I thought it was pretty clear that Bill’s “flirtations’ had crossed some kind of line and rubbing her pussy until she came was far more than just flirting. Still, I found it incredibly exciting and when Susan shrugged it off as harmless play between a boss and his secretary, I let it go. The next evening, I was surprised that she finished at 5 when I did and we rode home together for the first time in a week. She said her day had been less busy than usual and that Bill had tricked her into taking off her dress at lunch and that she had worked the whole afternoon wearing only her bra and panties while she took dictation and typed. I was astounded imagining my wife working under these conditions and at her nonchalant reaction, giggling that he had made her take dictation sitting on his lap. It was difficult not to imagine her pretty ass clad only in skimpy panties squirming on his lap like that, feeling his boner as they “worked” together.
She then surprised me by letting me know she was coming home early because she had to get ready to accompany him to a trade show in Chicago the next morning. She said they’d be gone two nights and she had to pack and get her hair done. She was very eager to see Chicago, a bustling city she had never visited and seemed genuinely interested in attending the trade show.
That night, I sat on the bed as she packed her suitcase and talked excitedly about her trip. She said the trade show was huge with companies coming from all over the country and that it was an excellent opportunity for Mr. Hinton to network and broaden our company’s presence in the market. I couldn’t help but notice as she packed her prettiest lingerie and sexiest sheer nightgown but didn’t say anything for fear of causing an argument. When I asked about her hotel accommodations, she grew silent for a couple of minutes then casually said that his decision to take her along had been last minutes and all the local hotels were completely booked so she ended up having to share his suite. She tried to make light of it telling me she hoped he doesn’t snore as they’d be sharing the king sized bed!
This really got me! She was going to be going away with our boss for the weekend and openly sleeping in the same bed with him! This made me both crazy jealous and very excited imagining that they wouldn’t be getting much sleep. I was so turned on, I tried to get her interested in sex that night but she said she had to get her “beauty sleep” and just turned her back to me. I lay there all night thinking about what seemed to be happening and ended up jerking off right before the sun came up.
The kids and I took her to the airport and I’ve never seen her look lovelier or sexier as she kissed the kids goodbye and headed through security her little suitcase in towI didn’t hear from her the whole weekend and their flight had some sort of delay on Monday so they ended up having to stay an extra night in Chicago and she didn’t get home until Tuesday afternoon. She seemed tired but happy as she eagerly recounted the highlights of the conference glossing over the time spent back at the hotel. When I did question her about their hotel room and about how he had behaved her tone changed and she seemed more reluctant to give details.
Drawing her out, I learned that Mr. Hinton had tricked her into a bet about football. I was very surprised that she’d even go there as she knows next to nothing about football. She lost which meant she’d have to go topless for the whole evening in their hotel room. She said he had mercy on her though and made another bet with her, letting her go “double or nothing.” It was a bet about baseball this time though she also doesn’t know much about the game. She lost and ended up spending the evening completely naked except for her black pumps. She said he mostly behaved himself but took a lot of pictures and played with her tits whenever he felt like it.
She said that she felt so self-conscious walking around nude in their suite that when he said it was time for bed and that she could put on her nightgown she felt so relieved even though it’s very short and very sheer. She was also surprised to learn that Bill likes to sleep in the nude. After they’d turned off the light, he had suggested that they play Truth or Dare. He’d given her the choice of describing how she likes to masturbate or taking a Dare. Susan is very private and couldn’t imagine talking to her boss about masturbating so she took the Dare. He dared her to kiss his dick! She was blushing as she told me that she really didn’t want to do that but she had agreed to play and it was too late to back out.
I couldn’t believe my wife was sitting here with me describing how she kissed his cock but she was doing exactly that. He was apparently very hard and she gripped his shaft with both hands and just gave him a quick peck right on the tip of his boner, barely touching him with her lips. He said that wasn’t enough, that it should be a “real kiss” like in the movies and he had pulled her head down so that his cock tip slid between her lips and into her mouth. He made her kiss him like that for several minutes and then all of a sudden, without any warning, he had an orgasm and squirted a whole load of semen into her mouth. Susan was shocked as she had never had this happen to her before. She said she tried swallowing it all but there was so much that she just couldn’t and a lot of it oozed out of her mouth and dripped onto her nightgown. She said Bill was a real gentleman about it though and had apologized telling her that it was an accident. I thought “accident my ass!” I’m sure he did that on purpose.
Susan said she didn’t want to talk about it anymore, feeling very tired and just wanting to go to bed. I was so turned on I tried to get her to kiss my dick like she had done for Bill and she said that she had just done that on a dare and wouldn’t be making a habit of it. I stayed awake again that night and jerked off 3 times imagining Susan kissing Bill’s cock like that.
The next morning when she came out of the shower I noticed that she had shaved her pussy and she sheepishly giggled saying that it was the result of another bet she had lost with Bill while in Chicago. I thought about Bill making her shave and about her naked pussy all day. She got home about 10 that night and I asked her to tell me more about her time in Chicago. She told me about an interesting lunch they’d shared with a politician and about a visit to the Fire Fighting Museum. I asked her if she slept well and she quickly replied that she had though added that Bill had sometimes made it difficult to sleep.
When I asked her to elaborate, she told me that on more than one occasion, he had initiated a ‘tickle fight’ where he would grab her around the waist and dig his fingers in, tickling her mercilessly while she squirmed and laughed so hard she could barely breath. She was blushing as she told me that in trying to elude his grasp, he was tenacious and held on tight so that when she rolled on her back, he was pulled over on top of her. She said suddenly she could feel the tip of his cock pushing against her pussy and as she squirmed this way and that she felt it start to splay her labia, starting to push into her pussy. She tried to get him to stop, tried to cry out but she said she was laughing so hard she couldn’t get any words out. As she writhed and squirmed beneath him, her legs akimbo, her little nightgown riding up over her breasts, she grew very wet and his cock pushed further and further into her and she didn’t get his attention until she could feel his full balls up against her ass.
When he finally stopped tickling her, she panted that his cock was inside her and he had to stop immediately. She told him that he was having sex with her! Mr. Hinton firmly denied this and said it was entirely unintentional and he even apologized to her promising he’d pull it out right away. Susan said that when he did start to pull out, it felt like she might have an orgasm so she gasped and asked him to push it back in. When he did that she said it mashed hard on her clit and that made her feel like she might cum too. Afraid for him to pull out or push further in, they just lay there for several minutes. Mr. Hinton suggested that maybe she could just cum and get it over with but Susan didn’t want to do that, afraid that would be considered having sex. After a few more minutes of thinking, Susan hit on the bright idea that they could gently rock, like when her car had gotten stuck in the snow, just gentle rocking back and forth had gotten it out.
They started gently rocking like that and at first it seemed like it was working, little tiny thrusts got to be a little bigger and then bigger until he was coming halfway out before pushing back in. Susan said her pussy grew so hot and wet from the rocking that she felt as though she might have an orgasm. She wrapped her legs around him and continued rocking harder and harder, hoping that he’d come all the way out before she came. She told me she was chagrined with she felt herself starting to cum and she could no longer control herself, shamelessly humping herself up and down his stiff boner. She said that Mr. Hinton apparently sensed this and kissed her deeply. As she came over and over, he apparently did too, filling her pussy with his hot sticky cream.
Though they had both cum, he would later deny that he had sex with her, that they had just been playing and it was sort of an accident. Susan seemed OK with that explanation but I had serious doubts. It really sounded to me like they had sex.
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