I turned my boyfriend into a sissy.


I have a story to tell you about, I will try to keep it short. I met this guy Keith on and add that I ran in a paper. He actually called me but I had another guy contact be before he did. I decided to meet the first guy and if it did not work out I could hook up with Keith the second caller. Well the first one did no work out at all so hesitant at first I went to meet Keith. He was all right but not the manly man I was hoping for. I stayed with him for a week but had to go down south for some business I had to settle.

Thinking I probably would not come back to Keith, I informed him of my problem I had to leave and get settled. Surprisingly to me he asked to accompany me on the trip. I decided I would take him along after all it was going to take a full week and it would be nice to have some company. During this week-long trip we discussed a lot of things including kinky things. Now I am into kinky things, at least I will try most anything once.

One of the things he informed me of was he likes sexy panties on a girl. I asked if he had ever tried on panties him self? With his hesitation I knew he had and sure enough it came out that he preferred wearing panties over male underwear. I asked him how long he had been wearing panties? He told me he started when he was twelve at home taking his sister. I asked if he ever had been caught in his panties? No,  he had not been caught but was sure that his mother knew when he lived at home.

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Once he fell asleep I decided it might be alright to stay with this guy and have a little fun. The next day I ran differed ideas through my head on how to sissify this guy. I acted cool around him but I was always thinking on what angle I wanted to play. I decided to buy him four pair of panties once we returned from out trip. He put them on once I demanded he do so since he acted as if he had never worn panties before. I stayed with him and had him dressing mostly as a girl when ever home. I would have him watch gay male sex videos with me as often as I could. This was to get him interested in having sex with men. I was determined to make him a cock sucking sissy. This was starting to work because after a couple of months of this I got him to eat his own cum.

I had not had any sex with him in the last seven month’s. I only made him jack off as I watched, that was all the sex he was allowed. He was falling right into the sissy trap I had planned. Next I subscribed to two magazines which I made him read.  One was “Boy to Girl weekly” the other was a once a month publishing called “Sissy Magazine”. I would make him tell me about the stories he read in the magazines. Now I had Keith dressing as a sissy and I would call him Kathy whenever he was dressed. I had him masturbating only to see him eat his on cum. He was watching male on male sex videos and reading sissy magazines. I felt the time had come to have him suck a cock. I planned carefully since I knew this was something he did not want to do.

I called an old friend Bill who was bi-sexual and told him about Keith and my plan to make him have his first bi-sexual experience. Bill and I kept in contact, between the two of us we came up with a plan. Bill was going to come over and seduce Keith into having sex with him. The day came and Bill showed up just as planned. I acted as if Bill was an old friend that I had not seen in several years. Keith knew nothing about Bill at all so the day had arrived. We sat around talking and having drinks when I invited Bill to stay and eat with us. He agreed but I had to run to town to get some items for the meal. During this time Bill was going to make sexual advances on Keith. I pointed out I would be gone for at least two hours.


When I came back I had no idea if anything had happened between them so I looked for signs from Bill. He nodded his head and winked at me so I knew something took place. While making the meal I told Keith to go change into Kathy. I was firm when he looked at me like I was crazy.  Keith go put on your sissy clothes so your dressed proper for supper. He turned a deep red as I proceeded to tell Bill that Keith had a cross dressing fetish and liked to dress as Kathy. I think it is time that Bill seen who you really are now go change into what I laid out for you. Keith left the room and I asked Bill what happened while I was gone. He told me he made advances on Keith but he rejected them all until Bill put his hand on Keith’s cock. Keith made no effort to remove Bills hand. Bill rubbed Keith’s cock until it started to grow then took it out with no resistance from Keith. Bill knew not to let Keith cum or it would be all over. About that time I returned from town and all the playing stopped. I went in to check on Kathy to make sure she was not waning on her cock. She told me she was embarrassed to go out dressed like a slut. I told Kathy she could come out as a slut or Bill could make her his whore?


Kathy came out behind me dressed as a slut in only lingerie and you could see her erection. I told her she looked very nice and sexy in front of Bill. Bill agreed also and told Kathy  how nice she looked, then went up to her and gave her a hug and kissed her on the lips. Kathy kissed back and I knew it was on. Once we ate and I had Kathy serve us a few more drinks Bill made advances on Kathy. I informed Kathy that tonight she could be the sissy slut she was or Bill could make her a real girl by having intercourse with her. Bill took of his cloths and then proceeded to play with Kathy. Kathy let Bill do what ever he wanted to do but when Bill sucked her cock I thought she was going to blow her load. Telling Bill this he stopped and before long Kathy had her first cock in her mouth. That night Kathy became a real cock slut by sucking all bills cum out of his balls and swallowed it.


Over the next month Bill visited Kathy every week and I ended up moved on, knowing I had made Keith into a cock sucking cum slut he was meant to be. They became lovers and I still keep in touch with them. Bill is feminizing Kathy more and more and they are going to move to a state that allows same-sex marriage. Yes, Kathy will be the bride.

My name is Laura, I continue to make sissies out of guys that I feel should be sissified.

“SM” Sissy Maker.


2 thoughts on “I turned my boyfriend into a sissy.

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