Debbie’s Embarrassing Day

by TB · December 9, 2022

Debbie’s Embarrassing Day – By David2505

Usual Disclaimers:

This is an adult story, intended only for those of legal age with an open mind and a sense of humor. It involves sexual situations and haircutting. If this is not your cup of tea, please read no further. It is a work of fiction. Any resemblance of characters to people you know and love is a figment of your own overactive imagination. Enjoy.

I appreciate your feedback. Please send comments to David2505@aol.com

It was time to come clean about it. Debbie and I had been having great sex for a couple of weeks, but she didn’t know what I was thinking the whole time. Every time I ran my fingers through the thick brown hair that fell in waves to her breast, I imagined cutting it all off. I heard the sound of the scissors crunching through it, saw how it would pile softly on the floor. I hadn’t said anything, because I didn’t want to scare her off. But tonight was the night. I was going to admit my fetish.

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I was lucky that Debbie seemed to enjoy how I constantly played with her hair, but I feared how she would react when she learned why I enjoyed it. I was particularly generous with my affections in bed that night, and we finally collapsed in exhaustion, her head on my chest, and her hair draped across me. I slowly stroked her hair and searched for the words to express myself. “Do you have any weird fantasies, any little kinks that really turn you on?” I asked, expecting “No” for an answer. I was surprised.

Debbie paused and took a deep breath before speaking. “I don’t know how to explain it exactly,” she began, speaking quickly. “I was in this sorority in college. One day, as part of pledging, they made us dress in kind of sleazy outfits, really short skirts and high heels, and go on a scavenger hunt downtown. We had to ask all kinds of embarrassing questions at various stores and stuff. For some reason, I got real excited. I wasn’t in control of the situation, and I was a little embarrassed, and a little humiliated, but mostly I was aroused. I don’t know what it was- the loss of control, or feeling so exposed the way we were dressed, or the embarrassment of the questions, the minor humiliations. I was really into it. I’ve always wished I could do it again, only, you know, more sensually, like with a lover.”

She blurted all this out, almost in one breath. When she stopped and looked at me, her face was red, with an embarrassed-little-kid expression. I realized she had just confessed something that she had hidden as carefully as I hid my hair fetish. Then, without another word, she started making love to me again. Passionately. I tried to digest what she had said (difficult under the circumstances), and decided to put off telling her about my fetish for a while.

When we had finished making love again, I thought for a bit, and finally figured out a way to make us both happy. “Would you like me to take you out and make you embarrass yourself in public, like you did back then?” I asked. “Yes!” Debbie exclaimed. “How about tomorrow?” I felt her tense up for a few moments, while she contemplated what I had said. Then she relaxed: “OK.”

The next morning, we agreed on a code word Debbie could use to stop the action if it got out of control. Then I sent her home with instructions. She was to be back in an hour, wearing clothes that she wouldn’t mind ruining (or losing, although she didn’t know this). She was to be showered and nicely made up, but was not allowed any jewelry.

When Debbie came back, I told her to take her car key off her keychain and some cash, ATM card and driver’s license out of her wallet. The wallet and keychain were to stay in the house, and I checked that her pockets were empty. We drove to Woolworth’s, and went directly into the toy department. I picked out a gaudy, bright pink plastic “play purse” for her, the kind you would buy for a three year old girl. She paid for it, and I told her to put her keys, license, ATM card and money into her new purse.

Next we went to the bank, and she took money out of the ATM. I explained that since this was her fantasy, she would have to pay for everything today. Debbie agreed. I then sent her inside the bank, with instructions to get change. She had over $150 on her, and I told her to get $20 in pennies, $40 in nickels, $60 in dimes and the rest in quarters. When she came out, I checked the rolls of coins, and made sure that she didn’t have any paper money left. I broke open some of the rolls of coins, and stuffed as much as would fit into her new purse. It was pretty heavy. “Now we’re ready to go shopping! Aren’t you excited about paying for everything with the money in your new purse, sweetie?”

Once we were back in the car, she asked if I was really going to make her buy stuff with all that change. “Do you want to stop our game?” “NO!” “Great, let’s go.” I gave her directions to a lingerie/adult toy store in a poor part of town. “We’re going to start at your feet and work up, OK?”

When we arrived at the store, I told Debbie to buy some spiked heel shoes, and that I would watch, but not help her in the store. She walked in and explained to the clerk what she needed. The clerk saw me watching, and saw the pink purse and smiled a little, then helped her pick out a pair of wildly spiked heels. I knew we would have to limit our walking, because they couldn’t be very comfortable, but I nodded my agreement. I watched from a few feet away as she wobbled over to the register to pay for them. She had to dump most of the purse out onto the counter, and slowly counted out enough to pay for her shoes. The store clerk was trying not to laugh, but a few chuckles came out, and Debbie turned bright red. As we were leaving I told her to give the clerk her old shoes to throw away.

In the car, I refilled her purse with more of the coins, and then we headed for a super-discount department store. I had her try on the shortest skirt in the store, and a cotton tube top. Once she had on a combo that fit her well, I told her to give me her underwear. Her eyes went wide for a moment, then she wiggled out of her undies, and handed them to me. “Great, leave your clothes in the dressing room, and go pay for your new outfit!.”

She looked at what she was wearing, and then looked at me. I smiled and shrugged. There was no way she would be able to show the woman at the register the tag on that short skirt without exposing herself. She turned red again and headed for the checkout.

I watched the ritual of her paying for her purchase. The clerk here didn’t have the awareness of the people in the other store, and stared at her like she was nuts as she tried to let the clerk see the tags on the skirt without seeing too much else. It was impossible. Then when she started piling up all the change, the clerk lost it, muttering about the crazies that keep coming into the store.

When we got back into the car, as I removed the tags from her new clothes, she was all over me, kissing me and stroking me and begging me to go home so we could make love. She was aroused to the point of distraction. I smiled. “We haven’t finished yet.” I gave her directions to the fanciest shopping mall in town, in a very upscale area. She looked down at what she was wearing, and turned to me with wide eyes. “Please, look at how I’m dressed…” she whimpered, but since I didn’t hear the code word, I refused to listen. “Do you need me to punish you for misbehaving?” The whimpering stopped, and she shook her head no. “Good. To the mall, then.”

Since I knew what was happening next, I wanted to go slow and enjoy the anticipation. We walked slowly around the mall. I kept looking at how she was dressed, and how her hair fell over her bare shoulders. She still had no idea about my hair fetish. I leaned over as we walked and whispered in her ear. “Are you embarrassed walking around like this, all exposed in your short skirt with nothing underneath?” She nodded. “Do you like it?” She nodded again, faster. “I’m not through exposing you yet.” She bit her lip. “And if you don’t behave, I’m going to punish you.” She replied, very quietly: “I’d like that.”

As we approached the cutlery store, I stopped her. “Do exactly what I say, but do not say a word, no matter what, OK?” She nodded her agreement. I told her to smile, and we walked into the store. There was an attractive young girl behind the counter, and we walked slowly around looking at the knives, until we finally came to the barber’s shears. I asked to see a pair with 3″ blades. I picked them up and examined them, opening and closing them slowly. This time I was the one excited to distraction. After playing with them for several moments, I reached over and took a small handful of Debbie’s hair, about 4″ long, and snipped it off. She gasped, but I stared at her, and she smiled at me, then at the clerk. “We’ll take them!” I announced. “My friend here will pay for them.” The clerk was dumbfounded as Debbie dumped the pile of change onto the counter and began to count it out. Debbie gave her a warm smile (and exact change!), but never said a word. When we left the store, I told her to take the scissors out of the bag, and hold them in her hand. I also gave her the lock of hair to hold, telling her to hold them both so everybody could see them. We continued walking through the mall, and I stared at Debbie’s beautiful hair with the 4″ clump missing on one side. As we walked through the food court, I abruptly stopped walking, and Debbie took another step or two before she realized, and turned to look at me. I spoke in a moderately loud voice. “You should have offered to buy me ice cream! I think I’ll have to punish you for being so thoughtless!” I held out my hand, and she stared at it. “The SCISSORS!” I finally said, and she meekly handed them to me. I snipped off nearly 8″ this time, before handing back to her the scissors and the newly shorn lock of hair. People were staring at us, as we walked to the ice cream counter.

After our snack, I quietly asked Debbie if she wanted to go home and make love now. She nodded furiously. I instructed her that while she made love to me, she would have to cut her own hair, so it was all one length again. She agreed, and we headed back to her place.

She did as I asked, cutting her hair slowly as moved on top of me, and gently stroking me with each lock of hair that she cut off. When we were done making love, she had hair that just brushed her shoulders, cut bluntly all the way around. It was cut quite evenly given the conditions, and I didn’t think anyone would give it a second look.

A short while later, as I made her put on her new outfit again, she commented about how she enjoyed feeling the ends of her freshly cut hair moving against her shoulders, and how much she liked her new haircut. Then we went back out. We got into the car, and she asked where we were going. I told her to find a barbershop. She looked at me sideways, and started to drive. After driving around for a bit, we found a shop. I gave her a paper bag. “Go into the shop alone, and sit down in one of the waiting chairs. I’ll come in a few minutes after you, so the barber doesn’t know we are together. When it is your turn, tell the barber to give you a brush cut, about 1/2″ long, using the clippers. Also, you want to save all the hair.” I pointed to the bag in her hand. “As soon as you’ve told him what you want and he has started cutting, I want you to start touching yourself. If you can’t orgasm before he’s finished giving you your haircut, I want you to fake it. Loudly, like in ‘When Harry met Sally.’ Do you understand?” Debbie smiled at me as she opened the door to get out. “I don’t think I’m the only one in this car who has a secret little kink, am I?”

When I walked into the barbershop, she was sitting directly facing the barber’s chair. She turned to me and slowly ran her fingers through her shoulder-length hair, while rather suggestively licking her lips. She then smiled as my erection grew obvious. I sat down next to her, since it was pretty obvious that we knew each other. The barber finished with his customer and looked at us, not quite sure who his customer was. Debbie got out of her chair and climbed into the red leather barber’s chair. She ran her fingers through her hair again, then shook her head wildly, sending her hair flying about her. The barber asked what he could do for her. “Clip it all off!” she exclaimed, “Leave me about half an inch. But, please, do it very, very slowly. I want to savor the moment, if you know what I mean. And I’d like you to put all the hair that you cut off in my lap as you cut it, so I can save it.” She gave the barber, who was slowly shaking his head, a winning smile. “I guess the customer is always right,” he muttered. “But sometimes I wonder.”

He did as she asked, slowly clipping her hair. She did as I asked, obviously touching herself under the cape. As her hands moved, I watched the growing pile of hair in her lap being tossed around. The orgasm was fake, but quite impressive anyway. I’m not sure the barber, not knowing Debbie as I do, could tell that it wasn’t real. By this point he was pretty amused anyway. When he finished, he gathered as much hair as was still in her lap into the bag for her, and after Debbie got up, she swept up the remaining pile off of the floor. I didn’t want to put the poor barber through the small change routine, so I paid him myself, with a generous tip. Debbie and I went home, with me spending the whole trip running my hands all over her freshly shorn head, while she struggled to concentrate on her driving.

When we got home, she said the code word, and announced that she was taking control for the remainder of the day. She did, and I enjoyed it. She even let me keep the hair!