Don was quite small the first time he put on his older
sister’s pink silk panties but he liked it. He was quite
upset the first time his sister and her girlfriend caught
him wearing these panties.
“What on earth are you wearing,” Jane said as she and
Judy walked into the room. They stood staring at Don
wearing nothing but pink panties.
“You’re not supposed to be here yet,” was all the young
Don could say but he knew he had been caught.
“Wait till I tell Mom,” Jane laughed.
“No, please you can’t tell Mom,” Don pleaded.
“Oh, you just wait,” Jane said as she and Judy giggled.
Don was both upset and embarrassed because the girls kept
looking at him. He finally came out of his daze and
pulled the sheet off the bed to cover himself.
“Oh, it’s too late to cover yourself. We have seen it
all,” Jane said. “I tell you what Don, if you’ll do what
I say I might consider keeping this our little secret. Is
that ok with you Judy?” Jane quizzed.
“Yeah, I don’t care,” Judy quickly replied.
“So what about it you little sissy boy?”
Don did not feel he had much choice.
“Ok, what do you want me to do?” he asked not really
wanting to know the answer.
“What do you think Judy? What should we have him do?”
Jane asked her friend.
“Why don’t we have a good look at him wearing the
panties?” she answered.
“Ok, that sounds like fun. Get rid of that sheet Don and
let’s take a look at you,” she commanded.
“No, I don’t want to,” he whimpered.
“Ok, Judy, let’s go down and wait for my mother,” she
said and they turned to leave.
“Wait, I’ll do it,” Don reluctantly said as he let the
sheet fall and just stood there in the pink panties. His
body was thin and there was little hair anywhere. He
watched as the girls inspected. As they did he felt
something stirring in him. He could see them looking
directly at his little dick and it began to swell.
“Oh no,” Don thought to himself as his dick became hard
and poked out of the panties. It was clear the girls were
staring directly at the little budge in the panties.
“Look at that Judy. My little sissy brother is getting
hard on.” They laughed as Judy pointed at his little
“I want to see it,” Judy said.
Don was beside himself. His sister had seen him naked
many times but never like this and never with a hard on.
Don’s face was red with embarrassment as he stood before
the two girls. However, there was also something exciting
about it. Don did not know much about sex but knew it
felt good to rub his little dick. He also was surprised
that he liked the girls looking at him and his little
dick became even more erect.
“I don’t think so,” Don said.
“Oh yes we are going to have a little show,” Jane said.
“Push those panties aside you little sissy right now,”
she said in a stern tone.
What could he do? He pushed one side of the panties from
his crotch. As they slid over his dick it plopped out
from one side and the girls giggled. Don was embarrassed
but he noticed it also felt quite nice standing naked in
front of his sister.
“It’s not very big,” Judy said.
Don’s dick was about 4 inches when erect and now it was
its full 4 inches.
“No, it’s not,” Jane answered. “But it is large for a
little sissy,” she added.
“Turn around and let’s see that little sissy butt,” Judy
Don turned around and they even had him bend over. They
examined his asshole and his little scotum sack as it
hung between his legs.
“Wow, that is weird. I would hate to be a boy and have
all that hanging between my legs,” Judy said.
“Yeah, I couldn’t stand it,” Jane replied.
They had walked up close to Don as he stood bent over
with his ass in the air and his legs spread for his
sister and her friend’s inspection. He could feel the
cool air on his tender asshole. He could also feel his
dick wobble as it began to hurt a little because it was
“I want to touch it,” Judy said.
“Ok, go ahead,” Jane said giving her permission without
asking Don what he thought.
Judy tentatively reached over and pressed down on his
dick. Don’s dick went down from the pressure of her push
and then plopped by up again. The girls noticed Don’s
intake of breath.
“I think you like this,” his sister said.
“No, I hate it,” Don said but was not very convincing.
Jane took her turn and pushed his dick down. As she let
go it sprang back up. The girls laughed.
“I have an idea,” Jane said. “Come over here Don.”
Don walked across the room and flinched when he saw what
Jane had in mind. She was holding a small vacuum cleaner
with a hose on it.
“What are you going to do with that?” Don asked afraid of
“Oh, you’ll find out,” she said as she winked at Judy.
“No, I don’t think so,” Don said as he back away.
Judy was standing behind him and grabbed his arms.
Jane turned on the vacuum and stuck the open hose on
Don’s dick. Whooossee. The hose sucked up Don’s dick all
the way and then began to pull on his skin. Jane pulled
the hose back just enough so it was not against his skin
but still sucking the air past his dick.
“Ohhh, what are you doing Jane?” Don gasped but was
feeling something new. His dick had never felt quite like
“I am giving you a blow job.” Jane and Judy laughed but
both girls were noticing a bit of wetness between their
legs. They glanced at one another and each recognized the
gleam in the other’s eye.
Don did not know what he was feeling. He did not know
what a blow job was but he knew his dick had never felt
like this. There was a strange pressure building and
suddenly his dick began to swell and he felt his balls
“Oh, something is happening to me,” he said. Don had
never cum and did not know what was happening as he near
his first real sexual experience.
Jane and Judy noticed what was happening. “It’s going to
blow,” Judy said and they both laughed.
Judy was watching both Don’s dick and his facial
expression and could see the shocked rapture as he near
his first ejaculation. She also felt other things and
fought the urge to let her hand go between her legs.
“Ahhhhhhhhhhhh,” Don screamed as his little dick erupted
for the first time. The vacuum suck up all his cum into
the little clear cylinder where it whirl around making a
mess of the little vacuum cleaner.
It did not take long for Don’s spasms to subside and Jane
mercifully turned off the vacuum.
Don slumped on the floor.
“What happened?” he asked. “Did you hurt me?”
“No, of course not. You just had your first cum. Did you
like it?” Judy said.
“I don’t know. It was weird but it felt good too,” Don
said still somewhat dazed by the experience.
Judy looked at Jane and they could see they had both
enjoyed their new little playmate.
“Come on Don. We are going to play some more,” Jane told
“I’m tired of playing,” Don complained.
“You want me to have a little talk with Mom,” Jane
“No, you said you wouldn’t.”
“Ok, then we are going to have some more fun. You enjoyed
that. You will enjoy this too,” Jane said. “Come on into
my room. Mom won’t be home for two or three hours.”
Don reluctantly followed the two girls. He was still
wearing the pink panties.
Neither Judy nor Jane had any real sexual experience
other than a few orgasms from masturbation. They knew the
mechanics of sex and like to talk about boys. They had
even watched a few porno tapes one of the girls had.
Today though their fun was going to be a little
different. They were going to play dress up with Jane’s
sissy little brother.
“Let’s see what would look good on you,” Jane said
looking into her closet. “I have some old clothes that I
have outgrown that might just fit you Don.”
Don did not know if he liked the sound of this. On the
other hand he felt a bit of excitement growing thinking
about dressing up in girl’s clothing. He tried to hide
the fact that his little dick was beginning to grow
again. However, wearing nothing but silk pink panties
left little to the imagination.
“Ooooh, look Jane. He little willie is growing again,”
Judy pointed out to her friend.
“You really like this don’t you Donny,” Jane said. She
walked over to Don. Don took a step backward but that did
not stop Jane from pulling the panties aside and freeing
his little hard dick.
“If we are going to dress you like a girl we can’t have
your willie sticking out like that,” Jane said. “What
should we do? Get the vacuum cleaner again.”
“No, don’t do that,” Don said. It felt good at the time
but he did not like the idea of his dick stuck in a
vacuum cleaner hose.
“Why don’t you do like that movie Judy?” Jane suggested.
“What do you mean?” Judy asked.
“Why don’t you suck his little cock and make it cum. The
lady in the movie loved it.”
Judy thought about this for a moment. She could still
feel the wet spot between her legs and her little clit
was slightly swollen enough to rub against her pussy lips
in a delightful sort of way. Judy would never have
thought of sucking a dick but now that the Don’s dick
presented itself to her it sounded like a good idea.
Jane could not believe it when Judy walked over to Don.
Don could not believe it either.
“What are going to do Judy?” Don asked.
“You just stand there and be quiet,” Judy said as she
knelt down before Don. She looked very closely at Don’s
Jane was watching Judy very closely not believing what
she was seeing.
Judy reaches forward and licked the tip of Don’s dick.
Don tried to take a step backward but Judy pulled him
forward. She reached around and grabbed his butt cheeks
and held them as she took his dick into her mouth. She
felt the head rub between her lips.
“Ahhhhh, that feels great,” Don said thinking this was a
Judy could not believe the taste of this little cock and
what it was doing to her. She felt her pussy becoming wet
and her clit was shouting to be rubbed. As Judy continued
suckling his dick she allowed one hand to slip down
between her legs and rub her pussy.
Jane continued to watch this and did not miss this fact.
She was watching her best friend suck off her brother
while she masturbated herself. Jane could not believe how
this was affecting her and soon her hand was between her
legs as she watched the show.
It did not take long for Don to begin to moan. It’s
happening again. His first two cums came within minutes
of one another.
“Ahhhhhh,” he said as he buckled his hips into Judy’s
face. He shot a load that hit the back of her throat.
Judy could do nothing but swallow and gag but this did
not stop her attention being placed to her little pussy.
“Ohhhhhhh,” Judy managed to say as the last bit of cum
hit her in the face and her clit responded to her touch.
She slumped down onto the floor with her legs spread as
she finished herself off.
“Mmmmmmm,” could be heard from the other side of the room
as Jane also finished herself off.
It was a great afternoon for all present.
*** Chapter 2 ***
It was almost a week later before Judy and Jane found
“You girls don’t get into anything while I’m gone. I’ll
be back in about two hours,” Jane’s mother said as she
prepared to leave.
“Okay Mom,” Jane said as she watched her mother walk out
As Jane’s Mom drove off Jane looked at Judy, “Let’s go
play dress up with Don.”
“Sound like a great idea,” Judy said and smiled.
The girls found Don sitting at his computer playing a
“Don, we want to play a little game,” Judy said as they
entered his room.
“What kind of game?” Don asked. He had mixed feelings
about this. Their previous game had been fun and had felt
really good but it also was frightening. Don would never
admit this to the girls but he felt really strange after
“We want to dress you up?” Jane said.
“Dress me up. What do you mean?”
“We know how you like to wear panties. We will make you
look like a girl. You will love it,” his sister said.
Don’s mixed emotions again resurfaced. One part of him
was extremely excited about this possibility. To actually
wear girl’s clothing was very thrilling. Even letting his
sister and her friend dress him was very appealing.
However, there was another part that was afraid of the
very thing that was so exciting.
“Come on Don. Let’s go into my room,” Jane said as the
girl took him by the hand and lead him away from the
When they were in Jane’s room the girls began to unbutton
“What are you doing?” he asked in alarm.
“We are taking off your clothes silly,” Judy snickered.
“I don’t know if I want to do this,” Don said as his
shirt came off.
“You know you had great fun. And you don’t want me
telling mother about your panties do you?” Jane said as
she pulled down his pants. As his pants fell Judy grabbed
is underwear and soon he was standing very naked. It did
not take long for his little dick to stand up straight.
“Look at that, his dick is already hard,” Jane said as
the girls inspected her brother’s body.
“Yeah, is your dick always hard?” Judy asked. Judy
remembered his dick tasted quite good.
“No, it is not always hard,” Don answered.
“I guess maybe we need to get it down again,” Jane said
and winked at Judy. Jane knew Judy loved her first oral
sex experience. They had talked about it quite a lot.
“Yes, I think that would be a good idea,” Judy said and
kneeled down in front of Don.
“What are you doing?” Don did not like how these girls
were controlling him.
“Not much,” Jane said as she watched Judy begin licking
the tip of her brother’s dick.
“Maybe I don’t want this,” Don said but he was lying. He
loved Judy’s lips on his dick. And he loved it when she
took his entire cock inside her mouth and sucked on it.
The feelings intensify and Don could see his sister
watching as he began to hunch against Judy’s face. He was
Judy was also enjoying it. Only a week ago she had her
first experience of sucking Don off and she loved it. She
loved the smell and the taste of his dick. She also could
not wait to have another load of cum in her mouth.
“This time I want a little taste,” Jane said as she
watched and knew her brother was getting close to cumming
in Judy’s mouth.
“Uggggghhhhh,” Don said as he first large load erupted
striking the back of Judy’s mouth. She gulped and
swallowed most of it.
Jane quickly knelt down and was the next load she took
over the sucking. She got a good shot and tasted the
strange taste as she let herself swallow. As she pulled
her brother’s dick from her face the next shot landed on
her nose. She giggled but could feel a nice warmth
building between her legs.
Jane looked over at Judy who had been watching closely.
Judy reached over and licked the cum off Jane’s nose.
They then kissed sharing the taste of Don between
themselves. They had never kissed like this allowing
tongues to touch and explore the insides of their mouth.
Judy could not believe it when she felt Jane’s hand begin
to rub between her legs. Judy quickly reciprocated and
they fell to the floor in a passionate embrace.
Don sat back on the bed with his now limp dick beginning
to gain new life as he watch the two girls on the floor.
They were rubbing each other’s crotches as their tongues
played with each other.
“Mmmmmm,” Judy said as she felt the first wave of her
first lesbian orgasm.
Her moaning and petting were enough to send Jane over the
“Ahhhhhhhh,” Jane cried as she entwined with her friend
in a strong orgasmic embrace.
Judy and Jane came together and wave after wave of
pleasure engulfed them as they lay on the bedroom floor.
“Damn,” Judy said as she finally came back to her senses.
They looked over at Don sitting naked on the bed and they
“We’re going to get you dressed up but now we don’t time.
Mom will be back shortly but on Saturday she is going to
visit her sister and will be gone all day. Don’t make any
plans for Saturday Don,” Jane said as Don put on his
*** Chapter 3 ***
Don was anticipating Saturday with both positive and
negative emotions. His playtime with his sisters was most
enjoyable but he did not know what they would do next.
“Jane, you and your brother are going to be okay today,”
Jane’s mother said as she prepared for work. “I don’t
like leaving you for the entire day but I have to work.”
“We will be fine Mom. Don’t worry so,” Jane said.
“Ok, I will be able sometime after 6:00 this evening.”
“Everything will be fine,” Jane replied as he mother
Jane had some good ideas of the fun she could have today
with her brother. Her friend Judy would be coming over
soon but Jane decided it was time for her brother to wake
“Don, get up,” Jane said as she pulled the covers off her
She noticed immediately he had a morning erection. As Don
began to awaken she reached down and opened his pajamas
bottoms and let his dick stick out.
“What are you doing?” Don asked as he felt his sister’s
hand grab his dick.
“Just playing a little,” Jane laughed. “Get up and take a
shower and then I will dress you up to show Judy.”
Don did not know if he liked this idea or not.
“Jane, I am finished with the shower,” Don said as he
walked down for some breakfast. He was wearing his shorts
“Those clothes will not do at all,” Jane said as she
handed him a bowl of cereal. “Eat your cereal and then we
dressed you proper.”
Don ate his cornflakes. He knew what Jane’s idea of
proper dress for him was. He also knew he liked the
“Come on up to my room,” Jan shouted from upstairs.
“Ok,” Don had finished and walked up to her room.
“Take off all those clothes,” Jan instructed.
Don complied now somewhat used to his sister seeing him
“Put these on first.” Jane handed him some pink panties.
As Don put the panties on he could feel his dick awaken.
“Make that thing go down,” Jane said as she noticed it
poking out of the panties.
“I can’t,” Don said.
“Yes you can. Take off those panties and pull on your
dick until you shoot off and then it will go down,” Judy
“I can’t do that right now in front of you.”
“Yes you can. I have seen you shoot off when Judy sucked
you. Now pull on it back and forth.”
Don did not feel comfortable with this idea but decided
it was best to comply. Jane could get him into a lot of
trouble and it was kind of exciting pulling on dick
especially with Jane watching him.
He began rubbing it back and forth and it felt good. Jane
watched him closely and then she reached down and began
to pull on it. Don liked this and soon could feel his
dick begin to swell. Jane cupped his balls in her other
hand and Don felt them begin to contract. It was about
time as the head of his dick swell and he soon felt the
rush. A large glob of cum squirted to the floor in front
of him as his dick began to erupt.
“Mmmmmm,” he said was the wonderful feeling engulfed him.
All too soon it ended.
“Now clean up that mess you made,” Jane said as she
reached down put some of the cum on her finger. She
remembered she had liked the weird taste the other day
after Judy had sucked him. She had also taken his cock
into her mouth and got a shot of cum.
“Wait a minute,” Jane said as she savored the taste of
“You lick it up.”
Don could not believe what he heard. “What?” he asked
“You lick up your own cum. Do it right now or I will tell
Mom about the panties.”
Don knew his sister would tell his Mom and his Mom would
believe her. So he knelt down and began to lick up his
own cum. The first taste was kind of bitter but not too
bad. He was able to get most of it up and by the time he
finished did not mind the taste at all.
“Did you like it?” Jane asked as she watched Don finish
licking his own cum off the floor.
“Not really,” Don lied. He was beginning to find being
humiliated quite a stimulating adventure.
“Put back on your panties. You dick is small enough now.”
Don put on the pink panties.
“Here let me help you with this,” Jane said as she held a
small training bra that just barely fit around Don’s
chest. “Yes, this will do nicely.” She put a small
crumpled up tissue in the cup of the bra given Don a
“Ok let’s see what we have here.” Jane looked through her
closet and found a white blouse and a small blue skirt.
“Put these on.”
Don put on the blouse and as he buttoned it up Jane
helped him with the skirt.
“Now for some pantyhose.”
Don put on the pantyhose and was almost all dressed.
“Come sit down here,” Jane motioned and prepared to add
some rogue to Don’s cheeks. She also applied some
lipstick and some eye shadow.
“Now what can we do about your hair?” Jane asked herself
“I know.” Jane went into her mother’s room and in the
closet found a blond wig.
“This will do nicely,” she told Don as she slipped it on
“Stand up and let’s have a look at you.”
Don could not believe what he was seeing. Looking at
himself in the mirror he looked like a girl. No one would
recognize him. He did not recognize himself.
There was knock on the door.
“That will be Judy. Wait until she sees you.” Jane went
to open the door.
“Judy come on in. I have something for you to see.”
They walked up the stairs. As Judy entered the room she
exclaimed, “Oh my God, is that Don? I can’t believe it.
“Yes that is my new little sister,” Jane said as they
stared at Don.
“He looks just like a girl. You could not tell the
difference. He could fool even his mother,” Judy said.
“You what I’ve thinking would be fun?” Jane asked Judy.
“Let’s take Don to the mall.”
“Wait a minute. I’m not going to the mall dressed like
this,” Don protested.
“It’ll be great fun Don. No one would ever recognize you.
It is lots of fun being a girl.”
“Yeah, you will love it,” Judy added.
The mall was only a few miles. They were getting to get
into Judy’s mother’s car but as they walked out of the
house Jane noticed a problem. Don’s dick was hard again
and poking out of the dress. It was just enough to be
“We’ll have to do something about that,” Jane told Judy
as they went back into the house.
“I’ll take care of that,” Judy said with a smile. She
knelt down in front of Don and pulled up his skirt. She
pushed his panties off his hard dick and took it into her
“You’re getting quite good at that,” Jane commented. “How
about me too?”
Jane knelt down and Judy gave her a go at Don’s dick.
Jane suckled it and licked the head.
Don was in heaven. “Mmmmmm,” he grunted as both girls
took turns sucking his dick.
Don’ balls again began to swell for the second time that
day and he felt the rush. Jane had Don’s dick in her
mouth and prepared herself for a blast of cum. It hit in
the back of her throat and she quickly passed Don’s cock
to Judy who took the rest of his cum. They did not even
get a drop on their clothing and did not mess up Don’s
“There that ought to take care of it for a while,” Jane
said as she licked her lips.
“But what will we do if it gets hard again?” Judy asked.
“I have an idea,” Jane said and went back to her room.
She came back with some hose.
“Pull up his dressed and pulled down his panties for a
moment,” Judy did as Jane asked.
Jane took the hose and managed to use it to hold Don’s
dick and balls between his legs.
“That hurts,” Don said.
“It will be okay. Just let me adjust it. There that is
fine,” Jane said. “Now if he gets hard his dick will not
They were now ready. They got into the car and took off.
Don was very nervous about this but also very excited.
However, his dick did not have anywhere to go.
They arrived at the mall and walked in the main entrance.
Don was nervous but felt very good in his little dress as
he walked along with his companions. They looked at
dresses and then even looked at fancy lace underwear.
“I have to go to the bathroom,” Judy said.
“Come on let’s go,” Jane replied.
“I can’t go in there,” Don complained.
“Sure you can, you are a girl.”
They walked into the main women’s restroom. Don had never
been in the women’s restroom. He went to stall and shut
the door. He managed to get his dick so he could pee and
then put it back into its hiding place. As he walked out
a middle-age lady was trying to adjust her bra.
“Could you help me?” she asked Don.
“Me,” he said in a girlish voice.
“Yes, hold my bra in front while I adjust it,” she
The girls came out to see Don holding a woman’s bra while
she pulled on the strap in the back. They giggled when
one of her rather large breast slipped out right in front
of Don’s face. He just looked around. The woman made her
adjustments and then slipped her boob back into the bra.
“Thanks you very much. You are a very nice girl for
helping me,” the lady commented as she got up to leave.
“You really had a bit of fun there didn’t you Don,” Jane
said after the lady had left.
“Gosh, she had the biggest boobs I have ever seen,” Don
“Yeah they were large,” Judy laughed.
“Let’s go find some older guy and have a bit of fun,”
Judy said with a twinkle in her eye.
“What do you mean?” Don asked.
“You’ll find out. It is lots of fun to tease older guys,”