From Family Man to Bottom Bitch

If someone had told me that one day I would be sucking on a seven inch cock like a starving puppy and happily slurping up the cream from that cock, I would have shaken my head in disbelief. If someone had then told me that I would be offering up my asshole for that same cock to fuck and begging for a fresh load of cum deposited deep in my rectum, I would have said that you were hallucinating.

I was a straight man with impeccable heterosexual credentials. Never in my life had I ever looked at a man with any sort of desire or even taken so much as a glance at gay porn. I had absolutely no interest in men or the male sexual organ and the very thought of touching one would have made me nauseous. Even now I find the whole idea of having sex with a man completely disgusting.

I had been married with several children and my sexual interest had always been exclusively female. In fact I barely even noticed other men because my attention was always focused on women. I loved women. I loved talking to them. I loved looking at them. I loved licking and sucking their pussies. I loved fucking them.

So it was that I found myself exploring a chat site that allowed the members to watch each other's web cams and chat with one another. I was fascinated by the site but one young woman in particular took my fancy. Every night she sat in front of a sheet draped behind her of Pooh Bear and his friend, Piglet. She lived somewhere in the Philippines.

She was very beautiful with long straight hair that she dyed various colors and a little smile as she watched the other web cams. Very rarely did she chat or even respond to my greetings or compliments. Finally one day she did engage me in conversation and thereafter we would chat a little every day. Often she disappeared for a while and then reappeared.

She told me that her name was Isabel and I told her my name, Sean. That seemed to increase the intimacy between us and we steadily spent more time conversing with one another.

The months went by until one night, she was agitated about something but I couldn't get her to tell me what was bothering her.

I asked her, "Isabel, please tell me what's wrong?"

She said, "Sean, I can't tell you because you will be upset with me".

I pleaded with her, "Of course you can tell me, why would I be upset with you? You haven't done anything to me."

She responded, "I have not been honest with you. I have lied to you."

I was incredulous, "How have you lied to me? I don't understand what you are talking about. Please explain what you mean by this?"

I was really confused by the whole conversation and nothing she said made any sense to me. Why was she talking like this?

We engaged in more back and forth about her distress until finally she seemed to come to a resolution. She said, "Sean, there is something I have to tell you. I am not a girl."

Now I was really confused. Not a girl? She was obviously a girl and a very pretty one indeed. Everything about her was small and delicate and feminine. What did she mean by this? Was it some kind of joke?

I told her, "Isabel, I don't understand what you are telling me. Of course you're a girl. Why are you saying this?"

Then she changed my life by what she said next, "Sean, I may look like a girl to you but I was born a boy. I have a cock."

To say that I was dumbfounded doesn't even come close to what I was experiencing. How could this be? How could someone who looked like her actually be male with a cock between her legs? I just could not accept it. I refused to accept it. It could not be true.

I told her, "I don't believe you, Isabel, and I don't understand why you are saying these things. This makes no sense to me at all."

Determined to make me understand what she was saying, she said, "I guess that I am going to have to prove it to you since you don't believe me."

She got up from her chair and then pulled down her jeans revealing a pair of flowered panties. I hardly had time to notice the bulge in her panties when she took them off and exposed a circumcised penis about six inches long hanging down between her legs.

"Oh my God!" I exclaimed. I didn't know what to say. There it was, just as she said, a male sex organ on the body of a young woman. I just looked at her in wonder. I had never imagined that something like this could exist. How was it even possible?

While my mind was reeling from the shock of what I was seeing, I felt something else stir deep within me. Desire.

I was ashamed of what I was feeling but I did not want to make Isabel feel bad about her revelation. I gently told her, "It's okay, Isabel, you are still the same person. Nothing has changed between us."

She was very surprised and she asked me, "You mean that you are not mad at me?"

I said, "No, I am not mad at you at all. It's okay, don't worry."

Far from being mad at her, I was mesmerized by her body and I could not deny the feelings of sexual desire that I was experiencing.

I wanted her cock. I wanted it in my mouth. I wanted it in my ass. I just wanted it as I have never wanted anything in my life. I adored her cock and I told her so, "Actually, Isabel, I don't know why but I love your cock."

It was her turn to be speechless, "What are you saying, Sean? You like my cock?"

"Yes, Isabel, I like it but it's so much more than that. I want it. I want you." Somehow confessing to my desire made me feel better.

She smiled at me and then wrapped her hand around her cock. It quickly sprung to life getting hard and erect. Like an animal it seemed to have a life of its own as it pointed upwards throbbing in its excitement. "Do you like it like this?" she asked me as I watched her play with herself.

"Oh God, Isabel." I replied rubbing myself as I stared at the big hard prick in her hand. If thousands of miles had not separated us, I would have taken it in my mouth without hesitation. Even worse, I knew that I would have bent over and asked her to fuck me with it. I felt overwhelmed by my feelings looking at her - I just wanted to lie down and let her do whatever she wanted to me.

She continued to fondle herself and I frantically ripped my pants off to free my own rock hard cock. I gripped it in my hand and jerked like a man possessed. She could see me jerking and she said, "Yes, I can see that you really do like it, Sean."

"Yes, Isabel", I groaned as I watched her beating her cock meat while she got more excited. I was jerking myself hard but all my attention was devoted to her stiff penis. All my desire was focused on her orgasm and I begged her, "Please cum, Isabel. Give it to me, darling."

She grunted and pulled at her boner as the creamy jets of cum spurted from the cock head and I wished that every drop of her spunk was in my ass. I hardly even noticed my own orgasm as I shot cum all over the floor in front of my computer.

"Thank you, Isabel." I told her, "That was amazing. You looked so beautiful while you were cumming."

"Really, Sean?" she laughed, "I guess that you did like it."

After we cleaned ourselves up, we talked a little more about what had happened. She was obviously relieved that I was not mad at her and happy at how things had turned out. She told me, "I never imagined that someone like you would be interested in a girl like me."

She was right. I never imagined it either. Of course I never imagined that girls like her even existed. I had never given transgender people a thought in my entire life up until then.

Later that night, I thought about what had happened. There was no denying my own desires but what did they mean? I was so confused.

Did this mean that I was gay? How could I be straight if I wanted her cock so much? She still seemed like a girl to me even with her big cock. How was that possible? Could you be a girl and still have a cock? Could I still be straight even though I wanted a girl to fuck me with her cock? Did this mean that I wanted guys to fuck me with their cocks? Oh please, no!

I had so many questions about myself. I had always thought that I was a perfectly normal guy who was only interested in women and pussy. That was all I had ever wanted until the moment I saw Isabel's cock. I asked myself, okay now what?

In the months to come, Isabel and I continued chatting and sometimes jerked off together. During our sexual interactions, I confessed that I wanted to suck her off and for her to fuck me in the ass. She was amazed and excited to hear this.

She told me that she had had an Australian boyfriend but he had always fucked her. Now that she realized that maybe she could be the one doing the fucking, she loved the idea. The best part for her was the fact that I was straight and had been married with children. She had never thought that she would be able to fuck a guy like me.

I struggled to accept my desires and what they meant for my future. I still wasn't ready to take the next step and actually go visit Isabel. If I actually went to see her, I knew what would happen and I would not be able to deny who I was.

I had always been the man with the cock who fucked the woman with the pussy. I liked this arrangement and I never had any problems with it until I met Isabel. If she fucked me, did that mean she was the man and I was the woman? I didn't want to be a woman - I was a man, I had always been a man and I never thought of myself as anything else. At the same time it was impossible for me to think of Isabel as a man. Sure she had a cock but nothing about her was masculine, not her voice, not her face, not her slender body and not her small perky breasts.

Sadly, my relationship with Isabel was never consummated and I lost track of her. The site where we had met became a dating site and our means of communication, Yahoo Messenger, finally disappeared after our messages had become more and more infrequent.

It would take many years of soul searching before I was ready to take the next step through the door that Isabel had opened for me.