Billys Introduction to a Sex filled Weekend
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Billy's Dilemma -Chapter 2 free porn video
Billy's Dilemma - Chapter 2
At Billy's house that night, things were different.
Billy offered to help his mom June clean up the kitchen after the family
supper. Billy's dad Ralph and Billy's younger brother Jack looked at
Billy in disbelief - for offering to help in the kitchen.
Why would a guy help clean up the kitchen? That was women's work. Ralph
and Jack got up and went into the den to watch whatever game was on TV.
Billy's mom June was delighted that one of her sons offered to help in
the "kitchen" - "a woman's domain."
With an alpha male for a husband and two boys, June was often at her wit
ends with the men in her family to be more civil to women.
"Billy, it is very nice of you to help your mom. You can be such a good
dear at times" (not like the other two - she thought to herself).
"Oh, it's nothing mom. I figured you could use the help."
Billy cleared off the table. June washed the dishes and pans while Billy
wiped them all dry. When the last dish was dried, Billy turned to his
mom.
"Mom, I ah, eh, eh - I need to ask you something."
"sure dear - what is it?"
Billy had a look of desperation on his face. His mom could feel his
uncomfortableness and pain.
She put her arm around him and whispered in his ear.
"Honey, what is it? What is troubling you?"
Looking down at the floor, "Mom, eh, eh - may I borrow a pair of
your...your panties?"
Panties! A pair of MY panties - raced through June's mind
Trying to show support for her son who was truly reluctant to ask his
mother for something so personal, so girlie, she quickly offered:
"Yes, Billy, of course you can borrow a pair of my panties. And,
anything else you that would like to borrow is fine, just fine."
"Ok, honey."
She held him tight. He was so relieved that he almost cried in his frail
emotional state.
"Mom, mom, thank you, but no, I don't need anything else (right now)."
"Ok, honey, then let's go upstairs and get you a pair of (my) panties."
Billy followed his mom. His face was red as he walked by the den, but
June's face was full of happiness and with a big smile. Oh, she thought -
if only she had a daughter - this would be so much fun - borrowing
clothes and all, even panties, especially first panties.
In his parent's bedroom, Billy stood close by his mom as she opened a
drawer full of panties.
"Billy, this is where I keep all of my panties that I wear every day. In
this drawer is where I keep my bras and camisoles. In this drawer I keep
my socks. And in this drawer I keep my" naughty's - things like garter
belts, seemed stocking and such."
"Mom, I don't need a tour. I just need a pair of your panties."
"Oh, yes, I forget. I guess I got carried away. I just wanted to show you
where thing is in case you wanted to borrow something - sometime."
I haven't been able to show or share any of my things with anyone,
especially with two sons she mused. This is so fun for me.
"Well, do you have something in mind"?
"Nothing really, I don't know."
"Well, what color or type of pantie do you like? I have full briefs,
bikinis, boy shorts, and even thongs!
"Mom, just a regular pair."
"Well ok. How about this?"
She opened her "naughty" drawer and pulled out from the back a pair of
panties which were quite feminine. They were a white sheer lace, with
little purple and yellow flowers.
'this is one my favorites."
Billy, in desperation, quickly agreed.
"Yes, they are a very pretty pair of panties mom. I will take them.
Thanks."
"Do you want anything else, honey"?
"No, mom this is all I need. Thanks again."
"Well, if you want any more panties or anything else, just let me know.
You can borrow and wear any of my things you know. OK, honey."
Billy, now quite embarrassed, left with his panties stuff deep in his
pocket.
He went into his room and quickly put them under his mattress and then
went downstairs into the den.
Well that was not as bad as I thought. Gee, my mom thinks I want to wear
her clothes, girl clothes. What is she thinking?
Maybe now I can satisfy Rachel and be done with this ordeal once and for
all.
June meanwhile, could not get over her oldest son asking her for a pair
of panties - her panties.
What is going on with Billy, she thought?
Must be some kind of joke or contest or bet.
Hmmm, but she was also hopeful that maybe he really wanted to try on a
pair of panties. It was not that unusual for a young teen boy to try on
his mothers or sisters clothes -was it?
Just then she went into the back of her closet and took off the hanger
the matching baby doll top to the panties.
"Oh, I love this little baby doll top. It is so feminine and delicate. I
never wear it any more.
I wonder if Billy would like it."
With a little gleam in her eye, she took the cute little baby doll and
went into Billy's room where she decided to put her baby doll under
Billy's pillow.
He will find it tonight and then he can decide whether he wanted to
explore her other 'things."
She saw no harm in this.
In fact, she was quite excited and hopeful that Billy's would like, no
love, to wear her things - girl things.
Later that night things started to happen in two of the bedrooms - the
boy's bedrooms.
Jack, being 12, had stolen some cigarettes and had finally decided to try
smoking one of them. He lit the cigarette. Since it was cold outside he
did not open a widow but instead pulled a blanket over his head.
Billy, meanwhile, had found the baby doll top his mother had put under
his pillow.
Billy lay in bed for some time before he decided what to do.
"What the heck. I wonder what it would be like to try on the baby doll
outfit. No one would ever know."
He was alone and it was dark in his room, so he felt safe.
Bill got out of bed and retrieved both the top and the panties. He pulled
the panties up his legs first and then put on the top.
Immediately, he felt different, a feeling he never known before. It was
weird - yet exciting. He did not know what he was feeling, but he knew he
like it - too much, that is.
He now wanted to see what he look like wearing the baby doll so he turn
on the light and went over to his mirror. OMG I look like a Girl - a teen
aged girl. Yikes! He liked what he saw and felt.
He quickly turned off the light and jumped back into bed where he was
safe again under his covers. He felt naughty wearing the baby doll with
no one knowing. Though he was dressed like a young teen girl ready for
bed, he had one difference - a big difference. He had a major hard-on
erection!
Billy had started to masturbate early that year and he quickly found
himself stoking his rock hard penis through the soft, silky panties.
While touching himself, he felt like he was a girl wearing the baby doll
and showing off. Billy thought about how he would walk around and have
others see him, so cute and so feminine, just like a girl.
It did not take long - nor could he have done anything about it - before
he convulsed into a big spasm and exploded into his mom's favorite baby
doll panties!
"OMG - what have I done"?
It was the biggest and most explosive climax of his young sexual life
Yet instead of getting up and cleaning up right away, Billy lay in his
bed with a glow, and reflected on what just happened.
He thought about what his mother would think if she knew he had worn the
baby doll and panties. She did leave them in my room. Did she know that
he would try them on? Did she know that he would jack off while wearing
them?
And what would his dad think? His dad would kill Billy for sure.
And Billy's brother Jack? He would harass Billy until Billy was dead, and
that was for sure.
Jack meanwhile across the hall in his bedroom, started to cough loudly so
he took the covers off of his head. A cloud of smoke quickly rose to the
ceiling where the smoke detector alarm went off in full blast mode
June woke up immediately and pushed Ralph out of the bed.
"Ralph, Ralph, get up, get up. The house is on fire. We need to get the
boys out."
Ralph half asleep, stumbled out into the hallway where he noticed the
smoke coming from Jack's open bedroom door. Jack was already standing
in the hallway looking extremely nervous.
"It's only a cigarette." Jack murmured, "No fire."
"I am going to kill that kid" Ralph yelled as he started to approach
Jack.
Billy also stumbled out into the hallway and was half asleep and did not
pick up on what was happening. He also forgot how he was dressed!
Billy of course was wearing a complete baby doll outfit - panties and the
top!
A 14 year old boy in the cutest, most feminine baby doll outfit one could
imagine was now standing in front of his entire family. Not only was
Billy's dress a shock to everyone, but on the front of his baby doll
panties was the largest, cum soaked mess imaginable, and it was starting
to drip down Billy's left leg. There was no mistake as to what had
happened with Billy while he was wearing his mothers" pretty baby doll.
"OMG" June mumbled as she covered her mouth with her hand.
Being a caring mother she quickly put herself between her "gurlie"
dressed son and his father who had now turn toward Billy mid-stream.
Ralph was mad as hell with Jack, but with Billy, Ralph was stunned for a
second before regaining his anger back.
"BILLY, what the hell is going on? Why are you wearing that shit? Where
did you get it from? Are you some type of fag"?
Billy started to cry.
June reached first Billy and shielded him with her body from her husband.
"Ralph, Ralph, - you take care of Jack and I will deal with Billy."
Billy was crying with convulsions now. He was almost out of control. He
wanted to die. This was the most embarrassing thing on earth that could
have happen to him. This was a 1,000,000 times worse than what Rachel had
threatened him and Alan with.
He did want to die- right then - right there.
Ralph took Jack by the ear and led him back into Jack's bedroom. Within
seconds, Jack was wailing as his dad spanked him hard.
Billy could hear also hear his dad yelling at Jack.
Billy thought his turn was next. He hated when his dad yelled at him.
But then he felt his mom's arms around him leading him back into his
bedroom and into his bathroom.
His mom bent down and took off Billy's cum soaked panties for him. He was
so embarrassed at his mother having to deal with his sperm soaked
panties.
What would she think of him? He felt so small and childish standing next
to her. She was helping him like he was little, a little girl.
She quickly rinsed out the panties and hung them up to dry on his shower
bar.
Oh, now I have a pair of panties drying in my bathroom - ugh.
Then she wash his cum laden penis and left leg with a warn wash cloth.
"Billy, tomorrow I will show you how to get that stain out of your
panties. OK?"
"Now, stand right here and I will be back in a second."
When the bathroom door opened again, Billy thought it would be his dad,
but no, it was his mom, with a fresh pair of pale yellow panties - for
him.
Yikes! She is going to keep me in panties?
"Here, put these on, darling."
She bent down and help pull up the clean pair of panties.
They were a "bikini" style panty and they felt very secure on Billy. He
liked that.
"Yes, honey, these fit you quite well, I guess we are the almost the same
size. Isn't that great"?
My mom always tried to find something nice and good in everything
"Billy, with these panties you should tuck your little fellow up
underneath. OK"
I quickly did as requested.
"See, how much better you look now. Just like me," she said with the
biggest smile.
She then pulled up her night gown up to show me her panties.
OMG! My own mother is now showing me how her panties fit her.
"See, we both now have cute little "mounds" and no ugly bulges!"
This is too much.
She then led Billy over to his bed and tucked him in for the night.
I guess she expected me to sleep in my baby doll and panties.
As long as my dad did not come in, that was ok by me as I felt quite
natural and good with them on me -strange.
"Honey, don't worry about anything that happened today. I will speak
with your father. Everything will be ok. Trust me."
With that, she gave me a kiss on my check, turned off my light and shut
my bedroom door.
Back in my parent's bedroom, my dad was still wound up and turned to my
mom.
"What the hell is going on with Billy? I could not believe my eyes -
that a 14 year boy would be dressed like that. What is going on with him?
Where did he get that 'outfit'?"
"Billy asked me today if he could borrow a pair of my panties. I think
young boys sometimes want to experiment and try on their mother's or
sister's things. I was glad he asked me and did not just take anything.
He is a very nice boy. And besides, I was the one who gave him the top.
He did not ask for it, nor was I sure if he would even try it on."
"Well he did try them on and you saw what he did with them. What a fag."
"Ralph, don't judge him like that. He may be just going thru a phase."
"Well, I never when thru a 'phase'."
"Ralph, let's go just to bed now and we can talk about this in the
morning. OK"?
Yes - what a night June thought - some bad, and yet some good, some very
good- she smiled.
In the morning over coffee, June brought up the subject again of Billy
experimenting with girl's clothes
"Ralph, as I mentioned last night, I have been reading that some boys go
thru a phase by experimenting with their mother's or sister's clothes. In
fact, research shows that if you go overboard, almost like it is a
punishment with the idea of being like a girl, he will eventually reject
this type of behavior - forever. It becomes a type of punishment, not a
pleasure. I think they call it - "petticoat discipline."
June was outright lying to her husband, but she wanted to have a daughter
so bad, even it f it was for only a brief period of time.
"I think we should do this with Billy - that is, expose & and maybe even
forced him to try girly things. He will then eventually reject all of
it. We have to look at this long term. We do want Billie to grow up and
be happy and secure."
"June, I don't know. I don't want to see Billy running around here like
some type of fairy."
"He will not be some type of fairy. I can assure you of that. He will be
a proper young lady. And he will not embarrass any of us. Ralph - you
need to trust me on this."
"June, I still don't know. What is Jack going to think about his brother
and all of this girly stuff?"
"I will talk with Jack. I am sure he will help his brother with this
challenge."
"Well, I don't care then what you do, I guess. I am so disgusted with
Billy right now. He pause, "Ok, if you need my support, just let me
know."
"I will need your support."
"Don't worry. Billy will do as you say. I will SEE to that."
Geraldine
- 03.01.2023
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