My Transgender Love: Week 1

After I returned from my trip to Hong Kong to visit a Filipina transgender woman, I never heard from her again. So I spent the better part of the next year online looking for someone with whom I could connect mentally. If she was an attractive transgender top, well that would be great too.

After many online chats and web cam conversations with numerous people, I found a young woman in her thirties living in Manila. I thought that she was beautiful and sexy but I wondered why she was interested in an old retired grandfather.

After my Hong Kong adventures, I knew that I would be happy as a pure bottom so when I saw her profile titled "Active for passive", I knew that she was the woman for me. I hoped that this relationship would work out better than the last one.

We spent the next year chatting with each other almost on a daily basis. I stopped talking to anyone else and focused on her exclusively. I had not been sure about visiting her but finally I made arrangements to spend three weeks together. Although I found her very attractive, sometimes it seemed as though we didn't really click together. This visit would be a kind of test of our relationship.

My flight to Manila had been delayed for several hours and she had been forced to stay at the airport waiting for me from midnight until the early morning hours. I was tired from the long flight from Los Angeles to Hong Kong and I was ready to sleep. When I finally arrived, we had some hectic moments trying to find each other among all the people at the airport.

She was taller than I had imagined with a skinny body and the pretty face I had been seeing for so long in the camera. We embraced and after a quick kiss, she led me to find a taxi to get to our hotel. She had checked in already so once we arrived at the hotel, we could go straight to our room. Sitting next to her in the taxi, I got used to being in her presence.

After we arrived at the hotel and went up to the room, we immediately got undressed. I don't even remember discussing what we were going to do or who started undressing first. We just did it and then I could see her naked. It was obvious from her raging boner that she was excited about what was going to happen.

I was both nervous and excited by the idea that she would soon be penetrating me with her beautiful penis. It was much bigger than my five inch dildo that I practiced with at home - could I handle her? At the same time, I was filled with desire for her. The woman in Hong Kong had a small penis and there were times I really wished that she had been larger. Now my wish was about to come true.

She told me to lay on the bed on my side. I had applied lubricant to my anus in preparation and she got herself lubed up as well. This was the moment of truth! After all the chats and all the waiting, she was finally going to stick it in. I told her to go slowly and as I lay there, I could feel the head of her cock pushing into my tight wet hole.

Although I was not an anal virgin, I felt like a bride on her wedding night letting her partner take control. I just concentrated on letting my sphincter muscles relax, and then suddenly she was able to thrust her cock all the way inside.

Jesus! My entire consciousness was centered on my asshole and feeling the entire length of her shaft filling my rectum. We had fantasized about this moment for so long it was hard to believe that it was happening. We were actually doing it!

Once that she had mounted me completely, she began fucking my hole slowly and tentatively at first but then building up speed as she got hornier and more determined. I lay there panting and moaning like a bitch taking the brunt of her assault while she jack hammered her throbbing cock into my hole. I was being introduced to the reality of ass fucking by a massive cock and I was loving every minute of it.

Soon she pressed her groin tight up against my butt cheeks and thrust her cock in deeper than I thought possible. She was boring into the very center of my being to deposit her load. I could actually feel her orgasm as her penis made very small jerking movements inside my rectum.

At that moment, I knew that she was breeding my ass and completing our mating. I was so happy sharing this magical moment of sexual release with her. Our union was the fulfillment of all those months of flirting and conversation.

Within ten minutes of being in the room, we were now lovers in real life. After she was spent from her orgasm, she pulled her softening cock out of its temporary home and rolled onto her back. I cuddled up next to her and we slept contented with our arms around each other.

Before my arrival, we had talked about various fantasies that she wanted to realize including having a threesome with another transgender friend. She loved the idea of having me suck her while another girl fucked me in the ass. The fantasy of being spit roasted excited me too especially when she showed me a photo of her friend and told me what a big cock she had. When she talked to her roommate about my visit, they agreed that at the very least she would get a lot of fucking out of it.

Now that we were together, she told me that she felt that our first intercourse was an act of marriage and that we were now married to one another. She didn't want to share me with anyone else and her fantasies would have to wait for the future. For now I was hers alone and that's the way we both wanted it.

We woke up much later that day, in the afternoon, and we fucked again almost so that we could be sure that it had not been a dream. I crouched on the bed in a submissive position and offered my ass to her. She took my breath away as she penetrated my hole with her sex organ and had her way with me. Again I felt her finish deep inside me.

Every time she ejaculated in my ass, I kept expecting her cum to leak out or drip out while I lay on the bed afterwards. This is what had always happened to me with the woman in Hong Kong. Now I was convinced that with her much longer penis, my girlfriend was able to deposit her semen so deep inside my bowels that it never came back out. I could only assume that my body absorbed its nutrients. I loved thinking a part of her was inside me for safe keeping.

After dinner, we went to a bar close by the hotel named Mixed Nuts. It's a bar where guys go for sex with the transgender women who work there as hookers. It was kind of overwhelming seeing all these beautiful women as they danced for our pleasure. We did not talk to any of them since we had no intention of taking any of them back to the hotel with us. I was just happy to be going back to the hotel with my girl.

Later that night she woke up horny and ready for sex. This time she put on a condom to protect her tender penis. It gave her less sensitivity but she was able to fuck for a much longer time before she came. I liked having her inside me and fucking for a long time but after she had her orgasm and pulled her dick out of my ass, I was sad seeing the condom with her cum inside. I felt deprived not getting what I needed and wanted: her cum up inside me raw and bare.

Why did I want it so bad? While it was true that I felt emotionally connected to her after making love, I had a deep sense of well-being and satisfaction knowing that she had inseminated me. Was it strange for a man to feel this way? Probably but I had long since given up trying to analyze how I felt. I resolved that I would just enjoy our experiences together and not worry about anything else.

The next day we took a taxi from the hotel to her apartment in the afternoon. It was strange being in the place that I had seen so often on the webcam. It had seemed so much bigger than it was in real life. It was kind of depressing to me although I didn't say anything to her. She deserved so much more than this.

Upstairs in her little room on her bed next to the open window, she fucked me doggie. I always made a lot of noise moaning while she fucked me and this time was no different. I moaned like a bitch as my top girl rode my ass. The neighbors might have heard us as we fucked but it did not stop us from completing our mission.

That night, we went back to Mixed Nuts and this time, we decided to talk to one of the hookers and buy her a drink. I saw one beautiful girl who playfully but very forcefully humped another girl on the dance floor. This was who I wanted to talk to. She had beautiful natural looking breasts that she showed us and my girlfriend touched and squeezed them. She wanted breasts and so she was evaluating this girl's boobs to see how she liked them. I would have liked fondling them myself but I didn't think it was a good idea. The hooker was very opinionated and talkative. I liked her and agreed with her opinions but of course I preferred my girlfriend.

When we got back to the hotel, we were both horny and I cleaned myself out by putting water up my ass with a small bulb syringe. Unfortunately this left some moisture up inside my rectum and created some resistance. I could tell that sliding her cock in and out of my ass was not as smooth as it normally was.

Finally she was able to get stimulated enough to cum! She said that she loved seeing her stiff boner sliding in and out of my ass hole and I thought that I would love seeing that too. I had hoped that one time she could take a little video so I could see how it looked but it never happened. I still have hopes of making a little video some day so I can see myself being impaled on her monster cock.

In our sex life, I generally let her decide what to do and how to do it and when to do it. For the most part, I am submissive in bed and like to please my partner. Even when I fucked biological women, I always placed their orgasms above my own. Sex was never good for me if I had orgasm and my woman did not, so I made sure that this NEVER happened.

With my girlfriend, she was the top and for the bottom, it was all about making sure that she had a great orgasm. There were a few times I was very close to coming while she fucked me but I wasn't really focused on my own orgasm. To tell the truth, I didn't care if I came at all. I just wanted her to cum and be satisfied. All of my pleasure was in being fucked and her satisfaction with fucking me.

When I was with the girl in Hong Kong, I didn't spend much time sucking cock. I was so busy learning how to bottom that I failed to learn how to suck cock. Worst of all, sometimes I scraped my girlfriend's sensitive cock with my teeth! I loved having her erect penis in my mouth but I was not yet skilled enough to make her cum just using my mouth. So she jerked her cock with her hand vigorously while I had the knob in my mouth waiting for her cum.

When her orgasm was close she released her hand and I sucked as she finished in my mouth. While she was ejaculating, my mouth filled with a warm liquid - not as hot nor as salty as I expected. In fact it was easy to swallow her semen without feeling any disgust or distaste. I thought that I might not like it and I would have to force myself to swallow but this was not the case. In fact it was surprisingly easy to cross this frontier and become a real cocksucker.

The strange thing was she thought the idea of swallowing someone's cum was disgusting and something that she herself never wanted to do. However she admitted that she thought it was hot for me to swallow her cum and she always wanted me to do it for her.

That night, we made sure that I was well lubricated and she fucked me spooning in a nice long fuck. Afterwards I snuggled next to her and told her that I loved her. She lay on her back next to me spent from her orgasm and smiled but said nothing.

Although I was happy to suck her off and swallowing her cum was very exciting to me, oral sex never gave me that "in love" feeling. Of course it was satisfying giving her what she wanted but there is something about having her cock and her cum up my ass that sends me to the moon. Even if I was a little annoyed or upset with her, being fucked always made me fall in love with her. Why is that? It made me realize why women love to be penetrated by their men - it probably gives them the same feeling.

It made me understand women more by being a bottom. Sadly I realized that I had been selfish many times with my ex-wife. She would want me to fuck her but instead I was busy with something or other. Of course I did fuck her but I really should have just fucked her whenever she had asked me to. Why not? If it made her feel so good, why didn't I? I now understood what she had been craving. I should have just fucked her several times a day whether I was horny or not. It was sad thinking about what a fool I had been with her.

My girlfriend likes to drink and we had gone out drinking with her girlfriend. In the early hours of the morning the friend came back to the room with us and fell asleep on the other side of the bed. My girlfriend's cock was rock hard in the middle of the bed but there was nothing that we could do about it with her friend there. In the afternoon, after the friend left, we repeated the oral sex experience of the previous day. Again she jerked herself with the head of her cock in my mouth and I swallowed my second load of cum in two days.

Like my ex-wife, I was horny to be fucked and my girlfriend had excuses to avoid fucking me. It was definitely karma coming back to me. That night when I went to bed, my feelings were hurt and I was a little mad at my girlfriend. After I was asleep, she decided to fuck me while I was lying flat on my stomach. She straddled my legs just below my ass and lubed us both up. I woke up to the pain of her cock entering my ass hole but it stopped hurting as soon as she pushed her whole fuck stick up inside. She fucked me hard trying different ways of thrusting in and out and she raised her body up and down, sometimes lying on my body and other times holding herself up with her arms.

I was out of my mind with desire for her and I moaned and grunted, "Fuck me hard" as she brutally jack hammered my ass. I wanted her to tear my ass wide open and get inside me completely. In her excitement, it seemed like she was trying to do just that. Finally she gripped me tightly and holding me, I felt her cock throbbing as she ejaculated a pool of spunk into my rectum.

Afterwards she lay still on top of me with her cock in my ass for a minute or two. She never does that and I loved feeling her on top of me after cumming. I wanted her to stay knotted up inside me forever. She rolled off me onto her back next to me and lay there exhausted and spent.

The next day she waited most of the day before she decided she wanted a quick blow job before we went to the movies. It took a lot of sucking and jerking before her cock exploded in my mouth. Of course I swallowed every drop of her semen and then we went to the movies. As I sat there in the theater I could still taste her cum on my lips and tongue. It made me feel really close to her next to me but it also made me feel like a real whore and I loved it. I almost wanted to tell the other people in the theater that my girlfriend had just shot off in my mouth.

That night I fell asleep naked lying on my stomach and I woke as she sat on my upper legs and poured lubricant over her penis and up along my ass crack and into my hole. She slid her cock up and down my ass crack sometimes poking a little in my hole until she was rock hard. Then she pushed the knob inside and applied a gentle but continuous pressure until my sphincter muscle relaxed and opened up for her.

Straddling me she tried different movements from fucking me with fast strokes in and out to sliding in balls deep and thrusting hard into my ass. I lay there conscious of nothing except her cock inside me feeling every sensation as she fucked me like her bottom bitch. She owned me completely and she pumped in and out of my ass hole until she couldn't take it any more. Deep, deep she thrust and then stopped until I felt the small movement that meant she was pissing her jism into my bowels.

Would I ever get tired of this? Every single time it felt amazing as she lay on top of me finishing her orgasm. Then she was still and we lay there together for a little while until she pulled out and rolled off of me.

The next day, after she came out of the shower, she was naked and I was lying on the bed with my head on a couple of pillows. She straddled me while kneeling and put her flaccid cock in my mouth and started to face fuck me. I sucked and licked her big sausage until she was really hard and ready. Then she took her cock in her hand and started jerking vigorously. Occasionally she would put the knob in my mouth for me to suck or lick.

She looked down on me at times while I was looking up at her. I felt as though she was dominating me with her huge hard rock in my face showing me its strength. I could tell that she was enjoying her dominance over me. To tell the truth I was enjoying it myself. Although I loved looking at her penis, it was more than that, I actually adored it. It was so big and strong and beautiful that I felt honored to be the one chosen to service her. I was in awe of its size and its power. Every time I saw it, I just wanted to immediately bend over so she could mount me like a bitch.

I thought that she would cum in my mouth at the last second but instead she sprayed my face with the gobs of hot cum that exploded from her big throbbing cock. She used her cock like a hose so the jets of cum landed all over my lips and chin and nose. My face was covered with her love juice and she looked down at the mess she had made. She smiled in satisfaction before quickly wiping her cum off my face with her hand. This was the first time that either of us had done this.

At the end of the first week, I had experienced my first facial and first oral sex to completion. My lover had experienced twelve orgasms, one on my face, three down my throat and eight up my ass. More importantly I was totally in love with her and I wanted to be her one and only lover forever.