Gary to Gigi Ch. 01

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A young guy goes to college and finds and finds himself.
9k words
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Part 1 of the 2 part series

Updated 06/07/2023
Created 04/02/2016
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steviet
steviet
696 Followers

I had never really liked my family, we inherited a truckload of money when my Dad died and my Mom was more interested in partying and re-living her youth than spending anytime with me. So I pretty much raised myself with the aid of a huge trust fund and when it came time for me to head off to college I put as much distance between us as possible. I doubt she would even remember which school I had chosen if anyone ever asked her.

I had done my research and purchased a small two bedroom apartment within walking distance of the college, Dad was always way more help to me, even after he had died. I set about finding a roommate as while I was financially very secure I wasn't silly and splitting bills made sense and it would be a way to meet a whole new group of people.

Ashleigh was the third person I interviewed and new she was the person I wanted almost straight away, she was bubbly, new to town and we were going to be studying the same course so I offered her the room on the spot.

"The room is yours, if you want it." I offered as she stood up to leave.

"Really?" She seemed surprised.

"Yep. If you don't mind sharing with a guy."

"Not a problem, I grew up with a two brothers. I'll take it, thank you."

We sorted out the details and the next day my new flatmate arrived with her stuff, which turned out to be four massive bags and two large boxes of clothes, more than I imagined anyone would ever need or wear.

"Wow, is that all clothes?" I asked incredulously.

"Pretty much, a girl can never have too many." She replied with an embarrassed smile

"You're going to need way more hanging space."

"I'll manage." But I didn't want to be a bad landlord and after a few protests she conceded and we started shopping on-line for some new flat pack cupboards.

Ash and I really hit it off and after a few days we were best of friends, travelling and from school together and having most of the same classes forced us together a lot.

We'd been sharing for about a month when one day I was hanging out my washing and grabbing Ash's in, when I threw her clothes on to her bed I noticed a cheerleaders uniform on top of one of the many pile of clothes that covered her room. I was drawn to it as I didn't know she was a cheerleader, upon closer inspection I realised it was an old one from her high school as the it didn't match the colleges emblem and it was clearly not a new uniform. I'd never held one before and I was confused by my desire to examine it, like most guys I'd always found cheerleaders attractive but that was the limit of my interaction with them. I was totally fascinated with the uniform and as I knew Ash wasn't due home any time soon I decided to try it on, we were about the same size so why not. I had no idea why I was so fascinated by it but I just had to see what it felt like to have it on.

I quickly got out of my shorts and t-shirt, leaving them in pile on Ash's floor, and pulled the stretchy uniform over my head and wiggled it down my torso tugging it down by the hem before smoothing it over. I turned to look at myself in Ash's full length mirror and was shocked by what I saw, the uniform hugged my slender body, my narrow waist and slightly built upper body make me look slightly feminine and when I turned to check out my rear I was even more shocked by how girly my skinny legs looked under the skirt.

"You look better in that than I ever did." Ash said as she appeared in her door way.

"Fuck!" I yelled in surprise and fear at having been caught in her room, my stomach began to churn. I was about to lift it off, but quickly realised that would leave me standing in just my underwear and instead just froze in panic.

"No, seriously." She said admiringly.

"Oh my god, I'm so sorry Ash." I began, trying to think of an excuse.

"Stop! Calm down." She said as she walked towards me and put a hand on my shoulder, it had the desired effect and I just stood there, in her room, wearing her clothes and feeling terribly embarrassed.

"I don't know why I even tried it on." I murmured while staring at my feet.

"It's totally cool, I honestly don't mind." She said soothingly as she looked me up and down. "You really do look good in it, I'm a little shocked at how good actually."

"Um, thanks, I guess." I said unsure of the compliment.

"Mmmm...this gives me an idea." She mused as she circled me.

"What?" I asked nervously.

"Do you trust me?" She asked flatly as she stood in front of me and stared into my eyes, she had a cheeky little smile on her face that I'm sure most people found hard to say no to.

"Yes."

"Well good, now you need to do everything I say. OK?"

"OK." I replied slowly, a little worried about what she had in mind.

Ash's smile spread across her face when she heard my reply and she quickly turned and began rummaging through a pile of clothes, then a drawer, then another pile, collecting various items from each before dumping them on the bed.

"Ok, put these on, I think they'll fit." She told me as she handed me a pear of tan tights and some some white and pink sneakers. I sat down on her bed an began to slide the tights up my legs, shocked at how good the smooth nylon felt against my legs, she was correct about the shoes which were an almost perfect fit for my feet. When I stood I noticed that I looked even more girly with my leg hair hidden and the girls trainers, I was shocked at just how much I looked like a girl, even with my short hair.

"Wow." I muttered to myself.

"Yeah, I know." Ash responded as she handed me a small white padded sports bra.

"Really?" I asked.

"Yep, lift that up and I'll help you put it on."

Once she was done, she helped me pull the tight dress back down and while I was smoothing it she slipped a long black wig onto my head.

"I had it left over from Halloween, now check yourself out." She said with a sly wink as she held my shoulders and turned me to the mirror.

"Oh my." Was all I could manage, starring back at me was a person I didn't even recognise, I was looking at a really hot cheerleader.

"God damn, you are smokin girl." Ash said as she swatted me on the behind startling me out of my trance.

"Um, thanks." I offered, unsure of how to respond.

"You're going to need to work on your voice, it will never pass." She told me as she adjusted my small fake breasts.

"Pass what?"

"When we go out."

"What the fuck! I'm not going out like this." I told her in no uncertain terms.

"But why not. You look as hot as fuck and I need a friend to go clubbing with."

"You think I'm going out clubbing dressed as a girl." I asked.

"Yep, you will. I can tell you like it."

"But this is the first time I've ever done it."

"But that doesn't mean you're not really into it." She said as she looked down at my erection clearly bulging the front of her cheer uniform, I quickly covered it with my hands as she winked at me and walked out.

I got changed out of her clothes a few minutes later and back into my own, before going to talk to her on the sofa, he looked up at me a warm smile as I sat down next to her.

"About what happened in there." I began.

"Look, it's totally cool. But you really are a smokin hot girl." She informed me again.

"Thanks but it's all a bit sudden, I don't even know why I did it then next minute your telling me I'm hot and we're going clubbing, it's a lot to take in." I explained.

"Well I thought it was really fun to help you dress up and if you ever want to again I don't mind helping or sharing my clothes with a hottie like you." She said with a cheeky wink before turning the TV on. We just sat there for what felt like ages while I digested the days events.

The next morning was just like normal, we had breakfast together before making our way to school and since almost all of our classes were the same we spent most of our days hanging out and chatting like BFF's. We never mentioned what had happened and when we got home that night we both went into our own rooms to unpack before I sorted dinner.

"Garry!" I heard her yell from her room.

"Yeah." I yelled in reply as I walked towards her door.

"I want to ask you something." She told me when I poked my head around the corner.

"What?" She was standing in front of her mirror and holding two different dresses up in front of her, looking at each in turn before swapping back to the other.

"I want to go out tonight and I can't decide which one to wear." She held up both dresses for my appraisal, one a very short aqua dress and the other a slightly longer black one with a diagonal hem and one shoulder strap.

"You'll look good in either." I offered.

"Thanks but I'm struggling."

"Who are you going with?"

"Right now, no one." She said slightly dejectedly.

"Oh, so this is a trick to guilt me into dressing up again."

"Maybe." She replied coyly.

"Damn it Ash!" I said as I turned an walked away.

"Wait." She yelled so I turned to hear her out. She explained that she really enjoyed dressing me up, that it was like playing grown up dress up's, that she never had a sister and she wanted one more go to convince me of just how sexy a girl I'd be. I was initially hesitant but as usual she talked me around, I agreed to do what ever she wanted and if at the end of the night I didn't like it I wouldn't have to do it again.

"You've got tonight only, better get started." I said, finally giving in.

"Great." She yelled excited and jumped up an down before leading me into the bathroom and issuing instructions to remove all my face body hair with her depilatory cream, I began to protest but she reminded me of the promise I'd made and that it would grow back, not that there was much of it anyway.

I emerged back into her room a few minutes later, newly smooth and wearing a towel, admitted I did feel quite strangely excited at being hairless.

"What next?" I said, resigned to my fate.

"These and don't argue." She said as she threw me a padded black strapless bra and lace panties. I went back into the bathroom and slid the black lace up my legs which gave me an instant hard on, great I thought to myself as I put on the bra and checked myself in the mirror. Fuck, I did look hot in the sexy lingerie, my boner was betraying me too. I wrapped the towel around my waist and went back in to see Ash.

"Damn." She whistled. "You need to lose the towel though."

"But I."

"Drop it!" She said sternly

"OK" I said meekly and I followed the instruction, letting her see my small erection hiding in her lingerie.

"Wow, you look as hot as fuck." She said as she handed me the black dress from before, I took it and lifted it over my head eager to hide myself. The dress was made of a very smooth and stretchy material I'd not felt before but instantly loved the feel of as it slid down my torso, girls clothes certainly did feel good. Once I'd finished arranging myself in it Ash pointed to the small bulge in the front.

"Can you tuck that away, it's going to ruin the look?"

"I'll try." I said before disappearing into the bathroom. It took me a little while to work it out but I managed to tuck myself back between my legs, it did make me walk a little differently but I wasn't worried as it wouldn't be for long I reasoned.

Ash had donned the short blue aqua dress while I was in there and was holding some black high heels in her hands which she put on the ground and beckoned me to step into them. Our feet must have been identical in size because they fitted perfectly, I wobbled a bit as I stood there.

"Now sit down while I do your make up."

I slowly wobbled over to the dresser and sat down as she set work applying my make up, I was mesmerised as she transformed my already quite softly featured face into that of a stunning young girl. When she was finished she capped it all off with the long black wig she'd used last night and the illusion was complete, she stood back to admire her work.

"Time for the mirror."

I stood slowly and prepared myself for what I was about to see. The full length mirror revealed what I already knew, I was now a absolutely stunning raven haired beauty. I was in shock, my lipstick covered lips were open as I stood there agog at what I was looking at.

"Girl, you look fucking stunning." Ash whispered to me as I slowly turned around to admire her work.

"Wow. I don't know what to say." I stammered.

"Well we are definitely going out now." She informed me as she slipped on a pair of equally tall white heels and grabbed a white purse off her bed.

"But..." I stammered still in shock about how hot I looked and unable to fully process what she had said.

"This is yours." She said as she handed me a small black purse and led me by the elbow to the door. "The cab will be here soon."

"What cab? Where are we going?" I asked as it dawned on me what she was saying.

"Girl we look to hot to sit around the house all night. Plus you promised me one night so shut up and follow my lead."

I did as I was told, following Ash out of the apartment and onto the street, trying not to look to awkward as I walked in the heels. We were waiting on the kerb when all the questions hit me.

"What if anyone recognises me?"

"You didn't even recognise you, so quit worrying?" She reassured me.

"But I can't walk properly in these heels? What if people talk to me?"

"We'll be in a night club, you can barely hear anything. Just speak really quietly and try to sound like a girl." She advised me as she looked up and down the street for the cab.

"That's not much of a plan." I said, making my voice a bit higher, trying my best to sound like a girl.

"Not too bad, see, you'll be fine." I found her confidence comforting but was still really nervous as the cab pulled up and I tried to get in for the first time wearing a dress and heels.

We arrived at a local college bar, Ash paid the driver and we were ushered straight in, I hadn't even thought about being asked for ID but then I should have realised two smoking hot girls would have been welcome in most bars. It was crowded, dark and noisey inside, full of college students, most a few years older than us all drinking and dancing and having fun. Ash led me straight to the bar and ordered us our first drinks, drinking out of a straw was a bit strange but I followed Ash's cue so as to not be found out. We quickly downed two more and then Ash dragged me out onto the dance floor, spurred on by alcohol I followed, trying not to trip in the heels I could only imagine how awkward I must have looked.

We made it to the middle of the crowded dance floor and Ash turned to me and began to dance, slowly at first, allowing me to follow her moves. Soon she had me dancing with a confidence I'd never felt and I was even starting to enjoy it, it didn't take long for a two guys to start trying to dance with us. Ash must have sensed my unease and led me quickly away back to the bar.

"I hadn't thought about guys hitting on me!" I yelled in her ear once we were back at the bar and she had handed me another drink.

"I'll deal with them, don't worry gorgeous." She yelled before ordering another drink, I was starting to feel quite drunk but needed the confidence so I didn't argue.

A few drinks later Ash guided a very drunk me back out onto the dance floor, I was feeling the music and spurred on by Ash who was dancing more flirtatiously I copied her moves, bumping and grinding with her as best I could.

I don't remember how much time had passed but I was snapped out of my alcohol induced daze when two well build young men made a move on us. I was more shocked that I had forgotten I was dressed up as a sexy woman and was dancing with my hot flatmate in a night club, but now I also had unwanted male attention to deal with.

Ash must have had other ideas as she was quite receptive to the advances of one of the guys, a tall well build blonde guy that looked like a senior, that forced the attention of his friend on to me. I tried my best to not look interested or make eye contact as we danced on in tight group of four, but floor was crowded and Ash was now dancing face to face with the guy. The guy that was hitting on me was also pretty tall about 5 inches taller than me, even in my heels, build like a footballer but with short dark hair and a deep tan it was becoming increasingly tense as Ash was clearly into his friend. He was a pretty good dancer and soon had worked his way around so that we were face to face, I glanced over at Ash who was now dancing up close to her guy who had his hands on her hips. When my guy made the same move on me I froze for a brief instant when I felt his big hands settle gently on my dress clad hips, I was in a total panic but continued to dance on, not wanting to raise any suspicions. I stole a quick glance at the guy but quickly looked away when our eyes met, 'Fuck' I thought to myself, I hope he thinks I'm really shy.

When I saw Ash put her arms around her guy and look up at him I knew they would kiss. I was in a total flap, would I have to kiss this guy? Well I was dressed like a girl who wanted to pick up and I had let him hold me for the last two songs, 'FUCK' I screamed to myself over and over again as we continued to dance. I couldn't believe I had let Ash talk me into this, but I was even madder at myself for letting it get this far, what did I think was going to happen. I could now see Ash and her new man making out out of the corner of my eye, 'FUCK'.

I risked another look up at the guy who was slowly pulling me closer as we danced and when I did he took it as an opportunity to lean down and kiss me. I figured it would be better to go for it than be discovered now so I accepted and opened my mouth for my first kiss with another man. It felt weird, not as weird as I'd thought it would, but after a few seconds I'd accepted things weren't about to change anytime soon and went with it. I could feel the guys hands slowly sliding around to my arse as his tongue and mine danced, he tasted of beer and I could feel his stubble rubbing against my face as our kiss got increasingly heated. I couldn't have ever imagined being in this situation just a few hours ago, I was even more disturbed when I felt my cock twitching for release from between my legs. Was I actually enjoying this?

My arse was getting a right thorough groping and my beau certainly didn't appear to have any idea I was a guy, I could feel his boner sticking into my belly as we rubbed our bodies together, I was worried my dress would ride up so I tried to pull it down with one hand as my other roamed across his muscular back. God, I must have looked like a total hussy letting myself get mauled like this by a guy in public but I was actually getting quite into it.

After a few minutes of making out and having my arse squeezed Ash interrupted us, grabbing my elbow and leading me away, she said we were heading to the bathroom. The boys looked quite disappointed and strangely I realised I was too.

"You go girl!" Ash exclaimed excitedly as we entered into the relative quiet of the ladies room, I blushed in reply, still unsure of what had happened.

"I think I need to go home." I told her after using one of the stalls.

"Yeah, lets. It's been a big night." She responded as she gave me a quick inspection before leaving the bathroom. We quickly made our way to the cab line and travelled home in silence.

Once we were home Ash helped me get my make up off and I was in bed not long after, I don't think I slept at all that night and must have looked terrible when I met Ash in the kitchen for breakfast.

"Tired?" She asked looking up from her cereal.

"Yeah." I moaned.

"Feeling OK?"

"Yeah, just thinking about last night."

"Well I hope you had as good a time as I did." She beamed her mega watt smile at me and my mood was instantly lifted.

steviet
steviet
696 Followers