Sleepwalking Daddy
- 2 years ago
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Sleep Part 3 free porn video
Sleep 3:
I was standing in the middle of my bedroom wearing a bra and panties and
trying trying to look masculine as I put on my slip. I was having a
reality check - I could not be more ridiculous could I? This wasn't
what real men did was it?
And Lorraine in order to encourage me to transition more quickly had now
started calling me "Phyllis."
A man called Phyllis?
I looked at my face in the mirror. Oh my God! What had I let Lorraine
do to my eyebrows? She had arched them in an unmistakably feminine way.
Why had I let Lorraine do this without checking my face in the mirror
before going to work?
And then there were my mascaraed eyelashes - I could not believe how
feminine my eyelashes looked!
I started to cry.
That wasn't what real men did either was it? I looked in myself in the
mirror. Ok this was another first. I had forgotten the sight of many a
girl after a disco with her mascara running down her face and now I
looked like one of those girls!
Lorraine heard me and could not suppress a giggle at the sight of her
"man's man" of a husband standing there in his bra and panties and slip
with his mascara running down his cheeks.
I giggled too.
I realised I must have looked comical.
"What am I going to do now? How can I face people at work knowing I
looked like this earlier today?"
Lorraine started cleaning my face as she said:
"Not quite, you didn't have mascara running down your face did you?
Look, you have to step it up a gear. You are out of your comfort zone
and you need a guide here. You need someone to hold your hand as you
find your way. Trust me I know what you need."
Lorraine finished cleaning my face.
"After what you did to my face?"
"What you spend a day in mascara and you are already an ungrateful
bitch! And just after I cleaned the mascara off it?"
"No, I meant what you did to my eyebrows and eyelashes earlier!"
"Hey it wasn't like I did this, was it?" Lorraine said rubbing her
finger on my bottom lip.
"Did what?"
"Do this" Lorraine said closing her mouth tightly and then rubbing her
lips together. I had no idea what I was doing but I copied her
"Perfect!" She said.
I suddenly realised it was not her finger on my lips.
"That was lipstick wasn't it?"
"I told you you need to trust me. Of course it was lipstick. It's what
you need. The point here is 'more is less'!"
"What?"
"The more you dress like a woman, my little bitch, and I know about
dressing like a woman - that's why you have to trust me, the less like
a girl you will feel."
I looked puzzled.
"When you put on your slip, panties and bra you reacted like a girl
right?"
I nodded.
"That's why I gave you a girl's name. Now the more you dress like a
woman the less you will feel like a girl. So you drew no reaction at
work with your eyebrows and mascara? We need to think how to crank this
up. Close your eyes let me massage you. You are so tense." I felt
Lorraine massaging my eyelids.
I tried to digest what Lorraine had just said to me. Was she saying I
would feel more manly if I dressed like this or more womanly?
"This should do it! Now open your eyes."
I saw myself in the mirror. "Shit!"
"That's really unladylike language!"
"But I'm not a lady."
"You really want to be known as my little bitch? Or would you prefer to
be a lady? Come on which would you prefer?"
"Neither I am a man."
"Take a look at yourself in the mirror again and say that."
Apart from my hair I looked like a woman. Lorraine had added false
eyelashes and eye shadow so that my eyes looked as unmistakably feminine
as my lipstick coated lips.
"What have you done?"
"I am trying to force you to confront yourself. Your reaction is good.
It means you recognise that this is not normal. Now where do you go
with this in your mind? Are you Phyllis or Phillip? What is normal?
Are you a man in a fancy dress costume or a woman trapped in a man's
body?"
I look at myself in the mirror as Lorraine started to fiddle with my
hair.
Where was she taking me? How could I be more manly looking like this?
She then put this long pink wig on my head. The wig just screamed
"Girl!" Men don't really wear pink all that much and pink hair? I also
noted it really suited me. It was unnatural. I was unnatural. Or was
I? I started to brush my pink hair...
Who am I? That must be someone else in the mirror. I'm not this
beautiful woman I am looking at am I? I am a man, aren't I?
"Hold your hair up and look down, Phyllis" Lorraine said as if she could
read my thoughts and was answering my last question in the negative -
no, you are not a man you are Phyllis.
I felt her putting a necklace round my neck.
"Ok you can look up now."
I was wearing a necklace. I could have guessed what it said before she
put it on it said "Phyllis". It was defining me. I am Phyllis not
Phillip. Phillip wouldn't wear a necklace that said Phyllis.
We had a long passionate kiss.
"I expect you to wear this necklace unless you decide you are not
Phyllis. Right now that doesn't look like that's going to happen any
time soon, right?"
Of course it wasn't the fact of wearing the necklace imprisoned me in
this identity. Except was this really a prison or was being Phillip a
prison.
I nodded as we kissed again and she squeezed my butt.
I am free! Being Phillip was a prison.
"Here, I have bought you this anklet. It symbolises our new roles. I
am the teacher and you are my student. Put it round your anklet and
always wear it next to your skin to remind you who is in control in our
relationship - me."
I put on my anklet.
"It makes you look so girly!"
What? Had she lost her mind? What about the make-up, wig and lingerie?
Didn't that make me look just a little girly? Why was I bothered
though? Lorraine was helping me to discover my real self what did it
matter what made me look like what I am.
"Take your slip off."
I was quite overwhelmed with all these new feelings and sensations and
no longer capable of resisting Lorraine's guidance as I now saw her also
as my teacher.
"Your bra just doesn't look right. Let me fill it out a bit. That's
better!" Lorraine said pressing my new breasts against my chest. "You
need to get dressed. We are having guests for dinner tonight and
they'll be here in 10 minutes."
What? Other people were going to see me like this? No! How did I get
this bra off.
"Stop panicking! You look beautiful and anyway you might just about be
able to remove the adhesive from your breasts but there is no way you
would get your make-up and wig off. "More is less" remember?"
I stopped in my tracks.
Lorraine said I needed to put on the fishnet pantyhose she had bought
for me and then step into the dress she had bought for me. I liked the
look of my anklet under my fishnets. I would never have thought of
myself as someone who owned fishnet pantyhose before but now it seemed
natural.
I did as I was told and stood still whilst Lorraine zipped me.
Then the doorbell rang.
It was Pat and Bob.
Pat was clearly delighted at what Lorraine had done to me and my
discomfort but would appear not to have told Bob anything.
"Wow. You look amazing Phyllis!" said Pat.
"Hi, I'm Bob" my best friend said clearly not recognizing me.
"Hi, I'm Phyllis," I replied. "I'm one of Lorraine's friends."
"You are hot," Bob said. "But you sound a bit like my friend, Phillip."
"That's because she is. This is your best friend, the man's man. Sexy
isn't she?" Pat laughed enjoying my total humiliation.
I felt like Pat had undressed me and I was naked in front of my best
friend, his wife and my wife and I rushed out of the room and locked
myself in the bathroom.
What I did not see (because I locked myself in the bathroom) was Pat
telling Bob that a bet was a bet and he was going to have to prove
himself a woman of his word.
"What bet?" Lorraine asked pretending not to know about it.
"Well, you see Bob here, he told me that any man who would let his wife
put him in a dress must be gay, and no real man would allow his wife to
do this."
"What a homophobe!" Lorraine replied.
"Exactly. I told Bob that gay men are as much real men as he was. He's
not going to think of himself as a real man anymore now he's going to
wear his first dress! I have the perfect outfit. And I also told him
that many straight men were crossdressers. Men just like him. I would
bet him that the most manly man he knew, your Phyllis, would be in a
dress before the evening was out and if she was so would he be."
Then she twisted the phrase we would always use about honoring a bet
when one of us tried to step out of it:
"So Woman up Bobbie! Lorraine and I will help you to discover who you
are as you are not a real man anymore."
Pat then went out and came back with some bags. I do not know what role
each of the women took in making a woman of Bobbie, as she didn't tell
me but the next thing I knew was a tap on my bathroom door.
I opened the door to see a French Maid cleaning my bedroom with a
feather duster. I could see her panties, garterbelt and fishnet
stockings.
I slapped her butt. She spun round.
"My mistress said I am to teach you to walk in heels."
Shit! The French Maid was my best friend Bob.
"Why are you dressed as a French Maid Bob?"
"I had a bet with Pat and you must call me Bobbie now by the way or they
will have you dressed like this too."
"Did the bet have something to do with my atire when you got here Bob?"
"Yes."
"Sorry mate. You look really hot though." I couldn't believe that I
really wanted to have sex with my best friend. Did that make me gay? I
was not sure. We were both on our way to becoming women now but were we
thinking of each other as men or women? Was I now a lesbian?
"Thanks and so do you."
And the next thing was her tongue in my mouth and my tongue in hers and
then we were on the bed and then my panties were down and well, this is
a family show, let's just say that by the end of the evening I, Phyllis,
was no longer sure if I was bisexual, homosexual or lesbian... And our
wives had also been involved... My manhood was a distant memory...My wife
had made a woman of me... I fell asleep.
I was woken by someone poking my shoulder.
"I tried to warn you, Phyllis," Bobbie said "But I guess old habits die
hard. They heard you calling me Bob so now we have matching outfits."
I looked up in the mirror and noticed that I had been dressed in my own
maid's outfit for cleaning the house, a silk black outfit that revealed
a lot of my breasts and finished some way above my knee with a white
apron and bonnet.
I was also now wearing black fishnet stockings and a garterbelt. I saw
the black court shoes that Bobbie had trained me to wear and walk in
last night and hurriedly put them on.
Bobbie told me
"You now have your own handbag with your mobile phone and purse in it."
"I'm late for work," I said grabbing it and rushing for the door.
I think I heard it ring on my way to work but I had to move quickly and
concentrate on how to walk in my heels so I didn't answer it.
When I got to work they did not recognize me.
"It's me Phyllis," I said forgetting that they only knew me as Phillip.
My phone rang again.
It was Bobbie. It was on loud speaker.
"Phillip the girls rang in to say you were sick and would be taking the
day off."
"Oh great why didn't you tell me before I left now everyone at work has
seen me like this!"
My boss then came and told me to take a few weeks off whilst I sorted my
head out and I was whistled at and asked to do a twirl. I noticed my
dress flare up and I think everyone saw my panties and garterbelt. I
blushed and everyone laughed. I had no-one to blame for this but me.
If only I had answered my phone on the way to work. I curtsied and left
the office as quickly as I could.
Avriella
- 03.06.2020
- 13
- 0
