Sissy and Her Neighbor Pt. 01

[intro]

[House 1]

Charlene: Asian, 30 years old, 180cms, 80kgs, fit body from regular workout, closet crossdresser.

[House 9]

Dan: Asian, 52 years old, 173cms, 90kgs, single, rich.

[This is a story about sissy and the shenanigans happening in her neighborhood complex.]

Hi, I'm Charlene. I live with my parents somewhere in Asia in a residential complex made up with 11 houses. My parents are retired and are almost always at home. The houses in our complex are all identical and sit on both sides of the land with a small road in the middle. I have to express how much I hate non apartment houses in Asia. 4 stories with no elevator? I live on the third floor, and I cannot express with words how much I hate climbing stairs. Call me lazy.

I have recently quit my full-time job as my parents are getting older and they need a caretaker. I'm grateful that we are somewhat fortunate and have some savings so I can take some time off to be a full-time caretaker at home.

I'm a closet crossdresser, have been since I was in high school. (You'll know if you've read my Making of a Sissy series.) It's hard to find a daddy since I live in a rather small town and people don't really care for a good conversation before demanding to meet up on dating apps here.

I'm pretty athletic, I work out 5 times a week in the morning, and I go to our local swimming pool for the hot tubs and sauna occasionally. It is so refreshing to jump into a hot pool and just relax after working out or a long day.

Dan is a regular at the swimming pool. Sometimes he'd bring over pre-paid tickets for my dad and they would just go chill at the hot pools at night. He's a really nice guy and always brings over stuff to our place. I guess he and my dad just get along nicely. I'd see him at the pools sometimes when I go at night. We'd chat about everything while being massaged inside the hot pools or sweating in the sauna and steam room. I'm kind of a loner and I like it but it's nice to have good conversations with someone.

Everything happened one night. My routine is pretty fixed and simple. I wake up at 5 in the morning and start working out at 6. I'd rush home after that, and the chores don't stop until after dinner. Pool time for me is usually at around 8p.m. That specific day I was exhausted plus I haven't jerked off in a week! I guess you can say stress and anxiety built up overtime and I just couldn't hold it in that night. I needed an outlet.

I went upstairs after dinner to prepare for the pool. I wanted to do something kinky. I put on my medium size butt plug and my sports thong. Then I put on my comfy boy clothes on the outside. Next, I put my speedo and towels into my bag and headed off. I usually ride a motorbike to the pool as it's quite close to my place. As I was leaving the driveway Dan pulled up next to me in his Porsche and asked where I was going.

"Hey Dan! I'm going to the pool! Where are you headed?" I said with a smile.

"I'm heading to the pool as well! Race you there! Haha." Dan said while laughing before storming off the complex.

I followed right behind him. This was the first time we'd leave around the same time for the pool and that thought got me nervous. I'm still wearing a thong under my shorts.

I arrived 7 minutes later. Dan's Porsche was already parked in the parking lot along with two other cars. I'm assuming he's in the changing room. He likes to take his time to change into his swimming gear while chatting with the guys there. There are 8 shower rooms in the changing room on either sides and stainless-steel stools in the middle. Nobody really changes in the shower rooms.

I walked to the counter and the lady greeted me.

"Evening Sam!" she said while smiling.

"Hi Jenny. Not so busy tonight?" I smiled back and asked.

"Not busy! Thank goodness for that. Dan said you'd be coming. He's already downstairs in the changing room." she replied.

I handed her the ticket and walked in.

As I walked down the stairs leading to the changing room, I got quite nervous as I heard chatting and laughter. Dan was talking to another regular.

"Finally, we can have some peace!" Dan said while laughing, "Oh there he is! Motorbike Sam!"

I walked in with an awkward smile. "Hey guys! Quiet night tonight." I said.

"We can finally lay down in the sauna ha-ha right, Dan?" the regular said as he walks out. "Well, this is it for me boys, I'll see you next time. Enjoy the quiet night!"

"Catch you next time Rex!" Dan said. At this point he's already changed into his speedo. I can see a bulge in the middle.

I started to decide if I should get changed in the shower room or just wait for Dan to finish changing. I can't let him see my thong! He's going to think I'm a pervert and probably tell my dad!

"What are you waiting for Sam? Get changed and let's go have a nice dip! It's not every day you get the pool to yourself!" Dan said while laughing.

"Yeah sure." I replied, "You go in first! I'll be right behind you."

"More room for me then! Haha." he said as he walks out with his backpack.

I was checking if he walked upstairs before starting to get changed. I took off my t-shirt and my shorts and started to admire my physique in the mirror. I naturally have minimal body hair and I shave my armpits and pubic hair regularly. The thong really compliments my bubble butt I worked so hard for in the gym and my abs and V line are so visible and sexy. I could see in the mirror that my grey thong was getting wet. I quickly took it off and changed into my speedo and walked out.

Dan was already in the hot pool, vibing to the classical music playing on the speakers in the building. He saw me and started waving and shouting, telling me to hurry up.

I quickly put my bag in the storage area next to the pool and walked towards him.

The hot pools and sauna/steam room are on the opposite corner of the counter with a waist height wall in between the pools and the entrance. Dan had both arms on the ledge. His head tilted up and eyes closed. He seems super relaxed.

He opened his eyes as I got close and it kind of felt like he was checking me out as he stared at my body. I didn't think much as I was desperate to relax my body and mind in the pool.

I sat down next to the pool and put my legs in to get used to the temperature.

"I never knew you had beautiful legs Sam!" Dan jokingly said.

"Quit goofing around Dan! You're making me embarrassed." I said as my face slowly blushes red.

"Ha, thought I'd crack a joke. So why do you shave your legs?" he asked curiously.

"I don't have much hair anyway, so I thought why not?" I replied with a smile.

"Lucky you! Look at mine!" he said as he raised his left leg. It was really hairy and toned. "Sometimes mosquitos get trapped in them."

We both cracked out a big laugh. I slowly dipped into the hot pool.

"Ah, so good!" I let out a sigh and closed my eyes.

"Feels good, doesn't it?" Dan asked.

"For sure. Especially when it's nice and quiet. You guys chat a bit too much." I joked.

"It's only you and me tonight. So just relax and let yourself go. Don't worry about me." Dan said softly as he closed his eyes again.

I pushed the button on the side to start the air massage in the pool. It feels really good except for the part on my butt. I can feel my butt plug betting pushed against. It's slowly turning me knowing that Dan doesn't know I have a butt plug in my boy pussy.

"How are you parents doing?" he asked. "Your dad took a raincheck tonight. He would've loved the peace."

"They're feeling pretty tired tonight. We all do. He decided to stay in and sleep early."

"Tough job, isn't it? I had to take care of my parents too. I know how it feels." he said.

"Sure is. But as long as they're taken care of, I'm happy." I answered.

"Plans on getting married soon? I haven't seen you bring a girl home in a while. How's the love life?" he continued.

"There is none." I laughed. "I feel like staying single would be better for now. I don't really have time for other people.

"Wise choice. You get used to it over time." he said.

"No offense Dan, but why aren't you married?" I asked.

He turned around and looked at me for a second and laughed.

"To be honest, I don't know. I just haven't met the right one I suppose and now I'm a bit too old for that" he laughed again.

"You're not old! I feel like your age is like the sweet spot. Who doesn't like rich, mature men like you?" I said while laughing.

"You'd be surprised!" he laughed loudly. "Being rich is one thing. I guess I'm just not easy on the eyes like you."

I laughed, "I'd rather be rich than handsome ha ha."

"We all want things we don't have. This is why life is so interesting. You have to always try new things and explore. Don't live a boring life kiddo!" he answered.

"Oh that's for sure! I'm always down to try new things." I answered confidently.

"We'll see about that." he laughed and got up. "Wanna jump in the sauna?"

"Let's go!" I replied.

We got in the sauna and sat on opposite sides of the room.

"You must put in a lot of effort at the gym. Your body looks amazing." he said while checking me out. "Not in a gay way haha."

"Thanks. It's tough to maintain but I can't stand myself not being in shape." I replied with a smile.

He slapped his belly and said, "Think I can still get in shape? Haha."

"You look good the way you are Dan." I replied. I've always liked mature men who has big belly. Not sure why but that's what turns me on the most.

"Wait, so you're saying if you're a girl, you'd go out with me?" he asked while laughing.

"IF I was a girl, yes. Just because I'm in shape doesn't mean my girlfriend has to be!" I replied.

"Interesting. Too bad you're not a girl haha. I'd totally take you out. You have a pretty face and perfect body." He said while looking directly at my body.

"Come on Dan. I have a dick just like you haha. Pretty big as I've been told, too." I jokingly replied.

"Very confident I see." he laughed, "How about a bet?"

"What is it?" I asked.

"Let's see whose is bigger! Since we're the only ones here we can do whatever." he said.

"Haha I don't think that's appropriate, Dan. Why would you wanna see another guy's dick? Plus I'm your neighbor!" I replied. I was shocked and excited at the same time. I wanted to see what he would say.

"Well, to be honest with you, and this stays between you and me ok?" he said.

I nodded.

"I am.... into femboys." he said slowly.

"OH MY GOD." I thought to myself.

"And seeing you tonight made me feel like you'd make a perfect femboy haha." he added.

I swallowed a big gulp of saliva. "I hit jackpot!" I thought to myself.

"I hope you don't look down on me or anything. It's just my thing." he said.

"Of course not. Don't worry Dan. We are all weird in our own ways." I said.

"Thank you." he said, "Now for the bet! You in or out?"

"Let's do it." I said.

He stood up so quick and stripped off his speedo. I was shocked at what I saw. He was soft, dark, uncut and at least 8cm while soft. Pubes trimmed nicely.

"Don't be shy now! Haha." he laughed with is hands on his waist looking proud. "I'm a grower too!"

I stood up and slowly took off my speedo. His eyes got so big and I saw him swallow his saliva. He was speechless at what he saw. A shaved, cut, light skin with a pink head, 6cm dick hanging from my body.

"Hey! I'm a grower too okay!" I said proudly.

He tossed his speedo to the side and sat down. I did the same.

"Why do you.." he said

Before he could finish I said, "Shave down here? I just like it this way. Looks and feels better."

"You should try shaving or waxing. It's a totally different feeling from trimming." I added.

"Cool." he replied.

"What's the matter? You okay?" I asked as Dan became pretty quiet suddenly.

"Truth is, you are probably one of the best looking person I've seen. I feel bad for saying this to you." he said while covering his cock.

"Thank you Dan." I replied with a big smile. "Why are you covering your dick? Don't tell me you are getting excited looking at me!"

He nodded and said, "I actually am. I know this isn't right but you look so damn good."

His compliments really gave me an ego boost and courage. Dan is everything I've looked for in a man. And he's getting excited looking at me!

"I'm glad you like what you see haha." I laughed, trying to break the silence.

"Do you mind standing up and spin around?" he asked.

"Wow. You really just said that." I replied. "Is that part of the bet?"

"You don't have to if it makes you uncomfortable Sam. I guess I'm just over my head tonight, I'm sorry." he replied.

I looked at him for a few seconds and stood up. I got on my toes and slowly spun around like a ballerina while holding onto the wall. Making sure my bubble butt is as good as it can get.

I can see him in shock.

"Want to see something cool?" I said with a devious smile.

"Surprise me!" he said. Looks like he's slowly recovering from the awkwardness.

I turned my back to him and bent down. Revealing my heart shaped butt plug to him. I stayed in position and turned my head to see his reaction.

HE WAS HARD.

His cock is at least 20cm long and 5cm thick. It looks like his head is strapped in and about to burst from his foreskin. I started to get excited.

Here's a little note. I rarely get hard when I'm with men. I just get semi hard and super wet.

"I don't understand." he said quietly.

"I guess, just between you and me, they call it bisexual. I like men too, sometimes." I said with a smile and slowly getting up.

"So you've dated men before?" he asked with a surprised look.

"Well I wouldn't say dated." I replied.

"I like girls. But for men it's only for sex I guess. I've never really developed feelings besides lust for men. I can't understand why but that's just how it is." I explained.

"Wow." Dan is still in shock. "But how?"

"I wouldn't call myself a femboy but I'm what you would call a Crossdresser haha." I said.

"You? Dressed as a girl?" he asked with his mouth wide open, in more shock.

"And a pretty one, too!" I said proudly. I can feel my precum soaking the seat. "Wanna see photos?"

"Heck yeah!" he said eagerly.

"Let's get dressed. Wait in the hot pool. I'll go get my phone." I said as I started putting on my speedo.

"We're closing in 45 minutes Sam!" Jenny said as she sees me walk toward the storage area.

"Okay! We'll be out of here soon! Just got to show him some stuff on my phone!" I replied.

I quickly grabbed my phone and walked back to the hot pool.

Dan had his eyes locked on me as I approached him.

I got in and we had out lower bodies in the pool and upper bodies on the side, making sure I don't accidentally drop my phone in the water.

"So this is me with make up." I showed him a photo of me with full make up. Purple eye shadow, fake eyelashes, dark purple lipstick and blonde short wig.

"Get out of here! That's a real woman!" he said just loud enough.

"Look at that nose. That's me haha." I replied.

"You look just like a girl. Wow. I'm blown away, Sam." he replied.

"This is me in heels and black dress. This is school girl uniform." I kept scrolling through my album, showing off how good I look.

Next photo shocked both of us. It's a screenshot of the video I took during my last hookup with a guy. I was riding his cock with a tiny chastity lock with pink straps around my waist. I quickly scrolled left but it was too late.

"Show me again!" he said.

"You weren't supposed to see that." I replied with a shy tone.

"Aw don't hide it now!" he laughed and put his arm around my shoulder.

"Fine." I complied.

I went back to the photo. It's me in cowgirl position, eyes closed, mouth open and hands on my chest squeezing them together.

"What a beautiful site." he said with a straight tone.

"Thank you. It's still embarrassing to me for you to see this." I replied shyly.

"Imagine seeing this in person." he said, "You'd make me cum so quick."

"You wish! Haha." I jokingly replied, trying to hide my embarrassment.

"I would really like to see you dressed up as a girl, Sam." he looked me in the eyes and said.

"For real?" I was surprised and excited. "Like, you don't think it's awkward because we're neighbors?"

"It only makes it easier." he replied.

"True." I said, "How about we get out of here? My parents should be asleep by the time I get home. I'll bring some stuff over to your place and dress up?"

"Sounds good! Let's get out of here!" he said and immediately stood up. His cock was right in my face. Rock hard under his speedo.

"But only dressing up! Nothing else. Maybe you can help me take some photos but that's it." I said.

"That's a promise!" he replied and started walking towards the changing room.

I followed right him.

"Alright boys! Get showered up and get out of here! I need my beauty sleep!" Jenny said as we walked towards the storage area.

We grabbed our things and walked downstairs. I put my bag on the stools in the middle and headed into a shower room. I left the door open. Dan got in the shower opposite of mine and left his door open, too.

I turned my back towards the door and slowly took off my speedo. I knew he would be looking and I wanted to give him a show.

"Like what you see?" I asked as I turned around.

He was naked too. His cock is rock hard. I would love to run to him, kneel down and just start sucking it but I had to keep my composure.

He nodded and pointed his finger to his cock. "See what you've done?" he said while laughing.

We quickly showered and got back out. We stood in front of each other as we dried our bodies. I pulled out my thong and put it on.

"Perfect." he said as I put on my thong. "Look at your cake!"

"I know." I gave him a wink. "Hurry up now. The night is still young."

We quickly got dressed and headed out.

As we got to the parking lot he said, "Come over whenever you're ready. I'll leave the door unlocked and wait in the living room."

"See you soon!" I replied.