The First Timers Club
Copyright© 2022 by Alex Weiss
The Fairer Sex
Coming of Age Sex Story: The Fairer Sex - Ashley and her three best friends are high school outcasts. Four virgin nerds who have never dated or even kissed a boy. At Ashley's sixteenth birthday party, the four girls strike up an unlikely friendship with a new acquaintance of Ashley's parents. A handsome older man with a dark past who agrees to become their sexual mentor. But Ashley's mom has plans of her own for the mysterious new stranger in their midst.
Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa Ma/ft ft/ft Fa/ft Mult Teenagers Consensual Drunk/Drugged Reluctant Lesbian BiSexual Heterosexual Tear Jerker MaleDom FemaleDom Light Bond Rough Spanking Group Sex Anal Sex Cream Pie Double Penetration Exhibitionism First Facial Massage Masturbation Oral Sex Sex Toys Tit-Fucking Voyeurism BBW Menstrual Play
Denise held the wine bottle up to the light to check its fullness, then topped off her glass and returned to her chair behind the kitchen island while I finished preparing dinner.
“Oh, wait! Hold on. Okay, I’ve got another one. Why did the bicycle have a kickstand?” she asked, snickering at the punchline already.
I rolled the contents of a sauté pan over the burner and shrugged. “I don’t know. Why?”
“Because it was too tired!” Her full throated laughter filled the kitchen. “Come on! Don’t you get it? Two tired?”
I shook my head and lifted the corner of my mouth. “Oh, no ... I get it,” I said, pushing the contents of the pan onto a cool sheet pan to rest. “That was good.”
She pouted her lip and pawed the air. “Oh, you’re no fun tonight. Why don’t you have another drink or a ... fucking quaalude or something?”
I checked my watch and said, “A quaalude? Who the fuck takes quaaludes anymore? Is that even still a thing?”
She paused with her lips on the rim of her glass and snorted into it. “The fuck I know, but it sounds like something I’d do!” she laughed.
I turned and smiled at her, still shaking my head. “You probably would.” I wiped down the pan and started on the next batch of vegetables.
Even though she only worked six blocks from my apartment, I hadn’t seen Denise in weeks before the salon trip with the girls. When she texted me about hosting a happy threesome dinner party, I jumped at the opportunity to reconnect with an old friend and have some real adult conversation that didn’t include discussions of video games and high school finals. I also hoped the evening would bring a welcome respite from the drama of Erin Mitchell and the First Timers Club. I checked my watch again.
“Relax, fuck face. She’s almost here,” Denise said, noticing my fretful clock watching. “She texted earlier that she was pulling onto your street.”
“It’s all good,” I said, playing it off. “I’m just timing the food.”
Hosting these parties with Denise had become something of a tradition for us over the years. Every once in a while, one or the other of us would meet a woman whom we believed might be interested in a threesome with the other. We’d invite them over and see if the chemistry happened. Most of the time it didn’t, but every so often it led to a night of sensual pleasure for all three of us. Although Denise and I had never had sex with each other, we always enjoyed sharing the same woman in bed. I’d never had a better wingman than her.
“I was going to step out for a quick smoke before she gets here,” Denise said. She pulled a pack of cigarettes from her purse and held it up to me.
“I’m good for now,” I said, then narrowed my eyes and pointed a spatula at her. “Okay, so what’s the difference between a romper and a jumpsuit, anyway?”
“Length of the leg,” she said, indicating the wide flared leg of her outfit. “Jumpsuits are full length, rompers are short.”
Her strappy, baby blue satin jumpsuit clung to her body like silk to a balloon, and every time she moved, her large breasts swayed freely, unrestrained by a brasier. A knock at the door caused Denise to pop her eyes open and form a small o with her mouth.
“Oh! That must be her,” she said excitedly.
I slung the tea towel I’d been holding over my shoulder and crossed to the small vestibule to open the door. As I put my hand on the handle, I noticed the door hadn’t fully latched from earlier, when Denise had left to fetch her bag from her car.
“Hey, Denise!” I yelled over my shoulder as I pulled open the door.
“Yeah?”
“The door sticks! You have to pull it all the way shut, okay?” I said and turned to greet her friend.
“Hey, dude.”
Courtney and Brittney stood on the other side. I closed the door slightly.
“What the fuck are you guys doing here? I’ve got company.”
“Hey, Courtney!” Denise called from the kitchen.
Courtney leaned over and grinned, waving at her over my shoulder.
“Wait. You’re the friend she invited?”
Courtney’s grin faded. “She didn’t tell you?”
I felt a hand on my shoulder as Denise came to my side holding her wine. She pulled the door all the way open.
“Oh, you brought a friend!” she said when she saw Brittney. She leaned forward to put her arm around Courtney’s neck for a quick hug. “Hi, Brittney! I’m so glad you came,” she said when she reached up to welcome the tall redhead with another friendly hug. “Oh my god, you both look so fucking good! Come in! Come in!”
“Dude, what the fuck happened to your wrists?” Courtney asked quietly as she and Brittney shuffled into the apartment.
“Nothing,” I said, and shut the door behind them.
I followed the three of them into the kitchen as the girls pulled off their coats. They’d worn the evening outfits Ashley had bought for them at the boutique and they indeed looked so fucking good. Courtney’s black low-cut party dress showed off plenty of cleavage and Brittney’s long, off the shoulder sweater dress fell to mid-thigh, hugging her curves and flattering her tall frame. A pair of black hose completed her look.
I put my hand on Denise’s shoulder and guided her toward the slider door leading to the balcony. “Can I talk to you for a second, please?” I asked her under my breath, then turned to the girls and said, “We were just about to step out for a smoke. Be right back.”
“Can I join you guys?” Courtney asked, but I waved her off.
“Just make yourselves comfortable,” I said. “Wine’s on the counter and glasses are above the sink. Feel free to snoop around. We’ll be back in a second.”
I pushed Denise out onto the balcony and closed the slider behind us. “What the fuck do you think you’re doing, Denise?”
She gave me a surprised look. “What?”
“Why the hell did you invite them here?”
She studied my face and shook her head. “Alright, first of all, I only invited Courtney, okay? She must have brought Brittney along with her.” When I shot her a skeptical look, she held up three fingers and said, “I swear.”
“Fuck. She must have needed a ride. Look, I’m sorry, but they can’t be here.”
“Why not?”
“Because...,” I said before I realized I couldn’t really tell her why. I wiped my face. “I can’t get into that with you right now but trust me, they’re not the kind of girls you bring to our dinner parties.”
“Why not?” she asked again, but this time her tone had taken on a scornful edge. “It’s just dinner.”
“Because they’re in high school!”
“That didn’t stop you.”
I paused for way too long before I responded. “That’s none of your...”
“ ... fucking business. Yeah, I know! That’s your stock answer any time you don’t want to talk about something,” she chided, cutting me off. “I like her! And I think she might like me too.”
“Denise...,” I began, but what else could I say? She was probably right.
“She called me, okay? For makeup tips. But we really bonded at the salon yesterday.” She smirked at me. “I saw that little porno she made, you know?”
“Jesus...”
She laughed and said, “You really don’t understand how salons work, do you? All the gossip comes out, baby, and let me tell you, I got an earful about all your little escapades down at the pool house.”
So much for our sanctuary. Between my drug-induced disclosure, Erin’s camera, and the chatty gossip of four teenaged girls, I wondered if anyone existed who didn’t know what went on in there. I slicked back my hair and waved my hand around, thinking of some objection that didn’t sound like complete, patronizing bullshit. When Denise saw the look on my face, her expression softened.
“Hey,” she said, putting her hand on my arm, “what’s going on with you? You’ve been acting like someone ran over your dog ever since I got here. Why are you being so overprotective of these girls?”
What could I tell her? That an obese psychopath basically kidnapped and sexually assaulted me a few hours ago and threatened me with prison? That after taking on the solemn task of deflowering four virgins, I lived in constant fear of hurting or traumatizing them? That I felt the crushing weight of responsibility to teach them how to not get fucked over by every asshole they meet?
“Those girls ... they’re very special to me, okay? They’re sensitive.”
Her eyebrows drifted apart and she smiled at me. “You’re talking to a woman with a daughter. Trust me, I know how they are at that age,” she laughed. Then she straightened my collar and brushed the front of my shirt like any mom would do. “You know how this goes. It’s just dinner and we see if the magic happens. And if it doesn’t, I’m fine with that. I promise.”
In a world where I had very few friends, Denise was one of my closest. If I couldn’t trust her, whom could I trust?
I nodded and said, “You’re right. I’m sorry. Let’s get back inside before they think something’s up,” I said. When I turned, the girls stood watching us from the other side of the glass.
“They know something’s up,” Denise said as she pulled open the slider and flourished her hand to usher me back inside. “They’ve been watching us the whole time.”
“So you said this has both eggplant and peaches in it?” Denise asked as she took another bite of the caponata I’d prepared. “That’s a pretty unusual combo. Totally works though. The peaches are so juicy, and the eggplant just kind of ... bursts in your mouth.”
She and the two girls sat distributed around one corner of the marble topped island while I stood across from them on the kitchen side. I preferred eating meals that way, especially for intimate little gatherings like this one. I’d always found the formality of a dining table removed too much of the spontaneity and casualness that a good dinner party should foster.
“Mm! And what is this creamy white sauce on top?” she asked. “Delicious.”
I took a bite and smiled at her. “Just something I whipped up myself.” I pointed at the corner of my mouth. “You’ve got a little ... right here.”
Denise snaked out her tongue to lick the sauce off her face. “Mm. Well, let me tell you, fuck face, I love the way your sauce tastes. I think I could drink a gallon of it. Well done.”
I flashed her an appreciative smile. “I’m glad you like it,” I said.
At just a smidge over forty, Denise looked classically beautiful, with a gorgeous smile and soft, brown eyes, but also confidently sexy in that particular way older women do as they approach the peak of their sexual maturity.
“What?” she asked when my eyes lingered on her for a bit longer than usual.
I lowered them to my plate to prepare another bite. “Oh, you know...,” I said, lifting my lips.
“You’re a persistent son of a bitch, I’ll give you that.”
Courtney and Brittney looked on as Denise and I bantered, having said less than ten words between them the entire meal. Denise leaned over to commiserate with Courtney, touching shoulders with her.
“This guy’s been dying to fuck me for years, but he won’t do it,” she said.
Courtney’s eyes widened at the abrupt introduction of sex talk at the dinner table. It had become a common tactic Denise and I used during our dinner parties to gauge the interest of our guest. It helped us set our expectation for what kind of evening we should prepare for.
Although Courtney and the rest of the First Timers had only just recently begun to feel more comfortable speaking openly about sex with me at the pool house, I assumed that they’d never participated in this sort of talk with older adults in a real world setting before. As Courtney eased herself into the conversation, I wondered how she would handle it.
“Why not?” she asked, looking from me to Denise. “You’re gorgeous.” She’d done a good job covering up her acne with makeup, and I assumed that’s why she had called Denise in the first place.
“Aww. Thank you, sweetie!” Denise said, casually putting her hand on top of Courtney’s and leaning against her a little more. She peered at me from the corner of her eye. “I think it’s because he’s too chickenshit to take me up on my deal.”
“What deal?” Brittney asked, trying to pull herself into the conversation, which wasn’t normally like her. She’d done up her makeup as well, and her wavy hair looked redder than usual against the soft cream color of her sweater dress.
Denise grinned her gorgeous smile as she talked. “I told him, I’ll let you fuck me any way you want, but I get to fuck you first.”
I rolled my eyes and flashed her an embarrassed smile, as I did every time she told the story at one of our parties. It had become our favorite sexual ice breaker.
Courtney didn’t get it. “Why wouldn’t he want to let you have sex with him?”
Denise moved her hand to Courtney’s forearm and said, “Because, he knows I’d bring Rocco with me.”
“Who’s Rocco?”
“My strap-on dildo.”
When the two girls processed the implication, their faces reddened and Courtney snickered. I lifted my eyebrows and shrugged, taking another bite.
“I’m still considering it,” I said noncommittally. “Rocco’s pretty big, though, and I’m pretty delicate.”
Denise leaned her head on Courtney’s shoulder and laughed, rubbing her arm, and the two girls shared in her amusement at my expense. Courtney didn’t seem bothered by Denise’s touches, but she didn’t return them either, or even appear to acknowledge them as the obvious signals Denise had meant them to be.
I could sympathize with Denise. Everything I’d done with the girls so far had come at the expense of lots of explicit instruction and explanation. Their naivety about sex in general probably created a huge blind spot when it came to same sex flirtations and signaling. Denise certainly had her work cut out for her tonight.
“Wait, you have a daughter?” Courtney asked after we’d moved the party to the living area.
She and Denise sat next to each other on one of the leather sofas, while Brittney sat on the loveseat by herself. I reclined in a large, stuffed chair with a tumbler of whiskey glittering in my hand. I’d lit the floating Swedish fireplace, more for ambiance than warmth, while music played softly in the background.
Denise nodded and pulled out her phone, flipping through her photo album. “Zoey’s fifteen and the absolute joy of my life,” she said with a sentimental sadness as she turned the phone to show Courtney. “Here she is. This is my most recent picture of her.”
Courtney nodded, saying, “She’s very pretty. I can see she takes after you. Is that her dad?”
Denise warmed to the compliment, favoring Courtney with an appreciative smile, but acknowledged the question with barely a nod. She put her phone down next to her and then grabbed Courtney’s hand and pulled it into her lap. As one empty wine bottle had turned into three, she’d become bolder with her flirtations and Courtney seemed to enjoy the attention of the gorgeous older woman.
“I thought you were a...,” Brittney started to say, but hesitated to finish the sentence.
“You can say it, Brittney. Lesbian?”
Brittney blushed and said, “Yeah. How did you...”
“I had Zoey before I came out,” she explained. “When Jared and I separated, Zoey went to go live with him. They live out of state, so I only get to see her every couple of months, but she and I always spend a long holiday together every year. Just the two of us.”
Courtney noted the melancholy tone in her voice and put her other hand on top of Denise’s in a gesture of empathy. The two of them shared a look and Denise smiled at her, fighting to keep her lip from trembling. She took a deep breath and turned her head away, fanning her face with her hand.
“Whew!” she breathed. “Sorry about that. Talking about her can make me kind of mushy sometimes. So, anyway...,” she said, turning her head to face me. “I’m dying to hear about this First Timers Club.”
I moved my eyes between Courtney and Brittney. “What are you talking about?” I asked in a guarded tone.
Denise recrossed her legs and leaned against Courtney to put her head on her shoulder. “This guy and his fucking secrets, am I right?” she laughed. “I’m curious, are you this tight-lipped for their benefit, or for yours?”
The wine had definitely loosened her tongue. I flashed her a dirty look and took a sip of my drink. “You know I don’t talk about what happens behind closed doors,” I said. “You want to know something, ask them.”
“Mr. Discretion!” she said in a deep mocking voice, but her tone had been playful and joking.
Brittney smiled at Denise’s comment, then gave me a long look. When I smiled back, hers widened. Then her gaze grew more intense. I’d seen that look before. Hunger. She discretely patted the empty cushion next to her, but I decided to hold off. For now.
“What do you want to know?” Courtney asked Denise. Their hands had shifted from Denise’s lap to Courtney’s, where Denise fidgeted with the hem of Courtney’s dress.
“Why don’t you start at the beginning. How did you all meet?”
An hour later, Courtney and Brittney’s retelling of the First Timers Club saga approached current times, and Denise’s demeanor had shifted significantly in the interval. Courtney now sat reclined in Denise’s arms while Denise absently stroked her bare arms and legs. I’d known Denise a long time. Long enough to know when she was aroused, and I’d rarely seen her this worked up before. Her eyes lingered over Courtney’s body whenever she looked at her.
“Wait. So, you guys haven’t had sex at all today?” Denise asked, and Courtney shook her head.
“Not yet,” Brittney replied and Denise looked at her and affected a shocked face.
“Uh oh! You better watch out,” she said to me. “I think someone’s feeling a little heat in her coochie for you.”
I expected Brittney to react with her usual embarrassed blush, but instead she lifted her rosy cheeks into a smile. “More than a little.”
The wine had worked its magic on all of them, it seemed. Denise shifted in her seat and tightened her arm around Courtney’s waist.
“Speaking of warm coochies,” Denise said, “mine’s pretty wet after hearing your story,” she said to Courtney. “I’m so jealous of you girls. I never had anyone like fuck face over there to teach me about having sex when I was your age.”
“Why do you call him ‘fuck face?’” Courtney asked, laying her arm over Denise’s and stroking the back of her hand with her thumb. The first time she’d reciprocated with touches of her own.
Denise giggled, “Has he ever done that thing where he goes...” She sat up straighter and puffed out her chest, then deepened her voice to sound more manly. “‘Come over here, baby, and sit on my face so I can eat your little pussy’?” she asked with a laugh.
Brittney choked and snorted wine from her nose back into her glass.
“Oh my god, dude!” Courtney said. “She sounds exactly like you!”
Denise chuckled and settled back into the sofa. “I’ve never met a man who loves to eat pussy more than this guy, and there was this one woman we knew who wouldn’t shut up about how much she wanted to fuck his face, so I started teasing him about it and the name kind of stuck, because he has such a fuckable face, apparently.”
I looked off to the side and smiled, holding the bridge of my nose and shaking my head while the girls had a giggle at my expense.
“Very fuckable,” Brittney agreed.
Denise and Courtney paused and then snorted and laughed some more. When everyone settled down, Denise ran her fingers through Courtney’s hair and sighed.
“Fortunately for me, when I finally allowed myself to acknowledge the fact that I’d always been attracted to women, I met someone who helped me discover myself. She guided me through the coming out process.”
I rose to refill everyone’s wine glasses and fix myself another drink. We’d come to the part of the evening where Denise would make her move.
Courtney looked up at her and asked, “When did you first know?”
Denise smiled and said, “I think I’ve always known, you know? But I grew up in the kind of household where you didn’t talk about those types of feelings, and they would never, ever be allowed to be expressed, so I hid them as best I could. When my ex and I started having problems in our marriage shortly after I had Zoey, I decided it was time to stop lying to myself and finally accept who I really am.
“I’d met this woman, this amazing muralist named Valentina, several years prior through some mutual friends and I knew she was gay. I called her one day and asked if she’d meet me for coffee and I just opened up to her about everything. I told her about my attraction to girls when I was growing up and about my troubled marriage and how I didn’t want another man in my life if I ended it with Jared and ... I guess I just needed to talk to somebody who would understand what I was going through because she’d gone through it too.”
Denise stroked Courtney’s temple and softened her voice. “We talked for hours that day at the coffee shop. She was older than me, but I found her to be so elegant and feminine and funny and charming. We ended up back at her house and we talked and talked and as night fell, I found myself in her arms, just like this.”
Denise leaned over to put her face just a few inches from Courtney’s. “She looked at me, the way I’m looking at you now, and she smiled this beautiful smile that took my breath away and she asked if she could kiss me. Just like that. No hesitations, no beating around the bush, no awkward apologies. She just asked and I said yes and it was the most life affirming kiss I’d ever had because I knew right then who I was and what I wanted.”
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