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First Time CDing
🕑 Added 2022-06-02 05:00:00 +0000 UTCSo, I am a closeted cross dresser. I have never had the nerves or really the chance to explore my fetish with someone. So one day I decided to just cruise the on-line ads. I saw an ad posted by a Fem Dom. As I read the ad, with all fetishes listed, I see "crossdressing". I thought why not, I'll reply. So I send an email explaining my fetish. I didn't really expect to get a reply, but I did.
After a few emails we had decided to set up an appointment. We had discussed that I would bring panties, stockings, a garter belt and a see through nightie top.
I show up at the agreed time, we met in the drive way and chatted for a minute. She then took me around the property to a small building. I guess you could say it was like a dungeon, but not the dark creepy kind of way. There was a bed, a small table and chair, a window with curtains. Quite comfortable actually.
She has me lay out the items that I had brought on the bed. She also had a few items. She sits in the chair and tells me "get completely naked. Pose for me and slowly turn around". So I'm all the way naked, she gets up and walks around me. She pulls the curtain from the window, "turn around slowly again". It was so exciting knowing that someone could possibly see me!
She has a long silk gown, she has me put it on. She also has a wig for me to wear. Along with a little make up and some nice red lipstick.
She has me get naked again. Leaving on the wig. She gets up and walks behind me as I stand there naked. She bends down, running her hands from my ankles to my neck. Not missing a single spot. Slowly running her finger along my ass crack, gently breezing by my cock and balls.
She then grabs me tight from behind, whispers in my ear, "your going to get fucked, and like it".
She sits back down in the chair, and instructs me to slowly and seductively get dressed for her. First the panties, black lace thongs. " I want you to lay them on the floor and step into them. Then bend all the way over and slowly pull them up. Now turn around, put your leg up here next to me and slide on those black stockings". As I was sliding on the stockings she was rubbing my legs and crotch area. Oh it was so nice. I then slid the garter belt up the same way as the panties. Next was the black see through nightie.
Now the outfit is complete, and the fun starts. She says "get on the bed, on all fours"! She smacks my ass, then gently rubs it. She continues to run her hands over my dressed body.
She then tells me "get on your knees. Take off my pants". As I pull the pants down, I see a nice hard strap on. She slapped my lips with the cock and slowly put it in my mouth. I was so excited now! She kept going back and fourth, put her hands on my blonde wig and pushed my head on the hard cock. I enjoyed taking that hard thing.
She then had me get back on the bed, ass up with my head in the pillows facing her. She grabbed some lube and starting massaging my ass, working her way to the center. She said "relax" as I felt something cold pushing against my ass.
She worked the toy in slowly, going deeper and deeper each time. It felt so good, the toy going in and out of my oiled ass.
She asked "are you ready"? With excitement of what would happen next as I nodded my head yes. She turned around and pulled out a bigger strap on! I was ready and didn't even know it. She gets behind me , my ass is still up in the air with my knees on the bed. She slapped that big hard strap on against my ass cheeks and slowly slid it over until it was directly on my hole. She spread my cheeks apart and slowly pushed the cock in. Apply a little more lube, she started going faster, deeper, faster, deeper. Before I knew it she had her hands on my hands on my hips and was pounding my ass! It suprisingly felt very good, being taken like that.
She said, "it's time to roll over baby, lay on your back and put your legs on my shoulders, pull your panties to the side and slide forward placing your ass right against my hard cock"! So I did, she slid it in again, this time going much slower, pulling the tip almost out and pushing it right back in. While she was teasing me, her hands were up and down my stockings, grabbing my ass cheeks and brushing over my exposed cock.
At this point I can't hold back, I said "I'm Cumming" in a small girlish whisper, and it went! That was the best orgasm I have ever had.
This story is true, oh so true and I hope everyone enjoyed. Please let me know
