Chapter 3: New York with Linda I didn’t really get a lot of time to think about what I had just done with Carlos. I fell asleep shortly after he left due to all the drinks I put away during the night. I actually fell asleep on my couch, still full dressed except for my jacket and shoes. When I woke up, I had a headache and was starving; I never even had a piece of the pizza Carlos brought. It was 2:00 in the morning and I was scared to look in the mirror.I took a shower to clean off the make up and put away my outfit. It really didn’t require a wash, but the skirt needed to be ironed. That could wait. I ate a piece of pizza, went to bed and slept until 8AM the next day. It was a Saturday and I had to do a few errands, as I was leaving Sunday for a business trip to New York. I was hung over, but by the time 5:00 rolled around I was feeling pretty good and went out for a couple of drinks. I couldn’t believe that I was back in my “normal routine” of drinking in a bar and trying to score with chicks the night after my first full cross dressing and sexual experience as a “woman”. I left early that night, went home and gave a nice hard pumping to my inflatable friend and fell asleep.Sunday was here and I was flying to New York, I took an 8:00 flight from LAX to JFK and was upgraded to business class. Since there was no weekday traffic, I was in my Manhattan hotel by 6 PM. I was feeling great, I had a full nights sleep, had four or five free cocktails on the plane and was in New York City. I took a shower, changed clothes and left my hotel. I grabbed a bite to eat at a great bar at 46 th Street and 8 th Avenue. This bar had the best hamburgers in the city (in my humble opinion) and I washed it down with a couple of beers, then I had a couple of scotches and watched part of a Rangers game on the television at the bar. I went for a walk and ended up in another bar and had a couple more drinks and was feeling pretty drunk and especially horny. I went to a liquor store and bought a fifth of Johnnie Walker Red Label to have in my room for the week in New York. I poured a drink upon my return to my hotel and decided what to do, it was about 10 PM and I was not tired.In those days, it was pretty easy to find a hooker in New York and if you wanted, you could also find some recreational drugs in this part of the city. So I thought, why not? The meeting I was attending did not start until noon the next day (Monday), so I walked down to 8 th Ave and scoped out the scene. I was always careful on how I approached any woman that I thought was a hooker, as I did not want to get arrested. I finally saw a tall girl on the corner that was alone and was obviously a hooker.“Hi Honey, what’s going on?” I said to her.She was as tall as me and was wearing boots above the knee in black patent. A red skirt that just reached the top of her boots, black tights, a black top and a long coat that reached her calves. I would guess she was about my age and had dark skin, but not really black. I guessed she might be from the Caribbean originally.“You ain’t a cop, right?” she said.“No, I am not, are you?” this is pretty standard conversation between a hooker and a “John” on the streets of New York.“Why don’t we walk together for a while” she said. “My name is Linda”.“Great idea Linda, I am Tony”.“What are you up to? A white boy like you in this part of town is trouble.” She half spoke and half laughed this last statement, making light of the situation. “I hope you want to have some fun”.“Absolutely, how much will the fun cost me”? I asked while we approached the next corner.“Well that depends what you want to do. Do you want to party? I assume you have a hotel room near by.”“It is still early, I would love to party for a while. I am staying about four blocks from here, where can you get the party supplies?” I asked.“You like the pipe, Tony?” Linda posed.“Sure honey, as long as we start now, I don’t want to be up all night, Linda.”“OK, give me $20, and I will get us a couple of rocks. We can smoke in your room and we can play around, for another $20. I will go down the street and get the stuff; here you hold this so you know I am not going to run off with your cash”.She handed me a brown paper bag out of her purse and I looked inside, there was a crack pipe and a couple of small plastic bags that obviously had some crack cocaine inside them. “See there is already $20 worth of shit in there. I’ll buy us two more and we can party for a couple of hours. You will be asleep by 2:00” she explained.“Great, I will meet you in ten minutes at 47 th and 8 th , this side of the street.” I said“OK honey, get ready for a fun time in the city, ha ha” she laughed.Twenty minutes later we were in my hotel room ready for the party to begin. I poured myself a scotch with some ice and a splash of water and looked at Linda. She said “That looks good honey, how about pouring me one?”I poured her drink and she took off her coat. She was even fuller figured than I thought, but like I said before I am not too picky, plus she was the supplier of the crack. She unzipped her boots and slipped them off. She slipped off a wide black patent belt that was around the top of her skirt and breathed out, “That feels so good to take that off.”She took the brown paper bag I had laid on the nightstand and she sat on the bed. Linda removed the pipe and the two bags of crack. She took a small wire brush out Çukurambar escort bayan of her handbag and the new two bags of crack she had just purchased and laid all of the plastic bags on the night stand. She then used the brush clean the pipe by inserting it in the length of the glass pipe and moving in back and forth. She then put a small piece of material that looked like steel wool in one end of the pipe and then placed a couple of small crack rocks on top of the “wool’. She motioned me over to sit next to her and she lit the pipe with her lighter while inhaling on the pipe. The rocks began to sizzle and the edges started turning red and then black, the sizzling got a little louder as she drew harder on the pipe. As she was about to exhale she pulled me over to her and put her lips on mine, I opened my mouth and she exhaled the smoke into my mouth and deeply into my lungs. It is such a great feeling the first hit of crack, the smell and feeling is so intoxicating, it is easy to understand how addictive the drug can be. I had never had anyone do this exhale process to me and it was so cool. I felt like I had a direct hit off the pipe without the heat, just the pure “coke’ hit. “Wow! That was so cool!” I said after I held my breath as long as I could before exhaling to maximize the ‘hit’.Linda looked at me and said “Tony, I think I can teach you a few things tonite and have some fun”.We took turns on the pipe and reloaded until we had smoked the first packet. She was awesome teaching me the best way to “hit the pipe” to get maximum hits. She would make me exhale completely before any hit, either direct or from her “exhales’. I was truly high and feeling great. I love the feeling of crack much better than regular cocaine and this was the best high I had ever felt. We had a cigarette and drank some of our drinks. We talked about random stuff and I really was starting to like her company. Suddenly she leaned over and kissed me. “I like you, do you think I am sexy?”I said “Linda, you are good looking, but I find the sexiest thing about you is the way you act and carry yourself. You are so cool and I like partying with you.”She pulled me closer and started unbuttoning my shirt. She didn’t take it off me, but just left it unbuttoned. She loaded the pipe again and she did the exhale trick again on me. She looked at me and said “I love how you get high. You are so mellow and I like how you take my hits”.I stood up and removed my shirt; she unbuckled my belt and started to remove my pants. “Hey baby” she said as she was looking at my small cock, I won’t be able to fuck you tonite, just a blow job….wrong time of the month”.“That’s ok, but please take off your clothes, I want to see you”. As I finished this statement, she was sucking my cock and making me hard.“You know I think you might be able to fuck me in the ass, your cock isn’t too big. But you have to keep a secret if I let you fuck me.” I was now hard and wanted to fuck that ass of her so bad. She had a nice ass, kind of big, but I love fucking chicks in the ass.“Sure, honey, anything.” I said.She stood up and pushed me down on the bed. Linda told me she would be right back, she turned off the overhead light from the light switch in the hall and went into the bathroom. She returned a minute later wearing nothing except a pair of black panties. She left the light on in the bathroom, so there was enough light to barely see, it was still very dark. Through this dim light, I could see she had a full body, but I was surprised by her chest. I could see her large tits with big round nipples; I was hoping she would bend over the bed right now so I could kiss those nipples! I wanted to suck on them and squeeze those big ass tits. She climbed on the bed and lit another pipe load exhaling through my lips and deep into my lungs. She then held the pipe to my lips while she started sucking my cock again. This time she was really going at it, she seemed to glide her lips and tongue up and down on my cock. She would lick the underside of my balls and stick her tongue up my ass crack and lick my asshole. Then she would engulf me in her mouth looking up to me so that I could see the whites of her eyes, like she was in ecstasy sucking my dick. She slid her mouth up and down on my cock and would suck on it in a way that made me shiver. She went up and down so fast it seemed her head was on a spring. She reached into her handbag and brought out a condom which she placed on my cock… I was almost sorry she did that, because she was giving me the best blow job I have ever received.She also had some lubricant that she pulled from her bag and slid it on her hands and placed her hands inside the back of panties. She was obviously “lubing up” her ass for me to fuck her, and boy was I ready. She gently stroked my cock to keep me hard and then lit up another pipe load. This was our third rock and we were both so high, but at that perfect state, where you still want more, but are feeling so good. When you are at this perfect level of ecstasy, your cock can stay hard a long time, but not too high where you can’t do anything…it was pretty close to bliss.She turned her back to me and slid off her panties; she then slid on the bed with her back to me and directed my cock with her hand into her ass. She had her hand wrapped around her back holding my cock and in the Escort demetevler dim light I could see and feel me enter her. She moaned in pleasure and then started lifting her ass up and back down to get my full length in her. “Oh yea, baby. Fuck me good, I love your cock in my ass. God, that feels good…oh God I love your cock!” she yelled.After riding my cock for about three minutes, Linda got off my cock and came off the bed. She motioned me to get off the bed too…I slid off and she came around to the side. She took my hand and brought it to her crotch, what I felt in her crotch was not a wet messy pussy, but a very soft penis…yes; you guessed it she was a she-male. “This is my secret” she whispered. “Do you still want to keep fucking me?”I stood behind her and bent her upper body over the bed; I spread her ass cheeks apart and inserted my cock back in her ass. “Does that answer your question, Linda?”I never fucked harder in my life. I was like a small jack hammer pounding her ass as my balls would actually bang into her balls as I pounded harder. “Fuck me baby, fuck me more.” Linda screamed.I pulled out and rolled her over on the bed so that she was on her back and I could look into her eyes. She slipped her feet on top of my shoulders and I slipped my cock in her ass and started fucking her again and now I was able to feel and squeeze her tits. She was a perfect fuck, nice tight ass, big tits and begging me to fuck her harder. I was about to come and she felt that I was ready. “I want you to come in my mouth, come fuck my mouth as hard as you fucked my ass.”I pulled out of her ass slipped off the condom and put my knees on each side of her head and slipped my cock in her mouth. She was working her magic again and started fucking my cock with her mouth. She put her hands on my ass and shoved my cock in her mouth by pulling my butt toward her face; she wanted me to face fuck her. I started fucking her mouth as hard as I could, and she kept moving her tongue while I fucked her. I loved feeling my balls hit her chin and I felt so powerful. The entire time she looked like she loved it and that made me enjoy it more. I exploded in her mouth and she drank every last drop.When I finished cumming and she had licked my cock and balls clean, I asked Linda if she would teach me how to suck cock so well. I guess you know what I did the next thirty minutes. She told me that she had difficulty becoming hard due to all the female hormones she was taking, but to please try playing with her. I took another strong hit of the crack and started to go to work on her nick cock. It was about the same size as Pedro’s, but a little thicker. Linda said she couldn’t afford to have the final surgery too have her cock and balls removed, but she hoped that in the next year she would be able to. So in my mind I thought enjoy it while you can! I exhaled my hit all over her cock and balls and she gasped, it was starting to work as her cock began to stiffen. She guided my every move, told me when to open my mouth wider and when to close my lips around her stiff dick. She told me how to use my hand to stroke her dick and when to lick her balls and to stick my tongue up the crack of her ass. She taught me to look at her face as I licked her cock up and down, to always smile and look like I love sucking cock. Linda started moaning as I continued to eat up her delicious cock and then she came! She shoved the back of my neck down so that my lips were all the way at the base of her cock and she shot her load down my throat. It was fantastic.We finished up the last rock and soon Linda was gone. It was the best two or three hours I had experienced in a long time. I never saw her again, but I have never forgotten anything about her!The rest of my trip in New York I was wishing that I was back in Los Angeles practicing how to suck cock and to dress up like a little whore and seduce more unsuspecting men. I came up with a few ideas on what I could do to have more fun with my secret, without getting caught. I was kind of in a day dream the entire trip after my night with Linda and my memories of Carlos. It was strange, I had no attraction to men, but I had this strong desire to be a woman. And when I dressed as a woman, I knew that I was going to be very anxious to find guys and suck their cock to the very end. The week dragged on and I was so anxious to get home, I arrived back in Pasadena on Saturday night and I was ready for some more fun!Chapter 4: Sandy, Tony and Sheila When I arrived at my apartment it was around 6 PM on Saturday, I decided to take a shower and head downtown and have a drink and a bite to eat. I had a couple of drinks at a bar on Colorado Street; it was a local dive with pool tables and a “regular” crowd. I had been there on several occasions, but did not know any of the people that hung out there. I drank a couple of Coors and was starting to feel a nice little feeling of alcohol hitting the blood system. I started thinking what my plans should include tonite and was also doing a little soul searching.I was thinking about my current situation. I really had no close friends in Southern California. Most of my closest friends were living in Arizona or were my work friends that were scattered around the country in places like San Francisco, Seattle, Dallas and New York. I had broken up with Beth completely dikmen escort about two months ago. I had acquaintances that hung out at my local bar, but no close friends. I think that is why I was confident that I could keep my secret being a cross dresser. It was still just a one time event (two, if you count the little swim in the pool), so I kept thinking about how I could continue to dress without getting caught.I finished another beer said good bye to the bartender and drove a couple of blocks to a cool section in Pasadena called Green Street. I had dinner at the Hamburger Hamlet and had a couple of scotches and then went next door to the Saw Mill Bar and Grill and had a couple more. I was feeling really good and talking to an average looking woman named Collette. She was African-American about ten years older than me and had a very nice set of tits. Collette was a little drunk, but not enough to agree to let me take her home that night. We exchanged numbers and I decided to go home. I was only home about 30 minutes when Collette called and explained she changed her mind and wanted me to come over to her house. I was very tempted, but I didn’t want to go out after being home…I was already out of the shower finished shaving and starting to dress up in my female attire. I agreed to meet her tomorrow and we would see what would develop.I finished dressing up, applied my make up and wig and strolled out my apartment door and down the hallway, with a much higher level of confidence than the first time a week ago. It was a little after 10 PM and there were very few cars and people in my residential area. I decided to walk up to the main street (Colorado St.) which was about three blocks away. There were lots of people walking on Colorado, so I tried to keep a low profile so people would not notice me. It was very uneventful, but again it gave me confidence to be in public and not being immediately identified as a cross dresser.I returned back to my apartment and entered through the parking garage and approached the elevator to take the ride up to the first floor. I thought going through the parking garage instead of the main entrance would be a good test. I was more likely to see one of my neighbors as we all drove everywhere we went and very few times would you see someone in the main entrance. I was always trying to test my new appearance, but at the same time always worried someone would know I was a man, and even worse would know it was Tony in apartment
13.As I reached the elevator, I pushed the call button and was waiting for the elevator to arrive. I heard a sound behind me that sounded like the click of high heels on the ground. The sound was getting louder as the person walking was approaching the elevator. I had not noticed any car “running” in the garage, but there must have been someone that pulled into the garage before my arrival. As the door to the empty elevator opened, I heard a nearby voice call out “Please hold the elevator”.I really did not have a choice, so I held the door open and within seconds, a woman about my age appeared and said “Thank you”. She had obviously been drinking as I could smell alcohol and cigarettes on her breath and clothes. “I could not find my house keys; I have been looking in my car for ten minutes.” She laughed a little and then said “They were in my pocket, and I was looking in my purse and on the car floor, everywhere. And they were in my coat pocket…do I feel silly!” Some of the words she were saying were so slurred, it took me a few seconds to understand what she was trying to say.“Well, I am glad you found them. You must have had a good time tonight.” I was speaking in my new found “Sandy voice”. I looked her over and I found her very sexy. Not a “10” by any means, she was about 5’6” a little overweight, long brown hair with the most beautiful brown eyes (they did have a little redness to them from the drinking). I couldn’t tell much about her body, she was wearing a loose fitting dress and a long purple knee length lightweight coat.The elevator door closed and she said “Do you live here? I have never seen you before.” She was definitely drunk; I had to figure out what she was saying as all the words were slurred.“No.” I replied “I am staying with my brother, actually house sitting for him and he doesn’t like me to smoke in his apartment, so I stepped out front to have a quick cigarette”.“Wow, I could use a cigarette right about now, I have been drinking for a few hours and I was bumming cigs all night from Betty. She’s my friend I was drinking with, hey if you want come up to my apartment and have a smoke later. My name is Sheila; I live on the 3 rd floor. Shit, I forgot to push my floor button!” We were stopping on the first (my floor) and the doors opened.“Are you sure?” I asked as I held the door open button. “I would love to come up; I have a bottle of wine and a bottle of scotch, if you want to have another drink?”Sheila said “Sure, bring the scotch if you like, I have plenty of wine. Give me about ten minutes; I am in 328, what’s your name?”“Sandy, see you in a few!” I said as I stepped out of the elevator and let the doors close.The doors closed and my mind was rushing 100 miles per hour. Why did I say I would come up? What if she knows I am a cross dresser? Maybe she would not notice, how drunk was she? But I kept thinking what should I do? What do I have to worry about? If she knows I am a cd, so what? She doesn’t know me; she doesn’t know my apartment number. I finally was able to stop all of these thoughts rushing through my head and made a decision. What the hell, I am going to go up and party with Sheila.I walked down the hallway and was so nervous; I almost fell off my heels.