Sissy and Her Neighbor Pt. 02

We got to know our kinks and decided to see where it leads.

My parents were already asleep as I got home. They're deep sleepers but I still quietly walked upstairs, trying to avoid confrontation.

I pulled out my white nail polish and quickly applied them on my toes and fingers. I then grabbed my makeups and put them in my bag along with some girly clothing. Next thing was to put on my chastity lock. I just love seeing my clit being locked up. It's so cute. I didn't want to waste too much time picking out clothes so I just grabbed my school girl uniform, knee high socks and a pair of open toe wedges.

I snuck downstairs and across the complex into Dan's house. He had dim lights in the living room. I opened the door and he was sitting on the couch waiting for me. He had light music playing on his home theatre system and two glasses of wine on the table.

"Hi, Sam!" he stood up to greet me with a hug. He's wearing boxers and tank top.

"Hey!" I hugged him back and asked, "So where should I get changed'?" I asked.

He locks the door and points at his bathroom. "Use whatever you need in there. I'll be here waiting. Take your time." he said.

I walked towards the bathroom. His house is fully decorated with luxurious marble and wood finish. The bathroom was like a hotel. Everything was screaming luxury.

I quickly put on my makeup. Pink eyeshadow, mascara, big red lipstick and I put on my school girl uniform and socks. I held my high heels and walked out 20 minutes later.

Dan was watching a documentary as I walked out. He turned towards me and was in awe.

"Is that really you Sam?" he asked.

"Call me Charlene." I replied with a smile.

I slowly walked towards him. The skirt on my uniform barely covers half of my ass. The top is quite short as well, revealing my abs.

"You are so beautiful Charlene. I can't get over how amazing you look." he complimented me with sparks in his eyes.

"Thank you Dan." I said as I sat down next to him.

He handed me a glass of wine and we had a toast.

"To Charlene and her perfect face and body!" Dan said happily.

"Those guys are really lucky to get with you Charlene." Dan added.

"Well, I'm here right now aren't I?" I laughed as I gulp down my wine.

Dan stood up to get the wine bottle from the kitchen. I could see his hard cock dying to break free from his boxers as he got up. I took out my phone and as he walks back I asked, "Care for a photoshoot?"

"Put on those heels and do some catwalk for me lady." Dan smiled and answered as he takes my phone.

I got up and started a full on runway show in his living room. Striking poses as Dan guides me on what to do. I enjoyed being submissive when I'm Charlene.

"Now get up on the couch on your knees facing the wall. Let me capture those delicious peaches." he said.

I did what I was told and started posing like a slut. I am super wet at this point and my thong is soaked to the point precum started to get through it.

I turned around and lifted my skirt. "Can you help me take this off Dan?" I asked as I pointed at my soaking wet thong.

He walked towards me and gently took off my thong. He was so gentle. As he pulls down my thong he caressed my thighs. I let out a soft moan.

"It's getting hot. Mind if I take my top off?" he asked.

"Why don't you just take everything off? You can't be the only one enjoying a show hehe." I replied.

He started taking off his tank top and I helped him take off his boxers. His hard cock bounced right up in my face. It's been a few months since I've been with a guy and the smell of cock just flipped my Charlene switch ON.

"Remember this is all we're doing right?" I asked with a naughty tone.

"Of course. I won't do anything you don't want to." he affirmed.

I can see precum dripping out of his foreskin. It looked delicious.

"More photos now!" he said happily.

I started doing more slutty poses. The wine is slowly kicking in as I became intoxicated little by little. I'm happy. The stress is gone. This is peace.

"Let the camera see your boy pussy." Dan said.

I got up into doggy position and spread my butt cheeks, exposing my buttplug.

"That's it! Hold still!" Dan said.

After a few shutter sounds I felt a hand on my right butt cheek.

"Now a photo like this, and this." he said as he moved his hand from my butt cheek to my butt plug.

I started moaning. I was so excited. It's been too long since a man has touched me. I then started to feel him playing with my butt plug, pulling it out slightly then pushing it back in. Next thing shocked me. He spit a little on my butt crack and placed his cock in between my peaches and started dry humping me.

I immediately got up.

"What was that, Dan?" I questioned.

"Sorry. I just couldn't help myself. You're so sexy, Charlene." Dan apologized.

"Well I guess if you put it that way, I should feel flattered?" I replied with a cheeky smile, "No more for tonight, okay?"

"Yes ma'am. Whatever you say!" Dan replied shyly.

I started to wonder what kind of kink Dan was into after his words. He called me ma'am. Is he into being dominated, too?

"Dan, tell me your kinks. I'm curious." I sat down and asked while gesturing him to sit next to me.

Dan sat down slowly.

"Well. I find crossdressers/transgenders more attractive than real women." Dan began to speak.

"I am a top for sure but sometimes I like to be.." Dan started to stutter.

"To be what, Dan?" I questioned.

"I like to be dominated sometimes." Dan said quietly.

I was in shock.

"But I don't bottom, that's for sure. I just like the idea of being dominated by a Queen, if you know what I'm saying." he continued.

"I see." I said as I tried to process my thoughts.

"I've never been a dominatrix before, Dan." I responded, "This is something very new."

"That's fine. This is more than I've ever hoped for!" Dan turned to me and said passionately all of a sudden.

"Should we call it a night then?" I asked nicely with a smile.

Dan had his head down again. "What's wrong?" I asked.

"Would you mind if I jerk off while looking at you?" Dan asked shyly, like a little boy, even though he looks like a bear.

"Sure, Dan. It's the least I can do for you right now I guess. Would you like me to pose for you? Hehe." I jokingly asked.

"That would be awesome!" Dan got excited again. That smile was back on his face.

Part 3 coming soon. Things are starting to get kinky! Stay tuned.

If you enjoyed this story please like and follow. A comment would mean the world to me. See you soon xoxo. -Charlene Cross.