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My First Time 'Helping' a Couple
Party Friend Fun
Making Each Other's Fantasies Come True
It Started in a Hot Little Club
My Wife took her Panties off in the restaurant
My Wife Discussed Sleeping with Other Men
Her Cheating and Open Relationship
Lee is Gone
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Sissy training
10/07/2017
When I first met Barry, I was attracted to his amazingly gorgeous butt. I had noticed him standing in line at Starbucks in a pair of jeans that he
was poured into. It wasn't just me either. The girl directly in front of me was looking at her phone and glancing at Barry's butt intermittently. I
have to admit, watching his ass made me think of spanking him. Anywho...

I waited until he was walking past me and looked up to smile. It was then
that I noticed that he had an amazing smile and was more good looking than
I had initially imagined. I smiled at him and gave a little wink. He
smiled back. After I got my coffee, I walked towards his table and saw him
glance up to see me. So, I stopped and introduced myself. We made small
talk and eventually he gave me his number. We were hanging out all the
time, just after a few weeks. Barry had a very playful spirit. We did not
shy away from flirting, which explained why he was purposely wearing the
tightest jeans ever made. I felt confident that his playfulness concealed
a part of his personality that needed to emerge...the kinkster hidden
within Barry.

In order to test out whether he had some kink to him, I set up a test. The
test was that I had invited him over to my place for a little role play.
When he came into my apartment, I just handed him a cheerleading uniform to
put on. He gave me a puzzled look. I gave him a "I mean business" look.
He gave a little eye roll and started walking towards my bedroom to change.
I knew then that it was a GO. I gave him about 60 seconds and barged into
my bedroom, catching Barry by surprise and in the state of undress. He
stood motionless in only a purple thong and blushed slightly. "Damn baby,
you look good", I said. He smiled and continued to put on the cheerleading
uniform. "And why exactly do you want me to be your cheerleader?", he
asked.

"Oh, I think you know why", I replied.

He just looked puzzled and continued dressing. When he got the top and
short skirt on, he just stood there with his hands on his hips. He was so
adorable and I noticed that his legs were clean shaven.

"Perfect", I declared, "now, let's go."

"Go? Go where?", he asked.

"To the mall, of course, we have some panty shopping to do", I answered.



Barry's mouth dropped open and he blushed.

"Wha...um, panties...I don't....", he stammered.

"Yes, panties, thong panties is what we are getting and what you will
wear", I clarified.

Barry's mouth dropped open again and he slowly nodded yes. "But, I...", he
started.

"You'll be fine, you're the damn cheerleader, let's go", I asserted.



On the drive to the mall, I could tell he was a little uncertain. Barry
finally said,

"I feel a little embarrassed, I mean, I...um, well, this is embarrassing."

"Barry baby, get used to it, you are so damn adorable, so sexy when you are
embarrassed", I said.



Upon our arrival at the mall, we parked and started walking in. I could
see Barry pulling on his skirt as if he could make it longer. But it was
no use, the skirt was designed to be very short and very short it would
stay. We walked through the mall, gaining some looks as we went because
Barry was dressed as an adorable cheerleader. I could see him blushing and
biting the corner of his lower lip in embarrassment. We stopped in front
of Victoria's Secret. Barry was looking around to see who was watching
him.

"Remember Barry baby, you ARE the cheerleader", I stated.

He nodded and looked into VS, probably gauging who he could see in there.
We walked in and approached an attractive college age girl. She saw us
approaching and smiled at Barry being a cheerleader. We stopped in front
of her.

"Is there anything I can help you find?", she asked with a big
smile...almost giggling.

"Tell her Barry what you need", I directed.

"Thong panties", Barry said in a quiet voice, as he rolled his eyes and
blushed.

"Oh really? Thong panties? For you?", giggled the salesgirl.

"Yes", Barry replied with more blushing and another eye roll.

The salesgirl giggled again and then said, "follow me, we have some very
cute thongs to choose from."



When we arrived at a section of wall covered in a variety of panties, the
salesgirl grabbed a black thong and said, "how about these, classic black."
The salesgirl held the thong up in front of Barry. She still had this huge
smile on her face as if she could bust out laughing any second.

"Oh, he will need several different pair, he will be wearing panties
everyday", I reported.

Barry looked at me shocked and then looked back at the salesgirl and
started to bite the corner of his lower lip again. We could easily tell
that he was embarrassed.

"He is, after all, my adorable little cheerleader", I added.

"I can see that", the salesgirl giggled.

"So let's be sure to get a variety, but definitely several pink panties in
there", I instructed.

"Oh, we have some very pretty pink ones", she replied as she gathered
several thongs.

"Barry...tell her that you are the pretty pink panty princess", I
instructed.

Barry blushed and said, "I am the pretty pink panty princess."

"Very cute", the salesgirl said as she continued to assist Barry in panty
selections. Barry and the salesgirl carried 20 pair of thong panties to
the register for purchase.

The other salsgirl there was laughing and said, "why is he dressed like a
cheerleader?"

"He is not dressed like a cheerleader," I clarified, "he is a cheerleader."
"Isn't that right Barry?", I asked.

"Yes it is", he said starting to giggle. Barry blushed again and both
salesgirls began laughing. Barry blushed even brighter red, put his hands
on his hips, pursed his lips, scrunched his nose up and glared at them. At
this, they laughed even harder. Barry rolled his eyes and said, "uuggghhh,
this is so embarrassing."

The salesgirl rang up the sale and said, "enjoy those pretty pink panties
under that cheerleading skirt."

Barry glared at her and blushed.

"Barry, tell them that when we get home that your pretty pink panties will
receive a powerfully proper paddling", I asserted.

Barry looked at me and his mouth dropped open.

The salesgirls began snickering.

"Tell them Barry", I demanded.

Barry responded, "my pretty pink panties will receive a powerfully proper
paddling."

At this, he giggled, blushed and rolled his eyes. We then left the store
and walked towards the exit. Before we reached the exit, I took the VS
bags from Barry and instructed him to do a cheer for me.

Barry thrust his hands on his hips and said, "you have to be kidding."

"Does it look like I am kidding?", I stated as I gave him a look. "You've
already doubled the number of paddlings you will receive, the longer you
delay, the more paddlings you add", I informed. At this, Barry immediately
launched into a cheer.



"Ready, and, I'm your little rah-rah, and I do what you have said, I am so
embarrassed and my face is so red, yes I'm your little rah-rah and in my
place I've been put, and when we get home you're gonna paddle my butt. I'm
your little rah-rah and I'm naughty as can be, and when we get home you're
gonna take me across your knee."



It was so adorable.

On the way back home, we stopped at the grocery store and I took Barry in.
We got a lot of looks from people because Barry was the cheerleader. At
the store, we went to the bakery and purchased a double-layer chocolate
cake. Well, actually Barry did. When we walked up to the bakery counter,
there was an attractive girl working there.

"May I help you?", she inquired.

"Yes", I stated, "this cheerleader would like to order that chocolate
cake."

The girl looked at Barry and he smiled a flirty smile.

"Why are you dressed like a cheerleader?", the girl asked.

"Because I am a cheerleader", he stated.

"Okaaaayyy", she responded, "who are you a cheerleader for?"

"I could be your cheerleader", Barry answered.

The girl smiled and and looked his uniform up and down.

"Cute", she said.

At that Barry raised his arms in the air like he was flexing his muscles
and began wiggling his hips back and forth and loudly stated, "RAH! RAH!
RAH! YEAH FOR THE BAKERY GIRL! GOOOOOOOOOO BAKERY GIRL!"

The girl laughed and blushed and Barry joined her laughing and blushing.

"Wow, I've never had my very own cheerleader", she said.

Barry smiled and winked at her.

"Hmmm, you are so delicious", she giggled.



I think Barry thought the cake was for some kind of celebration. When we
arrived back at my apartment, my friend Sara and her boyfriend Brandon were
waiting for us. Barry was embarrassed that they saw him as a cheerleader
because he knows Sara. Inside my apartment, I took Barry across my knee
and flipped his little cheerleading skirt up and started spanking him with
my ping pong paddle. When I was half-way finished with the 100 firm swats
he had coming, Brandon surprised Barry by suddenly standing in front of him
nude. Brandon's erect penis was directly in Barry's face.

"You know what you need to do Barry", I warned.

Barry immediately responded by taking Brandon's penis into his mouth and
performing a blowjob. Based upon Brandon's response, I would assume that
Barry is quite good at giving blowjobs. Just as I was finishing Barry's
panty pounding, Brandon was filing Barry's mouth full of his creamy
essence. Barry swallowed it all and stood up rubbing his sore warm butt.

Barry was then lead outside and instructed to do another cheer. He, of
course, complied.



"Ready, And, I'm your little rah-rah, two, three, four, thanks for the
spanking, my butt is so sore, I'm your little rah-rah, my world you did
rock, by paddling my panties and making me suck cock"



After Barry finished his flirty little cheer,

I took the chocolate cake and shoved it into Barry's face with a SPLAT! I
could tell that it surprised Barry because it knocked him back on his butt
with a THUD! Barry just sat there in the ground...his hands on his hips
and his mouth wide open in surprised embarrassment. Barry was thoroughly
embarrassed. However, this is just the beginning for my little cheerleader
Barry.
Poster: Brittany





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