Driving with Uber An Unexpected Benefit Chapter 7
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It was a Wednesday in July and Khrys had invited me to go with her to a Cubs game. She had gotten some tickets right behind home plate from one of her clients, and she knew that I loved baseball. It turned out to be a great night with the weather cooperating and the Cubs walking away with a “W”. After the game we headed to the VIP Lounge I was a member of over at Casey Moran’s, a great bar across the street from Wrigley Field.
During the course of our conversation, Khrystiana asked me if I could join her and Klara the next Saturday night for dinner at her place. She reminded me that Klara had not visited her this past weekend as she had joined friends to spend the weekend in Green Bay. The main reason for the visit was to hit up the gambling casino run by the Oneida Indians. Casino gambling had been allowed for years in the United States on Native American Indian Reservations. Khrystiana was a bit reticent about reasons for the invite but I was happy to accept. We made plans for that Saturday with me bringing the wine and the girls taking care of the dinner.
Saturday came and I found myself once more sitting with two absolutely beautiful Scandinavian women. Over dinner, I realized that while Khrys was her normal very chatty and bubbly self, her sister was not. I noticed that she seemed to be totally preoccupied and twice I had to repeat a question that I had asked her. I thought it was very odd that she did not want to talk about her weekend in Green Bay. We finished dinner and did our usual cooperative clean up. We then headed out to Khrys’ balcony to enjoy the city lights as they started coming on.
We had been sitting outside about fifteen minutes when I finally just looked at Klara and asked her if she was feeling ok. I told her that she had been somewhere else the whole evening and I was a bit concerned about her. Khrys looked at her sister and asked her if she wanted to tell me what had been on her mind that evening, in fact, what had been on her mind all week. I simply sat there a little confused as these two young women had a vague discussion about what Klara wanted to do. Klara finally looked at her sister and said, “No, Khrys, I do not want to tell Chuck what has been on my mind all week. I know that you feel I should but I do not want to. However, I have been thinking a lot about what you told me a couple of days ago and, even though I do not want to, I actually have to agree with you. Once I discuss this with Chuck and we move on, I will feel better”.
Klara stood up and walked over to pour herself another glass of wine while also offering both Khrys and me a refill. She sat down, took a sip, placed her glass on the table and then sat back on the sofa next to her sister.
“Chuck, you asked me how my weekend in Green Bay was. Actually, we had a lot of fun and Saturday night at the casino started out to be really great but it did not end up being so great. I went to the casino with $200 knowing that I could afford to lose it. I would have had a lot of fun with the cost being $200. For the first couple of hours, I won a little then lost a little but had about $250. I guess my luck changed at that point because within about an hour I had lost it all. I should have quit then but decided to go to the ATM and pull out more cash. I know that part of the issue was that the free drinks made me think I was not going to lose. But bottom line, I had soon zeroed out my checking account.
“When I woke up Sunday I realized that I had really screwed up because I had written and mailed a couple of checks on Thursday that would be cashed on Monday or Tuesday and both of them were going to bounce. I had just dug a much deeper hole for myself.”
I looked at Klara. “I don’t need to tell you, Klara, how irresponsible your actions were. It is obvious that you already know that. What did you do? How much is the bank going to charge you for the overdrafts?”
Klara looked over at her sister and then looked back at me. “Actually they did not bounce, Chuck. I called Khrys that Sunday afternoon after I got back to my apartment and she came to my rescue. She wired $500 from her account to mine Sunday evening so that it was there on Monday. Big sister to the rescue!”
“Why are you telling me this, Klara? When I asked how the weekend was you could have simply told me that you had a lot of fun but you had lost some money gambling. Almost everyone does that. Why did you decide to go into the details.”
“Chuck, I think that you know the answer to that question”.
Klara had snapped an answer to me. From the look on Khrystiana’s face, it was obvious that she was upset and disappointed in her sister.
“No, young lady, I do not necessarily know the answer to that question. If you simply wanted me to know the details, that is one thing. However, if you want me to be involved in this or if you want me to take any sort of action you need to tell me what you want.”
I saw that Klara was a little embarrassed at the tone I had taken so I softened my voice a bit as I went on.
“Klara, you are well aware that your sister and I have a very special relationship. I will admit that it is also somewhat of an unusual relationship. However, it is one we mutually decided upon and agreed upon after some very long and honest conversations. Interestingly enough, the first time that she and I actually acted upon that relationship it was over her handling of money. When we finally did agree as to how our relationship would be we came to an understanding. I explained to her that the first time she felt that she needed to be punished she would have to ask me to punish her. I do think that I know what you are leading to but I am not going to try to read your mind. Have you and Khrys talked much this week about this situation?”
Klara actually giggled slightly when she told me that this was about the only thing that they had discussed all week and that they had been on the phone a good amount each night. She told me that it was obvious to her what Khrys felt her actions should be. Khrys had very bluntly told her that she needed a spanking. She also told me that even though she agreed with Khrys she simply did not want to be spanked. She said that in the past she never had the option to not be spanked, her dad simply did it. This was different.
“Khrys told me, Chuck, that if I were to ask you to punish me for this you would probably do so even though you would prefer not to. I saw for myself when you spanked Khrys a few weeks ago that it was not something you were enjoying. She also told me that the spanking would most likely be hard and severe. She knew that from personal experience. The last thing she told me though is what has been keeping this whole mess in my head. She told me that tomorrow I would feel a lot better about the whole thing. I would know that I really screwed up but the screwup was paid for and forgiven and hopefully, I would have learned from it.”
Klara sat forward and took another sip of wine before sitting back but reaching out for her sister’s hand.
“Chuck, I really do not want to ask you to do this but I have to. Will you please punish me as you think I deserve for last weekend?”
Khrystiana decided to add some comments. “Chuck, I really wanted to discuss this with you after the game this past Wednesday but I felt I did not have the right to do that. This was something that Klara had to talk with you about and not me. I did want to forewarn you that Klara could possibly bring this up and, if she did, I wanted to ask you to please do as she asked. I really think that she needs your ‘special friendship’ right now.”
I looked at both girls and then focused on Klara.
“Klara, you saw a few weeks ago the spanking that your sister got for drinking and driving. If you really want me to step into this situation, I will do so. But before you ask again, know that the spanking you will receive will not be as severe as the one I gave Khrystiana but it will be close. Do you really want me to do this.”
“God, no, Chuck. I do not want you to do it. But I need you to do it. There is a huge difference. Please do punish me as you think I should be punished.”
I stood up and walked over to the sofa and held my hand out to Klara. She looked up at me, reached out and took my hand. I led her off the balcony and back into Khrys’ living room. Khrys followed and closed the door behind us. She sat down on one of the chairs in her living room. Klara had kicked her shoes off when she was sitting on the balcony. I stood in front of her and simply unbuttoned the front of her blouse and dropped it off her shoulders. I handed it to her and told her to fold it and place it on the table. She returned to me and turned her back to me so I could unsnap her bra which she added to the table. I unsnapped and lowered the zipper on her shorts and allowed her to step out of them and then did the same for her panties. I then told her to go face the wall with her hands on top of her head.
“I want you to think about the situation that you have put yourself into, Klara. I want you to think about how sore you are going to be in a few minutes. I also want you to think about whether your money management behavior last weekend was worth what is going on right now and what will be going on for the next half hour or so.”
I sat next to Khrys and simply looked at Klara’s rear. Her shoulders were about the same width as her sister but they tapered to an even thinner waist line before flaring out into her hips. Her bottom was a little flatter than Khrys’ but she, like her sister, was very fit and toned. Her tan lines were very obvious. Her love of sun bathing was very obvious. While I was sitting there Khrys had reached out and taken my hand.
I finally stood up and moved into the dining area to get a straight backed chair to put in front of Khrys angled so that Klara’s leg would be pointing towards her. I sat down and asked Klara to come over to me. She moved to my right side and, since I am left handed, had to bring her so that she was facing my left knee. Klara looked at her sister and then back to me. She said, “I am really sorry, you guys.”
As I reached out for her hand Klara slid over my lap. I positioned her and started rubbing her very cute backside and continued the lecture and scolding I had begun. I then brought my left hand down sharply on her left cheek and then her right. Klara jumped. I then continued the spanking bringing my hand down to cover her bottom and upper thighs as her bottom grew brighter and pinker and warmer. Outside of some mutters and some “ow’s” and “ouches” and “sorries” Klara took the spanking more quietly than her sister did. Eventually, I did stop and, very much like her sister, Klara took a few minutes before realizing that I had stopped. I helped her up and motioned her again to the wall reminding her not to rub and keep her hands up.
After a few minutes, I asked Klara to face me and put her hands to her side. She did so. It was readily apparent that she was embarrassed about standing in front of me with her breasts and vaginal area fully exposed. I asked her if she was ready for part two. She asked me if there really had to be a part two as she told me that she had really learned her lesson. Based on her body language I did not feel that she had learned the lesson I wanted to impart so I simply shook my head. Klara dropped her head. Khrys had told me that when she had told Klara about the fact that I had spanked her that Klara had asked for details. This was obvious in Klara’s next comment.
“I guess I have to go find Khrys’s slipper, correct?”
I nodded. Klara disappeared into Khrys’ bedroom and quickly returned with slipper in hand. I wondered if she had located it earlier in the day in case she needed it. She brought it to me and without any coaxing from me returned to my lap. I pulled her close and decided that I had better place my left leg over her legs based on how she had kicked when I was using only my hand. As I did Klara grabbed my right leg with both her hands and just hung on. I started with the slipper over and over covering her entire bottom and sit spot and upper thighs. This time her vocalizations were louder and her gyrations over my lap were much more vigorous. I finally felt Klara almost collapse and all the fight went out of her. I gave her a couple more spanks and then dropped the slipper.
I started very softly rubbing her now very red and very hot bottom. I kept her there until she wanted to get up. She slowly turned and sat on my lap, put her arms around my neck and started sobbing onto my shoulder. I just held her and rubbed her back letting her cry. I finally stood Klara up and she took my hand and started leading me into Khrys’ bedroom. Once again she was showing me that she “knew the routine." Khrys in the meantime stood up and told us that she was getting some ice water and towels. Khrys brought the supplies in along with the tube of aloe lotion. She whispered to me that she would be on the balcony and left the room. I stayed with Klara about fifteen to twenty minutes before she dozed off.
I headed to the balcony and realized that Khrys wanted me to stick around for a while as she had brought out a bottle of brandy and a couple of glasses. After we had sat down she leaned over to me and gave me a soft kiss on the lips.
“That is my way of saying thank you. I am sorry that we had to ask you to do this. Klara is going to be physically feeling pretty lousy tomorrow but will be better by mid-week. However, I know that tomorrow she is going to be much, much better emotionally. She has been in a real funk this whole week.”
We continued our chat for about a half hour and I decided it was time for me to head home. I told Khrys that and she told me that she had one more thing to tell me before I left and also had a request to make.
“Uncle Chuck, I had noticed a few times in the past whenever I was watching daddy spank one of us that sometimes I got a bit excited about it. I know that you are going to think that I am a pervert or something but the same thing happened tonight especially when you were hand spanking Klara. I actually got turned on some. I wanted to let you know that and hope that you don’t think badly of me.”
“Khrys, we have kind of talked about this before. I don’t feel badly about that at all and it really does not surprise me. We have talked about how there is a thin line between pain and pleasure and that spanking can be very sexual in nature. So, no, I do not. But what is the request you have of me?”
Khrystiana grinned as she looked at me.
“Klara is heading home tomorrow about 5:00. Can I come to your place tomorrow evening. I think that I need a reminder spanking.”
I laughed as I gave her a hug and told my darling young friend that I would see her tomorrow around 6:00 or so and that we would grill some burgers before getting down to business. She kissed me good night as I headed out the door.
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Hi Y’all,Well I guess you can only go so long without being recognized as the Uber driving slut mom. I live outside of Joint Base Lewis McChord in Washington state. Just yesterday when after dropping the k**s off at school I decided to turn on my Uber app and see if I could make some money before needing to complete some errands and clean the house some. Within seconds of turning on the app there was a request just down the street. It was a young guy who turned out to be late for high school...
Alice made up her mind to stop the driver and tell her husband to come and get her. Then Ann Marie’s face appeared behind Kevin. “Come on, baby! She’s gone! Let’s finish what we started.” Kevin’s phone abruptly shut off. “That bastard! He and that tramp are still going at it!” Alice pushed the driver away. She lay back in the car seat. Tears welled in her eyes. The driver was right. They were laughing at her. They all knew. They had always known. They were laughing at her behind her...
Alice collapsed in the driver’s lap with his cock on her cheek. It continued to pump his hot jizz on her face. Her nostrils filled with the musky sexiness of his aroma. She inhaled deeply. It was a narcotic, freeing her mind and lowering her inhibitions. She had come a long way since running from her humiliation at the party. She wiped the cum from her face with her open palm. The iPhone buzzed. Lost in the enormity of what she had done, she lay back in the passenger seat and pressed the...
Three Weeks Later - April 6th, 2019 (Several Weeks After The Prologue (Chapter One) (Savannah has moved in with Melanie and Brock) It’s been three weeks since Savannah moved in with Brock and Melanie. Savannah and Melanie have been stripping and driving Uber almost every day since then. The girls had settled into a daily pattern of sex and humiliation at Melanie’s trailer. Savannah only worked the motel when she stubbornly refused to obey her brothers. Savannah and Melanie worked dayshift...
So this occured a few weeks ago.I had been at a house party and called an uber to go home as I had been drinking that evening. I wasn't drunk but I was certainly in that nice buzz phase. At the time I was wearing a black lace top with a blazer over it and a leather mini skirt with a slit on my right side. I was somewhat horny as I had fooled around at the party but hadn't really done anything.So anyways my Uber comes and I proceed to sit in the front passenger seat. We make small talk and I...
Hey Y’all,It’s been too long. It’s not that I haven’t been having naughty fun. It’s just that I haven’t been sharing it with you except maybe on my Twitter. But today I had some fun I just had to share. It was the nasty, naughty type of fun that I love!Since moving up to Kirkland, WA I’ve started to pick up people from Paine Field a bit, as a way to get longer Uber rides. Most people are going to places like Kirkland and Bellevue so it makes for nice long rides as well as great tips.Today was...
Hi Y’all,A quick story of a quickie I had with a Uber rider last night. I don’t normally work Friday nights but we’re trying to save up to take the k**s to Disney this summer and see the Star Wars Galaxy’s Edge opening. So I decided to work the evening and see if I could get some good tips from the happy hour crew.Around 7PM I got lucky enough and picked up a very cute guy in his 20s from Bellevue Brewing which looks more like it should be a dentist office then a brewery but I guess you serve...
Hi guys im a cd from Orange County and i had the sex ever last night with someone I never expected. So it was around 1 and i had just soent the night with my “friend” well I had just blew him and watched a movie and he got me an uber so i kissed him and left when tge uber came and I went on my night. He told me it was a white truck and espanic i went in and told me my “friends” name and we drove off. It wasnt even 10 seconds and he said what was my name i told him i was “. “ and he said nice to...
So, I don’t know where to start. It was a Friday night and I was on a date with a guy I met earlier that week. We went out to dinner (where I had too many drinks) and then we decided to go to a bar afterwards. I didn’t really like my date too much, maybe it was because I had so much to drink and he was just boring. Either way, around 1am I decided to call an Uber to go home. My date didn’t like that too much. I was waiting in the parking lot and of course my date was trying to get me to stay...
Oh, it's a lesbian couple, how sexy? A hot light brunette with a pretty dirty blonde," I muttered, pulling up to them."Thank you for coming," the blonde said, getting in the back first."You're welcome. I'm Cynthia," I introduced myself as the brunette got in as well."Cool," the brunette added, before kissing the blonde. "Why are you staring? Do you not like lesbians?""Oh, no, of course not," I made clear, putting my hands up a bit. "You're both just stunning if that's okay to say," I...
Voyeur"Oh, it's a lesbian couple, how sexy? A hot light brunette with a pretty dirty blonde," I muttered, pulling up to them. "Thank you for coming," the blonde said, getting in the back first. "You're welcome. I'm Cynthia," I introduced myself as the brunette got in as well. "Cool," the brunette added, before kissing the blonde. "Why are you staring? Do you not like lesbians?" "Oh, no, of course not," I made clear, putting my hands up a bit. "You're both just stunning if that's okay to say," I...
LesbianSame Day - April 6th, 2019 (Melanie’s Big Sister Nicole and her Nephew Jonathon have arrived) “Hi Sis, I brought wine!” Nicole smiled and held up a bottle of zinfandel. “You also brought luggage,” Melanie observed that her sister had come to stay. Nicole giggled and reminded Melanie that she was naked. Nicole was covering her son Jonathon’s eyes. “Are your neighbors going to mind you standing in the doorway like this?” Nicole asked with a twinkle in her eye. “You’d be surprised,” Melanie...
It had been three long, grueling months since Nicole visited Melanie. Today just like almost every day since Nicole’s arrival, the three women were naked on beach chairs positioned behind the trailer. The only thing they wore were black leather dog collars emblazoned with the Warlock emblem and the names Dimbo, Savannah, and Nic-Hole. The beach chairs were new. They could afford them because between the three women, they were earning quite a bit more now stripping and turning...
Hi Y’all,From time to time I meet a guy that while I didn’t suck or fuck them initially, I stay in touch and eventually have fun with them. That’s exactly what happened with a guy I met named Tom. He is probably in his late 50s or early 60s but in great shape and very handsome, in a refined way. He told me he use to be in the Navy and flew F-14s and he looks exactly like that kinda guy. I met him while Ubering and didn’t admit any of my slutty ways to him until we started to exchange emails and...
Hey guys, I am Nikhil and I am back with my new sex story. For those who haven’t read my last stories, I am a 21-year-old boy living in Kolkata. I am six feet tall, milky white in colour and my dick size is 6.3 inches. I have always been interested in matured women as their boobs are always so firm and curves are indeed attractive. So, one fine day, I was waiting for the cab to arrive at the roadside and to my surprise, this woman in her late 30s was sitting in the car at the backseat. Let me...
Justin pulled up outside the club, looking at all the people standing around outside. There were all shapes and sizes of women, dressed in all ranges of sexiness. As he parked he spotted a young blonde girl looking around as if she were waiting for a ride. In your dreams, he muttered to himself. She was standing with another woman a few years older than she, and Justin noticed they were both very hot. The blonde had on a very short red cocktail dress that clung to her petite frame and the...
Oral SexHey Y’all,Thanks for all the encouragement to finish the story of the guy I met while driving for Uber and blew outside the old Candlestick Park in San Francisco. After that dominant fun, he asked if I’d like to join him back at his place for even more fun. I was so horned up that I wasn’t about to resist.He had a nice walk up condo close by and he didn’t waste any time once I walked into his place to get back to business. He was ordering me to lean over a desk with my boobs pressed flat...
We went out Saturday night and went to a few bars. She was dancing all night and we had a few guys that she was really getting along with and when they found out we were looking to have a threesome they got freaked out. She was super drunk and extremely horny by the time we left the bar. At around 3 we called an Uber and waited outside for it. She was that level of drunk were she just wanted to touch and kiss and was really suggestive in her comments to anyone and everyone that would listen....
So after drinking a little too much to walk back to my hotel in Salt Lake City I decided to call an Uber and be safe, some of the downtown areas of SLC can be a little seedy after dark. My driver showed up and he was a very upbeat and clearly a feminine like guy of no more than 21 or 22. He was in a very good mood and wearing very short shorts, like retro gym shorts when I was a k**.After pleasantries I said to him those are short shorts!! How does your cock not fall out! He laughed and said it...
I’m retired, but I’m also an Uber Driver. I work a few hours a day to supplement my income. Mostly local trips with occasional long trip here and there. On this one particular day I got a notice from the app for a pick up near where I was. So I drive to the location and I see a man on the side of the street and he his waving at me so I assume he’s my ride. He appears to be a fit gut in his forties. I pull up and he comes around and gets in the passenger seat next to me. It surprised me a bit as...
Hi Y’all,Last weekend I was contacted by Tom my retired Navy pilot friend who had gangbanged me with a group of his older friends. He asked me if I was interested in some more fun but this time it would be to dance and have some fun at his son’s private high school graduation party with a select group of his son’s friends. That was a wild offer and while I couldn’t imagine my own k**s having such a party I had heard of dads taking their sons to whore houses and figured I could likely provide...
'Would you like me to suck your cock?' I asked my sexy Uber rider.It was out of the blue but I was so horny and he was just too sexy not to ask. Besides we’d been flirting since he got in my Honda.'I would love that.'Without hesitation I was making the slide into the back seat that I’ve become addicted to. In a fluid motion I was landing next to him, unzipping his pants and pulling out his cock like I the practiced slut I am.My rider took a sigh and sat back as he played with my ass while I...