Sam will take this lying down
From Torg Adventure
You can't find any reason to disagree with Sam's suggestion. "Well, since you do have your little heart set on the missionary positi-"
"I do not have my heart set on anything with you, Peewee!" Sam is indignant and embarrassed, although you sense she also realizes at some level you are teasing her as well. "Don't delude yourself that this is anything other than me honoring our agreement." She turns and climbs onto her bed, slowly then. "But on the other hand, I'm not going to be a poor loser on this one. Even though this is in no way how I wanted or expected to lose my virginity, I'm not going to sandbag my way through this." She lays back on the bed then, carefully letting her hair settle under her head on her pillow. "I'll be... cooperative. I may not have any experience, but I'll do what I can to make you enjoy it. And I won't fight it if I start to enjoy it myself, if you think you are man enough to make me climax."
You sit down on the edge of the bed by Sam. "Lisa was woman enough to make you climax."
Sam colors slightly. "I thin Lisa has more experience than everyone else in this family combined... Mom included. She knew... just where to touch me."
You put your hand between Sam's legs. She involuntarily tries to shove her ships down further into the bed, as if to get away, but your hand still settles over her mound. She is still a little wet from her mutual masturbation session with Lisa, so you use her wetness to coat your fingers as you trace them over her opening. She has what some people call an 'innie' pussy, kind of a peach shaped mound, broken by her slit.
"Did she touch you like this?" You keep moving your fingers up and down her moist pussy.
"Some," Sam admits, breathing a little heavy. "She played with my... button mostly though."
'Button'. Same can't even say clitoris. That doesn't stop you from moving your wet fingers to it, and rubbing it in a circular motion. "Like this?"
Sam gives a little moan. "Yeah, kind of like that. She was better, though."
"You're not enjoying it, then?"
Sam blushes again. "You know damn well I'm enjoying it. I didn't say you were bad at it... just that Lisa was better. Like I said, she has more experience with sex than you."
"Fair enough." Lisa's experience in matters sexual was not in doubt in your mind, although you wouldn't mind getting some first hand experience of that. Sam first, though. Still rubbing her clitoris, you climb on top of Sam on the bed. She helpfully spreads her legs so you can get your body positioned. "I may not have Lisa's experience, but I do have something Lisa doesn't." You take your hand off of Sam's clitoris, and puts it on your cock, encased in the condom.
Despite herself, Sam can't help but look down at your cock. "No, Lisa definitely didn't have that." Then she twitches as she feels the head of your cock pressing up against her pussy. "Fuck. Remind me never to make a bet with you again, Peewee. Or any other stupid standing offers for guys who fight me."
Your only response is to start pushing forward then. To her credit, Sam doesn't try to move away from you on the bed as you push forward, although she definitely seems to be making a conscious effort not to do so. Still, she twitches again when you press up against her hymen.
"I'm sorry, Sam," you apologize. "This is probably going to hurt a little."
Sam rolls her eyes. "I've dealt with pain before, Max. It will be like when I dislocated my shoulder. You just have to... put it in the right spot quickly, and then you're past the pain." When you hesitate, she looks a little frustrated. "Damn it, Max, I'm not a fragile doll. I can take a pounding." She clearly meant a pounding in a fight, although she realizes the more immediately relevant meaning of the word, and blushes again. "You know what I mean. Just do it already, Peewee, before I change my mind about this entire mess and make you get off of me." She moves her long legs even further apart.
Worried that she may actually change her mind if you dally anymore, you take her advice and do put your cock in the right spot quickly, with the right spot being deep inside her pussy. She's tight, but Lisa's previous work on her sister's pussy made the going easier for you. Sam inhales quickly as you take her virginity, but other than that, doesn't show that she's in any pain.
She exhales them, much more slowly. "Not as bad as they say it is. Still, I'm glad that only has to happen once."
"You doing okay? You want to me stay still for a bit?" As much as you want to start fucking your sister in earnest, you don't actually want to hurt her. At least, more than what is going to happen due to her being a virgin.
Sam looks annoyed. "I keep telling you I'm not some timid little girl. You don't have to worry too much about hurting me."
You pull out a little and thrust back in again. If Sam feels discomfort from it, she doesn't let it show. "You're so tight though. Like a timid little schoolgirl."
"Tight is good though, right?" Sam looks up at you questioningly. "That's what guys want, isn't it?" She seems a little self-conscious about how her pussy feels to you.
"Yeah, tight is very good, Sam." You keep thrusting in and out of her slowly.
"I can be tighter, I bet." She squeezes her pussy around your cock, and suddenly she is so incredibly tight around you that it feels incredible, but is impacting your ability to move. "How's that?"
"Really tight, Sam. I can barely move, though."
"Sorry," she says contritely, and loosens up a little. "Maybe if I just squeezed a little, now and then..." Her pussy contracts on your rod, just as you're pushing into her, not as tight as before, but tight. You moan at the way it feels on your throbbing cock.
Despite herself, Sam laughs. "I think I could be really good at this. It's just another sport to master."
"I'd be more than willing to help you practice, Sam," you say truthfully.
Sam scowls again, but keeps squeezing her pussy around your dick as you move in and out of her. "Fat chance, Peewee. We do this the three times as we agreed, and that's it." You note happily that at some point she apparently consented to the three times you mentioned earlier, due to Lisa interrupting your first attempt. "Besides, I'll bet I'll be pretty damn good after three times."
You suspect Sam is right. It's her nature, even her gift to pick up any kind of athletic skill quickly, and excel at it. Why should fucking be any different?
Sam's mind continues to look for ways to improve. "Maybe if I start doing this..." She starts pushing her body back down against you as you push into her, creating more resistance. "Yeah, that feels good for me, at least." She keeps moving her body, while her pussy keeps squeezing you.
She wraps her arms around you. "Don't think I'm getting romantic, Peewee," she warns. "I need the leverage."
"What's wrong with a little romance?" You lean down to try to kiss her.
"Fuck that, you're my brother," she says, turning her head. Your lips touch her cheek instead.
"We're already doing far more than kissing, even though I'm your brother."
Sam bites her lip. "I know, even though I'm trying to ignore that part of it. But kissing is somehow... more intimate. At least on the lips."
You kiss her throat instead then. It's a long, elegant throat, with Sam's characteristic silky smooth skin. "So here is okay?"
Sam moans a little, probably from the fucking, although her neck also seems to be sensitive. "If you have to."
You kiss her neck again, and feel her shiver beneath you. "I have to." You keep kissing her neck gently, then move up to kiss her earlobe. "But I'd really like to kiss you on the lips."
"Max, no," she protests. "Can't you just be happy with having sex with me? I've given you my body."
"You've never even kissed a guy before, have you?"
Sam sighs. "No. And I would prefer not to start with my own brother. Like I said, it's more intimate somehow."
"You said you would cooperate..."
Sam's shoulder's slump. "Fine." She turns her head back to you. "Kiss me, then."
You kiss her then. Sam shows more involuntary resistance to this than she did to you putting your cock into her. She doesn't turn her head this time, although she does press her head back hard into the pillow as your lips touch hers. Her lips are locked shut as you kiss her gently.
"Come on, Sam," you goad. "You can do better than that."
Reluctantly, Sam's mouth opens a little and she kisses you back, timidly. You keep kissing her, and her lips lose some of their tentativeness as instinct takes over. Finally, it's you that breaks the kiss, to give yourself time to breathe.
Sam catches her breath too, something that is becoming increasingly difficult the more excited your bodies get. "Satisfied then, Max?"
You smile down at her. "Not yet, but I'm getting there."
Sam smiles wanly. "Yeah, me too. Like I said, I wasn't going to fight it, if it was going to happen." She moans softly. "And I think it is going to happen."
You keep fucking her, harder this time. She has never stopped squeezing your cock and moving her body, and matches your increased tempo. And now, when you move your lips back down to hers, she meets you halfway.
"I suppose practicing kissing couldn't hurt, either," she murmurs softly. "That's all this is, really... practicing. You're just helping me develop some skills, like when I make you hold the pads for my kicking."
"Are you sure that is all this is?" you ask softly.
She looks back at you, a look in her eyes. Fear? Desperation? "That's all it is, Max. That's all it can be. That's what it has to be.
You decide not to press her on the subject, and instead just keep pressing your cock deeper into her. You kiss her again, and feel her hot breath against your mouth. her breathing is deep and rapid, as both of your bodies are getting swept up in a tide of hormones and lust.
"God, I hope I didn't mess up the condom," Sam pants. "Maybe you were right... I just didn't think I could trust you..."
"It will be fine, Sam," you say soothingly. You don't know if the tiny hole you made in the condom, or Sam's inspection and sloppy handling of the condom would be enough to make it break when you came. You're certain that some cum is definitely going to get out through the hole you made. You're counting on it, in fact. Sam shouldn't notice that, you'd think. If it does break though, Sam would definitely notice that. How would she react?
"It has to be," she says, fighting to get the words out as her passion grows. "I can't get pregnant... not from my own brother." She looks up at you. "I should have you pull out, before you finish."
You keep fucking her, and she doesn't stop fucking you back. "That wasn't part of the agreement."
"I know." Sam holds you closer with her arms. "And I won't make you do it. I just know I should have you do it, if I wanted to be safe."
"I want to be in you when I cum." If you aren't, your cum won't get into her.
"And I kind of want you to be in me when I climax, too," Sam admits. Then she hastens to add. "At least my body does. I... need the practice."
She groans then, her arms and pussy squeezing you tightly again. "God, this is a workout. I'm all sweaty and gross."
"You're beautiful Sam." She is. Even drenched in sweat, her entire body flushed, she's still just as hot as ever.
Sam manages to blush even more at that point. "You're... you're just saying that because you're my brother..." Then she laughs nervously. "God, that was stupid. To be concerned over a compliment from my brother, while he's having sex with me..."
Then her eyes widen a little. "Oh fuck, what are we doing, Max? What am I letting you do to me? This is incest... this is so wrong. My own brother's cock inside of me, making love to me..." For the first time, she stops squeezing your cock. Her body stops moving under you.
"Its okay, Sam," you say soothingly, still fucking her. She hasn't told you to stop, and you're not sure if you could at this point. "Everything will be okay."
"No, it fucking won't," she moans desperately. "I'm getting fucked by my own brother, and it's the best thing I've ever felt in my life, and no decent girl should be liking it this much." Of it's own volition, her cunt starts squeezing yours again. "I got my cherry popped by my own brother, and... and... he's about to give me the biggest orgasm- ohh!" Then her body arches under yours as an earth-shattering climax rocks her body. If you wanted to, you couldn't stop cumming at that point if you tried. But you don't want to. You want to cum, just for the pleasure of cumming at the same time as Sam, and also in the hope that some of your sperm will make it out through the hole in the condom, and to Sam's fertile egg.
You feel the cum rush out of your cock. You feel some of it against the tip of your cock, so you know the condom didn't break, at least entirely. You feel another load escape as Sam quivers beneath you, but you aren't in the best position to tell where it's going.
"Oh God," Sam moans, as orgasm continues to rock her body. Her concerns of a few minutes ago are lost in her current ecstasy. You kiss her while the two of you are in the throes of orgasm, and she kisses you back hungrily, and the kiss lasts for the rest of the orgasm.
Sam collapses under you then, panting heavily, her eyes closed. You are worn out too, and lean a little of your weight on her. Her hot, sweaty body feels good pressed against yours.
Then Sam's eyes fly open. "I feel... wet, Max," she says. She tries to look down between your two bodies, but they're pressed too closely together. "Get off me, you big ox. I have to see it. I have to see if it held."
Did it break, or does it still look intact?
