Just the Tip Ch. 02

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2nd meeting with Jennifer.
3.9k words
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Part 2 of the 2 part series

Updated 06/09/2023
Created 11/09/2019
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It took some time to work out the next visit, lots of effort. Jennifer was having doubts about being able to "be with" a married man, but she also could not deny that deep down, barring any consequences she really wanted him. David felt much the same, the only reservation he had was that if something ever did come up he didn't want Jennifer looked at in a negative light, or anyone to have bad feelings towards her.

When his spouse had stated that she didn't really mind, he was free and clear to have a "hall pass", he shared that information with the younger lady he really was eager to kiss again. His wife didn't want any details, didn't want to know if it had happened or not, never wanted to discuss it and told him the only time she'd ever discuss it was if she was really horny and wanted him to tell her a story. He could make it up or he could tell her about his adventure, either way she never wanted to know if it were true or not.

He figured it boiled down to her own guilt from her two past wrongs over the last 20 years. The second of which hadn't been a one-time thing, she had caught feelings for the guy and they had actually almost divorced because of it. The funny thing was it was not the anger or betrayal that had upset David the most, while it had infuriated him and all the things one would expect someone to feel it had been her refusal to apologize or talk about it that made things the most difficult. She had been the one who thought she wanted a divorce, but through a few days of gentle reminders that they had a family and he still loved her, he finally convinced her to seek counseling.

Now as he thought about it, and even replayed some of those conversations in his head he knew that he still was deeply in love with his wife, but his thought process had always been that you could love more than one person at a time. Look at families, you can love more than one child, why couldn't you love more than one woman? Why couldn't you share the feelings of closeness and intimacy without feeling guilty? American and Christianity type societies said you couldn't and that was why. Many societies had men with more than one wife, or a much more open social acceptance. Some countries were even known to allow for a one-day pass per year, where there were no boundaries to the normal etiquette that was a normal standard. It was believed that if you were given one day a year to act on desires with someone other than your spouse or significant other, someone that you lusted after from the past or present you would be much less apt to stray throughout the rest of the year.

He laughed as he thought about this. Once a year would be tough if you knew you could play with another person. But realistically for 24 hours those two people would join as often and as hard as they could to get it out of their system. He had talked to Jennifer via text numerous times since that first night. Knowing that towards the end of the night she had started to feel guilt. Neither of them reaching orgasm, well he knew he hadn't, he wasn't sure about her, she had definitely enjoyed the brief interlude but he wasn't sure there was enough foreplay or sex that would have provided the necessary stimulation for her.

So after nearly a month he had gotten her struggle down to much more passive and he knew what she wanted. She wanted a night alone with him, every bit as much as he did with her. He had admitted that he wanted to kiss her again, deeply, long and a lot. He had been slightly tentative that night when he kissed her, while he had been the one to start it, it came as a bit of shock when she kissed him back. He had gotten instantly hard and wanted to make her pull over the car right then and there in a parking lot.

Anyway, back to the story, as Jennifer came to terms with her wanton desires, she just had to know what a night was like with him. Deciding that she wouldn't allow guilt to creep in this time, her body needed to feel the caress, the exertion of a physical acts that she couldn't just go out and randomly get. She just wasn't that type of woman, which is what made this all the more confusing to her now. Once she decided to give up the guilt though, she reached down in the shower and touched herself, noting how wet she already was, how swollen her clit was and just how every single drop of water from the shower head felt like little beads of pressure arousing every inch of her skin. How those little single beads so numerous and teasing her had merge to group into rivers of warmth running over and stimulating her most erogenous zones, her nipples standing hard, her clit feeling their caress as it peeked from under the hood. Jennifer closed her eyes and captured her clit between two fingers and began to rub back and forth and within seconds she bit her lip nearly drawing blood as she struggled to not scream out as orgasm crashed over her. She quickly sat down in the tub and finished strumming herself until her legs were shaking and she could stand no more.

Jennifer grabbed her phone from inside the shower and took a quick picture without thinking. Strategically hiding her nipples and clit from view, but wanting to tease the man and let him know that his conversations and writing had finally broken her, she was more than willing now to meet him and fulfill both their fantasies. She was nervous as she sent the pic, but she knew he would keep it hidden, hopefully he'd save it elsewhere and then delete it from their text conversation. She'd have to talk to him about that, hopefully he'd delete that conversation as well or at least the racy parts so that no one would ever see them.

She sent the pic along with the message, as soon as we can if you still want. . Within a few seconds of sending she got her reply, he sent her an address and the question, can you make it tonight? She didn't even look up the address she checked to make sure her mother would be home tonight with her son and then after securing the childcare needed she told asked what time and what should she wear.

"Well since nothing isn't an option. LOL. How about A skirt, something you could wear to work, with stockings and either a thong or nothing underneath. A light blouse or a sweater. Just know I won't keep you clothed long, well maybe the stockings will stay but that's it. OMG! I can't wait to see you."

Jennifer laid out the last of her clothing and then slipped them on. She had about ten minutes before she left, she quickly texted David, "I'm super nervous man."

"Hey," he replied, "I'm in the car on the way, I have a little liquor with me, and some of that other stuff you like. We'll take a quick puff, then I'll go in, get a room and come back out to get you and the "luggage". We'll make it look natural, we'll go to the room, share a kiss, turn on a movie, turn on the spa tub and we'll see what feels right. If you change your mind or feel uneasy all you have to do is say the word and we'll just cuddle and watch a movie and talk, or we'll go bowl or something."

Jennifer felt herself get wetter if that were possible. She had planned on going without panties, just for the naughty experience but decided at least until she pulled into the hotel she was going to keep some on, she didn't want to leak all over her skirt or car seat. She blushed thinking about it, it had been a while since she anticipated anything like this. She had settled down a lot since having her son and her sex life had been reduced to fingers, toys, and one sexual encounter since then.

David drove to the destination for the evening, feeling his cock tenting in his pants, he was already aroused and desiring this beautiful woman immensely and he knew that he'd have to be careful or he'd explode as soon as she touched him. He didn't know her feelings on oral sex in depth so he'd been consuming pineapples daily for a few weeks, first he loved pineapple, but it was a widely known fact/myth that pineapple made cum taste sweeter and not bitter. It couldn't hurt to make things better if she was willing to do that. Geez, he nearly exploded just thinking about her in anyway making him cum. Ok, calm down, he told himself. Don't pressure her, just lead a little more this time and then see how things go.

As David pulled into the hotel he saw Jennifer's little white car and she hopped out and slid into the passenger seat of his vehicle. "Well hello sexy," he stated with a gasp upon seeing her stockings. Jennifer had already decided that she was going to let him lead more this time as well, and she immediately through that out the window as she leaned over and kissed him and grabbed his hand. Sliding it up under her skirt she let him feel the wet apex between her legs.

"Well, let's spark this bowl, and then run inside," he exclaimed excitedly, "I'll need it to calm down or I'll be walking into to get the room with some major wood leading the way."

He quickly lit the bowl and took two puffs and handed it to her. As she puffed he leaned over and kissed her neck and gave her swollen nub just a quick flick, nearly pushing her over the edge as well. "Ok," she breathlessly whispered, "go get that key and come back and get me. I can't wait much longer."

This was so uncharacteristically unlike either one of them, yet exhilarating at the same time. David rushed in and was back within 5 minutes grabbing a suitcase out of the back. She'd later find out just what it had in it, but they dashed into the lobby and to the elevator and headed up to the room. As soon as the elevator door shut, David stood behind her and pulled her ass back against him, brushing her hair to the side he kissed the back of her neck and slowly slid his hands up her ticklish sides.

Once the elevator stopped they walked, fighting the urge to run, to the room and then as he slid the card into the slot she ran her hand down the front of his chest, "Hurry please," she begged as that hand slipped down more to grab and give his hard shaft a quick stroke.

The light to the door turned green and the lock disengaged, as it did he turned the handle and opened the door. Stepping in he grabbed her hand and pulled her with him. Locking the door quickly as he pushed her up against it. He kissed her once deeply and then with no warning dropped down to his knees and lifted her skirt. He grabbed an ankle of hers and lifted it up so her knee was over his shoulder and then leaned in and began to lick and suck her clit. He teased her fluttering his pierced tongue against the bud of pleasure as his fingers found their way into her slick center.

With her back against the door Jennifer quickly started breathing faster and harder, knowing her orgasm was immanent and wanting to cum while he was pleasuring her with his mouth. God, this felt good she thought as he continued to taste her wetness. She could feel her moisture trickling down her thighs, knowing that she had been starting to drip as soon as her panties had come off in her car. As she began to cum she shook and shivered and grabbed onto the back of David's head. "Fuck yes, David, I'm cummmmmmmmmming!"

As soon as it eased she started to push him away. "Oh no dear I'm not done yet, I don't know how you feel about what comes next but if you don't like it just tell me," he said with a smirk as he looked up at her. Jennifer had no idea what might be upcoming but she decided to keep an open mind. That's when she felt herself flipped around. There was a hook on the back of the door for jackets and David quickly slipped a piece of rope around her hands and cinched it as it tossed the end over the hook. It had plenty of play and she could have easily lifted her hands away from it and gotten off the door, he had made it erotic and not creepy by leaving her lots of room for escape or refusal to go down that route.

As she felt his hands run up the back of her thigh she thought that was the surprise he had mentioned. It wasn't until he was squeezing and kissing up the back of her thighs that she wondered if there were more. And that's when he pushed her legs apart and kissed her ass. He gave it a soft bite to each cheek, which tickled as much as sent shivers up her spine. Then as she caught her breath she felt his tongue tease it's way between her cheeks and it pushed and teased her backdoor. She wasn't really into anal anything but this felt so good she was going to let him play until if felt weird or uncomfortable.

She quickly decided it felt really good and he teased her clit and slipped a few fingers inside her wet pussy as he rimmed and dipped his tongue into her ass. Jennifer found herself pushing back against him wanting more. Just as fast as it started he moved up kissing her back, reaching around to unbutton her blouse, his hand slipping in underneath the bra cup and teasing her nipples as his breath warmed her neck. "If you want more of that later I'll definitely return to give you pleasure there," he teased, "but for now just hang out here while I get mouthwash before I kiss you again."

Jennifer, even though she was aroused beyond belief giggled at his joke as she felt him pull away and heard the suitcase open. In an instant, he was back and lifting the rope away from the door before leading her by it to the bed. He removed the wrist loops and then pulled off her blouse. Reaching around he somewhat clumsily removed her bra, a sure sign he was still a little nervous, but it was endearing at the same time. Before he could do any more she spun him until he was standing next to the bed and gave him a shove. "Now it's my turn," she informed him as she unhooked his belt and unfastened his jeans, "I need a taste too."

With that she tugged his jeans and boxers down and let her mouth follow. He was by no means huge, but nor was he tiny, if anything it looked like he'd be just the perfect fit for anything they tried tonight, depending on how things went, he may even be a little too big for one area that didn't see much action. She smiled to herself as her tongue ran down his shaft and she looked up at him as she slowly sucked each of his balls into her mouth, running her tongue over them. Stroking his shaft the entire time, as she slipped back up she saw the bead of pre-cum pooled on the tip, and had the overwhelming urge to taste it as she gave a tongue swipe across the head of his cock. "MMM," she hummed, thinking to herself this was very sweet tasting, she'd have to remember that.

David warned her after a few minutes she may want to take a break or he was going to cum. She pulled back a minute, "Wow, even a gentleman while horny and wanting to cum," she said flirting with him, "well you just made this an easy decision."

Jennifer stroked his shaft faster and began to bob in sync with her hands as she had decided she really wanted to taste his cum and more importantly make him cum with her mouth. Normally she'd never be this blatantly slutty but this may be the only night they got, she was going to make sure it was ingrained in both of their minds forever.

Pulling back one more time, she upped the coyness, "I want you to cum in my mouth David!"

As soon as she dropped her head back down he moaned and she felt his hand on the back of her head and she took him all the way to the base of his shaft. "OH FUCK YES, JENNIFER!' he began to cum, she noticed he didn't push her down just rested his hand on her head, she felt his fingers curl and knew that he wanted to hold her down, she wouldn't have objected but it was just as hot knowing that he wasn't going to force her to do it.

As soon as his orgasm subsided she began to pull away, licking and teasing the still hard shaft until he pushed her away. "No," he gasped, "too sensitive, give it a few minutes, that was amazing!"

Jennifer hopped up to get the mouthwash as well, and was surprised to feel herself pulled back to the bed and kissed. "Hey, you just swallowed my cum, there's no reason to not kiss you," he said before kissing her deeply again.

He sat up on his haunches and pulled her skirt off, leaving her stockings though and as after leaning down and kissing her wet lips below he kissed her clit, then her belly and then moved to her chest, he was going to tease and play with her nipples until she was humping against him and whimpering for his cock. That's exactly what happened until Jennifer pulled him up for a kiss and locked her legs around his waist and pulled him into her. His cock slid in with ease from her arousal and the attention it had already been given. Slowly she pulled him deeper until he could go no deeper. She felt so full and happy right now she kissed him again and smiled against his lips.

"I know," he growled against her neck as he started to slide in and out, his hands slid up her body, caressing her until he caught each of her hands with his and pinned them above her head. She was a little worried and exhilarated at the same time, Jennifer had really expected this to just be hot sex. This was slow and methodical, it was sex, and it was hot, but it was tender and loving as well. She put any other thoughts out of her head and decided to just really enjoy this.

After a few minutes David leaned over to the side and pulled her with him. Positioning her on top of him, "Goodness you are beautiful," he said cupping a hand behind her head and pulling her down for a kiss as she slid up and down on his hard penis. Slipping his other hand between them he rested his thumb against her clit and rubbed helping her reach another climax. It didn't take long and she was sure if they had neighbors tonight they were hearing her cum.

David hadn't cum again yet and as she finished this round she slipped off and turned around putting her head down on the pillows next to her hands, raising her ass in the air, "Fuck me from behind, pound my tight little pussy David!" she said with a wiggle. Before she finished her sentence, she could feel him pushing inside from behind.

"You are so wet, yet so tight, you feel amazing Jennifer," he told her between deep breaths. Squeezing her ass, giving her playful swats to gauge her reaction. He slid his hand up and tugged her hair as he began slamming his hips into her sexy ass as he pounded her wet pussy as she had so eloquently suggested. What had started this evening as soft, slow and sensual was now a furious fucking and just good hard sex. One hand wrapped in her hair, the other now swatting her cute ass, he instructed her to rub her clit as he fucked her harder.

Jennifer whimpered again, moaning louder and louder trying to not scream when she felt him swell inside her and suddenly begin to spurt. As soon as he finished cumming he pulled away and lay on the bed, grabbing her and bringing her with him, kissing her as soon as her lips were near. "That was definitely worth the wait and every last effort it took to get you here," he informed her.

She couldn't have agreed more, she was still struggling to catch her breath and wasn't even sure she wouldn't be hoarse tomorrow. She did wonder if he had anything left, a little sad to admit even after all of that she was still horny.

"I know what you're thinking," he said softly, "I'm thinking the same thing. Yeah there's still some left in the tank, at least once or twice more. I wasn't sure if you could spend the night or not, I know everybody is fine at home, and as long as I'm back by 10 no one will think a thing about it. They think I'm up in Maryland visiting my buddy Shawn who is on base up there."

After a nap, realizing it was still pretty early they popped a movie in and watched while drinking a few drinks. David hopped up and turned on the spa tub, he pulled her in with him and sat her in front of him as he washed her back and caressed her front slowly, not rush, no pending need, just enjoying every inch of her body. This made her next words even better.

"So, if you wanted to explore that other area, I'm not sure how much I can take or if I really enjoy it a lot, but I'm willing to try." Jennifer blushed as she said this, not sure what made her willing besides the fact that she knew if it was nearly as good and he took time with that like he did everywhere else it would probably have to be somewhat enjoyable.

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