My Bff My Pimp

I was sitting in the break room at the spa when I got the text message. My sometimes play partner, Janet, had a death in the family and had to cancel on our plans.

'Shit," I said.

My best friend, Sheila, looked up from her phone.

"What?"

"My plans fell through for the weekend."

"That sucks. What went wrong?"

"Janet has an emergency and can't go. Now I can't go to the party and I can't get my money back for the hotel either."

"Why can't you go to the party?"

"No unaccompanied males allowed. They want to keep it balanced."

Sheila and I had gone to massage school together and become best friends. We were each going through divorces or breakups during school and bonded over our troubles. There was nothing between us other than being besties. She was also 14 years younger than me and still in the last few years of getting her kids up and out. And she knew that when I said "Party" I meant a play party. She knew that I like BDSM and occasionally went to the city for events. We shared everything with each other. We worked at a spa in North West Connecticut. Lots of money and snooty massage clients. But pretty good tips if you didn't mind their attitudes.

"Damn. Why not just go to the city and enjoy the weekend? Go out to dinner? See a show?"

"Meh. No fun by myself. You want to go with me? The room has two queen size beds. You could go and do some shopping or whatever?"

"That might be fun. Let me see if the kids are all set. When do you need to know?"

"I have the room Friday and Saturday night. I was going to go down Friday afternoon."

"I'll let you know."

I didn't think anymore of it. I figured she wasn't serious. I might go on my own, but I would decide on Friday. Thursday she sent me a text.

'I can go. Do you want to see a matinee of the new musical Saturday'

Not high on my list, but it might be fun and would salvage the weekend, I thought.

'sure. Sounds good'

Friday I picked Sheila up and we went to the train station. We got into the city and went to the hotel and checked in. We wandered around checking things out and found a not too expensive place for dinner. It was fun. She and I got along so well and always laughed a lot. We went back to the hotel, spent time on our own ipads or whatever and finally turned in. It was a little odd sharing a room but we had done so many massage exchanges in school and out it was almost normal to see each other in pajamas.

Saturday morning we had breakfast and did some shopping and went to the show. It was fun. I just could never take musicals seriously. People randomly bursting into song never made sense. We were walking around talking and just killing time.

"If I went with you, could you still go to the party?"

I looked at Sheila.

"What?"

"If I went with you, you wouldn't be an unaccompanied male. Could you still go?"

"I could, but you don't want to go."

"Maybe. Depends. Would I have to do anything? I don't want to get naked or be spanked or anything. But I could go with you."

"Yeah. You could go and not do anything yourself. But you're be seeing everyone play. You'll see naked people and lots of BDSM."

Sheila thought for a few minutes.

"Let's go then. I know how much you were looking forward to it."

"Are you ok seeing me naked? Or me playing?"

"I've seen almost all of you anyway. What's the difference?"

"Alright," I said.

"I don't have any leather, but I brought some black clothes. I wasn't sure I would go through with it, but I thought about it."

I looked at my watch.

"We've got about an hour. We should go get ready if we are going to go."

I couldn't believe she wanted to go. She was never shocked at anything I told her, but I just figured she was super vanilla. We got to the hotel and she showed me what she brought. Basically, just all black clothing. A skirt that came almost to the knee, low boots, black stockings, black tank top and s leather biker type jacket.

"That's perfect. And you'll look like a Top so no one will bother you."

"What are you wearing?" she asked.

I blushed. I rummaged in my bag and pulled out a collar and a leash.

"This is my outfit."

"That's hardly fair," she said. "I'm dressing up and you're going in jeans and shirt? And just adding a collar and leash?"

"No. Just the collar and leash."

Her eyes widened.

"Oh. You want me to hold the leash?"

"Would you?"

"Yep. Sorry I was a little slow on getting that."

I emptied my back pack and Sheila got changed. She was my height barefoot and her boots made her a little taller than me. We headed out and walked the couple blocks to the building where the play space was. It was in the loft of a warehouse on a side street. We rang the buzzer and I gave the password and we got buzzed up. There was an anteroom where they checked my name, verified that I had paid and we signed the rule sheet. Then we got passed into another room.

I took out the collar and leash and took off all my clothes. I felt a little awkward standing in front of Sheila. Especially since I hadn't told her about my chastity cage. She just watched with a slight smile on her face. I put my clothes in the bag along with our phones and handed it to the attendant. I fastened the collar around my neck, clipped on the leash and handed it to her. She turned on her heel and led me into the playspace.

There was every combination of sex and BDSM going on. Naked women. Naked men. Women spanking women. Men in stocks. Women getting hot wax poured all over them. Sheila took it all pretty well. She asked questions or sometimes shook her head in amazement. It would have been nice to play but I wasn't going to ask that of her. She was leading me naked on a leash. I was happy.

"What about that over there?" she asked pointing. "Looks like something from the middle ages."

It was a set of stocks with a big hole for the head and two smaller ones for the hands. She led me over there and started fiddling with it. A dungeon monitor came over and showed her how to open it and she put me in it. She leaned own and put her mouth to my ear.

"This is hilarious. Good thing they took our phones. I would take a picture of this to tease you with."

"Haha," I replied.

I heard my name and I struggled to look. A woman came up and started talking.

"I was hoping you'd be here. I've been looking forward to our scene for months."

I really couldn't see much, but I knew who it was. She and her husband often came to parties. She and Janet had concocted a scene they wanted to act out. Actually, it was the couple's scene, Janet just had a role to play. Me too, of course.

I stayed there bent over in the stocks while I heard Sheila and Susan introduce each other and Sheila explained that Janet couldn't make it. Susan went off to find her husband and Sheila squatted next to me so we could talk.

'What is she talking about? A scene you had agreed on?"

I was really unsure what to do. I didn't think I could tell Sheila what they wanted. I wasn't sure I wanted to go through with it. It was a big jump for me. Sheila knew me too well. She could tell I was hesitating.

"You may as well tell me. You know you tell me everything in the end."

So I did. I told her what Susan and her husband wanted. And the role they wanted Janet to play. Sheila made me tell her the plan twice. She couldn't believe it.

"And you want to go through with it?" she asked me.

"Yes," I replied. "But I'm really nervous. I've never done it."

"Okay. I'll play the role. And I'll be here with you the entire time."

I thought my heart would explode. Susan and her husband came back. Susan started talking to her husband. You could tell they were play acting.

"Honey, you promised. You said if I let you fuck that blond girl last month you would do what I wanted this month."

Her husband said something I couldn't make out.

"Thank you, darling."

Susan started talking to Sheila.

"I want to watch my husband to fuck your slave. Is he available for rent?"

"He is, but I doubt you could afford it."

"Why? What makes him so special?"

"He is a virgin," Sheila said. "I'm going to auction him off later. I expect his cherry to go for a lot."

I told Sheila to play act and she was going for it.

"Oh my god. I have to watch this. I really want you to bust his cherry. How much?"

"Twenty five hundred."

Holy shit. Where did Sheila come up with that number? We were just acting out a scene, but still. I didn't know whether to laugh or what.

"You can't be serious. Twenty five hundred just for ass?"

"Virgin ass. How often do you find that. Virgin ass bent over in the stocks. There is only one first time. You'll never get an opportunity like this again."

Susan and her husband walked away and talked quietly. Susan came back.

"Two thousand. Best offer."

Sheila bent over and whispered in my ear.

"Should I negotiate more?"

"Only if you want to."

Sheila stood back up.

"Deal."

Susan left the room for several minutes and came back and handed Sheila an envelope. Sheila stuffed it in her jacket pocket. Susan and her husband stood behind me and started rubbing my ass. Sheila pulled up a chair and sat in front of me so she could look at me.

"Are you ok? Are you sure about this?"

I nodded.

I felt someone putting lube in and on my ass. The dungeon monitor came over to make sure that they were practicing safe sex and wearing a condom. I felt a finger go in and out of my ass and then something press against my asshole. I could hear Susan egging her husband on. She was really excited. Sheila took my head in her hands and lifted my head up.

"Look at me. Just focus on me."

I kept looking at Sheila. My eyes popped wide and I gasped. His cock had slid into me.

"Oh my God," I moaned.

"It's ok. Focus on me."

Sheila held my eyes with hers as he started fucking me. It was overwhelming and intense. Not just the physical sensation but also emotionally. I was being publicly fucked in stocks in front of my best friend. Soon I just stopped thinking. The only thing I knew was that I was getting fucked and Sheila was there for me. I could feel him getting more urgent in his thrusts.

"Wait, honey. Don't come yet," Susan said.

She stood where I could see her out of the corner of my eye and pulled out a Magic Wand. She pressed it against my chastity cage and turned it on. I started shuddering. Her husband picked up the pace and started to cum. He was hitting my prostate and the vibrator was driving me nuts. I got complete tunnel vision and could see nothing but Sheila's face and I came. I came like I never came before in my life. I think I screamed as I had an orgasm in the cage. I must have blacked out. The next thing I knew my head and hands were free of the stocks and Sheila and Susan were helping me walk to a chair. I sat down gasping for breath. Susan left to do something with her husband. Sheila sat next to me holding my hand. When my breathing had slowed she handed me a bottle of water.

"You doing okay?"

"Yeah. Just overwhelmed."

We sat there while I drank the water. Without talking we got up when I was done. I cleaned up in the bathroom and we went to the anteroom. I got dressed and took off the leash and we walked back to our hotel. We sat at the bar and had an appetizer and a drink. We didn't talk about the party. I think we were both processing what we had done or seen.

We went to bed. I slept like a rock. Sunday morning we had breakfast and caught the train back. Sheila reached into her jacket pocket to get her phone and pulled out the envelope that Susan had given her. She opened it and pulled out a wad of cash.

"Holy shit. This is real money."

She quickly counted it. Twenty one hundred dollar bills. She looked at me.

"I thought we were play acting. This is real. What do I do with it?"

"You keep it," I said. "You earned it."

"I can't keep this. I can't take money for selling your ass."

"As far as I'm concerned, that's yours. Your reward for going with me to the party."

She gave me a searching look and put the money back in the envelope and back in her pocket.

"I should go to parties with you more often," she said. "I really should."