Joining Mother's Outing part 2

Characters
Caleb- son
Anna- mother


Anna enjoys her friends company as they've decided to go on a shopping spree starting with shoes and ending in underwear, with that decided she stands up still with her unknown passenger and walks with her friends her ass cheeks rub and grind against  head, after walking a while you feel her slow down and guess they made it to the store, suddenly you feel Anna sit down hard forcing you further into her ass.
Anna sits down as her friends celebrate her 45 birthday by treating her like a queen telling her to sit down as they pick out clothing for her the first item to return was a pair of tall heels shining in white Anna excitedly bent forward but was stopped by her friends who undid her straps and sliding her current heels off before putting these new heels on trapping  feet one again but this time it was like a vice, happily Anna stood up and did some steps and returning to her seat happy with those shoes she put her original ones back on before seeing one of her friends return with a long dress that looked tight, with a smile she stands up and walks to a stall and closed the curtain looking in the mirror she smiled before turning around and undressing her loose skirt falling pass you allowed you to see out, looking to right you could see Anna's pre occupied face smiling as she raised her arms and started to put on her dress you tried to pull head out but only caused the butt plug to slip a bit causing Anna to feel it, looking to her left she saw a pole, so with both hands full she lined her ass up with the pole a thrust backwards pushing you back to square one, feeling the butt plug back in her ass she smiled as she continued putting on her dress finally it reached her lower back and the dress started to struggle but after some jumping her dress finally made it over her ass sealing you in deeper then before and restricting  air supply.

Anna ran her hands over the dress feeling her curves fill the dress nicely she opened the curtain to see her friends smiling and nodding a worker walked up and asked if everything was alright,  Anna nodding then asked "can I wear this out" even hearing the muffled  version it was shocking to you the clerk nodded the rang Anna up with her friends paying for the dress and the heels, before they decided to reveal their surprise, quickly putting a blindfold on Anna they guided her to her car, after getting the keys she sat in the middle back whilst her four friends took up the rest of the seats, unaware of where they were taking her she wiggled in her seat.
Caleb could feel wiggling again but being in tighter dress he could move nor make any sound as his Anna's butt plug muted him, after 30 mins you felt the vibrations of the engine stop and felt  Anna slide out of the car, due to her being blindfolded she couldn't see the uneven ground which caused her ankle to bend putting a lot of force on  ankle causing so much pain you pass out when you wake  Anna is laying down and you hear snoring, signalling she's asleep, suddenly you hear a female voice say " wow this will be a long job that's a lot of hair and will take a lot of wax" unsure if what the woman is referring to you feel something warm it the back of  head before pressure is applied, without warning a strong tug pulls on your head but it doesn't move from  Anna's ass instead you feel pain on the back off your head, just the it all clicks for you, the hair that woman mentioned it was yours and she thought i was  Anna's hairy ass as you think this you felt another bit of your head targeted, this time it was much worse and you passed out, the last words you hear us the woman saying "wow she's a heavy sleeper".

Anna wakes up and feels her ass a hand running down her ass cheeks and along your head unfortunately as the woman was a pro , Anna didn't notice a difference between her ass and  your bald head, with a satisfied smile she goes to get dressed taking the cloth that was covering her lower section from her ass to her feet with her, not seeing her thong she decides to go commando as her tight dress won't flap in the wind happy with her dress she walked out to the waiting area where her friends were waiting asking if she was ok, with a nod they paid and left after that they hopped back in the car once more before one of her friends had an idea she drove to her house once there she guided Anna to a room and said "I want to give you a new outfit i think will look good on you" "ok"  Anna responded before her friend left and came back with black heels, black pantyhose, black pencil skirt and a white blouse "try this on I think you'll like it"  Anna's friend said as she left the room for privacy.

Anna undressed until in only bra then slides the pantyhose up feeling the nice fabric on her soft skin was nice, as it fit well around her ass, next came the pencil skirt as  Anna wiggled into it the snug skirt went into place next was the blouse with that fitting well  Anna sat down to do her heels her ass sinking into the mattress, finally doing up the heels she looked down at her new outfit and loved it.
Caleb could feel cool air as Anna undressed but it was short lived as Anna put on pantyhose sealing their feet together, Caleb could feel the smooth fabric rise up his body before it reached the back of his head, unfortunately it seems this pair of pantyhose wasn't clean and a faint but rotten smell invaded his nose, trying to breath Caleb tried to pull his head back but his body having taken a beating refused to listen, just then he was compressed more as a new skirt was placed on his Anna's ass, and when things couldn't be worse, you felt like you were in free fall before having a big weight on you.
Anna's friends walk in and approve of the new look, just then something you were dreading was said "can I use  bathroom" "of course hunny" with that confirmation you felt  Anna walk, terrified of hat will happen  heart beats faster with every clack of her heels, until she stopped and you hear a door closed and lock.

Anna enters the bathroom and turn to face her ass to the toilet, next she lifts up her skirt and pulling through the pantyhose and pushing she felt her butt plug slide a bit before coming out with a pop, satisfied Anna pulls her pantyhose down and sits on the toilet to take a shit.
You feel a pull on your head and a push from the butt plug so you use all you strength to pull back, hearing a pop you looked relieved until you realise you still had a butt plug in your mouth, just then you see  Anna's ass rising, no you were falling,  you greedily sniff some fresh air, but trying to stay quiet as to not let Anna see you.
Anna finishes her business on the toilet and goes to wipe, however there wasn't any toilet paper, with a shrug she stood up and raised her pantyhose, feeling her Butt plug rise as well she pushed it back into her unclean ass
.
You could hear a sigh and then waited to hear some wiping, but that never came instead you were lifted until you were level with  Anna's anus, still brown with some shit on the outer rim, wide eyed as  Anna's hadn't cleaned herself you tried to resist but  Anna's powerful arm was stronger then  neck, slowly you see the butt plug enter Anna's anus until it came to a stop,  lips just inches away from her rim, and then just like any other time, it got worse as  Anna pulled her skirt back down causing  lips to make contact with her rim still covered in shit.
Anna stood up flushed and washed her hands, thanked her friends and was about to leave when one of them said "wait I got you a present" as she gave you Anna a gift bag with a tight hug from all her friends she bid farewell and headed for her car, plopping into her driver's seat she let out a deep sigh smiling as she thought of how today went, before starting up her car and heading home, one home you heard  Anna call your name, however you couldn't respond, just then you heard someone terrifying, "oh that's right he's gone camping for a few days, that means I have plenty of time to myself" the last part was said with a devious smile but of course you couldn't see that.
After taking off her heels Anna walked upstairs into her room carrying the gift bag before undressing only leaving her butt plug in, before falling back into her bed and scooching backwards until she was comfy opening the bag she was delighted to see a dildo, long thick and purple.
"This is going to be fun you faintly heard"

End of part 2