It was spring time in grade 9. For the past few weeks I had noticed this guy Sam in the
locker room. He was in grade 10 or 11 but was often changing and taking a shower at the
same time as us.
What caught my eye was his underwear. When everyone else was wearing
boxers he was wearing a thong. God, a thong. Where did he get them? It didn't look as pretty
as the ones I had been sneaking from my sister's drawer but if I could get some like his I
would be able to wear them all the time.
One day after school I found myself walking behind him across the parking lot. There was no
one else around. What the hell, it was now or never. I hurried to catch up with him.
"Er, Sam."
"Yeah."
"Um, I, er, um, like wanted to ask you something."
"Yeah."
I felt my self going red. My face was burning. I was embarrassed but I knew if I didn't do it
now I never would.
"I was wondering where you get your underwear." There, I said it. Sam looked at me. If
possible I felt my face getting redder and redder.
"Forget it. Sorry." I turned, and started to move away.
"Hey, wait a minute. You really want to know?"
"Yeah."
"Well, I get mine at The Bay, but all the stores have them."
"Oh, thanks, Sam."
"You're welcome, kid. See yer around."
Dinner time that evening brought another tough conversation. Luckily tonight Mum and
I were the only two at home. Mum had always bought my underwear. I finally managed to tell
her that I wanted to buy my own in future. It didn't seem to faze her but she wanted to know
why. I just told her that most of the guys were not wearing boxers any more and I wanted to
buy the ones everyone else was wearing. She gave me the Mum's ‘I know what you're doing'
look but just said OK.
That weekend I went to the Mall. Sure enough, just as Sam had said, there they were in the
underwear section. Not much to choose from. A couple of colours and two or three makes.
Nothing like the selection I could see across the aisle in the girls section. I bought three pairs
in different colours. When I got home my sister was hanging around. She wanted to know
what I had bought. I told her some underwear. She snatched the bag out of my hands and
pulled out the packages.
"Ah, finally got some of your own, eh?"
I felt myself going red. "What do you mean."
"You think I'm stupid. I know you've been trying on mine. Maybe you'll leave my stuff alone
now."
I tried to bluff my way out but it was no use. It turned out that a few weeks ago she had seen
me. It seems that I had not closed my bedroom door properly and she had seen me. As she
told me about it I remembered the day. It had been a day when I thought I was home alone. I
had snitched a couple of pairs of her panties from the laundry basket and was trying them on
in my bedroom. She had come home early and for once had not slammed the door when she
came in so I didn't know she was home. I had tried on both pairs, walking around my room,
watching myself in the mirror. Of course I got a big hard-on. I lay down on my bed wearing
one pair of her panties my hard-on sticking out. I put the other pair over my face and started
to stroke my cock. The kitchen door slammed. Fuck, someone was home. I noticed my
bedroom door was not closed. I got up quickly to close it and heard my sister calling out if
anyone was home. Nearly caught, I thought. As I now found out, it wasn't nearly; I had been
caught, she just had not done anything about it until now.
Sam was in the locker room again that week. I made sure he could see that he could see that I
was wearing a thong too. I could tell that he had noticed me. He followed me out.
"Can I walk a ways with you, kid."
"Sure."
"I see you found some decent underwear at last."
I felt myself blushing again.
"Yeah. Thanks. I got them at The Bay, like you said."
"Not nearly as pretty as the ones in the other section, though."
My face was burning.
"Bet you try your sister's sometime."
I didn't know where to look. "Well, um, er, I, um ..."
"Oh don't worry about it. I started out that way. I don't have to worry about it anymore. The
first thing I do when I get home is to change into some really nice undies. I live with my
cousin and she doesn't mind at all, in fact she helps me. You could come over some time if
you like and do some dress-up."
"Well, I don't know. Sorta sounds neat."
"Oh well, think about it and we can talk next week. See yah."
The next few days went by in a bit of a haze. I couldn't get the thought of Sam out of my
mind. What did he mean by dress-up. Did he really wear girl's undies all the time. And he
was soooo cute. We are about the same size, 150cm and 55Kg. He had beautiful, shoulder
length brown hair - brunette I guess. It looked so soft and shiny. I'm going to let my own
grow. It is not exactly short now, but I want it down to my shoulders, just like Sam. I couldn't
wait a whole week.
I finally caught up with Sam after school on Monday.
"Hi, Sam."
"Hello kid. How yer doing?"
"Pretty good. Sam, did you mean it when you said I could come round to your place fro dress-
up?'
"Yeah."
"When ?"
"Hmm. Do you know what I mean by dress-up?"
"Well, I guess we can wear girls panties and things."
"It's a bit more than that. When I'm at home I am a girl. I never wear any boy things, even
when I go out. Would that bother you?"
"Geez, no. I'd love to be able to do that."
"OK then, do you want to come over now?"
"Oh please."
"Well, there is one rule which I'd better explain. My cousin is very strict and she does not
allow any boy things in the main house. You have to be girl-dressed or naked. This means we
have to go in through the basement and take off all our clothes before we go upstairs. Can you
do that?"
"I guess."
"Come on then."
I was surprised to find that Sam lived only a block away from us. We went round to the back
of the house and into the basement. We entered a room somewhat like an office reception
area. Sam explained that his cousin worked from home and that this is where she received her
clients. He pointed to one door and told me that was her office where she worked.. There
were two lights by the door and he explained that when she was in her office one of the lights
would be on. The green one meant it was OK to go in to see her, the red one meant that she
was working and could not be disturbed. Both lights were out. Sam started to undress. I
noticed that he put his jeans and runners away in a small closet. He saw me watching.
"That's where I keep all my boy stuff." he explained. "Just fold your stuff up and put it on the
table there. Make sure it's neat ‘cause if Sue comes through she'll be mad if things are
untidy."
I took my clothes off and folded them up and put them on on the table, my runners neatly
lined up on the floor. It felt strange to be naked in a place that looked like an office. Sam
picked up his socks, thong and t-shirt and went through a second door that lead to the private
part of the house. He could see I was little uncomfortable.
"Come on, you'll soon get used to it."
As he passed through the basement towards the stairs he tossed the rest of his boy clothes into
a laundry basket. We went up the stairs to the main house. As we came out into the hallway a
voice called out.
"Hi honey, I'm in the kitchen."
Sam took my hand and gave it a squeeze. "You'll be OK. Come on."
He lead me into the kitchen. "Sue, this is my friend Brian. Brian, this is my cousin Sue."
I was looking a gorgeous blonde. Oh god, I was getting a hard-on. My face was beet-red. I
could feel my whole body blushing.
"Hello Brian, nice to meet you." I mumbled something. "Why don't you girls go and get
dressed. I've just put some cookies in the oven so they should be ready for tasting by the time
you've made yourselves presentable, though I like what I see now."
Oh geeze, I had a full blown hard-on. Sam looked down and saw it.
"See what you mean, coz. Come on."
He took me down to his bedroom. By the time we got there I saw that he was as hard as I was.
As he stretched out on his double bed he said "I think we had better get rid of these before we
dress.".
He patted the bed beside him. "Come on, there's plenty of room for two."
I lay down beside him and started to stroke my cock. I felt a little strange as I had never jerked
off in front of anyone before now. It seemed as if it only took a few strokes and Sam was
spurting great gobs of goo all over his chest and stomach. Then he did something that really
surprised me. He dipped his finger in his goo and then sucked his finger. He did this a few
times until he had scooped up all his goo and swallowed it. He looked over and saw that I had
stopped stroking while I watched him. He smiled. There was a few little spots of cum still on
his chest and one gob right in the corner of his mouth. He saw that I had stopped stroking my
cock while I watched him.
"Come on. If we don't get dressed soon we will miss the cookies coming out of the over, and
that's when they taste best. Here, let me help."
Sam leaned over and started to stroke my cock. My whole body twitched. I don't remember
anyone ever touching my cock, certainly not when I was hard. I closed my eyes as Sam
stroked. It felt so different when someone else did it. I could feel myself coming. I spurted. I
could feel my warm cum on my chest and on my stomach. I just lay there. I didn't want to
move.
"Well, are you going to eat that or can I have it?"
I opened my eyes. Sam was looking at the cum on my chest. "Go ahead" I said. He bent over
and began to lick the cum of my body. The feel of his tongue over my chest sent shivers down
my body. When he sucked on my nipple I thought I was coming all over again. He worked his
way down my body, sucking up every last drop of cum. He even stuck his tongue in my belly
button. I felt myself getting stiff again. Sam noticed it too.
"Come on girl, if we don't get dressed soon we'll be here all day."
He rolled off the bed. Going over to a dresser he opened the top drawer.
"Panties and bras in here. Take your pick. I think for today we'll just stick with a nice skirt
and blouse. Next time you're over we can have a proper girls dress-up session. OK?"
OK? Geeze this was more than OK. There was going to be another time. Oh my god, am I in
heaven or what? Sam quickly found a pair of boy-cut, blue, lace panties and a matching bra,
but then, of course, he knew what she was looking for. He stepped into the panties. I was
fascinated as she shrugged her way into the bra. I had never watched a girl putting on a bra
before. I was going to have to learn to do that. I still hadn't started to get dressed. There was
just too much to choose from. I was used to a quick snatch from the laundry basket or a grab
at the first thing that was in the drawer. Here there was just too much choice. There was
different materials to run my fingers through; nylon, cotton, silk. There were all sorts of
colours: solids, stripes, patterns. There were the styles: bikinis, hi-cuts, briefs, thongs, just
plain panties. I was in paradise just looking, feeling.
Meanwhile, Sam had finished dressing. She was wearing a pale green mini-skirt with a tight,
yellow top. She looked stunning.
"God, will you stop drooling and get dressed."
"Sorry."
"Just kidding. I have some idea how you feel. You need someone to take charge today. Here,
put these on."
She handed me a pair of plain white panties. "Now where's the bra?"
"Do I have to?"
"All the girls our age wear one. Now, padded for big tits, or a trainer for real? Hmmm. I
haven't worn one for a year or so, but, yeah here we are."
She was rummaging around in a bottom drawer. She pulled out a white, cotton bra with a
pattern of little, pink teddy bears.
"Come, slip this on. See it does up in front."
I put my arms through the straps and pulled the front together, clipping it closed with a little
plastic hook. It felt exciting having something tight round my chest. I don't have any tits but
it seemed like there was a fullness in the cups. Imagination. I found myself feeling my
breasts, massaging. Maybe it wasn't imagination. I'm sure there was a fullness there.
"Hey, come on perv. Put this on." she passed me a plaid min-skirt. I stepped into it and
fastened the waistband.
"It's really lucky that we are nearly the same size. I think we will be
able to share clothes. Stand up straight while I check your bra straps. Just a little adjustment
here I think. There. How does that feel."
"Oh, just wonderful."
"Great. Now get this on while I finish up."
She passed me a white blouse. It had ruffles down the front, long sleeves with ruffles at the
cuff. I struggled with it for quite a while until I realized that the buttons were on the other
side. This was a proper, girls blouse. The buttons were on the LEFT. It took a couple of
minutes but I finally figured it out. It was too small.
"That's not going to work. I've got an idea.".
She went to her closet and brought out a plain white blouse almost like a one my own dress
shirts. Again it took me a little while to get it on - those damn buttons on the wrong side. A
much better fit. A pair of white knee socks and black Mary Janes and I was dressed.
We went back to the kitchen where Sue had a plate of fresh cookies on the counter.
"Well hello. This must be your friend Brian."
"Hi, ummm ."
"You can call me Sue. Sam's being telling me a little bit about you. Do you like dressing as a
girl?"
I felt myself blushing. "Well, umm, it's sorta kinda nice."
"Come on, help yourself to the cookies and Sam, help your friend get something to drink
while we have a little chat."
I don't know why but in the next half hour or so I found myself telling Sue some of the things
that had been bottled up inside me for so long. She was so easy to talk to. Time just seemed to
fly by.
"Oh is that the time. I've got to get home. Mum will be wondering what's happened to me."
"Well Brian, are we going to see some more of you in the future now you know where Sam
and I live?"
"Well, I'd like to, Sue, if I may."
"Sure you can dear but I don't think we can go on calling you Brian when you're here dressed
like that. Do you have another name that we can use?"
"I've never really thought about it."
"Well, I've got a suggestion. Why don't we just use Brian but pronounce it slightly
differently. If we made it into two syllables we could say Bri-ann. We would just have to add
an ‘ne' to the end and there we are, Brianne. We can always change it later if you don't like it
or come up with another name. What do you think?"
I turned her suggestion over in my mind for a few seconds. Even said the name out loud a
couple of times.
"Yeah, it's kinda cool. I like it."
"Good, then that's what it will be. You'd better get off home now."
She gave me a hug and a kiss on the cheek. Sam took me downstairs to basement where I
changed into my boy clothes, and then headed off home.
Comments
brinne hi
ok now what happend?good but to short,
[email protected]
mr charlles r purcell
verry good story i wood love to see a lot more of this all i can say is wow verry good thanks for shareing
Hello Brianne
Is this the first chapter in a series ? It will be interesting to see where you go with this story if so.
May Your Light Forever Shine
May Your Light Forever Shine
Please Please Please
Tell us you are going to continue with this.
Melanie
Fun Story
Enjoyed it...
Bri-Anne hallo
Well. you have made an interesting start, but it can't just stop there. There is so much to develop here. What will Brian's sister say? How will his Mother take it? How will relations with Sam and his carer develop?
Infinities of possible outcomes are hanging there in the air, waiting for you to write them down. A pretty good start IMHO and I think everyone will agree you should please continue.
Briar
Briar
Brianne - more
This is a faction story.
The events are based on my journal entries for the time but have been re-written into a story format.
Although it is not a serial, there will be more.