Frat Sister

Copyright M.C. Questgend 2017 – all rights reserved

Reproduction and copying by any means is not allowed under copyright law. This is a work of fiction.  Any resemblance to characters, living or dead, business establishments or events are entirely coincidental.

WARNING: This book contains material of a very explicit sexual nature and is intended for adult audiences only.  The author does not condone unsafe sexual practices.


For the last five years, I’ve had a pretty happy life. It wasn’t always that way. I fought like hell to live the life everyone wanted me to until there was no more fight left and I accepted the life I was really meant to live… my life as a woman… well at least a beautiful facsimile of one. After graduating from college, I took some time to travel through Europe and get my new identity established and legal paperwork in order, before returning to the States and settling down in a new town with my new job and new life.

Living my life as a woman, at least at the beginning, was eventful, to say the least, but eventually got lonely for me. I dated a lot but never got too far passed giving fantastic blowjobs and getting an occasional massage of my breast implants. As time went on, I found myself going out with girlfriends or just spending time at home alone… Fearing my surprise would be discovered. I knew my life couldn’t continue this way. Fortunately, a postcard in the mail would change my life forever.

A few weeks back I picked up my mail and found a large brown envelope from my mom. My family knew about my decision, but couldn’t accept it.
My mom and I stayed as close as we could without actually seeing each other and every so often I would get a package from her filled with my mail. I guess she thought it was easier than just telling the mailman to forward it or maybe it was her way of coping… as long as I was still receiving mail, she never really lost her son.

As I went through a stack of letters, most of them found their way into the trash can, but one thing caught my eye. A postcard from Devin; an old college buddy and fraternity brother. He sent me a short note to let me know the fraternity brothers from our graduating class were getting together for an unofficial reunion. My initial thought was to add it to the stack of trash, but there were a few problems with that. One, Devin and I were good friends and I knew he wouldn’t stop looking for me. The other problem was I really wanted to see him.
The rest of the frat brothers I could miss, but not Devin. I secretly had a crush on him all through college. He was a year older than me and was my protector during my four years.

A big part of me wanted to go, if for no other reason but to see him and tell him how I really felt about him, but I couldn’t do that in front of everyone. I thought about it for the next couple of days then sent Devin a letter with my email address. In it, I informed him that I would not be attending. After thinking about how everyone would react, I thought it would be best just to remain absent. A day later, I received an email from Devin who was rather upset that I was not joining them. He included his phone number in hopes that I would call him to explain, but I was too afraid to, so I tried to ignore him, but the emails kept coming.

I finally gave in and said that while I would not be attending the reunion, I would agree to meet him for dinner the night before. I told him things would become clear at that point and that was the only way I would agree to meet with him. He quickly replied and we were now going to have our first date, although, I don’t think Devin considered it the same way I did.

I drove into town a couple of days beforehand and prepared myself for our dinner date. I bought a new outfit and kept thinking about how he was going to react. I was taking a huge risk by exposing myself to him and well I figured if I was I would do it right. After taking a long bath and shaving my legs and other unmentionable areas, I rubbed lotion all over my body. I then slid on a pair of lace panties that barely concealed my surprise gifts. After putting on the matching bra, I slid on a pair of black nylons and a garter belt. Then came the dress. A beautiful red dress with a plunging neckline and a nice slit that ran up the side. I loved the dress and knew that red was Devin’s favorite color. I slipped on a pair of black pumps and after fixing my hair I sat in the hotel room scared to death to leave.

What was he going to think?
How was he going to react? Would he just leave or humiliate me? The more time I had the more frightened I got. I found myself going nuts just thinking about all of the bad things that could happen, that I was almost late for dinner. I rushed to freshen up, grabbed my purse, and headed down to the hotel restaurant. Before the elevator doors opened, I took a deep breath and confidently stepped out.

I walked down the hall and as I approached the restaurant, I could feel my heart beating faster and faster.
I looked around the half-empty restaurant and didn’t notice him anywhere so I decided to sit at the bar for a few minutes. After a half hour, I was planning on leaving, when I saw Devin walk in. He walked up to the bar and after ordering a drink he started to look around nervously. I took a chance and decided to try and strike up a conversation.

“You look a little nervous,” I said.

“Yeah, I am running really late and I think my friend may have bailed,” Devin said.

“Yikes, bet she’s not happy, why don’t you call her,” I suggested.

“I would if I had her number, we had been chatting over email.” he replied, “I was looking forward to meeting up with an old friend of mine.”

“Why don’t you email her again and explain?” I asked.

“I don’t know, my friend was not really keen on meeting with me.” he said, “I think he is pissed at me.”

“He?” I asked, “Sorry about that, I thought you were meeting with a young lady.”

“It’s okay.” he replied, “I would just like to see him.”

I talked him into sitting with me at a table where we could talk more privately without having to talk over the crowded bar. After he emailed “me” we continued the conversation.

“I don’t want this to come out wrong, but it sounds like you and your friend were close, did something happen?” I asked.

“Well, we hadn’t seen each other in a few years and to be honest, we didn’t part on the greatest of terms,” he replied.

I was confused because I didn’t remember us parting on bad terms. So I asked, “What happened, did you steal his girlfriend or something?”

“No, nothing like that.” he explained, “We were hanging out and both drank a little too much and he mentioned something that I wasn’t expecting and well let’s just say, I didn’t handle it the right way.”

Now I was really worried about what I might have said that made him react that way. He seemed very upset by it and I wasn’t sure how he would react to me now considering why he showed up in the first place.

“Is that why you think he isn’t here?” I asked.

“Well, I hope not, but maybe.” he replied, “We were supposed to attend a reunion tomorrow night, but he said he wasn’t going to attend. I can only think that is why.”

“That doesn’t make sense,” I said.

“He was very private and when he opened up to me, it was a little strange. I think he may think I shared his secret with our frat brothers.”
he explained.

“Did you?” I asked.

“Are you kidding,” He replied quickly, “I loved him.”

I couldn’t take it anymore and was fighting back tears when I handed him my phone that showed his email on the screen. Devin looked up at me and just stared for a second.

“It’s me, Devin,” I said.

“Mikey?” Devin asked as he continued to stare.

“It’s Michelle now actually,” I said.

He quickly got up from the chair and put my phone down in front of me and looked at me very seriously, but didn’t say a word. He just stood there frozen.

“Devin, I am sorry, I was so nervous and didn’t know how you would react.” I tried to explain as I got up from the table.

As soon as I got up he wrapped his arms around me and pulled me tight.

“I am so glad you are here,” he said.

“Me too,” I said as I slowly brought my hands up to his back.

We sat back down and ordered another round of drinks and he spent the next several minutes apologizing for how he reacted five years ago. While I was still dumbfounded about what really happened all those years ago, I was even more astonished about how he reacted to seeing me as a woman.

As we started to relax and open up more, I said, “I am really sorry that you have been carrying all this baggage around with you, because to be honest I don’t remember any of it.”

“I felt so bad all these years, I just wanted to see you face to face and say I’m sorry,” he replied.

“I know this is going to sound stupid, but what the fuck did I say to you?” I asked.

“You said that you wished you were a woman so you and I could get together,” he replied.

“Oh my god.” I said, “I am the one that should be sorry for making you feel so uncomfortable.”

“Uncomfortable or not, I shouldn’t have reacted the way I did.” Devin explained, “And when I tried to get a hold of you, your folks said you had left the country.”

“Well, I am sorry about that.” I said, “I had a lot on my mind obviously.”

“Sure, and it looks like you found what you were looking for.” he said, “You look fantastic.”

“Thanks.” I replied, “Still working on things, but I have to admit, I’ve never been happier.”

“Do you mind if I ask you a personal question?” he asked.

The restaurant was filling up and I wasn’t sure how personal he was about to get, so I suggested we go for a walk instead. Devin paid the bar tab and we left the restaurant. As we walked through the park across the street, I held Devin’s arm and he didn’t seem to mind. We continued to talk and I was really enjoying his company.

“What did you want to ask me?” I asked.

“It’s not important,” Devin replied.

“Devin, it’s okay.” I said, “You can ask me anything you want.”

He hesitated for a minute and fumbled his words as he asked, “So, did you have the full surgery while you were in Europe?”

“I had the breast implant surgery, but I am still packing I guess you’d say,” I replied.

“Oh… okay… “ he replied.

“Does that bother you?” I asked.

“No, I was just curious,” he replied.

He quickly changed the subject and I could tell he seemed a little disappointed by my answer, so, I didn’t press him on it and decided to ask about him and his long-time girlfriend.

“So how’s Gina?” I asked.

“Well, I don’t really know, we broke up a year after college,” he replied.

“Oh, I’m sorry,” I replied.

“It’s okay, it was for the best. She was going away to med school and I couldn’t go with her,” he explained.

Devin then brought the conversation back to me as we worked our way back to the hotel entrance.

“So, how long are you going to be in town?” he asked.

“Well, I live an hour away, so it’s not a big deal.” I said, “Are you staying here at the hotel?”

“Actually I am staying at a hotel by the airport,” he said.

“Oh, I just assumed since we were meeting here, you were staying here.” I replied, “I went ahead and got a room here, just in case.”

“I am really glad you and I could get back together,” Devin said as he looked at me with a much different look.

“Me too,” I said as I looked deep into his eyes.

I don’t know why, but I then just took him by the hand and asked, “Would you like to come up to my room with me?”

He looked at me hoping I would ask and simply nodded his head and the two of us headed upstairs.
I held his arm down the hall and opened the door. As I asked him to come in and I shut the door, I turned around to find him standing in front of me. He quickly grabbed me by the waist and kissed me passionately as he pressed me against the door.

My leg found its way up and around his waist as I wrapped my arms around him digging my fingers into his back and shoulders. As we continued to kiss, he picked me up and I quickly wrapped both legs around him as he moved his hands to cradle my butt. He moved me to the bed and gently laid me down. He began to nuzzle my neck and I began to remove his suit jacket and pull his shirt that was tucked neatly into his pants. He began to pull up my dress and I immediately grabbed his hands.

“Are you sure you want to do this?” I asked.

“Yeah, I want you right now,” he replied quickly.

“Then roll over,” I said as I rolled him onto his back.

I slowly slid my hands down his chest as I unbuttoned his shirt, continuing down to his pants, gently massaging his thighs while pulling his legs apart. I looked back up at him and noticed his eyes shut and his head firmly pressed against the pillow. I began to unbutton his pants, keeping an eye on any signals he may be giving off – just in case he started to feel uncomfortable.

I slid his pants off and slowly ran my red fingernails back up his legs and across his inner thighs causing him to shake slightly. I looked at his bulging cock, pressing on his underwear, and carefully pulled them down, exposing his enormous gift to me. I dropped to my knees and kissed his inner thighs, which seemed to be a sensitive spot for him – and worked my way up as I gently took hold of his meat and began to stroke him slowly.

“Oh yeah.” he whispered, “Yeah, that feels good.”
“You like that baby?” I asked.

“Sshhhh…” he replied.

I continued to stroke him;
Firming up my grip as I could feel his cock begin to swell. I then moved closer – keeping one eye on his face and the other on his massive cock. I gently kissed the tip and his legs pressed against my sides. I knew he was really enjoying the foreplay so I continued to make him happy, toying with his cock by running my red lips down the shaft and returning to the tip with my tongue.

“Oh yeah baby…” he said as his hand found its way to the back of my head, “Yeah baby, just like that…”

Getting confirmation that I was giving him what he wanted, I decided to give him that much more as I slowly slid his cock over my lips, and with them pressed together, I push his cock through my tight lips, penetrating my mouth.

“MMMmmmm…” I said with a mouthful.

“Yeah baby… YEAH… YEAH…” he replied.

I continued to mouth fuck him, applying just the right amount of pressure on his cock to make his legs rise in the air as I moved my other hand down and tickled his balls.
We were both getting what we wanted, but I was getting the better of the deal as I had dreamt of this moment for years.

As I kept pleasuring my dream date, he began to pull my dress up trying to take it off. So I pulled back and helped him. As I pulled the dress off, he leaned forward taking off his jacket and shirt. I dropped back on him making sure he stayed hard as a rock and he fell back on the pillow behind him.

“I want you so bad,” I whispered.

“Oh yeah, I want you too baby…” he replied.

“Do you really want me baby?” I asked.

“Oh yeah…” he replied.

I wasn’t sure if he was serious or just caught up in the moment, so I just figured I would finish off his blowjob and see how he reacts, but I didn’t get the chance. He sat up and pulled me up by my shoulders and kissed me passionately.

He then leaned over kissing my neck and whispering in my ear, “I want to make love to you.”

I was blown away. I tilted my head down then looked back up to him and asked, “Are you sure?”

He didn’t respond, but with a seductive look and a smile, I knew what he wanted. So as he slid to the edge of the bed, He held my hands as I stood up. He then stood up in front of me and firmly grabbed my ass. He then spun me around and threw me onto the bed.
He grabbed a hold of my hips and pulled me up to my knees.

“Yeah baby, I want it… give it to me baby.” I said.

“SSSHHHH…” He said as he playfully spanked my butt.

I turned around and closed my eyes, just waiting for him to penetrate me, but instead, I got even more.

“AHHH…. OOHHH… YEEEAAHHHH….” I uttered as I started to shake when he began tickling my pussy with his tongue. “Oh yeah baby… I love it when you lick my pussy.”

He ran his hand up and down my inner thighs before latching onto my cock and firmly stroking it. I was so excited and really surprised that he would even consider what he was doing to please me.

“Oh yeah… fuck… that feels so good…” I said, “I want you inside me baby… please fuck me…”

He stood up as his fingers penetrated me and I could feel my ass get wet as he spit onto my pussy and his fingers start to heat up. Then he pulled out his fingers and the next sensation I felt was his rock, hard, thick cock entering my body.

“OOOOO…. MMMM… FUCK YEEAAAHH…” I shouted as he slid inside me.

“Are you okay…” he asked.

“OH YEAH BABY… GIVE ME THAT BIG COCK.” I demanded, “FUCK ME… YEAH… STICK THAT COCK ALL THE WAY INSIDE ME…”

He complied with thrust after thrust of his cock sliding in and filling my hole. I occasionally turned to watch his face as his eyes remained pressed shut as he enjoyed the tight pressure of his cock being squeezed by my even tighter pussy.

“Yeah baby, I love it… stick that cock in me…” I said.

“Yeah baby… uh…uh… UH… UH… YEAH… YEAH… OH YEAH…” he said as he was nearing his climactic finish.

“Come on baby, I want you to cum all over me,” I said.

He quickly pulled out and I moved into position as he exploded all over my face.

“Oh yeah… baby,” I said, “That’s it… give me all of it.”

I grabbed a hold of his cock and continued stroking him, squeezing out the rest of his white hot cum as it dripped off his cock… and my chin… down onto my tits. I wiped his cock against my face covering the tip of his cock with his gift and immediately took it back into my mouth, playing with it a little before swallowing.

I pressed my head against his midsection as he placed his hands on my shoulders. I could feel his heart racing through every part of his body – slowly calming down as I caressed his legs. He then brought me back to my feet and held me against his chest.

“I’m sorry,” he said.

“Sorry? For what?” I asked.

“For not seeing this sooner,” he said, “For rejecting you like I did years ago.”

“Don’t apologize, you have given me more than I ever dreamed,” I replied.

“Are you sure you don’t want to go to the reunion?” he asked.

“What do you think?” I replied, “Do you honestly think you can walk in and look at me and not feel something?”

“I guess you’re right.” He replied, “Maybe it would be best… at least for now.”

“I know that someday I will have to face them, but not now,” I said.

“Can I see you again?” he asked, “Maybe after the reunion?”

“Who knows…” I said, “Maybe… besides, you may be a little late for the reunion.”

I then reached up and kissed him passionately and began kissing my way back down his body for some more playtime.


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