New Adventures

** This is about a recent experience where I got the courage to do something I've thought about many times **

*Background* Even though I've been crossdressing most of my life, I'm basically still 'in the closet' with my dressing. Living alone, I can dress at home as much as I like, but I've never been able to apply makeup without looking like a toddler gave me a makeover so I don't go out fully dressed. I have gone out wearing female clothes under my normal male clothes and have dressed in private for a few men I've met.

OK, on to my new adventure...

I got an email from a guy I had met up a few times with that I met on a popular hook-up site. He wanted to get together again and have some fun. Being that I love sucking cock while I'm dressed like a cute, slutty girl, I replied and said I'd meet him at a near-by park at 9:30pm and we could come back to my place. I took a shower, shaved everything below my waist, and got dressed. I put on sheer black thigh high stay up stockings, red satin panties with a matching bra filled out with my 36 C breast forms, a black pencil mini skirt and a white satin baby-doll top. I put my blue jeans, a pair of black Nike sneakers, and my cammo jacket on over top and head out the door at 8:30. It doesn't take me long to get to the park, but I want to smoke a little before he got there to relax my nerves. He arrives right on time and I hop into his pickup. It's just getting dark, so I say instead of heading to my apt let's go for a drive.

We drive for a while till we're away from the downtown area and on some of the back roads, all the while with my hand rubbing his cock through his pants. I'm getting hornier with each stroke I give his thick cock, and I think to myself it's now or never, so I undo my belt, slide my jeans to my ankles and take off my jacket. He lets out a low moan and I go back to stroking him and myself. He reaches down with one hand and undoes his belt and unzips his pants. I reach in and free his bulging cock and feel the warmth in my hand. He then reaches over and strokes me through my panties, making me twitch and leak some pre-cum in them. I duck under his arm and put my face in his lap. I start licking along the head and over the slit tasting his pre-cum as I do. I want his cock down my throat soooo bad now. I lick my lips and plunge my mouth down on his cock as far as I can and hold it there a few seconds before I begin slowly bobbing up and down the whole length of his 8 inches. As I'm enjoying this, we hit some bumpy areas and the way my head bounces around it feels like I'm being face fucked, which makes me even harder.

He's stroking me through my panties and my face is bouncing on his cock when he tells me he needs to pull over so he can suck me for a bit. I sit up and notice we're on a one lane road with no streetlights and nothing but trees on both sides. He leans over, takes me into his mouth, and starts deepthroating my 7 inches. His mouth feels so warm and soft, and he soon has me bucking my hips in synch with the finger he's plunging in and out of my ass. Soon he has three fingers fucking my ass while he's sucking my 7 inch clit. I can't hold it in any longer and shot my load into his mouth. Oh my God did I want his cock back down my throat, so I get him to sit up and I bend over on the seat with my ass in the air and bury my face in his lap again.

As I'm sucking on his sweet cock he reaches over me and starts finger fucking my ass again, I'm in heaven! I take a short breather to tell him I want him to cum all over my face and then I want him to fuck my with that nice cock and fill my ass with cum too. I go back to sucking as much of him as I can and he reaches down and slides his pants down further so I can have better access to his whole cock. He's working his fingers in and out of my ass deeper and deeper the more I suck and slurp on his hard cock. After about ten minutes of blissfully taking him in my mouth, he pulls out and holds my face down sideways and jerks off till he shoots six large, hot ropes of cum across my face and in my waiting mouth. I gobble up what's in my mouth and take his cock down my throat again to clean the remaining cum off it while leaving the rest on my face.

I keep sucking till he gets hard again and, to my dismay, he pulls up his pants. I look at him pleading and he smiles and says don't worry, we're not done. He then gets out of the truck and walks around to my door. He opens it and I know I must look like a slut as I step out with cum on my face, my skirt hiked up with my panties showing and my jeans still around my ankles. He turns me around and bends me over into the seat and starts massaging my cheeks till he has me wiggling my ass back and forth aching for him to fill my ass. He steps in closer and rubs his cock between my cheeks, spreading the saliva from it over my waiting hole.

Of course it was already pretty well lubed and loosened by his fingers, so his cockhead slipped in rather easily and he started to slowly plunge more and more in to me till I felt his groin resting against my ass. All 8 inches were buried in my tight ass and I felt every throb as he moved slowly in and out of me. I started thrusting my own hips back in time with his and soon he was withdrawing almost all the way and then plunging back in to the hilt. I just love being fucked slow and deep like that.

After going at it like that for ten minutes, he pulls out and turns me around to face him. He tells me to sit on the edge of the seat with my legs out the door. When I do, he lifts my legs and pushes his cock back into my open ass. He fucks me this way while I stroke my clit in time with his pounding. After a few more minutes, I cum for the second time, spraying my load all over my self and as I do he groans and thrusts one more time deep into me and I feel his cock throb and pulse as he unloads another large load filling my hungry ass. I scoop up as much of my cum as I can and lick it off my hands as he pulls out of me and pull up his pants.

When he dropped me off near my apt it was after midnight and I had dried cum on my face and on my baby-doll top with cum leaking from my well used ass as I walked home. Now that I've had a taste of how exciting car fun can be, I'll definitely being enjoying it more!