A Sissy Life

I was surprised that Cara and Melanie asked me to take care of their cats while they went on vacation. Sure, we occasionally talk if we see each other coming or going, and sometimes our cats would meet in the hallways of our apartment complex. But other than complimenting each others cats and saying pleasantries we weren't really friends or anything. But I guess it made sense they'd ask a fellow cat-owning next door neighbor to do such a simple task.

I headed across the hallway for my first official cat sitting visit. They already showed me where everything was and what needed done, but it was still weird to be going into their apartment by myself. Bambam was happy to see a human, but I couldn't find Pebbles anywhere. I checked under the couch, on top the cabinets, in the cabinets, under Cara and Melanie's bed, nothing. Finally, I noticed the closet door in the bedroom was cracked ever so slightly, and checked in there.

Bingo. Way in the back behind a plethora of dresses, jackets, and shirts, Pebbles' green eyes stared warily back at me. I knelt down and tossed her some treats but didn't dare grab her. I was just happy to verify the cat was indeed alive and still in the apartment. Standing back up, I couldn't help but notice all the clothes I've seen Cara and Melanie wear over the years. It was strange to see it not actually on them. They were a painfully cute lesbian couple. Always out and about living their best life, and looking damn good while doing it. I was always a little bit jealous seeing them looking amazing all the time, while I was stuck wearing jeans and t-shirts everyday.

I gently dragged my fingertips down one of mini-dresses hanging in the closest. Its crazy that a fabric could feel so soft. It was just a plain black dress with stripes of mesh around where your cleavage and abs would go but man it looked awesome. I wonder what it would feel like to be able to where something like that? I pulled the hanger with the dress out of the closest and marveled at it in the light. I guess I'll never know. .....well, why not? Here I am with the dress in my hands. What's stopping me? The idea was ridiculous, but its not like I would be hurting anyone or anything. Fuck it.

I stripped down to my boxers in my lesbian neighbors bedroom. My heart was starting to pound, this was a ridiculous thing to be doing. I threw the dress over my head, and adjusted it down my body. It felt amazing on my skin, like nothing I've ever experienced before and well, I guess that's because I never have. I was immediately aroused and my cock started poking the dress forward. Can't have that. That ruins the whole aesthetic. I flipped it up and held it down with the waistline of my boxers.

Why was I even wearing my boxers? That doesn't make much sense. I took them off and added it to the pile of my guy clothes. My freaking boner was once again pitching an unsightly dress tent . I carefully opened a few dresser drawers until I found the one I was looking for. Damn, women's underwear is so tiny. And so soft! Holy crap. I grabbed a pair and pulled them up my legs, Good god, they felt nice. I tucked my raging boner into the side of it. It was uncomfortable, but in a strange way, I absolutely loved the absurdity of all this.

I carefully rummaged around their drawers a bit more and found some black pantyhose. Maybe those will make my legs look better? I slid them onto my legs, and fuck, it felt nice. I admired myself in the mirror. I actually look pretty good, well not as bad as I would have thought anyways.

They had a makeup stand by the window. I figured there's no stopping me now. I played around a bit with mascara and lipstick. It was more difficult than I thought, but the red lipstick looked pretty cool on my face. God, this was making me so horny. Imagine if someone saw me like this. What would they think? I wonder if I looked good enough for some guy to want to fuck me or something? They'd probably just mock me. I look stupid. Then again, who knows? Guys fuck anything, right? I always thought it would be interesting to give someone a blowjob at least. I think I would be pretty good at it for some reason.

I decided I wanted to play around a bit more like this. Maybe jerk off while all these thoughts were running through my head. I needed to head back to my place, I had a few toys I wanted. I cracked open the apartment door and there was no one to be seen in either direction. I held my apartment key in my hand, ready to unlock it as quickly as possible. I stepped out exposing my new cross-dressing fetish to anyone who might enter the hallway. I was only in the hallway for maybe 10 seconds, but my heart was racing and my cock was diamonds. I breath heavily while leaning backwards against my closed apartment door. I made it, I was safe.

I decided I wanted to do some light bondage stuff. The ridiculous predicament of me being helpless while looking like this was just so fucking hot to me. I grabbed 2 pairs of handcuffs, the key which was already frozen in an ice cube, a funnel, and some tape. I scurried excitedly back across the hallway to my neighbors apartment.

I've done this a few times, it's fun foreplay I guess. I put the ice cube containing the key in the funnel, and taped it to the ceiling in the shower. I figured I could jack off there too and have an ezpz cleanup. After about 30 minutes, the cube will melt enough for the key to fall through the funnel and I would be able to retrieve it.

Back on the bed, with the clock now running, I laid on my back and cuffed my left wrist to my right ankle and vice versa. My arms criss-crossing between my legs caused them to spread wider than usual and the dress immediately rose waist high, showing my ass and lingerie covered balls and boner to the empty room. My cock is throbbing painfully hard right now. I wish I could start jerking off right now but I have probably 20 more minutes before I can head to the shower and free myself.

I laid there for awhile, thinking only of how dumb I look and what people would think of me if they ever saw this sight. My dick was oozing precum nonstop into Cara or Melanie's panties. God, I want to jerk off this very instant. I rocked back and forth until I was able to get on my side at the edge of the bed. Rotating ever so carefully, I plopped feet first onto the ground, hunched over as my ankles and wrists were bound together. I could only hop, and do tiny baby steps towards the bathroom.

Finally, I got there and to my surprise there was no key on the shower floor yet. I looked up and saw the silhouette of the key....sideways.....too big to fit through the funnel. My heart stopped. That has never happened before. What even are the odds, Fucks sake, I never thought that could happen. Ok, no need to panic, I can just throw something up there, and jar it loose, no sweat.

Except I couldn't. With my restrictions I couldn't even throw things half the needed height. Ok no problem, I will just grab a broom or something and poke at the funnel. I wobbled as fast as I could to the broom closet, where to my dismay I found I couldn't open doors. I could reach high enough no matter how hard I tried and far I stretched. Fuck Fuck Fuck.

I baby-stepped around the apartment for over an hour looking for something that could work. There was nothing, there was fucking nothing. Exhausted and beaten, I fell over to rest. What have I gotten myself into? I have to do something. Fuck, fuck, fuck, I have to do something. I maneuvered my cell phone out of my jean pockets. Who the fuck could I call? The apartment is locked and I can't even unlock it. Even my closest friends couldn't help if I could even bring myself to let them see me as the crossdressing self bondage idiot that I am. The police? Firemen? God, what a scene. I can't do that.

I guess the maintenance guy could help? He's just one dude, he's probably obligated to not talk about what happens in peoples apartments or something, I don't know. I could always move to another apartment building and never see him again too. Yeah, what the fuck else am I going to do. I found the emergency maintenance number in my contacts, placed the phone on speaker and called, my heart thumping at the impending prospect of having to explain my situation.

He answered on the 2nd ring. "Hello, Damon speaking, how can I help?"

I forgot how cool this guy was. I've only seen him here and there working on other tenant's apartments. He always seemed to have his shit together. He was probably mid 30's, black hair, crew cut, always had the prefect 5 o'clock shadow somehow. You could tell he was a working man. He was a solid built dude.

I hesitated then dove in, "Hi, hey, so I'm I guess, stuck... you would say, and...sorry I don't know if you can help or not but no one else has a key to the apartment."

"Stuck? What do you mean?" He replied

I can't believe this is real life.... "Well, someone handcuffed me and then left and I can't reach the keys to free myself." That was a good lie! Now I won't look too weird maybe!

"I see, ok. Well I can certainly stop by and help you with that. I have this number listed as Apartment 230. Is that correct?"

"Uh, well I'm actually in apartment 235 right now"

"I would need apartment 235's tenants to call me then sir."

Fucking hell. Shit. Shit. Shit.

"Nooo, its fine", I pleaded. "I am cat sitting for them. They are on vacation. Look, it's really nothing, it's stupid. I just need help getting a key. It will take less than a minute. Please, Damon"

He waited a few moments to respond. "Very well, sir. This is a one time thing. I'm being nice and bending some protocols here because you've never asked for anything before."

"Oh my God, thank you so much, you are a life saver, thank you, really." A wave of relief came over my body.

"I'll be there in 15 minutes, ok. Sit tight."

"Can't do much else" I said slightly chuckling.

He returned a chuckle, "No I suppose not. See you soon."

He hung up, and I laid on my side happy that this ordeal was close to being over. Its going to be humiliating to be seen like this but what choice do I have now. I'll take it in stride as best I can. I positioned myself to a squatting position. My arms pretty much covered up my balls and cock so that was good. I couldn't get rid of my boner though. It was harder than ever knowing I was about to be exposed. But with good positioning, I could probably get away with a little bit of my decency intact.

Finally there was a knock at the door. "Damon here, anyone home? He hollered.

I hollered back, "Hey, come on in!" The butterflies in my stomach came out of nowhere now that this was actually happening.

I heard the door open and close, as well as Damon talking to himself I guess. "Entering room 235, "he was saying, "no signs of forced entry". I guess he was doing his due diligence or something.

"The key is in the shower!" I shouted. "In the funnel above!"

I heard him walking down the hallway, but he walked past the bathroom and turned into the bedroom. He had his phone out, recording. "Here's the tenant from 230, appears to be in the situation as claimed. Though he didn't mention he was in women's clothing and makeup"

I turned my face from the camera, embarrassed beyond belief and annoyed that he was doing that. "Hey, stop that!" I snapped. "The key is in the shower, please get it for me"

"Sorry", he replied. "I needed to cover my bases in case you were lying. This is technically illegal for me to enter this apartment."

"Ok well let's just get this over with, the key is in the funnel in the shower" I said sharply. Still avoiding showing my face.

He laughed. "I came here to help you,and you're going to boss me around like that?"

What's this assholes deal? "Sorry, it's just been a long day." I looked back over at him to show my distress and he was still fucking recording. "Will you stop that?!" I snapped again.

"Sorry my man, but it's a funny situation, no one is going to believe this happened. " he shook his head in disbelief, grinning ear to ear. "So you're wearing women's clothing in your neighbors apartment, and someone locked you in this position and made it so you could get the key out of a funnel in the shower? Why would someone do that to you?"

This fucking guy. "Ok look it was all me, I thought it would be fun"

He walked over to me still squatting on the floor. With one finger to my shoulder he pushed me and I tumbled onto my back exposing the lingerie I was wearing and a everything contained in them.

"Look at that view!" he exclaimed, laughing and still recording. I was beat red now and entirely speechless. He put the phone inches away from my bottom while I laid there helpless.

"Is that a boner you're hiding there?" He asked while getting a shot that answered his own question. I said nothing.

"You went all out. A cute dress, pantyhose, women's underwear, makeup. I think I'm embarrassed for you." He finally put down his phone.

"Tell you what, you let me have some fun with you, and then we pretend this never happened. No one ever sees this video."

Is this guy for real? "What do you mean fun?"

"Oh you know, sex. I fuck you like the little sissy you are. You ever done that before or do you just get your thrills from dressing up and jerking off?"

If I wasn't red before, I was definitely red now. What could I say, no? He would leave the apartment with a humiliating video of me and would he even free me? I have no choice. He's right anyways, look at me. Why am I this way? I've wanted to be fucked my whole life.

"o...ok" I said timidly.

"Ok what? He asked.

"Fuck me, and then free me" I said.

He smiled. He got what he wanted. And he wants me, that's kind of flattering in a way, I guess?

He then picked me up off the ground, making me feel like a baby with the ease that he was able to do it. He threw me on the bed, stomach up. Then he dragged me across the mattress so my head was hanging off the end. I looked at him upside trying to see what he was doing.

His pants were off in no time and his cock slapped me in the face. I had never seen another guys cock in real life let along touch one, and now there was one laying on my face. It was gigantic. It must be twice the size of mine and I'm pretty average. God damn.

"Head down, mouth open" He said while forcing my head into position. I opened my mouth as instructed. He slammed his cock down my throat. I didn't even have time to process it. It filled my entire mouth with heat, a hot hot meaty heat. My tonugue pressed up against it and it felt good, it felt right. It even tasted right. He thrust in and out slowly, letting me acclaim to my new situation. My mouth was producing so much saliva that it was spilling out onto my face each time he pulled out.

He reach for my cock, and stroked it over top the lingerie. It felt soooooo good, I could have came right then if he didn't stop as quickly as he started.

"Let's get these off" , he said while tearing the underwear off my body like they were nothing. My cock sprang upwards entirely free for the first time in awhile. "That is one cute cock you have there", he said. I couldn't respond with his own mammoth cock fucking my face. He grabbed mine and just held it. His rugged, manly hands felt weird on it. Nothing like my smaller soft hands.

"I own you now", he said while firmly grasping my cock and fucking my face. "You hear me, I fucking own you"

He pulled out of my mouth for the first time since he started, but kept holding firmly onto my cock while I laid there helplessly staring back up at him. My face was almost entirely covered with my own saliva. I panted heavily, not realizing how little I had been able to breath that whole time.

"Who owns you?" He asked, looking down at me.

"You do" I said without even thinking. Moments later questioning why I would say that.

He thrust his cock back towards my mouth and I happily received it. It was only out for a few seconds, but I already missed its warmth and taste. I started using my tongue more liberally to give him as much satisfaction as possible.

He started grunting and going faster and faster. I have a feeling he's about to blow. He started jerking me off with all the precum that I had been leaking, Oh, now I'm about to blow. Thursting his cock deep into my throat and jerking me off I let loose the longest most powerful orgasm I had ever had. My body was convulsing as his rough man hands finished rubbing every last drop of cum out my cock and onto my chest. All the while still fucking my face like an animal. Then he started to hold his cock deep in me, and spontaneously thursting off of his usual rhytm. Then it hit me, and it kept hitting me over and over and over. My entire throat and mouth was filled with steaming hot cum and his meaty alpha cock.When he was finally done, he held his cock deep in my mouth. I played with it with my tongue, knowing sadly it would soon be gone

"Hold your lips tight as I pull out, sissy. It's your job to do the cleanup."

I did as I was told, hugging every inch of his cock with my lips all the way until the head finally popped out of my mouth.

"Good job." He took his phone and snapped a picture of me. Saliva and cum oozing down my face, in my nose, on my eyes, my own jizz on my chest. I slowly started to swallow his cum. There was so much of it and I didn't want to get it on Cara and Melanie's carpet. It took 5 or 6 swallows before I could talk. By that time Damon already had his pants back on. He tossed me the key to the handcuffs.

"Until next time, he said, starting to leave.

"Wait" I said quickly without knowing what I wanted to say. "Can I call you?" I asked awkwardly.

He winked, "I own you, remember? I'll let you know when you're needed" And then he left, leaving me alone with my thoughts and a body covered in his and my cum. Fuck, I hope this dress isn't ruined. My cum was all over it.