Juicy Lucy

Lucy couldn't believe she'd lost the bet. Sure, she was aware of the tradition among all the cross-country senior girls to have a big sleepover after the end of the season with no one else allowed. And she'd heard that in the past groups had played a game where the loser had to do something embarrassing. But Lucy hadn't even expected to be invited to the slumber party.

Although she was a senior and one of the faster girls on the team, she'd never been particularly close with her teammates. With her petite stature, glasses, and mousy brown hair, she looked younger than her age, even compared to the other cross country girls. She wasn't as social and certainly didn't go to parties, a lifestyle motivated in part by her Catholic faith. While they'd never displayed particular animosity towards her, she was surprised when they gave her the invite. The entire senior class was going -- 8 girls in total.

It turned out that the game this year was just a high-stakes Uno match. While that was innocent enough, the punishment for the year was announced beforehand. In past years the losing girl was made to do something like wear an embarrassing outfit to school or posting a singing video on social media, this year the unluckiest girl would have to go on a blind date set up by the other girls. While this didn't sound as overtly embarrassing as some years, Lucy had never even gotten close to dating and certainly wanted to avoid the punishment.

Unfortunately after a wild 45-minute game, she found herself with several cards still in her hand as the second-to-last girl gratefully played her final card. The other girls teased her a bit, and said they'd find someone fun for her to grab coffee with. Lucy felt her cheeks go red but tried not to say anything that would reveal how nervous she was about the idea.

All Lucy had to go on was that her date, "John" was going to meet her in the coffee shop at 2pm that Saturday. He knew that her name was Lucy and that she'd be wearing a blue dress. Lucy wasn't sure what else her friends had told him about her, let alone who he was or where they'd found him. Lucy sat nervously at a seat near the back of the shop, anxiously tapping her foot and looking around as the meeting time approached.

"Hi, are you Lucy?" a male voice from the side asked. She looked to her left to see a pudgy man old enough to be her grandfather, his gray hair and wrinkles placing him around 60 at least. "Your friends were right, you are beautiful."

"Oh! Um, hi John," Lucy said politely, internally in near disbelief that the other girls would have set her up with this man. "Yes, I'm Lucy, and thank you," she managed to squeak out.

With a sense of casual comfort, John sat down at the table across from her. "I know I may be a bit older you're used to dating, and I don't know what your friends told you about me, but they think you're a really mature woman, Lucy. And they said you were attractive, but you just look so smart and sexy to me."

John's instant flattery caught Lucy off guard. She never been spoken to so directly like this, let alone by a man his age. While she had turned 18 a few weeks ago, she'd never been close to a relationship. Still, John seemed so confident that it was almost easiest to just go along with what he was saying. He made it easy to engage in conversation like the guys she knew from school never had been able to.

After a little while Lucy even forgot that they were on a date, and she found herself telling John about herself like she was catching up with an old friend. She also learned more about him -- that he was 62 years old, retired, and had been divorced for seven years. John had spent most of his career as a mailman, and wow it obviously hadn't made him a ton of money it afforded him a comfortable enough retirement for himself. He had two children with his ex-wife, both of whom were in their 30s now. Lucy had a brief moment of shock when she realized how much older even they were than her.

But for some reason the age difference sunk to the back of her mind. The conversation continued to flow, although it was only after a while that it actually started to feel like a date. John continued to pepper in compliments on her appearance and her maturity, and receiving such attention started to make her feel good, even from such an unexpected source. Lucy didn't expect to see him again after today, but he was pleasant to spend some time with for the afternoon.

"It's been great meeting you Lucy. Hopefully this doesn't have to be the last time we see each other. Oh, I've been meaning to ask you, do you enjoy wine?"

"Umm, I've never had it before actually, you know since I'm like not old enough to drink yet."

"Well in my opinion you're more than old enough. And it could be just a taste. I have quite the extensive collection and would love to show you and teach you to develop a sophisticated palette. Trust me, these types of things come in handy as you grow into adulthood and are looking for ways to connect with others."

"Oh, well I guess that does sound nice John. But I'm not sure I should."

"It's ok Lucy, I only live a few blocks from here, and it's my understanding you walked here as well. It would just be a short little stroll and would be a fun thing to try."

Lucy thought for a second before responding, but realized how comfortable she felt at the idea and agreed to go with John. He had a good point, she was technically an adult and yet she'd never done anything yet that was different than her earlier teenage years. She had to grow up sometime, and this seemed like as good a time as any.

Walking together to John's house, Lucy felt a sense of excitement. She had no physical attraction to this man, but he was pleasant to spend time with and he was treating her more maturely than anyone ever had. Plus, there was a sense of rebelliousness in the idea of trying alcohol for the first time.

After a few minutes the duo arrived at a modest ranch home. "I know it's not much," John said as they walked in the door. "But there's plenty of room for 'ol me." He walked through the living room near the front entrance to the kitchen, where there was a wine rack next to the table holding a couple of dozen bottles. "I don't suppose you have much of an opinion on wine at this point, but I think we should go with something sweet and white, just like you are Lucy."

Lucy blushed at the compliment, and nodded in approval. John grabbed a couple glasses from the cabinet and gave each one what seemed like a generous pour. He handed her one before taking a sip himself. "It may taste a little funny to you the first time, but that's normal," he said reassuringly.

Lucy looked down the glass at the liquid swirling inside, then took a deep breath followed by a small sip. It was actually sweeter than she was expecting, although there was a definite bitterness behind it as well. Beyond the recognizable flavor of grapes, there was little else she could say about it, but a strange feeling of accomplishment washed over her after having tried an adult beverage for the first time. "It's good!" she exclaimed.

"Haha, I'm glad it didn't scare you off! Let's go sit down on the couch while we drink. I'll bring the bottle so you can have as much as you like."

Lucy plopped down on the end of the couch with her glass, and John sat directly next to her, closer than she was used to someone placing themselves. His wide body lightly pressed against hers, his considerable weight upon the cushions causing her smaller body to almost fall into his. His right arm reached up around her shoulder as he set the half-filled bottle on the end table, but even after releasing his grip, the arm fell down around her shoulder. Lucy was now snuggled into John's partial embrace, and while a bit taken aback, she chose not to say anything.

The two continued to chat as they sipped their wine. Lucy told John about school and her time running cross country and volunteering through her Catholic church. He would ask questions, crack an occasional joke, and occasionally brush his fingers against her shoulder. As she got towards the end of her first glass, Lucy started to notice a change in her mood. It was nearly imperceptible at first, but the words started to flow easier, and her head felt lighter as she got more comfortable settling into John's side. Before she could finish her last sip, John smoothly refilled her glass as well as his own.

"Could I tell you something Miss Lucy?" John asked, leaning over towards her. "You're a beautiful, impressive woman and I don't think you realize how sexy you are."

Lucy was shocked at John's words but strangely accepting at the same time. The wine was definitely making her feel more loose, which muted her reception to John's next move as well as he started to lean towards her. Lucy realized that John was leaning in for a kiss, her first kiss ever, and to her own surprise she didn't move her head away as his lips made contact with hers. At the same time his embrace tightened, holding her firmly in place as she experienced her first moments of intimacy with the 62-year-old man.

The experience was unexpected and Lucy would have recoiled had she been able. Thankfully she had set her wine glass on the table as her arm flailed in confusion. But John knew what he wanted and she acquiesced as his tongue split her lips and met hers. She had no idea this was what kissing would be like, but it did have a much more naughty feeling than she'd realized. Especially this kind of kissing. Lucy became aware of how close she was to John and how under his control she felt.

Finally he pulled away. "I think you and I are going to get along just fine Lucy," he said to her. "Was that your first kiss?"

"Yes it was" she meekly nodded. "John, no one has ever talked to me like that before. I'm not sure how I feel about it. You're a great guy but this is moving a bit fast for me. And I feel a bit dizzy from the wine."

"This is normal Lucy, don't worry. And I don't think it's the wine, I think it's another feeling that you're just not used to. Your body wants you to have fun, and sometimes you have to listen to it." Before she could do anything, he leaned in and kissed her again, and this time grabbed one of her small breasts over the top of her dress. Amid her surprise, Lucy became aware of a new kind of feeling that she'd never experienced in its entirety before, an excited embarrassment that she couldn't place a finger on.

After a few seconds, John pulled back again and looked into her eyes. "Lucy, let's go to my bedroom," he said as he sat up from their somewhat asymmetrical embrace.

"What are we going to do in there John?" Lucy asked, a look of confusion on her face.

John responded with a bemused look before a wave of realization crossed him. "Lucy dear, do you know what sex is? Did your parents tell you about that?"

"Ummm, not really, they said they would before I went off to college but I don't really know what is is," Lucy said, embarrassed. And it was the truth. Her conservative Catholic family had never been open with these sorts of things beyond the surface-level behaviors of chastity, and they'd opted her out of the health classes back in middle school where the topic had been discussed. She knew it had something to do with love and kissing, but this was already unfamiliar territory for her.

"Come with me," John said, taking her hand and leading her upstairs to a well-appointed master bedroom. "Lucy, you're going to lie down on the bed."

She did as John told her.

"Lucy, sex is something kind of like kissing that two adults do. Unlike kissing where each side is equal, in sex the woman lets the man do everything to her as she submits to him. You may not realize it yet Lucy, but you are a very beautiful, sexual woman, and I am looking forward to making love to you.

Some of the things I'm going to do may feel wrong at first Lucy, and some of these may feel uncomfortable. You need to trust me and I'm going to make this the best possible time for you. Do you understand?"

Lucy nodded meekly, and as having received confirmation John did yet another thing Lucy didn't expect. He grabbed the bottom hem of her dress, which even with her lying on the bed extended nearly to her ankles, and began to pull it up over her waist, revealing her slender yet toned legs beneath. Lucy instinctively moved to stop him and yelped. "John, what are you doing?"

"Lucy, sex is about bodily contact. I know this may feel wrong to you, but we are both going to get naked. Your parents may have taught you modesty, which is good most of the time, but in this case since we are in private I'm going to see everything. Just let me undress you dear."

Lucy gulped and remained limp as John continued to pull the dress up. Up over her waist, revealing her white cotton panties, and further past her torso and finally over her head. She allowed her arms to be pulled up with the sleeves of the dress as the whole thing finally came off. And then Lucy was lying in only her bra and panties. John tossed her dress to the side and removed his own shirt, followed by his pants. He stood in front of Lucy in only a pair of boxers that curiously seemed to extend out in front of him. He looked his age, his large gut distending down over his waistline and graying body hair covering his chest, arms, and shoulders. Lucy felt incredibly vulnerable and still wasn't sure where this was going.

"Lucy, do you know what men have between their legs?"

"Umm, it's a penis, right?"

"Yes honey, that's right. Have you ever seen one?"

Lucy shook her head no. In response, John lowered his one remaining article of clothing, and out popped a firm looking log of flesh pointed directly at her. Lucy wasn't sure what she was expecting, but this was a much larger and more aggressive-looking implement than she had anticipated. Yet the strange stomach-churning feeling she was experiencing only grew stronger. This felt wrong, like it was something she shouldn't be doing but was going along with anyway.

"Penises get hard like with when we see a beautiful, sexy woman Lucy. You're that woman, and you have a lovely little body. I'm excited to see the rest of it." John leaned forward and reached around Lucy's back, delicately unclasping her bra and lifting it up over her arms. She instinctively put her hands over her breasts, and John firmly yet gently pushed them aside.

"You have surprisingly perky breasts Lucy, I didn't expect you to be a B cup. That's very sexy." John next grabbed the waistband of her panties and quickly slid them off of her legs. Out popped an unshaven bush of bright red hair that no man had ever before laid eyes on. Lucy's feeling of vulnerability grew, but John continued, climbing onto the bed and pushing her legs open so he could kneel between them.

At that moment Lucy felt a completely new type of contact. Skin-on-skin sexual contact. John's fingers rubbed the tight slit buried under her curly red hair, and an unbelievably intense sensation spread from her groin across her entire body. Lucy involuntarily bucked beneath John, both responding to and seeking to escape this new kind of touch, but his much larger frame held her in place.

"Mmmm, your pussy is WET Lucy. You're a juicy little Lucy. I like that."

Lucy was feeling scared and confused. "Is that bad John? I'm sorry, I didn't realize, this just all feels so new. I'm not sure I -- OHH!!" she yelped as he rubbed her slit again.

"No my darling Lucy, your sweet little pussy will get wet when your body is excited to have sexual contact with me. It's perfectly natural and a sign that you're now a woman ready for intimacy. It's clear that we're both ready and excited, Lucy, so I won't keep you waiting any longer. It's time to show you what sex is and make you a woman."

John removed his hand and settled more fully on top of her, his large stomach squishing down on her much smaller frame. Lucy still felt some pressure on the sensitive spot between her legs. She realized that both of John's arms were up by her head, which could only mean one thing. Suddenly she felt the pressure increase, and a newly intense and unsettling feeling emanated from her groin. The stiff appendage that could only be John's penis was PUSHING into her. And her slick vagina was opening to let it inside! This couldn't be right, could it?

"Fuck, you're tight Lucy, you feel so good. This next part is going to hurt, but only the first time and only for a bit, then it will go away. I'll do everything, you just let it happen sweet thing." Lucy opened her mouth but before she could speak a word she released a scream of pain and surprise as John pushed his penis several inches deeper into her, breaking through something inside of her and causing a burning sensation. John pulled his hips back before pushing into her again, even deeper this time. The pain continued as Lucy squirmed and moaned, but she was unable to form any words while John took her as his own.

While clearly conscious of her pain, he continued to piston steadily in and out of her, pushing slightly deeper each time until his pelvis lightly slapped against hers. The pain faded, too slowly for Lucy's comfort but enough that she could come to grips with the feeling of penetration. She had no idea sex involved something like this, so intimate and dirty at the same time. It felt like she was being a bad girl, a sensation only heightened by the way her body seemed to allow John's invasion of her most private spot, lubricating the way for his pulsing rod.

John's face hovered only inches above her, and after her panting in pain had calmed down her planted a firm kiss on her lips while he continued to make love to her. Lucy was still wordlessly enunciating, but her sounds had evolved into rhythmic moans that crescendoed with each thrust of John's hips. While the feeling wasn't as unpleasant anymore, John was clearly enjoying the experience very much, and he began to whisper to her in a very different tone than she'd ever seen from him.

"Yeah, that's a tight little cunt. Ohhhh that's so GOOD Lucy. I knew you were a naughty girl, I knew it would be so easy. You like this don't you? Take that DICK little bitch!"

Lucy was taken even further off guard but the surreal change in tone coupled with the indescribable sensations of her first every sexual experience. John's dirty talk made her feel ashamed of the feeling between her legs. It was still just as intense, but different now -- almost something like pleasure? But it was a different, more forbidden kind of pleasure than she'd ever known. And she hated herself for liking it even a little bit. This wasn't what Catholic girls were supposed to do, but she'd been too dumb to know when to stop it. She supposed that John was right, and this was something she'd had coming anyway.

John's pace had picked up and now maintained a steady rhythm, his penis penetrating over and over again into her wet hole. Lucy's light moans coupled with his grunts and occasional comments that all sounded very dirty to her. With the intimate contact of both the eyes and sexual organs, Lucy was closer to John that anyone she'd ever known -- family, friends, teachers. And she'd just met him a few hours ago. And he was making her feel differently than all of those people. A feeling of dirty pleasure that was continuing to build within her. Lucy was powerless to stop it just as she'd been powerless for this entire experience. Her high-pitched moans grew louder as John's pace continued to increase.

"Mmm, yeah you love that dick I can tell. Little virgin pussy, so wet and tight. You gonna cum for me, juicy Lucy? Oh yeah you like that. I'm gonna fuck you so good, oh yeah that body is mine."

Lucy felt so exposed and vulnerable from the combination of John's comments and the intensity of their sexual connection, and the waves of sensation built higher and higher as her hips seemed to spasm in cadence with his thrusts. She still wasn't sure what has happening or when this would end, but she squealed in response to the growing, pulsing, tingling concentrating between her legs. Finally, around the sense of probing fullness, it came to a point of ecstasy, and Lucy cried out as she lost all control of her body. John's face also changed in that moment, as he finally stopped his thrusting and held himself at the deepest point within her, stretching her virgin hole that could barely handle him.