Page 32 of Daddy's Little Matchmaker

“Should be,” Connor said. “With green beans, hard boiled eggs, tomatoes, olives, and romaine lettuce with a lemon dressing.”

She took a bite. “Mmm, it really is good.”

After they’d both had a few bites Tessica asked, “What about you? What are you looking for in a Little?”

“Well, my work schedule has been a problem for most of the Littles I’ve played with. Being gone for a day or two at a time has been difficult for them. So, I need a Little who doesn’t need to be Little every day.”

“Really? You’re not just saying that because you know I’m not Little very often, are you?”

“No. It’s been a genuine problem for me in the past. But it hasn’t escaped my notice that our kinks match up quite nicely. I would love to have a private playdate with you and one of the Littles you play with regularly who’d be willing to let me join in.”

“Oh.” The vein in Tessica’s neck pulsed faster. “Yes. I-I’d enjoy that very much.”

Connor put a hand on her knee. “Me, too.”

Tessica put her fork down and fanned herself with her napkin. “I’m going to be thinking about that all week.”

He moved his hand to her thigh. He leaned over and kissed her again, with a bit more intent than last time.

She responded with a tiny moan and a parting of her lips.

He forced himself to pull back instead of diving in further. He took a drink of wine. “I’d like to see you in Little mode in private next Wednesday night, and then on Thursday I’d like to co-top one or some of the Littles at the club with you.”

Tessica nodded, but then froze mid-nod. “Are you suggesting we try dating?”

“Absolutely.”

“But you live in Juneau.”

“True, but I’m a pilot, so I fly for free. I can spend my days off in Portland, and we can get to know each other better.”

“And if things work out between us?” she asked.

“Let’s cross that road when we get to it.”

After a short pause she nodded. “Okay.”

“Okay?” Connor could hardly believe she was agreeing so easily. He figured he’d spend a week or two trying to convince her.

“Let’s give it a try,” she said decisively.

CHAPTER TEN

Tessica lay in bed, but sleep was the furthest thing from her mind. She kept replaying bits and pieces of her evening with Connor. He wanted to date her. He wanted to see her Little side. He wanted to see her Mommy side. He wanted to sleep with her.

She cringed at the thought of him seeing her naked. Her body wasn’t what it used to be at thirty-four, which was the last time she had been naked with a man. She didn’t look bad for her age, but she’d never had plastic surgery, so shedidlook her age. And from what he’d shared, Connor was used to sleeping with women a lot younger.

She checked the digital alarm clock and sighed. It was almost midnight, and she had a seven-thirty appointment tomorrow morning. But after such a rich and filling dinner, there was no way she could have gone to bed any earlier than eleven without feeling ill. After their salad course, they’d shared a small tray of cheeses. Then crème brülèe for dessert, followed by a coffee.

After the cheese tray arrived, Connor made an offhanded comment about his granddaughter hating cheese, and the rest of their evening had been spent discussing their kids and grandkids. Intentional or not, the discussion had never returned to kink.

They parted ways when the Uber driver dropped Tessica off at her house before taking Connor back to his hotel. Connor had promised to email his flight schedule for the following week once he had it finalized. He said he’d try to get Wednesday, Thursday, and Friday off. Tessica frowned and wished for the hundredth time that Connor lived in Oregon.

She checked the clock one more time and shook her head. Tessica knew of only one thing that sometimes helped put her to sleep when her mind wouldn’t settle. And she’d been surprisingly horny after Connor suggested co-topping a Little with her. Normally she wouldn’t think twice about sticking her hand into her panties and bringing herself to climax, but it seemed weird to do it while thinking aboutConnor. Especially when she doubted he’d approve, considering his reaction to finding out she’d been doing herself for so many years. But he hadn’t told her not to, and he’d probably want her to get afewhours of sleep.

Decision made, she reached down and slid her panties all the way off. She dropped them on the floor beside the bed, and then shimmied her nightie up to her waist so that her entire lower half was naked. When she spread her legs wide, her clit pulsed in anticipation. She put both hands on her breasts and used her fingers to tweak her nipples. As the jolts of pleasure started, she imagined Connor being her Daddy and making her dinner while she colored.

She tried to make it last, but the thought of Connor taking care of her made it impossible not to touch her clit. As soon as her finger hit the sensitive nub, the jolts of pleasure tripled. A few short minutes later, her entire body tensed as wave after wave of ecstasy coursed through her. She lay there breathing hard for a few moments, and marveled at how quick and easy it had been to come before she finally slipped into sleep.

---