If you’d like to start from the beginning, please check out the previous story, entitled “Jennifer and Allison – part 1.” My stories are an attempt to bring an exciting read to people who aren’t into incest and pedophilia. Honestly, who gets off on that gross stuff, anyway? As always, your constructive criticism or compliments are welcomed.
Jennifer gazed down at Allison, who was completely exhausted, and almost completely naked except for her bikini top pulled off to the sides of her breasts. Sweat glistened across every inch of Allison’s body, and cum was dripping lazily out of her pussy. “So…” said Jennifer tentatively, after awkwardly making eye contact with Allison, “do you think he would let me try some of that with him, too?”
Allison sighed, still coming down off her incredible orgasm of only a minute ago. “I dunno…” she said breathlessly. “He’s a boy. Give him a few minutes to recharge and I bet he wouldn’t mind a little more action.” Allison smiled coyly at Jennifer.
Jennifer shifted her weight uncomfortably, still inwardly torn between her desire to experiment with Ryan, her fear that he might not want her, and her conscience continually screaming at her that fooling around with boys was just plan wrong.
“I don’t know…” Jennifer said tentatively. “Do you think he’d even be into me?”
“Jenny, are you kidding?” Allie replied incredulously. “Half the guys at school want to jump you, they just don’t even try because they think you’re an ice queen. You don’t really flirt much, you know. I’ve heard from a few different guys that most of the senior class thinks you’re one of the hottest girls at school,” Allie continued, attempting to bolster her friend’s confidence. “Plus, one secret I can share is that boys are just horny.” With a coy smile, Allie finished, “If a girl offers sex, there’s almost nothing that would make them say no.”
“Well I don’t know if I’m ready for, like, real sex!” Jennifer quickly interjected, not wanting her best friend to think she was some kind of slut. “I dunno, maybe just to make out and feel each other up a little bit or something,” she continued, her conscience quickly losing its control over her.
“Jenny, you do what you want,” Allie sighed. “But whatever you do, just move out of the way. You’re blocking my sun!” she continued with mock indignation.
“Alright, well I’m going to go inside really quickly and…find another thing of sunscreen.” Jennifer said, glancing over her shoulder at the house. “This one is almost out,” she lied, grabbing the half-full tube of sunblock and starting to back towards the house. “I’ll be out in a few minutes.”
Jennifer started to slowly walk towards the house, her heart pounding. She had been looking for any excuse to go back into the house where Ryan was upstairs taking a shower. She gave a silent sign of relief that Allie hadn’t noticed she was lying about the sunscreen being empty. At least that way Jennifer would be able to go inside and decide what to do without her best friend putting any pressure on her.
Jennifer was hit with a blast of cool wind as she walked through the patio door and into the air-conditioning. Her nipples stiffened under her black bikini top, poking out against the smooth fabric. Jennifer looked down at her body, noticing the erect nipples and the deep chasm between her breasts. I look hot, Jennifer said inwardly, trying madly to convince herself that Ryan wouldn’t be grossed out by the prospect of fooling around with her.
As Jennifer mounted the stairs, she could hear the water running in the bathroom. The bathroom adjoins my bedroom, Jennifer thought. She wondered if Ryan had been naked in her room at all before going into the bathroom to shower. The thought of it made her feel a familiar tingle between her legs as she finished climbing to the second floor of the house.
Jennifer pushed open the door of her bedroom and shut it behind her, but didn’t lock it. Just in case, Jennifer thought to herself. What if I chicken out and I need to get out of here?
She peeked out the bedroom window, which overlooked the backyard. She saw Allie sprawled out in the lawn chair still, only now Allie had taken the liberty of removing the rest of her bikini, the red fabric lying forgotten in the grass next to the chair. Allie is so beautiful, Jennifer thought to herself. No wonder Ryan likes her.
Jennifer’s eyes traced the perfect contour of Allison’s firm breasts, standing straight up on her chest as she tanned. God, my boobs are too big, Jennifer complained to herself. I look ridiculous…but maybe Ryan likes big boobs…I just don’t know…maybe I should just wait and find out if he likes them or not…
Jennifer turned abruptly when she heard the sound of the water shutting off in the bathroom. She jumped away from the window and sat down on the edge of her bed, doing her best to look calm despite the beating of her heart. Her eyes wandered over the floor, scanning a couple bras and panties of hers that she had forgotten to put away. She was embarrassed and hoped that Ryan hadn’t looked at them on his way to the bathroom. Then she noticed Ryan’s swim suit tossed carelessly into a corner of her room. He had carried it inside with him after he left Allie in the backyard, Jennifer remembered.
If Ryan’s swimsuit is here in the room…Jennifer thought to herself…then I wonder what he’s w… –
“Hey, Jenny, what are you doing in here?” came the voice from the bathroom door. Ryan stood, framed by the doorway, stark naked and dripping with water.
Jennifer was surprised and stifled a gasp, trying her hardest not to stare at Ryan’s penis. It wasn’t as big and hard as it was before, but it definitely wasn’t completely soft either, she noticed. Wow, Ryan looks amazing…Jennifer screamed inside her own head. She felt herself start to get a little wet gazing at Ryan’s naked body standing in front of her.
“Sorry I didn’t know I’d have an audience when I got out of the shower,” Ryan joked, but made no move to cover himself. “So…what’s going on?”
“Umm…” Jennifer faltered. “I just…it’s just that…well, it looked really fun what you and Allie were doing down there,” she stumbled over her words. “I just thought maybe, if you weren’t too…you know…like, tired or anything…maybe you could show me a little bit of that…”
Ryan started slowly walking towards Jennifer. He approached her on the side of the bed and stood only inches in front of her. Her eyes raked his smooth chest and she raised her head up to look into his eyes. “I thought you’d never ask,” Ryan whispered as he leaned down and planted a gentle kiss on Jennifer’s lips.
Goosebumps erupted all across Jennifer’s body as their lips met. “Ryan…I know it’s, like, super lame, but I don’t know if I’m ready for, you know…real sex, right now. So maybe we could just do some other things…” she said uncertainly.
“No problem,” Ryan cooed into her ear as he reached down and took her hand. “Just let me know when to stop.” he said reassuringly.
With that, Ryan put his hands on Jennifer’s waist and helped her to scoot up onto the bed. Jennifer felt the soft covers under her back and she wrapped her arms around Ryan as he sunk into her and started to kiss her repeatedly on the lips.
Jennifer let out a small gasp of surprise as she felt Ryan’s cock brush against her inner thigh. It felt like it was starting to get pretty hard again. Jennifer spread her legs open to give Ryan a place to lie. As they continued to explore each other’s mouths, she tentatively touched her toes to his and played a small game of footsie as they made out on her bed.
Oh my God, I can’t believe I’m making out with Ryan Bradshaw in my bed and he’s totally naked, Jennifer thought to herself. This can’t be happening for real! I feel like a humongous slut!
Ryan’s hands started to wander. He stroked up and down her bare arms, sending soft waves of bliss running up and down her skin. His hands strayed over to her torso, feeling gently around her waist, and ever so slowly inching higher. His thumb brushed against the side of her breast, and Jennifer jumped with surprise at the touch.
“Is this okay?” Ryan moaned into Jennifer’s mouth as his thumb continued to idle near the side of her breast.
“Yes…sorry…just nervous,” Jennifer whispered back in between kisses. Feeling bold, Jennifer took his hand and guided it onto the center of her breast, inviting him to explore to his heart’s content.
Ryan didn’t have to be told twice, and immediately started to rub and squeeze Jennifer’s large D cup breast through her tiny black bikini top. Jennifer’s breast was firm and supple under Ryan’s touch, and he moaned appreciatively as he gently pinched her still-erect nipple in between his thumb and first finger. “Wow…you’re way hot…” Ryan’s voice trailed off as he snaked his tongue inside her mouth.
A shudder of pleasure shot across Jennifer’s body as Ryan tweaked her nipple. Oh God, I’ve never felt anything like this before, she moaned to herself as she arched her back, forcing her large breast more firmly into Ryan’s palm. I can’t believe he actually thinks I’m hot!
Jennifer felt her pussy become wetter and wetter as she and Ryan continued to kiss and feel each other. Ryan’s cock was now fully hard and Jennifer could feel the entire length of it pressed into her stomach as he writhed around on top of her.
Under Ryan’s eager touch, the already-too-small black triangles covering Jennifer’s nipples were starting to bunch up and cover even less than they did originally. This bikini was totally made for a girl with smaller boobs and ass than me, Jennifer thought dryly to herself as she felt the slender strings of the bikini cut lightly into her breasts.
As Ryan continued to fondle Jennifer’s breasts, he started to gently rock his body back and forth. Jennifer moaned as she felt his long penis rub smoothly against her stomach and front of her bikini bottoms. Her pussy was absolutely on fire by this point, begging to be fingered, or licked, or something…Jennifer wasn’t even sure anymore what she wanted. She just knew that she was horny as hell and her crush was totally naked and on top of her in her bedroom.
Jennifer’s hand absentmindedly wandered down near her hips as Ryan continued to gyrate on top of her. Her fingers started unconsciously playing with the ties on the sides of her bikini bottoms. She tugged gently and felt the knot start to come undone. Before she realized consciously what she was doing, she had pulled the little string all the way out and the knot on her left hip came undone.
Oh my God, Jennifer thought to herself as she realized what she had just done. The only thing separating me from Ryan’s dick is one more knot and a little piece of cloth…
The thought sent a spasm of pleasure coursing through her pussy. It would be so easy…her mind tried to convince her. No, I can’t do that! Her conscience tried to intervene. But I can always ask him to stop if it’s too much, her brain tried to argue.
Responding to her brain’s argument, Jennifer’s right hand started to slowly reach for the knot on her other hip. She toyed with the string in her fingers, fighting within herself to know if she should take the next step or not. I can still ask him to stop…she repeated to herself again.
Jennifer’s fingers gently started to tug at the string, even as she and Ryan continued their fevered kissing. This bikini is so small it’s barely even covering me anyway…might as well just have it off…Jennifer thought to herself as she continued pulling on the knot on her right hip.
Finally the knot fell open, and Jennifer felt the tension of the string against her flesh slack as the ties fell away. Ryan continued to rock himself slowly back and forth on top of Jennifer’s body, and the motion naturally started to push the tiny scrap of fabric covering Jennifer’s pussy lower and lower until finally it fell completely away between her legs.
Jennifer gasped as she finally felt the entire length of Ryan’s cock pressed against her body with nothing in between. She gently started sliding her body upwards under Ryan, never breaking contact with his mouth. She felt his cock slide lower and lower down her stomach until it slipped in between her legs.
Ryan broke their kiss for a moment and looked down towards where only a moment ago, Jennifer’s bikini bottoms had been covering her. He was surprised to see that the tiny bottoms had come off and were now lost somewhere amongst the rumpled bed covers. “What happened?” Ryan whispered, moving in for another kiss.
“I don’t know…” Jennifer lied, uncharacteristically. “They didn’t really fit anyway…they were so tiny, I guess they just came untied,” she cooed into his mouth as their tongues continued to explore each other. Her heart was pounding. She didn’t want Ryan to think she was being a slut by letting things go too fast, but if just by dumb luck her bikini bottoms had come untied…well…then maybe that was ok, she tried to reason to herself.
“Do you need to retie them?” Ryan asked, not wanting to pressure her into doing more than she wanted to. Ryan knew he could get some more action with Allison later if Jennifer didn’t want to, and he didn’t want to ruin his chances of keeping Jennifer as an option for hooking up later when she might feel more comfortable.
Jennifer’s mind was racing. Ryan was being so sweet and not pressuring her at all, but she was so horny and her body kept begging for some sort of release. Should I let him take my virginity? She thought to herself. I could just ask him to finger me or something…that would be less slutty…but what if I don’t get another chance with Ryan? He’s so gorgeous and nice. Maybe I should just do it…
“Well…” Jennifer started to say, uncertainly. “I…I don’t know. I mean…I’m a…well, it’s just that I’ve never…done anything like this before…” she hesitated.
“You’re a virgin?” Ryan asked, staring into her eyes.
“Yes…” Jennifer said as she broke the gaze. “Sorry, that’s probably super lame.”
“No, not at all,” Ryan reassured her. “I don’t want you to do anything if you’re not comfortable,” he continued. “Plus it would probably hurt a little bit your first time.”
Jennifer frowned, genuinely conflicted. “That’s what I was afraid of,” she said, still able to feel Ryan’s rock hard dick nestled in between her thighs, only inches from her incredibly exposed and wet pussy. “Well, could we just try a little bit and stop if it hurts too much?” Jennifer tried to compromise.
“Sure, we can just go slowly, and you let me know if we need to stop,” Ryan said, smiling down at her.
Jennifer, feeling slightly mollified, spread her legs a little wider, giving Ryan better access. Ryan slowly pushed his hips forward, letting the swollen head of his penis finally come in contact with Jennifer’s wet pussy lips.
“Is that okay?” Ryan asked as he started to slowly drag his cock up and down over the outside of Jennifer’s moist folds.
Jennifer moaned with pleasure. “Oh wow, that feels really good,” she said.
“Good, I’m going to go a little deeper,” Ryan warned and gently pushed his hard dick forward, parting the outer folds of Jennifer’s pussy. Their juices mingled and Jennifer’s lips opened easily, allowing Ryan’s swollen tip to slip inside her body. Ryan felt the familiar resistance stop his progress that signified that Jennifer was, indeed, a virgin. He didn’t go any deeper, but instead slowly drew the tip of his long cock in and out of Jennifer’s pussy, letting her acclimate to the feeling.
“Mmm, that feels really good,” Jennifer murmured. I can’t believe I’m letting him do this! Jennifer screamed to herself inside her head. I’m probably the hugest slut ever, she chastised herself. But God, it feels so amazing…I don’t want him to stop.
Jennifer’s instincts started to take over, and she rocked her hips back and forth in time with Ryan’s small thrusts, starting to feel the pleasure of matching her rhythm to her partner’s. She felt the lips of her vagina stretching to accommodate Ryan’s cock. The sensation was pleasurable. It was tight. There was friction, but plenty of natural lubrication to overcome it. She felt Ryan’s cock bottom out against something before he even got very deep into her. She knew that if they wanted to really enjoy themselves, this barrier would have to be broken.
Jennifer spread her legs a little wider, hoping to improve the angle, and rocked her hips a little further than before. She felt Ryan hit the barrier, and she winced in pain as she realized that this might actually hurt a little bit.
Hearing her sharp intake of breath, Ryan drew back and asked, “Are you ok? I’m not hurting you am I?”
“It’s ok,” Jennifer said. “It’s not too bad. God, I just really want to do this…”
“Are you sure?” Ryan asked, concern showing in his voice.
“Yes, I’m sure,” Jennifer said, even though she was the most nervous she had ever been in her life. I don’t care if this is slutty, Jennifer thought to herself. This feels right, and I’ve come too far to give up now.
In answer, Ryan slid his cock back inside until he heard Jennifer gasp in pain again. He tried to be as gentle as he could, slowly rocking back and forth, trying to get a little deeper each time.
Jennifer felt like her vagina was being ripped wide open. Tears sprang to her eyes, and it took every ounce of control not to cry out. She lost track of the time as she felt the pain radiating from her groin and out to the tip of every limb in her body. God, this hurts, she screamed in her head, sucking in quick gasping breaths.
Jennifer cried out as she felt a huge wave of pain rip through her body, but oddly, the pain immediately started to abate rather than remaining at the same intense level. Her pussy throbbed with pain, but she felt it start to diminish, and wondered if Ryan had given up.
As she opened her eyes and looked down, Jennifer was amazed to see that Ryan’s cock was completely buried inside her. She looked up at Ryan, who leaned down and planted a tender kiss on her lips as he started to slowly slide his long cock back out of her.
Jennifer gasped as she realized that the sensation she was now feeling from her vagina was pleasure, and not pain any longer. She felt Ryan’s cock slide back out of her until she could feel just the tip nestled inside her outer lips. Then Ryan immediately changed directions and buried himself back inside Jennifer’s body.
A low moan escaped Jennifer’s lips as she felt herself penetrated, her pussy walls spreading to accommodate Ryan’s large dick.
In answer, Ryan smiled down at her and continued to pump in and out of her. Wow, this feels amazing, Jennifer thought. I can’t believe I am losing my virginity to Ryan Bradshaw…I’m such a slut…but I don’t even care. She smiled and started to rock her hips back and forth in time with Ryan’s thrusts, intensifying the pleasure for both of them.
Ryan propped himself up on his elbows as he continued to draw his long cock in and out of Jennifer’s wet pussy. He couldn’t believe his luck. First Allie, and now Jennifer, the biggest prude in the whole school, both on the same day. He smiled and reached up to play with Jennifer’s large, round breasts.
Jennifer’s breasts were starting to bounce up and down as Ryan accelerated his pace. Ryan gazed hungrily down at Jennifer’s ample chest, covered very immodestly by the tiny black triangles of her bikini top. The triangles were already bunched up from his explorations earlier, and the already skimpy top was now just barely containing Jennifer’s perfect D-cup breasts as they bounced in time with the teens’ love making.
Jennifer and Ryan were both panting and moaning loudly by now, and sweat glistened from Ryan’s brow. Jennifer grabbed the sheets with her hands, trying to steady herself against the incredibly intense waves of pleasure that coursed through her body with every thrust of Ryan’s smooth cock.
The repeated motion, combined with the top that was already too small for her, caused a knot on Jennifer’s bikini top to slip. All of a sudden, the strings which had been so tight against Jennifer’s breasts slackened, and her large round breasts bounced free.
Ryan saw Jennifer’s perfect tits spring free from their top, and he felt his cock ripple with pleasure at the incredibly erotic sight in front of him. Jennifer’s tight and toned body was now completely naked underneath him. He gazed from her soft and graceful facial features down to her full breasts, now completely uncontained and bouncing wildly up and down. His eyes continued down to her flat and toned stomach, and finally to the amazing sight of his own cock sliding smoothly in and out of Jennifer’s incredibly tight pussy.
Ryan grabbed the bikini top from beside Jennifer’s body and impetuously tossed it aside, where it landed amongst the bras and panties already littering the floor. Despite his effort to make himself last, Ryan started to feel the familiar sensations that preceded his orgasm. He knew it was only a matter of seconds before he would cum, and that there was no avoiding it now.
“Jenny, I’m about to…cum,” Ryan gasped in between thrusts.
“Oh my God, me too,” Jennifer moaned as she felt her pussy start to tingle. “Don’t cum in me, I don’t want to get pregnant,” she gasped as she felt herself move closer and closer to the edge of orgasm. “Can you hold it for a few more seconds?”
“Trying…” was all that Ryan was able to utter as he focused every fibre of his being on not cumming inside Jennifer’s amazing body.
“So…close…” Jennifer gasped as she reached down and started to rub her clit in time with Ryan’s thrusts.
Jennifer felt her pussy tighten, a wave of pleasure spiraling outward through her whole body. Her back arched, her toes curled, and she grabbed the sheets with her free hand. She tossed her head back and let out a brief, but intense scream as her whole body shivered and rocked with her orgasm.
Seeing Jennifer writhing underneath him, wracked in the throes of an incredible orgasm, sent Ryan over the edge. “Fuck…can’t hold it…any more…” Ryan grunted as he ripped his cock out of Jennifer’s pussy just as the first jets of sticky, white cum erupted from the tip.
Cum exploded out of Ryan’s cock and landed all across Jennifer’s amazing breasts and stomach. Ryan panted and moaned as he continued to launch ropes of cum all over Jennifer’s body.
As Jennifer started to come down off of her intense high, she felt the sensation of warm, sticky liquid hitting her in the chest. She looked down at Ryan, who gripped his long cock in one hand and pumped up and down as cum continued to spray from his tip. She felt the warm cum dripping down into her cleavage. She reached up and cupped one breast in her hand, feeling the slick cum coat her hand. She squeezed gently on her breast, and rubbed her hand back and forth, spreading the cum all across it’s round, firm surface.
Curious about what it tasted like, Jennifer brought her hand up to her face, her fingers covered in the white, milky liquid. She timidly inserted a finger into her mouth and sucked the cum off. Mmm, it’s actually not too gross, Jennifer thought as Ryan finally finished cumming and collapsed on the bed next to her. I can’t believe I just did that, thought Jennifer as she stared at her bedroom ceiling. Am I some sort of slut now or something?
The two teens gasped for breath as their bodies started to calm. Jennifer felt Ryan’s muscular body pressed up against her, and could feel the pace of his breathing slow. Ryan propped himself up on one elbow and reached with the other hand over to Jennifer’s amazing breasts. He ran a finger across one nipple, causing it to stiffen, and continued to trail his hand deep into her cleavage, coating his finger with cum.
He brought his hand back up to Jennifer’s mouth and watched as she licked his own cum off of his fingers. Ryan leaned down and was about to give a soft kiss to Jennifer when they were both startled by a noise from the doorway.
“Wow you guys, that was so hot!” Allison stood, naked, framed by the doorway to the hall.
To be continued…