I did not want this. At least in the beginning. I swear not. This was the third time she asked me. ‘If you wanna just play, without all the… other stuff, I’m in’ I had told her the second time. We met when we were kids in a chess club and were fierce competitors. I just, stopped playing the game in a few years but she continued- winning tournaments and all. We remained friends though, and to be honest, I always had a little sapphic crush on her. How could I not! It was perfect, the way she would tower above me when we walked side by side but bent over a little bit, her hand with those soft long fingers on my shoulders, her black, plaited hair brushing me as she flew a little with every step. Her breasts, her waist, her ankles- I don’t want to objectify her- but she was SUCH A BEAUTIFUL person. I wanted her and now her proposition seemed so goddamn tempting. A game of chess and whoever wins gets to fuck the other with the strap on I got for secret Santa last Christmas. I shouldn’t have told her about it. This might see like it comes from no where but that’s how she is. Impulsive. Wicked.
And it’s not our first time doing something sexual. Or was it even sexual. Argh this is confusing!!!! We have kissed before. It was a windy Tuesday and we had tried alcohol for the first time, we cuddled like we usually do and I went for it. And she kissed me back. We never talked about it though. I don’t even think she remembers that. But I do, oh I do. She tasted like candy and alcohol and a lot of giggles. She smelled like me.
How badly do I want to smell myself on her again is something she will never know. And god this temptation? I just can’t. and when she mocked me even more, calling me a coward with rusty chess skills and a fear of losing, I like, burst out.
‘Okay. Let’s do it’
‘Really?’ she tied her arms behind her back and bent forward
‘Yup. Now. Like now-now.’
And so, it began. She laid the chessboard on the floor of my bedroom, keeping the strap on on the bed.
“You better pray today, honey. You are gonna lose so bad!”
“I’m going to play black”
“haven’t got enough in you to do the first move, eh?”
“okay I’ll play white”
“So you are going to give in so easily, Ari?”
I remained silent and moved e2 to e4
E7 to e5
Nf3
“you are going with the Ruy Lopez, eh?”
She smirked. I didn’t speak much. I was angry. Really angry. It was not fair! Here am I trying to get over this stupid stupid girl crush and here is this stupid stupid wonderful girl poking me with a stick. Her fingers as she moves the pieces from place to place, her legs as she changes her sitting position, her eyes as she thinks. God I want to kiss that face, that body. Lick it. Inhale its scents. Trace its ups and downs.
I can’t get distracted. So, I concentrate. Her smirk fades away in a bit. It’s replaced by nervousness. Then with concern. She first makes jokes about me being better than expected. It’s only a few pawns, a bishop and her King left right now. I move my queen to G7. Lolli’s’ mate.
She looks at me as I take the strap on and lick it. We don’t speak for a while as I lube it all up. “You didn’t see that coming, did you, *honey*?” I asked. She tried to giggle and she shook her head.
I didn’t feel this confident since a very long time. I pulled her close “may I?” I whispered in her ear. “Yes.” She spoke. And I kissed her neck.
Strap on in hand I moved downwards, sucking her nipples, nibbling them gently as I slid in two fingers inside her. She was wet. And she moaned. “You have no idea how long I have wanted this”
I don’t know what made me say that. No no no no no. the dynamics are off now. I lost. I lost. I lost. She’s going to… I don’t know- stop this.
But to my surprise, I see that evil smirk on her lips. And it dawns on me.
“you…. You wanted this! Ari you witch- you wanted this too”
And then I wore my strap on and fucked her like the happiest girl in the universe.
Hours later, as we lay kissing and snuggling on my bed. I turn and ask her with her smirk on my lips, “How about a rematch?”
Source: reddit.com/r/eroticliterature/comments/tjgjp5/checkmate_f4f_wholesome_strapon