I'm going to skip ahead in my timeline with Darcy. After we started dating, I learned a lot more about her past: hookups, breakups, and other dirty details. You can read about some of that in my earlier posts, but I want to get into the real cuckolding that she put me through.
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After her humiliating me with Daniel, and my quiet revenge with Mona, Darcy and I actually went steady for a while with no real issues. The sex was good, the dates were fun, and we had a good school year together. But, it was her last year in college. She graduated and moved to the San Francisco / Silicon Valley area to look for work. We decided to do long distance while I finished my degree. Big mistake.
Darcy got a job as an executive assistant at a successful mid-size company. Her duties were basically to run around and make life easier for the CEO, COO, CFO, etc. Scheduling meetings, managing schedules, and meeting managers. I was already a little bit worried about this, because Darcy had a thing for slightly older men with money or in positions of authority. That's what had drawn her to Daniel, and it was something she would mention on occasion. We even tried some role-play to satisfy that urge for her, but I was still worried that her being bossed around by the C-suite would lead to her sending signals and one of them making a move on her. Turned out I was right to be worried.
During the summer after she graduated and got the job, I stayed with her and would drive her to work in the mornings. She often dressed like an "office siren," but the workplace also allowed more casual dress. At one point she got in trouble with HR for wearing leggings. She seemed confused, because other women in the office wore leggings with no issues, but this is when I realized trouble was coming. Darcy had a sexy little body and really nice ass, and I realized men were staring. That's the only reason there would be an HR issue with her and not others. I told her this, but she brushed it off. This was a pattern with her. She would be flirtatious with other people, give those subtle slutty cues that let men know when a woman is open to them, but when I would point it out she would act innocent and clueless. I still don't know whether she was lying, or whether her inviting behavior was subconscious. Maybe it was somewhere in between.
My suspicions were confirmed though. At one point I went to a work event with her, and watched as multiple men from her office tried to chat her up. One of them was clearly flirting with her even though I was standing right there. To make things worse, this particular guy did actually end up having sex with her much later on, but I'll get to that another time.
First, I have to focus on what happened between her and one of the executives she worked for. This guy was clearly into her. She would talk about how nice he was to her, how he would look at her, and how he would request her help with things more and more often. They got along well. He was about 10-15 years older than her, married, but obviously had a crush. I could see it in the way they greeted each other at that work event I mentioned earlier. Over the course of the year, I could tell they were getting closer from the way she would talk about work over the phone. He was slowly requesting her services more and more, relying on her more than the other execs. From the way she spoke about it, I could tell she was attracted to his status at the company. She clearly enjoyed the attention. I became even more suspicious when he got her some expensive gifts during office holiday events.
Eventually he made his move. She must have been sending him strong signals for him to do something so bold, because he took a pretty big professional risk to try it.
The company was holding a meeting between higher ups at the West Coast and East Coast offices. So, this exec and a few other employees flew out to New York for a week. He had come to rely on Darcy a lot, so he decided to bring her with him.
I was already pretty stressed about this, so imagine my horror when she told me, after having been there for 3 days already, that he had her staying in his hotel room.
She called me one night and explained the situation. She had been out drinking with coworkers, but during our long distance relationship she still called me almost every night. She finally confessed that she had been staying in her boss's room, and that her coworkers had been gossiping about it. She told me "he wants to have sex with me, I can tell he wants to have sex with me, we're in the same room and the executives are supposed to have their own room. He even invited me to his bed but I said no, I have a boyfriend." Something in her voice told me she really wanted to fuck him, though.
I don't know what came over me. I felt so sick and upset, but something deep in my gut was awakening, and telling me I wanted this more badly than anything. I just blurted out. "Do it. If you want to just do it."
She took a long pause, then she half laughed and half moaned, loud, into the phone. She just said "you are perfect for me." Before hanging up. I didn't sleep at all that night. I was so turned on, so confused, frustrated, excited.
The next day, she told me that on that night she had accepted his invitation and crawled into his bed. He touched her with shaking hands, and she went down under the covers, undid his pants, and sucked his cock. I could never cum from blowjobs, so she rarely went down on me, but he had cum fast and hard in her mouth. I was too stunned to speak or ask many questions. I just kept repeating "holy shit." I finally asked, "will you do more?" And she just reminded me that there was one more night of the trip.
When she got on her flight back, I drove all the way over to SF to see her and stay for the weekend. We could barely hold ourselves together when we saw each other again. Once we were alone, we started passionately kissing and undressing, and I asked her what had happened.
On the last night of the trip, the executive had her come into his bed again, and this time they had sex. He put on a condom (clearly he had planned this) and fucked her doggy style, pulling her hair, slapping and grabbing her ass, fondling her tits, and pushing her face down into the mattress. Eventually he was close to cumming and she flipped over on her back. She said he had fucked her desperately until he pulled out, tore off the condom, and came all over her stomach.
She told me that she hadn't cum with him, and felt so pent up that she had been squirming all through her flight and our drive back from the airport.
I ate her out until she came hard, legs quaking and gasping for air, then I fucked her hard in missionary, but I was so turned on by her story that I came in just a minute or two.
It was after this that I realized I was a cuck, even though I didn't know the word for it yet. After this experience, it opened us both up to so much more, which I'll get to in future stories. To this day, stories about women sleeping with their bosses are a huge turn on for me, because it makes me remember this time with Darcy.
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