My First Crossdressing Meetup

My first meetup was in some woodland near my home. I'd got chatting with another crossdresser online. Eventually, talk of meeting up happened and we agreed to meet that evening in a location that we both knew.

The excitement was building as I put my outfit on. As I fastened the basque, I couldn't believe that this was going to happen. What if I got caught? I pushed down the feelings as I pulled up my stockings. What if the other person was crazy? I pulled my calf-length boots on. Will I be able to drive in these? What if I have an accident? No time to think of that now, I need to go out for my meetup. What if I get stopped by the police? I'll wear regular clothes over the top, so no-one will know as long as I don't end up crashing my car.

This is so exciting. I am literally shaking, thinking of what might happen. I've never met another crossdresser before. I've never touched another cock. Will I be able to do it? Before long, I'm pulling into the dark, secluded car park for the woods. Another car pulls in. I can see that it's the person that I've been chatting with. He's wearing a wig, women's glasses and the full outfit! Now I have to go through with this!

He gets out of the car and moves carefully to the woods. He's wearing high heels, so his footsteps are cautious, deliberate. I quickly pull my guy clothes off and I'm just wearing my slutty outfit. Basque, stockings, lacy panties, leather-look vinyl miniskirt, short jacket, all in black. I pull my shoulder length wig and shiny black boots on. I’ve seen myself in the mirror wearing this outfit before, but never worn it outside the house. Now I'm wearing it and ready to have my first ever bi crossdressing encounter.

I lock the car and hobble slowly to the woods on my high heeled boots. These things are so impractical, but I love wearing them! Through the gate. Oh God, it's so dark but my eyes are getting used to the dim moonlight. I can see him. He's about the same height as me and he looks slim and sexy as fuck. His outfit is similar to mine. His wig is a different style, but he’s wearing a silky blouse, longer fabric skirt, stockings, and a trenchcoat. He is wearing high heeled shoes. He even has a pair of women’s glasses, earrings and makeup. He’s definitely more experienced at this than me.

I greet him and we kiss. I feel his hands pulling my miniskirt up and his fingers quickly find my cock. I can tell that it is so swollen and standing for inspection. My body is shaking, I don't know if it's cold or if it's the adrenaline causing the shaking. I touch his cock through his lacy panties, pull the skin back and feel the heat of the tip. It feels so smooth, firm but soft at the same time, not like all those dildoes that I've played with and fantasized about having inside me.

He sighs and drops to his knees. He's got his hands on the back of my thighs, now one hand on my cock and balls, urgently pulling my panties to one side. He takes my cock in his mouth. It slides in between his lips so easily. He makes a low sound from his throat and I can feel it vibrating my cock. It's so hot in there. I can feel the lipsticked mouth sealing around my cock, his powerful suction compelling me to come inside. He caresses my ass and I can feel his fingers brushing my asshole, not going inside but just touching the hole, perhaps hoping for it to open a little, maybe checking if I'm willing to let him try his luck.

I can't handle it anymore and I start to come. He pulls my cock out of his mouth and I come over his face, down the front of his dress and on the floor. He says that he's enjoyed making me come.

I want to do something for him now, but what? I ask him what he wants to do. I'm atill shaking, partly from the cold and partly from the excitement. He asks me to fuck his ass. I can't, I've just come and I'll not be ready for that for a while. I ask if he'd like to fuck me instead. He eagerly agrees and I turn around to face away from him. I bend over and I can feel his hot cock being pressed urgently against my willing hole.

In a few moments he's opened me up and he's inside. I can feel his hands on my hips, one hand moving skillfully over my outfit as my first cock fills me from behind. I've only had dildoes in there until now. This is so different. It's wonderfully smooth but so firm.

He's really pumping me now, telling me how good my asshole feels, how he's going to shoot his come soon. I'm shaking, I'm ready to have that hot come sprayed inside me.

He starts to groan. I want the come inside me so much. He pulls out and comes over my ass. So disappointing! He rubs his come over my pale white ass, making me feel like the whore that I am. I re-arrange my panties and skirt to cover myself up.

Fuck me, that was so good, but I wanted him to come inside me, to feel that firm cock pulsing inside and the hot gush of come flooding me. Maybe next time!

Without many words, we make our way back to our cars. I pull my wig and boots off and my guy clothes on over my slutty outfit. Before long I get home, but what a fabulous memory to remember!