A [f]irst ti[m]e for everything (and one of many to cum)

So I just stumbled across this sub, and I feel like it is the perfect outlet for my little adventures. I'm in a long term committed relationship, and therefore do not have anyone to share my rendezvous with. But all the guys I've met are through reddit, so I figured why not give back to the community that is giving [it] to me?

Some stories will be hot and heavy, others will be an expression of my disappointment; I hope you will follow along with my adventures and share the excitement with me. I'll start with the one of the most exhilarating experiences I've had so far:

I had a post in a particular sub to which this gentleman replied. We started chatting via kik, and turns out he doesn't live in the same city as me but makes regular visits for work. He's planning a visit soon, and we arrange for dinner at a very nice local restaurant. Very hot and sexy chatting happens in the meantime, with discussions of experiences and preferences and the like.

The day finally arrives, and I tell my SO that I have a client in town that needs to be entertained and will be home late. I meet up with this guy for a pre-dinner drink, and we sit and chat over a couple craft cocktails. The first meeting is always nerve racking, but a couple of drinks will help build my courage. He's about 20 years my senior (I'm in my mid twenties, he's in his mid 40's), and much bigger than I am (I'm about 5'3, he must be 6ft+ w/ the typical 40-something body). Turns out we work for the same giant corporation, so not only am I planning to fuck an older and much larger man for the first time, but a coworker too!

After cocktails we make our way to dinner, where we drink and eat and chat some more. He eventually reaches out and touches the back of my arm, and my body immediately starts tingling all over. He moves his hands to my knee, working his way up my thigh and closer to the short hem of my dress. We're leaning in close together as he continues to caress me. Dinner is winding down, and he leans in to whisper in my ear:

"Why don't you go to the bathroom and take off your panties for me?"

With the rush of alcohol and adrenaline, I smile and nod my head and do exactly as I'm told. I walk out of the bathroom with my short, A-line dress swaying and a cool rush of air hitting me in the hot spot between my legs. I sit back down and cannot hide the giant grin on my face. Never have I ever gone commando in a dress, much less at the request of a man. He returns to caressing my thigh, working his way higher and higher up my dress until he reaches the point where my panty line would be. Satisfied that I've obliged with his command, we make our way back to his rental car.

Holding my hand on a busy street the whole way back with me pantiless, he pulls me down an alley, pushes me against a brick wall and starts making out with me. He is completely encasing my body with his. As our tongues explore each other's mouths, he reaches a hand down under my dress and slips it between my soaking wet lips and onto my clit. My head tilts back and I let out a gasp, my arm around stretching around his neck and my leg lifting up around his hip. He then slips a finger in my moist, hot little hole, and I can't help but let out a moan from his touch. Thrusting his finger inside me over and over again, I feel my body clench as I get close. He feels it too, stops, and takes me to his car. Once there, he leans over and slips a finger back into my pussy, then two. My legs spread out on the dash, he fingers me the whole drive back to his hotel.

Once in his room, he takes me into the kitchenette and immediately strips me of all my clothes. Before I know it, I'm completely naked and he lifts me and plots me onto the granite countertop. Cold granite against my hot ass, he kneels in front of me and pushes his face into my spread legs. His tongue explores my clit, my hole, my clit again, lapping up my juices. He focuses on the very tip of my clit and slips a finger in me, and then another, just as in the car. But this time he's going to let me cum. I feel the rush and leaning back on the counter let out a giant moan as I the orgasm overtakes my whole body.

He then lifts me up and throws me over his shoulder like a rag doll, takes me into the bedroom of his hotel and tosses me onto the bed. He pulls me by my legs to the edge and after putting on a condom, slides his throbbing cock inside of me. Finally, I feel so full and so stretched. He lifts my legs and holds them up with his hands as he stands at the edge of the bed and fucks me over and over again, pounding my tight, wet pussy. My back is arched and my hips are rocking in an attempt to keep up with his rhythm, but the feeling is so good and so intense that I just can't manage.

He flips me over and climbs onto to bed behind me, again sliding his cock into me again and pounding me as he pulls the back of my long, black hair.

SMACK.

I suddenly feel a sharp pain on my ass and let out a very shocked yelp. It hurt, but felt oh so, so good. He laughs and asks, "Did you like that?" Between the hair pulling and the pounding, all I can manage to muster is a small nod and an "uhhuh!" And then before I know it..

SMACK.

Another sharp pain hits me, this time on the other cheek of my ass. My body starts to tighten again, trembling all over as my orgasm gets closer and closer. When I think I'm about to hit the moment of no return..

SMACK.

I feel a sharp pain in my ass from his giant hand in the same spot as the first and I completely loose it, cumming around his cock and letting out a loud moan as I collapse onto the bed.

"So, you like it rough, huh?" he asks as he lays beside me. Out of breath and through a huge smile I pant out an "I guess so.. heh."

"And how do you want it next," he wonders outloud as I try to compose myself.

"I want to make you cum," I eagerly respond.

He immediately jumps up, grabs a pillow, and opens the door to the balcony of his hotel room overlooking the skyline. He drops the pillow in front of him and gestures for me to kneel down. I again oblige, and take his cock into my mouth as the humid night breeze swirls all around us. I swirl my tongue around the tip, then drag it down the shaft before working my my back up to the tip and taking the whole thing into my mouth. He grabs my hair and thrusts his cock into my mouth over and over again, spit dripping down the corners of my mouth. I take his shaft in my small hand and work in the remaining spit while sucking hard on his tip and working my tongue all around. He lets out a moan and leans back as he explodes into my mouth. I look up and him for my next direction. "Swallow," he says; I again oblige.

"You've made my legs wobbly," he says as he lifts me up off my knees and steps behind me. We lean over the balcony naked and take in the view, reeling in our night of adventure.

As I get dressed, I notice 3 large handprints on my ass. "How am I supposed to hide these from my fiancé?!" I say in panic. "Just don't let him see your ass," he commands. I get home and very carefully oblige for the last time that night, making sure to hide my bare ass from my fiancé for the next day and a half until the hand prints finally fade.

Source: reddit.com/r/gonewildstories/comments/3fw4wv/a_first_time_for_everything_and_one_of_many_to_cum