A Date With Mandy

Author's notes:

It has romantic elements as well as sexual situations.

Please skip it if this is not the kind of story you like. There are many great stories on this site with more explicit sex.

Please do not read this if you are under 18, or are not allowed to read it in your region...

Please do send feedback and comments, they are greatly appreciated.

Special thanks to AnotherWannabe and Visioneer for their excellent feedback.  All mistakes are the author's however.

A Date with Mandy

Jon Leland hurried down the street, checking his watch. Friday night was a busy night in the trendy downtown area, and the closest parking space had been several blocks away. Already 5 minutes past 9 in the evening, he was late to his date. The girl he was meeting, Mandy, had sparked something subtle, but very real within him. Her hold on him was surprising.

As he walked to the bar, Jon smiled widely despite himself. In fact, he had been grinning like a silly teenager all week. Some of the women at his office had picked up his sudden happiness and good-naturedly teased him about it. Despite his rather transparent denials that he hadn't met someone, he was the subject of much water cooler gossip.

It was awkward to be dating again, and he wasn't sure if he had a future with this particular girl, but he really hoped so. Mandy was so completely unlike any girl Jon had ever dated, even before his long, broken engagement.

She was not only younger than him, but had several large tattoos (and said she had more he couldn't see) and a pierced eyebrow. He would have sworn she had had a different hair color each of their dates, but that was probably his imagination.

Physically, she was shorter than most girls. She often wore heels or platform shoes, but confided to him that she was only 5 feet 2 inches without them. The little jiggle when she walked away, the certain look she gave him right before she smiled, the little way she bit her lower lip when she was embarrassed—these images were burned indelibly into Jon's brain.

But more than anything about her looks, it was her personality. She was passionately into new artists, plays, bands, and clubs. Jon was surprised at how much he enjoyed some of the new music scene and developing artists. Mandy wasn't surprised he would take to it. She had said Jon had an artistic heart inside that mathematical mind, which is why she agreed to the blind date in the first place. It hadn't made sense at first, but he understood later.

Mandy was one of the most—he could only describe it as alive—people he had ever met. She had an effortless, easy way with others, was quick to laugh, and had a playful sense of humor. She had a genuine kindness and sincerity that came out whether she was talking to him, a waiter, or strangers on the street. He wished he could see her more often, but she never agreed to meet him, or even talk to him, except once a week on Saturday evening.

Their very first blind date had been brief, a two hour chat over drinks at a far too hip for him bar further uptown. The blind date had been set up by a mutual friend, Catherine, Jon's boss at a previous job. He had known almost nothing about Mandy before the date.

When he begged for details. Catherine laughed at him, and only said, "Jon, I know you and I know her. I think you may well hit it off. Are you questioning my judgment or my taste? You are done feeling sorry for yourself, and are going to be a gentleman and take out my friend for a nice evening out."

Jon tried to refuse, but no one ever really said no to Catherine van Neumann. So he went, knowing nothing, and a little nervous.

Jon had been surprised at how gorgeous Mandy was when they first met. He thought back, remembering their first date. It had been at once wonderful, confusing, enthralling, and frustrating. So it was with all his meetings with her. Despite the differences in their age, during dinner they always conversed easily.

Mandy had a curious mind, and a quick wit. She was remarkably well read, and Jon suspected she might be far smarter than she believed herself to be.

When they had reached the club, Jon noticed it was quite trendy, not a place he would usually enjoy. He realized that he was probably the oldest person there. However, Mandy made him feel completely at ease and they sat and talked over the noise. He was having a decent enough time, despite his discomfort, but then Mandy heard "her favorite song" play and literally jump out of her seat. Jon never danced, and refused her pleas to join her until the buxom young woman playfully, but forcefully, dragged him onto floor.

Jon felt like an idiot on the dance floor, especially surrounded by younger dancers who were writhing to some tune he had previously heard only in passing. He had never enjoyed discos even as a much younger man. He was too awkward, too self-conscious even in his college days. But he somehow enjoyed himself. Mandy made him feel like the coolest, hottest man in the club.

She danced as if she wanted their bodies to press into one. Her plump apple-shaped ass ground into his groin. As she pressed into him, Mandy couldn't help but feel him involuntarily harden. She squeezed his hand hard and turned her head to look at him. She smiled at him with lusty approval as she bumped her ass up and down his erect penis with the beat.

Later, after many songs, they went back to their table. Jon leaned over to try to kiss her. Suddenly, Mandy put her hand over her mouth to stop him.

"John, I really like you," she whispered breathily into his ear. "I mean a lot. But we can't have sex or even kiss. It is not that I don't want to...I just can't. I can't explain it. I just can't."

Her words cause Jon's heart both to soar and plummet at the same time.

Mandy saw the confusion on Jon's face, and continued. "Don't worry, honey, it's not like I have a boyfriend or something. I haven't had a boyfriend for a long while. It is just that my situation is kinda...complicated. Please don't be mad with me. I so like being with you, and you are so cute."

Later as they sat, she held his hand as she pressed close to him. As they chatted, Jon apologized twice for how poor a dancer he was compared to her. He also mentioned, in his insecurity, how he was too old for her.

Mandy giggled drunkenly, leaned over, and whispered, "Jon, don't you get it? You are the hottest guy in this bar, a man among boys. I got so wet when we were dancing that I'm soaked through my thong. So I decided to take it off in the bathroom." Then she discreetly slid the side of her skirt up over her hip to show him, being careful to keep her feminine charms well covered.

Mandy's phone suddenly rang, and she excused herself to speak privately. After a few minutes she returned, "I need to go now. It's late and I have work tomorrow. I've already called taxis for us both."

Jon noted the pattern was the same as in their many later dates. They'd make a strong connection. She would be incredibly hot and sexual, but she would allow nothing more than a peck on the cheek. And always a phone call that ended with her abruptly going home.

Was she crazy? Or married? What was her deal? It was incredibly frustrating, but he was determined to see where this went.

The blast of a nearby car horn brought Jon back from his memories of their first date. He looked at his watch and redoubled his pace.

Jon did not expect anything different tonight as he entered the small bar to meet the short, perky girl. They'd have a wonderful time, with a warm and soul-changing conversation, with questions he'd ask but she would never answer. An evening sexually charged, yet stiflingly polite, then not even a kiss goodnight.

As he entered the bar, he saw that Mandy was already there. It was a rather quiet place, but upscale. The bar was narrow and intimate, a stylish holdover from the 40's, with its original aged brass and teak. There was a carpeted area in the middle around the bar itself. It was livelier and more open than the rest, where perhaps two dozen young professionals mingled. Beyond, in a tight, single file row were the small, recessed tables.

Mandy was waiting for him in the front area, standing beside a tall, narrow table. Jon was surprised to see with her a statuesque woman—Catherine, Mandy's friend and for Jon's former coworker and friendly acquaintance. The pair was catching a lot of eyes in the bar. Mandy was very pretty, but in cute girl next door way. She had a perky sort of hotness and wide feminine curves.

In contrast Catherine looked like a Greek statue. She was very tall—even taller than Jon when she was wearing her high designer stilettos—with a classical, sharp face, graceful neck, and impossibly toned legs. She had long straight blonde hair, bound into a ponytail reaching to her leather-cover ass. And that ass was probably the nicest Jon had ever personally seen, except perhaps Mandy's. She had a broad smile with perfect teeth and her lips were shaded a shocking blue. John had never seen her wear anything but designer clothing, projecting her confidence, but also feminine power. Catherine could have easily have been a model or actor, if she had not gone into the business world.

As soon as she noticed Jon, Mandy's face immediately lit up. She rushed over to meet him with a warm hug and kiss on the cheek.

Mandy held his hand as she led him over. "Jon, I need to talk to you about something. You remember Catherine?"

Of course, Jon remembered Catherine von Neumann. No one ever forgot Catherine. She was a former manager in his firm, and they had stayed in touch over the years. Catherine had been the fastest rising executive at his company before getting a better offer from a larger firm. Despite starting junior to him, Catherine had soon leapfrogged him and several other managers at the company. But she was so smart, so energetic and so sincere, that Jon did not resent her.

When they had worked together, Catherine was in her mid twenties, and though a bit of a workaholic, she had a reputation for dating quite a bit. It was rumored in the office she strictly preferred accomplished older men, and that she never stayed in a serious relationship for long. But Jon never paid attention to rumors. He only saw that Catherine never dated anyone, as far as he could tell, nor had any sort of personal photos.

Despite her stunning looks, she somehow kept every business interactions entirely professional. He later did meet someone who had gone out with her, a senior executive at a different company. Over drinks, the other executive, who happened to be in his 50's, had cryptically said that dating Catherine was the most intense relationship of his life. He emphasized that it was not only incredible sexually, but also emotionally, intellectually and even philosophically. Jon did not know the man well enough to question him further, and the matter had dropped.

Suddenly, Mandy stopped and looked in Jon's eyes. Her voice was incredibly nervous. "Jon, Catherine is more than just my close friend. I actually, well, how to put this...OK, I will just say it. I sort of...belong to her."

Mandy rushed ahead. "I mean, that means lots of thing that I can't go into, but the big one is I will not make any major decision without consulting her first. And then what she says goes. It is a long story, but my trust in her saved my life in lot of ways. If it's all right with you, she wants to talk with you, about you know, about umm, about your and my thing, I mean relationship... maybe potential, maybe relationship..."

Jon was speechless, his mind spinning a mile a minute. What did Mandy mean by "belonged to"? He pushed down the stab of fear, even betrayal. She had said she was single. And why would Catherine even set them up if that was the case?

Was Mandy gay? It might explain her weird standoffishness. But it seemed impossible that Mandy could deceive him for so long; it was not in her.

Was he being played with, some evil joke of the alien younger generation? Then Jon forced himself just listen, to leave his own head. And he saw Mandy was genuinely afraid but trying to hide it. He had not seen her like this before, and John had to understand what exactly was going on in order to help her.

"Well here goes nothing." Mandy's voice warbled with uncertainty as they approached Catherine.

Catherine kissed Jon, first on the left cheek then the right. This was her typical greeting. As she looked at them, she smiled an almost bemused smile. After a long pause she motioned towards a private table, marked "Reserved party of three."

Catherine sat, relaxed, one arm over the back of another chair. It was Jon's date, yet she seemed more at home that either he or Mandy. She waited, looking them over, before she smiled thinly and leaned forward.

"Mandy," Catherine said at last, "please move closer and sit at Jon's side. I want you to reach under the table and hold his penis through his pants. You may massage it, but not too much. You are not to let go of him the entire time he and I are talking, and you are not to speak until I leave. This conversation is between Jon and me, though it is about you. You understand?"

Wait, Jon thought. What she just told her to do—is this some sort of weird prank?

He tried to steady himself, to look as cool as he thought Catherine looked. He noticed that Mandy suddenly and strangely relaxed when Catherine gave her the bizarre order. In fact, a brief flash of joy floated over her face, with a little mischievous smile.

Jon began to panic. Would she really do it? What if people saw? Someone from the firm might be in this bar.

Mandy looked down, but answered clearly and calmly, "Yes, Catherine. I understand and will obey."

Catherine looked Jon directly in the eyes. "Jonathan, I need you to answer a few questions about your feelings toward Mandy."

Thus started very strange, but short conversation. Catherine and he talked for less than ten minutes. Jon only answered Catherine's questions; she put her finger to his lips when he tried to ask one of his many burning questions. Catherine asked him to explain in his own words how meeting Mandy had made him feel, and his feelings after some of their dates.

Mandy never spoke. However, Mandy's hand never left Jon's lap, where she lovingly massaged his now full erection through his pants.

Jon was completely freaked out, but didn't dare leave. He had do know what would developed next. Was this how the mythical threesome started? Was he that sort of guy now? And at the bottom of it: he had waited so long for Mandy's sexual touch, and it was happening. Even if they were caught, humiliating as that would be, it would be worth it.

Near the end of their talk, the waiter came over and, after about a minute, noticed what Mandy was doing. She and Mandy made eye contact, and Mandy blushed with extreme embarrassment and dropped her eyes. However she never stopped her slow, deliberate hand job through his clothes. The waiter stammered something.

Catherine turned; her shoulders squared and looked the waiter straight in the eye, holding her gaze. "My friends and I are almost finished. We require nothing more. I will take the check, and thank you, your service has been to my standards."

Catherine was so confident, her tone strong but utterly casual.

The waiter never broke eye contact. "Of course, Ma'am. Right away." She left.

Catherine made it clear she herself would not be involved sexually with Mandy and him, dashing the threesome fantasy that Jon had already started working out in great detail in his head. Catherine refused to discuss her and Mandy's relationship, sexually or otherwise, and only said Mandy would tell him in her own time. Jon could see that the tall, sharp-featured blonde cared very much for Mandy, but he was not sure how far it went.

Catherine controlled the conversation and asked him question after question about his feelings towards Mandy—all very personal. Jon tried to change the subject, but had a hard time concentrating as Mandy lovingly kneaded his rock hard erection.

Suddenly, Catherine stared at the couple with complete sincerity and warmth. "I am very happy to see you two hitting it off, just so very happy. See Mandy, I told you Jonathan is one of the good ones. And now you probably agree that older men really are sexier. I have to be running, but I did know you two would hit it off. Jonathan, you take good care of her, or I will know, and I will be angry."

Catherine stood to go, putting on her a stylish and expensive overcoat. Before she left, she paused, then took an object off a jeweled charm bracelet on her wrist and placed it on the table. It was a tiny key, too small even for a briefcase, and seemed to be made of sterling silver. Jon noticed a couple a few other tiny keys in addition to the other charms.

Mandy immediately let out the quietest of moans. Jon glanced to see her biting her lip very hard to keep herself from making any noise, but her eyes broadcast her happiness like a beacon.

"Oh, I almost forgot," Catherine said. "Jonathan, I think I will leave this with you. You may use it tonight if you and Mandy wish. Mandy will return it to me in the morning."

Then Catherine turned and left the bar, never looking back. Only after the door closed did Mandy suddenly begin to talk.

She spoke in rapturous, overlapping bursts, her thoughts tumbling over themselves. "Oh, Jon, you said so many wonderful things about me. Just so touching...I wanted so much to say something, but couldn't. You are so kind and understanding...I...I..."

Then she kissed the older man, deep and passionately, and, without breaking their kiss, she shifted so she was sitting on his lap, straddling him belly-to-belly in his chair, trying to get as close as possible, to merge her mouth and tongue into his. Jon felt her tears wetting his face.

After she finally broke the kiss, she stayed on his lap, tracing the line of his rough jaw with her finger, and wiping the trace of her tears from his cheek.

Mandy looked in Jon's eyes and said: "I'm sorry that I cried. I'm just so happy. I had a rough time, the last few years."

After a few minutes Jon quietly asked, "Mandy, sweetie, one question—and I have a lot more for later—why, uh, why did Catherine leave that silver key? It's too small to be an apartment key."

Mandy's smooth porcelain skin flushed as pink as humanly possible. She looked around, then pulled Jon's hand under her skirt and guided it between her legs. Jon's eyes widened at the feel of metallic rings, not panties.

She pulled him close. "You know I have piercings, not just my eyelid and ears. My nipples as well. I love the way my nipples look with them. I also have a couple of ring piercings...down there. "

She continued, smiling as she saw the look on my face: "I know you are 'Mister Sheltered,' but it's no big deal, lots of girls have genital piercings. Well, there's a little more, I also have this smooth little ball lock to hold the rings closed. I lock it before I go out. Catherine had the only key, before now. It rubs my clit sometimes, which makes me super horny, but it's worth it in the long run.

"You see, Jon, I have been in chastity, by my own will, for over a year, but I am ready. Catherine is not my lover, and we don't have a sexual relationship, not like that. She is my Mistress and has total control over me, but only because I begged her to. I needed a strong hand in my life, someone who didn't have their own agenda."

She blushed and paused for a moment, and then as I opened my mouth with the first of a hundred questions, she gently put her finger over my mouth.

"I can answer your questions, and I'm sure there are many. But for now, take me home and make love to me, Jon Leland."