The Cherry Jubilee
by sevispac in collaboration with Jenna T
The Interview
We’re going to use her real name, Jenny, not her hooker name. She’s been working at the Phoenix branch of Her Daddy’s House Teen Bordello for almost a year, even though she’s just short of her fourteenth birthday, which means we can’t show you her picture. We interviewed her for our story about Teen Sex Today. Here is the second of our five part series:
Republic: What do you like best about working in a bordello, aside from the sex and the money?
Jenny: Believe it or not, I like being able to give back to my community. Her Daddy’s House really does believe in community outreach. This month we’re sponsoring the Cherry Jubilee. It’s a giant party for virgins of all ages - well, all ages past puberty - to help them get rid of their virginity and start enjoying life! I’ve been mentoring some of the girls that want to attend so they understand what to expect, and I’m volunteering to have sex with any of the boys that don’t want to fumble around with another virgin for their first time.
Republic: So you’ll be fucking them for free? Isn’t that a no-no for a girl in your profession?
Jenny: Well, I’m hooking to make money, but that doesn’t mean I can’t have sex for fun. Plus which, lots of the boys come back later as customers.
Republic: What about the girls?
Jenny: (giggling) Sometimes! but we’re always hiring, so they’re more likely to be selling!
Republic: Tell us more about The Cherry Jubilee.
Jenny: It’s next Saturday night. It starts at 10 o’clock and goes on all night. It’s free for virgins, and if they’re scared to join in they’re welcome to just watch. Then if they change their mind they can join in later. We cover the main ballroom with couches, bedding, pads, pillows, and everything to make it comfortable. We have experienced volunteers like me help the ones who are too shy to play with each other, but they usually get over that pretty fast. They can stay all night and they’re only virgins at first. The ones I’m with learn fast. Her Daddy’s House provides a live band in the ballroom, and private rooms for the shy kids, but everything gets video taped. Everybody gets a copy, but we usually make a profit after we post it on our porn site.
Republic: That doesn’t sound much like public service.
Jenny: Oh it’s a service, alright! (giggles) Remember, I’m doing it for fun, and it’s free for all the participants. Some of them even get discovered and go on to careers in porn!
Republic: Is it true there’s free food and alcohol?
Jenny: Of course, silly! We always have a free buffet and an open bar. That’s another thing I like about living here.
Republic: And is there any truth to the charge that the food is drugged?
Jenny: Some of the girls think so. They say that’s why we’re always so horny. But I’ve always been that way. Anyway, it’s easy to get anything you want to party with here anytime. (winks)
Republic: Sounds like a great job.
Jenny: Well, some people think you and I are in the same business.
The Favor
“You wanted to see me, Miss Wilcox?”
Charlotte Wilcox looked down at Frankie. She was pleased with the way she’d grown in the last year and a half. Frankie wasn’t so pudgy any more, and what little remained of her baby fat had settled into the right places. She couldn’t button the top button of her Girl Scout vest any more, and the second button was getting too tight.
“Yes, Frances. I want to talk to you about The Cherry Jubilee. Since you don’t have your ‘V’ pin on your VOA badge, you’re eligible to attend. Are you planning to go?”
Since Charlotte had helped Frankie discover her talent for oral sex, she’d blossomed from a shy, overweight wallflower into a cute, fun loving little Lolita. Charlotte had watched with pleasure. She was a committed Scout Mistress and took delight in seeing her girls develop into sexually active little nymphettes.
“I’m not sure,” said Frankie. “I want to, but I don’t know if my parents will let me.”
“Why don’t you pick up one of the brochures so they can read all about it. I bet if they see that it’s a safe, fun party right here in Her Daddy’s House they’d be glad to let you attend. Be sure to tell them that everything gets recorded on video and they’ll get a free copy afterward!”
“OK. They’ll be here to pick me up at 9 o’clock. They didn’t know the meeting was going to get out early.”
“Oh. All right. While you’re waiting you’ll have time to talk to Jenny here. She’s just about your age and she can answer all your questions. And if you’re interested she can tell you all about getting a job here. And don’t forget, you can earn all sorts of Merit Badges at The Cherry Jubilee.”
Frank Advice
I asked Jenna T what advice Jenny would give to Frankie about The Cherry Jubilee. (Jenna’s response looks like this):
She would suggest diving in head first and throwing caution to the wind....though I doubt Frankie would do it.
If you're going to go there, it makes no sense to do it half assed, especially since it would make sense that (since it is for virgins) the inexperienced girls and boys there are probably going to go in the same timid things as they've always been and make it the biggest group of wallflowers you ever saw until the ice breaks. The ice breaker might as well be Frankie. :)
What would I want to hear if I were in her position?
That isn’t at all where I was going. It was better. Here’s what Jenny said when Frankie asked her what to do at the Cherry Jubilee:
"Walk into the lobby and split your cherry open on the first hard cock you see and leave that little burden as a red stain to be mopped up by the janitors. After that, dive in literally head first and lick every unattended cock or pussy you can find. Better yet, sheath every cock you can get so you can find out what fits you best AND so you can lovingly force those virgin boys into the manhood they've been denying themselves. As far as pussies, burst what cherries you can but leave some for the cocks. Either way, don’t go home anything less than caked in cum and pussy juice."
Thank you for those words of wisdom, Jenna. This raises the intriguing question: Will Frankie do it?
The Invitation
Miss Frances Cunningham
1232 Horizon Rd
Chandler, AZ
Dear Miss Cunningham:
We are pleased to enclose your invitation to The Cherry Jubilee at Her Daddy’s House Teen Bordello, 1521 48th St, Phoenix, AZ, starting at 10 pm on Saturday, June 21. Also enclosed is your Cherry Pin, personally engraved with your name on the back. Please be sure to bring both the invitation and the pin, because both are required for admittance.
- Breaks your hymen with his penis, or, if your hymen is already broken,
- Ejaculates into your vagina for the first time.
Please check your pin to confirm the correct spelling of your name, since it is likely to become a treasured keepsake of its ultimate claimant. Also note that it is designed for several possible methods of display depending on your personal desires and availability of clothing. It can be pinned to your outer garment (if any) or worn on the enclosed chain as a necklace. In addition, it can be affixed to most types of piercings using the eyelets provided. This is a popular method of display, and we recommend titty or horizontal clit piercing displays, with the caveat that they must be visible when you enter the facility and at all times until they are surrendered.
Regardless of your status as a virgin, you are qualified to claim Cherry Pin(s) belonging to any man or boy you have sex with if he is a virgin at the time. Please note that this is a one time opportunity for all concerned. Most Cherry Jubilee participants go on immediately to a wide variety of partners and kinds of sexual intercourse, often resulting in hazy memories of exactly who did what to whom. This should not be a concern, because we are careful to record all sex acts on video for your later enjoyment.
We’re proud to provide an extensive, all night buffet and unlimited open bar continuing through the night until nominal closing at 7 am the next morning. We emphasize ‘nominal’ because many of our participants end up sleeping well into the following afternoon and are welcome to stay until they are ready to leave. And girls, if you’re under the age of 20, Her Daddy’s House is always looking for new, live-in employees!
We also want to remind you that there will be live music to accompany the main orgy in the ballroom, and private rooms for those who are shy about public displays of affection. In our experience, participants quickly loose their shyness after one or two enjoyable encounters, so we encourage you to share your activities with as many partners as you desire. We believe the more truly is the merrier!
Finally, congratulations on being invited to The Cherry Jubilee, and we wish you a joyous experience on what may well be the most memorable night of your life. We hope that it will be the beginning of a long and fulfilling sex life for your and all your future partners!
The Cherry Hop
Jake
Some people might say it’s funny that I’m here tonight. Me, a 19 year old male virgin at a party the parents throw for their kids before that orgy they call The Cherry Jubilee. It’s funny because my mom wanted me to go. Yeah, I have to admit I was tempted. Who wouldn’t be tempted by a room full of naked girls eager to lose their virginity, even if most of them are six or seven years younger than me? Not all of them, though. There’s a blond here who’s 24! And here I am, but not for the party.
Never mind. Best not to think about it. I’m here because I work at Food Fresh Express, ‘cause we were hired to cater The Cherry Hop.
It’s fairly innocent. A lot like Prom, including what usually comes afterwards; except at The Cherry Hop everybody knows the kids are going to get laid instead of just suspecting they will.
My name’s Jake. Like I said, I’m here to cater for FFExpress. Let me tell you, it isn’t easy holding onto my principles when I’m surrounded by horny little virgins who know they won’t be that way for long (Virgins. Not horny.) But I made a promise a long time ago before True Love Waits got subverted and perverted, and so far I’ve kept it.
It hasn’t been easy. Thank God I’ve got a break coming up and I can get away from the dance floor, eat some dinner and maybe cool down a little. Thank God we don’t cater the Jubilee!
...
Mary
It isn’t as bad as I thought. I never wanted to be here, and I still don’t want to be here, but at least people aren’t making fun of me. That’s not something I’m used to. My little sister Margie is the worst. Ever since she went to The Cherry Jubilee last year I’ve had to listen to her tease me about the fact I’m still a virgin, even though I’m 15. Well, what’s wrong with that? It isn’t like I’ve never been kissed. I have a boyfriend. I go to dances and movie dates. Just because I haven’t let a boy fuck me doesn’t mean I’m a bad person. And I’m NOT scared, either, no matter what Margie and all her bratty little friends keep saying. Mom and dad pretend that they don’t hear her, but I think they secretly agree. And now even my friends are starting to make fun of me!
I’m tired of it, so here I am at the hop, getting ready for my big night. Danny wasn’t invited, because he didn’t meet the main requirement. I don’t understand why, because they have ‘helpers’ to take care of us if the other virgins are too shy, but for some reason they wouldn’t let Danny sign up. Well, he was glad I was going anyway. He knows if I like it he’ll be getting what he’s wanted ever since we started dating.
Mom and dad made a real production of it. This gown alone cost them almost a thousand dollars. I love it, even though I would never have worn such a thing anywhere else. After they took me to get my hair done at The Purrfect Pussy they said I had to have something to show it off. I guess they’re right. I have to admit the little butterfly shape looks great on my mound, and the waxing just hurt so much I have to do something to make it worth while. I haven’t passed a single boy who didn’t stare. It’s embarrassing, but I guess it’s kind of fun, too. Anyway, guys keep asking me to dance, and I love to dance. Never mind they keep rubbing their cocks up against me. I can’t really object, the way my gown leaves my pussy bare, it’s an open invitation. I guess it’s kind of fun, too.
8:30. Just an hour and a half left before the Jubilee. Maybe it won’t be too bad, but I’m getting out of there just as soon as I surrender my pin.
All I want is for Margie to shut up.
Cold Feet
Mary
Okay, I was pretty horny when I got to the Jubilee. Besides dancing with a dozen different boys and getting felt up on the dance floor, I know they spiked the punch at the hop, and I got into the Limo feeling a very pleasant buzz, both in my head and my pussy. There was more champagne on the ride over, and the bench seats were set up so the passengers faced each other. The boy across from me was in my homeroom, and he was openly rubbing the bulge in his pants while he stared at my pussy for the entire trip.
The chaperones made sure we didn’t drink too much. It wouldn’t do to pass out before we got to the Jubilee. The girl sitting next to me was playing with the boy beside her with her right hand, but she put her left hand on my leg and started caressing my thigh. Normally I would have slapped her hand away, but tonight if felt really good. And besides, she wasn’t actually touching my pussy. I kind of wanted her to, but I was embarrassed to ask her.
By the time the Limo pulled up to the red carpet outside Her Daddy’s House I was looking forward to what was to come. The local press was there, interviewing the attendees like it was the Oscars. I was too shy to talk to them, but of course they focused on my gown. I blushed bright red, but really I kind of liked it.
The eight of us from the Limo all walked in to the ballroom together. Except for one boy who must have been over 18, I was the oldest, but nobody else looked as nervous as I was. The boys were gazing around at everything that was going on, and the girls were looking pretty eager, too. I started to hang back in the group. I couldn’t believe the things I was seeming. All over the room kids younger than me were doing all kinds of things I had never even heard of. Kissing, fondling, pulling off each other’s clothes... Over on the dance floor they were fast dancing. Most of the girls were topless, and they were rubbing up against their partners. Everywhere on the couches, carpets, chairs were kids partly or completely undressed, playing with each other’s bodies or just frankly fucking.
An older boy spotted me and walked over. He was way taller than me and wearing a suit, but he’d loosened his tie and unbuttoned his collar. “Hi, I’m Glenn. Wanna fuck?”
He wasn’t wearing a cherry pin. It was too much, too fast. I shook my head and shrank back, walking into a chair. My knees gave way and I sat down hard. He smiled. “Sorry, I didn’t mean to scare you. Did you just get here?” He noticed my cherry pin.
When I didn’t reply he smiled and reached down to the zipper of his pants. As he lowered it I was literally faced with the first cock I’ve ever seen so close up. It was huge! There was no way that thing was going to fit inside my little pussy! Suddenly all I could think of was how much it was going to hurt, tearing into me. What had I gotten myself into?
I was trapped. The chair was overstuffed and hard to get up from, and he was standing there blocking my escape. Behind him, a girl in a scout uniform was enthusiastically sucking on a guy’s cock while jacking another off with her hand. I’ve always been disgusted at the thought of touching a penis, let alone putting one in my mouth. It’s so dirty!
It really is dirty, too. Guys use it to piss, not to mention they want to put it up into where girls pee. And some guys even want to put it in our ass! That’s not even counting the kinky hair all over it or the sweat and muck if they don’t wash it. I can’t understand why any girl would ever do that! I’ve even heard of girls letting two guys go into them at the same time!
But as disgusting as it was, it was the only way I could think of to save my cherry from a very painful tear. As the boy started to rub himself against my pussy lips I reached out and took his shaft in my hand. I was a little surprised at how smooth and warm it was. He let go when I shifted forward in my seat and brought my lips toward the little slit at the top of his dick.
...
Jake
It was just like waking up in bed, except I couldn’t move or see. I could feel the sheets and the pillow, so I had to be in bed. My legs and arms were stretched out but I couldn’t feel anything like a rope or handcuffs, just something soft and smooth holding me spread-eagled on the bed. My eyes were open, but I must be blindfolded because everything was dark.
The last thing I remember was eating dinner in the kitchen at the Cherry Hop.
“Hello,” I called out, “is anyone there? Help me, please!”
The bed moved slightly, so I knew someone was there. I could feel I was naked, and I began to be really scared. What in the hell was going on?
“Hi, Jake.” It was a girl’s voice. A young girl, probably a young teenager. She seemed to know me and she sounded familiar, but I didn’t recognize her voice. Still, she sounded reassuring and my mounting fear began to recede.
“Remember me?” I felt a hand brush my face and pull away the sleep mask that had been over my eyes.
“Jenny!” It must have been at least two years since the last time I’d seen her. Our moms were old friends. It’s not quite true to say we grew up together, but her mom used to bring her over pretty regularly. She’s about five years younger than me, so we didn’t play together, but she was a sweet little girl and I sort of liked having her around. I always wondered why her mom stopped bringing her over.
My fear vanished, even though I was lying tied to a bed in a girly bedroom. Did I mention Jenny was wearing a miniskirt and stockings, but no top? That would explain the fact that I had a raging hard-on sticking up from my crotch, but not how it got that way before I actually saw her.
“Welcome to the party, Jake.” She smiled at me from where she was sitting, next to me on the bed.
“Just what do you think you’re doing? Untie me right now! How did I get here?”
“Relax, lover, you’re in good hands,” she said, reaching out and grasping my cock with her soft fingers. “I’ve been wanting to have a quiet talk with you for a long time.”
I was confused, outraged, and still a little scared, but her hand felt like an electric coil around my dick. I groaned loudly as an orgasm wracked my entire body. Jenny reacted with the grace of a ballerina, thrusting one slender leg across my waist as she pulled my rock hard cock to leverage herself into position. Before the first blast came rocketing out, Jenny had pushed the head between the lips of her panty-less, slick pussy and thrust herself down to meet the erupting geyser. “Ahhhh-yyyyeeeee!” she screamed as she expertly transformed my unexpected ejaculation into a mutual explosion of lust. Her entire body bucked as she made up for my enforced restraint while my virginity flooded out of me and into her slurping cunt. Her violent motions lifted her completely off my gushing hose, but her incredible talent brought her pussy crashing back down to engulf me again every time! On and on she bucked, bounced and bobbed while I thrust myself up to meet her again and again. In the end she collapsed on top of me, her soft little boobies crushed into my chest, her soaking wet skirt nearly coverng our entwined genitals, and her sweet, innocent face pressed against my shoulder.
My emotions were going crazy. Love and hate, outrage and acceptance, joy and sorrow. If I could have embraced the darling little angel who was now lying helpless on top of me while her pussy sheathed my still rigid cock I would have done so, but the scarves that bound my arms and legs to the bedposts dictated otherwise. As my exhaustion dissipated (admittedly starting in my penis), my outrage rose again.
“Just what the hell did you do, you little brat?” I demanded. “This is rape, you know. You could go to jail for this. And even if you don’t, what do you think your mother will say? What will MY mother say?” She shifted slightly and raised her face to look in my eyes, but she gave a most amazing twist of her hips that brought life back to my wilting cock. We looked at each other.
She gave me a naughty little girl smile, one I remember from when I was supposed to be baby sitting her. “What would YOUR mother say?
“... how do you think you got here?”
Epilog
Mary
I found my gown and used it to wipe off some of the fresh cum before I stumbled out to the desk, naked. “Hi, can you call my parents and ask them to come pick me up? My name’s Mary Reynolds. She looked at me in surprise.
“Oh! You’re Mary. I have something for you.” She reached behind her desk and pulled out a leather bag. “I’ll need you to count that and sign a receipt. There’s $1,543 in there.”
“What? There must be some mistake. I don’t work here, I was just here for The Cherry Jubilee. What time is it anyway? I must have slept all morning.” I was groggy and couldn’t remember a lot of detail about last night. But I sure did remember a montage of cocks in all sizes and shapes and in all times and places. The memories were coming back.
She was grinning at me now. “It’s only 8:30 in the morning, but it’s Monday, not Sunday. I’m supposed to tell you that your parents came to pick you up yesterday morning, but you were still... busy, shall we say? It seems they didn’t want to disappoint the boys and girls in line waiting for their turn with you, so they asked us to let them know when you were finished.”
Even after everything I’d done in the previous, uh, 24? no, 36 hours, I was shocked to hear that my parents had been there to see it. She must have been able to guess from my expression, because she said, “Oh, don’t worry! They thought it was great you were finally getting over your shyness and starting to enjoy being a girl. Gang bangs will do that!” She giggled, and so did I, as much out of relief as amusement.
She was still smiling when she stopped giggling. “Anyway, after everybody finished you passed out from exhaustion and we just let you sleep. I’m not sure what happened after I went home, but when I got back on Sunday you were fucking in the ballroom again. Lot’s of our regular customers saw you and asked if they could join in. Are you sure you don’t remember this?”
I did remember a haze of sexual excitement that seemed to go on forever. I remembered how it tasted when that first boy came in my mouth. And I remembered that sexy little Girl Scout and the great way she could suck one guy after another. And how she got in a contest with me, both of us squirting cum on the other as we sucked and jacked off boy after boy, until she starting licking my still-virgin pussy. Guys were standing there shooting their loads all over both of us when one grabbed her and another grabbed me and they both started fucking us side by side on one couch. And yes it hurt. Bad. But only for a few minutes. By the time he unloaded his spunk way up inside my pussy and made off with my cherry pin I was permanently addicted to fucking. From there on it was a blur of cocks and pussies, cum and girl juice, in me, on me, everywhere. But there was something else nagging at me, something I didn’t quiet remember yet.
“So anyway, you made quite a bit of money after the Jubilee was over. You mean you didn’t realize what was happening?” I shook my head, trying to get my mind around the last two days. Whatever I was trying to remember was part of the haze, but I know it happened in the daylight, so it must have been yesterday morning. I came and came and came hundreds of times in the last two days, but sometime yesterday morning was the best of all, the orgasm that made me a permanent slut, and now I remembered: I got off from being licked even more than from being fucked!
“Oh, and we have something else for you, too.” She handed me a plaque. It had five cherry pins neatly embedded in it, next to engravings of the names of the former owners. “It was a special night for a lot of kids, but we thought you’d want to have a keepsake. There are five guys on here who will always remember you.”
And I’ll get started on trying to remember them, too, I thought.
She handed me the bag with the money. “I’m really not sure if I should take this,” I said, “people might think I’m a whore!”
She giggled again. “Well of course, silly, that’s what being a whore means! Take the money. You earned every penny of it, and we have the pictures to prove it!
“One last thing,” she said. Don’t forget she needs a ride, too. She’s in room 12.”
“Who?” I asked, puzzled. She started giggling so hard this time that she couldn’t answer. She just pointed down the hall.
I had recovered enough to walk without stumbling, but I didn’t bother knocking. The two girls on the bed didn’t take any notice of me as I opened the door, they were too busy licking each other. But then the one on top looked at me and the memory of my earth shattering orgasm on Sunday morning came flooding back. I had been in the middle of a gang bang when I felt a soft wet tongue on my sloppy, sore pussy. That’s when I looked down and saw the cum covered face of my little sister,
“Margie!”
---
Jake
So The Cherry Jubilee changed my life even more than most, and even though I tried my best not to go. Jenny was oh-so-kind enough to untie me before she went off to tend to her duties as a volunteer. Before I headed out to the ballroom looking for other lives to change, we had that quiet talk she’d been wanting for so long. She explained to me how our moms had gotten to be such good friends, and why we played together so much when we were little.
You see, her mom was a very well known and much sought after hooker. She’d been grooming Jenny to follow in her footsteps, and Jenny had been a natural for the job. The day finally came when Jenny hit puberty and was ready for the life. But what her mother hadn’t planned on was her precocious little girl wanting to get a head start.
“I’ve had a huge crush on you ever since I can remember,” she told me. “Last time we were alone, in May last year, I was trying everything I could think of to get you to molest me. But I just couldn’t come right out and ask, and you were too much of a gentleman to figure out why I kept sitting on your lap.”
Yeah, I was that stupid. It never even occurred to me that little tart really was asking to be fucked. I thought I was the one who was too horny!
“So how did I get here?” I asked her.
“That’s not so simple. First you need to know that your mom and mine were friends because they used to have the same job. But your mom quit about the time I was born, when you were still too little to remember. Mom says she still sees some of her favorite clients for old times sake, but she’s not a professional girl any more.”
By this time I was getting numb to shocks. There didn’t seem to be any question that Jenny was telling me my mom was an (ex?) hooker. Well, she certainly had me fooled, but I guess it explained some things about my beautiful, elegant mom who was financially very well off for no obvious reason. It also explained why mom made so many “business trips” out of town, especially on weekends. I had wondered a little bit about that. And she was only in her mid thirties.
“Anyway, your mom was disappointed that you weren’t getting more fun out of life, especially when my mom was bragging about me.” Did she blush a little when she said that? “So when she couldn’t talk you into attending The Cherry Jubilee she got with us about what to do. That’s when we brought in daddy.”
“I didn’t think you knew who your daddy was, any more than I do.”
She chuckled, then turned serious. “Oh but I do! He’s always come to visit me and mom. I love him bunches. He’s rich, and he owns all sorts of businesses. For instance, he owns Food Fresh Express.”
Light began to dawn.
“So when mom asked for help, he was glad to set you up to work The Cherry Hop, and it wasn’t any trouble for him to make sure you got a very special dinner. After you passed out you looked like just another drunk kid who needed help getting to the real party. A couple of his guys brought you over and helped me tie you to the bed, and that’s how you got here.
“Oh, I almost forgot to mention. He also made sure you got a very strong dose of Viagra with your dinner. That’s why I wasn’t too surprised by your reaction.” She wasn’t so serious anymore. In fact she was grinning from ear-to-ear.
“Wow. That’s a lot to take in. Any more surprises?”
“And one more thing, Jake...
“...It’s also YOUR daddy’s house.”
And that’s the story of how I lost my virginity to my very own sweet little sister.
