Cross Dressing Sissy

By John Nail

Published on Apr 6, 2009

Transgender

I spent the whole day Saturday with Jennifer being playful talking,laughing and basically just enjoying each other's company. I left there Saturday evening with her needing to run some errands and basically needing to get ready for work.

I was loving this I couldn't believe it things were moving quickly and I did not want to get off this train. I got home and started doing the normal cleaning I did on Saturdays and since my home I was renting was small and I kept if pretty neat during the week it only took me about an hour. I sat down with a beer and turned on the T.V. and was watching it when there was a knock on the door. Standing at the door was Tim and Amy and I told them to come on in.

Tim asked as Amy went into the kitchen to get herself some water," So how did things go we noticed you weren't home for most of the day."

I looked at him and smiled and said," She is fantastic and I can't get her out of my mind, not that I want to. She showed me that she was born genetically male but it didn't matter to me."

Amy came into the livingroom and sat down by Tim and she looked at me.

She said," You found out Jennifer is special anatomically haven't you? Tim and I already know she wasn't born genetically female, but she is all lady."

Tim laughed and said," Remember, Theresa , she was an easy and good lay."

Amy shot a dirty look after the comment.

I said," I know Tim you just have to remind me don't you. Well I never thought that I would go out with a cross dresser. She told me that she is saving up for sex change never had it when she was a child because it was too risky. I am falling in love with her and it doesn't matter."

Amy said," I thought she would be good for you that is why I told Tim to send you to Jennifer's."

I looked at them and smiled, I should have known Amy set this up.

Tim said," You are lucky I love Amy the way I do or you wouldn't have Jennifer."

I shot back," I might have had to settle with Amy."

After that we both laughed and just shot the bull for another hour.

.Well Tim and Amy got up and Tim said," We have to go and eat at her parents and Amy still insists I shower and clean up."

Amy shot Tim another dirty look laughed and said," I still have to put up with this animal."

They walked out and I sat down in the chair and was watching America's Most Wanted when there was a knock on the door I looked up and saw it was Jennifer and my shirt was unsnapped decided to leave it unsnapped.

I opened the door and said," Jennifer sweetheart why don't u come in my small palace." I did an exaggerated bow.

Jennifer giggled and came into the house.

Jennifer said," I don't know where I begin and I never thought I would be asking this. John I have been falling deeply in love with you and you have accepted me as a lady even though genetically I wasn't born female. Other guys I have been out with looked at me as just a curiosity and not as a lady.

I would love to have you move in with me and we can really be a couple."

I looked at her stunned because I have thinking about moving in with her.

I told her," Jennifer I would love to move in with you, if you can wait a couple of months until my lease up, but I will start slowly moving my stuff over so by the time my lease is up which is about a couple of months."

Tears welled up in her eyes and she grabbed me in a passionate embrace and smothered me in kisses.

She got up and I walked her to the door and we kissed goodbye I watched her walk to her car and started up and leave.

I looked at my watch and saw what time it was and decided it was time to go to bed.

Part 2 of Ch.4 Jennifer's Story

I can't believe it John said yes about living with me this is a dream come true. I have fallen in love with him so quickly since Amy had Tim set us up. Oh seems so long ago since I moved here from Chicago even though it has been only 6 months. It feels so natural to be with John. He holds me so tenderly and I know he loves me as much. I love seeing his pickup in my driveway which will soon be ours. This will be a whirlwind of activity with him gradually moving his things here. I have told my parents about him and they were thrilled especially when they found he accepts me for me.

Amy and I were talking the other day when I broached the subject about asking John to move in with me and Amy said that he would probably move in with no hesitation.

She told me about the changes that came over John since we met that he wasn't quiet as wild as he used to be. She told me how John used to go from woman to woman and she sees him getting ready to settle down with me.

I am just picturing sitting on the couch with him and laughing and talking and kissing and with him coming home from work and being at a ranch where he is helping to brand or whatever. I love everything about him and I am ready to spend my life with him and I hope he is ready to spend his life with me like Amy said she thinks he is.

Next: Chapter 5


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