I have been dressing in women’sclothes since I was little. My grandmother used to dress me up in her old dresses and pretend I was her granddaughter. As I grew older it started becoming more of a sexual fascination and turn on for me. I have been more a closet cross dresser getting clothes here and there and then dressing up and having incredible masturbation sessions looking at tranny porn. Only in the recent couple of years I have discovered about sissy maids and bondage and bdsm and how it pertains to cross dressing. I had a girlfriend once that dressed me up for Halloween and she was really the first person that had ever seen me en femme. My most recent ex girlfriend had shown an interest in bondage and being tied up. One night we were making love and she wanted to be tied up, so I was more than happy to oblige. While I was doing the knots I was growing extremely hard and her in her g-string and cute little ass with perky little b cup tits was enough to push me over the edge.
But being calm, cool, and collected, I was able to keep myself at bay until we climaxed together. I asked her later how deep her kinky side was. She told me that she had always fantasized about being completely dominated and how she always wanted to try anal. She then turned to me and then asked me if I ever had a fantasy that I wanted to play out. I told her no at that point and that I wanted to have a very wild, erotic, kinky night with her. After that I went online and did some shopping. I bought a couple of cute dresses, a few pairs of six inch fuck me heels, stockings, bras, corsets, garters, panties, and a couple of wigs. I called her up after I made my purchases and told her that we would get together at a hotel room for the night. We usually hung out at my place or hers but I wanted that night to be special, like a little trip away. I booked a hotel room for the following week so that my items would have time to be shipped and arrive at my place. That night we got to the hotel room and I had a bag with my new clothes in it and she had a bag of her own. I told her to get ready first, she went into the bathroom and about ten minutes later she came out and my breath was taken away by the sight of her. She is a petite little blonde standing at 5’4” and about 115 lbs. She has cute perky little tits with a tight little butt with shoulder length blonde hair.
All she was wearing was a black garter belt attached to black sheer stockings and 8 inch platform stiletto heels. She came over and sat on the bed and I put her hands behind her back and I tied them together using rope and put a ball gag in her mouth. After I had done that I had gotten on my knees and played with her clit to get her nice and wet. About 5 minutes of flicking her little knob with my tongue, she had an amazing orgasm. After that she was lubed up enough that I put a 9 inch vibrating dildo into her and turned it up half way and I told her that I would be right back. I went into the bathroom and put on a black garter belt attached to thigh high stockings and I also put on a pair of 6 inch pumps. I then slid up a pair of satin ruffle panties so that they could easily be removed later. I then put on a black corset that had red lace boning up the back. On top of that I put on a black halter style dress that had a choker part that went around my neck, I then finished it off with a pink wig that I had found online that was more for a sailor moon cosplay costume but it looked cute to me so I got it for this outfit. I emerged from the bathroom and her eyes just lit up. If she didn’t have that gag in her mouth, she would have been speechless anyway. Walking over to her, I tried to act as sultry and as sexy as I could. She just kept staring at me while I walked over to her and put my hands on the inside of her thighs and started rubbing her, by this time she was already worked up again with the dildo still vibrating inside of her. At this point I pulled out the dildo and set it to the side and I inserted 2 fingers inside of her dripping wet pussy.
As I was fingering her I had my tongue on her nipple sucking ever so gently so that way she would squirm around. I stopped sucking I loosened her gag so that she could speak, she looked me in the eyes and asked me how long I had been dressing this way, I told her about the past and I asked her if she was freaked out by it, she said that I should have told her sooner because she wanted to put me in panties before this, I just smiled and put the gag back in her mouth. After I had put the gag in her mouth I went back down on her for a little bit more. After licking that sweet little cunt I flipped her over so that way she was face down on the bed and her legs hanging off the edge. I took her juices from her soaking hole and started rubbing them into her arse. God, she was tight, hehe. I put one finger in and she started to squirm a little bit and I worked it in and out. Then another finger, and another until I had 3 fingers in total in her tight little butt. By this time she was moaning in pleasure. She kept moving her hips back and forth riding my fingers that were in her tight hole. At this point I grabbed the vibrator and I spit on it and slid it in. It was such a sight to see her with that thick, long, cock inside of her while she was helpless tied up and gagged, I just sat there staring at her while my own cock started to come out of my panties.
I have a nice thick cock at 8 inches long that I love to have in panties, but at this point I took them off. While she still had the dildo inside of her I flipped her onto her back and slid my cock in her juicy pussy. Her eyes lit up from the feeling of having both of her holes stuffed with big cocks. I screwed the living crap out of her until I filled her with my sticky cream. Then I got down on my knees and sucked every drop of my cum out of her cunt and swallowed it. As soon as I got done sucking she had an amazing orgasm. I pulled out the dildo and sat her up and pulled out the gag. She told me that it was an amazing evening and that she wanted to do it again soon. And to my amazement, she also said that she wanted to invite another girl into our playtime so she can have her first lesbian experience. We hugged and kissed, then we put our panties back on and went to bed.
Hopefully there will be more form me…
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