Secret Friends with Benefits

Note - This story originates as a secondary plot in another series under the "Mature" section, titled "Neighbor Fantasy, chapters 1-3". This story can be read by itself, but those chapters provide some context as to how this story came to unfold. See my other works to find it.

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Two days had passed since Jennifer had snuck into Brad's room at night to discuss the photo she had taken earlier that day. Without Brad being aware, both Jennifer and his sister had been home as he lay in the neighbor's yard with Mrs. Roberts, both of them quite nude and drinking before spending the night together, bodies locked in passion.

There was zero intention to blackmail Brad, or even to tell anyone about the rather taboo relationship with his neighbor, Mrs. Roberts. Instead, Jennifer had worked up the courage to ask Brad if he would, quite privately, mind spending time with her, to learn a few things to satiate her sexual curiosity. Since they had known each other for years, and she was the best friend of Brad's sister, he agreed.

Brad spent a good deal thinking about this on Sunday evening, having had a wonderful night prior over at Mrs. Roberts' home. Now that she would be away on business for a few weeks, he thought it a good opportunity to find a time and place to meet Jennifer.

He sent a simple message with his phone:

"Hey, still up for what we talked about?"

The reply was almost instant:

"Yes! When?"

They went back and forth, looking for a time when they could get together, but it was not particularly easy given their conflicting university schedules. Monday and Tuesday were no good for either of them. Wednesday seemed promising until Brad remembered a group project he would have to attend. Thursday would work if they met at eleven in the morning, since they both had afternoon classes, but then it felt like they might be rushed. Finally, they decided on Friday night.

"Your sister is going to a concert with her bf, so I'll be free. My parents are going away for the weekend."

Brad thought about this for a few minutes. He would love to meet sooner, but given the events of the last two weeks, he valued the idea of privacy and not being in any hurry.

"Sounds great, I'll come by at eight."

"Bring some wine ;)"

Brad laughed at the message, at the absurdity of it all. Jennifer was probably one of his sister's best friends, and here he was planning a clandestine meeting with her. Still, he was looking forward to it.

The week started as it normally did, leaving Brad with almost no time to do anything but his schoolwork. He had not heard from Jennifer at all since their messages on Sunday, and he wondered if she had changed her mind. He sent her a quick message on Thursday, simply saying, "Still good for Friday? No hard feeling if you get cold feet."

She did not reply right away, nor after an hour. Brad wondered if she had in fact changed her mind, when finally the reply came: "Sorry, in class. Can't wait :)"

Brad grinned, excited at the prospect. The phone vibrated again with a new message, "What are you going to teach me?"

He was not expecting the question, despite the nature of their gettogether. He replied by asking, "Well, what do you know so far, and what do you want to learn?"

A few more minutes went by and she replied with a long list:

"I guess I should learn to give a good handjob, and with my mouth, and to know what guys like to do."

That was terribly general, but it was more than he knew before. He replied with a simple, "Cool, we'll keep it light."

Friday afternoon finally came and Brad found himself anxiously awaiting the end of his survey class. Once back home, he showered and prepared for his evening, his mind running through what they would do together.

Taking the chilled bottle of wine from the fridge he had left that morning, Brad sent one more text, giving Jennifer one final opportunity to bow out gracefully should she be too shy to meet up, all while saving face. She replied stating that she was ready and waiting for him.

That was it then, Brad thought, taking his mom's car for the evening.

Having never actually been to her house, it took Brad a little longer than he expected to find it. He did not want to cause Jennifer any trouble, like by the neighbors comment to her parents about the boy who came over with wine as soon as they left for the weekend, so he parked a block away and made his way quickly to the door when he thought no one was around to see him.

Jennifer must have had the same idea, as she was waiting for him at the door, letting him inside and closing the door behind him in one swift motion. She wore a flattering black dress that hugged at her petite frame. As Brad said hello, he saw it was a wrap dress, the tie knotted at the waist.

Jennifer said hello and turned awkwardly, nervously, up the stairs. Brad followed, aware of her nervousness, but calm himself now that he was here.

"I brought some wine," he said, heading towards the kitchen to find some glasses. Jennifer turned and followed him, obviously having seen the bottle but not being focused on anything in particular.

He took two wine glasses from the counter that Jennifer had set before he arrived, asking, "Where is the living room?"

Jennifer led Brad out of the kitchen and down the hall. The living room was rather simple, with a large television against the wall and two couches on the other side. One was a long couch that could fit three, and the other was more of a recliner-style armchair and a rectangular coffee table with a glass top.

"Why don't you have a seat," he said, dimming the lights and then placing both glasses on the coffee table. He opened the bottle of wine. Jennifer sat rather awkwardly, not quite sure how she should sit, while Brad poured two glasses and handed one to her. She took it, while Brad sat in the middle of the couch, next to her.

"Here, sit facing me, and put your feet on my lap."

She moved without question, and he leaned forward to take the glass in his hand. "Cheers," he said, touching her glass with his, and they both took a long drink of the cool, sweet wine.

Brad placed his glass on the coffee table, placing his hands on Jennifer's smooth legs, she watched his hands closely as he gently moved his fingers along the skin, around the knees, tickling her softly without meaning too.

"Sorry about that," he said.

She took another long sip of her wine, as Brad shuffled away from her a little bit down the couch. Now, her feet were on his lap, and he took one into his hands, beginning a firm massage of her sole. In that instant, Jennifer felt everything melt away. Her nervousness completely gone.

As Brad worked the soles of her feet, he asked Jennifer about everything that was going on with her. He asked about her courseload this semester, how her family was going, what shows she was watching, or not watching, because school was in the way. They chatted about this and more, all the while finishing their first glass of wine, and then a second, and then what was left of the bottle. By the time they finished their last drink, the sun had set, and in the dimmed light of the living room, both felt their heads swimming with little care in the world.

It was then that Brad stood up, extending a hand to Jennifer, and said, "Why don't you show me to your room?"

She stood more quickly than she should have, and nearly fell over from the wine. She took Brad by his extended hand and walked him out of the living room and towards the stairs. Once up top, she led him into a room that was clearly not hers, but her parents'.

Brad said nothing to this, and instead took Jennifer by the hips, sitting her down at the edge of the bed. Then, he stepped back and began to undress. He took off his shirt, folded it, and placed it on the dresser. He undid the buckle of his belt and the three buttons of the fly, taking off his pants and folding them as well to place on the dresser. All the while, Jennifer watched the show, her mouth open as she stared, fascinated with his body.

Only his black boxer briefs remained now, and so he said, "Will you help me take these off?"

Jennifer stood from the edge of the bed and stepped forward. She reached out with one hand first, and then the other, placing her fingers inside the elastic, and begin to pull down. Her eyes focused on the semi-erect cock before her, letting the boxer briefs dropped to the ground.

"Thank you," said Brad, taking them and placing them on the dresser. Standing naked now in front of Jennifer, he reached towards the tied knot around her waist, giving it a gentle tug, letting the sash come undone. He took apart the wrap, first with the outer layer, then with the inner layer on the other side, revealing that Jennifer wore no bra or panties. Her breasts were on the smaller side but perfectly matched her petite frame. She sucked in her breath as Brad revealed her nakedness, and to calm her, he said, "You look beautiful," to which she smiled, but did not meet his gaze.

Brad looked over at the king-sized frame, and said, "Why don't you lie in the middle of the bed," which she did. She too had wondered what they would do first. Would she handle his cock with her hand, or her mouth, or something else? Brad had a different idea.

He lay beside her, watching her chest rise and fall with her anticipation showing in her breathing. He moved in close to her neck, and kissed softly, which made Jennifer moan softly, surprising her in the process. Brad smiled, and asked, "Have you ever been eaten out?"

Jennifer shook her head from side to side, and Brad nodded. He moved overtop of her, supporting himself on his elbows, kissing her neck, shoulders, breasts, and working his way down, down, pushing softly for Jennifer to part her legs, which she did without resistance. Soon Brad placed his hands beneath her legs, his face directly in front of her warm lips. Carefully, he began by kissing at her thighs, running his tongue all around her lips, simply to get her used to having a man so close to it for the first time.

Then, bringing one hand up and ever so gently, he placed his fingers on her clit, moving it in small circles. Jennifer shut her eyes and moaned more loudly now, enthralled in the new of being touched by someone other than herself. Brad removed his hand and replaced it with his mouth, gently running his tongue back and forth along her clit. Jennifer moaned in ecstasy, never had she experienced such a sensation before. Brad made sure to keep things slow at first, thinking she would need more time to get used to the feeling.

Soon however, he found that she was moaning loudly, totally enthralled in the feeling of his mouth on her clit, and so he kept at it, urging her along until her breathing became ragged. Her hips began moving more erratically, until finally she shook and squeezed her legs around Brad's head, her orgasm taking hold. Her mouth went wide, and she let out a series of longer moans.

When the rush began to pass, Brad moved up and overtop of Jennifer's body, laying on his back next to her as she recovered. Her breathing was still short but slowly returning to normal, and when Brad thought she was sufficiently in control again, he asked, "Did you like that?"

She turned to him, a massive grin on her face, "I fucking loved it!" came the reply, "I didn't know anything could feel so good!"

"Yeh, it can be pretty amazing," he replied.

Jennifer looked down at Brad's semi-erect cock, finding herself still a little shy, despite the wine and the orgasm that shook her body. Seeing this, Brad took her hand, and guided it down between his legs, where she grasped onto his awaiting cock. She loved how it felt between her fingers, and watched it grow rapidly as she stroked it. In no time at all, Brad was rock hard.

Jennifer watched with wide eyes, "It gets hard so fast," she said.

"Yeh, well, I've had some help watching you,"

She stroked it, moving her hand to different positions, getting the feel and weight of it in different ways. "Does that feel good?" she asked.

"Yeh, it feels nice when you stroke it."

"Will you cum if I keep doing this?"

"Yeh, if you did it long enough, and at the right pace, I'm sure I would."

She kept moving it, sliding it up and down, smiling and laughing softly as she pulled the skin up and over the tip.

"It's a little weird," she said, poking at the shaft with her finger. "What should I do now?"

"What do you think of giving me a blowjob?"

Jennifer nodded enthusiastically, "I haven't done it before."

Brad nodded, "Well, you try it out, do whatever you think is good, and we'll go from there."

Jennifer slid down Brad's body, moving his legs apart in the same way he had her do earlier. She was now between his legs, hips in the air, giving Brad a perfect view of her ass. She took his cock in her hand, and gently placed the tip into her mouth. Brad smiled and watched as she slowly worked the tip in and out of her mouth.

She tried different things, like stroking him while sucking the tip of his cock, then trying to take as much of it into her mouth at once, getting about half of it in before gagging. She licked at the shaft, and lightly at his balls, all with the goal of seeing how we would react to each act. Brad moaned with each one, enjoying the feeling of Jennifer exploring with her mouth.

A good while passed, and Jennifer stopped every so often to ask how it felt, or if she should do something different. Brad offered suggestions based on what he liked, but also kept saying that everyone likes things a little differently. Eventually Brad found himself almost losing himself in the sensation, and decided to dial it down with another lesson for Jennifer.

"Ok," he began, "Let's try something else now. Come lie next to me again."

She did as she was told, lying on her side facing Brad.

"Lie on your back," he said, turning onto his side to face her.

She did so, and felt his hand start wandering around her hips, moving around her thighs, lightly spreading her legs apart, which she again opened without hesitation.

"I'm going to touch you now, but we'll do something a little different. You need to guide my hand, and tell me exactly how you want to be touched."

She nodded, and asked, "Why?"

"Because if the guy doesn't know what he's doing, and you're too shy or don't know how to tell him what you want, you won't enjoy it, and he won't learn."

Jennifer smiled, remembering from experience the few guys she had been with, all of which were clueless. If it happened again, this would certainly help. Brad had let his hand rest on Jennifer's thigh, and so she took his hand and placed it on her still warm and wet lips. She ran his fingers up and down, making her clit wet with her juices. Then, she placed his middle and ring fingers on her clit, before placing her fingers atop his, and began moving in small circles.

She moaned with pleasure as she used Brad's fingers to rub her clit, and after a few moments, removed her fingers, leaving only Brad to work her body. This went for a while, without much change, until Brad said, "Do you want me to do anything different? If so, you need to tell me."

"Move a little faster," she said softly, eyes closed tight. Brad complied, and Jennifer moaned and her breathing quickened. She began giving Brad instructions, or making small changes to the speed, or the type of movements, all the while smiling at how wonderful it all felt, and how easy it was when she spoke to him and told him what she liked.

"Put a finger in me," she said.

Brad moved his fingers down and began exploring her entrance with his middle and ring fingers, gently pushing in, stretching her hole as she twitched her hips at the sensation she felt. "Harder," she would say, "faster," she would add. A while later she said, "now go back to my clit," and Brad did, running the tops of his fingers in circles on her clit, until it all became too much for her once more. She grasped onto Brad's shoulder, turning and burying her face in his chest as the second orgasm shook her to her very core. Her legs clasped hard around his hand, and Brad found it painful for a moment, but also enjoyable to make her feel this way.

Brad moved his arm up and over Jennifer's head, pulling her into his chest, to lay there in the post orgasm bliss. He of course was still rock hard, but he knew that this was likely as far as they would go, and that this was about her, and not him. On the bedside table, Jennifer's phone beeped, signaling the arrival of a text message, which she ignored.

Jennifer breathed deeply now, doing her best to calm down. She was overwhelmed, in a wonderful way, but the way she was feeling. Before today she had assumed she would enjoy these things with the right partner, now she was sure of it. She had experienced everything she wanted from Brad. Or at least, everything but the last thing.

Jennifer thought for a moment, and then decided. She turned away from Brad, reaching over to the nightstand. Brad had thought it was her phone that she had picked up, but then she turned back and slid down his body, kneeling beside his rock hard cock, and opened the condom wrapper.

He said nothing, watching as she removed the condom from its packaging, placed it at the tip, and rolled it all the way down. She threw her leg over his, straddling him, and with one hand held firmly onto his cock. Brad moved his hands to her hips, gliding his fingers up and down the skin, lightly teasing, making her smile and reassuring her that this was the right choice. She lifted herself up slightly, enough to line up the tip of his cock, and sit back, gently taking in the first inches of his manhood. She gasped, lightly, as he entered her, and smiled.

She had only had sex once before, but she would sooner forget it even occurred for how awkward it had been, and how rushed they were. She had barely become accustomed to his meaty hands moving too roughly, and it was over almost as soon as it had started.

This however, this was like night and day. The wine, the oral sex, how he used his hands, all of this had warmed her up and left her ready to take his cock. She was so wet that there was almost no resistance, and as he filled her up, his cock hit places she had not felt before. Slowly, she began to move up and down on him, sliding about halfway up before moving back again. She cupped her breasts as she did, feeling her hard nipples between her fingers, and giving them a light pinch. Brad meanwhile stayed calm beneath her, grasping firmly her hips, helping move her up and pulling her down.

Jennifer bit her lip as Brad held onto her. She maintained this movement for a while, until Brad sat up, hugging her with his arms and sucking on her breasts. She loved the feeling, placing her hands around his head and pulling him close to her. Brad went to lie back down, gently pulling her with him, until she was almost lying on top of him. He pulled her head down until he could kiss her neck, and gently flicked his tongue against the skin of her neck.

Brad moved his arms down to Jennifer's knees, and pulled them slightly higher up on his body, towards his chest, before placing his hands firmly on her hips and thrusting deep, slightly faster than she had been moving.

Jennifer moaned deep into Brad's ear, as he whispered, "When you're on top, you can do the work, or I can do the work, in these different positions."

He continued thrusting into Jennifer, who continued to moan as he did so. She had her arms near his head, and moved them underneath his neck, holding tight onto him. He kept this up and felt her breathing again become shortened, another orgasm nearing.

Brad stopped then, and rolled Jennifer off of him, much to her surprise and disappointment. Brad sat up, moving behind Jennifer and pulling her waist up and spreading her legs. From behind now he entered her, going deep and making her moan once again. Brad knew she would not last long in this position with all the stimulus she had felt so far, and so he began the same strong, steady thrusts he had used on Mrs. Roberts the week before.