Friends with Benefits

Not sure how many parts this will end up being, just following a thought.

*

It was Fall in the Midwest and the shorter days and inevitable colder weather were turning the hardwood trees into a kaleidoscope of beautiful color. Most of the team worked remotely across the country, but a few times a year they all gathered in Chicago at the home office to train and have the opportunity to work together for a week. It was a nice change of pace, and everyone always enjoyed the face to face time. There are nine people on the team who do a variety of different things ranging from customer service to data development. The working sessions were always good, but the co-worker bonding that occurred after work was the real reason they all liked these week long events. It was always fun to leave work behind and socialize with everyone, and Chicago is a great place to do that!

The team had all gone out for dinner together in River North, and afterward stopped at a couple of bars on Hubbard. It was always lively there, and it didn't take long to realize that the younger part of the team was headed for a long night of partying, while the rest were starting to fade out. Eventually four of them, Dan, Jennifer, Eric, and Mike, all said their good nights and caught a cab back to the hotel. The story of Dan and Jennifer begins here.

Dan had made it back to his room and settled in, grabbing a beer from the fridge in his room and had changed to lounge pants and a t-shirt. It was about half an hour afterward when his work phone buzzed. He picked it up and found a message from Jennifer.

'Hey, if you're not doing anything, would you mind helping me with a few techy things for my presentation tomorrow?'

He texted back, 'Sure, what do you need?'

'Not too much, just a few questions I can't answer. Might be easier to show you - want to come up?'

He finished his beer and thought about whether to change or not and decided not to.

'Yeah, no problem - what room?' He sent that, then added another. 'Want a beer?'

A couple minutes later his phone buzzed again. 'Do you have some? That would be great! Room 217.'

'OK I'm actually just down the hall I think. Be there in a few minutes.'

Dan went to the fridge and grabbed two beers, thought about it and grabbed two more, then stuffed the card key to his room in his pocket and headed down the hall.

Jennifer had arrived back at her room, put her hair up, and took a fast shower to freshen up. She then called her husband Jim to let him know what she had planned for the rest of the evening. With a few days left in Chicago, this was the night. She too had changed, to a pair of very tight yoga pants and a loose top without a bra. She was already nervous with anticipation when she heard the tap on her door. She walked over and opened it to find Dan standing there with two beers in each hand.

"Hey Dan, come on in." She turned and walked into the room slowly, and he couldn't stop himself from staring as she walked to the table. Jennifer is very pretty 39 year old. A petite blonde, just barely more than 5 feet tall and quite small from the waist up, a thin waistline, and a surprisingly full pear-shaped ass that Dan had never really noticed before, but the tight yoga pants she was wearing were a shot straight to his core and he wouldn't be forgetting that ass any time soon. She was a stark contrast to Dan who was well over 6 feet and a thin to medium build. He was in great shape at 48 years old due to a steady regimen of cycling, running, and weightlifting.

"I brought a couple extra beers for you. I always pick up a 12-pack when I travel - cheaper than sitting in the hotel bar."

She laughed. "Thanks, I should do that too. It would be easier than trying to slide a liquid dinner through on an expense report!"

He chuckled and handed her a beer, kept one for himself, and put the other two in her fridge. He twisted the cap on his and Jennifer handed hers to him. He handed his open beer to her, opened the second one and said "Cheers."

She smiled and answered "Cheers!" and tilted the bottle toward him before taking a long drink.

He nodded toward her open laptop and asked "Shall we?"

"Yes. Here, you sit and I'll show you where I'm stuck."

Dan sat in the task chair in front of her laptop and tapped the pad. The screen flashed and opened to a power point slide. He felt her lean against him slightly as she reached across and opened one of the slides.

"Here. I don't know how to calculate the specs for storage capacity here. Actually there are a couple of slides with this, but if you can show me how to do it I'll take care of those."

"Ah I see. Sure, it's pretty easy once you know what to add in. I'll put the calculation in the slide and you can leave it there or move it to a cheat sheet for yourself if you want, then you'll have it in the future."

She squeezed his shoulder and said "Oh thank you, that would be perfect!"

Dan spent the next few minutes explaining what he was doing and adding quick instructions to her slide. She took over and did the next one to make sure she understood, and satisfied, closed the computer.

"Thank you for showing me Dan, that will be so helpful in the future."

He smiled. "No problem, happy to help. Need anything else, or am I free to roam around the building?"

Jennifer laughed. "Nope, that's all the work either of us need for one night. I could use another beer though and looks like you're empty too?"

"Thought you'd never ask."

She chuckled and walked over to the fridge as he stared intently, her full butt jiggling softly with her steps. She bent at the waist to reach for the bottles, stretching the already strained fabric into the crease of her ass. 'Fuck me' he thought, did she know what she was doing to him?

Jennifer did know. She knew and did it on purpose, just as they'd talked about. 'Jim would love this' she thought, smiling to herself. She wasn't wearing panties and the stitch line pulled tightly into her soft flesh. It felt so good, and she wondered if Dan was watching her. She glanced back quickly to find him focused pretty intently on her. She swayed slightly as she grabbed the beer then stood and turned, catching him quickly looking away. She smiled softly to herself. She didn't know if things would work out as she hoped they would, but she was going to find out soon enough.

She walked back over and handed him the beers to open, then picked up her phone and sat on the little couch next to the table. She picked up the phone, then smiled and tapped a few keys and set it down beside her.

"So what have you been up to lately Dan? Spending lots of time with your kids?"

Dan smiled and said "Yes, as much as I can manage at least. It's the same old divorce routine I guess, every other weekend and a few visits in between. I'd like to have them more though. Hopefully we can work that out."

He took a drink and said "How about you? Are you and Jim still planning that trip to Jamaica?"

She took a drink and frowned. "No, I don't think we're going to be able to go this time. Jim has another round of physical therapy he needs to get through first, so we're postponing it until that's done."

"How is he doing with all of that? It's been a couple years since the accident, right?" Jennifer didn't talk about it much, but a couple years prior, her husband was riding his motorcycle home from work when a car pulled out in front of him. There was nothing he could do to avoid hitting the car, and it had thrown him from the bike, breaking his leg in three places. Sadly that wasn't the worst of it though. When he hit the ground, he rolled sideways into a light post in the center median of the road and broke his lower back, leaving him paralyzed from the waist down. It had been a rough couple of years for them, and Dan felt a great deal of sympathy for his friends.

Jennifer smiled and teared up a little. "Thank you for asking Dan. It's actually getting closer to three years now believe it or not. Jim's doing well all things considered, but it's a challenge. He'll never have use of his legs again, so the therapy is focused on day to day things, how to get himself in and out of bed, that sort of thing. Our house had to be remodeled to make it wheelchair friendly, and we lowered some things to make them more accessible. Not that I mind, everything seems tall to me anyway." She chuckled and cleared her eyes and glanced down as her phone buzzed. "Speak of the devil, that's Jim calling now."

Dan started to stand, but she waived him off. "Don't go - I'll just be a moment." He sat back in the chair and she picked up the phone and answered.

"Hi honey, how are you doing?" She glanced at Dan and smiled slightly.

"Yes. We had a great dinner and a couple of drinks, then some of us came back and the kids are working on tomorrow's hangover."

Dan laughed and picked up his own phone, not really paying attention.

"No, I haven't talked to him about any of that yet."

Dan heard her and looked up to find her looking at him with the phone to her ear.

"Yes pretty badly actually, but I'm not sure how. Uh huh, yes that might be a good idea." She smiled at Dan. "Oh...I think I like that idea. We'd find out pretty quick at least, or I'd die of embarrassment. Do you want to talk to him? OK, just a second."

Dan was looking at her with a very confused expression on his face.

"OK." she said and stood up. "Dan, Jim would like to talk to you for a few minutes, is that OK?"

"Yeah sure I guess. What about?"

"He'll tell you. Here you go, I'll be back in a minute." She handed him the phone and walked over to the bathroom.

He held it to his ear and said "Hi Jim, how are you doing man?"

"Good Dan, as good as I can be anyways. I do kind of miss my legs working though." He laughed, and Dan chuckled a little with him.

"I can't even imagine how hard that must be. Is the PT helping?"

"Yeah it really does. I'm able to do most things on my own now, though Jen tries to take over all the time and won't let me. It's actually great for me to have her gone now and then. It forces me to fend for myself, and to tell you the truth I need that. And she needs it too."

Dan took a drink from the bottle and said "I guess that makes sense. Have you figured out how to start riding again? I can't picture you not doing that?"

Jim laughed. "Yeah, I'm actually talking to the local dealer about setting up a trike with all hand controls. Don't tell Jen though, that's going to be a surprise and it'd probably be better if she were here for it. She'll want to punch something, and I'd hate for it to be you."

Dan laughed at that, and Jim continued. "Anyway Dan look, there's another reason I wanted to talk to you."

"Yeah, what's that?"

"That accident was a real bitch for all the obvious reasons Dan, but there are other reasons that aren't obvious. You know I'm paralyzed, but there are other things that happened to me that aren't obvious, and unfortunately they have had a really terrible impact on Jennifer too. There are medical reasons I could get in to, but for the sake of time I'll be blunt. Nothing works anymore below the waist, and I don't mean just the legs."

Dan remained silent.

"Do you understand what I'm saying Dan?"

"Uh, I...I don't know Jim, and I'm not sure what to say if I did." He sat, rather uncomfortable with the conversation.

"I can't perform Dan. My dick is an ornament...it doesn't work anymore. And you don't have to say anything, I'm alive and well as I can be, and I've accepted it. It sucks, but there's more to life they say. The problem for me is what it's doing to Jennifer. We've tried everything known to man and science, and we can still have our fun, but the reality is what it is."

Dan cleared his throat and answered. "Jim, I'm really sorry about all of this, but honestly this is getting to be a bit uncomfortable of a subject for me. I'm not sure why you are telling me all of this shit dude?"

Jim answered. "I know Dan, and I'm sorry. This is the second time I've had this conversation with anyone except Jen, and it hasn't gotten any easier to be honest. The brutal truth is Jennifer has needs and I can no longer take care of them. We are one-hundred percent committed to each other, but for her sake and mine, we have a agreed to open our marriage."

Dan stammered "Why are you telling me this?"

"I'm telling you because Jen likes you a lot, and she's attracted to you. Before you say no or run away, let me explain a few things. Since we agreed to do this, she has tried twice...once sort of successfully and once not. We both thought she could do it anonymously and believed it might be better that way, but we both figured out quickly that a one night stand is not going to work. She needs to be able to trust her partner and so do I, and the only way we can do that is if it's someone we both know."

Dan was trembling slightly. "Jim, I don't know what to say. This is pretty overwhelming, and I'm pretty tempted to just put the phone down and run out of here before she comes out of the bathroom." He was almost frantic, fuck, what if she comes out here in the middle of this?

Jim chuckled. "I understand Dan, and if that's what you want to do please do. I know this is unexpected and uncomfortable, but please know that it's something that we have agonized over, and that you were not chosen randomly. The truth is you are the only person Jennifer and I truly like and respect enough to even think about this. And Dan, Jennifer is genuinely attracted to you and she wants this, but she and I both will respect your decision either way, and regardless of what you decide to do, we want to remain friends."

"Jim, are you asking me to sleep with your wife?" Dan whispered into the phone.

"Not exactly. I'm giving you my permission and blessing though if that is something that you also want."

Dan set his empty beer down on the table. "I'm still speechless, but I'll admit to being intrigued - Jennifer is a beautiful woman, maybe more so than I thought I knew, and it would be a lie to say I didn't find her attractive. This is a pretty crazy step though. I don't know if this is a good idea or not."

Jim laughed softly. "It's OK. Jen isn't coming out of that bathroom until you tell her to. She's as nervous about all of this as you and I are, I assure you. We talked, and she is going to stay there until you either leave or ask her to come out. If you are willing to stay and hear me out, I'll try to explain how we think this would work, although to be honest we don't exactly know either. This is all very new to us."

Dan chuckled. "I don't know what I'm going to do, but I'm still here, so I'll hear you out. I wish I had brought a couple more beers though."

Jim laughed. "Don't worry, I've got a bottle of scotch here for both of us. Just so you know, we tried this twice as one-time things and both times were less than ideal. They both were with a younger man who picked Jen up at a bar and they went to a hotel. I won't go into detail - she can do that if you want her to, but it was quick, clumsy and left her completely unsatisfied. The second time was with the same man, kind of a do-over, and that time she broke it off before they even left the bar. There was really nothing for her. That was over a year ago, and initially I was certain she was done with that experiment. But as time passed and as our own attempts showed more and more that she needed more than I can do for her, we started talking about it again, but this time with a lot more clarity. She needs an emotional attraction along with the physical act, not a falling in love thing, but a caring partner if you follow. She also wants to be free to do the things she wants or needs to do but she wants to know that I am OK with that too. So we talked about it, and decided that in some way I would also be involved. It's for her comfort in all of this, whether I'm there or even on the phone or something, she knows if I have a problem I'll say something. And with you, we both feel like if I did say no, you would respect that. I know this is all weird as fuck, but I hope you understand."

Dan thought a moment and answered "So while we would be doing things, you'd be there?"

"Yes, correct or on the phone maybe."

"Hmm. That sounds a lot weird. Are you sure you're really cool with all of this?"

"Yes, we both are eager to try it, and we hope you will be too. At least eager enough to try. This evening was all completely set up between us weeks ago, down to the computer help, and what she is wearing. You might not know it, but she has a spectacular body, and I know how those yoga pants make her look. She wears them around the house all the time on purpose because I'm an ass man. My dick might not work like it should, but I spend a lot of time drooling over that ass. Admit it, you checked her ass out at least a couple of times tonight, didn't you?"

Dan laughed. "Why do I feel like I'm going to get a call from HR tomorrow morning? OK, yes I'm an ass man too, and I sure as hell did, she's got the most perfect butt I've ever seen. Those pants are what, two sizes too small? It was pretty hard not to notice." He thought he heard a soft giggle from the bathroom.

Jim laughed loudly on the phone. "Yes, something like that. Did she bend over for you? She does that to me all the time, sometimes with a plug in so I can see the outline of it. Drives me fuckin' crazy." Jim laughed. "So the question is are you interested in trying this?"

"I don't know man. I guess part of me wants to and the other part isn't sure if I should. There's a lot of potential to really fuck up some friendships here."

"I get it Dan. We want you to be comfortable in enjoying all of this too. I know it's strange, but we've grown very open with each other through all of this and that's really what this is all about for us. But it's not all about just Jen and I. We would never ask you if we both didn't trust and respect you, and we obviously expect the same. We'd all be learning and figuring out how this works together. I know it's a lot to ask, and the decision has to be yours. You can leave, no questions asked and we all remain friends. Or you can ask Jennifer to come out of the bathroom, and if you do that, we can all talk about this together. What do you think?"

Dan thought a moment before answering. "Jim, I don't know what to say, this is all overwhelming, but I'm not running away yet, so I guess I'm willing to see what happens next."

"I'm really happy to hear that Dan. If you're ready, tell her to come out now and put the phone on speaker."

"OK. You'd better pour me a scotch." Jim laughed at that, and Dan changed the phone setting to speaker. "Alright, you're on speaker now. Jennifer?" he called out. "You can come out of hiding."

He looked toward the bathroom door and watched as the handle turned. Jennifer stepped around the door and stood in the doorway. She smiled sheepishly at him and said softly, "I'm glad you're still here."

Jim's voice, sounding a bit different on speaker called out "Me too!"

Dan laughed. "I'm still a bit tongue-tied to be honest. Jennifer, it sounds like you and Jim planned a lot of this, and I'm pretty shocked by all of it. Are there any other surprises in store, or is there anything else you want to say?"

She leaned against the door frame and crossed her legs as she stood which accentuated her hips tremendously. "I don't know exactly what was said, but I assume Jim filled you in on what we are asking?"

Jim's voice came through the speaker "I didn't go into great detail, but he knows that we want him to be our friend with benefits."

She looked at Dan and smiled softly. "Yes, that is true. I've thought about it for quite some time, since Jim and I really talked about and came to terms with his accident. We've learned more about what makes us both tick sexually because of having to be so honest with each other. Did Jim also tell you that he has always fantasized about seeing me make love to other people?"