I almost cheated

I had been married for 10 years and was in my early 40s. Like far too many people, the passion was lacking. 

By so many measures, things were great. Great kids, nice home, good jobs, etc. 

One problem we had always had sexually was that my wife was too uncomfortable with herself to enjoy receiving oral. And I love giving oral. 

When I was in my teens and 20s I was always freaked out about not being able to last long enough to please a partner. A couple of bad early premature ejaculation experiences had me terrified. 

So I developed very good oral skills. I figured that if I provided a couple (or more) really good organs through oral at the beginning, then maybe subsequent short comings would be less of an issue. 

I had ample experiences with multiple partners to know it was something I was good at. But my wife didn’t let herself enjoy it. 

As the passion waned, I really wanted to give mind blowing oral to a woman. I watched porn that focused on that and it was a regular fantasy. 

I discovered reddit and then stumbled across RAOMD. I had never really considered cheating. I travel frequently for work and had several opportunities, but for many years did not act on them. 

But in scanning RAOMD, I saw a post from a woman who would be traveling to the same city I would be in two weeks later. Our schedules overlapped by two days. 

Somehow she decided to chat with me, out of all of the messages she surely received. 

No, I didn’t send a dick pic. I don’t have any of those. But we chatted by text, then phone, then facetime leading up to the trip. 

Swapped some sfw photos. Some of hers were suggestive only in that I have a thing for a woman in business attire and heels.

We really seemed to click.

I am a pretty average looking 40-something guy with some extra weight and less than extra hair.

She was eight years younger, with three kids, and beautiful. At first, I was sure I was being catfished. But facetime proved her to be real. 

She said she was 5’8″, she had brown hair, was slim with what appeared to be B cup breasts. And such a pretty face. Angular with high check bones. Gray-blue eyes.

She did not have a dead bedroom. She said she and her husband had sex almost every night (something he liked to brag about to their friends), but it was usually a couple of minutes of missionary with no orgasm for her. She married soon after college and had never had a man go down on her. Her husband would not.

Her only experience receiving oral was one time with another girl in college. She had always wondered what good sex was like and if her memories of oral were as good as she remembered, or if she had mythologized the memory.

Before marriage I had done some online dating and a lesson I learned was that no matter how great someone looked, or how well the conversations went, there is no way to anticipate physical chemistry until you are in the same room with someone. 

Since we had two nights in the same city, we planned to meet for drinks after work for an hour, and if there was no chemistry then there would be no harm and we’d go our separate ways. But if there was, we would spend the next night together. 

We both had work dinners at 7 p.m. so we planned to meet at 5:45 at a downtown bar. 

I got there a few minutes early, and she was already there in a booth at the back of the bar. 

She looked even better in person. 

She was dressed in business clothes. Pencil skirt, button up shirt, high heeled pumps. All very work appropriate, and just tight enough to highlight her shape. 

With the heels she was taller than me. The heels really accentuated her calves and ass. The skirt knee-length hugged her ass to show a perfect little bubble.

We hugged and then sat down to talk. Sadly, there seemed to be no chemistry. There was no electricity in the hug. The conversation that flowed so well on the phone was not awkward, but not like it had been on the phone. 

We both had to leave a little before 7, so I decided this was going to be a bust and I’d stay until the agreed upon time and then we’d not see each other again. 

About 30 minutes in she mentioned that her feet were killing her from the new heels she bought just for our meeting. 

I made some throwaway comment about them needing a good massage. Something like, “Well since it is my fault your feet hurt, the least I can do is relieve the pain. Lift them up and I’ll massage them.”

As bad as things were going, the last thing I expected to hear was her asking if I was serious. 

“It seems I am the cause of your discomfort, so the gentlemanly thing would be to help relieve the pain,” or some such nonsense. 

I’d barely gotten the words out and both of her feet were on my legs. One on each thigh. 

I am not necessarily a foot guy. I love worshipping a woman’s body, so I have played with many feet, but I don’t have a thing for them above other body parts. 

I was instantly hard. But what do I do? She called my bluff. The bar is packed with the happy hour office crowd. We are slightly secluded, but not totally out of sight.

My heart was racing. As bad as things had been going, I was not expecting this. I temporarily froze.

Then decided, “what the fuck.”

I took one foot, removed the heel and started gently caressing all around her foot. Then I took my thumbs and began deeply rubbing the ball and sole of her foot. After a few minutes I started working up her ankle and calf. I massaged to her lower thigh and massaged her inner thigh a bit. 

Even though her legs were long, it wasn’t possible to get much higher in a public place and under the table, and I wasn’t sure where this was going. 

Did she think this meeting was a bust and figured she’d at least get a foot massage out of it, or was she into me?

As I said, I am pretty average looking and she is at least a 9 by any measure, and a 10 with my particular likes. So my insecurities added to the bad start had me unsure how far, or in which direction, to take things.

I finished that foot and placed it on the seat between my legs, but was not bold enough to place it on my dick. 

I picked up the other foot, removed the heel and started to repeat what I had done to the first foot when I felt her foot against my dick.

At first I wasn’t sure if it was an accident. Then her toes started teasing it lightly and I knew. Then there was more pressure as she starting rubbing her foot up and down.

She is looking me right in the eyes as she is doing this. It is one of the hottest experiences of my life.

I haven’t had premature issues since my 20s, but I was afraid I going to explode right there. 

I kept massaging the new foot, then calf, then thigh. And as I finished an urge came over me to lick her foot or suck her toes. I was holding her foot up and looking down at it.

She must have sensed my dilemma and she said, “Suck my toes.”

I didn’t even look around the crowded bar to see if anyone was looking. I was drunk with the cum building up inside me. 

While keeping eye contact with her, I lowered my head and lifted her foot until I was sucking her big toe. Then licking between her toes and then her sole.

She was working my dick vigorously with her foot and then I realized I was in a crowded bar and I let her foot drop. 

Her foot stopped its action when I did. 

“Well this was fun, but we are now both a little late. Put my shoes back on then let me go freshen up in the bathroom quickly and I’ll meet you outside.” 

I put her shoes back on and she could resist using her heels to stroke me up and down with firm pressure a few times. Then she popped up and went to the bathroom. 

Of course I watched her ass and legs as she walked through the bar.

It was 6:50 and my dinner was only about a 10-minute walk away. People always straggle in at these dinners, so I had a few minutes of cushion.

I walked through the bar knowing that my suit pants would not disguise my erection if anyone looked down. I waited outside for a few minutes.

When she came out she immediately grabbed me and kissed me deeply. She ran a hand around my chest and then down to grab my dick. One firm tug. Then she put her hand in my pocket. 

She pulled her hand out and pulled away from me and told me not to reach into my pocket until she was gone, and to not masturbate before seeing her tomorrow. “I earned the cum you are filled with, don’t waste it alone and don’t give it to anyone else.”

Then she turned and walked on her way. I watched her amazing ass and legs until she turned the corner. 

I had to walk quickly to not be too late. I was still as hard as I have ever been. I was hoping it would gone down during my walk. 

She and I purposely hadn’t planned to do anything that night because my new division CEO had made it clear she wanted all of us regional VPs to bond as a team. She said we would likely be out until midnight, if not 2 a.m.

It wasn’t mandatory. A couple of ladies always bailed early. But I liked the new CEO and wanted to support her.

Even though I knew that these events usually ended up with a couple of the late 40s women going to the hotel straight after dinner, most everyone else going back by 10, and 4 or 5 of us staying out way too late. 

There were two seats together left when I arrived at dinner but people were getting drinks and discussing which appetizers to get for the table. So I hadn’t missed anything, and the new CEO was not there yet. Guess I’ll get to sit next to her. And look like the ass kisser.

I sat down and was getting acclimated when I pulled my phone out of my pocket and something fell out. It was a pair of panties. As I reached down to pick them up I saw someone pulling out the chair next to me to sit down. 

It was the new CEO. I grabbed the panties and tried to hide them in my fist. And then sneak them back into my pocket. 

She didn’t see them, did she?

The new CEO is beautiful. No, not beautiful. She is cute. In a very sexy-cute way.

She is about 5’2″ with large breasts, full Cs or Ds, and great curves. She is very fit, but not skinny. And has a face that looks much younger than her age of 42. Round face. Big eyes. Clear skin with no wrinkles.

She was wearing jeans and a tight v-neck t-shirt. We usually dress casually for the first night dinner. But I didn’t have time to change so I was the only one still in a suit. I made an excuse about seeing an old friend between work and dinner.

Then the texts from my new friend started coming.

“Did you like the gift in your pocket?”

“Are they still wet?”

“How do they smell?”

“I am at dinner with clients and I am dripping down my legs.”

I was so turned on. And I realized I had yet to smell them. So I excused myself to the restroom to have a quick whiff. 

That was a mistake. They were still wet. And smelled and tasted amazing. I wanted to jerk off right there. But she told me not to.

Then she texted a photo of her wet finger. 

Wow. This evening had really had a quick turn from the strike out I thought it was going to be.

The texts above and similar came throughout the evening, which included Top Golf and then karaoke with coworkers. 

I got back to my hotel around 1. I sent my new friend a text telling her I was sucking her panties and loved her taste.

She FaceTimed me and told me show her me stroking myself with her panties.

She took charge and directed me. Harder, faster, slower, softer. She heard my breathing get faster and louder and then told me to stop. 

Her camera only pointed at her face. I’d still never seen her naked. And then she came. Her face looked so sexy and she came over and over. I swear was covering her now reddened face.

She then told me to remember not to cum until tomorrow. 

“Remember,’ she added, “You said you don’t require reciprocation, so we’ll see if you even get to cum tomorrow.” 

The next morning I slept until my alarm and was rushing all morning. About 10 a.m. a work “crisis” came up back in my home state. 

There was no choice. I had to head back right away.

I let her know as soon as I could. I don’t know if she believed me or just thought I was backing out.

When I got on the plane she told me to go to the bathroom and to jerk off and cum into her panties and send me a picture of her cum filled panties. 

I did as she asked. I came so much. 

I’ve never even tasted cum, but had she asked, I would have sucked her panties clean right then. But she didn’t. 

I never saw her again. Our schedules just never lined up.

She told me later how she was so worked up that on the night I bailed, she fucked a 30-year-old guy who worked for her and rode his face while thinking of me.

We swapped texts, etc. for a few months. But it just kind of fizzled away. 

That has to be one of the hottest experiences I ever had. And I never even got to cum with her. 

Maybe I’ll tell the story about the new CEO one day. It is not as good as this one, but still fun.

 

I 

Source: reddit.com/r/eroticliterature/comments/o04ymq/i_almost_cheated