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Truth or Dare with Apple [mf] | 2016

I was nineteen and in college. And I’ve got five paragraphs of this kind of background information but bear with me because a lot of it will be relevant later on. Apple (not her real name but her real name is just as weird) was a year younger than me. We were both enrolled in the same program and even though we didn’t have any classes together we hung out with the same group of friends and we saw plenty of each other.

Apple wasn’t a looker but she was pretty. A good solid seven and a half all around. Boobs? Seven and a half. Ass? seven and a half. Face? Well she was a redhead and she had freckles so that bumps her up a point or two in my book. Personality? She was one of my favorite people to hang out with so I give her ten out of ten on that one.

I’d been pursuing Apple for a full year. I’ve read a lot of stories on this site about a couple of eighteen-year-olds who go at it on the first date (or even before any date at all) Let’s just say that for me it never worked out that way. Not for me and not for any of my friends either. Not when we were eighteen. These days we’re a bit over thirty and sex on the first date does happen. People know what they want and there’s a lot less beating around the bush but when we were eighteen the girls we hung out with sure made us work for it. I’m not saying quick and easy sex doesn’t happen for some eighteen-year-olds but the regular average guys like me we had to work for it.

Girls like Apple wanted you to become their friend before they’d even consider having sex with you. So I did. For a whole year we hung out at school. First it was with friends and it took a while for me to get to know anything about her. Then I asked her out on dates. Typically dinner, movies, drinks, that sort of stuff. Then there was summer and we didn’t see each other for a few months. Then more dates.

There’s no way you can fake friendship with someone over that long a period of time. We truly were friends. I wanted to get in her pants but I knew it would probably not happen so I just enjoyed the friendship. She was a cool girl.

Things changed for us somewhere around the fifteenth date. Instead of dinner or a movie she invited me over to her place for drinks. If you’ve read that lengthy intro just above you should know that this was a big fucking deal. That got me pretty damn psyched. I didn’t walk in there expecting sex but at least I knew it was now a possibility.

Her parents owned a triplex. The family lived on the ground floor but they didn’t rent out the basement apartment. With two grown-up kids the middle apartment alone felt a bit too small so they used the basement apartment as a kind of basement for extra space. It was a small one-bedroom and it was furnished, like a lot of family basements, with all the crap furniture they didn’t want to use in the main living area. Crappy uncomfortable couch. Crappy sound system. Crappy single bed in the bedroom.

Apple and I sat on that crappy couch and for the first couple of hours we caught up with what had happened in each of our lives since our last date a few weeks before. I’d brought some wine and as the evening went on we got looser and the conversation got more personal and intimate. Instead of “have you seen any good movies?” it was now more like “have you kissed anyone?” More personal and also more about sex.

If this had been when I was thirty and if this had been a third date I’d have made a move right about then. But I’d known this girl so long and I was so used to keeping my hormones in check around her that I couldn’t bring myself to do it just then. What I did instead definitely wasn’t the smoothest move in the book but sometimes that doesn’t matter: I asked if she wanted to play truth or dare. She did. Alright I thought, the sex door just might be open.

We started slowly with simple questions and simple dares. After a couple of those I got almost daring. “I’ve almost never seen you with your hair down. Would you untie it for me?” She did. She always used to wear her hair up in some kind of ponytail or other. I’ve read somewhere that old poets used untied, loose hair as a metaphor for a woman who’d just had sex. Yeah, that describes pretty well the effect that her letting her hair down had on me right about then.

For her next dare I got even more daring. “I’ve never seen your legs. Would you show me?” She hesitated. “You want me to take off my pants?” She sounded defensive, like that would be a definite no. “You could wear a short skirt” I said. “I don’t have a skirt here” Alright, not a definite no on that. “If I can find one would you wear it?” She said sure.

Necessity is the mother of invention and sometimes a horny nineteen-year-old will turn into a goddamn MacGyver if that might get him laid. “Stay right there” I grabbed a pair of scissors in the kitchen, I took the crappy pillowcase off the crappy pillow on the crappy single bed. Snip, snip, snip, I cut off the closed end. I shortened it too for good measure. “There you go!” The crappiest tube skirt ever made. I still think Armani would have been proud. Unless he’s gay that is. In which case I have no idea.

She smiled. Ka-ching I thought, sex door still open. She asked me to turn around while she put it on. The sound of her jeans hitting the floor was the hottest thing I’d heard in a good long time. “Turn around” She’s standing there and that thing is about six inches above her knee. Man I really cut that shorter than I thought. And it can barely hold her hips. It’s stretched so tight it’s a wonder she managed to pull it up. And it’s kind of see-through. I’m not sure she realizes it but I can see the lace of her panties underneath. Yeah, c’mon Giorgio, give me a fucking round of applause here.

After giving me a moment to check her out she sits down. The thing rips. Never mind, she says. That door now looks pretty fucking wide open.

On my next dare she asks me to take my shirt off. Happy to. Then on her turn she probably thinks I’m going to ask her to take off her shirt so I throw her a curveball. “Can I give you a massage?”

We go to the bedroom and she lies down face down on the bed. You can’t really give someone a massage over their shirt now can you? She takes it off. I take my time. I want to make it good. I figure if she thinks I’m good with my hands then sex is definitely on. Her bra’s in the way so after a while I unhook it. She doesn’t say a word. After a while longer I get even more daring and I start massaging her ass. She’s purring like a kitten. I pull the ripped skirt off. The panties come down with it.

I massage her legs, I massage her back, I massage her ass. I spread her legs and reach down to the soft spot between them. She’s sopping wet. “Stop”

The last thing I wanted to hear. But again, go back to that lengthy intro up there because that’s what it’s there for. To explain why at this moment I didn’t freak out or anything. For a whole year “stop” is what I’ve been hearing from this girl. Not “no” but “take it slow”. So fine, I do. My cock’s pretty fucking hard right about now and that makes it pretty fucking difficult to take it slow, but I do. I go back to massaging the rest of her. After a while longer I ask her if she wants to turn around. She doesn’t say anything but she does it.

It’s the first time I’ve seen her naked and my heart wants to jump out of my chest. My cock’s so hard I don’t know where it wants to jump to but I’ve got a pretty good fucking idea. Her skin is so pale she looks almost like one of those porcelain dolls. Excuse the cliché. Her dark nipples pop out on that pale skin and they look almost red. She’s got small boobs but they still look like two good little hills with her lying down like that and the nipples stand hard and straight on top of them. And between her legs? Just the softest, whitest little pussy I’ve ever seen. With her legs mostly closed there’s no trace of inner lips, just a cleft under a bare little mound.

I massage her shoulders, her arms. I go for her boobs. She’s got her eyes closed and she just breathes in. Clearly she’s enjoying that. I stay on the boobs a good long while. I stroke, I caress, I pinch and pull at her nipples. She’s breathing heavily. I go down. Her thighs, her hips. I reach under her to squeeze her ass. I part her legs again. “Stop”

Fuck. Take it slow, take it slow. I repeat it like a fucking mantra in my head. I go back to her shoulders, her boobs. “Truth or dare?” I ask her. She’s surprised. She didn’t think we were still playing. “Dare” Let’s try a different tack. “Can I kiss you?” She licks her lips. She’s thinking about it. “Yes”

I lie down on top of her to kiss her. The lying down on top of her part wasn’t in the dare but she’s not about to say no. Her legs open under me and she wraps her arms around me and we kiss. We start slow. It’s the first time we kissed. Only lips at first then our mouths open and our tongues touch and caress each other. I kiss her neck. I kiss her boobs. I lap then suck at her nipples a good long while. She’s starting to moan a bit and her breathing gets heavier still. I kiss her stomach. I kiss her pussy. She’s so sopping wet I don’t know how she can control herself. It must be just as hard for her to keep saying “Stop” as it is for me to hear it. “Stop”

Take it slow, take it slow. I move up again. We kiss. She’s really getting into it. Her hands are on my back, in my hair, on my ass. My bare chest is pressing against her boobs. My cock is stiff under the fabric of my jeans; I reach down and unbutton them. She’s so wet my cock glides easily over her lips but I’m not going in. We kiss some more. Finally I reach down and press the tip of my cock against her cleft. “Wait”

Wait is better than stop. Wait sounds pretty fucking good right about now. I can take a dozen of those waits no problem. My cock stays out. We kiss some more. I move down to suck on her nipples. I move back up and we kiss again. My cock is slick from her juices and it’s pressing against her pussy again.

“I met someone else”

The dame must be on crack because she’s not making any fucking sense. The sex must have gotten to her head or something. Clearly she’s delirious. We keep kissing. I push my hips forward only slightly and the tip of my cock, just the tip, slides inside her maybe half an inch.

“There’s another guy” What is she saying again? “What do you mean there’s another guy?” The tip of my cock is still inside her and I’m trying hard not to move but it’s pretty damn awkward with my hips raised like that. “I met him a month ago.” What the fuck do I care? I care of course but I would have cared a whole lot fucking more thirty minutes ago. Or thirty minutes from now. Just not at this particular moment. “Have you had sex with him?” “No” “Have you kissed him?” “No” “How often have you seen him?” “Three or four times” “What do you mean there’s another guy?”

I kiss her again and she can’t answer right away. I can’t wait any longer. I thrust in and my cock slides all the way in. She takes her lips off mine and she moans. I start thrusting in and out slowly. “Wait, wait”

I keep still. My cock is pushed all the way inside her. Her slick juices cover the top of her inner thighs and mine. “I think I might love him.” Well that’s worse than I expected. “And what about me?” “I think I might love you too.” Well that’s that at least. I don’t know what to say so I kiss her some more. I kiss her mouth, I kiss her nipples. My hand caresses her hips and her butt. Nature takes over and I start thrusting again. Her thighs press against me. Her legs wrap around my ass.

“I can’t do this to you” “Do what?” “I don’t want to have sex and then have to push you away because of him” That’s sweet, toots. Any other time that would have made me go all soft inside. But I’m sorry but my dick has taken over right now. The heart’s on an extended vacation right at this moment. Leave a message and it’ll get back to you right after I’ve taken care of this little thing right here.

“I’m not asking anything of you” I say. Yeah, that seems to confuse her more than anything else. “I’ll take from you what you’re willing to give. I’m not asking for anything else.” She looks me right in the eyes. “Are you sure?” We’re still fucking. Slowly, but we’re still fucking. “I want all of you but if I can’t have it I’ll take what you give me.” She seems to like that. “I can share you. I want all of you but I’ll share you if that’s really what you want. Or if you don’t want any of me then I’ll let him have you.” We fuck faster. Her legs are pressing me into her. “Do you promise?” We’re really fucking now. Hard and fast I’m thrusting into her. She starts moaning again. “Do you promise that if I say I don’t want us to see each other again then you’ll be okay with that?” She’s got her eyes closed again and she doesn’t see me when I answer. But I mean it, what I say to her. I’m not going to lie to her. I’ve known her too long I’m not going to try to play her or screw her. Even for sex. “I’ve been waiting for you for months. I take what you give me. Dates, dinners, movies. I didn’t even ask for a kiss all this time. If you give me sex I’ll take that. And if you fuck this other guy I’ll be happy to share you with him and take only the part of you you’re willing to let me have. And if you tell me we’ve got to go back to the way things were I will. And if you tell me to go away completely and let you be with him, then it’ll be hard, it’ll be fucking hard, but that’s what I’ll do. I promise.”

Fuck that was a long speech. I’ve got myself almost convinced that I’ve already lost this girl. My thrusting has slowed down to a crawl. But she’s still got her legs pressed against my ass. She opens her eyes and we kiss. Slowly at first but quickly it’s much more intense. I’m thrusting hard again. She moans and she takes her lips off of mine. “Oh just fuck me…”

***

And as people do with these things here’s some closing info. Birth control? No. But after we had sex I look at the sheets and there’s a red spot. And I look at my dick and there’s a bit of blood on there. And for a while I’m confused. I ask if she was a virgin. No, silly, but her period had just finished the day before so she figured unprotected sex was okay. She didn’t get pregnant. The other guy? Yeah she quickly forgot about him. Sorry dude I got there first. Did she become my girlfriend? She did and we were together a couple of years. The relationship got stale, she kind of found someone else but nothing came of that that I know of, then she got a job in another state and that was that. Did I really say all those corny things to her? I’m afraid I did. It was a long time ago and my memory may have embellished a little but we talked about our first night a lot when we were still together and that was the gist of it. That’s how she remembered it too.