Working as a Male Stripper

"Thanks!" I stood there with my clothes in a bundle under my arm, my cock still at half-mast. I was still horny as hell, but I got the distinct impression, we were done for the evening.

###

The next morning, I woke with a desperate need to brush my teeth. I hadn't used the toothbrush the night before, but certainly needed the morning after. While brushing my teeth, the daughter knocked on the door. "Are you decent?"

"Yes," I chimed, mouth full of paste.

She stepped into the room. "Good morning. We have some Danish if you're interested, and coffee."

I stepped out of the bathroom naked, to say hello. She was dressed in a long t-shirt which hugged her lovely breasts and fell to just above mid-thigh.

She smiled, "I like your pajamas."

I stepped into the small bathroom and spit out the toothpaste. "Thanks, I'm not a coffee drinker, but the Danish sounds incredible." Stepping back out, I notice she was sitting on the end of the bed and the door was still open. "I don't typically wear pajamas and I figure you saw it all last night. No need to hide."

"Thank you, for last night and this," she says gesturing to my naked body.

"Anytime. Should I go out to breakfast like this?"

Eyeing me over, she shook her head. "As much as I'd love it, I think my mother would prefer you put on at least a shirt."

"Is a shirt enough?"

"If I remember right the tails are long enough to cover you."

I smiled. My shirt was draped over a chair on the other side of the room, so I had to pass by the daughter to get to it. As I did, she reached out and caressed my hip. She probably would have stopped there, except I stopped. Her hand felt nice. And although I wasn't hard, I was still very horny. Understanding the unspoken offer, she glided her hand over, running her fingers through my pubic hair. As her fingers slid along my cock, it responded rapidly growing with her touch.

Three or four caresses later, I was sticking straight out. "I'm not sure I should go to the breakfast table with a hard on."

"I don't know." Caressing my cock, she gazed on with fascination. "If you can cover it up enough before you sit down, it might be fun." Her nipples were poking out at the thin t-shirt fabric, hard as nails.

I reached over and lightly touched her breast. She took in a deep breath but didn't move away. Her free hand slid to the edge of the t-shirt draped over her legs. Pulled it up to reveal she was wearing nothing under her night shirt. "See, we would both be going commando." Her dark pubic hair was thin, lying neatly against her body. The lips of her vulva engorged and slightly separated showing the top of her clit.

It was everything I could to not to just fall onto my knees and bury my face between her legs. Instead, I turned to her, my cock pointing right at her face. I squeezed her breast and moaned.

She wrapped her hand around my cock and squeezed. She looked at my cock and sighed. For a moment, I thought she might suck on it. I knew if she did, there was no turning back.

Then, from the hall, her mother called, "Lindsey, John, breakfast is ready."

As she raised her head to look me in the eye, leaned back slightly and spread her legs. She was soaking the back side of her t-shirt. "Fuck, I want this. But my mother is expecting us." She took her free hand, then ran a couple of fingers along her cunt. She shuddered, pulled the hand up, and rubbed the wet fingers along the seam of my cock. Finally, squeezing my cock, she said, "Get your shirt on."

Using my cock as a hand hold, she stood up. Still holding on to my cock, she pressed herself to me, sliding my cock between her legs, soaking the top of my cock. My butt clinched and my cock throbbed. My hand was resting on the back of her waist. I felt the urge to put my hands under her ass, lift her up, and fuck her right there. But her mother was waiting.

After a heavy sigh, Lindsey left, and I put my shirt on. I needed to hold the edges of the tails down to keep my cock from sticking out the front, but I managed to get to the table without showing too much to my boss.

I was seating at the head of the table again, Lindsey to my right, and my boss to my left. We had heated Danishes, coffee, and milk. Well, I didn't have coffee, but I did enjoy a couple glasses of milk. The conversation was uneventful. Some of it was talking about how to market the new service; some of it was talking about the one gig she already had, the reason she wanted me to do this is the first place. It was a regular client, who ordered a half dozen telegrams a month, and willing to pay a sizeable extra for the stripper. My first job was going to be at a warehouse on Friday, for the female accountant.

Lindsey cleared the table while my boss walked me back to the guest bedroom. When we stepped in, she closed the door. I started to take off my shirt. Once undone, I turned to her, my cock still half-mast. She stepped forward and took hold of my cock. I leaned in to kiss her, but he stopped me with her other hand. "John, as much as I can appreciate this," she squeezed my cock and started slowly stroking it. "I am old enough to be your mother and have been divorced three times. This couldn't possibly be anything more than a fuck, and I value you as an employee. I don't want to screw that up like I have my marriages." She was wearing tan polyester pants and a loose shirt. She slid inside the front of her pants and obviously stuck a finger (or two) in her cunt). Sliding it back out, she pulled her hand up to my nose, her other hand still caressing my cock. The smell of her juices was intoxicating. "Obviously, I want you, but I need to say no. I hope you understand."

My head said yes, but there was no part of my conscious mind that agreed. As much as I wanted to fuck her daughter half an hour earlier, I was more than willing to dive onto the bed and do my boss. I was beginning to twitch.

She realized how close I was to cumming. She stopped stroking and looked down at my cock. "Mmmm," she hummed. "You are pre-cumming." A thick ball sat on the head of my cock. In slow motion, she bent over and lightly took the tip of her tongue and licked off the pre-cum.

Fuck! It wasn't enough to start me cumming, but it did make my balls ack!

When she stood back up she said, "My daughter hasn't made the same mistakes I have, but I already know that if you and her were to, well, it would end badly, and she'd be heading down the same path I did. So, I'm asking." She gripped my cock like a handshake. "If you can, don't sleep with her either."

I grunted my assent. Or at least I think that's what happened. I grunted, and she took it that I agreed.

###

The warehouse job went off without a hitch. Lindsey was my 'bodyguard' always riding with me to the various appointments to ensure nothing went wrong, and the customers were happy. Afterward, Lindsey wanted to drive to her house to relax. I knew that wasn't a good idea. Even though the strip at the warehouse was generic, stripping is still a turn on. If I ended up at Lindsey's house, we would end up in bed. I made up an excuse that I had an early morning with my other job the next day. It was a lie, but it prevented us doing something I would regret.

Three weeks later, three strips later, the same question popped up each time. "How about we head over to my place for a glass of wine or something?" After the fourth strip, I told Lindsey I'd promised her mother I wouldn't miss business and pleasure. I didn't give all the details about how close I'd come with her mother breaking that same promise, but my sentiment was earnest. Lindsey drove me to my apartment and never mentioned it again.

Occasionally, she would tease me saying, "Just so you know, I'm going to go home and masturbate. I know you can't come along because of your promise. I just thought maybe you'd want to know what my plans are this evening." Eventually, I started teasing her back saying, "Yeah, well, me too. But I'm not going to tell you who I'm thinking about when I do."

Over the few months I did two to three strips a week, steering clear of sex with either Lindsey or my boss. It wasn't enough to really pay the bills, but it definitely helped.

###

Six months later I got hired to strip at a local strip joint. It was to happen on a Wednesday evening as a birthday gift for one of the strippers. The joint only had female strippers on staff and didn't really cater to the crowd that would enjoy watching a man strip. However, Wednesday's were slow, so the manager was going to let me show off for the girls.

I arrived at the club, handing the bar tender my tape, and sat down in the audience. Lindsey, dressed in a dark clingy top and long black skirt, lurked in the back corner, trying to look inconspicuous. Women didn't frequent the club very often unless they were looking for work. The room was dark; the only light coming from the lights bouncing off the stage, and the few lit signs behind the bar. My target wasn't on stage, but her friend, Darla was. She hired me and knew my act—stripping from a tuxedo to a tuxedo—so, when I walked into the room, Darla smiled ear to ear. There wasn't any other clients. She was dancing for me and the bar tender. The lack luster performance suddenly got quite animated.

Darla finished her three-song set then came out to talk to me. She sat down in just her G-string, wrapped her arms around my shoulders, and said, "I'm so glad you could make it. Do you want something to drink?" Her not so recently died long blonde hair was frizzy and flew everywhere. Her thirty-something breasts were large and hung naturally down her front. Eventually, years of dancing wouldn't be kind to her, but at the time Darla was reasonably pretty, even though her hard life was beginning to show around the edges.

Ever since the night of stripping for my boss and her friends, I avoid drinking when I'm going to strip. I can't afford to go too far. "Thanks, but not, maybe a glass of water."

"How about a coke? It won't look like you're a plant."

"Ok, a coke is fine."

Darla gave me a peck on the cheek and went to the bar. The bar tender announced the next act, "Gentlemen, put your hands together for Charlotte."

Charlotte was a busty woman in her mid-twenties. Long dark hair flowed about her broad shoulders. A light blue tube top allowed her breasts to bounce as she pranced around the stage, while her tight faded Daisy Duke cutoffs hugged her hips. She danced and gyrated for me on stage, while Darla played like I was her new sugar daddy, clinging to me, draping an arm over my shoulders, and rubbing her breasts up against me. She even went so far as to pull my hand off the table and down on to her thigh. After a few minutes, when it hadn't moved, she slid it further up, until I was inches away from playing with her G-string. I had a job to do. The position of my hand was making it so stripping to my G-string was going to be quite a show.

At the end of the first song, Charlotte took off her tube top to free her breasts. The bar tender interrupted the set to make an announcement. "Gentlemen, today is Charlotte's birthday, so how about we give her a treat."

Charlotte shielded her eyes from the lights looking for the bar tender, and to why he'd interrupted her set. She had no idea what was going on. Darla jumped up and grabbed a chair from the front of the audience. "Sit down, Charlotte, this show is for you."

The music from my tape began. Normally, I was a lot closer to my subject when the music began, so I had to take several quick steps to get up on stage. However, the moment I did, and the recognizable theme from "The Stripper" blaster over the speakers, Charlotte knew what was going on.

She sat attentive in the chair while I took off my jacket, vest, tie, and shoes. When I sat on her lap and started to undo my shirt, she enthusiastically grabbed my shirt and pulled, popping three buttons in the process. "oops," she said and grinned, then pressed her bare breasts to my chest.

My show wasn't over, and while I was enjoying the breast massage, I was here for a job. I slid off Charlotte's lap and unzipped my trousers. In typical style, I turned around to drop my trousers and let the audience (of one) see my tuxedo G-string first. Darla let out a whoop! I was half-way hard and praying I wasn't too stiff to finish the show.

As I kicked my trousers off the edge of the stage, the eager, waiting hands of Darla, I could tell my cock was enjoying this job a bit too much. While the G-string was still in place, it was a near thing. I'm sure if I were to let Charlotte rub her hands on me, my erection would be too much for the G-string to handle. I'd pop out and likely get arrested, no matter how much my target might enjoy the show.

I turned back around, but rather than hold my shirt in front of me, dropping it at the right moment, I held on to the sleeves to use the shirt like a boa around him hips. Shifting my hips back and forth in time to the music, the shirt kept my bulging G-string from being visible to the audience. I could tell by the look at Charlotte's eyes, she knew I was about to burst free, but no one else could tell. Reaching down, I took Charlotte's hands, and had her hold on to the shirtsleeves. I was dependent on her to keep the shirt up and the prying eyes of the audience, Darla and Lindsey, at bay. I grabbed the tie and slipped it behind Charlotte's neck. Pulling her head forward, I inched her closer to my G-string. Just as I was about to lift her head and give her a kiss, she took both sleeves with one hand, and slid the other hand to my cock. With a flick of her finger, I popped out over the top of the G-string. I was beginning to bend over as her head raised up for our lips to meet. She started stroking my cock as our lips and tongues pressed together. I was in no hurry to break the spell, but the music ended. Darla jumped up and started screaming. I could hear Lindsey adding her hands to the applause.

Charlotte and I broke off the kiss, and as graceful as ever, she slid my cock back into the G-string. I was too hard to really fit but sticking up the side was better than flopping over the top. Handing me back my shirtsleeves, she whispered, "You'd better get dressed."

At that moment, the bar tender announced, "And now back to our regular show." I got the hint. I wasn't going to draw customers in, so I needed to get off stage.

I grabbed my clothes and headed backstage to dress. As I was trying to figure out a way to keep my shirt closed without three buttons in the middle, Darla came bouncing back. "Oh my god, that was great. I've never seen her so embarrassed?"

"Really, I couldn't tell." I still had a raging hard on and needed to turn my back to Darla, so it wasn't too obvious.

"No, it was great, really. How much to have you do another show?"

"Out on stage? I don't think the bar tender would agree."

"No, backstage, sort of a private show for Charlotte. One where she can really enjoy the show and not feel embarrassed."

I'm pretty sure she did enjoy the show, but if Darla's willing to pay for another strip. "Let me talk to my boss. She's at the back of he bar."

The vest did a good enough job holding the shirt together that it didn't look obvious I'd lost three buttons. I met Lindsey and told her of Darla's offer. "How much for second strip? This one would be backstage."

"Well, we've already been paid for one. So, I guess it depends on what you want. I figure the money from this one is all yours."

"Oh, really, thanks!"

"But I think I should be present, just to keep things legal. It looked like things were getting close on stage."

"It was fine."

She nodded toward my trousers. Although they were black and the room was barely lit, she could see the outline of my erection. "I'm sure you enjoyed her grabbing your cock like that, and I'm also sure no one other than me noticed. But if things go too far, and someone complains, namely the customer, we could be in trouble."

"Charlotte's not going to complain."

"No, but Darla might. Part of the reason I think she wants you to do a private show backstage is so she can see you up close and personal."

"How do you know?"

"There's a difference when a woman's nipples get erect from excitement and when they're just naturally erect. Darla obviously has the hots for you."

"Oh." I looked over and Lindsey dark shirt was sporting erect nipples too. She typically didn't wear a bra, so the outlines of her nipples were generally obvious, but even in the dark, they are harder than normal.

"So, if it's ok with you, I think I'd better go backstage with you."

"Ok, good idea," although I didn't really think so. I was pretty such what would happen if Lindsey wasn't there and it was just me and Charlotte. Darla was an unknown and I didn't want to get arrested.

We went backstage as Charlotte finishing her set. I told Darla a price and she exclaimed, "Ooh, you're cheap. I charge twice that for a private party. But sure." She handed over the cash, which I handed to Lindsey. My trousers had pockets, but I didn't want the cash on me when I did the strip.

When Charlotte stepped backstage, Darla started bouncing up and down—still in her G-string mind you. "Charlotte, he's agreed to do another strip for you, a private one." And she winked and elbowed Charlotte in the arm.

Charlotte, wearing nothing but a G-string, so small, a tiny tuft of dark curly hair peaked out over the top, smiled. "So, do I need to get dressed, or am I OK like this?"

Darla spoke before anyone could get a word in. Oh, you're fine. He's the one stripping.

I stepped forward, "Charlotte, this is Lindsey, my manager of sorts. She's going to watch."

"Oh," Charlotte looks at Lindsey and then down at her breasts and the hard nipples. "You like to watch?"

Lindsey crossed her arms over her chest. "It's not that. It's just to ensure it's all legal."

Charlotte chuckles. "We're at a strip club. There's quite a bit going on here that's not legal, but I'm fine with that." She then turns to Darla. "Where should we do this?"

"In the back dressing room. It's small, but there's only four of us."

We headed to the back, to a small room off to the side. There was a chair, a mirror surrounds by lights, and a clothing rack with a half-dozen different bits of lingerie.

Looking around, I didn't see a tape player, "I don't have any way to play music."

"That's ok," Darla said with enthusiasm. "Just go with the flow."

I started to strip again. Being aware of Darla in the room and what Lindsey said, I was conscious of how creepy it was Darla always leering over my shoulder, wanting to get close, to be part of the act. The end result it helped me lose my erection.

By the time I got to covering my ass with my shirt, showing my G-string to Darla and Lindsey, I was back to normal. When I turned around and displayed my package to Charlotte, she noticed the difference too. A quick glance at her friend, and she understood why this strip wasn't quite as entertaining. I brought Charlotte in for a kiss, and it was nice, but there were no hand movements this time.

The kiss ended and Darla squealed, "Oh, I want one. Can I pay you for another strip, for me?"

I looked over at Lindsey, but it was Charlotte who spoke first. "Darla, sweetie, it's about time for your next set. Mica last song is about to end."

Darla cocked an ear and then swore like a sailor. She took two steps toward the door, then turned, "I'll pay you double if you'll wait."

Lindsey rode to my rescue. "Unfortunately, we have another gig in an hour, so we don't have time, not today."

I breathed a sigh of relief. Darla stepped out of the room frustrated and I bent over to reach for my trousers.

"Do you really have a gig in an hour?" Charlotte asked.

Lindsey didn't answer. She just looked at me giving me the out if I wanted it.