The Stepdad's Club

Everyone in this story is 18 or older. This is a fictional fantasy. It will be a slow burn and lengthy. If you like a quicker story, this is not the one for you. We are going to pretend STDs are nonexistent for this story. Pregnancy is a possibility.

"Tess? Pumpkin? I need you to wake up."

Theo's voice is barely above a whisper. He's softly rocking me from my deep sleep.

"I swear to God, Theo. If it's before 8am on a fucking Saturday, I will hurt you."

"Shhh! Your mom is just down the hall in her office."

I open my eyes enough to see a blurry outline of Theo's face as he kneels next to my bed.

"What time is it? Seriously. I'm not fully opening my eyes until you say-"

"It's 8:15. You can open them. I left the curtains shut."

I unravel myself from numerous blankets and sit up. I open my eyes fully as Theo takes a seat at the end of the bed. Life has been unexpectedly normal since we had sex for the initiation.

Mom has been home for over a week, now. Theo is holding it together, for the most part. He checks his phone every five seconds. Terrified he'll miss a call from the club. It's been silence since he submitted our video.

"I need you to go somewhere with me today. Can you be ready by 9:30?"

I finish stretching and yawning to semi-whisper back.

"Ugh, why?"

"The club called."

"And?"

"They're having a meet up. There's been a lot of interest since our visit."

I knew this day would come, eventually. I get the secrecy. That's pretty obvious. The last-minute scheduling is a pain in the ass.

"I need coffee."

Theo points to my bedside table where I see an iced coffee and my favorite breakfast sandwich.

"What else you got in your bag of tricks?"

"Your mom has brunch with some clients today. I told her we're running errands and grabbing lunch. That should keep her from coming home too early and buy us time."

I nod, still fighting to wake up. I was looking forward to sleeping in. Maybe tomorrow. Theo kisses my forehead and quietly exits my room.

I take a shower after eating my breakfast. I don't know exactly what you wear to something like this. I settle on jeans, a cute v-neck blue top, and a light jacket. Put on some makeup, fix my hair, and head to the kitchen.

"Don't you think that top is a little low cut?"

Theo can't decide if he wants to look at my eyes or my breasts. He decides on my eyes with a concerned look on his face.

"Might as well show off since there's a good chance most have already seen it on video. I'm shocked you're not wearing a gray sweatpants to show off your dick."

"Alright smart ass. Get in the car. We can't be late for our first official meet up."

He smacks my ass as I walk past him to the door. I bite my lip as I lock eyes with him over my shoulder.

"Keep it up and you'll have to go to the first meet up smelling and tasting like me."

I run my thumb lightly across his bottom lip. He swallows hard and crosses his hands over his crotch. I can see the gears turning. He shakes his head to rid himself of the preview he just saw.

"Just get in the car, Tess."

"Mmm, I like it when you get stern with me."

I lean in and he instinctively pulls me closer. He has a good grip on my hips when his phone vibrates and snaps him out of his trance.

"Seriously, Tess. Let's go."

I relent and head outside. I admire my new Lexus IS 500 from the passenger window of Theo's car. It's red. I love it. A lot less work than getting my first car. Mom barely asked any questions. Nothing is too good for Daddy's girl. Including expensive cars.

Theo sighs and turns to me, "Are you going to be a brat the whole day?"

I shrug and give him my most innocent smile.

"Well, if I don't get laid today, you'll fuck me some other way."

He hits the gas before I can respond. I'm expecting to go to "The Room" like last time. Theo drives in a completely different direction for almost half an hour. We eventually pull up to the semi-restored mill building on the edge of town.

"Well, isn't this homey. Are they going to finish the restoration anytime soon?"

"Tess, what will it take for you to rein it in until this is over?"

He watches me patiently as I contemplate my options. I lean over, place my hand on his thigh, and slowly work my way up his leg. My lips so close they almost touch his ear.

"I'll behave if you let me pick first. I can practice my oral skills on you so we know I'm ready. You seemed to enjoy them the first time."

His clenches his jaw momentarily. I cock an eyebrow and give him a naughty grin. He clears his throat and holds his hand out. Pinky extended like we have for years.

"Pinky promise."

We shake pinkies and then we put our phones in the glove compartment. Since we learned the club holds on to them it's easier to just leave them in the car.

We exit the car as more people arrive. Following others down an alley and into a side door. We walk through a series of hallways until we reach the final door. Through the door is a large space, similar to "The Room".

I see Mr. Blake waving everyone inside. Is he in charge? Otherwise, why would he be here before everyone else?

The room gets smaller as everyone files in. There's close to 100 people here. I spot Destiny to the right with Scott at a table. I grab Theo's arm and head towards them.

We take a seat at their table. Scott is grinning from ear to ear as he grabs drinks off the bar. Mocktails for Destiny and myself. After hellos, Scott begins to fill Theo in on what will happen next. Destiny and I try to catch up. We don't have much in common.

"So, how are things? Enjoying the attention little miss popular?"

"Don't ever change, Destiny."

"I'm serious! Nearly everyone in the club is here. What the hell did you do in your video?"

I look around and take in the sheer amount of people in the room. The space is massive and there are people everywhere. I turn back to Destiny in minor shock.

"Hold on. You think this is because of our video?"

She leans forward so only I can hear her.

"I know it is. The men can barely contain themselves when new members join. But this. This is the biggest group I've ever seen."

The music lowers and a new voice speaks causing everyone in the room to hush.

"Welcome everyone! Welcome! It's nice to see so many of you in attendance today. Of course, we must give a warm welcome to our newest members. Tess and Theo, it is an honor to have you join us. We hope you enjoy everything we have to offer.

A review of the rules, as always. Anyone can update their lists today. No negotiations or bribes are allowed to be on anyone's list. You can and will be asked to leave the club. Permanently. There are a minimum of two different pairings before you can repeat a past pairing.

While not against the rules, it's worth mentioning as we have brand new members. Please limit contacting members outside of meet ups that you haven't been paired with. Especially, during the week the pairs are together.

You are not required to submit a new or updated list today. Lists can be edited, submitted, and withdrawn during any meet up. The lock box is on the bar for any list submissions. You may leave at any time. We have the building until midnight so enjoy yourselves."

The music returns as does the conversational hum. I take Theo's hand and walk out the main door to the hallway. I round the corner to ensure we're alone. I lean close and we speak in hushed voices.

"We need to set our own rules before we talk to anyone."

Theo nods in agreement.

"There is a fuck ton of people in there, Theo. I don't think Destiny and Scott should be near the top of the list. It's a waste of a choice. Especially, so soon."

"Tess, that's bullshit. He got us in the club!"

"Would you calm down and listen for a sec?! Keep your voice down. We don't know who's around."

Theo looks around the corner and he confirms it's still empty.

"Why don't we just schedule a night with them? We swap one night on our own, and we use our lists for options we don't have direct access to."

Theo thinks it over for a moment and realizes I'm right.

"I'll talk to Scott. I'll have him send me some dates."

"Thank you. Next thing. We should both have two picks by the end of today. No need to rush. We're taking turns with my pick being first. Like we agreed in the car. Remember?"

Theo smirks and softly nods.

"I remember. We can add rules as we go. For instance, home is off limits. Can't bring anyone from the club there."

"Scott and Destiny count in that too. They can only come over for family things and no messing around during family or holiday things."

"Deal."

We hear the door open around the corner and decide to head back inside. Theo walks towards Scott and I veer left to a small group of stepdaughters. I see two familiar faces and join them. I'm introduced to the rest of the group, and quickly given tips from everyone.

I ask acquaintances to introduce me to people they've told me positive and interesting things about. I lose track of time as I make my way around the room. I feel a cool breeze on my back and see it's coming from the open doors of an expansive patio.

I see my opportunity and head out the open doors. I take a deep breath as I leave the noise behind me. The building sits near the bank of a river. The water is calming in contrast to the music and conversations. I take a seat and watch the steady flow of the river for a while.

I'm quietly thinking about the people I've met so far today. Many gave me business cards. I put short notes on each to give me more details to remember them by. I'm looking through the cards again when I hear footsteps approaching from behind me.

I place the cards in my pocket and look back to the river. Watching the steady flow to calm my nerves as the stranger approaches. He takes a seat at the same table to my right. My jaw nearly drops when I see who the stranger is.

Cyrus Russo. That explains how we got into this building. One of his many companies is a restoration business. Russo Restoration is currently restoring the mill building as well as multiple businesses around town. This building seems to be going exceptionally slow.

He owns restaurants, coffee shops, laundromats, bakeries, grocery stores, and so on. The rumors have been around as long as his family has lived here. They're laundering money for the Mafia, the CIA is surveilling him, or whatever conspiracy theory that got some attention on Facebook.

I don't know where the Russo's money first came from. I do know, Cyrus Russo is Italian and Greek. He is a very attractive man with great genetics and lots of money. His plastic surgeon is a fucking magician.

Cyrus is 46 years old. 5'10" with dark hair and eyes. He must dye his hair. There isn't a single gray. I bet he would look sexy as hell if he went salt and pepper.

"Hello, Tess."

His voice is rich and silky smooth. Hearing my name on his lips, I instinctively press my legs tightly together. I've met him before. The reaction is usually the same. I've seen him around town and at my school. His stepdaughter is Emmaline. Emma is what she usually goes by.

Emma is a 20-year-old college student. Incredibly smart and beautiful. She speaks three languages, English, Korean, and Italian. Emma's mom is Korean and Italian. She speaks five languages and works as a professional interpreter. Cyrus hired her when he visited South Korea 10 years ago. They married just a few months later and moved to the US.

"Hello, Mr. Russo."

"Tess, please. Not so formal. It's Cyrus here."

I finally meet his eyes and I can't look away. He's quite intense. I can see why so many people find him intimidating. He has a warmth to his gaze that slightly puts you at ease while peering deep inside you.

"Fine. Cyrus it is."

"I know you heard the rules announced earlier. Some of those are flexible if you trust the right people. I'd like to add my card to your little collection."

He offers me his card and I take it with a smile.

"I'm glad you're well acquainted with the rules and their flexibility, Cyrus."

He stands and walks around to my side of the table. He holds his hand out and waits patiently. I gladly take his hand and stand. I'm facing him and we're quite close. He lifts my hand to his lips and softly kisses it. His eyes never leaving mine making his gesture incredibly intimate.

Cyrus places his hand on my lower back and begins walking me back towards the open doors. I see Theo appear in the doorway and we stop in our tracks.

"There you are! Oh, Cyrus. I didn't know you were enjoying Tess's company. Alone."

Theo takes a few steps closer and looks around the patio to confirm it's empty. A worried smirk on his face. Cyrus speaks to him with carefree confidence.

"It's quite alright, Theo. We were just headed inside. Thank you for your time, Tess."

Cyrus disappears inside. I turn to see a disappointed look on Theo's face.

"Why are you looking at me like that?"

I cross my arms defensively and wait to see what he comes up with. Theo's eyes drop to my cleavage, and I remember my low-cut top. I'm hoping that will distract him.

"Cyrus Russo? You want to fuck a Mafia guy?"

Damn it. I wish I had known how long the drive was. I would have done more to loosen Theo up.

"What do you think of his stepdaughter, Emma?"

Theo's eyes widen at the realization of what I'm going to ask.

"Tess. No way. Cyrus Russo?!"

"Will you calm down?! He isn't in the fucking Mafia! He's going on the list. Maybe not top of the list, but Cyrus and Emma are definitely on it. Plus, you're spending time with Emma. Not Cyrus. I've seen how you look at her."

I see realization come over Theo's face. He knows compromise is the only way out of this.

"In the top 10?"

"Top three."

"Top five."

"Theo..."

"Fine! Fuck. Top three."

Another pinky promise and we finally head inside. The room has thinned out over the last hour. We take a seat on a soft green couch and pull out the blank list. We complete the top three and discuss the fourth.

Theo makes a solid stance about putting Scott and Destiny somewhat high on the list at number four. They're going to be on the list at some point, anyway. I agree and add them to the list. Scott is the reason we got invited.

We finally have our top four. Theo is still not pleased about Cyrus. I was shocked who he decided as his first pick. Theo liked what he saw of Shea and knew I wanted Mr. Esposito on the list.

Theo & Tess

1. Mr. Blake and Mei

2. Mr. Esposito and Shea

3. Cyrus and Emma

4. Scott and Destiny

Theo brings the list to the bar, and we leave. I check my phone the second we get in the car. Text messages are first. Boyfriend has to work late. Lame. Link wants to come home next weekend. That could be fun. Mom is having dinner with people she met at brunch. Cool.

"Theo? When was the last time you had sex?"

He chuckles and shakes his head.

"You were the last time."

I've had my suspicions that mom is sleeping with someone else. Their relationship isn't completely monogamous. However, you're not supposed to completely ignore your spouse.

I lean over towards Theo and put my lips close to his ear. I place my hand softly on his chest and slowly trace my fingers downwards.

"Mom is having dinner with friends."

He stays quiet as my hand travels lower. His breathing slowly increasing as the button comes loose on his pants. He keeps his eyes on the road.

"Yeah...saw the text from her."

We're driving on a winding two lane back road. We won't hit a highway for another few miles. I pull the zipper down and he's still not reacting. I reach in his pants and firmly grip his growing cock in my hand.

I slowly stroke as he rapidly hardens in my grasp. I'm kissing his neck and moaning in his ear as I nibble his ear lobe. I feel my pussy getting wet as he begins to thrust into my strokes.

"You like that, don't you Daddy?"

He's finally giving in and getting breathy with his answers. Tightening his grip on the steering wheel as I take his cock out of his pants.

"Mmm, Tess. Double lanes...in a couple minutes."

"You better be paying close attention then."

I look down and he's leaking precum. I see my opportunity and I take it. I dip my head under his arm and quickly put the precum covered head into my mouth.

Through gritted teeth I hear, "Shit, Tess."

My head bobbing up and down as I stroke. Keeping a good pace, sucking, and licking. I moan when I feel him throb making him more eager. I push him deeper into my mouth and reaches my throat.

"Double lanes...we're at the...double lanes."

I moan to let him know I hear him. He moans in return as the vibrations run from the tip down his shaft. His moans get softer and I know other cars are driving alongside us.

We should be getting close to the highway by now. Instead, the car begins to slow down. I don't let up. Sucking harder and stroking faster. He can't last much longer.

Theo sounds panicked as he's moaning through gritted teeth. The car is slowing until we're barely moving.

"Don't...sit...up. Please...damn. Don't sit...up."

My "mmhmm" is muffled as my mouth is full and I'm drooling down his shaft. We must be in traffic. He's taking advantage of the slow driving and thrusting into my mouth in rhythm with my head bobbing.

His cock is starting to swell. His breaths are short and quick. Daddy's close.

"Oh fuck. Tess, I have to cum."

"Mmhmm."

"No, go faster! I have to cum, now!"

I pick up the pace hearing how serious he is. I tighten my grip as I stroke and take him deep as much as I can with each bob.

"Yes, baby, yes! Oh fuck."

He throbs hard and I feel warm cum spill into my mouth. I slow my stroke and swallow as he cums. Moaning and sucking softly until he's twitching happily.

"Okay sit up. Sit up! Quick!"

I sit up wiping my mouth on my sleeve. Theo zips up just in time for us to pass three cop cars and two cops directing traffic. They gaze into the car as we slowly crawl by a massive accident.

"Shit. You really let me cut that close."

"Would you have listened if I said no? Pumpkin, I know better."

Theo cups my chin and kisses my cheek. We're finally out of traffic and make it home a few minutes later. I head to the kitchen. I'm grabbing a snack when I feel someone behind me. Strong hands on my shoulders. Massaging softly.

"It's your turn."

He moves my hair away from my neck and his lips are kissing my ear and neck. Warmth rushes through my body as he grabs my hips and turns me to face him. I drop my food and his lips are on mine.

Theo wasn't kidding when he said my turn. My arms are around his neck while he quickly removes my pants and thong. He lifts me up on the counter and spreads my legs. His middle and ring finger expertly slide inside me and my moan echoes through the house.

"Good girl."

He knew I'd be turned on after sucking his dick in the car. I pull my shirt down to expose my breasts and I feel Theo's warm mouth on my nipple. The licking and soft sucking makes me throb on his fingers.

He continues regardless of how hard I throb and moan. It just encourages him. He curls his fingers inside me as they go inside, while lightly rubbing my clit with his thumb. Not enough pressure so it feels like a tease.

His lips move from my nipples, neck, ears, mouth, clavicle, and lips. I grip at his hair, shirt, and skin the more my pleasure builds.

Theo drops to his knees and spreads my legs wide. His tongue finds my clit and I moan loudly. I'm shaking and squirming as he exposes the most sensitive spots. I watch him hungrily eat my pussy on the same counter he makes his morning coffee.

He looks up at me and softly sucks my clit. The muscles in my core tighten instantly as my eyes roll back in my head. I completely let go and give Theo control. He holds my legs open even though I desperately try to close them around his head.