by Amy DeMeritt
“Thank you.”
I pull my laptop out and start catching up on work emails while I wait for my team to arrive. The chair in front of me pulls back so I look up expecting to see one of my employees, but I’m pleasantly surprised to see it’s the brunette from the sidewalk. She sits down and I lick my lips with a smile as I lean back to fully appraise her while closing my laptop to give her my full attention.
“So, you’re just going to leave flowers on my table and not even ask me out?”
“Here you go.” A waitress sets my mojito down and then looks at the brunette, asking, “Can I get you anything to drink?”
“Oh, uh, I’m not staying.”
“I think you have time for a drink.”
She smiles and asks for a Long Island Iced Tea. After the waitress leaves, she looks at me with grin, and says, “So?”
“So, what?”
She releases a small laugh and leans forward with her head on her upturned hand, looking at me like she’s trying to figure me out. Her confusion and excitement are very enjoyable for me to watch so I’m in no hurry to help her to understand what I want from her.
“How about we start with names? I’m Lindsay.”
“I’m Jack.”
“That’s a very butch name.”
I laugh hard and her face spreads into a beautiful smile. I take a sip of my mojito and she watches my lips as I swallow and lick my lips clean.
Lindsay is of average build and height, has nice brunette hair just past her shoulders, rounded high cheekbones, nice red lips with a small dimple in her left cheek, and her eyes are light hazel.
“So, are you here to work? Are you like a bank investor or something, here to scope out the restaurant?”
“Halfway correct. I’m meeting a few of my associates here for a business meeting. I hate offices so I rarely go into work.”
“That must be nice. What do you do?”
“I hogtie all of the world’s biggest corporations by the digital balls and make them my submissives.”
She laughs really hard and runs a hand through her hair. “Ok, let me see if I can decipher that. Do you run an outsourcing IT company?”
“Nope.”
“But it has to do with computers, right?”
“Yes.”
“Ok, do you make something these companies need to do business?”
“You’re good at this. I develop computer software.”
“Wow, that’s very impressive.”
“What do you do?”
“I’m a teacher. I teach eighth grade.”
“Sounds very stressful. How do you like to unwind?”
I glance at her lips as I scan down her body in a meaningful way before meeting her eyes again, which makes her smile widen.
The waitress delivers Lindsay’s drink and promptly leaves. Lindsay takes a sip from her tea and looks me up and down for a moment.
“When are you going to ask me out?”
“I can’t do that because I don’t date. We can be friends with benefits, or I can just give you one very memorable afternoon, but I don’t do relationships.”
Her face falls in disappointment and she looks down at her glass while she twirls the straw, spinning the ice around the sides of the glass.
“I’m not that kind of person. I thought… I guess I should have known better. That move you pulled was just too romantic to be real. That kind of stuff only happens in movies and books.”
“The moment was a genuine gesture. It wasn’t a move or a tactic to lure you in here.”
“You didn’t expect me to come in here?”
“No, but it was a wonderful surprise that you did.”
“Why? Nothing will come from it. It was just a waste of time, as always.”
She stands up and pushes the chair in, looking very sad.
“Before you go, I want to say thanks for sitting down and sharing a drink with me. It wasn’t a waste, at least not for me. I hope you have a nice day.”
She looks down at me like she’s unsure what to do, but then she shakes her head and waves a hand in an overwhelmed dismissive way.
“Ok, bye.”
“Goodbye, Lindsay.”
I watch her walk back to the front of the restaurant, and as she gets her hand on the door, she turns around and starts walking back. Instead of sitting across from me, she sits next to me and leans in, but stops several inches away, as if she ran out of gas and stalled. I smile and caress her cheek as I turn to face her. She closes her eyes and leans her face against my hand. I press my lips against hers and she accepts me to fully kiss her. She releases a small sound and slumps into me as she places a hand on my thigh.
She pulls back breathless and glossy eyed. She scans my face and grips my thigh while biting her bottom lip in an aroused way.
“So, how does this work?”
“That depends on what you want.”
“Can I decide on being friends with benefits after… well… you know?”
I smile and kiss her lips. “Yes, of course.”
“Can I see you today, after your meeting?”
“Yes. Would you like to come back to my place, or do you want me to meet you somewhere?”
“Your place.”
“Here, put your number in here. I’ll text you when my meeting ends.”
She takes my phone and enters her name and number in my contacts. After I slip my phone in my pocket, she grips me behind the neck and pulls me into another kiss.
As she pulls back, she releases a small laugh and places her hands on her face, saying, “Oh, god, I’ve never done something like this before.” She looks up at me again, and quietly asks, “Will you be patient with me?”
“Of course.”
“I guess I better get back to my friends. You won’t forget about me, right?”
I kiss her lips and brush my hand through her hair. “No. I’m looking forward to this meeting ending so I can see you again.”
Chapter Seven
“So, any other questions on this new application?”
“Nope, we’re good, boss.”
“Great. Make sure you post everything to the board so I can log in and watch the beta testing progress. Let me know right away if you run into major issues.”
While my team packs up to leave, they discuss who they’ll assign certain tasks to and I send a text to Lindsay to see if she is ready to meet.
Lindsay: I’m across the street. I can meet you out front in a few minutes.
Me: See you soon.
I quickly pack up my laptop, and after signing the receipt, we stand up to leave. They chit chat for a few more minutes on the sidewalk, but as I start to walk backwards out of the group, they disperse. I wave to them as I turn to face Lindsay, who is leaning against the side of a car watching me. I walk over, offering her my hand, which she accepts with a cute shy smile.
“How was your meeting?”
“Very good. How was your lunch?”
“Ok. My friends spent at least half of it pestering me about coming to talk to you.”
“By the look they gave me when I gave you the flowers, I’m guessing they’d hate that you’re with me right now.”
“Probably.”
“Does that bother you?”
“No. Well, maybe if they knew it was just for sex. I mean, I wouldn’t be embarrassed to date you.”
“Here you go.” I open the passenger door to my Ferrari and her jaw drops.
“This is your car?”
“It is.”
She smiles really big and quickly gets in the car. I put my laptop bag on the backseat, and as I slide in the driver’s side, Lindsay leans over to kiss me. I start the car while we kiss, and she pulls back with an excited smile. I take her hand and pull away from the curb.
“So, uh, how old are you?”
“Thirty-one. You?”
“Twenty-nine. How did you get to have your own company? Did you inherit it?”
“No, I built it on my own. I started
my business when I was eighteen and still in a senior in high school. Have you always wanted to be a teacher?”
“No. For a long time, I thought I wanted to be a doctor, but I think that was mostly driven by watching too many medical dramas on TV. I think I ended up being a teacher as a default because I didn’t know what else I wanted to do.”
“Do you enjoy it?”
“It has its pros and cons. I love having the summer off.”
“What’s your favorite subject to teach?”
“English. I love to read and write. I love poetry and the classics.”
“You’re such a nerd. That’s adorable.”
She laughs and flashes me an adorable amused smile. “Yeah, coming from the one who creates computer software for a living. You are probably the coolest and hottest nerd I’ve ever met though.”
“Probably? No, I definitely am.”
She laughs again as she leans over to kiss my cheek, then rests her head on my shoulder. We drive in silence the rest of the way to my place, but as I pull up the long, wide driveway to my house, she sits up and gasps.
“Oh, my god. Is this your house?”
“Yes.”
“It’s huge.”
“It’s a modest house.” She gives me a sarcastic kind of smile and I laugh and nod. “Ok, it’s huge. I’m not sure if she’s home, but I have a tenant living with me right now. Please don’t feel the need to have a conversation with her. It’s not necessary.”
“Do you and her…?”
“No, I don’t sleep with tenants or employees.”
“Ok.”
I bring Lindsay inside, and of course, Carrie is sitting in the living room on her computer.
“Hey, Jack, can you…? Oh, you have a guest. Never mind.”
“I don’t want to get in the way of…”
“You’re not in the way. Can I get you a drink or anything?”
“A drink would be nice.”
I lead Lindsay to the kitchen, and while she scans the bottles of liquor on the counter and the wine and beer in the fridge, I send Carrie a text asking what she wants.
Carrie: It can wait. I just want you to read something.
Me: Ok.
Carrie: She’s pretty.
Me: She’s a teacher.
Carrie: I’m sure you’ll be playing that role soon. Have fun.
Me: Thanks.
“I don’t know what to pick.”
I pull two tumbler glasses out of the cabinet, and Lindsay slides up next to me with a cute content smile to watch me. I add a few ice cubes to each glass and pour a couple of shots worth of blackberry brandy overtop. She takes a sip and her smile widens.
“That’s really good. Thank you.”
I take her other hand and lead her out of the kitchen and towards my master suite, which is basically three rooms that are connected – my bedroom, bathroom, and sex den.
My sex den is designed with classy white and black furniture, including a bed, chairs, cushioned tables, a round stage, an electrical stimulus chair, and a couple of different contraptions for more intense types of bondage for the more adventurous women I fuck with. I have chains with leather cuffs hanging from the ceiling and attached to the walls and the floor. I also have several free-standing mirrors that I like to use to increase anticipation and arousal.
As I open the door, Lindsay’s hand tightens on mine and she freezes just inside the door, looking around with a terrified expression on her face. I release her hand and take her drink to set them on a side table by the bed. I pull my blazer off, tossing it to lay over the back of a chair, then pull my tee shirt off. Lindsay scans my body with her bottom lip between her teeth and allows me to pull her further into the room so I can close the door.
I press my body against hers, and as I position my lips to hover just in front of hers, I comb my fingers through her hair. Her eyes close as she leans into me while taking a fast-shallow breath of air. I trail my fingertips down the sides of her neck and down her arms. She inhales deeply and tentatively places her hands on my ribs.
I give her a soft kiss on her lips, then pick her up, having her wrap her legs around me. She giggles in an excited way and holds onto the back of my neck. After I set her down on the edge of the bed, she palms her hands over my abs and breasts.
“Are you going to hurt me?”
“I would never hurt you. This is a room of pleasure.”
“What are you going to do to me?”
“What would you like me to do to you?”
She looks around the room and swallows hard before saying, “I think I need more of my drink.”
I hand her the drink, kick my shoes off, and then crawl up to sit against the headboard. She shuffles to sit next to me and looks around the room while she takes sips of her brandy.
I trace my fingers along her jaw to her chin, turning her to face me, and ask, “What are you hoping to experience today?”
“Something amazing.”
“Can you put your trust in me?”
“Yes.”
“If there is anything I try to do that scares you or you’re not comfortable with, please tell me. I want you to enjoy every minute of this experience.”
“Ok, I will.”
“Are you ready?”
“Yes.”
She gulps back the rest of her drink, then I place both glasses on the side table. I pull her up to sit on her knees and engage her in a kiss that becomes intense very quickly. I pull her blouse off, and she watches me with glossy eyes as I palm up her soft stomach and up over her breasts. As I pull her bra off, she releases a sound of arousal and nervousness.
With a hand against her cheek, I give her light kisses on her lips and neck while I cup her left breast. I trace the pad of my thumb around her nipple, causing it to harden, and she releases another sound of arousal.
I glide my hands down her torso to the waist of her jeans, and as I tug her button apart and her zipper down, she grabs my head, pulling me back into a kiss. As I push her pants and panties down to her knees, she pulls back to lay down. I tug them off and her thighs fall open with her arousal coated folds rising in need.
“Don’t move.”
I climb off of the bed and get four lengths of chains with leather cuffs. I secure all of them to the headboard, then lock her hands above her head. I cuff her ankles so she can’t straighten her legs forward and has to remain spread open.
She’s breathing hard and slightly shaking, but she doesn’t object and she still looks aroused and excited. I pull my socks and pants off and put on a harness with a seven-inch-long and two-inch-thick shaft.
As I climb on the bed between her thighs, her hips rise and she grips her chains in her hands. I suck and bite the insides of thighs, hips, stomach, and breasts while I move in closer to penetrate her. As I press my lips to her panting mouth, I guide my shaft inside of her. She releases a gasping moan and bucks against me.
Her screams and moans increase as I grind against her and thrust deep inside of her. I alternate between a deep and hard thrust, with a slow and shallow pumping grind to rub against her clit, which causes her body to buck and spasm in pleasure. Her screams are erratic and loud while her face is contorted in a wonderful unabashed sign of pleasure. The headboard creaks with the tugs of her chains as she thrashes around, which seems to increase her arousal. Each time the bed creaks, she releases another moan.
As she cums, she screams my name and her chains clank loudly with her body spasming under me. I stop pumping and I lay on top of her with all of my weight while staying deep inside of her.
“Oh, my god, that was the best sex I’ve ever had. Oh, Jack, I can’t move. I’ve never cum so hard from being penetrated. Oh, god, you’re still inside me, and it’s so… Oh, god, I want you to fuck me again.”
I kiss her lips then get her repositioned on her knees facing the headboard. I cuff her hands, then slip a clit clamp on her, which causes her to moan. I grab a narrow anal plug, and after getting it lubed up really well
, kneel behind her. As I press my cock inside her vagina, I slowly push the anal plug into her ass. She screams loudly and bucks backwards against me, taking in my full length.
It doesn’t take her long to cum again with a combination of moans, screams, and whimpers, with obscenities and my name mixed in.
“Jack, oh, shit. I don’t think I can take anymore right now. Oh, it was so good. Can I lay down now?”
“Yes, of course.”
I remove my toys from her, then I help her out of her chains and guide her to lay on the pillows, where she lands with an adorable relieved happy laugh. I pull my harness off and climb up to lay next to her on my side with my head on an upturned hand.
“Just give me a few minutes, then I’m going down on you.”
“You don’t have to. I thoroughly enjoyed fucking you.”
“You came with me?”
“Just after, both times.”
“Can I accept that as a compliment, or is that normal for you?”
I smile as I pinch her hardened nipple. “It’s common, but it doesn’t always happen. You can take it as a compliment.”
“Would you enjoy doing this with me again?”
“I would.”
“Can we try being friends with benefits then?”
“Absolutely. You’ll have your own little toybox, till you decide to ditch me for a real relationship.”
She laughs a little as she rolls onto her side to face me. She suddenly looks nervous, and quietly says, “I guess it’s a little late to be worried about this, but… Please don’t take offense… Will I be at risk of any, you know, STDs?”
“No. I’m clean. I’m very careful, but I get tested every month just to be sure something didn’t slip by my precautions.”
“So, the stuff you used on me…?”
“Have only been used on you. They’re brand new. I don’t use toys on more than one woman.”
“That’s good to know. I want to kiss you.”
I smile and place my hand on the side of her neck, drawing her in closer. As our mouths begin to tumble together, she presses her body in closer. I grab her ass and pull in her harder, eliciting a sound of renewed arousal. She suddenly sits up and pushes me on my back as she straddles my hips. She bends down to kiss me while her hands rub my torso and squeeze my breasts through my sports bra. Her hand glides down my torso and slips inside my underwear. She releases a moan into my mouth as her fingers easily glide over my arousal glossed folds.