Chapter 28: Date Night

“So, what are you guys up to tonight?” asked Jessica. Her brother and his family were only going to be staying another couple of nights and she was curious about the kids’ plans. The four teens had decided to double date that evening.

Toby shrugged. “The usual - movie, Mickey D’s, hang out at the mall, go parking. I figure we’ll teach the girls about what to do in the back seat.”

“You know, just like they’re going to be doing back home.” commented Andrew loudly. Their uncle was over in the corner listening, and he just groaned at the thought. The twins giggled at his reaction.

“You two are not helping, you know.” commented his mother.

Both boys snorted and tried to keep the laughter out of their faces. For all of Jack Miller’s complaints about his daughters growing up and starting to date, he had been actively enjoying their newfound sexual skills for the last few days. Their oral talents had improved sufficiently that both boys had complimented them on them, and both girls had been introduced to having his cock stuffed up their pussies as well. The previous night, in fact, the three men had gangbanged the twins while Jessica supervised and played with herself.

“Oh? And what are you two going to do tonight?” Andrew replied.

“Well, we were planning on going down to the malt shop and having a soda together. Two straws, though, because I’m just not that kind of girl! I might let him hold my hand.”

“What’s a malt shop?” asked Toby.

Jessica just waved her hand at her eldest. “Forget it! We’re going to go out for dinner and drinks, nothing unusual.”

Toby shrugged and led the twins towards the foyer, but Andrew held back a moment. Lowering his voice, he asked “Planning on dressing like you used to on date nights?”

Jessica’s eyes snapped open. Her youngest son had remembered how she had told the boys about how she had dressed for date nights with their father, varying from sexy to slutty. “Exactly!” she answered. Andrew glanced over at Uncle Jack and smiled, and then nodded. He followed the others out the door.

Jessica called out to Andrew before he could leave. “Oh, honey, what are you going to do if your regular girlfriends find out about this?” she asked.

Andrew stopped in the doorway and turned to face her. “Piece of cake. I already told Tracy. If anybody asks, we’re just a couple of guys who got stuck babysitting their cousins.” He waggled his eyebrows at her. “And it’s true!”

“I don’t think that’s the kind of babysitting Tracy is counting on!” She shooed the teens out the door.

“And now it’s just you and me?” asked Jack, climbing from his chair and walking across the room.

“Yep. I need a shower before we go out.”

“Want help washing your back.”

“That kind of help won’t help! I’ll be back down here in an hour. Be ready then.”

Jack rolled his eyes. “An hour?” How in the world anybody took an hour to shower and dress was beyond him?

“An hour! Of course, I could always throw on an old sweat suit and sneakers if you’re in a hurry.” Jessica headed up the stairs, sure what the answer would be to that idea.

It was fifty-five minutes later that Jessica reappeared in the living room. Jack had taken a quick shower himself and slipped into chinos, a dress shirt, sport coat, and loafers. Otherwise, he was going commando. He whistled as his sister came down the stairs. “I bet you didn’t go out on dates dressed like that in high school.”

“You’d bet wrong, then! Daddy didn’t like it much, but Andrew sure did.”

“And what about Mom?”

“Mom didn’t care. She once told me she’d go upstairs and dress up like I did, and then work Daddy over in the living room.” explained Jessica.

“No wonder he had a heart attack! Did he die in the saddle, do you know?” asked Jack.

“I never asked her. It didn’t seem the question to ask, you know!” Jessica turned slowly around in the living room. “You approve?”

Jack eyed his sister. Both his late wife and his sister had similar builds, being relatively busty, with hourglass figures, but Rhonda had been quite a bit shorter, and had a somewhat larger rear. He had often considered her plush, and built for comfort and easy riding, a Cadillac. Jessica had been taller and leggier, and generally more muscular, a sportier ride, maybe like a Corvette.

Tonight’s outfit was another proof of this theory. When he and Rhonda had gone out, she had often worn dresses, often frilly and light, with stockings and heels, something that would flutter and waft around her enticingly. Jessica, instead, was wearing black ankle strapped stilettos, a tight black mid-thigh length leather skirt with several zippers up the sides, and a skin-tight black tank top, cut low in the front and back, without a bra.

“I approve!” he agreed. “So, are we going to hang out at the mall with our buddies, too?”

“For that I wear the sweats. Dinner and drinks, please.” Jessica pulled a black leather jacket from the foyer closet.

Jack joined her and opened the front door. A sports car, definitely!

Jessica gave directions as they drove through town. Jack was comfortable enough finding his way around but was surprised when she had him pull into a parking lot behind a rather nondescript building. He was on the verge of asking where they were when he noticed the sign on the side of the building - Adult World Emporium. “What in the world?”

Jessica popped the door. “Come on. We need to go shopping!”

“Uh, okay.” He got out and followed her, glancing around curiously.

“Haven’t you ever been in an adult store?” she asked. “You must have! I know for a fact that Rhonda had some toys she liked to play with.”

Jack blushed at the memory. “We got those online.”

“Well, come on, it’ll be educational. Jack and I used to come here occasionally.”

Jack rolled his eyes and followed his sister through the door. Inside he found a well-lighted room about the size of the average convenience store. He eyed Jessica curiously; she seemed to know her way around the store, and it was a revelation to him about his baby sister. Jessica stood inside the doorway for a few moments, then moved off to the right side of the store. Jack followed her.

She stopped in front of a wall of vibrators. Jack was amazed! He was standing in front of a wall of vibrators, six-foot-high and twelve-foot-long at a minimum, in plastic and cardboard blister packs, in every conceivable size, color, and shape. There were dozens and dozens of sex toys on display, and as he looked around, he saw another row of sex toys almost as large as the one he was in front of. “Good God!”

Grinning, Jessica picked up a gigantic twelve inch jumbo model and waved it at her brother. “The only difference between men and boys is the size of their toys!”

“That thing is scary!” She smirked at him and he asked “No, don’t tell me, you haven’t...?”

Her laugh was bright. “No, I’m not that brave!” She hung it back up on the wall. “We need to buy a few toys for the girls.”

He gave her a confused look. “The girls? Lizzie and Megan?” Jessica nodded. Jack’s eyes snapped open. “What?”

“Keep your voice down, Jack.” Jessica glanced around the small store but the clerk, the only other person present, hadn’t noticed.

Jack took his sister by the upper arm and pulled her close. “You want to buy my teenage daughters dildos? Are you mad?”

Jessica smiled and peeled her brother’s fingers off. “Jack, be reasonable. You know the twins aren’t virgins. You know they enjoy sex. Everybody enjoys sex. Now, don’t you want your daughters to enjoy themselves?”

Jack groaned. “They’re my daughters for Christ’s sake!”

She laughed. “Who fuck like bunnies, just like their mother, and she liked her toys, too!” She turned back to the display and pointed at the giant monster from before. “Now, while that thing might be too much for them, I’m sure there’s something here a little more their speed. What sort of toys did Rhonda like?”

Jack blushed. “You’re serious?” He looked around nervously and Jessica giggled and nodded. “Okay, she had several. Most were really kind of average, you know, about six or seven inches long.”

Jessica looked around the racks and moved a few feet further along, to a large display of average-sized models. “Like these?”

He shrugged. “Pretty much.” As he started to get into the spirit of things, he pointed out several models. “I mean, she had one that was smooth, another that was ribbed, a hard-plastic type and a latex one. You know, the usual.”

Jessica nodded in understanding. “Okay, life is complicated enough. Let’s just get each girl a couple of basic models.” She pulled a smooth six-incher off the rack; it was bright pink, and she pulled a matching green model off the rack to the side. Then she moved a bit further and pulled another matching pair of ribbed latex models off the rack. The vibrators were all handed to Jack, who juggled them briefly before getting them under control. Then with a naughty grin, she moved down the aisle and pulled a large double ended dildo off the wall. “I’ll bet Rhonda didn’t have one of these!”

“You’re kidding me, right?”

“Nope!” She handed it to him. “Listen, the girls have already told me they sometimes play together.” She snorted at his expression. “Oh, don’t look so amazed. Lots of girls experiment. Your daughters have kissed and touched a little already. So did Rhonda and me.”

Jack’s jaw dropped. “You and Rhonda! Oh my God!”

“You didn’t know? That’s so funny! She never told you? We were inseparable in high school!”

“I had no idea!” He gave her a curious look. “So, what sort of things, uh, did you two do?”

“Wouldn’t you like to know! You’ll just have to watch the girls going at it some night.”

“Jesus!” Jack shook his head in disbelief. Then, as they moved down the aisle, he spied something on an upper rack. Stopping, he handed some of the toys to his sister and reached up. He pulled a box off the rack and showed it to her.

“I think that’s a little advanced for them.”

“I wasn’t thinking about them.”

It was Jessica’s turn to blush. “Oh. Okay.” She moved down the aisle further. “See anything else, for later?”

Jack smiled. “This should do us, don’t you think? What’s the clerk going to think when we show up with all this shit?”

“Hell, he’s probably seen worse. If he asks, just tell him we’re having a party.”

Jessica’s prediction was almost exactly true. The only thing the clerk said was when he asked if they had batteries. They had to examine each package closely to see if batteries came with the toys, and if not, what types were needed. Again, Jack was startled by how much the store reminded him of a convenience store, only where the candy was kept near the counter, it was personal lubricant in a dozen different types and flavors. He added a small tube to the pile of items, causing Jessica to blush a second time, and which the store clerk totally ignored. He simply bagged everything and took Jack’s credit card without a comment.

Jack held the door open for his sister and led the way to the car, then opened the passenger’s side door for her. After she got in, he closed the door and opened the rear door. He tossed in the bag with the toys, but only after surreptitiously slipping the tube of lube into a jacket pocket, along with the box containing the last toy they had bought. He closed the car and went around, getting behind the wheel. “Now can we go to dinner?” he asked.

Jessica smiled. “Now we can go to dinner. Get on the highway and head east. There are a few places over in Byford we can go to.”

Jack shrugged pleasantly as he started the car. Byford was about twenty miles to the east by the interstate, and despite the higher speeds on the highway, it still took twenty minutes by the time they got through the traffic lights on the way to and from the highway. Jack followed his sister’s directions and they pulled into a large mall. “We’re going in here?” he asked. Jessica’s outfit of miniskirt, tank top, and stilettos was a bit extreme for going through a shopping mall.

She smiled at him. “Not precisely. The restaurant has a side door, over there.” She pointed and he followed her fingertip to a side entrance. “The place stays open late. Come on, you’ll like it.”

Jack parked the car and they got out. He held her hand as they made their way across the parking lot. As he suspected, more than a few heads turned as Jessica moved. Most eyes, certainly the male ones, were approving, but a number thought her clothing inappropriate. Once inside the restaurant, all the eyes were very approving.

It took a minute for Jack’s eyes to acclimate to the lowered light level in the place. It was a little loud, a little dark, and a little warm. Jessica was giving their name to a young girl in very tight clothes at a standup desk near the entrance, and then turned back to him. “It’ll be at least half an hour till a table opens up.”

“Can we wait in the bar?” he asked, raising his voice over the hubbub.

“Sure, we’ll call your name when we’re ready.” replied the hostess. She pointed the way and Jack followed Jessica deeper into the restaurant.

They quickly found a large bar, with a single barstool, so Jack laid claim to it and lifted his sister onto the stool. He stood next to her and waited for the bartender to come over. “It’s not what I expected.” There was some loud rock music in the background, but he couldn’t find a stage or dance floor. “Do they dance here?”

“It’s a bar and restaurant, Jack, not a club. I thought we were just going out for dinner and drinks?”

He nodded. “No, no, that’s fine. I’m just asking, is all.”

She grinned at him. “I didn’t wear my crazy club outfit, Jack.”

He looked at her curiously. Her clothing fit in well with the other women in the bar, most of whom wore short skirts, high heels, and tight tops. “Which is what?” he asked.

“Not very much! Andrew bought it for me a couple of years ago, and I need to be half lit-up just to leave the house wearing it! Maybe you and I can get away sometime and I can wear it out.”

“Oh?”

“Yeah! It’s illegal in forty-seven states and the District of Columbia!” she teased.

“Speaking of which, open your purse.”

“What?”

“Your purse, open it up.” He motioned for her to bring her purse up and open it. She had draped it on the back of the barstool, and she had to twist around to grab it and pull it onto her lap.

“What are you up to?”

Jack glanced around, then quickly pulled the package from his jacket and stuffed it into her purse. “Why don’t you try that on for size while we’re waiting?”

“Jack!” Jessica glanced down at the small box he had placed in her purse and flushed, quickly closing the purse up before anybody else saw what he had done. “No!”

He sipped his drink. “Go on, do it!”

“I can’t!”

The pair argued lightly for another minute before Jessica gave in. She stood up, allowing Jack to slide onto the barstool, and told him to order her another drink, then headed towards the restrooms. Inside, she quickly went into the first stall available and closed the door, latching it securely. It was crazy! It was insane! She hiked up her skirt and pulled down her thong, and sat down on the toilet to pee, but then she opened her purse and stared at what her brother had bought her in the adult store. It was a remote-control vibrating egg.

It took her a minute to open the packaging up and figure it out, and then she had to insert batteries, both into the egg and into the remote-control unit. A quick test proved it worked, shocking and scaring her with the results, and then she turned it off. Blushing furiously, she dried her pussy off and spread her legs wide, then inserted the egg. She nervously pushed it in, wondering what would happen if she dropped it into the toilet, but she managed to complete the maneuver, and then pulled her thong back into place. Standing, she adjusted her clothing and flicked the switch on the remote briefly. Power surged through her pussy, making her gasp, and she turned it off and dropped it into her purse.

Jessica left the stall and made some final adjustments in front of the mirror and then left the bathroom. If anybody noticed the flush on her cheeks, they marked it up to the heat in the room and drinking.

Jack was waiting for her at the bar, a smirk on his face, sipping his drink. A new drink was waiting for her, and she almost gulped it down when she came up to him. He graciously got up from the stool and she slid into his place. “Well?”

“Well, what?” she replied, not looking him in the eye.

He glanced down at her lap. “Is it, you know...”

Blushing beet red, she averted her face. “Jack!” she whined in protest.

“Well?” he pushed.

She looked at him and hissed “You know it is, you bastard!”

He chuckled and said “Cool. Let me have the control!”

Her eyes snapped open. “No way!”

“That’s not fair.” he protested. He moved his hands towards her purse.

Jessica settled the purse in her lap and held onto it with a death grip. “Not a fucking chance, mister!”

Jack laughed and relented. He sipped his drink and asked “So, does it work?”

Jessica slyly smiled and nodded. “Yes.”

“So, let me try it out on you.”

She shook her head. “Maybe later, if you’re a good boy.”

“Are you sure you want me to be a good boy?”

“At least through dinner.”

Their names were called a few minutes later and the siblings moved into the dining room. Jessica was surprised by how easily the egg stayed in place and wondered if it would be possible to leave it in without panties or a thong as insurance. She decided to try that some other night. Once seated, they ordered another round and then, after the waiter had left, she leaned over the table to her brother and asked quietly “So, how did you and Rhonda get started with toys?”

“Huh?” Jack was surprised by the question, and his face showed it.

“Well, when did you start with them?”

“You first!”

Jessica shrugged. “That’s easy. I got one as a gag gift at my wedding shower. Later, I showed it to Andrew. I thought he would get a laugh out of it, and he did, but then he used it on me that night. I had always thought that guys didn’t like them, they were intimidated or something, but not Andrew. After that, he would buy me toys for birthdays or anniversaries or such. Now, what about you two?”

Jack gave his sister a sheepish look. “Well, actually it was her idea, sort of.”