Convincing my older male colleague to creampie me [FM]

I ended the year with finally getting my older male colleague to fuck me.

***The story is pretty long, so I’ve marked the part of the text where the sex starts like this, for those who would like to skip the background.***

We’d been working together for a few months, but t’s only the last couple weeks that I have for some reason become obsessed with the thought of getting fucked by him.

So my colleague, let’s call him John. At first glance he doesn’t really stand out, apart from being very tall. I think he’s in his early 50’s, and looks pretty good for his age. Despite not being the most attractive, he’s one of those people who are just undeniably charismatic. However, he is always very professional. I honestly don’t know that much about him except that he’s divorced and has a daughter who’s a year younger than me.

I’m 26, I’ve got dark blonde hair and brown eyes. I consider myself to be cute, nothing out of the ordinary, but I usually manage to get what and who I want. I’m 5’4 and have a petite body, except my tits which are a little big larger than what would be proportional. I’ve always been turned on by being with men who aren’t typically attractive, or who are a lot older than me. I guess I enjoy having those men worship me, and I don’t get that the same way from “hot” guys my age.

Because of recent personal growth, I was convinced I was over my thing for older men, but turns out I was wrong. I’m not sure exactly what it was, maybe just plain boredom, but one day at the office I decided to start flirting with John. He quickly caught on, but he was hesitant. I would feel him looking at me from across the office, or in meetings, and I’d glance back at him with my clueless but horny look that I had perfected. When we were alone he still never said anything inappropriate. The furthest he would go was to put an occasional fatherly hand on my shoulder, or compliment my hair. I got the feeling that he didn’t believe I could actually be into him.

We were having a Christmas dinner at work, and I decided on wearing a black mini skirt. Since it’s cold where I live I wore it with tall boots and black stockings. With that I wore a cream long sleeved fitted top. It wasn’t sheer, but thin enough that you’d be able to hint at my nipples through it . It was a classy outfit, but it was definitely going to stand out.

As soon as I walk into the restaurant where the party is, I see John walking over, looking at me up and down, in what i read as a mix of disbelief and delight.

I reach my arms up to give him a hug, John’s a lot taller than me, which probably has added to my obsession with him. He gives me a tight hug and says “wow honey, you’re gonna give someone a heart attack tonight” into my ear. I just laugh as if I have no idea what he’s talking about, and then he says, “please tell me you’re sitting next to me at dinner?”

During dinner I try my best to behave next to John, after all most my colleagues are pretty conservative and I don’t want them knowing about my plan of getting a man almost twice my age to sleep with me.

However, he doesn’t bother to talk to anyone but me. When I move over a little so our legs touch, he puts his hand on my thigh, right where my skirt ends. I feel my whole body getting warm and tingly from his touch. He looks over at me as if to ask if I’m ok with this. I give him a little smile and I put my hand on his, guiding it further up under my skirt. I lean over and tell him “I’m leaving now, I want you to come with me but you should wait so they don’t see us leave together”.

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***I’m trying to find my coat when two large hands grab my waist from behind. John turns me towards him, leans down and kisses me deeply. He looks at me fondly and says “I couldn’t let you walk home by yourself in the dark sweetie. If anyone asks I was just walking you home.”***

The walk to my apartment is only a few blocks, but on the way there I can feel myself getting a little nervous. Maybe John could tell because once we’re inside he stops and says “Listen, I think you’re beautiful, and I’m amazed that you seem to be into me for some reason. But I’m a lot older than you… are you sure about this? I mean…”

“Yes John, I’m sure.” I interrupt him. “I’ve been planning this for weeks”, I say as I throw my coat on the floor and pull him into the bedroom. It seems this was all the ensuring he needed. “Come here” he says as he sits down on the bed and gestures for me to sit on his lap. He gently strokes my face and looks at me, almost in awe.

“What a gorgeous girl you are, look at you” he mumbles. I can feel myself blushing as he pulls me in and kisses me again. We make out for a little bit, and then he lifts me up so im standing in front of him, between his legs. He gently peels my shirt off, revealing my white lacy bra. Like I’ve mentioned, I’m quite petite, but my tits are pretty big for my size. You can see my pink nipples through the sheer fabric, and John lets out a soft groan as he cups my tits in his large hands. He kisses me all over, taking off the rest of my clothes until I only have underwear left on.

I glance down at his crotch and I can tell he’s hard, his dress pants look like they are about to burst. He grabs me and lays me over his lap. “Let me take a look at you baby girl, can I take your panties off and play with you?”

I’m already so turned on and I whimper out a faint “mhmm”. I feel him slowly pulling my panties off, spreading my thighs so he can get a good look of my smooth, glistening pussy. My heart is beating fast and I’m breathing a little uneven in anticipation.

“Oh you poor thing,” he says, “look how wet you are”. He runs a finger up and down between my labia a few times, teasing me. “Please…” I say and look back at him with a pleading look. “Good girl” he says, working circles around my clit, and gently pushing two fingers inside me.

I recently discovered that I get turned on by getting praised, and John was good at that. I loved the feeling of being exposed like this, letting him do what he wants with me and getting told that I’m being good.

John pulls me back up and puts me on my knees on the floor, in front of the big mirror on my wall. He stands in front of me, unzips his pants and pulls his thick cock out. I’ll be honest, I’ve seen some large dicks before, but I had never seen one like this. I grab it and start stroking it slowly, my fingers can’t even reach around it completely. “Can i please suck your cock John?” I say, looking up at him with an innocent smile. He looks at me like he can’t believe that just came out of my mouth, and groans approvingly.

I start placing kisses all over his cock, slowly kissing and licking my way up and around the tip. I make sure to look him in the eyes as I take it into my mouth and start sucking him. I can feel his dick getting even harder as I’m working him. I glance over into the mirror and I get so turned on by seeing myself like this- on my knees in front of this huge older man, trying to take his whole cock in my mouth. John looks down at me and says “I know it’s hard sweetie, but I need to try fucking your throat. If it’s too much just tap my leg and I’ll stop, ok?”

I look up at him to see if he’s joking. Apparently he’s not, so I tell him to give it a try. He grabs the back of my head and starts thrusting into the back of my throat, gently. At first it feels impossible, but slowly I feel him getting deeper and deeper with every thrust. “You’re such a good girl, there you go,” he mumbles in between moans.

Suddenly, he pulls out of my mouth, his dick covered in my spit that has been dripping down on my chest. He helps me up and holds me for a moment, kissing me on the forehead. Then he lays down on the bed, pulling me on top of him. I was thankful to be on top, I honestly I wasn’t sure if I’d be able to fit him inside me, but I had to try.

I grab his dick and let him push it into me, first the tip, and then slowly stretching my tiny pussy until I take all of him. I’m moaning and whining in his ear, trying to catch my breath as he starts thrusting into me with long strokes from underneath me. Somehow my clit is rubbing against him, and I can feel an orgasm start building. I reach down to rub my clit with my fingers, and I’m sure he can tell I’m close by my desperate noises. I feel my cheeks flush, right before the orgasm rips through my body and I lay down over him, screaming into the pillow.

Somehow him fucking me feels even better after I cum, and I can tell he’s close too now. As I’m clenching my pussy around his cock, I lean in close to his ear and moan “I can feel you’re close, will you please cum inside me? Please, please, please”. That sends him over the edge. I feel his cock pulsating and he groans as he’s pumping me full of his cum.

He actually ended up staying the night. We cuddled and he kept telling me how amazing I was and how he couldn’t believe this had happened. I definitely could, and I plan on doing it again.

Let me know if you’d like more stories! Also, English isn’t my first language so i apologize for any grammar errors.

Source: reddit.com/r/gonewildstories/comments/102i62i/convincing_my_older_male_colleague_to_creampie_me