Tim got home from work. He called out to his mom.
"Mom!" No answer. He walked into the kitchen and saw a note.
"Tim I'm going out after work I will be home later. Hope your day was good... Mom"
Tim smiled thinking about lunch with Bill. He still felt the fire in his stomach for him.
Tim changed into some shorts and wandered to his moms room. His feet slapping on the wooden floors. His moms room smelled of perfume. He went to her clothes dresser and looked in. T shirts, shorts and sweat pants. The final drawer held her panties and bras.
As he thought his mom wore granny panties, nothing sexy. Even her bras were boring, white or beige.
A little disappointed he went to her closet. His mom had dresses, skirts and shirts hanging up. Her shoes were lined up on the floor. He crouched down and looked. She had mostly flats but a few high heels. Nothing over the top. He picked out a pair of black shiny pumps. He thought they were about 3 inches tall. He slipped his foot in one and was surprised to find it fit.
With both shoes on he crossed his legs. Seeing the heels made his soft cock leak a little. He stood and almost fell over. Balancing on the bed he took his first step. "Click" He heard the heel sound on the floor. Heel, toe he started to walk. Feeling so sexy he walked down the hallway. Hearing his heels click on the floor and feeling the sway of his hips as he walked felt so feminine. He walked back to Moms room. Tim's underwear felt sticky on his skin.
He went into her closet and looked around some more. Seeing a pair of red pumps and black knee high heeled boots. Next to those was a black duffel bag. He grabbed the bag and walked back to the bed.
As Tim opened the bag he hit pay dirt. On top was a pink vibrating dildo. A bottle of lube and lingerie. He went through it. Panties of different styles and colors. Black, red, sheer, a pair of shiny black ones caught his eye. He picked them up. Black satin thong with a wide waist band. Tim couldn't resist. He slipped his shorts and underwear off. Standing there naked with just the black high heels on he felt so incredibly sexy. As he slide the thong up and positioned it into place. Feeling the soft cool material settle between his ass cheeks. His soft cock bulging a little in front. He walked to the mirror on the wall. The reflection floored him. His smooth milky skin contrasted by the shiny black satin and heels. He turned and saw his ass stuck out. He smacked it and moaned. Imaging Bill grabbing him and taking him for the first time.
Tim hadn't really thought about getting fucked by Bill but now the image blossomed in his head. He wanted it, he needed it.
Tim walked back to the bag. He found a black corset with garters and black thigh high stockings. On the bottom where it seemed forgotten he found a set of 3 butt plugs. Tim realized his mom was pretty kinky. Like mom like son.
He picked up the plugs. A small, medium and large. Tim had a great idea. His mom was leaving for a day trip the coming saturday and he was going to give Bill a surprise he won't forget.
As he packed the bag up he went and grabbed his phone. He didn't want to change but his mom was due home soon. Taking a quick picture of him bending over in the mirror he shot a picture of his ass with the thong highlighting his plump ass. He sent it to Bill.
As he waiting he packed everything but the small plug up and went back to his room missing the feeling of the heels and panties already. His phone chimed.
"Holy shit baby where did you get that. Your ass looks so good."
Tim wrote back "I found it and more in my moms closet. Don't jerk off till Saturday and I will take care of you so well. Wink wink"
"Oh man its only Wednesday! You better do something special baby."
Before Tim took a shower he researched anal sex. He found that some people enjoy doing it more than others and some people's bodies accept toys or cock more easier than others. Tim read that using plugs he should go slow and keep it in as long as it feels good. Of course he thought not everything on the internet is true but there was only one way to find out.
Later that night he was in the restroom. The plug sat on the bathroom sink. It was black firm silicon. About 4 inches long and the base flared out an inch with another inch of small shaft and finger holds.
Tim stepped into the hot water. Feeling the water splash on him. He washed his body quickly and propped his foot on the railing. With a finger he ran it across his hole. Feeling it pucker. Tim squirted some lube on his finger and smeared it on his boy pussy. Feeling little tingles spread from his butt around to his dick up to his stomach. He pressed and felt his finger slide in. It felt great. His arm was down in front and tucked underneath. His dick didn't get hard but he felt mini spasms going through him.
After a couple of minutes he withdrew his finger and smeared lube on the plug. With one hand on the wall and his legs apart he reached behind him and brought the small tip to his pussy. Taking a breath he started to put pressure. As his body opened up a moan formed in his breast. Feeling the flared part expand him Tim groaned. His body was electric. A slight cramp in his stomach then he had it fully in. His pussy closed around the thin shaft.
Tim lowered his head to the feel the shower run down his back. His legs shook as a deep spasm racked his body. He watched as his little dick oozed thick white cum. He rubbed his nipples and moaned. Every sense on fire.
Finally his body calmed and he took a deep breath. The plug felt great. He felt full and whole. He turned the shower off and stepped out. Feeling the plug move in him sent shivers up and down his spine.
As he got dressed he heard his mom come home. Tim still had her butt plug in when he went to great her. He felt so naughty and sexy.
Friday finally arrived. Tim had been able to fit the medium plug in him. It felt huge and hurt a little but he hoped he was open enough for Bill. When he got up saturday morning he heard his Mom getting ready for her trip. He walked out and kissed her goodbye. She would be gone till tomorrow.
As her car pulled away his butterflies really started to get going. He went into the bathroom and stripped. He had bought an enema kit and a douche. Filling the enema with warm water he put the tip up his ass not even really feeling it. With the plunger down he felt himself fill up. It was intense and he felt full. He held himself then finally released. Two more times and he felt completely clean. After a shower he did the douche. A sent of strawberries filled the bathroom. Now it was time to get ready.
Tim looked at the clock in his moms room. Saw it was 1130 already. He grabbed his phone and texted Bill.
"Hey baby be over about 1230 if that works." The reply was almost immediately.