Life after Sylvia Ch. 03

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Michael finds out what it's like to be a stripper.
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Part 3 of the 8 part series

Updated 06/10/2023
Created 12/04/2020
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m_storyman_x
m_storyman_x
10,449 Followers

Chapter 3

Dating had gotten quite complicated in the months after the canoe trip. I was still seeing Crystal, and with her consent, yes I really did ask first, I was seeing Donna and Tanya, neither all that seriously, but frequently enough that I wasn't at a loss for someone to have sex with when I was interested. Donna had made it a point to seduce me at work on several occasions before I agreed to date her, and Tanya, having less opportunity at work, frequently stopped by my house unannounced. She seemed to always show up in some manner of provocative dress, including on one occasion, completely naked. She seemed to be searching for the one outfit that would entice me to have sex quickly, something that she never seemed to fail at, though sometimes with more effort than others. I wasn't sure she was really interested in a long term relationship as much as a physical one.

But Crystal was still my first choice and my most frequent date partner. Dinner, movies, talking, walking, taking a hike in the woods and even riding bikes. I'd introduced her to fishing, one of my favorite pastimes, and had gotten her all the appropriate clothing for deer hunting, which started in only a few weeks. She seemed to be honestly interested in building our relationship aside from the sex. As she put it, "I could get all the sex I wanted any time I wanted from any number of women," but she seemed to want to convince me that my lower head and my heart weren't necessarily attached. I was beginning to suspect she was right, but try as I might, I was still having a hard time getting past the guys playing with her and touching her during her show. I think she still new that, especially when we were having sex.

Crystal had taken to coming over most nights that she worked, letting her sexual energy vent on me in bouts of wild sex, often followed by long quiet nights sleeping together. She'd promised not to do any more guys in the dressing room, unless I either said she could, or told her we were done. To date, I'd told her I didn't control her, but she was still set on trying to make me her sole sexual partner, even while she was encouraging me to have sex with the ladies at work.

The problem was, the more I saw of Donna and Crystal, the harder it was for me to think of being with only one of them. I was definitely developing feelings for Donna that were starting to rival the intensity of the almost instantaneous feelings I had for Crystal. I wouldn't believe in love at first sight if it had not been for my ex-wife, but that's what Crystal felt like, intense love at first sight.

If I were pushed to choose one right now, I doubted I could. I also knew that keeping both of them, especially in this way, was impossible in the long or even relatively short term. As if things weren't complicated enough, Marge had become an occasional sex partner. She made visits or took me on short trips which almost always ended in some form of sexual play, including several very seductive lap dances. Sometimes she'd just stop by my office to ask how things were going, and sometimes she'd come by my house in her red Mercedes for an evening of casual sex, always culminating in a discussion of how I was feeling and doing. She seemed genuinely interested in helping me sort through my confusing jumble of emotions and find an appropriate, willing, sexually active partner, even if it meant an end to our periodic interludes.

Of course, she was contributing to that jumble in some ways. I always felt guilty having sex with the boss's wife, no matter how many times she had assured me that it was fine by all concerned. I'd talked it over with Crystal on several occasions, and each time the discussion ended in both rather energetic sex, and her pronouncement that this was just something my heart was going to have to sort out on its own, and she was quite willing to wait for that answer. Of course, she hoped that it ended in her favor, which she was doing her best to encourage.

Let's face it. The only real reason I was hesitating was because of her stripping. I just had a problem getting past that, even though Marge and Donna had on several occasions reminded me that I was executing a classic double standard, given my current arrangement of partners. It didn't particularly surprise me to find out that Marge had sought out Crystal and gotten to know her, the two now being quite friendly. I was a bit more surprised to find out that Marge took the time to know which nights Crystal worked, ensuring that she didn't come by and "use me up" before Crystal could come by after work. All in all, this was a sexually satisfying time and an emotionally tumultuous time.

"Hey there lover boy!" Marge said as she walked into my office late one Wednesday afternoon. It was more than late enough to quit for the day, but I still had some paperwork to finish up on the project I was working on, which had kept me a bit past my normal quitting time.

"Marge. What's up?" I asked, looking up from my computer and swiveling my chair to face her. She was dressed in a VERY short dress, the hem of the skirt so short that I could see the tops of her thigh high stockings peaking from under the skin tight red skirt material. The top of the dress was sleeveless and quite obviously backless. The entire front of the dress seemed to be little more than loose folds of material circling around her neck and hanging down until it attached to the waistband of the skin tight skirt portion. The material hung down loosely over her big breasts, which seemed to almost show through the thin material as they wiggled side to side, completely unrestrained.

"Well, I'm taking you out," she said, setting two large shopping bags on my desk and then turning to close my office door. "But you definitely can't go out like that," she said, pointing to my button down dress shirt and dockers. "I got you something more appropriate to wear."

"Oh?" I asked as she stepped back to my desk and started to pull items from the two bags.

"Of course. Go ahead, get undressed," she practically commanded, pausing her unloading to stand and look at me. "Unless you want me to come do it myself, which I wouldn't mind at all!"

"No, that's fine. I'm sure I can undress myself," I said, shaking my head as I pushed my chair back and bent over to untie my shoes. By the time I had my shoes off, she had the bags unloaded and was standing next to my desk looking at me expectantly. I stood up and she reached for my shirt and started to undo the buttons.

"You know that I care about you, right?" she asked as she undid the buttons of my shirt and pushed it off my shoulders.

"Yeah," I answered as she pulled my t-shirt from my pants and pulled it up over my head.

"I care about you both as a good friend, and as my lover," she said as she tossed the shirt aside and reached for my pants, quickly undoing my belt.

"Yeah, I understand that," I answered her curiously as she squatted on the floor in front of me, pulling my pants down, waiting patiently for me to lift my feet so she could pull them off. She reached up for my briefs and pulled them down as well.

"These need to go too," she said with a grin as she pulled them down my legs, leaving me standing there in nothing but my socks. "Ohhhhh yes. Such a nice cock. What say we make this all nice and hard?" she added as she leaned towards me and engulfed my cock with her wet lips.

"Oh geez," I groaned softly as she quickly sucked my half hard cock, causing it to grow rapidly.

"Mmmmmm," she said, pulling her face from my cock. "I know I said I wouldn't have sex with you at work anymore, but how about we have dessert before dinner today?" she asked as she stood up. She reached behind her neck and pulled the looped material over her head, dropping it down the front of her, leaving her bare from her hips up. With a smile she reached for her hips and wiggled them, pushing the red dress down over her hips until it slid down her legs. She stepped from the dress, leaving her in nothing but a pair of thigh high nude stockings and five inch red high heels.

"Marge..."

"Shhhhhh," she said putting her finger to my mouth for a moment. She smiled and reached down to my arms and steered me back to my chair, pushing me back until I had to sit down. Reaching for the back of my chair for support, she stepped herself over the chair, her thighs resting on the arms and her legs spread wide in front of me. "Why don't you help guide yourself into me?" she cooed softly, rocking herself up on her thighs to lift herself high enough for my cock to move under her pussy.

Knowing that she was not to be denied when she got an idea into her head, I reached down and pressed my cock towards her pussy, letting her slowly lower herself down until my head engaged into the entrance to her sweet tunnel.

"Ohhhh yeah lover. Just what I need," she moaned as she slowly lowered her wet pussy down my shaft.

"I think someone's been thinking about sex for a while today," I said, reaching up to cup her large tits, squeezing them slightly and running my thumbs back and forth across her hard nipples.

"You have no idea!" she moaned softly as she began rocking herself on the arms of the chair, using her legs to lever herself up and down and her arms to balance herself. Up and down she moved, lubricating more and more of my shaft until her bare ass was slapping lightly against my thighs, my cock driving up into her until my head pressed against her cervix and the end of her tunnel.

"Ohhhh God," I groaned as she rode up and down, my own hips trying to stroke up into her in time with her motions, driving us both wild.

"Michael... You know...that I care about....you deeply...Right?" she asked breathlessly between strokes as she drove herself up and down my fat shaft.

"Uh huh," I agreed with a groan.

"And you...know that...I wouldn't...do anything...to hurt you...right?"

"Uh huh."

"I want you...to do something...for me...tonight."

"Sure, what?" I groaned, feeling my climax growing closer by the second, her pussy starting to quiver and clench around me as her own orgasm inched ever closer.

"Trust me...and do whatever...I ask tonight... Okay?" she practically begged, her legs and arms trembling.

"Okay," I groaned as her pussy spasmed around my cock. "Oh shit," I grunted as my orgasm hit, causing me to jerk and jam my cock up into her spasming pussy. I felt my cum surge up into her, filling her pussy as my body jerked over and over again, her whole body shaking and trembling as she sat on me, her arms moving down around my neck and pulling her chest toward my face.

"Ohhhhh God yesssss," she moaned softly as her trembles and shudders started to subside. I wrapped my arms around her waist and held her as she pressed her breasts gently to my face, her lips softly kissing the top of my head.

"So what do you want me to do?" I asked after I could breathe more normally again.

"You'll find out. I just want you to promise that you'll do what I want and not ask questions."

"Kind of unusual."

"I know. But you trust me, don't you? You know I wouldn't ever do anything to hurt you."

"Yeah, I believe that."

"Then trust me tonight. Know that no matter what, this is something I believe will help you in ways you can't imagine."

"Now you have me very curious."

"And that curiosity will just have to wait," she said with a smile, pushing her body back from my face so she could look down at me. "Michael, I care very much about you, but I also know that what we have is fleeting and temporary. It can't last, so while I can, I would like to try and do something that can last. You'll just have to trust me that tonight is more about your happiness than anything else. Okay?"

"Kind of mysterious, but okay. I'll trust you."

"Good," she said with a cheerful smile. "Time to get dressed then."

"If you say so," I said as she pushed herself off me, my cum dripping from her spread pussy as she slid back off the chair.

She turned to the desk and pulled a cloth from her purse and wiped my cum from her pussy, holding the cloth against her pussy while she clenched her legs together to keep it there to catch our combined cum. "Here, start with these," she said, holding out a pair of bright red silk boxers.

"Seriously?"

"No questions remember?" she prompted with a little tilt of her head and raised eyebrows.

"Yes ma'am," I agreed.

"You know Michael, someday you're going to have to stop calling me that."

"Yeah, I know. I can't help it."

"Do you do that to Crystal too?"

"Actually, I do," I said with a chuckle as I stepped into the boxers.

"Wait a second," she said quickly kneeling down. "We don't want to leave cum stains in your boxers, not tonight." She grinned, leaning towards me and engulfing my cock in her mouth again. She only sucked and licked me for a few short minutes, and by the time she was done, my cock was half hard again but cleaned of any sign of our recent coupling. "There, that's better," she said as she stood back up.

I chuckled and pulled my boxers up while she turned and got a pair of soft denim pants off the desk. She turned and held them out for me, leaning her nude body against the desk to watch me dress.

"Perfect," she whispered as I pulled the pants up. She held a shirt out for me and I unfolded it, revealing a western style shirt with pearled snaps on the pockets, down the front and on the cuffs. "OH Yessss!" she said quietly with a grin while she watched me snap it up. "Have I ever told you that for a thirty-five year old man, you have a pretty sexy looking body? Not rock hard, but firm in all the right places, showing just the right amount of muscle."

"Yeah, I think you say that every time you get me naked."

"Mmmmmm. Good. I'd hate for you to not realize just how sexy you look," she said as she turned again. She pulled a box from the desk and opened it, pulling out a pair of very fancy looking pointy toed cowboy boots.

"Seriously?"

"Gotta have my cowboy looking like one all the way to his feet, right?" she said holding the boots out.

I stepped into them and frowned. "They fit perfect. How did you figure out what size?"

"I have my sources," she answered him.

"Uh huh. These look suspiciously like a pair of boots that I tried on a few weeks back for Crystal at that big western store. The ones that I said were way too expensive for either of us to buy."

"Huh, imagine that?" Marge said with a crooked grin. "Guess I better dress now."

"I suppose," I said, bending over and picking her dress off the floor. It took me a moment to find the right combination of holding to get the skirt open for her to step into, pulling the material up her legs and over her hips. She smiled and waited patiently for me to straighten the front of the dress and then pull it up as she dipped her head down to allow the floppy loop of material to go over her head.

"You know, you've gotten quite good at re-dressing me. Do you actually enjoy doing it or do you just do it because you feel like you have to?"

"I kinda like it. Besides, it gives me a last chance to play with your body," I said as I reached into the front of the dress and cupped both her big soft tits, teasing them inside the red material.

"Ohhhh, you bad boy! You know how sensitive my nipples are after we've had sex!"

"Uh huh."

"You keep that up and I'm gonna have to pull your pants down and let you bend me over the desk."

"Mmmmmm, that might be fun."

"I KNOW it'd be fun. But not tonight. I have other plans for you. But I promise, any other day you want, all you have to do is ask, and that delight will be yours!"

"If you insist," I said, slipping my hands from her dress.

She leaned towards me and pressed her body against mine, lifting her lips to mine in a soft seductive kiss. "God you're a sexy man!" she whispered before pulling away from me. "Now, off to dinner."

"Yes ma'am," I answered as I bent over and picked up my clothes. She took them from me, stuffed them into one of the shopping bags and then headed to the door with the bag, my clothes, keys and wallet all now under her control, exactly what she apparently intended.

I followed her through the office area, getting a little wolf whistle from the one of the female engineers that was still there working late. "Seems like I'm not the only one who thinks you're hot looking," Marge said as we walked out the front door towards her car.

"So it would seem. I take it that's part of your plan. Am I your boy toy tonight?"

"You promised me no questions, and no, you are NOT my boy toy, or any other kind of toy!" she said a bit sternly as she started the Mercedes. "You are an incredibly intelligent, sensual, sensitive man. One I care about almost as much as my husband. I would never consider you as disposable as a TOY!"

"I'm sorry. I didn't mean to offend you."

"I know," she said quietly. "But as I said, trust me, and don't ask questions. Just go with the flow tonight, please!?"

"Okay. I'll try," I said, reaching over and giving her stocking covered thigh a gentle squeeze.

We sat quietly the rest of the drive, the Mercedes turning and twisting down little back roads around town until we pulled into our destination. To say I was surprised wouldn't even begin to cover it. "Here we are," she said as she pulled into a parking space in the lot in front of the strip club where Crystal works.

"Um..."

"Michael! No questions! You promised!" she said sternly.

"Okay," I said a little defensively, wondering just what she was up to. I got out of the car and followed her to the front door which was opened, not by a burly bouncer, but a young guy in a pair of very tight pants, a white collar and no shirt. Normally the club is filled with guys leering at the dancers on stage, but tonight the club was filled not with men, but women, ranging from twenties all the way to the fifties, all sitting around the tables eating. Men dressed similarly to the young guy who opened the door milled about, filling drink glasses and carrying away empty plates.

"Ah, here we are," she said as she led me to a table with a gold "reserved" placard sitting on it and several young ladies sitting at the table eating. It only took a moment for me to realize that I recognized two of them, one being Tanya, wearing an extremely sexy spandex dress, and Donna in an equally sexy strapless dress that was formfitting to her big breasts. "Girls. Glad you could make it," Marge said as she sat down. "Michael, you of course know Tanya and Donna. You might remember Samantha, although the last time you saw her I believe you were making a mess on the hood of my Mercedes."

"Oh Lord," I groaned, covering my face with my hand briefly.

"Oh don't worry. You two still owe me a car wash, but I'm willing to wait to collect. I'm looking forward to helping the two of you wash it," Marge said with a smile. "And this is Jennifer, a friend of mine," she added, motioning to a tall thin blonde woman a bit older than I am. She had on a blue dress that was quite flattering for her slim figure, and a pleasant smile as she held her hand out across the table for me.

"Pleased to meet you," I said as I shook her hand gently, noting that there was one empty seat at the table yet.

"My pleasure, trust me!" she answered with sexy smile, her eyes looking up and down my body like a piece of meat at a delicatessen.

We were no sooner settled when a young man came by, setting a drink down in front of each of us, without any prompting for an order. To my surprise both drinks were our normal choice, mine a light beer and hers a margarita.

"It would seem we were expected," I said loud enough for her to hear me over the din of the several dozen women talking.

"So it would seem," she responded noncommittally. "Trust me, remember?"

"Alright," I said a little nervously.

m_storyman_x
m_storyman_x
10,449 Followers