Friends With Benefits Pt. 01

Dan looked at her thoughtfully and Jim remained silent. "No, not exactly in that way. It seemed like this arrangement was more for your benefit than for his own."

Jennifer laughed. "Oh, it's definitely for my benefit, and rest assured Dan that this is something I really want. But don't let him fool you, he wants this as much as I do. He might not be all in order physically, but they say sex is 90% mental, and it turns out he's fantasized about seeing me with other men and women for a very long time. I never knew that about him, and I don't know whether I could have indulged that before the accident, but I've come to grips with it and I think I may have a bit of that fetish too. Did he tell you that I also have a girlfriend?"

"No, he didn't."

"Well I do. She is a lifelong friend who I knew all along was bi-sexual, and we have had a few encounters with her. All three of us I mean. If you like me, you'd love her...taller, redhead, big boobs and an absolute nympho in bed, regardless of partner. There are still a few things Jim enjoys doing, and to be honest I've found I like seeing him do them with Sheila too." She raised her bottle and drained it then set it on the bathroom counter-top.

Jim spoke. "Honey I didn't tell him about that - I wasn't sure if you wanted him to know or not, but cat's out of the bag now. And Dan, there are no more secrets in that regard between us. If you are wondering, I don't have any interest in other men other than seeing Jen with them. I wouldn't say we're swingers either, at least in the sense of different partners all the time. I've enjoyed playing with Sheila and even more have enjoyed seeing them play together, but neither of us have any interest in any other women in our bed. It would be the same with you."

Dan laughed nervously. "Well, this is all pretty crazy I guess. I'm trying to find something to say, and having a pretty hard time with it. It sounds like you both are all in for this." He looked at Jennifer and smiled sheepishly. "Jennifer, you are a beautiful woman. I've always thought so, although I don't know if I've ever considered that in a sexual way before now. I suppose because I knew you were married and it just didn't occur to me to look at you in that way."

She giggled. "Well, as Jim said the cat's out of the bag. Do you see me any differently now that you know all of this?"

"You as a person no, I don't see you any differently than I always have. But you as a partner, as someone I might sleep with? Yes, I see you now in that way, and you are even more beautiful than I ever thought before."

Jim laughed softly on the phone. "Well said. Honey, you were right...I think he's the one."

Jennifer was blushing and glanced at the floor. "I knew it. You always know the right things to say Dan."

There was a bit of nervous silence before Dan finally spoke again. "I guess I haven't exactly said it, but regarding everything, my answer is yes I'm willing to, um, see what happens. Damn, I still don't know what to say here."

Both Jennifer and Jim laughed at that. Jen spoke "Well, don't worry about it. We'll just play it by ear and see what happens. We're not going to do anything tonight. I know I can't ask you to be committed to me or to us, but I want you to know that if you are in, Jim and I would be committed to you and you alone as a man in this relationship for as long as it lasts. That could be one time, or the rest of our lives for all we know. This isn't really as easy for us, well for me, as it might sound. I tried to make it easy, to have a one night stand where I could lose all inhibitions and do whatever I wanted, and I couldn't really enjoy it. I chose you because I really like you, and more importantly, I trust you. I love Jim and will never leave him, but I have to have some emotional connection for this to work. I don't know if that is really love in the deeper sense or not, but it's something I need. I will continue to have a relationship with Sheila, and I wouldn't rule you out of that if you and she agree. I need you to really think about this before you say yes or no. Do you understand?"

"Yes, I think I do. And I agree, I DO want to really think about it and not get tangled up in this moment right now without having a cooling off period."

From the phone Jim spoke again. "That is more than we could ever ask or hope for Dan. We have had the benefit of this discussion for months but it's all new for you. We talked about this a lot, and we both think that nothing should happen tonight. I'm going to hang up now with that in mind. Jen, I think you should kiss him goodnight and let him escape back to his room. I'm sure he's dying for a drink right about now. I love you, talk to you tomorrow."

Jennifer walked over to the bed and sat down on it. "Well, I'll bet you weren't expecting all of this?"

Dan looked at her and smiled, still pretty nervous about everything. "No, I sure wasn't. I do wish I'd brought the rest of that 12-pack over though."

She laughed with him. "Yes, I do too. So now that it's just the two of us, do you have any other questions?"

He looked at her and suddenly got a bit more serious. "Yes I suppose I do. I'm pretty shocked by all of this, but I'm really curious why you picked me of all people?"

"It wasn't hard after the second attempt we made to...to get involved with another man. I thought it would be easier if it was more anonymous, but the truth was it was incredibly frightening. I managed to get through it once, but I got nothing out of it at all, and when we arranged a second date, I couldn't go through with it. I was scared, I didn't really know the guy, Jim wasn't involved in any way. It was just terribly awkward and scary."

She looked at him and he saw some pain in her eyes. She continued "All the times we've been together for these work things, you have always taken the time to make sure I am OK, even if you didn't realize it. When Jim had his accident, you talked to me about it - hell the whole team did, but you continued where everyone else stopped. I'm the only woman on the team and all the other guys talk to each other about sports and all of that guy stuff. You're the only one who takes the time to talk to me about anything else. You're a caring person Dan, and when all of this came to light, I realized that if I'm going to have a friend with benefits, I want it to be truly a friend. I'm not going to fall in love with you and leave Jim, and you shouldn't ever expect that. But I DO care about you and I think you care about me. I care enough to be intimate with you in every possible way because I know you wouldn't hurt me. In fact, I think that if you even thought you might hurt me, you would never do this."

Dan stared at her, somewhat surprised at the depth of her admission. He finally spoke "You're right about all of that Jen, and if I have a hangup here, it's that. I do consider you both friends and I don't want to jeopardize that."

She smiled at him. "That's exactly why we asked you. And Dan, there's something else too. I really am attracted to you sexually. You're tall, I love your gray streaks, you're in great shape. You make me laugh and you make me feel comfortable. I don't know anything about you in that way, but I know you would be a considerate lover. And I know you're not attached to anyone right now, so you wouldn't have to worry about that. If you were, I would never even consider it."

Dan smiled. "You and Jim have left me more speechless than I've ever been in my life. I have always thought you were beautiful, but I never let myself go further than that. I would be lying if I said that I won't be thinking about it now though. I'm secretly wishing that there were another couple beers over there just so I could watch you get them out of the fridge again."

She laughed. "You liked that huh? I always dress conservatively for work, but I picked these on purpose for you. I was hoping you'd notice."

"Oh, I noticed alright. I don't think I'll ever shake that out of my head." He laughed and she joined him. "But for tonight, I think I'd better get back to my room."

"Yes, I agree. But kiss me goodnight first. A real kiss."

They both stood and she held out her arms, welcoming him. He started to step toward her when she suddenly said "Wait!" Dan paused and stared as she put her hands down and grasped the edge of her top, pulling it up and over her head. She wasn't wearing a bra, and her apple-sized breasts jiggled as she tossed the shirt behind her. She cupped them and brushed the nipples lightly making them swell. She turned and slowly lowered the yoga pants as she bent from the waist, exposing her round buttocks and as she pushed lower, her pussy came into view. She stood and turned, completely nude and gave him a moment to ogle her before stepping toward him.

"You might as well see what you're getting in to. Now kiss me."

Dan stepped into her arms and reached around her waist, leaning down to meet her lips. She pushed firmly into him and their tongues met, wrestling wildly. She sucked on his lightly and he did the same, feeling his erection growing between them. She felt it too and grasped his hands, guiding them to her full, round ass. He squeezed softly as they kissed, and she grasped his too, pulling him tightly against her, feeling his lengthening tool pressed into her belly. She groaned softly as he squeezed more firmly, and finally broke away from his lips with a slightly gasp. Her hands slowly dropped and taking the hint, he let his slide down too cupping her hips. She smiled up at him and reached down, running the palm of her hand along his length.

"That was some kiss Dan." She smiled and rubbed him softly. "It appears you liked it too."

Dan was stunned, at her nudity, her stroking, and the passion in her kiss. "You are incredible." was all he could say.

She squeezed then released him. "You feel pretty good too. Now go back to your room and have very sweet dreams."

Dan laughed softly. "I don't know if I'm going to be able to sleep after that, but yes I'm going." He turned, a very visible tent in front of him and stepped to the door. "Goodnight Jen."

"Goodnight Dan."

He stepped through the door and made his way quickly to his room. With everything else that had transpired, the last thing he needed was to be caught in a hotel hallway with a huge erection. Finally safely inside his door, he went straight to the fridge and grabbed two beers, then went to his bed, placed them on his nightstand and shed his clothes. Regardless of everything else, his hard cock was going to need attention before he had any hope of thinking about anything or sleeping. He opened a beer and drained half of it before setting it down and picking up his personal phone. He opened a browser and navigated quickly to a porn site, but found himself thinking about Jennifer and unable to concentrate. Jim was right, she had a spectacular body and he couldn't stop thinking about it as he slowly stroked his erection. He was concentrating, eyes closed when his work cell phone buzzed. He ignored it for a few moments and it buzzed again.

"Fuck." he muttered and picked it up. There were two messages, both from Jennifer. The first one read 'thanks for helping with my presentation' and the second one was a phone number and another message, 'this is my personal cell, send me yours.'

He tapped the numbers into his own cell phone and a message 'this is my personal cell' and hit send. A few moments later she replied 'got it'. He grasped himself and stroked again slowly, then tapped out 'can't sleep, at least I have beer!'

A moment later she answered 'lol...me neither.' A few moments passed before another buzz and a little message that said 'downloading' appeared. A few moments later an image appeared of her thumb and finger with a strand of clear liquid between them. 'You're a very good kisser...this is what you did to me'

Dan jerked himself quickly, the image of her wetness sending a jolt to his cock. His phone buzzed again. "Still there?'

Tap tap. 'Yes, still here...daydreaming. You are a very good kisser too. You're still having quite an effect on me too.'

'lol good, I'm glad to hear that. Try to sleep, we'll talk more tomorrow.'

He opened the browser back up, desperate for release now and started a video with a petite blond. His phone buzzed, another message from Jennifer. He opened it to find another picture of her squeezing one of her nipples between her moistened thumb and fingertip.

'hope this helps you sleep. good night!'

He groaned and stroked faster as he stared at the image, reaching his peak quickly and grunting as ropes of semen flew up his chest and across his stomach, shuddering with the intensity of his release. He finally released his grip and sank back into the pillow, not noticing the dribbles of cum rolling down the side of his rib cage, and drifted slowly to sleep with her nude image consuming him.

Wednesday morning.

Jennifer woke with a start, sure she'd missed her alarm going off and slowly realizing it was still dark. A quick look at her phone showed 5:11 am, an hour before she planned to wake up. She tossed and turned but it was no use, her mind was already busy, planning the day, thinking about her presentation. And last night. What did Dan think, was he going to do it? She thought about the kiss, it was even better than she'd hoped it would be. She felt it...felt something. Whatever people call chemistry, it was there, like a ball of fire in the pit of her stomach, slowly spreading through her. She rolled on to her back, stiffened nipples brushing against the cool sheet, sending a shiver through her. Her stomach tightened and she felt the heat coursing deep inside her. She'd held it off last night, forcing herself to wait, but her lust was consuming her now and there was nothing she could do to stop it.

That kiss, she knew he felt it too - he must have, he got so hard so fast! She thought about how he felt against her, holding her tight, erection prodding her high on her belly. How his hands felt caressing her bare ass. She licked her lips and pushed the sheet down, exposing her breasts and grasped them, flicking her long nipples quickly as her hips slowly raised and lowered. The raw feelings raced through her and she felt their intensity, and needed to reach down and satisfy that beautiful ache. She didn't, not yet. How much control did he have? His hands on her hips, holding her lightly and not daring to press her naked flesh further as she let her palm fold across his hard cock. If he'd moved, had felt for her sex she wouldn't have stopped him, but he only held her, staring into her eyes. He felt deliciously thick and she wanted to take him in both hands, to release him. She wanted him in her mouth badly, to squeeze his heavy balls and feel his cock swell in the back of her throat, twitching violently as he fed her his seed, holding her head and making her take it all.

She lifted her hand to her lips, sucking her middle finger and imaging it was something else, then wet her nipple with it. She kicked the covers off and slid her hand down, wishing it was his, and felt the glowing heat. She squeezed gently, her middle finger slipping easily into the dribbling wetness. God, how could she be so wet already? Sliding further, her fingertip brushed across her perineum sending a shiver through her, then back to her wet opening and plunged quickly inside. It wasn't enough...she added another finger then a third and slowly eased them in as far as she could, feeling the sweet ache as her tight hole stretched around them. Moaning softly and wetting her lips again, her free hand found her nipple, pulling and twisting it as her hips bucked into the cock she imagined thrusting inside her.

So close...

She released her nipple and rolled over to her stomach, burying her face in the pillow and arched her back, pulling her fingers free and groaned at the sudden emptiness. Her hips raised and lowered, fingers slipping noisily between her folds and spreading her arousal, and she grunted softly as they found her most sensitive flesh. Her other hand shot down, gripping one of her full ass cheeks tightly as her hips bucked, grinding into her fingers as they tortured her pulsing clit, and with a sharp cry into the pillow she came hard. Her fingers found their way higher, slipping inside, and she felt the tight gripping of her cunt, whimpering like a metronome keeping time with her contractions. Her gasps became more and more apparent to her as she slowly slipped down from her peak, and with a soft sigh she let her fingers free and cupped her hot sex the way she liked her lovers to do. Her eyes closed, she imagined the hot wetness she felt was Dan's seed between her fingers.

Finally spent, she drifted off in a half sleep until her alarm startled her back into consciousness. It was going to be a long day.