From Family Man to Bottom Bitch Ch. 03

After a couple of years chatting and jerking off with webcam girls, I was ready to meet someone in real life or IRL as it was known in the chat rooms.

I had asked the model from Singapore if she would ever be willing to meet me and she said yes, but she disappeared before I was ever able to make arrangements to do so. It gave me some ideas that it was possible to take things to the next level if I could find a suitable woman. The question was, how to find her?

Around this time, I discovered some dating sites that had thousands of transgender members from all over the world. One of them, Thai Friendly, focused on Thai women, both genetic women and transgender women. The other, Pina Love, concentrated on Filipinas.

After chatting with the Thai trans women, I discovered that many of them did not speak English well enough to pursue a relationship. Unfortunately those with good English skills were hookers or bar girls looking for customers. Some of them were funny and interesting but I had already dismissed the idea of sex with a working girl.

On the other site, almost all of the Filipinas were regular women looking for a man for a relationship, hopefully long term but short term was okay for many of them. A lot of them worked in beauty salons and a surprising number worked in the call centers. The call center women spoke very good English and although they were not well paid by Western standards, they were white collar professionals. In fact many of them had gone to college.

I paid for a membership on Pina Love and went to work, screening the women and chatting on cam with the most promising candidates. A lot of these chats were disastrous in various ways. Many women photoshopped and filtered their photos so much that they were almost unrecognizable on camera. Many of them had traits that I found difficult to get past like deep voices or masculine features. Some of them were not shy about asking for money or offering cam shows for money.

For me the real problem lay in the fact that most transgender women see themselves as women in every way including sexual roles. I could completely understand this so it was not surprising to find that almost all of the women were either bottoms or versatile. Only about one in twenty was a pure top and a large majority of those were rather masculine in appearance. Finding a feminine transgender woman who liked to to top was like looking for the proverbial cock in a haystack.

One day I saw an attractive woman named Angel who worked in a Manila call center. Chatting over text, I broached the sensitive question of sexual roles. She was up front about herself saying, "I am a pure top. I have a big hard cock and I do all the fucking." Music to my ears!

When I saw her on the camera, she looked just like her photos, pretty and feminine with long jet black hair. Although she used a lot of makeup it was well done and I found her very attractive. There was not a trace of masculinity in her voice or her appearance. Could she be the one?

As we talked it wasn't long before she got horny and she asked me, "Do you want to see my big cock?"

"Yes, please." I answered trying to control my excitement.

On the camera, I could see her lifting her skirt and pulling down her panties. She stepped out of her skirt and lay down on her bed in front of her camera. Her penis was already engorged and throbbing, ready for action. She positioned it with her hand displaying at least six inches of fuck meat topped with a purple cock head that meant business.

"Oh my God" I muttered as I savored the sight of her erect sex organ. Would I ever get tired of seeing the stiff pricks of these lovely women?

"How are you doing?" she asked me as she grabbed hold of her raging boner.

"Okay" I answered softly, "I want it so much."

"Nice to hear." she chuckled. "Do you want to sit on my cock like a girl and take it in your tight asshole?"

Her dirty talk left me feeling weak and dizzy as though I was under a spell or a drug. All I could say was, "Oh my god, yes I do."

As she stroked herself, she continued with her horny talk, "In bed, I will be the man and you will be the woman. Do you understand? What do you think about that?"

Actually it excited me to hear her say this and I imagined lying before her with my legs open like a woman waiting for her man to mount her with his cock and fuck her. I wanted to take her fuck stick into my body and feel her thrusting inside me. I told her, "I want you to fuck me."

"Yes, baby, I will do all the fucking. You will serve my cock like a bitch in heat. Will you be my bottom bitch?"

I felt like a bitch in heat and I wished that she could do everything that she wished. "Please be my top." I whispered to her.

For now I had to be content watching her massage her stiff penis with her manicured hand as she told me, "You will be my wife in bed and I will be your husband. Your ass will be the pussy I fuck with my cock."

"Jesus" I moaned. How did I feel about this graphic gender bending? This woman did not mince any words about our sexual relations. Was I okay with having my ass referred to as a pussy? With being the woman in bed? To tell the truth it made me horny as hell and I was jerking my cock in a frenzy.

She could see me in the camera and she laughed, "It looks like you want to be my bitch. Give your husband your ass pussy, darling, and be a good wife."

By now, she was getting close to her orgasm and she was panting with excitement telling me, "Open your legs and give me your cunt. I am the man and you are my woman for me to fuck and cum."

She was making me wild with desire for her as I watched her jerking her male sex organ. I would have done anything to help her cum. I had to help her cum. After all, it was a wife's duty to make her husband cum.

So I told her, "Yes, my husband, fuck my pussy with your big cock. I want your seed inside me now. Please make me pregnant. I am your wife."

Of course it was a ludicrous idea but these words sent her completely over the top. She gasped and mouthed, "Oh fuck! Oh fuck, you bitch!" as she spasmed in the throes of her climax. Her cock pulsed with the force of the hot semen shooting up through her shaft and she ejaculated long thick ropes of cum all over her chest and belly. It was an amazing display of her sexual prowess and I was in awe of the power of her cock.

As usual I hardly noticed my own orgasm until I felt my fingers sticky with the jism that had spilled from my own cock while mesmerized by my partner. I had been so obsessed with her orgasm that I almost felt it more than my own. Had I been a good wife for her husband?

Afterwards I had to admit that her words had made me incredibly horny but I wondered why? I never had any desire to be other than what I was - a heterosexual man. I didn't want to wear female clothes and I certainly didn't want to be a woman. So why did it stimulate me so much to think of myself as the woman in bed pleasing her man sexually? What did this mean?

There was something perverse about it but also a kind of truth. I had to admit that I had always been a man with a female spirit within me. I was a very nurturing and loving father and I was happiest when I was helping others and taking care of them. Small children and animals had always been drawn to me because of my gentle and caring nature. Could it be that my desire to sexually service a woman by taking her cock into my ass and mouth was part of that nature? Yes, I was definitely a man but an unusual one to be sure.

I think that I could have made a good partner for Angel but she was worried that I had never been with a transgender woman IRL. She told me why.

"I met a man like you online and I liked him very much. We seemed to be compatible sexually and everything was wonderful. After we chatted for a couple of months, he made plans to visit me. So he came to Manila and I brought him to my apartment. We kissed and fondled each other for a bit and everything seemed to be going well. Then I took off my panties."

I suspected something went wrong so I asked her, "What happened?"

"When I took off my panties and he saw my big erect cock, he panicked. He apologized but he said that he couldn't continue. He said he thought that he would be able to have sex with me but now he realized that he had to leave. He hurriedly fixed up his clothing and repeating how sorry he was, he left my apartment. I never heard from him again."

"Oh no!" I said. "How awful for you!"

"Yes" she said. "It was awful. I felt very bad about the whole thing. It made me doubt myself for a long time."

"You are okay now though?" I asked her.

"Yes, but I must insist that you get some sexual experience with a transgender woman before you come to see me. I must be sure that you will not be like him."

"What do you suggest that I do?" I said.

"You should get a hooker in your town and have sex with her. If it's okay for you then you can visit me."

"I really don't think that's necessary" I told her, "I am pretty sure that I will be fine."

"No, I won't go through that experience again so I am not taking any chances." She was firm about this request.

That was how we left things. Of course I did not go to see a hooker as she suggested although I probably should have. Instead I continued chatting with transgender women on Pina Love and I met someone that I was to disappoint deeply.

Years later, after I had met a Filipina in Hong Kong who fucked my ass nineteen times in a week, I contacted Angel and told her that I now had experience, a lot of experience. She was mad at me upon hearing the details and stopped talking to me. I never heard from her again.