I knew pretty early in my life that I was not going to be the most manly of men. I would love to dress in my mom’s heels and her dresses and put on her jewelry. When my Mom caught me one afternoon, she was actually thrilled and told me I make the cutest girl. After the initial embarrassment, I let my Mom do my makeup and we spent the rest of the night playing dress-up.

As time went on, my mom treated me more like a daughter than a son. We bonded over her helping me with makeup and having “mother-daughter” time. But as I got older, I tried to get past those feelings. I tried to fit in with the popular kids and even started dating girls. Of course, the whole time I was secretly wishing I could be like them and wear their clothes.

Eventually, I found a girl who I fell for who didn’t seem to mind that I was not very masculine.

So, for Valentine’s Day, I bought her some sexy lingerie and was going to surprise her with dinner and some romance at her apartment. I told her I would pick her up after work and take her out to a restaurant. Instead, I would surprise her with a meal fit for a queen. I left work early, went to her apartment, and started to get the night prepared. I laid the lingerie out on the bed and was going to prepare dinner.

As I finished up meal prep, the desire to try on the lingerie was overwhelming. I thought, “I still have plenty of time before I am supposed to pick her up.”

So, I slipped out of my clothes and put on the lacy bra and panties. It felt sooooo good. In fact, it felt so good, I thought, “Why not finish the look with some makeup? I still have a few hours.”

I had forgotten how much fun it was to be dressed and feel feminine. I remembered how free I felt as a girl.

I was starting to get very aroused and even began to rub my cock when, suddenly, I heard a click and the door open. Oh gawd, is it her!?!?! Oh no, I’m caught.

But it wasn’t my girlfriend. It was a guy breaking into her apartment looking for money that she owed him. I was frozen. I tried to hide, but he saw me and grabbed me thinking I was Lexie.

When he spun me around, he said, “You’re not Lexie! Who the fuck are you, bitch!”

I couldn’t speak, I was frozen in fear.

“Oh damn, you ain’t even a bitch, you’re a bitch boy,” he said. “Where’s Lexie!” he shouted at me.

“I…I…I don’t know”. I stammered.

“Well, you better find her! I want my two hundred dollars.”

“Two hundred dollars? What does she owe you for?” I asked.

“She is behind on her weed bill and I want my cash!” he said.

“I…I don’t have that kind of money…” I told him, forgetting I was dressed in her Valentine’s gift.

“Well, either I get my cash or I get what she owes me in other ways.”

“Holy Crap!” I thought. My girlfriend is a whore…for weed. I didn’t even know she smoked.

He kept looking at me, undressing me with his eyes, and it didn’t go unnoticed. Something awoke inside of me. I started to get turned on. All those afternoons spent playing dress up and feeling girly with my Mom came flooding back.

Maybe it was the lingerie, maybe it was the inner sissy that I tried to keep repressed for all this time, maybe I was just angry that Lexie had been lying to me, but all I knew was I wanted him deep inside me and I was going to make him cum inside me.

I slinked over to him and purred, “What kind of payment plan is Lexie on?”

“Well, the one that usually starts on her knees,” he said.

“I could try and pay off her tab, if you like…” I whispered in his ear as I felt his crotch.

His eyes got big and he said, “I think we can work something out.”

I unzipped his pants, pulled down his underwear, and out fell a thick, huge cock.

“Mmmmmmm! I see why Lexie likes to do business with you," I purred.

Mr. Big Dick responded, “Why don’t you open up that pretty little sissy mouth and say Ahhh!”

The next thing I knew, I was getting twelve inches of gorgeous, thick cock jammed down my throat. I gagged and choked, he was huge. He got harder and harder as I made as sloppy of a blowjob as I could.

He placed his hands on my face and said, “Damn, bitch, your mouth is so talented!”

I got even more turned on and went to work like a good sissy is supposed to.

As I was sucking this guy's cock, the door flew open and Lexie was being carried into her bedroom by her boss.

He screamed, “What the fuck is going on here, what the hell are you doing in my apartment!!!”

Mr. Big Dick said, “Well, I was looking for the two hundred dollars that you owe me, but this sissy bitch decided to pay your tab.”

Lexie looked at me and just laughed, “Well, well, well…I always suspected you were a little sissy, now I know! Ha ha!”

I retorted, “Well, I suspected you were a whore, and now I know.”

Then Lexie purred to her boss, "Well, if you don’t mind an audience, why don’t you fuck my brains out, while sissy boy pays my tab!”

“I don’t give a fuck, just let me at that pussy,” her boss said right in front of us. It was surreal, my girlfriend was getting fucked like a whore, moaning and moaning with pleasure, and I was in heaven wearing sexy lingerie and blowing a big, thick cock

Then, Lexie said, “If you want to swap, there’s lube in the drawer.”

Then the next thing I knew, Lexie was getting fucked and moaning with Mr. Big Dick deep in her pussy, and Big Boss Man had me on the floor, face down, grabbing my hips and using me like a sissy fuck toy. I never felt more feminine. I kept grinding my ass on his Big Boss dick. Then, he moved onto the bed and they both took turns fucking us. I don’t know who was moaning louder. Lexie and I even made out while the guys thrust deep inside both of us.

After Lexie and I had multiple orgasms, the guys covered us both in ribbons of delicious cum. Lexie and I licked up every yummy drop from each other.

While we were all eating, Mr. Big Dick said, “You know, we could probably turn your little bitch ass out and make some serious cash tonight.

Lexie just laughed, “If she fucks, as good as she cooks, we can make some serious dough.”

"Who’s this we?” I said. “If you are going to turn me out, I’m keeping what I earn!”

After cleaning up a bit, and Lexie helping me reapply my makeup, they took pictures of me in the lingerie. Then Mr. Big Dick sent some texts out and he led me to his car. Lexie called out to me.

“Hey, make sure you get top dollar for that ass baby, I might need you to pay off some other debts ha, ha, ha.”

I smiled back and said, “ Oh no, sweetie, this is for my new lingerie fund, ha ha ha!”

After a little while, we finally arrived at Mr. Big Dick’s place. He offered me a drink and we started getting cozy again, until his doorbell rang. He led two of the biggest guys I’ve seen into the apartment.

“Damn playa! you were not kidding. Look at that sexy little sissy bitch!”

The other guy kept licking his lips and rubbing his groin. I knew this was going to be a good night for me.

I led both of these studs into the bedroom and immediately got on my knees. They both dropped their pants and out popped two huge cocks. Within seconds, I started caressing their balls and licking their shafts. Both of these chiseled studs were looking at me like fresh meat as they got rock-hard. “Go ahead and get your money’s worth Playas!” said Big Dick man.

I was hotter than lava in August, my inner sissy was on full display. They were both so big, and I was intent on giving them an experience that was next level. I was in pure sexual bliss, feeling like a bad, bad sissy girl.

Two gorgeous guys, with huge dicks, fucking my mouth and my ass, and I couldn’t get enough.

They each took their turn leaving their thick, creamy cream pie in my ass. I licked up every drop that came out. Delicioso!

After they left, Mr. Big Dick, said, “You got any energy left? I got two more friends that want to get a taste of your sissy ass.”

I purred at him, “As long as they fill me up with plenty of milky protein, I can go all night and all day!”

“Damn bitch, I think you found a new calling!”

I stuck my tongue in his mouth, kissed him deep, and purred, “Sometimes, you never know what you’re good at until you try. And baby, I think I want to be the best!” Then I slinked into the bathroom, wiggling my hips and ass, to freshen up for my next opportunity.

Suffice it to say…I have a whole new appreciation for Valentine’s Day!