Holly

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Pegging

He stared at the sign. The Executive Men’s Salon. He’d heard great things about the place. He didn’t usually come to these fancy men’s haircut places. The chains at the mall were generally enough. But he’d also heard that the female barbers were not only good but extremely attractive. So, while he wasn’t here for anything more than a haircut, at least it would be nice to have some eye candy.

“Can I help you?”

Charles had entered and looked up to the attractive girl at the counter. “I have an appointment. Charles.”

“Hi, Charles. Welcome to the Executive Men’s Salon. If you’ll follow me.” She led him through a big room with four barber chairs on either side, and then down a hallway with enclosed rooms. She led him into the second room. “Have a seat. Your stylist will be right with you.”

“Good afternoon.”

Charles turned to the angelic voice. He was instantly smitten. She was beautiful.

“Charles?”

Then he recognized her. “Holly?”

“Yes.”

Her smile was mesmerizing. She was even more beautiful than he remembered. They’d known each other since elementary school, their families had lived around the corner from each other. He’d watched her grow into a gorgeous young woman. But she’d attended a private all girls high school, and he a public high school, and so, they’d seen little of each other through those years. Their younger sisters were close friends and had even engineered them dating a couple of times—literally a couple. And then it had been off to different colleges hardly ever to be seen again.

Until now.

She had taken his breath away the two times they’d dated. And she did so again now—to the point that he felt light-headed.

“Are you okay, Charles?” Holly asked stepping closer to the barber chair.

He smiled nervously. “I seemed to have taken a little trip down memory lane. But I’m back now.”

Still smiling, Holly asked, “Memory lane? And what was there?”

“Missed opportunities. I remembered a beautiful girl I dated a couple of times.”

Holly seemed to blush. “Missed opportunities? With me?”

Charles shrugged. “Perhaps only in my mind.”

“I never knew you wanted more.”

“I guess at the time, neither did I.” He took a deep breath. “So, you’re back in town?” Charles asked. “I heard you had moved to New York.”

“I did.”

“Fashion design or something like that?”

“Yes. Went to a school there, graduated and worked in the fashion industry for a while.”

“And now you’re cutting hair?” he asked with surprise.

“When I graduated fashion school,” Holly explained, “one of my instructors suggested I learn another trade to fall back on. She said the fashion industry could be tough. She said one could always find work as a barber or stylist. So, I learned to cut both men’s and women’s hair. She was right.”

“Were you . . . did you . . . what—”

“I’m divorced. That’s what you really wanted to know, wasn’t it?”

“Uh, well, uh—”

“I met a man in New York. A year or so later, we were married. When I lost my job in fashion, I decided I wanted to return home, but he refused to leave Manhattan. We couldn’t agree on a compromise. That left only one solution. It wasn’t really a tough decision. It wasn’t a particularly loving marriage.”

“I’m sorry.”

Holly shrugged, picked up her scissors and a comb. “So, I returned home and here I am. What can I do for you?”

“Well, I guess I’m here for a haircut.”

“What’s your pleasure?” she asked draping the barber’s cape over him.

“Are you any good?”

“Best you’ve ever had,” she said seductively.

“I never had you.”

They both laughed and it reminded him of their second date. They’d gone to dinner, and afterward, neither wanted to do anything else, but neither did they want the evening to end. So, they went to a coffee shop and talked for hours about their hobbies and aspirations. And there was laughter. Just like now.

Holly read his thoughts. Softly, she said, “I remember that night in the coffee shop.”

“I didn’t want it to end,” he admitted.

“Neither did I.” With her experience, it was easy to see the kind of cut he had, so she started trimming.

It was a revelation, not to mention a slap in the face to Charles. His expression showed his surprise. “Really? I had no idea.”

Holly shrugged helplessly. “You never really ever asked me out. Our sisters arranged the two dates we had because neither of us had anything else to do on those nights. So, I figured you didn’t really want to date.”

Charles let out a regretful single chuckle. “You were so popular; I didn’t think you’d really date me except when you had nothing else to do.”

“That would not have been true. But what is really interesting is that of all the things we talked about that night, the one thing we really did not discuss was us.”

“Missed opportunities.”

“Indeed. So, what about you?”

“I manage an insurance agency. Nothing exciting. It’s a istanbul escort living.”

“Married?”

“Was. I’m divorced also. Met a girl at the first job I had after college. We dated. She eventually started pushing to get married, and I gave in. Being married to her and living with her was way different from just dating her.”

Holly nodded her understanding. “Yeah, some people really change from one lifestyle to another. You liked to write back then. You wanted to become a writer. What happened to that?”

Charles shrugged. “I still write. Quite a bit actually. But only for my own enjoyment.”

“Did you ever submit anything to be published?”

Shaking his head, Charles grimaced.

“Why?”

“I want to write what I want to write,” he explained. “I don’t want to have to conform to some saleable format. Actually, some of what I’ve written is not really publishable.”

“Not publishable. What does that mean?”

Charles didn’t expect to have to explain. “I, uh, I, well, some of it has some very descriptive—”

“Sex?” She finished for him. “You write adult stories?”

He shrugged helplessly, somewhat embarrassed.

“I want to read them!” Holly said excitedly.

“Really?” Charles was more than surprised.

“Like you wanting to write . . . what . . . you want to write, there are many novels I’ve read that I thought some parts needed greater description,” Holly explained.

“I get it. That’s one reason I started writing such stories. If you’re serious, let me know where to send them.”

“Or you could bring them.”

Charles hoped the hidden message he was hearing wasn’t wishful thinking. “Bring them? Well, that sounds like an invitation.”

Holly lifted the barber’s cape to his waist and climbed into his lap, straddling his legs, and facing him. “If you want to.”

Just watching her since she appeared wearing tight black pants, almost leggings, and an equally as snug collarless shirt that highlighted her large breasts, Charles’s dick had been on the verge of getting hard. Now with her sitting on him, her pussy almost pressing against his cock, it fought its way to a full erection in the confines of his pants.

Holly’s eyes widened. “I hope that means you want to.” She cut what of his hair she could from this position.

“That’s a solid assumption.”

“Solid indeed!” She rubbed her crotch against his causing his cock to pulse. “Mmmm. You’ll fit in very well.”

Charles took that as maybe her commenting on his size, but he didn’t offer a response in case he was wrong. “When would you like me to bring them?”

“You’re my last appointment for the day. If you don’t have other plans, I could fix dinner. Do you have any of your stories with you?”

“They’re all on my laptop in the car,” He said. “If you want hard copies, I—”

“Of course, I want hard, but the stories you can email.”

That caused his cock to expand again. Nothing shy about her.

“But it doesn’t seem like hard is going to be a problem,” Holly added.

“Not where you’re concerned,” Charles had to say.

As he’d gotten older, Charles had become less picky about haircuts. But then, he’d always gone to places that were known to have good barbers, whether male or female, and so, he’d always been satisfied with the results. As for Holly, she could have scalped him, and he would have been okay with it. However, it turned out to be one of the best haircuts he’d ever had, and he wasn’t being generous because it was Holly. It really was exceptional.

* * * * *

Having followed Holly home to her apartment, Charles was still a few minutes behind her. She left her front door ajar. He entered and was greeted by a trail of her clothes down the hallway. It was too tempting not to follow.

He did the polite thing and knocked on her bedroom door.

“You don’t need to knock,” Holly called out. “Just come in.”

So, he did. She wore only the most alluring and revealing black bra and panties.

“I usually slip out of my work clothes when I get home,” Holly explained.

“And what do you slip into?”

“Whatever I’m in the mood for,” she replied, but in a tone that was open to suggestion.

“And what are you in the mood for?”

Standing next to her bed, Holly drew back the covers. “Sometimes, I just slip into bed.”

“That sounds cozy.”

“It is. It’s even cozier when someone slips in with you.”

Charles nodded. He liked where this was going, but he also had to ask, “How often does that happen?”

“It hasn’t since I’ve been back. But I’m eager to give it a try. Are you?”

Charles was suddenly taken aback. Of course, he had hoped to eventually end up in bed with Holly since reconnecting with her. He had dreamed of such a moment for years. But he certainly hadn’t expected it to happen so soon. “You don’t waste any time.”

“You said it best. Missed opportunities.” Casually, Holly reached avcılar escort behind her, unclasped her bra, and let it fall. Her breasts were as perfect as he knew they would be. Without skipping a beat, she pushed her panties down and stepped out of them.

If that didn’t take his breath away, nothing would. Holly held out her hand for him to take. How could he refuse?

But instead of taking his hand, Holly reached for his shirt and started unbuttoning it. She was very dexterous and had it undone and off in seconds. Next, she went for his pants, and likewise, had his belt undone, pants unfastened and zipper down in no time. When his pants dropped to the floor, he quickly stooped to remove his shoes and socks. He’d barely stood back up when she pushed him onto the bed on his back.

She instantly climbed on and knelt one knee between his legs and the other on the outside. She held her upper body up on her arms and pressed her lips to his. There was an urgency to her kiss. They’d done some minor kissing so many years ago and he remembered her as being good at it then. Now, it was divine.

Pulling back, Holly sat on her haunches. Charles was drawn to her beautiful tits to suck her nipples. But she didn’t allow that for long, wanting their mouths together again. That also did not linger as his cock was now as hard as it had ever been, and she felt it poking her abdomen. She quickly slid down, grabbed it at the base and pointed it toward her mouth. A moment later, he felt warm saliva dribbling down his shaft as half of it disappeared between her lips. Damn, she was good.

Eager though she was, Holly took the time to sensually suck him. It felt wonderful to have a cock in her mouth again. Particularly, this cock. She knew it would be sizeable, remembering the bulge in his pants from so long ago. Dragging her tongue along the full length of it, she felt it pulse in happy response. She couldn’t explain it, but there was just something exciting about going down on a penis, having it fill her mouth, even taking it down her throat. It made her feel like a real woman.

However, as nice as that felt, it was no comparison to putting it where she really wanted it. So, she fell onto her back, pulling Charles with her.

But he had other ideas, and Holly felt his tongue dart between her labia and then tickle her clit. And as bad as she wanted his cock inside her, she decided his mouth on her pussy felt good enough to let him have at it. He was very delicate with each labium, but also experienced and the sensations she felt were driving her wild. She screamed out her pleasure. And if that wasn’t good enough, Charles shoved two fingers inside her vagina sending shockwaves throughout her body. But he didn’t stop there. She then felt him press up, and suddenly, unexpectedly, she exploded in a bone-rattling orgasm.

He’d found her g-spot. It was so intense, she could not endure it for very long, and she had to push his hand out of her pussy and his mouth off her clit. Her entire body was shaking, and it took a couple of minutes for her to recover. And when she did, he dragged his tongue up her pubic bone and abdomen, letting the tip of his tongue dip into her belly button—which sent a minor tingle through her body— and between her breasts. There, she grabbed either side of his face lifting his head and pulling his lips to hers.

“That was so good,” she said, catching her breath. She happened to glance down and saw his cock inches from her pussy, so she reached down, jerked it a few times to make sure it was good and hard—it was—and she guided it into her desperate pussy. The climax had been fantastic, but there was nothing like the feel of a big, hard dick sliding between her labia and up her vagina. It was soothing, and yet, electric. And he filled her just right. In fact, she’d never had a cock inside of her that felt so filling, so . . . right.

It was no less thrilling for Charles, if Holly’s whimpering and heavy breathing were any clue of her enjoyment. Even though they’d only had two dates when they were younger, Holly had made such an impression on him that he’d never forgotten her. He’d always thought of her as the one who got away. And he’d always fantasized about what it would have been like with her had they somehow been able to stay together. But even his most erotic dreams about her were never close to this real moment. He was in heaven, on a cloud, and he never wanted this time to end.

Charles pumped her slowly wanting to feel every millimeter of her vagina. All the clichés were coming true: she felt like a velvety glove, the only organ in the body designed purely for pleasure. His head was spinning. He’d had intercourse many times, but now he was fucking for the first time.

“Oh, that’s it, baby, fuck me,” Holly purred. She reached out, grabbed his ass cheeks, and pulled, urging him to go faster.

Charles complied, but not to the extent she wanted.

However, Holly had her own şirinevler escort remedy, and Charles was too invested to deny her. She pushed him off her and onto his back, mounting him cowgirl. Once she had him inside her again, she rode him like the wind.

He had to admit. There was nothing wrong with her method. But she slowed to a compromising speed. It was also exciting watching her breasts swaying above him, her abdomen doing a belly-dance-like motion, and his cock sloshing around inside her very wet pussy. He didn’t know how much longer he could hold out. He reached out to rub her clit and hasten her orgasm. He wanted to make certain she came again before he did.

It worked. Holly’s vocal accompaniment became more intense. She even rolled onto her back again pulling him with her, his cock never leaving the warm embrace of her pussy. She pulled him as close to her as he could be with her arms wrapped tightly around him. She kissed him passionately, muffling her throaty cries of fervor as her climax overcame her. He was amazed at her strength by the firmness with which she held him.

Charles did his best to withhold his own orgasm until he was certain she was finished. When her body finally went limp, he announced that he was going to come.

“Not inside me.” It sounded like a warning.

“No, of course not,” he agreed.

“No, I mean I want it in my mouth. I want to savor every drop.”

And if that wasn’t enough to make him blow his nuts, nothing was. Charles quickly pulled out of her and moved up to her face. Holly forcefully grabbed his cock and pulled on it, placing him in an awkward position. She opened her mouth and got the tip in just as he began hosing her tonsils. She couldn’t take it all, and when she closed her mouth to swallow, he painted her lips, chin, and cheeks with pearly white liquid. She used her fingers to scoop it all into her mouth.

“Mmmm, yummy!” Holly said.

“Wow! Never had a woman do that,” Charles noted.

“Sorry, it’s been a while for me,” Holly offered.

“No need to apologize. It was wonderful.” Charles laid down beside her.

“Yes, it was.” She turned to face him. “Where have you been all my life?”

“What do you mean?” Though he thought he knew.

She shrugged. “Like I said earlier, I wouldn’t have shied away from a relationship with you. But like I also said, the only times we went out were the two times our sisters fixed us up. You never asked me out on your own, so I assumed you weren’t interested in a relationship—at least, with me. And now, I’ve been—we’ve been missing all this great sex all these years.”

“I’d like to think we’ve missed more than that,” Charles said.

“I agree.”

“But as I mentioned earlier, as popular as you were, I didn’t get the impression you were interested in me.”

“The only reason I was so popular was because of these.” Holly cupped her breasts.

“They do make an impression—in your shirt.” He grinned at his joke.

“Ha-ha. Don’t tell me you never noticed.”

“Of course, I noticed,” Charles admitted. “But the two times we went out you didn’t really dress to . . . display what you had. So, I found other things I liked about you.”

“Such as?”

“You were cute as hell. I mean, gorgeous. You still are.”

Holly smiled to cover her blushing.

“You were also very nice and intelligent.”

“You’re already in my bed, you don’t need to butter me up,” she said with a smirk.

“l mean every word.”

“I’m sure you do.” Holly reached out and cupped his face. “So, where do we go from here?”

“I’m glad we reconnected today.”

“But?”

“No but. I’d like to get to know you. All we have are two dates many years ago when we were teenagers, and tonight. How have we changed over the years? Let’s see if it was meant to be between us. If there is a second chance.”

“I agree.” Holly grinned. “As long as there are more nights like tonight.”

“I’d like that, too. But I don’t want to build a relationship on sex alone.”

With a frown, Holly said, “Sounds like something I should say, but I agree to that also.”

Charles shrugged. “As long as we both agree on what we want.”

“And now, I promised you dinner.” There was weariness in her voice. “And that means getting up from this cozy, comfortable bed with you.”

“No, you don’t. We can order out for something, if you want.”

“Are you sure? That would be fabulous.”

And so, they did; pizza being the easiest and most obvious. Fortunately, Holly had a nice bottle of red wine to go along, and they sat in bed to enjoy their meal. It was oddly enjoyable sitting cross-legged on the bed completely naked eating pizza and drinking wine. They chatted about nothing in particular, Charles unable to really focus on anything serious with Holly in all her beauty sitting there splendidly nude; and likewise, Holly couldn’t help stealing glances at his magnificent cock that, while flaccid, she desperately wanted him back inside her.

With most of the pizza consumed and all the wine gone, Charles arose to discard the box and bottle. That done, he began to dress.

“You don’t need to do that,” Holly told him. She patted the spot in the bed he had previously occupied. “You can stay. You’re welcome to stay. I want you to stay.”

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