As the day for Joy's "detention" session approached, it became increasingly difficult for her to focus on anything else. Her first Correction Match with Jennifer had been emotionally draining and humiliating, and she had no doubts that detention was going to be worse. It felt so childish for a grown, 41-year old woman to be required to attend "detention" and subjected to humiliating punishments. But Joy kept reminding herself that it was an alternative to prison and that made it all necessary, as unfair as it may be.
More than once, the thought of asking her boyfriend Jeff to help prepare mentally for her ordeals had crossed Joy's mind. But if she came fully clean, what would he think about Joy having been arrested? And what would he think about her hiding from him that she was in the Correction Match program until she was so far along? While Joy ultimately opted against telling Jeff everything because she was afraid of what it could mean for their relationship, she did come up with a plot to try to enlist his unwitting help.
Jeff was a few years older than Joy and, like Joy, divorced. He had two daughters, eleven and thirteen, who he saw every other weekend and one weeknight each week. He'd just celebrated his 20th anniversary as a city firefighter, and when he wasn't working or spending time with his daughters, he occupied himself with a vintage car he'd been restoring. He was an attractive man with a fit physique and a seemingly perpetual five-o-clock shadow.
On Sunday evening, three days before Joy's detention session, she met Jeff for dinner at Giovanni's, a local Italian restaurant. She had to admit to herself that she looked very nice as she pulled on a black dress and gave herself a once over in the mirror before leaving the house. Dinner was really nice, and she even managed not to think about Correction Match for the entire time. When the waiter brought the dessert menu, Joy leaned over and whispered in Jeff's ear.
Come over to my place for dessert.
Jeff grinned and nodded before quickly paying the check. When they arrived at Joy's house, she got right down to business. "Come upstairs -- there's something I want to show you," she said, not even bothering to go through the motions of offering actual dessert. Jeff playfully pinched Joy's bottom as he followed her upstairs. The sex in their relationship had been good, but reasonably vanilla so far. Jeff was therefore slightly surprised when he turned the corner into Joy's bedroom and saw an array of sex toys. There was a pair of leather wrist cuffs, a leather paddle, a bottle of lube, and a black silicon anal plug.
"I was 15 minutes late to meet you at the restaurant earlier," Joy said. "I shouldn't have done that. I want you to punish me for it," Joy finally said, looking directly into Jeff's eyes almost bashfully.
Jeff processed what Joy had just proposed. He wasn't so naΓ―ve that he hadn't encountered sexual roleplaying before, although in their relationship to date, Joy hadn't given off a submissive vibe or anything else suggesting she might be into play punishments. Nevertheless, it intrigued him.
"Oh, yes. This could be fun," Jeff responded.
Joy immediately corrected him. "No -- don't make it fun. Give me a punishment. I shouldn't have treated you like that. "Tell me what my punishment is going to be," she implored, her eyes darting over to the butt plug.
One of the things that kept weighing on Joy's mind was the possibility that she'd receive an anal insertion as a punishment during her detention session. She'd vetoed that option for her first Correction Match session, but doubted she'd be able to do so at the detention center. Joy had always been tight and inexperienced there, and feared that whatever they might dole out would be intensely painful and embarrassing.
"Well judging from those supplies, I think you're getting more than a couple of swats on your ass," Jeff commented with a little chuckle.
"All right, then, Joy," he began, feeling his way into the disciplinarian role that he'd unexpectedly been thrust into. "I'm very disappointed that you kept me waiting for 15 minutes at the restaurant. And you're going to get a punishment for it. Take off your dress and bend over the bed," he said, the order coming almost naturally as he walked over to the table and picked up the paddle. He inspected it a little and took a practice swing in the air as Joy peeled off her dress, revealing a black lacy thong and black bra underneath.
"Yes, of course. It was wrong of me to keep you waiting," Joy murmured. Her heart raced as she glanced over her shoulder at Jeff and then walked to the bed, leaning over it, her soft, pale ass sticking out. She had inspected herself carefully earlier to be sure that no marks remained from the spanking Jennifer gave her at the first Correction Match session, and saw none, but couldn't shake an irrational fear that Jeff would discover that she'd been spanked recently and inquire further.
Once Joy's soft ass faced Jeff, he slid a hand between her legs and touched her over the thin fabric of her thong. "Someone needs to be punished for being a bad girl", he remarked as he traced very light circles around the hypersensitive nub of her clit over the thin fabric of the thong.
Joy shuddered and let a slight moan escape her lips. She felt herself getting instantly aroused at Jeff's touch. But this isn't what she needed, Joy thought to herself.
"Ah, no, that feels too good. I don't think I'm going to learn my lesson that way," Joy mumbled, her face pushing down into the bedsheet.
Jeff was a little confused, since he still was under the impression this would be a fun foreplay game, but decided to oblige. He peeled Joy's thong down to reveal her full, bare bottom, and rubbed it with one hand. He was starting to enjoy this and felt himself begging to harden at the roleplay. Just a hint of Joy's tan lines were still visible on her ass.
Yes, you do need to learn a lesson tonight, don't you?
Mmmhm. Yes, Sir. I'm ready to accept my punishment.
Jeff waited no longer, swinging the paddle and letting it crack against Joy's ass, causing her to wriggle and gasp into the sheets.
*CRACK* went the paddle as it landed for a second blow. Joy gasped and struggled to hold still. It felt different from when Jennifer had spanked her; this was more intimate. But it still hurt.
*SMACK* came the next stroke, interrupting Joy's train of thought comparing this spanking to her court-ordered one. Then another and another. Wow, Jeff is strong, Joy thought to herself, although that thought too was soon interrupted by a deep stinging sensation across her entire ass. After the eighth smack, Jeff set the paddle down onto the bed.
All right, Joy thought, collecting herself. It wasn't as severe as she'd likely receive at her detention session, but the spanking wasn't too bad for Jeff's first time. First time with her, at least.