This story was hard to categorize. I put it in anal because that’s a lot of the action, but it’s mostly a “first time” story. Also, there are incidents of members of the same family being in the same room while they’re having sex (but not with each other). I don’t think that counts as incest, but fair warning if that’s over the line for you.

As with many of my stories this one is longer and doesn’t get to the action for a while. This story is actually longer than most; I wondered about splitting it up, but it didn’t flow right when I did that. Apologies if that puts anyone off.

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Finally, after 18 years, Billy Dupree finally believed God might have decided it was his turn for some good tidings.

Chuck Baker, varsity quarterback, had never stopped ragging on Billy for his “deadass boring straightedge punk” existence. Billy didn’t join in rating the other girls at college with his teammates. He didn’t go to the bonfires Chuck or some of the others held where alcohol and possibly other things flowed freely. He was one of the only people on the team that hadn’t been with Sadie Hawkins (who lived up to her name; she asked the guys. For everything) for reasons other than age. He skipped the New Year’s “banging balls bash” that was rumored to feature a midnight orgy where the goal was to cum right when the new year hit. He kept his grades up more than the bare minimum to stay on the team, and he went to church on Sundays and could actually say what the sermon had been about afterward. He suspected he would have been a much less recognized member of the team if he hadn’t been on the defensive line; he was pretty sure Chuck would have shut him out.

Billy knew he wasn’t exactly a model material, but genetics hadn’t screwed him over either. He had a nice enough face according to most, hadn’t suffered with any major acne or skin conditions, hit puberty on schedule and despite stopping just shy of six feet he was still tall enough that most girls could wear heels next to him and not feel awkward. Plus being on the football team and maintaining himself for that kept him in good shape.

His “boring” reputation came after he refused the infamous Sadie. She was good looking enough that she could turn heads when she cleaned herself up, but she already looked like a girl in her mid-twenties in high college, and not in a good way. She was hot for football players. You didn’t even need a letterman jacket; just make sure she saw you on the field. Nobody had caught anything from her and she hadn’t officially gotten pregnant, but there had been a few conspicuous stretches where she wasn’t in college.

Billy passed on her offer to blow him under the bleachers at halftime. She’d chuckled and teased that he wanted the full monty so he’d have to wait until after the game. When he’d simply left for home and not bothered to meet up with her, she put him on blast.

“Billy Dupree thinks he’s too good to be seen with me. The whole school knows how I feel about football players, and I’m just trying to show my support. What kind of aturns this down!?”

She’d included a picture of herself wearing a bikini that barely covered anything, mostly featuring strings and small patches of fabric in strategic locations.

She’d been suspended, mostly so the college could claim it was tough on cyber-bullying, a toughness that evaporated a mere two weeks later when a student most people had wondered was female began developing a noticeable moustache.

Billy endured the ridicule and teasing, mostly from his teammates. A lot of girls he knew subtly gave him props for not “fucking that complete skank” but they didn’t publicly stick up for him. Jillian McCoy had gone with him to junior prom, and they’d finished the night in traditional fashion, but after that she dropped him, plainly telling him she was sorry but she was losing her friends because of his reputation with the upper echelons of high college society. No other girls would touch him after that. He stuck to his straight edge approach anyway, something that thrilled his parents, particularly his mother, but didn’t get him many favors or friends otherwise.

But all his patience and endurance paid off after the Thanksgiving game his senior year. He’d made an interception and run it back for a touchdown in the 4th quarter. With 4 minutes left and his team up by 12, Billy had basically eliminated the other team’s chances of a comeback, particularly since they followed that up with a three and out right after.

Billy had gotten his 15 minutes of fame with his classmates and the families, as well as at least two older gentleman who’d pointedly asked him where he’d applied for college. Then Prudence Luther had introduced herself.

The introduction was a formality; Billy and every other person at college knew who she was. She’d transferred in at the beginning of senior year. Rumor had it her family moved into one of the houses on defunct farmland near the outskirts of town. When she’d showed up in college, everyone was given a first hand lesson in the advantages of “good, clean, Christian living.”

Prudence had the “farmgirl next door” look nailed without trying. Honey blonde hair with natural waves that went down to her back, high cheekbones and bright blue eyes, straight white teeth, full lips, and eyebrows just a little more on the brown side. She all the time wore dresses made of heavy fabric to college and her mother had put in for a PE exemption so nobody saw her in gym clothes either, but her body was only barely contained. Based on the ski slope her breasts made out of the front of the dresses, girls who were “in the know” claimed her chest couldn’t be anything less than a D cup, and double or even triple D were more likely. Also she couldn’t remain standing at attention all day, and the spread of her hips when she sat, and the press of her dress against her backside when she bent over even a little had the entire student body convinced she was a dime piece wrapped in a burlap sack.

Martin Milnitzky, the college troublemaker and source of unsolicited “hot takes”, declared one week into college that “Prudence Luther is what you get if you take Kim Kardashian’s sex tape body and stick Taylor Swift’s head on it, without the black eyebrows.” While everyone was appropriately dismissive of his crude language, nobody actually disagreed with him.

However, she was already not in the good graces of many people, because she’d quickly established herself as a moral crusader and loud Christian. She’d publicly and loudly told off a number of guys in the college, accusing them of inappropriate behavior and harassment enough that no guy wanted to risk any contact with her by the end of her first week. The girls who’d tried to befriend her had quickly learned her tolerance for her own gender was possibly worse; she’d dismissed the entire cheerleading and dance squads as “barely better than strippers”, girls who asked how they looked got lectured if they were showing skin above the knee or below the shoulders, and any girl that hinted she’d had sex would be interrogated about feasible sexual assault unless they admitted it was consensual, at which point Prudence dismissed them as “too stupid to deal with their urges correctly, and too vulgar to keep it to themselves.”

She became the college’s Everest. She was a cold, dangerous figure to be admired from afar, though a few brave souls claimed they would try to climb it even if they died in the attempt. Apparently some odd schooling enrollments made her 18 at the beginning of senior year, so all the underclassmen were out of the running immediately. Jimmy Canton became a cautionary tale. He’d gotten an in with the family because they attended the same church. He had the tea on Prudence’s mom being a widow due to her father being lost overseas in combat. His behavior and reputation as senior class vice president had been enough for him to get the green light to take her to homecoming.

Everything had seemed fine at the dance. Prudence had worn a dress out of the 1800s, with puffy shoulders and full coverage all the way up to the top of her neck, but even then it was tighter up top than anything she’d ever worn before, and everyone at college was looking at her. The couple only participated in two slow dances and on both occasions maintained enough room between them someone could have slipped in and still not touched either person.

What happened after the dance was eventually public record, but people still questioned it. All anyone knew for sure is that Prudence and her mother, Carla, were in the police station the next morning, and Jimmy was under arrest by the afternoon. Two months later he was a registered sex offender, having pled no contest to a sexual assault charge, something the judge only allowed because the assault in question had been a stolen kiss in his car, while both Prudence and her mother claimed it had merely been the begin of who knew what. Jimmy had dropped out and was rumored to be working toward a GED, whatever school prospects he’d had completely evaporating.

When Prudence approached Billy after his stellar game he was shocked, but she’d dismissed his confusion and explained that she grew up in the south; of course she followed football. She’d also been impressed by his playing and his reputation. So, she wanted to date him.

Billy felt like he was the first person who’d figured out that Sherpas were a thing and said yes.

Trying to stave off the fate that had befallen Jimmy, he’d showed up at Prudence’s house on Sunday afternoon and specifically asked for her mother, making sure to bring flowers and some cornbread from his mother. Both of the items were for Prudence’s mother.

Carla Luther was good looking in her own right, and seemed more like her daughter’s sister than her mother. But then Prudence’s actual sister Chastity had shown up. Billy got a quick, unofficial lesson in genetics at that point.

Mrs. Luther’s body had clearly been what she passed down to her younger daughter. She was even curvier than her daughter, though in her case it was a few extra pounds and the effects of children that gave her larger proportions. But her hair was ruler straight and brown, along with her eyes. By stealing a quick glance at a few photos, Billy figured out that Prudence’s hair and eyes, and her sister Chastity’s body, were her father’s legacy; the departed Mr. Luther had been near or over Billy’s height, had a buzz cut that looked like light fuzz on his head due to its blonde color, and was all lean muscle.

Chastity had the long, straight brown hair of her mother, but she was almost Billy’s height. Based on how her dress hung, she did not have the other women’s curves, and the flash of calf he saw showed muscular tone. If Billy had to guess, he would say her body was probably built like a runner’s, or a swimmer’s. Mrs. Luther shooed her daughters away and sat Billy down.

“Billy I have to say you’re the best boy I know of in this town. With what my girl went through before I figured we’d just have to wait until college and roll the dice, but your reputation and you coming here, it’s a blessing and an answer to prayers.”

Billy almost said “amen,” but he figured that would be pushing it.

“I just want to know what…um…what are your expectations and what is your daughter, um…”

Billy was frustrated with himself; he’d had a nice speech prepped in his head when he’d driven over but now, in the middle of the reality, his tongue failed to obey. The woman seemed to take pity on him.

“Look, Billy, I’m not dumb. I see the news, I go to stores. My daughters watch shows, they have the internet, we all watch movies together, and yes, the movies are ones made in the last 40 years, and they aren’t all rated G. We’re Christians, but I wouldn’t be doing my daughters any favors trying to keep them ignorant of the world when I send them out into it.”

“Okay,” Billy said, not entirely sure where things were going but very sure this was not the lecture he’d expected so far.

“Look, Billy, would you be offended if I were direct with you?” she asked.

“Um, no ma’am,” he said.

She grimaced but with a smile, “Oh dear child, please never ma’am. I know it’s the south but I’m not ready for that. Carla would be great, Mrs. Luther if you must.”

“I think I’ll go with Mrs. Luther if that’s okay,” Billy said.

“Well we’ll work on that,” she said, patting his hand, then her expression got serious.

“Look Billy, I’ll just say it. My daughters are not ignorant girls. They know all about their bodies. They know you boys get absolutely mesmerized by breasts. They know they have vaginas between their thighs, and they know you have a penis. They know you put the two together to have a baby, and they know that isn’t exactly a chore for guys, especially at your age. And yes, they know that they’ve got a thing called a clitoris, and they know exactly how that works too. I’m hoping that last bit isn’t news to you?”

“Um…no?” Billy said, now totally lost in the conversational waters.

“Right, so, my point is my daughter is not some shrinking violet that was freaked out because Jimmy tried to give her a peck on the cheek. I was there, and he was going for a full on makeout session that she didn’t want. No means no, and I expect that to hold up, you understand?”

“Yes ma-yes Mrs. Luther,” Billy said.

“Right, so. My daughters and I have a pact with each other. There’s to be no fornication. That’s pretty clear in the Bible. That means nothing of yours goes into her, and vice versa. I’m not interested in arguing interpretations and what “counts” as sex. Just use that standard; if it’s part of your body, and it’s inside her, that’s a no-no. I’ll make an exception for tongues in mouths, because I know how things go; I’m not gonna get bent out of shape. Just do me a favor and don’t flaunt it in front of me. Mr. Luther’s been gone seven years and I ain’t exactly been on Tinder lately.”

“Okay,” Billy said, still thrown completely by the level of intimacy in the conversation. He expected the rules of behavior, he hadn’t counted on commentary on how long it had been since her mother got any.

“My best advice to you is let her take the lead and make sure to ask before you get adventurous. You do that, and everything will be fine. Also make sure you come by for Sunday dinner every so often.

-=-=-=-=-=-

So had begun his courtship of Prudence Luther. The climbing Everest analogy became ever more apt as time went on. The pace of their physical relationship was a very slow climb. Kissing with body contact only became a staple of their time together after a month. He finally felt one of her breasts over her clothes after two, and there was so much fabric involved he felt like he got more titillation from squeezing the memory foam pillows on his bed. He’d had to go home embarrassingly early on a Friday night when she’d given him permission to touch her back; she’d worn a skirt and top rather than a dress. But she’d given him so many warnings about going below her waist or anywhere near her breasts that he’d tensed his muscles in panic during the whole affair and his arms had cramped painfully. He had felt slightly justified when he joined the Luthers for dinner that Sunday and received an apology from Prudence and reassurance from her mother that the fault was more her daughters for not being clear. Chastity had barley controlled her snickers the whole time.

Then things seemed to snowball as prom approached. He officially asked her even though them being each other’s dates was a foregone conclusion. She’d squealed like a normal teenage girl and said yes. Then two weeks later Prudence told him her mother wanted to talk to him.

He’d gone to their house on a Saturday, and Mrs. Luther informed him when he got there that Prudence and Chastity were out dress shopping.

“So look Billy, like I said, I know how the world works, and I have no interest in denying my daughters experiences they should expect to have at numerous stages in their life. Prudence is gonna prom with you, and everyone knows what happens after prom, don’t they?”

“Um…I’m not sure if I know what you mean Mrs. Luther,” Billy said cautiously.

“Are you really dense or do you just want to hear me say it?” she pressed. When Billy just shrugged, Mrs. Luther rolled her eyes and said, “Sex, Billy. People have sex after prom. I know my daughter’s pretty, and she’s told me how excited she gets with you. I don’t want to force her into a situation where she’s gonna have to fight her promise. So here’s my offer.”

She turned and fixed Billy with an intense stare.

“You two come here, straight after the prom officially ends. Or earlier. Prudence can text me. Chastity and I will discover somewhere to be. If you do that, I will lift my ‘no penetration’ rule for the night. I’ll speak with Prudence and we’ll make sure she doesn’t end up with any surprises down the line. But this last part goes for both of us; either of us hear about you bragging around the college about this, and not only does it not happen, but you’re going stag to that dance. We’d both like to think you’re with my daughter for more reasons than just biding your time to get in her pants.”

“I am, Mrs. Luther,” Billy said.

“Good. Then keeping this under wraps shouldn’t be a issue. Just remember what I said, and remember where you have to be.”

From then on, Billy felt like Prudence (or “Pru” as he’d come to call her, and she agreed to) had a direct line to his cock. Her looking at him made him hard. Her kisses and the feel of her body against him, even clothed, may as well have been sex. A few times he’d jacked off in his car after dropping her off because he felt like if he didn’t the friction on his boxers as he drove was going to make him spew in his pants.

The Saturday before the prom he and Pru were at a makeout spot and she’d pulled back for a breath.

“Is anyone around baby?” she’d asked.

“No,” Billy replied after a cursory look around the hilltop he’d driven his truck up to. It was off a dirt road, so he wasn’t sure how many people knew about it to begin with.

“Good,” she said, “I can not wait for the prom. And I’m really looking forward to after it. I started my special preparations last week. I think it’s making me horny; I can barely control myself. So I’m going to give you a preview.”

With that, she reached down and pulled up her shirt and bra, letting her breasts spill out.

His brain seemed to slow down time so he could watch the show. The massive mounds of flesh that dropped from beneath her shirt were everything he’d dreamed of. The breasts dropped and bounced, the skin rippling as they settled. They were near perfect teardrops, hanging down from her chest just slightly and swelling out wide enough that they almost touched without help. Her nipples poked out, each about the size of the end of a finger, and the areolae around them crinkled to support them. They were not large, maybe an inch and half across, leaving most of her breasts as creamy white, soft flesh.

“Touch them,” Pru said after Billy didn’t know how long.

He reached up slowly and let the bottoms of the breasts settle in his palm. He wasn’t totally sure if this was his first time touching real breasts, but he was sure this was the first one he’d remember clearly, because he might never see breasts like this ever again. He knew some guys preferred smaller tits or actually liked fake ones, but Prudence’s chest defined perfect breasts for him.

Pru giggled a bit as he took them in his hands, then groaned as he squeezed them, letting the flesh push between his fingers. He kept it up, massaging the tits in his hand and feeling the nipples rub against his palms. They were in his truck, turned in the seats to face each other, and he could see Pru squirming, moving her legs back and forth together. He thought if she was experiencing the female equivalent of his iron hard-on and was trying to get comfortable, or even get off.