking my time until I got him at full hardness. I then proceeded to suck him hard, slurping on his cock in a super sloppy blowjob. I really gave it my all for about ten minutes but he still couldn't cum. I usually really love sucking cock but I just wanted him to finish up so I could go. "Aren't you going to cum for me?" I asked as I looked up at him and batted my lashes. "I'm trying. You're doing a great job baby." I sucked hard for a couple more minutes but by this time even my well trained mouth was getting sore so I came up with an idea. "Let's try something new baby," I informed him and started sucking on my own index finger. "What are you thinking of doing?" Gary asked. "Nothing" I responded and put my mouth back on his cock. I snuck my finger up to his ass crack and started tickling it a little. "Knock it off Kara," Gary informed me but I didn't listen and stuck my saliva moistened index finger up his asshole. Gary immediately bucked his hips, grabbed my head, and jammed his cock till it felt like I had a third tonsil. I gagged and worried for a second I would throw up as I pulled my head away. I gagged a little more and yelled "Geez, watch it! At least give me some warning." "Gary just laughed at me and said "I could say the same thing." I took a minute to regroup. When I was ready to resume cocksucking, Gary said "No more hanky panky." "Whatever. You've got 5 minutes to cum and I'm going to make you cum." I stuck my finger back up his ass first this time before I put my lips around his cock again. Gary didn't stop me and I think he really enjoyed it as I fingered and blew him at the same time. I didn't find it very erotic though, it just reminded me how close I was to his asshole. Gary seemed to love it and minutes later was ready to cum. "Shoot on my face baby," I ordered him as I pulled my lips off his dick and continued to jerk him with my free hand. Soon he was cumming again but not in the glorious spurting jets of cum I was hoping for. It was just dribbling out a little so I held my tongue out and let him deposit his semen on my tongue. When he was done I swallowed it up with one gulp and licked my lips "All done" I informed him with a smile. "Good Girl" he praised as we apparently had broken from our hooker and john fantasy. "Fun as always daddy but I need to go." "Why so soon? You always leave so soon." I just apologized, made up a story, gave him a peck on the cheek, washed up, and left.