The First date.

It had been a little less then a week sense that fateful night but still it all seemed like a blur.

The little moments you and Monica were able to share were truly great but you still hadn’t gone on a real date.

That all changed the day you helped your mom move her stuff into Monica’s office and likewise helped your mommy move her stuff out to the car.

You weren’t of much practical help, being a femboy but they both really seemed to have appreciated the effort.

This being your first date not just with Monica but with any futa, would be big.

You had expected Monica to choose a classy local for the date but instead she planned lunch and a trip to the mall.

You didn’t quite know why she chose this, either she wanted to take things slow with you or she wanted to live out teenage dates she never got to go on.

Regardless it was made clear she would be paying for the expenses regardless where the date was.

Pulling up to the small diner you chose you caught many looks from both futa and femboy alike.

Stepping out of Monica’s sports car you felt nervous as eyes fell upon you both though luckily Monica was no stranger to this attention and took your hand.

She intertwined her fingers with yours and squeezed gently as to give encouragement and led you inside, and though it was a small act her opening the door for you felt nice.

You sat at your usually booth and your drink order was taken quickly by a new girl.

A little taller then you and with vibrant red hair she certainly wasn’t easy to miss, her name tag displayed her name as “Tracy” in big bold letters.

Your plan was simple, you were going to order the smallest thing here and at the mall you’d buy one small trinket.

Even after all this time you felt weird about letting her pay for your stuff even though she had money to spare you just felt bad about it.

Tracy walked back up to your table and you opened your mouth to place your small cheap order of a bowl of chicken noodle soup when Monica interrupted you.

“He will be having an order of the grilled cheese and a side of French fries and they had better be fresh or I WILL send them back.”

She wore an icy glare staring into her soul as she spoke, all the poor futa could do is nod and scribble the order in shaky penmanship.

Your eyes widened as you watch this warm loving woman speak in such a harsh and intimidating tone.

She proceeded to take her own order and allowed Tracy to scurry away back to the kitchen before turning her eyes to you the icy look now gone replaced with a warm smile.

At your surprised look she cocked her head to the side and asked a question in a tone you could only describe as comedically innocent. “Is something the matter dear?”

She asked as if the scene ripped straight out of “Good Fellas” hadn’t even happened which made you question if anything even had happened.

“N... no mommy....” is all you can manage to meekly say as she watches you lovingly.

The food arrived in record time and piping hot to boot, Tracy nearly stumbles over herself as she rushed to the table.

As she left you exchanged a sympathetic look with her, her no doubt thinking your in a sour relationship and you thinking she was having a terrible first day.

You would later turn out to both be wrong.

Monica has ordered herself a small salad, you offered some of your food at which she turned down stating an older woman like herself needs to watch what she eats.

Even then she hardly touched the salad instead opting to place her elbows on the table intertwine her fingers and rest her chin on the bridge, watching you with a warm smile.

She very clearly wanted to pamper you and you very clearly wanted to please her, you were both in a Cold War or wholesome love.

You ate your food not wanting to waste her gift which she appreciated as she watched you devour your meal.

During the course of the meal your small talk evolved into deeper topics and learning.

She told you more about herself and you did the same, she almost seemed to be actively memorizing all of your hobbies and interests as you talked.

You had thought you had only been talking for half an hour but when you glanced outside at the setting sun you were both caught by surprise.

As you both got ready to leave Monica left a tip of 100 dollars before taking your hand and leading you out to her car.

She went so far as to buckle you in before getting in herself and driving towards the mall.

It was growing clearer and clearer tonight just how deep her mommy dom fetish went and maybe if was because she was so beautiful or you had a genuine crush on her but the prospect sounded hotter and hotter to you by the second.

Arriving at the mall you both saw that it was surprisingly full, it was actually one of the only malls to still be a social hub for town.

Femboys went to experience buying naughty clothes in person and futas went to hit on the femboys.

And only then did it sink in just how much of an enviable position your in, any femboy would kill to be you right now.

Walking with a wealthy older futa her arm around you protectively as you step into the mall catching glances from others.

And as embarrassing as it was you kinda loved it, almost like you were bragging, it was a shitty thought but you kinda started to like the stares.

As long as Monica was with you you could handle anything.

Most of the time at the mall was spent wandering occasionally stepping into the stores.

One strikes your fancy quite a bit, it was a sex shop that had some lewdly posed mannequins in the window.

Catching your gaze she chuckles and lead you inside her hand wandering to your lower back as you stepped inside.

Lining the walls, shelves, display cases and hooks were toys, outfits, and things that stood in between them.

It was like a whole other world to you, dildos and buttplugs and corsets, cholera and chastity cages and underwear and more.

You didn’t know what you wanted here but you knew you wanted something, Monica watched you like a kid in a candy store as you ran from item to item inspecting them.

Enjoying the small fantasy that came with each item, how she would use them on you made your panties bulge slightly.

Your eyes land on a very strange item yet it felt like you needed to have it.

The item was a simple butt plug about 5 inches long and two or so inches thick, what made it so interesting was on the back end is a little puff ball like a bunnies tail.

Your mind was lost in thought when you felt two arms wrap around you from behind bring your into her.

You lean back softly using her breasts as pillows as her bulge lifted up the front of her skirt teasing your panty covered ass.

You chew your lip and in a spontaneous act of lust you pulled her towards the changing room your plan instantly becoming clear to her.

You close the small door to the changing room and you have your panties at your ankles in seconds.

Your bent over the changing bench with your face pressed into the wall of the changing room.

Monica pulls off her precum filled panties and shoved them into your mouth the taste of sweat and precum filling your mouth as she whispers in your ear.

“Shhhh~ don’t need you moaning too loudly~” she say as she lines her cock yo against your winking needy boy pussy.

She shoves it in, in chunks, first 3 inches, then 5 then pushing the rest inside.

Your eyes roll and you moan into her panties as you feel her push into your body her breasts now hanging out of her shirt pressing into your back as she nibbled your neck.

Just as she pulls out and hilts back in your let out a loud moan, even with the panties muffling your voice it may have just given you away.

You both look to the door and wait with baited breath as you wait to see if you were found out.