Confessions of a Sex Crazy Cross Dresser Part 8

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Chapter 15: Dangerous Duo I woke up the following morning to an empty bed. I went to the bathroom and when I came out there was a knock on the door. I looked out and saw Peggy with a bag and two cups in her hands. Upon opening the door, Peggy came inside and placed the drinks and bag on the table and gave me a kiss. “I thought you might want some breakfast,” she said. She had on a pair of white shorts, a light blue tank top and her sneakers. “I brought coffee and donuts.” This girl might be a hooker, but what a sweetie and beautiful, too. I kissed her again and she opened her mouth and kissed me back with warmth of a true lover. I was getting aroused again and she must have felt the same way because before we even had a sip of coffee we were making love again, much the same way we did last night. The only difference was Peggy was on top of me, sliding her juicy pussy up and down on my shaft. The pace was very slow again, but the desire and lust was very strong on both of our parts. We fucked for twenty minutes changing positions, but always fucking each other slow and very very deep. She made me feel like my cock was twelve inches long the way she reacted as I thrust my cock in her tight pussy. She cooed gently every time it went in and pulled me in her deeper and deeper. My orgasms were so intense. The cum shot out of me like a syringe shoots out medicine; strong and direct. We came together again looking in each others eyes. “Peg, I have never had orgasms like this before. You make me feel unbelievable,” I said. She started to cry a little bit and said, “Tony, I know it can’t be, but I am falling in love with you and I haven’t known you 24 hours.” We held each other for a while and then ate breakfast. I told her I had a very busy day and wasn’t sure what I was doing tonight. She told me her plans were to go back to her apartment and do some errands and then pack a suitcase and come back around five or six tonight. She was going to stay at a different motel down the street, as she never stayed at the same place twice in the short time she had been a prostitute. I told her that I was loose cannon. I didn’t like being tied down and that I didn’t have a girl friend. I had slept with a lot of girls and yes a lot of hookers. I loved sex and I loved picking up women. I wanted to tell here these things to share something personal with her, because she was sharing so much about herself with me, even the unflattering details of being a hooker. “Tony, can I ask you a personal question? You don’t have to answer if you don’t want to,” she said. “Sure,” I answered. “I don’t want to upset you, but I couldn’t help but notice you shave your body. I mean you have no hair anywhere except a neatly trimmed patch above your penis,” Peggy said. I remembered all the excuses I had thought of in case someone asked this question, but I thought it best I told the truth. I mean, what was it going to hurt if I told her? It was unlikely I would see her again. “I can’t lie to you, I am going to tell you the truth, but it is kind of weird,” I said. “I like to cross dress; you know dress like a woman.” “Really?” Peggy asked. I reached into my briefcase and pulled out the envelopes with my pictures. I selected the envelope that had one picture of each of my outfits and lingerie shots and passed the stack of about 15 photos to Peggy. She looked at the first photo which showed me dressed as the night I was in the bar at the Holiday Inn and she gasped. “No way this is you?” she said. “You look great! Do you ever go out in public?” I nodded yes and she looked through all the pictures. “I have to admit, it kind of turns me on a little thinking of you all dressed up as woman, especially when you dress like a hooker. Look at you in that black dress with the zippers!” Peggy commented. “It doesn’t bother you?” I asked. “No it doesn’t. I have to admit it is kind of weird, but what’s wrong with doing what you enjoy?” she said. “Well, there is a little more to it. When I dress up, I feel like a real woman and act like one as well,” I said. “You mean you are bi?” she asked. “No, not really, it’s a little complicated, but the bottom line is when I am dressed as a man, I am straight and have no güvenilir bahis desire to be with another guy. But when I am dressed as Sandy, that is my girl name, I like to be a slut and suck cock and get fucked,” I said. “I know how weird it is, but I have only found this out and acted it out the past couple of weeks. I even registered Cassandra Stirling at this hotel” “I guess we have both changed the past two weeks, then.” She laughed. “Do you want to see what I did last night?” I asked. “Sure,” Peggy replied. I pulled out the pictures of Kate, Ricardo and me in our fuck fest. Peggy was looking at the pictures intently. “Wow, you are some kinky slut when you get dressed. That guy has a huge dick and that girl has quite the body.” We talked about another half hour, I showed Peggy my wardrobe, my camera, my sex toys and she was a little weirded out, but it was cool to share everything with someone. She made a comment that we made a pretty weird partnership, her being a hooker, me a cross dresser and at the same time lovers. It was 9:00 and I had to start getting ready for work, we actually took a shower together and we knew we were going to make love in the shower. After we had washed each other and rinsed off, she stood a little bent over with her hands pressed against the shower wall below the shower jet. I slipped my cock into her pussy from behind and started to gently slide my cock deeper in her pussy. I had already cum twice in the past few hours, so I was sure I had nothing left inside me. However I was going to fuck her every time I had the chance, because she was so hot and she made me feel so good. I held her waist as I plunged my cock in her pussy. I loved looking at her perfect ass as I was starting to pick up the pace of my thrusts. Peggy was more vocal in the shower and started to give me directions. “Tony, fuck me honey. You are so deep in me. You are so fucking deep in my cunt.” Our love making was taking another turn; we had been the slow gentle lovers now we were also the lustful naughty lovers. I pulled my dick out so only the tip of my cock was in her pussy and then I gave a powerful upward thrust with my hips so that I buried my cock all the way into pussy so hard that my balls slapped her body next to her clit. “Fuck, that felt good, baby.” She was talking louder. “Take this, baby,” I said as I pounded her harder, then I doubled up and gave her two fierce thrusts. “Oh, Tony, fuck me good now, I am going to cum.” Peggy moaned. She had a powerful orgasm bucking uncontrollably and shoving her ass in my direction engulfing my cock in her wet cunt. I slammed my cock into her as hard and as fast as I could without falling down in the shower. I pulled out of her pussy and turned off the shower I stepped out of the tub and reached in and picked Peggy up. I carried her like a bride over the threshold and laid her wet naked body on the bed. I told to get on her hands and knees and I got behind her. Her body was so perfect, I slid my cock into her hard and she was instantly aroused again. When my cock was fully buried in her pussy, I reached around and grabbed both of her nipples and pinched them. “Fuck here I go again, I am cumming, fuck I am cumming again.” She screamed out the words this time. At that same instant my cock was ready to explode. “Baby I am going to cum, too.” She slid off of my cock turned around and pulled the condom of my cock and took my dick in her mouth. I shot my load instantly and Peggy drank every last drop. “I love you, Tony,” she said after gulping the last drop. “I don’t care that I just met you, or you’re a cross dresser or anything else, I love you.” She kissed me deeply and when I started to respond to her statement, she closed my mouth and told me not to say anything. Peggy left afterwards and we agreed to meet at my room at 7:00 PM. She wanted to “meet” Sandy and I told her she would be here. I was behind schedule so I really cranked out the work. I picked up my messages, made all my calls and rescheduled my last appointment so that I could fit everything in and be done by 2:00. I did all my afternoon paper work and phone calls and at 3:00 all my work was done. I went to the laundry at the motel and washed güvenilir bahis siteleri all of my machine washable Sandy clothes and underwear. I hung out some dirty stockings in my shower and waited for them to dry. Around 5 PM, I started to get ready for Peggy to come by. I didn’t do any coke or booze, just smoked a couple of cigarettes as I got ready. Peggy had seen most of my outfits in the pictures, but I remembered that my outfit that I wore to seduce Brian in the car had not been photographed, so I decided to wear that outfit. I laid out my white bra, tank top and button down shirt in one pile on the bed all freshly washed. Next to those articles I placed my plaid skirt, shiny white thigh high stockings with my white garter belt, white panties, my white patent pumps and my silk tube I use to hide my cock. On the top of the dresser that the TV sat upon, I lay out my jewelry. I chose silver ear rings that had very long dangles, which looked like silver icicles. In addition I chose two thick bracelets, a long silver necklace with a cross on the thick chain, two rings with fake diamonds and a new collar. The collar was about an inch thick and was white stretch cotton with a rhinestone heart in the center. I could wear it and it would look very sexy and would also hide my very small Addams apple. Lastly I packed my white clutch handbag with all my necessities and laid out my new long curly wig and brushed out all of the tangles. I took a long shower and shaved my whole body again. After drying off, I painted my toe nails and finger nails fire engine red. I applied my make up except for the mascara and lipstick and then put on my outfit. I slipped on my wig, then a huge amount of mascara and red lipstick to match my nails. I sprayed a generous amount of my new Calvin Klein perfume around my neck and sprayed a shot under my skirt. Voila, Sandy had arrived! I cleaned up my hotel room and looked at the clock; it was only 6:00. I left the room and hopped in my van and drove to the liquor store a couple of blocks away. Every guy in the store was staring at me as I strolled in dressed like a cheap slut. They might have thought I was a hooker, but let me tell you they could not take their eyes off of me. I bought a bottle of champagne and a box of plastic glasses and a couple of packs of Marlboro lights. I left the store and drove back to the hotel. I was only back a few minutes when there was a knock on the door. I opened the door expecting to see Peggy in her jeans or shorts, but what I saw made my jaw drop. It certainly was Peggy, but not in jeans. She was wearing a white very short, very tight dress. It was a tank top with a scooped out top line. The hem had a zig zag cut and went from her knee on her left leg to half way up her thigh on the right. She wore white fishnet stockings and bright pink high heel pumps. Her hair was curled and looked fantastic as a long curl fell across her face. She had gold jewelry, big hoop earrings a long thin necklace and bracelets. I could smell her perfume and it smelled like fresh spring air. She was as hot and sexy and beautiful as any woman I had ever seen. She laughed at my reaction and then said, “You must be Sandy.” Peggy walked in and she looked at me like I looked at her. “You are one hot woman.” Her heels must have been a little higher than mine, because we were exactly the same height as I stared in her eyes. I leaned over and kissed her and she kissed me back. “That was the first time I ever kissed a woman that way.” Peggy laughed. We talked for about an hour as we drank champagne and did a few lines and smoked cigarettes. I kept talking in Sandy’s voice and talked both about Tony and Sandy. Peggy commented how I spoke about Tony as a different person and I told her that is how I felt. When I was Sandy, there was no Tony and vice versa. Peggy said she could definitely hang out with Sandy as long as Tony would be available sometimes too. I asked her to take a picture of me drinking champagne and I took a couple of her as well. She told me that she rented a room at the Econo Lodge two blocks away and that it was Friday night and she had to earn some money tonight. She asked if I wanted to go out iddaa siteleri with her and explained to me how you worked the streets. In only two weeks she had learned so much from other girls. How to avoid getting arrested, what to do if a cop stopped you, how to find out if someone were a cop and other tidbits. I was very frightened, but agreed to go with her. She said there was a bar at the Econo Lodge that guys came into and knew they could find girls if they wanted. I grabbed my bag and put on a lightweight red coat that went down halfway between my waist and knees. Peggy borrowed a short black lightweight jacket and we left for the bar. We walked down the street in front of my hotel and then crossed to the north side of Van Buren. At 23 rd Street we saw a police car and I got nervous, Peggy told me to relax and we walked by without incident. Before we got to 22 nd Street a car pulled into a driveway and a parking lot directly in front of us. The car stopped and as we continued walking the driver’s side window came down and we heard a voice that said, “Hi Girls.” Peggy told me to wait and she walked up to the guy in the car. They were talking for a couple of minutes and then she motioned for me to come over. “He offered me $40 and another $40 for you if we go with him to my room. I told him you were on the rag, so only blow jobs, wanna do it? “ I was concerned he was a cop, but she was sure he wasn’t, as she made him unzip his pants and show his dick to her. I agreed and she talked to him for a minute and then she came back to me and we started walking. “He is going to meet us at the motel, I told him to meet us on the back side by the ice machine,” she said. Five minutes later we were entering Peggy’s room with the guy from the car. We learned his name was Brad and that he was from L.A. and she introduced us as Margaret and Cassandra (our formal names). Brad sat down on the bed and slipped off his shoes. He was wearing a dress shirt and trousers, looking like a business man who had finished his day and took off his sports coat and tie. I walked over to him and started to unbutton his shirt and Peggy started to slip off her dress. Oh my god she looked good, it was hard to concentrate on Brad as I saw Peggy in her bra, panties and thigh high fish net stockings; she looked like a goddess. “Ok, Brad we agreed $40 each,” she said as she did a little spin so he could see her body. “Sorry baby, but I can’t fuck you and do a strip tease as it is the wrong time of the month,” I said.Brad pulled out his wallet counted out four twenty dollar bills and gave them to me. I slipped them underneath my blouse and tank top and put them in the cup on the right side of my bra. By this time I had his shirt off and his undershirt removed and started on his belt. Peggy danced over to the desk where she had a bucket of ice and a bottle of vodka and orange juice. She asked Brad if he wanted one and he said no due to driving. Peggy poured a stiff drink took a sip and then brought it over to the bed as I had finished undressing a very nervous Brad. Peggy offered me the cup and I took a big drink and then Peggy finished the rest of the drink. As I stood up, Peggy pulled me in her arms and kissed me right on the lips. I reached behind her and took and unsnapped her bra, letting her gorgeous tits fall out. Brad was now as hard as a rock watching us kiss and looking at the beautiful body of Peggy. I slid Brad on to the bed so that he was lying down and I crawled up and started stroking his cock. It was a nice cock about six inches and reasonably thick. He was getting harder and longer as I stroked it up and down slowly. Peggy handed me a condom and I slid it on Brad’s cock as I licked underneath his balls and then took one of his balls in my mouth as I stroked his cock. “Look at Cassandra, she can’t wait to suck your cock, Brad,” Peggy said. I did want this cock in my mouth, so I took a deep breath and went down on him. In one plunge I swallowed his entire length. Brad’s eyes got huge as he saw me swallow his dick. I made eye contact with him and I gave a look of pure satisfaction with his cock buried in my mouth and throat. Peggy was now completely naked except for her stockings and climbed on the bed and straddled Brad’s chest. He reached up and started feeling her nipples and tits as I went to work on his cock in a feverish manner. Peggy was sliding around on his chest with her pussy as he played with her tits.

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