tagTranssexuals & CrossdressersSissyhood of Travelling Panties Ch. 03

Sissyhood of Travelling Panties Ch. 03

bydaddyslittlebitch©

Chapter 3: Carl

Blake's mind could not shake the image of the pair of sexy red panties hidden in his room. As he ran down the stairs to answer his mom's call that Carl, his best friend, was here, all he could think about was the sensual scarlet satin of the boyshort panties with their red lace details. His mind could not help dwelling on how he had rubbed his dick off through the panties until covering them with his cum. Just thinking about it and his dick was already becoming a little stiffer once more.

Carl had been Blake's best friend for years and spent a lot of his time hanging out around Blake's home. In fact, Blake's parents, Alex and Helen, were almost like a second set of parents for him, a set that were far more attentive than his actual parents. Like most of the other neighbourhood boys, he had checked out Blake's mom's hot body more times than he cared to admit. Certainly, the opportunity to stare at those sensual curves were another reason he spent so much time here.

Carl was a little disappointed, therefore, when he saw Blake's mom leave to go out with his dad. He had always wondered how an extremely ordinary seeming guy like Blake's dad could have got such a hot woman as his mom. He had always wondered and, at the same time, kind of fantasised that this would mean she would be on the look out for a younger model. Carl himself was tall but fairly slight with his scruffy brown hair tied back in a ponytail. He knew he wasn't much to look at, but figured neither was Blake's dad.

"How do you cope living with a mom that hot?" Carl asked his best friend once they were alone in the house, "I mean, even if she were my mom, I'd just be taking every moment I could to try and see her naked or go through her panties."

For many friendships, even one where one friend had a hot MILF for a mother, this would have been a pretty unusual remark, but Blake was used to it now, not just from Carl, but all his friends liked to go on about the hotness of his mother, almost willing him to admit to his kinky incestuous thoughts.

He usually just blushed and nodded. This time, however, he was surprised by quite how specific Carl had been about going through Blake's mom's panties. How specific, and how accurate to just what Blake himself had been doing earlier that afternoon when he'd jerked off into that pair of red satin panties he had mistakenly assumed were his mom's (rather than his crossdressing dad's).

Blake thought for a moment. He wondered whether he should share his dirty thoughts about his mother with his oldest friend. Carl, he guessed from what he had just said, would probably understand. Maybe he should share the sexy panties he had taken.

"I don't know about all that, but I've got something you might want to see," Blake smirked.

They went upstairs to the bedroom and Blake fished out the red satin panties. He wasn't sure quite how much to admit to his best friend, whether to tell him that he had jerked off into the panties, but he decided against it. He simply held them out.

"Look what I swiped from the laundry basket," he said, "How sexy are these?"

"Oh God, they're really her panties, your hot mom's hot panties," Carl gasped, taking them and rubbing the soft satin material between his fingers.

He had always slightly believed from Blake's awkward reaction whenever the subject was raised that Blake shared many of his friends' lust for his hot mother and now here was some proof. Blake had raided his mom's lingerie and came back with something pretty sexy. He knew he should judge Blake as somehow sick and twisted for stealing his mom's panties, but he was mostly just excited to hold a pair of MILF Helen's sexy undies.

Just touching the soft fabric, seeing the sexy lace pattern on the smooth red satin, and imagining Helen's pussy touching this same material as he now had in his hand, was getting Carl a little stiff already. He had to feel more of these panties against his skin, it was almost like feeling Helen's pussy. He held them to his face and sniffed, a strong musky odour that he imagined, for all he knew, might be the smell of that hot older woman's cunt, but was actually the intermingled cum of her husband and son.

"Man, you've got to let me take these, I'll do anything," Carl sighed, longing to get Helen's sexy panties home with him.

He turned and put the panties down on the table beside Blake's bed. Blake watched, still not quite sure what to do. Should he let his friend take his mom's panties? He guessed he could turn it to his advantage, he knew that Carl had a massive crush on his mom and the gift of her panties would certainly put Carl in his debt.

As he thought this, half his mind still on his mom and her hot panties, he couldn't help glancing over his best friend as he bent over the table. Carl was wearing a pair of tight jeans that gave the outline of a surprisingly feminine bubble butt, his long brown hair falling down his back made him seem almost like a woman from behind. A thought began to form in Blake's head that was too kinky to even admit to.

Mind you, he thought, he had already admitted to his friend that he shared Carl's lust for his mother. And he had shown him that he had stolen his mom's panties. This revelation of incestuous panty lust was kinky enough that he might as well give in to his feelings and take it a step further.

"OK," he said, "You can take mom's panties," Carl's heart skipped with excitement, his dick was already a little stiff at the thought, "But, you have to do something for me."

Carl didn't really have an inkling of what Blake was thinking, but even if he did, he didn't care. He really would have done almost anything his friend suggested to get that bit closer to his hot mom. His thoughts were already on the sexy satin panties and what to do with them. So much so that he was actually quite ready for Blake's next words.

"I want you to wear them," Blake said.

The weirdness of this didn't really sink in to Carl. He was already half imagining wearing the panties anyway, seeing rubbing his dick against the red fabric as the closest he could get to rubbing it against Helen's pink pussy.

"No, not just to wear them," Blake went on, "I think you can tell that I fantasise about my mom. That I want to fuck her. Well, if you want her panties, you have to dress up for me in my mom's lingerie. Dress up and let me do to you what I dream of doing to her!"

There, he had said it. He had asked his best friend to let him fuck him. Not only that, he had asked Carl to dress as his mom while Blake did it. It sounded so weird and wrong to say it, but it didn't stop him from getting excited by the idea.

Carl was a little shocked to hear this proposed. But what shocked him more was that he wasn't instantly turned off the idea. Some part of him was starting to find it actually pretty exciting. He had never thought about being with another man before, but somehow the fact that he had thought and fantasised so much about Blake's mom that an element of her seductive persuasiveness was projected onto Blake in his friend's mind.

More than that, the strength of the lust he felt for Helen and the feelings brought up in him from feeling what he thought were her panties were enough to make him feel like dressing up completely in her lingerie would make him feel as she felt, make him feel closer to the object of his desires than anything else.

This was what he told himself but a part of him was just a curious, horny 19 year old who wanted to get off any way he could.

So, both still a little in shock that they were actually going through with this, but neither backing out, Blake and Carl found themselves a few minutes later in Blake's parents' room. Both boys were filled with excitement to be going through Blake's mom's lingerie, picking out things for Carl to wear with his red satin panties.

Before long, Carl was not just wearing the satin panties but was rolling a pair of Helen's thigh high nylon stockings up his skinny legs and attaching them to a black lace garter belt. With Blake's help, he laced himself into a black corset that pulled his narrow waist in further, accentuating the girlish roundness of his ass.

With his ponytail untied, his long brown hair fell over his shoulders in a distinctly feminine style. A little lipstick and makeup, even applied with Carl's not so expert skills, brought out a girlishness in his facial features.

While he didn't look quite like Blake's mom, Blake also had to admit that his best friend equally didn't look half bad as a girl. He looked like a sexy stripper in his corset and stockings. The only difference being that there was already a sizeable telltale bulge in the red satin panties, panties that Blake couldn't help but recall he had jizzed inside before his friend had filled them with his bulging erection.

"What now?" Carl asked nervously.

He felt surprisingly good dressed in corset, stockings and those sexy satin panties, he felt like he could do just as Blake's mom would, be a hot sexy slut. He was really enjoying the feel of the corset pulling him into a girly shape, the stockings making his legs so smooth and, more than anything, the panties that he was sure, incorrectly though, that the object of his lust had had against her pussy. In fact, he was the third guy that day whose cock had rubbed against that satin and, at this rate, might be the third to cum in them.

However much he was getting off on wearing Helen's sexy lingerie, his dick growing in the soft panties, he still didn't quite know how to react around Blake. He sort of knew what Blake expected of him but he didn't really know how to proceed. Part of him really wanted to play the slut with his friend's cock, but part of him was still afraid of it.

"Now?" Blake answered, "Now I want you to suck my cock just like my mom would."

He pushed Carl to his knees and Carl did little to resist as his friend unzipped his pants and pulled out his dick. Blake had already cum once that day from fantasising about his mom in those panties, but seeing his best friend dressed up as his mom was getting him very stiff once again.

Carl had never been that close to another man's member before and it made him a little nervous to be here, on his knees dolled up in lingerie, with one dangling in his face. Nervous, but excited, increasingly the part of him that wanted to feel just what hot MILF Helen felt when dressed like this going down on a cock was taking over.

A little gingerly, he reached out and felt the throbbing warmth of his friend's erection with his hand. He held Blake's dick and slowly began to stroke the shaft just as if he was beating his own meat.

"Oh yeah," Blake moaned, "That's it, stroke my dick. Now open your mouth and lick it. Lick it like a slut, a slut like my mom!"

Carl did as he was told, his painted lips opened and his tongue flicked over where the purple head of Blake's dick poked out of his foreskin. A few gentle flicks of his tongue, watching the cock quiver and harden, and pretty soon Carl was licking all over his best friend's veiny shaft like licking dicks was something he had always done.

Pretty soon, he started to want that hardness inside him, wanted to swallow his friend's meat, feel it filling his mouth and throat. He grabbed Blake's cock, opened his mouth and swallowed as much of the shaft as he could, sliding it in and out of his painted lips until he could see smears of lipstick on the rock hard shaft.

"Oh boy, that's good," he gasped between slurping around his friend's hardon, "I never knew being a slut for cock felt this good. I love it in my mouth!"

As Carl bobbed back and forth on the hard cock in his mouth, Blake kept a rhythm with him, shafting his friend's face as eagerly as Carl swallowed. Blake had been a little unsure how his mad suggestion would go but now, looking down on his best friend, with Carl in corset, stockings and the very same panties Blake himself had jerked off into, he felt more turned on than he could remember in a long time.

For his part, Carl was really throwing himself into his role as corset and panty wearing slut. Indeed, the feel of those satin panties on his dick was making him feel so good that his own dick was growing harder and harder, stretching and straining against the soft material just as Blake's father had done, unbeknownst to either of them.

Carl wondered if this was how Helen felt dressed in the same corset and stockings that he now wore, if she longed to gobble cock like he suddenly desired. The dick in her mouth would never be enough for a gorgeous woman with a voracious sexual appetite like Helen, he thought. She would want more, she would want it inside her in other ways. He trembled with anticipation at where this was going to go next.

Blake was loving the feeling of face fucking his sissified friend, his dick was rock hard and, if he wasn't careful, would explode a sticky load of spunk right in his friend's face. But he was not truly satisfied yet. He wanted to know what it might feel like to fuck his mother and, for all that his friend in her clothes gave head as Blake dreamed his mother would, there was still one more step.

"Bend over bitch," he said, thrilled to see how responsive Carl was to being a crossdressed slut, "Bend over and spread those sexy stockinged legs. I want to fuck that ass like I want to fuck my momma!"

Carl was by now only too keen to submit, as much eager to get a picture of Blake screwing his mother as Blake was himself. He got up and went over to the bed, bending over so his ass was in the air, he spread his stockinged legs wide so the black garters holding up his stockings showed a path to the pretty red panties that felt so good on his dick.

Without even bothering to remove the panties that he had already jerked off into, Blake positioned himself behind Carl and simply pulled the red satin undies to one side to reveal his best friend's puckered little virgin hole. It was going to be a tight squeeze for Blake's rock hard cock.

"Oh boy that's good," Carl moaned in a distinctly girly fashion as Blake used his finger to slide inside Carl's ass and begin to loosen him up.

"Mmm, you wanna fuck?" Blake moaned back, shoving an extra finger in, "You wanna fuck like my mom?"

"Yes," Carl sighed, pushing his ass back against Blake's fingers, "Screw my ass just like you've always wanted to do to your momma!"

Blake did not need to be asked again. He withdrew his fingers and stuck the head of his dick, still lick with Carl's saliva, right at the opening of his friend's tight just fingered ass, and thrust forward, pushing in and opening up Carl's anal cherry until he was buried so far inside his friend that his thighs were rubbing against Carl's stockings.

For Carl there was a moment of pain as his friend tore into his ass, but it did not take him long to adjust to enjoying the feeling of being filled up back there, the feeling of a hard, thick rod impaling him, shafting into him. He kept his legs wide, his head down and began to rub his ass back up against Blake's deep thrusts. After a while it began to feel incredible, his own cock was every bit as hard as the one in his ass.

"Oh yeah, take it, take my dick, momma!" Blake cried, "Feels good as I fuck your ass, mom."

Blake was beginning to lose himself in the fantasy. From behind, the black corset pulling his waist in, the stockings on his legs and panties on that fine round ass, Carl, only visible from his long brown hair, could easily have passed for Blake's mom as Blake shafted his ass. The combined thought of fucking both his mom and his crossdressed sissy best friend was getting too much for Blake.

"Yeah, that's it, mom, feel my cock inside you, bitch!" he went on.

"Yes! Yes! Fuck me, Blake. Make momma your bitch," moaned Carl imitating Helen, the object of his lust as much as Blake's.

One thing that still reminded Blake that it was his friend's ass he was fucking and not his mother's was the feel of his balls slapping against where Carl's hung out of the red satin panties after Blake had pulled them aside to get access to his friend's tight hole.

Carl was surprised to feel Blake reach around his legs and start rubbing against the red satin of the panties to where his dick still pressed against them. He was surprised but he put up no resistance as Blake ploughed his ass and rubbed his dick together at the same time.

"Oh God, I'm gonna cum," Carl sighed, "I'm gonna cum right here in your mom's panties!"

"Don't worry," gasped Blake, "I already did."

Carl was shocked to hear that the panties that his friend had given him, seen him sniff and made him wear, Blake had already enjoyed, had already filled with his sticky spunk. Maybe earlier on that would have disturbed him, but now it just excited him further to be about to fill the same panties with cum just as his friend who was now fucking his ass had.

In a moment, Carl felt his release flooding through his body, his very first anal fucking and his first time dressed as a girly sissy were both enough to make this the best orgasm he could remember. As Blake shafted his tight ass and rubbed his dick, Carl started shooting loads of spunk into the red satin panties.

The feel of his friend cumming in his hand and into the stolen panties was enough to send Blake over the edge as well. Thrusting deep into Carl's tight hole, Blake's dick shot its second load of the day, streams of cum filled Carl's ass until it ran down his thighs and over Blake's mom's stockings.

"Wow, that was good," Blake moaned, "If only fucking my real mom were half that good!"

"Yes, I think I earned these sticky panties," Carl agreed, "I'm gonna keep them and every time I wear them think about your dick in my ass."

Carl was as good as his word. Later that night, once the two had done their best job of cleaning and replacing corset, stockings and garters, and Carl had cleaned himself of spunk and lipstick, Carl left the house to go home. As he walked out the door, Blake found himself almost unintentionally checking out his friend's round fuckable ass and noticed, just above the waistband of Carl's jeans, the red satin and lace of the stolen panties.

To be continued...

Report Story

bydaddyslittlebitch© 3 comments/ 24396 views/ 10 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartA_denzer, Stockcard12 and 8 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Ambrill12/26/13

This was sexy as hell. Love the way you described the lipstick staining Blake's cock, so sexy! Great story! It would be great if the son and father did something together too with some panties!

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 3 User Comments  or
Click here to leave your own comment on this submission!

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel