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"Dude, come on, it's not a big deal. I won't tell anyone."
"I already told you Shawn I'm not doing it. Why does it have to be me anyways?"
"Tyler, you're the only one of our friends who would pass for a girl. To get into the party everyone must be entering with a guy and a girl. I'll even pay you $200 to do it or pay to fix your laptop."
"It wouldn't work anyways, everyone would know I'm a guy. The money would be nice but still, not worth it."
"My sister will do your makeup, she's a pro. I've already asked her and she's actually excited to do it. I guarantee this will work."
I let out a deep sigh of frustration. "Still someone is going to recognize me."
Shawn let out a loud laugh. "You can't be serious. If you were in a lineup but dressed not like a weirdo, no one in your classes would be able to identify you. You're basically the university's Unabomber, you're just missing the aviator sunglasses. Although I think your hoodie and sweatpants are much baggier than he wore. Why do you dress like that anyways?"
"First off I resent the uncle Teddy comparison, I'm not sending anyone packages. Secondly we've had this conversation multiple times, I dress like this because I've got fucked up genetics that caused me to go through a puberty closer to a girls. I wear baggy pants cause it hides my ass, the hoodie to hide my hips and wear the hood up all the time cause I gave up on trying to keep my hair short since it grows so fast and thick."
He smiled widely, "I remembered, I just wanted you to say it again so you would realize that you're perfect for this!"
"Who would I even go as for the Halloween party?"
"That's easy, Tifa Lockhart. I'm going as Cloud. It will be perfect. I'll pay for everything you need. You won't have to spend a dime, we will have a great time and you will actually get out of the dorm for a change."
"Why would I want to go as a girl anyways? Sounds like this is a couple's thing. I won't be able to pick up any girls and neither will you."
"Nah, it's not like that. The sorority putting on the party wanted an equal number of guys and girls. Thought it would make for a better party. I'm sure there will be some lesbians or bi girls, so it should work out for you. If not, it will be a night of free drinking."
I let out another long sigh, "Fine, I will do it. You're getting my laptop fixed and no matter what happens, after this is over, we never bring it up again. I don't want to hear snide jokes about it for the next three years."
"You got it! After the party my lips are sealed."
The two weeks leading up to the party came and went just like every other day of my life but the nerves about what was coming up grew and grew with each passing day. By the day of the Halloween party I could not pay attention in class. I'm normally a top student but this day I was all out of sorts, not answering any questions and unable to even take any notes. The entire day went by without me able to concentrate on anything. I can't even remember what I had for lunch or if I ate at all.
After class I walked into the dorm to find Shawn and his sister, I presumed, already waiting for me. Shawn handed me a beer right away, I opened it and took a large gulp. Fighting down the urge to let out a burp with a girl around, not wanting to be rude.
"You ready Tyler?" Shawn asked, looking at me with anticipation in his eyes.
I let out a long sigh. "I guess so. I've already agreed to this, so let's get it over with."
"Sorry my brother has no social graces, I'm Claire, his sister." She smiled at me and then turned to Shawn, clearly annoyed. "Did you get everything on the list that I gave you?"
Shawn nodded, handing her a big bag and then upon noticing I had finished my beer, he handed me another one. His sister grabbed my hand taking me to our bedroom out of the common room we shared with other people. She closed the door behind us, dumping the bag out on the bed, smiling approvingly, grabbing a pair of black short skirt and black thong, and then handing them to me.
"Did you shave off all of your body hair like I told Shawn to tell you?"
"Yeah... not that I had much to shave to be honest."
"You not having much hair makes my job easier." She smiled gently. "I will turn around, take off all of your clothes and put on the shorts and underwear." She took a bunch of the stuff off of the bed, taking her things that she brought with her and getting set up on my desk.
I took off my hoodie, sweatpants and boxers. Slowly pulling the thong up my legs, feeling the piece of material settle in between my butt cheeks was an odd feeling. Felt almost like the start of a wedgie. I pulled the skirt up next, it was so tight I had a hard time getting them up but eventually I got it up and settled into place around my hips.
"Okay, I'm done." I told Claire.
She turned around looking at me, her eyes wide, she stood up and began to touch my hair. "My brother said you had really long hair, I wasn't expecting this. Wow! It's half way down your back!" She smiled warmly, gently turning me around and then back to face her. "Wow, Shawn really should have gotten you a longer skirt. The bottom of your butt cheeks are literally hanging out. But since we are going with this look we might as well go old school." She pulled the top parts of the thong above the skirt.
I had given it little notice but now that she had it in her hands I couldn't take my eyes off of it. In her hands was what looked like a skin vest that closely matched my skin tone with huge realistic looking breasts with pink nipples and areola. She motioned me to lift up my arms, I followed her instruction, and then she shimmied down the chest piece until it was settled properly in place.
She looked at them and shook her head. "Why should I not be surprised that Shawn got you huge boobs. I said 'decent sized,' not massive." It was her turn to let out a sigh. With my arms still up she pulled down what looked like a black sports bra and then a white crop top tank top over it. The crop top was smaller than the bra leaving the classic Tifa top look of white over top of a bit of black showing. The combined tops did little to cover up the boobs, other than the nipples, rather they seemed to push them up and together making the huge breasts even more prominent. Claire set aside the black suspenders, red gloves, the black half arm sleeves, black thigh high thighs and red high top sneakers.
She pulled me over to the desk, sitting me down in my chair and immediately went to work plucking my eyebrows into a thin feminine shape. Next, giving my face a wipe with a wipe leaving my face feeling tingly and refreshed. She began to apply foundation all over my face. I was surprised at how well it matched my skin tone, Shawn picked surprisingly well as I was sure it was him tasked with picking up makeup for me. She coated my eyebrows in black, putting some light brown eyeshadow on my lids, eyeliner over the edge of the lids, down past the corner of my eye, light pink lipgloss, and finally finishing with a set of false eyelashes coated in mascara. She finished off by styling my hair into Tifa's style, the modern version since my hair wasn't down to my butt as Tifa had in the original game.
She handed me the black thigh highs which with instructions from her, I carefully pulled over my toes and then up my legs. She helped me pull on the black sleeves over my arms which sat just over my elbows. She handed me the red high top sneakers which fit perfectly although given that Shawn would have just had to look at my shoes and convert the size to women's, made that easier than his near perfect match for the foundation. Next, we put on the red fingerless gloves. Finishing off with a quick detail of my fingernails and a coat of clear nail polish.
Claire had me stand back up, pulling the suspenders over my shoulders, attaching them to the front sides of the skirt and then attaching the garter belts from the top of the thigh highs to the top of the skirt. She took a big step back, a big smile covering her face, happy with her work as she pulled out her phone, taking pictures and then showing them to me. I was amazed, there was still a little bit of me left but the rest under makeup and clothes was entirely Tifa and more importantly for the party female.
I smiled at her. "Thank you Claire. I don't know why I agreed to this outside of Shawn agreeing to fix my laptop but at least I look good. Are you coming to the party?"
"You're welcome Ty, at least you're getting something out of this even if it's my parents money," she giggled, "no I'm not going, now that I've graduated I have no use for college parties."
"I get it, still it's unfortunate that you won't be there. I feel like I would have a better chance of not getting caught with you there."
"Ty, I know this is going to sound mean but it's not meant to be, if I'm being honest and I didn't know any better, I would just assume you were a girl. Nothing about you screams boy, other than maybe what words you choose to speak but that can easily be explained by being a nerdy shut-in regardless of gender."
I let out a sigh. "Yeah, I guess I didn't want that to be true but I think you're right. It's not like I haven't been called names about it my entire life." I took a large sip of the beer that I had been slowly working my way through as Claire got me ready.
"You will kill it out there tonight. Just remember to try to smile and try to have a good time."
I put on as big of a fake smile as I could muster and then walked out of the bedroom to the common room. Shawn was already there, dressed in his full Cloud Strife costume with the bleach blonde ridiculous wig all gelled up, in the middle of pounding a beer, upon seeing me it caused him to choke on it and he started coughing eventually turning into a huge smile once it cleared with obvious signs of attraction and arousal.
"Wow Ty, you look fucking amazing! You look like the spitting image of Tifa. You should seriously consider doing cosplay. You would get all the attention at the conventions." He winked at me.
I blushed a bit at the compliment. "I'm not sure that's the kind of attention that I want."
Shawn turned to Claire, "Thanks for doing this sis. I really appreciate it!"
"You're welcome bro. You two look awesome, let's get a picture and send it to Mom and Dad. They will appreciate seeing your Halloween costumes, you know how much they love it. With Ty by your side they might think you finally found a new girlfriend too." She laughed a bit.
Before I could get out of the way of the picture, Shawn wrapped his much stronger arm around my waist, posing next to me. Claire started taking multiple pictures, eventually I got into it as well and started posing too. She showed us all the pics and we picked out the best to send to their parents. Claire left shortly thereafter and Shawn ordered us an Uber to the party.
"Hey Shawn, can I ask you a question?"
"Sure, what's up?"
"What did your sister mean by finally finding a new girlfriend? Also why haven't you found one. You seem like the kind of guy who could easily find one. You're tall, in good shape, have hobbies outside of school and working out and you're relatively intelligent. The only knock I can see against you is your social graces leave something to be desired."
He let out a big sigh. "It's only been eight months, she really needs to get off my back. I dated the same girl all throughout highschool and when we found out we got into schools in seperate States, we broke up. I've met girls here but I keep comparing them to my ex and they all fail. That's not their fault and it's something I need to get past. It's why I wanted to go out tonight and meet lots of girls, maybe find the one."
I smiled at him, "I think if you open yourself up you will find the right girl who makes your heart thump. Although considering I've never even had a girlfriend, I'm probably the worst person to give advice.
He laughed at my comment. It was nice to have a genuine conversation with my dorm mate. The last few months since we met we really only talked about school and our shared interests. We never really talked about anything when it came to matters of the heart or even about our lives. I knew he had a sister who went to the same university, who chose to stay close by after graduation and his family was well off but that was about it.
Our Uber finally arrived, so we made our way down and hopped in. The driver made a comment of how cute of a couple we were. I could feel my face burning with embarrassment, Shawn just laughed but didn't reply. We got the sorority house and I don't think I've ever been more nervous walking up to a door. I was sure that whoever was checking people in at the door would see that I was a guy and tell us to get lost.
Shawn rang the doorbell and shortly thereafter a girl in a Jessica Rabbit costume opened the door. She smiled at us, leading us to the table where they had blank name tags and different colored bracelets to indicate your sexuality and what you were looking for. I almost wrote my real name on the tag, deciding, in the moment, to just lean in and write down 'Tifa'. I would say that it was short for Tiffany or something if asked. We walked to the kitchen, finding a punch bowl and a keg. Without asking or waiting for me to say something Shawn grabbed a cup, filled it with punch and handed it to me.
He smiled warmly, "I'm really surprised you picked the purple armband. We haven't talked much about sexuality but I didn't know you were bisexual. Also declaring to everyone that you're DTF takes some guts."
I looked at him with shock and concern. "Wait. You're kidding right? I was a little thrown off by what name to write down but I was sure that purple was the lesbian bracelet!"
"Close but no, that was pink."
"Shit, I need to go back and grab the correct one."
Shawn grabbed my shoulder, not with a lot of force but enough to show he wanted to say something and didn't want me to move. It made sense that he would want me to be close with how loud the music was.
"You should give it a shot tonight. Just leave the purple one on. It will be nice to get some attention. You can just tell people you meant to grab the bi one but didn't mean to grab the DTF one."
I thought about it for a moment. I've never received positive attention for my looks in my entire life, it would feel good, maybe he was right.
"Okay, fine. I'll do it. I'm just not sure how I'm going to get through tonight without being nervous out of my mind."
Shawn pulled a very small baggie of powder out of his pants. "I know you've said you're not into doing drugs but this combined with the alcohol will make it a great night."
I let out another long deep sigh. I had gone this far today. What was adding one more thing to the list of things I thought I would never cross off. I handed him back my cup, unsure of how much to add, he dumped in half the baggie, stirred it around by swirling the cup and handed it back. I downed the entire glass, coughing after drinking it. Wow it was strong, it must have been close to 50% vodka in the punch. Shawn laughed at me coughing, took the cup and refilled it.
We moved out of the kitchen to the living room area, where all the couches had been put away leaving a big open area where people were dancing. Shawn and I started dancing together, me way more awkward than him. At first I tried to match what he was doing but it didn't feel right, so I looked over to what a girl was doing and copied her. It was going better until she started grinding on the guy she was dancing with. I immediately turned that down in my mind, choosing to stay with the moves she was doing previously. As we were dancing, some guy dressed as Mario smacked my ass from under my skirt, not that it was covering much, I turned around to chew him out but he just mouthed the word purple and I instantly got annoyed with Shawn convincing me to keep the purple bracelet.
I looked at Shawn who looked mad like he was going to go after the guy, I just mouthed to him to leave it be. He couldn't stop looking at the guy, staring daggers at him, so I decided to pull his attention back to me by grinding my butt up against his crotch. I looked back over my shoulder, seeing a look of surprise on his face turn slowly to arousal as I felt a bulge in his pants begin to poke me in the butt. I looked back over at the girl who was still grinding on the guy and did my best to copy her moves again. Shawn put his hands on my hips, holding me tightly, it felt nice to have someone's hands on my body who wasn't family. I lost track of time as we danced, the drugs and alcohol hitting my system.
Shawn grabbed my hand, eventually, leading me back to the kitchen for a refill. It was a good thing too cause I had built up a lot of thirst from dancing, or was that the drugs again? Hard to say. We walked around eventually finding the door to the basement open with a note on the door that said "Quiet Place" so we walked down, finding where all the couches had been moved to. There was only one that was open, the rest had all be taken up by couples making out or out right fucking in the case of one particularly advantageous couple.
We both sat down, Shawn taking the corner, he stretched out his arm and put it around my shoulders. I wasn't sure what was taking me over but my head felt like it was spinning, so I put my head on his chest. He started rubbing my head gently. It was a sweet thing.
I looked up at him and whispered into his ear. "You know Shawn, you don't have to take care of me all night. This was supposed to be so you could find a new girlfriend. If you want you could head back upstairs."
He smiled warmly. "I'm having a good time hanging out with you. If I had known spending time with you would be this much fun I would have done it sooner."
"Well if we had done it sooner, I don't think we would be hanging out like this," I said through giggles.
He laughed back. "No, I guess not. I know this didn't turn out how either of us planned but still, I'm enjoying it."
My head was starting to feel a little better, I looked up at him to see him looking down at me, our eyes locked staring into each other, slowly our heads began to move closer to each other as if being pushed my an invisible force, our lips touched and our tongues began to explore each other mouths. His arms gripping tighter around me, time became meaningless. I was surprised that my first kiss, it being from a guy, felt so right. The distant hum of the music upstairs provided the soundtrack to our makeout session.
After a long period of time that seemed to pass by in a moment, Shawn broke off the kiss before kissing me on my neck and then whispering into my ear, "want to get out of here? I got what I came for."
I nodded slowly, as he adjusted one of his arms to fish his phone out of his pocket and book us a ride home. We continued to kiss until his phone vibrated informing us our ride had arrived. As soon as we were in the back seat of the car, the kissing continued until we reached the front door of our dorm. We moved through the hallways making the way to our final destination of our bedroom.
We lied down together in my bed, our lips meeting again, Shawn began to strip off his outfit, I kicked off the shoes and stripped off the gloves, deciding at that moment to leave the rest of the costume on. Shawn was eventually down to just his boxers, I reached down wanting to feel his cock, I grabbed it through his boxers, it was considerably bigger than mine but so was almost every average penis. It didn't feel massive or scary in my hand, it was a nice size without being intimidating.
I looked into his eyes seeking permission to go further, he nodded, and my hand went under his boxers, feeling his cock in my hand without the obstruction of boxers. Slowly stroking it up and down. He let out a groan as he reached down, rubbing my hole through the thong I was wearing. I looked back into his eyes, giving him the same nod, he put his index finger into my mouth, I sucked it, coating it in my saliva, as he pushed aside the material covering my hole. He took his finger out of my mouth, began to slowly push against my hole, everything from the night leaving me relaxed and allowing my hole to easily accept the intruder. He very slowly pushed in and out, once he felt like I was warned up, he added a second finger, pushing them both in, reaching and then rubbing my p-spot causing me to let out a loud girlish moan.
I helped him take his boxers all the way off as he fingered my hole. I took his cock into my hand again, feeling the pre-cum leaking out of the tip, using it as a bit of lube to continue to stroke his cock. We began to make out again as we explored each other's bodies. I broke the kiss and whispered into his ear, "I want you inside of me."
A big grin crossed his face, he pulled his fingers out of my hole, positioning himself on his knees, putting my legs on to his shoulders, putting his cock at my entrance, slowly pushing in. The size was considerably bigger than his fingers but my hole eventually adjusted to it. His cock felt so good pushing up against my p-spot. I let out loud moans as he fucked me slowly. He began to pick up the pace, his groans beginning to match the volume of my moans. He grabbed my hips for more leverage as his pace picked up to full speed. He slowed down a bit as I felt his cock began to throb. I knew what was coming but I didn't care. I could feel my own orgasm building and I wanted every moment of. I swung my legs off of his shoulders, wrapping them around his waist. He stopped fucking, looking at me in surprise at first but began to pick up speed again, letting out a loud groan as he released his seed inside of me. I let out a loud moan as I came feeling the hot liquid in my hole.
He collapsed beside me, smiling happily and kissing me on the cheek. "Well I'm sure happy about how this night turned out."
I kissed his lips, "I couldn't agree more."
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