Itchy Nipples

It started some years back when my wife Chris noticed that I was spending a lot of time looking at pictures transgender and crossdressers. She asked me if I liked them whether I thought they were sexy, Of course I could not lie - I told her that I did. So the story goes like this...

I travel a lot being a software distributor so it means's that I may be away from home for several weeks at a time. I never even noticed that she had been reading magazines and books on trans. gender so I did not even think twice when she said that I should start taking vitamins since I probably was not eating like I should wile I was out on the road. I told her it made sense to me so I started taking them that day. Little did I know that she thought that Chicks with Dicks were sexy too and intended to have one of her very own

As it turned out the vitamins were hormones. At first there was no signs of change (to my body) but I did feel like I had more energy, thinking back that was probably more in my head than any thing else. But as time went on I began to notice things like how my nipples would itch and be tender. Then one day I opened my bags (that my loving wife always packed for me) to settle in for a much needed rest after a long and lousy flight and laying on top was a pretty black bra not to lacy and not to plane .I was so tired from a bad flight that I just wanted to take a shower and get some sleep so I grabbed my things took my shower and went to bed. The next day went well I made a rather large sale so I stopped in the bar at the hotel were I was staying to celebrate before going up to my room.

After having a few to many drinks I made my way up to my room and decided to take a shower before bed but when I opened my bag there it was that not to plane and not to lacy black bra. I picked it up looking it over I noticed that it had to small of cups to be one of my wife's she was a large C or a small D and this was an A cup. I put it down again, picked up my things and headed for the shower. But as I stood there shaving it seemed that my beard had not grown as much as normal. After shaving I got into the shower letting the water run down my back I began to wash down the front of my body from my shoulders down. When I got to my chest I slowed down as my nipples seemed to responded to being rubbed with the soapy washcloth getting hard and sending out an almost electric tingle through my body and my dick started getting hard. After taking things in hand and getting the relief that was needed I dried myself and crawled into bed. But I started thinking about it again not to lacy, not to plain and black is my favorite color.

So I got up and went to my bag opening it I picked up the bra holding it up taking a closer look at it I started wandering what it would feel like to have it rubbing against my nipples. I went to the mirror and held it up to my chest to see what it would look like on me, In the semi dark room it looked kind of sexy. So remembering how I had seen my wife put hers on I put it around my chest backwards hooking it I turned it around slipped my arms through the straps and pulled it up into place. I felt great and my nipples started to grow hard as did my dick and as I stood there looking in the mirror slowly stroking myself I started thinking about the She-males in the pictures I had seen. Then I noticed how it seemed that I filled the bra rather well.

Slipping my arm out of one of the straps (not wanting to take off the bra) I turned on a light going back to the mirror I looked close it sure seemed like I was looking at a breast. Reaching up I felt it; it sure feels like a breast. I stood there and played with my nipples and stroked myself to another climax then went to bed. The next day I got a call from the boss telling me that since things went so well I deserved some time off with pay and to get home to my lovely wife. It was still early in the day and Chris was still at work so I grabbed a cab from the airport so I could surprise her when she got home. When I got there I decided that a bottle of chilled wine, candles and soft music would be a great way to welcome her home. So I ran in put the wine in the cooler to chill down. Grabbed my gear went in to the bedroom put my bags down where I always do (she unpacks them for me too. I am spoiled) and went to clean up and finish getting ready for the evening.

When Chris come through the door and saw the lights down low heard the soft music she knew it was a good trip. I came out of the kitchen with the wine and the snacks I had made for us setting then on the coffee table and taking her in my arms kissing and holding her like the angle she is. We sat and talked drinking the wine and eating the snacks but never once did the subject come up about the bra. Later that evening we went to bed and made love like to school kids with hormones raging out of control. In the morning I woke early and went to the kitchen started the coffee Chris woke a few minutes later and came to the kitchen to join me. Sitting there I relished how lucky I am to have her. She broke the morning by saying that she had to go to work but she would take Friday off so we could have a long weekend together. The weekend went by all too fast and Monday came around again and we found our selves back at work then that call come that meant I would be going out of town again.

That night I took Chris out for dinner at a very upscale restaurant when we got home we made love like we would never see each other again. The next morning it was off to another nameless city and another nameless company to do another demo in hope of another sale. This time when I opened my bag not only did I find a bra but a matching pair of panties. I picked them up and sat on the edge of the bed looking at them trying to imagine what Chris was up to. This went on for a couple of months the sexy underwear the itching and sensitivity in my nipples. Then one day I noticed that it was a B cup bra not an A cup, but it still seemed to fit. I decided that this time when I got home I would ask Chris why she was packing the woman's underwear in my bags. When I got in she had set out a bottle of wine and some snacks turned the lights down low and belt a fire, it was like some thing out of a storybook. We drank wine ate then made love right their on the rug in front of the fire. Later that night I asked Chris about the bra and panties in my bag when I went out of town. At first she seemed unsure how to answer but then she started to tell me all the details. It all started when she saw the pictures on a web site, it made wonder how they got that way so she asked one of the doctors at the hospital were she works about it. He told her that some were born that way and some were in the presses of having a sex change and that they do the photo sessions to help pay for the operation and some just don't go all the way. Then she asked how it was done and was told there were several ways but most all cases start with hormones. And sense I am small only 5' 5" in my bare feet with a slim build and I have soft thick hair that is sandy blond she thought I would make a pretty woman.

So she found out how much of what hormones to use to use to make the changes she wanted to make with out causing loss of the male sex drive. After she finished we made love again. I the morning she got up early and put on the coffee when I got up I put on one of her satin and lace robes and went to the kitchen for coffee with her. She gave me a puzzled look so I told her that I liked the feel and that I also liked the idea of being transformed but that it would cause some problems at work so I would need to keep under raps until we could work that out. We drank our coffee and talked about what was next and what we would do about my job she assured me that it would be all right. Sense it was Saturday we decided to start my training so I could learn to act and dress more like a woman. First we went and took a shower and she shaved my body not that I have much hair but it still made me look more feminine.

After powering me we went to the bedroom where she got out some boxes looking on intently I watched as she took out several articles of clothing telling me that she bought them hopping I would like the idea and want to go along with her plan. She laid out all the under things and said that she would help me learn to dress put on makeup do my hair, and that on my days off I should dress to get in to get the feel of being a woman. She also had bought a wig in my color for me to wear until my hair grew out. We started the lessons in dressing from the in side out putting on the bra then panties.

Next was a garter and stockings she showed me how to roll the stocking's and pull them up with out putting runs in them and how to put the straps through the panties so I could get them off so I could sit to go to the bathroom reminding me that girls don't stand to pee. Next we went to the makeup where she showed me how to do each steep starting with the base add some blush to highlight and give a little color and higher cheeks. Next we worked on the eyes Chris told me that the eyes were the make or break of doing makeup she plucked my eyebrows then highlighting them with a pencil the mascara to make the lashes longer and thicker. Next was the eyeliner she showed me that it can be done light to highlight or to look to get that hooker look we went for the highlight today after lipstick and stick on nails. Then came the wig and shoes after helping me put them on it was time to see the result of all our work.

Standing and walking on 2 inch heals was not to bad but still a little wobble at first but Chris said I would get the hang of it soon and would be able to go to higher heels before I knew it. Walking to the mirror I looked and saw a very pretty woman looking back at me. I did notice that my breasts were still small Chris said not to be in a hurry that they grow but if I wanted to we could get some pads if it would make me feel better, I told her no, I wanted it to be all me. I spent the weekend as Jackie we thought that sense my name is Jack that it would less confusing just make it into a girl's version. We even went shopping and out for drinks I realize that I had a lot to learn but, with Chris by my side I felt that it was going to be all right. Monday it was back to Jack and off to work but in the evenings it was Jackie I even slept in a nightie and did every thing as a woman in the evenings and weekends.

Chris made an appointment with her doctor friend so we could make sure we did not do any thing wrong or dangers we talked about all the options and decided not to do any surgery just take the hormones and let them do it for us. He said things looked great to him and wrote some prescriptions for some other hormones and upped the dose saying that things would Progress a little faster and that Chris should not have started the drugs with out me seeing a doctor first she agreed and we went home. Things went well my breasts kept growing and my body filled out and I got to the point that it was harder to be Jack than Jackie. I had to wrap my chest so no one at work would notice that I had grown breasts plus my boss started to squawk about my hair getting longer. So we decided that it was time for me to quit my job and move on to some thing else.

We had saved some money so that was not a problem but I would have to find some thing else sooner or later and the sooner the better as far as I was concerned. But first I would need to finish getting all the legal stuff done for my name change so I could work legally. Then what I would do was anther thing but sense I was now sporting a large C cup breast and my hair wag down to my shoulders it was pretty obvious that I was no longer a man nor did I want to be ever again.

I was not attracted to men although at Chris's urging we did bring another man to our bed so I could try it. Even though he was loving and gentle with me it was not what I wanted, and even thought he wanted to Chris did not have sex with him and we never tried it again. Some of the people around town including some of the people Chris worked with thought that Chris were lesbian lovers being that it was a small town we decide to move sold the house and moved to a larger city where we could live in peace. It was for the better at the time Chris went to work at one of the hospitals and I got a job with a large software company we settled in and I kept developing into the woman of Chris's dreams.