tagTransgender & CrossdressersStart of the Summer Ch. 01

Start of the Summer Ch. 01


The best times always seem to come at the start of summer vacation. It was the end of my sophomore year and almost everyone had gone home. It was just me and Brad left in the frat house, drinking beer and playing video games, killing time until our families came to pick us up tomorrow. It was fun, actually. Brad and I had gotten to be friends over the past two years but there were usually so many people around – frat brothers, friends, girlfriends, anyone and everyone -- that we never really got to hang together. But playing video games in our empty living room on our old tattered couch, an epic battle was shaping up. Brad won the first two games but I came back and won the next two.

"OK!" Brad said, "tiebreaker game coming up!"

"I'm going to make it 3 in a row and kick your ass!" I boasted.

"Yeah?" he challenged? "You think you can kick my ass?"

"Damn straight!"

"OK then, let's make it interesting," he suggested.

"A little wager? Twenty bucks?" I challenged.

"Hmmm, I'll tell you what," he said, "you win and I'll pay you $20. But if I win . . ." he paused.

"Yeah?" I asked.

"If I win . . . well . . . you have to tell me why you're wearing pink panties."

"Wha-?!" I gasped, looking down. Oh, shit! I completely forgot I was wearing my favorite frilly thong under my jeans. That morning I thought everyone was gone, so I figured why not wear panties, right? But when I found out later that Brad was still there I totally forgot to change. It was the first time I slipped up in two years at the frat house, and now a bright magenta whale-tail was riding up my back as I leaned forward with the video controller. It was lined with black lace, making me look extra girlish.

Brad looked at me with a big shit-eating grin on his face. He had me and he knew it. My face turned bright red and I just stammered and stuttered. "I . . . I . . . I. . ." I couldn't seem to form any words.

"Dude!" Brad exclaimed. "No worries! It's cool, and you don't have to tell me anything!"

"That is," he said as he pressed START, "unless you lose!" he laughed as attacking aliens appeared on the screen.

I couldn't even begin to concentrate on the game, and Brad crushed me. When Game Over came up he fixed me with an inquisitive stare. "Well?" he demanded.

I blushed. "OK, OK," I said with a sigh. I took a deep breath, looked at him and shrugged sheepishly. I hemmed and hawed but eventually admitted that women's clothes always fascinated me.

"Really?" he asked, sounding curious.

"Ummm, yeah," I confessed. "One time in high school when my parents and sister were away I . . . I tried on some of my sister's things . . ."

"Really?" he asked. "Like what?" He didn't seem disgusted or horrified, as I expected – it was more like he was kind of interested. That was a big surprise.

I didn't go into all the details, but I admitted I tried on panties and skirts and learned to put on makeup. He seemed to be getting excited and asked if I had a feminine name.

"Katie," I said shyly.

Brad then really surprised me by asking if Katie ever fooled around with guys. I wasn't sure how honest to be, but he seemed to be really eager to know so I thought, What the hell? I am what I am, right? Anyway, I vaguely told him that one time Katie got caught all dressed up, and one thing led to another and she ended up fooling around with a married guy and his wife at the same time.

"Really?!" he gasped, a look of surprise on his face.

"Uh-huh," I nodded cautiously. I left out most of the details, though, and I definitely didn't tell him about some of the other things I'd done dressed as Katie. Brad had known me for two years as just a normal guy (or so I thought). I figured it would shock him to know about the wild things Katie did.

"Yeah, some of us kind of suspected that you might go both ways," he said matter-of-factly, "but it's cool, you know. No one's judging."

"What?!" I shot back. Now it was my turn to be shocked. "You guys suspected me . . . and it was no big deal?"

Brad shrugged. "It's all good, Dude!" he explained. "You're cool so, like, whatever, you know?"

Wow, I thought. That's awesome.

Brad then said that the idea of me dressing as Katie and fooling around with guys had gotten him a little worked up, and suggested that later on he might have to take care of his "little problem." He blushed.

Now I was really surprised. I had no idea that Brad had any interest in girls like Katie. But from the bulge that appeared in his shorts there was no doubt. Also, I could tell that his "problem" wasn't so little. He looked huge!

"Wow, Brad," I said, "I never expected that you were so . . . interested . . . in anything other than cheerleaders and prom queens."

He shrugged. "Actually," he confessed, "I've read stories and watched some videos about guys dressing up and stuff, and it kind of turns me on . . . but I never thought it actually happens . . . just fantasy stuff, you know?"

I smiled knowingly and looked him in the eye. "This stuff does actually happen, Brad," I said softly.

Brad shook his head in disbelief. "Wow . . . do you have any . . . pictures of Katie I could look at?" he asked hopefully.

I smiled. "I don't, but the couple I fooled around with kept a few. Sorry, Brad."

There was an awkward silence between us. Where was this going? I wondered. I always had a secret little crush on Brad (as well as a few of my other frat brothers) but never, ever in a million years did I think anything could ever come of it. For one thing, Brad never had any shortage of hot girls around. He was a star varsity lacrosse player, over 6 feet and in great shape. He had a mop of curly blonde hair, blue eyes, and a chiseled, tan face. He was like the model for one of those marble statues you see in a museum. For another thing, he never acting like anything other than a super-macho ladies' man.

I, on the other hand, was one of the smallest guys in the frat. Girls hardly ever seemed to notice me and sometimes the guys called me shrimp, or Little Kenny and things like that. My athletic prowess was limited to being the guy on the crew team who sits in the front and shouts "Stroke!" Actually, that was a great gig for a guy like me – I got rowed around by a bunch of big, ripped guys and got to watch them grunt and groan as they strained against the oars. Best job in college sports! Of course I had to keep my weight down to make our boat as fast as possible, so I was nice and lean.

Breaking the silence, Brad said cautiously, "I bet Katie makes a pretty girl." I smiled. More awkward silence. To break the tension, Brad pressed Start again, bringing us back to reality. We played some more video games and talked, not really keeping score anymore, but the conversation kept coming back to me dressing as Katie. I noticed that Brad kept stealing glances at me.

"What?" I finally asked.

"Ummm . . ." he began, "I don't really know how to ask this, and I'm sorry if this embarrasses you but . . . when those two caught you dressed up . . . did you . . . did you like fooling around with a guy?"

I wasn't that surprised at the question, but I had to suppress a giggle. I was starting to sense that Brad wanted to make something happen here, that there was a little cat-and-mouse game going on, but he was too uncertain to be his usual aggressive self. He could talk a cheerleader up into his room in two minutes but this was way out of his comfort zone, so I decided that I had to be the cat and make him the mouse.

"Sure," I said, nodding, and added in a sultry tone, "it was pretty hot, actually . . ."

"Wow! Really?" he asked breathlessly. "Did you . . . kiss him?"

I nodded. "And it was a real kiss, too!"

"Wow," he exclaimed again. "Well . . . how far did you go?" he asked quietly.

I paused for a second, deciding to be coy. "Well . . . you know . . . "

His eyes were shooting laser beams into me now. "Did you . . . . touch. . . or rub him . . . or anything?" he asked tentatively. "You know . . . down there."

I nodded again, biting my lip.

"Oh, my god!" he whispered enthusiastically. He seemed more turned on by the idea of me fooling around with a man than I was.

I smiled and shrugged my shoulders. "Yeah . . . we went pretty far, actually," I said in a whisper. The conversation was turning very sexy now and I noticed that my voice was taking on a soft, sultry tone, as if Katie was trying to speak up.

"Wow! Did you . . . give him . . .a . . . a . . . a . . . " I knew exactly what Brad wanted to ask, but he couldn't get the words out. I was enjoying his frustration – it was like I was teasing him. I just looked at him with an innocent, questioning expression, as if I had no idea what was on his mind.

His face was bright red now. He was conflicted, but I could tell he just had to ask. In a soft whisper he finally sputtered, "Did you . . . . blow him?"

Looking him straight in the eye, I gave a subtle nod. "Uh huh," I purred.

"Wow, wow, wow!" he exclaimed. He just sat there, staring at me in astonishment. Finally, he asked, "did you like it?"

I nodded once again. I was admitting things I'd never told anyone before and blushing like crazy, but seeing how excited Brad was I decided to go for broke.

"Actually, I loved it," I said in a throaty voice. Brad seemed to swoon. "The truth is, Brad, when I'm dressed Katie with makeup and everything I actually feel like a girl. And it's totally hot being on my knees, blowing a guy."

"Wow," was all he could say.

"I've only done it a couple of times, but it turns me on like crazy." Brad's eyes were aflame. I giggled girlishly, then added in my sexiest voice, "and the guys seem to like it too!"

"Wow," he gasped. "You really like giving head?"

I giggled again, nodding slowly. We were all alone so I decided to see what effect talking dirty would have on Brad. "Well, the way I think about it is that I'm not the one who likes it, but Katie really loves to suck cock."

I paused to let the words sink in. Brad gasped with excitement so I continued. I gave him my sexiest look and purred, "Katie can be really bad sometimes . . . "

Brad looked like he was about to fall of his chair, so I turned up the heat. "Want to know a secret?" I teased.

Brad just nodded, his mouth agape.

I leaned into him, our noses almost touching. "Katie swallows."

Brad's involuntarily let out a groan, his eyes going wide. "Yeah, she just loves a mouthful of come . . . she can be a real naughty slut sometimes," I giggled, "she'll do almost anything . . ."

Brad was practically panting now. He said he would love to meet Katie some time, that she must be a real sexy girl.

I thought for a second – I didn't keep any girl clothes at the house for fear of being caught – so I gave him an apologetic smile and said, "I'm sure Katie would just love to get all dressed up for you, Brad, but she doesn't have anything to wear here . . ."

Brad furrowed his brow, frustrated, but then suddenly his face lit up. "Wait a minute!" he barked, "what about Rhonda's clothes?"

Rhonda was our frat brother Jimmy's girlfriend who got a campus job for the summer and just moved into Jimmy's room a few days ago.

"She won't be back for a week," Brad said, "and she already unpacked all her shit – I saw her doing it yesterday."

"Really? All her stuff is here?" I squeaked. Brad nodded. Rhonda was one of the hottest girls on campus with a whole wardrobe of sexy clothes, and I was pretty sure I could fit into some of them – at least the stretchy things. Just the idea of going through her closet made me tingle, and the idea of dressing up for Brad sent chills through me.

This was shaping up to be the greatest day ever, but I figured I should at least try to play it cool.

"Well, I suppose I might find something in Rhonda's closet that'll fit, but are you sure you want Katie to dress up for you?" I said innocently. "I don't want to shock you or anything."

He nodded urgently. "I'm totally sure!"

"Well, I don't know if it's a good idea. Katie can get pretty wild – are you sure you're OK with whatever happens?"

He just kept nodding.

I gave him an evil grin. "Sometimes," I purred, "she just can't control herself."

Brad was practically hyperventilating now, "I'm sure, I'm sure."

"OK!" I giggled. "But it's going to take me a while. Can you wait?"

"Oh, yes!" he assured me. "Definitely! I'll be here . . ."

* * * * *

I scooted up the stairs and took a quick bath, shaving my legs, arms and the light fuzz on my face. I plucked my eyebrows and powdered myself and then, with a towel wrapped around me, I slipped into Jimmy's room and scouted out Rhonda's things. It was so quiet upstairs. I felt so sneaky!

Rhonda's tops, skirts and dresses were lined up neatly in her closet, lacy underthings in drawers, makeup and jewelry on her dresser, shoes in boxes stacked against the wall. My eyes immediately went to a small, pink crop-top, low cut with buttons down the front. I held it against me – it looked like it might fit.

Dropping the towel, I found a padded 34C bra that just managed to reach around my chest. I hadn't dressed up since last summer and it felt so good to slide my arms through the bra straps and hook them together in front, then slide it around to bring the cups tight around my chest. I found some socks to use as padding, giving me nice, firm boobs.

I slipped into the pink top, leaving most of the buttons undone to show off my lacy bra. The top was tight, giving me curves, and left a few inches of my flat belly exposed. I was grateful about working out and staying slim for crew.

I found a short white pleated skirt and a pair of red panties. The panties were tight and just barely contained my small, hard penis but I tucked it to the side and pulled the panties snug. The skirt was short, above mid-thigh, and the pleats did a nice job of hiding my tiny bulge. I flattened out the pleats, stood up straight and checked myself in the mirror – things were coming along nicely!

I sat on the bed and rolled sheer, dark stockings up my legs, then searched through the boxes and found a pair of purple high-heeled ankle boots that accentuated my legs. They were tight but I could just manage to get my feet into them.

I decided that Katie looked very sexy in this outfit. I put on makeup, coloring my cheeks, highlighting my eyes and thickening my lashes. I found Rhonda's brightest pink lipstick and expertly applied it, making my lips wet and lush.

For my hair I had a really expensive, luxuriant, shoulder-length blonde wig that I was given two years ago (more on that later). It was the only girly thing in my room, hidden in plain sight on a ceramic bust of Marilyn Monroe that everyone agreed was a cool piece of art, never thinking anything more of it. No one had any idea that I ever actually wore it -- if only they knew!

I fixed the wig securely on my head, then explored Rhonda's jewelry box. I found a bunch of silver bangle bracelets, which I love to wear when I'm dressing up, and slipped a few on each wrist. I keep both ears pierced and sometimes wear a little diamond stud in just one, but when I'm dressing I liked to wear a pair of big, gaudy hoops to go with my long blonde hair. Fortunately, Rhonda had just what I was looking for. I slipped the silver hoops in my ears and looked in the mirror to see a stunning, sexy young girl staring back at me.

I was just about done when I found a bottle of bright red nail polish in the top drawer. "Why not?" I thought. It would take a few minutes but also build up the suspense. I opened the bottle and applied the red liquid to each of my fingernails, then waved my hand on blew on them to help them dry. I examined my reflection in the full-length-mirror in the hall and saw a cute, slightly naughty version of Katie starting back at me. I puckered my pink lips, blew myself and kiss and got ready to make my grand entrance.

* * * * *

Coming down the stairs I found Brad sitting on the couch, still playing video games. When I cleared my throat to get his attention his jaw almost dropped. He immediately put the game controller down, looked me over and said, "Wow!"

"You look so hot," he said in amazement. "I had no idea . . ." I walked over to the stereo to add soft music to the scene, then did a runway strut across the living room. I slowly twirled around, showing him the whole package from boots to blonde hair.

After sashaying around for Brad I noticed that the bulge in his cutoff shorts was even bigger than before. He was wearing a loose tank top that exposed his muscular shoulders, and he looked really cute with his curly hair and strong arms.

I stood in front of him with my legs apart and my hands on my hips, like Wonder Woman. "So, do you like Katie?" I asked suggestively in my high female voice.

He nodded as a huge smile spread across his face. On impulse I lowered myself onto his lap and put my arms around his neck. He was surprised at first, but when I pressed my panty-encased ass against his hard cock he groaned. My skirt spread open and brushed against his bare thighs as I shifted my tight butt in his lap.

"I like you too, Brad," I purred.

Brad started to stammer something but before he said anything I leaned in and kissed him lightly on the lips. Again he was startled, but I smiled hopefully at him and when I leaned in to him again he kissed me back. Tentatively I slipped my tongue out against his lips and soon we were sharing an intense, wet kiss, our tongues wrestling as Brad's hard cock nestled into the crack of my ass.

We finally broke the kiss and I looked deep into Brad's eyes, rubbing my hands all over his shoulders and back. "I'm so glad we're getting to know each other like this," I said, using my best feminine voice. He smiled and brought his lips to mine for another long, wet kiss. As we made out his hand was inching up my stocking-clad thigh, getting close to my tightly encased weenie. Dressed as a sexy girl, I was much more interested in pleasing him right then, so I pulled back and slipped down off his lap.

I fell to my knees on the floor between Brad's legs, looking up at him with my most devilish smile. I put my hands on his thighs and rubbed lightly, trailing my red fingernails along his skin, my bracelets jangling. Brad shook his head, like he couldn't believe what was going on.

I giggled, closed my eyes and kissed the inside of Brad's thigh, a soft, lingering kiss, followed by a long string of gentle kisses up to the edge of his cutoffs. I was in bliss as I nuzzled the skin of his thigh and the blonde fur of his legs, kissing my way back down his other thigh to his knee and back up. I purred and cooed as I explored between his legs, nuzzling and kissing and putting on a show for him, the smooth skin of my cheeks brushing against his thighs.

Finally I looked up and saw that Brad was panting and his face was all red. "You like Katie so far, don't you?" I teased, batting my eyelashes at him. He just nodded, as if he was in a trance.

"Well, soon I think you're going to like her even more," I whispered and then, keeping my eyes locked on his, I leaned forward and planted a soft, lingering kiss against the hard shaft straining inside his cutoffs. Brad gasped as I pressed my lips against the faded denim, kissing and nuzzling him lavishly until the fabric started getting damp.

"I wouldn't call this a 'little' problem,'" I giggled as I gently chewed on the firm lump in his shorts. "It seems like there's a nice, big problem in these shorts, baby . . . and it's a problem I can definitely help you solve . . ."

As my words sunk in I reached up to unbutton Brad's shorts, drawing yet another gasp from him. Slowly, I undid the snap, giving Brad another wicked grin and flicking my head to throw my long blonde hair back over my shoulder.

Report Story

byemelle78© 3 comments/ 31703 views/ 49 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: