The Charlie Saga, Part 2: cheating, fucking my boss, and enjoying a BBC [M/F] | 2016

Thanks for the positive feedback, you guys. The subject matter just had me a little worried about backlash. I've been reading this sub for years and have seen a wide range of reactions to certain controversial topics. Part 1 can be found here. Enjoy part 2.

We had arranged to meet at a plaza near the lake house at 5PM to carpool. Charlie told his family that he would be attending an annual work party that evening, and I had told Aaron that I was meeting an out-of-state friend up at the lake house. I tried to be as truthful as possible so that he would be none the wiser.

I had spent at least an hour preparing myself at home. I shaved everywhere, put on a heavy layer of makeup that I'd never have worn to work (as Charlie had previously commented that he liked the makeup look, and I wanted to appear differently than he normally saw me), and found the perfect outfit that showed off my ass and tits without being too revealing for the chilly weather of March. Afterward I kissed Aaron goodbye and told him honestly that I loved him. He wished me a good night with my friend and told me he'd miss me. Ouch, I thought. The exchange stung, but I couldn't bring myself to call it off now.

I found Charlie's car and parked next to it. We both got out and nervously sized up the other person. Charlie was wearing reasonably tight jeans, which were far different and more attractive than his usual track pants. And rather than a baggy sweatshirt he was wearing this black sleeveless undershirt with a classy long-sleeved button-down over top -- most likely also taking the weather into account.

I smiled and hugged him. Holding me close, Charlie grabbed my ass and whispered in my ear, "You look so sexy." I responded in kind, running my hands under his shirt and up his back and over his abs. Mmm. I could feel his hard-on twitch against my stomach, and I kissed him softly.

We took my car so that the neighbors would recognize it and find nothing unusual about our visit. I couldn't resist groping Charlie's crotch a little bit on the ride there, but mostly we just held hands, smiling the whole ride. When we finally arrived I gave Charlie the tour, showing off the huge porch, the seven different beds, the majestic lofted upstairs. The nights of March were still below freezing so we set our things down in the bedroom nearest to the fireplace and plugged in the space heater.

Quickly Charlie helped me start the fire and get it roaring, but by then my hands were already freezing cold. Pulling Charlie close to me by his belt loops, I smiled devilishly and ran my chilly fingers under his shirt and over his nipples. He let out a gasp-moan as I felt his cock quickly become hard against my stomach. It was on.

Suddenly remembering the true reason we were there, we wasted no time undressing. The sleeveless black undershirt showed off Charlie's chest and arms handsomely, and I couldn't help but run my hands all over his muscles. I had an appreciation for his broad-shouldered ~6'3" frame, noticing the difference between my usual skinny white boys and this sculpted black man in front of me. I ran my hands down over his taut ass and thickly muscled thighs before finally coming to rest on his huge, black cock. Fuck yes.

I was down to only my lacy panties and Charlie had been running his hands over my tits and ass. He was staring lustfully in appreciation, alternatively pinching my erect nipples and squeezing my ass cheeks.

I could feel his cock pulse and couldn't resist the urge to squat down and begin licking and squeezing his shaft, swirling my tongue around his glans before sliding my mouth over his dick. I had deep throated big cocks down to the balls before, but the shape of his thick black member only allowed me to swallow as far down as the back of my throat would allow. Amazingly there was still a third of his shaft left and I quickly wrapped my hand as far around the base as it would go, which was maybe 3/4 of the thickness. In comparison, my fingers perfectly wrap around my wrist which is 6" in circumference, so Charlie's dick had to be at least 7.5" in circumference. Holy fuck, I was amazed and excited. I considered the length and knew Aaron's dick to be 7", as I had measured it myself; extrapolating from that, Charlie's had to be around 8.5" long.

I sloppily bobbed my head up and down his cock, gripping and sliding my hand along the base. Charlie moaned; I found his deep baritone voice to be incredibly sexy. His precum was mixing with my saliva and forming a perfect slipperiness. After about 5 minutes Charlie pulled me up and onto the twin bed for better access. I continued to suck through various position changes, telling Charlie to straddle my face and fuck my throat -- which he scrambled to get in position for before thrusting in and out of my mouth fervently. After a few minutes I flipped us over and sat over his chest with my ass in his face so that the upward curve of his dick would slide down my throat better. I licked his balls and taint occasionally for variety and giggled a little at his higher-pitched moans. Finally I had an idea and ordered him to stand up while I hung my head off the bed, determined to try any position to be able to deepthroat him fully. Alas, it seemed there was a physical limitation in the way: the circumference of my throat was just smaller than that of his dick.

However, I was determined to make him orgasm through oral first and resumed the original blowjob position on the bed, with Charlie on his back and me on my knees in front of him. I quickened my pace and used both hands to slide up and down the base of his dick at the same time as my mouth. I wriggled my tongue over the head of his glans as he slid in and out between my lips. I knew Charlie was growing closer judging by his frequent moans, and his hands came to rest on my head for added pressure.

"If you keep this up," he managed to say breathily, "I'm going to cum."

I looked up at his euphoric expression and continued on, confident that this was only the first round of the evening. I could feel his legs squeeze against my body, his hands clench my hair, and he suddenly let out spurts of cum in my mouth and down my throat. I swallowed gleefully, still jerking his cock and tonguing the head through completion.

Charlie sighed happily. He pulled me up so that I was laying on top of him. "That was amazing," he cooed. "I can't believe you were able to finish me off with oral. It's been years since someone did that."

That was my first clue that Charlie's sex life wasn't exactly satisfying. Years? I gave Aaron a blowjob nearly every day because I loved doing it. The idea of being with someone for years and rarely if ever blowing them to completion was foreign to me. And with a cock like that, how could you resist?

We laid there cuddling for another 40 minutes or so, enjoying the skin-to-skin contact and having some deep discussions about our own fears and desires. Charlie requested that we leave the lights off because he felt more comfortable talking about such intimate matters in the dark, without my "piercing gaze". I thought it was funny because he was usually the one who initiated such intense eye contact; I just usually didn't back down from the challenge.

The darkness carried our voices, as if we were only our brains and bodies and the outside world didn't exist any longer. The silences were comfortable, cuddled up against one another's skin.

But finally Charlie had something serious he wanted to discuss.

"I am accustomed to having casual sex, though it's been a long time," he started. "But this is... different. The sex feels different. I don't consider this casual. I feel things for you that I shouldn't. And I wanted to know..."

"... if I felt the same way?" I finished.

"I suppose that's it."

"Charlie," I started, "that's a complicated answer."

"Okay."

I sighed. "Yes. I feel things for you. But I don't want to love you -- I don't want to be in love with someone or something I can't have. I've done that before, and it's not fair to anyone involved. That kind of forbidden love is intoxicating and soul-sucking and life-ruining. I don't want to break your heart, and I don't want my own heart broken." I paused. "That being said, yes. You're certainly more than just a friend to me, more than just a fuckbuddy or a no-strings-attached relationship. I think about you a lot, and I care about you, and I don't mind emotionally blurring certain lines, but the one line I won't cross is actively being in love with you."

I couldn't see his expression so I didn't know how he took this confession. After some more back-and-forth, Charlie seemed... a little disappointed maybe? confused? off-put? While he understood intellectually he couldn't wade through those waters emotionally.

But he seemed satisfied overall by my response, and he hugged me tight to him. I kissed him hard, realizing what a betrayal I just admitted aloud. I have feelings for someone else, I thought, the worst betrayal possible to Aaron.

I kissed Charlie hard, and he pulled down my panties finally. I took them off and kicked them towards somewhere in the room. At last, we were fully naked.

I decided to blow Charlie a little to get him fully hard as I was curious about how his somewhat-flaccid cock would feel. As it turned out, his unerect dick was the size of an average penis and merely lacked the rock hard intensity it normally had. But within a minute he was roaring back to life and moaning all over again.

He ran his fingers over my smooth vulva and started to play with my clit. "I can't wait to finally be inside of you," he whispered, despite there being no one else in the house. He slipped one finger inside of my pussy, then two, sliding in and out slowly and teasingly.

I couldn't take it anymore. But I had an urgent question that I had been putting off.

"Do you have anything?" I asked nervously.

"In my pants pocket." I could feel him point to the other room where his pants lay on the floor.

I laughed at my bad phrasing. "No, not a condom, I mean... STDs. Are you clean? Were you tested recently? I get tested really often so I'm definitely clean, and I'm on continuous birth control so there's no risk of pregnancy..." I trailed off.

This was ruining the mood a little, I could tell. I meant to bring it up sooner once I discovered how big his cock was. I understood condom sizing and I knew that condoms in the US had a max circumference that was way, way smaller than his dick, so it would basically make sex impossible if he wore one. Unless he ordered some from Europe, anyway.

He smiled. "I'm clean. It's been a while since I was tested but I've been exclusively with Nadine for so many years that it hasn't really been necessary. And I really hate condoms, but I'll use one if you want me to."

I had specific worries, such as herpes -- since doctors usually don't test for it. But I know that the stigma of herpes is usually worse than the infection itself. Still, Aaron was terrified of catching it, so we had agreed to always use condoms with other partners. Except that I found myself saying:

"I just want to feel you. No condom in the way. I trust you."

No, no. This -- this was the ultimate betrayal, it felt like. But, it was done.

And with that Charlie flipped us over so that he was on top of me in missionary. I wrapped my legs around his back, kissing him. He grabbed his huge cock and rubbed it along my slit, teasing me -- or himself, perhaps. But finally, after months of anticipation, he pushed into me.

I had two realizations at once: 1) Black dicks felt different. They had a shape and smoothness unique to themselves. Porn stereotypes were right about something after all. 2) Fuck, Charlie was thick. He was stretching me out in all the right ways as he eased into me, eventually bottoming out before pulling out and sliding back into me. It took me a while to adjust to his size, and I knew that I was probably bleeding despite having sex a hundred times before and also being incredibly wet, but I loved the mixture of pleasure and pain. I moaned, pulling him closer and deeper by squeezing my legs tighter around his back; I used my nails to scratch his back lightly.

He moaned, all deep and guttural, and then he grunted the single hottest thing I've ever heard during sex using his deep baritone black man's voice: "Oh, you feel good, baby." I literally blushed and could feel my clit pulse. It wasn't so much what he said (although no one had ever called me 'baby' before) but how he said it. I don't know what it was about that line, but the auditory memory has gotten me off for years since. I wish I had it recorded.

Anyway, he began to fuck me harder and faster, really slamming deep into my pussy, and then he was cumming I think because I could feel his dick pulsating inside of me, but he didn't stop and his dick remained just as big and still hard. He slowed for a little while and I found myself tightening my pussy around his cock, just to hear his reaction.

"You're so tight," he told me, between moans. "Fuck, your pussy feels so good."

My desire to remain nonchalant about his size had mostly faded away in the heat of the moment, and I found myself saying: "Your cock feels amazing. So big and thick...."

I began to kiss and suckle on his collarbone while simultaneously teasing and pinching his nipples with my fingertips. His dick would twitch at each pinch. It was glorious.

Since we had been fucking for almost a half hour, I could tell that Charlie was growing tired from holding himself up and thrusting for so long. I flipped us over and started to ride his dick, leaning forward so that my arms were propped up on his chest. I used my thumbs to pinch his nipples a little while I squeezed my pussy on his thick cock. Up, squeeze; down, squeeze.

I was enjoying myself but the soreness was catching up with me. My pussy, previously soaking wet, was now feeling the friction. Charlie sensed this and flipped us over again so that he could speed up and cum more quickly. I tried to focus on the idea of being filled up with Charlie's cum, letting it continue to turn me on despite the pain. A couple minutes later he was moaning and his dick began to pulse, and I knew now how dry I really had been because his semen added a significant amount of moisture.

We stayed together panting for a few minutes before he pulled out of me. I was finally feeling the soreness now that the sex endorphins had mostly worn off. I felt swollen and dry. It was worse than losing my virginity had ever been, which sort of amused me.

"So, boss, did you enjoy yourself?" I joked, referencing the awkward work situation where he would still be my supervisor when we got back. We had officially broken company policy.

He smiled, then grimaced. "Oh god, I had totally forgotten about that place. Please don't remind me. But it will be interesting for sure. And yes, it was... pure hedonism."

I knew then there was no going back. I had cheated. I could never tell Aaron about this amazing sexual experience, despite being so used to sharing those sorts of things with him. It was now a secret to take to my grave.

We tried to have a round three a little while later but I was too dry and sore for Charlie's dick to enter me, so we just sort of agreed that we had had enough for the night. I was mentally kicking myself for not bringing lube. That didn't stop us from cuddling naked for as long as possible, until our conversation ceased and we fell asleep.

I did see a little bit of blood on the sheets later, and I was sore and swollen for days... but it was worth it. To me, at least.

We continued fucking occasionally for a few years. Having regular exploits outside of work actually made us more productive and less easily distracted by the slightest hint of sexuality.

Eventually Aaron decided that he should be allowed to do whatever he wanted with other people but that I should still be monogamous. We were a near-perfect couple other than that, with our lives tied up together, so I (perhaps stupidly) stayed with him. To balance out the unevenness, I continued to fuck other people behind his back. Thankfully he never found out. I may wind up writing about some of those other side-exploits soon.