Confessions of a Retail Manager [MF] [cheating]

It all started in Dallas.

We were both managers for a very popular retail chain, and we were at the annual company-wide conference. While her store and mine were very close, we never really talked outside of the occasional district meeting. I had noticed her, though.

Anna was about 5 feet 4 inches, with straight blonde hair and an attractive face. What really caught my attention was her breasts. To say she was “blessed” would be an insult to blessings. They were huge (I would come to find out she was a 44J). The rest of her body was attractive as well, but it was hard to look past her enormous chest. As a breast-man myself, I would often find myself inadvertently staring, across the meeting table, watching the buttons on her shirt straining to keep her chest contained. At least I was never caught doing so, and I would be able to look away before embarrassing myself.

She was also married. I knew little about her husband except that he was overbearing, and members of her staff had come to me to vent about the frequent arguments she would get in over the phone with him. I didn’t know how to handle that – I didn’t want her to get in trouble so I didn’t report it up the chain, and I didn’t know her well enough to call her directly. I figured I would wait until Dallas, which was only a few weeks after the most recent complaint, and be able to talk to her one to one in a more relaxed setting.

One of the first nights in the conference, all the members of our district went to the hotel bar once the official business ended. There wasn’t much to do near the conference center, so unless we wanted to retire early, or find a taxi in to town, the hotel bar was our best bet. All of us were enjoying our night, and after a few rounds some of the younger members of the team retired, leaving only a handful of us “professional” drinkers. I found myself next to Anna, sitting beside her in the booth, crushed in by one of my colleagues on the opposite side. The way she was sitting, I could feel the tender flesh of her breast pressing in against my arm. It seemed that every time I moved to lessen the pressure, she would shift to put it right back. It was highly distracting, so, not wanting to break any sort of protocol, I decided to keep the conversation professional.

“You know,” I started, slightly hazy from alcohol, “some of your staff have come to me in confidence.”

“Yeah?” she said, seeming much more sober than I was, “What about?”

“They say you fight with your husband on the phone, and even when you’re in the back room, they can over hear. It makes them uncomfortable, but they don’t know how to tell you.”

She looked a little embarrassed, her finger moving to toy with her wedding ring. “Yeah,” she said with a sigh, “Tom and I have been fighting a lot. He’s been away on business a lot, but he’s so controlling, he calls me about every little thing. If I’m at work ten minutes later than I’m scheduled, he starts calling, wondering where I am. He keeps reading my email too, asking all kinds of questions about who a person is or how I know them. It’s infuriating.”

I nodded, trying to be a sympathetic ear. I could see she was in pain, but at the same time, she kept moving against me, pressing herself closer. I swear I thought my pants were going to rip from the strain of my erection. We spent the rest of the night talking, about our lives, about our stores, our hobbies, just getting to know one another. My eyes kept wandering to her huge breasts though, and at one point she actually said, “Hey, up here.”
I was so embarrassed. I apologize profusely, and not long after, excused myself from the conversation, returning to my room to sleep off my drunken fog before business resumed the following morning.

For the rest of the conference she and I were like best friends. We sat next to one another at every meeting and every meal, spent the evenings talking, and even found excuses to separate from the rest of the group to talk one on one. Despite all of my temptation to do so, I didn’t flirt, didn’t make any innuendos or veiled offers, and tried to keep from ogling her too much. Aside from a goodnight hug, nothing more happened during the conference, and I thought I had made a good friend in the process.

On the plane ride home, I was one of the first from my team to board, and took a window seat. As more of the group boarded and the seats started filling in, I knew it would be impossible to keep the seat beside me empty, so I just hoped it would be someone I knew. Anna sat down beside me. “This seat taken?”

“No, please,” I said, “I didn’t know you were on this flight.”

“I wasn’t, but, the morning flight out was overbooked, so I let myself get bumped to the next one.”

I was quite relieved, and even dared to get pleasantly excited when she lifted the arm rest to half-snuggle in against me once we were in the air. As we reached altitude, the hum of the engines putting most of the conference-goers to sleep, she shifted, once again pushing her soft breasts into my arm. I didn’t want to move, afraid she was also asleep, and I certainly didn’t want to wake her and ruin the moment.

“You know,” she whispered, “I’ve seen you looking. A lot.”

I let out a sigh, trying to find the words to apologize, to explain myself, to tell her I was trying, but as I hunted for the right thing to say, she slid her hand under the blanket to grab at my crotch. “I don’t mind.”

I was stunned. I couldn’t say a word as she deftly undid the button and zipper of my jeans to free my cock. Her hand tightened around it and she gave a pleased purr into my ear. “Big boy,” she whispered, and began to stroke.
I couldn’t believe this was happening. I held still trying not to call any attention to what was happening. Her hand felt amazing! She squeezed and caressed, letting her fingers glide up and down my shaft. It was all I could do to keep from moaning aloud. I know she could tell the effect she was having on me because she would giggle and quicken her pace, only to stop and squeeze any time someone walked by.

After a few minutes of this I could barely control myself. I could feel myself on the verge of exploding, my cock pulsing in her hand with every heartbeat. I let out a soft gasp, trying to hold back. She wrapped the thin blanket around me and whispered, “Can’t let you make a mess,” her lips teasing the outside edge of my ear.
It was too much, and with a sharp inhale I started to cum. She gripped the head of my cock through the blanket with her other hand, turning the thin material into a makeshift reservoir for my cum. I could feel it shooting out, her other hand pumping and milking me with expert motions. I was completely overwhelmed as I emptied, shuddering with pleasure.

She removed the blanket in one quick motion and balled it up, stuffing it into the pocket on the seatback in front of me, while I quickly adjusted my pants to hide my softening flesh from anyone who might walk by. With a contented sigh she leaned back against me. I tried to make a move, to touch her, to maybe return the favor, but she pushed my hands away, content to remain how she was.

She didn’t say anything for the rest of the flight, and when we got to the airport, she was immediately met by her husband. I watched the two of them leave the terminal, his arm around her waist. I smiled to myself, still able to feel the sensation of her hand wrapped around my erection. It was a thrill, a secret I would keep for years to come. I wasn’t sure I’d ever be able to look at her the same way again, and hoped that, in the coming months, I could maintain professionalism. Either way, it was back home, and back to real life, the brief dream-like encounter with Anna now over.

Or so I thought.

To be continued…

Source: reddit.com/r/gonewildstories/comments/6cx0ce/confessions_of_a_retail_manager_mf_cheating