Falling Through the Keyhole

"Enjoying yourself?" he asks, his teeth nipping at her ear. She once again feels her body melting into his, which drives his fingertips deeper into her waistband. After only a few days of knowing each other, he's driving her crazy with anticipation over what they might do next. It's easy to answer him honestly.

"Yes." It's surprising to her how much she enjoys just going with the flow of all the decisions; she'd become accustomed to having to come up with all of the answers to hard questions, and mediate decisions between those with the authority to do so but conflicting goals. The years since she'd been married to Mike had made her independent, and she was proud of that trait.

"Good," he says, and then it's their turn to order. She got a grilled chicken salad with a Diet Coke, and he ordered a burger and fries with a large regular Coke. As they took their seats, he teased her about being too skinny, and she teased him about eventually becoming overweight. Not that he had to worry about it for quite a while-he was quite a bit taller than she, and judging by the feel of him whenever she was pressed against him, had quite the hard body. The muscles in his forearms were well defined, something she hadn't expected from a tech geek. However, his comeback had her coughing on her drink.

"If you don't eat a little more fat, your tits will always just be teacups," he teased her. "Relax a little with your food intake, and I'll bet you get big enough to actually require a real bra instead of the trainers we got you."

Tina's cheeks flushed beet red from both the words and from choking on her soda, but she was always as good to give as to get. "You kids are all about big boobs, but they go saggy too fast. Smaller stay perky longer and will still having you blow your load before the girl you're with even starts to get her motor revving, let alone red lining!"

Dan's eyes narrowed with amusement. "You've had that much experience have you? Well, smaller tits get flashed to whoever's around when I lead you around by the shirt, while bigger ones just kind of bounce around. Besides, bigger ones would make you more confident."

Tina scoffed. "So you like bimbos with big boobs but no brains?"

Dan laughed at her. "Where did you get the idea that the bigger a woman's tits get, the less she thinks? I know you work with some chesty ladies-just look at Sierra." Tina has to acquiesce to that comment-Sierra was a solid DD, but also one of the most competent and intelligent women that Tina knew. "I'm just saying, that attracting a little more attention with your looks and you'd be an unstoppable force. That sex appeal would go to your brain and unlock potential you didn't know you had."

"And just how do you know all of this, oh Grey-Head-of-Wisdom?" Tina scoffed.

"Because you I can read like a book," Dan smiled at her. "Miss Once-Bitten-Twice-Shy, So Don't Even Look At Me Little Mouse," he teased before becoming serious. "Look, you'd be smoking hot with a little extra on your chest and a little effort with the hair and makeup. Women being jealous of you and men panting over you would have you realize that you're capable of far more than you've limited yourself to so far. But right now you're so hesitant that you second guess every decision you make on your own. When you're at work, you're fine-it's not your life you're deciding. But on your own, you're just whiling away the years and not really accomplishing anything."

Dan sat back, folded his arms, and contemplated her. Tina felt like a child again, even though she was his senior. "I tell you what," he said. "You and me become a regular couple. I'll push your boundaries respectfully for the next year or so, but you have the freedom to live your life. See if me pushing you lets you accomplish new things on your own, and we'll talk seriously about this again in a year and see if you've made progress. If you have, great-you're ready to start living. If you haven't, at least you'll have fun with a friend along the way. Deal?"

Tina contemplated. This wasn't what she'd been expecting-she'd expected him to want to be a couple and actually start dating, but he was keeping things much more casual between them. On the one hand, she was disappointed, but on the other, she was also filled with nervous anticipation. She reached her hand across the table. "Deal," she said as he took hers in his.

Dan winked at her. "That doesn't mean we can't have a little friendly sexual relationship on the side," he said teasingly. "Because if you're anywhere as turned on as I am, it'd be pure torture to NOT experience each other every now and again."

At his words, Tina looked down at her outfit-boobs almost falling out of her top, pubic region threatening to spill out of her shorts, derriere mostly exposed, and felt the return of the sexual energy that had started to drain out of her return with a rush. Without moving her head, she looked up at him through hooded eyes and nodded silently.

Dan sprang out of his seat and came around to help her up, then gathered both of their garbage to throw it in the trash. "In that case, I think we have one more stop to make," he said to her, before leading her from the mall by the hand. He helped her into the car, then rushed to the driver's seat. They quickly left the mall and headed to another part of town that Tina had rarely visited, even in her college days. It was known as the "Porn District", and Tina's heart thudded in her chest, her bosom rising and falling rapidly with nerves. He'd placed her hand on his thigh once they'd left the mall parking lot, and his was resting near her crotch on her bare thigh. Several times he slowed down in front of stores, only to pass them by, looking for something in particular. Finally, he seemed to make a decision and pulled into one.

"Let's go," he said, jerking her door open and extending his hand to help her out. "I think they're going to have just what we need in here." Tina looked at the store front where they were, "The Lion's Den". It was a plain, grey building with a tasteful red and white sign. A couple of cars were parked in the lot, which had the lights just becoming to turn on in the dusk.

Once inside, it was definitely a sex shop. Adult outfits were exhibited on one wall and there were several racks and shelves covering about a third of the floor space with more. A third of the space seemed to be movie racks, and Tina couldn't even begin to imagine all the smut that the store contained. Dan however, led her to the last of the thirds, the sex toys. A college-aged male was behind a counter there, and Dan led her straight to him.

"This is Tina. She's an uptight college professor and needs something to help her break the tension," Dan says to the young man. Tina blanched at the outright, possibly ruinous description of her, but couldn't help but notice the flush coming to the salesman's cheeks.

"Ummmm...what were you thinking?" The salesman stammered. Dan smirked at him.

"I don't know-I'm not a woman and I don't sell sex toys," he said roguishly. "That's why I came directly to you, so you could help her out."

The young man flushed an even deeper red, then quickly stepped out from behind the counter to lead them into the aisles. "What do you like?" he asked Tina.

Now it was Tina's turn to blush. "Um, I actually don't know," she said shyly. She couldn't look directly at either of the guys whose company she was in.

"Well, we can go pretty laid back to start, and if you see something you like, just let me know and we can look at it more," the salesman reassured her. Dan allowed her between himself and the salesman, who led them to a rack of finger vibes. "A lot of women like these," he said to them. "They're good for teasing the vaginal opening or using on the clitoris or nipples, but women don't seem to think they do much as far as vaginal stimulation. Plus, they're more in the lower-cost category, so if you buy one and don't get as much pleasure, you haven't lost much in the investment."

Tina was uncertain, but Dan quickly grabbed one off the rack for her. "I think she should at least try one, don't you?" he said to the young man. "What else do you have?"

The kid-Tina could see he was barely out of his teens, if he even was-then went to the simple dildos. "Some women really like these, but some think they're too vulgar," he offered, looking at Tina to gauge her reaction. She allowed her gaze to wander-they were in all shapes and sizes, and all kinds of different colors. The salesman slowly allowed them to meander a little, then guided them to another section with double dildos and more exotic kinds. Some of them made her blanche that anyone would try and fit such a mostrosity inside them, some were whimsical, some had double ends that she figured must be more for lesbians. Nothing really struck her fancy, and the salesman seemed to intuitively realize it.

They turned a corner, and were in an entirely different toy section-many different kinds of clamps. "Does the lady like her nipples being played with, up to and past the point of pain?" the young man asked.

Dan looked down at Tina. "Well, do you?" he asked.

Tina's eyes dropped in embarrassment to the floor. "I enjoyed when Mike would pull on them and bite at them," she told them.

"A lot of women do," the salesman said with more confidence. "Some enjoy having them clamped between some pinchers, some enjoy more the shields," he said, directing their gaze to a small showcase. Dan pounced. "I think she'd enjoy a couple of sets of these," he told the worker. Dan pushed Tina forward a little. "Pick a couple that strike your fancy," he directed her.

The store clerk stepped in, "Not all women's nipples are the same size, so she needs to be sized for a set," he informed them. Tina's eyes flashed up in shock, but the clerk was holding out a piece of cardboard with holes in it. "Just hold this in front of your breast, and find which size fits snuggly", he told her. Tina slipped it beneath her shirt and slipped her nipples into the holes until she found one that was comfortable. Placing her finger over it, she realized that Dan had been right earlier-by doing so, she had inadvertently given both of them a bit of a show. That realization made her nipples swell even more, and she gasped. "I'd tell you to get a size above, the size you think you want, and a size smaller," the young man said. "That way you've got quick play, longer play, and more acute play."

"Good idea," Dan said to him. He looked at the card and smiled in appreciation at Tina as he took note of the size. She picked out two different kinds-one with fancy edges that had a smooth ring for her nipple to fit through, and one that was more aggressive with little teeth all around the inside. Dan leered at her as he found three sizes of each.

"Just make sure to take them off every couple of hours," the salesman warned them. "Otherwise, I understand that getting them off is extremely painful." Seeming to think they were done, the salesman began to lead them back out to the checkout, but Tina caught sight of another kind of toys. These seemed to have multiple heads, and started to browse. Dan held the toys in one hand, his other splaying across her abdomen. His thumb teased beneath her breast, this little finger dipping below the waistband of her shorts. Tina craned her head back to look at him, and the salesman realized that they were no longer following him.

"Ah, I should have realized," he said. "Thrusters. Some have rabbit ears to stimulate the clitoris, some have rotating barrels to stimulate the g-spot better. All of them thrust in and out of the vagina, hence the name," he educated them. "Some have an anal stimulator as well, for the more adventurous. Some women swear by them, some think they're too noisy. I wasn't sure about you."

Dan reached for one with the rabbit ears and rotating barrel, dropping a couple of the shields in the process. Unthinkingly, Tina bent to pick them up, causing her shirt to slide over Dan's hand so that his hand was squarely on her breast. Instantly he began to squeeze and massage it, occasionally running his fingers over her firm nipples. He kept it there as she straightened, the salesman's eyes going directly to her chest as she did. "I think she'd look amazing with one of these running in and out of her, don't you," Dan said to the young man.

"Sure," the clerk croaked. "I think she'd look amazing regardless of that." Dan's finger pinched her nipple hard, making her squirm against him in pleasure.

"The trick is to letting someone see her do it," Dan replied. He began to pull a little bit and Tina gasped, her eyes going hooded. The hand arched, flashing a little bit of her breast to the clerk, and Tina felt her pussy gush at the experience. "Any ideas on getting her comfortable with opening up like that?"

His eyes fixed on the ripe flesh being shown him, the young man couldn't form a very coherent thought. "Just keep doing what you're doing," he finally stammered. "She seems to be enjoying."

Dan's hand switched to smoothing her skin, then he pulled his hand out from her shirt. "Ready?" he asked her brightly.

Tina wanted to scream, because she was ready to take him home and ride him the rest of the night but also didn't want the experience to end. She just pressed her lips together tightly and nodded, then followed the clerk to the desk. The toys were bought, and Tina was led back out to Dan's car. There, he kept hold of the bag after helping her in, and turned the light on to rifle through it. He offered her a set of the smooth but intricate rings. "Put them on," he ordered. Tina broke one free of the cardboard backing, then began to fish it under her shirt but Dan stopped her. "Take the shirt off first.," he ordered.

She looked at him. "Go ahead," he encouraged. "Take it off, let yourself enjoy it."

Slowly she peeled the tank top over her head, her breasts jiggling slightly.

"That's it," Dan encouraged her. She fed one nipple through the first shield, instantly feeling it swell against the cool metal. She quickly did the same to the other side, then gasped at the pleasure and raunchiness of the situation. Dan turned the light off, then put the car in gear. "Before we get going, take your shorts off," he instructed her. Quickly, she unbuttoned them and slipped them off, her new g-string staying on. Dan handed her the finger vibe and a battery to put into it. "All the way home," was his harried instruction. She looked at him, thoroughly aroused at all they'd done throughout the day, slipping the battery into the vibe before rotating the base to turn it on.

She started with one nipple as they pulled out onto the street, then switched to the other at the stop sign at the end. She barely noticed the group of people looking at her as they crossed the street, she was enjoying the sensations and memories of the day. Quickly, that became not enough, and she moved the vibe to her vulva. She could feel her clitoris becoming even more engorged and begin to peak through her lips. She resisted the urge to use the vibe on it right away, and instead just teased her outer lips, then progressed to her inner ones. She felt her nipples swelling even more against the shields to the point of just becoming uncomfortable and gasped in pleasure. Tina moved the vibe to inside her slit, and the sloppy sounds made her leak even more lubricant.

Just doing what felt good, Tina ran the toy from her opening to the root of her clitoris. The wet sounds were getting more prevalent as she played, and suddenly she gasped as Dan's hand came across and roughly pinched her nipple. Her eyes shot open as her gaze shot to him and she gave a guttural groan. Her free hand went to her other nipple, and she mimicked what he was doing. She started running the vibe up and over her clit occasionally, making her hips buck and writhe. She was close to cumming, and suddenly Dan whipped into a parking lot.

"Do it," he growled at her. "Cum."

For some reason, the instruction pushed her over the edge and she bit her lip to keep from shrieking. Her whole body convulsed in orgasmic bliss, and the whole car smelled of her sex.

Once Tina's breathing was getting close to being normal, Dan put the car into drive again, but pulled her upper body across the seat. He pulled his cock out, flopping it against her face. Her mouth opened of it's own volition as she took it inside. Dan's free hand pawed at her rear, and his words ground out again. "Keep that vibe going down there."

Tina kept working the vibe, more slowly this time, as she sucked Dan off. Within a few blocks, he was suddenly jerked the car into another parking lot and pushed down on the back of her head slightly, holding her in place as his hips thrust slightly and his penis throbbed in her mouth and throat. She hadn't done it in a while, but learned that Dan's ejaculate was more enjoyable than Mike's had been. She didn't mind swallowing as much as she could. Slowly, the throbs and spurts into her mouth ceased, and the hand that had wrapped itself in her hair pulled her head up.

"Did you enjoy all that?" Dan's voice came through. Tina nodded. "Good. Finish making yourself cum before we get home then, and we'll see what else we might figure out to do."

Tina once again stretched out against the seat and this time worked to make herself orgasm again more quickly, since she figured they were only a few blocks away from her car. She came again just as they were pulling in to the park parking lot. Dan allowed her to recover, then turned the light on so he could watch her get dressed again. He assisted her out of the car, then helped her move the bags to hers. Taking her in his arms, he gently kissed her.

"Play with those toys, figure out more of what you like," he instructed her. "And start dressing a little more sexy. I'll be around tomorrow and see what else we can get into." With that, Dan helped Tina into her car and watched her drive away, his mind on just how far he could push her.