My New Helper at My Cabin

My new helper at my cabin

I have a cabin back in the forest, miles off any paved road and a few miles down a gravel forest road. The road is on the other side of trees and my cabin in quite hidden from the road so it allows me plenty of privacy to spend the day as I like, which is either nude of cross dressed. One warm summer day I was at the cabin, it was too warm to be dressed so I was spending the day naked working on my storage shed. It needed a good cleaning and some organization, and I also wanted to build a new set of shelves. I had removed everything from the shed and started removing the old shelves, planning on how I could reuse some of the old wood while also using new plywood I had brought with me. I wanted the shelves to go along the back and both sides, still allowing me to get the tractor and gas grill in the center.

I framed out the supports for the back shelf and was cutting the plywood when I noticed someone standing behind me. I turned around and saw it was a young man in his early twenties, just standing there next to his bicycle with his mouth open as I was totally naked on the side of the shed with my circular saw in my hand cutting the wood on saw horses. Not sure what to say I asked him 'Can I help you with something", fully well knowing this was my land and he was trespassing. He kind of stuttered when he said 'I was wondering if I could fill up my water bottle', standing there with his empty bottle. I told him 'We will need to use the kitchen sink' and he followed me to the cabin as I told him "I hope you don't mind that I am naked, I wasn't excepting anyone to be here'. He told me "It's fine, are you always naked here when you are alone?' I told him 'Yes I am, I am a nudist and spend as much time naked as I can, the sunshine is good for your mind and body'.

As we filled his bottle and drank most of it before refilling it again we talked about what a nice day it was. I asked where he was from and headed to, he was from a town about 30 miles away and liked to mountain bike. This was his second time in this area and loved the scenery, usually biking until he found a nice place to eat lunch before heading back. We also talked about nudity, how long I had been a nudist, how I started and if I ever went to nudist resorts. I told him how I was a lifelong nudist, even as a kid I was always looking for places to get naked and that yes I have been to a few resorts and nude beaches. He asked 'What is it like to be naked with other naked people and how do you not, you know, get excited?' I told him after a while you do even think too much about being naked and that everyone else is naked.

He seemed rather intrigued by nudity and I asked if he had ever been naked with anyone and he told me no. I asked him 'Not even with a girlfriend?' and he told me no that he has had a hard time meeting girls. I asked him if he ever thought of nudity and being nude outside, 'Well I do like to swim nude when I get a change but it's always been by myself' he said. I asked him if that is part of why he bike rides, to find places to get naked and he admitted that yes it was part of it. I told him 'Not to find weird or anything but I would enjoy some nude company if you would like'. I could see he was thinking about it and finally said 'I don't know, this is all new to me. Are you sure it's safe? I don't want to be seen, what if someone comes?' I told him 'It's safe, you can hear cars coming down the road long before they get here so there is plenty of time to slip your shorts back on'. I could tell he wanted and told him he didn't have to but if he just wanted to hang out I was cool with that too, maybe he could help me with the shed. He agreed to hang out and help so we walked back to the shed.

I explained what I was doing and he helped me with the rear shelf as move moved the wood in and screwed it to the supports. It was a warm day in the upper 80's and much warmer in the shed, between no air movement and us two working at close quarters. He mentioned how warm it was and joked and told him 'It's not bad when you're naked' and he agreed I was right and took off his shirt. I joked again and said 'Don't stop there, you'll feel much better'. Without wasting another minute he slipped off his shorts, which to my surprise he wore no underwear. We are both standing there in the shed naked together, and he is starting to get hard which he said 'Sorry' and tries to cover with his hand. I told him he won't be much help if he's using his hand to cover himself and don't worry, it's a natural reaction as I also start getting hard looking at him.

He lowers his hands and we get to work removing the existing side shelf, him still with a raging hard on. We take the wood outside and I remove the nails and cut the boards to length for the new shelf. I can tell he is enjoying the outside air and being in the sun naked. As we work I ask him more about his lack of luck with girls and he explains he is just very shy around them and never knows what to say without sounding like a dork. He has gone on a few dates but they never amounted to more than that, a one-time date. I told him that things will work out when he finds the right girl and she will be very happy with him, but I'm not sure he knew what I meant. I was talking about sexually, he had a great body, slightly too slim and could use some muscle but he had a nice cock and a cute ass.

We finish one side shelf and start on the next one after walking to the cabin for a drink of water. Both of us are walking across the grass naked, him still hard and him holding his cock so it doesn't bounce as he walks. As we drink he asks more about the cabin and I show him around, first the kitchen which he has seen, then the living room with the loft, bathroom and finally the one bedroom. None of the rooms are huge but they are comfortable. As I open the bedroom closet he asks how often my wife comes with me and I explain she never does, this is not her idea of a good time so she stays home and how I am happy for my time here without her. He says 'Oh I thought since her clothes are in the closet she come often'. I explain 'Oh those aren't her clothes, they are mine. I wear them from time to time like when it's too cold to be naked or when I am just in that kind of mood'. He says 'Ok I'm sorry I thought they were women's clothes' and I tell him 'Yes they are'. I explain how I find men's clothing very boring and started wearing women's clothing when I was alone many years ago.

He asks if my wife knew and I told him no, she does not. He then asks if anyone knew I dressed like that and without going into too much detail I told him 'Yes a few people have seen me dressed as Amy' He asked who Amy was and I explained how when I dress up I am Amy. He asked what clothes I wore and I opened the closet and took out a few dresses along with skirts and blouses, then I opened the dresser and showed him the draws of panties, bras and stockings along with my heels and wigs. I could tell he didn't know what to say, I'm sure he has never had an encounter with a cross dresser. He asked how long I had been dressing like this and I told him how it started with wearing panties over 20 years ago and how it progressed to fully dressing when I had the opportunity to.

We finish out drink and walk back to the shed to finish up with the last shelf. I notice he has been quiet since we walked out and I ask him anything is wrong. He tells me 'No everything is fine but I have to admit this is a new experience for me, first being naked with another guy and you explaining how you dress up like a woman'. I told him I hope that didn't freak him out and he tells me 'No I actually find that all kind of exciting'. I ask him how so and he tells me he never met a cross dresser before but have seen some online and thought some really looked hot. I told him 'I'm not so sure I look hot but I do like to dress, the more feminine the better'. I am hoping he will ask to see me dressed and give him time but he doesn't ask. As we finish the shelf, I ask him 'Would you like to see what I look like dressed?' and he responds 'Would you do that for me?' I told him I would if he had an interest in seeing me and he said that yes he does.

We again walk back to the cabin together but this time we both have a hard on, just the thought of dressing can do that to me but dressing for someone has always been a turn on. I tell him to take a seat on the couch as I go into the bedroom to change. I start with a nice pair of black lace panties and a black bra with my silicone breast forms. I then slip on a pair of suntan thigh high stocking and sit to strap on my heels. I pick out my black and white striped mini skirt and a white blouse and put those on. I brush out my short light brown wig and slip that on my head along with a pair of earrings and a necklace. I look in the mirror and give myself a final look over before opening the door and walking out.

The bedroom open right into the living room and he sees me as soon as I open the door and walk over to him my heels clicking on the wood floor. I stand in front of him and ask how I look and he stutters 'Oh wow you um look great'. With that I sit next to him and as we talk I ask him how it feels to be naked while sitting next to a dressed woman. He tells me 'It's very exciting, almost too exciting'. I ask him if the girls he dated ever dressed like this and he tells me no, he has only had two dates and they wore jeans. We talked more about his dates as I sat there with my legs crossed and my heels dangling off my one foot. I ask him 'I hope you at least got to make out with the girls and he told me with one girl he did but just a quick goodnight kiss with the other girl. I joke and say 'So I'm guessing you didn't get a blowjob', he tells me no he didn't and actually never has, he is a virgin and that is not something he is proud of. I say 'Hmmm maybe that is something I could help you with, I man if you were interested'.

He is so naive he asks if I knew a girl that he could meet, for sex and I tell him 'Yes Amy'. I think it took a full minute for him to connect the name Amy with how I told him how when I dress I call myself Amy, but I knew the second it registered in his mind. He tried to speak but it all came out as 'Ah um, I, a, well um ah'. I told him to relax, it was an offer if he was interested and if he wasn't just forget I asked, all along hoping he accepts the offer. I could tell he was thinking about it, looking away and not saying anything, when he finally asked 'What would I do? I mean how will we do this?' I told him I would give him a blowjob but only if he was sure he would like me to. This poor boy has had a hard on for hours and I'm sure he was just aching for some relief, I'm also sure if would be over quickly, too quickly for me. He asks if I have done thing before and I admit to him I have but it's been awhile and how I am sure he wants to cum. He admits to me he wants to cum but never thought his first blowjob would be from a guy and I explain that my belief most guy's first experiences are with their friends as teenagers.

I think this makes him feel a little better about a guy sucking his cock and he says 'I guess I never realized that was so common and maybe it won't be so bad'. I told him he will love it and ask him if he wants to lie down or does he want to stay seated and I will be on knees in front of him, he chooses me on my knees. So I stand up and walk to the kitchen to get a drink so my mouth isn't as dry, trying to walk sexy and then get on my knees in front of him. I can tell he is he continues 'But what if I cum in your mouth?' and I tell him I was hoping he would unless he wanted to cum on my face. I didn't give him time to respond before I started by licking his cock up and down, starting at his balls and working my way up to his head. I can tell he won't last long and if I wanted any fun I better get to work. I take this head in my mouth and slide his cock down my throat until I get the entire length in my mouth. It took less than 30 seconds of sliding this hard young virgin cock in my mouth that I can feel him tense up and his cock start to pulsate. A huge flood of come fills my mouth as I clamp my lips on his pulsating cock swallowing, only a little escapes and I lick that up when I finally release his cock from my mouth. I finish with one last suck of his softening cock as he sits there breathless.

I ask him if it was all he thought it would be and he tells me 'It was all that and more'. I tell him I was glad I could help and get a towel for him to clean up and I get a drink for him and myself. He thanks me I tell him 'Anytime', which he responds by 'Do you mean it? Anytime I want a blowjob I can come over?' And I tell him yes, that maybe we can set something up and meet here a few times a month and do this again. We exchange phone numbers and I tell him I will let him when I am going to be here and maybe he will go on another bike ride that day. He loves that idea and gets up to leave looking for his shorts which I remind him are still at the shed. I tell him I will walk out there with him but first wanted to take these clothes off as it was too warm to wear them. He watches me sit down and take my heels off and then slip off the stockings, I then stand and take off my earrings and necklace along with my wig and set them on the couch. I pull the blouse over my head and pull down my skirt to remove it, now standing there in just bra and panties. I'm thinking how this poor boy has never seen a woman strip and stand there in bra and panties, watching a cross dressers is the closest he has come. I slip out the forms from my bra and remove it along with my panties which are wet with per cum.

We both walk to the shed where he gets dressed and hops on his bike to leave as we make plans to do this again in a week or so. Will it work out? I'm not sure but I am hoping it will as he heads down my driveway towards the road.