Straight Male / 42
One night playing truth and dare with some of my daughter's friends and my daughter, some of the questions got a bit dirty, quite perverted, and very very sexual in nature. At one point, my daughter laughed and said "TMI" and said she was going to bed. I understood it. Because it had really gotten bad. I think the reason she'd gotten up and left, truthfully, is because I knew at the time she was a virgin (14), and a couple of her friends that were there weren't. They had the experience that most girls either hadn't, or didn't talk about. Her one friend Crystal was 14 or 15, and very knowledgeable for a girl her age. The other friend Brittney I knew had experience, we'd heard rumors and gossip, and there had been talk about some of the stuff she'd done. Even my daughter said that people had heard around school that she got around, and had done quite a few of the guys in her class. Whether true or not, nobody could really confirm it.
I put this under embarrassing because I'm an older guy, and I know older guys aren't supposed to think about girls that age. But yeah, well I did. I'd never given it thought until that night, but the more we talked, the hornier I got. And after my daughter went to bed, I think I took it well beyond what was expected, because at one point, Crystal says to me "damn dude, are you horny or what?" and I just said yeah. I know it's kinda gross and shit, especially because of your age and Brittney, but sorry. Just couldn't help it.
Crystal looks at me, and laughs and says it's all cool. Guys get horny all the time. Girls do too. And Brittney laughs, says yeah, I get horny every single day. But never talked to a friend's dad about it and shit. This is kinda weird. I just laughed and said yeah. Sorry. Not a good conversation. Next. And Crystal says nah. I think it's cool. She looks at Brittney who shrugs and says sure.
Now we're hanging out in my den, talking, still making comments and cracking jokes, and Crystal says ever been with a chick my age? I just laughed and said no. Jail isn't appealing, so I've never acted on it, or really given it thought. Brittney says oh, so you'd actually do it? I just shrugged and said what guy, regardless of age, wouldn't want to tap some hot high school chick? If word ever got out though, yeah, his life is over. And Crystal says so don't let word get out? I laughed and said not that easy. Imagine a high school girl have some guy fuck her half blind? Get her off, soak her, and make her think she's gone on a trip to the moon? She's gonna wanna brag about it. And Brittney looks at me and says you can get someone off like that? Really? Do tell? I just said well I've done it enough, I think I know what I'm doing. And without hesitation, Crystal says to me prove it. Show me. I looked at her and said nope. Not interested in jail. And she says oh. That's too bad. I'd do you. I just laughed.
Then realized she was serious. And for the fleeing thought, I thought holy shit, I could actually fuck her I think. She's actually throwing it out there. I looked at her, and she laughed and said no. I've never really thought about banging a guy your age. I just said aw, that's too bad. It might be fun. And she looked at me, eyes wide, and said holy shit. Are you coming onto me? I just shrugged and said I dunno. Guess you can take it for what it's worth. Brittney looked at her, and said could you live with it, thinking about it later? Crystal say with a shrug I dunno, guess I won't know unless I do it. But yeah, I get what you're saying.
I was embarrassed, because I desperately wanted to fuck her. But I had no idea how to ask some teenage chick to have sex with me. Crystal looks at Brittney, and doesn't say anything. So I just came out with it, and said I'd fuck you. Seriously. No lie. Crystal says to me "you're asking? So if I said yes, you'd bang me?" And I came out and said I'd love to. It's been a fantasy of mine. But I'm embarrassed, and I don't want to sound like I'm begging. But deep in my head, yes, I was desperate, and I wanted to plead with her, embarrass myself, and beg her to let me fuck her.
Crystal said to me beg me. Ask me. Plead with me. Sound desperate. And damn if I did it. I asked her. I begged her. I pleaded with her. And she finally said I'd do it. If you're any good, which you say you are.
When Crystal started undressing, she told Brittney to get her a condom. Which she did. I'm in good shape for a dude my age, take care of myself and all that, and I eat right. I figured I'd be pretty good, even with a high school chick, and I'd fuck her good enough that hopefully she'd want more, and pray to God she'd never tell anyone.
When we finally got down to it, Brittney was laying there on the couch watching. I'd gotten Crystal naked, I was fingering her, I got her to cum, we were doing some kissing here and there, she was touching my dick, getting me harder, and said you're pretty big. Not too bad. I just said well thanks. And she said you should put your condom on. I kinda wanna fuck. I said sure.
When I got it on, and Crystal was on the floor, I went inside her. And I'm embarrassed to admit it, but I fucked her like four or five times, and I couldn't hold back. She was laying on her back, I'm sticking my dick inside her, pull back, look at the condom soaked with her juice, and I exploded as I entered her again. I just thrust, and gasped and said oh fuck. And I came. It kept going. I kept fucking her really hard, pounding into her, and after like 2 or 3 minutes, I was done. I stopped cumming, and although my dick was still hard, I knew I'd finished.
I just laid there for a second, and when I pulled out. Crystal said damn, you were pretty good. It felt good. You got me off like three times, and made me cum. But I guess I thought you'd last a bit longer is all. I felt stupid as fuck. I was just sitting there and said yeah. And she said but I liked it. It was fun. And got up quickly and started getting dressed. I tried to talk to her, and she talked back, but I knew it was over.
When I went into the other room, I heard Brittney say "I wanted to fuck him. I think I'd try it too, you know, maybe do a three or something" and I heard Crystal say "well he might last longer a second time. I dunno. I'd always heard guys would go forever at an older guys age and shit. But he was like 5-10 minutes. Not too bad. But I wanted more." and then I heard Crystal say "Nah. I'm gonna go to bed. I mean, it was fun. But I dunno if I'd fuck him again"
The next morning, she'd barely talk to me. We talked a bit, Brittney talked a bit, and they left that afternoon. What's really shitty is that I tried a couple other times when they'd come to spend the night, and nothing. I know it's because I came too quick. First and only time I get to fuck a hot little high school chick, and I blow my load too fast and can't get any more pussy again. Sucks.
I put this under embarrassing because I'm an older guy, and I know older guys aren't supposed to think about girls that age. But yeah, well I did. I'd never given it thought until that night, but the more we talked, the hornier I got. And after my daughter went to bed, I think I took it well beyond what was expected, because at one point, Crystal says to me "damn dude, are you horny or what?" and I just said yeah. I know it's kinda gross and shit, especially because of your age and Brittney, but sorry. Just couldn't help it.
Crystal looks at me, and laughs and says it's all cool. Guys get horny all the time. Girls do too. And Brittney laughs, says yeah, I get horny every single day. But never talked to a friend's dad about it and shit. This is kinda weird. I just laughed and said yeah. Sorry. Not a good conversation. Next. And Crystal says nah. I think it's cool. She looks at Brittney who shrugs and says sure.
Now we're hanging out in my den, talking, still making comments and cracking jokes, and Crystal says ever been with a chick my age? I just laughed and said no. Jail isn't appealing, so I've never acted on it, or really given it thought. Brittney says oh, so you'd actually do it? I just shrugged and said what guy, regardless of age, wouldn't want to tap some hot high school chick? If word ever got out though, yeah, his life is over. And Crystal says so don't let word get out? I laughed and said not that easy. Imagine a high school girl have some guy fuck her half blind? Get her off, soak her, and make her think she's gone on a trip to the moon? She's gonna wanna brag about it. And Brittney looks at me and says you can get someone off like that? Really? Do tell? I just said well I've done it enough, I think I know what I'm doing. And without hesitation, Crystal says to me prove it. Show me. I looked at her and said nope. Not interested in jail. And she says oh. That's too bad. I'd do you. I just laughed.
Then realized she was serious. And for the fleeing thought, I thought holy shit, I could actually fuck her I think. She's actually throwing it out there. I looked at her, and she laughed and said no. I've never really thought about banging a guy your age. I just said aw, that's too bad. It might be fun. And she looked at me, eyes wide, and said holy shit. Are you coming onto me? I just shrugged and said I dunno. Guess you can take it for what it's worth. Brittney looked at her, and said could you live with it, thinking about it later? Crystal say with a shrug I dunno, guess I won't know unless I do it. But yeah, I get what you're saying.
I was embarrassed, because I desperately wanted to fuck her. But I had no idea how to ask some teenage chick to have sex with me. Crystal looks at Brittney, and doesn't say anything. So I just came out with it, and said I'd fuck you. Seriously. No lie. Crystal says to me "you're asking? So if I said yes, you'd bang me?" And I came out and said I'd love to. It's been a fantasy of mine. But I'm embarrassed, and I don't want to sound like I'm begging. But deep in my head, yes, I was desperate, and I wanted to plead with her, embarrass myself, and beg her to let me fuck her.
Crystal said to me beg me. Ask me. Plead with me. Sound desperate. And damn if I did it. I asked her. I begged her. I pleaded with her. And she finally said I'd do it. If you're any good, which you say you are.
When Crystal started undressing, she told Brittney to get her a condom. Which she did. I'm in good shape for a dude my age, take care of myself and all that, and I eat right. I figured I'd be pretty good, even with a high school chick, and I'd fuck her good enough that hopefully she'd want more, and pray to God she'd never tell anyone.
When we finally got down to it, Brittney was laying there on the couch watching. I'd gotten Crystal naked, I was fingering her, I got her to cum, we were doing some kissing here and there, she was touching my dick, getting me harder, and said you're pretty big. Not too bad. I just said well thanks. And she said you should put your condom on. I kinda wanna fuck. I said sure.
When I got it on, and Crystal was on the floor, I went inside her. And I'm embarrassed to admit it, but I fucked her like four or five times, and I couldn't hold back. She was laying on her back, I'm sticking my dick inside her, pull back, look at the condom soaked with her juice, and I exploded as I entered her again. I just thrust, and gasped and said oh fuck. And I came. It kept going. I kept fucking her really hard, pounding into her, and after like 2 or 3 minutes, I was done. I stopped cumming, and although my dick was still hard, I knew I'd finished.
I just laid there for a second, and when I pulled out. Crystal said damn, you were pretty good. It felt good. You got me off like three times, and made me cum. But I guess I thought you'd last a bit longer is all. I felt stupid as fuck. I was just sitting there and said yeah. And she said but I liked it. It was fun. And got up quickly and started getting dressed. I tried to talk to her, and she talked back, but I knew it was over.
When I went into the other room, I heard Brittney say "I wanted to fuck him. I think I'd try it too, you know, maybe do a three or something" and I heard Crystal say "well he might last longer a second time. I dunno. I'd always heard guys would go forever at an older guys age and shit. But he was like 5-10 minutes. Not too bad. But I wanted more." and then I heard Crystal say "Nah. I'm gonna go to bed. I mean, it was fun. But I dunno if I'd fuck him again"
The next morning, she'd barely talk to me. We talked a bit, Brittney talked a bit, and they left that afternoon. What's really shitty is that I tried a couple other times when they'd come to spend the night, and nothing. I know it's because I came too quick. First and only time I get to fuck a hot little high school chick, and I blow my load too fast and can't get any more pussy again. Sucks.
