Hitchhiking teen crossdresser PT 2
- 2 years ago
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Hitchhiking Teen Crossdresser free porn video
It was a 200 mile journey from the city to the outskirts of a small town by the countryside where I live, I have hitchhiked this road many a time but this day proves to be an exhilarating adventure into my first cross-dressing sexual encounter, I had my large backpack I carried with me with my belongings including in secret my lingerie, heels makeup etc. about 60 or so miles out a 4 wheel drive hauling a horse trailer pulled up alongside me, rolled down the passenger window a man who seemed to be in his middle 40's asked if I needed a ride, hell yes I answered it's mighty hot out and I appreciate it, no problem was his reply as I was loading in my pack he seemed to look me up and down as if he was sizing me up for something, weird I thought but nevertheless hoped on in, we drove off to the beat of some old time country music on the radio, as we traveled down the road sharing info on each others life I found out that this cowboy was single no k**s and lived alone on a ranch he owned on the countryside around a 100 miles or so from where I lived, I was at ease with this man so I let him know that I was 18 and traveling about enjoying my new found freedom he seemed to perk up to that bit of info as I could tell by the big grin on his face he said he understood, we traveled a bit further when he asked if I was bored and wanted to read some magazines for the long trip home, sure I said, there underneath the seat below you sweety he blurted out, confused with that remark I searched below and found a stack of porno mags, interesting I muttered aloud as he smiled they were gay, and shemale mags, YES!! I said to myself, knowing I didn't complain about the type of magazines they were, the cowboy seemed pleased, ya know when I saw you on the road I thought you were a girl at first he said apologetically, no prob I said I was always thin and girly growing up my mother said I should have been born a girl since my looks seem to go there instead of a boy I said, not sure f I should have said that out loud but he seemed pleased with it by saying don't worry you are who you are never forget that, thanks I said quite pleased with my new found freedom of expression, he asked if I enjoyed the magazines, sure I said good subjects to boot, really?? he said, why not was my reply'', much respect to the ladyboys enjoying themselves openly, yeah I thought so too was his reply, ya know we could stop by a private swimming hole nearby if ya want to cool off before we carry on, if ya like.... sure why not we soon trailed off the highway to a path not so traveled it seemed, about 5 or so miles off the highway, I wasn't nervous for anything tho most normally anyone would in such situations, not me besides I can always handle myself, anyway we soon arrived to a seclude pond, nice'' I said yeah I come here sometimes on trips back from the city during the hot summers to cool off a bit before heading home he said, coolio I thought ya know we can skinny dip if ya want no one comes out here it's private property, belongs to a fellow rancher buddy of mine, OK why not we both shed our clothes and dove in to the cold water I noticed he was hung like a horse with the balls of a bull, I was thin n girly but nevertheless I was comfortable in his presence, we swam a bit and I relaxed by the edge of the pond he got up and walked out by the truck to take a leak so I paid him no mind, awhile later he returned with what appeared to be my personal belongings, shocked that he found my sexy lingerie in my backpack I was prepared to tell him some fucked up lie but was not sure what to say, what are these for he asked?? was going to get you your clothes when I found these, damn I thought not sure what to say staring at each other before he broke the awkward silence when he point blank asked if I was a crossdresser, for whatever reasons that day I remember blurting outright that I was not knowing what he was going to say or do, he looked at my nakedness up and down smiled and said nothing wrong with that ya are who ya are, he shocked me a bit when he said why don't ya put these on bet they look sexy on ya, kinda stunned I started to put on the lingerie he brought me oblivious to the fact my soldier was saluting straight up into the sky, I noticed he was hard as well, damn I thought what the hell, why not been done caught with my pants down so to speak so I figured I might as well show him the real me, so I put on my sexy black garter belt lace hose lacy training bra black spiked stiletto heels and threw on a bit of eye liner and pink lipstick, no need for a wig as I have naturally long hair, I was nervous yet somewhat comfortable revealing myself to this studly naked and hung cowboy. Looking back on when I first started cross-dressing and reading gay/shemale mags I was always infatuated with wanting to suck big cock, ''hoping one day my dream to do so would come true'' well well what do we have here says the studly Marlboro man looking me up and down, seems we have a teen faggot slut flaunting here ways what shall we ever do about this situation?? being found out and horny as fuck by now I nervously strutted sexily in my stiletto's towards him wrapped my hand around his horse cock and started to slowly stroke him, very nice he says, come here baby-cakes he said grabbing my ass and kneading them roughly and started kissing my neck working his way down to my flat non blossomed young titties how long have you been wearing women's clothes he asked?? since the seventh grade I stated, well there is no need to hide anymore sweety you can be all the woman you want to be out here I won't judge you, no one will, damn you look just like a teen girl, you look amazingly natural and beautiful, have you ever sucked on a mans cock before he asked?? no but I have always dreamed to I replied, well today your dream has cum true baby he said as he knelt me down and guided his massive cock to my eager and willing mouth, I wrapped my slut mouth around his cock head and nursed on it lovingly, damn I thought to myself I'm sucking a mans cock I couldn't believe it! every emotion was running thru my body talk about being drunk with lust, damn near blew my load right then and there, looking up at my man I started to suck his cock with lust written all over my face, he stares back smiling running his manly fingers thru my hair, meanwhile I am massaging his massive nutsack with glee, he says in a husky voice I know we didn't fully introduce ourselves I'm Jim and you are? Rhonda I replied thru slurps on his cock Rhonda Lynn Fox (my porn name), well Rhonda Lynn Fox I want some of that boy pussy ya got down there, he stood me up and we walked back to the truck in each others arms stroking, kissing one another exploring each others bodies, I can't believe were doing this I said, this has been a dream of mine for so long, Me too Jim replied in a sexy husky voice'' I have always dreamt I would someday pick up a young sissy boy hitch hiking these roads looking for a man to explore their inner faggot tendencies, well today is that day Jim baby, we made our way to the end of the trailer where he bent me over and proceeded to rub his huge cock all over my ass before he began to slide into me, his cock head plopped in past my sphincter my slobber served as lube, and then I felt him slide further into my aching anus, slowly until he was balls deep into me, he held my hips lovingly and began to pump himself into me slow at first then he got a rhythm going I was in cock heaven, slowly reaching under I grabbed his nuts and started massaging them tugging them with love as my cowboy lover started dirty talking me down calling me his faggot whore a young teen whore, who was I to argue I was one and ta boot I luv role playing I tried to pull away telling him maybe we shouldn't be doing this out here his reply was shut your fucking slut whore mouth!! who do you think you are seducing me out here with you slut ways thinking you can just end this and walk away free, no sissy slut will ever treat me that way I won't allow it!! and with that he slid out of me with a plop! then proceeded to grab me by the hair and drag me around to the truck where he grabbed several ropes he threw over his shoulder and dragged me off to a nearby tree, there he threw the rope up over a large branch, this was after he gutted me and forced me onto my knees after rigging up the rope he began to tie me up by the wrists then began to hoist me up, strung up like a deer to be butchered, he then tied up each ankle spreading me out to the maximum after being strung up in such a way Jim worked his way around then underneath and slid back into me and picked up were he left off pumping into me pleasuring himself, after catching my breath I pleaded to Jim that it doesn't have to happen this way that I will promise to be a good sissy boy and respect his very manhood that I'll obey his every whim, to promise not to deny his intentions, with that he slowed down his pumping and asked what are you willing to do?? anything for my man I responded'' prove it, prove me your loyalty, at that moment he forced my head around as he started pumping into me again I can feel his breathing on my neck I then looked over kissed him open mouth tonguing my man passionately, our tongues lashing in and out of each others mouths lovingly with lust with passion with out right purpose, we stayed this position for quite some time fucking loving one another's tongue and cock until he slid out again to where he untied me from my punishment for trying to deny his advances, his pleasure, but once untied I proved my wanting him so bad we walked together to the pond in each others arms I enjoyed stroking my mans cock kissing tonguing each other when we reached the pond we walked in to knee deep where he forced me onto my knees and proceeded to take me doggy style I explode with ecstasy when his cock filled me up again, as we were pleasuring ourselves Jim asked if I wanted to be with him to be his faggot sissy boy girlfriend I didn't hesitate I want you to be my man I responded, good he said satisfied with my quick response then we will go back into the city and we can shop dresses heels and lingerie for you before we return home'' yes baby that's what we will do but for now let's fuck, Jim and I crawled back to the edge of the pond where I proceeded to mount him slid that massive cock back into me as my lover held my ass I rode my man bouncing up and down on his manliness going cock fucking crazy as I kept yelling at the top of my lungs I'M A WHORE, I'M A WHORE, I'M A WHORE!!! Jim seemed to be in his own ecstasy as well as he was yelling OHHH, OHHH MY FAGGOT WIFE!!! OHHH OHHH MY FAGGOT WIFE!!! damn I caught myself thinking through the lust and mindfucking where is this going to lead to??? damn my crossdressing ways!!!
Arisha
- 09.02.2023
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