This is how I started down the road of being a sissy. I was a manly man and had no desires of being a cross dresser, sissy or anything else for that matter.
It started innocently enough, my wife was out shopping one Friday evening as I tagged along. One of our stops was in Vitoria Secret. She was looking at underwear and a pair caught my eye, they where sliver, light pink, and black mixed colors. Innocently and curious I reached out to feel the material which was shinny. My wife noticing this and asked if I liked them. I told her I was wondering what they felt like was all. She continued picking out some underwear then come over and was looking for her size in the ones I had felt the material on. Picking a pare off the rack we headed to paid for her items. We had a few more stops before heading home for the evening..
Saturday came and she was modeling her new items she had picked up from shopping the night before. She had a pare of slacks ,one dress, a top, and the last was some panties which looked great. Then she came out nude except for the last pair which had my full attention by now. I asked if she was interested in having sex now that she had me worked up. She said under one condition, by this time I was game for anything. She went to the bedroom and returned with the pink, sliver, and black shinny panties I had looked at. If you put these on and wear them the rest of the day we will have sex tonight. I told her now way and why would she want me to wear them. Her remarks where, you checked them out and also said you wanted to know how they felt. Now you can try them on and see, I picked out your size. Then she held them up and waved them back and forth saying sexy, sexy.
That my friend was the beginning of the end of me being manly. I confessed that they did feel nice and fit great. I continued to wear them the rest of the day. I had great sex that night and the next day was a repeat of the same. During the week she had teased me about the panties and how sexy they looked on me. She also pointed out how sexually aroused I was when she put them on me. She told me that if I liked the feeling of those panties I would like the feeling of pantyhose. I told her lets not get into dressing me up like a cross dresser. The following week end she talked me into trying on pantyhose. I liked the feel of them but preferred the panties but I told her that they felt okay.
She eventually over time talked me into shaving my legs and gave me a garter belt and nylons to try on. I loved the feeling of the silky material caressing my legs and once I put my panties on and looked in the mirror I liked what I was seeing. My erection was so hard I could not keep it in my panties. Sticking above the elastic top she noticed and said, how happy she was that I liked the lingerie. She told me there where more surprises for me provided I wear this all weekend. When I asked what they where she told me I need to get used to the lingerie first but my outfit was not complete with out a bra. Then I was handed a lovely lacy bra which she helped me put on. Now if you wear these clothes for the weekend, she would give me the other item next weekend.
This kept going until I was completely dressed as a girl. After several months had passed she told me I should start wearing makeup. This was more of a shock and I resisted and would not agree to that, at least not yet. Over the next few months I was parading around every weekend dressed like a hooker. I loved it and could not wait until I came home from work to shower and put on one of my outfits. My wife naturally encouraged me to put on my full lingerie and skimpy outfits for the evening. Now this had been going on for some time and only at home. She eventually talked me into trying a little makeup and I was impressed how hot I looked with just a little eye shadow some blush and lip gloss. The next time she offered to do makeup for me I told her to go all the way. Once completed she went to the closet and pulled down a box that had a wig in it. Putting it on and with a bit of styling I looked hot if I do say so myself.
My wife told me I really looked good and said we should take some glamor shots of my transformation. I agreed to it and she took about forty some pictures including me in just my lingerie. I felt great and I told my wife I felt confident enough to go out in public., she reassured me that I was passable. We planed a weekend out of town and had a lot of fun going out as to girls. We did this quite a bit over the summer.
Over time noticed she slowly cut back on letting me have sex with her. One day I asked her when where we going to have sex again as I sat on the couch in just my lingerie. She sat down beside me and we had a long talk, reassuring me she liked the new me and had no intensions of ever leaving me. She pointed out how nice I looked as a girl and was happy that I had adjusted to it so well. She also pointed out to me that she enjoyed going out as a couple of girls. However I was now a sissy and she only seen me as a sissy not a man. She pointed out that she was not a lesbian and did not want sex with a women or a sissy as far as that goes. You can imagine how I felt when hearing all of this. I was told that unless I find a lesbian that accepted me as I was, it probably was time to reconsider who I was going to have sex with.
When she asked if I had thought about having sex with a guy I naturally said no way. She asked for me to be honest with her reassuring me that she had no intensions of leaving me. She felt I was not being honest with her pointing out how I carried on flirting with guys when we where out at the bars. Looking down I told her I thought about it but worried what she would think. I did not want her to think of me as being gay. I was told that she did not see me as being gay I was now a sissy and it was only natural for a good looking, cute sissy to be attracted to cute guys. Sissies are suppose to be with guys, being gay is a man on man thing in her eyes. Since I was no longer a man but now a sissy she thought it was only right. I told her I was not ready to start dating or doing anything with a guy. She told me to just think about it and we could talk about it latter.
Over the next month or so she would drop little sexual hints. When watching a movie she would point out hot guys and say I bet he has a big cock. She made remarks about other guys and comment on cock size and their looks and if they would be good in bed. One evening she wanted to watch gay porn so we watched a few shows along with other small remarks she would make. Then one day while I was sitting in my lingerie she asked if I had given it any more thought about being with a guy? I turned the question back to her and asked if she had been thinking about being with someone else? With out hesitation she answered well of cores I have.
Just as she admitted to it my cock sprang up. Seeing this she looked me in the eyes and asked, do you want me to have sex with a guy? Because you got an erection as soon as I said yes. Well not really, I do not want you to. Well she pointed out my cock said different and maybe a big manly cock would be a nice change. I may even let you watch as I get pounded by a big cock. My dick was so hard thinking of the image of someone fucking my wife. You could suck his big cock sissy boy she said, would you like to do that.
That was three years ago we had that talk, I had been cross dressing for about a year by then and looking good. For the last year and a half I have become her house sissy boy. She has lovers from time to time and lets me watch some times. I have been practicing sucking on my dildo she bought for me. Some point in time she told me I will have to suck a cock. For now I am satisfied jacking off as she tells me about her love making while watching me do my thing. She told me now that I have found my true calling in life, maybe I should think of taking hormones or having breast implants. One thing at a time, I have not sucked my first cock yet. I know in time that it will happen. That is how it started for me, Bob now Bobbie.
(SM) Sissy Maker