Playing Dress-Up

Izzy was a punk rock chick with short, spiky, bleach-blonde hair, crooked teeth and tattoos that were far more badass and threatening than my own. She had a tough demeanor but she also had a great sense of humor. She was my kinda chick, for sure. Plus, in my humble opinion, she was hot as fuck. She didn't have an over abundance of tits or ass like Delilah but she had a really nice figure, a slight tan, a British accent and not to mention, she was a total slut and a pervert, like me and Delilah.

While I was on my cock mission, Delilah and Izzy had started hanging out more often. I'm not sure when or how they met. In fact, I'm not sure when I met Izzy! It just seemed like one day, she was at the apartment and it felt like we had seen each other before. Chances are, I met her sometime in the last year at one of our countless orgies, introducing myself by sticking my penis inside her, but to this day, I really don't know.

Izzy had a boyfriend named Daniel. Daniel was kinda timid. He wasn't very confident and came off like he wasn't fully convinced of his masculinity. He had a nervous smile, which gave me the creeps. I didn't dislike him, but I definitely wouldn't call him, "My kinda guy". That extended to his looks as well. He just looked like a regular guy, if not a little more puny or wimpy, with pale white skin, black hair and Central American features.

One day, Delilah and Izzy decided that we should have a double date. I told Delilah I wasn't into Daniel but she assured me "everything is gonna be great, trust me, I promise," etc. Whatever! Had Delilah ever steered me wrong thus far?

One sunny Saturday afternoon, Izzy and Daniel showed up at the apartment. Daniel seemed a little happier than usual. Izzy was wearing a short, black bondage dress and cowboy boots which actually had real spurs on them and she had a gym bag with her. When I saw that, I knew I was in for something weird.

"So Dick," started Delilah. "Me and Izzy were talking about having a foursome and you were the one holdout. So, I had an idea to do a little experiment. Something... a little different. Something I've actually wanted to try with you for a while."

Of course she puts me on the spot in front of everyone instead of asking me privately. She knew that would increase the chances of her getting what she wanted.

"Go on," I said.

"We want to dress you both up like girls," said Izzy. "And then see what you think of each other."

"See if you find each other more attractive." Delilah finished.

Somewhat puzzled, I looked over at Daniel. "What do you think of all this?" He actually gave me a much bolder response than I expected, by far.

"I mean, I would have been down to suck your dick anyway." He blurted.

"Ok," I said with a smile. "Thank you for your honesty!"

"Well...?" Said Delilah and Izzy, expectingly.

I gave them a long, stoic pause. It was all performance art, I actually loved this idea from the very start. I thought it the way they approached me about it was stupid, so I wanted to be uncooperative. But I was just fucking with them. So after my long, stoic pause, which was about the length of this paragraph, I said,

"I'm excited to try it! Let's get started right away, shall we?"

Izzy plopped this big gym bag onto the table. Inside of it was a bunch of really slutty looking women's clothing and sex toys. The kicker was, every single item was used and smelled like stale pussy and ass juice.

The two couples went to separate rooms so Daniel and I could try on different outfits and wigs. After going through a few different outfit options with Delilah, I decided to go with a form fitting minidress with quarter-sleeves and bare shoulders. If you were standing behind me, you'd have seen half by ass showing from the bottom of this dress and if you were standing in front of me, you'd have seen half my cock. Unfortunately, neither Delilah nor Izzy could find any women's footwear in men's size 15, so I had to wear my same old Adidas's I usually wore, with some rainbow striped thigh high socks. My hair was already pretty long at the time, so instead of a wig, Delilah just put some product in it to make my curls more dangly and pretty.

Once we were dressed, the girls blindfolded us and walked us out to the living room so we couldn't see each other.

Delilah and Izzy sat me and Daniel down in chairs with our backs to each other and removed our blindfolds. Delilah did my makeup and Izzy did his. Towards the end, Delilah did his finishing touches and Izzy did mine. Izzy was so fucking hot in that bondage dress, I would have been fine with just doing a regular ol' couple's swap. But if this is how they all preferred it, who was I to spoil a good time?

Finally Daniel and I were deemed ready by Delilah and Izzy. They stood us up, got rid of the chairs and turned us around to face each other. Wearing a pink pleather tube top with a matching miniskirt, white stockings and white high heels, Daniel was a sight to behold. Since his body was already puny and hairless and his posture was already very dainty, being dressed in sexy women's clothing was actually quite a fitting look for him. With the long, wavy, black wig he wore, along with the little bit of makeup he had on, he really did look like a woman. I've seen a lot of men crossdress and even when they pull it off and make it look hot, they usually still look like men in women's clothing, which is part of the appeal for me. With Daniel, he legitimately looked like a woman, but had a man's voice (even if he talked like a gay dude with no bass in his voice) and a cock which was also very appealing to me.

"You know what's interesting?" I said. "I didn't find you attractive at all before. But now, seeing you dresses as a woman makes me want to suck your dick!"

The girls laughed. Daniel was flattered. "Really?" He said in his soft ass voice.

"Really! May I?" I looked at Delilah and Izzy and asked, "is it ok to start now?"

It was smiles all around but I wasn't really paying attention to anyone but Daniel at this point. I didn't bother with kissing him or anything like that. Instead, I knelt down, lifted up his little skirt, put his halfway erect penis in my mouth and started sucking him until he was good and hard.

While I was sucking Daniel, Delilah and Izzy put on their strap-on dildos. Daniel got on all fours in front of me, face to face so we could make out while Delilah fucked him and Izzy fucked me. I'm not really that into having toys up my ass. I prefer a real cock any day. But it was still hot to change up the dynamic a little bit. I certainly didn't mind getting fucked by Izzy while dressed like a lady and kissing her boyfriend while watching him get ass-fucked by my girlfriend.

While they were fucking us, Izzy reached over and pulled a double headed dildo from her duffel bag. She and Delilah lubed it up with their mouths as they continued to fuck us. And then, when they were ready, they had me and Daniel turn around so we were rubbing our asses and balls together. Izzy shoved her side of the dildo up my ass and Delilah did the same to Daniel. Daniel and I worked the dildo up our asses until our cheeks were touching again. We continued fucking the dildo as Delilah and Izzy backed up so they could get a look at their handy work.

"Look at these little sluts we've created!" Said Izzy.

"I know," said Delilah, softly running her fingertips up the side of Izzy's ass. "Don't they look SO beautiful taking that cock together like this?"

"Mmm, yes they do," said Izzy before she leaned in for a long tongue kiss with Delilah. "You boys make pretty girls!" She said to us.

"You do!" Agreed Delilah. "Ooh, Izzy! You know what they need? They need dicks for their throats! Do you have anymore dildos?"

"Oh yes!" Said Izzy. "I got ALL the dildos! Here we go!"

Izzy pulled two dildos from her bag and handed one to Delilah. Izzy held the dildo in front of my face and while I kept steady eye contact with here, I swallowed the whole thing down to its plastic nutsack! Delilah took the dildo she had and just shoved it down Daniel's throat and started fucking his face super aggressively with it.

"Come on, you little bitch," she barked. "Take this cock in your dirty whore throat! Take it! TAKE IT!!!" Her screams and demands weren't loud enough to drown out the sound of him choking down the plastic dick in his throat.

I had the urge to turn around and see what was going on, but Izzy held me in place and said to me, "Keep sucking the cock in your throat. Keep fucking the cock in your ass. Be a good girl."

I did as I was told as quietly as possible so I could hear the abuse Delilah was subjecting Daniel to because it was turning me on. The sounds of Delilah repeatedly slapping, spanking, choking and insulting Daniel was just as satisfying as feeling my ass cheeks rub against his, with that dildo up both our assholes.

"You suck that cock like a good little whore," said Izzy as she bent to one knee and lifted her bondage dress. "Now you can eat my pussy."

I dropped the dildo that was in my mouth and dove my face into her pussy so quickly and dramatically, it was like the dildo was never there to begin with! Her pussy tasted like a mango marinated in salt water straight from the ocean. Delilah, however, had a different take on things.

"You suck cock like a little pussy!" Delilah shouted at Daniel. "Now it's time for you to lick my asshole, fucker!" She got right up in his face and shouted, "Can you handle that, FUCKER???"

Still gasping for breath with drool running down his chin onto his chest, Daniel nodded his head. Not that I saw what was happening, mind you, because he and I were still fucking that two headed dildo with our assholes. Delilah turned around so her fat ass was right in Daniel's face, flipped up her skirt, spread her cheeks, grabbed him by the head and shoved his face into her ass.

I ate Izzy's pussy until she squirted all over my face. And while Daniel licked and sucked Delilah's asshole, he reached the point of orgasm. It must've been the combination of Delilah's asshole flavor and the feeling of getting ass-fucked with that double-dildo. Cum was shooting out of his cock without anything even touching it!

After they took the dildo out of our assholes, I snatched it so I could stick both heads in my mouth suck up all the ass flavor from it. But then, I saw that wad of Daniel's cum on my floor, so I gave him the dildo to suck while I slurped his cum up off the floor. Then I grabbed Daniel by the hip and made out with him. That's when Izzy started sucking my dick. Then Delilah started sucking Daniel's. Just because he had already cum didn't mean he was finished.

With Izzy sucking my dick and Delilah sucking Daniel's, I reached out for Daniel's ass.

"Come on, bitch," I said. "I wanna taste your butt-hole now that it's all loose and I can get my tongue inside you. Come on, gimme your fucking butt-hole!"

I laid down and let Daniel sit his open anus on my face so I could bury my tongue in his ass. Delilah continued sucking his cock. Now that I was on my back, my hard cock was sticking straight up out of my dress. So Izzy sat her pussy down on my cock while I ate her boyfriend's ass while my girlfriend sucked his dick. It was a lovely Saturday afternoon crossdressing gender bending clusterfuck!

"Cum in my pussy!" Izzy moaned as she bounced on my cock. "Come in my pussy, you GIRL!!!"

Right about then, I heard Delilah growl at Daniel, "You're gonna cum in my fucking mouth while my man tongue-fucks you, faggot!"

Izzy kept riding me until I blasted my load, painting her inner walls with my hot cum, to her explicit delight.

"Now pull your tongue out of my boyfriend's asshole and take this cum in your mouth, you little slut," said Izzy. As little as I wanted to pull my tongue out of Daniel's hole, I wanted Izzy to dump the cum from her pussy into my mouth. As I pulled my tongue out of him, Delilah pulled him on top of her so he was riding her face with his cock in her mouth. She took one hand and put it on Daniel's ass, spreading it open for all to see as she guided him to fuck her face harder. Her other hand searched beside her until it found one of the dildos and shoved it up his ass, causing him to scream with pleasure.

"Yes, si, si, fuck me mami, fuck me," squeaked Daniel right before he busted another nut, this time in Delilah's mouth. After he dismounted her face, she stuck the dildo in her mouth to suck the ass juice off it, right before she grabbed me by the face, spit it all into my mouth and followed it up with a sloppy, passionate make-out session. To my other side was Izzy. I turned to her and started making out with her too. We all took turns making out with each other until we found ourselves just laying on the floor like a bunch of lazy sluts who just got fucked.

"Fuck, that was awesome," I said.

"Yeah it was!" Izzy agreed.

"Daniel, you make quite an irresistible woman," I said. "We definitely gotta do this again."

"Thank you, baby," said Daniel. "Next time, you gotta fuck me with that big, beautiful cock of yours!"

"You two didn't fuck?" Said Delilah.

"I mean, I would have," I said with a grin. "But Ms. Bondage Dress over here was hogging me!"

She smiled, "Yeah, so?"

We laid around on the living room floor for a while with the backs of our heads propped up against the furniture we could have just been sitting on, smoking weed and chatting about the sex we just had and sex to be had in the future.

"You both make beautiful girls!" Said Izzy. "I'm jealous, Danny boy might be prettier than me!"

"Bullshit," I blurted out.

"She's right," said Delilah, "You're a couple hot mamas! We should put you two little hobags on the corner to make us some money!"

Izzy laughed. Me and Daniel just looked at each other as if a light bulb went on in our minds.

"I'm DOWN!" Said Daniel, 100% seriously. "I'm not even playing, I'm SO DOWN!"

"Yeah?" Replied Delilah with a big smile. She looked over at Izzy, who was also smiling brightly. "What about you, Dick?"

I tried to think of a smart-ass response, but I couldn't. "You know I'll try anything once!"

Later that night, we all piled into Izzy's Honda Accord and she drove us to the corner of 53rd and 3rd, right by the Sleezy Breeze motel. The girls stayed parked where they could see us as Daniel and I walked up and down the street together.

As I said before, Daniel looked like an actual woman in his get-up. And that was in a well-lit apartment, standing mere inches from each other. The same could not be said for me. I'm over six feet tall with broad, muscular shoulders so even in the dark, from far away, you could tell I was a guy wearing women's clothing. But that didn't mean I didn't look sexy...

Within a half hour, we were approached by a guy who said he was looking for whores for himself and "a whole bunch" of his friends. I asked, "How many guys?"

"Mmmm, 'bout 20..." he answered.

20 hot scumbags stuffed into a tiny little crack hotel sounded like my exact idea of a good time. I would technically have been willing to do it for free, but the objective here was to make money. Without consulting Daniel, I started to negotiate a deal.

"$500" I said. "For the both of us." With my complete lack of experience in the field of prostitution, that sounded like a great deal to me. Apparently, the guy thought so too. So we went with him to the Crack Suite.

"Oh my God," Izzy said to Delilah back in the car. "They actually got picked up!"

When we got to the room, there were 20 drunk losers standing and/or sitting around, beating off to the porn playing on the TV - some blonde with fake tits getting fucked by a bunch of shitheads not much different from the ones in the room with us. Daniel and I stood in the doorway smiling eagerly.

"That's a lot of dicks!" Said Daniel in a low volume.

"I'm fucking ready," I said. "If you're scared, you can go back to the car if you want." I addressed the group, "I can make all 20 of these douchebags cum in no time!"

"Nuh-uh!" Daniel said. "I bet I get more cum than you, whore!"

Our playful bickering was exciting the already hot and bothered men. Daniel and I dropped to our knees and made our way around the room sucking cock after cock after cock. We called it a Cocksucking Contest just for fun, to give it a little competitive, game-like vibe. But at the end, neither Daniel nor I could tell you how much cum we swallowed. We could only verify that each guy came at least three times because Daniel and I were on a cocksucking, cum-guzzling rampage that night.

When we were done sucking all 20 dicks several times apiece and swallowing about half a gallon of strange loser sauce, the guy gave me the money and we left the room, trying to play it cool like this was something we always did. But as soon as we turned the corner, we were both going, "HOLY SHIT, can you believe we just did that? Can you believe we just made money doing that?? Holy shit, what a rush!"

This energy stayed with us as we got back into Izzy's car.

"What happened?" Asked Delilah.

"We got picked up!" I said, intentionally being under-informative.

"I know you got picked up, jackass. What HAPPENED???"

"We sucked 20 dicks!" Said Daniel.

"Yeah," I continued. "And we made $500!"

"BOTH OF YOU???" Exclaimed Delilah and Izzy in unison.

"$250 a piece," I said.

Delilah and Izzy looked at each other and hunched their shoulders like, "That's still pretty good!"

The success of this experiment made Delilah want to start pimping me out more often, which I found exciting. So, for the next few weeks, she started setting up "appointments" for me with other men. No more "dates", where I get to pick a guy and meet with him over coffee or something. These "appointments" were transactional and almost formal. It was always the same deal. Always very quick, very cold, little to no discussion involved. I would meet a guy or guys at some location dressed like a hot sissy slut. These were guys that Delilah had essentially chosen for me, met with in advance and worked out a deal with, in which I had little to no say. I would suck their cocks, rim them, let them fuck me, whatever Delilah had arranged with them. Then they would pay me and I would leave. I would give the money to Delilah and she would wisely park it in a savings account.

The more I did my new side job, the more I liked it. And the more I did it, the rougher and more degrading the situations became, the more I became obsessed with it. It drove me wild. It went from a humorous onetime experiment to a temporary revenue stream for me and Delilah. But all-in-all, it was a short lived venture.

As for Izzy and Daniel, that day led to me and Delilah having a full-on fling with them both. This was a very layered fling. People talk about love triangles... this was more of a sex octogan. There was my fling with Izzy, Izzy's fling with Delilah, Delilah's fling with Daniel, Daniel's fling with me and then there was the four of us! It was confusing, twisted and a lot of fun.

My fling with Daniel mainly consisted of he and I dressed like girls, frolicking through town, collecting cocks. He and I would spend many nights blowing, rimming and getting fucked by strangers. But sometimes, he and I would just get together, dress up and fuck. In those situations, I was usually the top because Daniel loved it up the ass so much. He had a sensitivity to anal stimulation that made cum shoot out of his cock over and over again, which I found very sexy and exciting. After playing with his asshole for a minute or two, his cock would start shooting cum almost involuntarily. It was beautiful!

As such, our girlfriends loved to use us to please the other men they were fucking. So one day, we had a little get-to-know each other party at the Orgy Spot. Izzy and Delilah invited a bunch of their male fuck-buddies over. Technically, it was an orgy. But in terms of execution, it was much more of a gangbang. The men outnumbered the women by a lot, even considering me and Daniel were playing the role of women.

Delilah and Izzy were getting fucked side by side on the floor. And all their fuck-buddies were taking turns fucking all four of us. It was all very hot and all in good fun.

At one point, me and Daniel were getting fucked side by side on the kitchen table as we held hands and kissed each other every time there wasn't a cock or an asshole in our faces. I was laying there, wearing this fluffy princess dress with my hair in pigtails as men took turns fucking me. One by one, guys would fuck us, cum in our assholes and then make way for the next fucker to do the same. I would turn my head right and there would be a man spreading his cheeks for me to taste his hole. Then I'd turn left to make out with Daniel whose mouth tasted like sweaty balls and assholes. With load after hot, creamy load shooting into me, I felt like I could do this for the rest of my life without stopping and be set.

But then, right as one guy was pulling his cock out of me and moving along to the next hole, I was mounted by a man who immediately made me think, "Oh fuck, who is this perfect man???"

Unbeknownst to me, his name was Victor and he had been fucking Delilah and Izzy for months! He was a thick, muscular Afro-Brazilian man with puckery lips and a perky muscular ass, much like the Brian Pumper lookalike from earlier in the story. I had been fucked by enough guys that day to lose count. But when he stuck his thick, black cock inside my asshole, it was like a key going into a lock. His cock just felt perfect inside me, like it was custom made especially for me! A perfect fit. I had to have more. I had more of myself to give to him.

So I told Delilah I had a thing for the guy after everyone had gone home. She told me he had said something about liking me too and said she would introduce me to him. Later that week, she invited him over to meet me. He was so fucking gorgeous, I could hardly control myself. I was smitten. And not only could I not hide it, but I felt no need to. I wanted him too bad to be inhibited.

Victor brought the bitch right out of me. Something about him just made me feel ladylike. As we briefly conversed, I involuntarily kept feeling my lips pucker, my back arch and my cheeks part. I felt my posture become light and dainty. The depth of my voice even seemed to lighten as I involuntarily and desperately flirted with him. I became all touchy-feely and suggestive, just like Delilah is with everyone. I'd never felt like such a girly little bitch before and moreso, I never imagined that feeling like such a dirty little bitch would feel so amazing.

Before long, I was sitting on his lap letting his big, strong hands explore my body... and then we were making out. I was already wearing a minidress with no underwear, so I just slid his cock up my ass and started fucking him right then and there. Why wait?

Not long after that I was sucking his cock and then of course eating his ass. I thought the original idea was for us all to have a threesome, but it just ended up with Delilah masturbating while watching us fuck. And just like all those times I watched her fuck other guys and sucked their cum out of her, she did the same with me after Victor filled me up. In reality, this was her plan all along. She knew that Victor had what it took to bring about a new me. A version of me that she was carefully curating to her own personal tastes. And as always, I was willing to be used in any way Delilah saw fit. When it came to sex, she had proven over and over again that she knew what was best for me, perhaps even better than I did. And now, Delilah was planning to take this theory to the next level.