Cheer up Watch This Striptease

This started as just a quick one-off story without a whole lot of emotional substance, just a little bit of fun between two friends. I think it will continue in at least one more chapter.

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"Wait a minute. You do what now?"

I couldn't believe I had said it either. Fortunately, I didn't sense any judgment in Chris's outburst.

I rolled my eyes, "I'm pretty sure you heard what I said man."

"Humor me. Pretend that I didn't."

"Well, alright. The cat's out of the bag anyway I guess, but I'm only giving you the short version." I took a deep breath, hoping to calm myself a bit, before continuing.

"Sometimes when I'm chillin at home I like to mess around like I'm a stripper. I get dressed up, put on some music, pretend someone is in the empty chair, and do a striptease. Occasionally, I'll go all out with a lap dance if I feel up to it.

"You hear me that time? Because that's all you get."

"Oh, I heard you the first time." He chuckled a bit, "I just wanted to see if you'd actually say it again."

"Very funny, a-hole", but I laughed a little too.

"You go male thongs or panties? All shaved? Other clothes on top? If it's panties, do you do makeup and stuff too?"

"Holy crap man! You sure you don't have more questions?"

"Enquiring minds want to know. Let's hear it!"

"Alright, short answers...panties, smooth from the neck down, which feels great by the way, clothing depends on the day, sometimes I skip it and sometimes not, no makeup or anything like that. I'm not trying to look like a girl or anything. I just like the other stuff. It's a bit of a clumsy mess I guess, and I'm sure I'd get shit for tips."

"Aw come on, I'm sure you'd get at least twenty, thirty, maybe even fifty...pesos"

"LOL! You're probably right. I'm selling myself way too short."

That was about the end of it for that night. I had mostly forgotten about the conversation when the topic surprisingly came up again.

I had just won a big hand that brought a big pile of chips my way, cleaning out a couple of the guys in the process, Chris being one of them. He just relaxed back in his seat to watch but Ryan got up and got ready to go, along with his buddy who had been waiting for him to finish up. We were down to just two of us and it didn't take long until I was able to chip away and take the final pot.

Chris was still sitting at the table as I finished putting the last of the beer bottles in the kitchen. I could tell he was a little down after losing. "Sorry about that man. I'm sure that stung a bit. At least you didn't buy back in twice like Ryan's buddy did."

"I know. I can't believe he did that. Anyone watching would assume that he had no chance of coming out on top. At least I'm smart enough to limit my losses."

I tossed him a bottled water. "Too true. But seriously, sorry that didn't go well for you. You got so close there."

"Yea, it would've been nice to come out ahead tonight."

"We've all been there. Well, except for Ryan. He never seems to care when he loses. Don't feel too bad about it."

"I know what would help." I could almost see the lightbulb light up above his head when he came up with a 'great' idea. "I think you should do a striptease. Seeing what you called a clumsy mess would probably cheer me up."

I responded before I really had a chance to think. I was feeling bad enough for him that I think part of my brain must have gone haywire. "Fine, but no laughing out loud. That could break me."

He was perking up a little already, "Alright, you said you'd do it. No backing out now!"

I turned to head toward the bedroom to get ready. Damnit, what the hell was I thinking when I said yes.

I was halfway down the hall when he called out again, "And don't think you're going to get away with some half-ass outfit or dance!"

And with that, there went any chance of making it a quicker, less painful experience. All that remained was to figure out how I was going to dress for this show. I was standing in my room with the closet door open, trying to decide, when I finally just said to myself, "Fuck it. I'm doing this so I might as well go all in."

After making that decision I went about putting together what I was going to wear. Fortunately, I had already shaved in the morning, so I wasn't going to have to waste any time on that step. All that remained was to get dressed and get some music queued up.

I slipped on a couple layers, connected my bluetooth speaker and headed back out. I had the music going when I walked into the room where Chris was sitting in one of the kitchen chairs facing me. He had finally changed from his work clothes into a t-shirt and pair of shorts. Why he hadn't changed before the poker game was beyond me.

He had to have been curious how I was going to look while he was out there waiting, and he seemed to be anxious to see how things were going to go. I couldn't tell if he was just waiting for the chance to laugh or if he was really interested in the upcoming show.

Regardless, I decided that the best way to get this over with was to get started. I started with some casual dancing as I tried to get my head wrapped around what I was doing. Usually, I was a little worked up when I started dancing and I was definitely not used to having an audience. I did my best to block that fact out and just went for it, slowly getting a little more suggestive as the seconds went by.

It wasn't too long until I had all but forgotten that it was Chris sitting just a few feet away. I had successfully let myself get taken up and was really immersing myself in the moment. I turned my back to the chair and bent forward to grab my ankles, legs straight and feet shoulder width apart. The tiny, pleated skirt that was barely covering the top half of my ass combined with the new stilettos to make my ass pop.

Chris was getting more of an eye full than I ever imagined I would share with anyone, let alone with one of my best friends. The thoughts in the back of my mind were all over the place. I just pushed the negative ones to the side and let the wild ones run free. Sure, maybe this was crazy, but I wasn't even close to being done yet. I stood back up and turned back to face the chair once again, then danced my way closer until my feet came to a stop between his.

Once there I continued to twist and turn, to gyrate, and soak up the attention. Worries that Chris was only planning to laugh had long passed. He was now just sitting with complete focus on the show. I turned to the side and then reached behind to unzip the back of the skirt, loosening it enough so I could let it fall past my round cheeks.

When it fell, the view from the side must have been a confusing one. To one side there was a smooth bubbly ass sticking out for him to see, while on the other there was a bulge protruding, barely contained, and not very well obstructed by the mesh and lace of the sexy thong. Chris didn't seem to be bothered by the juxtaposition. He was enthralled by the seeming opposing views in front of him.

I didn't linger long in that position though. Once again, I turned away, this time to bend down to remove the skirt the rest of the way. I took turns lifting each foot from within the circle of fabric, all the while giving Chris an unobstructed view of my naked ass, split by the thin fabric, my smooth legs that were hugged in matching thigh highs, and if you looked further, you could see the bulge still protruding underneath.

I remained bent over, ass pushed back and up, and went back to swaying and gyrating, now confident that I was putting on much better than just a mess of a show. Chris hadn't really moved or said anything to confirm, but I honestly felt like I was putting on a show that was easily worth what the regular price of admission would be.

Fully into the mood, I started to pump up and down, my smooth bubble butt gyrating up and down between Chris' legs, slipping closer to where he sat until I was hovering inches from his lap.

After a while I was getting a little antsy staying in the same place, so I stepped forward before turning back around, all the while still swaying and thrusting my hips. Once I was fully facing him again, I reached out and pushed his legs together, then inched forward until I was straddling his legs. I put my hands on his shoulders to hold myself up while I resumed the show. I was hovering dangerously close to his crotch as I worked my hips, coming oh so close to grinding on his lap.

From what I could see, it looked like Chris's former gloom was a distant memory. I wasn't done with my part yet though. I had finally gotten comfortable, and I had another position or two that I had seen but had yet to try out.

I worked my way back from his lap so I could dance freely again. Arms above my head I swirled and gyrated my hips provocatively and eventually turned until I was facing away from him. I continued there for a short while, alternating between arching back and bending forward, pushing my ass back toward him, then turned to dance up to his left side.

I slowly lifted my right foot and turned to place it on his thigh, giving him a good side view. I didn't waste time in that position. Almost immediately I started to turn, resting my hands on both of his knees as I lifted my foot high and stretched it further across him. I gave him a clear view of the cleft between my cheeks as I simultaneously spread my leg wide in front of him and pushed back.

With the extra height from the heels, my cheeks, split wide before him, were just inches above his chest and on extremely up-close display. I kept that position, gyrating in front of him, but I couldn't hold it for long before I had to lower down until I was once again straddling his lap, this time facing away.

Calling it a dance seemed a bit of a stretch at this point, but I continued. My weight was resting on my hands on his knees. That position gave me more freedom to work my hips in whatever direction they took me. Chris could still easily follow the narrow fabric of the thong down between my legs just to where it started to strain to contain the contents in front, but it no longer disappeared between my cheeks. I was too far spread for there to be any secrets back there anymore.

I pumped and swayed, the insides of my thighs repeatedly rubbing against the outside of his, but I managed to keep from dipping too low in the middle. I was barely able to see between my legs to see just how close I was to making contact without going to low. At times I would thrust up and down, approaching his crotch before once again pumping my ass back up toward his watching his gaze. Other times I would use my grip just above his knees to pull myself forward and then push myself back, giving him a view of his own crotch appearing before disappearing between my legs, just barely underneath me.

While looking down it finally clicked that my view was being partially obstructed by the front of the short tank hanging down slightly. Apart from that, it was also the final piece of the outer layer. The final matching piece to the thigh highs and thong was underneath as well, the lacy bralette that I was wearing for the first time. After coming this far I wasn't about to go without showing off my first ever bra. The tank definitely had to go.

I raised back up as best as I could, given where my feet were positioned, and crossed my arms to pull the tank up and over my head. It was an awkward position, to say the least, so I came to a quick decision. I wasn't going to be able to balance while I finished removing the last of my outer layer.

Resigned to my fate I broke the silence for the first time since the show had begun, "Sorry, this is a little awkward."

"Not at all."

And, with that, I leaned partially back forward and lowered until I was straddled across the uppermost part of Chris's thighs. I was fortunate enough to have landed where I was high enough to not be in contact with the skin below the hem of his shorts, yet barely low enough to avoid contact with his groin. That is, until I had to sit back and arch to get the tank over my head.

As my weight shifted and my hips rotated back, suddenly I realized I wasn't so lucky after-all. I had just delayed the inevitable. Fortunately, the top hid the sound as I gasped when felt his bulge pressing against me from behind, the topmost part of it pressing deep between my cheeks. I was frozen in place with my arms still above my head. I couldn't put my hands back where they were to take my weight, and I still had to finish with the top that was still enveloping my face and head.

Resigned to my fate, I just sat back while I finished that phase of disrobing. I was intent on not letting that not so little surprise interrupt the show, so I resolved to carry on. In the interest of both changing things up, and getting up off Chris's lap, I pushed up just enough to break the contact and then leaned my upper back against his chest. That way I could move freely again in the air above his waist.

With my mind once again free to wander I came to a realization, and I decided to try something, something that had been done to me during a lap dance as well. I slid down enough so that I came back into contact with the mound below me, but not enough to where I was stuck in place.

Once there, I resumed my gyrating, but at that point I was lightly grinding right on Chris's lap. I was able to confirm my suspicion. He was not fully soft beneath me anymore. Something had stirred at some point since the striptease ended and the lap dance really began.

After teasing like that for a little while longer I extracted myself from his lap and then turned back to him.

I pushed his legs apart a bit so I could slide over one of them. I was swirling my hips and thrusting up and down his leg. This was another part of the lap dances that I had in the past. I always loved feeling the girls dragging up and down my leg, so I thought I'd mimic the action.

While pumping and dancing I looked at him, "You know, it would probably be less awkward for me if I weren't the only one here in just my underwear. Just a thought."

"Well, I suppose I could ditch the shirt and shorts if you think it would help. I'd feel a little more comfortable if you turned around while I lose the layers. After-all, I'm not the stripper tonight."

"Alright. That's fair. I guess it's the least I could do."

I turned around and casually moved, sometimes my whole body and other times just the hips. I could hear him moving behind me, but I resisted the urge to look to see what he was doing.

Finally, the rustling stopped, "Okay, carry on." Short and to the point as usual.

That was the queue that I was waiting for. I didn't turn to face him though. I decided to keep the mystery, so I just started to inch my way backward without a glance back, unaware even of how he was sitting. It became clear as I got closer. I paused momentarily when felt the inside of his thighs against the outside of mine, figuring out how best to proceed.

With my legs parted slightly for balance I continued backward, the pressure pushing his legs further apart as I went, finally stopping when I was nestled in high up between his upper thighs. I settled in and started really dancing again, intent on making this the best lapdance that he had experienced. I wasn't the best dancer in the world, but I think I can really get my point across in the right situations, and this was one of those situations.

I was really working, pumping my hips and thrusting my ass up and down just in front of his lap. Up until now, Chris had been mostly subdued but that finally changed, "There you go."

I took the encouragement and continued with enthusiasm. I was really focused on putting on a good show. I continued to move my hips with the music, pumping, swirling, gyrating. All the while, I could feel the inside of his thighs rubbing against the outside of mine.

Without really thinking about it I decided to return to the position I was in on his lap a little bit before the short break. I pushed my hips back a little further and started to lower back down to continue the literal lap part of the lap dance. I was surprised when I made first contact. It was a little sooner than I had expected to feel anything.

I paused in place, a little shocked when, after a brief moment, I figured out why. I realized that it was the tip of his semi-hard rod touching the middle of my cheeks, rather than a bulge contained in the boxer briefs that I had always seen him wearing in the locker room.

I could hear the note of concern in his voice, "Oh, sorry about that man. Totally forgot I had gone commando today."

Hearing his words unfroze me. I realized that I wasn't really bothered so I continued what I was doing. "No worries, I still have a layer."

I think we both knew that was a pretty weak justification. What I had on was maybe half a layer at best, if you were being overly generous. Neither of us was going to voice that though. That settled, I carried on with the dance.

I continued my descent. As I lowered to where I had been gyrating before I felt the fleshy tip first push between my exposed cheeks and then slide up my crack until my cheeks touched down against his balls. Again, a shock went through my head, but it didn't prevent me from carrying on, lifting back up, and sliding back down.

Chris seemed to be more than okay with the newest twist as I could tell that his cock was no longer just half awake. His flesh had thickened, and it felt fully hard as I slid up and down with it in my crack and squeezed it between my cheeks. I continued to pump up and down and even clenched my cheeks tightly on him, thrilled at the reaction that my motions were getting. I didn't want things to get stale though. A good performer never sticks to the same thing for too long.

I wasn't ready to totally change positions yet, but a little adjustment was needed. I lifted off his lap then l quickly shifted both of our legs around until I was straddling him again. I pumped up and down in front of him, but I didn't make contact in the same way as before. Instead, I lifted as high as I could and then slipped back until my smooth, round ass came to rest against him, barely above the now moist tip of his manhood.

I slid down, careful to keep his protrusion in front of me as I went. With it pointing forward just enough, my descent succeeded in pushing it down underneath me, until it poked out in front of my still contained, but straining bulge. The dance had us both on the edge, but I was nowhere near stopping.

In case I needed further confirmation that he was okay with where things had gone, I felt his hands softly come to rest on my hips shortly after this new phase started. He kept them there while I worked it on his lap, not doing anything with them, but also not taking them away. That was all the encouragement that I needed to keep things going.

I kept my eyes directed down between my legs, watching as the tip of his swollen cock disappeared underneath before poking out again, my panty-covered balls dragging back and forth across its length. There were conflicting thoughts constantly going through my head, "What the fuck am I doing right now?" followed by "I suppose I really don't care, and it definitely seems like Chris doesn't either."

The only question was where to take things next, and further back in my mind, how far to take things. After gyrating on him in sitting reverse cowgirl style for a while I decided another change in positions was in order. I stood and quickly turned, returning to the same place but face to face with Chris instead.

His swollen member was standing tall so when I first assumed my position on his lap again it was trapped between us. I let it be for the time being, choosing to dry hump him from underneath, completely unaware that the music had stopped at some point.