Sheri's First Time
by Robbie Robb
Copyright© 2026 by Robbie Robb
“Fuck!” Sheri shouted in frustration as she threw her phone down on the couch beside her. The guy who was supposed to be picking her up in twenty minutes for a date just texted her and said he couldn’t make it, with no promise to reschedule. If that wasn’t bad enough, tonight would have been that mythical ‘third date’ and Sheri hadn’t been able to stop thinking about it all day.
She picked up her phone and sent off a couple text messages to friends. A few of them had plans to go out to a club tonight and Sheri had begged off because of the date. Hopefully she’d still be welcome. Within a few minutes the replies came in with news that a couple people weren’t feeling well so the whole thing was scrapped.
She sighed and looked down at herself. “All dressed up and no place to go,” she said aloud to the empty apartment. The slim brunette was indeed all dressed up. She had on the proverbial Little Black Dress that accentuated every inch of her five foot, three inch frame, highlighting the curves of her hips and the gentle swell of her B-cup breasts. She had even decided to forego underwear thanks to the firmness of her breasts mixed with her overwhelming desire to get laid.
“Fuck it,” she said aloud, once again to no one. “I’m going out anyway.” She grabbed her small purse and phone, summoned a rideshare and headed outside to enjoy the summer evening while she waited for her car.
The place she chose as her destination was more of a pub than a club but also featured a back area that usually had a live band as well as a DJ between sets. She sat down at the bar and ordered a drink from the bartender, nothing fancy, just a double rum and coke. She looked around the room, taking in all the people that were mingling about.
The front area was hosting karaoke that night so Sheri sat at the bar and listened to a few singers as she worked on her drink. The first couple were really good but the third one was pitchy and the song he chose was more than a little outside his range. She finished her first drink and was starting to feel it warm up her system. She motioned to the bartender for a refill.
After the bartender delivered her drink, she decided to take a walk around and check out the live band area. She headed back and was initially a little disappointed to find out that instead of a band, they were having a DJ competition where a group of deejays got to spin short sets. However, as soon as she felt the bass drop on the current DJ’s set, her mood changed and her body started to move in rhythm with the song.
She made her way to the dance floor and let the music flow through her, transforming her movements into a synchronicity of moves that rivalled even the best choreography. It only took seconds for Sheri to lose herself in the music, eyes closed and completely unaware of anyone else around her.
“I’ve missed this,” she thought. When out with her friends, she always felt like she needed to be present for them, unable to just shut them out and give herself to the song. But tonight she was alone. There was no one here who knew her, no one that she needed to pay attention to. It was just her and the music.
Songs flowed seamlessly from one to the next, break beats matching tempos perfectly, the bass line keeping her energy high. Sheri lost track of the number of songs as she danced. It wasn’t until the music stopped and the DJ thanked the crowd for her loud support did she even notice how out of breath she was and that she had finished her drink.
The music had been replaced by a canned playlist while the deejays swapped out their equipment for the next entrant in the contest, its volume set lower but still loud enough to keep the energy flowing in the club. Sheri made her way to the club bar and got the attention of the bartender. “Double rum and coke!” she yelled over the music. After getting her drink, she spotted a stool at a bar top table and took a seat to catch her breath.
Sheri was watching the equipment setup on the stage when a voice from behind her startled her, “You were amazing out there!”
Sheri spun around to see a woman, about her age, standing close behind her with a big smile on her face. “What?” Sheri asked, unsure of what she heard.
The girl gestured to the dance floor, still smiling, “Your dancing! You looked amazing!”
Sheri felt her cheeks flush with embarrassment, having forgotten that other people may actually pay attention to her. “Thanks! I didn’t think anyone would be paying attention to me.”
The woman motioned to the empty stool beside Sheri, “May I?” Seeing Sheri nod, she sat down. “You were impossible not to notice. I’m Sasha by the way.”
Sheri took in the woman as she sat down beside her. She guessed that she was about the same height as herself but had larger breasts. It was hard to tell under the black t-shirt the woman was wearing, but Sheri guessed maybe a large C-cup, but her small frame made them seem even larger. “I’m Sheri, happy to meet you. Were you out there dancing?”
Sasha shook her head, “Not that set. I had just finished packing up my stuff and needed to rest. I was sitting over by where you were dancing. Are you a dancer?” A look of horror crossed Sasha’s face. “Wait! No! Not like that!” she rushed out. “I meant are you a trained dancer, not a ... err ... well...”
“A stripper?” Sheri finished off, with a smile on her face, making her new companion aware that she didn’t take any offense. She shook her head, “Nope, not trained and most definitely not a stripper. I’m just a girl who remembered tonight that she loves to dance.” A look of relief washed across Sasha before Sheri asked, “Packing your stuff?”
Sasha thumbed towards the stage, “The ol’ ones and twos. I played the second set, two before the one you danced to.”
“Oh wow! I’m sorry I missed you! Will you get to play again tonight?”
Sasha shook her head, “Not tonight. But if I advance beyond tonight, I’ll be back next week for the finals. It will be close, but I think I have a shot of making it. Rob, the guy you danced to, is a shoo-in to make the finals and is probably the best DJ around. And he still does it all old school, with vinyl records, instead of using the new decks and mixers with digital audio. But I’ve got a few tricks up my sleeve that may help push me over the top.”
“I guess that means if you advance, I’ll just have to come back next week to see you perform,” Sheri said, smiling.
A wide smile formed on Sasha’s face, “I’d love that! Would you really?” To Sheri’s nod she responded, “Thank you! That means a lot! Do you live around here then?”
Sheri shook her head, “Not that close. Definitely not close enough to walk. Do you play here often?”
It was Sasha’s turn to shake her head, “Not very often, it’s a little far to lug all the equipment and I don’t have a car. I’m fairly regular at Bar None.”
Sheri looked surprised, “What? That’s just a couple blocks away from my place! You live around there too?”
As Sasha nodded, the music turned off and a new DJ took the stage, starting their set with a booming bass rhythm. “Come on!” Sasha yelled as she reached out and grabbed Sheri’s hand. “Let’s dance!”
The two women moved onto the dance floor and quickly found the rhythm. A couple seamless song transitions later, the track slowed down to a more sultry tempo. At that moment, Sheri had her back to Sasha and started to sway to the song, her hips working their magic as she flawlessly matched the music. She felt arms wrap around her waist and join together on her taut stomach. Somewhat startled, she quickly turned her neck to see Sasha there, her body pressed tight against Sheri’s back. They locked eyes and Sasha’s glimmered as she smiled at her new friend, “Didn’t mean to startle you, I hope you don’t mind!” she yelled over the music.
Sheri smiled in response and shook her head no. She turned back and placed her arms over Sasha’s as the pair started to sway together. “You looked so hot with your hips swaying that I couldn’t help myself,” Sasha said, her mouth up very close to Sheri’s ear. Sasha pulled back a bit, but not before lightly brushing her lips against Sheri’s neck. Sheri gasped at the touch and felt a shiver run through her body, from her neck down between her legs.
It suddenly dawned on Sheri that this woman was heavily flirting with her. Her mind started racing. She’d often wondered what being with a woman would be like. She’d even tried a few dating sites in the past but never was able to find the right woman. They either didn’t respond or ended up being crazy and borderline stalkers.
A shift in the music allowed Sheri to spin around so she was facing Sasha without breaking free from Sasha’s arms around her. Being close to the same height, Sheri’s eyes met Sasha’s and saw concern on them. She put her arms on Sasha’s waist and pulled her closer, moving her mouth to Sasha’s ear, “That felt nice. Really, really nice.” Pulling back she saw the radiant smile had returned to Sasha’s face and felt her exhale the breath she was holding.
“So ... then...” Sasha began with a questioning look on her face, being loud enough for Sheri to hear.
Sheri looked around, hoping to find someplace more quiet to talk.Spotting a side door leading to a patio and motioned for Sasha to follow. Once outside, Sheri put her arms back on Sasha’s waist and held her close. “So ... here’s the thing. That thing you did ... felt good. REAL good ... and I was already enjoying your company before that ... It’s just that,” Sheri paused. Sasha didn’t break eye contact during the silence, waiting for Sheri to continue. “It’s just that I’ve never been with a woman before so I’m more than a little bit nervous. But you also have me excited. VERY excited. So, if you’re okay with maybe going a bit slow and showing me-”
Sheri was silenced by Sasha’s lips pressing lightly against hers. She felt Sasha’s tongue at her lips and opened her mouth to let it inside. Their tongues danced for a minute, causing both women to moan, before Sheri sucked Sasha’s tongue into her mouth and kept sucking on it with just the right amount of pressure.
When she finally broke the kiss, Sasha pulled back, “Holy fuck! I’ve never ... That was hot!” She took a breath, “I think it’s pretty clear that I’m into you. And I’d really like to explore that further with you ... but this isn’t the place for that. I know you want to go a bit slow, and I’m good with that, but how about we grab my stuff and head back to my place? We can get to know each other a little better.”
Sheri broke into a big smile, “That sounds like a really good idea!”
Sasha took her by the hand and the two went back into the club. Sasha ordered a rideshare and the two of them quickly finished organizing her gear. Between the two of them, they grabbed her equipment and headed out the side door of the club, onto the street. They only had to wait a moment or two until the car pulled up. Loading Sasha’s cases into the trunk, the two climbed into the backseat, Sasha taking the middle seat to sit next to Sheri and the car pulled silently away from the curb
Sheri’s hand quickly found Sasha’s and the pair held hands the entire ride back to Sasha’s, the two of them exchanging frequent kisses. Sasha’s other hand would occasionally lightly stroke Sheri’s bare leg, to just underneath the short hem of the minidress, causing Sheri to shudder and moan softly into her new friend’s mouth.
“You are making this very hard to go slowly,” Sheri hissed quietly, with a devilish smile on her face. “I’m having some very naughty thoughts right now.”
Sasha’s eyes lit up, “Oh? You can tell me all about them when we get to my place!” She traced her finger over Sheri’s lips, “Or ... maybe even show me.”
Sheri’s eyes flared with lust at Sasha’s words and touch. She nodded, barely whispering, “Maybe.”
The car arrived at Sasha’s apartment and Sheri became aware of her surroundings, “You’ve got to be kidding me!”
“What?” Sasha asked, stopping just before her entrance.
Sheri pointed to the building across the street and a couple doors down, “Mi casa.”
Sasha laughed, “Well, at least you’re close to home!” She added quietly after, “But hopefully you won’t need that tonight.”
“What was that?” Sheri asked, having heard the other woman mutter something.
“Hmm? What? Oh, nothing,” Sasha smiled. “Come on, let’s get inside!”
They took the elevator up to the seventh floor and made it to Sasha’s apartment. She unlocked the door and went in, Sheri following her. “Just put the gear over here,” Sasha told her, piling what she was carrying in a corner.
After Sheri put down the case she was carrying she turned and Sasha was right there. She pushed Sheri against the wall and locked lips with her again, Sheri actively returning the kiss. Sasha finally broke the kiss, both of them panting. “Before I forget, that dress looks amazing on you! You want a drink?”
“Thanks! And yeah, a drink would be great. Whatever you’re having. It seems like it’s a little hot in here,” Sheri replied. She looked around the apartment and saw it was tastefully decorated with a small breakfast table in the dining area and a loveseat facing a wall mounted TV in the living room, end tables on either end.
“I love your place! It’s so welcoming!”
Sasha called from the kitchen, “Thanks! Have a seat, I’ll be right out.” Sheri sat down on the love seat and wiped her palms on her dress, butterflies doing loops in her stomach. A moment or two later, Sasha came into the living room carrying a tray with a bottle of rum, an unopened bottle of mix, a bowl of ice, and a couple glasses. “Ice?”
Sheri shook her head, smiling, “No, thanks. Not for my drink anyway.”
Sasha’s head flew up to look at Sheri, seeing her smiling at her. “That can be arranged,” she winked. She poured a good measure into each glass and cracked the seal on the mix. After topping off both glasses, she passed one to Sheri and took one herself, sitting down beside Sheri. “Cheers!” she said, offering her glass in toast.
Sheri returned the gesture, “To new ... friendships!”
“And maybe more!” Sasha returned.
Sheri nodded and smiled, “And maybe more!”
The two women each took a long drink from the glass, then set them down on the end tables. “So,” Sasha began, “Welcome to my home. This is the living room, that’s the kitchen, the bedroom is through that door, and the bathroom is through the bedroom. It’s small, but I’m a small woman and don’t need a lot of space. If I have space, I just tend to fill it with stuff I don’t need.”
Sheri nodded, “I’m the same. My place is about the same size as yours I think.” She paused, “Soooo ... what was that you mumbled to yourself outside before we came up here.”
Sasha blushed, “Nope.”
“Come on, tell me! I wanna know,” Sheri smiled.
“No way, it’s kinda embarrassing,” Sasha said.
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