Mikes First Transgendered

This is an absolute true story.

Mike loves transgendered

I had just turned 30 and was about 1 year out of my divorce. I was dating a Filipina lady named Mika who was not the best person for a relationship, for many reasons. During our relationship Mika used to take me to this Filipino dinner restaurant which had food and late night live musical shows. During that time, I met her friend Sara who was one of the performers. I was led to believe Sara was a woman, she had such a pretty face, long brown hair, very well endowed, talked in a high-pitched female voice and always seemed to be a classy woman. A short time after I ended my relationship with Mika, she called me and asked me if it was okay if Sara called or E-mailed me, because she missed me at her shows. I didn't seem to care so I said yes.

A few days later Sara called me. We spent a bit of time on the phone and at the end of the conversation she asked me if one day I'd like to meet her for lunch. Sara stated she missed seeing me and wanted to get to know me more. I agreed and told her over the next few days we plan something. It wasn't long that Sara and I were talking almost every day. We finally managed to find a day to meet for lunch and we ended up at a quaint little café near my house and sat and enjoyed each other's company. Over the course of the next few weeks we ended up meeting 3 more times for lunch. One day Sara called me and said she had a coupe things she had to tell me. I listened intensely as she admitted she had an admiration for me and was very interested in maybe taking things forward. The second and more important admission was that she was transgendered, as she called it "a shemale".

Sara asked me if I knew what a shemale was? I replied I did. Since the internet and internet porn had come of age, I had seen many porns involving shemales, bi or gay sex. See even though I had always kept it to myself and never acted on it, I knew I was bi-sexual and had always had a desire to have sex with a man. There were many nights (as most men do) I would masturbate but at times my thoughts would drift to homosexuality and of course once I saw shemales on the internet, I was surely hooked. I had experimented with toys and dildo's and even had purchased shemale and bi sexual porn and on occasion I would be riding my dildo while watching dick instead of pussy.

So, when Sara admitted she was transgendered and since I had always had the desire, my heart leapt and I was like, "yeah" we could surely see what develops. Later that night I got a couple erotic pictures from Sara via E-Mail. They weren't completed naked pictures, but in lingerie and on her knees with her ass in the air. They were rather sexy and quite a turn on and I could see her bulge and knew what is in-between her legs.

After a few more conversations I agree to another lunch with Sara followed by us going back to my house to be alone. On that day we ate and ended up back at my house. I was more nervous with her that I think I had ever been sexually. Even loosing my virginity. Sara had to go to the restaurant later that night, so she was dressed in a nice white button-down female shirt, brown women's trousers, high heels and a light coat over. We sat on the couch a bit slightly shifted towards each other. I didn't know if I was supposed to make the first move, or was she. We were lightly holding hands and just talking and even though I was comfortable with her, my stomach was doing flips and I was nervous and unsure.

Sara leaned over and placed her head on my should. I could smell her sweet perfume. When she looked up at me, I made my move and kissed her lips. It was a soft closed lip kiss at first, but then we moved to a full French kiss. We sat there quite a while with our tongues swirling around each other's mouth. Just looking at her face and with the clothes she was wearing, her big breasts, and the sweet smell of her perfume I felt like I was kissing a beautiful woman, but I knew there was a dick down there.

We ended up standing up and we had our arms wrapped around each other kissing deeply. My hands started wandering up and down her stomach and chest. I placed my hand on her breast, they were large and plump but fake, but I didn't mind. I started unbuttoning her shirt eventually getting it open and untucked from her pants. Sara slid it off revealing her beautiful bust and black bra. Sara reached behind her and unhooked her bra, exposing those breasts. My head dipped down and I started sucking on her nipple. Sara let out a soft moan and put her hand on the back of my head. I worked on kissing, sucking and licking both nipples. I returned to kissing Sara as her hands started pulling my T-Shirt up and off of me.

As we kissed deeper, she kicked off her heels and her height fell to just below me. I felt Sara's hand reach down into my crotch feeling my hard cock bulging in my pants. He hand rubbing up and down my cock getting me even more stimulated. I was so turned on. I had fantasized about this, fucked my ass with a dildo hoping for this and now I have this incredibly hot shemale at my house, with her hand in-between my legs.

I reached down in-between Sara's legs and felt a large bulge. It was amazing feeling that dick, even over the pants. My heart was racing, my stomach quivering with nervousness. Even though I wanted this, I was still so uneasy about going forward. Before I knew it, Sara had unbuttoned her own pants, sliding them down and off, leaving herself standing there in only her matching black panties, which were sticking out because her dick was hard. I reached my hand down into her panties as she started unbuttoning my jeans, grabbing a hold of her very large cock. I managed to wiggle my jeans down and I slowly grabbed, stroked and held her big dick in my hand. Sara reached down into my underwear, moaning as her hand hit my cock. We stood there in my front room kissing deeply and erotically, giving each other hand jobs. It was so hot!

I had to see her dick. I had to play with it more, I wanted to suck on it. I have been wanting dick for so long, I couldn't take it anymore. I pulled my hand from her panties, kissed my way down her chest as I started to get onto my knees. As I got down, I slid her panties down, getting my first look at her 7" cock. It was long, thick, circumcised and had just a patch of hair over the top, with the rest of it shaved. It looked so sexy. My mouth watered as I put it back in my hand stroking her off, looking up at her breast and smiling face. I leaned forward and put her cock into my mouth. It was so Erotic! I was hooked instantly. I didn't not know how to suck dick and outside of practicing and fantasizing with my dildos, I had never given head before. I just did what I felt was normal or what I believed she would like. Sara moaned in pleasure. Her hands on the top of my head as her big cock slid in and out of my mouth.

After sucking on her for a few minutes, Sara pulled me up to her, kissed me deeply and got down on her knees. She slid off my underwear, grabbing a firm hold of my erect dick. She put it in her mouth making me want to explode instantly. It was such a sight seeing the top of her head moving back and forth sucking me off. I was so hard. After a bit Sara stood back up and said. "let's go to your bedroom". She led me by the hand upstairs leaving all our clothes on my front room floor. The whole walk up the stairs I was just staring at her ass, her light brown skin, her sexy hips, clean shaven legs. Sara guided me to my bed and laid me down hinting for me to move to the middle. She climbed onto the bed sitting on her knees, her cock still hard and standing upright. She leaned over kissing me more, whispering in my ear how sexy this was. Sara made her way back down to my cock putting it back into her mouth. My hands were stroking her legs and lower back as she was giving me a blow job. She gave good head.

I was getting close to orgasm, but I didn't want to cum yet, so I pulled her away from my dick and pulled her towards me. Sara sat up a bit leaning her hips towards my face and pushing her hard cock down, so it could slide back into my mouth. I laid on my back sucking her dick. My head lifting slightly off my pillow as she gently pushed forward and down sending all of her deep into my throat. I must have laid there 10 minutes sucking on her dick watching it slide in and out of my mouth, listening to her moans and groans, heating the slurping sounds made while giving head. At that moment I couldn't have wanted anything more. My ass was throbbing to be fucked and I wanted to pleasure her. I was sucking dick and I was fucking loving it. Every now and then Sara would reach down and stroke my cock for a bit keeping me hard. Sara was getting close to cumming. Sara pulled her cock out of my mouth and laid on top of me, her breasts up against my chest as we kissed deeply.

Sara asked me if I was doing ok? I said yes, I am. She asked me if I was alright with this and I said yes, so far. Sara and I laid kissing and touching each other side to side, I played with her breasts, pulled on her dick, cupped her balls, as she pulled on my cock and even ran her fingers in-between my ass cheeks. I didn't want this to end. Sara swung around back on her knees leaving her ass just adjacent to my face. I watched her balls lightly sway back and forth as her body, neck and head worked on sucking me off. I wanted her to fuck me, but I didn't know if I was ready for that. It didn't take long for Sara to bring me to orgasm. The feeling was intense. I let her know in advance I was about to cum and she just kept bobbing her head up and down on my dick until I exploded in her mouth. Sara moaned when I came, as if satisfied she got me off and was able to taste my cum.

When she turned back around, she laid down flat and I rolled over onto my knees. I kissed my way down her stomach and put her hard cock back in my mouth. My head bobbed up and down on her dick making slurpy sucking sounds. My cock completely expelled, but my ass begging to be fucked. I tried taking her cock all the way down my throat several times, almost gagging on it. I cupped her balls and used my fingers to lightly rub her asshole as I just kept sucking her cock. I didn't know how long it would be until I made her cum, but I was having fun sucking her, so it didn't matter. I had never had a real dick in my mouth and I so wanted this! I didn't care if it took and hour, I was going to make her cum.

As Sara got close, she told me to lay back down, she slid up next to me putting her dick back in my mouth. She was thrusting herself forward as to face fuck me, bringing herself to orgasm. I lay back moving my head upwards trying to keep up the pace. Her balls were hitting the side of my face as she thrust back and forth. Within a few minutes Sara started moaning she was going to cum. She withdrew her cock from my mouth stroked herself over my face and within seconds squirted her cum all over my mouth and neck. I was in awe. My mouth opened to try and catch some. See I had never swallowed cum before, so I was anxiously waiting to see what it tasted like.

Sara finished and laid down next to me, stopping to lick and suck up her own cum, swallowing it down as I swallowed down what I had captured in my mouth. We laid there together under a blanket and just enjoyed the silence and the orgasm(s) we had just had. It wasn't too long after that Sara had to go, I got up and retrieved our clothes from downstairs and watched her get dressed. I watched her put that cock back into her panties and her bra back on just in amazement that I just sucked shemale dick for the first time. I drove Sara to work and dropped her off. As she was getting out of the car, she leaned in for a kiss and asked me if she could see me again next week. I said yes. All the way home, my mind was racing. Now the fear set in. Was I gay? Did I like her dick more than pussy? Would my friends find out? Would I be embarrassed? All things that never ended up mattering, but since it was my first time, I was freaking out a bit.

Later that night as I went to go to bed, I could smell her perfume on my bed. The scent brought me back to my earlier experience. I got hard thinking about her dick and those tits. I felt her cock in my mouth again, I could still taste her cum. I started masturbating thinking of her and ended up fingered myself in my ass, while stroking my hard cock thinking it was her big hard dick sliding in and out of me all while brining myself to orgasm again.

Sara and I eventually met up about a week and a half later and the second time was even better than the first.

To be continued...