The Nudist and The Sissy

Noticing that I hadn't moved, Fiona glanced over at me.

"Well go on, take a seat." She said, extending her leg and pointing to the other couch with her toe.

I did as I was told and walked towards the couch. I never took my eyes off Fiona as I sat down. Licking my lips, I gently opened my legs, and began rubbing my shaft.

Fiona look absolutely gorgeous. The sun from the nearby window made her skin glow. Her blonde hair looked like gold, and the way she moved her body as she masturbated was like art. With her eyes half open, looking at me, and biting her bottom lip, she gently slipped a finger inside of her pussy, letting out a little moan of pleasure.

My jaw hung slightly open as I stroked my fully erect cock. I opened my legs even more and pushed out my hips while leaning back a little. I had masturbated to this very scene a few times. While I had gotten pretty used to seeing her naked, seeing her full of lust and pleasure was a dream come true. We really needed to masturbate together more often.

Our breathing got heavier and heavier as the minutes ticked on. My stroking got faster, and Fiona's finger did too, until I was almost ready to pop. I think Fiona noticed this, because just before I came, she extended her leg once again, and beckoned me over to her by curling and uncurling her big toe a few times.

"Come here cutie-pie. I'll... I'll let you cum on me." She panted.

Without wasting any time, I got up and almost ran over, hand still on my cock. I stood in between her legs, looking down at her gorgeous and toned body. I stuck my tongue out and I could feel my face get redder and redder. I was naturally making an ahegao face without even meaning to.

"Oh... my... god.. you're face is so... fucking adorable!" Fiona panted. She was practically vibrating as she got closer to orgasming. "Let's... cum... together..."

I was so horny, I could barely speak, I just nodded in agreement.

"Th-three... two... o-o-one... cummmm!!" Fiona cried out.

And I came. I came a lot.

An eruption of cum shot out of my cock, coating her face, tits, and tummy. Likewise, an ocean of juices sprayed out of Fiona's pussy, soaking my tummy and my crotch.

The wave of pleasure was so intense that I fell forward, into Fiona. She wrapped her strong arms and legs around me as she shivered from her orgasm. My front was covered in a mess of our cum.

That was, quite literally, the best orgasm I had ever experienced in my entire life.

We stayed like that for almost an hour, just embracing each other as our orgasms slowly died down. I liked being held like this. I felt safe with her holding me. Her strong arms wrapped around my back and her big thighs around my legs. Gently, Fiona stroked the back of my hair. It was so soothing that I could've fallen asleep right there and then.

I was looking forward to these two weeks.

...

It had been four days since our mutual masturbation moment, and I had become a lot more relaxed about my boners, though, the nudity as a whole had stated to get to me, and I felt the urge to cover up, at least a little.

I knocked on Fiona's bedroom door.

"Come on in." I heard her call from the other side.

I opened the door to find Fiona sat at her desk, playing a video game on her PC. Pausing the game, she turned on her chair to face me.

"Hey sweetie, what's up?" She asked.

"Can I wear some clothes now?" I asked back. "Maybe not a whole outfit, but, just something to cover myself with. Maybe just a pair of boxers? Would that be okay?"

"Awwww, I thought you liked being naked?" Fiona said with a cute little pout.

"Oh, I do! It's just that, well, what if we have a package that gets delivered and you're in the bathroom? I don't want to answer the door with nothing on. That would be pretty scary." I told her. "Or, what about when we run low on food and have to go to the store. I know you walk around naked in public, but I would be terrified."

Fiona didn't say anything for a few seconds. Instead, she just looked at me, as if she had an idea. She squinted her eyes a little, tilted her head slightly, and a small smile appeared on her face.

"Uhhh, Fiona?" I asked, waving my hand in front of her face.

"I have an idea." She finally said. "Two birds with one stone."

She stood up from her chair and looked down at me.

"We're going shopping."

My eyes widened and my heart skipped a beat.

"Wait, what?" I asked, shocked.

"Yep, you heard me. We're going to the mall!" Fiona responded, taking my hand and leading me to the front door.

"Wait wait wait!" I called out. "Why are we going to the mall?!"

She stopped in front of the door and grabbed her handbag which hung on a hook nearby.

"It's a great idea!" She said. "We'll go to the mall, a place full of people, and you'll get over your fear of being naked in the public eye, and I'll buy you some clothes once we're there! It's perfect!" She was so excited about this idea.

Before I could argue back, the front door was flung open, and I was pulled outside towards Fiona's car. I just about managed to close the door on my way out. My bare feet felt hot under the warm concrete and I tried my best to cover my crotch with my one free hand.

"Fiona!" I cried out.

"Don't worry cutie-pie, you'll be fine." She responded, digging out her car keys and unlocking the doors. "Hop in!"

I quickly ran to the passenger side door and jumped in the car, still covering myself, now with both hands, while Fiona casually strolled to the driver side door and gently sat down, closing the door behind her.

"Ready to go?" She asked with a smile.

"Fiona, we're going to get arrested!" I pleaded with her.

"No we're not! Relax!" Fiona replied, starting up the car and driving away from the house. "You said it yourself, I walk around naked in public all the time. 8 years! Remember?"

She was right. For 8 whole years, Fiona had been living a clothes free life. Going to work. Going to buy groceries. Hanging out with friends. Doing all of it stark naked, and not once had she gotten in trouble for it. If she can do it for that long, then surely I'd be able to handle a few hours.

"There's a store on the top floor of the mall." Fiona began to speak. "We'll go to there and I'll pick out some clothes for you. You can wear them as soon as I buy them. Go in naked, come out clothed. Deal?"

Fiona sure makes a lot of deal with me, and since the car was already moving, I couldn't really say no.

"Fine. Deal." I responded.

"Good boy." Fiona replied with a wink and a quick rub on my thigh.

As we drove through the city, I looked out of the window at all of the people going about their business. I felt like each and every one of them could see into the car and see how naked the two of us were, and my face burnt red with embarrassment. I kept my hands covered over my crotch for the entire ride.

After a 20 minute drive, we approached the mall and drove through the multi-story parking lot to find a space to park. Eventually, we found a spot. Fiona parked the car and turned off the engine. Grabbing her handbag, she opened up the car door.

"Come on then sweetie." She said, stepping out of the car.

"Fiona, I don't know about this." I replied. "Are you sure we wont get in trouble?"

"We'll be fine, cutie-pie." She reassured me. "Look, everyone will be looking at me, not you. I'll shake my tits or something, you know, as a distraction."

I nervously looked around the parking lot, trying to see if there was anybody nearby. Thankfully, there wasn't. Taking a deep breath, I opened up the door and stepped out. Once again, the concrete was rough under my bare feet, but at least this time, it was slightly cooler.

"Good boy!" Fiona commented. We both shut our doors and walked towards the entrance to the top floor of the mall. "Now, here's a piece of advice. Don't cover up. Just walk normally. I'll hold your hand if you like?"

"Why can't I cover up?" I asked.

"If you just walk normally, you'll stand out less." Fiona replied.

I agreed and held out my hand for Fiona to take. Walking hand in hand, we entered the mall.

The rough concrete turned to cool, white tiles, and the air conditioned mall made me shiver slightly. There were 4 floors in this mall, with the more 'adult' themed shops being at the top. There weren't many people on the top floor, but it wasn't empty. As we walked, I spotted at least 5 other people around us, and all of them spotted us. Down below, the mall was packed with customers. I could hear their footsteps, their voices, their bags rustling, and I started to freak out a little.

There were a crowd of people below me, and I was stark naked. If any of them looked up at this floor, they would see us for sure.

Fiona didn't seem to care, and walked around like she owned the place.

Eventually, we arrived at the 'clothing store'. It was, in fact, a sex shop. Stepping inside, Fiona waved to the girl behind the counter. She was a thin, emo looking girl with jet black hair with a hint of green across her bangs. I did my best to avoid eye contact and kept my eyes to the floor.

This store looked like it sold everything and anything sex related. Dildos, buttplugs, fleshlights, whips, strap-ons, lingerie, sexy costumes, latex, ballgags, you name it, they sold it.

Fiona guided me into the small changing room in the corner of the shop. There were three booths, all of which were empty. Fiona brought me into one of them and sat me down on the bench inside. My feet didn't even touch the floor when I sat down.

"Okay cutie-pie, I know you're nervous, but I am so proud of you!" She said, giving me a quick and tight squeeze. "You just walked into the mall butt naked! Isn't this exciting?"

Exciting? Not the word I would use. Terrifying is how I would describe this.

"Okay, now you sit here, and I'll pick out something for you to walk out of here in, okay?" Fiona said with a kind smile.

"Wait, what? No this isn-" I tried to reply, but it was too late. Fiona had already disappeared back into the store and closed the curtain to my booth.

I kept my hands over my crotch in case somebody came in and saw me. I was so nervous and embarrassed by the whole situation. I could hear Fiona chatting to the girl behind the counter as she shopped for clothes, though I couldn't quite make out what she was saying.

A few minutes later, the curtain flew open, which caused me to panic. It was Fiona with a small handful of items.

"Here, try these on!" She said, handing me a dark blue satin thong, two pairs of deep blue satin scrunchy looking things, and a headband which had two, fairly realistic and fluffy cat ears on.

Before I could say anything, the curtain closed as Fiona went to find more clothes. I couldn't believe it. A thong?! This is what she expected me to walk out of here wearing? I suppose it was better than nothing, but still! A thong?!

I finally decided to give in, and put the thong on. Surprisingly, there was enough room for my cock and balls. This must be a thong for men. Do guys wear thongs? Well, anyway, it fit me alright. The string didn't even feel that uncomfortable between my ass cheeks. I didn't know what I was supposed to do with the scrunchies.

"H-hey, F-F-Fiona?" I quietly called out.

"What's up sweetie?" I heard her call back.

"What do I do with the blue round things?" I asked her.

"Put them on your wrists, like cuffs!" She answered back. "And put the other two around your ankles. Don't forget the cat ears!"

I slipped the scrunchies over my hand and over my feet. They were the same color and material as the thong. Finally, I put the cat ears on my head and turned around to look at myself in the mirror.

I looked so...... feminine. Sure, there was a visible bulge in my thong, but other than that, with this whole get-up on, along with my pink hairclip and thin, hairless body and pretty wide hips, at first glance, you would think I was a girl.

I guess I did look pretty cute. Maybe. Sort of. I kept looking at myself, posing a little, trying to look casual, but no matter how I posed, I looked rather pretty. I also felt a little relieved to not be naked in a public store.

I must've waited another 10 minutes before I heard Fiona call out to me.

"Oh cutie-pie! I've paid for everything! You can come out now." Fiona yelled.

"Is... is anyone else out there?" I answered back.

"Only Katie, the girl who works here." She replied. "There were a few boys taking pictures of me on their phones, but they're gone now. It's just us girls."

Slowly, I opened the curtain and walked back on to the shop floor. Fiona had quite a large shopping bag full of things she had bought for me in her hand.

Fiona gasped with delight when she saw me, and Katie's eyes opened as wide as her mouth.

"You were right." Katie said. "He does look freaking adorable!"

"Eeeek!" Fiona shrieked. "Oh my god oh my god oh my god!! Cutie-pie!!" Her voice was so high pitched. "Come on! let's get you home."

Fiona came up to me and took my hand yet again, and together, we started to leave the store, but, just as we got to the exit, she stopped.

"Oh! I almost forgot. Turn around." Fiona said with a sly grin.

I did as she asked and turned my back to her. What could she be up to?

Suddenly, I felt a collar wrap around my neck and buckle on.

"Ow! Hey!" I cried out, turning back around.

"Ta-da!" Fiona said with open arms. "Oh my god, look look look!" She took me out of the store and placed me in front of the store window to look at my own reflection. Around my neck was a thick black collar with one word written in big gold letters across the front.

'SISSY'

I couldn't believe my eyes.

"I...I... I'm not a s-sissy!" I cried out.

"Sweetie, you're wearing a thong and cat ears. In public." Fiona responded, reaching around behind be and embracing me in a hug, resting her head on my shoulder and looking at our reflection.

"B-but that's because you told me to wear them!" I replied.

"So take everything off. Get naked again." Fiona replied, giving me a little kiss on the shoulder.

She had me there. In all honesty, if my options were to be either stark naked in public, or wear something girly... I'd wear something girly. At least my cock was hidden.

"Let's just go home." I responded, somewhat defeated.

"Okay cutie-pie." Fiona answered back. "Let's go- OH! I forgot something else!"

Oh god. What now? Reaching inside her shopping bag, Fiona pulled out a small, metal buttplug with a pink crystal in the shape of a heart at the base of it. I couldn't believe what I was seeing. Did she- was she- there's no way that's-

"Can I put it in you now?" Fiona asked with a wide smile, looking at me like a kid asking their parent if they can get a new toy for Christmas.

"I-i-in me?!" I said back, stunned. "R-right here? Now?!"

"Of course in you, silly." Fiona responded. "I promise it wont hurt! This is the smallest one they sold. You wont even feel it. You would look sooo cute with it! Pleeeeaaaase?"

I didn't know how to react. If I said yes, I'd have a metal plug shoved up my ass, but if I said no, I'm sure we would stand here, in public, dressed like a sissy slut, until I said yes. I looked around and saw a few people below near the stairs which lead to this floor. If they saw me, they would take pictures of me, just like the guys did to Fiona while I was in the dressing room.

"Okay! Fine! But make it quick." I answered her.

"Yay! Okay, bend over the balcony." Fiona said, leading me to the edge of the walkway.

"But, people will see me!" I pleaded.

"Only if you make a noise that makes them look up." Fiona replied with a giggle.

Wanting to get this over with, I quickly walked to the edge of the walkway, held on-to the hand-rail. I spread my legs apart and pushed out my ass. God, there were so many people below me. If even one of them looked up, my face would burn redder and hotter than the sun. From this position, anyone below me would clearly see that I was, at the very least, topless.

I felt Fiona pull the string from my thong out of the way of my asshole, exposing it to the cool air conditioning. She licked the buttplug, coating it in her saliva, before rubbing it around my asshole, wetting that too.

"H-h-hurry up!" I cried.

"As you wish, sweetie." Fiona answered back, getting the buttplug in position before slamming it into me.

I almost let out a cry, but I managed to seal my mouth shut with my hands just in time. Fuck! That hurt! And it felt weird!

Fiona pulled the thong back in place, and pulled it up slightly so that it was more over my hips than before, putting it in more of a V shape.

"All done!" Fiona said, giving me a playful slap on my ass cheeks. "Now, keep that in, and let's go home."

With that, she took my hand once more, and lead me to the car.

Wildly enough, the feeling of having a buttplug in me, wasn't as bad as I thought it would be. In fact, I started to get semi-hard. The plug was so close to my G-spot, I could feel it. With every step we took, my cock got harder and harder. By the time we got back into the car, I was pretty much fully erect. My satin thong formed a tent shape, and once I sat down, I could hide it pretty well.

During the drive home, the bumps on the road shifted my buttplug a little, rubbing it more and more against my G-spot. God, why did it have to feel so good? My cock couldn't get any harder, and it was a pain trying to hide it.

When we were about halfway home, I decided to stop hiding. Fiona had seen me naked, shaved my pubes, watched me masturbate, let me cum on her, dressed me as a sissy, and shoved a sex toy inside me. Seeing me hard wouldn't be too much of a shock to her by now.

I put my hands to my sides, opened my legs, arched my back, and pushed out my hips, revealing all. I grabbed my cock over my thong and began stroking it wildly. Once again, my natural ahegao face made its appearance.

"Holy shit!" Fiona called out, darting her eyes between me and the road as she drove.

I didn't care about the people outside the car anymore. If any of them could see me, there was nothing I could do to stop them. I just had to cum.

Fiona had a wide and surprised smile on her face as she kept glancing over to me while I animalistically stroked my cock.

After a few more bumps on the road, I was done. My whole body shook as a spray of semen shot out of my dick inside my thong. The cum covered my lap, my tummy, and I got some on the seat. It was a mess. A white, sticky mess, but I loved it, and I think Fiona did too.

I was limp and breathing heavily as we reached the house. So limp in fact, that Fiona lifted me out of the car and carried me inside with her strong arms. She placed me on the couch and covered me with a blanket.

"There, there, my little kitten." Fiona whispered as she kissed me on the forehead. "Sweet dreams."

I slowly fell asleep as Fiona stroked my hair.

...

It had been two days since I became a sissy femboy, or at least, that what Fiona referred to me as.

At first, I didn't know how to react to it, but as time went on, I grew to accept and even like it. I had been around Fiona for so long that it felt nice to be accepted by her. She was a beautiful, excitable, sexual, naked woman, and I had become a cute, pretty shy, sexual sissy. We were a perfect couple.

I had gone through my whole life, not really being accepted by anyone. I was the lonely, geeky, scrawny guy that people ignored, but in Fiona's eyes, I was an adorable, cute, lovely sissy femboy. I felt accepted by her, and as I became a cute girl for her, I fell in love with it all, and her.

In the kitchen, Fiona was teaching me how to make cookies. All I was wearing were some black, knee-high stockings, pair of black panties, a frilly white apron, and of course, my pink hairclip. We were having so much fun together, laughing and giggling like girls.