After 10 years of marriage, my wife and I divorced and I moved to a new city. Soon after getting settled in to my new bachelor life, something happened that I would never have imagined. I live in a small community about a mile or so from the local grocery store. Perfect distance for a daily walk to fetch my day’s groceries. About a week or so of walking back and forth, I noticed a nice looking brunette approaching. Maybe I was just horny or she was just very attractive, but I couldn’t help but be drawn to her. As she passed by I knew I wouldn’t have the courage to say anything but hello, which I did. To my shock however, as she passed I realized the hot brunette was actually a transvestite. I still uttered my hello but I was nearly speechless. I had seen she-males before but never was I moved as I was that day. He/She responded to my hello with a smile and “Hi.”
Regardless of the obvious shock I was in, I still felt strangely attracted to her. I didn’t know what to do but keep on walking. Later when I got home and continued to think about her, I found myself searching for some shemale porn. I had been interested in she-male porn prior and found some good stuff to satisfy me at the time yet disappointed I didn’t strike up a conversation with the real-thing when I had the chance. Needless to say my daily walks were more and more frequent but as one, then two weeks went by without another encounter with my “secret” crush, I began to give up.
Then after about 4 weeks I see her approaching a corner from my right, literally reaching the corner at the same time and place.
“Hello,” I said.
“Hello,” she replied.
We both waited for a passing car before we walked into the crosswalk together.
“Where are you heading”? I asked.
She replied, “To the hardware store; I can’t get my cable tv to work and was thinking it might be a bad cable or something.”
I told her that I had done many cable installations and for a time worked as an electrician. I told her I’d be glad to help as I had nothing else going on.
Soon we reached the store and she said, “Well, I will grab something for dinner and if you can fix my cable, I will make a nice meal.”
Awesome!! I thought. “Sounds good,” is what I said.
Together we grabbed a few items and she was thrilled when I picked out a nice bottle of wine that she said was her “favorite.” We chatted and chatted on our walk home. Though in my early 40’s I am fit and relatively well built. She is in her mid-thirty’s and also well-proportioned. She was wearing a skirt, sandles and a modest top. Some makeup but not overdone. Though I could tell she was really a guy, you definitely would not know it from 5 feet away. I told her that the first time I saw her I wanted to make conversation, but then I realized that she was a guy and was a bit shocked. She asked if that “bothered” me. I told her I had been interested in shemales before, although never acted on it. She told me that she had only been cross-dressing in public for about 2 months. She too had been divorced as her wife caught her wearing her closes and couldn’t “deal” with it. It was actually kind of sad and I really felt for her.
When we got to her house I took a look at her cable tv problem. It took me about 30 seconds to realize that the connection outside her house was wet from recent rain and that opening the junction box and letting it dry out is all it took to get the cable working. Easy free meal I say! As we sat talking I really found myself more and more attracted to her. She was really really pleasant. She told me that she had actually never been with a man before. She said she was still attracted to females but was “tired of hiding” her feminine side. She told me she had started watching shemale porn about 10 years ago and found it very exciting. I told her I had watched a fair amount of tranny porn and had even done some cross-dressing here and there. As we were talking about all this my cock could not have been more hard. I tried to hide it with my arm but it was obvious since I was only wearing running shorts.
“Wow,” she said, “looks like I have the right amount of feminine sexuality for you.”
“Uh, yes.” Are you kidding, I thought.
She scooted over next to me on the couch and began to caress my arm and I hers. Pretty soon I was kissing her cheek and neck and lips. I could see her erect cock bulging in her skirt.
After about 10 minutes of making out, she said, “Wait here. This is my first and I want it to be perfect.”
She got up and went into her bedroom. I went into the bathroom to clean up and felt like I was about to explode at any moment. I turned out some lights and poured us a couple of glasses of wine. Soon she came out and… WOW!! She had put on a red corset, with thigh high stockings, 4 inch heels and done up her make up. Her lipstick was thick and red and luscious. As I kissed her I could not have been more horny. She is only just a little shorter than I am but as we embraced the feeling of our cocks tapping each other was great. She pushed me back on the couch and went to her knees, coated my cock with some numbing lube and began to give me the best blow job of my life. She really enjoyed herself. Licking my pre-cum and rubbing the head of my cock all over her face.
I really, really wanted to cum but she said, “I want you to be my first,” and pulled me on top of her.
I stroked her very nice cock and using some lube began to finger her ass. She was tight but one finger and then two and she was loosened up. I really took my time. 10 or 20 minutes of fingering and she was well prepared. She was moaning loudly as I began to press my cock into her ass. I could tell she was nervous, she was shaking and asked me to be gentle. I took my time. I was in no hurry. A little at a time I began to fuck her. Slowly and slowly, going further and further. At first just the head of my penis entering her, then more and more. Soon enough I was all the way inside her, her squirms and smiles affirming I had hit the right spot.
She was sooo tight around my shaft. If not from the numbing lube I would have only lasted a few seconds. As I pumped I pressed her knees toward her chest. Her heels pressing on my shoulders. I could tell it was an amazing experience for her as she had tears of joy running down her cheeks. It was all I could do to keep from cumming.
She told me, “I want you to cum inside me.”
That was all it took. I couldn’t hold it any longer. I exploded with a burst of cum deep inside her. She said she felt it; I sure did! Sliding down on her, and for the first time, I took a nice looking 6 inch cock into my mouth. My wife had given good blow jobs so I just tried to repeat what I had seen her do. I gripped her cock tightly with one fist on the upstroke and took her deep inside my throat on the down. I must have done pretty good as it only took a minute or so before she yelled, “I am going to cum!” I was enjoying myself way too much to stop and even quickened my pace. Her throbbing orgasm filled my mouth. Actually, it was surprising how much she came. I was happy to swallow every drop. I actually liked the taste. She squirmed and eventually went limp while I still fondled her now shrunken penis with my tongue.
We spent that night together and it was not the last…..to be continued.
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