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 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 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 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 #113.
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. All those worries and thoughts came back. I thought she was drunk, but wouldn’t she be able to tell pretty quickly that I was a guy dressed as a woman. Should I tell her? Should I just not show up? What should I do? I opened my door and grabbed my bottle of scotch and poured a stiff drink. Ok, just settle down, relax, you can do this. These were some of the thoughts in my mind. I finally decided I was going to do it; I was going to Sheila’s apartment and see what happens.
I decided to bring a bottle of wine and scotch and try to get her to drink a lot more. Maybe she wouldn’t notice the obvious signs that I was not a woman. I went into the bathroom and touched up my wig, make-up and lipstick. I sprayed another shot of perfume on my neck and chest. Wow, what would we talk about? Girl things? I bet she will think I am so slutty in my short skirt and mesh thigh highs. I was starting to get a hard on thinking of this whole adventure. I chugged down the rest of my drink, grabbed my purse, the bottle of scotch and an open bottle of chardonnay in my refrigerator and headed out.
I decided to take the stairs, instead of the elevator and this gave me even more time to think about my meeting with Sheila. Why would she invite me to her apartment after a 30 second meeting in an elevator? Well, maybe that is what girls do. Can I keep my Sandy voice the same way for more than fifteen minutes? Well I did ok with Carlos. SETTLE DOWN, what do you have to lose? This was my calming (or an attempt to calm down) thought. I had no more time for thought, as I reached the door to the third floor from the stairway. I had a last concerning thought…do I have a pair or two of Sheila’s panties in my apartment from my earlier thefts?
Arriving at Sheila’s front door, I exhaled strongly and knocked; “Sheila, it’s Sandy” I said. The door opened almost immediately and there was Sheila, but a lot different than she was fifteen minutes earlier in the elevator.
Sheila had changed out of her going out clothes and was now in her “relax at home” clothes. “Hi honey, I am so glad you came up…come in here and get comfortable and please let me have a cigarette, I hope you don’t smoke menthol.”
My initial feeling was, cool! She is making me so comfortable, but then again she thinks I am a girl. I quickly relaxed by exhaling deeply and said “Sheila, thanks for inviting me up, it is so nice to meet a new friend. I smoke Marlboro lights, hope those are ok.”
The apartment was almost identical to mine. The only obvious difference was no balcony, but other than that the lay out seemed identical. I walked in and placed the wine and scotch on the mini counter that separated the living room from the kitchen. She had an identical living room to mine and her couch, coffee table and television were in the exact same spots as mine. I was glad there was only one lamp lit and the only other lights on were in her bathroom and bedroom. A dim lighting was only going to help my charade.
Sheila approached me and I took note of her change in appearance. Her long brown hair had been pulled back in a pony tail. Her face was the same and her beautiful brown eyes were even more striking with her hair pulled back. The dress and long coat had been replaced by a long sleeve t-shirt and a pair of velour sweat pants, no shoes just a pair of white socks. There was no confusion now, this girl was built! Like I described earlier, she was a little over weight, but this was a body I could spend hours playing with. Her breasts were probably 36C, she had a nice tight ass (a little big) and you could see here legs were hot even hidden in the sweat pants. “Thanks babe!” she said as I handed her a cigarette and used my pink bic lighter to ignite her smoke.
I lit a cigarette for me and she said “Welcome to my little cheap place”. She was still slurring her words, but they did seem a little more coherent than the elevator.
“Thanks, Sheila, I love your place, it is almost identical to my brothers’. Now show me the ice tray and a glass, if you don’t mind. I need a drink.”
“You are my kind of girl, Sandy.” Sheila pulled out an ice tray and a tumbler for me and a wine glass for her. “Well, I guess I have to try the wine you brought.”
I took the glasses and poured a glass of wine for her and then put ice in the tumbler and poured scotch and a little water in mine. “Cheers, to new friends” Sheila immediately said upon clinking her wine glass against my tumbler. She took a healthy drink and a strong toke of her cigarette.
“Shit, I am fucked up, sister!” Sheila said. “Please forgive me; you must think I am a fucking drunk.”
I tried to stay calm and measure what I should say. “Oh Sheila, I am just so happy you invited me up to your apartment. It is so nice to meet someone here. Tony, my brother is coming home tonight and I have been so lonely, as I don’t know the area.”
“No problem, I thought you had been out tonight, based on how you were dressed, you looked like you had been out, not sitting at home.” She said.
“I had the best intentions, but I had no idea where to go by myself.” I replied.
Over the next hour, we had a few more cocktails and discussed very random items. Sheila had a great stereo system, so we listened to music and just chatted about where we grew up (she was from Denver), what we did for work (she worked in a doctor’s office). I just made up stories as we went along thinking Sheila was more drunk than me. “Well, I have to go down and see if Tony has arrived, he was supposed to be home a while ago.” I lied.
“Go down and get him, bring him up here and he can have a drink with us!’ Sheila said.
“OK, but I am getting pretty drunk, can I have your number and I will call you when I get downstairs and let you know?”
“Sure, it is 555-3636…call me right away, ok? I really want you guys to come up and have a few more drinks. It is only midnight.” Sheila slurred.
“No problem!” I stood up and kind of waddled toward the door. I kept thinking 3636 to remember her phone number; our prefix was the same, so all I had to do was remember the last four digits. I reached the door and said “Sheila, maybe I will see you in a couple, but if not thanks!”
Sheila immediately rushed towards me and gave me a big hug and kissed me on the cheek. “Love you, new friend! We would be dangerous out together, I can see you like to party like me!”
I kissed her back and said “I will call you in a couple, bye for now”.
Sheila closed the door behind me and I walked down the hallway to the elevator. I pushed the call button and rode the elevator down to the first floor. I didn’t see anyone in the hallway and I entered my apartment. I went into the bathroom and pulled off my wig and applied cold cream to my face. In less than five minutes, I had removed all of my make up, taken off my clothes and looked in the mirror at Tony, not Sandy.
I went into my living room and called Sheila. “Hello.” Sheila answered.
“Hi honey, this is Sandy from downstairs.” I said.
“Baby, I miss you, are you coming back up?” She asked
“No I am too tired, I have to wake up at 5:00 tomorrow to catch my flight. I hope you don’t mind.” I said in my best Sandy voice.
“I understand, is your brother going to come up and see me?” she asked.
I was kind of shocked, but was thinking this was a great opportunity. “I don’t know, do you want to talk to him?” I asked.
“Sure” said Sheila.
“Ok, thanks, honey for a fun time tonight, I will see you next time I am in town! Hey Tony, Sheila wants to talk to you.”
I waited about fifteen seconds and spoke in my normal voice “Hi Sheila, Sandy told me about you, I am surprised we haven’t met before.” I waited anxiously to hear her response.
“Hi Tony, I don’t know about you, but I haven’t really met anyone in this place, how about you?” She seemed to be even more drunk and talking in circles.
“You are right, I know no one that lives here, but would love to meet you, and it appears my sister left my bottle of scotch at your apartment.”
“Well if you need a drink, come up and have one with me, I hope you are as cute as your sister says…she also said you were a nice guy” she laughed.
“OK, I am on my way up, #324 right? And I will try to live up to my sister’s description.”
“Yes, #324, I will see you in a couple.” She hung up immediately after saying this.
Well, talk about nothing to lose, I had a drunken hottie in my complex that my “sister” had already done the set up for me to be successful. I put on some clothes, just jeans, a t-shirt and tennis shoes and took the stairs up to the third floor. I walked down the hall to Sheila’s apartment and knocked on the door.
She answered immediately and said “Tony, you really came up.” She had a big smile on her face as she was looking me over. “This is kind of a strange way to meet, huh?”
I looked at her and by the look on her face I knew that I was going to nail this girl tonight. “Yes you are right, can I come in?” I asked.
Sheila opened the door and I stepped in, as she closed the door behind us, I decided to become aggressive and put my hands on her waist and said “Well Sandy said you were cute, but not this cute.” She immediately blushed and made no attempt to take my hands away.
“Nice to meet you. “ I said as I removed my hands and extended my right arm to shake Sheila’s hand. She grasped my hand and I brought it to my lips and kissed the back of it.
“You too! Let’s have a drink, ok?” She walked towards the kitchen and refilled her glass of wine. “Scotch, right?” she giggled.
“Well if there is any left, Sandy usually drinks me out of everything”. I said. Sheila went to the freezer and started removing ice cubes and placing them in a clean glass. She poured a generous portion of scotch on the ice. “Do you mix it with anything?”
“A little water please.” I replied and she went over to the kitchen sink and topped off my drink. “Your apartment is almost identical to mine.” I said as I sipped my drink.
Sheila started to walk by me into the living room but instead stopped right in front of me. “That is what Sandy said. I can’t believe I invited a stranger to have a drink with me in my apartment all alone.” She looked me in the eyes with those beautiful brown eyes.
“Are you scared, or just excited?” I asked.
“Kind of both.” But the way she looked in my eyes, I knew I had her right then. I sat down my drink on her dining room table and placed her wine glass down on the kitchen counter behind her.
I placed my hands on her hips and pulled myself a little closer to her, she continued to look in my eyes and I slowly lowered my head down until my lips were about an inch from hers. I slid my hands around her back so that I held her in my arms, it was almost like a reflex; she placed her hands around the back of my neck and at that moment I asked her “How about now, scared or excited?”
She blinked once and then she closed the inch gap between our lips and pressed her moist sensual lips against mine. In a half second both of our mouths opened and our tongues were attacking each others. I pulled her closer and she started rubbing her crotch against mine as our kissing went to another level. She pulled the back of my neck resulting in our lips pressing harder against each other. I slid my hands under the back of her white t-shirt so that I could feel the skin on her back. There was no doubt now what was going to happen.
I let go of her and pulled back from the kiss, she immediately pulled out my shirt front and pulled up my t-shirt over my head and shoulders. After it was removed she did the same thing to hers, I reached out and unsnapped the clasps on the front of her bra, right between her large breasts. I slipped the bra off of her shoulders and was just staring and admiring her tits. My earlier estimates were right, they had to be at least 36C with large nipples and her olive brown skin just made them the sexiest set of tits you would ever see or play with.
Before I could reach out and play with her jugs, she took a step back, pulled down her sweat pants and a pair of red silk panties. She stepped out both when they gathered around her ankles and the pulled off her white socks. Wow, what a body, it was just the way I like a woman to look; nice and round, soft, tanned and naked. Some would think she was “fat” or a little heavy…ridiculous, she was awesome. As I was admiring her, she stepped forward and unbuckled my jeans and pulled them down to my ankles along with my boxer briefs. I kicked off my shoes and stepped out of my jeans and took off my socks. My cock was so hard, I new I would not last long, so I had to get to work.
Without us saying a word, I picked up Sheila and carried into the bedroom. Her bed was not made up and the blanket and the top sheet were already pulled down. I laid her on the bed and she looked at me with those incredible eyes, wow talk about sexy. I wasted no time and placed myself at the foot of the bed and started to make my way up her legs to her pussy. I started by kissing and licking the inside of her thighs and she started pulling at my head to bring me higher. I looked up at her and I could tell she was so fucking excited. I now had my head about two inches from her pussy. It was surrounded by black hair and was glistening from all the moisture it was generating. I started kissing her pussy and gently playing with it using the fingers of my right hand. Then I took my left hand and lifted her up slightly and stuck my tongue up the crack of her ass and stuck it right in her asshole. She immediately shivered and screamed out in delight. I continued to ream her butt hole with my tongue, while my index finger of my right hand slid into her very wet pussy. Another moan from her lips when I started to dart my tongue in and out of her asshole.
“Oh, my god! That feels so good.” She was half moaning as the words came out of her mouth. I started to reach further inside of her pussy with my index finger and curled my finger up and around to find her magic spot. “Fuck, that feels good!” she screamed.
I think I hit the target and I stopped tonguing her ass and concentrated with my finger in her wet hole. I tickled the inside of her and started licking her clit with my tongue and I could feel her orgasm approaching. Sheila was breathing very hard and sliding her ass sideways to stimulate my finger in her pussy. She grabbed the back of my neck and shoved my face further into her clit. “Oh, baby, Oh baby.” She repeated. “Yea, honey, oh Tony, I am so close.” She said.
I stuck my middle finger in her pussy as well and really started going at her “G’ spot with both fingers. Sheila’s hips were now bucking forward to take my hand further in her pussy. “Oh baby, I am cumming, make me cum!” She yelled.
I backed off licking her clit and started watching my fingers at work. I replaced my tongue with the thumb of my right hand and massaged her clit while I finger fucked her. I knew her orgasm was going to be intense, but I didn’t expect her to shoot a load of clear fluid from her pussy. Wow, this was cool, a stream of clear fluid was shooting out of her in spurts, and I could not tell what it was, but it very hot to watch. As this was happening, Sheila was starting to move her hips faster and faster as she was coming and my two fingers were fucking her like crazy. Her pussy was so wet and I continued to finger fuck her and rub her clit with my thumb. “Oh God, that was great, keep fucking my Tony, I love the way you feel in my pussy!”
I pulled my fingers almost out and then tried to slide a third finger in her pussy, it was tight, but in little time I now had three fingers going in her pussy and banging her pussy with my hand. I slid up so that my mouth was on her big tits and started licking her right nipple as I continued to fuck her with my three fingers. “Kiss me, I want to taste your lips.” She gasped.
I moved up and kissed her lips and our tongues immediately found each other. We kissed for about ten seconds and then I pulled away; she whispered “I can taste my juice on your tongue. You are driving me crazy, I think I am going to come a hundred times.” I kissed her again, and started to work my pinky into her pussy as our tongues were slobbering over each other.
My cock was throbbing it was so hard, but I controlled myself not to start fucking her with my dick and continued to work my pinky into her moist cunt. “God, that feels so good, fuck my fucking cunt with your hand.” I pulled my head away, so that I could watch me hand fuck Sheila. “What are you doing to me, I have never felt so hot!” She moaned. It was amazing, her pussy seemed to mold to my hand, it was not a loose saggy pussy, but I was now able to get four fingers in her pussy. I wanted to get my whole fist inside, but I knew it would never stretch like that. “Yeah, I am cumming again!” Sheila’s whole body convulsed with her orgasm and she started shaking from head to toe. She started moaning “yes, yes, yes, yes, OH MY GOD, YES!” and Sheila’s body relaxed and she collapsed down on the bed. I had not realized that her head and shoulders and back had actually left the bed and was almost sitting up during her intense orgasm. “Oh my God, Tony, what just happened?” She pulled me closer and gave me another intimate kiss! “Wow, that was the best fucking orgasm I ever had, or should I say orgasms, I think I came three or four times!” She held on to me tight and I slid right up on top of her.
Sheila kissed me again and asked “Do you want some water?”
I nodded and she slid out of the bed and started to walk into the living room, I followed her as she went into the kitchen and opened the refrigerator and pulled out a pitcher of clear liquid that was obviously water. She poured a tall glass and handed it to me. I immediately took a big drink and returned the glass to her. She took a big swig as well and then placed it on the counter. Sheila looked at me and said “I want you all night long, but I have to suck your cock right now!” She fell to her knees and immediately put her hand on my dick and put it into her mouth. I was so fucking hard’ I immediately started fucking her mouth.
There is one advantage to having a small cock, you can face fuck girls and they don’t have to gag. “Sheila, I think you are so sexy!” I said as I was shoving my cock in her mouth. I started to piston my hips back and forth fucking her mouth harder.
After a couple of minutes, I was so ready to shoot my load, but I pulled out of her mouth and said “Let’s go back to your bed!” We walked back to her bedroom hand in hand and when we entered, she pushed me on the bed.
“Lay down baby, my turn to make you feel good.” As Sheila said this she already had her head between my legs and started licking my balls very gently. She also probed her tongue under my balls and up my ass. “I love playing with you, roll over baby, lay on your stomach”.
You should have seen how fast I rolled over, I was already in a spirit of bliss, as this babe was giving me a tongue bath. Now on my back, Sheila immediately pulled my ass cheeks apart and stuck her tongue right on my asshole. “I am going to fuck your ass with my tongue, like you did me!” Sheila said in a very deep throaty voice. She was true to her word, as she started licking my ass long and hard and then shoving her tongue inside my ass hole. She also would wrap her hand around me and played with my hard cock as she tongue fucked me.
I couldn’t take anymore. I pulled myself up and turned around facing Sheila. I lifted her up so that both of us were on our knees in her bed looking into each others eyes. I immediately kissed her and she returned the kiss with a darting tongue. I could taste the remains of my ass on her tongue, but did not stop, instead I took her tongue deeper in my mouth. I lay back down and she crawled up on top of me and in no time, she slid my cock insider her incredibly wet cunt. She immediately sat up and started riding my cock up and down so that I was very deep inside her pussy.
“Oh that feels better than your fingers.” She whispered. “How do you like the feel of my hot wet pussy?”
“It feels good, Sheila, very good.” I said as I moved my ass up to meet her up and down movements.
Sheila started to moan again and I started pinching the nipples on her big tits. “Yea, honey, squeeze my nipples, it feels good when you pinch them hard, I love it.” She didn’t have to ask me twice as I increased the pressure on her nipples and she started moaning yet again. “Oh, yea baby, I am cumming again.” Sheila gasped loudly and started really fucking me hard.
As she finished her orgasm, I pulled her off of me and lay her down on her back in the bed. I spread her legs and shoved my cock in her as hard and as fast as I could. “Tell me when you are going to cum, I want your cum in my mouth.” Sheila said.
“OK, baby, here it is.” I pulled myself out of her and crawled up so that I was straddling her chest and I put my cock in her mouth. I started slowly fucking her mouth. I was so fucking hard that I wanted to come in her mouth quickly so I started shoving my cock all the way in her mouth and she took it all and was even pulling my ass with her hands shoving my cock in deeper. I exploded into her mouth with so much cum she could not drink it all up and as I pulled my cock out of her mouth I was able to shoot more of my seed all over her face and some on her tits.
Wow, what a tremendous hour of fun we had. I looked down on my newest conquest and loved how she was licking my cum off the edge of her mouth and picking up the drops on her tits and slurping it off of her fingers. “You are a great fuck, Sheila. I think we are going to have to do this more often!” She responded by sitting up and giving me a wet kiss that shared the taste of my cum in her mouth.
We fell asleep very shortly thereafter, due to the intense fuck session and all the alcohol. I woke up around four in the morning and we kissed each other and I said that I had to go home to be sure that Sandy got off to the airport. I left her apartment and wondered when I would see Sheila next time and if having a “fuck buddy” in the same apartment complex was going to be weird.
More to follow if you like the story.....
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<a href="https://www.lushstories.com/stories/crossdressing/confessions-of-a-sex-crazy-cross.aspx">Confessions of a Sex Crazy Cross Dresser Part 2</a>