My Naked Walk Around The Park

My Naked Walk Around the Park

A successful businesswoman loses a dare

by G. Lawrence

Like many stories on Literotica, this story could have multiple categories. It could be BDSM because of the handcuffs. In my opinion, it is not Nonconsent/Reluctance as the dare is agreed to by all parties. So, I am going with my default category, Exhibitionist & Voyeur. Please note that none of the events in this story really happened. It's a fantasy. None of it is intended to be taken literally or practiced in real life. There is nudity but no sex. And a warning, as much as I like my usual breezy comedic escapade stories, this entry is more thoughtful. It's not for everyone. All characters in the story are 18 years or older.

* * * * * *

High-end real estate is a competitive field. Having been selling exclusive properties for four years, my girlfriends and I often bet on which clients would put a particular estate into their vast portfolios. My guessing was generally good but not perfect. Those who lost bets would have to give up a dare. And even more audacious, we were allowed to sell someone's dare to another party, a danger intended to keep us on our toes.

I confess to having been on a four-year winning streak and maybe became too boastful. My name is Anne Montgomery, and many thought I was one of the prettier sales executives, with a graceful figure, nice boobs, long golden-brown hair, and an insolent swagger in my deep blue eyes. At 27, I was younger than most of the veteran agents. I had shown the Bradhurst Association a wonderful mansion being offered for sale well below market value and was sure they would buy it, betting my best friend Linda that I'd close the deal. I was wrong. At the last minute, my chief competitor from another firm swooped in with a property the association liked better. I lost my bet. I could imagine Wanda Manning gloating after the many times I bested her.

Our weekends were always busy with open houses. Mondays were devoted to contracts. Tuesdays were about paperwork. The girls' night out was on Wednesdays. By then the hectic pace would quiet down. I met Linda, who was only three years older than me, at the Blue Duckling, our favorite watering hole just around the corner from the office. Three other women joined us: Sandra, Judy, and Candace. The first two were in their mid-30s, generally polite though often jealous. Candace had been my apprentice until her recent promotion.

"So, Wanda finally snookered you," Judy said, rubbing it in. Her green eyes weren't trying to hide her joy.

"Yes. Wanda had an unlisted property that she was holding back," I explained. "Mrs. Bradhurst fell in love with it and overruled her husband."

"And you lost your bet to Linda," Sandra eagerly mentioned, on the edge of her seat. Her glee was obvious.

"I did, though she hasn't told me what my dare is yet," I replied, looking at her.

"It's going to be a surprise. A big surprise," Linda said with a hesitant grin that had me uncomfortable.

"We can hardly wait," Candace happily smirked. Five years younger than I, she was still a rookie who I had tried to help, though I think she took my advice as criticism.

I noticed Wanda Manning enter, 45-years old, tall and immaculately groomed as always, with her supermodel features and elegant chocolate brown suit. I hoped she wouldn't notice us, but Linda waved her over.

"Congratulations," Linda said, standing up to give her a hug. "That was a colossal sale. Can we buy you a drink?"

"That's nice of you," she agreed. "Are you sure Annie is okay with me joining you? After I kicked her ass?"

"You didn't kick my ass," I protested. "You found the garden Mrs. Bradhurst always wanted and convinced their association to buy it for her."

"Do you think that was an accident?" Wanda said with a wink. "It's all about getting to know the client and serving their wants. Nothing in this business is more important than serving wants."

"Annie, you do tend to talk more than you listen," Linda cautioned, and not for the first time. "Being pretty will only get you so far."

"I've been doing okay," I replied, impatient with their smugness.

"Well, since you seem to have it all together, is this a good night for our dare?" Linda asked.

"We should talk about that privately," I answered.

"Fair enough," Linda agreed.

The group broke up just before eleven o'clock after plenty of drinks. Wanda had been on her best behavior, less obnoxious than usual. A longtime veteran agent, she could be overbearing. The other girls appeared in high spirits, which I didn't quite understand. Their sales had been suffering while mine had been soaring.

On the sidewalk, Linda pulled me aside. "Let's discuss the dare in the park," she said, leading me across the street. It was one of those mile-square parks, with basketball and tennis courts, a golf course, soccer fields, and an outdoor amphitheater. Tall trees along the meandering running trails made vast portions look like a forest. We stopped just inside the park entrance near a bench. It was nearly deserted this time of night on a weekday.

"I've been waiting for this for a long time," Linda said. "You're my best friend, and I love you, but sometimes even best friends need a wake-up call."

"What do you mean?" I asked.

"To go the distance in our business, and in life, sometimes humility is needed," she answered. "You've been having a problem with that. I want to help you."

"I still don't know what you mean. What help?"

"Is our dare on? Are you ready?"

"Yes, I'm ready," I agreed.

"That's good. Take off your clothes," Linda ordered.

"What? Here?" I protested.

"You had Judy take off her clothes."

"At a pool party, in your backyard. Not in public."

"It set a precedent. And you had Sandra streak the gym."

"Yes, that was funny," I remembered. "But again, the gym is private. People walk around nude all the time."

"I don't think Candace was amused when you switched locks on her gym locker," Linda pointed out.

"She still had her towel," I responded. "Am I getting a towel?"

"No, you are taking off your clothes. Now let's get this going."

A dare was a dare. I knew the rules and never welched, as Linda knew. I sat on the bench to remove my sneakers and socks. Linda put them in a duffel bag. It was a warm night, so I hadn't worn a sweater. My blouse went next, and then my slacks. I got up from the bench, only my bra and panties remained.

"Can I keep these?" I requested.

"No," she answered.

"At least let me carry them," I asked.

"Stop delaying. Put everything in the bag," Linda insisted. The bra and panties came off, turning my face red as I stood bare ass before her. I watched her zipper the bag shut and set it on the bench.

"Happy now?" I asked, holding my arms out.

"Not yet. It's time for the handcuffs," she revealed, dangling them in front of me.

"Handcuffs? No, no one ever said anything about handcuffs."

"It will make the game more exciting," Linda assured me. I turned around and felt her close the cuffs on my wrists behind my back. They were double locking. Where did she learn about double locking handcuffs? I was now totally exposed under the park's nightlights, unable to cover myself.

I had nothing to be ashamed of. 5'8, a hundred and thirty pounds, slim and graceful with nice breasts. I played golf, tennis, and swam in college, though I had fewer opportunities for sports these days. Any guy would want me if I had time for dating.

"Please, Linda, this is going too far," I said, beginning to whimper. "What are you going to do?"

"Me? I won't be doing anything to you, dear. You see, I sold your dare," Linda replied.

"Sold my dare? To who?"

"Here she comes now," Linda said, stepping aside. Oh, my God, it was Wanda! She sold my dare to Wanda Manning! The fucking bitch!

"Linda, don't do this. Please don't do this," I begged.

"It's already done. Don't you always say a deal is a deal?" Linda replied with a dismissive gesture.

Wanda stood before me with a victorious grin, seeing everything as I cringed. It was a nightmare come true, naked and helpless, bound to obey the woman who was my greatest rival. Her hungry hazel eyes roamed over me with pure joy.

"I must say, it doesn't get better than this," she concluded. I felt utterly humiliated. And betrayed. I stared at Linda in anguish, unable to tell what she was thinking. It seemed like she had something to say but couldn't. She handed the handcuff key to Wanda and started off.

"Linda, are you going back to your office?" Wanda asked.

"Yes, I need to lock up," Linda said. Wanda retrieved the duffel bag and gave it to her.

"Leave Annie's clothes on her desk," Wanda instructed. "She won't be needing them until tomorrow morning." Linda looked shocked to hear that Wanda was going to keep me naked all night, but she didn't object. Some best friend she was.

"Oh, one more thing," Wanda added, looking at me with a devil's grin. She opened the duffel bag and dropped the handcuff key inside. "We won't be needing this until tomorrow morning, either."

Linda took the bag with my clothes and ran away into the night. I think she was crying.

* * * * * *

Our walk began before midnight. The park was emptying out as people had work in the morning, though there were probably still a hundred spread out over the large area. It felt strange to feel the cement walkway beneath my bare feet. And sometimes grass. Pine needles could be a problem.

"First time naked outdoors?" Wanda inquired.

"No. In college I was naked on a beach in Spain, and another beach in France. Friends once stole my clothes while we were skinny dipping at Lake Carlson. It was hard getting them back. Even good people can be mean sometimes. This is my first time naked in a city, though."

"Well, you look wonderful. I hope we can make this a regular practice," she laughed. "Your tits are just the right size for that tight body. Nice and firm. And your butt is perfect. You must work out. The wax job is very clean. It leaves nothing to the imagination."

I didn't have much to say about that. I wasn't sure of Wanda's orientation and didn't want to encourage her, thinking of myself as straight. Most of the time. "What are your plans, if I may ask?"

"My plans? We are going to enjoy this wonderful park together. And if I'm right about a few things, it's going to be very educational."

We began our journey along a winding path through tall trees. I wasn't sure how I'd react if someone saw me, and didn't have to wait long for the answer.

"My goodness, a naked slave and her mistress," a gray-haired old man said, out walking his labrador retriever. "A beauty, too. Did you buy her? Or did you catch her in the wild?"

"I rented her," Wanda said. "Isn't she something? Take a look."

Okay, I saw how this evening was going.

"She has many delectable qualities," the creepy guy decided. "Those tits are a dream come true. So round and squeezable. Her thighs look like silk. Ready to be stroked. And that pussy is heavenly. Clean and smooth. Begging to be exploited. Are you making good use of her?" It looked like he wanted to run his fingers all over me.

"No, we're not at that point," Wanda answered. "Not yet."

He was about seventy-five years old, tall but bent, with thin, scraggily hair and wrinkled skin. His dog looked wonderful, with a rich tan coat and attentive brown eyes. I had always wished that I could have a dog. Working 70 hours a week made it impossible. The old man seemed to take my naked condition for granted, as if it wasn't the least bit unusual.

This was different for me than standing on a nude beach, or even encountering hikers while searching for my stolen clothes. We were in my local park, not far from my office, surrounded by busy streets, cars, bicyclists, joggers, and all the evidence of everyday life. There was no separation from my daily reality to protect me. My face was turning red, and Wanda was enjoying every moment of it.

I was startled as a jogger suddenly went by, a middle-aged man trying to stay young. He looked at me briefly and kept going. Which was insulting. I believed myself worth more than a glance

"You've got a problem with this slave, young lady," the geezer said.

"What is that, esteemed sir?" Wanda replied.

"She doesn't have a collar. No slave is complete without a collar." And then, to my utter chagrin, he knelt and removed the collar from his dog! "Now my Athena doesn't really need a collar and a leash. She obeys just fine, like your slave needs to."

He handed the collar and leash to Wanda, who showed them to me with a horribly diabolic smile. "Thank you, sir, this is very generous," she said. "Come, slave."

Then Wanda made me stand before the old man while she buckled the black leather collar around my neck. The leash went in her pocket.

"This is very fine," Wanda gushed. "Is there anything I can do to repay you?"

"Too old for what I really want," the old man said, licking his chops. "Wouldn't mind giving her a slap on that nice ass, though."

"Well, slave, shouldn't we accommodate this friendly gentleman's request?" Wanda pushed.

I bowed to the inevitable, turned around, and bent over. Whack! He might have been old, but he had a strong swing.

"What the fuck?" I shouted. "That hurt!" The old man chuckled.

"Thank you, ladies, this has been delightful," the rascal said, doffing his hat. Then he wandered off, whistling for his dog to follow.

"That collar looks good on you," Wanda said. "You should make it a permanent part of your wardrobe."

"I'll give it some thought," I replied.

* * * * * *

After the encounter with the old man, we reached the amphitheater, where I received a very unpleasant surprise. One that, in many respects, would change my life forever. The lights were on, which was unusual for a weeknight so late. There were six people sitting on the stone benches. I recognized all of them. Three were so-called women friends from the office, the other three were their boyfriends. They didn't look like they had come to offer support in my time of need. They were laughing and drinking. It was a celebration. Only Sandra came forward.

"Thank you for bringing our slave, all ripe and naked," Sandra said, as catty as ever. "We'll take over now."

Sandra stepped up and hooked two fingers through my collar. I was doing everything I could to appear calm, but I was quietly terrified. Her army wasn't just looking for a good time. From their leering expressions, I realized they intended something far darker than that. Something that would destroy me. I trembled.

"What do you have in mind for her?" Wanda casually asked.

"That's none of your damn business, and we don't want any witnesses, so it's time for you to move along," Sandra warned.

"No witnesses?" Wanda said, realizing what I'd already sensed. She was looking at their expressions, too. The men were hungry, thirsting for my vulnerable body. Rubbing their crotches. The women were anticipating a deep revenge, the darkest of humiliations. Sandra left no doubt what they intended. It was getting hard to breathe. I wanted to run but wouldn't get very far barefoot. I was trapped and everyone knew it. They basked in it. Savored my fear. I checked for Wanda's reaction. All she had to do was walk away and leave me there. My whole life was literally in her hands.

"You forget that she is my slave," Wanda said. "I paid for her. If you want to buy her, it will cost you."

"We'll give you $100," Sandra said, tugging on the collar.

"Not enough," Wanda rejected, slapping her hand away.

"How much?" Sandra asked.

"I want $100,000," Wanda said.

"What? $100,000? Are you fucking kidding me?" Sandra exclaimed.

"That's my price, and it's not negotiable," Wanda insisted.

"This arrogant slut needs to be punished," Sandra demanded. "She's going to get what she's been asking for. Over and over, all night long. We've wanted this for a long time and no one is going to stop us. Do you hear me? Sell her at a reasonable price or face the consequences."

"Consequences?" Wanda said.

"That's right, bitch. If you don't like it, we can take you down, too," Sandra threatened.

Wanda's fist lashed out so fast Sandra never saw it coming. She staggered backward holding her bleeding nose. She would have a black eye in the morning.

"If you wish to punish my slave, we can discuss that," Wanda said. "Attempt to intimidate me again, and I will hurt you. Do all of you hear that? None of you worms get to fuck with me! Not now, not ever."

Wow, and they said I was arrogant.

"What form will this punishment take?" Wanda asked. "It better not be what I suspect, for if it is, you're all going to prison. Every single one of you, for a long, long time. I will see to that personally. Perhaps you only wish to spank her?"

Sandra stepped away to consult her partners, a handkerchief over her sore nose. There was a lot of disagreement. Some were shaking their heads. Two men got up and left.

"We would like to do much more than humiliate her, but we don't want to be arrested," Sandra decided. "The punishment can start with spanking."

"What do you think, slave?" Wanda asked. "Should I let them punish you?"

I looked at Wanda, wondering what kind of dangerous game she was playing. She was gazing at me with an unspoken question. A dare?

"Bring it on, mistress," I agreed. And then I turned to Sandra, boldly saying, "You would like to see me fucked before all these people, but you can't. So do your worst with the spanking, you sick spineless coward, because after I'm done fucking you with every client you ever had, there will be no one to protect you."

Sandra stepped back. She never imagined I would speak to her like that, for it was so out of character. I slipped past her, going to my now reluctant audience. They were anxious. Scooting back. I stood before them, naked and defiant, letting them see everything.

"Take your best shot, you fucking whores. And when I tell your clients what you did here tonight to a helpless woman in handcuffs, let's see what they think of you. When I tell their wives, and their husbands, and their boards of directors what a sick bunch of sadists you are, let's see how many of them will still do business with you."

To no one's surprise, all but Sandra got up and ran. Humiliating an unpopular co-worker is one thing, seeing their careers go up in smoke is something else. I had every intention of doing it, and they knew I could. Even Sandra was having second thoughts, starting to edge away.

"Get back here, you bitch," I ordered. Sandra hesitated before taking a few steps forward.

"Yes?" she asked in a quaking voice. I turned around and bent over, presenting my butt.

"You've gone to a lot of trouble arranging this ambush. I'm guessing you started planning it days ago after Linda told you what the dare would be. So go ahead and take a few whacks. At least you'll be able to remember spanking my ass tonight while I spend the next twenty years spanking yours."

Sandra took off.

Once the gang of six were gone, my knees went weak. I grew dizzy, looking for a place to land that wasn't cement. There was a patch of turf where I fell on my butt, the damp grass invading my most intimate areas. I started crying, and when I tried to stop, it turned into sobbing. I could barely breathe.

I expected Wanda to be applauding her triumph. It was obvious that, despite my last-minute bravado, Sandra's threats had broken me.

Wanda did not hover in victory. There was no gloating. I felt her sit down behind me. Her arms wrapped around my waist. Her legs encircled my thighs. She laid her chin on my shoulder. I found a way to breathe again.

"You may not believe this," she whispered, "but I did not buy your dare to humiliate you. Well, maybe a little. We've been rivals for so long, it's hard to resist. But I won't let anyone hurt you. I swear that's not what I want."