Intern Affair

Feeling the last of the pulsations flow through his cock, the last bit of cum draining deep into Tonnie and the inevitable shrinking of his manhood he couldn't help but think, "I've failed her again." As he caught his breath, his cock slipped out of her wet, unsatisfied cunt and he groans, "I'm sorry Tonnie."

Sliding off him, she quickly straddles his thigh whispering, "It's okay, I'll just finish here." She begins pushing her pussy against his thigh, lubricated by his cum as it oozed from her.

"Fuck," he thought to himself, "I fail her and she doesn't even realize it." Not sure if that was a good or bad thing, he reached up and cupped her tiny breasts, one in each hand. Using his thumbs to tease her nipples, he tried to speed her orgasm, since her grinding was now beginning to make his leg ache.

Finally, she cried out, "Oh yes, yes... ahh," ending with a feral growl and collapsing down onto him. Remaining still while she recovered, he could feel the cum running down his thigh and undoubtedly onto the bed sheets. They started on a towel, but her move onto his thigh moved the mess onto the bed.

"I just love lying in your arms like this," she said. "Let's just spend the whole afternoon here."

Wondering if she had left a bruise on his thigh, he merely groaned in response, hoping the feeling would come back to his foot so he could get up. Letting his young lover relax on him he pondered his situation. When he first started seeing her, she was fresh out of college, working at the company as an intern. As his business lunches with the group of interns slowly migrated to lunch with just her, he promoted her to be his personal assistant.

That soon progressed as lunches became small outings as he took her to some of the art galleries in the area, all in the interest in her professional development. Although he never tried to seduce her or anything during this time, they did get closer on a personal basis, discussing increasingly personal details of their lives.

In the course of her development, she learned of his disastrous sexless marriage. Granted his extra-marital dalliances in the past basically created the situation, but he was cautious about the real dirty details, letting Tonnie think the problem was all because of his wife.

While divulging a one-sided look into his private life, he was rewarded with some interesting details about his young associate. The one that interested him the most was that she was still a virgin. Remembering his younger years, he had never had a chance to deflower any of the girls he slept with; most of them had been more experienced than he had. Even his wife, he learned years after he married her, had much more experience than he did, even then.

The thought of introducing sex to a young woman, guiding her on a journey of sexual enlightenment intrigued him. Here was a chance to be the teacher, the one to introduce her to all the possibilities her young body held inside. He began putting together a plan to initiate sexual contact with her.

It was only a short time later that an opportunity presented itself. A convention in Atlanta would give him the perfect set of circumstances to seduce his protégé. It was not unusual for assistants to travel with their bosses on sales trips and conventions, so he scheduled Tonnie to make the trip with him.

This trip was her first business trip, so he got a real kick out of her exuberance during their ride to the airport and the wait at the terminal. She was a non-stop blur of energy, as she checked their email, made a few business calls, chased down some coffee for the both of them and then generally just barraging him with non-stop questions about the convention.

He just took it all in, hoping that this excitement would carry over into the bedroom. When they arrived at the hotel, she didn't have any problems when they suddenly discovered her reservation was strangely "lost" and she'd have to stay in his suite in an adjoining bedroom instead of having a room to herself.

"This will work out well, if you need anything I'll be right there," she said, "Much more convenient than if I was in another room."

From that point onward the seduction was on, as he took her to a romantic dinner at the posh roof level restaurant in the hotel, making sure she had plenty of wine. Afterwards, they visited the jazz club downstairs where he danced with her a bit, and basically treated her like a princess all night long.

They returned to the room a bit before midnight, but before she could head to her room he held her hand and pulled her closer to him. Gently brushing her brunette hair back from her eyes, he slowly tilted his head and softly kissed her lips, pausing there long enough so it was clear what the kiss was about.

Pulling back from her, he gazed into her eyes and seeing she was receptive, he leaned in and kissed her again, this time slipping his tongue in between her lips and toying with her tongue. He drew her against him and continued to kiss her, letting her feel his erection grow against her.

After a few moments he reached up under her hair, unhooked her dress and began moving the zipper downward. She was motionless, letting him carefully remove her dress and arrange it over the chair. He quickly pulled off his clothes, while she stood silently, watching his every move, her eyes locking on his hard cock as he pulled off his underwear.

As he moved toward her, she continued staring at his cock and said, "I've never..."

Touching two fingers to her lips he whispered, "Shhh... I know. I'll be gentle."

He stepped into the restroom and came back with a towel and condom. Placing the towel on the bed, he then tore open the wrapper so the condom was readily available and placed it on the edge of the towel.

She had already reached behind herself, removed her bra and then slipped out of her panty hose, finally standing before him in only a lace panty. He guided her backwards to the edge of the bed, where he kneeled on the floor and daintily removed her panties, watching her sit on the towel as she stepped out of them.

He paused a moment to look over this young woman. She was not the most attractive of his recent conquests, but her innocence more than made up for the minor deficiencies. Her breasts were not large, and the nipples and areola were just a faint pink, almost indistinguishable from the color of the rest of her breasts. The nipples did stiffen up nicely, looking almost something that could poke out an eye.

Noticing her shivering a bit, he leaned forward, opening her knees and sliding between them, so he could reach around her waist and hold her. "It's okay, we'll go slowly," he assured her, kissing her belly and then descending through her curly triangle of hair to her pussy. Just the thought of slipping his tongue inside her and tasting her fresh cunt had him feeling a bit dizzy, but he continued pushing his tongue deep inside her.

He could hear her breathing hard as he reached his hands up to her breasts and pushed her back, so she could lie on the bed. Sliding his tongue up the length of her slit he found her clit and slowly ran his tongue in tiny circles over it while moving his hand back down between her legs. Carefully working a finger inside her, he moved it up against the top of her cunt trying to stretch her hymen a bit.

Wanting to open her up as much as he could before penetrating her with his cock, he continued working two fingers in and out of her as he kept his tongue working on her clit. It wasn't evident if his fingers were causing any pain and in a few moments more, he could feel her lift her hips in unison with her fingers. She came quickly and noisily, crying out something he couldn't decipher. Leaving his fingers inside her, he felt her pulsate around them, moaning the entire time.

"Oh God," she groaned, "I've never felt like that."

"Is that the first time..."

"Oh no, I've come before, once even with a boyfriend, but it was nothing like that."

"Did he use his mouth on you?" he asked.

"No, he just fingered me. It was nothing like this."

Sensing it was time to go a step further he climbed up on the bed, kneeling between her widespread legs and asking, "Are you ready to try a little more."

"Okay," she replied tentatively.

He reached and pulled the condom out of the wrapper and rolled it down over his cock. "If it hurts too much tell me and I'll stop," he whispered in her ear as he moved his cock against her pussy. "Pull your lips open a bit and guide it in," he continued.

Feeling her fingers take him, he leaned closer, slowly easing himself into her opening. He pushed a bit and then felt a tightness inside her cunt. Pausing a moment, he took a breath and pushed harder, feeling resistance and then a sudden release as he entered her to the hilt.

"Ohhh...," she whimpered.

He paused, looking into her face. A tear had collected at the corner of an eye and he moved his mouth to her and kissed it, tasting the salty liquid. Slowly withdrawing, he noticed her wince just as the head passed what remained of the hymen. He then moved forward, thrusting back into her. He continued, slowly increasing his pace, noticing her begin to feel something more than the pain. Soon she moved beneath him, seeming to enjoy what they were doing.

Though he wanted to make her come that way, he knew she probably wouldn't this time, so he let himself go, feeling the sensations of her pussy on him and just thinking of how he was the first man inside her inspired him. Even wearing the condom, with a few more thrusts he felt the intense pleasure roll down his shaft and he spurted his cum into the condom, his cock buried deep inside her.

Recovering from it all he looked back at her face and noticed she was silently crying. He immediately held her head between his hands and said, "Oh no, does it hurt that much?"

"No, no. It hurt a little, it's just, it's just... well, what we... my first...."

"Shhh... it was so beautiful," he said kissing her lightly on the lips and then kissing her face all over, collecting the tears as he went. Withdrawing from her, he carefully removed the condom and laid it on the towel. There was some blood, but not a lot, all caught in the towel.

Looking back on it all, it was a beautiful thing, he thought, trying to wiggle out from the now sleeping woman. He was finally getting some feeling back in his foot after her humping his thigh and he wanted to limp off the pain.

"Hmmm, you awake?" she asked.

"Yeah, go back to sleep," he whispered, still trying to wrestle from beneath her.

"You didn't even fall asleep did you?"

"No, I was just thinking," he answered.

"About what?"

"I was thinking about that first time, our first time... your first time."

"Oh yes," she said, kissing him passionately on the lips, coming up for air she continued, "You know how much that turns me on: you thinking about that?"

Her hand grabbed his cock, but seeing it still wouldn't be ready for a while, she changed her plan, getting up on her hands and knees and tossing one leg over his head and lowering her pussy onto his face. "Damn," he thought, "this girl's gonna kill me." He turned his head and took a deep breath before moving back and plunging his tongue into her recently fucked pussy, thinking about the virgin taste of her just a few months before.

Fighting her for each breath as she ground herself on his mouth, he wondered what it might be like with a more mature woman, where you could just have sex once and then go to sleep. He thought to himself, "Somehow I've got to figure a way to get out before she kills me. I've got to figure a way to leave..."

She ground her pussy onto his face, her juices wetting him thoroughly. Trying to concentrate on her clit, her movements took over and soon she was basically grinding over his face much like she did to his leg. All he could do was fight to catch a breath here and there between her thrusts. Thankfully in just a few more moments her heard her loudly exclaim, "I'm coming, I'm coming."

Climbing off of him, she noticed him panting, trying to catch his breath. Kissing his face she exclaimed, "I love it that this turns you on so, look at how you're breathing."

"Yeah, it's so exciting," was all he could say, wondering how much longer he could take all this.