Jackson's Strip Tease

Jackson says, "I think I'm going to do the burlesque show soon. Doing a strip tease sounds kinda fun." in his usual cool, flat manor.

I try not to do a spit take with the tea I'm drinking, "What now?" I didn't want to spew it all over the steering wheel of my car.

Jackson isn't the kind that I thought would be up for that. We dont know each other super well, but we've been going to lunch together on most work days for the last few months. He rides his bike to work, and doesn't always bring his lunch, or want to eat at the work commissary.

One day he came by my desk, asking when I'd be going to lunch, and wanted to know if he could tag along. We usually just sit in my car, in the parking lot so we have some escape from the other chatty people at work.

He's about 5'7" with a mop of straight auburn hair hanging over his ears and an almost, but not quite wispy short reddish beard. He's mid twenties. Pale and thin, but thats just a guess as he wears baggie clothes that hide his body. He's cute i suppose, but he's never caught my eye. Jackson's super quiet and unassuming. He just kind of melts into the background at work. He's usually the same at lunch, where we don't talk too much beyond what video games we're playing or movies we've seen. 

He didn't seem to notice my reaction, but went ahead and elaborated, "I heard about it from my ex, and I went a couple of times with her, and it was pretty fun to watch. There were bands, comedians, and men and women that did strip teases."

He pauses to take a bite from his chicken sandwich, while I digest what he's said.

"What about the other stuff you could do at the burlesque? Why'd you pick stripping?"

Jackson looks at me with a glance while chewing on some fries, "Well, I'm not a musician, and I'm not funny. I've been told by girlfriends I'm a decent dancer... for a white guy."

"Ah, okay... well, are you comfortable with people seeing that much of you? How undressed are you going to get?"

"Oh yeah, it's not a huge show. There's a few dozen people, and they're all drunk or on their way there. I figure I'd get down to some skimpy underwear. It'll be fun i think."

"Well for sure... any reason you're letting me know about it? Looking for some moral support in the audience?"

"Um, yeah. That'd be good..." he pauses, more than usual, and finally seems a little awkward, "uhhh also... I couldn't help but over hear one time, you were talking about your ex-boyfriend. Are you bi or gay... or something?"

I dont hide my sexuality at work, I'm lucky to be a big, burly cis-gendered dude, so people can be shocked when a 6'5" bearded guy mentions dating other guys, but they soon forget it, and move on. Usually any way. 

I'm a big guy in my early thirties, I run and go to the gym some to keep the pounds off. I'm not ripped like Hemsworth or Jackman, but I've got a flat belly, nice biceps, and i get compliments about my butt and legs fairly often. with my full beard and hairy chest I guess I'd be considered a bear.

I reply, "umm, pretty gay. I haven't dated a woman since high school." I'm not sure where he's going with this. "Is it a queer show or something?"

Jackson shrugs his shoulders, "well, I would ask my ex. She's gone to male strip shows, but she'd probably find it weird if I asked her. Have you gone to one? The nights we went to the show there weren't any guys dancing, but people talked about it, so I dont know what exactly would be good to do."

"Ah, well. Ummm, I haven't been to a burlesque show, but I've gone to gay strip club before, and the bars I've gone to have had gogo dancers. That's a bit of a different intent, and they go a bit further than I think you're wanting to go."

Jackson sips his soda, and nods his head. "Well... the reason I was wanting to strip at the burlesque show was to test the waters... i could use some extra money to get my car up  and running before winter starts. It wouldn't interfere with this job, plus strippers can make decent money right?"

"Oh dude. I have no idea. Its been ages since I've gone. It was pretty wild." I chuckled, "it looks like they worked hard for it though."

He seems to think on that for bit, while some Tame Impala plays on my car stereo in the background. "Would... you be willing to talk to me about it sometime? I know it's weird, but I don't really have any gay friends."

I squint at him a little. I'm not sure if this is just a straight boy wanting honest help, or he's just jumping through hoops to get me alone. Some straight guys have a tendency to suddenly become curious. "Sure... I'd be free this weekend."

He light's up a bit, "That'd be great! I'll text you my address later." 

We finish up our lunch in general silence and head back in to work to finish out the day. I'm a bit distracted though, trying to figure out if this is going to be more than just pointers about stripping.

Jackson ends up texting me his address after work.

- heres my address, come by Saturday at noon and we can have a beer and hang out :-)

----

Saturday comes around finally, and I head over to Jackson's place. He lives in a modest looking duplex. As I get to the door, and im about to knock, the door suddenly opens, but it's not Jackson answering the door. A guy my height answers  wearing a road cycling outfit, with the shirt unzipped, showing off a hairy, defined chest. 

He's got his bike beside him and he looks as shocked as me for a second. Then he says, "Oh! Your my bro's friend from work, Zander, right?" He looks a bit like a bigger, slightly older version of Jackson.

"Yeah, that's me...," I can't help but check him out. The tight, spandex shorts don't leave much to the imagination. He's broad shouldered and lean, with beefy cycler's thighs, "and your name? Jackson didn't mention he had a brother."

"Oh I get it, he's a quiet guy. I'm not surprised. I'm Jordan by the way. Our parents like names that start with J, hah! Anyway, I'm gonna be out cycling with friends, and then I'm gonna crash at a friend's house. Y'all will have the place all to yourselves." 

He gives me a wink, and I step out of the way, so he can go past. I check out Jordan's ass as he goes by.

He looks over his shoulder at me and says, "Jackson is just getting out of the shower, go ahead and wait in the living room. He said you'd be here at noon."

I head into the front door, still thinking about Jordan's perky, beautiful ass and have to adjust my semi-hard cock. That isn't the kind of stimulation I think I need before hanging out with a straight dude who wants to talk about stripping. 

I've barely shut the front door, when across the dimly lit living room, and down a hall, another door opens which I assume is the bathroom, because Jackson walks out in a thin cloud of steam with nothing but a towel wrapped low across his hips.

It's my first time actually seeing his body at all, and I'm honestly impressed. He's thin and kind of small, bit not soft or twink-ish. He has lean, practical looking muscles. Jackson has a small patch of chest hair between his hard pecs that turns into a thin trail in the cleft of his 6 pack abs, and goes past his navel. With the towel so low, i could see a good portion of his moderately trimmed bush as well.

"Oh, Zander! You're already here. Just as reliable as you are at work." He gives me smile, and then suddenly realizes he's just in the towel and his shoulders hunch. "I'll be right out, lemme get dressed."

Jackson rushed down the hall, but i could see his pert backside for a moment and the little bit of hair on his back above his ass, that wasn't covered by the towel.

I was a bit taken a back, but got myself pulled together enough. He and his brother had a big TV, with several video game consoles. It looked like they even had a Super Nintendo. The walls had typical "bro-ey" art. Some Tarantino posters. And some Star Wars art. The couch was a big sectional that had seen better days with a messy coffee table crowded with a bong and other pot stuff. There was a kitchen and dining nook off to the side with a sliding glass door, looking on to an immaculate backyard. A big contrast to the frat house living room.

"Go ahead and sit down, I'll grab us something to drink. You like Cider right? I remember you mentioning that one time."

I'm Surprised he remembered that.

Jackson had come into the living room wearing some well worn basketball shorts, and a lose tank top. The ensemble showed off his hairy calves, and defined arms. It was hot catching stolen glimpses of his small pink nipples, and hairy pits as he walked over to the kitchen. He had a bit of a farmer's tan.

I found a spot on the couch to plop down on, and adjusted my growing semi again. It was a hot day, so I was wearing some khaki shorts, that could be considered a bit too short at mid thigh, but I liked how they accentuated my legs. The dark gray tshirt was a bit tight, and showed off my arms and pecs.

Maybe I was trying to see if he was up for seduction, or maybe I was dressing for the heat. The number of straight guys that have confessed being curious to me is not small, so I was preparing myself i suppose.

Jackson comes over to me at the couch. "Man it's fuckin' hot today isn't it? Here's a cider, I hope you like it." 

I can see a faint outline of his cock through the short's weathered, and shimmering fabric. I force my eyes to keep traveling up to his face though, which is looking more handsome to me now, with its sharp angles. He has a prominent Adam's apple as well. 

He sits down on the same side of the couch as me, about an arm's length away and spreads a bit turning his shoulders towards me some. His tank top exposes an armpit and a nipple.

Jackson takes a swig of beer, nods at the sliding door, "I've been working in the yard this morning. I did yard work for beer money during college, and now its just a habit."

"Yeah, even from here I can see it's nice back there. It's good work." 

"Ah, thanks man. Want to go take a quick look?" he looks genuinely proud of it, I haven't seen him actually enthusiastic about anything during our time at work or at lunch. He's usually such a cool customer.

I give him a crooked smile, "Sure." And start to get up.

As he's getting up, his shorts shift around it's obvious he's packing a sizable dick, and that he's wearing something that's keeping it all in place, briefs or something maybe. 

He leads me around the small dining table to the sliding door. Jackson's in front of me sliding the door open to let us out, and i see he has light freckles on his strong shoulders. That's not something I've found hot before, but it looks good on him. 

I shake my head. God, stop thinking with your dick you absolute perv. Not every guy wants on your cock. 

We step out into an immaculate backyard. The grass is perfectly green, and looks like it was trimmed by hand with scissors. There's topiary bushes around the perimeter, in front of the fence that are faultless, and surrounded by flowers that would put an English garden to shame.

"Wow..." I'm kind of speechless. It's not what I was expecting after the brodeo in the living room. 

"Yeah... i would do this for the extra money for my car, like I did in college, but it just wouldn't work with my current schedule." I can tell he's proud though. "I guess that means we can talk about the alternative eh?" He shrugs his head towards inside. "Wanna smoke out and talk about it?"

"Uh... sure? I haven't smoked pot in ages. I'll have to take it easy."

"No worries man, I like to smoke a bowl post yard work. It's a tradition at this point." 

We make our way back inside, and I catch a whiff of his soap as he walks close by me. I feel my senses on edge with how Jackson's opening up around me. I'm not sure if he’s noticing my cock starting to snake every so slightly across my hip. I'm not huge, but bigger than average at almost 7 inches. Cut, with a fat head, and I’m fairly thick. 

Since I'm wearing these shorts, I'm in a pair of bright red briefs, that have a little trouble containing my ass, and my dick when it starts getting hard.

We take our places back on the couch, but Jackson sits more sideways this time, with one foot behind the other knee, towards me. I don’t want to put my prick on display at this point, so I sit forward, but man spread a bit, and lean towards the coffee table and its paraphernalia.

"Could you hand me the baggie, a bowl and the ashtray, I'll get it packed." I hand him the bowl and baggie, and then set the ashtray between us. He methodically gets it all ready and says, "this is pretty good shit. Jordan gets it from a friend that grows their own." He's so different than he is at work. I feel like he's barely the same schlubby, mousy guy I have my lunch break with. 

When he's done he hands the baggie back to me, and points at the bong, which looks like it just got refreshed with new water. While I hand it to him I say, "well, I'm used to shitty southwest weed. This Oregon stuff always knocks me out. I'll have to be careful."

"Ah, your fine dude. This is a safe space. You can hang out as long as you need to feel safe to drive."

Jackson lights up the bong, and takes the biggest fucking rip I've ever seen. He tilts his head back, exposing his beautiful neck, and exhales while handing me the bong and the lighter. 

I at least have my shit together enough, not to take a giant hit. I offer it back to him, and he shakes his head so I set it back down on the table. 

We both take a swig from our drinks. I lean back and stare at the ceiling for a sec. When I glance over at Jackson, he has his arm resting on the back of the couch, holding his head up while staring off into space, seemingly lost in his own thoughts. I take the chance to scope out his body again. The way his bicep bulges, again an exposed nipple, and his package looks barely contained by whatever he has on under his shorts. 

I say, "I dunno if I've ever seen you this relaxed Jackson." I can feel the weed and cider slowly having a nice mild affect. 

He brings his head around to me, and seems to come back to Earth, “I don’t wanna make waves at work, so I try to be as low key as possible. All those team building exercises and trying to force us to be all buddy buddy wear me out… y'know what I mean?”

“totally man,” I reply a bit groggily. I scoot down the sofa a little to get comfortable, and put my hands behind my head.

Jackson drinks from his beer, and seems to settle in, “So anyway. Can you tell me anything about stripping? I mean, I’ve been to strip clubs, and gotten a lap dance or two from a chick. But are gay strip clubs different?”

Jackson is ready to talk business it sounded like. 

I shift my shoulders a little as I try to figure out how to talk about it, "Well I've never been to a straight strip club, I've seen them in movies and stuff I guess... So I'm not sure how different they are." 

I'd gone to a gay strip club when I first came to Oregon, just as a lark one time, I had been a bit buzzed too, so my recollections weren't the best. I stare off at the ceiling as I go over it. It feels a little awkward talking about it with a guy who's given me every indication he's straight. "There was usually just one dancer at a time, and then a few gogo dancers, from what I remember."

I look over at him and say, "This is gonna be some 'pretty gay shit'... You okay with me going into detail about it Jackson?"

He's still holding his head up with his arm on the back of the couch, and his other hand is holding his beer. "Well I'm going to be doing a whole lot more than just hearing about it eventually right? I'm an adult, I think I can handle it." Then he smiles, "if you can."

"Hah!" That gets a chuckle out of me. "Well, the gogo dancers danced in cages, I think mostly to keep the more lecherous old men away. There was a stage, and I remember 2 of the main strippers. One was this pretty hot Hispanic guy. His dance wasn't great, but... he had a wild closer..." I pause for a sec, and unconsciously adjust my dick. I hadn't realized I'd kind of put it front and center by scooting down the couch to lean back. 

Jackson doesn't seem to notice, but he's looking at me intently, "what'd he end up doing?"

"Well, he had just a gigantic dick, and he strips down to a shear thong. i think those are required? Anyway, he had to be probably 11 or 12 inches long, and you could see all of it. Fuckin' thick too, and he wasn't even all the way hard. So anyways, at the end he takes off the thong, lays down on the stage, with his fat cock just laying on his stomach, and flips his hips up so it's now hanging in his face, and proceeds to such on the first 2 or 3 inches of it. Just for a couple of seconds though, it's not like he blows his wad all over his face. It was memorable as fuck though."

With the pot loosening me up. I can't help being totally hard at this point. I dunno what to do about my cock which is now stretched across my hip. Thankfully precum isn't leaking through my shorts... yet.

Jackson says, "Wow... well, I'm not quite that flexible." He shifts a bit on the couch when I look over at him.

I look down at my crotch, sheepishly. "Sorry dude, between the pot and all..." I adjust my dick again, and shift around to make it a little less obvious, which isn't really working. 

He looks down at my crotch and he lingers for a second, "Oh, no worries dude. I get it, and I guess his show had the intended effect eh? He must've gotten some pretty good tips out of that. They get tips like at a straight strip club i guess?"

"Oh yeah, I think I slipped him ten bucks or something heh. Afterwards, he put on some white running shorts. You know, the kind that are really short, and have slit up the side?"

Jackson nods, "Oh yeah, I've got some of those that I wear, but I put on some compression shorts under them when I go out for a jog. I'd end up flying out of those otherwise," he says with a chuckle.

"Well he's down in the crowd, which is kinda small, but people bunch up around him, and we tipped him then. I stayed back a bit. I figured I'd have to deal with getting groped as much as him if i got mixed up in that crowd of old handsy dudes, without the benefit of the tips." 

Jackson arches his eyebrow at that, "So the people were pretty 'hands on' with the guys?"

"Very much. He eventually went off to a backroom with some guy when the next stripper came on stage. I don't think it was just to play some connect four or battleship, but who knows. I didn't quite have the desire or cash to see what the 'champagne room' was like. Probably, mostly it was the cash." I smirk.

That seems to give Jackson something to think about as he finishes off his beer. I watch as he tilts his head back to get the last drops. his Adam's apple bobs. I never really though of myself as a neck guy, but I can't help but fantasize about what his would look like getting stretched out by my cock while he's getting throat fucked. My dick pulses a bit with the imagery.

"You ready for another cider Zander?"

Jackson was looking at me expectantly, "Uh, yeah sure." I down the last of the cider, and hand him the empty bottle as he unfolds himself from the couch and gets up. 

I stare at his ass. The shorts cling perfectly to his cheeks and stick in the split between them. With his dick being held in so well, and his ass so exposed, it makes me think he's gotta be wearing a jock strap. My dick pulses thinking about it. It wouldn't be long before there's a wet spot from the precum if this keeps up.

As he walks to the kitchen he asks, "so what did the next dancer do? Anything as wild as sucking his won dick?" 

"Nah, the next guy was cute though. He was white. And had a shaved head, looked like he shaved his chest too. I like a bit of chest hair myself, but he still looked great. He was a much better dancer. He hit on me a bit when he came down off the stage after."

Jackson was coming back with our new drinks, which were already covered in condensation. He has an amused look on his face. "Oh really good to know about the body hair..." He pauses, and asks,  "Did you hook up with him?"

"Not gonna lie, I was tempted. I had work in the morning though, so I didn't have the time. He was sweet though. Had a country boy who came to the city vibe." I laugh and say, "He may have been looking to turn a trick anyway and I didnt have the money for that."

"Wow... sounds like there's not much of a line between being a stripper and a gigolo" Jackson has a little bit of a worried expression on his face as he gets back to the sofa. 

"I don't think everybody was selling sex but... it had the vibe." 

Jackson points at the bong, and i grab it to hand it to him. He checks the bowl before lighting it up and taking a more modest hit this time. He still tilts his head back to blow out the smoke after holding it in for a while. He hands it back to me, and I take another hit myself.

I lean back again, with my head resting on the back of the couch and tilt my head towards him.

I'm starting to feel pretty buzzed, but in a good way still. I care a bit less about how it appears, and openly drink in Jackson's body with my eyes. He doesnt seem to notice or care.

Jacksons says, "Do you remember what they wore when they stripped? Had to be easy stuff to get out of I'd guess."

"Hmmm, I remember one guy had tear away pants with some bootie shorts under that, then some bikini briefs, and finally just that see through thong. It's just a pouch really, so they can swing their dick around and stuff."

Jackson shrugs at that, "Oh... i don't have anything like that. I mean I've got everything else, but not a thong..." 

I laughed, "I think that's something you'd get when you strip. The thing looked so flimsy. I'm not surprised you don't have a stripper thong. Why does every straight dude have tear away pants though?" I asked in a bemused way.

Jackson smiles, but blushes a little. "makes sense when you're gonna go play basketball with friends, and want to feel like Kobe?" he chuckles, and then gets a little serious, but he's still blushing, "Could I put on that kinda outfit, and have you tell me if it looks good?"

I had kinda been waiting for this, but I wasn't sure if he would have the balls to try. "Um sure. It's good to get a second opinion."

He sets down his beer, gets up to head down the hall towards what I assume is his bedroom. "I'll be right back."

I let out a big breath, adjust my cock, and take another swig of cider. What the fuck have I gotten myself into? All I can think about at this point are his lips wrapped my prick, or his legs wrapped around my waist as I pound his virgin hole. 

I wonder what his moans would sound like as the head of my leaking cock pushes against his resistant, cherry pucker.

He has to know what effect this is having on me. I have to keep it at least a little cool though. I dont want to scare him. I like to be in control which can turn guys off. Not everyone likes someone dominating them. Plus, he may just be one of those guys that just likes attention from gay dudes. I've met those too.

Just as I start calming myself back down though, Jackson comes back into the living room.