Good Boy Pt. 01: County Fair

Glen and Emma had been together for a good five years or so. Things were hot between them for a good while, but like all long term relationships things cooled over time. It was normal, natural, and though they both had periods of sexual frustration, they made time for each other when they could and were loved well and mostly content.

Sadly, life set them back and Emma developed some health issues. Troubles with her heart increased and made them cautious with their sexual play activities, and a cluster of autoimmune diseases took most of her energy. A recent flare escalated to the point that an extended hospital stay became necessary.

Glen remained in good health and did his best to fulfill his role of caretaker while working two jobs. Nursing Em back to health was going to be a long task and a stressful one. The worry and the weight of responsibility took a toll on Glen; the quick wanks in his morning shower barely took the edge off his frustration and did little to relieve his stress. He needed something else, something to take his load off a little bit, something dirty.

A few weeks out of the hospital, Em was still weak, but her constant nausea and diarrhea had mostly abated, and her abdominal pain was manageable. She was getting antsy to get out of the house. On Monday, Facebooking with her friend Margaret, she got a hankering, and joined Glenn out on the lanai for a smoke.

"Hey, baby." Em said, lighting her cigarette. "The county fair is this week. Margaret has some stuff in competition."

"Oh, cool," Glen replied, not looking up from his phone.

"You think maybe we could go? Maybe Saturday?"

Glenn looked up, apprehensive.

"Well, sure. Maybe. Do you think you're well enough?"

Em shrugged. "It's been almost a week. I should be by then."

"Maybe." Glenn nodded. "Have to play that by ear. Tell you what, we got five days for you to recover. If you're well enough to suck my cock, you're probably well enough for the fair."

"Deal." Em laughed. "I'm so excited. I haven't been to the fair in years."

Em worked hard that week, pushing herself off the couch as often as she could, slamming down her aloe juices and protein shakes. She even managed to cook a meal on Thursday night. After Glen tidied up the dishes and a couple of evening smokes, they turned in.

As they lay in bed, not yet sleeping, Em remembered their deal. Glenn was on his side, turned away from her, breathing already slowed into sleep mode. He was obviously exhausted but she was sure he'd be receptive. After all it was his deal, and for the first time in months, she was ready. She spooned up next to him and began stroking his butt.

Glenn sighed and wiggled his ass a little. He always enjoyed a little backdoor attention, and any touch to his bottom got his attention. Em continued her light strokes, lightly tickling behind his balls. When she was sure he was ready, she struggled to her knees and pulled him onto his back.

Glenn was hard, eager. His cock pulsed in her hand. Em steadied herself with her other hand and leaned down taking him in her mouth. Glen groaned, thrusting gently up at her. She sucked gently and bobbed, working him as well as she could. She tired quickly though and leaned back on her heels, still holding his cock.

"I'm sorry," she whispered, stroking him weakly, "You're gonna have to..."

Glen's hand replaced her own, and he began stroking himself.

"My ass, please." He moaned, bending his knees up and spreading his legs. Em reached to the nightstand and grabbed the lube. Putting some on her middle finger, she snaked it between his legs and slowly slid it up his eager backside.

Glen licked his palm, then continued stroking. Em squirmed her finger, pressing on his prostate, firm and swollen under her touch. She leaned down on her elbow and hip and watched him intently.

"Oh, yes." He groaned, thrusting down on her. "Oh, god, another finger. Oh, please."

Em pulled out, leaving Glen to whimper, while she needlessly lubed her forefinger. She leaned back, resting her head on his thigh, and slowly worked both fingers in. Glen bucked, pushing down, eager to be penetrated.

"Good boy." She said, kissing his thigh. "Such a good boy."

"Yes." Glen hissed. "oh, fuck me. Fuck my hungry little asshole."

Glen licked his palm again and increased his pace, rocking on her fingers. Em held herself there, letting him do the work. She watched and waited. He would finish soon. When he gave the little grunts that she knew meant he was almost there, she leaned down and held her mouth open.

The first spurt spattered her lips and a little on her cheek. She lowered her mouth and took in the tip of his shaft. She sucked through the rest of his orgasm, swallowing, and kept sucking until he was spent and started to squirm away from the suddenly intense sensation.

She eased her fingers out and collapsed down onto his shoulder, cuddling him, basking in his glow. Glen shuddered a couple times as he came back to the world, and she held him.

"Was that ok, baby?" She asked.

Glen chuckled. "Yeah, that was ok. We can go to the fair."

"Yay!" Emma settled into Glen's shoulder and quickly fell asleep, the taste of her man lingering in her mouth. Glen laid, holding her, not easily falling asleep. Worried, second guessing the decision, anticipating. The sharp edge taken off his frustration, he ruminated on the encounter, still feeling the lingering presence of her fingers inside him. He needed it so much.

When Emma played with his ass, a peacefulness washed through him, pressures melted away, and he found a blissful escape. But it was fleeting. He needed a heightened experience, something more encompassing than a finger in the bum.

The next day he pulled out an old duffel bag that had some sex gear from his younger days. Things that hadn't seen much play with Emma. A leather slapper, some gags, and a leather harness. It had a couple of attachable plugs for the wearer and a base to mount a strap on. Fun for a girl and a boy.

There was no dildo though, and nothing in the bedside drawer would work. He would have to purchase something. The local dildo store was on the other side of town, not far from the fairgrounds. Glen decided they could make the quick detour after the fair day. He smiled and put the duffel away. He couldn't wait till tomorrow.

Fair day happened to be St. Patties, and they had shopped accordingly. They put the corned beef in the crock before heading out, and went into the bedroom to get dressed.

"Don't forget to wear something green." Emma said, "You don't want the leprechauns to pinch you."

Glenn laughed. "I wouldn't mind a little pinch on the bum, but ok. What are you wearing?"

"Oh, I've got green panties on."

"Oh." Glenn looked at her, wheels turning in his head. "Well, maybe, uh, you have another pair?"

Emma stared at him blankly, then quizzically.

"Yeah, uh, ya know, for me. Ya know, to wear."

They held their gaze for a moment and Emma turned to her drawer. She rummaged through for a few minutes, then pulled out a pair of hipsters with a green paisley pattern.

"These." Emma stated. "Try these on, let me see."

Glen dropped his pajama bottoms and kicked them off. He reached out tentatively.

"Go on." Emma encouraged. "Be a good boy. I wanna see."

Glen hunched down and stepped into the leg holes. The silky fabric felt smooth on his thighs and ass as he pulled them up over his hips. He adjusted his package as best he could. He was starting to plump up, almost beginning to stiffen.

"Ooh, good boy. Lose the shirt; show me."

Glen pulled off his shirt, and tossed it in his laundry pile. When he looked at Emma again, she was sporting a wicked grin. She motioned for him to turn around.

"Aren't you lovely. The leprechauns will sure be sorry they can't pinch this bum."

She gave him a little smack on the ass and he jumped. He turned back around and she was still grinning, staring down at his pantied crotch. She delicately licked her lips.

"I guess you like them."

Glen looked down at himself and his partial erection was clearly visible through the clingy fabric. It seemed to swell further from the attention. He reached down to adjust himself, amazed at how good it felt. It felt so naughty, but it also felt comforting. He felt softer, smoother, more yielding. Getting in touch with the femme side.

"Ok. Hurry get dressed. We want good close parking."

Glen threw on his clothes, making sure he wasn't going to flash anyone, and they headed off to the fair.

The drive over was pleasant, both of them grinning. Emma was excited talking about all the things they were gonna do, all the foods they were gonna eat. See the crafts, and the plants, and the cows, and ride the rides. Margaret had won several ribbons, including top place at the fair, and several of her items were on display. When they arrived and parked, the evil grin crept back.

"Thank you for bringing me, Baby." She slid her hand over his crotch, giving his package a squeeze. "I hope you have a good time too. Looking so pretty and all."

Glen nodded, feeling himself swell again. He adjusted himself as he got out and headed around to help Em out of the car. They headed to the ticket line, and Em found a place to sit and rest. Standing for ten or fifteen minutes was not a good use of her resources.

She watched Glen as he stood in line, happy with the luck of having him. She checked out his backside, making sure he wasn't peeking out. And she stifled a giggle. She was happy he was doing something to entertain himself. And having the sexy little secret was fun. She knew she'd be teasing him all day, keeping it sexy for him. It would bring her so much pleasure to give that to him.

Glen returned with the tickets. He helped her up and they entered the gates, and into the dealer's boothes. Em wanted to look at the jewelry, and they sampled some cheeses. Em stopped to pee, and Glen waited. When she came out she rested against the wall.

"You ok?" Glen asked, concerned.

"Yeah, just got excited and we went too fast. We'll go slower, ok?"

Glen nodded.

"You ok?" She pointedly glanced down at his crotch, flashing the evil grin.

Glen grinned and nodded, "Yeah, I'm feeling pretty. Pretty good."

Em took his arm, and they slowly sauntered into the fair. The craft booth was close, so they beelined there to check out Margaret's prize winners. The big prize was a crochet parasol, and it was prominently displayed. It was a fine piece of craftsmanship and they ooohed and ahhhed. They wandered around checking out the other entries, and then headed off to find food.

They shared some barbecue sliders, checked out the livestock, a live tiger show, went through the plant tent , and rode some rides. Glen got a little ride sick, and Em got to play caretaker for a little bit. They stopped for some lemonade and waited for the queasiness to pass, and Em could rest up a bit. Soon they both felt better and got up.

"Ok baby," Em said, "Better put on your big girl panties, we're going in the fun house."

Fun house, more gentler rides, another shared plate, and the end of a little family band concert took them back to the gate. It had been a couple hours, and though tired, Em did well and they left pleased at her progress. They got to the car and he got the door for her. She leaned in for a quick kiss, and whispered in his ear.

"Still feeling pretty?"

Glen nodded, getting a little goosey from her breath.

"Good boy. I think that's wonderful, cause you look lovely."

He helped her in the car, got in himself, and headed out of the lot.

"We gotta make a pit stop on the way home. I need to pick something up."

Em nodded. "K, Baby. That's fine."

Glen was nervous driving over to the adult toy store. They hadn't been in a while, since long before Em got sick. He wasn't sure of her reaction, afraid she would feel pressured, and a little shameful at what he was craving. But he stuck to his plan and soon they arrived. Em looked at the sign.

"Oh, oh my!"

What will Emma think about this? Will Glen find what he's looking for? How did the corned Beef turn out? Find out in the next installment.