Railed In A Sundress

This is a recurring fantasy I have had over the years that I've put to the back of my mind forever as I haven't 'allowed' myself to speak, accept it makes me hot, or write it til now :-)

I've booked a solo retreat in the countryside, somewhere I feel like I will be able to have some real privacy and take all my new dresses, underwear and accessories for a weekend of dressing up and starting to really explore my repressed girly side.

I'm completely hairless/waxed and feel so free in my nice, new smooth skin, as soon as I arrive I have to strip off and cover myself in a moisturising oil, luxuriating in the feel of it

I've always had larger breasts for someone born male, and they look so lovely in the mirror as I slide my hands all over them and really appreciate them for the first time in my life, and imagine other hands enjoying them as I do now. I don't even need implants as they are the perfect size already that I would have wanted.

Once I'm nice and oiled up all over I hit the back deck of the farmhouse, looking right down into a deep forest ravine, nobody for miles and miles. I rub my hands all over myself again, enjoying the sensation of the warm sun on my oily body and just being naked outdoors.

After a nice lie in the sun. I want to go put on something pretty. Going through my things I find the perfect little cotton sundress with a lovely yellow flower print on it. I love the way it feels as it slips over my head, cups against my breast and flows around my legs.

I don't bother with underwear, and the sensation of the dress rubbing against me is incredibly sensual.

I decide to go for a little walk down to the stream at the bottom of the hill as it's a hot day and a little dip might be nice. I'm so loving the feeling of the dress swishing around my bare legs and brushing against my cock, thighs and ass. I've taken the oil with me as I thought it might be nice to put some more on down at the stream while I have a sunbake.

Once I get to the creek I notice there's actually somebody fishing down there, about 50 meters away from where I am. I get suddenly nervous, wandering around as a man who feels like a woman isn't known to be the safest activity one can do in the country.

He waves, friendly like, and I feel a little relived, although he probably thinks I'm a female from a distance, even with my shorter hair.

I sit down with my freshly painted toenails in the water. The icy cold stream feels super refreshing. I look up and see the fisherman is coming towards me.

I brace myself for an unpleasant scene, but as he comes closer, I can see it's a younger guy, maybe 20's, and he is still smiling as he comes up to me, even though it's obvious by now I wasn't born female.

'Hey, sorry, I'm the owners son and I caretake here on the property- sorry not meaning to intrude- i live in the main shed up at the gate where you drove in and I'm just down here trying to catch some dinner'

'No worries at all' I say, 'I'm Claire, nice to meet you'

'Jamie' he says as he reaches out to gently shake my hand, holding just a little bit longer that he needed too. I start to feel little quivers inside, something is going on here, I'm just not sure what yet.

We make a little general chit chat, and I notice his eyes keep flitting to my thighs and my cleavage. I'm getting turned on by the idea he might be turned on. He hasn't raised anything yet regarding my gender so I'm feeling pretty relaxed.

'Look' he says out of the blue, "I know I'm not supposed to say this but you look really good in that dress, like super good...."

I leave a moment of silence to let this sink in. 'Well thank you, its nice to have someone notice and feel that way, because I like me very much in this dress too"

"I know this is a bit forward, but, do you think you might...I dunno...wanna fool around a little or something" he asks sheepishly. ' I've never been with someone like you before, and I'm not sure why, but I'm more turned on right now than I've ever been in my life right now".

I'm shaking a little, and I feel a twinge in my crotch as I get excited about being a turn on for Jamie. "Well, sure, maybe, what would you like to do, Jamie?" I ask suggestively.

"First I'd love to have a look at your boobs. Are they real? They look perfect". My nipples get instantly hard, and I say 'well since you asked so nicely', and slip the shoulders of the dress down my front, revealing my delightful little boobs, all oiled up.

Jamie can't help himself, he comes over and takes them both in his hands, leans down and starts sucking on my nipples, one after the other. My head is exploding with pleasure and sensation and the feeling of being desired.

He reaches down with one hand and starts grabbing my ass, getting so turned on I can feel him getting hard as his crotch brushes against me.

I gently pull back, sit down on the rock I had been on and start to undo his fly. The most glorious, rock hard dick pops out and slaps me in the face. I push his pants all the way down and get to work.

I start slowly licking, sucking, pulling on his balls as he groans and moans with each stroke. I've been practising my deepthroating on a dildo at home, so manage to get it all in, balls deep in my throat as he gasps at the feeling.

Jamie pulls out of my mouth to stop himself from cumming yet. ''Oh my good, you're too good' he says.

I'm feeling so turned on right now. I've never done anything like this with a guy before, only thought about it so this is almost taking my breath away.

'Jamie, I've never done this before either, but, if you want it, and i can take it, i want you to have my virgin asshole, right here, right now'

Jamie's eyes bulge 'absolutely, you don't have to ask me twice'

I grab the oil off my towel and start oiling up his beautiful hard dick, throbbing in my hands. I then give him the oil, turn around, hitch up my skirt and spread my ass cheeks. "Finger some into me"

Jamie proceeds to gently start fingering my ass and pushing the oil up inside til its incredibly slippery in there. I feel his dick slapping against the back of my thighs as he does this.

Suddenly, the moment is here, I feel the head of Jamie's dick pressing impatiently against my tight asshole. I try the breathing trick i use to get the dildo in sometimes, and it starts to work.

I gasp, and almost come immediately from the feeling of the bulk of his dick just suddenly popping right into my ass. He just holds it there for a minute, enjoying the sensation of my ass gripping his dick so tightly, as he reaches around a cups my breasts.

This is the most incredible thing I have ever felt, Jamie's dick just sitting there, throbbing hard and hot in my ass as he pinches my nipples and rubs my oily tits, with the sundress peeled down round my waist this feels indescribably erotic.

Slowly, Jamie starts to make little movements, and as my ass becomes more accustomed to this new sensation, I start groaning as I begin to start pushing back against his cock, trying to get it in deeper.

The feel of that huge greasy dick parting my ass cheeks and filling my hole is sending me wild. Its almost taking my breath away. I feel Jamie increasing his rhythm, pumping my ass back onto him with each stroke, really fucking me nice, rhythmically and slow.

Jamie slams into me from behind, gripping my boobs tightly and moans deeply, as I feel his cock pulsing and pumping a massive load of hot cum deep in my ass for the first time, and I come with him having the most unique orgasm I have ever had, feeling my cum dripping down my thigh as he holds me in position impaled upon his cock.

I feel another beautiful, new sensation as Jamie lets his dick slip out of my cum-filled asshole and I feel that head pop out of my ass, and the cum starts to leak all down my cheeks and back of my thighs. I'm in heaven.

"Thank you Jamie' I say a little breathlessly. I tease him a little by laying back on the towel, hitching up my dress and letting him watch his cum dripping out of my ass.

'No, thank YOU' says Jamie. 'That was the horniest things I've ever done in my life, no joking'

"I've never actually done that before, with anyone, just so you know, I'm very grateful you wanted to be my first time' I say, enjoying the sensation of warm cum still dripping down my ass cheeks and the back of my thighs.

"So....you're staying 3 nights right...?' Jamie leaves the question hanging. "just in case you need anything while you're here, my number is on the fridge for the front gate shed---anything you need, day or night..."

He smiles knowingly and then says 'now if you'll excuse me, I better get back to trying to catch tonight's dinner" and he smiles and turns back upstream with his fishing gear.

I lay back in the sun, my dress peeled down, oily boobs in the sun, a finger reaching down and feeling the cum still leaking out of my ass and feel so completely satisfied.

I'm already thinking of an excuse to give Jamie a call later on tonight and see what happens, but for now, I'm just thrilled to have been randomly railed in a sundress in the middle of nowhere...