Caught Mum with a Black Cock Part 1
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Caught By His Mum, Twice free porn video
Caught By His Mum, Twice
Tim ran the scarlet red lipstick slowly across his lips. He paused for a
moment before gently pressing them together, the way he had seen his Mum
do countless times before when applying lipstick. He stared directly into
the large mirror which dominated one wall of the front room of his house
and allowed himself a moment to reflect on his transformation. He had
certainly taken things quite far. As well as his beautiful lipstick he had
applied a light layer of foundation, a puff of blush to his cheeks, a
striking bronze eyeshadow to each eyelid and a swipe of mascara to each
eyelash. His blonde hair had been styled and pushed neatly back with a
burgundy velvet hairband; he had even found some clip-on earrings which
dangled daintily from each ear.
Tim pouted his lips briefly and smiled as he stepped away from the mirror
and into the centre of the room. He looked at the clock, 2:57pm. He took a
deep breath and made his way over to the armchair which was in its usual
place, pushed back against the far wall of the room. Instinctively
smoothing the back of his dress with his hands, Tim slowly lowered himself
into the chair and was immediately engulfed by a sea of petticoats.
Battling to keep control and remain lady-like, he calmly restored some
order and rested his hands in his lap, crossing his legs at his thighs.
After a few exciting but rather stressful seconds he became more settled
and was content with his chosen position in the chair.
Tim was wearing a beautiful 1950's vintage style dress, a stunning floral
design, a quite brilliant deep burgundy colour with various other shades
of red and white to complete the detail. While the bodice was designed to
be fitted, the knee length skirt expanded out into a magnificent sea of
stunning material. Only the best petticoat would do for this dress, and
Tim's petticoat didn't disappoint. It was perfect white, half a dozen
layers of magnificent tulle, adding significant volume to the dress and
thus turning the relatively simple task of sitting in an armchair into an
art. The dress was a perfect fit for Tim's slim body and average height,
it had a delicate series of buttons at the back and as the puffed sleeves
were only small, Tim had draped a long black shawl over his shoulders to
cover his arms and complete the outfit.
2:58pm. Tim sat still and waited. He spotted one of his Mum's fashion
magazines on the coffee table to his right so leaned over to pick it up.
Resting it in his lap, he opened it up about a third of the way through
and began to flick through the pages. While he dare not move significantly
to lose his comfortable position in the chair, his legs were still crossed
and he allowed himself a gentle rock of his top leg over the bottom one.
It felt good. He couldn't see his legs or indeed his shoes due to his
large skirt, but the feeling of pulling up his stockings and slipping his
feet into the cutest pair of Mary-Jane shoes he had ever seen was still
fresh in the memory. Tim had no problem admitting to himself, at this
precise moment in time, he felt incredible.
Another couple of minutes passed and Tim found himself a little more
relaxed. Everything was quiet, the only sound he could hear was the
ticking of the clock and the occasional car drive past on the street
outside. He took another deep breath and continued to flick through the
pages of the magazine, stopping every so often when he saw a picture he
really liked. He glanced up at the clock one more time, it was now just
past 3pm.
Then, suddenly, the door to the room flung open. Startled, Tim looked up
from the magazine, his heart skipping a beat as he did so. A mild panic
set in as he realised he was no longer alone in the room. He felt his face
immediately begin to blush.
"Tim?! Is that you? Oh my God!!" came an overly enthusiastic voice from
the woman in the doorway.
"Mum... you're... home early..." Tim replied, quietly, struggling to get
his words out. He wasn't sure where to look or what to do.
"Why on earth are you dressed as a woman, Tim? Is that my dress? It IS my
dress! Oh God!" She shut the door behind her and walked a little closer to
Tim. She was exquisitely dressed too, wearing a long dark green designer
coat, with black skirt and leather heeled boots peeping out from beneath.
She was wearing a red silk scarf and carried a Chanel handbag on the crook
of one arm.
"I, err..." Tim had no reply.
"Stand up so I can see you properly...." she instructed sternly.
Tim stood up, closing the magazine and putting it to one side. He took a
step forward and automatically smoothed the skirt of his dress again, this
time from all sides, allowing the petticoat to reform in shape and fall
back neatly into place.
"Give me a twirl then... and a curtsey."
"What?" Tim muttered.
"Give me a twirl, and a curtsey! Let me see you!" she demanded.
Tim did as he was told and slowly turned 180 degrees one way, and then
back the other, pausing for a moment to allow his dress to take shape once
again. He then followed with a perfectly executed curtsey. Clearly it was
not the first time he had ever curtsied for someone, he treated it as if
he was being introduced to the Queen.
"Wow, would you look at you... you sure make a pretty girl, don't you? I'd
say this isn't your first time dressed as a girl. Am I right? And you can
do make up too?!"
Tim nodded.
"And you're wearing stockings?"
He nodded again.
"Incredible..." she whispered, but loud enough to be heard.
Tim stood still, he had nothing to say. There was nowhere to run, he had
to just stand there and take whatever his Mum was going to throw at him.
"And how does it make you feel.... Tim?" she asked curiously.
"Huh?" Tim replied.
"How does it make you feel? Do you like being a woman?"
"I guess...." Tim sounded unsure.
"So you want to BE a woman then?! Shall I call the doctor to make the
arrangements?!" She began to giggle uncontrollably.
"What?"
"Do you want to be..." She was unable to finish her question this time.
"Stop!" Tim shouted.
"What? No, carry on..." she insisted.
"No Steve, I want to stop!" Tim shouted, even louder this time.
"Aww... bloody hell Tim, you were doing well there. That was the best one
yet!"
"It was going fine until you went off script! What was all that 'How does
it make you feel' stuff? 'Do you want to be a woman?' That wasn't in the
script!"
"Ok, ok, I went a bit off track there, sorry. I just thought I'd take it
in a new direction, dig a bit deeper into your character...."
"No Steve, you took it too far. You are meant to catch me wearing your
clothes and then come up with a humiliating punishment, not psychoanalyse
me and arrange an operation..."
Tim began to pace up and down the room, albeit slowly as he was still
getting used to walking in his heels. He was angry, but also quite
enjoying the movement of his petticoat swishing with each step he took. He
stopped and looked over at Steve, his so called friend of almost two
years.
Steve had called round several hours earlier and had told Tim his idea, to
create an elaborate roleplay where he, playing the part of Tim's Mum,
would come home early from an appointment to find her son, Tim, dressed as
woman, wearing her clothes and playing housewife. The scene had been
planned in fine detail, concentrating on the moment of Tim's Mum's
entrance and then her thinking up a subsequent punishment for him. They
had gone to the trouble of drawing up a script of exact lines for each of
them to say, but this was the second time the scene had come to a
premature end. Tim had been reluctant to take part at first, but was soon
persuaded by Steve's insistence that he should give it a go.
While Tim's transformation into looking every bit the beautiful woman had
become extremely thorough, Steve's transformation had been less dramatic,
and more rushed. The large coat he was wearing covered most of what was
underneath, and his make-up was less impressive than Tim's. Truth be told,
while Tim could almost pass as an attractive young woman, Steve looked
more like the boy who was trying on his Mother's clothes. But Tim didn't
say that out loud, he had agreed to go along with the idea for Steve's
benefit, although he would be lying if he said he hadn't enjoyed the day
up until this point.
"I think we're done now." Tim turned to the door.
"No, no... hang on. Let's do it through one more time. Please?" Steve
grabbed Tim's arm and pulled him back from the door.
"Come on Steve, we've done it twice already, and it's gone wrong both
times. I want to get changed..." Tim argued. "Remind me why we're doing it
again?"
"I told you why," Steve huffed. "I've been trying on my Mum's clothes in
secret for years, but I've always wanted to try your Mum's clothes on
too.... Your Mum wears designer labels and vintage dresses, they're much
more expensive than my Mum's. God if she heard me say that she'd kill me!"
"I get that yes, YOU like wearing women's clothes. But why bring me into
this?"
"I just couldn't believe it when you said you'd never done it before...
with a wardrobe full of dresses like your Mum has... so you just had to
try it yourself. And you've had fun today, right? You can't say you're not
enjoying it!"
"Ok, I have quite enjoyed it... but it's still a bit weird and I think we
should stop now." Tim was quite insistent.
"Just one more time, please. We'll go straight to the entrance part, were
I come in to the room. We'll play it from there for a couple of minutes,
then we'll finish. I promise."
Tim sighed "OK.." he replied, somewhat reluctantly.
"Excellent!" Ok, give me five minutes, then I'll come through the door
again. You don't have to be in the chair, maybe be standing at the mirror
or something else this time? Just act mortified when I come through the
door, OK?"
"OK... Let's just get it done" Tim watched Steve leave the room and close
the door behind him and then walked back over to the mirror to check his
make-up.
Tim ran the scarlet red lipstick slowly over his lips once again. His lips
still looked great so he perhaps didn't need to, but he quite enjoyed the
act of applying it. He was pleased to see that the rest of his make-up
still looked perfect. He had been amazed at how easy he had found putting
it on today, and how much it transformed his appearance. He took a few
steps back so he could see more of himself in the mirror, and in
particular the dress he was wearing. It was gorgeous, he felt like a
million dollars. He found himself unconsciously swaying gently from side
to side, he loved the way the dress moved, and how it felt.
Five minutes passed and Steve was due back at any second. Tim stood back
closer to the mirror and waited for the door to the room to open, he
remained relatively calm. Finally, after what seemed like an eternity, but
in reality was only a couple more minutes, he heard the door slowly begin
to open. Before it had had chance to open fully, Tim closed his eyes, took
a deep breath and waited for Steve, his Mum, to begin the scene again.
Suddenly, there came a scream from behind Tim. "Tim?! Oh my....." Steve's
voice was much more high-pitched and feminine than before. To Tim it
sounded like he had really put some extra effort in this time...
Smiling to himself, Tim opened his eyes. But his smile soon disappeared
when he saw the reflection in the mirror from over his shoulder. He turned
around in horror to see his Mum standing in front of him, open mouthed.
This time however, it wasn't Steve playing Tim's Mum, it was his real Mum.
This was not pretend any more, he was playing the scene for real. Tim
looked mortified.
"Mum?! Oh God. No...."
"Tim, what are you doing? Why are you dressed like that?" she asked
curiously.
"It's not what it looks like, I swear!" Tim could feel his face burning as
he blushed uncontrollably. He wanted to run away but it was too late now.
"Well what is it then?! Because from where I'm stood, I know what it looks
like!" She couldn't help but giggle to herself at her son's predicament.
"It was Steve's idea. He's here too. He wanted to wear your clothes so he
made me do it too. He's upstairs, he'll be coming through that door in a
minute..."
"Steve? Don't be so silly. Steven wouldn't make you do something like
this, he's a sensible boy. And anyway, he's not here. No one else is in
the house."
"He is here! He'll explain everything when he gets here, it's just a bit
of fun, I swear..." There was panic in Tim's voice as he tried to explain
the situation.
"Good choice in dress by the way... petticoats too... very pretty! She
teased.
Tim was stressed so appeared not to be amused by the comment. He wanted
nothing more in the world at that moment than for Steve to come through
that door and explain everything to his Mum. Thankfully for Tim, he didn't
have to wait much longer for Steve to show up, but unfortunately he was in
for another surprise when he finally did.
There was a knock at the front door of the house. "Come in!" Tim's Mum
shouted. "We're in here..."
"Mum, no..."
A moment later the door to the front room opened and Steve walked in. But
to Tim's dismay he was no longer wearing his Mum's clothes, he had changed
back into his usual boy jeans and baggy t-shirt.
"Hey Mrs Klein, what's up..." He then turned to see Tim, still standing by
the mirror, just as he had suggested. "Oh... hahaha, Tim. What the....?
Why are you dressed like that?!" He could hardly contain himself as he
spoke.
"What do you mean? This was all your idea!!" Tim shouted.
"My idea? I've just got here, you saw me walk in!" Steve laughed.
"Are you for real? Steve, what the hell? You were here just now, ten
minutes ago. You were wearing Mum's coat! This was all your idea. You made
me dress like this, just for your stupid roleplay!"
"Whoa Tim, calm down bud. If this is what you want to do when you have the
house to yourself, that's fine with me, but take some responsibility will
you? I've just got here. I was going to ask if you wanted to hang out,
I've not seen you for ages..."
"Well I don't know who to believe..." Tim's Mum looked at both boys in
turn, seeing if she could unravel the truth.
"He's lying Mum, it was all his idea..." Tim sounded close to tears.
"Steven, were you here earlier today? Did you make Tim do this? Please be
honest.
"No Mrs Klein, I swear. I've just got here. You saw me come through the
front door just now. This is the first I've heard of Tim wanting to do
this kind of thing..."
"You bastard. You know you were here, you've been here all day. You must
have snuck out the back door just now, and then come back in through the
front when you knew Mum was home..."
"Tim, mind your language. You're a lady now, ladies don't use words like
that!" She giggled and was soon joined by Steve who also laughed.
Tim took a deep breath. He had been stitched up by his so called friend
and there was no way out now, even his own mum was mocking him about it.
He just had to grin and bear it and see it through to the end.
"I suggest you go and get changed now Tim, ok? Put my clothes back in my
room and we can have a chat about this later, yeah?"
"Ok...." Tim agreed. He couldn't wait to leave the room.
"And I'm sorry you had to see this Steven, I wouldn't have minded this as
much if Tim could have owned up from the start, instead of trying to blame
it all on you..."
"It's fine Mrs Klein, he's just experimenting with something new I guess.
But now it's all out in the open, maybe he will be able to talk to you
about it more..." Steve replied. He was finding it difficult not to laugh,
having played such a huge part in Tim's embarrassment.
Without saying another word, Tim headed for the door, but not before
spotting a sly wink from his friend as he left the room. It had been a
humiliating experience for him, and he was glad he was now able to leave.
It remained to be seen whether the boys' friendship could ever recover
from this strange event.
Tim closed the door and immediately went up the stairs to his bedroom,
leaving Steve and Tim's Mum in the front room to reflect on what had just
happened.
"How did I do?" Steve smirked.
"Oh you did perfectly Steven! I don't think that could have gone any
better! His face when he realised it was me standing there was just
priceless, and then when you came back in and denied it all... it was
wonderful!"
"I know, he totally fell for it, all the way through!" Steve added.
"Did you stick to the script?"
"I did yes, I said all the lines we agreed on. I said I've been trying on
my Mum's clothes in secret for years... but always wanted to try on yours,
I couldn't believe he'd never done it before..."
"Perfect! Did he take much convincing?"
"No, not really. I mean once he was convinced it was my thing and he was
just doing me a favour, he went along with all of it....after the second
run he was on about wanting to finish, but with a bit of persuasion he
quickly agreed to do the third run. I even got him to choose his own
outfit and do his own make-up this morning."
"Did you take any photographs of him?"
"No, none. Just like we agreed."
"Excellent! And you wore the outfit I chose for you?"
"Yes, the green coat, black skirt and boots, red silk scarf, Chanel
handbag..."
"Perfect! I bet you looked a treat yourself!" She giggled.
"I guess! Not really my thing if I'm being perfectly honest, but it was
fun to do once for sure!" Steve admitted.
"Well you managed to persuade Tim that it's something you do all the time,
and now I apparently think it's something he does all the time, so you
sure know how to play a character!"
"I guess so..." Steve smiled, trying his hardest not to blush at the
compliment.
"Thanks for doing this, I mean I know it was a bit of a strange request,
but I was looking for a way to have a little joke with Tim, things have
been a bit difficult since his Dad left us, and he needs cheering up
occasionally. And I'm sure he'll come round and see the funny side soon
enough, I'll make sure it doesn't ruin your friendship or anything..."
"That's fine, and I'm sure it won't. I'll just give it a few days before I
call round to see him again!"
"Good idea. Oh, before I forget..." She handed Steve a plain white
envelope. It was sealed but had something inside.
"Is it the amount we agreed?"
"It is, yes. You did everything we agreed." She smiled.
"Thank you. I should go." Steve put the envelope in his pocket and turned
to leave the room.
"Ok, thanks again Steven. Say hi to your Mum for me." She gave one final
friendly smile as she showed her son's friend to the door. She closed it
securely behind him and immediately shouted up the stairs. "Tim, you can
come down now. He's gone..."
A few seconds later, Tim immerged from his bedroom and slowly made his way
down the stairs, meeting his Mum once again in the front room.
He was still dressed as a woman.
"We did it!" Tim squealed as he took his Mum by the hands. They
instinctively broke into a brief but well-rehearsed waltz around the room.
"Darling, you look incredible!"
"Thanks Mum!" Tim giggled as he let go of his Mum's hand so he could give
her a 360 degree twirl, followed by another expertly performed curtsey. "I
adore this dress!!"
"It's gorgeous isn't it?! Absolutely perfect for you. And your make up,
wow! You're really getting good at that."
Tim's Mum took her son by the hand once again and led him to the couch
where they sat down together. Once again Tim's petticoats puffed up and
surrounded him as he sat, much to the delight of both of them. Just as
before, he crossed his legs and laid his hands in his lap.
"So, how did it go? Tell me everything! Did Steven stick to the script?!"
Tim's Mum made herself comfortable on the couch, crossing her legs at her
ankles. She was dressed elegantly as usual, wearing a long navy blue
skirt, white silk blouse and a pair of designer heels.
"He did ok, I mean he said all the right lines, how he'd been trying on
his Mum's clothes in secret for years... always wanted to try on yours...
He wasn't all that believable to begin with, it was pretty obvious that
he'd never dressed up before, although once we started he got into
character and acted out the part quite well. He did go rouge a couple of
times and left the script which was a bit frustrating, but when I told him
I wanted to finish after the second run, he insisted we play it through
the third time, which is what we wanted him to do. During the second run
he actually seemed to get a bit of a kick out of seeing me dressed up, I'm
not sure whether he actually did, or whether he was just really getting
into the scene..."
"Wow. I didn't think Steve was going to be very good at this, clearly I
was wrong."
"Yeah me too, like I say, once he got into it, he was pretty good."
"And he didn't take any pictures of you, did he?"
"No, none." Tim shook his head.
"Good, I told him not to. But we got plenty of him, right?!"
"We sure did!" Tim smiled. "Cameras hidden in the usual places, caught
everything he said and did in this room, and in your bedroom. Plus the
security camera outside will have recorded him letting himself into the
house. All we have to do is bit of editing, change the time stamp of the
outside camera, remove the bits with me on from the inside cameras..."
"Perfect! So we have footage of him letting himself into our house,
helping himself to clothes from my wardrobe then announcing that he's been
trying on his Mum's clothes in secret for years?"
"It's better than that, he said your clothes are so much more expensive
than his Mum's clothes, and how she'd kill him if she ever heard him say
that!"
"Oh really?! So he really wouldn't want his Mum to see the footage
then..."
"Absolutely not!" Tim laughed. "How much does he think he's been paid for
this?"
"One hundred..."
"Wow, so he'll be pretty bummed out when he opens the envelope then..."
"Yep! Monopoly money. One fifty, two twenties and a ten! Plus a note
explaining we have footage of him dressed as a woman, and we're not afraid
to show it to his Mum!"
"Brilliant!" Tim struggled to contain his excitement.
"And he will never say anything, not now he knows we have the footage of
him. And he has absolutely nothing on you as he did as he was told and
took no pictures. It would be his word against ours, which is kinda ironic
considering the argument you just had with him. And he thought he was
screwing YOU over!"
"That's the beauty of it! He genuinely thinks this whole thing was your
idea, and that I went along with it thinking it was all his idea.... but
in reality it was my idea!!"
"Absolutely! It's genius! How many times have we done this now?" Tim's Mum
asked, curiously.
"We did it with Darren, James, Angela and Steve, so Steve was the fourth."
"Four times... And how does Steve compare to the others?"
"Well Angela was a disaster, but I think we know why.."
"It just doesn't work as well with girls..."
"Exactly! She was just suspicious all the way through and I don't think
she ever would have fallen for the blackmail. Darren wasn't great at
pretending, although I loved that scene we did, him locking me outside in
the garden for an hour. James was really good at all of it, a bit too
good perhaps... Steve wasn't too far off James once he got into it,
although James made a much better woman than Steve did, for sure."
"Oh God yeah. The footage we have of James... that coat really suited him,
I swear the first time I saw it I thought it was a recording of me!"
"He hasn't spoken to me since though, nor has Angela. Darren seems to have
come round now though, he's talking to me again."
"Well I think you've taken things up a level today, I've never seen you
look so convincing and comfortable as a woman as you do today, even when
we were shouting at each other, you still retained your elegance. And you
look absolutely stunning!"
"Aww, thanks Mum. I mean, this dress certainly helps..."
"It's yours, keep it, the petticoat too."
Tim was speechless. He leaned over and gave his Mum a hug.
There was a brief moment of calm, both Tim and his Mum were content with
sitting quietly together on the couch, enjoying each other's company. It
was Tim's Mum who broke the quiet, by asking a question.
"Do you still enjoy doing this?" she asked curiously.
"Of course, I love doing this."
"I mean, I'm happy for you to dress up anyway, you know that. We don't
always have to go through this whole rigmarole every time though, having
someone else involved. One day you'll just run out of friends to bribe and
blackmail..."
"No, I like it this way. At least for a little while longer. I'd been
trying on your clothes in secret for years, before you came home early one
day and finally caught me doing it. I was mortified of course, but at the
same time I found myself quite enjoying the feeling of being caught, I was
trapped in a situation, I was humiliated, but it gave me an incredible
thrill. Each time we do this, I get the chance to experience the thrill of
being caught again and again. And I guess, being caught by you is the
ultimate thrill, even if some of the time it is someone else pretending to
be you. Having someone else involved too, making up these backstories and
playing out these different scenes and ideas... even the embarrassment of
having you both stood in front of me, laughing at me, giving me nowhere to
turn... and then you take the other person's side, not believing that
someone could have put me up to doing this... I can't describe how it
makes me feel. I should hate it... but I don't. All I can think about it
getting to experience it all over again."
"I know sweetie. And I'm happy to help out as much as I can." She smiled.
"OK, well in that case, I think we should do this one more time. But we
need to go bigger, something even more elaborate, more humiliating for you
when you are caught. What do you think? Do you know anyone else we can
play with?"
Tim thought for a moment. "There's Andrew from college? I've gotten to
know him fairly well the past few months. I reckon he'd probably give it a
go, especially if you offer him money..."
"Ok then, Andrew is our guy. I'll start working on a new script right
away, I have an idea I've been holding on to for a while, I think now
might be the time to try it..."
"What's your idea?"
"Well like I say, you've set the bar so high today... I honestly think
there's only one place we can go with this now..."
"Where's that?"
"Oh you'll have to wait and see! But you will absolutely love it, I
promise!" She giggled as she grabbed a pen and a notepad from her bag.
"Now why don't you be a good little daughter and go make us some tea!"
Tim stood up and headed towards the kitchen. But before he left the room
completely, he turned to see his Mum, still giggling to herself. She was
still in earshot when she began to sing.
'Duh, duh duh, duhhhhhhh....' It was the tune of 'Here Comes the Bride.'
'Oh My God...' Tim thought to himself as he began making the tea. He
couldn't wait to find out what his Mum had in store for him this time,
although from her little clue, he had a pretty good idea what it might be.
THE END.
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