Cheri Ch 05

She waited till Friday morning before deciding to tell Cyd if she couldn't keep the date. Turned out she felt she could do it and felt she would be ok not using the gel that day.

I took her to the Chestnut Hill Mall to get a new dress and she had an appointment for her hair and makeup at a place Cyd told her to use. Cyd told her to meet her in the lobby of the Hiton at 8PM. When she came down stairs, she was breath taking to look at. Her hair and makeup made her look like a high fashion model and the dress showed enough cleavage to entice but not be vulgar. It was slit up one side to her hip and I noticed I couldn't see any hint of her panties. I figured she was wearing a thong till she hiked it up to show me her bald pussy. I knew the dress had built in support for her tits so other than her heals the only thing besides the dress she was wearing were earrings, bracelet and two rings. The rings looked like an engagement and wedding rings.

I asked her: "The rings are they yours?"

She smiled and told me: "Yes, other than my son this is all I have from my marriage. Cyd asked me if I had them and when I told her I did she said to wear them that the clients get off having sex with other men's wives. Even if they are paying for it. So, till you put yours on my fingers, when I am whoring, I will be using them."

I noticed the stone in the engagement ring looked about four carrots, so I will make sure the one I buy her is larger. Then I thought she could just use them when she is working as an escort, but then I felt once she has my rings on, I never want her to take them off. It doesn't mater if she has them on, I accept her being an escort, in fact it excites me that she is. Then she should wear my rings doing it, especially if it helps her to earn more money. She was taking a cab to the hotel; she had a small hand-held purse with her ID and lipstick and nothing else. Not even her phone that bothered me, it didn't fit in her small pure. Tomorrow, I need to get her a larger one or maybe a small flip phone for when she is working.

I was so nervous pacing the floor and she had only left less than a half hour ago. I was about to take out a bottle of whiskey when the phone rang. It was Cheri's mom Jan asking If I wanted to be part of her web show that night.

I told her: "Cheri is working her first date and I am nervous I might not be able to perform that well."

She said: "Honey believe me you will do just fine. Harry is here and looking forward to watching me suck you off and get you hard again to fuck me. We have Viagra if you need it."

I told her: "I probably need the distraction; I'll be right over."

Harry opened the door and she was right judging by the tent in his pants. Jan had changed one of the bed rooms into her studio for her shows. It had already started and she was wearing a see-through outfit that went over her head and was like a poncho so the sides didn't connect. I noticed she had two pink things sticking out from her pussy and her ass. Harry handed me what looked like a small remote control and I saw he also had one. He pressed the remote and Jan started to respond. I realized the remotes controlled the things in her pussy and ass.

Harry pointed to a monitor and I saw her on it and on the side, there was a list of people that were not only watching, but tipping her. I also became aware she was wearing a small mask to hide who she was. I pressed the remote I held and she started going crazy with excitement as she started to orgasm. The tips started to go up and I realized she was making about five hundred tokens a minute.

I asked Harry: "How much is a token worth?"

He told me: "Each token is a quarter; she is making a killing doing this and private shows she makes even more. She must split with the host site they get twenty-five percent to host and another ten to handle the money exchange. So, she clears sixty-five percent before taxes and overhead."

I asked him: "Does Cheri know how much her mom is making?"

He said: "She does and when she asked her mom to set her up. Her mom told her she would do better doing Only Fans."

I asked: "Why doesn't Jan do Only Fans?"

He told me: "She feels she is too old and she likes that the guys and women that watch her are the ones that would feed quarters into the video machines to watch porn years ago. Plus, she has videos that they can pay to watch twenty-four seven and pictures they can down load. Again, they pay to do it. She has wish lists with amazon that people buy and it is sent to her direct form Amazon for her to wear for them during private shows. Those vibrating things she is using were paid for by a viewer and he is paying her to send them to him used without being cleaned. You will be part of a private show limited to twenty people that are paying a thousand tokens each to be the first to see her having sex with a man. It is sold out already. She posted it when she hung up the phone with you. It only took five minus to sell out. Not only that it is going to be recorded and sold separately later."

Jan came over to us and said: "I needed a break and put the BRB on the screen. Are you read y to do this?"

I Asked her: "Since Harry told me how much you will be making from this, what do I get?"

She smiled and told me: "You get to marry my daughter and fuck me and her sisters whenever you want, what more do you need?"

I asked: "So, I am going to get to fuck Sue as well?"

She said: "Tomorrow night she will be at the party, I hope you have Viagra, you will need it. Now get out of those clothes we have a show to do."

She handed me a mask like the one she was wearing and after she went back live for a few minutes she announced the private show was about to start. She waved me over and had me stand in front of her as she knelt. She signaled Harry who started the live feed for the private show. Jan smiled at the camera and turned and started sucking my cock. That is not the right description, he was worshipping my cock. She led me to the bed and laid me down and raised my legs and shocked me when she started licking my asshole. Then she sucked each ball into her mouth and finally went back to suck my cock. This time she was a woman possessed the way she bobbed her head up and down. Three times she brought me to the edge of blowing my load only to back off. She had me stand and jerked my cock till I shot rope after rope of cum into her open mouth and on her face. She turned to face the camera and showed the cum in her mouth before swallowing it and showing her empty mouth. I noticed the monitor showed the BRB.

She asked me: "Do you need the pill or are you ready to start fucking me in a couple of minutes?"

I told her: "I better take the pill or I won't be able to fuck Cheri when she gets home."

I took the pill and we went back to the bed and the camera went live. We kissed and did a lot of foreplay; I ate her out and she sucked me. We were in a sixty-nine when the pills took full effect. I then started to fuck her. We changed positions several times rill Harry got our attention and we saw him pointing at the tip count on the monitor. Then he pointed at the comments at the right side of the screen. The twenty people were asking Jan to let me fuck her ass and then for her to suck my cock straight from from ass till I cum in her mouth.

I asked her: "You had that vibrating thing in your ass, did you cleanout before you did that?"

She said: "No. the guy wanted my shit on it when I send it to him."

I asked: "Have you ever done ass to mouth before even if you were cleaned out back there?"

She said: "No, I never even thought about that sort of thing."

I told her: "I am not to keen getting shit on my cock."

She said: "I don't want to lose any viewers but I am not ready to do that."

Harry said: "I'll post it will have to be another private show in the future."

She did and the offers went up. Jan said: "They all must be whales; I didn't think I had any of them."

We were still slowly fucking and I asked: "What the fuck is a whale."

She said: "Very rich people that will pay ridicules amounts of money to see what they want."

She looked at the screen and the offer was up to ten thousand tokens, that is twenty- five hundred dollars. I thought she might be changing her mind, hell if I was getting the money I sure would.

She looked at me and asked: "If I ask them to double it and they do, if split it with you, will you, do it?"

I glanced at Harry and he had his hands together as if he was praying and was saying please. I had a funny thought, if I did it, I might make more than Cheri tonight. Hell, shit washed off and, in this case, most will be sucked off. If Jan can suck my shit covered cock why not.

I said to her: "Just try not to throw up on me."

They accepted the offer to double the money. Jan handed me a tube of lube and I covered my cock. She got on all fours and I started to push my cock up her ass. I was surprise how easily I slipped in and found her ass felt nice even having shit in it. The vibrating thing from earlier must have pushed a lot of it back up her colon. When I was ready to cum, I pulled out and she spun around and didn't hesitate and started sucking my cock. There wasn't as much shit on it as I thought there would be, but there was shit on it. Twice I thought she was going to throw up, but she managed to not do it. She felt me about to cum and took it out and kept her mouth open to catch my load. I noticed some shit on her lips and I hoped it showed up on the camera. That way the people paying would feel the got their moneys worth.

I was surprised at the size of the load I shot given I had already cum earlier when she sucked me off. It went in her mouth and on her face. She made a show of pushing what was on her face into her mouth including the shit from her lips. She showed it and swallowed. Harry said were black and she ran to the bath room. We heard her throwing up and then brushing her teeth and gargling.

She came out and as I went to shower, she said: "I won't be posting it and if you tell anybody about it especially my girls, I will cut your balls off."

I told her: "Jan I don't want anybody to know I did it either. That was some fucked up stuff, the money made us to not think it through."

She said: "I better make sure Harry keeps his mouth shut as well."

I said my good by and headed home to wait for Cheri to return from her first escort date and being a paid whore. I woke at 9AM as I heard the front door open, the TV was on and I realized I feel asleep waiting for Cheri to get home. I looked up to see her coming in, her hair was somewhat decent, but she looked like she had been well fucked.

I asked: "Are you ok, you look like you took on the sixth fleet."

She said: "I feel like I did. Help me up to the bed room and draw me a bath please."

Once in the room I helped her out of her dress and she had cum running down her legs and dried cum on her tits and elsewhere. I was surprised her hair looked as good as it did.

I ran the tube and when it was ready I helped her in and asked her: "Would you like coffee or something else?"

She said: "Coffee would be great and do I have any of those pain pills left?"

I became worried when she asked about the pills. I told her: "There are two left, why do you need them is it your cervix that you need them for?"

She said: "No, my cunt is fine it is this splitting head ache, if it doesn't go away, I may need one."

I went to make the coffee and was glad she wasn't looking to take the pill then. I had a feeling the head ache was from booze so, I made some dry toast in case she wanted to eat something. I brought the coffee and toast to her and sat on the floor and stayed with her in case she needed anything else.

I asked her: "I thought it was you and Cyd with a male female couple for dinner and sex after?"

She said: "So did I, but when I got to the Hilton Cyd said the plan changed. The woman had finally gotten her divorce finalized and wanted to celebrate with a gang bang and wanted Cyd and me to be fluffers for her. Cyd got a few of her male escorts that weren't working and a few more from another agency she and Jake work with at times they need a more escorts for conventions."

I asked: "What about her male partner that was suppose to be part of the date?"

She told me: "Oh he was there he filmed the whole thing."

I asked: "If Cyd and you were only there to keep the guys ready, why do you look like you do?"

She told me: "It was going a long for about an hour when Jake and Yvette showed up. He handed the men Viagra to take and Yvette gave the woman a pill to take. Jake told her it would help her to enjoy her gang bang more. She was already drinking wine and it was affecting her already. Cyd was drinking, but I wasn't at that point. It was a two-bed room suite and one of the bed rooms could be accessed from the corridor. That is where they had room service deliver more beer wine and food.

The woman was really enjoying herself after the pill kicked in, her orgasms happened more often and were more intense. At some point I started drinking wine and was sure to only poor enough that I finished it before putting the paper cup down. Around midnight I was starting to get tired Cyd told me she had some pills that help boost your energy and keep you awake. I told her I would be ok and didn't need any. She popped one and chased it with water, saying if I did take one then don't drink alcohol. I stopped drinking the wine incase I decided to take a pill. A while later after I drank a lot of water, I asked Cyd for one of the pills. I went to the other bed room to get another bottle of water and when I got back the woman was passed out and I thought great it's over. Two guys picked her up and moved her to the other bed room. There were two queen size beds in the room she was being fucked in and Yvette started fucking on the other bed. The male client started filming her and soon Cyd stripped the other bed and was fucking also.

I don't know if it was watching Yvette and Cyd or the pill I took, but I wanted to be fucked also. Taking two guys hands we went to the living room and they turned the couch into a bed and I sucked one while the other fucked me. I have no Idea how many guys fucked me or I sucked off. All I know is I kept wanting more cock, around 6AM the guys were done and I slept till I was woken up a while later. It was the woman and she was thanking me for helping her to have the best sex party ever. She handed me my dress and my purse that she had put in the safe. The man she was with asked if he could have one for the road. I didn't catch on right away and she said he wants to fuck you. He didn't get laid turning the whole time he was recording the show. I figured what difference will one more make. He was great even after all the fucking I did, I could still feel him and he made me orgasm several times before he unloaded in me. After he told me he will be booking me in the future. As he went to shower, she told me she put something extra in my purse."

I asked her: "What is it that she gave you?"

Cheri said: "I don't know I didn't look."

I asked: "Why didn't you shower there?"

She told me: "Jake, Cyd, and Yvette came in the room and said we needed to leave. I put my dress on and we left, but Jake led us away from the elevators to a service door. When Cyd saw my confuse look, she said we can't go through the lobby looking the way we do. We took the service elevator to the garage.

In the car I asked them if this happens often. Cyd said they have done other gangbangs but nothing any where close to what happened last night."

I had to know and asked: "How much are you getting for last night?"

She said: "Cyd had told me the dinner date was five hundred and the sex after would start at one thousand and go up depending what happened. But that went out the window when it became a gang bang. I feel that when we started to also fuck that may not be part of the fee. All though he did take video of it, so maybe it is. I will have to wait and see."

I asked her: "Would you do another one like last night if it came up?"

She smiled and asked: "Would you be ok if I did?"

I told her: "First tell me this, did you enjoy it, were you in control of what you did and was done to you? How does your body feel after it? If you feel everything is good, it is your body and no matter what you do I love you and stand by what you want to do."

She said: "I was in control the pill did give me energy, but didn't affect me in any other way. I enjoyed it and my body was not harmed. I am tired from the long night and physical told of doing it for so long. I would consider doing it again if I had more time to prepare for it."

I asked: "Will you be ok to go to the party tonight?"

She said: "I just need some sleep and I will get a massage to loosen any of my muscles that are tight from last night and be good to go."

The water was starting to cool off so she drained the tub and took a long hot shower. After we went to the diner for breakfast and to see Kimmie. I dropped her back at her mom's house to sleep and get more clothes.

Her mom called me several hours later and said: "She is still asleep and has an appointment for a massage in and hour. Should I wake her or cancel the massage?"

I asked: "Where is the massage at?"

Jan told me: "The guy is coming here I have used him in the past."

I told her: "Let her sleep till just before he is due to arrive."

6PM my phone rang it was Jan she said: "Come over Cheris's massage is starting and you will enjoy this guy's technique."

I went around the corner and Jan was waiting at the door to let me in. She led be to a spare bed room and I saw Cheri nude on a portable massage table. The masseur was also nude and was massaging Cheri's legs. For the next hour I sat and watched as he worked her muscles and then he worked on her tits with one hand and fingered her pussy with the other. After he made her orgasm, he pulled her by the shoulders till her head hung off the end. Next, he offered his cock to her mouth and she gladly started sucking his cock. With her head tilled back his cock easily slid down her throat. He leaned over and started rubbing her clit and as I noticed him shudder as he shot his load down her throat she had another orgasm.

I asked Jan: "How much does he charge; I would hire him for her as a surprise once in a while."

She smiled and said: "He doesn't, he does it for free so he can enjoy the sex. He always fucks me after when I suck him hard again. If you two weren't going to the party he would fuck her. He will have to settle for me instead."

I asked: "How did you find him?"

She smiled and said: "On Craigs List back when my husband started with his girlfriend. I saw his post in the personal ads offering free sensual massage for women. We even dated for a while."

I asked: "How old is he?"

She said: "He was eighteen when I found his ad, I was almost old enough to be his mother at the time."

Finished he pack his stuff and Jan led him to her bed room. Cheri came over and kissed me and told me she was going to take a shower. When she was dressed, we went back to my house to get ready for the party.

I asked her: "Did you look in your purse yet to see what the woman gave you?"

She said: "No, I forgot about it."

She went to get the purse and came back to the living room. She dumped it out on the coffee table and we were both shocked. Along with her stuff was what must have been the woman's engagement and wedding rings from her just divorced husband. The wedding band had diamonds all around it and the engagement ring diamond was at least seven carrots and had three smaller diamonds down each side.

Cheri said: "She was wearing this last night when I met her and the whole time, she was being gang banged."