Dear Diary - His New Toy

AUTHOR'S NOTE

These events take place eight months after the events in Dear Diary - Habeas Corpus.

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May 8^th, 2020

Dear Diary,

Last night had to be one of the sexist things I've ever done. Watching Ryan fucking his new toy as I knelt behind him, playing with his balls while telling him what to do, listening to him moaning as he fucked it... and that scream when he came the second time? Just thinking about it is making me wet.

What I wouldn't give to be twenty-years younger so I could keep up with him. We'd be fucking all the damn time, so much so he wouldn't have time for any extra pussy... even a fake one.

We are absolutely, positively, going to have to do that again... but not tonight. Tonight my wingpussy gets the night off because it's my turn for a good fucking.

"UPS just delivered this for you, Ms. Burkes," Rachael said, her voice slightly muffled by her mask as she placed the rectangular box on my desk. "New shoes?"

I glanced at the plain brown shipping box and tried not to blush as I put my mask on. I'd timed my purchase so the damn thing was supposed to be delivered tomorrow, on Friday, when I'd be the only one in the office. Despite the company's promise of discrete shipping, I didn't want to risk anyone knowing what I'd ordered, and I didn't want it delivered to my apartment in case the shipping wasn't as discrete as the company promised. There were no obvious markings on the outside of the box other than the shipping label, and it was about the right size to contain a shoe box, so I went with it.

"Yeah. I thought I'd treat myself."

I saw Rachael's smile in her eyes if not her lips behind the mask. "I'll be so glad when this is all over."

I bobbed my head. "Yeah. Me too. I've never bought shoes, or any clothes for that matter, online before, but..." I said with a shrug, allowing my voice to trail away as I pulled the box off my desk and put it on the floor.

"A girl's got to do what a girl's got to do, right?" she asked before turning away.

"That's right," I responded with an unseen smile of my own.

I waited until she was out of my office before picking up the box again and turning it over in my hands to examine all six sides. There was nothing that indicated what the box contained. I looked at the shipping label and sighed in relief while pulling my mask off and laying it on my desk. Other than the shipping marks UPS used, the label had only my name, my firm's address, and an originating address. Not daring to open the package in the office, I returned the box to the floor.

Nobody knew about Ryan and me. Late last year, Ryan Kirkwood had talked me into his bed, and I never left it. He claimed he wasn't ashamed that he was fucking a woman old enough to be his mother, and I damn sure wasn't ashamed that I had a lover that was young enough to be my son. Ryan made me feel, for the first time in perhaps decades, sexy and desirable. Best of all, because he'd turned twenty-eight less than a month ago, I didn't feel like I was robbing the cradle... and Jesus Christ could the man fuck.

Ryan wasn't model handsome, but he was still a good-looking guy, trim and well built, especially when compared to men my age, and glowed with youthful vitality. Better than how he looked or fucked was how he treated me. He was absolutely his own man, and was clearly the leader in our relationship, but he treated me better, and with more respect, than my ex-husband ever did... the selfish prick.

For the first couple of months, I wanted him all the fucking time. Our relationship wasn't a secret, but except for an occasional dinner out, most of our time together was spent with him churning my butter. We were friends with benefits, he was fucking me six or eight times a week, and I was loving it despite my near continual soreness. I hadn't realized how sex starved I was until I wasn't anymore, but despite my desire, too soon I couldn't keep up that torrid pace any longer.

Then the world began to burn. Restaurant, theaters, and bars began closing, and people were forced to stay inside. Paul, the other partner in Chelsey and Burkes, and I began alternating our days in the office, each of us bringing in one paralegal to work with us, while the rest of the office worked from home. Valverde and Kobelt, the firm where Ryan was an associate, had all their lawyers working out of their homes, and they went into the office only if they had to meet a client. We continued to see each other, and still enjoyed our time together, but even with little to do but stay home, the frequency of our fucking continued to slowly decline. The reduction wasn't because I wanted him less but because in another month I'd be fifty-three fucking years old. I simply couldn't fuck all the time like he could and needed time to recover, especially after one of our particularly energetic sessions.

With so little other entertainment options available, I'd been concerned that if I didn't put out he'd drop me like a hot rock. I hadn't given him enough credit and we'd slowly settled into the rhythm we were in now. We were fucking Wednesday night, Friday night, sometimes Saturday and Sunday morning, but always Saturday and Sunday night. By the time we were done Sunday night I was aching and ready for a break. In the beginning, while I was recovering, I'd supplemented the fucking with blowjobs and hand jobs when we were together, but he'd gradually put a stop to those, claiming to prefer to hold me until we could enjoy ourselves together.

Ryan and I didn't sleep together every night, but when we did, he was always diamond hard when we went to bed. He always kissed, caressed, and teased me throughout the night, amping up the intensity of the caresses from both his lips and fingers after we went to bed. It was his way of letting me know he wanted me if I was interested, but he never tried to coerce me, and best of all, he tried not to make me feel guilty when I denied him.

The key word was tried... because I did feel guilty. I knew he wanted me, and Goddammit, I wanted him, but some nights I just couldn't, and trying and failing was worse than not trying at all... for both us. I felt guilty for winding him up and then cutting him off, and he felt guilty for 'pushing' me into sex... even though I always assured him he hadn't pushed me into anything and that I wanted it as badly as he did.

I glanced at the box sitting at my feet. Tonight, I was going to surprise him with something new. When my womanhood was having a little R and R--rest and recover--I'd have a wingman... or wingwoman... or maybe most accurately, a wingpussy to back me up. Not knowing for sure if he'd be willing to go for it, I'd first thought I'd buy the basic model fleshlight, along with the recommended lubrication, cleaner, and powder. When he couldn't fuck me, he could fuck the toy, and I could enjoy watching him, but then I discovered the clear one at the same price point. Being able to see his rock-hard cock fucking and then coming inside a pussy?

Oh fuck yeah! Sign us up! the devil that sat on my left shoulder had brayed.

I smiled to myself. One of these days, listening to that bitch was going to get me into trouble, but I couldn't hate her. She was, after all, the reason I had Ryan now. She was the one who kicked my angel's ass and convinced me to go home with him that night.

Our first time together, he'd taken me to nirvana six times over the course of the night, and had wanted to fuck me a seventh time in the shower the next morning. I'd wanted him, I'd desperately wanted him that seventh time, but that had been an indicator of things to come. I'd had to shut him down because I was simply too sore to accept him. No matter how hard I tried, I couldn't out fuck him. That was great because he always left me a panting, shuddering, mess, but at the same time, I was afraid I was leaving him wanting. He never complained, and often claimed that I'd 'worn his ass out,' but I didn't know if he was telling me that because it was true, because he didn't want me to feel guilty, or because he was stroking my ego. I damn sure hadn't been able to ride his cock four times in one night again, and having a tumble at night and then again the next morning was the best I could manage.

I glanced at the box again. Tonight, if he'd go for it, I was going to find his limit. I'd been fantasizing about my evil plan since I clicked on the checkout button. During that amazing night of passion, we'd gone twice almost without pause. After he came, he ate me to another shattering orgasm before fucking me again. After our second round, there'd been a few hours pause as we slept. While I was sleeping the sleep of the truly well fucked, he slipped away for food before we fucked again, and then I'd woken him in the middle of the night for a fourth round. I wanted to know, I desperately wanted to know, how many times he could come before going soft, and how many times in a night I could revive him.

We're going to wear that sexy motherfucker's cock out tonight!

We need to make sure he wants too, my angel countered. We don't want to make him uncomfortable.

Uncomfortable? my devil sneered in response. By the time we're done with him tonight, he's going to be so relaxed he won't be able to be uncomfortable!

I smiled to myself. I didn't know why it mattered, considering I had a hard enough time keeping up with him as it was, but the idea of fucking him to exhaustion had become a brain worm. Having my devil constantly yammering on about him fucking the toy all night, while constantly screaming and coming as he did, was making me crazy.

During my divorce, I'd pulled back from my friends. I realized now that I was probably being stupid, but it seemed like my friends had started considering me a threat to their marriage. That had all changed with Ryan. He made me feel good about myself, and if this stupid fucking pandemic ever ended, and my life returned to normal, I wanted to start trying to reconnect. My smile spread slightly as I imagined us sitting around in a hen party, wine glasses in our hands as we compared their husbands to Ryan, and them realizing I was no threat to their marriage at all. Only a fool would trade a thoroughbred for an ass... and nobody had ever accused me of being a fool.

-oOo-

I dropped my purse and the box on my bed, almost tingling with excitement. Ryan normally came here because he claimed he was tired of seeing the same four walls in his apartment. I didn't mind. We alternated weekends and Wednesdays, but the other nights, if we spent the evening together, he was here.

I had about twenty minutes before I needed to start dinner, and I was anxious to see my purchase. I hurried to the kitchen and returned with scissors that I used to open the shipping box. Inside was a smaller box with the product visible in a clear window, along with another small cardboard box that contained the lubricant, cleaning spray, and the powder that was supposed to extend the life of the toy.

I slit open the small box, checked the contents to assure it was all there, and then placed the box aside and turned my attention to the toy itself. I removed it from its box and examined it. Fleshlight was a good name for the product because it looked like an oversized flashlight, except on the business end, where the lightbulb would be on a flashlight, there was a thick rubber pad with a vagina molded in. I carefully inserted my fingers into the orifice. It was slightly tough going as I hadn't used any of the lube. I considered doing so, and trying it again, but I didn't have a lot of time. I placed the toy aside and glanced over the directions. The only part that wasn't self-explanatory was the section on cleaning and storing, which I quickly, but carefully read.

I glanced at the clock and tucked everything away in my bedside table before hurrying outside and tossing the all the boxes into the complex's recycling bin. I wanted to leave no evidence of my purchase to spoil the surprise. If he refused to use his toy I had no way to return it, but I'd be too embarrassed to return it anyway, so no harm done.

I was preparing our meal, Caesar salads with leftover grilled chicken, when I heard the bolt snap. I continued slicing the chicken. Ryan had offered me a key to his apartment a month or so ago, and I'd reciprocated by giving him a key to mine. We were still clearing each visit in advance but were letting ourselves in with our keys. We were taking our growing relationship in steps, but I liked the path we were on.

He hummed as he entered and closed the door. "That looks good."

"You don't even know what we're having."

"I wasn't taking about the food."

He's such a sweetheart, my angel murmured.

And sexy as fuck too! my devil agreed.

I smiled as scraped the chicken onto a plate, pausing before opening the microwave as he surrounded me in his arms and nuzzled the back of my neck. I stood, enjoying the slow caress of his lips until he pulled back. I popped the chicken into the microwave, started it on half-power, and then turned to face him for a proper greeting. He needed no other invitation as he pulled me into a slow kiss.

After a leisurely caress of my lips, he released me and took a step back, glancing at the bowls of romaine, croutons, parmesan cheese, and the bottled dressing on the counter standing like a soldier at attention. I'd settled on a salad because I didn't want to feel full, and because I was so distracted by what I hoped we'd be doing later I was afraid I'd make a mess of anything complicated.

"Salads?"

"Yes. Is that okay?"

He smiled at me in that mischievous way he had. "Sure. You know me... I enjoy eating pretty much anything you put in front of me."

He said it in a perfectly normal voice, but he was exceptionally good at saying things that had a deeper meaning. It made me feel so damned wicked when he said things like that in public, when we could still go out in public, his words meaning one thing to me and something else entirely to anyone that might have overheard. Best of all, he knew when to do it, and when not to, so to not embarrass me.

"So I've noticed," I murmured as I turned to the microwave again.

"I have keep my strength up," he whispered as he stepped in close and pulled me backwards into his chest again, the breath from his words tickling my neck.

I could feel his hardness pressing against my back. His hands were draped loosely around my stomach to hold me close as we watched the microwave tick down to zero. When the appliance beeped, I opened the door.

"You don't seem to have any trouble keeping your strength... or anything else... up," I said as I retrieved the plate, a small smile dancing over my lips.

"That's not on me," he murmured as I pulled out of his embrace. "That's on you." He paused a heartbeat. "Not that I mind, of course."

I snickered and shook my head as I forked the chicken onto the salad. Wednesday, during our lovemaking, he'd fucked my tits until he came when I started drying after my orgasm. "Don't you ever stop?"

"What? You're the one making suggestive comments," he said as he pulled two glasses from the cabinet.

"Me?" I exclaimed in mock outrage. "What about you?"

"What about me?" he asked, his tone teasing. "I'm taking about salads, and you're over there talking about me keeping things up." I slapped playfully him on his ass. "See! That's what I'm talking about! I'm trying to get our drinks, and you're groping me." When he paused, I turned to see what he was doing. He was watching, clearly waiting for me to turn to face him. "Not that I mind that either," he rumbled.

Giggling, I picked up the dressing bottle, twisted the lid off, and squirted dressing onto the salads. He was still watching me, so when I finished, I slowly drew a finger along the edge of the bottle, picking up some of the dressing before it dripped, and wiped it on my tongue in the most suggestive manner I could as I moaned loudly and writhed my hips. He broke into a smile as he turned to the refrigerator, but not before I saw him blow air out of puffed cheeks. I giggled again, enjoying our teasing banter.

We ate and talked about our days. Valverde & Kobelt specialized in divorce and was a larger firm than Chelsey & Burkes, with two partners and nine associates. I'd first met Ryan when he'd assisted my husband's lawyer during our divorce. It was through that brief interaction, tenuous as it was, that had led to him being in my life. Chelsey & Burkes was much smaller, with Paul and I the only lawyers, and we specialized in real estate. Not surprisingly, as the grip of the pandemic tightened, our work was drying up and Valverde & Kobelt's was growing.

After he helped me tidy after dinner, we settled on the couch to Netflix and chill. Ryan, being a typical guy, liked science fiction, superhero, and action movies, and in what I thought was an interesting change of pace, animation. We were working our way through Jessica Jones, and though I'd started watching it because he wanted to see it, I'd becoming invested in the show now and was enjoying it.

We snuggled, his hand slowly caressing my breast and arm as we watched Jessica and Luke. I groaned to myself during the sex scene when the two lovers broke the bed, and if the bulge Ryan's pants was any indication, he'd found the scene enticing into as well.

We'd like to break the fucking bed with this sexy motherfucker! my devil whispered into my ear.

I slid my hand from his thigh to his manhood. He didn't move, but he began to slowly stroke my nipple with a finger. We watched the rest of the episode in silence while occasionally teasing each other with our touch.

"Another episode... or bed?" I asked as the end credits began to roll.

"Lady's choice," he murmured as he tipped my face up for a slow, gentle kiss.

I turned the television off. It was still early, but I couldn't take the tension anymore. He slid his arm from behind me and rose, offering me a hand as he did. When I placed my hand into his, he drew me to my feet and into his arms.

"I want you," he whispered, his lips a hairsbreadth from mine.

He must have felt emboldened by my caress his package during the show because he knew our schedule and was rarely so... obvious... with his desire on our off nights.

"And I want you..."

"But...?" he asked, picking up on my tone.

I smiled. "No buts."

His smile spread slightly as he closed the remaining distance to my lips. He pulled me in hard, kissing me more fully and deeply, causing my desire for him to spool up. If I was going to shut him down, he knew now would be the time I would normally begin backing off, but instead of pushing him away, I lost myself in his kiss.

As our kiss dissolved, he attacked my neck with kisses and gentle nips. I gasped, squirming under his onslaught, wadding my fingers in his hair to hold his lips to my neck. I reached between us to grip his package, delighting with the feel of him in my hand and remembering the pleasures his manhood brought me. His lips left my neck before he took me into another torrid kiss as his left hand caressed and kneaded my breast.

"You sure?" he rumbled as he pulled back from the kiss. "This is normally your night off."

"I'm sure," I whispered. "I have a surprise for you."

"I love your surprises," he growled before pulling me into another kiss.

He'd turned the heat down on the kiss, but I was having none of that. I wanted him running hot, and as I cranked the passion up in the kiss, he responded in kind before breaking from the kiss and kissing down my jaw and under my chin to nuzzle the valley of my breasts.