Caught In-Between

"Well, good," Mandy said by way of a greeting, "looks like we're going someplace casual."

But Jason took it the wrong way. "I'm sorry. We can go someplace fancy. I—"

"No, no. I meant I'm glad. It's our first date so we should go someplace relaxing where we can just enjoy each other's company."

He breathed his relief. "Well, I have a couple of places in mind, depending on what kind of food you like. But if you have someplace in mind, I'm open for suggestions."

"I don't eat out much. I could be happy just ordering a pizza and relaxing on the sofa."

Knowing of her sexual predilection, Jason thought her implication was fairly clear. "That would be a little intimidating for our first date," he said. "Besides, I'd really like to take you out."

"Then out we will go. Steak, Italian, Asian are my favorites; Mexican, not so much."

"Perfect. How about Angelo's?"

"That would be perfect."

And it was. The food and wine were great and the conversation terrific. In a relaxed atmosphere away from the office Jason became quite talkative admitting again that he found Mandy not only very easy to talk to, but someone he actually wanted to talk with. He imparted that, growing up, he'd always wanted to be a lawyer, and listening to his father's frequent complaints about how unfair income taxes were and how illogically they were calculated pointed Jason in the direction of becoming a tax attorney, particularly since he was good in math and with numbers. He'd never been popular with girls, and so, not very forward with them. Over the years, there had been a few—very few—who had shown some interest in him, but he'd always been too awkward with them to have any lasting relationships. And so, as he'd gotten older, he simply avoided entanglements.

Mandy revealed that she had attempted college, but after four semesters of changing majors and still not deciding on a career, she switched to a vocational school to simply learn to become a paralegal so she could work for a while, earn some money and go back to school. However, she found she enjoyed what had become her occupation, and so, never got around to going back to college. Now, she particularly like being Nelson's paralegal and Julianne's administrative assistant. They both were easy going and not demanding.

"You're really good at what you do," Jason complimented. Then, with his usual hesitancy, he mumbled, "Where did you learn your other . . . talent?"

"What other talent?" Mandy asked with a frown.

"You know, your, uh, your carnal . . ." he bobbed his head from side to side for lack of the proper word.

"My carnal what?" Mandy shook her head. "Jason, if we're going to be friends, you can be frank. Just say what you want to say."

"Mandy, I'm a lawyer, and everything is about the words we use and how we use them. But you're right, if we're going to be friends, I should be able to speak more openly." He paused to rethink his question. "You seem too really enjoy sex. I've never met a woman who was so open about it. How did that come about?"

She shrugged. "You discover masturbation at some point in your youth, you decide you like it, then you realize you like it a lot and it almost becomes like a drug that you have to have. Then you graduate to intercourse. And nothing is better than that."

"So, if I'm not being too personal, how do you take care of that? Do you have a boyfriend?"

"If I did, I wouldn't be here on a date with you, would I?"

"I don't know. Would you? Maybe you play the field."

"Is that your subtle way of asking me if I fuck around?"

"No, no, of course, not," he stammered.

But his expression told a different tale. "Well, I don't. And I don't have a boyfriend. Haven't in a while. Truthfully, I haven't found one good enough to hold my interest, if you know what I mean."

"I surmise you are referring to someone good in bed."

"I am."

"Well, without making any assumptions about any future we might have together, that would be a lofty standard for me to aspire to," Jason said nervously.

"I wouldn't worry," Mandy said, reassuringly. "You rose to the occasion the other day."

He merely smiled, fairly certain there was a double-entendre in there. To quickly change the subject, Jason asked, "So, where would you like to go next?"

"I have nothing in mind. Do you?"

"Not really," Jason said with some embarrassment. As I said, I haven't dated much so I don't really know what people do. Go to a movie?"

With a shake of her head, Mandy said, "No, I'm not really in the mood for a movie."

"Oh, okay. Well . . ."

"I guess you can just take me home."

"Oh. Well. Alright." The disappointment was clearly evident in his voice; so much so that he was fairly quiet during the drive.

It amused Mandy. She chatted idly with him while riding, and he was polite enough to respond, but that he was letdown was unmistakable. At her apartment, Jason walked her to the door, and when she turned to unlock her door he was about to walk off.

"Where are you going?" she asked. "Aren't you coming in?"

He stopped. "Uhhh. What?"

"Don't you want to come in?"

"I didn't know I was invited."

Mandy knew she had misled him. She felt that if she had said, let's go back to my place at the restaurant he would have become all hyper and nervous. Still, she shot him a look of preposterousness. "Well, of course, you are."

"Oh, well, uh, if you, uh, want me to."

"Of course, I do."

So, with obvious nervousness, he followed her inside. She set her purse on a counter that looked out from the kitchen, and then went around into that room.

"How about a glass of wine?" Mandy offered.

"Uh, sure, yeah, that would be good." Jason walked behind her into the kitchen. He saw the bottle of red wine already sitting on the counter beside two wine glasses. "You planned this," he deduced.

She turned and grinned. "I'm devious that way."

"Why didn't you just tell me?"

"Didn't want you to have to think about it too much." She quickly uncorked the bottle and poured them each a glass. Handing him his, she took hers and sat on a small table in the corner, which was only a couple of steps away. Her dress rose high on her thigh.

Jason took a sip and faced her. "So, why did you feel you had to lure me back here?"

She shrugged. "Before we left here when I suggested just ordering a pizza and staying in, you said that would be intimidating. Then at the restaurant, you were worried about—what did you say?—a lofty standard to aspire to." He was close enough that she could reach out and tug on his forearm to bring him nearer. She ran her fingers through his hair. "I didn't want you to be tormented during the ride here. Now, you'll only have a few minutes to get nervous."

"You're so considerate."

Mandy let her hand drop to his cheek and neck.

"So, you're, uh, expecting me to, uh, have, uh, s-sex with you?" he asked, his voice wavering.

After a big sip of wine, Mandy set her glass down on the table beside her and slid her hand down his shoulder and arm to his hand. She then took his hand and placed it on her mostly exposed thigh. "I'm not expecting you to do anything. I was hoping you'd want to." Still holding his hand, she moved it up and down her leg.

"Uh, well, I, I had a suspicion you might want to do something l-like this."

"Yeah, I'm not too hard to figure out." Feeling that his hand would remain on her thigh without her having to hold it there, Mandy gently placed her hands on either side of his head.

"Well, I, uh, didn't, uh, want to take anything for, uh, granted."

Pulling his face closer, she kissed his cheek tenderly. "So, does that mean you want to?" she asked in a sensual whisper.

"Well, I, uh, I don't—"

"No need to be nervous. You've got experience."

Jason chuckled uneasily.

"I think you really want to, you're just too nervous to admit it."

"There would be some truth to that. I actually can't stop thinking about our first time."

"Neither can I," Mandy agreed, slowly pulling his shirt tail out of his pants. She shoved her hand underneath to rub the skin of his abdomen and up to his chest. She then unbuttoned and removed it. Holding his head again, she kissed all over his face and neck on down his chest, sucking each of his nipples. That made him shudder and suck in his breath. Finally, she pressed their lips together in a passionate kiss. He responded eagerly.

Jason's fingers had become slightly active on her thigh. After a minute or so, Mandy leaned back supporting her upper body on her arms. She lifted one leg and crossed it over the other causing her dress to slip even closer to her crotch. She wanted to see what he would do with his hand, and to her satisfaction, he ran it up the side of her leg until his fingertips made contact with the elastic leg hole of her panties. He stretched the elastic out, but did not go beyond. When he moved his palm over the top of her leg maintaining contact with the elastic, she sat back up trapping his hand between her legs and pressed against her pussy. She knew he could feel her wetness. His sudden inhale confirmed that.

Becoming slightly aggressive, Jason kissed her neck and shoulders, so she leaned back just a bit puffing her chest out. He took the bait and kissed down her cleavage until the material of her dress prevented him from going further. She liked that he was not only catching on, but becoming more of a participant.

When he pulled back, Mandy's hands went straight for his belt and zipper, which she had undone and open in seconds. She pushed his pants down as far as she could, somewhere around his knees, and then quickly kicked off her shoes off and used her feet to drop his pants to the floor. Surprisingly, he automatically stepped out of them.

From a quick glance down, she could see his erection stretching the thin material of his dark-colored jockey-style underwear. Pulling him to her, she could feel it pressing against her leg. To her further amazement, he pushed her dress up as far as he could with her seated. She rotated from cheek to cheek so he could free it and raise it to her waist.

Mandy stood to see if Jason would remove her dress as it dropped back to its normal length. They kissed again and she could feel his hands gathering the hem until it was again around her waist. Using the power of suggestion, she raised her arms up and he took the hint and lifted her dress up and off. She didn't wait for him to remove her bra because she felt that could be a long time in coming. Once she had it off, she wrapped her arms around him to feel her bare breasts against his naked chest. There was nothing like feel of skin against skin.

They kissed, and this time, she used tongue. He almost didn't know what to do, but her glossa coaxed his and finally they were able to dance. She was further thrilled when his hands sought her breasts, caressing them.

Mandy enjoyed foreplay as much as anyone, but there always came a point at which she didn't know how much longer she could hold out before having to have a cock inside of her. She was nearly to that stage so she thought it was time to head to her bedroom. She took his hand and he went without hesitation.

Once there, Mandy sat Jason on her bed. She stepped one of her legs between both his and her other leg on the outside of one of his and pressed her tits against his face. One nipple found its way between his lips. He naturally sucked it.

"Mmmm, yeah," she purred. "Just like that." After a few seconds, she aimed the other nipple at his mouth.

Jason took it a step further and kissed all around her breasts and in between them. Unintentionally, it seemed, his hand went to caress her thigh but landed against her pussy. As though touching something hot, he instantly pulled it away, but Mandy just as quickly guided it back. Now, comfortable with it there, he rubbed her vulva. And if that wasn't a step in the right direction, his other hand eased around back to cup her rear.

Mandy sat on his leg so their lips could meet again. In the back of her mind was also the picture of them both clad only in underwear, and there was something erotic about that to her. Gradually, she pushed him down so that he was supine except with his legs hanging over the edge. He bear-hugged her as they kissed.

It was now time to go to work on him so Mandy slid down placing kisses on his chest and abdomen as she went. She pulled off his underwear, and while in position, thought she might as well take hers off too. She took a couple of seconds to admire his hard cock standing straight up before taking it into her mouth.

"Uuuuuuuuunnnnnnhhhhh," was Jason's response.

Mandy sucked him slowly and softly. He was big and filled her mouth. She massaged his balls and then gave them each an obligatory bath with her tongue. But she really wanted the monster inside her, so she pulled herself up to sit astride of his cock. She resisted the urge to ram it in, and instead slid her spread labia along the length of his shaft. This was actually a neat maneuver and she enjoyed the thrill of her clit rubbing against his rod. On one trip up, she went too far causing his cock to slip right into her gaping hole.

The couple both moaned in two-part harmony.

Jason held onto her hips as Mandy pivoted back and forth. His head pounded, not in pain, but rather from the incredible feeling of his penis sheathed in this warm and wet pouch that was her vagina. Nothing in the world felt like this; nothing in the world felt so good. Overcome with emotion, Jason sat up with his arms around her to support her and buried his face in the crook of her neck. He just wanted to hold her and feel her against him.

Mandy sensed he was having an epiphany and allowed him the time to absorb it. It was also a somewhat unique occurrence for her to have a man inside of her while remaining motionless and being held in a very loving manner. The only movement for several seemingly long seconds was the expanding and contracting of his dick against her inner walls. She believed if they remained still like this long enough she could come just from that. Quite nice.

But finally, he rolled her over onto her back, his cock never leaving her pussy, and in the classic missionary position, they fucked. It was gentle, and with interspersed kissing, quite romantic. He pumped slowly, almost as though he didn't know how hard he should, but she actually enjoyed the pace. She locked her legs around the back of his thighs as her hands caressed his sides and back.

Becoming inventive—for him—he lifted her legs and linked his arms underneath her knees. While old hat for her, Mandy realized this was all new to him, and the notion of that lent a different perspective for her as well as another level of excitement. After all of the wild sex she'd had with Julianne and Nelson, it was actually kind of nice to get back to basics.

"Mmmm, this is so nice," she had to comment. And then, she just let herself come. It was a most satisfying orgasm, all encompassing, but not a big explosion. But it lasted a long time. "Ohhhh, that was sooo good. Let's try something different. On your side."

Jason quickly complied, and Mandy moved into a similar position, but more on her back than her side. She draped her leg over his hip, and then reached between her legs for his cock. It was covered by her juices, and she loved the creamy feel of it. She stroked it back to full hardness before guiding it back inside of her. He naturally started thrusting. Seeing his arm resting idly on his side, she grabbed his hand and placed it on her lower abdomen so the tips of his fingers were aligned with her clit. With her hand on top of his, she manipulated his fingers to rub her button. He quickly got the hang of it. She then twisted her upper body aiming her breast at his face, pointing her nipple toward his mouth. He understood what she wanted and covered the nub with his lips, sucking.

Mandy sighed, thinking he was her own personal fucking machine. She wondered if he could hold out long enough for her to come again. But with all of the attention he was giving her, it seemed in no time she was feeling the familiar pangs of orgasm. The combination of his mouth, fingers and cock had her climaxing more powerfully than the first time. She couldn't help but letting out a guttural growl to emphasize her overwhelming enjoyment.

Heavier breathing suggested that Jason was about ready.

"Come for me, baby," Mandy encouraged. "I want to feel your cum on me."

He grunted and pumped harder.

"That's it, baby, fuck me harder." She wasn't opposed to him coming inside of her, but she really wanted to feel his pearly liquid all over her body.

His "ungh, ungh, ungh," told her he was about to blow, so she grabbed his cock, pulled it out of her, twisted onto her back and jerked him until he sprayed his seed all over. He came so hard his spurts hit her tits and trailed down her abdomen. When he finished shooting, panting hard, she rubbed his semen into her skin with her free hand. Still holding his penis, a few more drops dribbled out when he saw her do that.

When he caught his breath after a few seconds, Jason said, "That was amazing! You are a dream come true. I mean, it just keeps getting better."

If he liked that so much, Mandy wondered how he would like this. Knowing she hadn't completely rubbed all of his semen into her skin and that there was still much liquid coating her abdomen and breasts, she pushed him onto his back and then got on top of him grinding those parts of her body into those same parts of his.

"Mmmm," he merely uttered. "That was erotic."

"And you were spectacular," Mandy exclaimed excitedly.

"You're just saying that."

"No, no. You were great! I feel marvelous. Don't you?"

"I do. I'm just not sure you really do."

"How can you say that?" Mandy challenged. "That was some of the best sex I've ever had. Try to have a little more self-esteem."

Jason hung his head. "I still just find it hard to believe that someone as beautiful and sexual as you would be interested in someone like me."

Still on top of him, Mandy pressed her mouth firmly to his. "Believe it. You just keep getting better. And so you know, it's not just the sex. It's everything about you. Yeah, you're handsome, you've got a big dick, but you're also smart, nice, a real gentleman; you're everything a girl could ever want."

Jason was overwhelmed, but managed to say, "Thank you. But that sounds like what I should be saying to you."

With a grin, Mandy said, "Okay, I'm listening."

He smirked. "What you said? Ditto."

"Good, because I'd really like to have a relationship with you—and not just as co-workers. And not just about sex—although, I still want to have a lot of that."

"I don't think I'll disagree with you about that," Jason said with a smirk. "But what about our bosses?"

"I don't know," Mandy responded, pondering that question. "We'll just have to be careful for now. Maybe as time goes on we can bring them around." However, as she said that, she wondered how this would affect her relationship with Nelson and Julianne.

* * *

And so, they tried the dating ritual. Jason was a quick learner. Not only did he become an ace in bed, but he also wanted to be a good all-around boyfriend—and he did. Mandy became a juggler, balancing her time with her new beau and still fucking her bosses just enough to prevent them from becoming suspicious. The thing was, she did still enjoy their threesomes, but all it would ever be was what it was. It would never be a relationship with a man, like it was becoming with Jason. She saw a bright future with him, not to mention the fact that he had a brilliant career ahead of him as an attorney.