The Nudist and The Sissy

The characters in this story are all over 18 years old.

...

Living alone can be kind of scary. Not just because someone could break in and you would be totally alone, but also because of the bills you would have to pay all by yourself. Now that David was gone, I had to look for someone to take his place.

The house that I live in is a rather small, one story, two bedroom home that my grandparents owned. They passed away when I was still young, and on my 16th birthday, my parents gave me the keys. I couldn't believe it. My own house! It was near the outskirts of the city, and I asked my best friend, David, if he wanted to come and live with me as roommates. He instantly agreed and together, we turned this little, old fashioned house into the ultimate geek paradise.

We were both outsiders growing up. We were the quiet kids that got bullied a lot at school. Neither of us ever had a girlfriend, and we went through life hiding our true, geeky selves from the rest of the world.

Those first few months were kind of rough but pretty amazing. Living off junk food and soda. I'm a pretty skinny guy, and I'm pretty sure most of the weight I gained went to my hips. We stayed up all night gaming, and we put our nerdy figures, statues, and posters all over the place. But of course, we needed cash to pay for everything. I had a part time job working in a small grocery store, and David worked part time in the mail room of an office that his father worked at.

Things were going great, until two years later, which is where we are today. I'm 18, and David has moved out. He got a promotion a few months back and was given a small apartment of his own, closer to where he works. After helping him pack his things and move, I was left alone in my little house. If I wanted to keep the lights on in this place, I would need to find someone to go 50/50 on paying the bills with me.

Now, I didn't have too many friends, and the ones I did have, all had places of their own with partners of their own. I'm a single guy, pretty short and thin at only 5'4''. My hair is black and shaggy and would be considered long on a guy but short on a girl, ending just past my earlobes and almost covering my left eye. I wear pretty thick, round glasses over my blue eyes, and unfortunately, I can't grow any type of facial hair. Not even one strand. The only hair I have below my neck were my pubes, and there aren't even a lot of those. Basically, I was that skinny, nerdy kid at school that you would see glued to the flag pole outside every morning, or getting his face dunked in the toilet daily. If I'm going to have a roommate, it's got to be someone who can at least tolerate me.

I jumped online and posted an ad to look for potential roommates. For the next few days, I looked over the people who applied, and most of them were either fat, unhygienic looking guys, or people who lived like it was Spring Break 24/7.

There was one girl who looked like she would be a good fit though. She was 26, 6'5'', didn't drink, didn't smoke, had a 9-5 job, and from her profile picture, I could see a few video game related items behind her in her room. She was gorgeous too. Like, wayyy too attractive to live with a guy like me, but, she did want to live with me. She had thick and wavy blonde hair, flawless skin, cute brown eyes, and a perfect smile. It almost looked like she was naked in her picture too, but she was most likely just wearing a shoulder-less shirt or dress of some kind.

I messaged her, and we hit it off pretty quick. She was hyper and excitable yet also cool and down to earth. We talked about our interests and hobbies, our likes and dislikes, and we found that we had a lot in common! She had a few pieces of exercise equipment that she would like to take with her, and I told her that it would be fine and that she could store all of that into the garage and turn it into her own personal gym if she wished.

Everything was going great and we eventually exchanged phone numbers so that we could talk about living together even more. She had a really attractive voice to match her equally attractive face. God, just thinking about living with a girl this wonderful gave me butterflies.

After talking for a little while longer, we agreed on a date where she could come over and look at the place. In just two days, a beautiful, geeky woman would be in my house. This was a dream come true!

...

Two days later, I got a text from Fiona, my potential new roommate. She told me that she was on her way and would be here in a few minutes.

The house was tidy, I wore my nicest yet geekiest shirt (a t-shirt with Megazord from Power Rangers punching Godzilla), my cleanest jeans, my hair looked the best it's ever looked, and I coated myself in deodorant. Now I had to play the waiting game. As the minutes counted on, I began to wonder if Fiona's profile picture was up to date, and whether or not I had just been catfished. Before my worries got too ahead of me, I heard a car pull up outside and the doorbell rang.

This was it. Come on Max, don't screw this up. Give a good first impression.

I made my way to the front door, took a deep breath, and opened it. What was on the other side was something I did not expect. Fiona looked exactly like she did in her picture; flawless skin, amazing hair and smile, but also... she was naked.

Stark naked.

Head to toes.

Nude.

No clothes what-so-ever.

Completely, and totally, naked.

"Uh.... uh... ummm..." Those were the only noises that could escape my lips.

"Hey Max!" She said rather loudly and happily. "Oh my god! You're even cuter in person!" Fiona remarked with a wide smile. "Nice shirt!"

"Uhhh, y-y-you're...." I stammered.

"Can I come in?" Fiona asked, darting her eyes between the inside of the house and my eyes and tilting her head.

"S-s-s-sure" I replied, gingerly stepping to the side and opening the door even more, letting her in.

Fiona's body was just as stunning as her face. She had visible abs under her 34DD beasts, strong legs, wide hips, a toned torso, and her body was hairless and had a perfectly clear complexion. She wasn't exactly a bodybuilder, but she was in great shape. Standing at 6'5'', she was like an Amazonian goddess with the perfect physique.

"Wow! This place is nice! I saw the pictures you posted, but this is a lot more cozier in person!" Fiona spoke as she walked around the house, looking around at everything.

"Y-y-you're n-naked..." I finally said to her. I couldn't take my eyes off of her perfect body.

"Well, yeah. I'm a nudist." She replied casually. "Nudists don't wear clothes. Like, ever. I did mention I was a nudist, right?" She asked.

Not once during any conversation that we had did she mention that she lived a clothes free life. Not. Once. A guy would remember that comment.

"N-no. I don't th-th-think that you did." I stuttered back.

"Oh. Well, I'm a nudist." She replied, opening her arms and smiling genuinely before dropping them and going back to looking around the place. "Ooh! Is this my room?" She was so nonchalant about her state of undress.

"Uh, yeah, can I just ask; w-why are you a n-nudist?" I asked.

Fiona walked into the empty bedroom, turned around, faced me, and sat on the bed.

"I just don't want to wear clothes anymore. Simple." She replied casually.

"Why no?" I asked, not really understanding her answer.

"I always got told what I should or shouldn't wear, or what style suits me, or how to wear a particular thing, and it just wore me down. So, I gave up wearing clothes when I turned 18 and I haven't worn a thing since."

18?! That means she's been naked for 8 years straight?! That can't be right.

"Wait, you've been naked since you were 18?" I asked, gobsmacked. "8 years. With no clothes. How is that even possible?"

"Well, I just go about my daily business... with no clothes on. It's that simple." Fiona replied.

"But, wont you get arrested, or, haven't you been arrest, or, WILL you be arrested?" I asked, stumbling over my words.

"Nah dude, everyone just kind of lets me get on with things. They stare, sure, but nobody has called the cops on me or anything. It's not like I'm walking around, constantly finger-blasting myself. Or at least, not in front of people." She replied with a cheeky wink.

This was insane. I will be living with a woman who spends all of her time butt-ass naked and possibly masturbates in public places.

"But, what about your job? H-how do you g-get away with being naked there?" I asked

"Well, I work in IT, so I pretty much live in the basement of the building I work at and tell people how to fix their problems over the phone. I doubt a lot of the people there have even seen my face. Whenever I'm not on the phone, I just spend my time messing around on the internet, watching porn, listening to music, watching movies, that sort of thing. Okay, so I can drive back and forth between here and my old place and bring my stuff over right now. That cool?" Fiona asked, standing back up.

"uh... cool." I spoke back, still a little stunned by the whole situation.

"Great!" Fiona jumped towards me and wrapped me in a hug. God, she was so tall! My head rested in between and a little below her boobs. Her skin was so soft and smooth.

"It'll probably take me a few trips but I think everything will be in here by the end of the day. See you in a bit!" And with that, Fiona skipped away, towards the front door, and got back into her car, leaving me speechless.

Was this real? A gorgeous, geeky, naked woman was going to be living with me. Me?! I had to take a moment and collect my thoughts.

...

A few hours later, Fiona had all of her stuff in the house. Honestly, she had some pretty cool things. Plenty of movie posters, a bunch of anime statues, though, mainly pornographic ones (you know the ones I'm talking about, don't act like you don't), she even had an original Playstation 1 in pretty good condition too.

She also had a lot of lewd things too. A whole box of dildos, buttplugs, vibrators, and other things that I'd never even seen before. There were a few alien dildos too, which, I have to admit, were pretty cool looking.

All of her exercise equipment was placed in the garage, giving her a little workout area to use whenever she wanted.

Once everything was settled in, we both sat on the couch in the living room, exhausted. I could barely breathe. I hadn't lifted that much stuff in my life. It felt like I had just done every type of exercise there is, but Fiona, she only barely broke a sweat.

"You know, you can use some of the stuff in the garage if you want. Help you build some muscle." Fiona turned her head to me and offered.

"I... I... I think I'd... die under... one of those weights..." I panted back to her.

"Hahaha you're funny." Fiona replied, playfully slapping me on the stomach. God her arms were strong. "Why don't you go jump in the shower, I'll start arranging my bedroom, roomie."

That wasn't a bad idea. I hadn't sweated this much since I was back at school in gym class, or whenever the school bullies were around... or whenever a girl talked to me...

I got up and walked past my naked roommate and made my way into the bathroom. Turning the shower head on, I undressed and jumped in.

As the warm water ran over me, I began to think about this situation a little more deeply. Yeah, it's cool to have a super tall, super attractive, nudist woman living with me, but how will I explain that to my parents if they visit? No, when they visit?? It's bound to happen one day, either for my birthday, or Christmas, or just to say 'hi'. How will they react?!

As I poured the body wash over myself, I looked down at my body. No muscles. Soft and skinny. I basically had the body of a girl, just without the boobs, and instead of a vagina, I had a dick which was only 4 inches hard. God, why did I have to get a majority of my mom's genes? Dad's quite tall and manly. Chiselled jaw and everything.

Living with someone as beautiful as Fiona would be quite intimidating. But, then again, she did say I was cute. I wonder what she meant by that. Am I cute like a guy in a boy band, or cute like a puppy? My mind raced and went on all kinds of tangents until I was finally done with my shower. Stepping out, I dried off with a towel and wrapped it round my waist. No way was I going to put my sweaty clothes back on. Besides, Fiona wont mind will she? She's stark naked. I doubt seeing me in a towel would cause much of a fuss.

I picked up my clothes, exited the bathroom, and placed my clothes into the washer.

"Hey! That's more like it!" I heard Fiona call out.

I turned around to see her looking up and down at my body. Instinctively, my shoulders stiffined.

"W-what?" I timidly replied.

"Oh, I thought you were going to join me. You know, walk around au natural?" Fiona said with a slightly puzzled look.

"N-no, I'm not a nudist." I replied back.

"Aww, shame. You'd look cute if you were naked like me." She replied with a little pout. "Although, with the towel on wrapped around you, it kind of looks like you're wearing a skirt hehe. That's even cuter." And with that, Fiona turned around and walked into her bedroom, shooting me a little wink before closing her door.

Weird. Very weird. I'd never been called cute before, except when my mom told me I was cute as I was growing up, but, to be called cute because it looked like I was wearing a skirt, now that was new to me.

I didn't see much of Fiona for the rest of the night. She spent her time in her room, presumably organizing it all to her liking. While I was in my room, browsing the internet like I did every day, I kept thinking about what Fiona said; 'I thought you were going to join me.' and 'walk around au natural'. Does she want me to become a nudist like her? Or does she just like the idea of having a nudist roommate? Or just seeing a naked guy every day? So many questions based on those two sentences.

I wont lie, I have walked around the house naked before, but only a small handful of times. I only ever did it when I was sure I was home alone. Mainly when I would get out of the shower and walking to my bedroom without a towel.

I looked at myself in the full length mirror on my wardrobe, wearing nothing but my pajama bottoms. Slowly, I grabbed the hem of my bottoms, and pulled them down to my ankles, revealing my naked body. I guess I don't look too bad. Maybe I am cute. Maybe I could walk around naked from time to time. Maybe Fiona will think I'm even cuter like this. Maybe... maybe she'll want to touch me. My chest. My body... My cock.

As I thought about all of this, I couldn't help but touch myself as I grew harder. The thought of Fiona gently running her hands over my naked torso, down to my waist, and wrapping her fingers around my dick got me harder and harder, and I began to stroke while looking at myself in the mirror.

I kicked the pajama bottoms to the side, leaving me 100% nude. I thrust my hips forward and jerked myself off even faster. With one hand on my cock, I began to touch and rub my nipple with the other hand.

Faster and faster I stoked. My jaw couldn't help but fall open, and drool started to gently drip out on to my cock. As the pleasure grew more intense, I fell to my knees, still jerking away. The tip of my cock rubbed against the mirror as I rubbed up and down my shaft, until finally, I threw my head back, and cum shot out of my dick harder than ever before. String after sticky string, until the bottom half of my mirror was coated.

I fell on my back, which caused my cock to aim at the air, and the last few spurts of cum shot upwards and land on my tummy.

I was exhausted for the second time today.

...

It had been almost a week since Fiona had moved in and she had settled in pretty quickly. We worked different hours since she had a full time job and I only worked part time, so I spent more time in the house than she did.

The words she said to me when she first moved in still played in my head over and over, until I finally decided to act. One day, while Fiona was at work, I decided to slip out of my clothes and walk around the house naked. I set a little challenge for myself. It was 11am, and I tasked myself with staying completely nude until at 4pm. 5 whole hours of total nudity. If she can go 8 years without clothes, then I can go a few hours.

The first hour was pretty awkward and exhilarating at the same time. It felt like anyone could knock on the door at any moment.

Not only was I worried about being seen, I also felt pretty horny too. I mean, I'm an 18 year old single guy with the house to myself for a few hours, and I was nude. What would you do if you were me? You'd get on the internet and start watching porn, of course, which is exactly what I did.

I browsed PornHub for a little while, flicking through video after video, edging myself as I went. So many tits, pussies, and cocks on screen.

I lost control and found myself watching porn for a whole hour. My cock would've exploded if even a gentle breeze blew over it. Finally, with a few final pumps, I came into some tissue that I had at the ready.

Well, that was 1 hour gone. I still had 4 hours left.

After I came, I felt the need to get dressed, but I decided against it. I was going to complete this little challenge of mine. I went to the bathroom and cleaned myself up a little, before heading into the living room.

It felt a little odd walking around somewhere so familiar yet in an unfamiliar way. I tried to get comfortable by sitting on the couch and turning on the TV. The cool brown leather felt pretty nice against my bare bottom and back, and, to be honest, it was kind of relaxing sitting butt naked on the couch.

After a little while, I turned on my Xbox and began playing some games to pass the time, and before I knew it, it was 3pm. I was so invested in my game that I had almost forgotten that I was nude.

I had one more hour before I had to get dressed. I had spend enough time away from my cock and had 're-charged'. Before walking into my room and having another session on PornHub, I decided to head into the garage and check out Fiona's exercise equipment. This is where she would work out for an hour or two a day. There were weights, an exercise bike, a mat on the floor for push-ups and sit-ups, and a treadmill.

I walked towards the exercise bike and imagined Fiona riding it with her bare ass pressed against the seat. God, her ass was amazing, in fact, her whole body was, and she used all of this stuff to maintain it. I stood on the treadmill, sat on the bike, tried (and failed) to lift any of the weights, before lying down on the exercise mat on the floor and looking at the ceiling.

Being a nudist wouldn't be too bad. Sure, you'd get some funny looks, but at least you wouldn't need to wash your clothes after a heavy workout. Fiona uses all of this stuff every day. She lies on this very mat. Her bare back and bare ass touching the very thing that my bare ass and back are touching right now. Just thinking about her got the blood pumping to my crotch. I imagined her lying on top of me. Her warm skin pressed up against mine, her breasts in my face, her thighs locked on either side of my legs, and once again, I reached down and gripped my cock.

I gently opened my legs and began pumping away. I wanted to touch her. To feel her. To press my cock against her. There were so many things that I wanted to do to her. I looked down at my naked body, and watched my hand go up and down my shaft. I pictured her face in between my legs, licking my balls as she jerked me off.

It didn't take long for me to cum. An explosion of semen shot out and fell back down onto my tummy and chest. I was so engulfed in pleasure that I didn't even notice a few drops of cum landing on the mat underneath me.