Mary's 20 Labors

Saturday 2pm

We had been driving for about 90 minutes and had settled into very comfortable small talk when I told her we are getting close to our destination.

I ask, "Do you want to go toy shopping or clothes shopping first?"

She looked at me oddly and asked, "Toys?"

"So with that quizzical look toys first it is. We are getting you some sex toys. Vibrators, dildos, butt plugs and lots of lube. Then we are going to get you some sexy clothes. Summer dresses, lingerie and underwear to wear this weekend."

She stares at me a moment and stutters, "OK."

I get off the highway near our hotel. There is a larger mall nearby with some women's clothing stores, but our first stop is an adult toy store about a mile or two down the road. We pull up and park and I walk around to open her door and help her out. As we walk in she is just looking around in utter amazement. I don't think she had ever been in a store like this.

I take her chin in my hand and tilt her face up to me.

"I want you to go get yourself some toys. These are to be toys you will want to use and enjoy. I don't want you to get anything you don't think you will like or enjoy, but I do want you to get at least a vibrator, a double headed dildo & a set of butt plugs."

Her face is still shocked and confused.

"Lots of plugs come in starter sets. small, medium & large. The double headed dildo is to watch you fuck your ass and pussy at the same time, and the vibrator should be obvious."

I tilt her head up a tad more, and kiss her deeply. I break the kiss and spin her around and smack her ass. "Now go!"

I walk up to the counter and ask to pick an order I had placed for pickup. As the girl hands me the package and lets me know she had charged it as requested.

"Great thank you."

I step off to the side and start the pairing process I had memorized. I turn on the vibrator and sync it to my phone app. Now I will be able to remotely buzz her anytime today when I want to. Once I put it in her that is.

I stay up front waiting and she walks up holding a few things. As she puts them on the counter I ask the 30 something woman behind the counter, "Are these are good choices Mary made?"

"Well the vibe is a big seller, customers seem to like it, and this is the new 2.0 version. The butt plugs are nice but I think the beaded version is better. And well the dildo is nice if you have a friend to use it with."

I chime in, "No friend yet but i was hoping to see her use it on her ass and pussy at the same time. We came down this weekend for a strictly adult fun time. She will have used all of these before we check out Sunday AM."

She smiles and looks at Mary, "Well then you are going to want some lube, and shall I get you the beaded plugs?"

Mary looks up and meekly says, "Yes please."

After paying for everything I ask, "Is there a changing room?"

"No, but you didn't buy any clothes. What would you be trying on?"

I answer, "Well not on but more putting in, and I hold up the insertable vibe."

The clerk grabs a sample packet of lube and looks at Mary, "Step up here it's well covered in case someone walks in, and I would love to watch."

Mary looks at me nervously and just fidgets.

The clerk looks at Mary, "Just step around here honey."

As Mary steps around to the clerk the woman drops to her knees, reaches up and pulls down Mary's shorts. When they are down to her ankles she taps an ankle for Mary to step out of the shorts, and Mary freezes.

The woman looks up and says Mary, "You know it will go in easier if you spread your legs."

Mary lifts her leg and the clerk slides her shorts over her foot. She looks up and Mary's smooth pussy and says, "Oh a fresh waxing I see."

I tell the clerk, "I would really like this to be a memorable weekend for Mary."

"OK then let's make this visit to our store a memorable one." She puts out her hand to me. I realize she is asking for the toy, and I give the saleswoman the toy.

She says to Mary, "Look at me."

Mary looks down at the woman.

"Would you like me to put it in for you?"

"Umm no I think I can."

The woman pouts a little but takes the lube packet and puts some on the toy and the rest on Mary's hand. "You better rub that in. It will slide in a lot easier."

Mary rubs the lube in, and the woman is just staring. "Ok here, pop this bad boy in there."

After Mary has inserted the toy the clerk asks me, "Do you want to test it?"

"I absolutely do." I buzz it up to about 25%, then 50 watching Mary flinch with each step. I then pop it to 75% and she gasps and I put it up to 100% and she falters and is leaning on the counter for support.

Looking at the floor Mary is gasping and moaning, "Please not here."

She looks up and I turn it off. Panting, she looks at me and says, "Thank you."

"Get dressed, we have some new clothes to buy." She sighs and reaches down to put her shorts back on.

As we are pulling into a parking space at the mall Mary asks, "Can I take the toy out?"

"Does it hurt?"

"No, it feels weird."

"Good weird or bad weird?"

"Just weird."

I turn off the car and grab my phone and open the app. While looking at her I ask, "Do you not like the toy? Does it not feel good?"

"No, the lower speeds are nice, but the higher ones are too much. I don't think I could stand it long."

"Stand it long, as in it will be uncomfortable or that you would orgasm?"

"I would orgasm. In the store my legs were getting shaky and I thought I might fall to the floor, and the floor behind that counter was disgusting."

I laugh and give it just a small bump on and she jumps. "Now that was a good weird, and it will only get better. That is if you behave while we are shopping. Behave and you will be rewarded. Misbehave or refuse me and I turn it on high and leave it there until you are a quivering puddle of goo. Do you understand?"

"Yes sir."

"Great let's go."

We walk into a nicer women's clothing store that has a full line of clothes, bras, panties & lingerie. A saleswoman walks up and asks, "Hi I am Jen, can I help you?"

"Absolutely. We are her on a surprise weekend and my girlfriend has no clothes with her. She will need a nice sundress that maybe could double for a nice night out. Some underwear and a nice teddy or two." I tell her.

The woman's eyes light up a tad imagining I am sure a sales credit.

"Let us walk around a bit and browse and maybe you can help us when she needs to try something on."

She smiles, "By all means just let me know."

I look at Mary and swing my hand out as if to say lead the way. I want to see what she picks out. She walks towards some conservative dresses and holds 1 or 2 up. Outside of it being sleeveless it went from her neck to past her knees.

"No no no. You have a curvy woman's body. We need to show off your curves a bit." I go a rack or 2 over and find a mostly backless, deep cleavage and above her knees. I hold it up and ask, "What size?"

"Oh my I am not sure I can wear that."

I reach for my phone and tap her up to 50%. She spasms, gasps and holds onto a rack for balance.

"That's 50%. Do you want 100% right here and now?"

"No! I am sorry I will wear it."

I bring her back to zero. "Now answer me honestly, it felt good didn't it?"

"Yes."

"But you said no to avoid any public embarrassment?"

"Yes."

"Good to know. Now what size?" She tells me her size and I grab the dress. "Great now let's find some panties."

I again let her lead the way and she goes over to Mom underwear. I take her by the hand and pull her over to a display with sexier panties and matching bras. They were all on a 3 for sale so I tell her to get 3 matching sets. She sighs a bit and shakes her head but doesn't complain.

I waive the Jen over and she takes Mary over to the dressing room to try on the dress. Mary comes out a few minutes later, and to me the dress looks a tad big. I look at the sales woman and ask, "Isn't that supposed to be a bit snugger. Is that size too big?"

She walks over and asks Mary to spin. She kind of pulls on the body of the dress. "I think you could go a size smaller, but I think you have the wrong size bra too."

Mary looks a bit confused.

"Don't worry honey lots of women make that mistake. You step in the dressing room, and I will get you the right sizes and be right back."

Jen returns with a new bra like the one I am holding and a new dress, and walks into the dressing room. I can just hear pieces of the conversation, "Better fit..looks sexier for boyfriend..better lift and separation." Man I can't wait to see.

The woman steps out and holds back the curtain for Mary to walk out. Man the smaller size did the trick. It's hugging her womanly hips and ass and looks great, but the cleavage is deep enough that although her new bra does do wonders she can't wear it with this dress. None the less I tell her she looks great, and I mean it. She smiles and blushes.

Jen then adds, "This dress is really meant to go without a bra. It has some built in support. You can wear the right strapless bra, but I don't have any in stock. Do you want to be daring and try it on without it? I think you will look great."

Mary looks at me and I just wave my hand a bit with the phone in it, and she quietly says, "I could try."

"Great step back in, and I will make sure the dress is adjusted right on the neck strap to give you some support."

I hear some muffled chit chat, some moving around and then I hear the woman say, "Oh my, I think an anti-theft device was left on the dress." Then a little more ruffling and I hear, "Oh...that's not an anti theft tag." I know she has found the antenna for the vibe.

I speak up, "No that's her new remote control vibrator I just got her. She has been a good girl so I am now going to reward her."

I tap the phone and put it at about 20% with a random vibration and pocket my phone.

"Did he just turn it on?" I hear Jen ask.

I am assuming she nodded her head since I heard no reply. "Well you look great in the dress but there is one thing missing." I think I hear Mary gasp a bit but a minute later the woman opens the curtain and holds it aside for Mary to walk out.

She looks great. The dress is just snug around her hips, just right to look great but not tight. Her bare back and side look awesome without the bra but her cleavage is just Wow! "Bravo you look GREAT." I say.

Since the cat is out of the bag if you will with the vibrator I take out my phone and look straight at Mary, "Would you like a little more or a little less as a reward?"

Mary glances at Jen and then at me, "A little more please."

I reach my hand out to Jenn with the phone in it. She just stares for a minute. I look at her, "I think I have you to thank for Mary's hard nipples poking out of her dress so I will give you the honor."

She takes the phone after a minute and just stares at it. She puts her finger on the screen and the toy jumps to about 75%. Mary groans and flinches.

"Oh my god. I am so sorry." The woman slides her finger down so the speed is a little lower than it was. "Is that better?"

Mary nods yes.

"Mary I didn't hear you." I tell her.

Mary looks at Jen says, "Jen, thank you for lowering the speed that feels nice."

"You are welcome. He isn't wrong by the way you look Great." Mary just smiles and blushes.

I reach out to Jen and she hands me my phone, which I put back in my pocket as I suggest we go look at some lingerie.

I am looking at the different frilly things and settle on a see through lace baby doll set. Holding it up to Mary I ask Jen, "Don't you think this would look good on her?"

"Oh yes it would look very nice."

I grab a different color and hold it towards Jen. I don't get too close but look at it and say, "I think this color would look great on you."

Jen takes it and reaches to put it on the rack. I am thinking she is shooting down the subtle hint when she reaches for a different size and holds it up to her body. "I am a little bigger up top. I need the next size up from Mary."

I turn to Mary and ask, "What do you think?"

"I think she would look beautiful."

I double down at this point and ask Jen, "What time do you work until?"

She just looks at Mary and says, "Six o'clock."

"Do you have any plans after work?"

"None right now."

How would you like to join Mary & I for dinner & maybe a little desert after?"

She looks from Mary to me and back again.

"Well I would have to go home and get changed."

"Don't be silly. I will get you this, and I take the baby doll from her hands, and get you a sundress like Mary's. Every man will be jealous of me walking into the restaurant arm in arm with you two sexy women."

Jen looks at Mary and asks, "Are you ok with me joining you two?"

Mary bits her lip and nods her head.

Mary I couldn't hear you, "What are you ok with?"

She looks at Jen and says, "Yes I would love to have you join us for dinner and desert."

I can see the two of them just looking at each other. Their eyes speaking volumes of nerves and excitement.

I walk back to the dressing room and grab the larger size dress Mary had tried on.

Another customer walks in and Jen says, "A bit louder come up to the register when you are ready." and goes and greets the other customer.

I ask Mary, "Are you excited to have Jen join us tonight for dinner, and then to have her for dessert?"

Mary blushes and says, "Yes."

"Great, let's go pay for everything."

We walk up to the counter and when Jen comes over I tell her, "I had promised Marry a reward if she was good in the store. Do you think Maru has been good?"

They are staring at each other and Jen says. "Oh yes. She has been a very good girl."

I take my phone and bump Mary to about 40%. Mary flinches and places her hands on the counter. Jen reaches out and takes Mary's hands in hers. So I bump her to 60%. She grunts a bit and her hips buck a bit.

Jen whishers, "Are you going to orgasm?"

Mary nods her head.

"Mary you know I want to hear your answers." I tell her and bump her to 80%.

She gasps, and looks at Jen. Jen is squeezing her hands and says, "Say it honey. Say it and do it."

Mary gasps, "I am cumming." Her face scrunches up and she drops her head onto Jens Hands holding hers, and shivers. I turn off the vibe.

Mary takes a deep breath and stands up. Jen looks her in the eyes with pure lust and says, "I have never seen anything that hot and sexy in my life." She releases Mary's hands and gently pushes some loose hair back behind Mary;s ear and holds her face for just a moment too long. She then seems to realize where she is. Clears her throat and says, "So 6PM?"

I tell Jen, "We will be right outside of the store on the bench at 6pm."

I have Jen ring up her dress separately so she can have proof it's paid for leaving work, and the rest we take with us. Mary walked out wearing the dress with her other clothes in the bag.

She smiles a bright smile and says, "See you then."

It's about 2 hours until then so I take Mary's arm and say, "Lets go check-in, find a nice restaurant and come back and get Jen."

Mary hugs my arm a bit and says, "OK" and walks with me to the car.

We pulled up to the hotel, and I walked around the car to help Mary out. As she stands up, I tilt her chin up to me and give her a passionate kiss. I kissed her for a good 15-20 seconds and then broke the kiss. Her face is full of conflicting emotions. Lust, confusion and maybe a little fear.

I tell her, "For being such a sexy good girl at the mall I am going to put the app on 100% random. I honestly have no idea what you are in for, but you deserve another nice orgasm like you had in the store. We walk into the hotel and are greeted as Mr & Mrs as we are checking in. I can see Mary blush a bit, but I am unsure if it's because of the Mr & Mrs, or what the vibrator is doing to her. She hasn't let go of my arm since getting out of the car. I am guessing every flinch or tighter grip I am feeling is a change in the random setting. A bell hop offers to bring our bags up and loads then on the trolley. We get to our room and the boy is unloading the trolly when Mary says, "I will take that." Meaning the paper bag from the toy store.

As he passes it to Mary I can see the handles separate, and I can tell that he sees the toys. He blushes a bit, and stammers a little. I hand him a tip and say, "it's going to be a memorable night."

"Um, ah yes sir." he stutters and backs out of the room.

Mary shakes her head with a small smile and a look of embarrassment, and I just laugh. We are unpacking, the toys on the nightstand with the lube for later, and I hung up the nighties. Mary was hoping I think for sex and kind of started to rub up against me.

I turned to her and said, "You are going to stew and just be teased until we come back tonight."

She looks up at me and pleads, "Please! This thing is maddening."

She has been buzzing on and off since we got to the mall. I click over to the app and shut off the remote. You can see the change in her face.

"I'll make you a deal. If you can get Jen to agree to come back to the room and have a threesome with us tonight. I will allow the two of you to decide together who gets the vibe and who gets the phone while we are in the restaurant. Whoever has the phone gets to control the other one until we are back in the room and you are both in your nighties on the bed."

Mary pouts and says, "Yes sir."

I hit record and point the camera at Mary, "So look into the camera and ask her."

"God you are horrible sometimes. Jen, would you come back with us tonight to the hotel room? Would you please join us for a threesome and have sex with me? Would you please be the first woman I have sex with? Please say yes."

I stop the recording. "Perfect." and I tilt her head up again kissing her deeply. Letting my hands roam over her body. Feeling her boobs through the dress. Letting my hands wander down her bare back, and further down to cup her dress covered ass.

I then stop and look at her, "You really want to get fucked don't you?"

"God yes."

I pat her ass, "Sorry you still have to wait."

She sighs and giggles, "God you are an ass."

"I will show Jen this entire video while we are having our drinks before dinner. If she declines I will still bring you back to the room and fuck you until we check out Sunday morning."

She smiles, and says, "OK"