A Sleepless Night

Author's Note

Dear reader,

This is a gentle start to a series of stories inspired by and written for my wife, my Lucy. I hope you will enjoy it, and pass on whatever ratings, criticisms or compliments you feel it deserves.

Many thanks to my editor, GottaStartSomewhere, for volunteering much time and even more patience to get this as far as it's come.

Lucy rolled onto her side and sighed. She guessed at the time. Three o'clock? Four? She had been solidly awake since she and Mike went to bed just after midnight. After a couple hours, she'd forced herself to put away her phone.

The night had started with promise. A little-too-big edible (the effect was finally waning, but only just), a nudity-heavy 80's comedy and a full evening of Mike spooning her on the couch in their pajamas. By the end of the first act, she had her arm behind her with her hand down his PJ bottoms and had spent the next hour gently fondling his balls. He hugged her close, alternately cupping her breasts and slowly rolling her nipples between his fingers. This was how they spent their evenings more often than not. It was a coin toss whether it would lead to sex, and they were usually both happy with either outcome. But tonight, by the time she realized she was desperately in the mood, Mike was snoring softly. She could barely rouse him enough to go to bed. She'd hoped some stupid games or social media would tire her out. It hadn't helped.

She couldn't complain. Their relationship, always rock solid, grew stronger year after year. Their sex life was better than ever. Mike had always been... Muted? Stodgy? Repressed? No, that wasn't quite it. But it wasn't far from it. She was too high to think of the word. And horny - she didn't think well when she was horny. Suffice it to say, starting with that first blowjob on the uncomfortable wood easy chair with the pancake-thin cushions in her college apartment, initiating anything intimate almost always fell to her. Whether it was a kiss goodbye before work or her asking for some painful nipple play, she wished he'd take the lead more often.

Even the great fun of the small kinks they had shared was muted by the nature of her always having asked for it. Like one time last summer, when Mike was doing dishes. She'd come downstairs, freshly showered, wearing her favorite yellow sundress with the lilacs on it. She'd asked if he could help her with something: she couldn't remember if she remembered to put on panties. He'd hiked up the back of her dress, bent her over the counter, called her dirty names for "forgetting" to wear them and fingered her until she squirted all over the tile floor. When he was done, he licked his fingers, slapped her ass and told her to clean herself up. It had been incredibly hot... but how much hotter would it have been if he suggested it? She was well aware that she and Mike had an excellent sex life by any standard. But she wanted... more.

That wasn't to say he wasn't growing. Of late, Mike had been opening up to her more. He was initiating sex once in a while, and actually talking during it. Honest-to-God talking! And this was no chit chat - he'd been describing his fantasies in detail. She couldn't explain the sea change, but holy fuck was she ever happy about it.

She wasn't into all of his newly confessed fantasies, but she'd give a good number of them a try. At least, none of the new crop disgusted her, which had seemed to be his biggest worry. Why was he so forthcoming all of a sudden? She wanted to ask, but was afraid of making him feel self-conscious. She did not want to do anything other than encourage.

Anal sex had been the first new fantasy he'd shared in a very long time. He ate and fingered her asshole any chance he got. She'd asked him why he never tried to fuck her ass. The simple answer surprised her: she'd said that was a hard limit just after they started dating. She didn't recall that decades old conversation, but felt simultaneously touched and guilty that he'd been yearning for it for so long.

A few over-the-top moans and groans and thrusts of her sphincter the next time he fingered it was about all it took for him to shyly broach the subject. After an agonizingly careful, loving few minutes of fingering her asshole wider and wider, they both experienced anal sex for the first time. Though she had been curious, she was shocked to discover she loved it as much as he did. She recalled his hot breath on the nape of her neck as he whispered how much it turned him on to be buried in her asshole... the wet mist of her juices on her thighs as his balls slapped against her gushing pussy... the exhilaration of ceding the only hole she hadn't been fucked in to the man she loved.

Why had it taken them both so long to try anal? It was difficult not to look back with remorse at the sex that could have been. She wondered what other carnal delights their prudishness might be causing them to never experience.

Sighing, Lucy reached for her phone, turning her body to block the light from Mike's face. Three thirty four. She was going to be exhausted tomorrow if she couldn't get to sleep. She mulled the problem over. She was too horny to sleep. There was cock three feet from her pussy. She was unwilling to interrupt Mike's sleep to get it. No need for them both to be bleary-eyed tomorrow. She sighed again.

She let her free hand absentmindedly drift down her body, fingertips barely breaching the waistband of her pajama bottoms. The weight and warmth of her palm on her belly failed to provide its usual comfort. Her hand drifted farther down. She felt the softness of her pubes, pinching them lightly between her fingers and tugging, enjoying the tingly promise of pain. She white-knuckled a handful of hair and pulled slowly for a few moments, the promise becoming fully realized. Putting her phone back down, she slid her newly freed hand up under her shirt. She cupped a breast momentarily before zeroing in on her nipple. Tonight was not a soft caress kind of night. She pinched it, hard. The dull, hot ache between her legs worsened. Her hips started to thrust involuntarily. Frustrated, she begrudgingly took her hands out of her pajamas. Staring at the ceiling in the darkness, she consciously unballed her fists, laying her palms flat on the mattress and tucking them under her thighs slightly. They had a mind of their own tonight, and their goal wasn't sleep. They could stay pinned to the bed for a while.

Lucy weighed her options. No sex. No sleep. Fingers would be... insufficient for masturbation. Her thoughts drifted to her favorite purple vibrator in the nightstand. It would be noisy in the quiet bedroom. If Mike slept through it, mission accomplished. If he woke up... Lucy's cheeks flushed at the thought of being caught. Why was she so embarrassed? He'd be thrilled to wake up to her pleasuring herself; he'd be turned on for weeks. She wanted to do it. He would want her to do it. But the thought of him discovering her with a big vibrating toy in her pussy and then rolling over to go back to sleep was too mortifying to contemplate, no matter how far-fetched it might seem. She'd masturbated for him before, but always after they started having sex, when she could gauge his mood and knew he was horny. Her rosy cheeks turned a deep crimson in the darkness as shame and lust battled in her head. No, it was too much, she decided, chastising herself for her cowardice. They'd each been pushing their boundaries lately, but apparently she was going to play it safe and miserable tonight.

One of Mike's recent nudges at boundaries had been the arrival of a large nondescript cardboard box. He'd ordered an unreasonable number of sex toys one night while way too horny. Unable to hide the box that arrived a week later, priggish Mike was obligated to explain lecherous Mike's purchases to her. She'd revelled in his embarrassment, his eyes daring only fleeting glances into hers as he sheepishly described ordering the box full of goodies, almost apologetically scanning her face for signs of disgust as he proffered a strap-on harness and cute little dildo for her inspection. He'd never admitted to wanting to be ass fucked before.

As they lay in bed, Mike took something out of the box, keeping it behind his back until he repositioned his head on her pillow. A metal butt plug with a red ruby heart. Pretty. Big. He handed it to her. Her bemused appreciation of his awkwardness turned to shock at how heavy the toy was. Solid metal, not chrome coated plastic, as she'd initially assumed.

Mike's furtive glances got more focused, steady, piercing as he fleshed out his scenario for using the ruby heart butt plug on her. She imagined what it would feel like inside her: the physical sensation of having the biggest thing, plastic, metal or organic, she'd ever had slowly shoved up her back passage. Her heartbeat quickened.

When he finally did fuck her with it for the first time, weeks later, she learned she had correctly estimated how much it would hurt, and vastly underestimated how much she would like it. They'd since used it a lot; it was her go-to couple's toy now. It didn't hurt nearly so much as it did that first night, when she almost used her safe word to make the pain stop. She missed that virginal pain and the delightful shame of being penetrated so intimately. Weirdly, Mike seemed to understand her disappointment, and had been creative in trying to replicate their first time. He'd taken to not just shoving it in her, but actively fucking her with it. In and out, in and out, her sphincter getting looser with each thrust. He'd pause at the plug's widest spot as he pushed it in and take photos of her stretched out asshole. After discovering she loved for him to tap the base of the plug, he eventually tapped it so hard he pushed it into her. It had taken half an hour, two fingers and a thumb for him to coax it back out. He admonished her for begging for anal, calling her dirty, slutty, a whore. But as much as they'd explored their interest in anal, as much as they'd moved the goalpost, her mind always returned to the same question: what's next?

Realizing those memories weren't going to help her sleep, she actively pushed the thoughts from her mind. But an idle mind is an unruly thing, and soon the memories of that night returned, the two of them laying face to face as he introduced each of his new purchases, accompanying each with a vivid scenario. She recalled the way he struggled for words and the courage to say them at first, quickly replaced by that stony, unfettered confession of his most perverted fantasies. The way he paused when she wouldn't admit to wanting Mike and another guy to fill her pussy and asshole together, or she mumbled inaudibly into her pillow when he asked her if she had ever fantasized about their mutual friend Jake, or she pretended to not hear when he asked her if she ever tried a butt plug without him. She recalled her desire for him to punish her for her lack of cooperation, to spank or flog or choke her. Physical intensity was so much easier to cope with than mental. But all she got was that maddening pause. He knew he was going to get what he wanted - complete, honest answers to all of his questions. He just had to wait for her to realize her faux pas, then accept and admit to her depravity. He showed no uncertainty, no anger, no impatience. His absolute confidence was incredibly hot. She shifted her hips again uncomfortably.

Fine. If she was horny, too chicken shit to go out on a sexual limb, and not going to sleep, she might as well lean into it. Mike's birthday was coming up. She could order them a new toy. A flogger? Butt plug? Dildo? She reached for her phone again and browsed a few sex toy sites. She found a few things he'd like, but she wanted something he'd be truly excited about. She tried to put herself in his head. What had he been excited about lately? Immediately, she thought of their intimate photos he'd been posting on a variety of subreddits. He liked to DM with strangers about her, answering all questions, no matter how personal; he'd read their conversations back to her afterwards, showing her the dick pics they'd inevitably include.

Maybe she could get him a new camera or tripod? But she didn't know anything about photography. She browsed his reddit post history for inspiration. Another wave of horniness swept over her as she scrolled through pictures of the two of them. Well, really they were mostly of her. Mike took the photos, so couldn't get many good ones of the two of them together. He kept trying, but they were almost always awful.

She was about to put her phone down when a post in a local gone wild subreddit caught her eye. It read "M4A: 42m in town next week. Looking for something fun to fill my night." Lucy was surprised by the length of the post: almost a whole screen of background on the poster. He was more thoughtful and serious than most. She read it start to finish, thought for a bit, then read it through again. She composed a DM. Finger hovering over the send button, fear gripped her. What if the poster laughed at her? What if he was a creep? What if Mike was hurt? She jabbed the button before her insecurities could win out. Done. Can't be undone. She placed her phone back on the nightstand and closed her eyes. She had a plan. If it worked, it would be a hell of a birthday - for both of them.

Hours later, worriedly mulling over the possible repercussions of what she'd just done, Lucy fell asleep as the birds outside her window started their morning symphony.