tagTranssexuals & CrossdressersA College Sissy Ch. 03

A College Sissy Ch. 03


There was the time I was playing hide and seek at my friend's house. I was hiding. I ran upstairs, looking for some place to sneak into so I wouldn't be found. I felt my time slipping, but before it was too late, my friend's sister caught onto the game we were playing and waved me into her room. Her name was Stephanie.

I was a shy kid, and my face turned red when I walked into Stephanie's room and saw a pink bra with rhinestones and lace strewn on the edge of her bed. She must have noticed because she giggled and said, "Do you want a really good hiding place?"

She was stunning; a senior in high school. I was just at the age where maybe I knew what attracted me to her, but no, not really. I remember her waist tapering in, perfect and soft, behind a tight, low-cut, white cotton t-shirt.

"Yeah," I said. Stephanie tossed me the girly bra I'd been ogling. I caught it and felt a stir in my belly like I'd only felt secretly looking through the Victoria's Secret catalog that came in the mail to my mother.

"I won't look, but put it on," Stephanie said. She turned and reached into a drawer and pulled out a matching pair of panties. They were soft and shiny and cut like a bikini, I thought, with a triangle in the front that turned into a full-butted cover in the back, with two elastic pink satin bands connecting the two at the hips. Stephanie stretched the panties with her thumbs and tossed them over to me. "Then I'll look for a dress that'll fit. We look like we're the same size."

I turned into the corner of her room and awkwardly pulled the panties up and fumbled with the bra. I couldn't clasp it behind my back. "How do you get this on?" I chuckled nervously, going with the whole game because I was, well, young and inhibited. And curious.

"Put it on backwards around your belly, clasp them in front of you, then turn it around and pull the straps over your shoulders," Stephanie said with a laugh. "Ooh! I forgot about this."

Stephanie pulled down a curly blond wig from the top of her closet and brushed it with her fingers. "I went as Marilyn Monroe on Halloween a couple years ago!"

She placed the wig on the bed, and racked through clothes in her closet. She pulled a dress halfway out, looked at it, looked me up and down, all lanky and shy in bra and panties, and she said, "Perfect!"

She pulled out a satin white dress, with a rhinestone buckle in the middle of the waist. It had two thick straps that went from the breasts over the shoulders and met at the collar on the back of the neck. The back was sheer white until it got to the butt, where it turned back to satin. The dress was long, with a slit going up the side of the left leg.

"I wore this to prom two years ago," Stephanie said. "Everyone said it was so pretty, but it's not like I can wear it again."

She waved me over to her and helped me slide into the dress. Feeling the satin against my skin was another bolt of lightning like I'd rarely experienced before. I didn't know clothes could be so evocative.

"Oh, this is good," she said. "Now some makeup."

Stephanie led me over to her dresser. As the dress stretched and rubbed against my panties, it created a friction and stir in me for what felt like the first time in my life. "You have such natural skin and a great bone structure, so we won't need much," Stephanie said. She put something colorful on my eyelids, some blush on my cheeks and some lipstick. Then she fixed the wig on my head and started to style it with pins and a flower hair clip she had on the dresser.

Stephanie leaned back and looked at me. "Stunning," she said. "He's never going to know where to find you," Stephanie said, and I remembered I was in a game of hide and seek. "I'll open the door and we'll paint our nails and he'll think you're one of my friends. You look like my friend, Natalie, anyway!"

I couldn't stand the thought of my friend catching me dressed like a girl. He was the kind of kid that'd go and tell everyone in school that I was a faggot and I'd never have a chance with making any friends, or girlfriends, ever again. But the truth was I liked looking like a girl, at least looking like this girl. And I liked that a girl as pretty and popular as Stephanie was in control.

Stephanie closed the blinds and turned on a few soft lamps. She pulled up a bag of nail polish and told me to pick a color. I picked a light, sparkly green and Stephanie giggled. She got up from the bed and said, "Ready?" and opened the door. My heart began to beat harder, but I didn't really look like me anymore so maybe my friend wouldn't notice.

Stephanie grabbed my left foot and started to paint the big toe. "So, do you have a crush on anyone?" she asked.

"Um, no," I said.

"Alex," she said, whispering, "Play the part."

"Oh," I said, turning my voice into a girl's. "Well, yeah there is this one boy."

"Who is it?" Stephanie said. I wasn't sure if she was giggling to keep up the role-playing or if she was giggling at how quickly I'd turned into a girl.

"Just this guy on the football team," I said.

"Giggle," Stephanie whispered. "My brother's coming."

I giggled in the girliest way I could pretend and flipped my hair back over my shoulder.

"Steph, have you seen Alex?" my friend asked coming into the room. He stopped in the doorway and looked at me. He smiled. I'd been caught.

"Brandon, have you met my friend... Natalie?"

"No," he said. "Do you go to our school?"

"No, she doesn't," Stephanie said, speaking for me. She must not have trusted my voice. "Ew, Brandon, stop looking at her like that."

I realized my friend had been staring at me the way I'd been staring at Stephanie earlier. I blushed.

"It's fine," I said to Stephanie, leaning forward to touch her arm lightly. Brandon turned red.

"OK, bro, get out of here," Stephanie said. "Go play your stupid little game. Aren't you too old for this shit anyway?"

Brandon brushed her off and turned to leave. "Bye, uh, Natalie," he said as he left.

"Ew, Brandon, go!" Stephanie finished painting the nails on my foot. "You know, you shouldn't break guys' hearts like that. It'll come back to bite you one day."


I woke up. I was back in bed, in college, with a lavender slip on. Bo was gone from the other bed. My mind started to come awake.

Was it a dream? Was I going down this road again? And what of the dream I'd had the night before — did that really happen, did Stephanie really feminize me when I was younger? Did she really take a photo of me and promise to show only her friends? Did she really then take that photo and pass it to everyone on the football team; on my football team? Did the football coach then really pull me into his office and ask if I was a 'tranny'? Did the upperclassmen post the photo on my locker and put pairs of panties in my backpack? Did I really have to leave transfer schools and promise to never think about this again? To block it out of my memory? To commit myself to being a regular guy who likes regular girls? To so thoroughly suppress the urge to go shopping for women's clothes or try on my sister's panties or pretend to be a girl online that I killed that part of me, and killed a part of what makes me human and happy? Did I really kill my true identity?

Or was it all a made-up dream? Did Abby slip into my room after the fuckfest the other night and whisper stories about how I've always been a girl into my ear? Did my brain turn those stories into memories so that I dream of them as if I've been denying my true calling in life: to be a woman who so deeply craves validation that she'll do anything other women say and perform any act on any man that comes by?

What confusion.

I was thirsty so I reached for my water cup. There was a note on my bedside table. I opened it. It read:

Hi cutie! You were wonderful at the fuckfest the other night. You showed your master and I that you're ready to be serious about becoming a woman, and acting like one. And even better, you showed me that you're a good girlfriend. So good in fact that I'd like you to come to our sorority rush party today. I think the girls will love you, and you'll finally have that sisterhood that I know you're craving. Meet me at KKG house at 3. I hope you've been practicing your makeup, your hair and your walk. Wear the clothes I laid out for you in your closet. Look hot. It's going to be a big night. Lova ya, baaatch.

I put the note down back on the table and smiled. Whatever transformation was happening — and whether it started years ago or really just this semester — was turning out to be a good one regardless. There were growing pains for sure, but that's because I had to overcome a lot of obstacles in my subconscious, it seemed. It required aggressive femininity to become a girl, and now that was on the other side, I was glad I had made the effort.

I got out of bed and put on the pink bathrobe Abby had given me. I didn't mind walking down the hall of the dorm to the bathroom anymore; girls scoffed and guys looked, but I had adopted this attitude that whatever I am, I am desirable. I'd gotten dozens of guys off, and I was starting to look like an actual normal college girl. That's what I told myself at least.

I hopped in the shower and shaved my legs and the little bits of my chest. I had gotten really thin after switching diets to look more feminine, but by butt was still a bubble that I'd learned to sway back and forth when I walked. I finished my shower and plucked my eyebrows in the bathroom. A nice boy from the down the hall, Rob, walked by and whistled playfully. He was one of the guys whom I'd sucked off in the basement the other night, and he patted me on the ass as he walked by and said, "Stop by anytime, Ali." He was clearly one of the guys who reacted well to the gangbang; some boys who were insecure in their masculinity and sexuality looked like they wanted to beat the shit out of me. I kind of liked the feeling of subverting their sexuality and fucking with their minds.

I went to leave, but instead paused and turned toward Rob's shower stall. I thought I'd thank him for his kindness. I put my robe on another hanger so it wouldn't look like we were in the stall together. I slid open the curtain and snuck in behind him. I reached my arm around him as he was washing his hair and grabbed his cock.

"What the-" he said. "Not here, man."

"Shh," I said. "And just pretend I'm a girl, 'k? Like the other night?"

I remembered the aweomse feeling of being a woman in control of a man. I dropped to my knees and took his cock in my mouth. He was hard already; I knew he liked me. Water came pouring down from his body down onto my face, making it hard to breathe with his cock in my mouth, so I pumped my head back and forth as fast as I could, rubbing my tongue underneath his cock.

He put his hand on the back of my head, and it occurred to me that this was the first time I was naked and having sex with a guy. I had internalized my femininity so much that I didn't need clothes or makeup to justify my girly actions.

Rob took the back of my head in both hands and pulled me down on his cock so my nose touched his stomach. He shot a massive load deep into my throat and I moaned in delight, swallowing as fast as I could. The warm jizz slid down my throat as I kissed the top of his cock, got up from my knees and left like it was nothing. I grabbed my bathrobe and went back to my room.

I opened the closet to see what Abby had laid out for me. I was shocked. Arranged neatly on the top of the dresser was the pink rhinestone and lace bra and panty set that I'd dreamed about the night before. The panties were satin and stretchy, and so sexy. The bra was so feminine, and felt so much like an expression of my style and identity. And then I saw the shoes: patent leather heels in the same shade of green Stephanie had painted on my toes in my dream, or when I was younger, or... I don't know when but they were the same.

I slid on the satin panties and tucked my cock into them. I loved the feel of the full satin bikini on my ass, and I couldn't keep my hands off myself. I slipped the bra on, and this time had no issue with the clasp; a subtle womanly quality I'd acquired over the course of the last few weeks.

Then I pulled out the dress Abby had picked out for me: a white, tight satin cocktail dress with two thick straps that met behind the neck. The back was full and sheer, and tapered down to just above the butt, where it returned to tight satin. Unlike the dress in my dream, it tapered off as a cocktail dress, like it had been altered from a prom dress to an adult woman's evening dress; like I'd graduated from playing games of dress-up to realizing that I may have always been better off as a woman.

I slipped the dress on, and it hugged all my curves. It came down mid-thigh, and my tan, smooth legs looked incredible in them. I put the heels on and squealed in delight. I had to tuck my cock back into my satin panties, becoming ever more a hindrance, to keep from showing my excitement.

I did my makeup for the event as a symbol of how I felt on the inside: playful, bold, exotic and utterly feminine: Big sparkly eye shadow that faded from silver to green from the inside of my eyes out; big thick lashes; a bright, cherry red lipstick that shined with gloss. I went heavy on contour, bumping up my cheekbones to highlight my eyes and make my face more feminine.

I was getting startlingly good at this.

I grabbed the long brown designer wig I'd bought and styled it like a pinup model got a makeover from someone on Jersey Shore. I puffed up the front of my bangs, clipping it on the top of my head, and straightened the sides, letting some strands fall before my shoulder, but the rest in the back.

I put on a string of pearls, because that's what Southern ladies do, I was told. I put on some pearl studs, too, and sat at my desk to paint my nails the sparkly shade of green from my dreams.


I was a little fashionably late to the sorority house. I knocked on the door and two young girls dressed in classy white peplum dresses invited me in. They giggled, but were very nice to me, and one said, "Come on in, Ali, it's so nice to meet you."

The two girls looked so perfect and pretty that it made me feel a little silly to be so done up and to have convinced myself that I was turning into a girl. They had hips and small waists and perfect little breasts; their hair was natural and long and stunning. They walked with grace I hadn't yet learned.

But as soon as I got down on myself, I was led into the banquet room of the sorority house and a group of 50 stunning young women were waiting to welcome me. They went into some kitschy chant about sisterhood, and Abby came from seemingly out of nowhere, and led me into the middle of the circle. All the girls were wearing the pretty white peplum dresses, with perfect makeup and perfect hair. They were smiling and clapping and cheering me, and I felt loved. I felt like a sister.

"Pledges, you are excused," Abby said. About 15 of the girls left the room, and the last one shut the door.

"Now," a blonde girl said. She was a Stepford wife type. "Abby here has told us all about you. And part of what we do as a sisterhood is welcome in girls who need some help becoming more feminine."

"But it's not a free proposition," Abby said, cutting in. "In order to be a Kappa, you need to prove to all the sisters here that you're committed to femininity, and committed to doing whatever it takes to become a sister. Does that sound like something you want to do?"

"Absolutely," I said in my new feminine voice. I heard some girls on the side giggle, but the blonde girl, the sorority president, Meredith, shot them eyes and they shut up.

"Perfect," Meredith said. "Well, you've done most of the hard work for us. You and Abby, at least."

"She looks great, doesn't she?" Abby said. The group of girls gleefully said yes in chorus.

"Thank you, girls," I said.

"Oh you're welcome, Ali," Meredith said, pacing back and forth in front of me. I watched as she gracefully walked in heels, a perfect model of womanhood. "Now, are you ready for your one and only challenge to become a Kappa?"

"Yes," I said, sitting up and arching my back. My legs crossed at the ankles like I'd been taught.

"Great, then come with Abby and I," Meredith said. "Say goodbye, girls."

The group of sorority sisters said goodbye in unison. The small group of pledges opened the door of the banquet room, and the two girls who let me in waved me to the front. Abby and Meredith followed behind me. When I got to the front, my vision went black.

"Now, we're going to blindfold you for just a little bit," Meredith said. "We do this for every girl who does this."

"OK," I said, nervous. It was hard enough to walk in heels with full vision.

We walked for about five minutes until I heard the deep bass of men's voices. I was led up some steps and into a building. I walked along a wood floor clacking my high heels, with the two pledges guiding my arms and Abby and Meredith talking quietly behind me, saying hello to guys as we walked down the hall. I could feel the atmosphere change; there was a lot of testosterone in this new building.

Finally we stopped walking, and the girls let go of my arms.

"On your knees," Abby said. I obliged. I heard the laughter of a pretty large group of guys. The blindfold was removed.

I looked around and I was in the middle of a circle of about a hundred guys. On the inside were about 20 naked boys around my age. They formed an immediate circle around me, Abby and Meredith. On the outside, the rest of the guys sat on chairs, stood in corners or rested on furniture with beers in hand, talking to each other and cracking jokes.

"Say hello to our new pledge, boys," Meredith said laughing. She had this disengaged quality about her that was unlike what Abby had shown me in this period. I was a tool for her, it seemed like, and I was beginning to learn that she hated everything about me.

The guys started laughing at Meredith's request, giddy with the prospect of humiliating me, and so I hated her, too, for that. Some of the guys made sarcastic catcall sounds, some were less tactful and said, "Look at that bitch," or worse, "Look at that faggot."

A good-looking guy in a blazer with broad shoulders and combed hair came out of the shadows and approached Meredith. "Hi Mr. President," she said sweetly. How quickly she switched from dom to sub in the presence of a strong man; Abby had done that with Bo, too. They whispered things in each other's ears, seemingly finalizing plans.

"Gentlemen of Delta Chi," the president said. "This is the culmination of our fall rush. Our 21 pledges stand before you, all with the hopes of becoming a brother of our organization. They have done everything we have asked of them. Not all who started have made it until today, but the ones who do stand here have earned the right to do so. This final contest will serve as the final challenge of rush."

The crowd of guys burst into cheers.

"Now, upperclassmen, you know what is about to happen," the guy said. "Before us we have a sacrifice from the Kappas. This... thing... is a sissy little bitch that the lovely Abby here has made as feminine as possible."

The crowd cheered again. For Abby, I'm guessing, because she raised her arm in the air and waved.

"We've set up a challenge to see how dedicated these pledges are to the fraternity. This tranny whore will do everything he... or, uh, she... can to turn on our pledges. The first pledge to get a boner will be kicked out of the fraternity," the president said. "That is, unless they have sex with the tranny right here, in front of all of us."

The crowd whooped into a holler. The 21 pledges looked at each other, and then at me, and then back at each other. I felt so humiliated, and not at all like a woman. I felt like what the guy'd called me: a sissy tranny faggot.

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