Sleepwalking
- 1 year ago
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I was always a bit modest about appearing in my underwear in front of my
girlfriend Lorraine and Lorraine was rather more confident than me and
didn't seem to be bothered about standing in her bra and panties in
front of an open window. I guess you could say she was a bit of an
exhibitionist.
After a few years living with Lorraine I thought one I noticed one
morning how I had stopped wearing pyjamas but also how uncomfortable I
was when I woke up with my hard on trapped in the boxer shorts I was
wearing.
What was it about the discomfort I felt that had me externalising my own
clothing?
I told my girlfriend Lorraine about my discomfort and she suggested I
try wearing her slip.
I told her not to be daft. Men didn't dress like that.
"Come on, Phillip, aren't you man enough to DRESS in a slip?"
Should the way she emphasised "dress" have set off alarm bells in my
straight vanilla mind?
Man enough to dress in my girlfriend's underwear? Put like this, my
masculinity was at issue. Lorraine was saying that a real man would not
be threatened by wearing women's clothing. Was this why I was so
nervous about appearing in my underwear in front of her? Was I not man
enough?
After two more nights I decided to try what she suggested.
I drew the curtains as she went into the bathroom and picked out one of
her lacy pink slips I felt even more nervous. I didn't want her to see
me as I took off my boxer shorts or as I put my head through the bottom
or my arms through the straps. So I turned off the lights and quickly
took off my boxer shorts with my back to the door and closed my eyes as
this amazing lacy silky material slid down my arms over my head and down
over my chest and I was already stiff by the time it reached my backside
but my hard on was not constrained in my slip as it had been in those
boxer shorts.
It was true it felt more comfortable.
It was then as I turned round and opened my eyes that I noticed that the
lights were on and I was standing in my girlfriend's slip in front of
her.
All she said was "You could have asked me first big boy" as she took a
picture of me on her mobile 'phone.
I felt my face redden and I dived under the sheets of our bed as quickly
as I could.
"Listen Phyllis, I mean Phillip, the point of wearing your slip is for
you to be more comfortable both physically and psychologically with what
you are wearing."
"What d...d...do you mean?" I said pulling the sheets over my almost naked
body...
"You are pulling those sheets over you like you are naked underneath
them. Are you? Are you really a girl Phillip? Should I call you
Phyllis - Is that who you really are? Or are you just a man in a slip?
If you are just a man in a slip you should be confident about letting
not just me but the world see it because it is not who you really are
but a disguise. However if really you are your anima, and I think
Phyllis is a great name for her, then you are semi-naked in a slip and I
can understand your modesty. I'll let you sleep on it," Lorraine said.
Was I a girl trapped in a man's body? Was that why I felt semi-naked?
Was that why I had always felt different? Was what Lorraine was saying
right? Should a real man be confident for the world to see him in a
dress because that was not who he really was? Or should a real man
never think of wearing a dress? I rubbed myself under her slip. I was
normally hard when I woke up not when I went to bed...
Gradually as my mind pondered these questions my hard on subsided and I
fell asleep dreaming of wearing panties, fishnet stockings and a garter
belt and patent black court shoes under a black silk ballgown and a
shoulder-length pink wig.
When I woke the following morning the first thing I noticed was that I
did not have the same problem with my morning hard-on in my slip as I
did in those boxer shorts and I didn't register that Lorraine had opened
the curtains and the windows as I stumbled to the bathroom. Obviously I
had noticed that I was wearing a pink slip by at least the time I had
reached the bathroom but it was only as I opened the bathroom door that
I realised I was looking straight out into the street...
I quickly went back into the bathroom and shut the door. Had anyone
seen me? What should I do? Take my slip off obviously. But should I
wrap a towel round my waist like a skirt in the way that a man would as
I took my slip back to the bed or should I cover my chest with the towel
in the way that a woman would and wrap a towel round my head like a
woman would in case anyone had seen me?
I decided to wrap a towel round my chest and another round my head like
a woman would in case someone had seen me. Surely they could not have
seen that I was a man wearing a slip from the street and if I came out
wearing two towels like a woman they would think they had seen a woman
coming out of the bathroom yet I could just about pass for a man wearing
these towels whereas I certainly could not wearing a slip. I headed for
the bedroom wearing the towels and holding my slip.
"Morning, I see you are still not sure whether you are Phyllis or
Phillip," Lorraine said.
"You could have told me that you had opened the curtains," I replied.
"What and miss the opportunity to photograph you in your slip?" Lorraine
replied. "Were you more comfortable than in those horrible boxer
shorts?"
"Yes I was lot more comfortable in my slip," I reluctantly admitted.
"I think we had better buy you some more. Any colour preference
Phyllis, I mean Phillip?" Lorraine replied.
As Lorraine was saying this I had hurriedly drawn the curtains, took off
my towels and put on some boxer shorts and noticed fairly quickly how
tight they were again. I finished getting dressed, took the towels back
to the bathroom and went down to have breakfast.
When I had finished Lorraine said it was time that we went shopping and
we headed into town. When we got to town we met Pat who was having
coffee on Costas as Lorraine and I went to buy our coffee. She said Bob
was not with her today and did we mind if she tagged along with us?
"Of course not," I replied.
We walked through the shopping centre. At this time in the morning
before I was really awake my eyes would follow anyone in a skirt and as
usual there were a number of beautiful women in miniskirts. I tried to
pretend I was not looking at each of these beautiful women and engaged
in the conversation with Lorraine and Pat, who were themselves as usual
both looking stunning too. Before I knew what was happening I found
myself with Lorraine and Pat in Victoria's Secret. Lorraine had started
picking out slips...
"What do you think of this one, Phillip?" she asked holding it up in
front of me. I was grateful the lighting was quite dark inside the shop
and hoped that Pat had not noticed my face getting redder.
It was a silky red slip with a black lacy trim round the bra and straps
and the base of the slip. I said it was an attractive garment.
Pat giggled. "You're not buying it for Phillip, are you?"
"Oh no, of cooourse not!" Lorraine said, a little too sarcastically.
I was hoping Pat did not pick up on this.
"But I like to know whether he likes the look and feel of my clothes."
I was still red and hoping Pat had not picked up on this as I saw
Lorraine grab a second matching slip.
"He's very good, Phillip, Bob would never come into Victoria's Secret
with me," Pat said.
"It's self-interest," Lorraine replied enjoying my discomfort.
I started to reason that Pat may just think that Lorraine was saying
that my self-interest was in how Lorraine looked in bed as I left them
to go to the toilet.
I later found out that Lorraine had then told Pat about how she had
persuaded me to wear one of her slips last night and I had picked the
pink one!
"Seriously? Your man's man Phillip in a pink slip? I would love to
have seen that!"
Lorraine then showed her some pictures of me wearing my slip.
"No! I would never have believed it!"
"Yes, the most girly of all my slips! I have bought a dozen matching
slips so we are both dressed the same from now on and I have bought him
a few pairs of panties. I hope to be taking him bra shopping soon.
Then we'll work on some other things."
"Do you think I could get Bob into a slip?"
"Why don't you bet him that he's not man enough to wear one? Then when
he says real men don't wear women's clothes challenge him to say whether
he thinks Phillip is a real man."
"But how would I then reveal this to Bob?"
"I have an idea," Lorraine said as she saw me coming back. "I'll get
back to you on that."
Eisley
- 04.10.2021
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