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Introduction:

Tyler's disguise proves to be a little too convincing and gets him in over his head

During my freshman year of college I decided I wanted to rush a fraternity. For those of you that don’t know what rushing is, it’s a process where you basically get to interview with all the different fraternities and they get to interview you. You find out the frat’s interests, meet some of the members, and basically see if you fit. Then on the final day of rush the fraternity sends out their list of bids to the individuals that they want to have join.

All of that went fine and I ended up getting a bid to the frat that I wanted.

After the rushing process, depending on the fraternity, there are a number of different initiation rituals that you have to go through.


My pledge classes first initiation was “Disguise Day”. On Friday all the pledges were supposed to dress up in a disguise for the entire day. It was pretty simple actually. Pledges needed to try and not be found from 8:00 in the morning until midnight. During that time you needed to have photographs taken of you in at least five different locations around campus. These photos would later provide both proof that you were actually on campus and not hiding in a hotel, and provide humor to the entire frat. What this meant is that you needed an accomplice. Either a fellow pledge or someone else you could trust. The accomplice had to take a couple of pictures of me at different times and locations. Just some simple documentation.

That’s where my friend Kelsey comes it. She was a sophomore and knew a thing or two about the campus. After being at the school for a year she was well versed on all the obscure hiding places. Plus she had everything I needed for my disguise. I was going to be a woman.

At 6:00am it started. I left my dorm and made my way over to Sigma Kappa sorority and was promptly met at the door by four sorority sisters. All sworn to secrecy and all with a deep desire to pull one over on their brother frat.

I was led up to a massive bathroom and told to strip.

Over the next hour I had my legs, arms, face, and begrudgingly pubic area shaved. My finger and toe nails were painted dark blue to match the dress that they were planning on me wearing. My eyebrows were plucked. I was dressed in black stockings, black panties, a black padded bra which was all covered by a tea-length dark blue dress. My hair, which was shoulder length, was teased, ironed, blown, braided, twisted, and fluffed into a very cute look. Finally, make-up was applied.

When the sisters finally allowed me to look in the mirror I was shocked. You always have this image of who you are in your head. So, when I looked in the mirror I flinched when the “normal me” wasn’t looking back. I looked pretty. I looked almost “too” good for a college campus. It didn’t hurt that I was smaller in size to begin with. Being 5’6” and only 130 pounds made it easier to disguise. Some of my other pledges were well over 6 feet tall and could never pull this off. But, from the look of it I could.

“Wow. I can’t believe that’s me,” I almost whispered.

“Here Tyler. Try these on,” one of the sisters said as she put a pair of black heels next to my feet. “I think they should fit.”

I stepped into the heels and watched myself rise up three inches. They were a completely different feel from my typical sneakers but so was much of what I was wearing. Stockings squeezing at my thighs. Silk panties gently holding my cock in place. A dress holding me snuggly at the waist. It was all very different.

After a few minutes of “walking” training we hurried outside to take picture number one. It was of me standing in front of the sorority house.

The day went by quickly and Kelsey and I had taken a number of pictures proving my existence on campus. But all the while there was a constant buzz on my phone as a text was sent out announcing that my fellow pledges were being discovered. By 6:00pm only 4 of the original 35 pledges were still not found. We only needed one pledge to make it the whole day for the pledges to not have to endure some untold initiation punishment.

At 10:00pm it was down to 2 pledges remaining undiscovered.

The last task requiring photographic evidence was to attend a party. It didn’t need to be my fraternity’s party. It just had to be a campus party.

The problem with all of this was every campus party would be policed by all of the fraternity’s brothers. They would be out in full force trying to find someone, anyone that looked out of place. Someone dressed with a fake mustache or hair covering their face. Maybe oversized clothes or someone hiding in a corner. Everyone would be checked and rechecked.

For this to work I needed to attend the party and get a picture. I needed to be there just long enough to get the picture and get out.

Kelsey, the accomplice sisters from the sorority and I all made our way out to what we thought would be a rather quiet party.

We were wrong.

We heard the music from 10 houses away. The quiet party was bouncing and we were heading right toward it. As we got closer I recognized a few of my fellow pledges walking on the road half heartedly looking around. They must have been put into service looking for the last two pledges.

As we came up to the door of a frat house we were greeted by a young man. “Damn!!! You ladies can go right in. That is if you give me your phone numbers,” a smiling freshman said hoping to get the girls to give out there numbers.

The freshman door monitor smiled at me as I walked in. Either he was drunk or I had just been flirted with. By a guy.

We made our way into the body of the party and found the bar.

“What do you want to drink?” Kelsey yelled into my ear.

“A beer,” I responded. Kelsey shook her head side to side and ordered me a Margarita.

“A beer is too masculine. I got you a margarita instead. We have to keep up appearances for just a little while longer.” The only problem is I had never had tequila before. I didn’t know what it would taste like or how it would affect me.

As the night started to progress Kelsey got a picture of me at the party which was the last picture that I needed. Now all we needed to do was get back to the sorority and not be seen before midnight.

I was standing there with my back to the room when Kelsey got a text. She looked up and announced that she would be right back and walked away.

“Wait here. I’ll be right back,” Kelsey said and walked away. I was alone. Standing in a room full of people drinking and having a good time all while the brothers of my frat were looking for me.

The catch was that I didn’t even know most my the existing frat brothers.

Two guys walked up to me and started talking. I didn’t recognize either of them but seeing that I had only been on campus for two weeks that wasn’t a big surprise. The hope was that they didn’t know me either and that I was different enough from any picture they had of me that they wouldn’t be able to recognize me.

The guys introduced themselves as Shane and Kendrick. Shane was about 6’2” and had a slightly muscled frame. Kendrick was a handsome black man that stood 6’6” and had a very pleasant smile and friendly personality.

They were flirting with me a lot but the benefit of that was that they were doing most of the talking. When Kelsey came back and joined the group she looked different. There was a panic in her eyes but I had no way of knowing what was going on. Kelsey’s phone buzzed again and again she looked at the message.

“I’ll be back in a minute. Then we need to get going. Okay?” Kesley asked. Kelsey looked at both of the guys standing with me and stared hard at me. I nodded and again she left. I didn’t know what Kelsey was trying to say to me. I nodded again.

“Hurry up. We can leave anytime,” I said looking at Kelsey. Kelsey turned away and left me alone with Shane and Kendrick.

The conversation was pleasant and flirtatious. They got me another margarita and we just talked. I could feel the alcohol causing me to relax my guard a little.

“Do you smoke?” they asked to which I replied that I had, a few times but not much.

“C’mon, let’s go outside,” Shane said.

Kendrick took my hand and led me out into the backyard and over into a dark corner behind the garage. Shane reached into his pocket and pulled out a joint. He lit it and took a long drag. He passed it to me and I did the same. Between the margaritas and the pot I was felling really good.

Standing there I looked up at Kendrick and smiled. It was really just a reflex action but he took it as an invitation and leaned closer to me.

Kendrick put his hands on my sides. “You’re really pretty. I don’t know if it’s weed or you but I’m really fucking horny.” Kendrick leaned in and kissed me. I pulled back.

What the fuck am I doing. I’ve got to get out of here. This guy wants to have sex with me.

Kendrick leaned in and kissed me again. He slid his hand up the side of my neck and held my head in place.

I felt Kendrick’s tongue slip into my mouth and we started kissing deeply. Kendrick stopped and took the joint from Shane and took a hit. While Kendrick was smoking Shane leaned in and kissed me. My senses were reeling. I could feel a stirring in my groin.

Kendrick got closer to me and took another hit of the joint and blew the smoke into my mouth.

The effects of the pot was causing me to smile and giggle.

“Have you ever been with a black guy before?” Kendrick asked as he took my hand and placed it on the bulge between his legs. I couldn’t talk so I shook my head side to side indicating that I hadn’t. I looked down at my hand on his groin. I was moving my hand up and down. Caressing him through his jeans. I liked the feeling. I loved the feeling. I could feel the heat. I could feel the shape of his cock and balls.

I loved when girls had done it to me. How they would rub my cock through my jeans. It would make me so fucking horny. I looked over and Shane and smiled while I reached down and placed my hand on Shane’s crotch and caressed him through his jeans, too.

My brain was spinning. I couldn’t believe I was caressing another guy’s cock. Not just one but two of them.

Kendrick kissed me again.

I felt Kendrick unbuckling his belt then he unbutton his pants. Finally he his pants down over his hips. This time I reached out and took ahold of Kendrick naked cock. Shane did the same. I was holding two cocks in my hands and stroking them.

I was confused. I knew I wasn’t supposed to be doing this. You don’t stroke another man’s cock. I could rationalize it but I couldn’t stop. There was something about the warmth of the cocks in his hands. Something about the feeling. I could feel my own cock getting hard.

“You sure you want to do this?” Shane asked.

“Yes!” Tyler answered in a whisper.

What the fuck am I saying? What the fuck am I doing? I have to stop.

“You’re so fucking hot. I want to fuck you so bad.” Kendrick whispered between kisses.

“I…I…can’t. I’m…It’s my period,” I blurted out knowing the disaster that would happen if they undressed me.

I leaned forward and kissed Kendrick and then Shane. Kendrick looked at me and smiled, “I have a feeling that you know how to use those soft lips. Yeah, I think you’re probably pretty good at it too?”

I wanted to stop everything. I wanted to scream out that I was a man. That I had a dick and balls under the dress but I couldn’t. The alcohol and pot were causing my brain to swirl and there was something about how hot and hard the cock between my fingers. I looked down and saw the fingernail polish on my fingers as I stroked the thick cocks. My hands looked feminine and small against the size of the cocks.

“I might have done something like that once or twice,” I lied with a grin. What the fuck am I saying.

“Kneel down. No one can see us,” Kendrick whispered into my ear. I could feel Kendrick gently pressing down on my shoulder. I hesitated and looked at Kendrick before allowing myself to kneel.

Kneeling in front of Shane and Kendrick I kept stroking the thick cocks. I need to stop. Fuck! I have to stop. I don’t do this. How do girls do this. His cock is so big.

Kendrick moved in closer. His cock was hard and sticking straight up right in front of my face. I was shocked at how big it was. I can’t do this.

Shane’s cock wasn’t as thick but it was equally as long. As I stroked both of them a droplet of clear precum appeared at the tip Kendrick’s cock. I knew what it was from jerking off but I had never seen it while I was on my knees with two cocks pointing at my face.

Oh! My! God! what am I doing. I can’t.

“Go ahead baby. Let me feel those soft lips. There’s even a nice little drop of precum for you. You like the taste don’t you.”

What? No? I don’t know. Fuck me! Fuck me! I can’t!

Kendrick’s hand slipped behind my head. I could feel myself being gently pulled forward.

“You sure you want to do this? We can stop.”

“I want to,” I whispered softly not believing the words that were coming out of my mouth.

“Open those sweet lips,” Kendrick said. I looked at the cock in front of me and partially parted my lips.

I closed my eyes and felt the tip of Kendrick’s cock touching my lips. The precum smearing on my bottom lip as Kendrick slowly pushed his cock into my mouth. As Kendrick pushed forward my mouth naturally opened and cock tip slipped in.

What the fuck am I doing!!!

Kendrick’s cock easily filled my mouth. I was straining to take the girth as he pushed deeper. I was letting him do everything. He was slowly sliding his cock in and out of my mouth. Finally, I started to take control. I didn’t feel Kendrick’s hand on my head anymore. All I felt was the thick cock sliding between my lips. I took a little more each time I went down on Kendrick’s cock. I was thinking about the feeling of his thick cock gliding across my lips. The world disappeared. There were no sounds from the party There were no concerns or cares. There was nothing but Kendrick’s cock filling my mouth and hand.

I started stroking Kendrick’s cock at the same time that I was sucking him. I tried to remember the times I had had my cock sucked. What had those girls done? What did they do that made it feel so fucking good. I slipped my mouth off of Kendrick’s cock to catch my breath.

“Damn girl. You need to slow down a little. You keep going like that and I’m going to lose it real quick.”

I looked toward Shane and pulled him to me by his cock. I kissed the tip like I had seen in porn videos. Instead of just taking his cock in my mouth I played a little more. I licked around the tip and made him wet before taking him in my mouth.

Shane’s cock was easier to take deep in my mouth because it wasn’t as thick but he was still really long. After sucking Shane for a few minutes I stopped and turned toward Kendrick.

I looked at the tip of Kendrick’s cock and saw the moisture glistening and licked the very tip. I tasted the precum leaking from Kendrick’s cock. I took Kendrick’s cock back into my mouth and started to work the shaft with my hands and mouth. I could hear Kendrick’s breathing getting labored and low moans escaping from his throat. I knew he was going to cum but I also knew that it was too late to stop. I should have stopped a long time before this.

“I’m cumming!!!”

Kendrick clinched my hair and pulled me close and held my head still. His thick cum surged across my tongue and spreading in my mouth. He held me tight as he kept squirting his cum into my mouth. I slipped Kendrick’s cock out of my mouth for a second and swallowed. Letting the thick liquid slip down my throat. I took him back in my mouth and softly sucked his softening cock.

I turned toward Shane and smiled. Shane stepped forward and let me take his cock into my mouth.

———

In the silence of the evening I thought I head a woman’s voice. A familiar voice saying,

“Yeah, it’s 1:00am. I haven’t found…her yet. I’ll keep looking. I’m at PSK. I’m going to go in and see if I can find her,” Kelsey said into her phone.

———

Shane and Kendrick didn’t seem to hear the soft voice. The girls from Sigma Kappa were looking for their dress up project. And here I was on my knees sucking a cock, two cocks, on my first night as a girl.

Shane started to thrust into my mouth. It didn’t take long and Shane stopped and let out a grunt. A thick surge of cum erupted from his cock into my mouth. It was quickly followed by another. Shane’s cum hit me in the back of the throat and caused me to choke so I pulled my head back. Another surge sprayed half into my mouth and half on my chin. Shane pushed his cock back into my mouth and his cum continued to spill out of his cock..

I swallowed as best I could but some dripped down onto the borrowed dress.

Kelsey turned the corner and suddenly stopped. “Oh, ummm, sorry. I heard something and thought it was my friend. And…um…I guess you found her,” a shocked female voice said.

I looked up and saw Kelsey standing there. Shane’s cock right in front of my mouth and cum on my chin. Kendrick’s soft cock still hanging out of his pants. There was no mistaking what was happening.

“I…umm… guess I’ll just wait over here….while…umm…you finish what you were doing.”

Shane kept stroking his softening cock and I looked up at him and took him back in my mouth. As Shane stroked his cock I felt a small surge of cum spread on my tongue.

“Keep sucking. Nice and soft. Ahh fuck yeah. That’s nice,” Shane said. I did as I was told. I really didn’t need to be told because I was doing it anyway.

Ten feet away Kelsey could hear Shane talking to me. Instructing me on what to do. She stood there in shock. Her hand over her mouth. Unable to do anything. Her phone buzzed to life with a text, “did you find him”.

Kelsey quickly tapped out a message and pressed send, “he was at PSK having a few drinks. we’ll be back in a little while”

“I have to go.” I whispered and got up and started to walk from behind the garage.

“Hey, wait. What’s your number. I really like you and would like to hang out again.”

When I turned the corner Kendrick and Shane were close behind. Shane was still fixing his pants and trying to buckle up. I had cum on my chin and on the pretty dress.

“C’mon. We need to get you home,” Kelsey said as she got close to Tyler. “Wipe off your face and fix your hair.”

“Hey, what’s your name?” Shane called out.

“Put your dick back in your pants. She has a boyfriend back home. Bye guys!” Kelsey said as they walked away.

———

Kelsey and I walked in silence back to the sorority house. The only words that were spoken were about Kelsey sending me the pictures we had taken during the day. When we got back I went upstairs and put my clothes on. Washed my face and left the dress and bra lying on the floor. I snuck out of the sorority house and back to the dorms.

I forwarded the pictures that Kelsey took of me throughout the day to the frat president. They would be used as evidence that I was never caught. I didn’t think much about it as I laid in bed listening to my roommate snore. Instead the memory of the evening came rushing back to me. I couldn’t believe what I had just done. To be honest I had never thought about giving a blowjob. I had never wanted to be with a guy. But things just happened. Things were just crazy and I did it. Even more shocking was that I liked doing it.

I slipped my hand down under the covers and touched the silky material of the panties I was still wearing. With my other hand I lightly traced my lips. Remembering the feel of the cock slipping in and out of my mouth. Tasting the cum that was on my tongue. My cock harden. Just the thought of sucking cock was making me hard. I started to stroke my cock lightly and felt the sudden rush of my orgasm coming on. I squeezed tight on my cock and pulled down. My balls rising up as the cum squirted under the covers. I could feel the warm liquid my stomach and chest. My cock pulsing cum everywhere under the sheets.

Fuck even thinking about sucking cock turns me on. I can’t even stroke myself 10 times before I came.

I fell asleep but didn’t rest well. I must have masturbated three more times. Each time just as powerful as the last.

———

I woke up at 9:00am the next morning. I grabbed my shower kit and walked into the bathroom. It was empty when I got there and I had the large shower room to myself. Twelve shower heads and one lonely individual. I’m not sure how I would have reacted had someone else walked in. Would I have looked at his cock? Would I have gotten an erection?

The frat president wanted everyone to gather in the living room of frat at 10:00am. So, I finished my shower, dressed and headed across campus. The 10 minute walk seemed to take forever. My mind was racing about what I had done the night before. I was surprisingly horny. I had sucked two, not one but two guys off. I don’t know why I did it. Maybe I was caught in the moment. Dressed the way I was. Feeling the silkiness of the panties on my cock. Maybe I just wanted to do it.

I walked into the Frat house and sat in the living room by myself as the others gathered.

“Hey, did you hear. They couldn’t find someone. We won’t have to do anymore of this crap,” one of my pledge brothers announced to me. “Do you know who it was? Where did they hide?”

“Me! I wasn’t found!” I said in a mumble.

“Okay, everyone shut the fuck up! Let’s do this. The meeting will come to order. You fucking panty wastes are the first group to ever succeed at this. But before we present the person that saved your asses we’re going to have a little fun. We’re going to show you all the pictures of how you were dressed, any pictures you may have taken while you trying to evade us, and what you looked like after you got caught,” the frat president announced.

The slide show took about 15 minutes and was accompanied by the required laughs. Then the president stopped. “Now for the savior of the pledge class of 2016.” The president clicked a button on a remote control and a picture of me standing in front of the sorority house came on the screen.

The pledges were cheering. The president spoke, “She’s prettier than some of the girls I’ve seen you guys hanging around with.”

The next picture was taken of me standing in front of the the Science Building. Another in front of the football stadium. A few more rolled across the screen and hoots and howls as the pictures of a pretty girl stood in each of them. The final picture was of me at the party.

“The amazing thing about last night is that some of the brothers actually saw this pledge. They thought he was a girl and moved on. The brothers actually talked with her but never figured it out.”

“Brother Tyler Hanson please stand up.”

I didn’t hear the request. I was too busy trying to hide my face.

“Brother Hanson! Please stand up.”

Slowly I rose to my feet. There was a thunderous roar by the pledge brothers as I got up.

“Come up here please.”

I walked to the front of the room and stopped in front of the president. The president reached out his hand to congratulate me on the success of not being found out.

I turned around and saw the faces of the pledge class and all the existing brothers.

Standing there at the back of the room was Kendrick and Shane. Staring at me. There eyes shifting between the picture of the pretty girl on the screen and the guy standing in front of them. The guy that has sucked them both off less than twelve hours earlier.

“A big round of applause to the first ever survivor of Disguise Day.”

Everyone clapped except Shane and Kendrick. The just stood there glaring at me. I couldn’t help but thing that a few hours ago I was on my knees with their cum in my mouth. Now they were looking at me like they wanted to kill me.

As the meeting adjourned and everyone made their way to the door I had this sinking feeling.

Kendrick stepped in front of me and stopped me.

“Mr. President! I would like to suggest that brother Shane and myself take on the task of training Brother Hanson personally. Seeing that it was us that failed to recognize the pledge it’s only fair that we teach him the ways of the frat and take this opportunity to get to know him better,” Kendrick said.

“That’s a great idea.”

When I finally walked out the door I was happy for my pledge class and the fact that we wouldn’t be having to endure the initiation process as pledges but at the same time I had this feeling that my initiation was just beginning and wouldn’t end until Kendrick and Shane graduated three years later.

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