Writing this was very cringe. I still turn red when I think about it.
Sometimes I’m bad at sex, y’all.
I’m not very good at role play. Theoretically I guess rough sex is role play in a way, but I have a hard time playing actual characters.
For someone who is epically bad at this, I’ve had a weird amount of role play sex. It always seems like a good idea at the time.
So a guy once asked to fuck me in cheerleader uniform for his birthday and I agreed to try. I had to order one from Amazon because I was too embarrassed to ask my roommate who was an actual cheerleader to borrow her uniform.
So if I’m going to do this, I’m going to do it right. I wear pigtails, get knee high socks, and put on the sluttiest uniform I could find online. Physically, I have nailed this.
The problem? I don’t really know how to act like a cheerleader. You’re reading the words of a woman who was once an emo chess nerd.
My boyfriend walks in and initially REALLY digs what’s happening. He stands in the doorway for a while and asks me to twirl.
I. Feel. So. Awkward.
It’s noticeable too. He bursts out laughing as I turn bright red.
“Ok… so like what now?” I ask.
“What do you mean?”
“Like, do I do cheerleader things?”
“Sure.”
“So like… Give me a B! Give me an H!”
“Wait?” He interrupts me. “What are you spelling?”
“I hadn’t gotten that far and now I’m not sure where that was going?”
He starts laughing. “Do more cheerleader things.”
Im actually really flexible (thanks yoga) and just instinctively do a headstand and then roll over into a splits. I’m giggling now though because I feel so weird. “Is this a cheerleader thing?”
“I think you’re supposed to be more like a slutty cheerleader.”
“I can put my leg over my head,” I offer.
“That could work.”
I do it and then awkwardly say “ta da!” Because that’s obviously really sexy. “Do you want to just spank me? This could be a dirty school girl thing.”
“I’m kind of enjoying this actually,” he laughs.
“You have to help me out, I feel so awkward. Like… give me a scene here. What’s my mood?”
“You’re naive.”
“I’m a slutty, naive cheerleader?”
“Yes. Like, you don’t yet know you’re slutty. And then we won a huge game so you’re excited and want to fuck.”
“I’m in college right? This isn’t an underage thing?”
“Yes, you’re in college. You’ve been sheltered your whole life and now you’re curious.”
“Oh dear… ok.” I get so awkward. I try my absolute hardest to get into this character but this is just not me. “I’m really excited we won this game! It’s making me a little too excited.”
He’s graciously trying not to smile as we continue this. “Are you excited enough to suck my dick?”
“I’ve never done that before.”
Then he really looses it. “I’m so sorry, V. The thought of you never having sucked dick is kind of funny.”
“Woooow.”
“I’m sorry. You were doing so well.”
“Really?”
“I mean… You were getting there.”
“Ok… so like, I’ve never sucked dick before but I will try it. You’ll have to walk me through it.”
He holds back a snort but motions me to come towards him. “Get on your knees.” I hit the floor and try to look innocent when I stare back up at him.
“Now what?”
He unbuckles his belt, pulls himself out and sticks it in my face. “You put this in your mouth and suck.”
“Do you want me to do a cheer about how big your dick is?”
He laughs and shakes his head. When I take him in my mouth initially all goes well. Despite my cheer persona, I have in fact sucked a lot of dick and I’m great at it.
Then he starts talking.
“Are you being such a slutty cheerleader?”
I burst out laughing. I can’t do it. “I’m so sorry. I just can’t imagine myself as a cheerleader.”
He starts smiling and sinks to the floor. “I thought it would work. You’re small and blonde. I thought this would be a natural role play.”
“We can keep trying.”
“How about I just turn you around and fuck you in that uniform. You do look cute.”
“I can spell more things out if you want.”
He rolls his eyes as he grabs my hair and pulls me on the floor. He flips me around. “You’re not wearing underwear?”
“I thought it’d be a waste.”
He fondles me for a bit and lightly spanks me before he pushes himself inside of me. I shudder and moan as he pulls one of my pigtails. “You really do look hot, by the way.”
“You can get rougher if you want.”
He flips me on my back and goes back inside of me. He throws a hand over my throat and chokes me lightly as he starts going harder and whispers something about how I’m a dirty slut who has to take it.
He pushes my head into the floor and tells me I have to beg him to come inside of me.
“Please come inside of me,” I beg. “Please.”
He pushes my head harder into the floor until I hear him gasp and shudder above me.
We’re both lying on the ground afterwards and he apologizes for coming before I did.
“I’m fairly certain I’m incapable of climaxing in this outfit,” I laugh.
I’d like to say I learned my lesson and stopped role playing, but I did indeed try again. It never went well.
Source: reddit.com/r/gonewildstories/comments/v1d0sz/when_i_dressed_up_as_a_cheerleader_and_it_was_an
Before I married my ex-wife, we did the football player and band geek roleplay (which was weird because we each did those things in high school). She made one attempt to be sexy while talking about “blowing on my instrument” and we both laughed for so long that we didn’t even actually have sex.
Seems good in theory, but roleplay just seems to be awkward and funny more than new and sexy.
You’re hilarious, and I can’t get enough of your writing
For what it’s worth this would make for a perfect porn parody. You can call it “Being It On: Hoe or Nothing”
Given your willingness to try stuff out, I bet you’d be good at role playing if given the right character. If or when you do discover what character that is, please do keep us in the loop. But until then keep cringe-ing shit up lmao cheers Ms. V!
My first serious(ish) boyfriend asked me to tie him up once. After I did, he asked me to talk “sexy” to him. So, in the most sultry voice I could muster, I said the first thing that popped into my head: *criss, cross, applesauce*.
I was still pretty new to sex back then, that’s the best explanation I’ve got.
You’re very good at sex V.
This amused me because I had to do some roleplay today as well lol…Man, my best/boyfriend sprung a cat outfit on me today so…
I wore the whole get up. Thigh high socks heels….and then cat ears, collar with a leash and a buttplug tail up my ass lol… I had to do my best to roleplay as a cat for him…lol…
It was mostly normal cowgirl sex with me just making cat noises, meowing and purring and rubbing my face/cheeks on his face…lol couldn’t stop laughing.
The worst part was the whole “time for some milk Allie cat” as he came in my mouth T_T
I too did not come from this romp.
Role play like the DMV. Make him take a number, fail him on his driving test for not using turn signals and threaten to make him do it all over again unless he puts your ass through the drywall in the break room.
Aftercare is lukewarm instant coffee in a styrofoam cup and being reckless with the label maker.
Haha this was great! Sense of humour during sex is so important. Sounds like you had fun regardless, don’t let this be too embarrassing ;)
… my girlfriend has agreed to some… explorative stuff. She’s as nasty as me, sometimes more.
So I ask her to do xyz, sure, no problem.
I ask her if she’d call me this, let me call her that. All good.
I ask her if she’d wear cat ears. Not really her thing exactly, but hey, love is a series of compromises.
Then while we’re fucking and ramping up the dirty talk… I say one of the most embarrassing things I think I’ve ever said in bed. I shit you not, I told her: “tell me you want to have my kittens.”
Yes. I said that. And yes, she burst out laughing immediately.
But I’ll ask you to bear in mind that 30 seconds earlier she was happily calling me Daddy and asking me to hurt her, punish her and breed her… so…
Honestly there’s no getting around it and I’m still incredibly embarrassed 😅
All through high school I was a drama nerd. I was 5’11”, I ran everyday, and thanks to an older girl, I learned how to eat pussy. I never had actual intercourse, but, on occasion, when I went down on girls they would reciprocate. On occasion a girl would tell me I had a nice dick, but I thought they were just being nice. Flash forward to the year after I graduated I actually started dating a cheer leader who a senior in high school. She loved the cheer leader sex role play. She could give me a B L O W… It was hot and worked for me for about 6 months. She was also the first girl to actually take a rule and measuring tape to show me that my dick was not small. I think the cheerleading role play only works if one of you was actually a cheer leader.
This is golden. I haven’t laughed this hard at the start of a workweek in a long, long time. :)
> You’re reading the words of a woman who was once an emo chess nerd.
This is way hotter than you think it is for at least some of us.
Intelligence is hella sexy.
The first time my (now husband) asked me to talk dirty to him, the first thing I thought of was “cum big” and we both just started laughing and now I sometimes just say it as a joke
Lol. Very cute you tried tho
>“I can spell more things out if you want.”
I nearly snorted out my breakfast cereal when I got to this line!