Playing For Keeps - Bottom's Up
Ennis got busy as soon as Jack drove away. There were three big boxes and four smaller ones. He got the steam iron from the back, hung the shirts and trousers on a tall rack and started steaming, He was through the second box when he heard knocking on the front door. He checked his watch. Jack had said he’d be back in half an hour, but almost an hour had gone by. Punctuality was obviously not one of his strong suits.
He made up for it though, Ennis decided immediately, by looking good enough to strip down and eat right there on the street. Ennis twisted the lock and pushed the glass door open just wide enough for Jack to get in, breathed deep as he slid by, his body brushing against Ennis’ as he came through the door. He’d taken a shower, smelled fresh and clean, like scented body wash and shampoo. He was dressed similarly to Ennis, in faded jeans and a tight white t-shirt. Ennis could see dark hair in the vee, and his nipples were hard under the thin cotton. Ennis swallowed hard - if the store was ready by the morning, it would be a miracle.
Ennis shut and relocked the door, shoved his hands into his pockets. Jack was looking at the sale shirts folded neatly on the table, messing them up, of course. “I’ve never been shopping in here before. I get most of my clothes at the mall, Abercrombie and Fitch and places like that.”
“Most of our clients are older than us, at least in their thirties, and usually pretty well off.”
“Yeah, I guess so. This stuff is way expensive.”
“They like it though.”
Jack nodded. Ennis led the way back to the area where he was working. “You’re part owner of this store, aren’t you?”
“Yeah. My dad and uncle started it when I was just a kid. My dad and mom retired, moved out to the beach last year. I’ve worked here since I was a teenager, so when he got ready to leave my dad just gave me his share.”
“That’s cool.”
“I guess. It’s not really my dream job, but it’s a good living, and I get to meet lots of interesting people.”
Ennis took a minute to show Jack what he needed him to do, and for a while they worked quietly, talking some about the clothes and the store. Ennis told Jack about what a crackerjack his uncle could be, and about his eccentric Aunt Evelyn who ran the cash register and did the books. They talked some about sports, and Jack told Ennis about life at college. He was going for a degree in graphic arts.
Jack took up the thread of their earlier conversation as he opened the last box of golf shirts and put them on hangers. “Do you get many women customers here, or is it mostly guys?”
Hmmmmmm...... “We get women shopping for their dad’s and husbands. Younger guys seem to like to do their own shopping. We get a lot of them too.”
Jack nodded, said, “Cool,” then got quiet, focusing on the task at hand.
After a few minutes of comfortable silence, Ennis asked, “You’re not standing anybody up to do this, are you? Kinda surprising that you don’t have a date tonight.”
Jack shook his head, and the blush was back. “No. I broke up with my b...... umm....... with the person I was going out with a couple of weeks ago. I haven’t started seeing anybody else yet.”
That was an interesting slip. Ennis decided to quit fucking around and ask the question. They were almost done with the clothes, and the accessories wouldn’t take that long. “So... this person you were going out with..... did they pee standing up ?”
Ennis watched, amazed at how red Jack's face got so quickly. But he didn’t lie or even stall much, just nodded. “Yeah. His name was Michael. But it’s not a big deal. It’s not like I was in love with him or anything.”
“Oh. I see. Well, that’s good then, I guess.” Ennis wasn’t sure what he was supposed to say to that, so he just went for safe. Jack looked like he had more to say anyway.
“So I told some of my friends that I was delivering stuff here, and one of them said he’d seen you at Dudley’s, with a guy.”
They stared at each other over the mostly empty boxes. Dudley's was a gay bar. It had been several weeks since he’d been there, but he had been with a date that night. They’d only gone out a couple of times, didn’t really have much in common and had had the sense to realize it before things got messy.
“Yeah. I go there sometimes.” Ennis saw the little twitch at the corners of Jack’s mouth again, but he just nodded, said, “Me too,” and stayed busy with the shirts. Silence fell again, and after about thirty minutes, they were done -mannequins dressed, clothes wrinkle free and on the racks, belts and ties and sundry items all in place. They quickly gathered up the trash, stuffed it all into the biggest boxes and drug them out back to the dumpster.
Ennis checked his watch as they went back into the store. It was 10:15. Still time to go out for a drink, have a late dinner......fuck....... suddenly he wanted nothing more than to take Jack home with him to his townhouse on the bay and make love to him all night long. But Jack, it seemed, had other plans.
“Where’re we gonna do this?”
Ennis didn’t follow at first, was still thinking about food and bed and sex. “Do what?”
“You know..... finish up. You were gonna punish me, remember? Guess I owe you, for being late and screwing up your evening and all.”
It was on the tip of Ennis’ tongue to say ‘Forget that shit - just screw me and we’ll call it even,’ but the look in Jack’s eyes stopped him. The innocent boy was still there, on the outside, blushing and nervous, but there was more to him deep inside that Ennis hadn’t had the chance to explore yet, and it was showing through, a wicked gleam in his eyes, the way his tongue kept sneaking out at the corners of his mouth. And he was sweating again, even though the air conditioner was turned down low and the store was close to chilly. The smell of Jack’s excitement sent the blood flowing back to Ennis’ cock in record time, almost leaving him dizzy when it surged south so fast.
“Don’t worry. I haven’t forgotten,” Ennis assured him, wrapping long fingers around Jack's bicep and shoving him gently back towards the office. Ennis walked fast, anxious to see some skin, and Jack hurried, almost stumbling to keep the pace.
The office wasn’t huge, by any means, but it was spacious enough for a desk and a couple of chairs for visitors. The chairs were nice - cast-offs from Aunt Evelyn’s never-ending need to redecorate. Ennis had come by most of the furniture in his townhouse the very same way. These particular chairs were from her most recently discarded dining room suite. They were armless, wide bottomed and sturdy - perfect for eating a nice meal, or delivering a sound spanking.
Ennis slammed the door behind them as they entered the room, held Jack for a second as he stopped to lock it - just in case the opera let out early, then pulled Jack over to the chairs facing the massive wooden desk. “This looks like as good a spot as any. Don’t you think?”
Jack’s eyes were big and panicked as he looked around the room. It was a very basic, ordinary office, nothing scary at all, with nice, bland pictures on the wall and a dusty potted plant in the corner. If Ennis hadn’t sensed Jack’s excitement earlier, he might be worried now that he was really afraid, but Ennis was becoming more and more convinced as every second passed that this was Jack’s fantasy, and that he was just using him to play it out. Ennis had never been used to fulfill a fantasy before, at least not to his knowledge, and it made him feel special and good.
“Yeah. Guess it doesn’t really matter where. At least this is private. This is embarrassing enough as it is - don’t want the whole world knowing about it.”
“’Course you don’t. This is just between you and me, I promise,” Ennis assured him, and even though they hadn’t gone there yet, Ennis cradled Jack’s stubbled jaw in his hand and gave him one soft, sweet kiss. Jack responded to the kiss with parted lips and a little bit of tongue. It was hard to pull away, but Ennis did. Sex would be awesome, and Ennis felt fairly certain they’d do that later, but for now, he didn’t want to leave Jack wanting. He sat down in one of the chairs.
“I don’t know how your dad usually does things, but when I was a kid, all my spankings were on my naked ass. Far as I’m concerned, that’s the only way to do it.” Ennis looked up, met Jack’s worried gaze staring down at him as he reached for buttons.
“I don’t know, Ennis. That might be more embarrassing than I can handle.”
Ennis grinned. “How come?”
Jack blushed. “’Cause........”
Ennis drug his finger down the hard ridge of flesh jutting out to the side from Jack’s fly. “’Cause a this?”
Ennis was amazed Jack had enough blood left to sustain his erection, as red as his face was, but there it was, big and hard beneath his fingers. Jack just nodded and said, “Yeah.”
“You always get one of these when you get your spankings?” Ennis asked, slowly unbuttoning the fly of Jack’s jeans. The whole package was less than a foot from his face, and there was no way Jack was going over his knee without him having a taste of that first.
“Ummmm....... not... ummmmm........ usually.........” Jack said, his breath uneven, making little hitches in his talk.
“That’s probably good. It’d freak your dad out, I bet.”
“Probably. Doesn’t bother you though?”
“Not at all. All I’m interested in right now is your ass.......” Ennis assured him, but made a liar out of himself the very next second, because as soon as he got Jack’s fly unbuttoned, his dick popped out, and Ennis had it in his hands before he could stop himself. “This is nice though... perfect........ just so you’ll know.” And then he kissed it, in case Jack had any lingering doubts about how much he wanted him, and Jack grabbed his head and held him still while he pushed in and thrust into his mouth.
Ennis pulled off after a minute, and Jack let him go easily enough. “Kinda getting ahead of yourself there, aren’t you?” Ennis asked, as soon as he could breathe and speak again. His fingers were locked onto Jack’s naked hips. He forced them to let go, then slid them down Jack’s thighs to the jeans that were hanging there and pushed them all the way down past his knees. Jack’s dick was still there, fat and full in his face, glistening with his spit and Jack's desire, and Ennis kissed it one last time before he pushed him off to the side.
“Get over my lap, Jack. You know you got this coming.”
“Mmmmmmmmm,” was the only response he got, but Jack did his bidding and was soon bent over his lap. Ennis pushed him forward till he felt Jack’s dick catch between his thighs, leaving his ass high and ready, his butt cheeks tight and round... perfect. Ennis smoothed his hand over them, caressing them. Jack moaned softly, hands flat on the floor, braced for what was to come.
“How many licks does your dad usually give you with the strap?”
Jack was quiet for a few seconds, then answered. “Twenty.”
“So if I’m only using my hand, guess I should give you more, huh?”
More quiet, then Jack answered. “Think that’s your call. I’m not in much of a position to say.”
Ennis grinned, rubbed his hand over Jack’s bottom one more time, letting his fingers trail up his crack. Ennis couldn’t wait to be done with this, so that he could do other stuff to Jack’s ass, but the way his dick was feeling right now, he probably wouldn’t be good for much more than sticking it in. He wanted their first time to be better than that...... Maybe they’d come fast the first time just doing this, then go to his place and make love like it was meant to be done.
“You ready?” Ennis asked, felt the motion when Jack nodded, heard a belated “Yeah” coming from down below.
Ennis gave the pale white cheeks one final rub, then lifted his arm and sent his hand crashing down with a loud “smack!” Jack lurched on his lap and groaned. Ennis felt the swollen tip of Jack's dick dragging against this thigh, but he tried not to think much about it. One lick down and who knew how many to go. The last thing he needed to be thinking about was Jack’s dick. He had unfinished business with his ass first.
And business with Jack’s ass was definitely not a bad thing. Ennis watched the spot he’d slapped go from white to red in an instant, saw his handprint taking shape..... yeah....... that was awesome..... He drew back and fired again, a flurry of slaps that had Jack rocking on his lap, moaning louder as the sting built up to a firey burn in his bottom. Ennis wasn’t counting, had no idea how many times he swatted him, all he knew was the sound of Jack’s cries, the feel of his dick sliding hot and hard against his leg, the view of Jack’s ass, legs spreading wider as the spanking went on, till - towards the end - Ennis could see his asshole winking up at him through a thin covering of hair. Once Ennis got an eyeful of that, the spanking was pretty much done. With a last, hard round of slaps, he finished up.
“Think maybe you’ll be on time next time, Jack?”
Jack groaned. “Shit, Ennis! I’ll be on time right now if you keep goin’!”
“Is this the way you want it, or you want something else?” Ennis asked, his hand settled into rubbing him in spite of all he could do to hold off.
He could barely hear Jack’s quiet answer. “Something else might be nice.”
“Come ‘ere.” Ennis pulled him up off his lap, brought him around quickly to straddle his legs and sit on him. They were kissing in an instant, and Ennis had his dick out seconds after Jack landed on him.
“I wanna make love with you, but I think we’re both too far gone for that. Don’t you?”
“I’m gonna come in about thirty seconds, Ennis, with or without you.” Jack had his arms twined around Ennis’ neck, nothing touching his dick but air, but Ennis believed him, he was that fired up. His legs were spread wide, wrapped around the chair back, and his asshole was stretched tight. Ennis reached up under him and fingered it, got an agonized moan in return.
“Fuck that feels good, Ennis.”
Jack seemed at ease with the touching, but Ennis vaguely remembered his earlier curiosity about whether or not Jack had had a lover before. He wished he’d asked before they got to this point, but there’d never been a good time, and now wasn’t either. Ennis couldn’t focus on anything at this point but sex. They kissed for another minute - Ennis loving the erotic play of Jack’s tongue, dancing in and out of his mouth, feuding fiercely with his own tongue, then sucking and licking sweetly at his bottom lip. Ennis felt the need to come tightening in his belly and his balls. He massaged Jack’s asshole harder.
“Ohhhhhhhh goddamnnnnnnnn that feels so fuckin’ good........” Jack moaned, and he threw his head back, kissing forgotten as he wiggled his ass into Ennis’ touch. His own hands had found their way down to Ennis’ dick, were wrapped around his swollen shaft, squeezing him tight, stroking him fast as he squirmed on Ennis’ fingers, until finally his hole gave up the fight and two of Ennis’ fingers slid right in.
“Oooooooooooohhhhhhhhhhhh fuckkkkkkkkkkk!” Jack cried, working
himself hard on Ennis’ hand, upping the action on Ennis’ dick in time with his movements.
It all created a total pleasure overload for Ennis. He whispered, “Kiss me,” and as Jack’s lips came slamming down on his, teeth and tongues crashing together in a wet, passionate frenzy, Ennis gave up the fight to last, let pleasure overtake him as his orgasm rolled through him and he shot off, spurt after long, hot spurt of come into Jack’s hands. Jack kept riding his hand hard, and within a few more seconds he was there too, coming furiously, spewing jizz all over Ennis’ chest and belly.
They clung to each other in the aftermath, both craving the closeness and the comfort of the other’s touch, and when they finally pulled apart, they didn’t move far, made room only for more sweet, after-sex kisses, until their hearts were calm and their minds were clear, and they felt ready to handle whatever came next.