Going Back for More

Going back for more

This is the story of my most enjoyable transexual adventure. My understanding wife has always tolerated my sexual transgressions during business travel, and where better to transgress than in Germany, the land of permissive sex worker laws. Friedrichshafen, in southern Germany, is where I had come for a convention at the Messe, a large exhibition center on the shores of Lake Constance. Springtime here is wonderful, with fruit trees in bloom and the Swiss Alps in the background. Friedrichshafen does not have the big brothels of Frankfurt or Berlin, but it does have several small red-light houses. I had visited one previously, where I had a rather unsatisfactory fuck with an attractive Italian woman who was better at giving criticism than pleasure. (What, you can't do better than that? What's wrong with you!) On my way out of the door I noticed that upstairs they had a "Transwohnung" or tranny house. It piqued my interest, as several years previously I had visited an enormous dance club in Jakarta, Indonesia where I discovered that the lovely "girls" up on the third floor were not girls at all!

Several nights later, I was feeling horny and decided to wander over and see what was on offer. I knocked on the door and was greeted by a tall and slender girl with a nice hourglass figure. Only when she spoke was it clear that she was not born as a female. She was quite passable, with a feminine face and disposition as well as a shapely behind and long legs. I was a bit nervous as she did not speak English and I was not sure my slightly better than high-school level German would be good enough. She assured me that it was fine, and that German was not her mother tongue either, being from Costa Rica originally. I asked a few questions about her services and the price and told her I would return later after the Viagra kicked in! My previous tentative explorations of sex with a tranny were interesting but not complete as the newness of the experience freaked me out a bit, and I had been unable to maintain an erection.

Later that evening, feeling fortified by an extra dose of the little blue pill, I knocked on the door again and was invited up the stairs to her room. As I walked up the stairs behind her, I took notice of her shapely ass and the inviting way she moved her long smooth legs. "You do know I am a lady-boy, right?" she said when we got to her room. Oh yes! Money exchanged for an hour's visit, she left the room and indicated that I should use the bathroom to clean up. I made sure to be squeaky clean and was pleased to see that my cock had reported for duty and was standing at full attention. I was really excited about this visit and waited with great anticipation back in the bedroom. Chantal returned, this time gloriously naked and with a beautiful and partly erect penis. I was genuinely aroused by her body which encompassed both male and female forms in an intoxicating hybrid. Her breasts and shapely ass combined with her hard flat stomach were a sight I had never imagined before. She seemed pleased to see me fully erect "Oh Ja!" and walked over and kissed me. The way she kissed was quite amazing, with an eagerness and directness I have never experienced before. We spent several minutes passionately making out, with her ample breasts (obviously artificially enhanced but skillfully so) and stiff cock pressing against me. I could detect a slight taste of tobacco which is normally a turnoff for me, but it along with her perfume made for a heady mixture. After a bit, she reached down and put her hands around both of our cocks and rubbed them together. "Look!" she said, "they are almost identical!" It was true, and I was glad to see that she was circumcised as I am.

At that moment, I made an impulsive decision and dropped to my knees in front of her and put the head of her cock into my mouth. In my previous explorations, the oral sex had always been with a condom, and I had been put off by the taste of latex. I had done some online research and was reassured to find that the risk of HIV transmission to be extremely low for oral sex, so I felt that the reward was worth the risk. I gently grasped her balls and put more and more of her cock into my mouth, reveling in the wonderful taste and sensation. I made a point of being very gentle and not letting my teeth get in the way. Her groans of pleasure seemed to indicate I was doing an OK job. I was amazed to find that I was almost able to deep throat her, the tip of her cock nudging into my throat. "Let's lay down on the bed for this" she said and lay on her back on the bed with her cock eager for more attention. I positioned myself over her and spent the next ten minutes luxuriating in the feel of her cock in my mouth. She then reciprocated by giving me a slow and sensuous blowjob in the 69 position, our bodies forming a perfect circle on the bed.

Not wanting to come yet, I said with my Canadian accented German "I want you to fuck me now, eh?."

She got up, walked to a table, and rolled on a condom from the stack sitting in a bowl. She indicated for me to get up on the bed on all fours and positioned herself behind me. I didn't know what to expect and was surprised when she put her mouth to my anus and started gently licking. This was something I had experienced only once before with my wife, and to say that the feeling was stimulating would be an understatement. After a minute or so of gently thrusting the tip of her tongue inside of me, she put some lube on her finger and gently probed my opening. Getting on to the bed behind me, she placed the tip of her cock at the entrance and gently pushed inside. I was shocked mainly because there was no discomfort at all, only the feeling of being very full in a good way. She slowly worked her way into me, back and forth until her balls were gently slapping against mine. I really loved the feeling, especially knowing that she was in up to the hilt. I pressed back against her as she thrust into me, aware of my own erect penis swaying back and forth in time with her. After a few minutes, she said "let's get you on your back." I rolled over and she put her hands under my knees, raising my legs until she had a good angle for access. She pulled me to the edge of the bed so that she could enter me while standing. She eased her wonderful cock into me while leaning forward to kiss again. The taste of her lips now had the addition of my ass mixed in, but I was if anything even more turned on by this. Her thrusting become more insistent, and I was really enjoying kissing and fucking. She paused for a moment and demonstrated her flexibility by leaning down to take the tip of my cock into her mouth, even as the tip of hers was in my ass. She went back to vigorously fucking me in the missionary position, until I could hold back no longer and spurted my ejaculate up on to her smooth belly. Gasping for breath, I collapsed back on to the bed with my heart beating furiously. After a few minutes of holding each other in our arms, she bent down and licked the remaining cum off my cock before taking it in her mouth and nursing it back to life. I was amazed to see her efforts resulting in another hard-on, and I felt as if I had become twenty years younger.

Then she said with her Spanish accented German, "I want you to fuck me now, eh?."

She got another condom and rolled it on to my once again fully erect member. She positioned herself in front of me on her knees and rubbed a bit of lube on her asshole. I put the tip of my cock against it and pressed ever so gently. This was clearly not her first rodeo, and she eased back against me to force my cock deeper inside. I really like anal sex but am acutely aware that the women I had done it with before were not as eager as I was. There was no hesitation here, and Chantal clearly liked it when I would vigorously thrust into her. The firm grip of her channel around my cock was a revelation, nothing like a woman's vagina. I grasped her ass with my hands and pulled her back to me greedily, in and out for what seemed like an eternity. I could feel myself coming close to the edge of the waterfall but did not want to come again yet so pulled out of her.

I lay back on the bed and she knelt beside me. She was clearly turned on and started stroking her cock vigorously. She asked, "Where do you want me to come?" and I said almost without hesitation "In my mouth." I took her cock into my mouth and gently grasped her balls with my right hand. She fucked my mouth a few times and then gasped as she propelled a thick jet of sperm into my mouth. I could not take it all, and some spilled out on to my beard. As she continued to come, I was able to gulp down the rest and found myself surprised by the warmth and somewhat bitter taste of it. I was really pleased to see how aroused she seemed to be and hoped that it was not all an act. As I pulled my mouth away from her cock, I squeezed it a bit and saw a last rich white bead of cum out of the end. I licked it off with my tongue, savoring the taste. Wow!

My balls were almost bursting by this point, and she started firmly stroking my shaft. I was laying back on the bed and had the most incredible feeling of being on the edge of ejaculation for an uncommonly long time. Finally, over the edge of the waterfall and a stream of come spurted from me, covering her hand like a warm blanket. As the orgasm subsided, we both lay back on the bed in exhaustion. I told her that it had been the best sex of my life. We talked for a bit, at least as much as my German would allow. As I got up and cleaned up a bit, I was shocked to see that we had been at it for almost two hours. I was feeling sheepish that I was taking advantage having only paid for an hour but she seemed quite satisfied to leave things as they were.

As I walked back to my hotel in the darkness, my head was spinning. I have never considered myself in any way homosexual and have no interest at all in men, but I have to say that a "chick with a dick" is close to the best thing I have ever experienced. After I got back to the room, I continued to replay the evening's frolicking in my head and found my cock stiff as a board again. I started to stroke myself, but then thought "what the heck am I doing here?" So back out into the darkness, retracing my steps to the Transwohnung. I rang the doorbell, and a very surprised girl leaned out and said "My Sweet, you are here again?" I walked up the stairs and said to her "Your kisses were so sweet I must have more." I was soon back in her bed again, taking turns sucking and fucking until I reached another orgasm. Three in one night, this must surely be a record. After the second session I was completely exhausted and headed to the hotel. As I fell asleep, and even now years later, I recounted the nights events in my mind. It really was a peak sexual experience, one that will probably never be repeated. I'm just glad I was brave enough to go through with it!

End.