u/VersionWonderful1772

While in high school I never really secluded myself to one group. Most people at my school didn’t really have a diverse set of friends. The football players were friends with the football player. Baseball friends with baseball. Nerds friends with nerds. Seniors with Seniors. And so on and so forth. Not me though. While I was considered by most a “jock” because I played hockey and baseball, I certainly didn’t act like it outside of sports. I had friends who were nerds, popular girls, skaters, stoners, jocks, and of course you… the tomboy. My senior year I took what was considered a freshman level class just to get an A and boost my GPA for applying to colleges. That’s where I met you… ____. I was assigned a seat right next to you and based off our first conversation i immediately could tell we were gonna be friends. “Wow could you look like more of a douche?” You said as you sat down and without missing a beat I replied, “wow could you look like more of dude?” From that point on we were talking all the time in class, then I introduced you to my friends and you were one of the guys.

We kept in touch after I graduated. At the start of every semester you would always ask for the rundown on so and so teacher. We were still friends, but the connection wasn’t what it once was. Fast forward to the start of my senior year of college. Giving some freshman tour I noticed a certain someone in the crowd… it was you. You ended up going to the same college as me where we eventually became best friends. We did everything together. Homework, studied, bar hopping, football games, you were almost like a sibling to me… not a sister but a brother.

Fast forward two years and my brothers getting married. I had a date already so I wasn’t worried… that was until about two weeks before she sent me the breakup text. I wasn’t even sad about her breaking up with me, I was mad. I was telling my parents all about her the week before and how “great” she is. Now I’m dateless.

That was until I thought of you. I called you and it went like this. “____, I need a big favor. Like a massive favor. You already know this entire situation with Ella and how she was gonna be my date to the wedding and she dumped me last minute.” I let you respond. “Well my parents non stop have been talking about how they’re ‘so excited to meet her.’ So what I need for you is just for the night to pretend and act like my girlfriend. I will repay you tenfold I promise… but you do have to go out your comfort zone and wear a dress instead of dressing like a redneck white supremacist. You think you could do that? I’ll do anything you want in return.”

Don’t get me wrong, I love the fact that you’re a tomboy. Being able to treat you like one of the guys without having to worry about your feelings made you such a blast to be around.

But sometimes, when I’m alone and my mind wanders I imagine what it would be like with you on the other side. Rather than wrestling you, you’d get a tap on the ass while I tell you how good you look in this sundress. Or rather than trying to outdrink you, you would just smile and bend over to grab me another beer from the cooler when I demand it.

I’ve got a one set ups for how I could fuck the tomboy out of you, but please feel free to suggest your own. As long as you go from wearing basketball shorts and having your hair up to only owning cute dresses I’ll be very happy!

1 : I’d assumed after years of being your best friend you’d figured out we’d never date; hell you were usually the one I told about any girls you found hot. Considering my type was super feminine girls who knew more about makeup than football we were totally incompatible.

But when my parents invite me home for Christmas and the girl I’d been bragging about to them for months breaks my heart 2 days before I’m meant to go I’m not left with many options. “Look you just have to act like my girlfriend for like a week- they won’t know the difference and I can say we broke up in a month or whatever?” I say to you.

“Ugh fine, you owe me though;” you figured it could be fun, no doubt we’d be laughing our asses off with you acting like one of my usual slutty girls for a whole week- anyway it’s not as if you had plans of my own. Once I explain about how traditional they are you realize what you’ve committed to, but you already promised.

Unknown to you as you packed a bag, I had already packed one for you, before we’re about to head off with me in my super old jeans and t-shirt I hand you the dress. It’s something you would never wear- literally never. You had worn a suit to your own prom so this was a pretty significant departure from your usual wardrobe.

“Look day one just wear that, then you can dress like normal after that? I just wanna give a good first impression!” You shoot you daggers with my eyes as you spit out a, “fine. You owe me tenfold now though.” And head off to get dressed. As you sit in the car you don’t entirely understand my wide eyes and the stammering over my words- it would never occur that I might actually find you hot. Wanting to claw your face off the entire way over from the heavy you can’t wait to change into something actually comfortable that doesn’t make you look like brainless eye candy. No doubt you’ll be enraged when you open your bag to find exclusively the most feminine outfits possible.

Going into the week you assume you could never actually care about being hot or living to be bent over the nearest available surface and getting a load fucked into me, but coming out of it you’ll wonder how you would ever lived without it.

So this is the only idea I’ve got, if you can’t tell I desperately want to be make someone into your typical girly girl! I love the idea of me never realizing how stacked of a body you had as well. I just want the Tomboy to be turned into a super model.

I really hope there’s a girl out there that wants to be shown why embracing their femininity will make them so much happier. Please message me through DM’s or PMs, I’d be happy to move to another platform if we get on well too 🙂

I am 18+ and all participants and characters must be 18+

Don’t get me wrong, I love the fact that you’re a tomboy. Being able to treat you like one of the guys without having to worry about your feelings made you such a blast to be around.

But sometimes, when I’m alone and my mind wanders I imagine what it would be like with you on the other side. Rather than wrestling you, you’d get a tap on the ass while I tell you how good you look in this sundress. Or rather than trying to outdrink you, you would just smile and bend over to grab me another beer from the cooler when I demand it.

I’ve got a one set ups for how I could fuck the tomboy out of you, but please feel free to suggest your own. As long as you go from wearing basketball shorts and having your hair up to only owning cute dresses I’ll be very happy!

1 : I’d assumed after years of being your best friend you’d figured out we’d never date; hell you were usually the one I told about any girls you found hot. Considering my type was super feminine girls who knew more about makeup than football we were totally incompatible.

But when my parents invite me home for Christmas and the girl I’d been bragging about to them for months breaks my heart 2 days before I’m meant to go I’m not left with many options. “Look you just have to act like my girlfriend for like a week- they won’t know the difference and I can say we broke up in a month or whatever?” I say to you.

“Ugh fine, you owe me though;” you figured it could be fun, no doubt we’d be laughing our asses off with you acting like one of my usual slutty girls for a whole week- anyway it’s not as if you had plans of my own. Once I explain about how traditional they are you realize what you’ve committed to, but you already promised.

Unknown to you as you packed a bag, I had already packed one for you, before we’re about to head off with me in my super old jeans and t-shirt I hand you the dress. It’s something you would never wear- literally never. You had worn a suit to your own prom so this was a pretty significant departure from your usual wardrobe.

“Look day one just wear that, then you can dress like normal after that? I just wanna give a good first impression!” You shoot you daggers with my eyes as you spit out a, “fine. You owe me tenfold now though.” And head off to get dressed. As you sit in the car you don’t entirely understand my wide eyes and the stammering over my words- it would never occur that I might actually find you hot. Wanting to claw your face off the entire way over from the heavy you can’t wait to change into something actually comfortable that doesn’t make you look like brainless eye candy. No doubt you’ll be enraged when you open your bag to find exclusively the most feminine outfits possible.

Going into the week you assume you could never actually care about being hot or living to be bent over the nearest available surface and getting a load fucked into me, but coming out of it you’ll wonder how you would ever lived without it.

So this is the only idea I’ve got, if you can’t tell I desperately want to be make someone into your typical girly girl! I love the idea of me never realizing how stacked of a body you had as well. I just want the Tomboy to be turned into a super model.

I really hope there’s a girl out there that wants to be shown why embracing their femininity will make them so much happier. Please message me through DM’s or PMs, I’d be happy to move to another platform if we get on well too 🙂