Confessions of a Sex Crazy Cross Dresser
- 2 years ago
- 24
- 0
Confessions Of A Sex Crazy Cross Dresser Part 8 free porn video
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 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 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 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. She leaned over so he could take them in his mouth and he started sucking loudly on her tits. I was going up and down on Brad’s cock and he was responding by bucking his hips shoving his beautiful cock deeper down my throat. I slid my finger between his ass cheeks and when I went all the way down on his cock I inserted my finger in his ass.
Brad moaned in pleasure as I sucked his cock to the hilt. I stopped for a second and rose up, as I could feel Brad almost ready to shoot his load. Peggy slid down his chest so that her pussy was right above his cock.
“Fuck that was the best blow job I ever had in my life, baby,” Brad said to me as Peggy mounted his cock.
She slowly slid down the length of his shaft taking his full length inside her cunt. She cooed as she was in a pleasurable state as she slid up and down his rod. Brad told her he wanted to have her on her back, so she climbed off and laid down on the bed and spread her legs. I was so envious, I wanted to fuck her so bad and I wanted Brad to fuck me as badly. Instead Brad stuck his long pipe into her pussy and I had a front row seat. I climbed back on the bed and started kissing Peggy as her pussy was being pounded by Brad. Between the blow job and Peggy riding him, he only had about two or three thrusts in him before he shot his load. He wasted no time in getting his clothes back on got ready to leave.
“You two are amazing. Cassandra, by far the best blow job and Margaret, you are the sexiest fuck I ever had,” he said as he opened the door.
Brad was gone, we had made $80 in twenty minutes and I had turned into a legitimate hooker.
Chapter 16: The Duo Continues
Peggy went into the bathroom and started the shower and washed off her body. I came in and dried her off explaining how badly I wanted to attack her body whenever I am next to her. We stayed in the bathroom and we re-worked our make up. Peggy showed a better way to lay a foundation of make up and I couldn’t wait to try it and improve my appearance. She also suggested false eyelashes as a way to make my eyes look even better.
I gave her the $80 from my bra and she said that I earned some of it, too. I said not to worry; just to be with her was worth it. We chugged a quick drink and then left her room and went to the bar downstairs that was attached to the motel.
It was exactly 9 PM when we entered the bar. It was a good sized bar and was pretty crowded. It was not a high scale establishment at all, but we did not look out of place all dressed up. Some guys had on suits with their ties loosened; some were dressed in t-shirts and jeans. There were a couple of other working girls and the smiled when we walked in. I guess they recognized Peggy and it was a friendly competition. They were dressed in tight pants and tops, a much different look than ours.
We sat at the bar and ordered screwdrivers and talked about our adventure. Peggy told me that she gets excited when she is fucking the guys, but never gets totally into it as she needs to be sure to keep all of her alerts on high. She was so more relaxed when we were together, because it would be almost impossible for someone to trick both of us.
About five minutes later one of the guys in a suit with the loosened tie sat next to us and bought us a drink. He was hitting us up for information on where we were staying and asking in a very discreet way how much it would cost for us to go to his hotel room. I let Peggy handle the negotiations as we enjoyed our free drink. I learned his name was Neil and he lived in Denver and I was introduced as Cassandra. He was staying at the Motel 6 and Peggy (Margaret) was assured he was not a cop. She told him we worked together and it would cost $80 to go to our room and gave him the same details that she told Brad. Or he could drive us to his hotel and it would cost him $120.
He did not appear too drunk, so I was ok with him driving us and he was much more comfortable going to his room instead of “ours”. We finished our drinks and told him to pick us up in the back of the hotel in five minutes, so that we didn’t leave all together at one time. Neil picked us up in a basic four dour sedan rental car. I sat in front and Peg sat in the back. I apologized in advance that I was “on the rag”, but that he would still have fun. I rubbed his thigh as he drove the two blocks back to the Motel 6.
His room was on the complete opposite side of the motel from my room and was on the third floor. When we entered his room he walked into the bathroom and turned on the light creating a very dim light that made it possible to see, without being too bright. Neil was an average looking guy. He was about 40 years old with thin hair a round face. He was about my height but about forty pounds heavier.
Peggy and I already had established a little routine from our last outing and we took the same approach here. I started undressing Neil and half way through asked him for the money. He gave us a crisp $100 bill and a $20 bill as well. I placed the money in my bra and removed the rest of his clothes and led him to his bed. He pulled me down on the bed with him with his hands under my skirt and firmly holding my ass through my panties. My chest was on his chest so I slid down so that his already hard cock made contact with my crotch and I rubbed it back and forth trying to get him hotter.
While I was entertaining Neil, Peggy slipped off her dress by the bathroom door, so Neil had a good view of her body. “Fuck you are fucking hot Margaret. Get over here so I can feel up those fucking tits of yours,” he said.
Peggy strolled over losing her bra and panties on the way and lay down beside him. I placed a condom on him and started licking his cock and balls and got a good look at his dick. His belly hung over his waistline so I couldn’t really see his dick until I got down on it. It was short and thin only about four inches long. But that was about $30 per inch the way I looked at it now.
Neil was pumping his cock in my mouth as he played with Peg’s tits. “Fuck Cassandra, you know how to suck cock. Slow down or I am going to fucking cum already,” he said.
Peggy wasted no time as I slid off the bed; she rolled on top of his chest and straddled his huge stomach with her legs. “You want to fuck me, Neil?”
“Oh yea, baby. Climb on board and ride me!” he said.
Peggy slid her pussy over his cock and started to ride his short dick up and down. Neil started to buck his hips to drive his penis further into her cunt and again he was getting ready to cum. She looked so hot in her thigh high stockings and nothing else. I wanted to switch places with him and let her fuck my brains out.
“I need to slow down, your pussy is so good, and it is going to make me cum,” he said.
Peggy slid off his cock and straddled his chest so he could play with her tits. He was like a kid in a candy store squeezing them and pinching her nipples. She spoke, “Neil, we can’t go much longer, maybe if you want something special, maybe Cassandra can fuck you, too.”
“I thought she was on the rag,” he said between squeezing her tits.
I knew what she was talking about, so I interjected. “There is one hole you haven’t filled yet, baby. $40 more and I will climb on top of you and let you fuck my ass.”
Neil did not hesitate, he reached over and grabbed his wallet and pulled out $40 and handed the bills to me. I placed them in my bra and then I slipped of my plaid school girl skirt. Then I took off my button/tied blouse so I was still in my tank top. In the dark light there was no way he could see anything and Peggy remained sitting on his chest as I slid my panties to the side so my ass was available. I knew his cock was so small it would have to be really hard to get started in my ass hole, but when I went back down to look, it was harder than ever. I climbed on the bed and my back rubbed against Peggy’s back. I slipped my cock out of its sheath and held my balls and cock in my hand against my stomach to keep them hidden and then I lowered my ass gently on his cock.
Even though it was small it still had the same pleasurable sensation when it broke through and entered me. I moaned in pleasure as Neil cock entered my ass.
“Ohhhhhhhhh yea baby," I said. "Your cock feels so good in my ass,” I said.
Peggy slid of his chest so that she was beside him and he could play with her tits, but also knew he wanted to see his cock go inside me. I rode him up and down and he could see my backside as I rode his cock like a cowboy on a bull.
“Fuck me Neil, Fuck my ass,” I said.
Neil did not stand a chance, he was so turned on he shot his load inside me on the fifth time I went down. I could feel his cock spurt inside my ass and I had a black out moment as my mind raced in ecstasy. Peg was quick to climb back on his chest so that I could re arrange myself. I slipped my hard cock in its sheath and slid it down between my legs and up my ass crack. I pulled my panties straight and stood up and put on my skirt. I walked up to the head of the bed as Peg climbed off to get dressed.
I removed the condom from his cock and had never seen one so full of cum. He had shot a full load as he fucked my ass.
“Thank you, honey,” I whispered to Neil. “You are a great fuck. If you lasted a couple more minutes I would have cum all over myself.”
I kissed him on the cheek and by that time Peg was dressed and she said something softly to him and kissed him as well. We left his room walked downstairs and went to my room.
We went inside and started kissing passionately. It was only 9:45, in less than two hours we had made $240. I wasn’t sure if I was more excited about getting fucked, sucking cock, hanging with Peg or the money. What a cool night and Peg told me it was the first time she has had fun being a hooker.
Peg went into wash up as I went down and got some ice. When I returned she was drying off and I stripped down and also took a shower leaving my wig and earrings on. We got dressed together and did a couple of lines a coke with our drink and smoked a cigarette. We placed most of the money in my room safe and got ready to leave the room. It was 10:30 when we left the room again and started to walk down Van Buren this time in the opposite direction. We had not even walked a block when we saw a car drive by us very slowly and saw a man driving obviously checking us out. When we reached 25 th St. we crossed over to the North side of the street and reversed direction. We saw the car that slowed down make a right turn a couple of blocks further down the street.
Peggy told me that he was going to turn around and come back to either check us out again or try to pick us up, so we should walk into the convenience store to make it easier for him. She told me that this way we could be discreet as we would be at the store, not talking on the street. She was 100% correct, as we walked across the parking lot of the Circle K shop; the car pulled into the lot and parked. Peg and I entered the store and bought a pack of cigarettes. When we came out, we each went to the side of the store and lit up a smoke. The guy from the car came over to us and asked if he could buy us a drink. I let Peggy handle the deal again and sure enough at 11:30 we were leaving his hotel on 20 th Street with $120 in my bra. We decided to walk to Peggy’s hotel and have a drink in the bar.
We got lucky at midnight when a guy who had just checked in the hotel came in for a drink. He immediately hit us up and we ended up in his room for a quick two time blow job for $40. We went to Peggy’s room and grabbed her duffel bag with all of her stuff and walked back to my hotel. It was 12:30 and we had made $400 in one night.
We took another rinse off and got dressed again, as we were unsure if we were going to go out again. We had a couple lines of cocaine and a screwdriver from her vodka and orange juice. I went over to Peg and pulled her out of her chair. I pulled her in my arms and slipped the straps of her dress off her shoulder. I slid her dress down her body and she stepped out of it completely. I stared at her beautiful body in the tight bra, panties and stockings. She unbuttoned my blouse and slipped off my tank top. Then slid off my skirt and we were dressed identically except for my garter belt and the texture of our stockings and the color of our shoes.
I held her tight and we kissed like lesbian lovers. Our tongues danced over each others neck and shoulders. I unsnapped her bra and removed it from her shoulders and attacked her tits with my tongue and mouth. She leaned into my ear and whispered, “I love you Sandy.”
She reached out for the front of my bra and slipped it off of me and she returned the favor to my breasts. I felt alive as she treated them softly and then roughly. My nipples felt like they were going to explode as they became stiff. I led her to the bed and laid her cross ways so I could remove her panties and put my face between her legs. She spread her legs wide open and I went down on her pussy. She moaned as my tongue played with her clit and my hand explored inside her. In less than two minutes Peggy had her first orgasm, it appeared to be a mind blowing strong one as she pulled my face deep into her pussy as it quivered and shook with my tongue deep inside her box.
“I have a surprise for you, honey,” she said.
She stood up and told me to remove panties. I slid them down and off but left on my shoes, now we both were topless and without panties but with stockings and shoes. I slipped off my sheath and my cock stood up at attention, but I didn’t mind, I still felt like Sandy. Peggy pulled out a long dildo from her duffle bag. It had to be at least two feet long and had a cock head on each end. It was not straight but shaped more like a horseshoe and somewhat flexible.
Peggy came over to me and showed me the horseshoe dildo closely and I immediately took one end in my mouth. She did the same with the other end and we lie down on the bed. I kissed her on the mouth as I lay on my back and slid a pillow under my butt. She applied some KY jelly to my butt hole and started to apply pressure on my ass with the dildo. It was pretty wide, but it broke through and the first half an inch was now in my ass. God it felt good to have it inside me and it was going deeper as Peggy was feeding into my ass a half an inch at a time. Deeper she shoved it in my ass and now I had a full four inches in and more to go.
“Oh, Peggy. Give me more give me more,” I squealed.
Peggy kept going until I had at least a full eight inches of dildo cock in my ass. I was in so much pleasure as Peggy was servicing me. She let go of the dildo and left it loaded in my man pussy while she slid up and kissed me on the mouth. I played with her breasts as she straddled my chest. I stopped fondling her and grabbed the dildo about three inches from my ass hole and bent it around so that is was aiming at Peggy’s already wet cunt.
She slid down my chest and spread her legs and her pussy came into contact with the other end of the dildo. Her body relaxed and I blindly pushed the dildo so that her entered her cunt.
“Oh yea Sandy.” She cooed. “I love you; share this big cock with me.”
She slid down farther on the dildo and now her pussy and my ass were sharing this horse sized double dick. We both had at least eight inches inside us and Peggy lay on top of my body we kissed for minutes, barely breaking our kisses to get breath. We were both taking every inch we could but sharing at the same time.
“I am cumming on our cock, Sandy,” she said. “Fuck, fuck, fuck”
I was holding on to the only part of the dildo exposed between her cunt and my ass and she was shoving down her pussy to take every last inch of the massive cock we shared. She slowly raised her chest up and pushed herself up using her hands so that the she was sitting up on the cock. She screamed in ecstasy and she started riding the cock up and down with each thrust she moaned and shoved the dildo further in her cunt and further into my ass.
We were now both screaming in pleasure I kept hearing myself say, “Fuck me. Fuck my fucking ass!”
Peggy started to shake in an enormous orgasm. “I am cumming,” she yelled as she bucked down on our shared cock and then collapsed on top of me. .
We lay still for a moment and then Peggy climbed off of the cock and slowly withdrew it from my ass. We lay side by side kissing and cuddling and I whispered to her, “Since we are in for the evening, I think I will shower and let Tony come over.” I started to laugh and so did Peggy.
I took off my garter and stockings, wig and jewelry and went into the bathroom. I removed all my nail polish from my toes and fingers and washed all of my make up off. I washed my entire body and about thirty minutes later I came out of the bathroom with just a towel wrapped around me.
Peggy had changed into the t-shirt I wore last night and nothing else. I came up to her and kissed her. We turned off the lights and went to bed. I made love to her gently and passionately like the night before. I didn’t use a condom, as she promised she had been very safe and she wanted to feel my cum inside her. We came together in a long extended orgasm and I filled her box with so much cum that she had to go to the bathroom to let some out. We slept together and the last words I told her were, “Good Night, Peg. I love you.”
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 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 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 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. She leaned over so he could take them in his mouth and he started sucking loudly on her tits. I was going up and down on Brad’s cock and he was responding by bucking his hips shoving his beautiful cock deeper down my throat. I slid my finger between his ass cheeks and when I went all the way down on his cock I inserted my finger in his ass.
Brad moaned in pleasure as I sucked his cock to the hilt. I stopped for a second and rose up, as I could feel Brad almost ready to shoot his load. Peggy slid down his chest so that her pussy was right above his cock.
“Fuck that was the best blow job I ever had in my life, baby,” Brad said to me as Peggy mounted his cock.
She slowly slid down the length of his shaft taking his full length inside her cunt. She cooed as she was in a pleasurable state as she slid up and down his rod. Brad told her he wanted to have her on her back, so she climbed off and laid down on the bed and spread her legs. I was so envious, I wanted to fuck her so bad and I wanted Brad to fuck me as badly. Instead Brad stuck his long pipe into her pussy and I had a front row seat. I climbed back on the bed and started kissing Peggy as her pussy was being pounded by Brad. Between the blow job and Peggy riding him, he only had about two or three thrusts in him before he shot his load. He wasted no time in getting his clothes back on got ready to leave.
“You two are amazing. Cassandra, by far the best blow job and Margaret, you are the sexiest fuck I ever had,” he said as he opened the door.
Brad was gone, we had made $80 in twenty minutes and I had turned into a legitimate hooker.
Chapter 16: The Duo Continues
Peggy went into the bathroom and started the shower and washed off her body. I came in and dried her off explaining how badly I wanted to attack her body whenever I am next to her. We stayed in the bathroom and we re-worked our make up. Peggy showed a better way to lay a foundation of make up and I couldn’t wait to try it and improve my appearance. She also suggested false eyelashes as a way to make my eyes look even better.
I gave her the $80 from my bra and she said that I earned some of it, too. I said not to worry; just to be with her was worth it. We chugged a quick drink and then left her room and went to the bar downstairs that was attached to the motel.
It was exactly 9 PM when we entered the bar. It was a good sized bar and was pretty crowded. It was not a high scale establishment at all, but we did not look out of place all dressed up. Some guys had on suits with their ties loosened; some were dressed in t-shirts and jeans. There were a couple of other working girls and the smiled when we walked in. I guess they recognized Peggy and it was a friendly competition. They were dressed in tight pants and tops, a much different look than ours.
We sat at the bar and ordered screwdrivers and talked about our adventure. Peggy told me that she gets excited when she is fucking the guys, but never gets totally into it as she needs to be sure to keep all of her alerts on high. She was so more relaxed when we were together, because it would be almost impossible for someone to trick both of us.
About five minutes later one of the guys in a suit with the loosened tie sat next to us and bought us a drink. He was hitting us up for information on where we were staying and asking in a very discreet way how much it would cost for us to go to his hotel room. I let Peggy handle the negotiations as we enjoyed our free drink. I learned his name was Neil and he lived in Denver and I was introduced as Cassandra. He was staying at the Motel 6 and Peggy (Margaret) was assured he was not a cop. She told him we worked together and it would cost $80 to go to our room and gave him the same details that she told Brad. Or he could drive us to his hotel and it would cost him $120.
He did not appear too drunk, so I was ok with him driving us and he was much more comfortable going to his room instead of “ours”. We finished our drinks and told him to pick us up in the back of the hotel in five minutes, so that we didn’t leave all together at one time. Neil picked us up in a basic four dour sedan rental car. I sat in front and Peg sat in the back. I apologized in advance that I was “on the rag”, but that he would still have fun. I rubbed his thigh as he drove the two blocks back to the Motel 6.
His room was on the complete opposite side of the motel from my room and was on the third floor. When we entered his room he walked into the bathroom and turned on the light creating a very dim light that made it possible to see, without being too bright. Neil was an average looking guy. He was about 40 years old with thin hair a round face. He was about my height but about forty pounds heavier.
Peggy and I already had established a little routine from our last outing and we took the same approach here. I started undressing Neil and half way through asked him for the money. He gave us a crisp $100 bill and a $20 bill as well. I placed the money in my bra and removed the rest of his clothes and led him to his bed. He pulled me down on the bed with him with his hands under my skirt and firmly holding my ass through my panties. My chest was on his chest so I slid down so that his already hard cock made contact with my crotch and I rubbed it back and forth trying to get him hotter.
While I was entertaining Neil, Peggy slipped off her dress by the bathroom door, so Neil had a good view of her body. “Fuck you are fucking hot Margaret. Get over here so I can feel up those fucking tits of yours,” he said.
Peggy strolled over losing her bra and panties on the way and lay down beside him. I placed a condom on him and started licking his cock and balls and got a good look at his dick. His belly hung over his waistline so I couldn’t really see his dick until I got down on it. It was short and thin only about four inches long. But that was about $30 per inch the way I looked at it now.
Neil was pumping his cock in my mouth as he played with Peg’s tits. “Fuck Cassandra, you know how to suck cock. Slow down or I am going to fucking cum already,” he said.
Peggy wasted no time as I slid off the bed; she rolled on top of his chest and straddled his huge stomach with her legs. “You want to fuck me, Neil?”
“Oh yea, baby. Climb on board and ride me!” he said.
Peggy slid her pussy over his cock and started to ride his short dick up and down. Neil started to buck his hips to drive his penis further into her cunt and again he was getting ready to cum. She looked so hot in her thigh high stockings and nothing else. I wanted to switch places with him and let her fuck my brains out.
“I need to slow down, your pussy is so good, and it is going to make me cum,” he said.
Peggy slid off his cock and straddled his chest so he could play with her tits. He was like a kid in a candy store squeezing them and pinching her nipples. She spoke, “Neil, we can’t go much longer, maybe if you want something special, maybe Cassandra can fuck you, too.”
“I thought she was on the rag,” he said between squeezing her tits.
I knew what she was talking about, so I interjected. “There is one hole you haven’t filled yet, baby. $40 more and I will climb on top of you and let you fuck my ass.”
Neil did not hesitate, he reached over and grabbed his wallet and pulled out $40 and handed the bills to me. I placed them in my bra and then I slipped of my plaid school girl skirt. Then I took off my button/tied blouse so I was still in my tank top. In the dark light there was no way he could see anything and Peggy remained sitting on his chest as I slid my panties to the side so my ass was available. I knew his cock was so small it would have to be really hard to get started in my ass hole, but when I went back down to look, it was harder than ever. I climbed on the bed and my back rubbed against Peggy’s back. I slipped my cock out of its sheath and held my balls and cock in my hand against my stomach to keep them hidden and then I lowered my ass gently on his cock.
Even though it was small it still had the same pleasurable sensation when it broke through and entered me. I moaned in pleasure as Neil cock entered my ass.
“Ohhhhhhhhh yea baby," I said. "Your cock feels so good in my ass,” I said.
Peggy slid of his chest so that she was beside him and he could play with her tits, but also knew he wanted to see his cock go inside me. I rode him up and down and he could see my backside as I rode his cock like a cowboy on a bull.
“Fuck me Neil, Fuck my ass,” I said.
Neil did not stand a chance, he was so turned on he shot his load inside me on the fifth time I went down. I could feel his cock spurt inside my ass and I had a black out moment as my mind raced in ecstasy. Peg was quick to climb back on his chest so that I could re arrange myself. I slipped my hard cock in its sheath and slid it down between my legs and up my ass crack. I pulled my panties straight and stood up and put on my skirt. I walked up to the head of the bed as Peg climbed off to get dressed.
I removed the condom from his cock and had never seen one so full of cum. He had shot a full load as he fucked my ass.
“Thank you, honey,” I whispered to Neil. “You are a great fuck. If you lasted a couple more minutes I would have cum all over myself.”
I kissed him on the cheek and by that time Peg was dressed and she said something softly to him and kissed him as well. We left his room walked downstairs and went to my room.
We went inside and started kissing passionately. It was only 9:45, in less than two hours we had made $240. I wasn’t sure if I was more excited about getting fucked, sucking cock, hanging with Peg or the money. What a cool night and Peg told me it was the first time she has had fun being a hooker.
Peg went into wash up as I went down and got some ice. When I returned she was drying off and I stripped down and also took a shower leaving my wig and earrings on. We got dressed together and did a couple of lines a coke with our drink and smoked a cigarette. We placed most of the money in my room safe and got ready to leave the room. It was 10:30 when we left the room again and started to walk down Van Buren this time in the opposite direction. We had not even walked a block when we saw a car drive by us very slowly and saw a man driving obviously checking us out. When we reached 25 th St. we crossed over to the North side of the street and reversed direction. We saw the car that slowed down make a right turn a couple of blocks further down the street.
Peggy told me that he was going to turn around and come back to either check us out again or try to pick us up, so we should walk into the convenience store to make it easier for him. She told me that this way we could be discreet as we would be at the store, not talking on the street. She was 100% correct, as we walked across the parking lot of the Circle K shop; the car pulled into the lot and parked. Peg and I entered the store and bought a pack of cigarettes. When we came out, we each went to the side of the store and lit up a smoke. The guy from the car came over to us and asked if he could buy us a drink. I let Peggy handle the deal again and sure enough at 11:30 we were leaving his hotel on 20 th Street with $120 in my bra. We decided to walk to Peggy’s hotel and have a drink in the bar.
We got lucky at midnight when a guy who had just checked in the hotel came in for a drink. He immediately hit us up and we ended up in his room for a quick two time blow job for $40. We went to Peggy’s room and grabbed her duffel bag with all of her stuff and walked back to my hotel. It was 12:30 and we had made $400 in one night.
We took another rinse off and got dressed again, as we were unsure if we were going to go out again. We had a couple lines of cocaine and a screwdriver from her vodka and orange juice. I went over to Peg and pulled her out of her chair. I pulled her in my arms and slipped the straps of her dress off her shoulder. I slid her dress down her body and she stepped out of it completely. I stared at her beautiful body in the tight bra, panties and stockings. She unbuttoned my blouse and slipped off my tank top. Then slid off my skirt and we were dressed identically except for my garter belt and the texture of our stockings and the color of our shoes.
I held her tight and we kissed like lesbian lovers. Our tongues danced over each others neck and shoulders. I unsnapped her bra and removed it from her shoulders and attacked her tits with my tongue and mouth. She leaned into my ear and whispered, “I love you Sandy.”
She reached out for the front of my bra and slipped it off of me and she returned the favor to my breasts. I felt alive as she treated them softly and then roughly. My nipples felt like they were going to explode as they became stiff. I led her to the bed and laid her cross ways so I could remove her panties and put my face between her legs. She spread her legs wide open and I went down on her pussy. She moaned as my tongue played with her clit and my hand explored inside her. In less than two minutes Peggy had her first orgasm, it appeared to be a mind blowing strong one as she pulled my face deep into her pussy as it quivered and shook with my tongue deep inside her box.
“I have a surprise for you, honey,” she said.
She stood up and told me to remove panties. I slid them down and off but left on my shoes, now we both were topless and without panties but with stockings and shoes. I slipped off my sheath and my cock stood up at attention, but I didn’t mind, I still felt like Sandy. Peggy pulled out a long dildo from her duffle bag. It had to be at least two feet long and had a cock head on each end. It was not straight but shaped more like a horseshoe and somewhat flexible.
Peggy came over to me and showed me the horseshoe dildo closely and I immediately took one end in my mouth. She did the same with the other end and we lie down on the bed. I kissed her on the mouth as I lay on my back and slid a pillow under my butt. She applied some KY jelly to my butt hole and started to apply pressure on my ass with the dildo. It was pretty wide, but it broke through and the first half an inch was now in my ass. God it felt good to have it inside me and it was going deeper as Peggy was feeding into my ass a half an inch at a time. Deeper she shoved it in my ass and now I had a full four inches in and more to go.
“Oh, Peggy. Give me more give me more,” I squealed.
Peggy kept going until I had at least a full eight inches of dildo cock in my ass. I was in so much pleasure as Peggy was servicing me. She let go of the dildo and left it loaded in my man pussy while she slid up and kissed me on the mouth. I played with her breasts as she straddled my chest. I stopped fondling her and grabbed the dildo about three inches from my ass hole and bent it around so that is was aiming at Peggy’s already wet cunt.
She slid down my chest and spread her legs and her pussy came into contact with the other end of the dildo. Her body relaxed and I blindly pushed the dildo so that her entered her cunt.
“Oh yea Sandy.” She cooed. “I love you; share this big cock with me.”
She slid down farther on the dildo and now her pussy and my ass were sharing this horse sized double dick. We both had at least eight inches inside us and Peggy lay on top of my body we kissed for minutes, barely breaking our kisses to get breath. We were both taking every inch we could but sharing at the same time.
“I am cumming on our cock, Sandy,” she said. “Fuck, fuck, fuck”
I was holding on to the only part of the dildo exposed between her cunt and my ass and she was shoving down her pussy to take every last inch of the massive cock we shared. She slowly raised her chest up and pushed herself up using her hands so that the she was sitting up on the cock. She screamed in ecstasy and she started riding the cock up and down with each thrust she moaned and shoved the dildo further in her cunt and further into my ass.
We were now both screaming in pleasure I kept hearing myself say, “Fuck me. Fuck my fucking ass!”
Peggy started to shake in an enormous orgasm. “I am cumming,” she yelled as she bucked down on our shared cock and then collapsed on top of me. .
We lay still for a moment and then Peggy climbed off of the cock and slowly withdrew it from my ass. We lay side by side kissing and cuddling and I whispered to her, “Since we are in for the evening, I think I will shower and let Tony come over.” I started to laugh and so did Peggy.
I took off my garter and stockings, wig and jewelry and went into the bathroom. I removed all my nail polish from my toes and fingers and washed all of my make up off. I washed my entire body and about thirty minutes later I came out of the bathroom with just a towel wrapped around me.
Peggy had changed into the t-shirt I wore last night and nothing else. I came up to her and kissed her. We turned off the lights and went to bed. I made love to her gently and passionately like the night before. I didn’t use a condom, as she promised she had been very safe and she wanted to feel my cum inside her. We came together in a long extended orgasm and I filled her box with so much cum that she had to go to the bathroom to let some out. We slept together and the last words I told her were, “Good Night, Peg. I love you.”
Oceana
- 01.02.2021
- 21
- 0
- Category:
- Crossdressing
Confessions of a Sex Crazy Cross Dresser
- 2 years ago
- 27
- 0
Confessions of a Sex Crazy Cross Dresser Part 4
- 3 years ago
- 28
- 0
