Teacher and a Shop Girl

Background, I am a 38 year old high school teacher. I've been teaching for about 15 years. In that time I've had sex with a number of my former students. I have been married during most of that time. But this isn't a story about one of my students though it does involve one. This takes place 3 years ago.

I was currently sleeping with Jane, a student who had just graduated. Jane is mixed race (Vietnamese and black and maybe some white too). She is maybe the sexiest girl in school. 18 years old at the time. 5'4'' with great curves that standout no matter what she wears. The poutiest lips and beautiful, smooth caramel-colored skin. We had been seeing each other for about a month, usually meeting for sex at a hotel during the day.

On this day, I decided to take her out shopping. I get a real thrill from financial spoiling my side women with my wife's money. The town we live in has a very big mall that everyone in the area shops at. To avoid detection, we went to a mall about an hour away and was the opposite direction from where my wife works. It also had some higher end stores.

We had already bought some lingerie from La Perla and pair of Kate Spade high heels. Our final stop was to get a couple nice dresses for Jane. Jane is looking at some dresses on one rack and I am a few racks away. A store clerk comes up to me and asks if I am looking for anything specific today. She is about 26 years old, white with long, wavy, light brown hair. About 5'6'' with a nice figure. She is wearing a short dress with a blazer that show off her legs and a work-appropriate amount of cleavage. Her name tag reads, "Alexandra."

I tell her, "The young lady needs a cocktail dress. I want something tasteful with long sleeves and a high neck, but is tailored to hug her figure. I think dark green or purple would suit her best."

"Oh, the gentleman knows what he wants. That's refreshing. I think we have something over here." She leads to another rack of dresses. "Is this for a certain occasion?"

"Nights out and entertaining" (She thinks I mean entertaining guests. I mean entertaining me).

She pulls out a green dress that meets my description. She says, "I think your girlfriend would look fantastic in this."

"She's not my girlfriend. I am married."

"Oh, I'm sorry. I..." - I cut her off, "She's my mistress."

She is stunned by my bluntness for a second. "umm, uh, Well she'll look great in this." She looks away out of awkwardness, but then I notice her look me up and down and subconsciously lick her lower lip. She then gives Jane a once over. I suspect she evaluating herself against Jane.

We then go over to another rack and she has me pick between two purple dresses. Jane comes over with a black mini dress she has picked out. Alexandra leads us to the fitting rooms. There is a sofa and some chairs to the side where I sit. Alexandra takes Jane into a stall and hangs up the dresses. She closes the door and stands next to me.

"Those are some fine choices, sir." I hadn't noticed her calling me "sir" before this. I like it.

She looks down at our other shopping bags. "I see you've had a busy day."

"Yes, I like to take good care of my women... in every way I can."

"I am sure you do, sir." She has a knowing smile that I return.

Then Jane came out of the dressing room. She's wearing the green dress. It looks a bit loose. I say so and ask Alexandra to get her the next size down. "Right away, sir." She returns in a minute and Jane takes the dress and goes back in.

"It's so kind of you to take such good care of your... um... mistress." She says mistress like she trying to see how it feels coming out of her mouth.

"Thank you, but every woman deserves to be taken care of. Don't you agree?"

"Yes, sir." She blushes slightly.

Jane comes out. The new size looks perfect on her. I tell Alexandra we will take it. Jane give a bubbly school girl squeal and goes back in to try on the next dress.

I am getting a very strong vibe from Alexandra. She keeps stealing glances. Every time I say something she blushes or bites her lip. I look right at her. She looks down nervously and starts running her hand along the neck of her shirt.

I decide to be bold. "Has your man been taking care of you, Alexandra?"

With her head still tilted down, her eyes dart up and look into mine and she has a big smile. "I don't have a man, sir."

"That's unfortunate. Someone as desirable as you should be well taken care of."

"Thank you, sir." She blushes and stammers. She shifts her weight from one foot to the other. Over the past 15 minutes, she's gone from a totally poised and professional woman to a giddy, embarrassed young girl.

Jane comes out of the dressing room in the purple dress. Alexandra snaps into a more professional posture. I quickly turn from Alexandra to Jane. The absurdity of the fact that I am trying to cheat on my mistress and I chuckle.

Jane looks hurt. "No, that wasn't about you. Just something I was thinking about. You look fantastic. Show me the back." Jane spins for me. "Perfect. We will take this one too." Jane smiles and goes back in for the last dress.

I turn to face Alexandra. I stare directly at her. She turns back into the giddy, flattered young girl. She keeps breaking eye contact to look down. I hold my stare. After a while her smile breaks, "What, sir? Is something wrong?"

"Not a single thing. I'm just imagining how a man could fully take care of you."

Her smile returns with a lot of blush. She shifts her weight and almost falls down.

Jane comes out in the black dress she picked out. She looks like a Saigon whore. The dress is a size to small with too short a skirt and her breasts falling out. "I don't think we will be taking this one."

Alexandra takes the other two dresses and heads to the register while Jane changes back into her clothes. I stay on the sofa and continue to stare at Alexandra across the store.

After Jane comes out, I go to the register to pay and Jane goes to a rack near the front of the store to look at some pants or something.

Alexandra tells me the total. I hand her my credit card. Her hand is shaking and it brushes against mine. She takes three tries to swipe it. As she hands it back to me, take her hand. She freezes with her mouth open. I say, "I want to see you again."

Still in shock, she slides a card across the counter with her other hand that she's already filled out with her phone number. "In case you have any issues with the dresses."

"Yes, of course. The dresses."

She smiles and finishes packing things up. Jane and I leave. We have a reservation at a hotel nearby. I almost call her Alexandra when I cum.

The next day, I sign up for one of those Google phone number things so I can text Alexandra without giving her my real number. We text back and forth. We agree to meet for dinner at a nice restaurant near the mall. I tell my wife I am going out with one of my friends who is moving out of town. She likely won't see him again so she won't be able to check my alibi.

Alexandra texts me a picture of her in two different dresses and asks which she should wear. Both are very nice and completely classy. I pick one. Then I go to the La Perla online catalog. I pick out a bra/panty/garter set. I text the link telling her I want her to wear that too. I Venmo her the money to pay for it. She replies, "Yes sir".

We go to dinner a few nights later. She calls me "sir" the whole night. I'm not sure if she knows my actual name. The conversation is lively and flirtatious but never sexual or suggestive. At the end of dinner, I mention that the hotel across the street has a great view of the lake. She says she never been.

"Would you like to see it?"

Without hesitation while quickly standing up from her seat, "Yes, sir."

We head over. Luckily someone made reservations in my name for a room with a view of the lake. I ask for some wine to be sent to the room.

We go up and admire the view for a few minutes. The wine arrives. She takes a sip then excuses herself to the bathroom. After a few minutes, she emerges in the lingerie I picked out, stockings, a thing gold necklace, and her high heels.

"Thank you for your gift, sir"

"Thank you" She's breathtaking.

She walks to me confidently. I order her to spin around. She complies and I drink her all in.

"How do you feel about being in a hotel room in lingerie with a married man?"

"Scared... Dirty ... Incredible."

"Good. Slowly, walk over to that desk. Bend at the waist and place your hands and elbows flat on the desk."

"Yes, sir."

I am not sure what's coming over me. I don't usually do this much ordering around. I think it is the "sir" thing going to my head.

She bends over the desk. She is presenting her ass to me. I walk up. I rub her right ass cheek with my big hand. I slap it then grab the other cheek. She makes a shocked sound, then smiles very big.

I run my hand down her leg then slide it back up her inner thigh. I palm her pussy through her lingerie. With my other hand, I grab a handful of wavy, light brown hair and pull her head back. I kiss her deeply. When I break the kiss, I throw her head to the side.

I move close to her so my crotch is pushing against her ass. I slide both my hands up her side. I lean forward pushing harder on her ass and I grab her breasts. "mmmm, Thank you, sir. mmmmm."

I grab her hair again and kiss her. I then walk away from her and sit in the chair on the other side of the room. "Come."

She turns to walk. "On your knees."

She gets down on all fours with lust burning in her eyes. She slowly crawls to me.

"Pants." Her hands start unbuckling my pants. She pulls them down along with my boxers. She looks at my cock then up at me. "Thank you, sir."

She takes just the head into her mouth and swirls her tongue around it. It's amazing. She licks up and down the shaft on each side. She wraps one hand around the base and alternates between firmly squeezing it and pumping about half way up and down. She take the head back in her mouth and alternately between swirling and sliding up and down the top half. The other hand plays with my balls and does this thing she puts pressure on my perineum. It is incredible. I don't know how she can do three things at once so well.

An aside: This is why I will always prefer women in their late 20s or older. They fucking know what they are doing and they fucking love doing it. Teenagers and 21 year olds are cute and fun, but man oh man, women get so good with age. Back to the story.

I can only tolerate this for about 5 minutes. I don't want to cum too quickly. I pull her up and throw her on her back on the bed.

"You suck cock better than my wife" (She doesn't).

"Thank you, sir"

"Let see if you have a tighter pussy."

I pull her panties to the side. I slides my middle finger up and down her slits a few times getting it wet. I slowly slide it into her. I slide it in and out a few times. Then I start to slowly curl it up down the front wall. With my thumb, I press down on her clit. I eventually start caressing it.

Her head is thrown back with her eye tightly closed. She is moaning. With my other hand, I cradle her face. I rub my thumb across her lips. She starts to suck on it.

Eventually she comes. She never gets loud. Just more and more drawn into her own pleasure. I am sure for the last few minutes before she cums she wouldn't notice if the roof blew off and a marching band performed. I fucking love that. When they get lost in pleasure instead of doing the porn star performance.

After she cums, I crawl on top and we kiss some more. I start to push her panties aside and reach for my cock to put it in her. She slaps my hand away and says, "Allow me, sir."

She wraps both hands around and pushes the head into her vagina. She gasps. "Thank you, sir."

We start fucking. She keeps moaning, "Yes, sir. Thank you, sir." Each time each gets less intelligible as she gets lost in her pleasure. She cums once with me on top. I bend her back over the desk and take her from behind. She occasionally make eye contact through the mirror and says "Yes, sir." I pound her forcefully and slap her ass bright red. Sometimes I pull hair to get her to look at me in the mirror.

Soon she is completely lost to the world. I cum hard. We collapse on the floor and try to catch our breath. A few minutes later she starts returning to the world of the living. We stay on that floor, completely intertwined for an hour.

We end up seeing each for a couple of months. It's complete sexual dynamite for the first month. Eventually expectations are too high and stop getting met.