Cindys First Threesome
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Cindy's New Girlfriend free porn video
CINDY'S NEW GIRLFRIEND
By Tammy Richards
SYNOPSIS, This is a sequel to 'Jack and Jill.' Cindy helps Jack explore
his feminine side.
Cindy Carter sat in her living room enjoying a cup of coffee as she
watched her neighbor Jack Williams clean her apartment. Jack looked very
sexy in his black satin maid's uniform and high-heeled shoes. Cindy
smiled as she thought about the past 24 hours. After accidentally
discovering Jack wearing this same uniform yesterday as she tried to
escape a confrontation with her old boyfriend, circumstances had
conspired to keep Jack dressed as Jill for the rest of the afternoon and
evening. While Cindy felt sorry for Jack's embarrassment and discomfort,
she also found herself tremendously turned on seeing him dressed in his
beautiful, feminine clothes.
The night ended spectacularly with the most powerful orgasm Cindy had
ever experienced. After their lovemaking, they had both fallen asleep in
Jill's bed. When Cindy woke up early this morning, her cunt was on fire
and her juices were flowing. She needed to do something about it. Rolling
over she looked at Jack sleeping peacefully in his pink babydoll nightie.
He had a fire hose hiding in his panties that would solve her problem.
She cuddled against him and began to rub his cock. She could feel it
stiffen as he moaned happily and opened his eyes. She kissed him and
said, "I'm horny."
"Me too," he replied as he slid his finger into her vagina and rubbed her
clit."
"Ooh, that feels good," she purred. "But I need the real thing this
morning." She pulled Jack's panties down, rolled on top of him and
impaled herself on his shaft. She came almost immediately. As the waves
of pleasure washed over her, she began to gyrate her hips. Slowly at
first and then faster and faster, she rode Jack like a bucking bronco.
She felt Jack come, shooting his seed deep inside her. A moment later her
body was convulsed with a second more powerful orgasm. She collapsed on
top of Jack and kissed him passionately. "My God, Jill! That was
awesome."
"It certainly was a great way to get the day started."
When their pulse rate slowed Cindy rolled off him and snuggled next to
him. "What would you like to do today?"
"The first thing I'm going to do is clean your apartment."
"You don't need to do that. I was just joking last night."
"I want to do it to thank you for the most wonderful night of my life."
"I appreciate it. When you're done, why don't we go to the mall and do a
little shopping."
"As Jack or Jill?"
"As Jill. I'd really like to spend another day with my new girlfriend."
Jack frowned. "I'm not sure, Cindy. I'm still very nervous about going
out dressed as Jill. Besides all of my shoes have very high heels. I
think I would look out of place walking around the mall in them."
"Don't worry. There's a Payless shoe store just a few blocks away. While
you're cleaning my apartment, I'll go and get you some low-heeled shoes.
You'll look just like any other woman at the mall, except you'll be
prettier. What do you say?"
"If you really want to do it, I'm willing to try."
After getting showered and dressed, Jack had gone to work cleaning
Cindy's apartment and she had gone to the store where she purchased him a
pair of sandals and a pair of pumps, both with 1-inch heels. Now as she
sat waiting for Jack to finish the cleaning she reflected on her feelings
about him. After her experiences with that asshole Ed, she had decided
that she wanted nothing more to do with macho men. She wanted a man who
was considerate, sensitive and loving. In short she wanted a man who was
in touch with his feminine side. Looking at her neighbor in his maid's
uniform and high heels, it was clear that Jack was such as man. He was
also a fantastic lover. She decided that she wanted to spend more time
with both Jack and Jill. She also wanted to help Jack develop and enjoy
his feminine side.
Jack came and stood in front of her. "I think I've got everything done,
Cindy. Does it look OK?"
"It looks fine. You've done a great job." She handed him the shoeboxes.
"I bought you some shoes. Why don't you try them on and make sure they
fit."
Jack sat down and tried on each pair. "They fit fine. Thanks very much."
He paused. "Are you sure you want to do this? It would be embarrassing
for both of us if somebody read me as a man."
"Don't worry. Nobody will pay any attention to us. Come on. I'll help you
pick out something nice to wear." They returned to Jack's apartment.
While Jack removed his maid's uniform, Cindy looked through his closet
and pulled out a knee-length black A-line skirt. "Do you have a sweater
that you could wear with this?"
Jack pointed to the dresser. "They're in the third drawer down."
Cindy opened the drawer and selected a white cashmere sweater. "This
skirt and sweater, perhaps with a gold necklace will look very nice. I'd
suggest that you wear your new sandals without pantyhose."
When Jack was dressed he stood in front of the mirror and posed. "How do
I look?"
Cindy examined him critically. "We need to paint your toenails. Take off
your shoes and sit down at your vanity. I'll help you." After painting
his toenails red to match his fingernails, Jack slipped his sandals back
on. Cindy smiled at him. "You look very feminine in that outfit Jill. You
definitely won't have any trouble passing as a woman."
"I hope you're right."
They headed for the mall. When they got there, Cindy opened her door to
get out but Jack continued to sit in his seat, staring straight ahead.
She patted his hand. "Are you ready, Jill? We need to get in there before
all of the good bargains are gone?"
Jack took a deep breath and smiled. "I guess I'm as ready as I'll ever
be. Just stay close to me."
As they strolled through the mall Jack began to relax. Nobody seemed to
be paying them any attention except for the occasional appreciate glance
from some of the men walking around. They walked into Victoria's Secret
and checked out the lingerie. Jack whispered in Cindy's ear, "This is the
first time I've been able to openly shop for myself in here." Jack bought
himself a very sexy white satin camisole and panty set. From there they
visited numerous clothing and shoe stores where they tried on various
things. The smile on Jack's face told Cindy everything she needed to
know. Jack was having a wonderful time out in public as Jill.
For the next several hours they went through most of the women's clothing
and shoe stores in the mall. Jack had a wonderful time trying on dresses,
skirts and shoes just like all of the other women in the mall. He ended
up purchasing a very pretty tan knit dress and a pair of brown high-
heeled pumps.
It was late in the afternoon when they passed the Food Court. Cindy said,
"Why don't we get something to drink and relax for a little while?" They
each got a diet soda and sat at one of the tables sipping their drinks
and chatting. Suddenly a look of fear came over Jack's face. "What's
wrong?" asked Cindy.
"I just spotted your friends Jennifer and Marsha, and they're heading
this way."
They arrived at the table just as Cindy turned around to look. "Hi Cindy.
Hi Jill," said Marsha. "We thought it was you sitting here." They pulled
up a couple of empty chairs and sat down. "So tell us, how was your
evening with Kevin and Darryl?"
"It was fantastic. We had a wonderful dinner at Antonio's and then they
took us to a nightclub for drinks and dancing. We really had a nice time,
didn't we Jill?"
Jill smiled. "We certainly did. Kevin and Darryl are great guys."
"Did they happen to take you to Bunny's Club?" asked Jennifer.
"Yes they did. How did you know about that?"
"Kevin was telling me about it one day over lunch." She turned to Marsha
and explained, "Bunny's Club is a transvestite night club. Most of the
women customers are actually men in drag."
"Wow, that sounds wild! So tell us what it was like. Were they all really
ugly?"
Cindy replied, "Some of them were pretty obvious but others were very
attractive and feminine. If you saw them walking down the street you'd
never suspect they were men. No matter what they looked like they were
all having a good time. It was one of the liveliest nightclubs I've ever
been in."
Jennifer laughed. "It sounds interesting. We need to get Kevin to take us
there."
Cindy glanced at Jack. It was clear that the conversation was making him
very nervous. It was time to change the subject. "What are you two doing
at the mall?"
Marsha said, "We're on our way to Bloomingdales. They're having a big
sale so we thought we'd see if we could find some bargains. Would you
like to join us?"
Cindy knew it was time to get Jack home before something bad happened.
"We'd love to but we've been shopping all afternoon and we were just
getting ready to leave. I think we'll take a rain check this time."
Jack piped up. "I agree. My feet are beginning to get a little tired."
Jennifer and Marsha stood up. "That's fine. We'll talk to you at work
tomorrow. It was nice to see you again, Jill."
Cindy could see Jack visibly relax as the girls walked away. "Thank you
for getting rid of them, Cindy. I was scared to death that they were
going to figure out who I really was."
"It's clear that they don't suspect a thing. While it was a nerve-
wracking experience, it should give you more confidence in your ability
to pass in public."
Jack laughed weakly. "It certainly turned out to be a strange
conversation with me sitting right here."
"I agree. They would be shocked if they knew the truth." Cindy paused for
a moment. "You know, we didn't have a chance to have our intimate
girlfriend's dinner last night. How would you like to do it tonight? I
really want to see what you look like in your red evening gown."
That brought a smile to Jack's face. "I can't wait to show you. Let's go
home and get changed."
When they got back to their apartment building, Cindy said, "I'll just
get dressed in my apartment for tonight. What time would you like me to
come over?"
"Why don't you come about 7,00? I should be ready by then."
"I can't wait," she said and gave Jack a quick kiss. She went into her
apartment and put away her afternoon's purchases. Then she opened her
closet to pick out something to wear for the evening. She wanted to make
this a very special evening for both Jill and herself. She knew that Jill
would look beautiful in her gown and she wanted to look just as nice. She
finally decided on her black beaded evening gown. It had spaghetti straps
and a long straight skirt with a thigh-high front slit. It was the
sexiest dress she owned. Having made her decision, Cindy headed for the
bathroom to start getting ready for the evening.
It was 6,55 when Cindy checked herself for the last time in her full-
length mirror. She had spent more time than normal on her hair and make-
up to insure that it was just right. Her dress showed off her small waist
and ample cleavage. Under the dress she wore nothing but a pair of
panties, a garter belt and her shear stockings. On her feet was a pair of
high-heeled sandals. She was wearing a diamond heart pendant around her
neck that nestled invitingly near her breasts. She was also wearing her
diamond tennis bracelet and her diamond stud earrings. She smiled at
herself in the mirror. She was ready for her evening with Jill.
Cindy took a bottle of wine out of the refrigerator, walked across the
hall and knocked on Jack's door. Jack opened the door to let her in and
then closed and locked it. They turned to face each other and in unison
said, "Wow, you look beautiful." Then they both burst out laughing.
Cindy continued, "That really is a spectacular dress, Jill. Turn around
and let me see." Jack held his arms out and pirouetted. The dress fit him
perfectly, molding to every curve in his body. It was a red satin
strapless gown with a long straight skirt and a back walking slit. Cindy
could see the top of his breastforms and a little bit of cleavage but
there was no hint of the seams. They looked very natural. She marveled at
how gracefully he moved on his red stiletto-heeled pumps. He was no
longer blonde but had put on a beautiful brunette wig that cascaded
around his face in soft waves. "It looks like that dress was made for
you."
Jack laughed. "I doubt that the dress designer thought it would be worn
by someone like me." Cindy handed him the bottle of wine. "I've mixed up
a batch of cosmopolitans. Would you like one?" he asked.
"That sounds good. Thank you." While Jack went to get the drinks, Cindy
looked around the apartment. The lights were low and soft music played on
the stereo. The table was set for an intimate candlelit dinner. There was
a vase of fresh flowers on the coffee table in front of the couch. Jack
returned from the kitchen and handed her a drink. "Thanks," she said as
she took a sip. "It tastes great. The apartment looks lovely tonight,
Jill."
They sat down together on the couch. For the next half hour they sipped
their drinks and talked like two girlfriends. Cindy found it a surreal
experience. Jack looked and sounded like a beautiful woman. Yet Cindy
knew that underneath the gown was a virile male with all the necessary
male equipment.
Jack had prepared a delicious dinner. They ate slowly, savoring the food
and continuing to talk together. Then they lingered over coffee and
dessert. After dinner, they cleaned up the dishes and then returned to
the living room.
They stood together with their arms around each other and kissed,
tenderly at first and then with more passion. Their mouths opened and
their tongues explored each other. Cindy reached behind Jack and unzipped
his dress. Jack reciprocated. They stepped apart and allowed their
dresses to drop to the floor. Jack was wearing a tightly laced corset,
his panty girdle and shear stockings. His eyes opened wide as he starred
at Cindy's beautiful body. Taking her hand he led her to the couch.
Instead of sitting down next to her, he knelt in front of her and pulled
her panties down her legs. She slid forward on the couch and spread her
legs apart to give Jack access to her pussy. He buried his face in her
love nest as she draped her legs over his shoulders. Before long she was
writhing and moaning in ecstasy as one orgasm after another exploded
inside her. When she could take no more, she gently pulled his head away
from her cunt and said, "It's your turn, Jill. Let me help you out of
your clothes.
Jack laughed. "Why waste time?" He lay back on the carpet and spread his
legs. Reaching into the split crotch of his panty girdle, he pulled his
cock free. It pointed straight up in the air like a flagpole. Cindy
smiled as she knelt between his legs and kissed the head. Then she slid
it deep into her mouth. Jack was in heaven. He could feel the pressure
building and then he shot his cum into her mouth. After swallowing some
of it, she crawled forward on top of Jack and kissed him passionately.
When their mouths opened Jack got a taste of his own juices.
They continued to kiss as Cindy worked to bring his limp penis back to
life. When it was again standing at attention, she slid down on it,
engulfing his manhood deep inside her vagina. They took their time making
love, wanting to stretch their enjoyment as long as possible. When they
eventually both came, they collapsed together in exhaustion.
They lay together on the floor for several minutes. Finally Jack smiled
at her and said, "It's been an incredible day but we probably need to get
cleaned up and ready to start a new workweek."
They went to their separate bathrooms to get ready for bed. When Jack
returned to the bedroom, all traces of Jill were gone. The wig and the
breastforms had been removed and put away. His face was clean and
scrubbed. He had removed his long fingernails and cleaned the polish off
his toes. The only hint of femininity that remained was his pink satin
pajamas. They cuddled together in bed and kissed.
Jack looked into her eyes and said, "It's been a wonderful weekend. Thank
you for accepting Jill and treating me like a girlfriend the past two
days."
Cindy replied, "I've really enjoyed getting to know Jill. Now I'm looking
forward to spending some time with Jack."
THE END
Hortense
- 08.02.2022
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