Fist Time for Everything [MF] - Co-workers' first time | 2016

I'm very excited that my true story is also posted on Literotica! I posted a version here a week or so ago but this one has more detail. Enjoy, here or there! http://www.literotica.com/s/fist-time-for-everything

It's early Monday morning and I've just sat down at my desk with my coffee and bagel, and before I even open my email I get an instant message from him, "How many?" I look up from my screen across the hall to see him sitting at his desk and he's holding up 2 fingers. He raises an eyebrow then slowly sticks the other two up as well. I smile devilishly and nod my head.

He's been getting four fingers in me for a few weeks and lately he's been making comments about getting his whole hand in me. I haven't said no or indicated that I wouldn't do it, I love having his four fingers inside of me, and as I told him, I'm game to try almost anything at least once. Still, a small part of my brain wonders if that is even something my body can do?

I've been with some almost-freakishly-large men, so it wasn't the largeness of the act of fisting that concerned me, though that was certainly intimidating, it was the term. It just sounded so kinky, so dirty, just so much MORE than anything I'd done. 'Fisting' doesn't seem like something a woman should be into; it seems like an almost violent act that only extremely kinky people are into, not little 5'3" 120-pound me. It sounded severe, serious, and I considered myself pretty sexually tame, although in retrospect, I had actually been pretty adventurous in my 20s. Maybe I had just gone vanilla in the past 10 years.

It started like most of the times that he's fucked me. I go across the hall to his office and quietly close and lock the door. He's sitting in his chair, rolls backwards from his desk, and unbuttons my jeans and tugs them, and my panties, down over my hips. Honestly, I enjoy that part more than a little. My waist is considerably smaller than my hips, and my hips are part of why he's attracted to me - my ass being the main reason, but without these hips I wouldn't have such a fantastic ass. Anyway, it just feels very feminine and more than a little sexy to have a guy pulls clothes off of the most womanly area of your body.

He turns me around and almost-forcefully bends me over his desk. I actually wish he would be a little more forceful. Though he knows that I like it rough, that's not why he's being forceful, he is just showing me that he is in charge, which I definitely know, and I absolutely love.

I turn to look over my shoulder at him and he stares me right in the eyes as he licks one of his fingers and then slides it slowly into me. He's good; he hits my g-spot every time he puts his fingers in me, and I let out a little moan. He knows he is good, and not just because he pays attention to what makes me make noise, but because he aims to please. I know that sounds silly, but this guy gets off on getting me off. The control he has over me really gets his ego going, knowing what to do to send me over the edge, sometimes more than 10 times. Or, when he's feeling devious and I've been a bad girl and deserve to be punished, he'll finger me for 20 minutes and keep me on edge the whole time, just about to cum, but he won't let me. There is no doubt that he is in control and that he knows what he is doing.

Very soon he pulls out his finger and licks another, I don't require a lot of lubrication, and I take quickly to increasing size so he doesn't have to wait to start pushing more and more into me. Two fingers feels awesome. Two fingers and a mouth and tongue is probably my favorite thing, but there are so many other things that he does that feel amazing, I just let him do whatever he wants, though sometimes I do make specific requests that he fulfills without questioning. It really is a beautiful arrangement that we have, though I feel I get the most out of it.

Now he wets a third finger and this is when he starts noticeably enjoying himself. As he twists his three fingers inside me, I start breathing faster and that incites him to move them around, in, out, thrusting quickly, then slowly twisting again, then pushing deep. He frequently hits my g-spot, flicking his fingers quickly against it, and he has me close to orgasm but it's obvious that is not his goal at this moment. We both know that if he makes me cum now, there is no way he'd be able to squeeze his fist in me.

The fourth finger gets wetted and he slowly presses them all into me. Not twisting at first this time, I know he's paying attention to see if it hurts me. I'm not just pushing back on his hand because it feels really good, although, it feels REALLY good, I'm also letting him know that it doesn't hurt, that he may proceed. He then twists his hand and he pushes deliberately around all of my edges, moving around in a circle a few times. His goal is to get his whole fist in, so he is trying to stretch me out, and he's doing his job well. He's not just stretching me out, he's making it feel amazing.

I had never had four before he did it a few weeks ago, and even now, as I know what he's about to attempt, I trust him not to hurt me. And, he trusts me to tell him if something hurts or if I want him to stop. I also know my body, and anything that he has done to me that hurt, almost immediately turned to pleasure. I've never really let someone continue to do something after it has hurt, but I'm learning a lot about myself since I started messing around with this guy, I'm letting go of a lot of preconceived notions and it's exhilarating and extremely rewarding.

It was probably as much a surprise to me as it was him, that when he starting pushing his knuckles inside me, it felt incredibly good. Part of the sexy feeling was doing something new to both of us, but feeling every minute part of my hole being touched at the same time, with all of that pressure...it was an amazing sensation, and the thrill of knowing that he was about to push his whole hand into me made my mouth open as I sucked in air. I was now breathing so fast and hard that my fingers were numb but I couldn't help it, I was so enjoying these new feelings, though I made sure to gasp, "Oh my god that feels amazing!" so that he knew that I was okay, that he could proceed, and that I was very much enjoying it.

I'm bent over his desk, panting, his entire fist just having entered me and his phone starts to ring. I can't see him, but he doesn't do more than glance at the phone, I know because he continues to slowly move his hand into me and the release of pressure as his fist has entered me and is no longer stretching my outside parts is almost a let-down.

"I have my whole fist in your pussy," he whispers to me. Damn, that was sexy. I love the way he talks to me. I turn my head to look at him and the look on his face is almost looks hungry, he is so turned on at having conquered me. And being conquered by him is incredibly exciting and I enjoy being at his mercy.

He slowly turns his hand inside me and I can't help but let out a tiny, audible moan and I bite my own hand to try to stay quiet so our co-workers don't hear us. It's insanely hard because, though I can't tell exactly what it is that he's doing that feels so good, it is so good it's making my legs shake. He tells me later that he was rubbing my cervix. I had no idea that my cervix really cared about anything, but I made a mental note to check that out later when I masturbated.

Suddenly, his teeth lightly scrape my ass cheek and as I feel myself start dripping down my leg I try biting my other hand to stay quiet. It is not easy. He's now loosened me up so much that he is pulling his hand almost out of me, and then pushing it firmly back inside me and he is literally forcing the air out of my lungs and I have to put my hands over my mouth to stay quiet. It is all so intense and there is a small part of my brain that is freaked out that, "Holy crap, his whole fist is inside of me!" and the other 98% of me is thinking, "Oh my god, I can't believe this feels SO good!".

I turn my head towards him again and I see the look on his face and it is the face of a man with a rock hard cock that is insanely turned on, and that, along with the feeling of him brushing his hand past my g-spot and then turning his fist to rub and push on my cervix that makes me start cumming hard and my pussy clamps down on his hand as I have a very intense, very prolonged orgasm. I let out a squeak and bite hard on my hand and I'm leaking a lot of fluid at this point, soaking my pants that are around my ankles and it turns me on that he does this to me.

He isn't moving his hand much now, he can't, but he slowly shifts it, rotates it a little, and eventually starts to pull it out of me, and it still feels good. I am no longer biting hard into my hand but it's still next to my mouth and I look at it and laugh just a little at how many deep, red, bite marks there are.

He gets his hand free and I slowly rise off of his desk and turn around. He has his pants pulled down and his cock out of his underwear and he is so incredibly turned on it is just dripping with precum. It was all I could do to not jump on him and shove his dick in my pussy, but we hadn't actually done that yet and I was afraid he didn't want me to, and I couldn't handle that rejection.

He asked me if I was okay and all I could do was try not to fall over, and nod my head. My mouth was dry from panting, and my pants and panties were still around my ankles and soaked. He wiped his precum on his hand, licked some off, let me have the rest, and then he quickly tucked himself back into his underwear, pulled up his pants, then bent over to pull up my panties, the shock of the cold wetness making me jump a little. Then we yanked my wet pants over my hips and I jammed my mouth on his, hungrily kissing him.

What I'd just experienced was a first for both of us, but the kiss wasn't romantic or passionate for any other reason except that what we had just done was insanely hot and I was feeling high as a kite. I do not doubt that the sexual high after having an amazing orgasm (or many of them) is addicting. For me it is absolutely euphoric, but I got myself together, unlocked and opened his door, and walked across the hall to my own office.

I ran out of paper towels trying to soak up all of the cum from my jeans, but it was certainly worth it. At one point I had to make a mad dash to the kitchen for more, and it was a good thing that I did because he had his fist in me twice more that day.

I'm not necessarily a glutton for punishment, but I am absolutely a glutton for orgasms. This guy is so good to me, and he's conveniently located across the hall from me. I am a weak woman when it comes to getting something I want, so how could I not abuse that privilege? Also, it doesn't hurt that he is gorgeous. Tall, dark hair, fit but not a gym-rat, and his eyes...chocolate brown, and it is crystal clear when he is happy, horny, kinky, submissive, or my least favorite, completely numb. I'm not the romantic type, I don't fawn over anything and I don't usually go on about someone's eyes, but this guy gives me one glance and I can almost tell how many orgasms I'll have that day.

The second time he fisted me that day was in my office and, because I had told him I couldn't see the look on his face while he was fucking me, this time I sat in my chair facing him. He knelt on the floor in front of me and this time started with 2 fingers in me and his mouth on my clit. Jeez, it's like he's read my mind.

I run my fingers through his hair while he's looking up at me from between my legs, and he licks a third finger and squeezes it in me. It's terribly hard to keep from moaning or telling him how good it feels when he curls his fingers upward to rub my g-spot as he's sucking on my clit but there are people on either side of my office and I have to be quiet. I've already cum once today but it wasn't from having my clit stimulated and his tongue on me feels electric. He was still sucking on my clit when he slid his fourth finger into me and that stretched out feeling along with the orgasm building from his tongue on me sent me over the edge and I pushed his face between my legs harder as I came.

He didn't pull his hand out but kept his four fingers inside of me and waited for the contraction to release it's grip on him. His hand slowly started moving again as his lips gently kissed the inside of my thighs and I let out a little moan and slumped down a little in my chair. He raised his face from between my legs and intently watched the look on mine, all the while his hand didn't stop moving and as he rolled his wrist and pushed against me from the inside.

I live for the look on his face when he knows he is making me feel fantastic from the inside out. His eyes narrow, his eyebrows furrow, sometimes there's a wicked smile on his face, sometimes he looks almost wild-eyed and angry, though he's just determined to give me a wild ride and turn me into a wet, sloppy mess. Now, his face is phasing through a coy look, as he flicks his fingertips on my g-spot, then an aggressive look as he pushes his fist deep inside me, then, in the space of an inch, moving his fist in a rapid punch. When my mouth drops open at that feeling, his mouth opens slightly, almost mocking me but more-so mimicking my enjoyment, imitating the pleasure. He is so turned on that he has this power over me, and that I will let him do this to me, something he's never done to a woman before today.

At this point, looking him in the eye and feeling so high from the repeated orgasms, wanting nothing except more of whatever he would give me, I couldn't help but whisper to him, "More." There was no time to see the changing look in his eyes as he went from pleasuring me to fist-fucking me because he leaned towards me and wrapped his other arm around my waist, pulling me to him as he twisted his fist in me, rotating it in circles. I quickly built into another orgasm and wrapped my arms around him, clutching him desperately to me as he again brushed past and pushed against my cervix. These orgasms he was giving me with his fist inside me are different than anything I've felt before; I assume it's because I'm so full with his fist that everything squeezing it in orgasm is just reinforcing that wonderful feeling and these orgasms don't really stop, they just plateau a bit and keep going so long as he's still moving inside me.

"Harder!" I pleaded with him and he stopped trying not to hurt me and instead gave me just what I had asked for, and as he pumped his fist into me, I came twice more in a row, soaking my chair, arching my back and moving forward in my chair, pushing myself onto his fist. I couldn't stay quiet now, I was almost moaning in squeaks and he was forced to slow down, we knew we were making too much noise. He put his head on my chest as he slowed down and I put my hands on his neck and inhaled his smell as my orgasms subsided from the entire center of my body. My breathing slowed and I pulled his head up to mine and rubbed my cheek against his face. He nibbled at my ear which made me sit up straight and he pulled his hand out of me at that same time.

After helping me into my clothing again, he left my office and closed the door, which I appreciated since I needed a moment to regain my composure. After a few minutes he sent me an instant message, asking if I was ok. I replied that I was great, he was great, and I was going to be sore tomorrow-making sure to include a winky-face so that he knew that I was ok with that. "It was worth it." I said.

I must be addicted now, because with 20 minutes left in our workday I pleaded with him to do it again. "Are you serious?" he asked. "Yep." I simply replied.

He obliged and it was similarly orgasmic. He bent me over his desk again, and again I found myself dripping down my legs, wondering what it was about that position that made me so wet, and then also wondering where all of that wetness was coming from. I stopped thinking about it when, with his fist in my pussy, he slid his thumb into my ass. I was then glad to be laying on his desk because my legs gave out and I concentrated on all of the good feelings he was giving me and I ran smack into another orgasm. He led me right into another one because he removed his thumb from my ass and instead rubbed two of his fingers on my clit and and as I enjoyed those amazing sensations I felt his tongue in my ass and I was into another orgasm immediately, it joined with the last one and spanned across to another that he produced by pushing deep inside me and calling me his little slut and telling me I like having a fist in my pussy. His dirty talk alone makes me almost-orgasm and then he tells me to hold on, though he doesn't take his fist out of me.

I hear his belt come undone and I turn towards him, a confused look on my face and then I feel his hand inside me stretch out a little more. It hurts but I don't tell him to stop. I feel his thighs get closer to mine and then his mouth is next to my ear and he says, "You have my dick and my fist inside your pussy."

I whimpered and melted into the desk again as he moved inside me, not much because there was no room. He had me stretched to my limit but it was such a good pain and he was so turned on that I didn't care that it hurt. He pushed his fist, still wrapped around his cock, into me only a few more times until pulling his dick out of me, leaving his fist inside. I felt him stop moving and then I felt the head of his dick pressing into my asshole. My eyes got wide as I realized what was coming, I was about to have both my pussy and my ass filled and I was anticipating how awesome it would feel, even as I also didn't want it to happen - only because I wanted to savor the amazing day that had happened so far and keep something else amazing for later in the week.

I can't say no to him, I haven't ever wanted to, and I waited as he pressed himself against me, trying to loosen me up so that he could easily slide himself into me. I concentrated on relaxing, as counter-productive as that may be, and as he pushed slightly, bouncing his cock into me, I started moaning and anticipating feeling him slide in, and that's when I actually relax and his head slips into my ass. It is such a unique feeling, so sexy. He always gets me close to orgasm with just his cock in my ass so I push back into him. As I feel him sliding farther into me he remembers his hand and moves it inside me and I start panting. I whimper and push my ass back against his hard cock and his tight fist and he builds me into orgasm for the last time of the day. My pussy clamps down one last time on his fist and as I tighten around his cock I feel him release his cum into my ass, warm, wet, sticky, and incredibly sexy.

We both slump over onto the desk, his weight on top of me feeling like a reassurance. It's comforting to know that he has finally cum, after pleasing me all day, and I find it incredibly satisfying that his cum is inside of me, like I've won it, I deserve it.

He gently bites the back of my neck, slowly stands up and we say nothing, we don't need to, there's only sex between us and it's now time for us to leave. We clean ourselves up, completely unashamed of our bodily fluids, they're just part of sex and there are so many other good parts of it to concentrate on. I am ready to leave his office and I bend over, lightly kiss his lips, say thank you and then leave.

It truly is a great relationship that we have, and I'll hate it when it's over.