Celebrity Shemale Secrets: “Jewel’s Backstage Tryst”



By: Tag1702

(Trans/F) (Mast, Oral, Anal, Reluct, Pedo)

This story contains graphic sexual content. It also portrays singer Jewel Kilcher as a transsexual, which to the best of my knowledge, she is not. This story is not meant to be an accurate portrayal of Jewel’s lifestyle, or her habits. It is written purely for fun, and not for profit. If you are okay with everything mentioned, than by all means, read on.

Jewel Kilcher practically fell back into the chair backstage in her dressing room.
She loved performing live, and would probably never give it up, but these shows took a lot out of the thirty-three year old. A soft sigh escaped her lips as she took a deep breath. All in all, it had been a great show. The blond singer had been on fire, and the audience had been great. She was especially happy about their response to her new song, Stronger Woman. She’d been wanting to do a country album forever, and was happy that her fans were responding so well to the first song from that offering. She was very excited about the album’s upcoming release.

Now, she had about a week free before her next show, and was looking forward to the much needed time off. She would probably spend most of it locked away in her room writing. That was how she spent most of her time these days. Writing music and poetry relaxed Jewel in a way that little else did.

Standing up, and feeling a little bit better, she stood up and eyed the bed longingly. Right now she was so worn out that all she wanted to do was crash onto the bed and sleep for a week. Still, she knew that she couldn’t. Their was the little matter of the prize for the contest winner that she would have to deal with. A few weeks ago, her promotion team had created a competition for her fans. It was a poetry writing contest. Jewel had read every entry, and the winner was to be published in her next poetry book. Tonight the winner would be coming back to her dressing room to meet with her. The brown eyed musician loved her fans, and would have loved this under normal circumstances, but she was tired. Still, the winner, a fifteen year old girl named Haley would be here any minute.

Looking away from the coveted bed, she instead made her way to the bathroom. It wouldn’t hurt to take a quick shower. After all, she was all sweaty from the show, and had about twenty minutes before her manager would be bringing Haley around.

Closing the bathroom door, she reached into the shower, and started the water. As the water was running, she started to disrobe, admiring her form in the mirror. So close to thirty-four, she was still in great shape. She removed her white top, and bra, allowing her firm breasts to pop free. She cupped them, staring at the reflection in the mirror. They weren’t huge, but they were still incredibly firm, not sagging in the least. Her nipples were silver dollar sized, and bright pink. She brushed a finger across one, an felt a stirring in her crotch as the nipple began to harden. All of the excitement must have gotten her a little worked up.

Slowly, she pulled her blue jeans down. Jewel was never the type to dress up for her concerts. She liked the more plain image better. Their she stood in nothing but her plain white panties, staring at herself in the mirror. She had to admit that she was kind of horny at this point. Looking down at the gentle curve of her hips, and her long slender legs, she couldn’t help herself anymore. Jewel Kilcher bent over to pull her panties down. When she did, a ten inch cock sprang up between her legs. It was her dirty little secret. Her lover Ty was the only other person in the world who knew about it, and she’d been surprised by his rather positive reaction to it.

Jewel, looking at her feminine body in the mirror, wrapped her hand around her member, and began to stroke it softly. With her other hand, she began to squeeze her sensitive breast. It felt so good, and she was getting harder by the second. It wasn’t long before her engorged dick grew to it’s full twelve inches in her fist.

“Ohhh,” she moaned softly, “Ohhh yeahh…” Slowly, never letting go, she climbed into the shower, and slid the glass partition shut. As the hot water cascaded down her naked body, she began to jerk it faster. Her thoughts turned to Ty. She thought about him naked on his knees in front of her. She almost came when she thought about him wrapping his lips around her member, and taking it into his mouth. For somebody who swore up and down that he wasn’t gay, he gave great blowjobs.

“Mmmm… Ty!” she cried as she thought about fucking his face. The thought of sliding her dick deep into his throat and fucking it hard nearly pushed her over the edge, but she wasn’t ready to cum yet. Slowing her pace, trying to catch her breath, she reached behind with her free hand, and thought about how good it felt when he slid a finger up her ass while he sucked her off. Leaning forward, her upper body pressed against the tiled wall, she started to pump the finger in and out of her tight little asshole as she continued to jerk off.

“Fuck yeah…” she moaned between breaths. “Oh… Mmmm…Yeah…Ohhh.” Her breathing became erratic as her body started to slide up and down the tile. “That’s right… Finger fuck my ass… Suck… My… Dick…” She started jerking it harder and faster, as her finger increased it’s pace. Pulling her finger out, she thought about bending Ty over the couch and just fucking the hell out of his tight firm ass. She imagined his squeals of pain and pleasure as she would slide her organ deep into his ass, and then pull it out again. She imagined pulling his hair back, and just ass ramming him as hard as she could…

“Holy Fuck Ty…” she moaned. She was just about to cum, when she heard the door buzzer.

“Shit!” she shouted immediately dropping her swollen dick. She couldn’t believe that she’d been jerking off for twenty minutes. Sticking her head out, she shouted, “I’ll be there in a minute.” Turning the water off, she reached for the towel that she’d hung over the top of the door. She dried off as quickly as she could, thankful at least that the shock had killed her erection. Before long, she had slipped into the white, loose fitting jeans, and dark blue T-shirt she had picked out. Towel in hand, drying her hair, she walked over to the door and opened it.

On the other side, stood her manager, and the young winner, Haley. For a fifteen-year old, she was surprisingly attractive, and Jewel felt her dick move a little, tucked safely between her legs. The singer songwriter had been with a few girls in her time, but she would only go down on them. When it came time for them to pleasure her, she’d send them away, and take care of business herself. She’d always been extremely self conscious about her situation. Until Ty, she’d never been comfortable enough to share her secret with anybody.

Haley was about five feet nine inches tall, a few inches taller than Jewel herself, and had long auburn hair and dark blue eyes. She was thin, and her body was beginning to fill out nicely. Her breasts were probably just about B cups, and her hips were just starting to swell outward. She was wearing a loose fitting white button up blouse, her black bra clearly visible underneath, and a black leather skirt that stopped just above her knees. Her slender legs were clad in dark pantyhose, and she was wearing shiny black heels. Of course she was only fifteen…

Jewel, starting to feel desire overwhelm her and not really thinking about the consequences of her actions, began to hatch her plan right there.

“Hello Haley,” she said, extending her hand. The young girl took it.

“Hi,” she said, clearly nervous. “I’m Haley…” she paused, and appeared to think it over, “but I guess you already know that.” She shook her head, and appeared to be frustrated with herself. “Stupid,” she mumbled under her breath. “I’m sorry. I’m just so excited to meet you. I am like your biggest fan. I have all of your CDs, and your poetry book, and I’ve been to like three of your concerts. I’m just so excited to meet you.” Something about her nervous demeanor made her even more attractive.

“Thank you,” Jewel said calmly. “That means a lot to me… and Haley…”

“Yeah?” she said expectantly.

“You can let go of my hand now,” Jewel smiled.

“Oh… sorry,” she looked a little downcast.

“It’s okay,” the singer said warmly, “Why don’t you come in?” She stepped aside, allowing Haley to enter her dressing room.

“Do you want me to stick around?” her manager asked.

“I think I can handle a fifteen-year old girl,” she said. In fact, she thought, I’m looking forward to handling her. “You go home, get some sleep. I can call the car to pick her up when we’re done.”

“If you’re sure,” he said, looking a little uncertain. Of course he was just looking out for her safety. If anything happened to her, and he hadn’t stuck around, he would feel extremely responsible.

Jewel spoke quietly so her fan, who had taken a seat on the couch, couldn’t hear, “I don’t think she’s going to try to kill me or anything. She’s so nervous about meeting me, that I doubt she could think clearly enough to try anything.”

He nodded. “All right, see you tomorrow.”

Shutting the door behind him, she turned to her fan. “So, why don’t you tell me a little about yourself Haley.” She walked over to the couch, and sat down, leaving little space between them. Fortunately, Haley was too wound up to notice that anything was going on.

“Okay,” she said, “Umm, my name is Haley, but you already know that. I’m fifteen and just started ninth grade, which is pretty exciting. I’m really enjoying my drama class. Let’s see…” she appeared to have to think pretty hard to recall important things about her own life right now. Jewel just smiled at the thought. She was beginning to think that Haley would do just about anything she asked. She could feel her cock moving between her thighs at the thought. “I don’t have any brothers or sisters… Let’s see… I enjoy reading and writing.”

“Well, you obviously like to write,” Jewel said as she stood up, “and you’ve definitely got talent.” She started to walk over toward the mini fridge in the corner of the room. “You’re poem was really very good.”

“Thank you,” the girl said loudly. “That means a lot to me, coming from you.”

“I mean it,” Jewel said, opening the fridge, “You could be an incredible writer some day if you keep at it.”

Haley was apparently so in awe of her mentor that she could only repeat, “Thank you.”

Now it was time to put things to the test. “Would you like a glass of wine Haley?” Jewel was on pins and needles waiting for the girl’s answer.

“I… I don’t know,” Haley said nervously, and it was clear that their was a battle going on inside of her. Obviously, she was underage, and knew that she shouldn’t, but she also didn’t want to disappoint Jewel either. “I probably shouldn’t.”

Well, Jewel thought, if I can’t persuade her to have a glass of wine, there’s no way I’m going to be able to convince her to have sex with me. Time to lay it on a little. “I don’t think one glass is going to hurt anything,” Jewel said, wearing her warmest smile. “Besides, this is a cause for celebration. I think even you’re parents would agree with me on this one Haley.”

Silence. Horrible, impenetrable silence.

Finally, “Okay… I guess one glass won’t hurt anything.” Jewel breathed a sigh of relief. It was clear that Haley still wasn’t completely sure, but it was a good sign. It meant that she might agree to other things she wasn’t sure about later.

She took the bottle, and grabbed two glasses from the counter, and walked back over to the couch. She set the glasses down on the table, and filled each with wine. She took the glasses and handed one to her guest. “A toast,” Jewel said, “to your bright future as a writer.” She extended her glass out and tapped it against Haley’s. She took a sip, and watched in anticipation as Haley, after a short pause, finally took a sip.

“That’s pretty good,” she said, smiling if not a little uncomfortably.

“So, I want to ask you a question Haley. If it’s too personal, just say so.” She almost smiled as she watched the young girl take another sip of the wine.

“O… Okay…”

“Were you depressed when you wrote your poem?” Jewel waited. Now that she’d gotten Haley to drink, she knew that if she could get the girl to open up to her, then there wouldn’t be anything she couldn’t convince her to do. Haley also didn’t seem to notice that the singer was sitting sideways, with her legs on the couch, practically leaning over her.

“Umm… yeah,” she said, taking another encouraging sip.

“Can I ask why?”

“Well, my dad had just died in a car accident…” there was a long pause. “We were really close… and when he was killed…” She looked like she might start to cry.

“It’s okay, Haley,” she said encouragingly. “I’m sorry. Why don’t we talk about something else.”

“Thank you. I’d rather not talk about that right now.”

Jewel noticed that Haley’s glass was getting low. “Would you like some more wine Haley?”

“Umm… I guess one more glass won’t hurt.”

Jewel poured more in, filling her glass again. “So, do you have a boyfriend?”

Haley smiled nervously. “No. I’m concentrating on my schoolwork right now. I’m not really ready to date yet.”

“That’s surprising,” Jewel said, taking another sip from her own glass.

“Why do you say that?” Haley asked, glancing over. For just an instant, they were looking into each other’s eyes, and Jewel was sure that they’d shared a moment.

“Well,” the native Alaskan said, “Pretty girl like you. I’d think you’d have boys hitting on you all of the time.” Maybe a few of the girls too, Jewel thought with a smile. She happened to glance down, and was surprised to see that Haley had finished her second glass of wine. This was going better than Jewel could have hoped.

“Well,” Haley said softly, “There is one guy who just won’t leave me alone, but I’m pretty sure that he just wants to sleep with me.”

Jewel held her breath for a second before asking her next question. “Well, you’re both young. What’s wrong with having a little fun?” That was it. Haley’s answer and attitude would determine how the woman would treat the rest of the night.

“Well,” Haley started, clearly on shaky ground. “I just don’t know if I’m ready yet.”

“I see… Can I ask you another personal question Haley?”

“Well,” Haley said with a smile, that depends on whether I can have another glass of wine or not.” This was good. The girl was becoming much more comfortable than she had been when the night began. Jewel poured her some more wine.

“Have you ever had an orgasm Haley?”

Haley actually blushed, and stopped drinking her wine mid sip. “What?”

“I mean,” Jewel said, “Obviously you’ve never had sex, but have you ever fingered yourself, or used something to have an orgasm?” Haley was starting to look a little nervous again. “It’s okay,” Jewel said, “We’re both girls, and you’re practically an adult. If your writing is any indication, then mentally you’re just as grown up as I am. It’s just girl talk Haley.”

Haley seemed to calm down a little. “No, I haven’t.”

“Have you ever thought about sex?” Jewel asked casually, knowing that her moment was quickly approaching.

Drinking the rest of her wine down in one gulp, Haley whispered, “I think this stuff is going to my head. I feel a little light headed.” She giggled a little nervously.

“That’s normal,” Jewel whispered, “That’s how alcohol affects people.” She smiled, “That’s why we like it so much.” There was a pause, “So, have you? Ever thought about it, I mean?”

“I guess,” Haley said a little reluctantly. “I mean everybody does, right?”

“Of course,” Jewel said, “and there’s good reason for that.”

“Oh,” Haley whispered.

“Having an orgasm is the most amazing thing you’ll ever experience Haley. It’s absolutely incredible.”

When Haley didn’t respond, Jewel couldn’t wait anymore. Without thought, she leaned over and kissed the fifteen-year old girl firmly on the lips. Her lips were the softest Jewel had ever kissed. Of course, after a moment, the girl recovered from her shock, and pulled away. “What are you doing?” she whispered, clearly trying to catch her breath.

“That was a kiss,” Jewel whispered mockingly.

“I know what that was,” Haley said, “It’s just… I didn’t expect you to kiss me.” Their faces remained inches apart.

“I’m sorry,” Jewel said softly, “If you didn’t like it…”

“It’s not that…” Haley whispered, “I just…”

“You’ve never kissed a girl before right?” Jewel asked softly.

“I’ve never kissed anybody before.”

“So I was your first kiss?” the singer asked with a smile.


“Did you like it?” Now was the moment of truth. If she said yes, than the songwriter would continue with her plan. If she said no, then everything ended right here.


“Do you want me to kiss you again?”


Jewel Kilcher didn’t waste any more time. Once again she pressed her lips to Haley’s, savoring the salty taste of the girl’s supple lips. As they kissed, Jewel’s hands started to slide over Haley’s young body. One hand rested on her side, while the other began to squeeze her breast. It felt so soft in her hand. She couldn’t wait to feel it without the shirt and bra in the way. This made the young girl purr. This made the blond even hornier.

For her part, Haley was really getting into the kiss too, but her hands remained firmly at her side. Jewel pulled away briefly. “You can touch me if you want to,” she whispered into the brunette’s ear. As the kiss resumed, her words had the desired affect as she felt the girl’s hands roaming up and down the side of her body.

As Jewel used her tongue to pry her potential lover’s lips apart, she climbed over, straddling Haley on the couch. Her effort paid off, as she finally slipped her tongue into Haley’s mouth. They kissed for a moment, Haley’s hands on Jewel’s waist, and then the singer pulled away and started nibbling on Haley’s earlobe, and breathing gently into the ear. She was rewarded by her partner’s gentle gasps and moans.

While she slowly started to work her lips down Haley’s neck, her hands slowly started to unbutton the white blouse. She was actually surprised when Haley didn’t try to stop her. She actually pulled away. “Haley you’re poem made me feel something powerful, and now I want to help you feel something powerful…” she paused, “but if at any time you want me to stop, just say the word and I will.”

“I want to keep going,” Haley whispered timidly.

Jewel smiled, “Me too Haley.” She went back to kissing her way down the teen’s tender neck, her hands spreading the unbuttoned shirt aside. Jewel nibbled gently on the collar bone, as her hands pulled Haley’s bra cups down, revealing her small, developing breasts. “They’re beautiful,” the songwriter whispered with a smile as she once again looked her lover in the eye. Her hands began to squeeze the tender tit flesh as her tongue flicked across one of the nipples.

“Ohhh,” Haley moaned. “Mmmm”

Girl, you haven’t seen anything yet, Jewel thought with an inward smile. As her fingers began to tweak the left nipple, she wrapped her lips around the right breast, taking as much of it as she could into her mouth. She began to suck on the nipple lightly. She could feel the girl’s heart beating rapidly in her chest. After a moment, she switched breasts, biting down gently on the other nipple, and sliding her tongue back and forth across it.

Haley began to squirm on the couch. “Ahhh… Ohhh… Feels so good….”

It was time to show the girl where this was going. As she continued to nibble on Haley’s soft breast, her hand slid it’s way up her inner thigh. The fifteen-year old gasped, as she felt Jewel’s hands traveling up the pantyhose clad leg. Never one to be shy, Jewel started to rub Haley’s pussy. Even through the nylon, she could feel the wetness forming there. She couldn’t wait to taste it. The thought was making her cock throb.

“Oh god!” Haley cried.

Time to go in for the kill. Jewel pulled away from Haley’s tender breasts, and crawled down her body, kneeling on the floor between her now spread legs. Haley couldn’t talk right now. She could only watch as Jewel pushed the skirt up over her thighs. The girl lifted her but just a bit to slide it up further. Jewel pushed the skirt up enough to expose the belly button and began to kiss it, as her hands started pulling Haley’s nylons down. Now Jewel could see that bald little pussy in all of its glory. The tiny little slit beckoned to her.

Softly, she slid a finger down the crack, spreading the lower lips. She then held the finger in front of her mouth and licked it. “You taste amazing Haley,” she whispered. She slid the finger between her lips and began to suck on it, savoring the flavor of Haley’s tasty little cunt.

She leaned down and pressed her lips to the flesh just above the pussy, as her hand slid down. The finger she had licked slowly worked its way into Haley’s tight little hole.

“OHHHHHH…. YEAHHHHH…” Haley moaned as Jewel started slowly pumping her finger in and out. While her fingers were busy fucking the teen, Jewel’s tongue spread the lips once more and found the clit. She started to suck on it lightly, and felt the body beneath her begin to buck in rhythm with her finger. Finally, she pulled her finger out, and started rubbing Haley’s engorged clit. She hadn’t gone deep enough to break the hymen, and had decided firmly against taking away the proof of Haley’s virginity. She slid her tongue into the hole, and started tongue fucking her while her finger and thumb worked it’s magic.

It didn’t take long before Haley’s young body gave a large spasm, and she cried out from her very first orgasm.

Jewel smiled, and pulled away.

“That was amazing,” her young lover said in between gasps.

“Thank you,” the blond said, climbing back up on the couch. “It’s been a while, so I’m a little out of practice.”

“No, no… that was, like you said before, the most amazing thing I’ve ever experienced.”

“Well, thank you,” Jewel said with a smile. Now it was time to bring the evening to an end so she could take care of her own business. Her member was rock hard now, and craving attention. Seeing Haley sitting there, half naked in the afterglow of her very first orgasm wasn’t helping matters any either. “You should probably get your clothes back on. I’ll call the car to come around and take you home.” She stood up and started toward the phone.


She turned around to see Haley standing up.

“What is it?”

“Umm… Well, that felt so amazing and all… and… well… I mean… I’ve never done anything like this before… but… umm, well, I’d… I mean if you want… I’d like to repay you, or at least try to.”

Jewel smiled, “It’s okay Haley, you don’t have to do anything else.”

“I know I don’t have to, but I want to.” It was said with such force that it surprised the singer.

“Haley, it’s really okay. I did that because I wanted to do something special for you and…”

“Exactly. I want to do something special for you.” She was starting to look like she might not take no for an answer. That could be a problem. Teenage girls could be incredibly vindictive. If she left here angry, she might tell somebody what had happened here. That would be trouble. Aside from getting Jewel locked up for statutory rape, and labeled as a pedophile, it would also no doubt bring her secret into the public eye.

Still… Now Jewel was the one getting a little nervous. “Haley, I’m… I’m not like other women…”

“I know,” now she was walking across the room, stopping right in front of Jewel. “You are so much more amazing than other women.” She leaned up, and this time she initiated the kiss. For all of her reservations, Jewel Kilcher was powerless to stop it. She embraced the lip lock, her hands once again finding their way to Haley’s young body, stopping to grip her bare ass.

The girl’s hands were busy pulling Jewel’s shirt up, and before long her breasts were exposed. Haley started massaging them as they kissed. Now it was Jewel’s turn to purr. Obviously the girl had been paying attention.

Now those same hands were busy unfastening Jewel’s jeans, and all hell was going to break loose. The singer knew it would, but couldn’t bring herself to stop. Her body wanted this more than her mind wanted to stop it.

Once the jeans were undone, Haley started sliding them down. Jewel wasn’t wearing any underwear, and kept her thighs pressed tightly together, hoping to conceal her manhood. As the girl started sliding the pants down, she sank to her knees, head level with Jewel’s apparently smooth crotch. Maybe I shouldn’t have done this she thought, her conscience suddenly returning after it’s absence. Maybe if I hadn’t let her drink so much wine. Maybe…

She couldn’t help herself. As her young lover pried her legs apart, twelve inches of hard cock popped free slapping the surprised girl across her face.

“Oh… Oh my god!” she shouted, falling backward, simply staring at the huge member and balls between Jewel’s legs. “Oh my god!” She started trying to slide further away on her back.

“Haley. Haley, it’s okay,” Jewel struggled to try and comfort the shocked teen girl. “I told you, I’m not like other women.”

Haley’s eyes didn’t leave Jewel’s throbbing organ, “No, you’re a man!”

“No, Haley, it’s not that simple…”

“You pervert!”

“Haley, please let me explain,” Jewel was close to tears now. This had all gone so horribly wrong. Of course, if she’d been thinking she never would have started this encounter in the first place. “Please, let me explain before you leave,” she said between tears. Jewel dropped to her knees, covering her eyes and trying to wipe the tears away, “Please, you don’t understand.”

“Fine,” Haley said rather forcefully, “Explain then.”

That surprised Jewel, who’s member had started to soften, and was now hanging limply between her legs. She looked up. Between sniffles, she managed, “I… I was born male… that much is true, but I realized very young that something wasn’t right. I… I didn’t feel male. I knew I was really a girl.” She was surprised at how easily this was coming out. She’d only ever told this story to one other person. “My parents were very understanding, and I started taking the hormones before I hit puberty… I just haven’t gotten around to having the surgery yet…”

“Wow,” the girl whispered, “But don’t you have a boyfriend?”

Jewel managed a rather pathetic smile. “Yes, and he loves me for who I am. I was actually thinking about having the surgery a few years back but he urged me not to. Ty has been the most wonderful person I’ve ever met.

“Does that mean he’s…”

“Gay?” Jewel chuckled. “Bi maybe, but I think it’s more complicated than that. I just don’t think he cares about gender one way or the other. He’s in love with me no matter what I am.”

Within the span of about thirty seconds, the girl had gone from outraged to curious. Maybe her little indiscretion tonight wouldn’t destroy her. She sat down on the ground, crossing her legs, and noticed that, although Haley was still paying attention, her blue eyes were still trained on the blond’s rather impressive package.

“So, do you and he… you know?”

Jewel actually chuckled, “Yes, we have sex, if that’s what you mean.”

“So he…”

Feeling a little more comfortable, and knowing what she was asking by the look in her eyes, Jewel decided not to mince words anymore, “Yes, he actually enjoys sucking my dick, and he lets me fuck his ass too. Of course, I have to do the same for him. That’s kind of the arrangement.”

“Does it feel good… I mean when he… puts it in your butt?”

Jewel actually laughed out loud. “You mean when he fucks my ass? It’s okay, we’re both more or less adults Haley, you can say it.”

“Okay… Does it feel good when he…” she looked a little embarrassed, “fucks… your… ass?” She actually looked a little surprised as the words left her mouth.

Jewel nodded, “It does. I mean, it hurts at first, but after that it feels great. He feels the same way.”

Now Haley was staring at Jewel’s member again, and looking down, she realized it was growing again. Must be all this talking about Ty, she thought. Oh and the half naked girl sitting a few feet away probably isn’t helping either.

“Sorry,” Haley said, realizing that she was staring, “I’ve just never seen one of those close up before. I didn’t realize they were so… big.” She was whispering again.

“Well,” Jewel said with a little pride, “I am above average.”

“Can I…. Can I touch it?” Haley said quickly.


What now? The singer wondered. If I let her touch it, the situation could get out of control again. On the other hand, I really want her to touch it!

“Okay,” she finally said, “Come over here.”

Haley obeyed, dropping her shirt, and stepping out of her pantyhose on the way. That left little doubt in Jewel’s mind about what the teenage girl had in mind, even if she didn’t realize it herself. She sat down right in front of her, and slowly reached out.

“It’s okay,” Jewel whispered, “It won’t bite.”

Summoning every last ounce of courage, Haley slid her hand down the massive shaft, and pulled back in shock. “It moved…”

“It does that,” Jewel whispered, “It means it likes you.”

“Can I…”

“By all means.”

Once again, she reached out, and stroked Jewel’s hard cock softly. When it moved, she didn’t recoil this time. She started to pet it like she was handling a pet. The singer smiled, “You can use a little more strength… grip it with you hand… just like that… Ohhh… Gooood…” Haley started sliding her fist slowly up and down the shaft. “Mm… Right… Just… Like… That…”

As she jerked Jewel’s dick, she leaned in and kissed the singer on the lips again. It was a brief kiss before she pulled away, “I think I still want to repay you…” she whispered, quickening her strokes. “If you’ll let me I want to… I want to suck your cock.”

“Please,” Jewel moaned, completely lost in the pleasure now. Haley softly pushed Jewel onto her back, and got down on her hands and knees, looking down at the quivering member in her hand. Without pause, she wrapped her lips around the tip, and slid about an inch into her mouth. As she felt the warmth surrounding the head of her cock, she completely lost it. God she needed this! “Suck me!” She cried. “Suck my dick Haley!”

The girl worked another inch in as Jewel’s hips started to buck. For a beginner, she was amazing. It must have been intuitive. Jewel could feel every swirl of the tongue, driving her further over the edge. “Yeah!” She looked up and was immediately taken with the sight of the tuft of long auburn hair sliding up and down over the top of her dick. Without meaning to, she reached up, and gripped the sides of Haley’s head. She started forcing it down further and further. Two inches, three inches, five inches… she kept going. She could hear Haley gagging, but couldn’t stop herself. She used her hands to force fuck Haley’s throat for about five minutes, pulling her head off every so often so she could breath, and rubbing her cock all over her face.

“God!” she screamed. “Yes… yes… Fuck yeah… I think I’m…” Before she could finish, she sprayed her hot cum down the girl’s raw throat. She pulled her face off, and shot a wad all over Haley’s cheeks, and forehead, even getting some in her hair.

“That was amazing,” Jewel whispered, trying to catch her breath. “Fucking amazing… You… suck dick like a pro Haley.”

Haley apparently wasn’t done though. She started stroking Jewel’s cock again, and it wasn’t long before, to her own amazement, Jewel was hard again.

“Ohhh… Haley, what are you doing?” Jewel was never usually ready this quickly again, but this girl was different from anybody she’d ever met.

“I… I mean as long as we’ve already done this… I… I think I’m ready to have sex…”

“Oh,” was all Jewel could say. This little girl was full of surprises.

“Please,” Haley begged, and it was clear that she wanted this. Somehow Jewel had opened something in this girl tonight, something that had been dormant her entire life.

“Okay, get on your hands and knees Haley,” Jewel sat up. To her amazement, Haley did as she was told, and Jewel found herself staring at that beautiful ass, framed by the skirt pushed up over her back pretty little back.

Jewel positioned herself on her knees behind the girl. “I’ll fuck you, but first…” She leaned down and slid her tongue up Haley’s ass crack. Her body jumped at the surprise. She used her fingers to spread Haley’s ass cheeks, and slid her tongue around her puckered little asshole.

“Oh!” the brunette gasped, “Ohhh…”

The singer smiled as she pressed her lips tightly around the tight little hole and began to suck on it.

“Oh wow…”

She pulled her lips away, savoring the taste of Haley’s ass, and started to press a finger against the hole.

“Ow…what… Ungh… what are you doing…”

“You have to relax,” Jewel soothed, or this is going to hurt. “Trust me.”

“Uhh… Okay…”

Jewel forced her finger into the tight little hole, sliding it all the way in with one quick thrust.

“Ahhhhhh!” Haley screamed.

Jewel pulled her finger out with one quick motion, and slid her tongue in to replace it.

“Mmmm… Yeah… That’s…. Ohhh… Nice…”

Jewel tongued fucked her, sliding her tongue in and out as quickly as she could. Finally, she was ready. Without any warning, she got up, and pressed the wet tip of her dick forcefully against that tight little hole. “This is going to hurt at first,” Jewel whispered, leaning down over Haley’s ear, “You just need to relax, and it will start to feel really good. Do you trust me?”

“Yeah,” Haley said meekly.

Slowly, Jewel used her dick to force Haley’s tight little asshole open. No doubt this was going to stretch her to the limit.

“Oh god!” Haley cried in pain as Jewel’s organ started to penetrate. “It hurts,” she grunted.

“It’ll pass…” She continued to force it in, watching the hole expand around her dick. She could hear Haley’s grunts and groans, but she kept going. It was amazingly tight in there, and it almost felt like it would crush her cock. The pressure and warmth sent a tingle up her spine to the tips of her nipples. “You’re so fucking tight…” she moaned, continuing her invasion.

“Ungh… Shit….God!” Haley screamed.

About half way in, Jewel decided to take it home. In one forceful push, she forced the last six inches of her dick into Haley’s virgin asshole.

“OH MY FUCKING GOD!” the girl screamed, obviously having crossed the language barrier. It was clear that she was in a great deal of pain.

Jewel slowly started to fuck her ass. Thrusting in and out, and before long her lover’s groans of pain turned into moans of pleasure. “You like that,” the singer whispered. “You like having your tight little ass crammed to the brim with my cock?”

“God Yes!” she screamed. “Fuck my ass! Fuck it hard!” Jewel obliged, ramming her ass harder and harder, each trust pushing them closer to climax. With one hand, the singer reached down to rub Haley’s sensitive clit. The other reached out, and grabbed her long hair, pulling her head back.

The singer fucked her ass for what seemed like forever, before leaning down and whispering in her ear, “Are you ready?”

“God Yes,” the girl whispered back. “Please fuck my pussy.”

“You got it girl,” She pulled her dick out, and positioned it at the gateway of Haley’s virgin womanhood. “Now, this is going to hurt at first too, okay, but than it’s going to feel really good.”

“I trust you…”

“All I needed to hear…” Jewel started to slide it into Haley’s pussy. It was very tight, and took almost as much effort as her asshole had. Then she felt the hymen. With one quick thrust, she pushed through the membrane, breaking it.


“It’s okay,” Jewel whispered, “That was your hymen…” She pressed in further, and started to fuck.

“Mm… Fuck me Jewel! Fuck me!” Jewel started to grunt as she rammed the girl’s tight little snatch. Faster and faster. Before long Haley was getting into it, pushing back in time with Jewel’s thrusts. “God! Think I’m going to…” As she climaxed, she felt Jewel’s warm sticky load filling her up, and felt the weight as Jewel fell down on top of her.

They lied there for a while, neither one paying much attention to the time. Occasionally, Jewel would lean in and kiss her, or lick some of the dried semen off of her face. Finally Haley broke the silence, “Thank you,” she said, looking into Jewel’s deep brown eyes. “I will never forget this night as long as I live.”

“Me either,” the singer whispered, leaning in for another long kiss. “We should probably get washed up before you go home. We don’t want your parents asking questions.”

“Don’t worry, I’ll keep your secret,” she said with a smile, and something in her dark blue eyes made Jewel believe it.

“Thank you,” she mouthed. She stood up, member hanging limply between her legs. “Now, why don’t we take a shower and get dressed.”

Haley stood up, finally allowing the skirt to fall to the floor. “I think that’s a great idea. I would love to take a shower with you.”

Hand in hand they walked into the bathroom. They showered together, washing each other and stealing the occasional kiss. Then they dried off, and got dressed. Jewel called the car around, and before she left, stole one last long passionate kiss from her lover.

When Haley left, Jewel sat down on the couch, thought lovingly about Ty and how lucky she was to have him, and started writing a poem. It was about Haley, and it was a poem that Jewel would never publish. Tonight would stay between the two of them forever.

The End

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