Where do I start? How about at the beginning. My name is Cal I am divorced and living alone. I am not a bad catch I am five foot eleven, short black hair, green eyes and no visible scars. I am a regular at the gym so I am in shape but not ripped. A seven inch uncut cock that I can use well. I dress nicely and have a good job. My friends Don and Lisa were feeling sorry for me they knew how ugly my divorce was and how lonely I was so they invited me to their pool party last weekend. They said there would be some single women there and I might find someone I like. Me I thought I would go have a few drinkss then come home to my lonely apartment. Okay, I thought at least it gets me out of the apartment for an afternoon. I met some friends I knew there and mingled a little bit and several times Lisa brought over girls to introduce to me but after small talk the interest was not there. That is until I saw Leslie across the yard. She was medium height, shoulder length chestnut brown hair, brown eyes with what appeared to be a generous c cup chest. She was wearing a black string bikini top and a tropical looking sarong with what I assumed was a matching bikini bottom underneath but I could not see it. She wore flip flops and had painted toe nails. She was average in body type. Not slim but not chubby either. A bit of a curve to her hips but she wore it nicely. I put her around my age at about 32. I finished my beer and went over to her when I saw her at the desert table and introduced myself. She was cuter up close and had a sexiness that seemed to be natural to her. We chatted for some time and found a few common interests, enough for me to ask her to a little coffee house near work a few days later. She accepted happily and gave me her phone number. I was so happy that I finally felt a connection with somebody. It had been so long I was beginning to loose hope. A few days went by and I called her and set up a date for the following day. We both met after work and had what was suppose to be a quick cup of coffee but we ended up going out to dinner afterwards and I did not get home until almost eleven that night. I really felt my luck was changing in the romance department as she asked me out to the movies that Friday night. We went to an early show and since it was the weekend and neither of us had to work the next day we went to a late supper at a little place near the theater. As I walked her to her car just before she got in I gave her a hug and went to kiss her cheek but she turned suddenly and I planted one right on her mouth. She did not turn away but instead put her arms around my shoulders and I wrapped mine around her waist and we stayed that way for five minutes or so kissing. Her lips were soft and warm with nice moisture. Her ass felt firm and I squeezed it. I did not want to stop but she pulled away finally. “we could go back to my place” I said holding her hands. “no not yet Cal, lets go slow and get to know each other first. K.” “okay” I kissed her again. “ but lets not wait too long” I winked at her. “no no of course not, but lets not be too crazy either” So we parted ways there and I went home thinking I came on too strong and may have blown a good thing. A few days went by and I heard nothing and had almost given up on her when she called me out of the blue. She apologized for not calling sooner and said she wanted to make it up to me by making me dinner on Saturday. I excitedly agreed and counted the hours to seven on Saturday. She asked for casual dress, jeans and tee shirts were the expected and I wore my favorite Levi’s that were slightly too tight and a black button up silk shirt but left it un-tucked. I brought a bottle of wine and timed it to be there right at seven. She greeted me at the door in a pair of Old Navy jeans and a navy blue turtle neck short sleeve shirt that hugged her curves so nice I just wanted to hug and kiss her right there. I settled for a peck on each cheek. Her hair was in pig tails and held with pink elastics. She was just putting dinner on the table when I arrived and after a hug and another peck on the cheek, I poured the wine and we sat down to dinner and conversation. It was a light meal of salmon, rice and asparagus. Followed by a bowl of ice cream and fruit. We then went out onto her balcony overlooking the city and had a cup of coffee. We sat in the warm summer evening and enjoyed a breeze from the north. I was looking out over the city when I felt her fingers gently tracing along my arm. It sent chills through me to my spine, it was so gentle and intimate I started getting aroused. “Cal we have gone out a few times and I like you a lot” “ I like you too Leslie” as I turned to her. “before we go farther,... I want to go farther, really I do, more than I have with anyone in a long, long time, with you cause I think you are very sexy and I bet good in bed” “well I don’t wanna brag but” We both chuckled awkwardly. “listen I have a secret only a hand full of people know and if you and I are going to be lovers, you will need to know too, and have to be very comfortable with or its no go okay. Now, also I ask that it be our secret okay” “sure but what is it?” I was worried she had an STD of something of that nature. I was not even thinking what came next was even on the radar. “well you strike me as pretty open minded and non judgmental so lets go into the living room and I will show you” She took me by the hand and led me through the dinning room to the front room and turned on the small lamp by the arm of the couch and sat me in the middle of the couch, and took a seat on the coffee table facing me. She took my hands and held them. “you think I am pretty? right?” “y yes of course I do” I was thinking she had a weird scar or tattoo or an extra toe or something. Maybe? She began by pulling off her top over her head and as the shirt popped off her head her breasts gave a nice jiggle. She then cupped them they were being held in by a turquoise satin bra that was lifting and amplifying them. I licked my lips in anticipation. She looked at me and smiled as if to say she knew I was lusting after them. “Ya, you like my tits do you not, Cal?” she asked “very much, so much I want to taste them” she smiled. I was getting very anxious. She stood up and undid her jeans and just before she slid them down her legs she gave me a concerned looked. Even bit the side of her lip wondering if she should do it or not. She smiled than pushed the pants down and stepped out of them and kicked them aside. “this is what you need to see Cal” she said pulling up her boy short panties that matched the bra in colour but had lace frill on the waste and legs. That is when I saw it. The bulge in her panties. She had a cock. A big one. “well” uneasily she stood there. “ say something please” There was panic in her eyes. “so you are a she male then? are you? Is that a correct term?” “yeah it is an okay word, long ago I choose to live as a woman please do not tell any one” biting her lip I could see she was scared. “I won’t.....don’t worry. I am discreet” I do not know why, I had never thought of these things before, shemales it seemed such a nice idea. But I was getting more and more turned on. Maybe more than some, it wasn’t desperation for sex not at all. It was that I really liked Leslie and didn’t care what she was. To me she was just her. I began to rub her dick through the silky panties. She began to relax as she knew she was safe with me. I pulled down the silk and watched as her eight inch cock with a good two inches of girth came to life in front of me as I began to rub it. “can I suck it?" “ I-I-if you want" smiling down at me “or__ I could fuck you with it" “lets start with you mouth fucking me and see where we go" “K" She seemed pleased with the answer and my open attitude. She was looking much less scared and more relaxed. Her penis was actually beginning to harden as I touched it. I sat forward on the edge of the couch and took it into my mouth and began sucking on the head. She whispered softly as I played with her balls and took her deeper into my mouth. “god! are you sure you have never sucked a cock before because you rock it baby” she grabbed my head “not even gagging on my thick dick.” “never” I stopped and looked up at her as I grabbed her ass and smiled. “but this feels so right” I licked her balls. “why does it feel so right, and why am I good at something I have never done before?” She just looked at me with a warm smile. “good, it feels good because you aren’t hung up on anything. Just go with it honey” she stood me up and took off my shirt and undid my pants and slid to her knees and took my dick out of my underwear and started sucking me hard and fast. I grabbed the pig tails and guided her motions. “so” I groaned. “how does this work?’ “you are going to take me into the bedroom and fuck me silly?” I asked? “Then we rest up and do it all again” She giggled. “You are an anal virgin though, so I will be gentle, use lots of lube." She took me by the hand and led me to her bed. She slid open a drawer and took out a tube of lube and rubbed some onto my swollen member. “I know this is new to you but just do what feels right stud” she laid back on the bed and opened her legs. I knelt between her legs and spread them enough that I could get in. With little effort I slid into her tight ass and she moaned with pleasure. “doan hold back Cal love me as hard as you want, I won’t break” she wrapped her legs around me as I pushed deeper into her. Her arms were around my shoulders and she pulled me to her and kissed me as she scratched my back while I drilled her deep and hard. I could feel her hard cock rubbing against my stomach as we fucked hard and fast. The sound of slapping flesh was getting us both hotter and hotter when she began panting. “I am gonna fucking blow so hard, Jesus its gonna b b be” I felt her come hard in endless streams of come. It soaked in between our two sweating bodies making us sticky and stuck together. “you like that hunh” as I pulled out and turned her on her stomach. Pulling her onto her knees but her face still in the sheets, I stood on the floor and pulled her back onto my dick again and slapped both my hands onto her lovely hips hard enough to leave red marks. Gripping her thighs tight I slammed into her over and over as the bed shook and the frame squeaked. I again reached forward and pulled her pig tails and put one foot up on the bed. I was pounding hard and fast and she was growling and grinding onto me hard and heavy. “I am gonna come so hard” “god Cal come on my tits” she said. So I accepted. I pulled out of her again and she rolled back onto her back as I knelt over her and placed my greasy dick between her breasts which were still in that sexy bra. I pushed my dick between her c cannons and under the bra and pushed her jugs together. She put her hands over mine and pushed so her tits created a nice place to screw. As I thrust up she licked the tip of my cock. “do it Cal! wash my face and tits with your come!” I did not need more encouragement I shot four or five thick hot streams from the top of her tits to her hair line. She took a few minutes to use her finger to scoop up and swallow as much as possible. She just smiled and said she hoped there was more to come.
