Borrowing My Friend's Cheerleading Outfit

Hello again everyone, it's Rose! This is a follow up to my last story I wrote which you can find on my profile. Enjoy!

It was now after Christmas, and I was doing nothing but thinking about the encounter I had at the adult store. I hadn't set up another hookup with the man I sucked just a few days earlier yet, but I was planning to. My best female friend Diamond came over. She was really the only person who knew about my crossdressing and secrets and such. She had long, dark hair. Beautiful, milk chocolate colored skin, and was curvy in the right places. To be honest I wondered why she hung with me because she was sort of popular and I definitely wasn't. We got along great and even flirted a lot. I'll go more in detail about our relationship in later stories.

While she was over, she took my phone to look at something and found her way to my pictures. "Oh my god! What are these!?" She found the pictures that the man at the adult store had taken of me while I was dressed up. I took the phone in shock. "Were you gonna tell me about this!?" She said with a look of shock, but also a smile. "I was going to tell you today, but I didn't know how to bring it up..." She smirked, telling me that she already knew everything about me, so why hold back now. I told her all about what happened, every detail. She loved every second of it. Her eyes wide at every detail while she flipped through the pictures he took of me. "So, he didn't fuck you??" She asked as I got to the end of the story. "Um... no. I got his number at the end though." She started thinking. "Oh well then we're setting something up with him right now then! Hold on, I'm gonna go home and get something, I'll be right back." She left in a hurry, but we lived in the same neighborhood so she wouldn't be long. I was nervous and excited to see what was going to happen.

Diamond came back to my house rather quickly with a bag and we went back to my room. "I think you would look great in this!" She pulled out her cheerleading uniform. Long sleeve top with our school's letters across the chest and the frilly skirt that went along with it. She also brought her pom poms. "Well put it on, let's see!" I had dressed up with Diamond before, but nothing this revealing. I put on the cheerleading outfit. The top was a bit small and basically turned into a crop top. The skirt barely covered my ass. Luckily our school colors were red and white, so the stockings and heels I got from the adult shop matched perfectly. Diamond also did my makeup for me to complete the look. “My god you look hot! Ok, now we’re going to send him some pictures.” Diamond took my phone and started taking a ton of pictures of me, telling me how to pose and so on. “I’m definitely keeping some of these for myself!” She said while laughing a little. She sent the pictures to the guy and we waited

It didn’t take very long before he replied. The dirty talk started immediately. He loved the outfit of course. “Um… it says he wants to come over..” I was still nervous even though I really wanted it. “Well, tell him to get his ass over here then!” Diamond wasn’t shy at all. “I’ll let him in and just chill in the living room while you two fuck.” She was so excited and she wasn’t even the one who was getting any dick. We tell him to come over and he does. He got to my house in record time. Diamond answered the door and I can hear him come in and walk towards my room. Diamond opens the door for him. “There she is! All dressed up for you!” I stood up, still holding the pom poms and smiled nervously. “You were right, she does look like a pornstar!” The man and Diamond laughed a little at that comment. Can’t say he was wrong and I enjoyed looking like this. “Well I’ll leave you two alone. Have fun!” Diamond closed the door and left. “Well… it’s nice to see you again…” I didn’t know what else to say. “You too. I’ve always wanted to fuck a cheerleader.” He didn’t waste any time and walked towards me while unbuckling his belt.

He pulled his cock out, looked even bigger with proper lighting this time. “Well get to it slut!” I immediately get on my knees and happily start sucking his cock. All the nervousness just went away and the horny took over. “I hope you fuck as good as you suck cock.” I just kept sucking. And sucking… and sucking. As best as I could I slobbered all over his cock. He put his hands on my head and started moving his cock in and out of my mouth. “Fuck… you ready to have this cock inside you?” I backed off his cock, looked up at him, and nodded while biting my lip. I was done with dildos, I wanted the real thing. “Good. Bend over the bed ms. cheer captain!” He grabbed the lube as I lifted my skirt.

He lubed up and smacked my ass a few times before putting the tip right against my hole. “Spread those cheeks slut!” I grabbed my ass and spread it apart for him. He slowly pushed in until the head was inside me. A small moan escaped my lips. The dildo practice definitely payed off. He kept slowly pushing in. I was breathing as best I could. Before I knew it, he was balls deep inside me. Right up against my ass. “Fuck.. you’re tight. I’m gonna enjoy this!” He started moving back and forth. I can’t believe this was happening. My first fuck. Dressed up as a slutty cheerleader. Being fucked by a man in his mid 40s. All while my best friend could hear us in the other room.

He grabbed my wait and started pumping faster. My moans got louder and louder. “Oh fuck! Yes sir please keep going!!” That stirred something in him. He put my arms behind my back, I was face down, ass up now. “Oh you like that don’t you slut. Your friend can definitely hear you now. Moaning like the whore you are!” He wasn’t wrong. I was moaning loud enough for the whole house to hear. “C’mon slut beg for it!” I obliged. “Please sir! Pound me with your cock!” He started slamming into me. No mercy. As hard as he could. I was making so much noise now. Just moans of pure pleasure. “Fuck…. Fuck…. Fuck… oh my god! Yes daddy!” I couldn’t believe I just said that, but here we are, no secrets anymore. “Say thank you to your friend for me. You ready for my cum?” Of course I was. “Yes sir! Give it to me!” He thrust into me as deep as could and shot his load into me. I was in heaven. My head was fuzzy in a good way. “Good girl…” The man pulled out and cleaned up and left. This was my life now. Laying face down, ass up on my bed, dressed as a cheerleader, with another man’s cum deep in my ass. The more I thought about it, the more I loved it

“Hi there slut! Sounds like you two had a great time!” Diamond leaned into my room from the doorway. I rolled over and smiled at her. “You can keep the cheer uniform Rose, I think you’ll need it more than me!” Diamond laughed. “Thanks for pushing me to hookup with him again Diamond.” She smiled, “of course! Guess I’m your pimp now huh?” We both laughed as I went to clean up. Little did I know, she kinda would be my pimp for the for a little while….