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Category: Gay Stories

Author: tiffany

I started crossdressing one night while partying it up with Blanche my best friend, she was married and never cheated on her husband. One night while high and bored she talked me into letting her dress me up like a woman. I never told her that after a year of doing this it had made me bi curious.
I had started dressing up without her here when i partied alone. One night late dressed up i went out for a drive north to san antonio tx and back home. I used to truck drive and as i passed a rest area remembered that often they had gay activities going on at them.
A week later i had got good stuf and high as hell i put on my strapless pink bra, matching panties, red garter belt and blk stockings, that had a run in them, with my blk and wht plaid pleated skirt, back zip, and my pink button up blouse with short puff sleeves. In mirror i could see my bra thru blouse. I then put on my brown bob cut wig with bangs and full makeup along with clip on long earrings and a necklace. I then painted my nails a metallic blue and slipped on my blk 4" heeled pumps. The run in my stockings bugged me and as i got higher i decide to drive the 60 miles north to san antonio to a x rated shop with lingerie to get new stockings. It was 10 pm when i left my place.
On way up i start to loose my nerve. I had a pair of sweats and zip up sweat jacket with a pair of blk flats to wear into the store, but no way to wipe off makeup and my nails couldnt be hid. I stop at north bound rest stop and hit pipe several times for nerve and head on up to store. The parking lot empty except 1 car, i hit pipe again my head spinning, i say fuck it and go in just covering up my top with jacket. The cashier gave me a weird look and said "hi" as i walked in, "hi" i say back heading to the back where the lingerie was. I find plus size stockings grabbing a tan pair and blk back seamed pair nervous i pay for them and leave.
I drive back south stopping at picnic area just south of town pulling to far end where it was darkest in front of a pavillion with a single picnic table under it, it was 1 am as i sat in my car changing into the tan stockings then slipping on my heels again. I decide to hit pipe then ill head on south to home. A couple of semi's drive thru rest stop and i notice that picnic table was barely lit up when they did. It was cloudy a bit cool out wind picking up some with lightening in distance, going to rain. Higher yet i thought of the thrill ide get being outside dressed like this with the wind blowing my skirt up so i put on my jacket grab my cigs and freak out as i got out walking the 30 feet to the picnic table under pavillion. I sit on top of table my heels on the bench with my knees together i sit and light up a cig. After about 10 mins i get nervous when a car tops hill then drives by me im sure his lights had me seeable.
The wind picks up so i stand walking about the pavillion enjoying the wind blowing my skirt up. It was gusting at times blowing it up enuf that if anyone was looking they could have seen my pink panties and red garter straps holding up my new tan stockings. Just as a semi tops the hill a gust blew up my skirt as lightening struck making it daylight. I push my skirt down and freak out as the semi parks behind my car turning out his lights just as it starts to rain.
I sit on back side of table in dark freaking out trying to figure out if i should run to my car when the driver from semi gets out. Once close i see he is about 6' 4" tall and weighs about 250 about 100 lbs heavier than me and even with heels on he would be 6" taller than me. He wore jeans, t-shirt, cowboy boots and a cowboy hat a mid 20s white guy.
I figured i was going to get my ass beat. About 10 ft from me the lightening struck so he could see i wasnt a woman. " wow what a rain" he says walking past me to far corner " i was about to piss in my jeans" he says i glance over to see him pulling out his cock as lightening struck. I turn away. " so what brings u out tonight?" He asks zipping up now standing by me i get out a cig, "uhmm i uh just wanted to know how it felt to be outside" i honestly tell him. I drop my lighter and he grabs it. "You'll have to stand up to light it" he says, i stand and he lights it for me "thanks" i blush it rains harder.
"If you dont mind im gonna wait here with you till it lets up" he says and sits up on end of table. "I dont own this place so do as you please sir" i say "thanks sissy could i have one of those smokes?" He asks he had already given my lighter back it and cigs in my jacket pocket i wore half zipped up. "Yes of course" i say and turn moving in front of him getting out pack i hand to him he gets one out and in mouth i step closer lighting lighter for him, he makes me step closer between his spread legs to light it. As he draws from it i feel his hands slide around my waist. "Oh wow" i blurt out "uhmm you not into this sis?" He asks "i uhmm i dont know ive never been with a man before" i say looking down. He takes a hand from my waist and a finger to my chin he pushes my head up then takes his cowboy hat and puts on my head as he leans down pressing his lips to mine. I freak out at first then start kissing him back his arms ga around my waist as mine go around his neck. The wing gusts about then and his hands then go onto my pantied ass grabbing it pulling me closer to him between his legs. "Go on sissy undo my jeans you know u want to" he says rubbing my rear thru my pink panties. I look down as lightening strikes and undo and unzip his jeans. One hand on my rear he uses other to unzip my jacket and i take it off. The wind picks up blowing the rain to us getting us wet as i reach in his jeans pulling out his fat hard 9" cock. Looking down just as lightening strikes, "wow" i say as i hold it with one hand and lean down to it sucking its fat head thru my lips. My skirt blowing in wind has both his hands under it on my pantied ass. "Wow sis u r a good cocksucker" he says "but that aint all i want" he then unzips my skirt in back pushing it over my rear to ground as i suck his big cock.
He then stands me up and we kiss as he unbuttons my blouse and we get it off me. So, now i stood outside in a rest stop wearing only my lingerie heels and a cowboy hat. He then stands up and turns us so im facing end of table him behind me we are both soaking wet as he leans me over table standing in my heels legs spread him behind me he lowers my wet panties in back steps up between my legs and pushes his hard cock all 9 fat hard inches deep into my ass. "Oh fuck yes mmmm yes mmm god yes fuck me" i cry out wiggling my ass against him as he slowly starts easing his hard cock in and out of me. "Mmm yes sis u got one tight ass girl" he says fucking me now slowly. "Mmm god yes yes ur hard cock is so deep in me so hard yes fuck me like a little whore!" I cry out, he now slams in and out of me as i push back to meet him"oh god yes please cum in me please same time as i do please" i say to him "ok sissy i will" he says"oh yes mmm yes fuck me harder please yes oh god please cum with me now!" I scream and he slams in me his cock jerking hard deep inside me as i cum in my panties wiggling my ass against him. He snorts and humps as he fills my ass full of his cum untill done, then pulls out zips up and before i can stand up he fires up his semi and takes off. I stand still wearing his hat and put on my skirt and jacket grab my blouse and in the rain i go get in my car not believing what ide done. I hit pipe feeling his cum run out of me before i head south to home.