Winning

"Exactly what is your problem?" I asked the boy from Lunch and Should Have the second we were alone in the car. We'd been talking on and off for a few months and it always went the same way. The conversation would heat up until the point where any normal guy would make a move, at which point he would panic and run away. The last time I'd seen him he'd jumped at the chance to drive me home at the end of the night and spent 20 minutes kissing me in the car, but when I invited him inside for more I was met with a lame excuse about having to get up early in the morning. This night had gone about the same. I was wearing my cocksucker t-shirt when I went to see him play a show with his band. He couldn't figure out the picture and I had to explain it to him. We wound up having a text message conversation about it from opposite sides of the room:

Lunch: Wait a minute, does that mean that your shirt is a cocksucker or that you are?
Me: If you weren't such a fucking tease you'd already know the answer to that question.
Lunch: haha, just keep it in your mouth til I'm done.
Me: Of course I would. I didn't know there was another way to do it.
Lunch: well obviously you are not catholic
Me: Nope, just a heathen protestant trying to get in your pants.

I didn't get an answer to that.

I don't like being told no. I wasn't even being told no specifically, I was just being stymied by his indecision and whether it was due him being a good Catholic boy or just finding me intimidating the result was the same: I wanted to fuck Lunch and his crisis of conscience was keeping me from getting what I wanted. I was growing increasingly annoyed with this and probably should have written him off, but by then it had become something of a contest in my head and I was determined to win. And now that I had him alone again I wasn't about to let him off the hook. "I know you're attracted to me because you've said so and also you can't keep your eyes off me any time we're in the same room. And you know I think you're cute, so what is the deal with you?"
 
"I just don't know if it's a good idea."
 
"Why the hell not? I'm not trying to marry you, [Lunch], I'm just trying to get in your pants, but for some reason you're turning it into some kind of existential crisis."
 
"Well maybe that's my problem, we're not going out."
 
"Bullshit. You're making the whole thing into a much bigger deal than it actually is. I want to sleep with you and you want to sleep with me, but instead you'd rather just be a big pussy. You're ridiculous, man. And now you're going to drive me home and I'm going to ask you to come in and you're going to tell me no, even though you know that's what I want and you know it's what you want!"
 
"Well, what about your roommate?"
 
"He's not even home, he's at work."
 
"Yeah, but he might come home."
 
"No. Now you're just making shit up. You don't get to use that as an excuse, so here's what we're going to do: If just taking me home and dropping me off is what you really want to do then fine, take me home. But if you want to sleep with me, and I know that you do, then you need to man up right now and turn the car around so we can go back to your place."
 
He turned the car around.
 
I have to give him some credit. Despite making the whole thing a huge hassle AND despite the fact that he continued to argue with me about whether it was a good idea the entire way to his apartment (including what might be a clue to his reluctance when he asked me - twice - "But what if you think that I suck?"), once he conceded that I couldn't be talked out of it he went all in. The moment the elevator doors closed I was his: he pulled me against him and kissed me hard, his hands instantly under my skirt and gripping my ass. Inside his apartment he continued kissing me as he pushed me backwards into his bedroom stripping off my shirt and my bra as we went. He fell backward onto the bed and pulled me down on to.p of him, tugging my panties off and moving down o lick my very wet pussy. I noticed his pants had disappeared, I have no idea how or when he got them off. When he sat up to pull off his shirt I used the opportunity to take his cock into my mouth, but I didn't get to suck him very long before he was pushing me onto my back and sliding his cock deep inside me. I came almost immediately with my legs up on his shoulders. Then he pulled me back on top of him with his body half hanging off the bed, his hands pushing against the edge of the mattress and pushing him deeper inside me as I rode his cock hard. So hard in fact that right after the second time I came we fell right off the edge of the bed and landed giggling in a pile on the floor. We stood up and he bent me over the edge of the bed, his fingers digging into my hips as he pounded me hard from behind. I lost my balance and fell forward onto the bed. He fell on top of me, holding my arms down at my sides and slamming into me until I felt his cock throbbing inside me as he came.
 
He rolled off me and lay back on the bed exhausted. I crawled over and laid next to him, smiling. "Now explain to me," I said teasingly, "why you made me wait so long for that."
 
"I really have no idea. You feel fucking amazing," he answered.
 
I win.

Should Have

I should have made a move that first night. The night we met when you couldn't take your eyes off me. When you kept coming up with excuses to take more photos of me and when you asked me whether ribbed condoms really made a difference for her pleasure. "I'm very attracted to you," you'd blurted out, and I giggled and thanked you, but if I'd known that was the closest you'd get that night to asking me to come home with you I'd have done things differently.

It's a dark corner there where they've tucked away the two ladies rooms. No one would have noticed had I taken your hand and pulled you into the second one, locking the door behind us and kissing you hard as my body pressed against you and pushed your back against the wall. My fingers would have instantly started working on the buttons of your fly and when your pants dropped to your knees I'd have dropped to mine and taken your entire cock into my mouth at once. I'd have sucked you in long deep strokes, feeling your cock growing harder in my mouth and my pussy growing wetter and soaking through my panties. They'd have to come off. Realizing this, I'd have stood up and let them drop to the floor, taking your hand again as I stepped backwards out of them until I was half leaning and half sitting on the edge of the sink. I would have pulled you close and wrapped my legs around your waist, my hands gripping the edge of the counter as you held me by the hips and slid your cock inside of me. You'd have fucked me more roughly than you normally would for your first time with a new girl, but you'd have known that was what I wanted from you when I moved one hand from the counter edge to you ass to urge you deeper. You'd have felt my pussy pulsing around your cock when I came and my legs would have lost their grip around your waist and fallen open while I leaned back with my head against the mirror trying to get my breath back. I'd have smiled when I felt your fingertips digging into my thighs, pounding me hard until your cock exploded inside me. I would have pushed you away as I slid off the edge of the sink, snatching up my panties off the floor and kissing you while I surreptitiously stuffed them into your back pocket for you to find later on when you got home.

In hindsight I should have done all that, but there was no way I could have known that you wouldn't have the balls to invite me home with you later on or how long you would end up making me wait for it.