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My TS affair

  1. 2bi2Bboring
    2bi2Bboring
    Some things in life just happen, they aren't planned or plotted, but we have to remain open to the possibility of them or we end up regretting what might have happened. This is a story of one of those possibilities, a story of a time in my life when change was all around me and had I not embraced that change I would be living in regret. I was recently separated from my then wife, which was a good thing. We were entirely too young when we got together and I had often wished we were not married because no matter the sacrefices I had made in our relationship, nothing seemed to change it. We were not very sexually compatable, she was perfectly satisfied to go months without sex, where I would be content to have sex more than once a day. The content of our sex life was always a bone of contention as well, I was far more sexually adventurous than her and she was a prude. After years of this, I had finally had enough and we separated. It was a rocky relationship and would prove to be an even rockier divorce.

    I was staying with a female friend who had been my moral support pre-separation. She was having marital problems of her own and we'd leaned on each other for emotional strength during our time of trial. We talked on the phone for nearly two years, nightly, for hours. During these conversations we'd both found out from each other that we had bisexual fantasies. We vowed to never make our relationship physical as we were far too worried about loosing the friendship. She had encouraged me to leave my wife for my own happiness and when I did, she offered me a place to stay. During our two years talking on the phone, a strange thing had happened. She had many friends who were in alternative sexual lifestyles. Her new boyfriend was bi, he had several gay friends, she knew several couples into swinging. She would have get togethers at her house where these friends would discuss sex and whenever this happened, she would call me and let me in on the conversation. All the conversations were encouraging, and acceptence was precursory to being in the conversation. When I became free, we all had a big get together of the friends and celebrated my freedom. When asked what I was going to do about my new found freedom, I said I had no idea. My female friend announced she had "plans for me". Later she told me she had plans to take me to a bar. The next day, we went to this bar, it wasn't a regular bar but not so much a gay bar either. Instead it was kind of a mash of the two with open minded couples and singles of all sexual ilks looking to meet others to fulfill their sexual needs. Kind of an off-premise/ swinger/gay bar, so to speak.

    This is where I met Devin, she worked as a beer tub girl at the bar on weekends. She was quite beautiful, at 5'4" she was 9" shorter than me, a black girl with gorgeous cafe' au lait skin and striking amber-green eyes. She had a full bust and a very nice ass. She was finishing her shift when we arrived at 10:00 pm and sat next to me at the bar to have a shift drink. She struck up a conversation with me and we sat talking dispite the blaring music until it was nearly time for last call. She turned to me and asked if I'd like to go to breakfast, I agreed and told her we could take my car. She sat next to me in the car leaning on my shoulder and complaining how tired she was from her shift. We talked and ate at breakfast, and as she finished eating her food she turned to me and gave me a serious look in the eyes. She said to me, " I like you, you seem honest and very open about who you are." I told her I liked her too and thought she was very pretty. The she said to me, "well is it going to make a difference if I'm different?" I asked what she meant and that's when she said, " I wasn't born a girl". At first I didn't know what to say, I had no clue that she was anything other than a beautiful young woman. I had seen a few trans-sexuals before at drag shows and there always seemed to be SOMETHING that gave them away as a man. This time there was nothing, no adam's apple, no 5 o'clock shadow, no low voice, she was the most passable trans-sexual I had ever seen. I had been completely fooled but was also not the slightest bit angry or put off. I told her it made no difference to me. She smiled and said that she hoped not. I was more than intrigued, I had been in the Navy until recently and had seen many black guys on the boat in the shower. I saw their big cocks and was impressed and turned on by them but had never acted on these feeling for fear of being caught. At the time being in the military and being gay or bisexual was an instant path out. But, now I was recently honorably discharged and now felt completely free to do as I pleased.

    I took her home, where she invited me into her apartment. It was a small studio apartment decorated with tie dyed wall hangings of rainbow hues, there were pillows everywhere and a platform bed. I sat down on her couch and she sat next to me, turning and throwing her legs over mine. She stroked my face and told me how handsome she thought I was, then she kissed me, soft lips, no stubble, nothing but soft feminine skin. We kissed passionately for quite a while, lips, tongues, and lots of heavy breathing. She reached down between my legs and felt my swelling cock under my jeans, at that point the ice was broken and passion gushed forth. I felt her breasts through her clothes which were soft and pliable as any I'd ever felt before, not too small or too large, definately NOT implants. She gasped as I thumbed across her nipple through her top. She shifted between my legs and unzipped my pants and freed my cock. She kissed me again and rocked back taking my cock in her mouth. She looked so beautiful, her beautiful caramel skin against my white cock. She took all of me in her mouth, deep throating me to the balls. I gasped, it felt so luscious having the ring of her lips around the base of my cock, then to my surprise she stuck her tongue out of her mouth and licked my balls and pulled off my cock with her tongue licking all the way to the top of it. She rocked back and looked at me, saying, "I want you, naked, NOW!" She stood and walked behind an oriental screen near bed, I undressed and sat on the couch. Her skirt and top appeared over the top of the screen, as did her lace bra. I was stunned when she came from behind the screen,truly this was a creature any woman would be envious of. Here was this gorgeous creature, naked but for a small pair of thong panties, her heels made her still made her 3 to 4 inches shorter than I am. Her caramel skin was flawless, she nearly glowed in the soft warm light. Peeking from the top of her thin white lacey thong panties was a beautiful long cock. It was wider at the middle where it came out from over the top of her panties and the pink head was small. I could tell she shaved and had no pubic hair, which was totally sexy and only emphasized her femininity. She was truly stunning, full hips and a small waist, beautiful breasts that pointed up and away from each other. I stood and she came to me, I took her in my arms and she ran her hands up my back, looking up at me. I felt her soft skin against my own naked body. There was nothing but her erect member protruding from beneath the lacey top of her panties that gave away her true sex. We kissed and she bent her neck and bit my nipple as she reached for my cock again. I gasped as she stroked my cock and sucked on my nipple. SHe looked up at me and said to me, "lets go to the bed". I picked her up, and walked to the edge of the bed, this was rather easy because she couldn't have weighed 140 lbs. As I laid her on the bed she rolled across and beckoned to me to join her. She kicked off her platform heels as i joined her on the bed. She layed beside me, kissed me and said to me, "Is this your first time doing something like this?" I nodded and she kissed me, saying "don't worry, I'll make sure you enjoy it." I said, "You are SO beautiful, how could I not". She slid between my legs and took my cock in her mouth, swallowing it all the way to my balls, she wagged her head side to side as she pulled up to the bottom of the head with her lips and stuck her tongue in the small opening at the top, then plunged back down to the bottom again. Again and again she did this until I was ready to cum, I told her to stop or I would cum and she did. I was NOT ready to cum yet, I so wanted to wait and enjoy more of her. I slid down on the bed and turned her over on her back. I reached up and slid off the thong from her hips and legs and tossed it to the floor. This was the first time I had seen the entirety of her cock. It was 9" and her smooth shaved skin made it look so feminine, I had never seen a shaved cock before. She had a full head of highlighted straight hair that reached to the middle of her back, and was completely hairless but for that. I marveled at the sight of her. It was the first time I had ever seen a transgendered girl naked, she was so very sexy. I grabbed her cock at the base and licked along the bottom of it from the base to the bottom of the head. I looked up at her, she was looking into my eyes and softly said, " yes baby, don't worry it won't bite you". I took the head of it in my mouth and pushed down as far as could take it which was about half way. I had never done this before but was so turned on by it. I licked and sucked her cock and as I did she moaned and instructed me on what to do. Her soft smooth skin felt so luxurious in my mouth. Her cock was so hard and I tasted the pre-cum that presented itself at its head, it was salty and sweet at the same time. I was hard as a rock and SO very turned on, She saw my hard cock dangling between my legs and said to me, "that feels so wonderful,baby. But what I really want is you inside me. PLease put your cock in my ass." I pulled her legs toward me, and fell forward on top of her, kissing her and feeling her breasts. I pinched her nipples and could feel her cock against mine. She was nearly 3" longer than me, I grabbed both of our cocks and moved my hips back and forth feeling her cock slide against mine in my hand. She looked me in the eyes and again begged me, "please baby, I NEED you inside me. I asked if she had any lube, she reached to the nitestand drawer and produced a large bottle of lube and dowsed my cock with it. She wet her ass with it and slid my cock inside her gasping as it slid in. I fell forward and we kissed with tongues and bitten lips, I plunged in and out of her ass over and over, it was so tight. I could feel her hard cock against my stomach, it felt so warm and was still wet with my saliva. She wrapped her legs around me and grabbed the cheeks of my ass pulling me inside her as deep as she could get my cock. I felt a huge orgasm building inside, but I wanted to prolong this as long as I could. I sat up and pulled her as close as I could again plunging my cock as deep inside as it would go, she was basically sitting in my lap, with her legs wrapped around me. I noticed her cock was long enough I could get may face down far enough to get the head of it and about 2" of it in my mouth. She was moaning and bucking up and down, Plunging my cock deeper into her ass and as she came off it, deeper into my mouth. She moaned and bucked up and down. It was so sexy fucking her in the ass and feeling her beautiful cock slide in and out of my mouth. I again felt the orgasm build in my balls, I slid in and out of her ass as her cock slid in and out of my mouth. She slammed down on my cock and said she was going to cum, I took as much of her into my mouth as I could and felt her hot cum splash into the back of my throat. She came for nearly ten seconds, I swallowed her cum, which I had never done before. but I had tasted my own cum many times. The rush of her cum and her ass flexing on my cock spurred my own orgasm and I emtied into her ass. I buried my cock deep inside her and pumped her as full as I could. As I came, I fell on top of her and we kissed and she tasted her cum in my mouth. It was positively intoxicating, we kissed for a long time and as both out cocks went limp, I withdrew from her ass. We rolled on to our sides and she rolled over and spooned with me. I could feel the warm skin of her ass against me, she pressed against me and reached back pressing my face into her neck which I nibbled on. "That was so very much fun", she said. "I will want more of that again, soon." It was near morning and we soon fell asleep, her in my arms.

    Later than morning she woke me with her mouth on my cock. She was magnificent at sucking cock and was quite able to swallow it. THis was quite a switch from my soon to be ex-wife who was always timid about sucking cock, Devin excelled at it. She moved her ass up near my head and I quicky took her beautiful cock in to my mouth and we sucked on each other for quite a while. She moved on top of me as she sucked and fucked my face. I loved the way her cock was shaped. It's head was small and it widened as it got closer to her pubic bone to nearly 3" wide. I stopped giving her head and asked her if she would do something for me. "What would you like my lover?" I said, "I have never had a cock in my ass, I love the way yours is shaped and it's really beautiful. I know you are so feminine but would you fuck me?" "For you, I will do anything you like." I moved so she could get between my legs, she lubed me up very well and used a finger, then two, then three to loosen me up. She fucked me with her fingers for a while, sometimes licking or sucking my cock as well. THen she pulled back and lubed her hard cock up and slid it into my ass. It felt so good as she slowly pushed it in all the way. There was a little pain but it quicky subsided as she poured more lube over the shaft of her cock. Soon she was fucking me hard and grabbed my cock and stroked me as she pumped. SHe looked at me and said," I'm going to get you close and then I want us to come together again." SHe stroked me and slowly pumped my ass. I could feel her cock convulse as she neared orgasm, I was getting close too and I told her. She began stroking and pumping in ernest. I felt my ass tighten as I began to cum and she burried her cock in to the hilt and came what felt like a bucket full of warm slick cum in to me. She stroked me as I came and caught as much of it as she could on her tits and face. Again we collapsed into each others arms and napped after cleaning each other up.

    We had sex for 3 days, only breaking to eat and sleep. Devin was my first non-heterosexual experience, we had a relationship for about 3 months. I learned she had paid for lazer treatments to remove the hair on her face and was on hormone treatments which lessened it even further and made her breasts grow. She had used a vacuum treatment to stretch the size of her nipples. She was magnificent, to this day I have never seen a more passable male to female trans-sexual. It was unfortunately not to last, I had to return to my home state to take care of some family matters and by the time I returned, she had moved out of her apartment. I learned later that she had been saving to finish the transition of her male to female transformation and had flown to Thailand to do it. I left just a month before she left to have it done. I returned and spent three weeks there and then returned to my home state for good. I started a new life, but thought of her often. I had accepted her as she was and would have been perfectly happy to be with her but I had to return home. I heard she had asked my female friend what had happened to me, I had left in quite a hurry as the nature of my business at home was a family emergency, I had asked my friend to contact Devin at the bar and tell her what happened. She had no phone so there was no way to call her. It's one of those things where life got in the way of what could have been. But damn, it sure was fun while it lasted.
  2. tender2
    tender2
    Nice story. Very hot ;-)
  3. chicagom
    chicagom
    I loved the openness and the detail recalled. I was so riveted, I read this twice in the same night. Hope to read more 2bi.....2 thumbs UP!!!!!
  4. Plumhead2
    Plumhead2
    I love authors like you who can write erotic stories that combine sex with humanity. Sex stories should not be all about what one genital did with another! With your story, I felt I was peaking into a little bit of your life. Thank you for sharing your story. You must be an incredible lover with such a creative and imaginative mind.
  5. Indyguy
    Indyguy
    Enjoyed this, thanks for sharing, good job. Nice to see another Hoosier here.
  6. SilverRiverDad
    SilverRiverDad
    Great story here. Very real and honest from a true experience. Love to meet either or both characters. Well written.
  7. Heloisea3
    Heloisea3
    Thanks for sharing this story. I enjoy reading about these kind of unexpected encounters that people experience. They tend to open your eyes to new possibilities. Great job!
  8. sexy_runner
    sexy_runner
    what a wonderful and lyrical reconstruction of what was obviously a brilliantly memorable encounter! i thoroughly enjoyed the read, it was stimulating and touching!
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