Crossdressed and Fucked by Another Student

Ryan was at the top of his class. He was considered by many to be the brightest person at his college. He was smart, one of the smartest. His longtime crush and academic rival was Deva. They've been competing since elementary, always trying to top each other in grades. Now in freshman year of collegel, Ryan and Deva were both invited to a Halloween party, and Ryan couldn't pass up the chance to outdo his rival and possibly make a great experience out of it too. Ryan made a bet with Deva that he could score higher than her on an upcoming math exam. The winner would get to choose the other's Halloween costume. Ryan figured he had nothing to lose, if he won he'd get to see his crush wear something really cute, and if he lost he'd only have to wear something embarrassing for a night. (Little did he know...) Ryan studied day and night to assure his success. He was ready and confident on the day of the exam. He finished quickly and made a show of handing in his test earlier than Deva. Things looked good for him until the results came back, and not only did Ryan lose, but he failed the test. He accidentally skipped a problem early on, so all the answers bubbled in after were wrong. Deva walked up to him with a smirk. "Guess you should've taken your time and double checked, don't worry, I'll make sure to find you a good Halloween costume" she was taunting him. Ryan was upset but he figured that it couldn't be that bad. So he waited for the morning of the Halloween party when Deva was supposed to meet him to give him his costume before they headed off together. Deva arrived at Ryan's house wearing a mad hatter costume and greeted him with a cryptic. "I picked this one out just for you, I hope you like it." "Whatever, just hand it over already so I can put it on and get it over with." Ryan replied. When he looked in the bag that Deva handed him he was shocked. "No way! No!" Ryan shook his head. "Hey, a deal's a deal, too late to back out now. but tell you what, I'm feeling generous so if you wear this wig and I do your makeup nobody would recognize you." Deva grinned. "Fine... at least nobody will recognize me.. you're not allowed to take any pictures though! Promise?" Ryan asked nervously. "Okay, okay... it's a shame since you'll look so cute though!" Deva smiled and started on his makeup. She put a few layers of makeup on Ryan and before he knew it, he looked completely different. Once Deva was done, she put his hair into a hair cap and attached a wig to the top of it. The wig was blonde to match Alice in Wonderland. Deva asked Ryan to remove his clothes. Ryan was hesitant, but secretly had a crush on Deva. Ryan stripped down to his underwear. There was an awkward pause. Deva said, “I said remove your clothes.” Ryan stood there speechless. Deva went up to him and slipped down his underwear. He instantly got hard. Deva looked at his dick and smiled. She said, “Wow you are big!” Ryan didn’t say anything again. Deva pulled out a light blue thong from the bag and had Ryan step into it. She slid it up to his waist and tucked his dick into it. Ryan couldn’t believe that this was happening. He stuttered, “You are really pretty Deva.” She smiled and said, “You are about to be as pretty as me.” Deva put a match bra on Brian and slipped the dress over it. She then pulled out a pair of heels and had Ryan try them on. They were a little bit of a tight fit, but worked nevertheless. There were a few more items in the bag, but Ryan couldn’t see them. Deva said the last few items were a surprise. She told Ryan to lay face down on the bed. Ryan lied down on the bed and wondered what was about to happen. He felt some type of string being put around his wrists and legs. Perhaps it was some jewelry. Suddenly, the string tightened in all directions and his body was stretched out. Deva climbed on top of him and put a towel around his mouth. She said, “Shame to see some of your makeup ruined.” Deva slid a pillow under his waist. Ryan felt Deva getting off the bed and rummaging through the bag some more. He suddenly felt his dress getting lifted up in the back. Deva's hands clapped his ass and slid down his thong. Ryan screamed into the towel. Ryan could have probably broken away if he really tried, but he secretly liked what Deva was doing. Deva put some lube between his cheeks and slowly stuck one of her fingers inside of him. Ryan moaned a little in pain. Ryan heard the sound of velcro as Deva put on the strap. He knew what was coming next. Deva entered him and fucked him from behind. Deva started moaning too. Ryan was enjoying himself greatly and felt himself cum on the bed. Deva kept riding Ryan and reached over to pull the towel off his mouth. She said, “Look who is fucking who now. Everyone at college thinks you are so smart but look at you now. You are a pussy boy getting fucked in the ass.” Ryan didn’t have time to say anything as Deva pushed herself deeper into him right after she finished talking. Ryan got fucked for another 15 minutes or so before Deva got off of him. She used the towel that was tied around Ryan’s mouth and cleaned up the mess that was made. She slid Ryan’s thong back onto him and untied him. Ryan felt overwhelmed by what had happened. Deva hugged him and gave him a kiss on the lips. That made Ryan feel better. Deva checked her phone and said they were running late. Deva led Ryan out of the room and into the car. Both of them rushed off to the party. The rest of the night was pretty standard. Ryan never forgot the feeling of Deva fucking him and yearned for it.