How I started as a sissy.

 

We met on line and I invited her over so we could meet. She showed up at eight on a Friday evening, she was tall and thin with a great chest. I invited her in and we talked for about an hour then went down to the local bar for a drink. Once we finished at the bar we went back to my place around ten thirty. I figured she would be leaving but once we were in the house she asked if she could stay over. Naturally I said yes, and I showed her the gust room. She asked if I was kidding and I asked what did she mean? Her reply was I did not drive all this way to sleep by my self. I showed her my room and she stripped off her closes down to her panties and bra, then went to the bathroom to clean up for the night. I was shocked at how open and forward she was. I had never been with some one like this before.

I was in the living room kind of waiting for her to go to bed then I was planning on joining her. She came out of the bathroom and came straight to the living room. Standing in front of me she asked if I was going to come to bed now? I stood up and followed her to my room. She sat on the edge of the bed as I took off my cloths down to my under wear which were a skimpy string bikini for men. Oh so you’re a sissy panties wearer are you she asked? I looked at her and said no there for men, she smiled and said too bad you would make a nice sissy. I was shocked at what she had said and took of my underwear as she took off her bra and her large tits bounced free. Wow their nice I said! She took off her panties and asked how I liked her shaved pussy. It looks great to me I think you have a fabulous body. She smiled and climbed into bed. We enjoyed each others bodies and had a very good night for a first meeting!

The next morning I got up to get dressed and she lied there on the bed watching me. I put on a regular pair of tighty whites as to not get accused of wearing panties by her. She said that she liked the panties I had on last night better. She did not care for the tighty whities and told me to put the others on. I was taken by surprise once again by her open and boldness. Sure I have a different pair which I put on then finished dressing. I went out and made some coffee and she came out naked, sat down at the table and we drank coffee as we talked. She told me how she had a dominate side and likes to use it. She could see I kept looking at her big breasts and asked how I liked last night? It was great I said, I think you have a lovely body and I enjoyed it very much. She then asked if she could spend the rest of the weekend with me? Of course I said with delight knowing it was going to be a fun sexual weekend.

That after noon she said she was going to run into town to pick up some things. I asked if she wanted me to go with her and she said she wanted to learn the town on her own but would be back in an hour or two. She came back with a bag of groceries and a bag that I figured was her things she needed. She made the meal that evening and we both did dishes together. She talked about her past some and her parents. When we were completed she asked me to go to the bedroom with her. I was thinking that sex was starting early tonight and it would be a long night, smiling I said sure.

Once in the bedroom she took off her tops reveling her large breasts and said. I have something I hope you will like and accept without making a big deal out of it all. Then pulling out a couple of pair of lacy panties, garter and nylons. Holding them in front of me she told me that she wanted me to try them on! I was surprised and somewhat confused by what she was asking. What I asked? I would like for you to wear these today come on I will help you in them and you can do what ever you want with me. I was still in shock when she pulled my shirt over my head and pulled me to my feet. She dropped my jeans and told me to step out of them as she pulled down my under wear. Still confused she started to suck my cock at which I came back to my senses. She stroked it and sucked it until it was hard then stood up dropping her pants to the floor. Patting her pussy saying if you want any more of this then you will do as your told!

She then reached for the garter and bent down telling me to step into it which I did still numb from what was happening. As it was pulled up she kept telling me how fun it was going to be and how lovely I looked. Then told me to sit down and showed me how to put on a nylon, telling me not to put any snags or runs in them. Once I had them pulled up I was told to stand and she hooked the stockings to the suspenders. With my cock still hard she had me put on a pair of pink satin panties that hardly held my cock in. Oh you look so sweet just as I thought you would. Back from the shock and numbness of all that was taking place I looked into the mirror and seen myself dressed in female lingerie. You will remain in this all day do you understand? Okay I said.

Lets go to the kitchen as she pulled me by my hand. Laying back on the table with her knees in the air and her feet on the edge of the table she told me to sit down. She grabbed my head and pulled it to her pussy saying, alright my little sissy boy eat my pussy and do a good job if you know what is good for you. I could see she was glistening with wetness as I licked her wet pussy. She moaned in delight saying that’s it sissy boy do your job and do not miss a drop of my juices. I spent the rest of the day in my garter nylons and panties. She asked how I liked our session we had and if it was something I wanted more of? I told her that it was fine and I would like more if that is what she wanted.

The next morning before leaving she said that I should start wearing the panties she bought for me and shave all my hair. She would be back next Friday and turn me into a proper sissy for her needs. This immediately made me erect and she said, I see you do like being my sissy boy. Giving me a big French kiss she got into her car and left.

Sissy C.

“SM” Sissy Maker

 

 
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