High School Ex

The first option that jumps to your mind is your High School Ex Tommy, one of the star players on the school football team. You went out for a few months last year, but he ended up breaking it off with you when you wouldn't go all the way with him. You'd spent a lot of time together and while you really liked him and you enjoyed making out with him, he eventually wanted more than you were willing to give him at the time. Thinking back, you remember the feeling of sitting on his lap and the hard erection pressing against your ass as you tried to ignore it or the couple of times or the times, he convinced you to rub him through is pants. At the time, it had made you uncomfortable, but now the thought of his hard cock in your hand made you wet, just imagining it.

While the actual break up had been tough, he'd thrown accusations at you of being a prude, a cock tease, and of giving him blue balls; you had eventually gotten back onto being friendly again.

You ring him up and when he answers, you say, "Hey Tommy, it’s been awhile and I was thinking about you. I was wondering if you wanted to hang out and maybe catch a movie today?"

"Uh, I dunno Alana," Tommy responds uncertainly, his deep voice already sounding intoxicating to you. "I had some plans. I didn't think we really hung out like that anymore."

"I know it didn't end that well between us, but we're still friends and I figured it would be fun... for old times’ sake," you petition him almost desperately over the phone, hoping he'll bite at the invitation.

After a long pause, keeping you in suspense, Tommy replies, "I guess we could hang out today."

"Awesome!" you exclaim in excitement, as you get one step closer to getting fucked properly. "Did you want to catch a movie or something else?"