A Sissy's Day of Fun

A few minutes passed and he walked to a nearby cabinet. I stepped down and followed behind and watched as he opened the doors to reveal a huge collection of sex toys. I could feel my cock jump right at this moment. He had pretty much everything. Dildos of every size and shape, anal toys, cock toys, and even some BDSM toys. He picked out several items, returned, and after a brief session of French kissing, asked if I was okay with being restricted, to which I said yes. He started running his hands around my ass, so I lifted up my dress a little bit. He got two pairs of handcuffs and cuffed my hands together and my ankles together, tightening the chains, and then told me to get on the sofa and on my knees. I complied, which gave him full access to my sissy pussy. He continued to grope my ass before pulling my dress further up to my waist. He noticed my G-string now and pulled on it so it snapped against my skin before pulling it down and around and off my heels. He then played with my plug a little more before taking it out as well; The stainless steel shined with my ass juices. A couple hours had passed, he suggested that we get my pussy warmed up. I said,

"Do whatever you want with me. I'm yours."

Out of the items he brought over, he got what I thought was just a normal dildo. I told him to use a little bit of lube again since this time I actually didn't want lube to get everywhere. He applied some, and started inserting it into my ass. I could feel the dildo wasn't shaped like a regular penis, since it was getting slightly wider the further down it got. After it was mostly inserted, he left it there. All of a sudden, I could feel the dildo expanding. I looked back, and saw that it was an inflatable one! He was squeezing a bulb and pushing more air into the toy, causing my pussy to stretch more and more. It was a new type of feeling but I loved it completely. He left it in while he softly bit my ass and passionately kissed me. By the time he took it out, my hole was already noticeably looser. He then switched to a dildo that actually was in the shape of a cock, applied a little bit of lube at the tip, and pushed it into my ass.

"You like that, you slut?" He asked.

I could only squeak out "Keep going."

I got on my back, throwing my chained feet over my head. He continued, and each pump of the dildo became more forceful but smoother as it glided into my increasingly loose ass.

He uncuffed my hands and feet and got out a huge anal dildo. It was a wide cone with ridges along the sides mounted on a base. I took my dress all the way off before he told me to ride the dildo and suck his cock. I put the tip of the cone into my mouth to get it a little wet before setting it down. I had to stand for a second to position myself correctly, but the size of the dildo matched perfectly with the height I was squatting at, as I kept my 7" heels on. I lowered down onto the toy, penetrating myself. My ass was loose enough that it went in without any additional lube. I rode it hard, using almost all of it. I could feel it was stretching me out even more than the others. He watched me for a few pumps before moving closer. I took his rock hard cock and stroked it fast. I kissed the head and licked his shaft and balls before gliding my lips over the entire cock, sucking quickly while continuing to stroke it. I almost wished someone else could've been watching us; It was another incredible sight. I was wearing nothing but stripper heels, bouncing on a huge cone dildo while being fucked in the face. My sucking motion had synchronized with his thrusts into my throat as he neared orgasm. He took his cock out my mouth and shot loads and loads of warm cum into my mouth. Some of it got onto my face, so I took off a shoe, wiped its heel across my face, and worked my lips over and cleaned it dry. I then stuck the heel into my ass and started fucking myself as if it was a dildo. Before I put my shoe back on, I again sucked the heel clean, savoring my ass juices.

His cock got immediately hard again after watching me, so he fully undressed and lied down on the sofa, getting ready to fuck me in spoon position. I moaned through our French kissing when his cock slid right. He pumped hard while I gave him better access by raising my leg into the air. We fucked for a while until he sat up on the sofa and told me to ride his cock.

"Only if you eat my ass first," I said.

I stood up, used a hand to stroke his cock and the other to hold on behind me, and sat on his face while he ate me furiously. I moaned with pleasure, my high heels digging into the plush sofa. When I had enough, I spun around, squatted over him cowgirl style, and let his hands guide my hips onto his cock. We kissed while his balls collided with the entrance of my hole. He grabbed onto my ankles next to his legs and fucked me hard. My prostate was getting rammed by his massive cock, and waves of pleasure ran throughout my body. I got off and briefly took his cock into my mouth until I sat beside him and grabbed his throbbing cock in between my feet, giving him a sexy shoejob.

"You really know how to work those heels," he said.

I responded by stroking his cock even faster.

When we were done with this, he walked me over to the lounge's bar. I sat on a stool and kicked my heels off, wrapping my feet around its legs. He stood behind me and continued to fuck my ass. We moved once more: to the pool table. I bent over the table and we fucked standing for likely another while until we both exploded in orgasms. He unloaded more cum into me and I dry orgasmed.

Part 4

All of a sudden, the doorbell rang. He said,

"Ah yes, he's here."

I gave him a confused look but he told me,

"I invited a friend to join us while you were showering. Sorry. I should have mentioned it to you earlier but it was supposed to be a surprise."

I was taken aback, but new excitement replaced that feeling quickly, so I responded,

"Wow I certainly wasn't expecting a threesome. But the more cocks inside of me the better!"

"Take a moment to get ready and meet us in the front foyer."

He quickly got dressed and walked out to greet his friend. I was still recovering from my orgasm, but I eventually stood up and was about to go get my things until his cum started flowing out my ass and onto my legs. So I sneaked to the nearby bathroom to force out the rest of the cum and wipe up my legs.

Back in the lounge, I was going to first put my plug back in when I realized that my ass hole had been stretched so much that the now relatively small plug wouldn't stay in well, so I left it on the couch. I slipped my G-string back on and then my dress. Last, I went over to my heels and stepped into them.

I slowly walked over to the foyer, anxious about meeting his friend and having my first threesome. Regardless, I was still exhilarated for more cock. I peeked around the corner and saw that his friend had some great sex appeal. He was tall, well groomed, and even more muscular than him. I walked over to them, making sure to strut and tease my body. When his friend saw me, I knew I turned him on instantly. I said hello and he took my hand and gently kissed it. My date said,

"Why don't we go to the pool and relax for a bit?"

They continued to walk and talk while I followed behind them. It had gotten much darker and chiller, so I was kind of confused by his suggestion. But he took us to another part of the house and eventually to his indoor pool.

"Of fucking course he has another pool," I thought to myself.

We sat down by the round sofas near the water and my date turned on the TV. I crossed my leg again to show off my clear heel as we continued to small talk, allowing me to get to know his friend a little better. Eventually, he moved over next to me and started running his hands across my body, feeling my legs and tits. I brought a foot up on the couch and put my hand on his crotch and rubbed it.

It didn't take long for another fuck session to happen. Both my date and his friend got undressed while I stayed in my clothing. My date walked over to us and I squatted in front of them, starting to lick his friend's cock before I took it into my mouth. It was considerably girthier, and therefore made fitting it in my mouth harder. But I still sucked the cock with lust, using both hands to stroke it while my date began hitting my face with his. I began alternating between their cocks, mouth fucking one while stroking the other. Then, they threw me onto the couch and lifted my dress up above my hips. I got on my hands and knees and his friend squeezed and slapped my ass while my date walked in front of me and resumed fucking my mouth. I loved the slight pain, knowing my ass was turning red. His friend moved my G-string aside and thrusted his cock into my pussy. The sudden feeling and size would've made me yelp but I couldn't since my date began to fuck my face even harder. Now getting simultaneously fucked by two men, my date's balls hit my chin and his friend's balls hit my pussy's entrance after each of their pumps. My cock strained against the cage, and as it strained more, it only became another source of intense pleasure. They fucked for me for a bit before switching sides and continued. I took his friend's gargantuan cock back into my mouth and sucked it hard. Soon, he reached orgasm and shot streams of cum into the back of my throat. Continuing to get fucked in the ass by my date, I looked his friend in the eyes and swished his cum in my mouth, savoring the wonderful taste before swallowing it. I sucked his cock again to clean it.

"You really got lucky," he said to my date while he planted his seed into my ass.

"She's really a fucking sissy slut!"

My date asked us if I wanted to possibly move to the master bedroom. I could feel my pussy getting slightly sore from all the rough fucking, but I still wanted so much more, so without hesitation, I agreed. I said to them,

"You guys go ahead first. I'll be up in a moment."

I let myself relax for a minute before I stood up and readjusted my G-string and pulled my dress back down. Before I walked up the stairs, I went to the kitchen to get another glass. I lifted one leg up, spread my cheeks, and pushed the cum out of my ass. I drank the cum and went back to the lounge to get some toys. All I wanted was the cone anal toy and realistic dildo. I didn't take the lube because my spit and ass juices were more than enough for my gaped hole. I carried them in my arms and walked upstairs, my leg muscles stretching and the clicking of my high heels resonating throughout the quiet house. I arrived at the bedroom and my date said,

"Nice that you brought the toys up."

I took my G-string off and pulled my dress up a little before I walked past them and left the toys on his nightstand. I bent over onto the bed and shook my ass at the two, teasing them to come over. His friend kneeled on the bed in front of me, shoving his veiny rod into my mouth. My date walked behind me, spit in my pussy, and got ready to continue my rough ass fucking. I reached back and spread my ass while they fucked my orifices. After a while, I told them I wanted to ride the cone dildo. I set it on the floor and sat on it, letting it fully penetrate and stretch me wide before I began bouncing up and down. While I squatted over it, I took the other dildo and began fucking my mouth.

They watched my little performance and kept telling me how fucking hot I looked. As my prostate was getting hammered, they walked over to me and I once again furiously sucked their cocks in turn. I quickly arrived at another orgasm, one so strong that I almost fell over on my heels. Before I could recover, they threw me onto the bed and we all got in position for me to get double anal fucked. My date lied down on the bed while I leaned back on him and got fucked reverse cowgirl. His friend quickly positioned himself in front of us. He held my legs up and stuck his big cock in my ass. After all the pleasure I had experienced, I didn't think it could get much better. When the second cock entered, I screamed from the pleasure. Their rhythm was perfect: their cocks pumped in turn. My rectum was stretching to the fullest as they rough fucked my ass to oblivion. My little cock fought hard against its cage, and I moaned from the sensation. It felt so amazing that I was screaming obscenities in repeat:

"Uhg. Uhg. Uhg. Keep going. Fuck me. Fuck me. Fuck me harder. Harder. You know you like fucking my slutty ass."

In a few moments, I felt both of them tense up before they exploded. I could feel their pools of warm thick cum fill my insides. They took their cocks out my worn ass and shoved them in my face. I gave them hot blowjobs, cleaning the cum off the heads and covering them in my spit. I then flipped around so I was now riding my date cowgirl. We French kissed while the both of them stuck their wet cocks back in and continued to furiously double fuck my ass hole.

They both lied down on their backs with their heads on opposite sides of the bed. They squirmed closer to each other so that their legs passed each other and cocks would stand up right next to the other. I took off my dress and threw it on the floor, and knowing what to do next, I stood up on the bed in my high heels to position myself over the cocks. I squatted down so that both rods entered my hole. I began gliding up and down the double cock like I had ridden the cone dildo. I looked down to see my tiny cock bounce each time I slammed down onto their cocks and stretched my hole. I took the cock shaped dildo again and fucked my mouth.

We switched to another position. We all got off the bed and I got fucked by my date standing while I passionately kissed his friend. Out of nowhere, they picked me up, suspending me in the air, stuck their still rock hard cocks back in my ass, and lifted me up and down. I was facing his friend so I grabbed onto him to brace myself. I watched my heels dangle on my toes before falling onto the floor due to how hard I was getting fucked.

We finished this position and they lowered me back onto my feet. I put my shoes back on and squat down again to suck their cocks, cleaning them of my ass juice. I stroked them hard before standing back up. I told them,

"I want to get wetter."

Wearing nothing but high heels, I walked into the bathroom. They followed. I could feel the dumped cum in my ass about to leak out, so I squatted and pushed it all out onto the bathroom floor. I got on my knees and bent over, licking it all off the floor and swallowing it. The sight of me instantly made them hard again.

I turned on the main shower and hopped in and pulled them both in as we got soaked from the ceiling faucets. His friend lied down on the shower floor. I followed by squatting over his cock and mounting it, giving him a good view of my ass as he thrusted and fucked my ass. My date stood in front of me and forcefully fucked my mouth as I deepthroated his cock. He then lied down too and we began assuming the last position we did on the bed, so that I could sit down on their double cock. I set down my hands behind me, leaned back, and bounced as fast as I could, my moans resonating on the shower walls. Before long, I shouted,

"Oh my fucking god. Oh my fucking god. I'm gonna fucking cum!"

I continued to penetrate myself and threw my head back. My restricted cock gave me another dry orgasm. Nonetheless, I still felt a powerful climax from my g-spot.

The douche head was still attached, so standing in my heels, I bent over and pushed back. I let it fill me with water and they walked in front of me and I went back to sucking their cocks in turn. When my ass was full, I got off and turned around, prompting my date to stick his cock in my ass and pound it while his friend kept fucking my face. Water shot out my ass as it got fucked hard. My date exploded into my ass, filling me with his seed. Now spent, he stood to the side and stroked his cock.

His friend pushed me back onto the douche and refilled me with water. Keeping his cock in my mouth, he held me there for a minute before pulling me off and sticking his rod back in my ass. Water from my ass sprayed everywhere as my date watched me. It didn't take long before his friend climaxed too, shooting his seed into my ass. He stood off to the side and stroked his cock as well.

I turned off the water, leaned over, and sucked the douche clean. I then squatted down, held my hand under my destroyed anus, and shit out their combined cum. There was so much cum that I had to use both hands. I brought them up and poured the cum into my awaiting mouth. I looked at them as I swished the cum in my mouth, licked the cum around my lips, and played with my caged cock and fingered my ass hole.

We walked back to the bedroom and positioned ourselves on the couches. I looked over at the clock and didn't even realize that two whole hours had already passed of us passionately rough anal fucking. His friend didn't realize either, and said he had to go soon. But I pleaded with him to stay for a little longer. He agreed and we prepared for more fucking, not wanting to waste time. His friend sat back on the couch while I squatted over him reverse cowgirl and rode his cock hard. My date walked to the side of the couch and so I turned my head and blew him quickly. The couch was a little narrow, so I wasn't able to squat with my high heels as far apart as I would like, making access to my anus a little difficult. So I waited for him to get off the couch before I hopped back on but on my knees, anticipating deep penetrating doggy style. Now in a much more pleasurable position, my shoes tapped against his legs as we moved our hips in sync. My date had moved around to the back of the couch, where I used one hand to stroke and suck his cock while I used the other to reach behind and spread my ass open. It was probably another half an hour that had passed before we all climaxed together. My body shook in absolute pleasure from my prostate while they shot inside of my mouth and pussy. As they calmed down, I hopped up and squatted on the coffee table, pushed out the cum inside my pussy, and spit out the cum in my mouth. I stepped back down, bent over, and using my tongue, swirled their cum into one small puddle on the coffee table before sucking it all up and swallowing.

Part 5

It was nearing the end of the night, which made me a little sad knowing how pleasurable it had been. His friend said he really had to go because he had to get ready for an early meeting at work. So after he got dressed, I kissed him once more and said our goodbyes. My date told me he had to attend a big presentation at noon so it was best we called it a night. I looked over at the clock again. It was already the early morning of the next day. I agreed, and so I got the key out and freed my cock and threw the cage, my dress, G-string, and stripper heels back in the tote. I got dressed by putting back on my black panties, jeans, and halter top. My black strappy sandals from earlier had dried by now, so I put those on before walking back to the lounge to get my butt plug. Before I walked out the front door, he asked if he could see me the coming weekend. I tried my best to hide my excitement, so I simply nodded.

I teetered down the stairs in my sandals, the clicking of the stiletto heels filling the dead silent night as he closed the door behind me.