Shy Guy

Jack was about to leave the party when Samantha grabbed his hand and took him to the bathroom. He was unsure at first, but if you're partying at someone's house and they need you for something, the rule is, you oblige. Right? It helps if they're also one of the most popular girls in school. Samantha pushed Jack in, she followed behind, closed and locked the door behind her. She quickly took the drink from Jack's hand and set it far back on the counter, out of the way, and pushed him gently against the counter so that his back was towards the mirror. She stood in front of him for a moment.

"Listen Jack, here's the deal. We all know you're a virgin, and my friends and I picked straws to see who's gonna fuck you tonight and take your V-card. I drew the short straw. All you need to do is stand there, I'm gonna fuck you, and then you can go back to whatever it was you were doing, standing awkward in the corner. Got that?"

Jack shifted uncomfortably. While he had wanted to lose his virginity at some point, he was also incredibly shy; he didn't want to lose it this way. Samantha was as good-looking of a woman as any other senior in his high school class, but he was hoping for, you know, more of a connection. But he always had trouble speaking up, and that included now.

"I wasn't-"

"Shutup." She held a finger up and almost glared at him. "Don't spoil the mood. Tonight's your big night, Jack." He stood still as Samantha started drunkenly grabbing at his crotch. His body betrayed him, and he started getting hard even though mentally he was far from "into it". Samantha felt it, and paused.

"What... the fuck...?"

She looked him in the eyes for a moment and seemed to sober up a bit before she crouched down and undid the fly and button on his jeans. She ripped his jeans and boxers down at once and her eyes widened.

Before her, right at eye level, was Jack's swollen cock. The problem was, it was huge. Not what she was expecting on some shy kid. Her eyes widened as she took it all in, and she was worried. She estimated it must have been 8, maybe 9 inches, and thick. Like, really thick. She reached out and was about to touch it when it twitched, and she withdrew her hand. It wasn't even fully hard yet.

"Oh my God, I knew you were a freak. There's no way that thing is going inside me. No fucking way! I've gotta get outta here."

Samantha jumped up as Jack pulled his pants back up quickly, the spell over him broken.

"Don't you say a fucking thing" Samantha hissed behind her as she opened the door and disappeared.

Jack followed back to the rest of the party a moment later with his drink in hand again. Head hung low, dejected; he was hoping to just finish his drink and go. Why did I even come to this party he thought. He knew why. He was hoping that he could start remaking his image. Meet someone. Make some friends. Maybe even meet a girl. Ever since his mom died when he was 12, he really struggled to make new friends and had an especially difficult time with women. His dad was always at work trying to make ends meet, so he was largely left to his own devices. He was responsible, just socially awkward.

He was finishing his drink when he realized Samantha and her friends were all talking hushed and smiling, giggling. Another girl from the group came out from the kitchen, with an extra drink. Amy was her name. Maybe. She held it out to him. "Need another, shrimp-dick?" She asked, loud enough that several people turned to look.

"W-what?" He asked.

"I just asked if you needed another drink? Samantha told us how tiny your poor little cock is. So small she couldn't even pity-fuck you like we had planned. So I thought you must definitely need another drink to deal with that level of shame."

By now, several people had turned to look, and were watching the interaction. Jack's face went flush. He turned and walked into the kitchen to throw his empty cup away - even in bad situations he was still responsible and thoughtful - and hurriedly headed towards the front door. Head down, eyes burning, throat tightening, he tried to get out before the tears came and he really looked like a fool. He got about halfway through the front door before he felt a hand grab his wrist roughly and pull him a different direction. He was pulled off-balance, and followed.

It was another girl. She took him to that same bathroom, pulled him in, quickly closed and locked the door behind him. It was Hope, Samantha's older sister. Jack had never talked to her, he mostly remembered her from when she was a senior at the school three years ahead of him. Upon seeing it was Samantha's sister, Jack immediately went to leave. He had enough humiliation for one night, he didn't need more. Hope put a hand on his chest, gently but firmly, keeping him there against the counter. Jack refused to look up, but paused.

He could have pushed past her. At almost 6 feet tall and having kept pretty active through his teen years, he wasn't exactly a body builder but he knew how to use his size and weight. But once again, he couldn't bring himself to do it. He just froze, wanting it all to be over.

"Look. Jack, right? I'm Hope. Samantha's sister. She can be... Well, she can be a real bitch. We don't get along. At all. I heard what she was saying and heard what her stupid friend said. It's really fucked up. You're obviously a really nice guy. Hell, I saw you even threw your cup away before you went to leave - assholes just don't do that kind of stuff. You're going to meet a nice girl someday, OK? It doesn't matter how small your dick might be. Every woman is different; they need different things, some women can only handle smaller-than-average guys. You really have nothing to worry about. Highschool is hell, but once you're out in the real world, you'll see."

"Sure. Whatever. Can I go now?"

Jack's eyes still never lifted. He didn't care what she said. He knew he didn't have a "shrimp-dick". While he maybe didn't have the best self-confidence, he knew the statistics. He knew he was above, well above, average. But he didn't care to try and prove anyone right or wrong. He just wanted out.

"No. I'm going to show you that not all women are nasty cunts like my sister. Some of us can be kind."

"I don't need a pity fuck. You don't need to try to prove anything to me."

"This isn't pity. This is a 'thank you for coming to my party and not fucking up my house after my sister embarrassed you'. I'm a big girl, Jack. I'm allowed to thank my guests in any way I choose."

Hope smiled sweetly at him. His eyes didn't lift, and she could see the real pain in his eyes as they watered. She knew he wasn't buying it. He was hurt, really hurt, by what her stupid sister had done. They had not only said something so incredibly mean to him, but even made it a show in front of a bunch of people from school; that he would have to see again in just a couple of days. The betrayal was real. She felt bad for him and wanted to comfort him. Wanted to make it all OK. She looked at him for a moment while she decided how to proceed. After a moment she stepped forward, took Jack's head and held it to her chest. She wasn't sure what propelled her to do it, but something inside her knew he needed softness right now. Caring. To be held, in more ways than one. She could feel the burning heat of his cheeks, and what felt like just a prick of wetness; tears no doubt. She felt the way he gave in surprisingly quick, his weight shifting to settle into the soft warmth of her chest.

"There you go..." Hope said, cooing gently. "It's OK. It's all gonna be OK. Mama's here."

She had no idea why she said that, said "Mama", and looked at herself briefly in the mirror. Seeing Jack with his head buried in her chest, feeling the burning vulnerability of his tears starting to spread against her skin made he heart melt. She wanted to comfort him. Wanted to make it all OK. She rubbed the back of his head with one hand, and with the other, gently guided his arms up and around her waist. Once again he took to it quickly; not just simply not fighting her, but really holding her. She could tell he had needed this, probably more than he realized, for a long time.

After several moments, he lifted his head and looked at her chest for a moment before looking up at her. He looked into her eyes for a moment before letting her go and wiping his eyes on the heels of his hands. "Thanks, Hope. I should, umm... I should probably go."

"Not so fast, Jack. Here's something to remember the night by..."

Hope smiled sweetly as she pulled her breasts out over the top of her shirt. She had opted to go without a bra for the party, but the bras she normally wore were a 36G. She knew they were huge, and guys were always wanting a peek, staring at her cleavage. Hell, staring even when there wasn't cleavage. Jack was one of the few that hadn't, other than undoubtedly when his face was already pressed against them. He gasped just a little let out a small involuntary "whoah..." as Hope let him get a good look before putting them away. As she did, she noticed the bulge in his pants.

"Jack... Is, um... is that you? Like, is there something in your pocket?"

Jack blushed and started to turn away.

"Oh, uh, yeah, sorry, I, um, like I said, I should be going-"

"No, Jack. Stop... To start with, I'm absolutely flattered. Don't be sorry. I'd be more offended if you didn't get hard staring at my tits. I just... I mean, with what my sister and her friends were saying, I..."

"Yeah, I know. I'm not actually small. Samantha saw it and kinda freaked. I don't know why she's telling everyone it's so small."

"I... Can I see it?"

Jack looked at Hope, as Hope bit her lower lip, waiting for an answer. Like, actually waiting. Not just treating him like a piece of meat. Like a freak. He could see something in her eyes... An interest. But not strictly platonic. Not just a scientific curiosity to be investigated. There was... desire. Want.

"Um... yeah?"

She walked over to Jack and knelt in front of him as he started to undo his pants.

"No, Jack. Wait. Let... Let me do it."

He stood there quietly, watching her expression as she finished pulling his pants down, leaving him in just his boxers. She could see the bulge, the outline, of his half-hard cock, though it was quickly getting bigger with the attention. She gently gave it one soft stroke through his boxers before starting to tug down on the waistband. She watched as it appeared before her, her eyes drinking in the details of the veins charting lazy paths under the skin and the shaft that seemed to go on forever before the tip finally made an appearance. She let out a soft appreciative hum as his boxers fell to the floor. She looked at it for a moment as it finishes swelling under her gaze. Jack watched with apprehension until Hope looked up at him with a sweet, but almost concerned smile.

"You know, Jack... this... You have to be careful with a cock like this. Take this as your 'Uncle Ben' moment." She dropped her voice mockingly low as she said "With great cock, comes great responsibility." Hope chuckled at herself as a confused, but also amused face came over Jack.

"What do you mean?"

"Well... you said you know you're already bigger than average... uh, may I?"

Hope raised her hands towards Jack's hard member, and with his confirmation began to touch him. She gently grasped the base and moved her hand, watching as the skin slid over the underlying ripples and ridges, sliding her fingers along it to feel how heavy it was in her hand, including feeling the weight of his balls in her hand as she gently rolled them together. It was somewhere between sexual and platonic in nature, straddling the thin line between settling an almost scientific curiosity, and a growing hunger; a need building in both of them that they didn't quite recognize yet.

Hope continued as she snapped out a momentary trance, "As... As I was saying. You already know that you're bigger than average. do you... know how much bigger?"

"I mean, yeah, I guess, according to what I saw online."

Hope snorted a bit.

"Sorry Jack, I just... there's some things you just don't really grasp just reading online. Look, this thing you've got here... it's a blessing and a curse. You can... You can really hurt a gal if you're not careful. If she's not careful. That's why Samantha freaked out. And unfortunately, just like guys have a thing about everyone wanting a big cock, there's a similar sort of thing with women, especially young women, too. Like, if you find a guy with a big cock, you should consider yourself lucky. Like as if there's nothing bad about it, no downsides."

"Great, so I'm just a freak and I'm always going to have women running anytime I take my pants off?!"

Jack logically knew that wasn't true, but between the lingering buzz of the alcohol and the sting of earlier, being told that interactions like tonight would continue didn't exactly excite him.

"Well, no. But you're going to have a lot of women that don't know what to do. You'll have to learn for yourself, and then guide them."

"Yeah, but I have to actually have a girlfriend, first. I have to find someone that actually wants to sleep with me. That hasn't exactly worked out so far."

"Tonight's your lucky night, Jack. If you want it to be."

Jack's attention snapped down to Hope, his cock twitched as their eyes met and it looked like she was serious. She was still slowly moving her hands along his cock, her fingers couldn't even come close to wrapping around, but she was switching hands, allowing them to just slide against him, appreciating the beauty of it.

"Hope, I... We're not even dating, and I swear if this is some prank... I just..." Jack started getting worked up, worried that someone was going to bust through the bathroom door and say he was getting punked. Luckily it was a big house with multiple bathrooms so they had been left alone, but even just the idea of such an embarrassing episode tore through him.

"Jack, whoa, easy, easy."

Hope let go of his cock, placing her hands on his thighs to steady him. She paused, looking up at him with real warmth and concern. Something Jack hadn't felt from a female, or almost anyone, in a long time.

"Jack, this is no joke. I'm not saying we have to run away and get married and start a life together. You have a beautiful cock and not only have I had a little bit of experience, I'm a woman that tends to prefer them bigger. Though, I definitely still need some warm-up time. All I'm saying is, I can teach you. I can teach you how to start using this thing well and not hurt women. So you can have the confidence that even though there are dumb cunts like my sister, you'll be able to find the right woman and not hurt her. You'll start to learn how to wield this thing. What do you say?"

She had started gently stroking his cock again, almost nuzzling as she finished talking. She looked at Jack, and Jack looked down at her, then closed his eyes, thinking for a brief moment. He took a deep breath - he couldn't believe this was happening. Like this. Tonight. With Hope. He opened his eyes and nodded at her. Hope smiled and let out a small appreciative hum as she nodded back at Jack.

"OK. We're going to start at the beginning. First up, foreplay. Foreplay is always important, but for you, this is going to be doubly important. You need to make sure your partner is properly warmed up. This gets her much more ready, psychologically and physically, for something of this size. Every woman, and each time you have sex even, might be a bit different in what they want, and when. What turns them on. You'll learn what they need from each one of them, and you'll get into some rhythms. For tonight, especially being your first time, here's what we're going to do: I'm going to work on you first, and I'm going to make you cum. Get the nerves out of the way, and let me have a bit of fun with you."

Hope winked at him.

"Then, you're going to warm me up by eating my pussy."

Jack's cock twitched.

"Ahhh, you like that idea... Good. I'll tell you what to do and teach you. You're going to make me cum with your tongue. Then, we're going to get out of this bathroom and we're going to fuck. Sound like a plan?"

Jack swallowed hard, nodding nervously.

"Good. Now, lean back against the counter. You're free to put your hands on my head if you want, but no, absolutely no pushing my head down, or any other woman's head, you unless they explicitly say they're OK with it, got it?"

Jack nodded. Hope smiled and nodded back.

"OK. Now, relax, and enjoy. That's what this is really about..."

Jack leaned back against the counter, putting his hands on either side of himself, on the counter edge. He watched Hope's face as she initially just looked his cock over, using her hands near his base to gently stroke him. She watched hungrily as the skin moved over the underlying structures; she could feel his pulse through it. She watched the tip let out just a small bead of pre-cum. She watched it develop, and just as it started to roll down to the underside of his tip, she gave his slit a small kiss. Jack watched as a small string of precum connected his cock to her pouted lips as she pulled away, until she licked her lips and broke the connection.

"Mmmm... Jack, you taste good..."

Jack's cock twitched at that. At hearing a woman, especially one like Hope, appreciating him, wanting him. She licked along the large vein on the underside from base to tip, then took one of his balls into her mouth, still gently stroking him, his cock now resting against her cheek. He moaned quietly, trying not to let anyone else outside the bathroom hear. Hope could tell he was holding back.

"Don't feel like you need to be quiet, Jack. Let it out. I love a verbal guy. I love knowing I'm doing well, that I'm making you feel good. It makes me so... wet."

With that, she took his tip into her mouth, and Jack let out a noise somewhere between a grunt and a moan as he tried not to let his hips thrust into Hope's mouth. He could feel her tongue struggle to move around his head. She played with the tip for a moment before pulling him back out.

"This... your... This is almost certainly be the biggest cock I've ever had in my mouth."

She put her lips around him again, this time trying to take in as much as she could. She stroked him in time with her head bobbing, first only getting a couple inches in past her lips. She kept pushing, and bit-by-bit more and more went through. She used her hands to make a stopping point, and at a little past half-way, Jack could tell she was struggling to do more. He heard a light gluck gluck coming from her throat as his tip was bumping against the back of Hope's throat. She pushed once more, getting another inch in. She held it there for a moment before Jack felt, and heard, her gag reflex kick in. She held it for another moment as her eyes watered, then allowed herself to take his member out of her mouth. It was covered in thick drool and spittle, and it connected them momentarily before it fell from her lips, down on her chin and chest.

"Hope, you, you don't have to push so hard. It already feels amazing."

Hope looked up at Jack and smiled.

"Jack, I'm having fun. I love to push myself, to challenge myself. There's another lesson: Some women don't really like giving blowjobs, some don't mind, and others, like me, really enjoy it..." She turned her attention back to the stiff rod in her hands. "I really do think this is the biggest cock I've had in my mouth" she said mostly to herself as confirmation of what she was up against.

She paused, stroking his entire length now as she spoke. She used her spit as lube, paying special attention to his thick head to keep him heading towards his first orgasm for the night. She looked at it and quietly said to herself "I can't wait to feel this in me..." She looked up at Jack again, shuffling closer.

"I need to give my throat a break already. I don't know if I can take all of you down my throat tonight. I may need to... practice... a bit more" Hope said with a wink. "So for the moment, I want you to fuck my tits. I want to watch your cock come up through these babies." She quickly took her shirt off and Jack watched those large globes swing freely as Hope moved around, throwing the shirt to the side. She turned back to Jack and pushed her tits together, quickly engulfing Jack's cock. She gently started moving them back and forth, letting her spit keep things a bit wet before adding a little more. "Don't be shy, Jack. You can fuck them. You can move, too." She smiled at him as he started to shift his weight, his hips starting to thrust on their own. "Oh my god Hope... Your... Your tits feel amazing..." He watched as his cock disappeared and reappeared repeatedly between the soft mammaries before Hope tilted her chin down. She shifted slightly and stuck out her tongue, allowing her mouth to receive the tips of Jack's cock, the underside sliding against her tongue.

"Oooh fuck Hope... I... I'm getting close..."

"That's it baby, cum for me. Don't hold back. I'm here for you. Cum for Mommy."

Hope wasn't entirely sure why she said that again, the "M" word, it just felt right. Apparently Jack did, too. As she said that, he whispered a cute "oh fuck" before he came. She could feel his cock get harder between her tits, then felt it pulse once, twice. She watched as a small fountain of cum burst forth, missing her tongue and instead splashing against her cheek and nose, before falling onto her chest. Another shot out, this time onto her tongue, coating it completely. He kept cumming, and now most of it went into her mouth, at least at first, before falling back out onto her cleavage, where Jack was still pumping his cock. The cum coated both of them, acting as lubricant for the last few strokes as Jack's cum spread not only over the top of her chest, but was pull between them. As Jack's pulsing stopped, Hope looked him in the eyes and licked her lips, swallowing what was in her mouth, even showing her empty mouth after. His cock slid from between her now messy tits and as she let him go, she shook them a bit, showing off for both of them how messy they were; strings of cum and spit connecting between left and right.

"You made a proper mess... I love when I'm made a mess of."

She smiled at Jack.

"I'll clean up just a bit while you catch your breath. Then you'll eat this pussy like a good boy."

At that his softening cock twitched again, and Jack watched as Hope got a small towel from a closet, wetted it in the sink, and wiped herself off. Jack watched her body as she moved, her large breasts swaying back and forth as Hope bent over a bit, wiping between them and sliding the towel against her stomach. Hope looked up as she finished toweling off and smiled softly when she caught him staring. She threw the towel to the side, slid her panties off, walked past Jack and slid her finger against his chin as she did, locking eyes. She walked to the end of the counter, leaned against it with her feet separated a bit, and put one foot up on the edge of the toilet seat. She leaned back and slid a hand down her stomach to her shaved pussy, and used her fingers to spread her lips apart. She looked at Jack with a look that initially suggested hunger, but with softness behind it.

"Come here Jack. Come get on your knees and eat Mommy's pussy." Hope purred. That word was coming more naturally, Hope barely even registered it as it left her mouth.

Jack readily obliged. He stepped in front of her and kneeled down. Being presented with his first pussy, he was slightly taken aback at how beautiful it was. The way the lips opened up like a flower, a small bud on the top. The way the skin turned a darker shade as it got closer to the slit, the glistening of its own lubrication. He could smell Hope's scent, sweet and musky. He Looked at Hope and paused, unsure what to do.

"Being your first time, just listen to me. I'll tell you what to do. Now, first thing is, I'm sure you passed health class. You can see my clit, right?"

Jack nodded.

"It's very sensitive. Every woman wants something a little different, sometimes something different at different times. This time, we're going to start soft. I want you to use your tongue and lick from the bottom of my slit to the top, slowly, and repeat. Pay attention to how I move, and how I sound, as your tongue slides against different parts of me."

Jack nodded and moved in. He pushed out his tongue and sampled his first pussy, immediately loving the way it tasted. He licked from bottom to top, his tongue ever so slightly dipping in between her lips, listening to the way Hope moaned low and soft. He could tell when he ran over the clit as her body twitched a bit, her hips pushing against his tongue.

"Oooh, good boy Jack..."

He continued on, not changing anything, only adjusting how much his tongue slipped into her hole. He wanted to taste as much as he could, and return the favor from how good Hope made him feel just a few moments ago.

"Focus just a little bit more on my clit now, Jack..."

He started licking her clit more earnestly, loving the way Hope's hips pushed against his mouth. Her hands found his hair, running through and lightly scratching his scalp to compel him on while occasionally grabbing a fistful and holding his head as her hips rolled.

"Now suck on it baby... Keep licking while you suck on my little clit."

Jack did as he was told. He looked up as he made an "o" around her clit and created a vacuum, immediately eliciting a reaction from Hope. He watched as her tits bounced and shook while her body convulsed in slight tremors with each lick. She was moaning more and more, seeming more out of breath.

"Oh fuck Jack, you're doing so well. It feels so fucking good. Please don't stop... And now put... put a finger in me and... and... sorta... stroke my insides...." Hope made a quick "Come here" gesture with her fingers as she said it before having to use that hand to steady herself again.

Hope dropped her head back as she felt one of Jack's fingers slide against her, then inside.

"Uuunngghh"

Hope groaned as she felt him start to stroke her front wall as he continued to suck on her clit.

"Oh fuck Jack... Just like that... Just... Don't... Don't stop... You're gonna make Mommy cum baby..."

She tightened her grip on Jack's hair to hold him still as he continued on, keeping steady as she asked. She could feel the orgasm build, Jack held steady, not changing anything. She had previous partners eat her pussy, and had even told them what she wanted and needed. She'd never had someone actually listen as well, and actually hold steady as she asked. They all tried speeding up or changing technique and movements to what they thought she wanted. She thought about how good he was being, about how good it felt, thought about how much of a mess he made, and how she was going to be taking his virginity in just a few short minutes. His big, fat, beautiful cock would be sliding into her, stretching her out. With those thoughts she came, and hard. The wave crested, and her body convulsed and shook, her insides squeezing his finger.

"OOOoohh FUCK! Jack! UUGHHH"

Her mouth made sounds Jack had never heard. Somewhere between a guttural moan and a nearly silent cry of war, her body convulsing, muscles spasming outside of her control. He continued on as she held his head still, her thighs now threatening to crush his head, or so it felt like to Jack, but he didn't dare stop. Her hips pushed against his mouth as she pulled his head tight in by his hair, rolling in continued attempts to extract as much pleasure from his mouth into her clit as possible.

She finally started coming down, her clit suddenly becoming sensitive. She Jumped and pushed his head away, trying to catch her breath. Jack looked up from the floor, a bit astonished. Not quite hurt, more wanting to ensure he didn't hurt Hope. She could see the look on his face and smiled softly as she caught her breath.

"Don't worry. You did good. Really good. The clit gets really sensitive after cumming, just like your tip. It was just becoming too much. But you did good. That really was... I mean... Jack, that was really good."

Jack smiled, "I just did what you said."

"You did very well."

Hope slowly put her leg down as she regained composure. She took a couple of shaky breaths as she started putting her clothes back on, and Jack followed suit. She watched as his cock swung back and forth as he moved, eating her out definitely got him excited again - he was absolutely ready for round two. She watched as the heavy appendage swung as he lifted one leg and then the other into his pants, Hope unconsciously biting her lip gently as it bounced heavily off of his leg. She couldn't help but think of his balls bouncing against her soon. They looked heavy and full again, and she wanted to extract every bit out of them that she could. She kept watching as Jack pulled his pants up, still clocking the bulge in the denim. Jack finally looked up and caught her staring, and started to blush.

Hope saw and smiled sweetly. "Jack, you don't need to be embarrassed. I love your cock. And you're a really sweet guy. Really, you don't need to hide. Especially from me." With that, Hope stepped forward and placed her hand along the bulge. "Are you ready for round two? I have more to show you." Jack's eyes widened slightly and his pulse quickened, and he nodded. "Where's your room? Or.. should we go back to my house?"

"No, I have a better idea" Hope said with an impish grin. Jack looked at her confused for a moment before she took his hand and led him out of the bathroom. The party was still going, and seemingly no one missed either of them. They must have been fine using the other bathrooms in the house, as there wasn't even anyone immediately moving towards the now open bathroom, let alone any sort of line. Jack looked back towards the main area for a moment as Hope almost dragged him through the hallway the other direction. If anyone saw them, no one seemed to acknowledge it. They stopped at a door and Hope quickly opened it, pulled them both through, and shut it again, locking it behind them.

She turned on the light, and Jack looked around the room at the various posters and decor around the room. He couldn't place exactly what it was, but something didn't seem right. It didn't seem very... Hope. He wasn't sure what would have brought the decor in that direction, but it just didn't seem to fit. Even the lingering smell of cheap body spray was very... Samantha.

"If you didn't know already" Hope said, "This isn't my room. It's Samantha's. I generally try not to come in here, but, I think this seems fitting. There's be plenty of time for you and I to fuck in my room. But tonight, after what she did to you, I think it's only fair to make a mess of her 'inner sanctum' in the way she tried to make a mess of yours by fucking with your head. An eye for an eye, I suppose."

Jack chuckled nervously. He was, on the one hand, happy to have someone looking out for him. Someone that cares and wanted to get back at the people that hurt him or wronged him. But he also didn't want to face backlash. He still would have to go to school with Samantha, and worried about the fallout if they were caught. Hope sensed his nervousness and stepped close. She brought her hands up and cupped his chin, looking him in the eyes. She felt a sense of almost protective maternalism, wanting nothing more than to both soothe his anxieties as well as throw her sister out the window for what she did to Jack. While she hadn't known Jack well before this party, she knew of him. She remembered he had always been shy. That his mom had passed several years ago. That he struggled to make friends. A lot of this she had seen herself when she was in school, but some of it she heard from Samantha, though of course there was little sympathy in the way Samantha talked about him.

She tilted his head down a bit and kissed his forehead. "Don't be scared" she said softly. "I'm here. Just follow my lead. Focus on me, everything will be fine."

Jack's eyes almost watered a bit; this was not only the first time he had started to feel close to someone after his mom's passing, but also the first time he's allowed it to happen. He had been so closed off, and he started to feel the bricks in the wall he had built coming loose. It was one thing for a woman to want to fuck. It was entirely another for a woman to want to make him feel OK, to make him want to feel safe. He nodded as he looked into her eyes, shining as they held space for him. Hope nodded back, let a hand slip to his chest. "Wait here, I need to find something."

Jack stood in the middle of the room as Hope immediately started rummaging around in Samantha's dresser, checking a few drawers by digging under clothes. Whatever she was looking for, she couldn't seem to find it yet seemed sure she should. She checked under the bed, still nothing. Hope even checked in a nightstand. Nothing. Hope paused, looking around the room. She walked over to the closet, slid open one of the doors, and peered in.

"What are you looking for?" Jack asked.

"A box. I know it's here somewhe- hello..."

Hope reached down and picked up a large shoebox from the floor of the closet from behind some shoes. She took it to the bed, and Jack followed behind, watching the box. Hope set it down, and opened it. Inside was a small assortment of basic vibrators and small dildos. The biggest looked maybe 5 inches, and not very big around. Hope snickered quietly and picked it up, holding it between her and Jack. Jack looked at it for a moment before Hope spoke.

"This is why she panicked. This might be the biggest thing she's ever had inside her, and you..."

Hope motioned to Jack's crotch with her free hand.

"You scared her. But then she felt like she had to save face. Like I said, just like guys all talk about wanting to have a big cock, there's definitely a female version in some, especially inexperienced, circles of being able to take a big cock. Like, that a woman should be happy to be able to find a guy with one."

"That's not how it is?"

"I mean... I think it's a rarity thing. Curiosity. But honestly... too big can cause problems. And that's why we're actually digging in this box. Your lessons."

Hope grinned at Jack as she put the dildo back, and grabbed a small bottle of lube. She now held that up between them.

"This is your new wingman, Jack. Lube is important for any couple, but ESPECIALLY important for someone with your size. Women are generally self-lubricating to an extent, but, with you, don't be surprised if they often need help to at least get going, sometimes even as things are still happening. Foreplay helps a lot, but you and your partners may need just a little more help. Don't ever be afraid or embarrassed to use more lube. Better to use more lube and keep it fun for everyone than to "save face" and wind up hurting some poor girl. Hell, it makes it more comfortable for you, too. Too much friction is bad for everyone."

Jack watched as Hope went and set it down on the nightstand. She walked back, looked at the door to ensure it was locked. She looked back at Jack, who mistook the look for nervousness. "Hope, we really don't have to do it in here. I mean-" Hope put a finger to Jack's lips.

"Ssshhhhh... Let me take care of you. Of everything. I'm not worried. The door is locked. I just wanted to make sure we weren't going to be unduly interrupted. Now, What's going to happen is we're going to get undressed. You're going to lay down on the bed, and I'm going to ride that massive, fat cock of yours. I'm going to ride you first, because I need to take control. I need to guide that thing in me at my own pace, and that's your first lesson. You're going to have to learn to let the woman lead, at least at first, to allow her to figure out how much she can take without it hurting. Now, strip for me, and go sit on the bed."

Hope smiled as she took a step back. She of course saw Jack's body in the bathroom, but her mind had been elsewhere. She allowed herself the pleasure of time and mental space, for both of them, and watched as Jack took his clothes off. He wasn't very practiced at being sexy, but that's something they could work on, Hope reckoned. He first took his shirt off, sliding it up and over his head as if in a hockey fight. Not exactly sexy and smooth, but there was something cute in the inexperience. While he generally kept himself active, he wasn't too lean, either. The suggestion of muscles throughout his back rippled and moved as he got the shirt off and threw it on the ground. She looked over his body with appreciation, knowing that at this point it really was hers if she wanted it. And she did. When she first took jack to the bathroom, she wasn't planning on anything continuing after tonight. But now... Now she wanted him. Not just sexually, emotionally. Spiritually. She sensed a real connection, and planned to continue as long as Jack allowed it.

Jack blushed under Hope's gaze as he took his socks off next, then unbuttoned his jeans. His bulge already obvious, he was moving quickly. Partially out of excitement, partially out of anxiousness. He certainly never imagined he'd leave the party with a girlfriend, let alone losing his virginity. He had come more out of curiosity, as he didn't attend parties much. He had been hoping at most to maybe make a new friend, or at least just enjoy himself. He didn't know at this moment that Hope wanted to keep seeing him, to be with him. He was happy to even experience this for the night, and allow himself just a little vulnerability; the first real vulnerability in 6 years.

"Slowly!" Hope said quickly, snapping Jack out of his hurried trance. He had just brought his jeans down a couple of inches, and paused as his eyes snapped up to her. He smiled and slowly lowered his jeans, letting his gray boxers show bit-by-bit. Finally the jeans were down to his knees, and he let them drop. His bulge was more of a suggestion in his boxers as he hunched over with his jeans, but as he stood, the outline became clear. Hope unconsciously licked her lips as she traced the outline with her eyes, from the mass that was obviously his shaft and balls, all the way down to where she could see the flare of his tip through the cotton.

Jack felt a little more bold as he saw how close Hope watched him, and put his hands behind his head and wiggled his hips just a little, getting his cock to shift and bounce in his boxers. That snapped Hope out of her trance and she laughed gleefully. Jack smiled as he then slowly pulled his boxers down, though did his best to avoid hunching over this time, letting his hips stay forward. Hope stood watching intently again as he revealed his engorged member, bit-by-bit, slowly revealing an almost endless column of semi-hard flesh hanging between his legs until finally the head was revealed. Hope unconsciously inhaled a little sharply as she saw it, the thought of it inside her made her heart pound and her stomach flutter. Jack let the boxers drop to the floor and paused, letting Hope get a good look before he back-pedaled to the bed and sat down.

"My turn" hope said.

She stepped in front of the bed, and took her socks off first. Jack could see once again the way her breasts hung heavy and swayed under her shirt as she bent over. He was absolutely hypnotized by the motion. His cock continued to swell at just the thought of seeing them again, let alone getting to touch them. Hope then took her jeans back off, somewhat slowly, wiggling her hips side-to-side as she did. The view of first her hips wiggling, then her tits swaying again as she slid the jeans off was almost making jack lose it. Just like Hope, Jack of course had already seen her naked. But now he was watching as she stripped, intentionally putting on a private show just for him. He watched as her hips came into view, that swell from her waist that suggested a maturity over that of his classmates. The jeans dropped to the floor, and she was left in panties and her T-shirt.

She turned around so that her back was to him now and he could see the black panty she wore was thong-type; the strip completely disappeared between her cheeks. She first took off her top, slowly pulling the fabric over her skin. Jack watched as her back came more and more into view, first the small dimples just above her hips, then the shape of the long muscles along her spine, then the suggestion of the small muscles making up her mid-back, rippling under her skin as her shoulders flexed taking her shirt off. He could see the sides of her breasts moving up, then back down as she lowered her arms, throwing the shirt to the side.

She crossed her arms in front of her, trapping her breasts playfully as she turned slightly and looked over her shoulder to see Jack staring intently, his cock now hard. She was pretty sure she could already see a bead of precum starting - that was a good sign. Not that she expected anything less.

She turned again with her back to jack, and hooked her thumbs under her panties. She slowly bent over as she pulled the waistband down. Jack watched as the thin strip of cloth pulled out from between her cheeks, and she was left naked, her ass presented to him for a moment with her legs together. A moment that felt like it lasted forever and for the blink of an eye at the same time. He saw her pink slit pushed back, glistening in the low light, framed by her thighs. Her ass looked deliciously round, and he had a sudden urge to grab hold and bite it. He was suddenly aware of how almost painfully hard his cock was, how desperate it was to be touched.

Thankfully Hope stood back up and turned around, her eyes at first met jack's, before noticing his cock twitching in his lap. He was almost upright, leaning back on his hands. His cock pointing up proudly, waiting for her to take control and guide him. She smiled warmly, with just a hint of lust. "OK, Jack. Are you ready?"

"I... Yeah. I'm... I'm ready."

"OK. Grab the lube for me."

Jack grabbed it with an eager speed so quick, Hope couldn't help but giggle a bit. The sound made Jack's insides warm, like he would do anything to keep hearing that sound. He smiled sheepishly as he handed the bottle over, just as Hope straddled him. She took the bottle from him and pushed her hand against his chest gently, guiding him to lay down on the bed.

"Lay down and relax. First thing is, like I said, some lube. We've done some foreplay, we're both warmed up and ready to go. But like I said, never be afraid to use some to get things going, especially with a new partner, where you don't know if she makes enough herself."

She sat on his thighs just below his groin, grasping the base of his cock to tilt it straight up, against her stomach. She gently stroked it while looking at how far up her stomach it went, letting out a small "... jesus..." She let go of his cock and dragged a finger through his precum, smearing it on the underside of the tip before bringing it to her tongue and tasting it, smiling.

"Mmmm... Yep, I'd say you're ready to go."

She smiled at Jack before pouring a bit of lube along the underside of his cock, then slid herself along it. Her lower lips wrapped around either side of Jack's thick member, and she slid slowly up the entire length, rolling her hips to tease his tip at her entrance. Jack's hips involuntarily tried to push up into her before she rolled her hips back towards his base.

"Ah, ah, ah... Let me lead. Control yourself young man. We'll get there."

Jack grinned sheepishly again and nodded. He watched as she slowly ground her hips against him, putting just a bit more lube on as she went, making his cock a wet, slick mess. She closed her eyes and purred as she slid along him several times, and he watched her face soften into something almost contented, but still needful. Like someone who has been eating a fine meal, but is still hungry for more.

She opened her eyes and made eye contact with Jack as she slid up his length one last time, this time rolling her hips just right, catching his tip. She moved her hips, allowing him to enter her. At first just the tip as she slowly moved back. She let slip something between a sigh and a moan, her face contorting into something Jack hadn't seen before - that look of bliss when it finally happens. He watched as she slowly moved back inch by inch. He was in heaven, barely breathing. He could feel the hot, slick tightness of her insides; better than he had ever imagined. He watched and felt as the warmth spread, his cock slowly disappearing inside of her. He watched her face as it changed from pleasure to a new look, a mix of pleasure and concern. No, of concentration. She was about halfway down, 5 or 6 inches, and she suddenly slowed. Now to 7 inches. She paused, and breathed a deep breath, and started to grind and roll her hips.

"Most women can fairly comfortably take 5 or 6 inches. Maybe a bit more if you warm them up. You're so big... so thick... it's a lot of sensation. It feels good, but... I'm slowly getting towards my limit, I think. You're the biggest I've had, Jack. But I... I want to feel you. All of you."

"Hope, you really don't have-"

"I'm going to. Remember in the bathroom when I said I like a challenge? This is another challenge. I want to take all of you, Jack. And this is part of the lesson. If you're patient, if you're a good boy, you'll see that Mommy can take all of you. Can take you like no other girl will."

Jack's stomach fluttered at that as she continued rolling her hips, still pushing back slowly further and further.

"OOohhh fuck, Jack... Your cock is so fucking big, it feels like it's stretching me open in such a good way. UUUggghhnnn"

8 inches in.

Suddenly there was a pounding at the door.

"UMMM, HELLO?!"

Samantha

"I KNOW YOU'RE IN THERE. WHOEVER YOU ARE, DAWSON SAW YOU COME IN HERE. THIS IS MY ROOM, FIND SOMEWHERE ELSE TO GET FREAKY. LIKE, ANY OTHER ROOM"

Jack looked at Hope with a look of slight panic and started to try and get up. Hope pushed him back down and kept working herself farther onto his cock.

8.5 inches

"Don't worry baby, Mama's got you. Don't you worry about my sister, or anyone at the party. Just focus on me... I'm almost there... Can you feel it? Can you feel how much you're stretching Mommy's insides?"

Jack nodded as he looked into Hope's eyes, focusing on her. He actually could feel it. Where initially it just felt like sliding into something warm and wet, albeit tight, there was now a slight resistance.

"Play with my tits, Jack. Play with me."

Hope closed her eyes as Jack reached up and began squeezing and kneading her breasts, and playing with her nipples. Initially softly, tentatively, but gained some confidence as he watched her reactions. Hope moaned at his touch, sinking farther down.

"Oooh fuck, yes, just like that."

"HEY!! GET THE FUCK OUT OF MY ROOM!"

9 inches. Almost there.

The door knob jiggled violently, but the lock held. There was more murmuring outside the door; Samantha wasn't alone.

Hope kept grinding, feeling her own climax starting to build from all of the stimulation of being so full, so stretched, in her sister's room with this boy that she was claiming as hers.

There it was. All of him.

She felt her vulva brush against his trimmed pubic hair just before their hips connected, and she felt the last of him enter her. She was now fully on him, he was fully inside her. She shuddered a bit as a light orgasm took over, her clit sliding against his pubic bone as she continued to roll her hips. Jack watched with a smile as she shuddered, knowing that, at the very least, it was feeling good for her. But he could tell she had to work at it. Could tell the the lube and the pacing was important, and understood he couldn't just rush in. But he was in her. He had never been inside anyone before, and now he was fully hilted inside this amazing woman. She paused for another couple of beats, allowing her body to get used to something so large inside her.

Hope bent down and kissed Jack, passionately, softly. She raised her hips just a bit and sank back down, slowly starting to ride him. She started lifting her hips more and more, with a slightly faster rhythm.

"OOhhh, FUCK." she growled. She started making noises Jack had never heard outside of bad pornography, and started getting louder as she started to ride him more energetically.

Suddenly the doorknob started to jiggle again.

"I SWEAR TO GOD IF YOU TWO AREN'T ALREADY GETTING DRESSED AND COMING OUT BY THE TIME I-"

And with that, the knob clicked; apparently Samantha had found the key, or some other way to unlock the door. The door burst open and not only Samantha, but seemingly half the party along with her, fell into the room. There was a moment of stunned silence before Samantha spoke up. But not before Hope quickly whispered to Jack "Pay them no mind. Just focus on me."

"OH MY GOD HOPE WHAT THE FUCK ARE YOU DOING IN HERE?!?! AND IS THAT... JACK?!?!"

There was a pause while Hope kept sliding up and down Jack's cock, moaning, not paying any attention to anyone around. In fact, Hope played it up.

"Oh fuck, Jack, your cock is splitting me open! OH FUCK! Yes! Right there! Your big, fat cock feels so fucking good."

Some random guy spoke up. "I thought you said he had a tiny dick! That thing's huge!"

Another: "Dude's hung like Seabiscuit!"

The girl that called him shrimp-dick earlier just watched for a few moments, wide eyed, as Jack's cock disappeared and reappeared over and over inside of Hope. She turned to Samantha, but without taking her eyes off of the spectacle.

"What the fuck, Sam. I would have killed to have found that in the bathroom."

Samantha blushed deeply and her eyes watered from anger and embarrassment. She turned and pushed past the crowd and down the hall to hide or to get another drink; no one in the room knew or cared as the sounds of Hope's pleasure chased Samantha down the hall. After a few moments, Hope screamed out "OH FUCK JACK I'M GONNA CUM ON YOUR COCK!" And pretended to orgasm, once again playing it up. All the while Jack attempted to put on his own performance, which really consisted of playing with Hope's breasts and awkwardly, quietly, crying out generic pleasure phrases like "Fuck yeah Hope" and "that's it girl". None of it sounded very convincing. Of course, no one cared or even heard Jack. They were mostly focused on what was going on between their hips.

Hope slowed down, and a few people started to walk out. That seemed to be the catalyst for the rest to walk out. The girl from earlier was the last to leave - she hard a hard time tearing herself away. She kept watching Hope rolling her hips against Jack, and even kept watching as she very slowly closed the door.

Finally, they were alone again. Hope paused, grinned at Jack with a look of pure satisfaction.

"We fucking got her. I don't think she'll be bothering you again. Sorry for the performance... I just thought that might be a good time for another lesson: Women can fake it, and often people never know. Hopefully you never have to experience a woman that fakes it. I, for one, prefer to be genuine. But, sometimes being a bit performative is warranted. Don't worry though, I'll never fake an orgasm with you. Besides, I don't think that'll ever be an issue." She smiled warmly as she finally realized she was slipping more and more into talking about them with a sort of future certainty. She hadn't planned at any stage for things to go for more than tonight. Hell, even this wasn't planned. But she was more and more feeling like she wanted it to. Like she wanted to see more of Jack. To take care of him. To help guide and protect him. To be there for him. To be hers.

Jack smiled back. "Yeah, it seemed a little over the top, but, they seemed to like it. I guess... thanks? I almost feel bad for Samantha though."

"Almost"

They both giggled, and Hope started rolling her hips again, slower, more sensually. She looked him in the eyes and just sat with everything in the quiet. She felt his eyes on her, watching her. Trusting her. She felt the way his thick member slid back and forth inside her as she rolled her hips, filling her completely, more than she thought possible. She felt the way her clit grazed his pubic hair and rolled against his pubic bone, heightening the sensations. She noticed the way her body just felt a warm glow that she hadn't felt in a long time. Maybe ever.

Jack found himself in a similar state. He looked up into Hope's eyes, and felt her weight on him as her hands were perched on his chest, her arms pushing her tits together, making deep cleavage as they gently, slightly moved back and forth in time with her hips. The way his cock was completely enveloped by her, the warmth, the wetness, and how almost painfully tight she was. But it was also so inviting. It wasn't just something they were doing to each other. It was with each other. For each other.

"OK, next lesson."

Hope stopped, and slowly lifted herself off of Jack, not without an almost painful pang of emptiness as his tip came out. Jack waited for instruction.

"It's time for you to try taking control. We switch places. Missionary."

Jack got up and Hope took his place. Jack rolled off the bed, then walked to the end and kneeled in front of her, between her legs. He looked down at her and took her in for a moment; her legs were pulled up and away to give him access to her. Her breasts were pulled down from gravity, held in place only by her arms as her arms hooked around her legs. She looked soft, warm, inviting; he felt something in his chest soften. She was smiling up at Jack, inviting him in, physically, emotionally. She saw the look on his face and her hands let go of her legs, and she reached up to him, a final invitation to not only fuck, but to be accepted.

Jack moved farther up between her legs and slid himself along Hope's slit, the underside of his cock sliding against her sensitive clit. He leaned forward, and Hope put her hands on either side of his chin, holding him. She smiled warmly and closed her eyes for a moment, feeling Jack's hard, heavy member sliding against her. She glanced down and saw how far up her stomach his tip was as his balls lightly grazed her lips, his hips pushed forward. Her stomach fluttered slightly, and she looked back up at Jack, their eyes meeting. She bit her lip and nodded slightly, and Jack took that as the sign that it was time. She was warmed up, ready.

He slid his hips back and let his tip drop, using one hand to steady himself as he found her hole. He moved it against the entrance for a moment before slowly pushing it in. He felt her take him in, and Hope let out a light, breathy moan as she felt him enter her. He continued at a slow pace, watching for signs of discomfort. He paused once, about two-thirds of the way in, when Hope made a face that was a little too close to a grimace for his own comfort. She first looked puzzled as to why he stopped, then smiled when she realized that he was simply that attuned to how she was doing, and encouraged him.

"It's OK Jack, you can keep going."

He continued slowly until he was completely in her. He felt his hips rest against hers, and paused. He allowed some of his weight to settle down against her as Hope's insides once again got used to the size of Jack. She pulled her legs around him, holding him there. She put her hands behind his neck, and gently stroked the nape. He let his head drop slowly until their foreheads were touching. The feeling of Hope fully enveloping him, physically, emotionally, soothed deep pains and longings he didn't even know he had. After a moment, he felt Hope shift her hips up, gently encouraging him to continue. He kept his head low, not wanting to break the spell, but began to move his hips. He pulled out slightly and slowly pushed back in, and again. Slowly working his hips, staying in the present to allow himself to fully experience everything: the way Hope's hot, wet pussy gripped his cock and didn't want to let go. They way her legs hooked around his hips to keep them from drifting too far. How her hands held him lightly, but not restrictive. The sound of Hope's breathy moans as he moved. He was getting lost in the experience, lost in her.

"You're doing great, baby... you feel so good, and you're being so careful with Mommy..."

He felt the way her body responded to his movements, and seemed to understand the cues instinctively. He felt the way her hips began to rise up more to meet him with each stroke, encouraging to push just a little faster, a little harder. As Hope's body continued to warm up to Jack they both gained more confidence in what he could do. Hope felt herself open to Jack, both physically and emotionally. She had never felt so connected, and the overwhelming flood of endorphins almost made her head spin.

Jack began to pull himself out a little more, Hope responded by pulling her hips back and down as well in time with his movements, allowing for each stroke to be as long as possible while staying in this position. She could feel everything; his thick shaft stretching her, the ridges of his cock making her insides ripple, the flare of the tip spear-heading its way deep into her with every thrust. The fullness, the friction, the emotion, it all helped to build an orgasm that Hope felt welling up from somewhere deep.

Jack's head dropped lower, resting in the crook of her neck and collar-bone. His arms slid under her, both supporting his weight and drawing her in closer. Hope closed her eyes, letting the sensations take over. She could feel the rhythm of his breathing, hot and moist on her chest and neck. She could feel the steady thrusting below, and she could feel him start to tense up. She felt his tempo falter briefly and knew he was getting close. His breathing started getting a bit more ragged, uneven. His tempo faltered again, and Hope could sense the question, the conundrum, building in Jack's mind.

"It's OK baby, you can cum in me. Cum in Mommy, Jack. Fill me up" Hope said breathlessly. "Whenever you're ready baby, give it all to me."

She felt Jack nod ever so slightly as his tempo resumed. Hope felt her own body continue to tense, the energy coiling inside her. It was built in layers of not only the raw pleasure but also by Jack's unconscious consideration of her and her needs. She tightened her grip on him where she could: her legs pulling him in tighter, her arms wrapping tightly. Her hips rolled more, trying to both keep the length of each stroke extended, but now more to pull him in close, pull him in deep.

She felt him tense; not just his arms or his core, but his entire being. She could feel his cock get stiffer, bigger, if that was even possible. She heard Jack grunt and whisper "Fuck, Hope... I..."

With that, his cock pulsed as he pushed deep into her. She felt him cum, releasing a flood of warmth into her. The warmth and pulsing sensation on her already sensitive walls brought on her own climax, her velvet insides pulsing almost in time with the hard flesh inside her. As he was flooding her she was trying to pull him in deeper, trying to milk every bit of seed out of him. This wasn't the same raucous orgasm she's had with other boys. No, this was something different. Deeper. Overriding. More endorphins, more oxytocin. Jack pushed into her deeply, instinctively wanting himself as deep inside of Hope as possible, and she pulled him in to allow it.

It lasted no more than 15, maybe 30 seconds. But for them it lasted minutes. Hours. Time stopped completely as the rush of chemicals flooded both of their brains. Jack felt himself start to relax, letting himself sink into Hope. Hope relaxed as well, letting her legs let go of Jack's hips, her hands relaxing as she realized her nails were dug into his back as if she had been trying to impale him to keep him steady. The both breathed heavy for a moment before Jack pulled his head up to look at Hope. He looked at her with a sense of need, but not strictly sexual. There was something that felt good, felt healed, by what had just transpired between them.

Hope let her hands cup Jack's face, looking into his eyes for a moment. She didn't know why, but she knew she wanted to be with him and finally just allowed that to be. She wanted it for more than just tonight. More than just for a couple of one-night-stands. She pulled him down gently and kissed him softly, sensually, lovingly. Jack responded by sliding his tongue gently into Hope's mouth, and as their tongues met, they softly tasted each other's after-glow.

They broke the kiss, and Jack pulled back, slowly sliding out of Hope. Hope half purred, half moaned as she felt the softening cock slide out of her, the ridge of his tip sliding against her soft tunnel once more before leaving her almost painfully empty. She could feel the cum almost instantly spill out of her, though she didn't bother to clean anything; Samantha could deal with it. Jack offered to get something, but Hope declined. She asked for her panties instead. Jack got up and looked for them and Hope sat up, leaned back on her arms watching Jack move around the room, looking for them. She couldn't help but watch once again as his now mostly-soft cock swung between his legs as he looked, shiny with the evidence of what just transpired. Hope unconsciously replayed what just happened in her mind. What would almost certainly happen again, and soon. She licked her lips as he finally found her panties. He turned to look, and caught her staring, licking her lips.

He had a similar reaction seeing her. Taking in the full picture of Hope on the bed, her hair messed up, her large breasts hanging deliciously, her face holding a look of hunger that he somehow knew only he would satisfy, and her slit facing him, a complete mess of fluids that they both equally contributed to. He felt his cock twitch, some blood trying to flow back in to thicken it in anticipation of what was likely to come later that night.

He paused to soak in the view before handing the panties over. She took them, and pulled them on while staying on the bed. She pulled them up, Jack watching as she trapped his cum in the panties. "I'm keeping you with me all night" Hope said, winking at Jack. Jack smiled as he pulled his own clothes on. She found her pants and Jack watched as she bent over, her large breasts swinging as she put them on. She found her shirt next, Jack's eyes still tracking, almost hypnotized again, as she picked it up and put it on. Her nipples strained against the fabric as she watched Jack watching her, noticing his bulge, now in his pants, staying prominently visible. Hope couldn't help but giggle at him a bit. She reached her hand out and took his. She led him to the door, and as her hand grasped the knob and turned, she could instinctually feel Jack unconsciously hesitate and almost pull away, a bit of anxiety as he faced leaving the warm safety of the bedroom, and back to real life. Hope opened the door, turned to Jack, and took his hand in her other as she looked in his eyes.

"Don't worry baby, I've got you."