Greg's Best Day

As Jill recovered from her illness, she promised me a time I'd never forget!

© SouthernCrossfire - 2024. All rights reserved.

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It was Monday, but my mind wasn't on work.

No, I was thinking of something else. I was thinking of how it was going to be the best day.

In comparison, the previous Thursday had sucked. Work was work but when I got home hoping for a good time with Jill, my wife of nearly twenty years, she met me with the bad news.

"Gregory, I'm sorry but I'm still feeling like crap. The antibiotic that Dr. Wylder gave me hasn't seemed to help a bit so I'm going back tomorrow to see if she can give me something else."

"So you don't feel like having a little fun tonight?"

She gave a little sigh and rolled her eyes. "Fun for you maybe if I don't pass this bug along to you. I'm sorry, honey, but I can't."

"I'm sorry, sweetie," I said. "I didn't mean to pressure you. Say, why don't you go to bed early and get some rest. I'll clean up downstairs and be up in a little while."

She'd been sick and moody for almost two weeks, so while I wanted to help her and help with the household chores because I loved her, I wasn't being entirely altruistic. After the dishes were washed, the scheduled household chores were finished, and Jill was in bed, I was able to go down to the basement and take care of a bit of my frustration with the help of a point-of-view video starring a bleach blonde with really nice tits, strong thighs, and a great looking pussy. Her eyes caressed the camera as if it was her lover as she fucked the lucky bastard whose body stood in for that of the viewer.

Then came Friday, of course, which was good only because it was the end of the work week. When I got home hoping that Jill would be feeling better and in the mood for a good time for a change, she said, "Dr. Wylder gave me a different antibiotic and said for me to monitor my progress."

"Think we can—"

"No. She said for me to get plenty of rest to let it kick in, hopefully by Sunday but she was sure it would be working by Monday at the latest. If it's not and I'm not feeling better by Monday morning, she wants me back there for a full battery of tests because it could be something worse. She doesn't think it will come to that, but it's still a little scary."

"I'm so sorry, sweetie," I said, worried about her but not telling her I was feeling almost as sorry for my lack of action as I was for her.

I love Jill but I tend to be a selfish bastard.

It was a redhead in the video later on Friday night. I swear, I think her tits were even nicer than the blonde's on Thursday and the freckles on her face and across her chest and breasts were practically hypnotic as they moved to her motions. With Jill asleep upstairs, I took it slow and steady, giving myself a delicious buildup as I watched her ride, imagining the motions, the feel, and the coming release.

When it came—well, they don't call it coming for nothing. As for those enticing freckles, oh, the dots I could have connected for her as my huge ropes flew in the basement bathroom. The pearl necklace with which I could have graced her! Still, my balls told me it wasn't nearly enough.

And then I realized what I'd done and had to clean the fucking bathroom!

Yeah, Friday actually sucked too.

Saturday, on the other hand, had been a very good day. I met some friends for a round of golf at 7:45 a.m. and then, with Jill out of commission, I headed home to put my main plans for the day into action.

Those plans centered on Elaina Muñoz, the brunette with big knockers from a few doors down, and easing my ongoing frustrations that the blonde and redheaded video stars hadn't quite taken care of despite the temporary relief. With her husband and kids having gone to see his parents, Elaina was available for the afternoon and she told me she was looking forward to making the most of it.

Elaina had been unhappy in her marriage to Manuel, a former single-A baseball player who now worked primarily from home as a product marketing representative when he wasn't visiting clients. Like so many athletes who have trouble adjusting their caloric intake and exercise level after retiring, Mani had put on a lot of weight over the ten years of their marriage, and Elaina wasn't pleased with him or where she feared they were going together if he didn't change. So far, he'd resisted her efforts and her nagging, which was probably at least part of the reason he'd seized the opportunity to get away from it all for a little while.

Like Elaina with Mani, I loved my wife but I'd become somewhat bored with my marriage and needed something more. Jill had been so much fun, so affectionate, during the early years of our marriage, but after we decided to not have children, she slowly changed, becoming more focused on her career and less focused on me and on continuing the fun times we'd had in the past. I missed that and it weighed heavily on me over time.

With the two of us at least somewhat displeased with the situation at our respective homes, Elaina and I had grown closer over the past three years since they'd moved into the neighborhood. Elaina laughingly claimed that her situation was worse in that Mani mostly drank beer, belched and farted, and then fucked her for fun whereas I ran and golfed to stay in great shape and got to fuck her for fun and fuck Jill for the practice.

Whenever Jill would let me, anyway.

Elaina was in her mid-30s, with an olive skin tone, dark hair, and almost-black eyes that reflected her Hispanic background and sometimes fiery temper that was usually directed at Mani. However, she had a ready smile at times, a frequently generous laugh, and a rather insatiable appetite in bed. Having given birth to four children and having to work at a desk job outside of the home, Elaina also had a generous ass and nice-sized tits that had probably produced countless gallons of milk over the years.

While definitely not wanting any rugrats of my own, I almost hoped that Mani would knock her up again while Elaina and I were involved so I could have a sample. The thought, which had become more frequent in recent days since Jill's illness had put her off limits, made my toes curl and my dick as hard as steel.

Telling Jill goodbye, I said that I was going to the office to catch up on some claims and would be home around 6 o'clock or so on Saturday evening. And just like that, I was off to continue the heated affair that Elaina and I had begun about six months before. I'd lost track of the number of times since starting that we'd pulled the wool over the eyes of our spouses, making up excuses that were never questioned, that were always believed.

This time, I turned off my cell as I pulled out of our driveway and then parked my car a few blocks away behind a business that was closed on Saturdays. The car was safe there and I knew it wouldn't be seen. It was a relatively warm but windy day in late March but I didn't want to be recognized by anyone in the neighborhood, so I slipped my plain black hoodie on and flipped the hood up before exiting the car and walking back to our street. I made my way straight up Elaina's drive, through her garage, and into her arms.

"Oh, lover, you've come. Now, get ready because I'm going to make you do just that," she said with a grin.

She pushed me back against the kitchen counter, her tongue probing my mouth, as her hands unfastened my belt. My pants fell away and she dropped to her knees before me.

"Oh, yeah!" she practically squealed. While Mani and I were both within an inch or so of 6-feet tall, he had about seventy or eighty really unneeded pounds on me. Elaina had told me in the past that she liked that my belly didn't get in the way when she needed my cock.

With the path clear and my cock hard, it was in her mouth and down her throat in seconds. As I gave a sigh and enjoyed the sensations, I knew my little subterfuge with my wife would be well worth it once again.

Elaina's pretty under usual circumstances but at no risk of winning any beauty contests; however, when she's on her knees in front of me and her head's going up and down on my rod, she's about the most beautiful woman imaginable and I tell her that in no uncertain terms.

She loved my encouragement and I loved what she was doing to me, bobbing up and down, shallow and deep, kissing, licking, and stroking me, making me tingle and my balls yearn to explode. As ready as I was, it didn't take her long before I couldn't control it and had to let it fly. When I did, she found herself happily gulping what felt like a quart of my pent-up spunk.

She often tells me that Mani takes her for granted, so whenever we're together, I keep the praise coming so she'll do anything for me and so I can keep fulfilling her needs. This time, I was gripping the counter to steady myself as I pulsed and fought to keep my knees from collapsing. Then, as she milked the last dabs from my length and sucked me clean, I praised her, saying, "Good God, Elaina, you're really wonderful and so fucking good at that. That's made me feel better than I've felt since our last time together. Now, let me do something special for you, beautiful, so we can get down to some real business."

Yes, this was very nice for a start, and, just like Jill, she was smiling at me, believing every word of what I said because she wanted to believe it. Feeling the wonderful rush pass over me, I grinned, knowing this time it was true, and she was grinning back in anticipation of what was to come.

Taking her in my arms again, we stood with me propped against the counter and her pressed against me in her thin, little dress that showed all of her curves. From what I could see and feel, I knew she didn't have on a bra under it, and, I suspected, if she had on panties, they had to be a practically non-existent thong or a G-string.

The afternoon got even more interesting from there as I stripped Elaina's little dress up and over her head, finding that she, yes indeed, had absolutely nothing on underneath it. I was cupping and suckling those knockers, imagining her milk trickling into my mouth as I pulled up one leg and slid my fingers home into her warm, wet depths.

Within moments, I'd positioned myself so I had two fingers inside on her G-spot and my thumb on her clit. Then I started working her and Elaina was moaning in no time.

After so many kids, Elaina's pussy's not quite as tight as Jill's, but free pussy is great pussy, no matter how you fuck it, and I've fucked Elaina's a lot.

A whole lot.

First, though, I set her on the counter, pushed her legs up and wide, and went to town on eating her pussy with a hunger that made me throb. Highlighted by a dark, trimmed bush, her clit is large compared to Jill's dot and it doesn't take much for it to get her off. My fingers went back to massaging her G-spot as I tongued her, taking her up, bringing her down a bit, and then back up again. Then she moaned out loud and her thighs clamped about me as her face slowly relaxed and she whispered how much she loved me doing that for her.

We'd agreed long before that what we had wasn't love and that neither of us wanted it. While we weren't completely happy with our respective situation at home, we weren't all that upset and weren't planning to get out of our respective marriages either.

That didn't mean we couldn't have fun though. A lot of fun.

"Oh, Greg, you make me see stars, lover. Great big fucking stars! You think you're ready to give it to me for real?"

"Yes, ma'am!" I replied. "Let's see if we can see those fucking stars together!"

With my rod like a rock again from my great dining experience, that's what we did for the next round, again right there on the countertop, my cock in her pussy from behind, slamming against her generous ass that makes Jill's admittedly really nice one look small. Elaina gets loud when she gets close, and she got close really fast this time, with me pushing her over the edge as I filled her again, from below this time, and she came all over me.

I'm glad she got to clean the kitchen floor instead—

***

The phone rang, startling me, and bringing me back to my early Monday afternoon efforts, ripping me away from my sweet memories of our fucking and how I'd eaten her out again and fucked once more later in the afternoon.

Glancing down at the claim I'd been reviewing, I shook my head and made a note to recheck it after finishing on the phone.

The caller ID line on the phone listed "Natalie," our receptionist and switchboard operator, which made me want to pick it up even more. Whereas Elaina was a mom I already loved to fuck, Nat was a 24-year-old beauty who'd been on my Want-To-Do List since even before I started with Elaina.

"Hi, Nat. What's up?"

"Hi, Gregory, looks like you have a great afternoon planned! Somebody's sent you a big box of flowers. You need to come up and sign for them."

I wasn't expecting anything but I knew at once what they were, an offering from Jill, to keep my motor running throughout the day as I looked forward to the fuckfest we'd have when I got home.

***

Yes, on Saturday, I took a quick shower at Elaina's after we were done and then ran the few blocks back to my car, breaking a sweat as I did to cover up any smells of sex or Manuel's body wash. When I entered the house, I complained to Jill that it had been a warm day but that the air conditioner hadn't been on at the office and that I'd had a hot, sweaty time.

That it had been at Elaina's and hadn't been as miserable as I implied was left unsaid.

"Jill, let's go upstairs and make love," I started. "You've been sick and we haven't gotten to do it in like two weeks."

Guilt often works wonders on her, but not this time.

"No, Gregory," she practically moaned. "I told you, I can't. Not until at least tomorrow and probably until Monday when the new antibiotic has had time to fully kick in and lick this bug."

"I'm sorry, sweetie. I'm thinking with my little head that's craving action more than my big one that knows better," I groused. "Maybe if you can lay your wonderful healing hands on me tonight and give me a release?"

Jill's hand jobs aren't quite as good as her blow jobs but they're far better than nothing and maybe that guilt still had a chance? I could see her thinking, about to break and offer me something.

She was teetering on the edge, about to cave when, to my surprise, she shook her head and my heart slumped. Then she threw me a lifeline.

"I'll tell you what, assuming I keep improving like this, I'll be feeling better by Monday and we'll be able to make love again then. Let's plan on having a fun time Monday night to make up for all the times we've missed recently, okay? In fact, I'll make you a promise. I'm going to make Monday a day you'll never, ever forget."

She said it with a grin, the first time I'd seen her smile at all in days.

"Oh, really? Are you sure, Jill?"

"Yeah," she said, nodding, her smile beaming. "In fact, I'll make a deal with you." Her fingers trailed over my chest, enticingly.

"If you'll promise me that you won't come between now and Monday night—no, no unscheduled releases in the shower, no trips downstairs to the basement bathroom or anywhere else, not even once—after we make love the first time, I'll give you a blow job—and you can come on my tits—no, wait! I'll tell you what, you can come wherever you want. And then—"

She paused, causing my racing heart to take a break as I held my breath. A wicked grin crossed her face.

"—I'll lick up every bit of it. How about that? You like?"

Oh, my, did I like! My heart thumped like crazy at the thought, threatening to leap out of my chest. When Jill gave me a "complete" blow job, she always wanted my jizz shot deep in her mouth and down her throat where it wouldn't make a mess but where I couldn't enjoy the visual. Seeing my semen spray in her mouth, on her cheeks and forehead, and maybe even into her hair, was a rare dream come true. Watching her wipe a finger through my thick cum and lick it off—I practically shivered at the thought.

"Fuck yeah!" I shouted.

She was grinning and laughing harder than I'd seen her laugh in years. "Hold on, honey! We're not done yet!"

She said it like the announcer on all of those TV game shows and I couldn't help grinning, wondering what else she might throw in to sweeten the pot.

"And after that, if you can get hard again, with a little, or maybe a lot of help from yours truly," she added before a pregnant pause, "I'll, ahem, let you, ahem—"

She looked like the cat that ate the canary as she whispered, "—fuck my ass."

"No way!"

That was the Holy Grail, something we'd done maybe six or seven times in nearly twenty years of marriage. Okay, maybe I'd been a little too enthusiastic the first time and it hadn't been good for her as her tight little hole squeezed me to an incredible orgasm while I drilled her, but I'd learned my lesson and had been much more careful and considerate in the relatively few times she'd let me do it since.

"With me being sick for so long, I've been thinking of ways I can make it up to you and I realized we hadn't done that since Dan and Linda's party a few years ago. I'm sorry, honey. You know I don't particularly like it, but I like to do it for you sometimes because I love to make you happy."

"Oh, Jill, that's so sweet! Thank you! This will be a night we'll remember for a long, long time."

"Uh huh," she agreed. "You better believe it. Remember though, no coming between now and Monday night. I want every single bit of your cum saved up and ready for me." She stressed "every single bit," hitting each word hard and pausing so I'd remember them.

Jill's hand was down my pants, cupping my balls. "In fact, I want these so fucking full when you get home on Monday night that you'll barely be able to walk, and when you come for me—over and over again, I hope—that you feel like it's an atom bomb going off every single time, okay? Deal?" Again, she stressed "every single time" like before so I'd know she was serious.

In actuality, I've read that doctors say men don't store up semen, but I knew in my case that thinking about sex and being on edge for hours on end in preparation for what I expected to come made my testicles feel like they were inflated like basketballs. Then when I come in jets afterward—oh, baby!

"You'd better believe it," I agreed. "I'm looking forward to fucking you six ways from Sunday."

"Monday," she said teasingly, while knowing the idiom. "In fact, I want you thinking about it all weekend and making as many of those little swimmers as you can. Hey, you might even want to get off a little early that night so we can make it count."

"Definitely!"

***

As I walked through the office that Monday with my hands shoved deep in my pockets, I was concentrating, hoping my hard cock wasn't too obvious in my trousers as I approached the lobby but knowing all the while that it was. My balls already felt swollen and I suspected that my boxer briefs were coated in precum that had been leaking off and on all day as I looked forward to what was to come.

I peeked around the opening to see that Natalie wasn't looking my way before entering and then positioned myself next to the desk where she couldn't see my problem.

If the courier guy saw my bulge—well, he could just be fucking jealous as far as I was concerned.

"Hi, package for Mr. Gregory Blish from his loving wife, Jill. You're Gregory?"

"In the flesh," I said, "and damn lucky to be."

"Yeah, based on this, I'm guessing so," laughed the courier, who had Tommy embroidered on his shirt in a cursive script below a light jacket that hung wide open. He was holding a big flower box with at least a dozen roses I guessed, and maybe two or three.