Terrys Date Night final chapter
- 3 years ago
- 17
- 0
Terrys Date Night free porn video
Terrys date night
By Lucille
Chapter One
Terry Wagner didn't know what to think as he sat down in front of his
mother as she told him the news. Was she mad? Did she flip out finally?
What was going on? He just stared at her and said, "What?"
She stared back at him. "You heard what I said. Don't get mad at me. You
were the one that asked me for help and I helped you. You could not ask a
girl out yourself so you asked me to. I did exactly what you asked. The
one I found will only go out with you if you go as a girl. Your sister
and I make you a girl for her, tonight. So let's get started will we?"
He refused to budge and said, "No way. I am not doing that. When I asked
you to help. I didn't think I would be dating a freak that wanted me to
be her girl. I will find my own girl, thank you."
His mother shook her head, "It is too late to back out now. She will be
here tonight. And she expects you as a girl. You have had years to do it
on your own and never even got up the nerve to even speak to a girl on
your own. You start shaking and make an idiot of yourself. I tried to
find you a normal girl but, normal girls aren't attracted to guys like
you. I just got laughs. I found you a girl and now it's out of your
hands. She agreed to come meet you if you go with her as a girl. I agreed
to her terms to give you away. Now you must comply, or I will spank you.
"
"What, you're crazy. There's no way I am letting you dress me like a
girl. I am leaving. "The boy stood up to leave and was suddenly blocked
by his mother and sister. They tackled him and forced him down to the
floor. His older sister held him as his mother got a brush. She pulled
his pants down and started spanking him as he screamed.
After five hits on his bare ass with the brush, his sister got a better
idea and said, "Mother I think he needs some more persuasion. Try using
the bristles of the brush and rub them on the head of his penis. Do that
for a few minutes and see if he is more willing. And little brother,
Jethro is outside if you manage to get away. "
He really started screaming as his own mother took his cock in her hand
and held it as she rubbed the bristles of the brush on him. After a few
long minutes of him withering and screaming in agony, he was more subdued
and willing. Terry said, "Fine Il do this just once then I am done."
He didn't know what was going on tonight. He asked his mother to help him
find a girl with the understanding that he could back out of the deal.
But something was going on and they seemed willing to force him to date
this girl. She wanted him to dress like a girl too. Why was his family
doing this too him?
He stood in the center of the room now slowly removing his clothes in
front of his giggling older sister and domineering mother. "Your
underwear too son. Then it will be time to shave your whole body. Not
that there's much to shave but your underarms your crotch and balls. And
legs and that will be about it. "
That didn't take very long at all. His sister lathered him up with
shaving gel and took her time shaving his whole body from his legs to his
crotch chest and arms. Within fifteen minutes he was totally shaved
clean.
"Now that is finished we can start making you sexy. Sit in the new chair
we got and if you have a problem with it, Jethro will come in and hold
you down."
"I hate that man, Mom. He tormented me all though high school didn't you
see how he beat me up almost every day after school?"
She giggled, "Yes for the first year then somehow you two seemed to get
along better, and he took you places."
A single tear went down the boy's face, "That's only because I agreed to
meet him for special favors if you know what I mean. He enjoyed that
better than beating me. I didn't get bruised ribs or black eyes. But now
I wish I didn't make that agreement. I think that might had been worse
than the bruises. It was sick." And maybe that's why he had such trouble
with girls now.
His sister laughed. "I guessed as much but you did it, so don't cry about
the agreement you made with Jethro now. Let's start painting your nails."
He sat in the styling chair humiliated as they made him hold his feet and
fingertips in a warm bowl of water for about 30 minutes. Then they did
some things to them to hold the skin back. His sister called it said she
was pushing his cuticles and she filed the edges before she finally got
around to paining his fingernails and toenails pink. Then she put toe
rings on his feet and bright purple stars and stones in his fingernails.
After that, his sister and mother got tweezers and told him to hold still
as the did his eyebrows. They went to work on his face with the tweezers.
The two were working like mad and the tweezing was ferocious. They were
like machines working and thinning his eyebrows. It went on for fifteen
minutes. She looked at his face and smiled, "You look pretty my son. "
Now lets start on your face. His mother began with a thick foundation.
Lathering up his face then she did his eyebrows in a purple shade of
eyeshadow. She painted his lips pink and put in false eyelashes. A final
touch of red blush made him look totally enticing to anyone.
Then his sister washed his hair out and brushed it straight. But added a
hint of pink tips to his already blonde hair.
Looking in the mirror he cried out, "I look like a girl now! Why does a
girl want you to do this to me?"
She just smiled and said, "She thought you would be very pretty. Shes
kind of domineering and wants a feminine boy to dress up each day."
"Oh great," he said.
"Sara," His mother said, "Do you have the panties picked out, and
everything else he needs for his date tonight."
Sara smiled and said, "Yep of course. I had to go online but I got a sexy
pair of crotchless panties I got from Fredrick of Hollywood. I got a
waist clincher, garter belt nylons and a neat bra that has its own gel in
the cups to make him look like he has natural breasts."
She looked at her daughter unsure for a second or so. Worried that she
was enjoying this all too much. "You know he's not yours. He will be this
woman's after tonight."
She smirked. "Of course. Let's get started. Brother put on the panties."
He was shaking as he grabbed the thin silk material and slid them up his
legs. "This is so humiliating, Sara."
She smirked some more and said, "Hey you did it for Jethro so this is
nothing new."
He frowned and said, "Why is there an opening in the back?"
"Because silly. Their crotchless panties. Their made for women who want
to have fun without taking their panties off. You might thank me you have
them tonight. Now, can you put on a garter belt?"
"Yes," he hissed in anger. "I've done it before. Let me do this." He took
the flimsy thing and wrapped it around his hips and hooked it.
His sister snickered. "You have done this before having you. Now the
waist clincher. She wants you to have a female form"
Both women had to work hard for that one. His mother pulled and twisted
it together as his sister laced it. He was begging for them to stop as it
crushed his waist into a feminine shape.
His sister finished the final lacing and admired her work. Then she
watched as she forced her brother to put on his own bra and clipping the
back like nothing. "Brother you know a lot more about women clothes and
most boys should."
He glared over at Jethro and said, "I had a lot of practice. Thanks
Jethro." As he carefully slid up his nylons making sure not to yank them
to hard. Then hooked them to the garters and finally sliding his feet
into the heels provided by his sister.
Standing in front of his mother and sister wearing red bra and panties,
nylons and garters were humiliating enough. Then she brought over a tight
black pencil miniskirt he was forced to slide into and zip. And a sexy
top that showed way too much chest and his midsection.
She smiled and said, "It's about time for your date to show up.
He sat there waiting for a few minutes. Waiting for something and
dreading it. He looked at himself in the full length mirror and cried
out, "Mom I look like a bimbo!"
There wasn't much terry could do about it now so she said, "That's
allright. That's what he wanted his date to look like."
This was a set up, Terry thought. "HE, what are you talking about, Mom."
"You are dating a man tonight."
As If on Q there was a knock on the door. His sister said, "Go answer
it." He went over and opened the door. To his horror, there was a young
man that seemed to be in his mid to late 20s. Powerful broad shoulders,
hard face. He smiled at the feminized boy and said, "Hello sweetie. Are
you ready for our first date?"
He cringed back and cried out, "Oh My God, what is this Mother."
She pushed her son back into the chair and said, "Now listen up. We went
to every girl your age in town. None would even consider dating you. They
either laughed or sneered that you were too weak. One girl even said you
looked to gay and suggested finding a man for you. This man wants you and
we said yes. You will go out with him. You will do what he tells you. And
he will bring you back after the date. We agreed no all-nighters. That
can wait. So go along.
Then she looked at his date. "And Toby, remember. Only oral for tonight.
No anal understand."
He struggled against the older mans grip as he lead him out the door
screaming, "Noooo Help me mother."
He heard his mother whisper, "No anal, unless he asks for it."
The man smiled and said, "Terry, will ask for it."
They drove around town for a few hours with Toby's hand continuously
caressing his nyloned thighs. Terry was uncomfortable and kept cringing
but he remembered what his mother told him so he didn't fight back. He
just accepted it all. Knowing there wasn't much he could do about it. He
could resist but he was a short slim and almost effeminate looking
eighteen year old boy. The boy beside him was a powerful broad shouldered
muscular man in his mid 20s. Terry knew he didn't stand a chance
resisting this man.
They pulled into a movie theater and walked in. Terry felt humiliated
beyond all belief as he walked in holding the mans hand. People looked
over but didn't think anything. Everyone assumed terry was this mans
girlfriend. He looked exactly like a girl holding her boyfriends hand.
Terry felt even more emasculated and smaller. Toby bought them both
tickets and went in and sat beside each other. Terry felt himself being
pulled uncomfortably close to this older boy but he knew not to make a
scene here. It was natural for a girl to sit in close touching her boy in
a theater. He silently endured the boys squeezing, caresses and even
kisses though the two and a half hour long show. He even let the older
boy pinch his butt cheek a few times. They went back to his car and terry
asked, "That was fun now are we going back home?"
Toby shook his head, "No your mother said to have by five in the morning.
We can spend a few more hours at my place." He flashed a smile and Terry
cringed. What were they going to do now?
Toby looked over and said, "For tonight, you will be Anne."
Terry felt a tear roll down his cheek. Why had his mother set him up on a
date with a man?
Makenna
- 25.05.2022
- 15
- 0
Terrys First Time
- 4 years ago
- 20
- 0
Not Quite a White Knight Book 2Chapter 8 Date Knight
- 3 years ago
- 19
- 0
