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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 Ankara escort 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 Ankara escort bayan 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.
As the show they are watching plays Tim begins to rub Bills crotch. His cock is clearly outlined.
“God baby I’m so turned on I bet I’m going to cum so fast.” Tim kissed Bills neck and whispered. “Its alright sexy we have all day.”
Tim began to slowly undo the button on Bills jeans. Running his painted nails across the waistband. Feeling the hair on his stomach. He inched the zipper down. Exposing a large lump in Bills underwear. A large wet spot has formed in it.
The tv was well forgotten and the nervous tension filled the air. Tim could feel the heat baking of Bills enlarged cock. He ran his finger nail along the outline in the underwear. Tim wished he had long nails but was very happy with the red nail polish.
Finally Tim pulled the waist band up and saw Bills mushroom tip. Glistening with precum. In a quick motion he pushed the briefs down and grasped Bills hard cock.
“Oh god yes.” Bill hissed out. Tim slowly moved his hand down stretching the skin tight. A little bubble of liquid oozed out. Tim lowered his head and licked it up.
Hearing Bill moan drove Tim wild. He picture the scene in his head.
Tim with his head in his bestfriend’s lap. Dressed in sexy lingerie about to give a blowjob. Tim opened his mouth and lowered a little more. Taking the hard cock into his mouth made him moan. Feeling it slide past his teeth and over his tongue felt so right. Tim closed his lips and began sucking gently. Pushing saliva into his mouth, making the hard cock slippery. He moved his head up and down keeping suction on Bills cock. After a few motions Tim raised off of it.
Bill gasped as Tim gave his mouth a rest. Wrapping his hand around it and stroking up and down. Using his own spit and Bills precum as lube.
“Do you mind if I do this baby.” Tim asked with a wicked grin.
“Oh hell no but be ready I’m almost ready to cum.”
Tim leaned in and kissed Bills neck sucking lightly. He then lowered his head back down and flicked his tongue around the crown of Bills cock. Tims hand was moving from base to crown and his tongue was bathing the tip.
“I’m coming!!” Bill annouced. Tim clamped down and felt a wave of come shooting into his mouth. Bills shaft spasmed and pumped what felt like a gallon of warm sticky juice. Tim let it fill his mouth then swallowed loving the texture and the way is slid down his throat.
Bill finally stopping coming and Tim sat back. Feeling so good. So hot. Bill had his head laid back. His cock going back to its semi soft state. Tim swung his leg over Bill and straddled him. Feeling Bills cock press against his ass. Tim sat down.
“Am I too heavy for you?”
“Oh no babe. I like feeling you like this.” Bill was looking right at Tim. Tim lowered his head and brought his lips to bills. The kiss was gentle and warm. Bills hands ran up and down Tims back. Cupping his ass. Tim began to explore Bills mouth feeling Bill suck on his tongue and bottom lip.
“So you like dressing as a woman?” Bill asked.
“Oh yes. It feels so good. I found a bunch of Escort Ankara mom’s old stuff. Wanna see?”
“Lead the way” Bill said and smacked Tims ass. Tim felt some more precum ooze out of his cock. His thong was soaked already.
In the bedroom they pulled out the bag. They quickly laid down next to each other. As they kissed Tim explained how he had been using the plugs to open himself up.
“I want you to fuck me but please be gentle.” Tim whispered between kisses.
“I will baby I don’t want to hurt you.” Bill kissed Tims neck and kept going down. Feeling his mouth and tongue on his bare skin sent electric shocks throughout his body. Tim grabbed a pillow and propped his head up.
Looking down seeing Bill’s curly head kissing further down. Tims legs on the end of the bed. Black shiny heels and stockings then creamy skin. Bill reached his thighs and kissed around the top of the stockings. Sending fire up into his belly. Bill kissed further up towards his thong. Tim was moaning and gasping. He felt Bills mouth right on top of his soft wet cock.
“What should we call your dick since it’s not getting hard?” Bill asked looking up. Tim was amazed at how sexy this was.
“It’s my clitty.” Tim moaned out. Bill lowered his head and Tim felt him sucking at his clitty.
Tim watched as Bill nuzzled the fabric aside and felt his tongue bathing his clit.
“Oh fuck yes!!” Tim screamed out. Wrapping his nylon covered legs around his head. Forcing Bill down.
Tim felt his thong being moved out of the way. Bill’s mouth was electric. Sending shocks up and down. Making Tim squirm and moan. All of sudden Tims body spasmed and he arched his whole body. Feeling Bill snake his tongue up his asshole.
“Oh fuck yes lick me there. Eat my slutty pussy!” Tim screamed out. Bill took the cue and grabbed Tims legs. Pushing them up to expose his hole. Bill drove down with his mouth. Forcing it into Tim. Loud smacking sounds filled the room along with wet slurps as Bill rimmed out Tim.
Tim lost track of time until his legs were lowered back to the bed. Breathing hard and ragged Tim tried to calm down. But the fire inside raged he needed this man. Now.
Tim rolled over and got up on all fours. Bill reached over and grabbed the lube. Tim had his ass sticking up and head on the pillow. He felt the cool of the lube as Bill smeared it on his pussy. Tim gasped as Bill slid a finger in easily. He hoped he was open enough.
Tim reached behind and grabbed his cheeks. With his head turned to the side he tried to see Bill.
He more felt him. His cock head sliding across his hole. Gasping each time they came in contact. Finally Bill pushed against Tim. Tim tried to breath deeply but couldn’t.
“Ok honey here I come.” Bill pushed harder. Tim felt the pressure build and build. Bill grabbed Tims hips and pushed in. Tim’s world went red in pain.
“Oh god not so fast!” Bill had pushed in fast and hard. It left Tim gasping and groaning. The sheets bunched in his hands.
“Sorry. Do you want me to stop?” Bill asked softly.
“No I can take it. I need you so bad right now. Just slowly.”
Tim felt Bill push in slowly. So slowly. It felt like his insides where going to come up to his mouth. Bill was big and his pussy was so small. Tim breathed deeply and let it out. Relaxing his body. All at once the pain went away and felt his pussy wrapped around Bills cock.
“Oh yes thats it. Give me all of it.” Tim moaned out. Bill grabbed Tims hips firmly and pushed. Tim felt it go all the way in. Their balls press together. Tim moaned a deep sigh.
“Damn you feel good honey.” Bill said.
“Ok sexy use my pussy make me your sissy whore.”
Bill began to rock back and forth. He would slide out and then push in. Not hard but forcefully. Tim wanted to talk dirty but couldn’t. He felt so sexy taking this wonderful cock. To be used by this man. He felt his prostrate swelling until a full orgasm wracked his body.
“Oh fuck yes fuck me thats it im cuming.” It felt like Tim had to piss but his little clit flowed with cum. He felt his pussy clamp down on Bill and felt Bills cock explode in him. Flooding him with his cum. Tim could feel each jet of cum coat his insides.
He must have passed out a bit. When he came to. Bill and him were laying next each other spooning. Bills cock still inside but softening. He felt Bills lips on his neck sucking hard making a hicky. Marking his slutty bitch.
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