Cheri Ch. 02

Once the diner closed and Kimmie finished what she needed to do to clean up. The three of us went to a nearby restaurant for dinner. Before going back to my house to begin the evenings activities.

Once we were in the bed room and all naked, I asked Kimmie: "Cheri told me you have Viagra and was bringing me one so I hopefully last the night."

She said: "Yes, but let's wait till later when you will be needing it before you take it."

I went to turn down the lights when Cheri stopped me and said: "Leave them on, I want you to be able to be able to see with a clear view."

They then started to make out and feel each other's tits. Kimmie pushed Cheri back on to the bed and kissed her way down her body. Stopping at Cheri's tits to suck each of her nipples. As she did that, she started to finger Cheri's pussy which caused Cheri o start moaning. I moved down on the bed to get a better view of Kimmie fingering Cheri's pussy. She had two fingers in her pussy and was using her thumb on her clit.

Cheri was breathing heavy and said: "I am close oh fuck that is good, harder make me cum."

Not half a minute later Cheri said: "Fuck yes, I am Cumming don't stop."

She had the biggest orgasm I had ever seen a woman have. It went on for over a minute when suddenly, she ejaculated. I didn't know women could do that. At first, I thought she lost control and pissed herself. Till I noticed it didn't look like pee. Kimmie let her calm down before she started to lick and suck Cheri's pussy and clit. She made Cheri cum several more time before taking a break. These were not as strong as the first one but Cheri wasn't complaining.

Kimmie said to her: "I guess you like having a woman pleasure you like that?"

Cheri through dreamy eyes looked at me and said: "I love your cock and what you do to me with it and you are great at eating pussy, but that was on another level. Did I wet myself?"

Kimmie told her: "No, you squirted it is the same as the fluid that lubes you when you are turned on. Some woman pee as well when that happens, you didn't, but if I didn't stop when I did you may have. So, are you ready to return the favor?"

Cheri said: "I would be and asshole if I didn't after what you did to me. You need to tell me what to do."

Kimmie told her: "Just do to me what you like being done to you. Believe me it will come naturally to you, it does to all women."

Kimmie laid on her back and when Cheri went to go down on her. Kimmie reached for her and pulled her to her so, they could kiss. Cheri caught on that Kimmie wanted foreplay like she did to Cheri. The seine repeated with the roles reversed. Kimmie didn't squirt, but she did have powerful orgasms. Cheri looked possessed the way she feasted on Kimmie's pussy. I began to worry I would become a secondary player in Cheri's life. When Kimmie was satisfied they headed to the shower.

They returned and Cheri started to suck my cock as Kimmie watched and used a vibrator on her clit. Then Cheri had me lay on my back and mounted my cock. I loved watching her tits bounce and she rode me. She leaned over so I could suck her nipples.

Then she surprised me when she told me: "Bite them pull on them with your teeth."

I wondered was she one of the women that enjoy pain with her sex. I was not sure how I felt about hurting her like that. I did as she asked, but I didn't bite hard more like a gentle bite and pulling. She seemed to enjoy the way I was doing it and I felt she wanted to more for the stimulation than to be in pain. WE changed positions every time I was close to blowing my load. We had been going at it for about half an hour when I told her I couldn't hold back any longer. She was back on top in reverse cowgirl. I felt movement on the bed and realized Kimmie was down between our legs. I shot my load and filled Cheri's pussy. As I stopped shooting cum, I felt Kimmie pull me cock out of Cheri and start sucking me clean. Then she started eating my load out of Cheri's pussy. They went to shower, but before they did Kimmie gave me the pill to take.

I was relaxing thinking, here I was in my fifties having sex with a woman twenty years my junior and a second woman also younger than me by I don't know by how much. Dam how old is Kimmie I needed to find out. She had been at the diner for several years so she was certainly in her mid to late twenties. Guys my age are extremely lucky to ever be with a woman as young as Cheri without paying for it and here I am with two. One of which maybe only in her twenties.

When they finished in the shower and joined me back in the bed room, Kimmie said to Cheri: "See I told you the pill would get him hard for us again."

Cheri said to me: "Lover boy how would you like to have your cock in my ass while Kimmie fucks my pussy with her strap on?"

I said: "I thought you said you need to clean out before I could fuck you there?"

She told me: "First that is what took so long and second, you are not fucking me she is. You will just be in my ass feeling me being fucked. Kimme say most guys like it and they cum."

I'll try most anything once so, why not, I said: "Pass me the lube and Cheri bend over so, I can lube your sweet ass."

Cheri smiled and said: "You say the nicest thing to me."

Kimmie asked: "Is that the only thing sweet about her?"

I replied: "It is only one of the things sweet about her."

Cheri asked me: "What else do you like about me?"

Most guy may feel on the spot, but I knew everything I liked, no loved about her and said: "Your brain, you are the smartest person I know, your body is fantastic. You are the most sexual free spirt I have ever encountered. I hope to spend the rest of my life with you."

She said: "Wow, you don't think my tits are too big. or that I am a slut?"

I told her: "Your tits are perfect as far as I am concerned, and you are no slut. What you are is a woman in control of your sexuality, that is one of the many things I love about you."

She then said: "You said you want to spend the rest of your life with me, is that a proposal?"

I told her: "Even before we had sex together, I fell in love with you. If you will have me, yes, I want to marry you."

She hugged and kissed me and said: "Yes, I will marry you, but you should know my tubes are ties. I won't be able to give you any babies."

I told her: "I had three, even though I lost Jack I have the twins and you have your son, obviously you were not looking to have more kids. How do you think your mom will react to it?"

She told me: "Before we had dinner, mom told me she thought you would be a good match for me. She didn't say husband, but she did say partner. "

I said: "I don't think your dad would be happy about it if he was still alive."

Cheri said: "You're probably right my dad wouldn't, but my father has no say about it."

I said: "I don't understand?"

Kimmie said: "I will leave you two alone."

When she was gone, Cheri told me: "Mom got knocked up the night of her prom by the guy she was with. When he found out he skipped town and we have no idea where he is or if he is still alive. I was five when mom met dad and he was a widower with two daughters. Leanne was three and Sue was almost one. His wife died in child birth having Sue. Someone broke into our apartment and Dad was the first cop to respond. A week later they ran into each other at a coffee shop and he paid for her order. To thank him she invited him to dinner. He told her he had two small daughters and didn't know if he could get a sitter. Mom told him to bring them and soon after we moved into his house and a year later, they got married. Mom wouldn't let him adopt me because she would lose the financial aid and health care, she was getting for me."

I said: "Your mom and my ex-wife were close and Laura never mentioned that."

She said: "I doubt mom ever told her, in fact she most likely would be upset I told you."

We went to find Kimmie and found her drinking wine in the kitchen. I poured us each a glass and we headed back to the bed room.

Kimmie said: "Are you ready to feel me fucking her with your cock in her ass?"

I just nodded my head and laid on the bed face up. Cheri straddled my legs and guided my cock into her ass. She sank down slowly till my whole cock was up her ass. Then Kimmie got between our legs and guided the dildo into Cheri's pussy. I immediately felt the dildo sliding he Cheri's pussy, it was putting pressure on my cock through the membrane separating Cheri's pussy and asshole. The feeling was incredible and I knew what Kimmie said was true, it would make me cum.

Cheri was very vocal saying: "Fuck me, I never thought I would love cocks in my cunt and ass together, I need to have a real cock in my cunt next time. I wish there were more guys here to fuck me."

The woman I love just informed me she wants to have multiple men fuck her in her pussy and ass together. She wants to be gang banged and I had a feeling it will not be a one and done. Then I realized I was about to cum and it wasn't from just my cock feeling Kimmie fucking her. It was also the thought of her being gang banged. There it was I love her being a slut and that she would be my slut wife. I knew then if she wanted to do sex shows online for money, I not only would be ok with it, I want her to do it. Any money she makes will be hers I don't want it or need it. We will need to have separate finances, so if she crosses a legal line they can only go after her money. Then we will still be ok financially with my income.

The house is protected by the trust that owns it. My income comes from three trusts, my grand parents' individual trusts and my parents' family trust. I also start taking my pension when I turn sixty-two. When my employer was bought out, I accepted a buyout instead of moving to another state. I invested it and I am getting a monthly return I have been using. That coupled with a Cheri's disability from the service, and her pension which I don't think can be attached. We would be all set money wise.

I came twice before Cheri told Kimmie she needed a break. My cock was still hard, I knew I needed to call my doctor to get a scrip for more pills. Cheri and I went to take a shower, when we came out the door bell was ringing. Kimmie said: "I got it." We went to the kitchen as Kimmie also got there carrying a pizza, she was nude.

I asked her: "Did you answer the door like that?"

She said: "I always do if I am naked and I let him finger my cunt as a tip."

Cheri asked her: "I know I said cunt while you were fucking me with the dildo, but I don't usually use that word. But you always use it why is that?"

Kimmie told us: "Women like yourself that have sex with a lot of different people are sluts and sluts have pussies. Women that fuck for money are whores and whores have cunts. I work part time as an escort which part of that job is to have sex with the client in exchange for cash. So, I am a whore and have a cunt."

Cheri asked her: "How much do you make for a date?"

Kimmie said: "The date part is three hundred and hour, one hundred to the agency and I get two hundred. An all nightery is fifteen hundred,"

I asked her: "Then why do you work at the diner?"

She said: "Two reasons, I only work as an escort once or twice a week. That is all I can stand having sex with pompous asses. The other reason is I own forty percent of the diner and I love the inter action with the customers."

Cheri asked her: "If you had to give up one, which one would it be?"

Kimmie said: "Easy, I would stop being a whore. I only started when my mother became sick and needed twenty-four-hour care. It was the only way I could afford it. Mom past a year ago and I just do it as easy money to put aside for when I retire someday."

I was wondering about Cheri's interest about Kimmie being an escort. Was she considering do it herself, if so, how do I feel about it. Laura was a whore and I couldn't accept it, but she was a drug addict and cheated on me. If Cheri decides to try being an escort, she wouldn't be hiding it from me. The other thing was Laura brought it into our home, not only the whoring, but the drugs. The fact that I was paying rent and the house was owned by the trust it was safe from being seized. This was a totally different situation. My ex was like a two-bit whore, Kimmie is like a high-class call girl. Then I realized, I already told her I was ok with her having sex with others. What's the difference if she can make money doing it, if she was doing porn, it wouldn't be much different and I know I would be ok with that. Tomorrow, I need to have a talk with her so, I know what she is thinking.

I was brought out of my own mind when I heard Cheri said to Kimmie: "My mom does sex shows on the internet and is making a ton of money and she doesn't have to have sex with anyone. You could do that instead."

Kimmie asked her: "How old is your mom?"

Cheri told her: "She is fifty-two, but looks like she is in her mid-thirties. Her tits don't sag and her body is toned. I guess she would be considered one hot MILF."

Kimmie said: "Help me out here, you did twenty in the service and your mom is only fifty-two. Even if you were eighteen when you went in and she had you at the same age. She would have to be older."

I knew Cheri entered the Air Force Academy when she was sixteen, but her mom should be older.

Cheri told: "I was double promoted twice in elementary school and my service time started when I entered the Academy. Mom was double promoted three times by the time she graduated high school. She lost her virginity prom night and nine months later I was born. I did twenty-one and a half years."

I knew her mom looked great for her age, now I know why she is young than I thought and must take extra good care of herself. Cheri was right her mom could pass for mid-thirties. But hearing what she looks like under her clothes I would love to see one of her shows.

It was time to get back down to business, the pill hadn't worn off and I wanted to continue enjoying these two hot naked women.

I said: "Junior is still looking for action with you two hot ladies."

Cheri said: "Since I have you in that condition, tell me. Would you be ok with me doing sex shows on the internet or maybe trying escort work?"

It wasn't fair for her to ask me that now. Kimmie was sucking my cock and I wanted to cum so bad.

I told her: "Not fair ask me when we are done for the night. I am so worked up I might agree to what ever you want without giving it the thought it needs."

She said: "That is why I am asking you now."

I thought want did I want from her if I say yes it took me a bout five seconds to know what I wanted. I told her: "Arrange for me to watch your mother's next internet show."

She laughed and said: "I had already asked her to let you watch. Harry was there and thought it was a great idea. In fact, he said she should let you fuck her tits during the show. Tell you what, if you say it is ok for Kimmie to arrange an interview where she works as an escort. You can fuck her if she lets you."

I told her: "I am ok with it, but I will not have any type of sex with your mother. I am good just watching."

She said: "That was easier than I thought it would be. What can I do now as a reward for you being so understanding?"

I said: "I need time to think about that, how about a rain check for now."

Cheri asked Kimmie: "What was the wildest thing you were ever ask to do as an escort?"

Kimmie said: "The wildest was a guy wanted me to teach his twin daughters how to pleasure another woman. The weirdest was an Arab Prince offered me ten grand to suck and fuck his dog, I passed on that one."

Cheri asked her: "Did the guy watch you with his daughters?"

Kimmie said: "No, in fact it didn't happen till he was out of town. He doesn't know it but his girls are now working as escorts with female clients."

I asked: "Why are they doing it, their dad must be rich so they don't need the money?"

Kimmie told us: "They do it because they know their father would be embarrassed if it came out. They both hate him, their mother was his mistress and he has never been a father to them. That and the fact that several of their clients know their father."

Cheri asked me: "Would you feel better if I only did female clients or maybe couples?"

I told her: "I have already accepted we have an open relationship. Saturday night we are going to a swinger's club with Leanne and her husband. You and I are going to have sex there with other people and I one of them is your sister. The difference between that and you being an escort. Is one you have sex just for the pleasure and the other you are compensated for the sex. Ether way you will be having sex with other people.

I know what I want you to do as my thank you. Get my phone so I can record you helping Kimmie suck me off. When I cum I will paint her face with it and then I want you to lick it off and swallow it, while I record it on my phone."

After that we called it a night. Kimmie stayed over and slept in the bed with us. I woke up to movement around three thirty in the morning. I looked over to see Cheri with her face buried in Kimmie's pussy,

When they noticed me, I said: "Don't stop on my account, I presume you will switch places at some point, just remember I will need the same treatment when you two are done with each other."

Cheri never even looked up, she just kept eating Kimmie's pussy. Kimmie said: "I already took care of Cheri. Besides I have to get ready to go to the diner soon."

Kimmie had two orgasms before going to take a shower. Cheri moved over and swallowed my cock. When I came, she lifted her head and opened her mouth to show me the cum. Some dripped back down on to my cock. She swallowed what was in her mouth an engulfed my cock again to clean off what had dripped on it.

She moved up and we cuddled as we went to sleep. She woke me up at nine thirty and handed me a cup of coffee. She then headed to the shower. I drank half and went to join her.

We dressed and were at the diner around ten, the morning rush was over and the only others that came in were picking up take out orders. Kimmie took our orders and after we finished eating, she came over to talk.

Cheri said to her: "Thank you for last night and this morning."

Kimmie said: "I love being with a woman for her first time. Am I still making the call for you to have an interview to be an escort?"

Cheri turned and looked at me, I told her: "The decision is yours; I stand by what I said last night."

Cheri said: "Make the call before I change my mind and chicken out."

Kimmie went to make the call, she cam e back ten minutes later and said: "You have an interview in half an hour. They want to see both of you together."

I asked: "Why do I have to go; I am not looking to be an escort?"

Cheri asked: "There are more than one, I think talking about this with two guys will be to intimidating."

Kimmie said: "They are a married couple and she is also an escort that happens to own the business with her husband. She wants both so they know he is aware of what you will be doing. Married women and women with boyfriends must bring their partner to the interview. It avoids problems if the partner wasn't aware of what she is doing."

We left my car and took a cab to the address Kimmie gave us. It was a multi-story building on Boylston Street between Clarendon and Dartmouth Streets. The office was on the top floor. When we entered, we were met by a receptionist, she was young and well dress in what I think is called sexy sheik I had a feeling she hadn't turned twenty yet she looked so young.

She told us: "Have a seat they will be with you shortly."

A few minutes later a buzzer rang at the receptionist's desk, she said: "You can go in now,"

She pointe to one of the two doors to the side of her desk. I opened the door so Cheri could enter first and heard her say: "Oh."