Lucky Over 40 Ch 10 Date With Jj

Author's note: This is the tenth part of the story of two single 40somethings that met on-line and started an adventurous sexual relationship. It's about exploring their completely heterosexual kinks. You do not have to read previous parts to enjoy this, although several things would be better understood.

Please DO make use of the story Tags to see what you may or may not like. If anything there bothers you, it might be best if you move on to another story, otherwise, I hope you enjoy reading. If you like it, please add some stars at the end, and even a comment; they do help inspire me to continue writing.

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I've been dating Jill for a couple months, and we've been having pretty incredible sex for about half that time. I feel like the luckiest guy in the world to be with her. Jill had "lent my (sexual) services" to two friends in order to "help them out," as she put it. One of them, JJ -- who I called Jill-2 -- owns a sex toy store, where we first met her. JJ recently kicked out her really shitty boyfriend and the realization how bad he had been left her self-confidence shaken. Jill decided I could help fix that...

After work on Wednesday I went home to shower and change clothes before going to pick up JJ at her house for our date. Jill called me, saying, "Hi Tiger. I think I forgot to tell you, or be sure you understood, that what Jill-2, I mean, JJ needs, or wants from you today, is to have several hours of really passionate sex. She and I both know it's not going to turn into anything more between you. She hasn't had any passion in a long time, and the whole betrayal thing has her feeling poorly about herself. I'd like it if you could let her feel like someone really cares for her by making it all about her, and not just sex. I know you can do that, right?"

"Um, yeah, I think I can," I said, trying to process what that all really meant. "I think I can act passionate for her. But, yeah, it's you I'm in lo..., ugh, um, in lust with. Oh shit, Jill. I'm in love with you, even if I'm still scared to admit it. I'll do my best to show JJ a really good time, though."

"Yeah, I bet you will, Tiger," she said with a laugh. "I really love you too, Rob. But I want you to go and make love to Jill, shit, I mean JJ tonight! It seems odd, but just do it for me... well sorta for me."

"You are so weird with these 'helping a friend' things," I said, shaking my head to myself. "Yeah, I'll do my very best to make her feel loved. I guess that's the idea. I have to run. Thanks, Princess."

"I know you will," she said. "I love you and I'll have you make love to me, soon enough. Now go get her Tiger! Love you! Bye."

When I got to JJ's she greeted me from her side door as I got out of my car. She was wearing a pretty yellow, low cut V top that showed her lovely cleavage, even at a distance, and a loose fitting flowered skirt that went just past her mid-thigh. Her wavy dark hair was flowing down below her shoulders, and she looked hot.

"Hi Rob," she said with a big smile as she came out the door.

"Hi JJ, you look great," I said as I approached. "Are you ready to go right to dinner?"

"Thanks," She said, as she came up and gave me a kiss on the cheek. "Yeah, I'm starved. Is it Ok if we just get going?"

"Sure, I'm pretty hungry, too," I said, just a little surprised that she seemed to be more, I don't know, reserved, than usual. Last time she greeted me, in her store, she kissed me full on the lips right in front of Jill.

I opened the car door for her and she sat on the seat facing out, lifting one leg in and letting her skirt slide up with her legs parted to briefly expose her shaved pussy before pulling her other leg in. I'm sure she wanted to arouse me, and she succeeded. I closed the door and walked around to my side of the car, making a little adjustment in my pants.

As I got in she said, "I'm kinda eager to have dinner and then get back here, for some reason."

"Ok, I'll keep that in mind," I replied with a smile, catching on to her continued tease. "Maybe we can get desert to go, and have it back here."

"Oh, I'm planning on something creamy for dessert," she said as I pulled the car out. "And maybe I'll feed you some of it, too," she added as she put her hand on my thigh. "If you don't have any place special planned, could we go to the little place down on the pike by Robertson? Do you know the one?"

"Yeah, that's fine. I was going to ask if you had a preference. I pretty sure I know where you mean, and I've been there a few times. Simple fair but it was always good."

"I like their wines," she said. "And it's usually quiet on a weeknight, or used to be. It's been a while since I went out to dinner. This'll be really nice." She gave my leg a little squeeze and moved her hand back to her lap.

We chatted idly for the rest of the sort drive and after I parked the car, she got out before I could come open her door. We went in and JJ found us a nice booth away from the bar, in the back. "I don't want to deal with other people, if this is Ok with you." I indicated it was fine and we sat. The waitress was there quickly and we both ordered some wine and perused the menu. We decided on our meals in time to order as soon as our wine came.

Once the waitress left I thought I should offer a little toast, so I raised my glass and said, "To good wine and good friends" (I'm really clever on a date).

JJ lifted her glass, quickly adding, "And good sex," before sipping some wine while slyly looking over the rim of her glass at me.

"I don't have many friends down here in Florida," JJ said after setting down her glass. "I guess I don't have many at all anymore. It was nice to meet Jill, and you, and to start to get to know you two. I'm hoping we can do more together. I've missed socializing."

"Yeah, we've sure gotten to KNOW each other, like in the biblical sense," I chuckled, thinking about the few sexual encounters we'd already had. She smiled and gave me a wink. "But, I understand what you mean. My social network isn't very big ether, but I bet Jill's is, though I've yet to meet much of it. She's far more outgoing than I am. Plus I haven't been around here all that long."

"I didn't used to have trouble meeting people and making friends, I just haven't had the free time. Anyway, I really do want to get to KNOW you better," she said, taking other sip of wine and winking at me over the glass. I felt her foot lightly rub against my calf, briefly.

"That sounds nice," I said as I took a sip, and slipped out of my shoe to stroke her leg with my foot. "You look very pretty. I like your top, it's..."

"Revealing?" she interrupted, as she pulled one side of the V to the side, exposing more of her luscious breast, almost to the nipple. She stared at me with a very knowing smile. She let her top slip back just before the waitress approached with our salads and some bread.

We chatted about how we each ended up in Florida, and stayed pretty tame while we ate our salad. When we finished and waited for the meal to arrive, she started to rub her foot up my leg again. I was able to catch her foot with one hand and pulled her toward me, watching her surprised look as she slid forward in her seat. It was very unusual for me to catch JJ off guard, and I enjoyed it.

I rubbed her foot with both hands and she wiggled her toes. "Oh, that IS nice, Jill was right. Do you have a foot fetish? Would you like me to give you a foot job?"

"No," I replied with a chuckle. "I just thought you might like it. There are a few other parts of your anatomy that I find much more sexually appealing."

"Oh, such as these perhaps," she said as she used her hands to pull her shirt open, this time revealing both her erect nipples. My cock instantly started to stiffen, but it was trapped in my pants in what became an uncomfortable position. I lowered her foot between my legs as I tried to adjust things.

JJ caught on, saying "Need some help there?" and wiggled her foot against the bulge in my pants.

"I just need to straighten something out," I said with a little grimace. Her actions were making things worse, as my cock grew more. "Shit, that feels...ung...good, but it's making matters harder to deal with at the moment."

"It's making something harder," she giggled. She pulled herself back in her seat and teased my cock with just her toes. I was able to reach in my pants and pull my stiff dick up straight, finally gaining some relief, which apparently showed on my face. "Everything better now?" she asked with a big grin while rubbing along my shaft.

"Oh the things you do to me," I said with a smile, and stroked the top of her foot with one hand.

"Just wait `till later," she replied as she removed her foot and readjusted her top to contain her boobs before the waitress returned with our dinners. Her nipples were still pretty obvious. I gazed at her chest, smiling and wiggled my eyebrows. She smiled back and dabbed her mouth with her napkin while adjusting her shirt beneath it so the waitress wouldn't notice as she set down our plates.

"Anything else you need?" our server asked. "Would you like another glass of wine?"

"I would," JJ said, then added, "but we have a busy night ahead so I'll play it safe and just finish this one." I shook my head to indicate I didn't want more, either. "We're all set, thanks."

Once the waitress had gone, JJ laughed a bit and pulled the front of her top taught so that her nipples poked hard against the fabric. As I smiled at them, she gave each a pinch, as if trying to be sure they were sticking out enough to keep my attention. "Is that better?" she asked me. "I want to be sure you have a nice view, and I want to keep you concentrating on me tonight."

"You know I will be, and you're always a nice view. Sorry I can't return the favor, but I don't have much to look at." I said in response.

"Oh yes you do," she said with a smirk. "Maybe you should stand up and let me see that tent in your pants." I chuckled and started to eat my dinner. "No, I mean it. Stand up at the end of the table and let me see. No one's around, go on," she coaxed.

I was reluctant, but I knew she wouldn't let it go, so I put down my fork and slid out of the bench seat to stand by the table facing her. My pants were bulging and my cock was still off kilter. I decided I might as well push it up straight from outside my pants, thinking she would like seeing that.

She smiled her obvious approval. Before I could sit back down she said, "Since no one's around, and you have your back turned if anyone does come this way, why don't you open that zipper and pull it out for me to see?" I started to say that I didn't think that was a good idea, when she reached out and pulled down my fly. "Come on, I gave you a show, so now it's your turn."

Figuring I wasn't going to win and so might as well get it done quickly, I reached in and pulled my dick though the opening in my pants. The embarrassment had made it deflate a bit, but it was still partly stiff, and her ogling got it to start growing again.

She smiled broadly as she watched it, then said, "Keep it out when you sit down, won't you, please?" Again, I knew it was probably worse to try and argue, so I grabbed my napkin and covered my lap as I turned and slid back into the booth.

The waitress came by a few seconds later saying "Did you need something?"

"No," I replied quickly. "I, um, just spilled some water in my lap and needed to clear it off before it made a mess. Thanks, but we're all set now." She seemed satisfied and left. I sighed in relief.

"Yeah, I'm glad you got that out before it made a mess in your pants," JJ laughed. She slid forward in her seat and I felt her toes rubbing my exposed dick. "You sure you don't want a foot job, stud?"

"Maybe later, but not right now," I said with a little embarrassment. I tried to cover by saying, "I'd rather finish eating this dinner so I can eat you for dessert."

"Oh, now that sounds promising," JJ said, withdrawing her foot. "I'm also looking forward to getting some of your creamy filling."

I started to put my cock back in my pants when I noticed it had leaked some precum. I gathered it on my finger and showed it to her. "If you're a good girl and promise to eat your dinner right away, I'll let you have a little taste of dessert."

"That's a deal," she said as she opened her mouth for me to put my finger in. She sucked hard on my finger and teased it with her tongue, while looking intently in my eyes. When I pulled my finger out she said, "I'm looking forward to having something else, bigger than that, in my mouth."

"So am I," I replied with a big grin as I dropped my napkin over my still exposed cock. I decided it was too stiff to push back in my pants right now.

We both tucked into our dinners, eager to finish and be on our way. We continued teasing, with a lot of innuendo and some double entendre thrown about, but our focus was really on getting out of there and moving on to much more direct contact.

The server returned just as we were finishing. I asked for the check and handed her my credit card at the same time, saying that we had a lot to do that evening. Before she returned, I put my cock away and JJ casually flashed me one of her boobs, tweaking her nipple as she did.

When the waitress dropped off the bill and my card, I added a generous tip as JJ got up. When I started to get out of my seat, JJ turned her back to me and lifted the rear of her skirt to expose her beautiful bare ass for a couple seconds, before dropping it and heading for the door. I followed as quickly as I could, putting my wallet away as I rushed to catch up with her. We passed the waitress on the way out and she said "Enjoy your evening," with what appeared to be a knowing smile.

I took JJ's hand as we walked to the car and she leaned in close to me, putting her head against my shoulder for several steps. I opened her door and she stepped in, swishing her skirt up to flash me a glimpse of her bare pussy again as she got in the seat. I thought I saw a little something glistening there. She definitely had a sexy smile on her face and a gleam in her eye.

I got in and as soon as I had fastened my seat belt JJ put her hand on the bulge I my pants, saying,

"Just wondering if my dessert is ready. Mmm, I think so. Would you like a little taste of yours?" She took her hand from my lap and lifted her skirt, sliding two fingers between her labia and then bringing them to my lips. I inhaled their sweet, musky scent before touching them with my tongue and taking them in my mouth to fully enjoy the flavor.

"Mmm, delicious," I told her. "I can hardly wait to really indulge myself, beautiful. You are as delicious as you are lovely." I started the car and pulled out of the lot.

She straightened her skirt again and said, "Thanks. It's been quite a while since I've gotten any compliments like that." She was looking down at her lap, smoothing her clothes. She looked up at me and continued, seriously, "I really want to thank you for a nice dinner, and in advance for the rest of the evening."

"You're very welcome. I don't know when I've had a dinner like that. Even with Jill," I chuckled. "And I'm sure I'll enjoy the rest of the night even more." While we were stopped at a traffic light I looked over at her and saw her nipples pushing out against her top again. "Damn, you are hot."

She watched the light and as it turned green she pulled her top up, catching her boobs so they pulled up with it, suddenly dropping out below. They bounced and jiggled; her erect nipples prominently displayed. I stared until the car behind me honked and made me start driving. She pulled her top back down to cover herself, saying "Can't have any distracted driving. I guess I should have waited until we're home."

I just grinned and shook my head as I tried to pay more attention to the road. Fortunately, it was a short drive back to her house. My cock had really been straining my pants, but was a bit more relaxed by the time I parked in her driveway. I walked around the car and opened her door for her, then swatted her once on the ass when she was out. She lurched forward, then ran to the house, giggling.

As soon as I stepped into the house she turned, put her arms around me and pulled me into her. She kissed me hard, pushing her tongue past my lips and into my mouth. I responded and our tongues tangled as we kissed deeply. My cock also responded as she grabbed my ass with both hands, groping it and grinding herself against me.

"Jill is right, you do have a very squeezable ass," she said when she came up for air. "And you're a good kisser, but somehow I don't think your heart was really in it just then."

"Well, I um...I was a little surprised," I stammered.

"Yeah, Ok, that's all right," she let go of me and stepped back a bit, holding my hands. "Before we really get started let me explain, in case Jill hasn't fully done that already. Look, I know that you're committed to her, and she to you. If you two weren't involved I might have other ideas, though," she said with a sly grin not unlike Jill's.

"No, Jill called me earlier and I think we're on track. I just wasn't quite ready for that I guess." In actuality, I didn't know what I was ready for. I knew what was expected, but I wondered if I could really pretend I was in love with her -- or even in lust -- the way I was with Jill.

"Good," she said, sounding relieved. "This is kind of like role play therapy for me. Can you role play with me? Can you get into your role, pretending you're really attracted to me and make passionate love to me? Are you Ok with that?"

"Yeah, I am. And I don't need to pretend to be attracted to you, JJ," I said, that part certainly being true. "Sorry I sort of got us a little off track, but I'm glad we cleared that up. Can we start over? Role playing that I I'm really nuts about you and wanna have hot sex with you shouldn't be very hard at all."

"I sort of figured that when I noticed that something was hard," she teased as she stepped back towards me and took hold of my belt. "Let me get you out of those pants so I can get a better grip on that cute butt, and see how just hard you are, stud."

She undid my belt and pants, letting them fall, then grabbed my briefs and said "these are cute, with that nice bulge in front, but I'd love to see you in a little pouch number I have some place. Maybe later. Let's see what you have for me now."

She pulled the waistband of my briefs out, peeked in and said, "Yeah, he's nice and hard, and looking good, as always. Mmm. C'mere, honey." She dropped to her knees as she pulled my briefs down all the way, taking my erection in her mouth as it popped free. While she sucked my cock, moving her head up and down on it, she helped me out of my shoes and pants.

Once free of all clothes below my waist she pulled her lips off my cock and stood. "Let's head to the bedroom and get more comfortable." She took my cock in her hand and led me to the bedroom. I pulled off my shirt and then reached out to grope her firm ass under her skirt as she walked. She hummed, "Mmmm," approvingly, and squeezed my dick.

When we got into the bedroom I pulled her towards me again and kissed her deeply, my tongue fully exploring hers. I slid my hands up under into her skirt and caressed her ass. She purred.

"Oh that was better," JJ said after the kiss. She took a couple steps back and looked at me, trailing her eyes down to my fully erect cock. "Oh, and that's looking even better, too," she said smiling.

"My turn," she continued as she crossed her arms and grabbed the hem of her top, pulling it down nearly taught. It stretched over her full round breasts and her large erect nipples poked out as if trying to puncture the fabric. "Let's try this again when you can pay better attention, shall, we?" She lifted her arms catching her breasts with the hem of her shirt, lifting them with it, until it could no longer hold them and they dropped free, bouncing and jiggling before my eager eyes.