Confessions of a Sex Crazy Cross Dresser Part 5

I hope you enjoy Sandy’s continuing adventures. Please comment and let me know if I should include the next two chapters. Chapter 9: Joe’s Pizza Sunday morning I got up pretty early. I decided to call a cab and go over and pick up my van from Glenn and John’s. After I got back I decided to do some sit ups, as I had not been exercising as much lately. A quick shower after my exercises and then I decided to get ready for my trip. I spent a couple of hours packing as I was going to be gone for at least ten days. First I packed up all of my samples that I needed for my work appointments. Secondly I packed all my work clothes that required hangers in a garment bag. Next I packed a duffel bag that carried all my socks, underwear, jeans and toiletries. Lastly, I packed a suitcase with several of my “Sandy” outfits. In this suitcase I put all my sex toys I wanted to bring and my camera. I got a call from Collette the girl I met last Saturday night and she wondered if I wanted to have a late lunch or early dinner. Since it was 1:00 and I had all my chores done, we agreed to meet at 3:30 for appetizers at a restaurant near where we met last weekend. I had a couple of hours to kill and I decided to do my new favorite hobby, shopping. Whenever I had any free time from work, I would always go shopping and buy little items or new outfits. I was totally addicted to shopping in cheap stores trying to find bargains to expand Sandy’s wardrobe. So I took all my suitcases and sample cases down to the garage and loaded them into the van. I put everything in the back and this left both front seats open and the bench seat (middle row) of the van clear. Today I went into an adult book store, because there was something I needed to have for my adventures. I stopped at a drug store and picked up more rubbers, KY, fingernail polish remover and a couple of make up items. Next stop was a small mall in Alhambra a town next to mine where Diane the bartender lived. I knew they had a photography store there and I picked up a tri-pod. Then I browsed some stores and I picked up a couple of new outfits between the stores. I packed up all the goodies into my suitcases except for the two new outfits and drove home. I returned at 3:00, just in time to wash up and walk down to the restaurant to meet Collette. I arrived a few minutes early at the restaurant, a really nice place called The Tea Room. There was no one else in the bar except for a bartender and waitress so I sat down at the middle stool and ordered a beer. Collette walked in the door a few minutes later. She looked much better than I remembered. She was probably 40 years old, with long black curly hair, a very curvy body, with an incredible set of legs. She was wearing a white denim skirt with a fuchsia sweater. The sweater fit tight across her chest showing off her incredible set of tits. She was wearing flat beaded sandals so her legs just went on forever. I stood up as she approached and gave her a kiss on the cheek. “Hi Collette, you look fantastic!” I said. “I am so glad you called, I have been wanting to see you.” “Thanks Tony, same with me. I thought we had a fun time the other night.” She replied. Collette ordered a cosmopolitan. I loved these drinks, but never ordered them as they were very feminine. I did take a sip of hers, and within an half an hour she was on her third cosmo and I had joined her and was on my second. We had potato skins as an appetizer and then a spinach dip as well and were now full and were on our way to a nice buzz. We talked about a lot of stuff; I explained that I was kind of a free spirit, not looking for relationships or commitments right now. She was separated from her husband for almost a year and was also enjoying the single life. We enjoyed a few more drinks and it was almost 5:30. I told her I had to go home, as I was leaving tomorrow. She offered to give me a ride home, but I knew she lived only a couple of blocks away, so I told her no. I walked her to her car which was located in the second floor of a parking garage behind the restaurant. As she opened the door to her car, she turned to me and we kissed. It started out innocent, but in seconds we were really kissing hard. My tongue was in her mouth and hers in mine and we were holding each other very tight. She opened her back door and told me to come inside with her. She had a big car with a huge back seat. We immediately started kissing and I stuck my hand on her thigh and rubbed up her leg. She spread her legs wider and I slid my hand up underneath her white skirt and felt her black thighs while maintaining a lip lock on her. I slid around so that my knees were on the floor of the back seat and slid her skirt up all the way to her waist. I slid down her white panties all the way down her legs and over her sandalized feet. I stuck my head between her legs and starting licking Collette’s pussy with my tongue. I went right at her clit and found a big thick clit that felt wet from her dripping cunt. I continued to lick her clit and moved my hand up her thigh until I found her pussy and inserted my index finger inside her cunt. Her moaning increased as I continued to lick and nibble on her clit as my finger went in and out of her sticky and very moist pussy. “Tony, that feels so good, don’t stop. Keep eating my pussy! She panted out between moans. I didn’t stop; I picked up the pace and inserted a second finger inside her. I tried to mix my licking with a gentle bite of her clit. This sent shivers throughout her entire body and she grabbed my head with both hands and shoved my face right into her wet pussy. I shifted my position and started to lick the bottom güvenilir bahis of her cunt and crept my tongue into her ass crack and I felt her lift her butt up so that my tongue could find her puckered asshole. When I found my target I moved my middle finger inside her pussy to try to find her “g spot”. At the same time I started sticking my tongue into her asshole. This time her shiver shook her body so severely Collette let out a huge pant and moan. “Fuck Tony, what are you doing to me?” She screamed. I kept working my fingers and looked up to see Collette pulling up her sweater and unfastening her red lacy bra. I kept my attention on licking her ass and repeatedly sticking my tongue inside her asshole. It was so tight and clean. Even though the light was dim, I could see her black skin and pink pussy and taste and feel the warm juices flowing from her cunt. I stuck my tongue as far as I could up her ass again and worked my middle finger inside her cunt and hit the magic spot. Collette started pinching her beautiful big black tits and started moaning in ecstasy. “Fuck me baby, fuck me now.” She screamed in the car. “No baby, I want you to come all over my mouth.” I said. Seconds later Collette exploded in an orgasm. She had both hands on the back of my head and shoved my mouth into her ass and my tongue reached further inside her. My two fingers were going along for the ride as her whole body buckled and twisted and she moaned. “Yes, fucking yes! Fuck I am cumming, so hard. I am still cumming. I can’t stop! Fuck my ass with your tongue, baby! Make me keep cumming.” She was in an uncontrollable state for about thirty seconds, bucking and twisting on the car seat. I slid my head up and started playing with her tits with both my hands and lips. I had to taste and feel these beautiful big breasts. As I was kissing her, I felt her hands go down to my crotch and unbutton my pants. We shifted positions so that I was on the car seat and Collette wasted no time in stripping my pants down to my ankles and without a word came up and sat on my stiff cock. My dick slid into her pussy so easy and she whispered in my ear. “I had to have your cock inside me. Now fuck me good we need to get out of here before we get caught.” It didn’t take much as we were both so hot. She rode my cock and I bucked my hips so that she could feel my entire dick inside her pussy. We only lasted about two minutes and I could feel my cock ready to spurt a huge load of cum. Collette was in the middle of her second intense orgasm and it was sending me over the edge. “Baby, I am going to cum so hard.” I said. She immediately climbed of my cock and put my dick in her mouth to finish the job. In seconds I was shooting a big load of cum into her mouth. Collette was pulling on my cock to drain every last drop of cum out of me. “How was that for a first date, honey?” She asked. “I can’t wait for the second, baby.” I replied. My first thought was I have another fuck buddy! This has been a good week for finding girls to have casual sex! But my second thought was she was the hottest girl I had fucked in a long time. She had the most beautiful skin, great body, perfect personality and didn’t want to get in a relationship. We kissed good bye, I promised to call her in a couple of weeks when I got back and I was gone. I left Collette and started my walk home. It was just past sundown and I enjoyed the short walk home after a great fuck session with a new hottie. I arrived at my apartment and took a hot shower shaving my body all over to get ready for my trip. It was about 7:00 PM when I got out of the shower and I dried off and spread powder all over my body. I had never used powder before, but since I started shaving, I loved the fresh feeling it gave to my body after a shower. I couldn’t wait to try on my new outfits I bought earlier. I poured myself a scotch and had a couple of sips. The first one I tried on looked very sexy. I had been inspired by the look that Jules had worn to Tango’s last night. I bought a short red and black plaid mini skirt and a white button down top that I could tie at my waist line. I liked how it looked with my new white bra and white tank top that I wore underneath. I also found some frilly white ankle socks and white patent high heel pumps during my shopping. I thought I looked very cute and sexy in my new outfit. I put it back in my shopping bag and tried on the second outfit. It was a denim mini skirt with a blue chambray button down shirt. I also bought short cowboy boots and a red bandana to tie around my neck. When I started trying this outfit on, I knew I had to go all the way. I refilled my drink and I put on all the accessories including my new “hide the dick sheath”, panties, nude color thigh highs and tons of silver jewelry. I put on my make up and wig and was fully dressed up. I looked at myself in the mirror and was amazed that I looked better each time I dressed up. I poured another drink and thought of what I was going to do for dinner. I didn’t want a late night as I had to leave rather early tomorrow on my trip, so I decided I would order pizza. When I thought of pizza, I thought of my first adventure with Carlos, but I wanted something different. I thought of a great idea. I grabbed a grocery bag and put in my bottle of scotch, a big baggie filled with ice and put my handbag on my shoulder and strolled out of my apartment. I remembered I had to return Sheila’s key to her apartment and I thought I would make a little adventure out of it. I walked upstairs seeing no one in the hallways and opened up the door to Sheila’s apartment. It was exactly as I had left it yesterday. güvenilir bahis siteleri I put down my things and then I looked for her phone book. I found a delivery place I had never called before, I called placed the order and sat back to wait to see if I would get lucky again. I passed the time by snooping around Sheila’s apartment. I did a more thorough job of looking through her lingerie and found a couple of items I missed the first time. Wow, I would love to see her in a couple of these items. But even more than that, I wanted to try them on myself. But that was going to have to wait for some other time. When the intercom buzzer rang, my heart started to beat fast and I couldn’t wait to find out who was delivering my pizza. The voice on the other end of the intercom was very bland and I couldn’t tell anything about him. I gave him directions to the apartment and buzzed him through. Two minutes later there was a knock on the door and I opened it to see a very tall and young black man. He looked to be about 18 years old and was at least 6’ 2” tall. “Hi, come on in.” I said. I turned my back and started walking towards the dining room table. I could hear him step in and I turned around and saw him watching my legs in my short denim skirt. I instructed him to put the pizza down on the table and he looked down at me and said “Twelve dollars even for the pizza, ma’am.” This was a first someone calling me ma’am. I gave him a twenty dollar bill and like Carlos the first time, I asked for three dollars back. “I am sorry ma’am, but I only have a one a five and a ten.” He said. “That’s fine, I will take the one. A nice young man like you deserves a big tip.” I said. “Thank you.” He said. He handed me the one dollar bill and again, I pretended to accidentally drop in on the floor. This time I bent over to pick it up so he could see all of my legs from the back. I could feel my excitement rising as I knew he was checking me out. I picked up the dollar and when I turned around I “accidentally” bumped into his hip with my shoulder. “Excuse me.” I said. “I am so clumsy. I have already broken two glasses tonight and this is my friend’s apartment, not mine. She is going to pissed when she sees her glasses missing.” I giggled after saying this and picked up my drink and took a swig. “Maybe it is because I had too many of these, te hee.” “Thank you again, ma’am for the tip. You are a very beautiful woman.” He said. I set my drink down and walked by him towards the front door, when I brushed by him, I could see he either had the start of one, or was already posting a hard on. I remembered myself at that age and I got hard when I looked at a girl, so with my little show, I was sure he was getting excited. I got to the front door, but he was not following me. He was watching me walk away. “What are you looking at young man?” I said. “I am sorry ma’am, but I was just looking at you.” He said. I closed the door half way and looked at him. “Come here.” I said. He walked over towards me with a very nervous look on his face. He was still carrying the “keep warm” box the pizza was carried in and he was carrying it in front of him at his waist line. “What is your name?” I asked as he approached me and the door. “Joe” he replied. “What are you hiding, Joe?” I asked. “Are you getting excited watching me?” “Yes ma’am. I should be leaving, I am sorry.” He stuttered. “It’s ok, baby. Do you want to leave right now? I don’t think so.” I said. I leaned against the door and gently shut the door. “How old are you Joe?” “I just turned 18.” He said. “Really?” I asked in a very inquisitive voice. “No, I am 17” he stuttered. “Have you ever been with a girl?” I asked. “Well, I have played around some.” He said. I took the carrying box from his hands and threw it on the floor. I could see the conversation had not taken down his excitement level. I came up close to him and whispered “Do you want me to make you cum?” “Yes, please.” He said. I took him by the hand and let him to Sheila’s bed. I sat him down on the edge of the bed and unfastened his blue jeans and slid them down to his ankles, he kicked off his tennis shoes, so that I could take them all the way off. He was not wearing underwear and I could see the most magnificent cock in my life. It was so smooth black and shiny. It was like a rocket ship about 8” long and very thin. I couldn’t wait to suck it. I laid him down on the bed and he was very quiet. I could tell how nervous he was, but also how excited. I spoke in a very authorative but feminine voice. “Relax baby, but promise me one thing. This is our little secret, I don’t live here and I can’t let people find out I was sucking cock of a minor in my friend’s apartment.” “Yes ma’am, I won’t tell anyone.” He said this as I started stroking his cock. “Oh, wow, that is so good.” I couldn’t believe the length it continued to get longer as I stroked it. I crawled up on the bed beside him and kissed Joe’s mouth. He didn’t kiss very well, but after about 30 seconds, he was getting the hang of it. His mouth started to anticipate my tongue and he started to wrap his tongue into my mouth. Throughout the long kiss, I continued to stroke his long cock up and down. He took is right hand and started to untuck my shirt from my skirt and I let him as I stroked his cock. He kept his hand on my stomach and then slid it under my bra. “Sorry baby, I have small tits, but you can play with them if you want.” I said. I stood up and unbuttoned my shirt and unfastened my padded bra that gave the appearance of tits. I left my shirt and bra on my shoulders and in the dim light, I was sure Joe could not tell he was about iddaa siteleri to suck on a man’s set of nipples. He went on them like a baby starving for milk. He kissed them, sucked them squeezed them and his cock was getting ready to shoot. I wanted this cock so bad in my mouth that I pushed his hands off of my chest and his mouth as well and crawled down to his crotch. I placed his cock between my tits and used my hands to create a look of breasts rubbing up and down on his cock. His face was in ecstasy and he was ready to come. I went down further and put his monster cock in my mouth and went down as far as I could on the first plunge. He was so ready to cum and I could feel it. “Baby, I want you to shoot your cum all over my tits, ok?” I said. I didn’t have to wait long as I lay down on my back and he straddled me and started to stroke his cock. After two strokes I got to see this big rod shoot a load of white cum all over my tits, chest and finally my mouth. I slurped up his sweet cum from the edge of my mouth and then scooped up a big load on my left tit and swallowed it “Thank you, honey. I was so horny and you just gave me what I needed. How was that for a secret to keep? I asked. “That was great ma’am. I have never had that before.” He said. “Well if you ever get a delivery request for Sandy, you might get even more next time.” I said as I was licking off the last of his cum from the tip of his dick. When I was doing this, I noticed he was getting hard again, but I knew I could not do anymore right now. I pulled up his pants and he got dressed, I walked him to the door and gave him a big kiss. “Don’t forget you pizza case and don’t forget this is our secret.” I said as I escorted him out the door. “Yes, ma’am.” He said. And then he was gone. I washed all the rest of Joe’s cum off my chest with one of Sheila’s dirty towels. I did a quick inspection that I did not leave anything. I packed up my bag with my scotch and ice and glass and my pizza and left her apartment. I locked the door then slid her key underneath the door and walked down to my apartment. I knew for sure that I was going to have an excellent road trip! Chapter 10: Drinking at the Hotel Bar I felt very refreshed Monday morning and was very anxious to start my road trip. I knew I was going to be successful on my trip as the new line of product I received in New York was perfect for the customers I was showing this week in San Diego and Phoenix. I packed up my briefcase with all of my work papers. I grabbed a couple of beach towels, a blanket, my half empty bottle of scotch and my shopping bag with my two new outfits. My Monday was uneventful. I had two appointments one in Carlsbad (north of San Diego) and one in La Jolla (very close to San Diego). I checked into a Holiday Inn in San Diego. At the check in desk I told the agent behind the desk my fiancé would be arriving later and would like her name on the room as well. I told them her name was Sandy Stirling. This was something I was going to do at all the places I stayed, in case I wanted someone I met as Sandy to call me at my hotel. I borrowed a luggage cart and went to my room with all my suitcases. I got to my room and unpacked all of my suitcases. I couldn’t believe how many things I had brought, I had a full closet and two drawers were filled. I spent about a half an hour getting things together from my work day and headed downstairs. I had the front desk fax all my orders to the corporate office and I went to the bar in the hotel. It was a nice small bar kind of dimly lit and featured a bar with about ten stools, three booths and a three pub style tables. There were about six guys in the bar at different places all with shirts and ties, a group of traveling salesmen like myself. I had a beer and an appetizer and then left. I stopped by the front desk to pick up the faxes I sent and went back to my room. I took a shower and then selected an outfit to wear. I poured a drink as I chose and lay out a conservative outfit, but with some sexy elements. I wore a black skirt that went just below my knees, but featured a long slit in the back that went half way up the back of my thighs. I wore black fishnet stockings that were kept on with a black lacy garter belt. I chose high heel black boots that went up to the hem of the skirt. My top was a black wool sweater that was loose fitting in the top but tight at the waist. Underneath I had a black lace bra with a matching camisole and black lace panties with my “secret keeper”. I wore my black patent belt with matching buckle, gold jewelry and my henna wig. I finished my third drink in my room and then I grabbed my black handbag with all my necessary items and walked to the elevator. I went to the lobby and entered the bar I drank in earlier. It was now about 9:30 and there were only two groups of guys left in the bar. They all looked pretty drunk, as they had been drinking for at least two hours watching a football game on the television. I strolled in and sat down at the bar stool at the end of the bar and closest to the entrance. Even though I knew I was totally passable, I still wanted to sit in a dimly lit section and a place for a fast exit, as this was my first time out in a public place by myself, other than a walk around the streets. The bartender came over to me and was very nice. I noticed for the first time what a difference the treatment a woman gets in a bar versus a guy. “What can I get you young lady?” he asked. This was the same bartender that served me earlier and he had no idea I was the same person. “Do you make a good martini?” I asked, batting my eyes a little. “Sure, how would you like it?” He replied. “I will take a Cosmopolitan with Stoli vodka.” I said. “You got it beautiful.” He said this and turned away to prepare my drink. I pulled out a newspaper that I brought down with me and opened it up to pretend I was reading.