My Bff My Pimp 02

In this part, I try to tell the story from Sheila's POV. Same characters, just narrated by Sheila.

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I was sitting in the break room looking at my banking app. Too many bills. Not enough money. I loved what I did as a massage therapist, but you would never get rich at it. Tim walked in and he saw the disgusted look on my face.

"What's up?" he asked.

"Usual. Broke."

"Ugh. Sorry."

I laughed.

"I could really use another of those parties we went to," I said.

Tim didn't reply and I looked at him. He was obviously thinking about saying something. I raised an eyebrow.

"Well.......if you're serious."

I started to say I was just joking, but the two grand I got at the party had helped a lot. Could I do that again? I had thought it was a once in a lifetime experience. Someone else walked into the break room and we couldn't continue. We each had clients anyway. I thought about it while I worked. It was kind of fun, if you didn't mind watching your BFF get fucked in a set of stocks, and the money really helped. I hung around after my last client till Tim was done and suggested we get coffee. Once we were seated and had our drinks, I jumped into it.

"Is there a party coming up?" I asked.

"There is an auction. I don't know if I can get us in. Do you want me to try?"

"What's an auction?"

"I got to work at one as a server. Drinks and things. I didn't get to play. But it is very discreet and high end."

"But what is the auction part?"

"Rich people come and buy entertainment. Dommes and subs go on the auction block and people bid for what is on offer. Sometimes it's a session from a domme or a session to punish a slave. Sometimes it is to watch a scene put on by a top and bottom."

"I definitely don't want to be played with. Or play with anyone else," I said.

Tim nodded.

"Yeah, I agree. We could offer a scene. You could be the Domina and you could dominate me for someone's entertainment. I know there are people who just want to watch."

I thought for a long time. Last time I just led Tim on a leash and we watched others play. This would be more.

"I am so tempted. I could use the money, but I don't know if I could pull off be a dominatrix. I don't know anything about it. Just what I saw at the party."

"If you want me to try, I'll contact some people and see if we can get an invite. I was thinking of going as a server again anyway. If we can get invited to the auction, we could come up with a list of things you could do. You could just have a preplanned scenario to offer."

"I can't believe I am thinking about being my bestie's dominatrix," I said.

"Life is weird," Tim said laughing.

"Ok. Let's try," I said.

I got a text from Tim two days later.

'we are in. next Saturday'

I gulped a little. I had said yes, but I half expected it not to happen.

'okay. Great. What next?' I texted.

'we should get together and decide what you can do.'

We were both off on Saturdays so I would go to Tim's house and we would go over all his toys. I took a selection of clothes from my closet. I didn't have anything specific for this, but I took anything that was black and hot. Tim let me in and offered me iced tea. He could tell I was nervous. He was too.

"Well. We should figure out what we want to do since we are committed," Tim said.

I nodded.

"I think if we should do something like at the last party. You dress up as the Top and keep me leashed and collared for the cocktail party. Then for the auction we offer a one or two hour scene. We can go over the toys that I have and pick what you feel comfortable with."

"Cocktail party?" I asked.

"Yep. The first part is just social. You'll have to circulate and socialize. Let people get to know you or ask questions about what you are offering at the auction."

"Oh my god. I don't know if I could do that. I thought I could do the auction, but I can't pull off being a Pro Dominatrix like that."

"You don't have to. Just be yourself. Have fun."

"And you circulate with me?"

"If you want. You can have me help serve or keep me with you. Whatever you want. You're the boss, remember."

"I'm definitely keeping you with me. What are you going to be wearing?"

"Same as last time. Collar, cage and leash."

"Let's look at the toys," I said.

We went into Tim's dining room. His table was covered in things. Some were obvious, like paddles. Others weren't. Tim told me what each thing was and how to use it. We decided on taking mainly sensation toys. Floggers, paddles, clothes pins, Wartenburg wheels, et cetera.

"What about candle wax? Do you think you could do that?" Tim asked.

"I don't know. Is it dangerous?"

"No, not really. I like it a lot. As long as you drip it from at least 18 inches it is safe," he replied.

"Put it in the bag," I said.

We had separated all the toys except for a pile of straps and dildos. I pointed at them.

"Ah. The strap on harness," Tim said.

He picked it up and arranged it so I could see what it was. I started shaking my head no. Before I could say anything, Tim spoke.

"Before you say no, just think about it. Janet used to say wearing it made her feel powerful. It helped her get into the mood. Plus, it will definitely get you attention at the party."

"Do you realty want me to......"

I couldn't bring myself to say it. We were besties. I couldn't do that.

"Up to you," Tim said.

I didn't say anything.

"Do you want to practice with anything today?" Tim asked.

"No. I want to decide on what to wear and then I have to run."

We went through my clothes and picked out a couple of possible outfits. I usually didn't wear heels very often since I am tall for a woman, but I did have some. I left the outfits at Tim's house and left. The next week was a little surreal. We chatted in the break room. Never about the upcoming party, but it was always in the back of our minds. Finally, it was Saturday night. I was nervous driving to Tim's house. Tim opened the door and let me in. I was early, so we had some time to relax. We each took showers and I laid out my clothes in the spare room. I got dressed and did my hair and makeup and walked out of the room. Tim was waiting in black pants and a white button down shirt. I laughed out loud and Tim looked at me quizzically.

"While I was getting dressed, I thought to myself that it felt good to dress up. I hadn't had an occasion to do it in a while. Then I remembered it wasn't date night."

Tim laughed.

"Yeah. It's certainly an odd feeling."

Tim picked up the bag of toys and we walked out to the car. On the drive to the party we went over our fictional backstory. We kept it simple. I was Lady Astrid and Tim was Patrick. We were lifestyle Top and Bottom. Not married. No kids. Didn't live together. I was a Domme and he served me. I felt I could bullshit my way through cocktail conversation and keep any other details vague.

Tim pulled up to a gate and gave the proper responses to the gatekeeper. We drove up a long driveway to big rambling house. There were plenty of cars there already. We parked and went it and went through the security procedure. Tim was vouched for by the host and then we had to put our phones and other stuff in a locker. Tim stripped and put his clothes in the locker. They went through the toy bag and my pockets to make sure there were no cameras or phones. I attached to the leash to Tim's collar and we went into the party.

If you overlooked the nudity, leashes, collars and overabundance of black or red leather, it was your normal, everyday rich person cocktail party. I circulated with Tim on my leash (that still seems weird to say) and mingled. I stuck to drinking water. I didn't think alcohol would help. I moved in and out of several conversations. Most people seemed fairly normal. People asked about us and I described our fictional relationship and what we were doing for the auction. Some were interested. Some weren't when they understood it was demonstration only and they couldn't take part. I wasn't used to wearing heels so much and I sat on a couch. Tim knelt before me and started giving me a foot massage. I looked down at him.

"This I could get used to," I said.

Tim just smiled. I looked closer at him.

"Are you getting hard in your cage? Does this turn you on?" I asked.

Tim nodded. It did feel wonderful. One of the advantages of having another massage therapist as a bestie. I enjoyed his touch on my feet and then they announced the auction. Tim put my heels back on my feet and we took our place. It was interesting to watch and see who went for a lot and who didn't. Obviously, physically attractive slaves went for a lot. Scenes where the bidder could take part went fairly high too. It was our turn and I led Tim onto the stage and described the scene we were offering. We did ok. We had several people bidding, but not nearly as high as the previous scenes. It came down to the final two bidders and it looked like one woman was determined to win. And she did. We walked off the stage and a servant led us to a side room. The woman paid the fee, half to the auction house, half to us, then the servant led the three of us to a separate play room. The servant would stay quietly in the corner as a monitor for safety. The woman introduced herself as Betty. She was an older woman. I guessed around 70. She had the look of a very well preserved, very rich society woman. Thin, impeccably dressed, tasteful jewelry, iron gray hair pulled back in a bun. I asked her if she wanted anything in particular.

"Yes, I do. Tim reminds me of my first husband. I want to see you punish him."

Tim laid out the all the toys on a side table. Betty and I looked over all the toys. She picked out a paddle and handed it to me. I told Tim to bend over on the table and started slowly spanking him. Betty got a glass of wine from the bar and watched as I paddled Tim. His ass was red and he was starting to squirm. Betty motioned for me to stop and she rubbed Tim's red ass.

"I should have done this to my husband," she said. "He wouldn't have liked it."

We went back to the table and she selected the bag of clothes pins and the Wartenburg wheel. The heavy table in the middle of the room had restraints on it. Tim lay on his back and I attached the wrist and ankle cuffs and tightened them down so he couldn't move. Then I spent at least an hour tormenting him. I put clothes pins everywhere from his nipples down to his thighs. While he was writhing in pain from those I ran the spiky Wartenburg wheel all over the rest of his exposed flesh. Betty went to get another glass of wine. I leaned in close to Tim.

"Are you ok?"

"Yeah. I'm fine."

His eyes were a little glassy and his breathing was ragged.

"Should I stop?"

He shook his head no. I watched him for a moment. It was my job to make sure he was ok. We were still within the limits we had agreed on. I stepped back from the table and shook my head in wonder. My best friend was bound naked to a table and I was torturing him as entertainment for an old woman. I couldn't believe what I was doing.

Betty came back and was looking at the table. We had less than half an hour left of our time. She fingered a lot of the toys and then looked closer at the straps and dildos. She handed me the harness and the largest and most lifelike of the dildos.

"I want you to fuck him," she said.

I tried to say something. I couldn't do that. It was one thing to torture Tim, but he was my best friend> I couldn't fuck him with a strap on. I thought I might just wear the strap on for show, but not this.

"It's my show and this is what I want," Betty said.

I looked over at Tim. He gave me a little nod. I mentally shook my head. Ok then. This wasn't going to work with the skirt I was wearing. I closed the door to the room so people couldn't watch and unzipped my skirt. I had black tights on underneath and I pulled the harness up, inserted the large fake cock into the holder and tightened it. I walked over to the table and picked up a bottle of lube. Tim was right. Wearing the strap on did make me feel powerful. Is this how men felt when they had an erection? Like they were king of the world?

Back at the table I released Tim's ankle cuffs and pulled his hips to be bottom of the table. I asked the monitor to reattach his wrist cuffs over his head at the other end of the table. I was still wearing my leather jacket and I was getting hot, so I hung that up on a peg.

I lifted Tim's legs so his calves were resting on my shoulders. I squirted lube all over the cock and moved forward. I looked at Tim's face. His eyes were wide and he was panting. I lined up the cock with his ass and started to push but I couldn't get in. I backed off and added more lube. I lined up and pushed again and felt the cock start to enter. I held still and pushed some more. Once more I pulled back and added lube and pressed again. I got the head in and Tim's eyes rolled back in his head.

"Look at me," I said.

Tim looked at me and I slowly entered him till I was all the way in.

"Are you ready?"

Tim nodded.

I started slowly pulling out till just the head was in his ass. Then I pushed all the way back in, making sure my hips were pushing hard against him. I wrapped my arms around his legs to keep him immobile and started a faster rhythm fucking him. It was incredible to watch his face. Sometimes his eyes would close and then I would stop. I wanted him focused. Betty moved right next to me.

"Fuck him harder," she said.

I started moving harder and faster. Tim seemed to be able to take it so I kept it up. I never realized how much work it was fucking someone. My abs were getting a workout. You could hear the slap every time my hips hit his ass. I had to keep pulling his hips down to the edge of the table because I was fucking him so hard. I almost forgot about Betty standing next to me till she spoke.

"I'll give you a bonus if he comes," she said.

I looked at Tim. Could he really cum from this? At the last party the woman put a vibrator on the cage to make him cum. Tim tried to say something. He had to clear his throat before he could speak.

"Push my legs toward my shoulders," he croaked.

I put my hands on the back of his knees and pushed them toward his shoulders. The angle of his hips and ass changed.

"Stop. Right there," he said.

I held his legs in that position and starting thrusting again. I must be hitting it just right because every time I got all the way in Tim jerked and moaned. I looked back at his face, but he wasn't looking at me. Or not at my face anyway. He was staring at my chest. I was just wearing a black half bra, with a thin silk chemise over it. I looked down and my nipples were clearly hard and visible. I was actually getting aroused. Betty noticed the interaction.

"I'll double the bonus if you cum too," she said.

I reached down and fumbled and found the button on the dildo. It started vibrating in the harness. It wasn't perfectly lined up, but it was pretty close. I started getting really hot.

"Talk to me," Tim whispered.

I leaned forward so our faces were closer together.

"You want my cock?" I asked.

"Yes," he whispered.

"You want me to fuck you hard?"

"Yes."

"Will you cum for me?"

I kept saying things like that and Tim reacted to it. He was begging for me to fuck him harder and telling me how much he loved my cock. Soon I could see his chest start to flush and his breathing got really rapid. That pushed me over the edge. I let my head fall back and I moaned as I came pushing hard into him. I slowed down.

"no.....don't stop," Tim moaned.

I looked down at him again and started pounding his ass.

"cum for me" I said.

That pushed him over the edge and he started jerking and pulling against the restraints. He moaned and spasmed and I could see cum dribbling out of his half hard cock in the cage. I slowed down and came to a rest with the cock still in his ass. I let him recover for a moment before I slowly slid the cock out of him. The monitor came over and undid his hands helped him roll over on his side and then covered him with a sheet. While he rested I went over to the toy table and cleaned up and took off the harness. I put my skirt and jacket back on and knelt next to the table to check on Tim.

"Are you ok?" I whispered.

He opened his eyes halfway and gave me a week smile.

"I'm ok. Just need a minute to recover."

I stood and Betty approached me.

"That was amazing. Thank you so much," she said.

She reached into her purse and pulled out an envelope. She opened it and started to count out some bills, but then stopped and handed me the entire envelope.

"I really enjoyed that."

She reached back into her purse and pulled out a card and held it out."

"If you do private shows, please call me."

I took the card and nodded with a smile. Betty left the room and the monitor and I went back to the table. The monitor got some handy wipes and helped Tim clean up. I cleaned and put away the toys. When I was done, Tim was sitting up on the table drinking a bottle of water. Somehow he looked very different from earlier. During the cocktail party he seemed comfortable and confident following me naked on the leash. Now he seemed a little deflated. I know I often felt the need to wear something after hot sex. We didn't have anything for him. Tim finished the water and stood up. I put the leash in the toy bag and we walked out of the play room together. I took some money from the envelope and tipped the monitor and thanked her. Most people were leaving or finishing their scenes. We went to the lobby and got our things from the locker. Tim dressed and we drove home. We were both quiet on the drive. I think we both needed to process the evening. At Tim's house I changed my clothes and got ready to go home. I pulled out the envelope.

"We should split this," I said.

Tim stopped me and shook his head.

"You keep it," he said firmly.

"That's not fair," I answered. "We did this together."

Now Tim looked nervous.

"What's up?" I asked.

"I'd rather you give me something else," Tim said shyly.

I waited.

"I'd really like it if you would fuck me again sometime."

I was surprised. I thought this was just a show. But I it was also hot. And I had climaxed while doing it. I looked at him for long time. He looked very vulnerable right then. Like he had really opened up and was scared of rejection.

"Would you like me to stay the night?" I asked.

Tim stood and silently took off all his clothes. He was still wearing the collar and chastity cage. He knelt before me.

"Yes."