How To Train Your Girlfriend 01
Added 2025-08-13 12:00:16 +0000 UTCAuthor’s Note: Continuing this series of first chapters, I had an idea for another modern story with yet another cuckquean scenario. There might be a novel’s worth of story in this concept one day, but for now, it’s just a first chapter I wrote up to introduce you to the idea. Let me know what you think! Especially in relation to the other firsts, like the Pirate Wives of Penn, Liberty Legion, etc.
~~~
Mary was starting to hate girls’ nights. She got along with each of her friends individually, but when their book club met, it turned into a conversation about uncomfortable topics. This month’s book was an erotic romance, as many of their books had been. Werewolves, vampires, witches, and gratuitous sex seemed to be present in every book her friends read. The less spicy, more romantic period pieces were always Mary’s picks.
As usual, the night began with snacks and wine, the girls greeting each other, and piling into Barb’s living room, filling the couch, the two recliners, and an extra chair from the kitchen. Mary sat in the corner of the sofa, surrounded by her friends. Karen and Lisa sat on her left, sharing the couch with her.
She knew Karen from work, which was where Barb knew her, too. She preferred vampire romances, which contrasted sharply with her bright, bubbly, and ditzy personality. Her appearance reflected her absent-minded nature. She looked like she’d been late her whole life, but she refused to apologize for it. Her hair was a stormcloud of black curls, half-pinned and plotting their escape. The quarter-sleeve shirt she wore frayed at the edges, and darker colors long ago baked into the denim stained her knees.
Lisa was harsher in appearance, but did her best to soften her sharp features with wild, wind-tossed hair and loose clothing that hid her rectangular frame. Her loose dress had a floral pattern that ran from the hem at her calves to the squared neckline at the top, with two broad straps holding it in place. Her reddish-brown hair covered her shoulders, with whisps occasionally escaping before she tucked them behind her ear.
Sandra and Vicky sat on her right, each in a recliner with their feet tucked under them.
Sandra, Sandy to most of them, was a personal trainer and proud of it. Her long limbs rippled with muscle as she moved, and she wore denim shorts, flip-flops, and a spaghetti-strapped tank top to show them off. Her tan skin and ebony hair showed her Latina roots, and she was proud of her heritage. She moved with determination and grace that Mary could only envy, strong and confident in every opinion and decision. Her self-discipline had always impressed Mary, who respected her opinion more frequently than her own.
Vicky was the sluttiest of Mary’s friends and had proudly held that title since they’d met in college. Her red hair was chosen from a bottle, since she’d had brown hair when Mary met her. It was bright and intentional, the type of color that became a signal fire Mary could spot in any crowd. It announced her presence without apology, and Vicky’s brown eyes held the effortless boldness of someone who stopped asking permission years ago. Mary envied her freedom and the comfort she found in any environment she entered. Her body drew the lines of an hourglass, but she carried it like armor, not bait. Her every gesture, laugh, or quick turn of her head proved how unshackled she was, as if she’d already lived enough to know exactly which rules to ignore.
Barbara took the chair from the kitchen, playing host with the snacks and wine glasses laid out on the coffee table, which they surrounded. She was the oldest of the group and their most avid reader. Her thick-rimmed red glasses were half fashion statement, but all prescription. She’d worn a plain blue sundress tonight that made Mary feel underdressed for the occasion in her jeans and t-shirt. Barb had an elegance that she carried effortlessly, despite the effort Mary knew went into it. Her makeup, hair, nails, and posture showed her attention to detail and how everything she did had its purpose.
It was no surprise that her house was pristine enough to be a real estate model.
The house evoked an elegant charm with soft beige carpets, wooden ceiling beams, and a soft green paint like the dark green moss carpeting a forest glen. Paired with the stone fireplace, the oak DVD shelves, and the comfortable brown furniture, Barb had made herself a haven for TV-watching and hosting, nestled between her open-plan kitchen and the hallway that led to the bedrooms. Mary almost felt as though she were enjoying a garden party instead of a book club meeting. Fortunately, the air-conditioning worked, keeping them safe from the August heat beating against the windows as the sun set.
“So the house is all yours now?” Karen asked, looking around with her eyes lingering on the fireplace. The stonework above and below the mantle protruded from the wall, featuring jutting layers that made it appear climbable. The shifting shades of gray and white stones made it appear vibrant and gave it the illusion of depth. Black soot and gray ash flecked the tall, square opening from the burning logs. More logs waited patiently for their turn in the flames in a neat pyramid stacked to the left of the fireplace. The fire inside flickered and danced, providing atmosphere without increasing the temperature in the seats across the room.
“Yup,” Barbara said, shrugging. “My mom left it to me in her will. My step-brother tried to fight it, but the lawyers handled it.”
Mary took a sip of her drink at the mention of Barb’s mom. She missed the older gray-haired woman who passed a few months ago. Barb had been a mess when it happened, but she was holding up okay, and Mary was glad for the book club, giving her an excuse to socialize.
“Oh, I’m sorry he was a jerk about it,” Lisa said. “Death can tear a family apart.”
Barbara nodded. “We weren’t close. His dad dated and married my mom well after I moved out for college.”
“It wasn’t that long ago.” Mary protested. “We only graduated, like what… three years ago?”
“Four for Barb.” Vicky corrected with a small smile. “And we’re still paying our loans!” She raised her glass in a ‘cheers,’ and the others rolled their eyes and joined her.
“You’re ahead of all of us,” Sandra said to Barb. “Now all you need is a husband, and you can start a family.”
Barb laughed and waved her hand, dismissing Sandra’s silly notion. “No, thank you. I don’t want any kids, and that includes having to take care of a grown ass man on top of my full-time job.”
“You don’t even want a boyfriend?” Sandra asked, surprised. “I mean, sure, it’s tough to find the right guy, but you gotta try, right?”
“Nah.” Barb shrugged.
“You don’t get lonely?” Vicky asked.
“Of course I do, but that’s what the apps are for,” Barb said. “You want to fuck a guy? There’s an app for that.” She chuckled. “Long-term relationships aren’t for me. The guys always grow complacent and end up being a burden. I’m happy for you, though.” She raised her glass to Mary and then to Vicky.
Mary raised her glass, then sipped it as Barb drank from hers.
Vicky shrugged. “Honestly, I’m thinking I should break up with Barry.”
“Oh, no! I liked Barry. What’s wrong with him?” Sandra asked, leaning forward. The only thing Sandra loved more than romance was gossip.
Vicky held up her thumb and forefinger wide apart, then brought them close together about an inch and a half apart. “Turns out size does matter.”
The girls cracked up, with Sandra shaking her head in disbelief.
“Oh my god, really?” Lisa asked.
Vicky nodded. “It wouldn’t be so bad if that were the only problem, but he refuses to reciprocate oral. He doesn’t go down on me because he thinks it’s gross, but every time I put my hair up in a ponytail, he acts like I’m teasing him and asks for a blowjob. He gets all whiny if I say no. I’m over it.”
“See, this is why you should switch sides,” Lisa said. “We don’t need dicks to have a good time, that’s why we invented dildos.”
“Science, bitches.” Karen cut in to general laughter.
“Not that your love life is any better, though.” Barb cracked at Lisa. “When’s the last time you held down a steady girlfriend?”
Lisa gave Barb the middle finger, and the girls laughed it off as they settled into their seats. The clock ticked closer to eight, when the meeting technically started at seven, and no one had mentioned the book yet.
Mary blushed and looked down at her hands. She didn’t participate in the banter, as usual, but she cleared her throat and lifted her copy of the book from her lap. “Should we talk about the book?”
“Oh, come on.” Vicky gestured at Mary. “You’re the only one of us besides me with a boyfriend. You can’t joke around a little bit?”
Mary shrugged.
“Okay. How does Henry compare?” Vicky asked. “Tell me when.” She clapped her hands together and slowly spread them apart, looking at Mary for a signal.
Mary shook her head, refusing to participate. Vicky’s hands grew further and further apart, until even the women who read smutty fantasy romances with fae dongs larger than any known human anatomy realized the impossibility.
“Oh, come on, Mary!” Barb protested.
“How would I know?” Mary asked. “We’ve only been dating for six months.”
The girls all turned to look at her. Every head carried out the slow-turn stare at the same pace, as if she’d said something so unbelievable that reality itself slowed down to verify her words.
“You’ve been dating him for six months, and you don’t know his dick size?” Lisa asked. “You haven’t seen him hard?”
“I want to wait until marriage,” Mary said. “He knows that.”
The girls stared at her.
“I know you thought that way in college, but still?” Barb asked. “Seriously?”
Mary shrugged. “It’s important to me.”
“Honey…” Vicky said, as if consoling a child. “You can’t be serious. You don’t do anything? Not even hand stuff?” She mimed the gesture as if someone with a dick were sitting next to her and she was pumping him for several quick strokes.
Mary shook her head, staring at Vicky’s pumping hand working the air. “He said he’d go at my pace and follow my lead, so we haven’t done anything.”
“But you masturbate, right?” Barb asked.
Mary blushed. “That’s not important!”
“Oh, girl,” Karen said, shaking her head. “You don’t even do hand stuff with him? Mutual masturbation? Jerk off instruction? Nothing?”
Mary’s blush deepened into a darker crimson. Shame heated her cheeks, as if she had some moral shortcoming compared to those who embraced sex long before their relationships had any long-term viability.
“Okay, everyone, back off. Mary’s relationship is her business. We shouldn’t peer-pressure her into sex.” Barb said. “Even if she is aiming to be a thirty-year-old virgin someday soon.”
“I am not!” Mary said. “I just want to make sure he’s the one.”
“Sure, but how is your boyfriend dealing with it?” Vicky asked, curious. “Barry would have dumped me six weeks ago if I told him no sex for six weeks, much less months or years! Fuck! I couldn’t go six days without at least masturbating.”
“Don’t be mean,” Barb said. “You know it’s been a thing with every guy Mary’s ever dated.” She said.
The accuracy of that statement hurt more than the teasing. Mary looked up at Barb in surprise.
“Sorry, but it’s true, right?” Barb asked. “Each one of your past relationships said they’d be fine with it, but sex is part of love and romance, honey. They all got tired of it eventually and left, right?”
Mary nodded. Would Henry do that? No. Of course not. He loved her and told her she was beautiful. They went on dates, romantic ones, and adventures together. They laughed together, and their connection outstripped the ones she’d had with other guys.
“What was the longest relationship you’ve had with a guy?” Karen asked curiously.
Mary did the math. “Six months.” She said quietly, realizing she was a week away from being in her longest ongoing relationship.
“Maybe he’s secretly gay,” Lisa suggested.
“Or asexual.” Karen countered.
“Ten bucks says he’s gay,” Sandra said.
“He’s not either.” Mary protested.
“He’s gotta be one or the other,” Karen said. “Either asexual, or ass-sexual.”
The girls chuckled, except for Mary.
“I’ll take that action,” Barb said, offering a ten-dollar bill from her purse.
“My money’s on asexual,” Karen said. “Mary’s finally met a guy who’s into her for more than her body.”
At least that sounded complimentary. Mary didn’t think her boyfriend was either. Was he? Now that she thought about it, he’d been a gentleman on their dates. His gaze and touches were respectful, careful to avoid brushing her anywhere she might not want him to touch. Most of her ex-boyfriends couldn’t keep their eyes off her chest or butt.
Mary was one of those midwestern girls with a broad, round chest protruding from her flat stomach and farm-girl shoulders. Her dirty blonde hair wasn’t gorgeous, but she cared for it well, keeping it looking nicer than it would naturally. Her tall stature and wide hips elongated her legs, complemented by her full thighs and strong calves from horseback riding. Her round backside was the object of some fascination for her exes, but Henry had never once slapped it or tried to grope it as others had.
Was he gay? Asexual? Or just a gentleman?
“We were just joking around,” Barb said quickly as she watched Mary’s expression. “Please don’t get upset. I’m sure Henry is just being respectful. Is he religious, too?”
“I’m not as religious as I used to be.” Mary protested automatically. “And no, he used to go to church as a kid, but he hasn’t been since.”
“Well, you still have your hangups, obviously,” Vicky said. “Maybe he does, too?”
“I just… I don’t know how to do any of that stuff.” Mary shook her head. “I don’t want to be bad at it, and doing it before marriage… I feel like I’d lose something.”
“That’s purity culture talking,” Lisa assured her. “And it’s damaging as fuck. Helped me figure out I was gay, though.”
“Don’t you want to, though?” Barb asked. “You don’t have any desire for your boyfriend? You don’t want to rip his shirt off and bring him to his knees?”
Mary shook her head, refusing to answer verbally.
“If you think Mary’s a top, you don’t know her at all.” Sandra chimed in. “She’s a bottom if there ever was one.”
Mary didn’t answer.
“Would you rather make him kneel and turn him into your sex toy for a night? Or have him push past your limits and make you his sex toy for a night?” Vicky asked.
Mary’s blush was nearly as bright as the sun by the time Vicky finished asking her questions. Her imagination pictured Henry greeting her at the door and physically ripping her clothes off with his bare hands and muscular arms. Her body responded to the idea as if it had melted her inside; her heart fluttered, and she bit down on her lip to hold her responses back.
“Let’s stop teasing her,” Barbara said, holding up the book. “We should start talking about this anyway.”
“But I’m curious,” Vicky said, eyeing Mary. “I mean, you read the same books we do, right? You can’t say you don’t know how when you’ve been reading it in every other book. You’ve never tried any of that with your boyfriend?”
Mary shook her head. “I wouldn’t know where to start, and reading and doing are different. It’s fun to pretend, sure, but in real life? I’m not sure I’d know what to do with it if Henry showed me his… y’know.”
“Girl, I’m desperate enough for a good peen that if you give me ten minutes to break up with Barry, I’ll come over and show you what to do with it,” Vicky said, laughing.
The girls laughed, letting the room erupt with playful laughter and light-hearted rebukes for Vicky’s desperate sluttiness. Mary was blushing too hard to say anything, and she did her best to shrink into the corner as the attention of the room shifted away from her to Vicky.
“Just go on the apps, Vick,” Barbara said. “The guys are desperate for hookups. Just pick one you like and fuck his brains out.”
“Speaking of fucking and apps - what did you think of that app in the story? The magic one?” Sandra asked. “Weird, right?”
“Yeah, it was a little weird.” Karen agreed. “Hot, though. The way it could manipulate the guys she liked.”
“I’m so glad this book was Why Choose. I love when the girl doesn’t have to pick between the guys and can have all of them, sometimes at the same time.” Barb said, chuckling.
“We love a reverse-harem.” Vicky agreed.
The conversation about the book took flight from there, focusing more on the spicy scenes between each boyfriend and the final orgy, than the story or the moral implications of an app that could ‘influence’ others. Using it to remove inhibitions and allow for the reverse-harem in the first place seemed unethical to Mary. She didn’t appreciate the protagonist as much as the others did. Then again, she was more traditional than the others.
“You didn’t think it weird that she didn’t have to choose?” Mary asked, finally breaking into the conversation after half an hour of letting the others talk. “Shouldn’t love be between one person and another?”
“It’s not that deep,” Barb said, shaking her head.
“And plenty of people enjoy ethical non-monogamy.” Lisa chimed in.
“Was it ethical, though?” Karen asked. “The magic app is borderline.”
“Yeah, but Vlad was the one true love of the group,” Vicky said. “The others weren’t really romances, so much as hookups and stuff. Their relationships are nowhere near the depth and love she shared with Vlad.”
“Sure, but it was only the first book of the series.” Barb protested. “They might explore the other relationships more in the other books.”
“I guess.” Karen shrugged. “But it seemed like it was love between her and Vlad, and lust between her and the others.”
“Isn’t that wrong?” Mary asked. “If it’s ethical non-monogamy, shouldn’t it be equal?”
The others looked at Mary with kind, condescending smiles. She recognized that look. She’d seen it before, and too often when conversations about sex arose.
“There’s nothing right or wrong, but thinking makes it so.” Vicky quoted. “What matters is consent, and everyone in the group consented to sign up for the app, and to the relationship.”
“Yeah, nothing’s wrong with lust.” Lisa chimed in. “I just wish it wasn’t so hetero focused.”
“There was at least one chapter with gay sex when she had three of them together,” Barb said. “And the orgy at the end.”
“Yeah, but it’s not the same. I’d rather it was four women getting it on.” Lisa chuckled. “Is there a lesbian version of reverse-harem?”
“Regular harem?” Vicky ventured.
“There’s a ton of good harem fiction out there,” Karen said. “Should we read one of those next?”
“Gross.” Barb crinkled her nose. “One guy and a bunch of sexy women hot for him and willing to share? Talk about your typical male fantasy.” The derision in her tone was unmistakable.
“Didn’t we just enjoy a book with one woman and a bunch of sexy men hot for her and willing to share?” Mary asked, pointing out the hypocrisy. “Why is that okay, and the reverse isn’t?”
“Both are valid fantasies,” Vicky assured Mary. “Hell, I wouldn’t mind indulging in a little experimentation if there was enough of Barry to go around. I’m sure he’d love a threesome.”
Mary rolled her eyes.
“Don’t knock it until you try it. Sometimes it’s hot to watch your lover fuck someone else, then reclaim him afterwards. I did that with an ex once. And that reclamation sex? Woo.” Vicky fanned herself. “I still masturbate to it in the bathroom after I’m with Barry.”
The girls laughed, but Mary closed her eyes and tried to think about anything else. When she opened them, she found Vicky waiting for her.
“If you and Henry ever want a third, let me know,” Vicky said, giving her a wink. “I’ll show you what I mean.”
Mary didn’t answer. The girls laughed it off as Vicky being Vicky and resumed their discussion of the book’s weaker plot points. Mary joined in when she could, but thoughts of her and Henry’s relationship distracted her. Was he going to break up with her if she didn’t give him something? Should she get over nearly two decades of indoctrination after all this time away and try something sexual? The thought made her heart race, but Vicky’s offer lingered in the back of her mind for the rest of the night.
~~~ Henry ~~~
Henry was halfway through a mission in Red Dead Redemption 2 when his phone buzzed against his desk, and the screen lit up. It was late on Friday night, almost Saturday, so whoever texted probably needed something. Glancing at it, he could see that it’d come from Mary. He paused the game and set aside the controller as he checked his phone.
Mary: Hey, are you awake?
He checked the time on his phone. 11:42 PM. Her book club must have gone late tonight. His first thought was that something had happened. Her car battery must’ve died, or she had a flat tire and needed his help.
Henry: Yeah, I’m up. What’s up?
Mary: Can I come over? This needs to be an in-person conversation.
Henry’s heart rate spiked. Those kinds of conversations had historically never gone well for him.
Henry: Is something wrong?
Mary: No, not exactly. I need to talk to you about something. Tonight. Before I lose my nerve.
So she was breaking up with him. Henry racked his brain, unable to think of a single reason why. He supposed she’d tell him when he got here. Could he convince her not to? He honestly loved her, and he couldn’t imagine his future without her. They were taking things slow, sure, but that was at her request, wasn’t it? Did she find someone else? Did she realize that he wasn’t what she wanted? Was she coming out of the closet?
Mary: Is that okay?
The notification brought him back to the conversation. He swallowed his panic and typed his response with his thumb swiping between the keys on his phone.
Henry: Yeah. I’ll leave the door unlocked for you. Or should I meet you outside?
Mary: Either works. I’ll be there in ten.
She lived twenty minutes away, so either she was coming straight from her book club meeting, or she’d already been on her way when she texted. Either way, Henry had a maximum of twenty minutes to clean the apartment, which meant the hall closet was about to become a lot more packed.
He and his roommate, Mike, didn’t have a steady chore schedule. They cleaned whenever something bothered them. They kept their clothes in their bedrooms for the most part, and Mike had a girlfriend who sometimes spent the night, so there weren’t too many dishes to do that he couldn’t hide in the dishwasher. He had the place straightened up and ‘tidy’ inside of eight minutes. Except for his bedroom, but the piles of clothes he had strewn about in there didn’t matter. Mary had never asked to see his bedroom when she came over. They spent their time on the sofa watching movies, and cuddling was as far as she wanted things to progress.
Henry wanted more, of course he did, but he felt like an asshole for wanting something Mary didn’t want to give. She had trauma she didn’t talk about, or hangups, and Henry knew that going into this relationship. She’d been very clear that she wanted to wait until marriage to have sex. She was more traditional, and honestly, Henry admired that about her. He was still a guy with desires, though. She never asked him about porn, and he’d never asked if she considered it cheating. He assumed they had a ‘don’t ask, don’t tell’ arrangement about it, so he spent most of his nights after their dates jerking off before sleep.
That was another reason she probably shouldn’t go into his room.
Henry caught his breath at the kitchen counter with a minute to spare. He turned and headed toward the balcony, looking out over the second-story railing to watch for Mary’s car.
The apartment layout was simple. The front door opened to a small section of carpet, with the open kitchen to the left and a wall to the right. The right-hand wall continued to the back of the apartment, where the balcony overlooked the parking lot.
The living room was a large open rectangle between the balcony door and the kitchen. The left wall held a door, a TV, and another door. Across from those doors, two other doors rested on the right wall. The ‘hall closet’ was closest to the door, on the right wall, next to Mike’s room. Henry had the ‘master bedroom,’ which had an adjoining door to the bathroom, which was closer to the kitchen on the left side of the apartment.
The ‘breakfast counter’ between the kitchen and living room served as their table and provided most of their counter space. Their wooden counters bore a coating that made them look like marble. The dishwasher, stove, oven, and fridge were all old as heck, and as white as the painted cabinets above and below the counters, which was to say more of an eggshell than white.
The apartment was small, cozy, and most of all affordable. Luckily, the space’s proximity to the kitchen meant it smelled like whatever you cooked last, and Henry had lasagna for dinner. The whole place smelled like his mother’s homemade lasagna.
It struck him as he breathed the fresh air of the balcony that he might appreciate the nostalgic smell of his mother’s lasagna more than Mary did. He went back inside and rushed to the hall closet, struggling to keep everything he’d packed in there from spilling out as he fished through the debris for a scented candle. They’d had one last Christmas, hadn’t they? He dug, and eventually his fingers wrapped around the squat glass container of green wax that the label promised would smell of Christmas Tree, which he assumed meant pine.
He cracked open the lid and sniffed the candle, letting the sharp scent of pine needles tingle his nostrils. It faded quickly into something more languid, and he shrugged. How they fit Christmas into a jar was beyond him, but he supposed Christmas in August was better than lasagna.
He lit the candle with matches from the junk drawer next to the stove, not to be confused with the junk drawer next to the sink, or the one in the ‘island’ breakfast counter. The atmosphere was slow to change over its aroma, but sniffing as he walked convinced him the change was taking place. He squeezed some Febreeze into the bathroom, just in case, and put the bottle back under the bathroom sink as the knock of tender knuckles against his front door let him know that Mary had arrived.
Henry rushed to the door, but opened it slowly, as if he hadn’t nearly collided with it in his panic. “Mary, hey!” He said as he swung the door open. “Come on in.”
Mary smiled to see him, standing with her right hand gripping her left in front of her, holding her purse. Her jeans and t-shirt looked casual and comfortable, but flattered her figure. She’d tucked her t-shirt in, which was a rarity, and showed off her narrow waist. She stepped in, and Henry turned his eyes away from her to prevent himself from watching her ass. She had a great ass, especially in those jeans, but if she was upset, the last thing she needed was him leering at her. He checked the hallway, but there was no one behind her, so he closed the door.
“Is Mike in his room?” Mary asked, as if nervous.
“No, he’s at his girlfriend’s place tonight,” Henry said. “Can I offer you some food, or something to drink?” Henry asked as he strolled into the kitchen and opened the fridge. “We have water, or…” He hesitated. There was one beer left, but Mary didn’t drink beer. The orange juice container had approximately one mouthful left, forming a ring around the interior protruding plastic hump. There was no milk, which meant Mike had the last of it this morning with his cereal and hadn’t replaced it yet. “We have water.” He amended his statement.
Mary smiled softly, leaning against the kitchen breakfast counter with her hands. “No, thank you. Can we sit and talk?”
“Yeah, of course.” Henry nodded. “Kitchen or living room?”
“Uh…” Mary glanced around, spotting the empty sofa with a recliner on the far side. “Couch is fine.” She said.
“Okay,” Henry said and moved toward the couch. He gestured for Mary to sit first, and she sat on one corner of the sofa, and he sat on the other. Both of them sat straight and uncomfortably, not resting against the furniture, but rigid. Both rested their hands on their knees and turned slightly toward each other, facing the center of the sofa at an angle. “So, what did you want to discuss?”
Mary pulled her bottom lip into her mouth and looked down, staring at the empty seat between them as if it might answer for her.
“Is everything okay? Did something happen? Are you okay? Are we okay?” Henry asked. The questions rushed out of him in a flood that betrayed his panic.
“I’m fine,” Mary said, holding up her hand to stop the questions. “I’m okay. I’m sorry, I didn’t mean to panic you or anything. I just–this is important, and I figured if I didn’t broach the subject with you tonight, I might never work up the courage.”
“Okay,” Henry said slowly. “So, if nothing’s wrong, what couldn’t wait? What did you want to discuss?”
“Do you love me?” Mary asked, which surprised Henry. They’d exchanged ‘I love you’ already, and said it to each other pretty regularly.
“Yeah.” Henry nodded. “I love you. Do you still love me?”
“Of course!” Mary said quickly, lifting her eyes to his as if she couldn’t believe he’d even ask her that question.
“Just checking,” Henry said, suddenly feeling as if he needed to defend his reasoning for asking the question. Instead, he dug deeper. “Why do you ask?”
“Because I wanted to make sure before I asked you this next question,” Mary said, as if that explained everything. “Are you gay?”
Henry stared at Mary, his brow wrinkling in confusion as it furrowed his forehead. He wanted to ask her to repeat the question, as if he might’ve misheard her, but no, she’d asked about his orientation. “I’m straight.” He said, as if no one had ever asked him that before. “Not that there’s anything wrong with being gay, I just think being gay is like blue cheese.”
Mary’s confusion was unmistakable, but Henry wasn’t finished.
“Some people enjoy blue cheese and think it’s the best thing ever! Other people enjoy it, but only occasionally, or about half the time. And for some of us, it holds no appeal whatsoever.” Henry explained. “So yeah, I’m one of those people who doesn’t like blue cheese. I like my partners without penises and my cheese without mold.”
Mary stared at him, then burst out into laughter.
Henry chuckled, but it was small and dry compared to Mary’s laughter. He still wasn’t sure what this conversation was about or why they needed to have it so immediately, since they had plans to see each other tomorrow anyway. “What about you?” Henry asked. “Do you uh… prefer blue cheese?”
Mary seemed to consider the question genuinely, then shook her head. “I’m straight. I find you very attractive.”
“Why did you hesitate?” Henry asked. “It’s okay if you do. If this is you coming out to me as gay, I, well, I don’t know how to feel about that, to be honest, but I love you.”
“No,” Mary said, reaching out for his hand and scooting closer to him so that their knees almost touch as she held his fingers in hers. “I’m not gay. At least, I don’t think I am. I guess that’s part of the trouble, really, but no. I know what I’m drawn to, and I find you very attractive.” She reached up and brushed some of his hair out of his face, sharpening the part on the left side of his head.
Henry wasn’t a movie star, but he was ex-military and still kept in shape. His time in the army had paid for his school, and once he’d gotten out, he’d found work at a manufacturer nearby. They needed welders, and the work was challenging, but the money was good. He was building his savings and living frugally to put down a down payment on a house one day. If things went as well as they were for a while, he’d be able to afford the downpayment on a modest rancher in about ten years, and still be able to afford the monthly payments.
His hazel brown/green eyes found her blue ones, and he offered her a grin that dimpled his left cheek above his sharp jawline.
Mary melted inside, squeezing his fingers and steeling her resolve. “Okay, if you’re not gay, are you asexual? Do you not have sexual desires for me?”
Henry looked confused. “I have sexual desire for you, just in case that wasn’t clear.” He said. “I’m not asexual. Why would you think that I was?”
“Well… you’ve never pressured me to do anything with you,” Mary said. “You’ve never moved my hand into your lap, or tried to feel me up when we kiss. You don’t even touch my butt. Everyone touches my butt. Even Vicky slaps it goodbye.”
Henry raised both eyebrows. “You told me when we started dating that you weren’t comfortable having sex until marriage.”
“Yeah.” Mary agreed. “I remember.”
“So I told you that we can go at whatever pace you’re most comfortable with, and that you can set it,” Henry said. “You never pushed things further, so I didn’t either. I was trying to respect your wishes.”
“But don’t you have needs, like other guys?” Mary asked.
“Of course I do,” Henry said, shrugging. “But you’re more important to me than the occasional urge to stare at your ass or push things further when we kiss.”
Mary restrained the tears in her eyes. She wasn’t sad, but touched. His words melted their way through her ears and turned her eyes to mush. She swallowed, steeling herself as she straightened her spine.
“Okay,” Mary declared. “I want to see your penis.”
Henry laughed. It was a sudden, unstoppable bark of laughter that escaped his throat without warning.
Mary looked crushed.
“I’m sorry,” Henry said, holding up both hands to assure her. “I’m not sure what I was expecting you to say next, but it wasn’t that.”
“I’m sorry,” Mary said, quickly diffusing Henry’s apology with her own and turning crimson as she pulled her hands into balls on her lap. “I’m not sure how to say it, but… I love you. I want to try sexual things with you. Do things that I’ve never done before, but I don’t know what I’m doing, or where to start. So, I thought, maybe if I saw your penis, I’d figure it out.”
“Okay,” Henry said, nodding slowly as he followed her logic. “Why don’t we try making out on the sofa for a bit, and then you can do what feels natural?”
Mary’s eyes fell to his lips. “I think I’d like that.”
“Yeah?” Henry asked, scooting closer on the sofa.
“Yeah,” Mary said, scooting to meet him.
He kissed her, and she kissed back, pushing her lips against his in a long, open-mouthed embrace that sizzled against their faces. They grew more passionate with every passing second, but Mary kept her hands on his shoulders, and he kept his hands on her waist.
“Okay,” Mary said, gasping as she pulled away. “What should I do next?” She asked. “Tell me what to do.”
“You want me to tell you what to do?” Henry asked.
“Yes, please,” Mary said, biting her lip. “This is uncharted territory. I need you to take control here.”
“Okay,” Henry said, agreeing to take control. “Take off your shirt.”
To their shared surprise, Mary didn’t hesitate. She pulled at her shirt over her stomach, untucking it from her jeans, and lifted it off, revealing her rather conservative bra underneath. The large, bulging, gray fabric cups had a single ornament hanging between them, a tiny purple silk bow. Mary’s large chest limited her bra options.
“Sorry,” Mary said, apologizing as she followed Henry’s gaze to the bow. “I wasn’t planning on doing this in the morning when I got dressed. I should’ve worn sexier underwear.”
“You make the underwear sexy, not the other way around,” Henry said, which made Mary’s blush deepen across her pale cheeks. The center of her chest turned pink at the top, flushing with heat as his eyes roamed upward from the bow, traveling the crevasse between the bulbous curves of her breasts to her face once more.
She turned her face away, still smiling. “What should I do next?”
Henry didn’t answer, but took his shirt off. She returned the favor, letting her eyes wander over his shoulders, following the cleft between his pecs, to his soft abs, where her eyes lingered. He straightened his spine slightly to show them off more, though sitting made it less impressive than he would have preferred.
“Are you comfortable taking off your bra?” Henry asked.
“I think so,” Mary said. She swallowed her nerves and reached behind herself. Her fingers fumbled over the straps, and she plucked at the hooks. Her nervousness made her clumsy, but the task tested her flexibility even under ordinary circumstances. She’d never had to do this with someone watching her before. The latches finally unhooked, and the back of the bra flew open.
She pushed the straps down and held the cups in place with her hands. She looked at Henry, and he looked at her. “Are you okay with this?” Mary asked. “Is this turning you on?”
Henry nodded. “Are you kidding?” He asked. “Yes, this is turning me on.”
“So how can I help you, uh… release your urges?” Mary asked. “I’m–I’m not sure I want to go all the way. At least, not tonight. But maybe I could use my hand?”
Henry stared at her hands, currently holding the cups of her bra in place. “I’m okay with that.” He said. “Should I stand up?”
“Will that help?” Mary asked, uncertain.
Henry shrugged. He unbuckled his belt and unbuttoned his pants. He lowered his zipper and pushed his pants and underwear down. As soon as his waistline passed his dick, it sprang up to say hello, bobbing in the air momentarily, until he gripped the base of the shaft.
Mary’s eyes flew wide, staring at his length as if she’d never seen a penis before.
Then it occurred to him that she probably hadn’t.
“Are you okay?” He asked.
Mary nodded, silently, not removing her eyes from the purple tip of his cock.
Henry pumped his hand along the shaft to demonstrate, and then released himself, nodding toward her hands. “Let go of your bra, and take hold of it.” He said, gesturing. “One hand at the base.”
Mary pulled the bra closer to her chest as if it were a blanket.
“Mary, we don’t have to–”
“No!” Mary said, cutting him off. “I want to!”
“Do you?” Henry asked cautiously. “It looks like you’re scared of it. It’s not going to bite you. I promise.”
“It’s just… bigger than I thought,” Mary said.
“Well, thanks,” Henry said.
“That’s supposed to fit inside of me?” Mary asked. “After marriage?” She added quickly.
Henry wasn’t sure what was happening, but he nodded. “Yeah, but it’s okay. The vagina’s a tough and pliable thing. It’s natural, and it has a lot of natural processes to help it along.”
“Like what?” Mary asked.
“Uh… like arousal? Have you never taken sex ed?” Henry asked, concerned.
Mary shook her head. “They only taught abstinence in my school. Basic biology, sure, but we didn’t learn about sex. They just told us not to do it, or we’d go to hell.”
“Yeah, that tracks,” Henry said, nodding. “Well, don’t worry. You won’t go to hell for sex. That’s a whole thing. But beyond that, sex is a very natural process. This isn’t going inside of you tonight anyway, right? So don’t worry about that right now. You wanted to see it, so I’m showing it to you. Do you want to touch it? Or do you want to call it here for tonight? Going this far was a big step for you. I’m really proud of you.”
Mary finally tore her eyes away from it to look him in the eyes. Her own eyes watered, but she didn’t cry. “You’d stop here for tonight? Without release?”
“Well, I’d probably take care of it myself.” He admitted. “But you don’t have to do it for me, that’s my point.”
“It’s just so new,” Mary said, shaking her head. “What if I hurt you because I don’t know what I’m doing?”
“I can teach you as we go?” Henry said, uncertain how to answer that. “It’s pretty tough to hurt me with a handjob.”
Mary crinkled her nose at the crass term, but let it slide, given what they were discussing. She lowered her eyes to his lap again and stroked her chin. “What if we used a… like a demonstration?” She asked. “If I had someone show me what to do, but I was here and giving you permission, and we were all consenting to it, it wouldn’t be cheating, right?”
“Wait, what are you suggesting?” Henry asked. “You want to watch a how-to video?”
“No,” Mary said, shaking her head. “You can’t trust porn for stuff like this. Even the stuff in my books, that’s fiction, right? It’s not feasible, and sometimes not even possible. Writers make up scenes that read sexy on the page, not stuff that’d be sexy in real life. Like shower sex. According to the girls, it’s terrible, but it’s always hot in the books.”
“That’s true,” Henry said, still confused. He wasn’t sure where shower sex came into what they were discussing, but he saw her point. Unfortunately, that left him no closer to understanding her suggestion.
“But if we had someone who knew what they were doing… would you be willing to let them touch you while I watched?” Mary asked, then she brightened considerably at the prospect. “I could learn all kinds of things, and you could get the release you need without cheating. You’d be satisfied, so then you wouldn’t leave me, and I wouldn’t have to betray my conscience by doing things before marriage. It’s perfect!”
Henry felt as if he’d missed something. There had to be some crucial clue he’d missed somewhere along the way. He reviewed the conversation in his head, all the events leading up to this moment, and no. He still came up empty. “Mary, I’m not going to cheat on you or leave you for not being ready for sex, yet. Whatever trauma you need to work through, you can–”
“No, it’s not about trauma,” Mary said, shaking her head. “It’s not about desire either. I want to, I do, but I’m afraid. I’ve got all these fears and worries running through my brain with no way to silence them, and all the baggage I grew up with, but I want to satisfy you. I’d be a terrible wife if I didn’t know what I’m doing in the bedroom, right? And then I’d have made you wait all that time for nothing. I want to learn from the best, and maybe then I’ll be able to overcome my guilt, or shame, or whatever this is in my head.”
“Okay…” Henry said, still trying to process. “So, porn? We can watch some together and–”
“Not porn,” Mary said, shaking her head. “Porn is unrealistic.”
“Okay,” Henry said, not arguing that particular point when he was this close to receiving a handjob. “So what, exactly, are you proposing? Do you want me to show you how I do it?”
Mary shook her head. “Are you okay if I call Vicky?”
Oh, she wanted to call Vicky to get tips on giving a handjob? That probably wasn’t the worst idea. It killed the mood a little bit, but it wasn’t the end of the world. He could endure a handjob while she was on the phone. And of all of her friends, Vicky probably had the most experience jacking people off. He shrugged. “If you want to, sure. I told you that you can set the pace and we can do whatever you’re comfortable with, or not.”
Mary beamed from ear to ear, dropping her bra and hugging him, which had a surging effect on his groin as he finally saw her bare breasts for a split second, and then they mashed against his shirtless torso. Her nipples stiffened against the air-conditioned air and his warm skin, and he felt the heat of her impossibly soft breasts pillow against him.
“Great!” Mary shot up from the sofa, holding her breasts again, and running to her purse on the dividing kitchen counter a few feet away. She unlocked her phone and called her contact. “Vicky? It’s Mary. Did I wake you up?”
Henry watched his girlfriend and smiled at her enthusiasm.
“Oh, good. You broke it off with Barry then?”
That surprised him, but whatever Vicky had done, it only seemed to lift Mary’s spirits rather than crash them. Vicky must have been happy then, rather than heartbroken, which made sense if she was the one to dump him.
Mary spun toward him, smiling at him as she lowered her arm to show off her naked breasts. Her broad, round breasts were smooth, delicious melons of flesh. They were heavy and called out for cupping in his hands where’d they’d overflow. The massive underside curve of her breasts ended at her moderately sized forward-facing areolas, her nipples pert and erect in stiff tips that made him lick his lips.
Seeing his girlfriend topless in his apartment for the first time drove all the thoughts from his mind. He barely heard the rest of her conversation on the phone. Something about meaning what she said at book club, the third, and something, something, end of phone call.
“Okay, see you soon!” Mary said and ended the call. She turned away to put her phone in her purse and broke his line of sight to her breasts. Reality slowly sank in as he remembered more of her phone call.
“Wait, see you soon?” He asked, disappointed. “Are you leaving?”
Mary looked confused. “No, remember, I told you I wanted to be here.”
Henry’s confusion didn’t fade.
“I want to watch Vicky give you a handjob so I can learn how to do it, you can get one, and I don’t have to feel guilty about it,” Mary said. “Remember?”
Henry replayed their conversation in his head, now with more explicit understanding than he had before. Even after she stated it, he still didn’t believe it. That wasn’t a thing that happened, right? But in a twisted way, Mary seemed to have made it make sense. Porn was nasty, but consent was good, and if she, Henry, and Vicky all consented to this, then they were good. Why she couldn’t just consent to do it on her own was what confused Henry, but he wasn’t in her head. He couldn’t make sense of it.
“Are you still okay with it?” Mary asked. “I can call Vicky and cancel.”
“No, it’s… I mean, I’m not sure how I feel about Vicky doing it, honestly.” Henry said.
“You’re not interested in Vicky, right?” Mary asked. “Romantically, I mean.”
“No.” He shook his head. Vicky’s promiscuous ways made her less attractive to Henry rather than more, even if she had a decent body. She was an attractive woman in that she had a hot body and showed it off when she could, but he had no interest in her as a partner. That made him feel guilty about the exciting prospect of benefiting from that promiscuity.
“Then it’s perfect! I trust you. I don’t have to worry about you getting the wrong idea or Vicky falling in love with you. You and I love each other, right? We’ve committed ourselves to each other, and we’ve both agreed to this. Just for tonight, to see if it’ll work. If we hate it, we don’t have to do it again. And you’re not doing it behind my back, because I’m here watching and learning the entire time. Vicky’s not a lover, like in the books. She’s basically a dildo, but for guys.” Mary said, rambling with excitement as she returned to the sofa.
“Uh-huh,” Henry said, still confused, but doing his best to follow her line of thought. He still wasn’t convinced this was real. Had he fallen and hit his head on something? Was he going to wake up to find out that, in his cleaning the apartment for Mary to come over and dump him, he’d slipped or tripped and traveled to Oz? A head wound made more sense than what Mary seemed to be suggesting. Calling or Facetiming Vicky while Mary gave him a handjob seemed weird, but doable. Having Vicky give him a handjob while Mary watched sounded like the hottest thing he’d ever done, but the mental gymnastics Mary went through to make it work created quite the hurdle for Henry. And on the other side of that confusing hurdle? A handjob. So maybe he should just let Mary do whatever she wanted.
“Are you okay?” Mary asked. “You look like someone died.”
“What? No, I’m okay.” Henry said, shaking himself out of his stupor and running his hands over his face to fix his expression. “I’m just… in shock, I guess. I’m not sure what’s happening or how to process it. I’m either in a coma, dreaming all of this, or I’m the luckiest man alive?”
Mary chuckled. “Face it, Tiger, you just hit the jackpot.”
Henry chuckled at the reference to Spider-Man and Mary Jane, but Mary’s recitation did nothing to assure him that he wasn’t dreaming. As he wrestled with the idea, his erection began to fade. As it faded, he realized he had to pee badly.
“I’m just going to pee real quick,” Henry said, gesturing toward the bathroom. “How long do we have before she gets here?”
“Not long,” Mary said, covering her breasts again. “I guess I could put my shirt back on.”
“Please don’t,” Henry said, smiling slightly. “I love your breasts. They’re perfect. I want to burn them into my memory forever.”
“Well, hurry back then,” Mary said, gesturing to the bathroom. “Vicky will be here soon, and I’m not answering the door like this.” She gestured to her torso, and Henry took her meaning.
He dashed to the bathroom, holding his pants up with his hand and refastening them afterward. He washed his hands and exited into the living room just as Vicky knocked at the door.
“You’re sure about this?” Henry asked Mary as he paused by the kitchen dividing counter. The knocking increased in volume.
Mary nodded her head rapidly. “Yes. Hurry up and let her in before she makes a racket.”
Henry completed the trek as Mary ducked behind the recliner, hiding herself from view of the door, without her shirt or bra.
Vicky burst into the room as if she owned the place, her eyes roaming over Henry without his shirt and lingering on the dark line of his chest hair as it curled in a patch on the center of his chest and traveled downward toward his stomach in a thinning line that ended at his navel.
“Okay…” Vicky said as Henry closed the door. “Let’s get this party started.”
Comments
I honestly have no idea how that happened or got through all the editing. Lol. Sorry about that! Fixed it!
S. E. Aeghann
2025-12-31 17:53:35 +0000 UTCShe stepped in and George turned his eyes away... who's george?
SovietDegendays
2025-12-31 17:48:15 +0000 UTCThis is pretty damn good, I havent read any of the other ones yet but I definitely want more of this
master19man
2025-10-30 03:07:44 +0000 UTCLots of potential here
Michael Henderson
2025-08-17 13:12:37 +0000 UTCadditionally, please never stop making generalized digs at religious schooling and the humiliating excuse for sex ed most of them utilize. they deserve it 🥰
MJS
2025-08-14 21:58:18 +0000 UTCYeah. Once she gives him the green light, the idea is that Henry takes it over and organizes it based on what he wants her to learn.
S. E. Aeghann
2025-08-14 20:43:56 +0000 UTCSo far, it seems like the gf is organising her training herself, but maybe the title will fit better in a few chapters’ time :)
saffy
2025-08-14 20:23:05 +0000 UTCkeep trying new things, king 👑
MJS
2025-08-14 13:53:13 +0000 UTCA fascinating start to Mary's journey of discovery. I look forward to subsequent episodes.
Flamethrow
2025-08-13 21:37:42 +0000 UTCIt definitely has a lot in common with HH for sure.
S. E. Aeghann
2025-08-13 19:38:55 +0000 UTCI like this better than anything else you’ve written excluding HH and LP. It in some ways feels a little more like HH than even the babysitting story which makes it more familiar and appealing as a result.
Prepared
2025-08-13 19:37:25 +0000 UTCI guess I implied it with her lowering her arms to show off her naked breasts rather than explicitly stated that she dropped her bra while calling Vicky. I can edit to make it clearer.
S. E. Aeghann
2025-08-13 19:25:16 +0000 UTCMeh, it could be good. I am still most interested in your superhero story. Also the male MC can't burn breasts he never saw into his memory, she never released the bra to show her boobs.
Joseph Snyder
2025-08-13 19:21:30 +0000 UTC🤯 This is an excellent start, great balance of characters and Mary deeply intrigues me. I'm looking forward to the next installment, please keep writing this one. 👊
Lennis Dynamiks
2025-08-13 16:59:38 +0000 UTCInteresting. I like it better than the other first ones. However, it might be difficult to maintain the dynamics if Mary wants to remain chaste until the wedding. If this remains her wish only temporarily, the relationship could develop in an exciting direction. Mary could both develop her own desire for sexual activities with Henry and discover a voyeuristic inclination within herself.
Nicholas Ramage
2025-08-13 13:51:48 +0000 UTC