Annual Meeting 1

I answered the phone cheerily in the car on my drive home and was met with the frustrated-sounding voice of my wife, Sarah. "I just found out the annual meeting is scheduled for the end of the month and I have to go this year as the representative for our team. It sounds like work-related activities until 6:00pm both days and then team-building stuff pretty late into the evenings," she said, annoyed.

"Where is it this year?" I asked

"That's the worst part," she said, "It's about an hour and a half away. Not far enough to be excited about traveling to and not close enough that | could come home to you and the kids after we wrap up for the day. I'm sorry," she said. "It looks like you'll be single parenting for a couple nights while I'm away."

"That's quite alright," I replied, "don't worry about us. We'll have a great time while you're gone."

We chatted for a bit longer and then hung up. The wheels were already turning in my head about the possibilities while Sarah was away. Could I arrange for babysitting and meet her at the hotel for a little getaway once her work stuff ended? I quickly decided against that, thinking of how bored I would be hanging out by myself all day. The next thing that came to mind was seeing if I could encourage her to have some fun herself while she was there.

A few years ago, I had mentioned my fantasy of wanting to see her with another man. She didn't seem interested at the time, and outside of the occasional role-playing with a toy had not shown much interest since either. I wondered if it was the idea itself that didn't turn her on, or if it was her fear of how I might react or whether it would change our relationship or if, as a relatively new mom it wasn't something she thought she should be entertaining. Whatever the case, I had tried a few times since to bring it back up and see if she had warmed to the idea at all - each time getting a gentle no in response, but never a 'forever' no, just a not right now.

Over the next few days, I decided that I would put together a little care package for her to use while she was away. A few things that, at the very least, she could use to enjoy some alone time in a hotel without the kids around. I discretely started packing a bag for her: some sexy lingerie that she could put on to set the mood for herself, a wearable vibrator that I could control via an app, a realistic dildo that we affectionately referred to as 'Ryan,' her magic wand and selfishly, our tripod so that she could send me some photos once she got worked up. I also snuck in a couple of condoms, should she see this as the opportunity to indulge my fantasy.

In the few days leading up to the meeting I could tell Sarah was feeling frustrated about having to go, stressed about packing and guilty about leaving me with the kids. While we were chatting in bed one night, I assured her it would fine and tried to point out the positives -- I would get to have some fun alone time with the kids, she would be able to sleep unbothered by waking toddlers, it would be a great networking opportunity at work and she would get to wear a few fancy outfits for the team-building activities after the official work day ended. I also pointed out that, in the worst-case scenario, she would get some fun alone time in her hotel room after a few drinks. She coyly asked what the best-case scenario would be if that was the worst.

"Some fun, not-so-alone time in your hotel room," I replied with a wink. "This might be a great chance for you to try out that fantasy of mine. Surely there will be a few co-workers you find attractive there. People are flying in from all over, so it could avoid any awkwardness of having to see them regularly at work afterwards. No pressure, but I want you to know you not only have my permission but also my encouragement to explore if you like as long as a few ground rules are followed."

"I wouldn't count on it," replied Sarah. "I'm sure I'll be tired from the meetings all day and will want to remain professional so I'll probably leave the team-building stuff as early as I can just to get to bed. But just out of curiosity, what sort of ground rules did you have in mind."

The fact that she was even asking was making my heart race and my dick begin to swell. "Well," I started, "Since I won't be there to see you in action, I'd want regular updates both to make sure you're safe and because it would be a huge turn-on for me. Who you're finding attractive and flirting with, how you're feeling, what sorts of things you're doing with them. If it gets that far, some action shots of the two of you. I'd love to see how you touch each other, how you suck his cock, what you look like being fucked by another guy and an after shot once he's cum so I can see where you decided to take it."

"Is that all?" She asked jokingly.

"Above all else, have fun." I said. I could tell that our chat had gotten her a little turned on, so I reached over and started touching her. Her pussy was already wet so after going down for a quick taste, I buried my cock inside of her. Both being a little worked up, it wasn't long before she let me know she was about to cum and we both climaxed at the same time. Cuddling up to each other afterward, I (already knowing the answer, but wanting to hear it from her) asked her if that little chat had gotten her excited. She mentioned that it was a hot thing to fantasize and dirty talk about, but practically would be very unlikely to happen. I responded that I was ok with that, especially if it led to sex that was that hot, but was secretly hoping that the fantasy turned into a reality.

Over the next few days, the topic of the meeting would come up in bed and turn into very passionate sex. Each time, Sarah would say it was just the fantasy that turned her on and not to expect anything to happen while she was gone. The end of the month rolled around and while I was helping Sarah to load the car, I mentioned the care package I had put together for her and slid it into the trunk. I kissed her goodbye and told her to have a great time.

She called me after she had checked in and unpacked and told me that she was very pleased with her care package, and excited to use some of it later that night after the team-building activities had ended. I mentioned that, if she was feeling up to it, she should slip the remote-controlled vibrator in after dinner while everyone was having a few drinks and let me know so that I could control it while she chatted with her coworkers. She didn't promise anything, but didn't immediately shoot the idea down either.

We texted on and off throughout the day, mostly about how boring her meetings were and how the kids were doing. After I had put them down to bed, I checked my phone and noticed one from my wife that just read "Open up your app ;)" and I was immediately hard thinking about her being that naughty so close to her coworkers. I did so, and sure enough she must have turned it on, because the toy connected and I was able to start sending some good vibrations her way. I would occasionally send a jolt her way, imagining her talking to some handsome coworker and having to try to hide the expression on her face as the sensations in her pussy increased.

Eventually, the battery must have died because I lost control of the toy. Not long after, Sarah called to tell me how much that had turned her on and how much she was looking forward to using the rest of her care package now that she was alone in her room.

Of course, I told her that I was a bit disappointed that she was alone in her room and asked her if she'd anyone she liked there. She mentioned that there were a few cute guys, but one especially that had been quite interested in chatting with her - Cal. She had worked closely with Cal a number of years ago, but he had moved across the country for another job within the company. They remained friendly via their work Teams chats, and he mentioned that he was hoping he would run into her at the meeting as he'd had a bit of a crush on her before he moved away. Of course, he would never have acted on it at the time because they were both married but he'd recently gone through a divorce and was hoping she was also available. Sarah had told him that she was still very happily married and while he was disappointed, they continued to chat and have a great time throughout the evening. I asked her if she had also had a crush on him, but all I could get her to admit to was that he was "handsome and charming." We talked a bit more before I said good night, so that I could leave her alone with her care package.

I woke up in the morning to some great photos: Sarah in various poses wearing one of the different pieces of lingerie I had packed for her, touching herself all over, using her magic wand and some photos of her and "Ryan" the dildo together. I came almost as soon as I started touching myself to them and was glad that the care package had worked as planned.

There weren't many updates for the rest of the day, until dinner came around. Sarah sent a photo of her dinner outfit, and to say she looked amazing would be an understatement. It was a medium length black dress that showed off her very generous cleavage and outlined her firm breasts as much as possible while remaining professional. It hugged her beautiful ass tightly and showed off a fair bit of her amazing legs. She then sent a photo of what she was wearing underneath and to my surprise, it was the second piece of lingerie I had packed for her. If someone caught a glimpse down her dress they would know that she was wearing something very sexy under her outfit.

I told her I loved it and asked her if she was wearing it for anyone in particular. When she replied "I thought I might show Cal later" I almost came without even touching myself. I asked if she was serious, and she responded "While I was playing with the care package last night, Cal kept popping into my head. As I was touching myself, I wondered what it would be like to have him touch me. As I was playing with 'Ryan,' I wondered what Cal's cock would look like, and what it would be like to feel it inside of me." I couldn't believe what I was reading. I was so hard that I thought I would explode any second. She followed it up with "That is, of course, if you're still ok with it. I think you're right, there isn't going to be a better opportunity than this. I trust Cal, I think he's attractive and he lives across the country so there won't be any awkward interactions later." I told her I was definitely ok with it, as long as she remembered the ground rules, and told her to have fun. Before she headed off to dinner, she sent one last photo of the remote-controlled vibrator inside of her and told me that she was going to have Cal download the app too.

I waited for updates during dinner but they were few and far between. I wondered if she had lost the nerve to go through with it, or if she was too busy enjoying herself to remember to send anything along. Just as I was starting to put the kids down to bed, Sarah texted me that Cal had been a gentleman when she mentioned the toy she was wearing. She had to explain to him that, while she was very happily married and intended to stay that way, that didn't mean she wasn't available. He was shocked but instantly excited. She sent him the app to download and told me he had been teasing her with it all throughout dinner. They were just heading to the team-building portion of the evening (aka drinking) and hoped that I would be near my phone for more updates to come. I quickly put the kids down and headed to the basement to try to distract myself with some TV while my imagination ran wild.

I received a few updates, all very short and all very hot:

"Absolutely soaked, had to take the toy out before I made a scene at the bar"

"Cal must have taken a peek down my dress because he told me he was excited to see more of what was under my outfit later"

"He took my hand and made me feel how hard I was making him. The answer is very, and it feels BIG"

Finally, Sarah called to let me know she had gotten back to her room. She said she had a couple minutes since Cal was going to grab a few more drinks from his room before meeting her at hers. I asked her how she was feeling and she told me how turned on and excited she was but wanted to give me one last chance to call it off if I wasn't comfortable. Of course, I told her to go ahead and keep my posted. She said she'd mentioned the ground rules to Cal, and he was happy to follow them. When she mentioned to him that I had packed her a tripod, he suggested they set it up and Facetime me before they got started so that it would feel like I was right there watching. Sarah said she had heard a knock at the door and told me she was going to go set up the tripod and call me back before answering.

It was only when I picked up that I realized that Sarah had ditched the dress and was now wearing just her lingerie. I heard her invite Cal inside and mention that I was already there watching. Cal and I chatted awkwardly for a bit -- he said he wanted to make sure I was actually ok with this, which I confirmed. He made sure to tell me what a lucky man I was to have such a beautiful wife and thanked me profusely for letting him 'borrow' her for the evening.

They opened their drinks and sat down on the hotel's bed together, sipping awkwardly. It was almost like they didn't know where to start now that they were actually alone together, so I took the opportunity to provide some direction. I told Cal that Sarah loved a nice foot massage after a long day in her work heels. He pulled one foot into his lap and started rubbing it with large hands. Sarah sighed with pleasure before offering him her other foot, which he worked on for a few minutes as well before moving up her legs. He paid some attention to her calves before slowly working his way up to her thighs. As his hands were moving towards her surely soaking wet pussy, she stopped him, indicating it was her turn to help him relax.

Sarah stood Cal up and slowly unbuttoned his shirt, running her fingers over a trimmed, athletic-looking chest. As she slid the shirt off him, she noticed his toned arms and stopped to admire them with her hands. She then started to unbutton his pants and struggled briefly to pull them down over his very obvious erection. Sitting him down on the bed, she started massaging his strong thighs with her hands, her eyes fixated on the bulge underneath his briefs. Looking back at me on her phone, she asked one more time if I wanted her to go for it. Nodding my very enthusiastic consent, she slid his boxers down and the largest cock she had ever seen sprang up from beneath them. Licking her lips, she reached out to stroke somebody other than me for the first time in 15 years. She gently teased up and down his 7.5 thick inches with her fingers, kissing his inner thighs as she did. Slowly her kisses moved to his balls, planting one on each. She then kissed gently up his shaft, pausing when she got to the head to admire him. Smiling up at him, she finally took him into her mouth. It took her some time to get used to the size of him, but she got into a rhythm and could tell he was loving her efforts.

After a few minutes, Cal pulled her mouth off him and laid her down on the bed. He kissed his way down from her neck, stopping to pay attention to her perfect breasts with his hands and mouth. Then he worked towards her pussy and pulling aside her lingerie, began to lick and suck on her soaking-wet pussy. Sarah was clearly loving his mouth, as her breathing began to increase in pace and her moans became louder. It wasn't more than a few minutes before she had her first orgasm of the night thanks to Cal. Sarah often needs quite a while to recover and pushes my head away after she's climaxed, so I worried that there would be a lull in the action but rather than push him away, Sarah held his head in place and started to grind her pussy on his tongue for another minute or two before pulling him up and telling him to fuck her.

Cal climbed up the bed and positioned his cock at the entrance of her pussy. She guided his head inside and thankfully, he went slowly to let her adjust to his size. Before long though, she was taking his entire length inside of her and loving every stroke. Occasionally she'd look at me on camera and noticed that I was stroking my cock watching her and that seemed to turn her on even more, because her moans would get louder and her words got dirtier. She was telling Cal how amazing his big cock felt, how wet her pussy was for him, and since she wasn't on birth control, how badly she wanted to have him cum in her mouth. Cal fucked her to one more orgasm before announcing he was ready to cum himself. He pulled out of Sarah, his cock covered in her excitement and knelt by her head where she sucked and stroked him for a few minutes. Finally, he announced that he was cumming and she clamped her mouth around the head and took him as deep as she could in her mouth. She held him there until his orgasm had subsided and then opened her mouth to show him and I that she had swallowed it all.

Cal collapsed on the bed and Sarah grabbed her phone to check on me, finding me cleaning myself up as I had cum at the same time as Cal. She asked if I had enjoyed myself, and I replied that it was the hottest thing I'd ever seen. I asked if she enjoyed herself as much as it looked like and she said absolutely, and thanked me for encouraging her to try it out. It was late and I knew I would be up early with the kids so Sarah and I said our goodnights and I encouraged them to stay the night together so they could have some more fun before checking out in the morning, reminding Sarah I would still like some photos and videos.

I drifted off to sleep and awoke to a number of messages and photos in the morning. Based on the time of them, it looked like they had sex once or twice more before falling asleep, and again early in the morning before going their separate ways. Sarah arrived home later that day and seemed nervous walking in the door, until I met her with a big hug and kiss and told her how much I loved her. She told me she had been nervous about how I would react to actually seeing it happen, but was glad that we had shared that experience together. I reiterated that it was the hottest thing I'd ever seen and that I hoped it wouldn't be a one-time thing. Sarah mentioned that Cal thought he might be able to justify a few trips out to her office for 'business purposes' and thought she could invite him to stay with us next time. It was all I could do not to rip her clothes off right there and reclaim her, but that came later that night. Since then, our sex life has been on fire and we are eagerly awaiting Cal's next visit out to see her.