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.
"Count on it my sexy sissy." Tim smiled. Was he Bill's sissy now? Maybe he was.
Tim grabbed the duffel bag and high heels from his moms closet. First came the panties. Slipping them up his legs he felt his skin tingle. The thong nestled in between his cheeks. He sat down and pulled out the black thigh high stockings. He slowly drew them up one leg and then the other. Feeling the silky stocking press against his skin. Tim slipped the heels on and stood up. The final thing was the corset. Black with silver highlights. It fit pretty good with a zipper up the front. The bust was loose but Tim still felt sexy.
He went to the mirror and looked at him self. His waist was sucked in and his hips widened. He turned and loved how his ass stuck out. He ran his hands up his stockings and rubbed his soft dick. For some reason he couldn't get hard with either the woman's clothes or plug in. He leaked a lot though. Just like a little slut he felt like.
He saw he still had some time. He was so nervous. He walked out to the kitchen hearing his heels click and ass swaying back and forth. He got out his moms bottle of whiskey and took a shot. Feeling the fire hit his belly and calm his nerves. He went back and sat down at his moms makeup table. He picked out a red polish and painted his nails. As he waited from them to dry he heard his phone buzz.
"I'm just about there baby."
Tim wrote back. "The door his unlocked. Come on in I will be out in a minute."
Tim heard the doorbell ring and his heart skipped a beat thinking it was someone else. Then he heard Bill's voice.
"Tim? Hey baby I'm here."
"I will be out in a second honey. Sit down on the couch." Tim called out hearing his voice crack a little. He was so nervous but so excited too. He took a deep breath and looked at himself in the mirror again. He was sexy. With a smile he walked out.
His heels clicked on the floors announcing his approach. As he rounded the corner into the living room and leaned against the wall bringing one foot up behind him. Looking right at Bill.
"So what do you think?"
"Oh my god your hot!" Bill shouted and stood up. Before Tim new it Bill had swept over and kissed him fully on the mouth. Tim melted into his arms and kissed back. Tongues dueling and Bills hands running up and down his back.
After a few minutes Bill breaks the kiss and looks at Tim. Taking in the heels, stockings and lingerie. He has Tim turn around and smack his ass. Tim feels it jiggle and moans.
"Lets sit down" Tim says. They sit and turn on the tv. Tim has crossed his legs feeling his soft cock slip down.
