Adventures of a Panty Wearing Sissy

ROBBIE

Taking the remainder of his sports uniform and shoving it in his duffel bag. Robbie untucked the towel from around his waist and dried the water that beaded on his chest, arms and back. The shower felt good. He loved playing, had a good practice and felt sore. He picked up the boxers off the bench and proceeded to dress.

'Hey. I thought I was the last one.'

Robbie turned and saw him. Blonde hair, blue eyes. Thick and bulging. All over. Thick neck, wrists. Big hands made for gripping a balls. Or stroking. His heart thumped in his chest, the throb echoed in his cock.

'Yeah, me too.'

Robbie murmured. He would not have been so nonchalant about being naked in the school locker room if he knew people were still around, especially him.

'I-I sorry, Mark. Let me get my clothes on.'

Robbie could not really hide his semi hard cock. So he quickly slipped into his boxers. His cock bobbing against his thigh. He glanced up at his friend and saw him checking him out. Mark's gaze practically brushing against his balls, then sliding down to the tip of his cock.

'Sure.'

Robbie and Mark had a complicated friendship. They met at tryouts, both being sports players. Then one day things changed. Robbie kissed his friend and Mark did not stop him. He kissed him back. Then he forced him down, ripped off his shorts and sucked his cock. It took about two minutes for Robbie to cum down his throat. Then after that they had a few mutual jerk off sessions. They did not label what they did, who they were, what they meant to each other.

'So who is she?'

They locked eyes again for a second then his friend looked away. Robbie grabbed his pants. Robbie zipped his pants and readjusted his cock. His nerves made him horny for some reason.

'Who?' Robbie asks. Truly stumped.

'What do you mean, Who. The girl.'

His friend continued to question him.

'What girl, man.'

When Robbie turns back to the bench and grabs his shirt his friend holds panties and announces.

'Dude, who's fucking panties are these!'

Robbie feels the blood drain from his face and for a few seconds things move in slow motion. Then he quickly recovers. Snatching the mocking pair of panties from his friend Robbie explains.

'They're my sister's.'

Totally honest answer. Embarrassing, but honest.

'What the fuck are you doing with your sister's underwear?'

'Dude, what the hell is your problem? She borrowed my bag and probably left them in there by mistake. You think I wear them?'

Robbie asked his friend.

'Forget I said anything.'

His friend replied. Moving closer to Robbie. Mark placed his hand against his chest, over Robbie's heart. Then softly, just for Robbie to hear.

'Can you forgive me?'

That simple touch. The gesture that became their way to say things that could not be said aloud, made a feeling well inside of Robbie and he sighed. With a nod he let his friend know, they would remain friends.

***

After school, at home alone, was his favorite time. He knew his parents would be at work and his little sister would be at band practice. He only had football practice for a couple hours. He finished and came home to find the house still empty. Graduation practice wouldn't be for a couple of weeks so he still had some free time. He went upstairs to his room to take some new panty pics.

There was a creaky step at the top step. When he paid attention, it gave him about ten seconds to conceal anything he would rather not have his parents or little sister see him doing. He turned the corner and opened the door to his room. The dresser was right behind the door and sometimes the door would hit the edge.

One shot showcased his entire body frame. All six foot three inches of his lean athletic build. The others were of his cock: close up. His nine inch cock and shaved balls looked great in pictures. The head of his cock was smaller than his thick shaft. Robbie took pictures of himself sitting in chair, legs open. Then moving to the bed posing and showing his cock restrained in panties. His cock soft, then getting hard and stroking until he came. Taking pictures of each step.

'Oh god yes! Fuck!'

Robbie lay on his back, in bed, rubbing his throbbing cock. The sheets wet with sweat. He gave his thick cock a squeeze. Cum soaked the crotch of the lacy pink panties he still wore. He was able to rub and stroke his cock longer and longer. Each time he wore the tight, lacy panties. His orgasms were so explosive. Sometimes he would cum so hard, then shoot another stream of cum just as strong. His legs shaking, breathing shallow

At 18, he was obsessed with his cock and cumming. Not so much sex yet. He wanted to explore fucking but was undecided as to what really turned him on. Then one day he got carried away and decided to play while wearing the panties, too. Usually he was a bit more aware of the noises around him. He left the door open a crack so he could hear the creaky stairs when anyone came up to the second floor.

'Ooooh, god.'

Robbie scraped his short clipped nails against his cock. He was still feeling light-headed, floating after cumming so hard. His skin was tinlgy, his cock was already semi hard again. He pinched his nipple and teased his shaft more, scratching his nails a bit rougher up the length of his cock to the head.

'Mmmm. Yeah.'

His balls were snug in the panties while his cock rode high over the thin elastic waist band. And, oh fuck. Running his finger nail along the underside of cock, over and over. He did not hear the stairs creaking, but he did hear the door bump his dresser.

'Robbie! What in God's name!'

The shriek of his mother's voice should have doused his lust.

'Mom?'

He just couldn't believe he had been caught playing with his cock AND wearing panties. Really? Wow! For some reason the look of horror on his Mom's face made his cock throb. It twitched when he saw her look at his cock. Her mouth widened.

'A-re those...?'

She moved forward. He smelled her perfume and felt her nails scrape his leg as she grabbed at the panties. Her face seemed so close in his lap, so close to his cock and all Robbie could do was moan. Pre-cum leaking from his cock.

'You little pervert! Get up, right now!'

He scrambled out of bed looked down at his Mom. With him being so tall she barely came up to his chest.

'Turn around.'

Robbie felt dizzy. All the blood in his body was draining to fill his cock. His Mom pushed his shoulders and he was bent at the waist. His ass angled to her. She yanked the panties down so fast they ripped, almost cutting into his tender cock and balls.

'AHHH!'

Robbie yelled. Then he felt her swat him.

'You filthy little pervert.'

Her hand was surprisingly strong. Swift, ample smacks to his ass had Robbie squirming and flinching.

'Mom! I'm sorry. Your dirty boy is SO sorry!'

Tears stung his eyes. His cock throbbed in time with her swatting his ass. If she kept hitting him he would fucking cum.

'Oh god, Mom, please!'

He wanted her to stop. Didn't he? His ass was on fire and she kept hitting him harder, faster. Oh god! His balls tightened and cum splattered his bed sheets. His Mom's hand caressed his ass. She leaned down whispering in his ear.

'Next time I will do more than spank your little ass if I catch you wearing panties again.'

Her nails scraping his raw ass sending a fresh streak of erotic pain gripping his cock. Oh man. WTF just happened...

***

Robbie ran his hand through his hair tousling the brown with blonde highlights. He peered closer in the mirror and examined his skin for any traces of the freakishly gross breakout that was just clearing up. He had taken more interest in his appearance, which he hoped had nothing to do with trying to get his Mom to notice him.

Having wet dreams about a girl he could say kind of sort of looked like a younger, hotter version of his Mom, was one thing. Actively envisioning his Mom naked, spanking him rubbing her tits on his back, ass and cock was another thing altogether. He questioned his sexuality before. Now he questioned his fantasy material. Jerking off wearing panties was hot. Wearing panties (still) and thinking about his Mom, made him cum even harder.

So far nothing had made her 'catch him' again. He tried leaving his bedroom door open, leaving the bathroom door open. Jerking off in the living room late at night. Nothing. So this weekend was perfect. His folks were having some weird neighbors get-to-know thing and they needed the kids there. He was almost finished in the bathroom when he heard someone rattle the door handle.

'Hold on.'

Was all he could say when the door slammed open. Some guy bigger than he was pushed past him and headed for the toilet.

'Sorry kid. Nature calls.'

Robbie was kind of impressed. This guy did not seem at all put out by the fact the door was open or that Robbie was still staring while he pulled his cock out take a piss.

'I know, huge fucker eh.'

Robbie felt a blush stain his cheeks. He man chuckled.

'Well look there. I colored you cuter.'

Robbie saw the man had stopped pissing and just held his cock. Now, he stroked it a bit, squeezing the shaft. His cock was much thicker than Robbie's. The cock head plump and red. Robbie licked his lips before he could stop his self.

'Say ahh. Why don't you shut that door. Give us a little privacy.'

The man walked over to the sink and washed his hands. Then the man walked up closer to Robbie. His breath smelled of alcohol but it was not overpowering. Robbie felt a flutter in his belly. What did this mean?

'No, no little fella. Just do what I say.'

Robbie obeyed and went to the door.

'Lock it.'

He saw the man sitting on the counter next to the sink with his jeans open more. His cock was not only thick but long. He cupped his hairy balls in his other hand, his head falling to his shoulder. Giving Robbie a sideways glance, he asked.

'Your going to give this huge fucker a kiss with that pretty mouth of yours.'

Robbie stared at the man, then lowered his gaze to his cock. Taking notice of this older man offering himself made Robbie's mouth water. His own cock began harden as he watched the man stroke. He wanted to free his cock, but he was wearing panties and was not ready to reveal that to anyone just yet. As if by some unseen force Robbie drew closer and knelt. He put his face closer to the man's cock. Breathing in the musky smell of him. Sweat and sex.

'I don't know what to do.'

The man caressed Robbie's cheek to his chin. His finger rubbed his lips.

'Open.'

Robbie parted his lush lips and the man pushed his thick finger inside. Robbie shut his eyes and let the motion of the man's finger teach him. Let the calloused digit rasp across his tongue and almost to the back of his throat.

'That's it pretty boy. Now suck.'

The man inserted another finger. Robbie wrapped his lips around the man's fingers and sucked. Slurping noises filled the bathroom as he pumped his fingers in and out of Robbie's tight, hot mouth.

'Oh fuck boy. You're a natural born cock sucker.'

The man's words had an effect on Robbie. Opening his eyes and stared up at the man and sucked harder. Licking his tongue along the underside of his fingers and moaning.

'That's it. Suck me good.'

The man began stroking his cock in earnest. Aiming his cock towards Robbie's face. Robbie's balls drew up, he was so close.

'Get ready. I'm gonna cum!'

The man's warm cum splashed on Robbie's face. His cock jerked as he came, soaking his panties. The man grunted and another stream of cum shot from his thick cock, landing on Robbie's chest. The man slipped his fingers from Robbie's mouth and after a couple minutes stood up and fixed his clothes.

'You're a tease. I like that. You ever want to give up your virgin ass to someone that knows how to fuck. You let me know. My name is Wulf Parker. Your Mom knows me. Real well.'

Wulf smiled and winked at Robbie. He unlocked the bathroom and left Robbie standing there. Stunned and cummed on.

****

Robbie was so glad school was over! He had this summer to either look for a job or whatever. His parents were not that strict. His little sister would be graduating next year. He glanced outside, through the kitchen window over the sink. He saw her sunning herself, while his Dad did some yard work.

He had not asked his Mom about Wulf yet. They were alone in the kitchen and for some reason the outfit she wore was sparking a lustful awareness.

'Hey Mom, you know a Wulf Parker?'

The dish she held slipped from her hands and crashed to the floor.

'Shit.'

She knelt to pick up the pieces. From this angle Robbie could see right down her blouse. Did she have to be wearing a lacy bra? Lace was his favorite. It felt so good against his cock when he wore lac panties. He moaned and hurriedly bent to help his Mom clean up the mess.

'I got it, Mom. Ow!'

A sharp edge of the plate cut his finger and blood immediately welled into the cut.

'Oh gosh, Robbie.'

His Mom grabbed his finger and sucked the tip into her mouth. Getting him to stand up by pulling on his arm. The warm, wet heat of her mouth sucking on his finger tip immediately transferred to his already aroused cock. Fuck! Not now! Robbie thought sternly. She sucked hard trying to stop the flow of blood. Pulling Robbie to the sink and slipping his finger from her mouth. He nearly moaned again.

'Where did you hear that name, Robbie?'

She ran warm water over the cut and held his finger tightly. At the same time she reached over the sink to the window sill, closing the window. Her husband and his sister were in the yard. She watched her shirtless husband labor at some task, sweat glistening on his tanned skin. Mona sighed, clenching her fingers as instant arousal hit her hard.

'I met him. Ow! Mom, that hurts.'

Robbie's protest drew her attention back to his wounded hand. She applied a bandage and led Robbie to the kitchen table. The pain of his cut did nothing to alleviate his erection. Openly staring may earn him another spanking. Robbie smiled at the thought.

'Robbie. Wulf is a person I know from social gatherings. I think at your age you are old enough to know a couple things about your father and I. In case you may have thoughts and feelings that are similar.'

Whatever his Mom was talking about, Robbie just nodded. She was so absorbed in thought. She hardly noticed her top two buttons came a loose and Robbie was getting a better view of her generous cleavage.

'We have an open relationship and we have other friends we associate with on a regular-'

'You fuck other guys, Mom?'

Robbie's Mom blinked then flushed.

'Well. Put bluntly, yes. I..fuck other guys.'

His Mom gazed at him. Her eyes looking soft. Her lips pursed. Fuck she was so hot! His cock ached.

'Mom, I think you are really pretty. I think any guy would want to fuck you. I would.'

The last part hung in the air. His Mom blinked rapidly and grabbed his hand.

'Your cut seems OK.'

He grabbed her wrist and pulled her closer.

'Did you hear me, Mom. I want to fuck you. You make me so fucking horny. I jerk off thinking about cumming on your tits.'

His Mom pulled back and raised her hand as if to strike him. Instead she placed her hand to her chest. She felt her shirt was unbuttoned and quickly snapped them close.

'We can't ever. Ever.' She was trembling. Robbie went to comfort his Mom. He stood over her and hugged her from behind. 'Oh! Robbie your-'

He pulled his hips back, so his hard cock wasn't touching her soft ass but kept his arms around his Mom.

'Sorry, Mom. You do it to me.'

His erection had pressed against the curve of her soft ass for a split second and though it was unintentional Robbie could not wait to do it again.