The Bad Girls Club
Copyright© 2012 by lametoad
Chapter 8: Beginner’s Luck
Erotica Sex Story: Chapter 8: Beginner’s Luck - Jerry's problem is simple. He's a romantic who has a thing for bad girls. Some characters from the No Strings Challenge appear.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Consensual Heterosexual Fiction Oral Sex Prostitution
Before I move on to my surprisingly eventful reunion with Emily or whether my encounter with Avery was AI enhanced, it might help to explain how my fixation on bad girls started. It may also help you understand why I’m so comfortable having sex with women who aren’t necessarily my age, though likely not in the direction you assume.
I took two gap years before going away to college as a prospective business major. To pay for my books, I got a night job as a valet at the town’s fanciest but smallish hotel. To pass the time on my solo nights, instead of doing my homework I’d often make up stories about the guests: matching their vehicles to possible jobs and family, figuring out the nature of their stay from glimpses of their luggage, listening in to bits of conversation. It was a late on an especially quiet night when a red Mercedes 500E pulled in. Anticipating a big tip from some asshole wannabe-king-of-the-world business guy, I hurried over to the semi-tinted windows of the driver’s side.
“Hi there!”
A woman’s voice.
“Welcome to the Redbud Lodge, Ma’am!”
The window went all the way down, revealing a gorgeous pair of brown eyes paired with the most seductive smile I’d yet encountered. “Do I look like a Ma’am to you?”
“My apologies, Miss! The car threw me off. I wasn’t expecting...”
“What weren’t you expecting?”
She unlocked her door, I opened it and held it open, and she stepped out. She was about 5’7” without her stiletto heels. Even taupe business casual didn’t disguise her figure. Her calves were toned, her medium-sized breasts were high and proud, and her butt was just enough out of proportion to push out her skirt just so.
“Honestly, I wasn’t expecting such a beautiful young woman to be driving an $80,000 car.”
Maybe it was her father’s?
She smiled. “You’re not the first person who’s been caught by surprise, and thanks for the compliment, both of them.”
I noticed that she was subtly eyeing me back. She handed me the keys. “Since you know so much about my car, I assume you’ll take good care of it.”
“Got it, no parking under trees, keep it away from other vehicles. I know the drill.”
“That’s a good boy! ... Or should I say young man!”
“A little bit of both at this point, to be honest.”
She winked. I wondered if she noticed how my eyes were fighting not to linger on her butt. It was genuinely hard to tell, but she might still be in her twenties, yet too poised and confident to be so young. She was clearly the sort of woman who took great care of herself: fit, perfectly applied makeup, freshly manicured pink nails, matching heels, everything coordinated just so. It was as if she dressed to look a little older. Was it for work or some other reason like a sugar daddy?
I unloaded her luggage from the trunk and radioed the front desk for Carlos. Carlos, the bellboy, however, wasn’t a boy. He was an older guy with a couple kids in school. It turned out he had to leave work early for a school event. “Miss, would you mind waiting a few minutes inside the lodge? I’ll be taking your luggage up to your room and need to park your vehicle first. We’re a little short-handed tonight and I’m finishing my shift.”
She nodded. It was late fall and cold. She wrapped her arms around herself to keep from shivering. I offered her my coat which she refused. We left her Mercedes at the front of the lot, I loaded the luggage cart, and walked her to the front desk. I stayed two steps behind her as she exchanged information with a very stressed new desk clerk.
“Let’s get you a table by the fireplace near the bar and something to drink compliments of the house while I get your car parked and your room ready.Your luggage will be safe here.”
“They’re keeping you busy tonight. Shouldn’t you be studying for finals?”
I laughed. “Guilty! Exams are after Christmas though.”
“Seriously, I can manage. Maybe you want to get back to your girlfriend.”
“It’s really no problem and I need to keep this job. They don’t normally hire freshmen.”
She looked me over again. “Wow, thought you were older.”
Was there a little disappointment in her voice?
“Actually, no girlfriend. At least not right now. It’s been a while.”
She looked me over again. “Must be by choice?”
I shook my head. “I took a couple years out after high school and I didn’t have many chances to date.”
I’m not sure why I felt the need to confess like this.
“Military service?”
“Not exactly.”
“Prison?”
Her tone was too flirtatious for me to take offense.
“Do I look like someone who’s been to prison? Besides, they haven’t caught me ... yet.”
“Well, you never know. Everyone has got their story. Some time, I’d love to hear yours.”
In my first couple months at the hotel, I’d repeatedly been fascinated by the stories of the guests whose cars I parked, this was the first time a guest had shown any kind of interest in mine. Meanwhile, I still couldn’t get a fix on hers.
We were interrupted by the desk clerk, “Miss Lindstrom, sorry about the delay. Here’s your key card.”
She grabbed a designer satchel, too big to be just a purse, from the luggage cart and clutched it as if it held something really important. I led her to the bar. Fortunately, a small table by the fire at the bar was still vacant. Multiple men’s heads turned as soon as I escorted her inside. She, probably purposely, sat with her back to them.
“There’s some sort of business conference at the college ... Is Irish coffee okay?”
“That would be lovely.”
She touched the back of my hand. “You said you were a business major. You should go to the conference.”
“But it’s not for students. Not for freshmen anyway.”
“You’re being too much of a rule follower young man. How do you think I got my car?”
I shrugged. I really had no idea.
“Connections matter.”
“Make yourself comfortable and I’ll be back in a bit Miss Lindstrom.”
“Please, call me Krista.”
“Jerry.”
She touched my hand again as she looked me directly in the eyes. A little jolt passed through me.
I hurried to her car and parked it in the safest space in the lot. The subtle scent of her very sophisticated perfume lingered. As I prepared to get out, I noticed the glove compartment wasn’t fully closed; a cord was obstructing it. My manager had mentioned that he’d fired two of my predecessors for taking drugs and cash out of guests’ glove compartments. I didn’t want to get blamed for the appearance that I’d opened it. I pushed the latch to get the cord out of the way and the door fell open revealing a twelve volt charger and a small pink vibrator, still surprisingly warm to the touch. Whoa! Apparently women had more than one way to keep from falling asleep on a long drive.
I pictured Krista Lindstrom in her not so business casual on her late night drive to the lodge less than a half hour earlier, one hand on the wheel and one hand elsewhere. My cock pressed against the elastic band of my briefs. If only!
I ran back to the lodge. When I got to the bar to let Krista know that I was ready to bring her luggage to her room; she was surrounded by three older guys in sport coats.They were clearly more than a little drunk and maybe even more clearly out of their league. She must have seen me from over her shoulder when I approached. “Here’s my date! Sorry gentleman!”
I took a seat. She nudged closer and put an arm around me, running her fingers along my upper arms.”Thanks for taking care of the car, babe.”
“Come on! Is this guy even old enough to drink?”
I wasn’t, at least not for several months.
“He just finished doing hard time. If you fellows don’t mind, my boyfriend and I have some catching up to do.”
The hard time bit was true, though more in a penile than penal system way. I liked the fantasy of being Krista’s bad-boy boyfriend.
I tapped my pocket as if it held a weapon and did my best impression of a convict staredown. The guys took a step back in unison. For a second, I wondered why no one noticed my parking valet uniform, then remembered that I still had on my jacket. Krista squeezed my outer thigh and quickly kissed me on the lips. “So baby, do you want to have a drink first or head up to our room?”
The bartender obviously knew me. I grunted, “Room!”
I liked this fantasy.
Krista spread her hands in a clearing out motion. As we entered the lobby, she whispered, “Thanks for the rescue.”
I hadn’t even noticed she was holding my hand. I turned to see if the men were still staring. They weren’t. “That was pretty smooth. Do you do this sort of thing often?”
It happens a fair amount when I’m on the road alone. It’s sort of flattering and tiresome at the same time. I’ve had some interesting experiences. It sort of depends on the guy or guys.”
“I see.”
“You were pretty smooth yourself, for a freshman. I loved the way you pretended to be packing.”
“What makes you think I’m not?”
Krista had the kind of laugh that would draw any man to her. I might have been packing right then, but it wasn’t a gun.
“Well, between us, those guys are in for a little surprise tomorrow at their conference.”
We got to the elevator, but the light was off. She was still holding my hand.Who was I to stop her?
The front desk clerk called out, “It’s going to take about half an hour for maintenance to fix the breaker and get it running again.”
“Krista, if you don’t mind, we need to use the stairs. What’s the floor?”
“Fourth.”
I looked over a the luggage cart. “I’ll have to make a couple trips. Let’s get you settled and away from getting hit on again!”
She nodded. As I lugged two of her bags, Krista, even in heels, was a couple steps ahead of me. I couldn’t complain about the view, but she was no longer pretending to be my girlfriend.
We got to her end suite. I helped her start a fire in the fireplace while she hung up clothes from a travel bag. A man’s three piece suit was one of the items. Oh well! Naturally, she was married or quite taken. Whatever fantasies I’d harbored since the glovebox discovery quickly leapt back over the wall from the remotely possible to the no chance in hell little boy side.
“This is the lodge’s honeymoon suite. We only have two rooms with a fireplace and a soaking tub.”
“I love a fireplace at this time of year. That’s the reason I requested it.”
At least she didn’t say “We”.
“I’ll get the rest of your bags.”
Another trip up the stairs. I knocked at her door with the last of her bags. “Come on in, I’m back here.”
I could hear the sound of the tub running. Krista’s business casual suit was folded neatly on her bed. What a picture! She shouldn’t have left her room door unlocked, though. Her bathroom door was just slightly open. I caught a glimpse of bare leg as she grabbed a towel from the rack.
“I’m putting your suitcases next to the others by your bed! I hope you have a nice stay!”
I locked Krista’s room door for her, closed it behind me, headed downstairs, and prepared to ride my bike to my dorm. At least I’d be warmed by fantasies about the babe in the red Mercedes. Before I got to the bike rack, the desk clerk called me back. “421 wanted you to know that you forgot something.”
I’d left without a tip. I’d always been a little shy and honestly had never gotten used to expecting or signaling for one. Besides, I was more than a little flustered by everything that had taken place so far.
“If she wants to leave a tip, I can pick it up tomorrow before my shift.”
“Are you sure? I saw her holding your hand by the elevators. Even I might change sides for a chance. What an outfit!”
The clerk was flamboyantly gay. I was maybe the only male staffer who was friendly enough with him to joke around with.
“She was just playing.”
“Even so, she was playing with you not some guy from the bar.”
“What the hell; it’s just stairs.”
“See you in the morning!”
The desk clerk waved and winked.
“Right, fat chance.”
Krista answered the door in her bathrobe. Her hair was down and some of her makeup was off. She looked even more gorgeous.
“Sorry, I thought you’d still be in the bath, but the desk said I forgot something?”
“I’m glad you came back up. I’m sorry I forgot you’d have to walk the stairs again. You must be a little tired.”
The fire was roaring.
“I’m okay. I used to run track. Lots of stairs in the off season.”
“I see. Look, please sit down for a minute anyway. I feel like we didn’t get a chance to finish chatting. Maybe enjoy the fire you started.”
The double entendre was not lost on me.
“I guess that beats riding my bike to campus.”
“At this hour? In this weather? Why don’t you let me get dressed and give you a ride back to campus.”
“No, that’s really nice, but you just got here. You’re a guest of the lodge, but I wouldn’t mind warming up a little.”
She placed a hand on my lower back and guided me to a chair facing the fireplace just in front of a white bearskin rug. “I think I can help with that. Let me get you a drink?”
She came back and handed me something non-alcoholic, then ducked back to the bathroom. I took a sip, put the glass on a nearby table, looked up, and WHOA!
Krista had opened her robe, revealing a black bra and g-string. Whatever questions remained about her figure immediately melted away. She let the robe drop to the floor around her feet then did a little striptease, nothing elaborate but enough movement to make it clear that she knew the effect her body had on guys and how to maximize it. “Maybe this might warm you up?”
As she turned to slowly peel off her g-string, I was mesmerized. To put it bluntly, I’d never seen a better ass. I still haven’t.
My mouth hung open. As Krista stood proud and naked on the bearskin rug and did a little turn, “Do you like what you see?”
I was suppressing a pant and shaking more than a little. Was this the end or the beginning of my tip?
“So tell me something; how old do you think I am?”
Knowing this was a tricky question, I guessed low, “Twenty-four, maybe twenty-five?”
“Thirty-two. Can you handle that?”
“I sure hope so.”
“Excellent. You’re very shy. I love to bring out shy gentlemen.”
She held out her hand and I stood up.
“You’re not a virgin are you?”
I hesitated. “Actually, no. Is that okay?”
“Of course. I’m pretty sure that bath is still warm. Would you like to join me?”
Krista slowly and seductively undressed me, kissing me on the cheek and stroking my hair throughout. I should have done the same, but part of me was still in shock. She led me to the bath where she pulled down my briefs.
“Very nice!”
She held the end of my erect penis between thumb and index finger. “This will do nicely. I think we’re both going to have lots of fun.”
My tongue finally relaxed, maybe slightly ahead of my brain. “You’re so incredibly hot.”
I kissed her lightly on the lips. Krista responded by opening her mouth and probing the inside of mine with the end of her tongue. We got in the bathtub. The water was still warm. Lit candles around the edge set the mood. Her breasts defied gravity, nipples pointing slightly up, and hardening as she encouraged me to soap them. Her stomach was taut. Her butt curved perfectly. Her light brown hair was soft and silky, straight from a shampoo commercial. She might be thirty-two, but her body had stopped aging at twenty.
“It’s okay for you to do more than wash me.”
I tentatively ran my fingers up her torso until I reached her neck. Her skin was wonderfully smooth and addictively soft. I lingered there, my palm getting involved and my fingers slowly relaxed. I then caressed her face and hair more confidently. I bent forward for another kiss. She opened her mouth again, but this time neither of us pulled away.
“You’re a very good kisser, young man.”
“For my age?”
Krista answered by taking my hand by my index finger and moving it to that part of her body I hadn’t dared touch yet. “Feel that!”
I did so tentatively. She was already slightly slippery.
“I hope you know what it means.”
I nodded; taking it as a signal, I continued to explore. She moaned softly.
For whatever reason, the man’s suit in her closet crossed was still making me nervous. “Before we go on, could I ask you something?”
Krista straightened. My hand reflexively moved to her thigh, though I kept rubbing my fingers together. “Let me guess, you wanted to know about the suit. I thought that might have been why you ran out.”
“Well, yeah! Are you maybe married?”
“If I say yes, will that turn you on or off?”
“Uh, maybe a little bit of both. It’s definitely exciting, but I’m still sort of a good boy. I am definitely wondering why you’re doing this. I mean, why me?”
She touched my cheek. “Wow! You are really young!”
My erection deflated and she clearly noticed.
“First off, technically ‘Yes’, but we’ve been legally separated for several months. We both consider ourselves very single at this point. He did get an early start with that. So, I guess I may not be your first, but I am your first married woman.”
“That’s his suit though?”
“He’s going to be at the conference. I think he left it at my place on purpose, like trying to still mark his territory. I’m already paying him spousal support. It doesn’t include my providing him storage space.”
Her eyes went wide. She was still clearly sad. I felt even younger.
“If I can ask?”
“We’re naked and you’ve gotten to third base here. That’s probably permission enough to ask whatever you want.”
“What happened?”
“I caught him cheating with a nineteen-year-old intern, a not very hot one at that.”
“So ... am I kind of like your revenge?”
“Maybe, more like my turn to mark my territory.”
Images of Krista on the road with a succession of valets, bellboys, waiters, but not desk clerks all of varying sizes and colors, all with much bigger cocks than mine, flashed across my imagination.
“Knowing how to treat a lady doesn’t have an age. I just noticed how attentive you were. You’re a gentleman. That and I thought you were cute. Also ... you could use a little experience.”
“I’m not a virgin. I’ve had girlfriends, really.”
I thought about the fact that she’d left the room door unlocked and her bathroom door tantalizingly ajar. I’d missed the green light.
“Jerry, I believe you. Let me make a bet here. You’ve never really had great sex.”
I looked up towards the window. It had started to rain. “My girlfriends seemed to like it okay. I mean I’m pretty sure they came. Two of them at least.”
“Orgasms are a physiological thing. Great sex is a lot more than that. And no, I’ve not been picking up random hotel employees or waiters for the last six months. You’re the first.”
“I’m flattered.”
“Well, it was either you or that cute desk clerk.”
“Uh, not sure he’s available that way.”
“I’ve helped a couple gentlemen discover they were more bi than they knew though safely. If I want a guy, I can be awfully persuasive.”
“I noticed.”
We got out of the bath. Krista kissed me on the cheek. “Sorry, I didn’t mean to break the mood, but it’s going to make things even better. Intimacy can make the difference between just giving a girl an orgasm and creating something more memorable.”
We toweled one another off, while alternately kissing. Krista reached down and ran her fingers along my balls, more of a tickle than a caress. I didn’t recover my erection completely, but it responded with a healthy twitch. She looked down and smiled. Ever the responsible employee, I suggested we blow out the candles to avoid burning down the honeymoon suite. Krista insisted that we do it together, cheek to cheek, shoulder to shoulder, our breath intermingled. Not overtly sexual, but the memory still gets me aroused. We next sat on the bearskin rug together in front of the fire as she ran her fingers along my body, occasionally touching my cock ever so lightly. “So, have you done this before?” I asked.
“Taken some inexperienced boy and initiated him into the mysteries of the lovemaking arts?”
“That’s me, I guess.”
“Not since the separation, but you’re not the first.”
“Okay, so this is something you enjoy?”
“Honestly, yes. Don’t freak, but I know my way around men, all types of men. I love sex with the right man or the right woman. Does that bother you?”
“Definitely not. It turns me on ... especially the women part.”
“So, maybe not so innocent. No threesomes tonight, but if you’re a really good boy.”
“I guess you and I will have to do.”
“Good! The ex is fifteen years older than I am, so you’re a welcome change.”
A pause. “Was he great at sex?”
She thought for a minute. “Sometimes, though not all the time, and definitely not lately. But it’s not the reason things broke down. He started off as my business mentor, then I passed him pretty quickly. Looking back, I guess he missed being the one in charge in that department.”
“I get it. So if I pass you at this, we have to break up?”
“Well, let’s see how you do with this first lesson.”
“Oh, it’s a lesson is it? Should I be taking notes.”
She poked my chest with her index finger. Again, my hotel staffer self got the better of me and I got up to add logs to the fire. When I got back to the rug, Krista motioned for me to lay on my back and she massaged my shoulders then started to kiss her way down. She looked up at me with her big brown eyes. “Trust me, Jerry. You won’t need notes to remember this part of the lesson.”
She licked her lips then ran her tongue around my nipple. Her hair fell softly against my stomach. I was certainly looking forward to Krista getting to her destination, but her comment about my being a gentleman stuck with me.
I gently interrupted her, pulling her up, and motioned for her to change places. “Ladies first.”
“This is a surprise, but I have to say I’m impressed with your attitude. If you haven’t guessed, this lady is pretty turned on.”
I’d gone down on girlfriends before. In fact, the two who had orgasms had them thanks to my tongue and maybe a little alcohol. One enjoyed it and wanted more. The other freaked out, got out of my car, then asked to be taken home. The next day she insisted she just wanted to be friends. Never date a rabbi’s daughter, even a rebellious one. Nonetheless, I’d convinced myself I’d figured out what to do down there.
Taking a cue from Krista, I worked my way down her body slowly, spending considerable extra time on her breasts. Her nipples were like mini-erections. I was on the right track. Her stomach was already moving with anticipated pleasure. “That feels so good, sweetie.”
“I feel incredibly lucky to be here with you right now. I’ll always know I’ve been with a perfect woman.”
“That’s nice, but it’s maybe too over the top. I’m far from perfect.”
“Can I at least say you have perfect breasts and a perfect body. I can’t wait to explore more.”
“Can I just say I may be doing a lot less teaching than I expected tonight?”
I kissed my way up Krista’s slender thighs. For the first time, I noticed the aroma of an aroused pussy. I loved it. I started with light kisses then moved on to little licks which were met with low moans. “That’s nice, Jerry. It feels really good.”
Excited by the praise, I sped up.
“Hold on! Okay if I offer suggestions as we go here.”
“Uh, of course!”