A Sissy's Day of Fun

Part 1

It was summer break, so I was visiting home after my first year of college. My parents were going to be gone for the next few days visiting old friends. Being by myself, I went online to a hookup app and searched for a match. In my ad, along with a picture of my ass in a thong, I said I'm a young male looking to get fucked by a top. It only took fifteen minutes for someone to respond. He was an attractive mid-thirties decently muscular man. Although he was straight, it turned out he was really into fucking crossdressers! He just got back from a business trip and lived alone, so I guess it was a stroke of luck we matched with each other. We talked and made sure that we were both free from drug use and tested completely free of STD's, since we wanted to fuck without any protection.

I finished the show I was watching and continued with my preparations; There was still a couple hours left before I had to go. I had already gone to the bathroom and cleaned myself out, but I decided to douche again just to be safe, hopping in the shower when I was done with that. After I dried off, I shaved my face and body free of hair and got my 3" stainless steel plug and teased my anus with it for a few seconds before inserting it. Since I still had to get dressed, I only used a little bit of lube to get it in so it wouldn't get my clothes messy. I still had some chores that I wanted to take care of before I left, so I left my bathrobe on and got those done.

By the time I finished the last load of laundry, my body and hair were dry, and I could feel that my sphincter was relaxing. I went back upstairs and into my walk-in closet to pick out the outfit I wanted to wear to his house. I decided I would wear a simple, yet sexy outfit to begin with. I put on black panties, a heavily cropped white halter top, and a pair of ripped skinny jeans. For shoes, I zipped up black patent 5" platformless strappy cage sandals that went a little above my ankles. I also planned to bring another outfit to change into if needed, but I didn't know what it would be, so I decided to bring almost all of what I had, since the black tote I was planning on carrying had space anyway. Next, I tossed in my chastity cage and clear 7" platform mules to give me the slutty pornstar look, which I knew I was going to want later. I looked in the mirror to make sure everything fit correctly.

Exiting the front door, I immediately attracted the attention of others. I had put on sunglasses so I wouldn't have to make awkward eye contact with anyone. But flaunting my outfit way out in the open, knowing onlookers were staring, gave me a rush as my high heel sandals clicked loudly on my way to the car.

Part 2

I pulled up to his house, and my jaw dropped to the ground. It was as beautiful as it was big. I parked my car in front of it and hobbled in my heels up the stairs and knocked on the door. He greeted me with a warm smile and invited me in. He told me to keep my shoes on while I looked around what was essentially the closest thing to a palace I had ever stepped foot in. We took a seat in one of his living rooms and chatted. I could tell he was eyeing up and down my body, examining my outfit.

The more we talked, the more our tones became more sensual towards one another. I gradually moved closer to him on the sofa; Eventually, I was right next to him. He started stroking my body and kissing my neck as I softly moaned and started moving my hand onto his cock. It was rock hard. From there, we started making out completely, finding each other's tongues and exchanging each other's saliva. I was slowly stroking his cock in his pants.

"You like that?" I whispered to him.

"Yeah baby keep going," he replied.

Before long, he got fully undressed while I knelt down in front of him. His cock was thick and a good 8", and I was excited to take it. I stroked his cock and took it into my mouth as I moved my head back and forth. The feeling of having a real cock was unexplainable, and soon, I was savoring his pre-cum. I started undressing and was about to continue sucking his rod with only panties on until he said,

"Put your shoes back on."

Hearing him say that only made me hornier, and so I did. I put on a show for him as well, slipping each sandal on slowly and running my hands over my smooth legs. He stood up while I squatted in front of him. I grabbed his legs and went back to giving him a pornstar-like blowjob while he grabbed the back of my head and fucked my mouth. After a few minutes, I could feel him tense up.

"I'm gonna cum!" he shouted, and shot wads of thick, sweet cum into my mouth. The taste was amazing.

We went to his backyard, since the weather was nice and it wasn't dark yet. The backyard was also amazing, with beautiful gardens, statues, and a huge pool area. Both naked, with the exception of my shoes and panties, we walked around while he showed me around. Eventually, I noticed his cock was becoming erect again as we ran our hands across each other's bodies. Anticipating more, I said to him,

"Tongue my ass hole."

"Sit over there," he replied, and we walked over to the pool chairs.

I took a seat and leaned back, gently running my hands across my body. We kissed again and I turned around and got on my knees and rested my face on a pillow. I reached back and spread my ass apart while he took off my panties and started tugging on my plug and twisting it around before slowly pulling it out and pushing it back in, followed by my moans. He pulled it out once more and held it near my mouth, prompting me to suck on it. He began licking and dipping his tongue slowly, gradually increasing speed.

"Oh yeah. Oh yeah. Keep fucking going," I moaned.

His tonguing had opened up my hole a little bit more, and he soon said,

"Why don't you go get the lube? It's in a little drawer in the living room."

I walked back in, making sure to show off my ass and legs. I came back with the bottle and got back onto my knees.

"Don't use too much. I don't want lube to get everywhere."

He squirted some lube onto my waiting hole, and a little on the tip of his now fully erect cock. He teased my opening for a bit before inserting it completely. There was almost no pain, just complete satisfaction. He started thrusting back and forth while I moved my ass back to match his rhythm. We moaned together as he deeply fucked me.

"Fuck my tight little ass," I said to him as I was taking his huge cock.

I could feel my sissy pussy stretching, and each stroke glided in my hole with increasing ease as my sphincter loosened. Five minutes later of fast fucking, I yelled,

"Let me taste my fucking ass!"

So I spun around and plunged his cock into my mouth and furiously started sucking it, savoring the juices of my ass in the process.

It didn't take long for us to switch positions again, and we knew exactly where we were headed next. He told me to get up while he leaned back on the chair with his shaft sticking up. I climbed on top of it reverse cowgirl and started riding him. I spread my ass while he guided my hips. I made sure to use his entire cock by standing up after each pump to where the tip met my hole, before slamming back down. My prostate was getting massaged to the fullest and I was feeling incredible sensations across my body.

"Let me fuck your ass now," he said.

I responded by climbing up and squatting on the chair itself. My leg muscles stretched as I balanced in my sandals. He began thrusting upwards, fucking my ass with fury. I looked down at his dick which was repeatedly pumping into me. I felt like such a sexy slut. The sight of us must have been incredible: a man rough fucking a younger sissy who was wearing nothing but high heel sandals. It didn't take long before I started screaming,

"Fuck me harder! Fuck me harder. I'm gonna cum!"

I reached my first intense orgasm of the evening and shot cum in front of me onto the ground while I jerked my cock. He slowed down his pumping while I sighed in satisfaction.

Suddenly, he spun me around so I was facing him in cowgirl. He wrapped his arms around my back thrusted into me while I reached back and spread apart my ass. We began passionately French kissing while the sounds of our bodies colliding and my heels clicking on the ground filled the air. We must've fucked like this for close to an hour until I said,

"Why don't we get a little more creative."

"What do you mean?" He responded.

I got off and held his cock and guided him closer to the pool.

"Fuck me in there," I said.

I saw that there was a portion where the water barely came up to our shins. Keeping my shoes on, I hopped in and bent over, teasing my waiting ass at him. The sight turned him on even more, causing him to jump in and immediately get to work on my ass again. He fucked me hard and I leaned back into him and held his neck as he kissed mine.

"Fuck my ass in the water," I told him in a few minutes.

I lied down into the water and got on my side, raising one high heeled foot in the air, waiting for him to spoon fuck me. He quickly responded, and his furious thrusting sloshed the water around us while my foot dangled in the air. Next, I got off and he rotated onto his back. I squatted and sat on his cock so I was facing him. I put my hands on his chest and he put his hands on my shoes. Our movements matched so I was slamming back down on his cock when he thrusted upwards. We fucked like this for another while until it ended with him suggesting we go to the couches near the grill.

At this point, I had a change in heart about keeping it clean with the lube since I was so turned on. I told him to get the bottle of lube and dump it on our bodies. He smiled and quickly retrieved it. Standing up, I leaned over and had him pour lube all over my ass so it ran down my legs. Then, I grabbed the bottle, held it above me, and poured it into my mouth, letting it run down my chest. I rubbed my body, making sure it was completely oiled up. He did the same and continued to stand while I sat down and started sucking his lubed rod. He spun me around so I was on my knees on the couch, and started fucking me doggy style with even more ease now since we were so fucking wet. After a while, I lied down on my back and rested my legs on his shoulders. He fucked me deep and softly kissed my feet. He then grabbed my heels and continued to fill my insides with his cock. It didn't take long before we both shouted, screaming in ecstasy, nearing orgasm.

"Fuck. Fuck. Fuck!" He shouted.

"Oh yeah. Oh yeah! Fuck me harder!" I screamed back.

Within a few more pumps he exploded inside of me and filled me with his warm cum. Since my prostate was being constantly prodded, I orgasmed again without even touching my own cock, shooting cum onto my stomach. We collapsed onto each other for a moment and kissed.

I asked him if he could get me a glass. He said sure and went over to the nearby bar and handed me a shot glass. I knew his cum would flow out as soon as I stood up. So I put the glass on the ground, squatted over it, and pushed his cum out my now completely loose ass and into the glass. I picked up the glass, caught the cum running off my body, and sat back down with my legs to the side. I slowly poured our cum into my mouth while I began fisting myself.

"You're such a fucking sissy slut," he said.

I savored the taste, swallowed it, and smiled.

"Just watch," I teased, and fisted my ass harder, stretching it even more.

I took my fist out to reveal a slutty, gaping hole. It didn't take long before he came over and started fisting me. It was so hot that I climaxed again within minutes. Even during my shivering orgasm, he continued to fist me hard.

Part 3

About an hour had passed after we had that session of rough, hot sex. But we both knew we weren't close to being done yet. I suggested that we take a shower to wash off all the oil on our bodies. He was the gentleman and said he would use another so I could have full access to the master bathroom. Before walking upstairs, I went back outside to get my butt plug and panties and to the living room to gather my cropped shirt, skinny jeans, and tote.

I couldn't stop myself from getting amazed by every part of his house. I strolled around the bedroom in awe before going to the master bathroom, which was basically just a luxurious spa. I took off my sandals and stepped into the spacious custom shower, which had water running down from the ceiling and steamers at the sides. I gave myself a full cleanse, but I also looked around the bathroom to see what else there was. I looked under the main sink and to my surprise, found an additional shower head. It took me a second but I realized it was a douche, so I decided to give myself another enema. I removed one of the faucets and threaded the douche on. Bending over, I stuck my ass out and backed into it. I cleaned my bowels out a couple times, and since I was technically already clean, I just emptied the water from my ass into the shower drain. When I finished, I was about to take a towel off the rack, but wanting to have a little fun, I went back to the douche, leaned over, and fucked myself as if it was a dildo. I loved the sensation of both the douche head itself and the jet-like water stimulating my g-spot. It got the point to where I was fucking myself so fast the water didn't have time to fully shoot out my ass after every thrust, and instead I just kept getting filled up. I neared orgasm but I kept working the douche. Right before I climaxed, I got onto my knees and stuck my ass high in the air. I moaned loudly and simultaneously shot all the water out my ass and cum out my cock. I lied on the floor, catching my breath before stepping out. I dried myself off and stuck my butt plug back in to keep my insatiable hole ready,

I tip-toed outside and peeked down the balcony, and saw him watching TV on the couch. I shouted down to him,

"Hey, I'll be down in a bit."

"No worries. Take as much time as you need," he replied.

So I did, and with excitement, I knew it was now time to decide what I would want to wear next. I laid out the clothes I brought onto his bed, wanting to put on a new outfit to transition into the evening. I decided not to opt for my lingerie pieces, feeling they didn't fit the mood.

I wanted to wear something that screamed stripper, something that would be very revealing and tease my body and accentuate my curvy ass. But I also knew I shouldn't choose something that would be too difficult to take off and ruin the moment. Nor did I want to wear just a thong or stockings; It would be too simple. I decided on a light blue strapless fishnet tube dress. It was extremely short, just barely going below my ass. I first put on a matching tiny blue lace G-string. As I was slipping it on, I realized the bulge from my cock - when it gets hard again - wouldn't work well with the tight look of the dress, since it won't be restricted like in my jeans from earlier. I thought about it for a second before realizing I had brought my chastity cage. It would be the best option to complete the outfit, even if I was a little worried. I actually hadn't used it before so I was slightly apprehensive, not knowing how it would feel. I thought to myself,

"This is probably the best time to try it out. I was already planning on not touching my cock at all later anyway. I want to orgasm only from my ass and if I use it I don't have to worry about self-control."

I took off my underwear and put the cage on. My limp cock from the shower fucking allowed me to lock the cage with ease. I put the key back in my bag and bent over to make sure my butt plug was still fully inserted.

I bunched up the dress, slipped it over my head, and pulled it down. It was the same color as the G-string, so although the fishnet material made it see-through, they blended perfectly so that it was hard to immediately distinguish one from the another, altogether creating a streamlined appearance.

To complete the look, I pulled out from my bag the clear 7" platform mules. The lack of an ankle strap would make them both look more seamless with my legs and allow me to easily take them on or off. I sat on the steps of the bathtub and set the heels down on the floor. Taking my time, I slipped my foot in and ran my hands across my leg. I did the same with the other. Standing up, I strutted over to his walk-in closet, balancing on the carpet and feeling the back of the shoe softly tapping my heel each time I lifted my foot. Inside, I stopped in front of the full length mirror, and examined my outfit. Everything fit exactly how I wanted: There was absolutely no cock bulge and the clear heels went with the blue very nicely. I sat on the nearby cushioned seat and took a few poses in front of the mirror, which only turned me on more. I could feel my cock pulsating against the cage, but I enjoyed it.

I exited his bedroom and walked down the hallway, the shoes clacking on the wooden floor. I went down the few flights of stairs before finding him in his living room watching TV. The sound of my approaching heels alerted him, causing him to turn around and say,

"That is fucking gorgeous."

"I hope I didn't keep you waiting too long," I replied shyly.

"You didn't. I was just finishing up this episode anyway, so it's perfect timing," he said.

He asked me if I wanted anything to eat, and although I was starting to feel a little hungry, I said no because I didn't want to have to worry about things getting potentially messy later. Still, he got up, took my hand, and guided me over to the bar. I jumped up and took a seat; He took the seat next to me. He said,

"It's only 9pm right now, still fairly early. Let's take our time."

I agreed, since I didn't want to fuck right away and possibly leave sooner than I would like. We chatted at the bar for a long time actually, mostly talking about random topics that came to mind, and occasionally talked about our lives, keeping our boundaries for privacy.

Our foreplay started at the bar. I started teasing him by slowly running my high heeled foot up and down his legs. We moved back to the sofa and took a seat next to each other. He suggested we watch something together, but we agreed to keep it from getting too long or else we would be missing the point of all this. While we were watching, we started to move closer to each other to where I was almost in his arms. At one point, I crossed a leg over the other so he could see my shoe. I started dangling it by flexing my foot and balancing the clear strap on my toes. I knew it drove him absolutely crazy. Twenty minutes later, he turned off the TV and said,

"Follow me, I want to show you something."

He gestured for me to come before disappearing into the hallway. I got up and quickly teetered over to him. Slightly anxious, I followed him into what appeared to be his personal office.

"Watch this," he said.

Just when I thought his house couldn't get any better, he hit a secret lever and a door opened up to a luscious private lounge. There was silk, leather, and felt everywhere. The carpet was so fluffy that it made walking in my heels a little difficult. The other piece that caught my attention was the slightly elevated stripper pole in the middle of the room. By now, excitement had me at a loss for words. He turned on some soft club music and took a seat on the velvet sofa in front of the pole.

"Dance for me," he teased.

I had never even touched a stripper pole before, much less seen one in real life. I was no pole dancer so I couldn't do any crazy moves, but I could still be erotic. I stepped up, held onto the pole with my hand, and slowly walked around it. If I made eye contact with him, I made sure to bite or lick my lips, and when I found myself in front of him, I squatted down so my back was facing him, allowing me to tease my ass and show off the height of my heels. Or, I squatted and faced him, reached up and behind me and grabbed the pole, and used my other hand to run it across my body and tease my crotch area.