The next few nights were spent with Jessica at his place or hers. She indeed was a glorious thing. Her sense of humor was through the roof; she was ready with conversation always, and not to mention her compliments of him were nonstop. He had no idea why she was still available. He was thinking hard about taking her off that market, asking her to be his girlfriend officially. He liked her that much.
The only thing holding him back was he wanted to see where this dinner date with Ms. Evans would end up. And that was tonight.
He had told Jessica he was busy with friends and wouldn't be available for anything more than a text. She had understood, at least he thought she did. He didn't want to dwell on it; he just needed to see where this drug called Ms. Evans would go.
To get ready, he trimmed all, and that means all, of his body hair, took a long shower to clean every crevice conceivable, cut his nails, put on his best boxer briefs, and ironed his going out clothes. When he was finished and all put together, hair perfectly coiffed, even he had to say he looked rather hot. He finished the outfit by packing three condoms; no better make that five instead. He had no idea if protection was needed with Ms. Evans, so better to be safe than sorry.
He intended to pound every last bit of sexiness right out of that cute ass of hers. With one last check in the mirror, he went out his door to knock at the next.
It swung open quietly with the touch of his knuckles. It was almost eerie; the house was silent, seemed empty save for the delicious smell coming from the kitchen. Should he just enter? He sent a text from outside still, "I am at your door. It swung open. Do I come in?"
Three dots appeared, and shortly after her reply, "Yes, come in, close and lock the door behind you. I will be out in a moment."
Stepping into her apartment, he noted the walls throughout the rooms and hallway, and he could see that the painting was done entirely. Her lines of cutting in different colors were precise, zero drips, and not a single mistake was visible.
As he looked at the kitchen walls, a door opened behind him; he turned to look and lost his breath. There stood Ms. Evans. Her grey hair pulled back into the neatest bun, sleek and tight. A pair of black tortoiseshell glasses, framing the green of her eyes, perched on her cute little nose, makeup on, yet muted. Below her chin, a circle of pearls choking her slender neck, a black dress hugging her form below that, a small amount of cleavage showed from between her pert breasts. But his eyes didn't stop there; they flowed down her form, with the lines, the dress coming just below her knee, there met by black hosiery that glided down her calves and into those black high heels he had seen, the ones with the red soles.
She was a sight to behold, the librarian fantasy complete. With his eyes finding the floor, he slowly brought them back up every inch of this sexy older woman. Seeing a bemused smile, he couldn't hold eye contact with her and had to break it off after just moments.
"Hello, Kyle, you look handsome all dressed up," the words curling out of her with a sensuousness that made his balls begin to tingle.
"Um, yeah, ha-ha, thank you, I feel underdressed now that I see you. Aren't you just the epitome of a sexy librarian tonight?" He fumbled with every word, trying to make eye contact and hold her gaze yet failing again and again as the power and strength she was exuding were just too much for him to handle.
"I would like you to change. The robe lying on the chair there is for you," as she said this, her hand directed his gaze to his right; there laid a grey silk robe.
He bent to pick it up and made to head to the restroom to change, but she stopped him with the command, "No, change right here, where you are. Hand me your things as you take them off."
Looking up at her sideways, he wondered if he should argue the point, and if he did, what the consequences would be? Decision made, he began untying his trainers, his butt resting on the arm of the chair.
He handed those and his socks to Ms. Evans and watched as she neatly folded his socks and tucked them in his shoes, setting them all on the floor near the door.
He removed his belt, watched that get looped, and added to the pile, then his chinos, which were deftly folded and lined up perfectly. They looked like something in a shop window. His shirt, unbuttoned, followed and was similarly handled. He picked up the robe to slip it on, leaving only his boxers, but somehow, he knew this was wrong. Looking up, he saw the disappointment in her eye.
Dropping the robe back on the chair, he slid his boxer briefs slowly down his legs, his cock, already semi-stiff due to the look and attention of Ms. Evans, sprang out, causing him mild embarrassment. Yet as he held the boxer briefs out to her, he noted her green eyes focused on that semi, and the faintest of smiles graced her dark red lips.
Standing fully nude before her now, he brought his hands in to cover himself, but with just a tiny shake of her head, she indicated that would be the wrong move.
After placing his now folded boxers on the top of the stack of clothes, she turned and stepped up to him. Her lips angled up toward his, yet didn't touch, just a fraction of width away from his, and there she stopped. Her right hand glided across the skin on his back, delicate yet determined. He felt her left hand on his growing erection and a slight pull toward her. Her fingers slid down the length of his shaft and dropped down to cup his balls. Her body was now pressed against his chest, her lips still not connecting with his.
Then she turned, releasing him so suddenly he fell forward a bit, though steadied himself quickly. Looking up, she was now holding out the robe to him.
"Put this on, and then it is time for dinner," she commanded. Her voice grew in strength each time she spoke to him. Taking his hand, she led him toward the dining table and, pulling out a chair, held it for him to sit. After he was seated, she pushed him into the table.
The way she had it set matched everything he had experienced thus far. It looked like a five-star restaurant, not that he had ever been to one, yet if he had, this was what it would look like, he imagined.
She brought the food in courses, and like everything else that night, it was perfect. The wine, a Zinfandel, added to every flavor. They talked a bit, but he couldn't seem to make conversation, yet she did respond when he complimented the food or an aspect of her that he appreciated.
"Are you ready for dessert," she asked at the end of the meal.
Strangely he was. Typically, he would be too full for dessert, yet as he thought back over the meal, each course had been a small portion, and although he wasn't hungry any longer, he also wasn't full. Nodding his head, he said, "Yes, please!"
He didn't get the dessert he had been thinking though. As he watched, she pushed back from the table and pulled up at the hem of her dress. His eyes followed her fingers and noted with a certain amount of delight that she had on a red garter belt clipped into the black hose. Rising off the chair slightly, just so she could pull her dress higher, he saw the garter belt. There were no panties, so her slit, with a trail of hair, was exposed just below the throng of red lace.
She pointed at the floor before her and said, "Come here and take off my shoes."
He didn't even think of saying no but quickly took the spot she designated and removed each shoe, in turn setting them aside.
Next, touching her thighs, she said, "Now these clasps, undo the front and back."
As he undid the front, she lifted her leg to his shoulder so he could reach the back. His hands were shaking at the sight of her exposed nether this close to his face. He wanted to duck in and taste her slit yet knew he should wait for her permission. Clearly, she was in control of the night, and he wanted to let it unfold the way she planned it, a new experience for him. He had always been in control in all his relationships through the years, yet somehow tonight, he wanted to be following her orders. The confidence she was showing turned him on immensely, and even just helping her out of her stockings was making him hard once again.
The other clasp followed the same show; the only difference, he felt her toes through the stockings rubbing against his skull just behind his ear. Her next command broke his reverie, "Now the stockings."
Gingerly he began pulling at the one he had just unclasped, "Careful, you don't want to be punished for ruining them now, do you?" She hissed as he was bringing them down over her knee.
"No, Ms. Evans," he replied, "I don't want to be punished."
"You may have no choice in that," she answered with a small laugh. It wasn't a friendly one, he noted, more mirthful and dangerous.
Her stockings removed, folded as neatly as he could manage, and set on her shoes, she slid her ass forward and placed a foot on either of his shoulders.
She said, "Dessert course one, you may lick my calves and suck on my toes, but do not go beyond my knees."
Her skin tasted of vanilla and coconut, no doubt the scent of the lotion she had applied to her slick, smooth, freshly shaved legs.
As he moved down across her ankle and toward her toes, she moved the big toe to his lips and pressed it in. Of course, he let it in and sucked lightly on it. Looking up toward her, he noted her eyes were closed, and her hand slowly slid down her taut body to find her now moistening slit and draw her fingers up, bringing the juices to her clit. A small sigh escaped her mouth, and she pressed her hand in farther.
He wanted to join the fun, so, letting go of the toe, he headed back up her leg, but as he crossed her knee, her eyes flew open, and she brought her hand firmly to the top of his head and pushed down. "I didn't give you permission to go past the knee, yet did I," her voice strong, her tone insistent.
"No, Ms. Evans, sorry," he gulped and headed back down the curve of her calf toward her foot and waiting toes.
Soon she had both her feet on his shoulders, her one hand buried in her slit the other rubbing at her breasts through her dress. He tried kissing past her knee again, and this time she grabbed him with both hands on either side of the head and quickly pulled him toward her waiting pussy. She brought his mouth against her and pulled him tighter as he started licking.
This time it was allowed, and so he ate as if his life depended on it. His hair being pulled, and his nose and mouth buried in her wet snatch, her flavor mixing quickly with the vanilla coconut already on his palate.
His breathing was difficult, with his face buried so deep. He was hoping to have her cum soon so he could suck in some air, and with just a couple more flicks of his tongue, she was gushing her honeyed liquids into his mouth as her body convulsed in the chair. His hair was pulled on very hard; he wanted to cry out in pain but felt it best to continue licking and even took her clit into his mouth and sucked on it, getting a fresh release of liquid as his reward.
Suddenly, the hands that had been pulling him into her began pushing him away, then a foot was on his chest, and he was pushed back, falling to the floor below the table, just barely missing hitting his head. He flopped back awkwardly, his knees getting caught up under him, his robe sliding up and opening so that his semi-erect cock flopped into view.
Her foot found the center of his chest, and she was standing above him again, "Are you ready for your turn?" she asked him, looking down with an air of superiority, exacerbated by the fact he was flat on the floor with her towering over him.
Gazing up her long legs, right past her pussy and the dress bunched at her waist, he looked her in those eyes, her glasses off and hair now falling from her bun slightly, he responded, "Yes, please, Ms. Evans."
She moved her foot and turned her back as she strode purposefully toward the second bedroom, opening the door and stepping inside, waiting for him.
He followed, the space lit by three big candles in one corner, the shadows dancing on the walls. He noted a twin bed with a metal head and footboard chained shackles attached to each corner.
She took his robe off and directed him to lie on his back on the bed. After he lay back on the sheets, she first bound his hands one at a time, closing the restraints with a click. Next, his feet were locked up, and she checked all the locks to see that they were solid.
Standing next to him so he could watch, she slid a nylon on and reattached it to the belt, then the same with the other. Her dress was smoothed down, and with a smile, she turned on her heel and left the room, shutting the door behind her.
What is she playing at, he wondered, why has she left the room? She said she was going to care for my needs.
He tried flexing his wrists and sliding out of his fetters, yet they were tight enough he couldn't slip them. In fact, the bed and those restraints seem perfectly fitted to his frame, all four of his limbs being pulled in opposite directions, not painful but not comfortable either.
After what seemed about fifteen minutes, Ms. Evans stepped back into the room, announcing herself by lightly clearing her throat. His eyes jumped back open at the sound, and he saw her now in the silk robe that had been his at the dinner table. He noted her glasses were back on and her hair perfect once more, fresh lipstick staining her lips, that deep red color again.
She looked at his now quite flaccid cock and, with a small smirk, slowly undid the robe, letting it slip from her shoulders, falling open to show her dark rouge nipples perky and pointing in the cool air. The garter belt and nylons still on, her high heels now on as well.
That smile still on her face, she bent down at his waist, and he could feel her breath floating across his dick. Just her presence there had him beginning to grow again, and then the breath was replaced by wet as her tongue glided up his length from his balls to the tip. With a swirl, her mouth fell over him, and she sucked him into her warm mouth. His cock was not restrained like the rest of him; it sprang forward and hardened.
Her mouth still on him, her hand found his sack, and she caressed his balls then gave them a light squeeze, a bit of pain but the feeling so sexual it brought on even more growth.
Standing, she slid a leg over him and straddled him. Taking his erection, she directed it to her slit; she sat down on it. Her heat swallowed his thick cock; he could feel her clamping on his shaft. She began to bounce, her eyes closed behind her glasses, her hair staying perfect, each breast bouncing slowly in rhythm with the movement of her hips.
Suddenly, he thought of the condoms he had brought and blurted out, "I brought some condoms. They are in my wallet –"
"Quiet!" she snarled. "I would have asked you for one if I wanted one." She slid off him and stood up, leaving the room and his shrinking dick behind her.
Man, I have blown it, and worse, I am still bound. What now? He wondered all this after she left.
Ms. Evans stepped into the room again, her pair of champagne-colored panties in a wad clutched in her hand. Stepping over to him, she stuffed them into his mouth, "Stay quiet, or there will be consequences," she affirmed.
He noted the panties were not clean, they tasted of her, and he could also tell of him. The mushroom flavor sealed the deal, these panties were still dirty from days back, and he began to gag a bit.
But that was short-lived as he felt her mouth on his penis again, resurrecting his hard-on with just a few dips of her head.
With him hard again, she once more slid on him and began rocking. The rocking gave him very little sensation, so it was more for her, not him. Her fingers found his nipples, and she began twisting and pinching them, her breath coming in shorter gasps, she clamped down on him again, and with several shudders, she cried out, "Oh god, Kyle, I, I, I'm cumming!!!"
He thought his nipples might bleed as she roughly twisted them as she came. They didn't, he noted as she released them, but they were indeed red and a bit puffy.
Standing again, she turned toward the door but did not leave; instead grabbed something from the dresser along with what appeared to be some lube. Turning back, he saw she had a small dildo in her hand and was rubbing the lube on it as if she was jerking it off.
He wondered, Why is she going to stick something small in her like that after my cock? Why not my cock again? Maybe it's for her ass?
A moment later, as she bent over him and engulfed his cock in her warm mouth, he realized it was for him as he felt pressure at the pucker of his ass. After a few moments of pushing it slid in, just her finger and thumb wrapped around the base, she slowly fucked him with it. At the same time, she bobbed on him, bringing his dick back to full mast. She buried the dildo in his ass all the way and again slid over him, taking his cock deep in her pussy. She began bouncing on him now, pinching her own breasts and twisting them, giving him the show she believed he wanted.
Pushing with his tongue as hard as he could, he forced the panties to tumble out of his mouth, and he tried to forget the taste of his own spunk.
She had set up the dildo in a way that it kept bumping as she rode him, each bump a nudge of his prostate. It was all quite too much for him to take, and he cried out, "Oh fuck, Ms. Evans, fuck, fuck, fuck," and with that, he came hard, strand after strand flowing from him, deep in Ms. Evans' pussy.
She rocked on him once more, and with a gasp, he felt her heat flow over his shrinking cock as she came again. She fell forward onto him now and lay shivering on his chest as he slowly came out of her. As he fell out all the way, she kissed and slid her way down his body; taking his now spent dick in her mouth, she sucked hard as she gently pulled the dildo from his ass. The removal of pressure on his prostate, along with the sucking draw, rewarded her with two more strands of his sperm as he came a bit more in her mouth.
Standing, she covered him with a blanket and unlocked all but one ankle from the shackles. She turned and at the door looked over her shoulder and said, "Get some sleep boy, you are going to need your energy in the morning." Tossing an empty water bottle on the bed, she added, "For when you need to pee." And with that, she exited, closing the door behind her.
Kyle lay there for hours, running through what had happened that night, not sure if he was comfortable with all of it and thinking he wouldn't sleep because of the ankle restraint. Yet sleep must have found him after a few hours because when he opened his eyes again, it was light outside, the blanket was off his nude form, and his ankle was free.
Getting up, he wandered into the front room to find Ms. Evans, but the house was quiet. He grabbed his phone instead and noted five messages from Jessica and one from Ms. Evans.
Opening her message, he read, "I had to run; you were dead to the world when I tried to wake you. Show yourself out. I won't be back until after two."
Along with a picture, a selfie of Ms. Evans with him on the bed behind her, his shackled foot showing. She had placed the dildo near his ass, and she was nude.
What does this mean? Has she come in for more fun and found him asleep, or is this a form of blackmail for the future? He wondered which it was but didn't dwell on it.
Scooping up his clothes, he put on his pants and shirt and showed himself out, and he locked the door behind him.
"I am out, and the door is locked. Why the picture?" He sent it to Ms. Evans.
Entering his apartment, he locked the door and took a deep breath in the familiar and safe surroundings. Sliding down to the floor slowly, his back against the door, he felt a bit of pain in his ass from the unexpected abuse it had endured. He had enjoyed the night overall, but it was still a bit disconcerting the way she had treated him. He didn't feel safe with her, and while there was a draw to that, he wasn't sure he was up for the challenge.
Opening his phone, he checked his messages from Jessica.
11:02 p.m. "Hi, hope you are having fun with your buddies." Smiley face emoji.
12:27 a.m. "I wish you were here, so horny."
12:27 a.m. A picture of her, her face with one nipple near her mouth.
3:06 a.m. "I can't sleep, used to having you in the bed with me."
9:19 a.m. "That's it, I want you in my bed all the time, I want you, and we must talk. Coffee this morning, say 11:00 a.m. at our spot?"
Glancing at the time, it was 10:42 a.m., so he sent, "Coffee sounds great, running slow today, could we make that 11:30 a.m.?"
Jumping to his feet, he tore off his clothes running for the shower. He wanted Ms. Evans off him, at least for the day. At this moment, he had decided what he wanted, and he would meet Jessica shortly for coffee and no doubt, giggles at their spot.