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The first time crossdressed and strapon

The first Time
Croasdressed and Strapon

It has been 9 years since the first time being made in to a sissy for my then girlfriend. Her whole f****y was going away for the weekend so she said she want to stay home, here parents where ok with her stay home for the weekend and even told her to uave me over to keep her company when they where gone and enjoy the weekend together. Friday morning she came to pick me up telling me she had a very exciting weekend planed out for the two of us. So when we got to her house she took me to her room. After we got in there she said she wanted to watch some porn to set the mood for the weekend to come. So I liked the sound of that, little did I know that the porn she had picked out was guy on guy action. I could tell she was excited to get to watch it so I just sat with her watching it, but began to wonder how this was to set the mood for the weekend. After about 15 to 20mins of us watching it surprised I found myself get drawn into it and even getting abit aroused by it. She noticed me starting to get hard and smiled saying that is a good boy. I didnt know how to respond but blushed alittle bit. She then reached over to the corner of her bed and pulled out a bag from Victoria secrets, in the bag was a very sexy pink silk camisoles top with matching thong, excited i asked if she was going to go put it on for me hoping she was going to say yes, she looked at me and said no she was not but being gay porn had me hard she wanted me to put it on. I sat confussed for about a minute but then shook my head yes. She got off the bed and said have it on and be ready when i return as she walked out of the room. Still abit confused but not wanting to disappoint her, I took off my clothes and put on this sexy lingerie. Surprised at how good it felt and nicely it had fit me, I felt a bit of pleasure over take me as i waited for her to come back to the room. When she returned she was still fully dressed. She order me to stand up and slowly turn so she could see her sissy boy. I did as she had order me to do. She then said well now you are Kelly the rest of the weekend. She then said come kiss your daddy. Not know what she ment i paused she then laugh say me you silly little sissy. As we started kissing i could feel her exploring my body from over top of the lingerie, then she pulled me in close to her and threw her pants i felt a bulge that i was soon to find out was that of a 9inch strapon dildo. She then barked at me well it is not going to suck itself bitch. Before i could think i found myself down on my knees opening her pants to suck her strapon cock. She stood watching as i reached for it slowly. Then she leaned back some to push it out of her pants and near my lips. She then said start slow you want to make it last. She keep telling me more and more to lick it, kiss down it, stroke it, make it wet, being the porn was still on watched to see how the guy on it was sucking dick and started to copy it on the dildo in my mouth. Aftet a good 8mins she told me to bend over the bed again without question i got right up bending over the bed leaving my ass in the air for her. She gave it a smack and said wow slut you got in position fast. I felt her lube my ass up some as she pulled the thong off to the side. She said to just relax she was in control and want me to enjoy the ride. I then felt as she got in position behind me lineup her dildo with my ass slowly she started to push it in me slowly it went in to me first the head of it then feeling more and more going in deeper pausing every few seconds to let me relax to the new feeling of the big dildo going in to me. 3mins had passed before she had all 9inches in me and i could feel the balls of the dildo pressed up against my ass. I had let out a moan. As soon as I did she said oh so my sissy slut enjoys it i answered yes immediately. In the mirror i could see the now big smile on her face. As she started to more back and forth in and out faster and harder. The pleasure build more and more she went for 25mins on me. Then she said well what are you thinking about slut, i looked back and told her i want a real cock in me. She smiled and said in time you will when i think you are good and ready for it, but until then I am that for you. For 5years we would continue this when ever we could but then it all ended before we ever got to find someone to join. Few years went by try to find another woman that would of pickup where ahe had leftoff but it was not to be. After finding my now wife and tell her she respected it but said she could not do that but loving her so much i know that it was for the best i close that chapter of sexual fanesty.

Updated: October 21, 2016 — 1:30 pm

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