Boys will be Gurls

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When Harry helps out a friend and becomes Harriet
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"Please Harry!"

Will was beginning to annoy me, he had been caught in a lie and now expected me to help. Normally I would, it was how it had worked for the last few years through school, but we were 18 now and even for Will, he was asking a lot.

I'm Harry, I'm 18 and I have just started my last year Scholam Boys School, a public boarding school in the countryside. It's a bit old fashioned, but my dad went here so I go here, it's alright though, I like it here, most of the time.

I'm not one of the cool kids, but I think everyone likes me, I not good at sports, in fact, I'm short and slight and pretty uncoordinated, but I'm clever, on the chess team, the debate team, that kind of stuff.

I'm not quite sure how me and Will became friends, we just kind of are. I think we were in the same classes when we were little and ended up sitting together, it's odd to think how that's all it takes to make a best friend.

Will also isn't good at sports, but he isn't very clever, I mean he's not an idiot, but he doesn't get great marks, he gets by, he could do better, he's that kid the teachers say "must try harder, must apply himself" about at parents evening.

However, Will has one problem, his mouth isn't connected to his brain and has come out with some real crap over the years. The housemaster, Mr Stepleton calls him a "black-catter", no matter what you do, Will has done something better.

This time, he'd been chatting to some other boys about the Senior Dinner, a formal dinner for the pupils in their last year. You were technically allowed to invite a date, not many boys did, because well, its a boys school, we don't know many girls.

When everyone else had been saying they wished they had a girl they could invite, Will had decided it was a great time to announce he had a girlfriend, he didn't, but that didn't stop him. Knowing Will, everyone called bullshit and Will decided to double-down, telling them that not only was she real, she was coming to the dinner.

I heard about this latest faux pas long before I saw Will, who was looking decidedly nervous when he walked into the dorm. He didn't even say hello as he came into my room, he just sat down on my bed while I was playing on my Xbox.

When I didn't say anything, he sighed, loudly.

"Hey Will, what's new?"

He sighed again, "I think I've fucked up man."

I was still watching the screen as I played, "Yeah, you and your big mouth."

He put his heads in his hands, mumbling through them "I know man, but everyone knows, I don't know what I'm going to do."

"Well the young lady isn't going to be able to attend, maybe she's ill, maybe you break up, maybe you just hope everyone forgets."

He raised his head out of his hands, "They aren't going to forget and they won't believe any excuses."

"Well you're shit out of luck then."

"Unless I can get a date."

I was still playing the game, "How are you going to get a date, you don't know any girls."

I could feel him looking at me, his eyes burning into the back of my head.

I paused the game and turned round to look at him.

He had an odd expression on his face, "Harry..."

So Will had asked me to be his date, it sounds stupid, and it is, but not as stupid as it sounds. I did drama, and in a boys school, casting a female role is difficult, as they aren't any females, I was small with a somewhat feminine physique, no facial hair and most importantly I didn't mind playing a female role. This meant I had acted as a girl in a few plays, even having to do my own makeup and sort the costumes.

It was stupid because, I wasn't a girl, I knew everyone at the school and they all knew me, and a lot of them had seen the plays. I couldn't believe for a second I would get away with it, so I said no. I was pissed Will had even asked, normally I helped him dig himself out of trouble, but this was ridiculous.

But there were a couple of things I didn't count on. One was the amount of shit Will caught, no one believed him about his date and everyone, even kids in the years below gave him shit for it, he didn't ask again, he didn't even bring it up, but he was really depressed.

The other reason was a secret, I liked dressing up. I had loved doing the plays, I had done the first one because one of the teachers had said more activities would look good on a University application, but I had got a real thrill doing it, so I had kept on doing it.

I don't know if it was the clothes or the make-up or that being on the stage mean that I, normally quiet, was the centre of attention, but I loved it. I hadn't told anyone, not even Will.

So in the end I agreed to it, I had already told Mr Stapleton I wasn't going to the dinner, so I wouldn't be missed and it cheered Will up a lot. I still thought it was a stupid idea and was really nervous, but I was also looking forward to dressing up.

I did have a couple of conditions, the first was that Will would pay for anything I needed, we wouldn't discuss this afterwards, he OWED me and lastly he wouldn't say anything stupid to anyone. I really didn't need him escalating the situation, so I told him he could say his date was definitely coming, but that was it. Surprisingly after a couple of days of him saying that, people started to leave him alone.

I shopped for girly clothes for myself for the first time. I couldn't do it in person but I borrowed Will's bank card and surfed the internet. His family was quite well off and gave him a decent allowance so they wouldn't notice my spending, but I had to be careful where I bought stuff, as they probably checked his transactions and would ask questions if he started spending money in women's shops.

I found a couple of dresses, that were nice but didn't show too much flesh, I bought some makeup to add to the school's drama kit that I had access to. I even found some shoes, I hadn't worn heels before but thought I could get away with some wedges.

Will did ask some questions, while we were hanging out, despite the fact we were pretending to go on a date, we still hung out like before.

"Harry, what about tits?"

It was out of the blue, we hadn't been talking, let alone about the dinner, concentrating on the game.

"Err, what about tits?"

Will paused the game, "Girls have tits."

"Full marks for observation, you only just notice"

"Dick. I'm taking about the dinner, you don't have tits,don't you think people will notice?"

It might sound stupid, but I hadn't really thought about breasts, in the plays I didn't do anything. Fuck, I hadn't thought about underwear either, I hadn't got a bra or panties, I had just planned to wear some tight boxers.

I didn't want Will to freak out, "Some girls have small tits, dickhead. I'll just wear a bra so it will look like I have small tits."

He hurumphed, "big tits are better."

He was such an arse, "Well you can always find yourself another date."

He didn't say anything else, but I realised I had gone a bit red, I was pissed off but also kind of embarrassed, like he had insulted my breasts, which was stupid, I wasn't even a girl.

That night, I borrowed his card again to get some more things, I spent hours looking at lingerie. I found some nice bikini type panties and a shoulderless bra with some inserts, not to give me breasts so much as just a bit of roundness.

A couple of days latter Will came barging into my room where I was finishing up my homework, he threw a bag onto my bed.

I sarcastically said "Hey Harry, how are you? Oh, I'm good thanks Will, you?"

He didn't even bite, "I got called into Mr Stepleton's office."

I sighed "What did you do this time?"

He blinked, "No, idiot. It was you."

I was thoroughly confused now, "What? Start at the beginning."

"Mr Stepleton checked my post, and found your stuff."

Fuck, just fuck. It hadn't even occurred to me, sometimes parcels were checked to make sure we weren't ordering anything we shouldn't. It was just part of life at a boarding school, I hadn't thought of it because I never did, I never ordered anything that would get me into trouble.

Fuck, the only stuff I was waiting for was the bra and panties. The dresses, the shoes, even the makeup I could blag were for a play, but not the lingerie.

I groaned and closed my eyes, I was afraid to ask "So what happened?"

He looked at me like I was an idiot, "I told him they were yours, that you used my card."

"WHAT?!" I had shouted, but calmed myself and repeated "What?"

He shrugged, that simple arsehole "I told him you had asked to use my card and I said yes, didn't ask what it was for, don't know what's in the parcel."

He had neatly sidestepped it, letting it fall on me. That fucking dick, the dinner was only a few days away and now my Housemaster knew I was ordering lingerie, he would either put two and two together and figure it out, or think I was some kind of freak.

But he had let Will have the parcel so... I didn't have any idea what that meant.

Obviously I was pissed at Will, and threatened to back out the deal. But the truth was, I was still looking forward to it and the idea that someone might know what I was doing was honestly exciting, so I let him bring me round.

I spent the next few days watching online makeup tutorials and practicing a more feminine voice. I even tried on the dresses, deciding on a emerald green vintage dress, it was really cute and covered my non existent bust. I practised walking in the shoes, even dancing in them.

But I didn't put it all together, so on the night on the dance, when I wore the lingerie, the bra's inserts giving me a more feminine shape, the skirts emphasising my hips and bum, the shoes, the makeup and the wig from the drama department, a brunette pixie cut, over my short hair. I was taken aback by what I saw in the mirror, a surprisingly attractive girl, no, young woman, I felt that I could pull this off, people wouldn't recognise me, I couldn't recognise me.

I had gotten ready in the gym changing rooms rather than my room, as I didn't to have to walk through the dorm dressed up. So I carefully stuffed all my stuff and my normal clothes into my locker and mentally prepared myself for the evening ahead, Will would be waiting for me on the quad, by the hall.

When I walked up, his face was priceless, he watched me as I came closer, doing a double take when he realised it was me. When I got close he whispered in my ear "dude, is that you?"

I smiled, and gave him a peck on the cheek, I was enjoying it already.

I looked up at him, even in my wedges, he was a good couple of inches taller "don't blow it now" I took his arm and started walking towards the hall, he had to step quickly to catch up.

"This is great, you look hot, like a girl."

I smiled at the compliment "that was the plan, idiot"

He nodded eagerly, "yeah, but you're like, you know, fit."

It was odd being called fit by your best friend when you are dressed as a girl, but it certainly wasn't bad.

Tom, one of the other boys in our house, stepped in front of us, he was looking straight at me.

"Hey Will, who's your friend."

Two thoughts crossed my mind simultaneously, the first amounted to FUCK, HE KNOWS! The second was slightly more prosaic, what was my name?

Despite everything, I hadn't even considered I needed another name, I didn't even know if Will had told people his "girlfriends" name.

There was an awkward pause, before Will blurted, "Harriet" my heart dropped, Harry and Harriet, not exactly a million miles apart.

But Tom kept looking at me, he stuck out his hand and I took it, there was a little shake and he stepped in and kissed my cheek. I was shocked, he really didn't recognise me.

Will, a few steps behind went "Tom Harriet, Harriet Tom, he is one of my friends"

Friends was pushing it a bit, they got on well enough but Tom was one of the ones who had given Will the most crap over the girlfriend thing.

Most of the evening passed in a bit of a daze, Will took me on a tour of the room, introducing me triumphantly to everyone who had disbelieved him, a couple of times I thought I felt someone touching me as we moved through the crowd. Will even introduced me to Mr Stepleton, who stood for a second, narrowing his eyes before shaking my hand and saying "pleased to meet you".

I passed, no one said a thing, not only that but there were only a couple of other boys who had managed to bring dates which pushed Will several steps up the social ladder. He was loving it, holding court with all the dateless wonders.

I don't remember much of the dinner itself, Will was pretty much ignoring me, focused on his new status, but one the boys next to me, Charlie was quite friendly. I didn't really know Charlie, he was in a different house, I didn't have any classes with him and he was in most of the sports teams so we didn't cross paths much but he was funny and kept me entertained. He cleaned up well though, he was tall, taller than Will, with short curly hair a strong chin and an infectious grin.

We were allowed wine with the meal, as we were all now 18, I had a few glasses but WIll was packing it away, becoming louder with every glass. Once the meal was over, I sat with Will while the dancing started. I like to dance and had hoped Will would dance, but I didn't think I should go and dance on my own.

I was thoroughly bored when Charlie appeared and asked me if I wanted to dance. I asked Will, but he was having a drunken conversation with another boy and waved it off. So I let Charlie lead me onto the dancefloor.

We danced for a while and I was having a good time, we were making each other laugh as much as actually dancing, but we were both smiling the entire time. Then the music changed, and a slow song came on, most of the boys, those without partners left the dancefloor, but Charlie smiled and shrugged holding his hands out. I was nervous, but took his hands and we started to dance, he was very close and I could smell his cologne. We danced closer and closer until my head was resting on his chest and his hands were round my waist, over the course of the song they drifted a bit south of my waist, but I didn't think he could really feel anything through the poufy skirts and honestly, I didn't want to ruin the moment by moving his hands away.

The song finished and we both stepped apart, somewhat reluctantly, the music went back to a more upbeat tempo and we continued dancing, though now we got closer than before and we both found excuses to touch each other.

I was completely caught up in the moment, I didn't even stop to think I was flirting with another boy, or that my friend and date Will was somewhere else. I don't know how it happened but during an r'n'b song, Charlie ended up behind me.

He was gently grinding up against me and when I didn't resist, he got bolder, with his hands on his hips he started to press himself against me. I got hot and bothered immediately and I was getting really turned on, I wasn't sure if it was my imagination but I thought I could feel his penis pressing against me through the skirt.

I didn't think about everyone else in the room, I didn't think about the fact I was a boy in girl's clothing I just thought about the strong hands on my hips, the attractive man behind men and the sensation of being wanted.

I started pushing back into Charlie, we were moving in time to the song and I could definitely feel him through the skirt, his shaft was sat between my butt cheeks, pressed against me. It was the sexiest thing I had ever felt.

I don't know how long we danced like that, not a breath of air between us, glued together, but it can't have been long. The music stopped and we stepped apart, I turned to face him, both our faces bright red, I could see him pressing against his fly, and I could feel myself straining against the fabric of my panties.

It was an odd sensation, there was a lot of pressure, which was uncomfortable but as excited as I was, there was a lot of stimulation. I had to glance down to check my excitement wasn't visible, I couldn't see anything, but couldn't be sure.

Charlie took my hand and asked if I wanted to get some air. I nodded, not trusting myself to speak. I was worried that someone would spot my erection and I would be outed, I wasn't sure which was a more worrying thought, being discovered or the evening ending so abruptly.

Charlie led me outside and across the lawn, into the headmaster's garden, it had some fairy lights but was pretty dim, we could see the hall and hear the music, but probably couldn't be seen among the flowerbeds and bigger plants.

He dragged me behind a bush and kissed me, it was unexpected, and ardent and amazing. I didn't react for a second, stunned but he didn't seem to notice, I could feel his tongue pushing at my lips, so I opened them, his tongue flashed in, touching mine.

I had never been kissed before, and part of me was thinking it was kind of gross, another part of me couldn't believe my first kiss was with a boy, but mostly I was enjoying it, I moved my tongue against his, wrestling, chasing, teasing each other, our tongues playing out their own game of flirting.

I loved it, it was without a doubt the most exciting thing I had ever done, it made me feel... sexy, like I was desirable. As we were pressed against each other, I could feel his desire pushing against me, I had to turn my body to the side slightly so my erection wouldn't give me away.

His hands lifted my arms up, over his shoulders, so they rested around his head and it seemed the most natural thing in the world to pull him in closer. I don't know if we were there for a second or an hour but I could suddenly feel his hands on my bum, cupping it, rubbing and massaging it through my clothes.

I moaned into his mouth, I felt so wanton, I wasn't thinking at all, I didn't want to, I devoted every iota of my attention to the experience, the sensations, all so new to me, so exciting. I was so wrapped up in it all, I didn't notice charlie bring my arm down from his shoulder, not until he pressed my hand against his crotch.

I could feel IT, hard, underneath his trousers. I was scared but also curious, I had never touched another person's penis, I had seen plenty, you don't live at a boys boarding school without seeing penis', in the changing rooms, the shower, around the dorms, but I had never touched one, I had never wanted to.

I would have pulled my hand away, but charlie's own hand kept it there, gently but firmly. We had stopped kissing, but we were resting against each other and I still had my eyes closed. I gently squeezed, taking him in my hand, I could hear his sharp intake of breath and the twitch that ran along his shaft.

He pulled me onto a nearby bench, I was sitting next to him, my hand still glued to his hard on. His breathing was coming faster, I was doing that to him, it was exhilarating. I surprised myself when I undid his fly and pushed my hand under his boxers so my hand was nestled against his bare flesh, I took him in my hand, enjoying the heat of him, the soft yet firm feeling.

I pulled him out of his trousers, into the cold night air, I didn't mean to, I didn't think about it I just did and let go so I could admire him. In truth I was slightly disappointed, he was bigger than me, but I already new I wasn't well endowed, I had expected him to be massive, but he was I suppose, average. He wasn't circumcised like me, his foreskin was partly pulled back exposing his bullet like head, wavering in the breeze.

He let out a little whimper that made me smile, I was being a tease. So I took him back in my hand and started jerking him off, just the way I liked to do it to myself, firm but gentle, long strokes all the way from the root to the tip. He started thrusting his hips up to meet my downstroke.

He was going purple, almost as dark as his helmet which was angry and engorged, I could feel him throbbing in my hand. Normally, when I did it to myself I liked to drag it out, but Charlie was close and as much as I was enjoying myself, I really wanted to make him cum.

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