So here's my fantasy of meeting a crossdresser for the first time...
I arrive at her front door and ring the bell. I'm pumped up with adrenaline as I've never done anything like this before. I've never been with a guy before, let along a crossdresser! It seems to take a lifetime before I hear the door unlock. It opens to reveal a slutty MILF. Black wig, black semi see-through blouse, short black leather skirt, stockings, suspenders and high heels! An amazing sight! She leads me in, and we're both immediately drawn to each other. We've been chatting online for sometime and had discussed each others fantasies, so what was about to happen was already almost scripted to perfection. We just had to make it a reality! She pulls me towards her and our hands are all over each other. I start feeling her nylon covered legs and she's squeezing my crotch. I'm working my hands up her legs and inner thighs to discover what's in her knickers.
So we're still in the hallway at this stage groping each others crotches. We move into the lounge and I take a seat on the sofa. She offers me a drink and disappears into the kitchen looking really slutty. High heels, stockings, tight skirt, tight top. 5 mins later she returns with my drink and sits next to me on the sofa. We turn to each other and place our hands on each others legs. I begin stroking her legs from her ankles up to her crotch. Each time getting closer and closer to her bulging knickers. She is undoing my flies and fighting to get my growing cock out of my jeans. She goes down on my cock, pulling back my foreskin. After a few minutes of teasing, I turn my attention to her. I pull up skirt to reveal her black thong holding in her bulging cock. I pull the thong to one side to release her cock and go down on her. She lifts up one stocking clad leg and places it over my shoulder giving me better access to her cock and ass. As I'm slowly sucking on her cock my teasing the entrance to her ass with my middle finger through her thong fabric. She's grinding on my finger beggin for it to go deeper into her ass....
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I remove my jeans and position myself with my head between her legs. Her legs are wrapped about my neck and she's still wearing those high heels. I move her thong away from her ass and slowly insert my finger. It goes in slowly and tightly without and lube up to my knuckle. She shudders from the pleasure!
Its time to slow down or the action will be over to quickly! We pull ourselves away from each other and she leads me upstairs. I'm walking behing her, her skirt is still pulled up revealing her cute ass and thong as we head up the stairs. We go into the main bedroom and fall onto the bed. She's laying face down and i'm lying beside her. I'm stroking her inner thighs and teasing her ass hole. I remove my shirt and roll her onto her back. I kneel over her head in 69 position, and lower my cock over her face and I go down on her. She plays with my balls with her tongue and teases my ass hole. I'm sucking on her cock and pulling her bum cheeks apart to get a better view of her little hole I want to fuck.
After a few minuted pleasuring each other in this position we roll over. This time I'm laying down and she's on top; This gives me a better view of her shaved ass. As i lick and suck her cock, I once again finger that tight little ass hole. I manage my middle finger in below the knuckle and then try for a second finger. Its tight and she's groaning from the pleasure everytime I go deeper.
I pull my cock away from her hungry mouth and grab the condoms. She helps roll one onto my stiff cock and she positions herself at the edge of the bed on all fours. I stand up and position myself behind her. I take the tube of lube and squirt a generous amount on her hole. With the end of my dick I rub the lub in and hold my cock pushing at the entrance to her ass. After a few seconds of resistance her muscles relax and my cock slides in with her letting out some groans of pleasure. My cock is fully inside her slutty ass. She's fully dressed, heels; stockings, thong pulled to one side, skirt rolled up, blouse partly undone. We take it slowly as its her first time at receiving a cock. We grind and pound each other trying to release our sexual frustrations. She lowers herself onto the bed so I'm laying on top and slowly fucking her ass until I come inside her. We're both sweating and exhausted from doing this for the first time. After a few seconds to catch our breath I pull my cock out of her butt. She rolls over and slips the condom off me and licks my co clean! What a slut!
I grab her cock thats still hard and slowly begin to masturbate her. It looks like its going to be my turn soon to get fucked! She grabs a condom and slips it on. I'm laying on my back with my legs wide open. She positions herself between my legs and grabs a pillow that we sliip under my ass to get better positioned. She takes the lube and massages some into my virgin hole. She takes a butt plug and slides it into my ass. It goes in easily without any resistance. She pulls it out slowly and then re-inserts it to make my ass ready. After a few minutes of this, its time. She pulls out the butt plug and positions herself closer, her cock hovering over my virgin hole. She pushes her cock into my ass, it resists at first but after a few seconds to relax my ass accepts a few inches of her cock. She waits, allowing me to get comfortable and then pushes further until I'm impaled on her cock completely. What a feeling! My cock begins to get hard again. She slowly pounds my ass with my cock in her hand. Stroking my cock with every pounding motion. After a few minutes she releases her load into me and she continues masturbating me until I come over my stomach. She removes her cock and she collapses from exhaustion onto the bed next to me. We lay panting from exhaustion.