The Charlie Saga, Part 1: cheating, fucking my boss, and enjoying a BBC [M/F]

I think I'm finally ready to tell this story. Please note that I will tell it without embellishment, and if any parts seem fake it's because real life is often crazier than fiction. I'm 5'7", a brunette, and at the time of this story was a normal weight but not thin, with a nice ass and tits and a cute face.

I was 18 at the time. I had just started a few months prior at a job with the state government. My job was acting as an aide and "living for a living", as I liked to describe it. Getting paid to lounge around a house, cook, clean, etc., which left the staff with a lot of downtime.

I had two bosses: one assistant "supervisor", who was technically above me, and one real supervisor. This story takes place with the assistant, so he was "a supervisor" but not necessarily "THE supervisor" — more like a coworker than a boss, but it was still forbidden because he was in a position of power.

Charlie had been out on sick leave for three months following a serious health disorder. Coincidentally, I started working there right as he went out on leave. So when we first met I already had the job down and there was little-to-no "supervising" that needed doing on his part.

We worked Saturdays together. It was relaxing work and we often had time to sit on the couch watching TV and chatting.

He asked me the usual questions, such as: "Wow, how old are you?"

"18. But I graduated high school a year and a half ago, so it's not like I'm fresh out of school."

"That's insane," he told me. "I wish I started working here that young, although I was pretty fucked up at 18 and you are clearly more mature than I was."

Everybody told me that. It was nothing new. I was the youngest person the agency had hired in over a decade, so this was the usual chitchat.

As the months went on, our conversations grew deeper and more philosophical. We started talking about our dreams and life goals and random shit like the books we were reading or the TV shows we were watching. It was intellectually stimulating and it was soon the highlight of my workweek.

I started mentioning my significant other but didn't know how to bring up that it was an open relationship without misjudging the situation and getting slammed with a sexual harassment suit or something, or at least that's the insane worry that held me back in my mind. Mostly I was fishing; by mentioning that I had a significant other I was hoping that he would speak up if he was also in a relationship. He did not, so I figured I had the green light.

Charlie was a very private person and no one seemed to know much of anything about him; everyone was surprised to see us getting along so well and having actual discussions, so I took this to mean that he, too, was genuinely enjoying our long talks. He had this very intense look in his eyes when he spoke, to me in particular it seemed. I rarely backed down from a challenge and the way he held my direct gaze sent tingles down my spine; regardless of what topic we were outwardly discussing it seemed there was always an internal exchange of thoughts via that eye contact.

I don't remember exactly how it started except Charlie began playfully touching my thigh when we talked and jokingly holding my hand in front of our "individuals" — actions so bold that I was having a hard time distinguishing between friendliness and the ulterior motive I was beginning to think was there.

I started really looking at Charlie. He was black, with long dreads that somehow made his face look attractive and feminine, broad shoulders that were hidden mostly by the baggy sweatshirts he wore to work. I had never been attracted to a black man before, but I also had never really gotten to know one since I came from predominantly-white suburbia. His age was impossible to guess — anywhere between 25 and 40, since black men don't really age. I decided to ask him: 34, he had said, a little less confident than usual.

I remember saying to my best friend at the time: "So, I think my sort-of-boss might be flirting with me…" and wondering how to distinguish between friendliness and flirtiness. I decided to start tracking the indicators of interest to get a more objective viewpoint, such as "today he put his arm around me jokingly but held eye contact and smiled afterward".

It all came to a head when I volunteered for an evening shift when I knew he was already working. We did our jobs swiftly early on in the evening so we would have more time to talk. And after our individuals went to bed Charlie made his move, pulling me closer on the couch so that we were cuddling before turning his head towards me and kissing me, soft and exploring.

On my end there were fireworks. Months of tension, second-guessing myself, and that damn intense eye contact had me thinking about this for so long that I could hardly believe it was really happening. I decided to just run with it, not getting hung up on the work aspect or him being my kind-of-boss or whatever.

"Wow," I told him. "I don't know why it took me so long to believe you were actually flirting with me."

He laughed but grew serious. "You had me really concerned for a while there since you weren't exactly returning my advances, just not rejecting them."

"Well, they were so obvious I started to question my sanity! Like holding my hand in front of the individuals? Holy shit, your boldness had me too terrified to make a move of my own. I'm usually much more direct."

I straddled him on the couch to make my point, feeling the rock hard erection through his baggy track-pants that were part of his usual work outfit. I stared deeply into Charlie's eyes before kissing him, letting my tongue swirl over his lips and enter his mouth. I began to kiss and lick his neck, sucking on his earlobes and biting his shoulder gently. The way Charlie was moaning was turning me on, and he responded by letting his hands roam freely under my shirt, over my back and stomach and coming to rest on my bra strap, which he quickly undid. I removed my bra and threw it next to us on the couch before laughing a little at the absurdity of it all.

Charlie only smiled before playing with my breasts, pinching my nipples and leaning over to lick them. I began to caress his stomach under his shirt — I could feel his abs well though they weren't visibly defined — and up to his broad chest, letting my fingers play over his nipples and down his muscular arms that had been oh-so-hidden by his outfits.

"I feel like a teenager again," Charlie told me. "Making out on a couch hasn't gotten me this turned on in longer than I'd like to admit." I agreed, telling him of the fireworks his touch was setting off all over my body.

He pushed his hips upward, letting his dick rub my slit through his pants and my jeans. The stereotypes were clearly true, at least in Charlie's case; I reached into his pants and underwear and gasped when I felt the thickness and length of his dick. My fingers couldn't even wrap 3/4 around the shaft and it was longer than the two hands I used to grip it. I tried not to seem too impressed though — he must get that all the time, and I didn't want to seem "young" or "inexperienced" — and just allowed myself to enjoy it for what it was: a beautiful, fully erect dick, with the unique shape that only black guys had.

I sighed, gripping his cock harder and listening intently for any sounds in the house. I started to become more aware of my surroundings, perhaps a little downright paranoid, remembering once again that we were at work.

"Fuck," I exclaimed, "I wish we weren't at work right now. I want you inside of me so badly."

He moaned and kissed me again, letting his fingers move into the waistband of my jeans. I unbuckled them and he moved his fingertips down into my underwear, caressing my slit and beginning to rub my already-engorged clit. My self-control was waning; the more he played with my clit, the more I began to lose any sense of being. I was riding a high I hadn't felt since I first started experimenting with sex. The forbidden desire mixed with absolute lust.

My brain was mush. Our supervisor could have walked in right then and there and I would have had no idea. I let myself moan into Charlie, sitting back on the couch to allow better access for his fingers but still tightly gripping his dick. I could feel the head beginning to drip precum… it was slippery and turned me on in a very primal way. I was about to lose my mind and either slip his cock into me or need to stop altogether.

In fear for my job, I did the latter. I sighed, moved Charlie's hands back to his lap, turned myself so that I was no longer straddling him, and cuddled up to his side.

"I want to fuck you so bad," I whispered. "And if I don't stop now I seriously will."

"And?" he asked, his eyes fuzzy and glazed over from desire.

"And we're at work!"

"Right." Charlie shook himself a bit, trying to clear his thoughts. "Oh fuck, you're totally right. I really got carried away there…"

"Also, how is it 8:45 already?! God, you leave in 15 minutes? Fuck, I wish we could just do this forever."

I suddenly laughed, looking down at our partially unclothed bodies and began to put on my bra again. I zipped my jeans and adjusted my clothes to look mostly normal, though perhaps a bit disheveled.

Charlie kissed me once more before putting away his cock and pulling up his pants. He stood up to adjust and I laughed at the huge tent his erect dick was making before he tucked it into his waistband.

We cuddled until it was time for him to leave, talking things over a bit. Charlie pulled me up by my hands, hugged me, and kissed me goodbye. I had to stand on my tip-toes because he was at least 6'2". I never seemed to notice his height before but it was so evident now that we were kissing.

Later that night I decided to stalk him on FB. I typed in his name, scrolled along until I saw his picture. I was captivated by his eyes even in photos, staring at his dreads and smile before I noticed the small mixed-race child sitting on his lap in the profile photo.

I gasped. Fuck, was that his kid!?

I continued to stalk his profile. Photos sitting next to this woman — pale white, dirty blond, a little curvy. I clicked the tag and it brought me to Nadine's profile, which said "in a relationship with Charlie".

Fuck fuck fuck. My heart sank right into my stomach. He had a child with this woman, whoever she was! And he had literally never mentioned her.

I pushed the jealousy and betrayal out of my brain — dude, I already had a SO of my own, it was simply irrational — and went about my week like usual.

My significant other, Aaron, sat me down for a talk the next time I saw him where he decided that we should close the relationship. I protested — but it had been going so well! and we never would have gotten together if we were going to be monogamous! and wtf, the timing!

He couldn't know about Charlie yet, could he? I was right about to bring it up after weeks of telling him about my flirty coworker — which he only encouraged, but I neglected to mention that the coworker in question was also my boss.

Do I dare tell him how about my new workplace romance? My SO would tell me I was being reckless with my job and that I should stop. And now that he wanted it closed I couldn't exactly tell him, could I? And with the new information I had — he was taken, with a kid — it all just seemed more ridiculous to pursue.

I decided not to tell Aaron any of this. I told him I thought we should remain open long-term but that we could close the relationship for now — temporarily! — to remain on the same page. And I would figure out what to do about Charlie another day.

The next time I had Charlie alone at work, I told him of my discovery. "Sooo, I was on Facebook, and I typed in your name, and, well, are you still with Nadine? Is it an open kind of deal or are you two separated or…?" I trailed off.

Charlie looked shocked. "Shit." He took a deep breath. "Yes, I'm still with Nadine. And no, it's not open."

Fuck fuck fuck. "And you two have a kid together?"

"Yeah. Zack is 5 now." He was matter-of-fact, not elaborating on any of this. So unlike him.

Ew. I tried not to picture his child. I pressed on. "And I assume she doesn't know about me."

"No. And I'd like to keep it that way."

"Understandable," I said.

"What about Aaron? You kept mentioning him…" He looked uncertain.

I sighed. "Yeah, Aaron and I had an open relationship until a couple days ago. Now I don't know where any of this stands. Fucking bad timing."

"Whoa, an open relationship? That's pretty cool. But I'm sorry to hear that. Life is complicated, huh?"

These revelations led to us just cuddling for a few shifts. We'd cuddle and talk about life and it was good.

I brought up an app that cheaters use to disguise their conversations, since we couldn't exactly text each other now that we both were cheating on our significant others. He quickly added it, smiling. We talked about our boundaries — we would never, ever tell our spouses, and we simply would never slip up or be stupid about this. No flirting in front of coworkers or the boss. Most days we would chat on the app late into the night, and I eventually brought up the possibility of meeting outside of work.

"But where?" he typed. "I live with Nadine, so that is a no-go. And you and Aaron live with your parents."

He asked his best friend if we could fuck at his house. His best friend said no for a bizarre reason: he, the friend, had yet to fuck anybody in his own house yet, so it was weird for him. Whatever. Such a bastard. My friends were all in college and didn't have their own apartments, and they all knew Aaron so I couldn't risk anyone telling him anyway.

I had an idea. "So my family has this lake house…," I responded. We set up the details. I would tell Aaron and my parents that I was meeting an out-of-state friend for the night up at the lake house. Aaron did not like this friend so he did not ask to join in. He wished me a good night and kissed me goodbye.

I felt guilty already.

I'm going to be horrible and stop here because this is cathartic for me, and if there's no interest in reading the rest I can continue it privately. But please feel free to comment with any similar experiences, or call me a horrible person, or give me critiques, or point out typos (I'm writing this on my phone), or whatever. Life has been a wild ride and now that enough time has passed I would like to start sharing my stories with you all. If it's well-received I'll post part 2 tomorrow.

Source: reddit.com/r/gonewildstories/comments/3gbco1/the_charlie_saga_part_1_cheating_fucking_my_boss