Chapter 6: Kate Finally Cheats

After the lingerie party, I didn’t hear from Kate for almost a week. It didn’t really surprise me given her reactions to past events and besides, I figured I would leave it up to her as to whether she wanted to continue our relationship given our last time together had been rather emotional and I wasn’t entirely sure how comfortable she’d been with that. Deep down, I knew Kate was madly in love with her husband, no matter how big a jerk he was. In her mind having sex with another woman was STILL sex and that meant she was cheating on her husband.

Over time I began to sense that the real reason she hadn’t masturbated in the past was because in her heart, that would be like cheating on her husband, even if it was just all a fantasy. Now in the past few months she’d made some dramatic changes in her lifestyle and attitudes, but I had to wonder if her husband was even aware of them!

Just as I was about to give up on her, I got a phone call out of the blue and it was none other than Kate. We talked about things, just general girl talk before finally the topic of the party came up. Even then, all she seemed to want to discuss was the modeling aspect without a hint of how she felt about our “private party” afterwards. The call ended up with us agreeing to get together for lunch in a couple of days, leaving me to wonder where her head was at. Kate had never been one to discuss personal things on the phone so I didn’t take the absence of any mention of her recent masturbation activities as a negative sign, but still, I had to wonder how the party had impacted her and if she was masturbating more or less since then.

We finally met at a local diner, nothing fancy with just a few customers which left us pretty able to talk about anything without having to worry about someone listening in. Again, we started with some general chit- chat while the waitress took our orders and then Kate leaned forward over the table an motioned for me to come closer.

“You should be proud of me - I can make myself cum now,” she boasted, as if she had just achieved some Novel Prize-winning achievement which, in a way, she had.

For anyone to go so long without ever having experienced an orgasm was virtually unthinkable to me yet I had to wonder how many other wives were in the same, boring, sexless lifestyle as Kate had been in when we met. If it hadn’t been for that lingerie party where we first met, she would still be home wishing her husband could get it up with no relief in sight!

“Does Bruce know anything yet?” I teased her, knowing full well her husband would probably be the last person in the world to find out his wife was playing with herself, finally achieving by herself what he’d never been able to do for her in twenty plus years of marriage.

“Oh god forbid no,” she quickly answered, then grinning even more broadly as she shared another juicy secret, “I even did it last night right next to him in bed while he was sleeping! Oh my god Kelly, I felt SO naughty!”

“So why don’t you do it in front of Bruce?” I asked, “Maybe it might provide some incentive for the poor boy downstairs to get back in the game again?”

Kate frowned and I almost wished I hadn’t asked. “He would just say I was being nasty. So far as he knows, I’ve never masturbated in my life and I don’t think he even cares if I cum.”

“Why he say it was nasty? I’m sure he jerks off all the time! What’s the big deal if you do the same?”

Kate’s eyes widened and she sat back a little as if what I had delivered some sort of revelation. “I wasn’t really honest with you I guess. Truth is, I’ve NEVER seen Bruce masturbate,” she confessed, “I’ve never even found a dirty magazine since we’ve been married. I just thought I should say ... well, I don’t know WHAT I thought when I told you that.””

Two thing immediately came to mind. Either Bruce had some serious sexual issues that were probably the root cause of his E.D., or he was doing one hell of a good of lying to his wife and hiding things! Fortunately, for once I managed not to blurt out my first thoughts and so I just left Kate to live in her fantasy world. Bruce didn’t masturbate ... yeah right! As my dad always said, ninety percent of men admit they masturbate regularly and the other ten percent are liars.

“So anyway...,” I injected, trying to change the subject before I said something I would regret later, “How often are you doing yourself now?”

Kate actually blushed and I saw her biting her lip just a little as if the answer was embarrassing to her. “Usually every day now.”

“Only once a day?”

Kate looked at me like I was some alien saying, “Why, how often do YOU do it?”

When I told her usually twice a day, sometimes three and once in a while more, her jaw dropped open in disbelief.

“But Kelly, you get laid regularly so why do you have to masturbate so much?” she asked.

Smiling, I tried to explain to her that it wasn’t that I HAD to masturbate, it was that I ENJOYED masturbating. For me, masturbation isn’t a substitute for sex, but rather something that compliments it. Sure I may do it more when I’m not getting the real thing regularly, but it’s not uncommon for me to do myself again even right after being fucked when the guy drops off, going for at least one more good orgasm! Simply put, I tried to explain, I just enjoy doing it for the sake of doing it, not because I am or am not getting the real thing.

“I guess I never really thought about it that way before,” Kate said with thoughtful expression as she seemed to try to mull this new concept over in her mind. “I just figured people only masturbated when they couldn’t have real sex.”

“Well, that just goes to show you shouldn’t feel embarrassed or feel like you’re cheating on Bruce just because you enjoy going solo,” I encouraged her, “Even if he WAS getting it up, that doesn’t mean you still can’t enjoy some personal quality time!”

We both giggled as the waitress brought us our order. She looked at us a little odd, probably wondering what we were so giddy about in the middle of the day but whatever, that was her problem.

“So tell me Kate, have your fantasies gotten any nastier now that you do masturbate more?”

Once again Kate got that “caught with her fingers in the cookie jar” look, as if she felt guilty for even THINKING such things, let alone tell me about them. “Oh my, it gets really BAD sometimes,” she said in a high whisper, as if afraid somebody might be listening to us. “I feel so guilty sometimes but yet at the same time, it’s really hot to think about stuff I know I’ll never do but still...”

“Oh? And just what might some of those be?” I inquired, actually quite curious to find out what this recently “converted” housewife might be fantasizing about.

“Well, there’s young man on our block who is JUST gorgeous,” she said, her face reddening a bit, “I’ve wondered what would happen if I needed someone to help me with some yard work while my husband was away on business.”

“Not bad, the classic naughty housewife,” I said, giving her a thumbs up, “But I KNOW you’ve been naughtier than that ... let’s go, confession time!”

Kate looked around, again as if fearful someone might overhear us but the nearest person was the waitress and she was twenty feet away at least.

“OK, here goes but you have to promise not to laugh,” she said with a smirk. I just grinned and nodded my head in agreement so she continued, “Well, you once told me about some of those bachelor parties you go to and the dirty things you do at them. Well, ever since the party we did I’ve been fantasizing about how it would be to dance in front of a bunch of horny men instead of a bunch of repressed housewives.”

Wow, now THAT wasn’t was I had expected to hear. Sheesh, talk about going from fairly innocent fantasies to hardcore in one giant leap! But then I thought again and realized she was just talking about the dancing aspect, not the sex. Or was she?

“Nude?” I decided to ask, pushing just a little but not going overboard.

Kate blushed and I knew I’d hit the nail on the head. “Well, isn’t that what you’re SUPPOSE to be when you dance at one of those?” I asked her.

Kate shook her head though and disagreed, “Maybe at yours but Bruce has been to several and he always assures me that the girls never get nude. OK, maybe topless but not completely nude.”

I ALMOST said, “And this from the guy who claims he never masturbates,” but pat me on the back, once again I held my tongue.

“Well, I’m sure that at some parties that’s all that happens but from my own experience, the guys want you to get naked - at least if you want to make the most money that’s what happens.”

“So you get nude when you do them?” she asked, suddenly very curious about my “side jobs”.

I explain that technically, I only “contract” ahead of time to get down to a bikini. Granted, it was the sort of bikini that would have gotten me banned from any public swimming pool, but still, I wasn’t technically naked. Once the party gets started, THEN it was time to negotiate what else they wanted from there. I learned early on that nobody makes a worse negotiator than a horny drunk guy at a party facing a half-naked girl he wants to fuck.

“So do you let them touch you?” she asked.

Again, I explained that it was all in what they were willing to pay. Letting guys SEE me naked wasn’t that big a deal but to touch me ... well THAT was a different story.

“OK, so how far DO you go if they are willing to pay for it?”

In response to that question, all I had to do was give Kate a naughty grin and a wink which she understood immediately.

“Oh my god Kelly, so you’re a WHORE?” she exclaimed, suddenly looking at me as if she had never really seen me before.

I quickly calmed her down and explained to her the difference between a whore and a slut. If I was really a whore, all they needed to do was simply fork over the money and then do whatever they wanted within the bounds of what they paid and I would do it regardless of how I felt about them. That’s why I never consider myself a whore - because I never give up control. Even if they are willing to pay for sex, I still make the final decision as to who and how. Even then, I don’t care how much they pay (non-refundable of course), if the guy turns out to be an asshole he doesn’t get laid.

Kate was still looking at me as if she was seeing me for the first time. I almost felt like she was disappointed in me, as if I had somehow degraded myself in her eyes. Frankly, it sort of pissed me off that she could be so judgmental but I decided to give her the benefit of the doubt and see where it went.

“Look, it’s not something I do at EVERY party, in fact it rarely happens. Usually it’s just a strip show and let me say AGAIN, I make the decision as to whether to go any further, no matter how much they want to pay me.” Kate just sat there rigidly, as if she wasn’t certain what to say which was probably a good thing. I smiled gently, trying to soften the mood and asked, “So Kate, how did YOU imagine doing a bachelor party with me?”

At the mention of her masturbation fantasy, Kate finally seemed to shrug off whatever it was that was distracting her and a smile returned to her face. “I guess sort of like the party we had last week, just getting up in front of them in some naughty lingerie and maybe pretending to play with myself for them. I just think it would be fun to see how turned on I could make them I guess.”

Somehow I think these new fantasies had to do with the lack of response she was getting from her bastard of a husband. It was too bad that just because a guy was unable to get it up that he cut off all sex with his wife. He could at LEAST still give her oral sex if he was any kind of decent husband, at least that’s how I felt about it.

My inner amateur psychologist was seeing a loving wife desperate for attention from her husband, so desperate she dreamed of displaying herself in front of other men just to prove to herself that SHE wasn’t the problem. OK, so I may have been totally off base, but I’ve found I’m usually pretty good at reading people when it comes to stuff like this.

“Would you really do it if you could?” I asked her. “I mean, go further?”

Kate seemed to visibly trembled at the thought and in a way, it made me almost want to laugh at her innocence and naivety. At times she could be such a sensuous woman and then in a heartbeat, back to being the silly little girl.

“Well, maybe when I masturbate but I would NEVER do it for real,” she insisted, shaking her head from side to side like an elephant on parade.

“Why not? After all, it wouldn’t be like you were being unfaithful or anything,” I prodded her, “What’s the difference between showing yourself off in front of a bunch of women and a bunch of men.”

“Kelly!” she huffed, as if she couldn’t believe I would make such a generalization, “There’s a BIG difference and you know it.”

“Not really,” I countered, “besides, imagine how much more turned on you’d get seeing all those men staring at you, every one of them wanting you and desiring you. All of them wanting nothing more at that moment than to take you in the back bedroom and fuck your lights out! Wouldn’t that make you feel good?”

“That’s EXACTLY what I worry about,” she huffed, “That I might like it. But I’m not a slut.”

“You mean like me?” I gently countered.

Kate’s mouth dropped open and I could see she was a little embarrassed now. “Oh Kelly, I didn’t mean it like THAT!”

“Then prove it,” I demanded, “I’ve got a party tomorrow night and it’s just a little one that shouldn’t be anything too wild. Come with me, I’m sure they won’t mind if I bring along a friend - especially if they get her for free.”

Kate obviously wasn’t even close to being sold on the idea but at the same time, she wasn’t shaking her head as strongly much as she had.

“How about you let me think about it,” she offered as a compromise. It was her usual response when she was trying to get me off her back about something so I warned her she needed to make her mind up fast.

“OK, let’s make a deal. When you go home tonight I want you to put on something sexy and then see what Bruce says. If he likes it, great. BUT, If he ignores you then I want you to think about what the guys would say tomorrow night if you wear that same outfit. THEN make up your mind and call me, deal?”

Kate just rolled her eyes at me, something she seemed to do quite a bit when we talked come to think about it. Well, I’d done all I could and there was no sense pushing her any further. I’d learned quickly with Kate that she was actually pretty open to suggestion but she had to be the one who made up her mind in the end. Nothing made her dig in her heels faster than feeling like she was being pressured into something she didn’t want to do.

We finished up our meal and she offered to pay. I left the tip and we parted, each going our separate ways. On the way home I wondered if she was just agreeing with me to stop me from pestering her further or if she really was going to go through with it. Personally, I would have given odds at best fifty-fifty once she got home and had time to think about it some more.

The next morning I was still in bed when my cell phone rang and I saw on the caller ID that is was Kate. I wondered what she was calling me about so early as in my morning fog I wasn’t putting it together with our conversation the previous day. Immediately when she started to talk, though, I perked up.

“Oh Kelly, I tried, I really did try!” she cried into the phone as soon as I answered, not even bothering with the small talk we always started out with.

I told her to calm down and get her to explain to me what was wrong.

“I did like you said. I wore the sexiest outfit I have; you know - the sheer black teddy you helped me pick out with the micro black lace panties. When I walked out of the bathroom into the bedroom, Bruce didn’t even give me a second glance! Shit, hardly even a first. All he did was ask me how much it cost, as if he was more worried about the credit card bill than my needs. How could he do that to me Kelly? How could he?”

She broke down again and started crying some more, leaving me there with my phone in my hand trying to figure out what to do next. I decided saying nothing was better than putting my foot in my mouth so I waited for her to collect herself.

“The kids are gone to school so I’m home all alone. God Kelly, I’ve never felt so worthless. Am I REALLY that unattractive? Why doesn’t Bruce want to even look at me when I dress up for him? I feel so ugly now.”

If I told her what I thought was the REAL reason, I would probably just make things worse. It was obvious. ED or no ED, her darling Bruce was cheating on her, I would have bet money on it. OK, so maybe she wasn’t eighteen anymore but she looked easily ten years younger when she got herself made up and I knew from personal experience it wasn’t for want of any sexual drive on HER part that nothing was happening with her husband. With the boob job, which no doubt she did to try and please him, she looked incredible! They looked perfect and REAL, not overdone like so many women where it’s obvious they are fake.

Then I reminded Kate of how even the women at the party we went to were attracted to her and if THEY were, to imagine how much more a group of men would be. Then I gentled tossed in a suggestion that maybe she should prove it to herself by going out with me tonight.

“I have to confess Kelly, I only agreed to do that so we wouldn’t talk about it anymore,” Kate said in a hushed tone, like it really was part of a confessional, “But this morning I woke up and I was SO horny and I wanted Bruce SO bad that even masturbating wasn’t enough to make it go away. I don’t know what to do now, I am SO confused.”

“Oh? So you’re still horny now?” I asked, using the opening to shift the conversation.

“Oh my god, you have no idea. I was so worked up last night getting ready for him that when he blew me off me it was like I wanted to explode!”

Again I suggested that she join me tonight to work off some of the “tension” and this time she hesitated a bit before answering.

“You’re sure it would be just like the other party, right? Just dressing up and showing off? Nothing nude or bad?”

Thank god we still don’t have video phones! I was grinning to myself at how naive she could be about such parties but I wasn’t going to say anything to dissuade her. Besides, so long as I was there I knew that I could control things enough that if that was all she ended up wanting to do I could most likely keep it at that level for her. As for doing anything “bad”, well ... that was all in how you defined “bad”!

“Trust me, you’ll love it Kate. It will be a ton of fun; something you’ll never forget. You’ll feel so much better about yourself afterwards.”

“I don’t know Kelly, what if they get pushy?”

“The we just leave,” I assured her. Actually, that was the truth and it wouldn’t be the first time I’d grabbed my things and walked out when guys got overly obnoxious or rude. It was rare, to be sure, but also why I always made sure I got paid up front!

“So what do I wear?”

Cool! While she hadn’t expressly agreed to go, her question was a tactic agreement and I wasn’t going to push for a signed contract or anything so this was likely the best commitment I was going to get from her. To answer her question depended on what type of party I was going to. Basically they broke down into two flavors - the ones where I arrived early and dressed up in another room and came out when they were ready for the show, or the alternative was I just showed up at the door, walked in and did my thing.

Each had their advantages and disadvantages. The first allowed for me to get more settled in and gave me greater costume options as I didn’t have to go out in public wearing it. The problem was you were there longer and before you could leave, you had to gather your things in the other room, making as quick getaway more challenging.

The second option was usually quicker as I was only there when I was doing the show. It also gave me a better feeling of security knowing everything I had was in the room and I just had to grab it and run for the door if things got out of hand. Fortunately, that had only happened once in my entire “career” but that was all it takes to make you wary. In this case, it was the “open door” party which was probably best for Kate as it minimized the time she had to spend at the house where the party was being held.

“Well, here’s what I suggest,” I told her, “Put on that same outfit that your husband wasn’t interested in and we’ll see what other men think of it on you.”

Silence on the other end. Then I realized what she was probably wondering about and continued on saying, “Oh don’t worry, that’s not ALL you’ll wear! Go to your closet and pick out what you would wear to a PTA meeting at school. Something with a skirt and a top that buttons - nothing pull-over though.”

“A PTA meeting?” she asked, sounding confused.

Then I explained to her what my plan was. I thought it would be hot to show up as a mother-daughter pair. Sure, Kate wasn’t THAT much older than me but she had that innocent look and naive attitude that screamed soccer-mom. I figured I would have her dress the part of the everyday mom while I would go as the slutty daughter. It should make for a great show. After all, just look at how many web sites cater to the MILF fantasy as well as to the mom-daughter thing.

Kate laughed on the phone, finally loosening up a bit as she listened to my concept for the evening. “You know, you really have quite the imagination,” she complimented me, “I’m just glad you’re not after my husband.”

Oh if she only know some of the naughty thoughts I’d had along THAT subject! Truth be told, her Bruce would’ve made a fantastic challenge for me and nothing would’ve been hotter than to have him do me behind Kate’s back at the same time I was trying to help Kate “seduce” him. As horny as such thoughts made me, I could never do that to a friend, though, so Kate was safe from any worries about me, even if she didn’t realize how close it had come to happening more than once when I was especially horny!

Now that she was on board, I then went through more details as to how the evening would go and what I expected to happen. Like the previous party, I would pick her up. We would drive to the house, ring the bell, and step in to what should be quite a party already in progress. No doubt there would be alcohol, porn, and who knows what else. We would dance and strip - as far as she was ready to go, and that would be about it. The arrangements, at least so far, were just for an hour’s show so we shouldn’t be there all that long and she would be home at a decent hour.

Kate cursed under her breath and when I asked what was wrong, she replied, “I just realized I have to come up with an excuse for where I’m going. Bruce would kill me if he ever found out.”

Her worries didn’t bother me as I knew she would think of something. Besides, she would be leaving in a “normal” outfit as nobody had to know what was underneath so there would be no reason for anyone to suspect her true motives for the evening. We got talking some more from there about everyday things. She liked to tell me about her kids at times like this and I listened patiently, again thankful for the lack of video so she couldn’t see the bored expression on my face. Eventually she was talked out and we hung up after I gave her a time to be ready.

Now that I was going with the mother-daughter fantasy gig, that changed my entire plans for the evening. I had planned to show up in a long coat with nothing underneath but a sexy bra, some hose and a garter belt, panties still undecided. It was an easy outfit to get ready, easy to take off, and all I had to do in the end was grab my coat and leave without even worrying about getting dressed again.

With Kate, however, now I had to play the role of “daughter” which actually had a lot of opportunities. My thoughts were to act as the “slutty” daughter who made my conservative mother mad at me for teasing the guys and acting nasty. Eventually, of course, she would get “excited” seeing me with the guys and want to join in herself. It was all terribly cliche, of course, but then isn’t most porn? Besides, it actually fit Kate’s real attitude perfectly. Indeed, she WOULD be aghast at my actions to start with but hopefully, she would get turned on and want to join in herself.

How far she would go, now THAT was the million dollar question. I was setting a personal goal of getting her nude. Even that would be a stretch but anything more than that was pretty unthinkable knowing Kate.

Looking through my closet, there was really only one thing to wear in this case. My usual outfits - the Catholic schoolgirl, French maid, naughty nurse, etc. were more for individual performances as I almost always worked solo unless my cousin Kristen was with me. Tonight I thought I would stick to something simple - my shortest shorts with a micro thong underneath.

On top I had the perfect black bra together with a sheer white shirt that I could tie up around me under my bust and then leave it unbuttoned to show off my cleavage. The bra and panties were for show as I didn’t want to be naked TOO fast with them. Besides, technically they hadn’t paid for me to get nude so I wanted something to use for bait that would lure them into opening their wallets for more. I didn’t charge all that much for a standard one-hour strip-to-my-underwear show. It was a classic bait-and-switch marketing ploy. I knew once I had them going that the REAL money was made when they were dying for me to go further. The trick was to get your foot into the door. After that, it was all hormones!

For the rest of the day, my thoughts kept drifting back to the coming events of the evening. I had all sorts of different scenarios play out in my head, most of the terribly unlikely but still hot to think about. Kate was the wildcard. Had I been going with my cousin Kristen, it would have been just the opposite. With her the question wasn’t how far would SHE go, it was how far would I go with her! A couple of time I found myself wet as hell and took some time to take care of myself, but other than that it was mostly just laundry and housecleaning with a nap in between to be sure I was rested.

I pulled up in front of Kate’s house exactly on time to the minute. She was typically prompt and I knew it frustrated her when I was late to things so I wanted to get the night started on the right foot. Sure enough, no sooner had I put the car in Park than Kate was coming out the side door by the garage, waving goodbye to someone unseen in the house. Anyone in the neighborhood would have thought it was just her as usual, meeting someone for a meeting at school or the library. She slipped into the passenger seat next to me, took a big breath, and let it out slowly.

“Oh my god ... Oh my god! I can’t believe I’m going to do this,” she sighed, “Bruce almost caught me putting on the teddy and I think I would’ve died if he saw me getting dressed with it underneath my outfit.”

“But it turned you on though, didn’t it?” I teased her as I pulled away from the curb.

Kate tossed her head back and giggled, “You have NO idea! You know, I’ve never left the house dressed like this It feels a little weird to be honest.”

“So you’re nice and horny now?” I pressed her a little.

She turned her head to me and I just caught a glimpse of her face as she grinned naughtily. “I did it THREE times today, can you believe it! I’ve NEVER done that before! I almost did it four times but the kids came home from school before I had the chance.”

I smiled as I drove, trying to picture her in my mind, lying in her bed doing herself while her family was out. I wondered what her kids would think if they knew of their mom’s new daily “routine”? Despite the fantasies you might read about on most porn sites, most likely they would be grossed out but then again, you never know!

“So tell me again ... what do I do?” she asked after we quite laughing about her new “record”.

“Just follow my lead,” I told her, “There IS one thing that is REALLY important though ... NEVER offer anything you’re not ready to back up.”

“I don’t understand. What do you mean?”

“Well, teasing them is fine - it’s even expected and they would be greatly disappointed if you didn’t. Just don’t ask them things like if they want to have sex with you or in any way make it appear like you are offering them anything - unless you want to do it.”

What I wasn’t telling her, because I didn’t want to scare her, was there was more than just the issue of taunting men to where you may get in over your head, there was also the legal issues that offering yourself to a man, potentially for money or other compensation, can cross the fine line between a stripper and a hooker. The LAST thing I needed was somebody getting pissed off or undercover and charging either of us with prostitution. I just imagine her calling her husband to bail her out of jail!

For the rest of the 45 minute drive we talked about ways to tease and what to do and NOT do. Kate touched a little bit on the issue of sex but I tried to steer away from that as I knew it would only frighten her off.