The Nudist and The Sissy

"Oh my god, cutie-pie!" Fiona said as she slid the tray of unbaked cookies into the oven. "Can I do your make-up?"

I gasped with delight.

"Oh my god, yes yes yes!!" I jumped up and down excitedly. This was so much fun! I had tossed aside any thoughts about trying to look manly, and while I was around Fiona, I wanted to be as girly as possible. I'm sure that adding make-up would make me look 10x cuter than I already did.

Fiona grabbed some make-up from her bedroom and sat me down on the couch in the living room. I crossed one leg over the other, took off my glasses, and rested my hands by my sides.

"Oh sweetie, you look so cute!" Fiona remarked. "Now, let's get down to business."

Taking a little brush in her hand, Fiona began to apply a little blush over my cheeks. Not too much though, as she wanted my face to still look natural. Once that was done, she added a touch of eye shadow, and finished it off with a tiny bit of lip-gloss that made my lips pop a little.

And just like that, I was done!

"Eeeeeekk!!" Fiona shrieked with delight. "Look look look!"

I put on my glasses and we stood up and walked to the mirror. I couldn't believe what a good job Fiona did. I looked like a real, actual girl. My heart started to race as I admired how pretty I was. My cheeks that made me look like I was blushing, the eyeshadow really made my blue eyes stand out, and the lip-gloss really made my lips look feminine.

Fiona may be beautiful, but I was adorable.

"Aaaahh!" I shrieked back with excitement. "Thank you thank you thank you!" I jumped up and down with my hands over my wide open smile before turning around and giving Fiona a big, tight hug.

"You're welcome, my little sissy slut." Fiona said, wrapping her strong arms around me.

I felt so safe and so accepted. Feelings that I had never felt before. Being a skinny geeky kid, I was mercilessly bullied all through my life. But now, with Fiona, I felt so much love coming from her.

I was happy.

...

A few hours later, Fiona and I were cuddled up on the couch watching TV. The cookies had been baked and put in the fridge. I had taken my apron off but I still had everything else on.

There wasn't anything that interesting on TV, so Fiona flicked through the channels looking for anything that grabbed our attention. Eventually, we stumbled upon the first Spider-Man movie, one of my favorites.

Putting down the remote, Fiona and I snuggled up closer together and started to watch the movie.

I had always admired the character of Peter Parker. He was a geek and a nerd, like me. He always wanted to do the right thing, even when it was the hardest choice. Since I had always been skinny, I dressed up as Spider-Man at Comic Con one year and had an amazing time.

As we watched the movie, I remember thinking back to when I was a kid reading Spider-Man comics. Peter Parker was in idol to me. My hero. I wanted to be like him when I grew up. He was a great guy with a beautiful girlfriend in the form of Mary Jane Watson.

As the minutes ticked by, I started to feel more and more hollow. What was I doing? I was watching a movie about one of my favorite characters, a character I wanted to become, and I was...... dressed like a girl? I was wearing make-up for god's sake. Peter Parker never dressed up like I did. He never acted girly. He never did any of this!

I had admired this character for so long, and I even believed I was Peter Parker for a while when I was a kid, but looking at the screen and looking at myself, we were two totally different people.

I felt the urge to get dressed. To wear clothes again. My clothes.

I stood up from the couch and made my way to my bedroom. Fiona must've assumed I was going to the bathroom because she didn't ask me where I was going.

Entering my room, I saw the chain still wrapped around my wardrobe door with the big padlock keeping it in place. I tried, and failed, to pull the lock off. I rattled the chain, tried to pull the door open, tried to cut the chain with a pair of scissors in my room, I tried everything. But it was no use. I felt angry. Annoyed. Used.

I stepped out into the living room and looked at Fiona.

"You okay cutie-pie?" She asked innocently.

"Can you... can you unlock my wardrobe please." I asked her quietly.

"Huh? Don't you like what you're wearing now?" She looked up at me from the couch.

"Just, just unlock it. Please." I said to her with a slightly louder tone.

"What's wrong sissy girl?" She asked me with puppy-dog eyes.

"I'm not a sissy!" I yelled back, causing Fiona to jump a little with shock. "I'm not a sissy! I'm a boy! You've taken away my clothes, forced me to parade about naked in public, forced me to wear stupid girly clothes, and put make-up on me! I'm not your toy! Why have you done all this? Why?!"

This felt weird. This felt really really weird. I had never stood up for myself before. Not to bullies, not to teachers, not to anybody. I don't think I liked this.

Fiona looked down, saddened and crushed by my words and my tone.

Shit. Fuck. No no no. Go back. Undo. I don't like this. What have I done? Shit! The adrenaline had left me and I felt my heart sink. Why did I say all of that?!

"I... I have a femboy fetish." Fiona finally said, still not looking at me. "Femboys turn me on. I've had boyfriends in the past, but they've all tried to be so macho and alpha. I just... I just like cute guys, okay? It's funny, the truth is, I didn't even need to leave my old apartment I lived in before moving in. I just wanted to live with a cute guy like you. I'm sorry I made you dress up like a sissy. I thought you liked it, so I carried on, but, I can see now that I took it too far. I'm... I'm really sorry cuti-... I'm sorry, Max."

I wanted to take everything I said back, but I felt so numb from the guilt that no words could come out.

"I'll go get the key to the lock." Fiona said, wiping a small tear from her eye and getting up from the couch. She made her way into the garage and came out with a small key. "It was in between two of the weights on my dumbbells."

Fiona walked past me and entered my room. She stuck the key in the lock and unlocked it, causing the chain to loosen and fall off. I followed her inside and stood by my door.

"Here you go." Fiona said, keeping her eyes to the floor and only looking at me occasionally. She walked past me and exited my room. She opened the door to her room, turned around and looked me in the eye. "I really am sorry, Max." And with that, she closed the door behind her.

Feeling more numb than I'd ever felt before, I slowly closed my door too. I turned around and looked at my wardrobe. I opened the door to it and looked at all my clothes inside. Clothes that I hadn't worn for about a week.

I slammed the wardrobe door shut and sat on my bed. I felt awful. Why did I have to yell at Fiona like that? Why?! This was a disaster! I liked dressing like a sissy, but I had stupidly tried to convince myself that it's not 'normal'.

Fuck normal! It's not 'normal' for someone to live completely naked, but Fiona does it, and she does it proudly.

I had to fix this. I had to make this right. I wanted to rush into her bedroom and apologize, but with emotions this high, I figured it would be better to try and do something in the morning, but what?

I've got it!

I jumped on to my computer and began shopping online. If I'm going to prove to Fiona that I like, no, love being a sissy, her sissy, then I need to perfect outfit to show it.

I managed to find a website that had an enormous selection of cute, girly outfits and accessories, and they had next-day delivery! Perfect! Our house typically got our mail delivered before everyone else, so whatever I ordered would be here by 7am tomorrow morning.

After browsing for around 20 minutes, I had filled up my online basket. A pair of black, leather panties with a little white bow on the front, a white shirt collar with a black tie and matching cuffs, a pair of fishnet thigh-high stockings, a pair of black high heel shoes, and a big white bow to go in my hair to finish it off. Since I wanted to show Fiona how much I loved being a sissy, I also added a 5 inch strap-on. I hit the 'order' button, and that was that.

Tomorrow morning, I was going to cook Fiona the best breakfast I could make, and apologise to her, and tell her everything I need to tell her.

...

The next morning, I woke up at 6:30am, eager to receive my outfit. I decided to stay naked so that I could easily get dressed as soon as the mail arrived, which thankfully, wasn't a long wait. Hearing a knock on the door, I rushed to answer it.

"Hi, I've got a package for- whoa!" The delivery guy was shocked to see me answer the door in my birthday suit.

"What, haven't you ever seen a naked girl before?" I answered back, taking the box from his hands.

"Uhhh, h-have a nice day." He quickly replied before returning to his car.

I closed the door and listened. I don't think Fiona had woken up. Perfect. Time to get ready.

I opened the package and found all of my things neatly packed inside. One by one I pulled them out and slipped them on. The cuffs, the collar and tie, the small leather thong which was just big enough to fit my cock and balls, the fishnets, my pretty white hair bow, my pink hairclip, and finally, my heels. I had never worn high heels before, so I walked around the house a little bit to get used to them. I found that, as I walked, my hips swayed slightly. I liked that. I liked that a lot.

I took out the strap-on and hid it underneath the couch in the living room.

As I continued to walk around, I ended up in front of a mirror. Wow, my make-up needed a touch-up. Fortunately, Fiona had left her make-up palette on the coffee table. Picking it up, I looked at my reflection, and did my best to make myself look as pretty as I did yesterday. Yesterday, just before I screwed everything up. No. Don't think like that. I was going to fix this.

After a few tries with the make-up brushes, my look was complete. Time to cook!

...

Fiona stepped out of her room at 8:10am, rubbing her tired eyes awake.

"Max? Are you cooking breakfast?" She asked, sniffing the bacon scented air.

"Stop!" I called out, standing in the middle of the kitchen with my hands on my hips, showing off my new outfit. "That's 'Cutie-Pie' to you."

Fiona was in disbelief. She had a confused and surprised expression on her face.

"Wh-what's going on?" She asked, walking in to the kitchen.

"Take a seat." I said, grabbing the bacon and egg filled pan and guiding her to the kitchen table. I poured the food on to a plate on the table, stood by Fiona, and took her hand.

"Fiona, I wanted to apologise." I started to speak, looking her in the eyes. "What I said yesterday, I didn't mean any of it. I love dressing like a sissy, and I love acting like a girl, and for one moment, I tried to convince myself that it isn't normal for a guy to act this way. And then I started to think about you. How you never wear clothes, even out in public. How you're always so open about your lifestyle and sexuality and fetishes, and how you do it all in spite of how people see you."

A small tear and a small smile appeared on Fiona's face as she listened to me.

"So..." I continued. "From now on, I'm going to be a sissy. Your sissy. No matter what. Even if people make fun of me, even if people think I'm weird, because you know what..." I stepped back and unleashed my boner over the top of my leather thong. "...It turns me on too."

Fiona let out a small, teary eyed laugh and stood up from her seat. Stepping over to me and bending down, she wrapped me in a big, loving hug. Fiona gently loosened our hug and got on to her knees in front of me so that we were eye-level.

"You... you really mean it?" She asked with a smile, wiping away a tear from her eye.

"I do." I replied, looking into her eyes. I plucked up all the courage inside me before telling her... "I love you Fiona."

Without missing a beat, Fiona pressed her lips against mine. Our first kiss. Our first proper kiss. She tasted so sweet. I wrapped by arms around her neck, and she wrapped hers around my back. We kissed again and again. When one kiss ended, another took it's place. Over and over.

"I love you too Max, my little cutie-pie." Fiona said, looking me in the eye.

"Go to the couch. There's something I want to show you." I said.

Fiona kept her arms around my back and lifted me up. Instinctively, I wrapped my fishnet clad legs around her waist as she carried me into the living room. Once we got there, she sat down on the couch with me straddling her lap.

"Ever since I met you, my life has been completely different." I started to speak. "Some of it has been scary, and some of it has been amazing. I know I got angry last night, and I wish I could take it all back. I do love being a sissy, and to prove that..." I stood up and reached under the couch, pulling out the strap-on. "...I want you to fuck me like a girl."

Fiona's eyes widened and she began to smile. Not only that, but another tear formed in her eye, only this one wasn't a sad tear. It was a tear of joy.

"Oh cutie-pie." She said, giving me a genuine smile and taking the strp-on from my hand. "I love you." With that, she stood up and gave me another soft yet deep kiss on the lips. "Lie down sweetie."

I did as she asked and positioned myself on the couch as she slipped on the strap-on. I pulled off my thong and opened my legs.

"I know it's not the biggest strap-on in the world, but I thought we could build up to bigger ones over time. Together." I said as Fiona got into position between my legs, resting one knee on the couch and her other foot planted on the floor.

"You ready cutie-pie?" Fiona asked, pressing the head of the cock against my asshole.

"Yes- wait!" I responded. "You've called me cutie-pie for so long, yet I've never given you a cute pet name. What should I call you?"

Fiona looked down at me, practically naked, wearing a feminine outfit, ready to be fucked in the ass, and smiled.

"How about you call me; mistress." Fiona said with a devilish grin, kissing me on the lips as she pushed into me, spreading my asshole open with her cock.

My whole body tensed up as she pushed deeper and deeper into me. As the cock slid further inside my ass, we never broke our kiss. Fiona's breasts hung over me and her nipples gently brushed against my torso. She was so tall that I had to wrap my legs around her waist so she could fuck me comfortably at an angle.

Once she was fully inside, slowly, she pulled back, letting my asshole get used to the sensation. Just before the head of the cock slipped out, she pushed in me again. Slowly and gently, I began to be fucked. I felt so helpless, like I was nothing but a fleshlight for this giant woman, and I loved it.

After a little while of gently fucking my ass, Fiona picked up the pace a little. As she did, my own cock began to stiffen. I wanted to reach down and stroke myself, but I felt so weak and at the mercy of Fiona, that I decided to stay still and accept my pounding.

My eyes went hazy and I let out a soft, little moan.

"Ohhh, you're liking this, aren't you?" Fiona asked, speeding up a little more.

"Yessssssss..." I moaned back. "Yes yes yessss."

By now, my cock had become fully erect, and every time Fiona thrust into me, my cock slapped her tummy. That gave me an idea.

I slowly started to focus, and I looked Fiona right in the eye.

"F-F-Fiona." I said, being pounded even faster. "G-g-get on th-th-the couch. S-s-s-sit d-d-down."

As if she knew what I had in mind, Fiona stopped moving her hips, pulled the cock out half way, and sat on the couch, picking me up and putting me on her lap. I kicked off my high heels and positioned myself a little better. Planting my feet on the couch either side of her, I began to jump up and down on Fiona's cock.

I was in control now.

"Oh! Oh! Oh! Oh mistress!" I moaned, bouncing on her cock.

Fiona grabbed my hips and helped, slamming me up and down on her lap. We looked each other in the eyes with pure lust.

"I-I-I-I'm going t-t-to c-c-cummm." I said as I felt my cock begin to pulse.

"Do it sissy. Cum. Cum for your mistress." Fiona replied, biting her lip.

Without missing a beat, I slammed down on to Fiona's lap as hard as I could, pushing her cock as deep inside me as possible, and a wave of pleasure went over me as cum shot out of my own cock.

Cum exploded between us, covering our faces and or torsos. We were both a white, sticky mess. All the energy had been drained from my body and I fell forward into Fiona, pressing our slimy bodies against each other.

As I tried to catch my breath, Fiona gently wrapped her arms around my back and held me before giving me a sweet, cum covered kiss on my cheek.

"I love you cutie-pie." She whispered in my ear.

"I love you too mistress." I whispered back, cuddling up to her even more.

...

END