Kinky Confessions: Humiliation Dating

When I first met Barry, I was attracted to his gorgeous butt. I had noticed him standing in line at Starbucks in a pair of jeans that he was poured into. I have to admit, watching his ass made me think of spanking him.

I waited until he was walking past me and looked up to smile. He had an amazing smile and was more good looking than I had initially thought. I smiled at him and gave a little wink. He smiled back. We made small talk and eventually he gave me his number.  

We were soon hanging out all the time. Barry had a very playful spirit. I felt confident that his playfulness concealed a part of his personality that needed to emerge… the kinkster hidden within.

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In order to test out whether he had some kink to him, I invited him over to my place for a little role play. When he came into my apartment, I just handed him a cheerleader uniform to put on. He gave me a puzzled look, and I gave him the “I mean business” look.” He walked to my bedroom to change.  

I barged in, catching Barry by surprise. He stood motionless in only a thong and blushed. “Damn baby, you look good,” I said.

He smiled and continued to put on the cheerleader 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 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 again.  “What… um, panties… I don’t…” he stammered.  “Yes, thong panties is what we’re getting and what you will wear,” I clarified.  

Barry slowly nodded yes.  “But, I…” he started.  

“You’ll be fine, you’re the damn cheerleader, let’s go,” I asserted.

On the drive, I could tell he was uncertain. Barry finally said, “I feel a little embarrassed, I mean…”

“Barry baby, get used to it, you’re so damn adorable, so sexy when you’re embarrassed.”

Upon our arrival at the mall, we parked and started walking in. I could see Barry pulling on his skirt as if to 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, attracting some curious looks. I could see him 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 smiled at Barry being a cheerleader.  

“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. 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.” She still had this huge smile on her face.  

“Oh, he will need several different pairs. He will be wearing panties every day,” I reported. “He is, after all, my adorable little cheerleader. Let’s be sure to get a variety, but definitely several pink panties in there.”  

“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 twenty pairs of thong panties to the register for purchase. The other salesgirl was laughing and said, “Why is he dressed like a cheerleader?”   

“He’s not dressed like a cheerleader,” I clarified, “he is a cheerleader. Isn’t that right, Barry?”

“Yes it is,” he said, starting to giggle. Barry blushed again, and both salesgirls began laughing. He 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, tell them that when we get home, your pretty pink panties will receive a powerfully proper paddling,” I asserted.  

Barry looked at me and his mouth dropped open, and the salesgirls began snickering.  

“Tell them Barry,” I demanded.  

Barry responded, “My pretty pink panties will receive a proper paddling.”  At this, he giggled, blushed and rolled his eyes. We left the store.  

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’m kidding?” I stated as I gave him the look. “You’ve already doubled the number of paddlings you will receive. The longer you delay, the more paddlings you will receive,” I informed him.  

At this, Barry launched into a cheer. “I’m your little rah-rah, and I do what you say. I am so embarrassed and my face is so red. Yes, I’m your little rah-rah, and I’ve been put in. When we get home, you’re gonna paddle my butt. I’m your little rah-rah, and I’m naughty as can be. When we get home you’re gonna take me cross your knee.”   

It was so adorable. His cheerleading routine definitely needed practice, so I made a point of making a few more stops before we headed home. That was just the beginning for my little cheerleader Barry.

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