Date Night. (+18)

(Updated)

I get everything ready. I put the ropes, whips, and ball gag into a bag. I put it in the toolbox of my truck. It's 3 pm now, so I take another shower. I brush my teeth and take care of my beard and hair. I pick the best clothes, and I have to give them my best. I get dressed and head downstairs by the time I get done. It's 5:15 pm, so I kiss Samantha and tell her I won't be back tonight and to be safe. Call me if anything happens. 

This is going to be a long night, but it's going to be worth it. I mean, how many guys can say they fucked five girls in one night. I pick up flowers on my way to Barbra's house; I reach her door about 10 minutes before 6:30 pm. And rings the doorbell. Jane opens the door. All the girls are downstairs, sitting in the living room. I wink at them, and they giggle.

My mom is upstairs finishing Up Mr. Rockefeller. You look so hot tonight.

I walk over and put my arm around her, squeezing her ass.

She lets out a moan. The other girls bite their lips. I kiss Jane's neck.

Flatter will get you everywhere, don't worry, I will fuck you real good tonight.

I hear footsteps coming down the stairs, so I separate from Jane. She looks a little sad but cheers up when her mom comes down. She is wearing a tight-fitting black dress that really hugs her body. Her hair is done amazingly, and she has the right amount of makeup. Her lips are a shade of dark red. She looks breathtakingly stunning. She also has 4-inch heels, making her legs stand out. 

I walk over to her, hug and kiss her, and hand her the flowers I got her.

Barbra, you look stunning.

Thank you, Tim; you look handsome tonight.

She blushes, and I hold my hand out. She grabs it, and we turn to the girls. She says, 

Jane, don't wait up for me. I don't know when I will be back. Have a good night, and call me if something happens.

You girls enjoy yourself.

Have fun, Mom, you deserve it.

Bye Mrs. Williams

We head out, and I escort her to my truck's door, opening it for her. I planned to eat at an Italian restaurant before we saw a movie; I picked out a movie that had some steamy love parts. To set the mood for later, I got to get the idea of having sex tonight into her head. That way, I can sway her when the time is right.

We make our way to eat; we get to the restaurant. I get out and open her door, helping her out. She wraps her arm around mine; we head in and get escorted to our table. We ordered our food, and while we waited, I got us some Renato Ratti 2019 Serradenari Nebbiolo wine. She tries to turn it down because it is expensive, but I tell her she is worth every cent. She blushes and we being to make small talk, I crack a couple of jokes and she laughs. We get the food and begin to eat.

Tim, I am really glad you asked me out. It's been lonely these last nine years or so. I have been trying to take care of Jane to the best of my ability. You have helped me out so much through these years. I don't know if I could ever thank you.

I grab her hands and use my soothing hand, holding them and speaking.

 Barbra, you don't have to thank me. I did what I thought was right. Helping you was what I should have done. It's what I was made for.

I bring one of my hands and wipe a tear from her eyes. I lean forward and kiss her. She returned the kiss, and we stayed like that for about four minutes, then we pulled away to finish our food. I hold one of her hands for the whole meal; she runs her thumb over my hand as she smiles. I pay for the meal; we both feel perfect after the food. We walk to the movie theater; I make sure that it is within walking distance. 

We walk arm in arm to the movie, get there, and pay for the tickets. We get popcorn and some drinks and head in. The theater is pretty empty, and the movie has been out for a while, but we both work, so we don't have much time to see films. We pick a pair of sets 3/4 the way up with no one around. We wait for the movie to start. I raise the arm of the chair that keeps us separated so that I can pull her closer. I put my arm around her and pulled her into my embrace.

She leans into it as the movie starts after the first sex part. I let one hand move and play with her arm, running my fingers up and down her arm. Tracing the word sex, she smirks slyly and puts her hand on my leg, running her fingers up and down, tracing maybe. She then moved her hand to my inner thigh, running it up and down. I lean over grabbing her chin and kiss her, we stay like that for 15 minutes. After the final sex part, I moved my hand that was around her. And start to play with her left breast. She covers her mouth and lets out a moan. She is nice and ready; I only need to get her home now. The movie ends and we make our way to my truck I open her door. Helping her in, I look at my watch, and it's 11:00 pm. I smile.

We go back to her house; she looks sad that we didn't go to my house. I grab the bag with the toys in it. I walk her to her door and kiss her while I grab her keys and open the door. I bring her into the living room while we make out.

We can't do this here; the girls will hear us. Let's go to your house.

Samantha and her friends are over there; it wouldn't be any different there. Plus, I have to pick up Amanda tomorrow anyway, so why not let me stay the night here? Plus, if you're worried about making noise, why don't you put this in your mouth? 

When I show her the ball gag, her face blushes, and she bites her lip. She is excited that I have it.

Why do you have something like that?

I thought maybe you needed something to help you let go of your worries and have someone take care of you.

I said as my hands made their way down to her ass, kneading her cheeks like I wanted to make a pizza. While the other hand makes its way to the zipper of her dress, she doesn't stop me. She looks down and to the side, looking at me from the corner of her eye while smiling. Greenlight boyz.

Her dress fell; she is wearing a lace bra and pantie style that matches their black with red as the sub color. Oh, how I am going to whip this sexy body. I start to kiss her while I move my hands to undo her bra, her tits are fucking amazing big DD tits I just want to motorboat. But I need to play her game before I can play my game. 

I start to kiss down her neck she covers her move when I get to her tits, I suck on one while I play with the other moving my frees hand down to her pussy. I can tell she hasn't been with anyone in a while. She is pretty sensitive; I start to kiss my way down until my face is level with her pussy. I pull down her panties; I can tell she just had her hair down and trimmed. It's an excellent triangle shape, not too big or small, just right. I start to eat out her pussy, giving it some long need love. She comes after 5 minutes of it; I set her on the couch and get the rope out.

Is he going to tie me up, oh god, when was the last time I was tied up, fuck I already am getting horny. Here he comes he starts with my left leg bending it to point outward making sure I can't stretch it out, it's just the right tightness. I can feel it dig into my skin; God, I missed this feeling. My pussy is throbbing. He is going to my other leg; every wrap is a new dig into my skin, making my pussy leak out. Next, he picks me up laying me face down on the ground and ties my arms nice and tight, a moan escapes my mouth, as I come. I can't believe I came from being tied up so fast the way he does; I don't know how to explain it. Now I am on the ground face down with my ass up. I watch as he takes of his clothes, he looks at me like someone that wants to abuse me, defile me, make me feel pain. Fuck!!! He is fully naked, and his raging cock is pointing to the sky. Shit, that's big. He grabs me by my hair and makes me sit on my knees. He is going to face fuck me!!!! Yes!!!!!

Open your mouth, you dirty whore. I am about to fuck your throat.

She opens it, and I slide my cock into her mouth. But what she doesn't know is that behind her are four girls watching her get face fuck. I grab the blindfolds and put them on; she can't see anything. And the only noise she can hear is my grunting. As I fuck her throat, her pussy is leaking out way more juice now. I keep going at it for like 10 minutes and unload my cum into her throat as her pussy juices explode out, making a puddle on her floor.

Shit, that was the best face fucking I have ever had; My Ex and my dead husband could never do it that good. What is he going to do now, fuck my pussy, Fuck my ass? God, I wish I could see what he is doing. He is putting the ball gag into my mouth.

I am going to punish you until you know who you belong to. I have this horse whip here, and that nice fat ass of yours is just screaming to be whipped.

I can see her pussy gasping; the thought of being whipped turns her on. Barbra, you're a fucking amazing woman.

HELL!!!! YES!!!!! WHIPS!!!!!!! TIM, I DIDN'T KNOW YOU HAD THIS IN YOU!! Tim, I need you in my life now. You made me feel like a woman again. It's your responsibility to take care of it now.

I signal the girls to take a sit on the couch and to get naked; I can tell that they are horny. That they want my cock right now, but it's not the time just yet. I take the whip and smack her left ass cheek. She moans, and saliva drips out the corner of her mouth. Then the right ass cheek, she does the same thing. I slowly pick up the strength, making sure not to hit her too hard. Just to the point right before she bleeds. She climaxes again, this time an even bigger one. She passes out this time; it's been a while since she has done bondage. So, it may have been too much for her. I walk over to Jane and whisper into her ear.

When I start fucking your mom, I want you to get naked and crawl in front of her pussy and start licking it. I will remove her blindfold at that time. I want you to play with her pussy and tits. Do you understand?

She nods her head up and down while looking at my cock. adorable

I am about to fuck you, Barbra. I hope you're ready.

Here it comes, he is about to put that big fat cock into my pussy. Fuck, I need it; he put me on his lap, reverse cowgirl style. Lowering me onto his cock the tip goes in, then it's halfway in, and it's in. I feel so stuffed. He holds my arms as he thrusts upwards. Wait, what's that feeling on my clit? It feels like a tongue. But that's impossible; the only ones here are me and time. WAIT! The girls, oh no. I need to stop this. I try to move, but the ropes dig in, making me feel more pleasure; a part of me is turned on by this. Oh, shit, the person is playing with my tits pinching and biting them and moving back down to my pussy. NOW TIM IS SPANKING ME!!! SHIT! I AM ABOUT TO COME!!! WAIT, THE BLINDFOLD IS COMING OFF. WHO IS IT!!! SHIT SO CLOSE I AM COMING!!!! They are seeing my pussy as I squirt my pussy juice. It was my daughter.