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"I've no idea. But I want her to get married, have kids, a successful career. Everything. Do what you can to help."
"Just like our business is going to be. Get middle class mothers to pay us to train their daughters. What was it you said. Get married, have kids, a successful career. That's worth a lot of money."
"I guess you can try with my daughter. See if it works at all."
"She needs to learn how to do stuff that's not on her phone. Does she have a driving license?"
"No."
"Does she have a Tinder account? Or Bumble? Or anything like that?"
"Maybe. I don't have a clue to be honest."
"Is she a virgin?"
Kathy gasped. Then paused. Then said "I've no idea. She's never been out on a date, that I know. But maybe she fucked someone when I was out at work."
"Boy or a girl?"
"I never considered girls, just boys, but who knows?"
"So she's our prototype. The first of hopefully many. Although maybe she's too close to home, and we should pick someone unrelated. I mean I don't want to have to do reports for you about your daughter for the spreadsheets. Maybe better if it is a more random stable-girl."
"I guess. But I do want her to get trained. I just don't want to hear all the details."
I laughed. "You don't want to know about your daughter's vagina?"
"Oh my god no. I spent enough time cleaning it up when she was a baby. I don't need to see it again."
"You've an MBA right?"
"Yes. What's that got to do with anything?"
"We could really do this. The stables are the perfect cover for letting ambitious parents train their Gen-Z daughters how to interact with men, or girls for that matter, and deal with dating and sex. Become adults. Everyone thinks they're learning to ride, and some of the time they are, but we are also training them in how to live life the way millennials and baby-boomers did. That somehow the youngest generation has never discovered because of too much social media. We could make a real business of this. After all, one thing you will not do riding a horse is be on Instagram."
"Are you going to fuck them all?"
"You want me to fuck your daughter?"
"Sorry, I was in MBA mode. Business plan. She was just a cell on the spreadsheet. But she's old enough, and it's her body, so it's up to her, not me."
"From my experience here in the stables, young-women today are not comfortable with men at all. I think we need to start with girls. They are so much less threatening. And the stable is full of girls. The girls that look after the horses, the instructors for the clients, even the clients, they are basically all girls. My spreadsheet of our employment statistics is close to 100% females."
"But they're all straight!"
"I have a lesbian friend who explained this stuff tuff to me. Almost all girls are somewhat bisexual, she said. Lesbians even have a term for getting a straight girl into bed. Bending her, they say. Apparently, it's not that hard. Like breaking a young horse."
"I've never heard that."
"Have you heard the term LUG? It means Lesbian Until Graduation. Girls have female-female sex through college, often with their roommate, then graduate, get a career, get married, and have kids. And never see a pussy again."
"Wow, I had no idea. In my generation, we just fucked a lot in college."
I laughed. "Mine too. Although as a a guy it was always a challenge to find a willing girl."
"You just had no idea how willing all the girls were. We all wanted to be fucked."
"I'm thinking on my feet here, but I think we need to train some of the girls who work here to be the breakers. The most important thing is not the sex stuff, it is being face-to-face with another person without being freaked-out. If it is a girl, that maybe works more smoothly."
"I guess. The yard-girls are less threatening than you."
I laughed. "Lesbian until leaving the stables."
"Gosh, this is starting to feel depraved."
"If we decide we want to teach them how to suck cocks we can worry about that later. I only have one cock so we will need to work out how to ‘scale' as the venture capitalists like to say."
"And teaching them to go on dates. Gosh. We need lots of young men. And there are next to none at the stables."
"We can train them to use Tinder to get men, then write all their texts for them. Send them on a date as if we are putting a ship to sea."
"Let's develop a plan. And a business model."
"It will be complicated," Kathy said. "Part of the offering is to be very discreet. But if we're too discreet we won't get new clients. But we don't want it to be all over social media as...well training the daughters of the area to fuck. How do we train them anyway?"
"Let's split things up. You do the business stuff, find new clients, collect the money. And I handle the training."
"Okay. I guess I can start with the parents of my kids' friends. They have younger daughters too. In time, they will grow up and be ready. Gen-Z or whatever comes next."
"We need to keep legal," I said.
"What do you mean?"
"We have loads of fourteen-year-olds learning to ride. But we can't take their panties off. Too dangerous legally, even if they would love it."
"They would. They all watch porn."
"How old were you when you first took your panties off?"
She laughed. "Fourteen."
"Wow, that's young. Did you do it?"
"Not full sex. But...let's say he got to see and touch everything down there."
"So I train the girls?"
"Yes. I'm the business manager. No panties off until they're legal. But how do we proceed then?"
"How about this for training a girl in the stables. Critique me as if I was doing it to teenage you. First question: what color are your panties?"
"Oh my god, I'd have been shocked if you asked me that in my late teens."
"Would you answer?"
"I guess eventually. It's a semi-innocent question."
Second question: prove it. Not really a question I know, but she, you, has to open up her riding pants to show the top of her panties."
"I'm liking this idea."
"Third question: well, not a question. Just take your pants off."
"So she'll be naked below the waist?"
"Not quite. If she dares to do it she'll still be in her panties."
"Wow."
"Fourth question. Are you shaved?"
"I've heard almost all girls are shaved these days. From watching porn."
"Are you?"
She laughed. "That is out there, you perv. But no. I still keep my hair."
"Next step, after asking if she is shaved or hairy is to get her panties off."
"You have no idea how terrifying that is for a teenage girl."
"Not as terrifying as the next thing. So I ask her to take her panties off."
"And she does?"
"Who knows? We're building a script here. Like an airplane landing checklist. Autopilot off. Wheels down. Flaps 15."
"Panties down. Lips 15."
"You're as bad as me," I said smiling.
"So we ask her to take off her panties. What next?"
"What do you mean by ‘we' here?"
"I guess the first time it will be you."
"Yes. The first time I guess it will be me. But we have to train the stable girls and riding instructors to do it too. So we have lots of parents paying and can make some money training their daughters."
"How about we ask them if they are VWMs, virgins-who-masturbate?"
"No, Kathy said. No girl will admit to that."
"Why?"
"Because in this day and age being a virgin seems like a failure, and no girl wants to admit she masturbates even though they all do. Porn on their phones and stuff."
"So next question: do you know what masturbation is? She will say something like: Yes, they told us in health class."
Then I ask: "Do you do it?"
The answer will be either ‘yes' or they will lie and say ‘no'.
"And if they say no?" Kathy asked.
"I don't know. I'm making this up as we go. But how about asking her if she knows how. I mean if you have a vagina and a hand, it's not that complicated."
"Next question is to ask her if she does it. Is she a VWM?"
"This is so scary. I've never even masturbated for husband."
"If you did it for me...or one of our girls...you'd trust me totally. It takes so much nerve to do it that you are totally committed if you do."
"Gosh, really?"
"I'm just guessing. Only that one girlfriend has ever masturbated for me. But, in some ways, it was the most intimate thing anyone has ever done for me."
"Like I said, I've never even done it for husband."
"So I tell her this is the most difficult thing she'll have ever done in her life. I ask her if she is up for it. She'll say she doesn't understand since she doesn't know what I'm going to ask."
"And you make her do it in front of you?"
"Yup. Is that too extreme?"
"It's very extreme. Imagine. You're at community college or wherever. You come to the stables for a riding lesson. And suddenly your riding instructor is making you take off your clothes and masturbate for her."
"Have you ever seen a girl do it?"
"Never. I've never seen another girl down there. I mean I've been in locker rooms at gyms, but you just see the top of the slit if she's shaved, and just a patch of hair if she isn't."
"I had one girlfriend who liked to do it for me. But mostly girls find it too embarrassing to do. You'd probably fuck me before you'd masturbate for me. And you're grown-up. Eighteen-year-olds are even more self-conscious, especially if they're virgins. They know how sex works from school sex-ed classes and porn, but they don't know how exhibition-masturbation works."
Kathy laughed. "Is that a phrase?"
"I've no idea, I just made it up."
"But that's who we need," Kathy said. "VWMs, virgins who masturbate. A good compromise. If they are already fully sexually active there is not much for us to add, they have started to get their lives together. If they haven't discovered porn on their phones and masturbation, they will take too long to train. VWM is the perfect combination."
"Were you a VWM when you were in your late teens?"
"You can't ask me that."
"If we're going to be business partners in training girls to be less social-media-heavy we can't have secrets about what we did. It's the basis for working out how to build the business. Especially your experience. Men will fuck anything that moves, so it's all about the women."
"Okay. Yeah. I was a VWM. In middle-school to be honest. When I went to college, I had boyfriends. So I was just a...whatever...student WM."
"Are you a wife WM?"
"Occasionally. I mean I get regular sex. But sometimes I do it when he's not around. Or just in the shower."
"So how do we find lots of VWMs?"
Kathy laughed. "You're smart, but sometimes you're slow."
"What do you mean?"
"This is the brilliance of this business model. You have a whole stable of VWMs. Literally a stable. I mean some are probably not V and some may not M, but most of your whole payroll here at the stables are VWMs. And most of your clients."
"Is your daughter Sandy a VWM?"
"I've no idea. I'm pretty sure she's a virgin still. And masturbation is not exactly an over-the-dinner-table topic. Especially with husband around. But she's smart, and got a phone, so I'm sure she's discovered it. So if I had to guess, she's a VWM."
"So how do we do this? Convert VWMs to trainers for our new clients."
"We need a training program. Like we are corporate."
"So we need two phases. The first when the stable girl gets...broken...in horse terminology. Then we train her to break new girls. We break the girls we employ and then they break the clients' daughters."
"Perfect. This might actually work."
"Can we make money?"
"Give me a few days to talk to the parents of some of the girls who are learning to ride horses."
"To find out if we can make a business of teaching their kids to ride cocks."
She laughed. "You can be so crude."
"I know."
"Here's how the business will work, I think. We take in little tweenagers like your stable has done for years. V who don't yet know how to M. They grow up. They learn to M so they become VWM. When they are old enough we break them. And then...I don't know. We need to have a program after they are broken. Getting a driving license. Using Tinder. Going on dates. Creating a résumé. Job interviews. Everything a young woman needs."
"So what is the key to break away from TikTok and Insta?"
"To masturbate in front of her trainer-girl. It will be the hardest thing that she's ever done. And after that she will trust the trainer-girl completely."
"Let's recruit your daughter to help. She's the right age demographic."
"I can't talk to her about this sort of thing."
"Okay. I'll try running the script on her and then we can all work to improve it."
Chapter 2
Kathy's daughter Sandy came into my little office. She was a student at the local community college but also rode horses, was one of our teachers, and was learning how to show jump.
"You wanted to see me," she said. "You and my mom are up to something."
I got up and closed the door. "Do you really want to know? Can you handle the truth? Like in that movie."
"Let's see if I can. Tell me."
"Let's start with the basics. Are you a virgin?"
"What?" she gasped.
"It's a simple question. And most Gen-Zers are virgins until much later than used to be normal. Compared to earlier generations. So I'll take that as a yes."
"OK," she said. "I am."
"Next, do you masturbate?"
She gasped again. "I have to talk about that?"
"You're a Zoomer. You had a smartphone from when you were in middle school. You discovered porn, I'm sure. I think you can do the math."
"Yeah. I've done it for years."
"Five vegetables a day."
She laughed. "Not that much but...let's just say...most nights before I go to sleep."
"So you're a VWM. A virgin who masturbates."
"I guess."
"Do you want to do the whole program your mom and I developed. Well, mostly me. It will be scary. If you start, I want you to try to commit to finish. Obviously, you don't need to do anything you don't want to, but it is important to go the whole way. Then you can help improve the program."
"Okay. I have no idea what I'm signing up for but I'm not naïve. I know it will involve some sex stuff. Do I have to fuck you?"
"No. I can't fuck all the stable girls, there are too many. The business can't work like that. I want your help improving how the business works. But first you have to go through it."
She sat down on the chair across my desk. "I'm ready," she said. "Don't be rough, as the saying goes."
I decided to run our script and see how well it worked with her. "What color are your panties?"
"Gosh. That was not what I was expecting. I guess I have to answer. Red."
"Prove it."
"What do you mean?"
"Open up the front of your pants and let me see the top of your panties."
"This is so weird. You're one of my mom's best friends and I'm opening my pants for you."
She undid the little button on her jeans, and slid the zipper down.
"I did not lie," she said as she opened up the vee to show the top of her red panties.
"Are you shaved or are you hairy?"
"Oh my gosh, I've never had a conversation like this. I shave. I think most girls do. I guess we are copying the girls we see in porn."
"Prove it."
"You mean take off my pants?"
"Yes."
"This was not what I was expecting to do today. Okay, here goes."
She stood up and slipped her riding breeches off.
"Behold my red panties," she said, holding her arms out wide.
"Take them off."
"I guess I committed to go through with this so here goes."
She stood up, pushed her panties over her hips and let the fall around her ankles. She kicked them away..
"This is a first," she said. "Nobody's ever seen it before."
"What do you call it?"
"My pussy, I suppose. But I don't recall ever talking about it."
As she had implied earlier, she was shaved. She had an innie. Big fleshy lips with no hint of the folds lurking within. Just a long gash below her belly.
"Spread your legs and show it to me properly."
"Gosh. I'll try. This is so extreme. Even I can't see down there. I needed to use the camera on my phone to see what I looked like."
She sat down and then slowly opened her legs. Her pussy spread partially open and I got to see the hint of the pink petals within. Fleshy outer lips and a little of her labia peeking out.
"Is it okay?" she said. "I've never seen another one."
I laughed. "You've been watching porn for a decade. You've seen thousands of pussies."
"Yes, but nobody's seen mine until now."
"It's perfect," I said. "Mother nature gave you a pretty one."
"Good. Girls are all worried they're deformed. It looks so weird when you put your phone down there. A sort of sea anemone lurking out of sight around the curves of your body."
"The giant squid between your legs."
"Now you are teasing me. Please don't. We girls are so sensitive about the stuff down there."
"Show it to me. In its full glory."
"You mean open it all up? Let you see inside. Like a butterfly spreading its wings."
"Yeah."
She reached down with both hands and put a finger on each outer lip. Then she spread them wide apart to reveal the pink folds inside. I could see the sheen of moisture from her excitement. Or terror. I had no idea if she was excited or terrified. Or probably both.
"Now I want you to do the toughest thing you've ever done in your life. Masturbate for me."
"This is going too far. I'm not sure I can do that."
"You're a VWM so I know you know how to do it."
"Yes...but...this is too personal. I've never done it with anyone watching."
"You committed to try to go all the way," I said.
"Okay, I'll try. But this is out there. Maybe I'll flame out. Not be able to do it."
"You mean not be able to cum."
"Exactly. You know me. If I'm going to do this, I want to do it properly."
"And that means orgasming?"
"Exactly. Well, here goes."
She reached down and put a hand on her pussy. She started to rub it. I could see a finger slipping between the lips into the cleft of her sex. She closed her eyes and, I assumed, tried to forget I was watching.
She reached down with one hand and spread her pussy lips so her clit was accessible. I have no idea if that is how she normally masturbated, of if she was aware she was putting on a show for me.
She ran a finger the length of her slit, from down near her asshole up over her clit. She let out a little moan each time her finger passed over her clit. Her fingers started slowly, along with her breathing. But gradually both sped up.
She made no effort to tell me when she came. It was just obvious. She was rubbing her pussy hard, moaning loudly. She focused on her clit for the last few seconds. She grunted as her climax hit, and a moment later she had a broad grin on her face.
She opened her eyes. "I did it," she said.
"Was it the hardest thing you've ever done?"
"Maybe there's something else like learning calculus, but...yeah, it was a challenge to do it. I mean it was a challenge to even start, knowing you were watching, and I was almost surprised that I managed to get all the way and cum. I thought I'd be too self-conscious. My first public orgasm."
"It's not exactly public."
"Well, my first orgasm outside the privacy of my own bedroom."
"It was hot to watch, I have to admit."
"Did it work?" she said as she came back down to earth.
"What do you mean?"
"Did I make you hard?"
"Yeah."
"Do you want to put it in?"
"But you're a virgin."
"I'm ready not to be."
"Do you know how to do it?"
"You know I've been watching porn since middle school. So I think I know how to do it. I've just never done it. Make me a...whatever comes after VWM. Woman WM or whatever. I was a virgin. Make me a woman."
"Take the rest of your clothes off. Let me see your boobs."
She sat up and a moment later was naked. She had cute little breasts, much smaller than her mother's, but they were firm and she had nice big nipples.
I stood up and took my clothes off. She lay there gently masturbating herself, keeping her pussy warmed up. I moved between her legs and pressed my cockhead against her pussy lips. I let her grasp it and decide how slowly we should go. But she wasn't in that sort of mood.
"Just fucking shove it in."
So I did. It was like ripping off a band-aid in one go. I thrust my hips forward. She screamed. And she was instantly no longer a V. My cock was buried in her cunt. I didn't move as she lay there for a moment panting like a horse at the end of a race."
"Gosh, that hurt like hell," she said.
I lay there motionless inside her body. "Are you okay?"
"Yes. I think I was in shock for a few seconds. But it's okay now. Do it. I can't believe these words are going to come out of my mouth, but fuck me."
I started to fuck her gently, trying to be aware that she would be tender inside her body. There was a little of her blood on my cock but she couldn't see because of the curve of her body. Plus her eyes were shut anyway.
"Okay?" I asked.
"More than okay. I should have done this in middle school when I first found out how it all worked. It's wonderful. You don't have to be gentle any more. I think I'm fine."
"If I'm rough?"
"Yeah. Like in porn. Pound me."
So I did. I hooked her legs around my arms so she was totally exposed. And then thrust hard back and forth into her. She had her second orgasm of the day almost instantly. The first orgasm of her life that was not of her own making. I let her relax.
"Where shall I cum?" I whispered to her.
"What are my choices?"
I laughed. "You're the one who's been watching porn since middle school. So I think you know the choices."
"I know it's maybe boring for you, but just come on my belly. I want to see it shoot out. It's my first time, remember. I've never seen it. Sperm. That sounds so clinical."
"Just say cum. Do you want me to stroke myself or do you want to try it?"
"Let me try. If I'm too incompetent you can take over. I'm still a student driver."
She reached out and grabbed my cock. One advantage of the porn-since-middle-school generation is that they know not to be too gentle. To stroke hard and fast. It only took a short time and cum shot out of my cock up between her breasts. I rubbed a finger in it and pushed it into her mouth.
"Taste it," I said. She licked my finger clean.
"Gosh, I've done so many things today for the first time."
"You need to do more. You just had sex but I'm not your boyfriend so we need to get you on Tinder and the other apps, so you can have lots more sex."
"You aren't going to have sex with me again?"
"Until we get you a boyfriend, I guess. But you need someone closer to your age. Is there anything you want to try?"
"Everything. But especially being licked."
"By me. Or by a girl."
"Oh my god, I've never even considered a girl. I'm not a lesbian."
"I have a challenge for you. Break one of the girls at the stable by the script. And make her lick you after she's masturbated for you."
"Gosh, my pussy just twitched. Who should we pick?"
"How about Jenny? Do you think you can break her?"
"I'll try. Give me the script. Being a virgin. Masturbating. Color of panties. Open up her pants, take them off. I forget exactly how it went when you broke me."
I handed her a printout. "Here's the script. Once you break Jenny you need to train her on the script too. So she learns how to break girls too. And you need to help her do a Tinder profile."
"Okay. I've no idea what to say. That I am a lady in the streets and a demon in the sheets or something?"
"No, that's too much of a cliché these days. Put your clothes back on, and then come back in a couple of hours and we'll write your profile. A cliché-free profile. And don't forget you're going to break Jenny."
"Okay. And I'll try to summon up the courage to break her tomorrow."
Chapter 3
Once her daughter had got dressed and left I called Kathy.
"The script worked," I said.
"Meaning what?"
"Your daughter masturbated for me. I broke her."
"Really? You're not teasing me?"
"Truly. She took her panties off according to the script and then rubbed herself until she came."
"What happened after that?"
"She wanted me inside her."
"Did you do it?"
"Yeah. Sorry. I took your daughter's virginity without discussing it with you."
"It's her body. She's not a child. You don't need to discuss it with me."
"Except that she's the prototype for our business plan. A VWM whose parents might pay for us to mature their daughter and straighten up her life."
She laughed. "You make it sound like aging wine."
"Maybe it is. We take girls on their eighteenth birthday and lay them down for a couple of years until they are truly ready to be an adult."
"So what's next?"
"Let me talk to Sandy. I know you can't talk to her about sex but I can. She masturbated for me. She committed."
"And you had sex with her."
"Sure. But it's the masturbation that's the true commitment. Fucking is much more common. You know the phrase friend-with-benefits. But they just fuck, maybe not even kiss, and certainly do not do exhibition-masturbation. Do you want to know what's next?"
"Probably not. But tell me."
"Now she needs to do it herself. Break a girl."
"I hope she can do it. Our business depends on scaling it up to lots of girls. It can't depend on you doing it all. Or even her. She has to do her college stuff too. That's her day-job. This is just a side-hustle."
Sandy came back that afternoon.
"Let's do your Tinder profile," I said to her.
"That I like to walk along the beach and to drink chardonnay watching the sunset."
"That's such a cliché," I said. "Let's make you stand out."
"How do we do that?"
"Guys don't read the profile anyway, so don't bother with all that chardonnay stuff. They just look at the photos. And mostly just the first one that shows up to swipe on."
"So one in casual clothes, one in a little black dress, one somewhere fabulous like Paris, where I've never even been?"
"No. That's a cliché too. Here's my idea. You don't do any of that chardonnay-little-black-number stuff. You just do one photo."
"Okay. But how does that work to make me stand out?"
"You only wear panties and have a thousand-pound animal between your legs."
It took her a moment to realize what I meant.
"On a horse? In just panties?"
"Yes. Guys will all imagine being between your legs too."
"Really? I know so little about boys."
"Can you ride bareback? Without a saddle and stirrups?"
"It's really tough to get on, but easy once you're up there."
"Do you have a pretty riding jacket or anything?"
"Just one from some years ago." She laughed. "I think my boobs will still fit into it. As you know, since you've seen them, they're not that large."
"Here's my idea. If you're up for it. Above the waist you wear the most formal riding gear you own. The jacket. Helmet. Whip. As if you're out for a real ride. Dressage even."
"And below my waist?"
"Nothing. Well, you can't be fully naked or you'll get thrown off the dating apps. But just panties. Bare legs. I was going to say riding boots but that makes no sense if you can do it bareback with no stirrups. Just some sneakers or sandals. Whatever you need to actually get around the paddock and get onto the horse. Have you ever seen a picture like that?"
"I don't think so."
"Me neither. So you will stand out from all the chardonnay-little-black-number crowd taking pictures on the sundeck."
"What do we do for the profile?"
"If you are up for it, just say ‘I like to ride'. It's a double meaning. Obviously, the horse. But it is also a euphemism for sex."
"That's it? Not dozens of photos and pages of profile text about...well, sunsets and chardonnay."
"No. One photo of you half-naked bareback on a horse. And a one-line profile."
"It seems too...I don't know whether to say out-there, or weird."
"You ride all the time, but in normal clothes, not your panties. But most people never see a girl on a horse, let alone half-naked. I bet you've never ridden in just panties before."
She laughed. "That's for sure."
"Photo session tomorrow."
"Okay."
I put my hand on her shoulder. "Are you really okay?" I asked. I wanted to make sure she wasn't freaked out behind her calm façade.
"Yes. I'm totally up for this. I can ride bareback in just my panties, not that I've ever done it before. I trust you that it's sexy if I do. Girls haven't a clue about what's sexy to men. Big boobs, small boobs, shaved pussy, a big hairy mound, anal plugs, piercings, tattoos."
"You've watched way too much porn," I said laughing.
She laughed. "Hooks up the ass, candle wax, golden showers, handcuffs, nipple clamps. I think I've seen most things."
"Was it weird seeing all that stuff when you were in middle-school? Still a child, really."
"Yeah. I'd no idea any of that stuff existed. I mean it was before my first sex-ed class, so I never had a clue how the stuff between my legs was meant to be used. I'd never even looked down there until I stuck my phone between my legs one day. My sea anemone."
"So you've seen the entire menu of porn."
"I think so. There's probably more extreme stuff I've never discovered."
"But you've never discovered a half-naked girl on a horse."
"That's true. You're right that these pictures might be a good approach, especially since you own a stable so horses are easy to obtain for any girls we train."
"Let's see what happens."
"Probably nothing. Who's interested in a no-name horse rider from this little town?"
"It will be the best photo on the whole of Tinder."
"Okay. I've never done online dating so I don't really know how this works. I really mean I've never tried to date before. My generation didn't make the effort in high school that you see in the movies. We're not the American Pie generation. I was a virgin until you made me masturbate for you yesterday."
"For the business model."
She laughed. "Yeah. Like you didn't want to watch."
"Now you're awakened."
"Okay. I'm not going to pretend I don't want to do it again now I've discovered what it's like. And I got the reaming over with."
"Reaming?"
"Yes. Vaginas are tiny. So the first time is like having a power-tool shoved in there. That's why I made you just do it. Just ream me."
"Are you available tomorrow for a photoshoot? I'll organize a photographer."
"You can't just use your phone?"
"The number one thing I've read about online dating is to get professional photos. They look so much better than the usual crap. Even more important for you. You're only going to have one photo in the end, even though a hundred will be taken as you ride around bareback in your panties. So let's get a real photographer to take it. He'll see you in just your little thong, so you have to be a little bit brave. But the results will be superior to an idiot like me taking the picture on my iPhone."
"I'll be more comfortable with a female photographer. With my...well, let's be direct, with my mound swelling out in a tiny thong. You've seen it—the only person in the world actually—so you know I'm...fleshy down there. It sticks out."
"Your camel toe."
"Is that what men call it? I've never heard that expression. I suppose it is a bit like a camel toe. I mean on a camel. As opposed to in my panties."
"I;m sure a woman photographer can be arranged."
I looked on the net and hired a female photographer to come the stable the next day, and gave her the outline of the project. A perfect photo of Sandy in panties on a horse with no saddle.
"Okay, as you heard me talking on the phone you already know the photographer is coming tomorrow. So go and try to break Jenny."
"In the words of Yoda, No Try not. Do...or do not. There is no try."
"OK. Then do."
"I'm scared."
"Be brave."
Early evening I texted her to find out if she succeeded.
"how did it go?"
"i broke her. that script is amazing. it's terrifying at the start, the virginity and masturbating bit, but it gets easier once her clothes are coming off."
"she masturbated for you?"
"yup"
"did you make her lick you afterwards"
"i did. that was amazing too. such an unusual day. my first time with a girl."
"your sea anemone got licked"
"yeah it did"
"the photographer is coming at 9 tomorrow for your photographs"
"i'd better pick my best panties when i get dressed"
Sandy rode around bareback over small jumps as the photographer took pictures. I was certain that this project was going to work. She looked so sexy riding a big horse in her panties. Let's face it, I don't care who you are, you've never seen a girl ride a horse in just her panties.
We had a few minutes left with the photographer
"Take off your panties," I told her. "We can't use it for your profile but who knows if you want it for your personal collection. Or my bedroom wall."
"Oh my god, you're going to put a picture of me in your bedroom."
"Yes. With your bare pussy pressed against the bare back of a huge animal you are controlling with your bare legs."
The photos turned out to be better than any of us had expected. We picked one and posted it for her Tinder profile. Girl with bare legs, just in panties, riding a big horse. Later we would copy that to all the other sites like Hinge and Bumble, but using the photo on Tinder was the prototype experiment to see if this approach worked.
As I had told her, I took one of the photos of her riding without any panties and put it on my bedroom wall. Riding is a little bit sexual anyway, bouncing the area between a girl's legs on a saddle. Bareback, with no saddle, is even more so. You really feel the horse. If you're a tweenager VWM you don't really know how close to actual sex it is to ride a horse without a saddle. Just panties takes it the next level, like most of the photos we took. And no panties is extreme. It's more like fucking than fucking.
Gosh, did it work. She got so many approaches. Of course, there's an aspect of sites like Tinder that some men swipe right on everyone. But apparently Tinder ignores people like that. So only a few get through.
But every guy Sandy decided to swipe right on matched instantly. The horse thing seemed to be a success.
"We need to talk about what you want," I said to her. "Do you want a relationship? Or do you just want to fuck a lot? At your age it's all fine, you don't need to settle down yet. And...well, let's face it, fucking is fun. And you might accidentally fall into a relationship?"
"How did it work in your day?"
"I tried to fuck as much as I could and then one of the girls turned out to become my wife."
"So let's go for fuck a lot and maybe one of them turns into a real relationship."
"The father of your future hypothetical children."
"Maybe even that. And in the meantime, I'll have lots of casual sex."
"so do you need my help in texting your matches?"
"let me try on my own first. i have to learn anyway"
Chapter 4
Later that day I was in the office with Kathy.
"Do you want to experience it? The heart of our business. The script?"
"What do you mean?"
"What color are your panties?"
"Oh my god, you're really going to do this to me. Run the script on me? White."
"Prove it. Usually a girl is in riding pants or jeans so she has to open up. But you're in a skirt. So just pull it up."
She reached down to the hem of her skirt and pulled it up. She was in white panties."
"Are you shaved or hairy?"
"You know I still have hair. I told you once before."
"Prove it."
"You mean take my panties off?"
"Yes."
She had to think about that for a moment. It was a big step. We were business partners. She was married. Finally, she decided to do it. She started by undoing the zipper on her skirt and letting it fall to her ankles. Then she slid her panties over her hips and let them fall to join her skirt."
She sat down and spread her legs. "Voila. My pussy, you naughty man. I should not be showing it to you."
"You're ahead of the script. At this point the girl has her panties off but not spread her legs yet."
"I don't really remember being eighteen, but spreading my legs in front of someone would've been super-scary. Not that I ever did it. But it would've been terrifying."
"Now masturbate for me. All the way."
"Gosh, really. I'll try."
She closed her eyes and leaned back. He hand slid down over her belly, through her pubes and I saw a finger enter the top of her slit seeking out her clit. She started to rub herself slowly.
"What are you thinking of?" I asked.
"I'm going to imagine you. Fucking me."
"In your pussy or your ass?"
"Oh my god, I've never done that."
"Then today will be the first time."
"You're going to do me in the ass. For real, not just in my imagination?"
"Masturbate first."
"Get your cock out. If I'm going to be this out there then you need to do something for me."
I undid my jeans. I was just going to get my cock out, but since Kathy was naked from the waist down I figured I should be too. I pushed my jeans and my underwear down to my ankles. My cock was already semi-hard as I slowly started to stroke it, watching her eyes absorbing the scene as her finger worked its magic in the furrow between her lips.
"You're big," she said. "How does it fit in my ass?"
I reached into one of my desk drawers and picked up an anal plug.
"What's that?" she said.
"An anal plug. It goes in your ass."
She laughed. "Do all men have anal plugs in their desk?"
"I've no idea. But I doubt it."
I stood up and moved to her side of the desk.
"Lick it," I said.
I pushed it into her mouth and watched as she twirled her tongue around the shiny metal. Then I reached down between her legs. She put her hands behind her knees and pulled them up to her chest. I positioned the plug on the asterisk of her asshole, and pushed. Her body resisted but I was firm, and gradually her asshole distended until the fattest part of the plug slipped into her body. It went the rest of the way easily and then locked into place.
"That feels weird," she said. "I've never had anything in there before."
"I'm going to fuck you anally once you've cum."
"I can't believe I'm not going to stop you."
"Has your husband tried to fuck you there?"
"Never. He just knows I'd say ‘no' so it's better not to ask."
"You're not going to say ‘no' to me."
"To be honest, I want to try it. Just don't hurt me. Go slowly like you presumably did with my daughter."
I laughed. "Sandy just told me to shove it in and get it over with. She calls it ‘reaming', having a cock in there for the first time."
"I'm getting close," she said. "Gosh, I should stop before I cum and then I don't have to be...reamed."
Her fingers started to move faster among the folds of her pussy. Just when I sensed she was on the cusp of her orgasm, I reached forward and roughly forced a finger into her wet hole.
"Nngh," she grunted in surprise. I felt her cunt clamp down hard on my finger as her orgasm began. I slid my finger back and forth in and out of her body as we both felt the pulsations of her vagina.
"Don't stop," she moaned, an instruction to herself as much as to me. She didn't stop rubbing her clit, and I didn't stop finger-fucking her. Finally, the last tremors died away and she lay there breathing heavily with her eyes shut.
I reached down and pulled the plug out of her ass. Before her asshole could close up tight again, I pressed my cockhead onto the brown pucker and thrust my hips forward hard.
She screamed, maybe a bit from pain but mostly from surprise at suddenly having a cock in her virgin rear entrance. She opened her eyes.
"I can see why my daughter calls it reaming," she said.
"I didn't do her in the ass," I replied as I slowly pushed forward and watched as my pink cockhead vanished into the tight brown ring. "She called it reaming in her virgin vagina."
"Are you going to do her in the ass too?"
"One day."
I forced a bit more of my shaft into my business partner. I rocked my hips back and forth, gradually working my entire length into her.
"I want you to cum," I said. "Anal orgasms are the best."
She laughed. "I don't think I can do that to order." She paused. "Oh my god, I think it's going to happen anyway."
She yelped like a dog as the first anal orgasm of her life flooded through her body, a stronger orgasm than the one she had earlier from masturbating. I held her knees back as I vigorously thrust in and out of her.
"Yeah, ream me," she gasped.
Her asshole spasming on my cock meant that I was close too. She sensed it.
"Cum in my ass, you dirty man."
"Squeeze me."
She tightened her asshole onto my cock. It jerked and I felt the first squirt of my cum shoot into her rectum. I don't think she could feel it, but she sensed it anyway. She rhythmically tightened and loosed her asshole as I pumped myself empty into her body.
I pulled out of her as I started to soften. She stood up, picked up her skirt, and put it back on. It fell down into place and once again she was my business partner, dressed professionally. Except that I knew she had no panties on since they were still on the floor. And she would have my jism seeping out of her asshole and running down her leg.
"Is that the end of the script?" she said.
"For today. But you are no longer an anal virgin."
"Nope. I can already tell I'll want it again one day."
"We should put an anal script together too. So the girls can seduce boys and not just other girls. But they have to take the boys in their asses."
"You have such a dirty mind. I love it."
,
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