It is week 3 of Carey's transition and she has come over with one of my female friends and boy look at the changes. Just 3 weeks ago she fought at the idea of estrogen and now she is on it. Her name has been changed to Karen and you can see the breasts started to develop. My friend Linda motioned me into the kitchen and we talked.
She asked," She is coming along nicely don't you think?"
I said," Oh she is coming along faster than even than I thought."
She asked," Do you have enough condoms?"
I said," I do but this might be a special occasion."
She said," Special how?"
I said," Bareback if I do her bareback she will know her role."
Linda said," Well, how many sissies have you barebacked?"
I said," One other but I think this one still has reservations."
She said," Well, it is time for me to leave you to your work."
She left and I turned to Karen.
I said," You are still trying to wear men's clothing I see. You still haven't gotten rid of all of your men's costumes."
She hung her head and muttered," I don't know if I can live my life as a woman."
I said," Strip off every piece of your male costume."
She asked," My underwear too?"
I said," Every piece"
She took off every piece of clothing and she stood naked.
I said," Since you are still questioning being a woman I want you to get down on all 4s like a dog."
She looked at me stunned but she submitted to me.
I got out some lube and worked it thoroughly into her ass.
She asked," What are you going to do?"
I said," I am going to thoroughly fuck and breed you."
I heard her whimper and begged me not to do it.
I started to push my cock inside her tight boicunt and kept pushing until my nuts were resting on her cheeks. After she adjusted to my intrusion I pulled 3/4s the way out and shoved it back in.
When I did that I heard her moan in ecstasy and I knew I had her. I pounded her boicunt for an hour and a half and than I flooded her with my seed.
I allowed my cock soften inside her and than pop out.
She laid in my arms for another 30 minutes than she said," I know now I am not a man but a woman."
I said," You are not to have anything penetrate it for 4 months we want it to tighten up for your man when you meet."
She got up and I helped her with her bra than she put on her panties and she stepped into her dress and pantyhose. She put on her heels and than she kissed me goodbye and I watched her walk to her car and get in and drive off.
I have another feminine man coming tomorrow for his/her first session.
I ate dinner that night and turned in early knowing that phase 3 on Karen will begin.