I am a white woman, thin/athletic/petite, early 30’s, fair skin, long brown hair, and at the time I was on a short term assignment for work where I would fly to another city for three days per week. During my travels, my husband and I agreed I could have play dates.
I matched with this gentleman online a few months earlier and the timing just never worked out. Either one of us was busy or out of town as we both had some travel requirements for work (mine being pretty obvious). Unlike a lot of the guys I had matched with, this guy was fairly removed. Our talk was always platonic, we never exchanged nudes, and somehow I was drawn to him. I wanted to meet and I couldn’t let go.
One week, that was it. I had to have him. I reached out, and he was both free and interested. A time was settled for him to come to my hotel.
A few hours before he was supposed to show up, he sent me a message. He wanted to know if I’d ever role played before or if I was interested. He was in to the idea, liked being told what role to play, and wanted me to pick a scene we could play. Having never role played before and being the introvert I am, I was nervous, but if there’s any time to make a fool of yourself, its with a stranger you can part ways with and choose to never see again. So although I was nervous, I was getting turned on, too.
So I told him: pretend to be someone from the hotel. Maybe there’s something wrong with my payment or you’re trying to get me to move rooms. He said OK and told me he was on his way. I needed something to pass the time, so I opened my laptop to try and get some work done.
Enough time passes for me to really get into my work. A client was having a problem and I really thought it would be a short fix. Suddenly there is a knock at the door and my heart drops. At this hour? Who could it be? Wearing my sexiest bedroom attire, a work volunteer shirt and pink cotton panties, I go check out the peep hole to see who it is.
Quiet as a mouse, I sneak over to the door and peak out. There he is – my match guy. Heavy spring jacket, zipped almost all the way up, jeans, casual shoes. Short brown hair and beard. He’s got his hands in his pockets and is looking down the hallway. He looks casual but alert. I open the door a few inches.
“Yes..? Can I.. help you?” I’m struggling to keep eye contact and not look him up and down. He’s a little taller and broader than I was expecting, but that’s pretty common for someone my size.
“Hi, yes. I’m with the hotel. I was asked to come speak with you regarding your payment. There is a problem; it’s been returned and the room isn’t covered. I’m here to collect a new form of payment, or..”
“Or what?” I cut him off.
“Or you will be asked to leave.”
At this point he’s begun to notice my t-shirt without pants. He’s also still standing in the hallway and is keeping it surprising cool. Meanwhile I’m struggling to use the door to hold myself up and refrain from showing how nervous I was. Keep it cool, girl, you got this.
“Oh, um, that’s.. wow. Do you.. could you.. please, maybe come inside?” I try to take a half step out pass him to look around. “We really don’t want to make a scene in the hallway.” He stands his ground so I’m forced to step into his space.
“Oh, I’m not su..” I cut him off as I take a step back and open the door, giving him the full view of my (in)complete outfit.
“Please, come in.” Simple and firm. ‘This is fine,’ I keep trying to tell myself as it gets a little easier to hold my composure. Cautiously, he steps inside. His hands are still in his pockets as he looks around the entry way. I shut the door and start to walk further in the room, calling over my shoulder to him, “Surely we can talk about this payment problem. There’s bound to be a simple solution here.”
At this point, I’m in the middle of the room. Not really towards the bed, but leading him far enough in the room that the scene just became about sex in a hotel room. Sex was easy for me, but role play was not. Shifting the theme let me relax a little.
“The bank sent your payment back. I need a new form or I’m here to ask you to leave.”
“That really can’t be. You see, I’m here for work and it’s a work credit card, and they really handle everything. At this time of night there’s no way I could resolve. Surely that’s understandable and we could leave this be tonight and resolve in the morning? I’m here another night and will be in the office tomorrow. I can work it out with them and resolve it with the hotel.” I start wringing the bottom of my shirt, trying to let my nervousness show. Would I really have to leave? And at this hour?
“No. Really, I insist.”
I take a step closer to him. “Surely it’s just delaying the notification, right? It’s not that we won’t resolve it.. just later”
“Now.. I don’t really have the authorization to do that. I would really be sticking my neck out. And for what?”
I take a step closer to him. I’m almost in his space again. “For helping me out.” Another step. “I could help you out, too.”
Our height difference makes him have to look directly down to me now because I’ve gotten in close. I’m almost up against him. His hands are still in his pockets. He pauses a little longer than I expected, looking around the room.
“I would need some sort of initiation. I need to be sure I’m not misinterpreting what you’re offering.” And with that he brings eye contact back. His nervousness is gone.
I reach my hand up and start unzipping his jacket, maintaining eye contact with him. “Is this the sort of initiation you’re looking for?”
“Yes”
I turn him a little and nudge him back to sit on the bed. I get down on my knees to start with his belt and then move to unbutton and unzip his pants. He starts to help me because I’m so turned on at this point that I’m fumbling around. I can tell he’s turned on too but not all the way hard yet. Well I can certainly fix that!
I take his cock in my mouth. It’s soft enough that it all fits in my mouth with no struggle and it feels so good. Slowly, I suck him from base to tip, running my tongue all over his head, working to get him hard. I am loving every inch of him and I can tell that he is loving it, too.
I start unbuttoning his shirt so I can run my hands up his chest. He’s hard now so I start to pick up my pace. Running my tongue all along the bottom of his shaft as I continue to take him in my mouth and down my throat. His cock feels so soft and hard in my mouth. The skin is so smooth and I can’t get enough.
I take him out of my mouth and grab the shaft with my hand. I lower my head and start licking and gently sucking on his balls while my hand keeps playing around his shaft and his head. I can hear how much he’s enjoying it and that makes me want to take him more. I put him back in my mouth and take him all the way in. Coming back up, I look up at him and that eye contact was all he needed.
“God you’re so fucking hot. I need to fuck you, now.” We finish undressing ourselves and he takes out a condom. “Sit on the bed, right on the edge.”
So I’m leaning back on my elbows, ass on the edge of the bed and legs up in the air. A real site to see, apparently, because he actually took a step back to stare for a second while he puts on the condom.
He starts by teasing me with the head. Running it along my slit and over my clit, using my own wetness to lube up. He puts his head inside and starts fucking me with just his head. I throw my head back in both pleasure and frustration. I try to start grinding my hips towards him. He must have gotten the message because I hear him say, “oh you want more?” As he finally fully enters me. We both let out this huge moan of pleasure as he slowly starts to pull it out again. In and out, slowly and agonizingly he continues.
I pick my head up and looked at him. He’s staring intently as he picks up the pace. It feels so good as we find our rhythm. I look down and start watching him. In and out, quicker and harder. Then he pulls out.
“Turn around, lean on the bed”
Let me tell you, this bed was the perfect height. I bent over on my elbows, ass back and really showing it off for him, wiggling my hips and shaking my butt.
“Oh, you’re really getting it now.” He comes up behind me and I can feel him grab my hips. Again he starts teasing me with his head. It’s really driving me crazy at this point and I’m just begging to be fucked. Finally he pushes himself all the way in and I let out a huge almost sigh of relief. In and out again as he builds up the motion and momentum. Faster, faster, and a little bit harder. Finally he picks up spead and he’s really pounding it to me and I am just loving it. Face down in the bed to muffle my moans and noises and he fucks me harder.
He lets out a big moan and I feel him pull out again. I turn my head and he’s walking around the side of the bed. I follow him with my eyes.
“Ok, my turn. You’re getting on top.” Ha, little did he know that’s my favorite way to orgasm.
I jump up on the bed and crawl over to him. I forget trying to be sexy at this point and focus on getting on top of that cock. He’s leaning back against the pillows and I straddle over him on my knees. I reach behind me and guide him into me as I slowly lower myself on top of him. Once he’s all the way in, I wiggle around for good measure, and then I slowly start to come up off of him. Just a few inches and then back down. Up and down and up and down. Then I start to go a little higher and back down. Higher and back down. Then finally I will pick up the pace and bounce up and down on that cock like it’s my favorite thing to do.
“Ohh more!” I said and I really picked it up. I’m leaning forward on him with my hands on his chest for support and balance, really using all I’ve got to fuck myself with his cock. He’s grabbing my hips and running his hands all over my ass and I am loving all of it. He pulls my head in to him and it changes the angle just enough that he starts rubbing up against my spot. The slight change really drives me wild and I kick it in gear. I fuck him like there is nothing more important than cumming.
Now normally, I can feel the orgasm coming, building, and I’m ready for it. But this orgasm just hit me out of no where. All of a sudden I’m at a 10 just screaming. And good for him for recognizing, because he didn’t miss a beat grabbing my hips and picking up where I was no longer capable of continuing to fuck him. He pounded my pussy continually while I road that orgasm for what felt like a solid minute.
Just as I thought my wave was over I feel him start to pick up the pace again, “Oh no, we’re not done” as he fucks me harder. I let out one more final moan as I hear him say he’s coming.
He gently shoves me off of him so we can both catch our breath. We lay there for a while, talking about the sex and my assignment/time in the city. Shortly after, he gets up to start getting cleaned up and dressed, and is finally on his way.
Source: reddit.com/r/sexystories/comments/cesxau/my_first_role_play_experience_and_the_amazing