Roleplaying the Lifestyle
Loving Wives Story

Roleplaying the Lifestyle

by Cum4thecumgod 19 min read 4.2 (33,400 views)
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I'm not sure when it started, the fantasy I had. It could have always been lurking in my head somewhere, even before I met my wife, Jordan. I distinctly remember a conversation early on in our relationship, when we were just dating, about certain fantasies. One of hers was a threesome with two guys, but as she put it, that will never happen now that 'we are together.' Some cowardice of mine kept me from speaking up, but at that moment I knew I wanted to see her get fucked by someone else. All these years later and that dormant fantasy has become forefront in my mind.

It was never about the humiliating cuckold fantasy, but merely a fascination on what it would look and feel like. I had a very robust sex life prior to meeting Jordan and had experienced much of what I wanted to in that regard. Jordan is the one for me. She, however, only had three lovers prior to me, and to hear her tell it, two were somewhat lackluster. I wanted to have her experience new sex, good sex and just plain different sex. It wasn't that I was lacking something, it wasn't that I needed a 'real man' to show her how it's done. I just thought she could and should enjoy something new and different. Plus, I think it would be incredibly hot to watch her fuck another man.

Anyways, outside of a few friends I told drunkenly years ago, I've never broached the subject. It has become a part of basically every solo session I have. I've bought Jordan toys, vibrators, realistic dildos, blindfolds and even a butt plug, but while she enjoys some on her own and occasionally we will play with them together, she seems to prefer sex with just me. Not that I'm complaining.

What enfolds below is about ninety percent true, with a few embellishments. It's also my first time writing something like this, so any constructive feedback would be nice.

Then, to celebrate our anniversary night this year, I decided to get a little more risque and see how she would react. Occasionally I work nights and was scheduled to over the weekend prior to our anniversary, which my wife knew about. Unbeknownst to her, I had gotten work off and found a hotel in town with a jacuzzi ensuite. While she was at work, I packed all of my preparations and set off to check in...

-

Once checked in, Quinn laid out two of his favorite lingerie sets Jordan had, out on the bed. One was a small blue lace two piece that was just thin enough to give one the hint of nipple and pussy. The other was a sexy black ensemble with garters and some tights. Quinn left Jordan a bottle of champagne, her vibrator, hand cuffs, plug, and lube out on the bed, bubble bath for the jacuzzi and paid for some pay-per-view porn that had a few threesome scenes in it.

He left a note on top of it all,

'Welcome to your suite. I can't wait to join you when I get off at about 10, but I've set up and planned out your evening so you don't have to wait for me. I'm sure you need to decompress after work, so pop your champagne and relax in the jacuzzi. I've bought you some watching material if you so choose to get yourself in the mood and I'm sure you can utilize some of these toys to your advantage. Your dinner will arrive at 6 and has already been paid for. However, I didn't leave a tip for your delivery man, you should find a way to 'pay him' that doesn't involve cash. I want you to trust me and remember I love you, Jordan! Happy Anniversary! -Your love, Quinn'

Quinn took off and made it over to her work at about 3:30. He sometimes stopped by on his way to work to say hi and give her a kiss. This time he came in with a bouquet of peonies and a card.

Jordan was surprised and delighted and jumped up to give Quinn a kiss.

'Oh my god, you shouldn't have! They're gorgeous!'

'Anything for my love! I have to run to work, but I wanted to drop this off!'

'You spoil me, I love it!' Jordan said as she reached for the card.

Quinn stopped her, 'Don't, not yet. You've got to read it after I leave and don't show your coworkers! Just trust me okay?'

Jordan raised an eyebrow and gave him a little smirk. 'What's this then? What are you up to?'

'Can't say miss, all I can say is I wish I could get off earlier if you know what I mean.'

With that, Quinn pulled her in for a deep kiss that lasted slightly longer than it should at work in view of her coworkers. He turned around with a wink and left out the front door with the biggest, most nervous smile he had ever had.

The card was a cheesy anniversary card talking about how they've survived another year, but its contents were anything but:

'Love of mine, I've booked you a special night tonight. I'll join you later tonight but for now please just follow your instructions. It will be a night you won't forget but I've planned a special timeline for you. No need to go home, you sister has the kiddo. No need to call her, I promise its all been taken care of. Just head to your hotel as soon as your done with work, there you'll find additional instructions. I love you 110% and I hope you'll enjoy your evening! With everything I have, Quinn'

A hotel room key was also inside.

He received a text message not 10 minutes later.

'What is this my love, what have you got planned?!' It was accompanied with a big grin emoticon.

'Just follow my instructions and I promise that you'll love it! I've got to go into work now, so have fun!'

Quinn drove as fast as he could back to the hotel and parked across the street and out of sight. He grabbed his bag he packed and changed into jeans and a tee shirt, clothes he had bought recently that his wife hadn't seen. He sat back and waited.

Jordan pulled into the parking lot slightly before 4, looks like she had gotten off early to see what this was all about.

By 4:15 Quinn received another text.

'OMG! You are so dirty!'

Another text.

'I love it.'

Quinn just sent back a smirk emoticon and a simple text; 'Enjoy.'

15 minutes later Jordan sent a picture.

She was in the jacuzzi, her dark brown hair done up and was cheering the camera with her champagne flute. Her breasts were seemingly floating on the jacuzzi bubbles, like perfect globes. They were distracting Quinn's eyes from her enchanting smile with lips done up in red lipstick that wasn't there that afternoon. Quinn got rock hard sitting in his car. He looked at the picture long enough that he could see in the mirror, behind the tub, the reflection of the tv. On it, it looked to be a blonde giving head to a rather large black cock. He couldn't even remember if the porno he had rented was interracial or not.

He put his phone down and drove away, on to his next move.

He arrived at her favorite Thai place, parked and walked inside. Thai was one of her favorites and it wasn't going to be too heavy. He thought it might be considered 'sexy.' He sat at the bar ordered her some to-go food, and him a small sake and a beer.

It took about an hour for him to finish his drinks and get the food and he hopped back in and drove back to the hotel. He hadn't heard from Jordan since her photo, but he had looked at the photo about a dozen or so times since.

Walking back to the room he felt nervous. He didn't know why, he knew it was just him walking up but he was curious if he could hold up his 'facade.' He knocked twice and masked his voice to the best of his ability and shouted, 'Delivery." He only just noticed the older couple walking down the hall as he did so. It was 6:05.

Quinn could hear his wife from seemingly far away shout, 'Just a minute!' through the door. he glanced over at the couple as they walked nearer in silence. he stepped away from the peephole so she couldn't see his face before she opened the door and waited. Within seconds, she pulled open the door wide.

Jordan was wearing the small blue two piece set. It hugged her late 20s body perfectly, accentuating her curves in all the right places. She was the most beautiful thing Quinn had ever seen. Her slightly damp hair was up and she had her glasses on. While he tried to pick his jaw off of the floor, her shocked expression gave way to a sexy smirk, to embarrassment when the couple walked passed. She told him later the woman looked away quickly, but the man stared as he slowly shuffled passed.

'Well come on in then, you can set the food down by the bed,' she said.

Quinn shuffled in, still unable to pick his jaw up and rendered mute.

'Thank you so much, I'm literally starving!' Jordan said, 'What's your name?'

'Umm, uh, Tony,' he stuttered.

'Well Tony, I can tell you like what you see.' Jordan said as she cupped her tits underneath he lingerie.

'I've been told my husband paid for this, but that I needed to pay for the tip. Let me see what I can do.'

Quinn set the food bag down and just stared. Jordan had opened the door in her lingerie and looked shocked, maybe even a little disappointed it was him. It was exactly what he had planned, but he had more than half expected her not to have done it.

She bent over at her waist to rummage through the empty bag of her stuff he had left, her ass facing him. Her lingerie had started to bunch up between her cheeks, it was all he could do to grab them and bury his face inside.

She turned around, 'Well it doesn't look like I have any cash and I can tell by the way you're looking at me and by that big bulge in your pants I've given you about half of what you deserve just standing here.'

With that she walked closer and rubbed his hard dick through his pants.

Quinn groaned and nodded, half dumbstruck at his gorgeous wife taking this role play farther than he had thought and half playing a young timid delivery boy.

She leaned forward as she gripped 'Tony's' hard cock, 'What if I let you touch my tits, would that be a good enough tip.'

He almost came, whispered 'Yes ma'am' and tried to lean in for a kiss.

She pulled back, 'I never said you could kiss me, I only kiss my husband.'

She arched her back and framed her tits with her hands, 'Go ahead, they're aching for you to touch them.'

'Tony' held back as much as he could and timidly started touching them through the lingerie. 'Oh my god, they're amazing.'

Jordan just smiled and leaned back a bit. 'Tony' got bolder and pulled her lingerie down, exposing her bare breasts. Her perky tits bounced slightly and her small, hard nipples popped out just begging to be licked and sucked. He slowly leaned forward slowly, taking one in his right hand and the other in his mouth, lightly nibbling and sucking while he rolled the other with his fingers.

Jordan moaned now, turned him so his back was to the bed and then pushed him down to sit on it. Her nipple began to slip out of his mouth and he bit down a little harder to keep it right where he wanted. She squealed and came down on her knees, straddling him.

Jordan grabbed the back of his head and pulled it closer, moving him back and forth between both of her nipples. She grabbed his left hand and pulled it down until it made contact with her mound. 'I think you deserve to feel that as well.' Tony started to rub her clit through her lingerie as she began to buck her hips against his hand.

'Oh, Tony, that feels so good.'

She wouldn't let Quinn forget their little role play and if his dick wasn't hard enough yet it was the hardest its ever been now. After a few minutes, she pushed him down on the bed, and crawled over to his head. She pushed aside her panties and told him to eat her out.

Tony started to lick her shaved lips back and forth and paid special attention to her clit, nibbling away. He grabbed her ass and pulled her closer, he wanted to inhale her, he wanted to engulf her. She began to rub his hard dick through his pants.

'Oh Tony, that's the spot. Oh, you eat pussy better than my husband!'

Quinn was sure she felt his dick jump when she said those words. One hand stroking his dick through his pants, one behind her grabbing his hair while she rocked her hips slightly back and forth as he dove into her snatch as best he could with his tongue.

Within a few minutes she began to buck and cried out, 'Oh fuck, oh fuck, oh fuck! Tony I'm cumming!'

She drained herself on his face, screaming Tony's name.

It took her a second, but she rolled off of him, and straightened out her lingerie. She walked over to her food that he had almost forgotten about, grabbed it and sat back down on the bed. He slowly stood up and looked at her a little confused.

Tony started to unbuckle his pants and before he could even say anything she said 'Oh honey, you don't expect me to play with your dick do you? You don't deserve that good of tip, you were five minutes late.'

Dumbfounded he kind of just stood there, 'Oh, but, I mean, I'm rock hard.'

'Well you might want to take care of that before you go back to work then, but as you can see I'm trying to enjoy my dinner so you can see yourself out.'

'Well can I at least take a picture so I can show the guys back at the restaurant why I was late?'

'No, Tony, you've gotten your tip so please leave.'

Shocked, turned on beyond belief and a little dejected 'Tony' turned around to leave. Quinn had thought that the 'evening' would probably be over once she knew he wasn't working, but she seemed to have planned to have it continue. So he buttoned up his pants and started to leave, he opened the door and looked back one last time. There she was looking sexy as hell in her lingerie, eating her Thai food and watching a TV show she just turned on, not even looking at him.

Quinn turned around and left. He was dumbfounded. They had never role played anything like this before but she had played that like a pro, and had exceeded any of his expectations. She took control. She was sexier than he had ever seen her and he had never had cause to complain in that department. He was just on a sexual high that he didn't know he could be on.

Quinn knew Jordan would be finding the note right about now, the note he had left in her food bag.

It read:

'I hope you left him a good tip and just the tip! Although this is your night, so whose to judge. Anyways, maybe soak some more or get some more inspiration from any video you might find. Whatever charges you might put on, I'll cover. Your next appointment isn't until 8. This one might be more of a hands on approach. I was able to find a masseuse I think you might like. Remember be as comfortable as you'd like and know that I will always love you!'

At this point, his plan was to go grab a drink at a bar nearby, but Quinn couldn't decide on which one and to deal with parking, and it was already 7. There was one thing he couldn't get out of his mind, so completely on a whim he decided to go to a sex shop not too far from there.

-

Like I mentioned earlier, we had experimented slightly with toys but had not done a lot and I've only ever ordered them online, I had never gone into a sex shop before. So I perused the dildo section, paying particular attention to the suction cup variety. I have learned and will be buying a few different selections I think for next time, but was happy with the result this time.

-

Quinn finally landed on a 9" black silicone suction dildo. He wanted a big dildo but not ungodly big, and while much bigger and thicker than his 7" cock, he felt like it wouldn't truly break her. After paying, Quinn realized he might be late again, so he rushed back over to the hotel.

In the parking lot he changed again, this time into a v neck and sweatpants, and put the dildo in with his 'massage bag' filled with some lube and oils. Quinn knocked on Jordan's door and didn't say anything and she only responded by opening the door a few minutes later.

This time, she opened the door completely naked. He was shocked again, she kept surprising him and looked sexy as ever.

'Oh, you must be the masseuse,' his wife said.

I nodded, 'Yeah, my name is Tom.'

'Pleasure to meet you Tom, my husband said I should be as comfortable as I wanted, and since I get massages nude, I figured I might as well start that way.'

Looking her up and down 'Tom' replied, 'Works for me.'

Still standing in the open hotel doorway nude, she ushered him in, 'Well, come on in then.'

'I normally tell my clients I'll get set up, but I don't have my massage table tonight, I broke it in a, uh, rigorous massage last week. Would you mind if we used the bed?' Tom asked.

'Oh really? Sounds like my kind of massage. No, not at all Tom, I think that just makes the whole thing easier.'

'Well, go make yourself comfortable, but I can see you already have, I need to get a few things ready and I'll meet you over there. You should put this on when you're ready. It, uh, helps you relax.' Tom handed her a blindfold. 'Do you mind if I use the bathroom for a second?'

'Of course Tom, I look forward to your hands all over me.' He watched her saunter over while holding the blindfold, swaying that ass as she went.

Once in the bathroom, Quinn took out his new black cock and washed it, dried it and stuffed it awkwardly inside his waistband. It held and was clearly noticeable, he had to try and tuck his real cock away to make sure the dildo was the one felt or seen.

When he walked back out, there she was naked as the day she was born, spread eagle on the bed with her blindfold on. It took everything he had not to jump on that bed and fuck her hard. It was then that he noticed the second, slightly opened champagne bottle. She must have gotten room service. Did she answer in her lingerie, in the nude, did she 'tip' the bellhop? Quinn had no idea and it drove him wild.

She heard him approach, 'Is this right where you want me Tom?'

'Yeah, that'll do, I never caught your name.' He whispered.

'Well, if my husband didn't tell you, than maybe its best if you didn't know.'

God, she made it difficult for him to continue. He put on a sultry, sexy Karma Sutra Massage playlist on and got to work. He had planned on giving her a full 60 minute full body massage, and he did. Quinn had always been good at massages, he was a competitive swimmer for a long time and gave massages to all the girls on the team during meets and had developed some very good techniques. He kept it sexy, bending over to breathe across her back, leaning over and brushing the dildo in his pants against her head and hands. She gripped it once and must have felt it to be larger than his own. It wasn't until 'Tom' got to her legs when he was peering down and looking at her beautiful pussy that he noticed that she was wearing her plug. They had only tried it once, somewhat drunkenly and while it was a small size it was almost too large for her and she wanted it out quick. There she was wearing it, its jewel just slightly sparkling in the candlelight.

Jordan was exceeding his expectations at every turn. Nearing the end of the massage, Tom gently whispered, 'Now, I know this might come as a shock, but some of my clients like to upgrade their massages. I do and can provide happy endings and, on occasion am willing to provide absolutely EVERYTHING to my clients. I have some, unorthodox techniques that have been met with rave reviews. Does that sound like something you'd be interested in?'

His wife's only reply was, 'Oh god yes.'

'Then turn over.'

Jordan rolled over almost immediately. Tom started with her tits, rolling both nipples between his fingers before leaning over and taking one into his mouth. He wasn't timid this time, because Tom wasn't timid. Tom took control and knew what it took to make his clients happy. As one hand slowly slid down his wife's stomach, he slowly kissed up her neck towards her mouth. As he got close and she leaned in for a kiss, he pulled back. 'Oh no, I don't kiss my clients.' Her sad pout was enough to make him smirk.

Tom made his way back to her breasts, biting them a bit harder now, causing her to moan loudly. His fingers had made their way down to her clit, teasing the folds of her vagina and rubbing lightly on her cute little button. He felt her hands go up his thigh and grab hold of the black monster in his pants.

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