Most all of my blogs will be stories. I have been writing erotic stories for the last twenty years. This story is about my very first transgender experience and how it changed the way I looked at transgender women. I will warn you. This is not a short story.
My neice had just graduated from college and had landed a great job in San Antonio. My step-sister called me and asked if I would help my neice find an apartment. I told her I would be glad to. So the next week I drove to San Antonio and spent the week looking for apartments. I found a few but they really weren't what I was looking for. So I called a friend and former business partner of mine who lives in San Antonio and asked him for a recommendation for a realtor who sold condos. Jerry said for me to give him a couple days and he would call me back. True to his word within two days he called me back with a name and number of a realtor friend of his. Her name was Jessica. So I immediately called her and told her what I was looking for. We set an appointment for Thursday of the next week. I called Jerry later that evening to tell him I was coming to town. I had not seen Jerry in five years so I was looking forward to it. He said for me to come in on Wednesday and that I could stay with him. I got there late that afternoon. Jerry had already thrown some steaks on the grill. We had a great dinner and a couple of beers and spent the rest of the evening catching up and talking about the old days. I asked him how he knew Jessica and if they had ever dated? He said no, "it was nothing like that, he had met her at a club a few years ago and they were just friends". I left it at that, thanked him for a great dinner and I headed off to bed.
I spent the next morning making business calls and sending some emails before my meeting with Jessica. I arrived at the specified address. I could tell at first glance it was exactly what I was looking for. I rang the doorbell and needless to say I was not prepared for what awaited me on the other side. The door opened and standing there was one of the most beautiful and sexxxiest women I have ever seen. Jessica stood about 5'7 and weighed 125 lbs. She was wearing a red long sleeve lace-up mini dress. Her hair was the color of golden wheat and fell to the middle of her back. Her body,,, was sculpted as her dress hugged every tanned inch of it. We shook hands and made our introductions and talked for a bit before looking at the rest of the condo. After our chat she grabbed her sales book and said "I guess we should get started"? I told her to lead the way. She started her sales pitch as we went from room to room. To be honest, I never heard a damn word she said. All I could see was that perfect, tight, lil body, those long toned legs and that great lil ass. She could have been selling me tupperware and I wouldn't have cared. We finally made it to the master bedroom. As Jessica went to turn the lights on she realized the bulb was blown. She said she would be right back. She went to the laundry room and got a ladder and another bulb. As she entered the room I took the ladder from her and set it up for her. I asked her if I could change the bulb for her but she said "it was no problem, it's part of my job".
As she started down the ladder her left foot buckled and she fell, luckily I was there to catch her. I carried her over to the bed and gentley set her down. Then I rubbed my hands over her foot and ankle, massaging it. I told her I didn't think anything was broken but that she would want to get out of those heels as soon as possible and get off of her foot to keep it from swelling. I put her shoe back on and reached down to help her up. As I pulled her up to me, she lost her balance and fell back on the bed. As she fell, she grabbed the sleeves of my shirt and pulled me down with her. I stuck my arms out to break my fall so that I wouldn't fall on top of her. As I laid over her, my arms stretched out and elbows locked in the push up position, I looked down at her and for one singular but very intense moment, a feeling of raw sexual intrigue started to ignite. We stared into each other's eyes as the intensity between us grew stronger. I had never wanted any woman at that point in my life, the way I wanted her. I asked if she was ok, then a long pause of silence. She had this look on her face. It was intense but deliberate. Once again I asked if she was ok? She reached up, clinched the collar of my shirt in both hands and pulled me down to kiss her. And did we kiss..... At first our kisses were passionate and sensual then they raged out of control with great urgency. Almost to the point of being reckless!!! I lowered myself on top of Jessica. Our kisses now raging like a wildfire. Kisses so hot,,, that I could feel the flame's from her lips. Taking my tounge, I began to trace her lips, then licking her lips with quick darts of my tounge, then pulling her lips into my mouth with my tounge while lightly biting them. Jessica's moans turned to whimpering. Then she ripped the buttons open on my shirt and began to run her hands over my broad chest while clinching my chest hair between her fingers. She ran her hands from my chest over my shoulders and took my shirt off. As our kisses intensified, she planted her mouth into my right shoulder and bit down while her fingers clawed away at my back. I couldn't take it anymore. I had to know how wet she was and what she taste like. I pulled her dress up and took it off. Then I took her bra off exposing her DD'S. I began to lick and suck her nipples, tracing them with my tounge with slow circular strokes, while biting them. My wanting desire for her was now out of control. With my tounge I began to lick and kiss my way down that sleek, sexy stomach of her's, as all I could think about was getting to what I wanted most!!!
WTF??? WTF IS THIS??? WTF,,, IS THIS??? For the last hour all I could think about was how bad I wanted her and now I find out my she is a he. I WAS WAS PISSED!!! MY BLOOD BOILING!!! In all my life I have never been attracted to a man. Not even when I played football and showered with them in the locker room. How could I not tell that Jessica was Trans? I had always heard the term "passable" but never really knew what it meant, til now. Everything about her was feminine. Her hair, Her makeup, flawless. Her skin, silky smooth. Her walk, Her talk, never a detection of being anything but a woman.
I WAS PISSED!!! I was pissed at Jessica. I was pissed at Jerry. I was pissed at Jerry for not telling me about Jessica and I was pissed about being put in this situation. My anger had now reached it's boiling point. My blood pressure was rising, I was sweating and my head was pounding so badly, I couldn't even see straight. The next thing I knew my left hand was clamped down on her throat, my right fist clinched and my arm drawn back as if to hit her. It was like being in a trance. And suddenly I felt this sharp, stinging pain. I looked down and I could see Jessica gasping for air. Her hands wrapped around my left wrist and her nails dug into my skin, clawing at my arm as she begged me to let go of her. Screaming at her, I asked "is this what you want"? I reached down, tore her lace thong from her body, grabbed her by her ankles and pulled her to the edge of the bed. I was pissed and I was going to make sure she felt every hard inch of my anger.
As I pulled her to the edge of the bed, I grabbed her by her hair and guided her mouth towards me. I shoved my cock in her mouth and forced her to blow me. I told her, blow me harder as I pulled my cock out and slapped her face with the weight of my stiff cock. Now I was fully erect. I squatted down low to maximize the power of my legs and shoved her legs forward pinning her legs by her head and then I leaned forward and pressed my chest on top of the back of her legs, pinning her to the bed. Then I grabbed my cock and burried in her ass. And I wasn't gentle about it..... There was no lube, there wasn't gonna be any foreplay and there would be no love making. This was about straight up, pissed off, unrelenting fucking. The fucking, raw, the pounding, relentless and the sex, brutal. The harder I fucked, I could hear her breathing getting faster as the weight of my body was causing her lungs to work harder. I rolled her over on her stomach and once again I plowed my hard cock deep into that tight lil ass of her's. Pounding her, hard, fast and deep. With every thrust I could hear her begging me to stop as she had the bed sheets clinched in her hands, trying to climb out from under me. So I planted my hands deep in her spine to hold her down but they kept slipping as her back was covered with my sweat. So I rolled her over. I wanted her riding me bareback. She climbed on top and mounted my hard, throbbing cock. I made sure her knees were pressed against my legs and that her knees were firmly planted in the mattress. But I wasn't done yet. I crossed her ankles and planted her feet in my stomach. Then with my right hand, I reached up and grabbed a handful of her hair and snatched her head back and curled my left bicep around her throat, pulling her body back flush with mine. With her body now at my mercy, I unleashed my final act of aggression. I could feel myself ready to EXPLODE!!! So I arched my back and lifted her up off the bed with my legs and I came hard shooting hot jolts of my seed into that tight lil ass. Once I had cum, I released my hold on her. I took my forefinger from my right hand and smeared my hot seed over her hole as it oozed out of her ass. I felt her body flinch as she said she was sore. At that moment something happened. I could tell she had been crying. It was the first time I realized I had hurt her. I was ashamed of myself and what my anger had driven me to. So I crawled behind her, took her in my arms and held her close until she stopped crying. I then spread the comforter over her, apologized, got dressed and left.
There is actually more to this story if anyone is interested? You will hear about my confrontation with Jerry and a secret I had never known about his life. You will hear about he and Jessica really met and you will hear about a letter she wrote me after our encounter and how it lead to many more sexual encounters for us.