Help me cheer up my mom

You were a little confused by ashleys request, you had met her mom on a million occasions and she always seemed fine. “What do you mean ash?” you retorted. Ashley still keeping her cool said “well its just she has been really down recently and i think part of that is a lack of a male in her life, she really could use someone like you”

“So what is it you want me to do?” you responded

“Okay well i was thinking if your up to it, i dress you up all cute and then when my mom gets home you have some fun with her” Ashley smiled but it did not help you look past the fact she wanted you to let her mom fuck the shit out of you.

“Ashley i want to help you but that's not really up my ally”

“Pleasssee Doug, my mom really needs this and i promise to owe you big time if you say yes” That did make this deal a lot better, and as attractive as Ashley was she was only a fraction of how great you thought her mom was.

“Fine Ashley you have yourself a deal”

Ashley practically jumped with excitement, she really did care about her mom. Ashley grabbed your hand and led you upstairs without saying a word. You remember when you were younger Ashley and you were relative in size and strength but now it was like being led by a giant hell-bent on getting you laid. You walked into her mom's room and admired the bed, it was at least a king possibly bigger, and had pastel pink sheets, your journey continued into a walk-in closet.

In the closet, you were met with a bunch of her mom's outfits but also a small section of outfits that clearly were not meant for her or Ashley, they were slutier outfits, all of which had no cover where your ass hole would be. Ahsley said “okay dougie ill let you choose” there were not that many great options so you chose the maid outfit with a small mini skirt and crop top with long sleeves. You began slipping out of your shirt and pants and got nervous stripping in front of ashley.

“Don't worry Dougie i dont mind you being naked,” she said and gestured for your boxers to be dropped. Not wanting any trouble you did as instructed and immediately moved from boxers to trying to pull this small minis skirt over you cute butt. Ashley waltzed towards you and grabbed your ass and the skirt with the other hand and managed to slip it right into place. Having your best friend grab your ass was a new experience for both of you but it was not bad, it was actually kind of nice her knowing exactly what to do with you. You slipped on the ctop top and asked how you looked.

“God this turned out great, if you were not with my mom and not my best friend i would fuck you raw right here right now” ashley smirked. “Okay now lets get you set up in her bed” ashley and you returned to her room and you hopped up on her bed and layed on your stomach, “okay pretty boy looking good, one last detai” ashley reached into her moms night stand and pulled out some lube before squirting some on your ass and leaving it nice and shiny. “Okay she is going to be home and minute so ill see you soon” ashley gave dougs ass a gentle smacked and went out the door. Doug thought about his predicament for a moment but soon he heard ashleys moms car pull up and you knew it was to late to escape. The only question left is what was up with ashleys mom.