Driving With Uber, An Unexpected Benefit, Chapter 11 free porn video

I had left Khrystiana’s place around 11:00 after having witnessed a totally unexpected turn of events after the dinner with Khrys and Klara, Khrys’ younger sister.  Klara had been very hurt by Khrys’ lack of confidence in her when she arrived at the beginning of the summer.  Klara decided, in front of me, to give her sister a very thorough and intense spanking.

Some background information would probably be useful.  Khrys had moved to the United States a couple of years ago after taking a job with a US firm as a cybersecurity specialist.  We had met when I had picked her up as a passenger while driving for Uber.  I had started doing that following my early retirement before I turned sixty.   During our conversation she had mentioned that she was heading to the bank because she had messed up financially.  I had teasingly told her that she should be smacked for that.  That tease turned into Khrys and I getting together a few times and getting to know each other.  Ultimately Khrys asked that I become sort of like a ‘strict uncle’ for her and be willing to spank her, seriously spank her, when she made serious mistakes.  Eventually Khrys had realized that she got turned on by spankings.  On occasion she would receive a reminder spanking.  At times, those reminder spankings turned into some sexual play between us. 

When Klara had come to the states for an internship between her college junior and senior years, we had met.  Khrys had been upfront with her sister about our relationship.  At least, a part of it.  She told Klara that I was a discipline figure for her.  However, she did not tell her about the reminders, playful spankings and sex play.  When Khrys finally told her a couple of months later, Klara had been upset.  Because of this Klara had decided when I was over for dinner that her sister needed to be given a very serious spanking.  Klara had done so in front of me to add to her sister’s embarrassment.  As I was leaving that night I had gone into Khrys’ bedroom to check on her and tell her goodnight.  She suggested that she might like to get together for drinks one night soon.

I got a text from Khrystiana on Wednesday asking if we could meet after work on Thursday. She indicated that she was heading to the West Coast on Friday for a weekend of sight seeing and work meetings on Monday and Tuesday.  We decided to meet once again at ‘Signature Room on the 95th’, a bar on the Chicago Loop with a great view of the Lake.  It was one of our favorites and we had celebrated Khrys birthday with dinner there.   We agreed to meet at 6:00 and Khrys told me she had to leave by 8:00 so she could pack for her flight the next morning.  I was anxious to get together with my friend so I could first of all find out how she was doing.  I was also very curious as to what she thought about the actions her sister had taken on Saturday evening. 

As expected, Khrys showed up about fifteen minutes late.  I got the attention of Tom, the bartender, and he started fixing Khrys a very dry, Bombay martini.  By the time he was pouring it Khrys had come over to me at the bar and kissed me on the cheek.  The host was holding a small somewhat private table for me so we headed over there.  I always got a kick out of being out with Khrys in public especially when she greeted me so affectionately.  I am a guy on verge of being sixty and more or less average in appearance.  Khrys was a young lady of twenty-five who on a scale of one to ten was maybe a twelve to fifteen.  She always dressed to kill and tonight the business suit she had on was a real complement to her figure.  I enjoyed the guys in the bar following Khrys and I with their eyes as we headed to our table.  I knew that the question in each guy’s head was ‘what does she see in him’.  I had to laugh to myself as I thought ‘if they only knew’.   What Khrys saw in me was a very good friend who had no problem in baring her bottom and giving her a very intense spanking when she had screwed up

The very first thing I asked her after we sat down was how she was doing.  She knew that I was concerned for her.  She smiled and told me that she was glad that the seats on the jet were padded.  She laughed as she told me that her bottom still had a couple of marks from the belt.  She also advised me that she was really sore on Sunday and that even today, five days later, her bottom still tingled some. 

We changed the subject to her upcoming West Coast trip.  Khrys had spent some time in San Francisco before (who in high tech in the States can avoid trips to the Bay Area?).  She loved the city and had made a couple of good friends there.  She was staying the weekend with one of them.  All of her previous trips had been during the week and filled with business meetings. Therefore this was going to be the first to give her a chance to visit Napa and other ‘touristy’ places.  Khrys was super excited about the trip.  I had spent a lot of time in San Francisco during my career.  We talked about a number of places that I especially liked.  I was amused when Khrys brought out her iPad and started making notes telling me she was going to discuss these suggestions with her friends. 

Before I knew it the time was about 7:30 and I had not even broached the subject I was most curious about. 

“Khrys, I wanted to find out from you what your thoughts were about this past Saturday evening.  I was literally shocked when Klara told you that you needed to be spanked.  I was more shocked when she actually went through with it.  Also, I was very surprised that you did not argue with her, try to talk her out of it.”

Khrys smiled as she looked down at her martini.  “Chuck, I was shocked as well.  This was not the Klara that I have known.  I don’t mean to say that Klara has not been possibly more aggressive than I have been.  I think that she has.  But this really surprised me.  However, I really did not realize how much I had hurt her.  Klara and I have always been very close.  In the past we have shared anything and everything.  She talked with me a lot about the idea of her losing her virginity with a guy she was dating.  The day after she lost her virginity she was desperate to tell me about it.  She has trusted me implicitly with everything, and I had reciprocated.  When she started telling me that she really could not understand how I could have told her about our relationship but not told her everything, I could see how much I had truly hurt her.  You say that you were surprised that I could not argue with her about the spanking.  The reason I could not was because 100% of what she had said had rung true.  I could not argue with her that I did not deserve to be punished for my lack of confidence in my sister given our history.”

“I also was thinking a lot about what she had said about the need of an emotional release once you do really mess up.  You and I have talked about that a lot.  After Klara’s trip to the casino, she and I talked about it a lot.  I had convinced her that unless she accepted a spanking from you she was going to feel horrible for a long time about that issue.  I realized that she was telling me that if I did not have an emotional release then I would be worrying about and carrying the weight of my guilt on this for a very long time.  I am absolutely certain that she was right about that.  Before Klara headed back to Milwaukee I hugged her again and thanked her again for taking matters into her own hands.”

“Uncle Chuck, I have been thinking about this a lot this week since Saturday night.  I came to the conclusion that Klara was absolutely right I in spanking me for not trusting her, for  my hurting her like I did.  I also came to realize that I had not been honest and fair with you.  I had told you that I had told Klara about the ‘uncle’ side of our relationship.  I had told you that I would eventually be telling Klara about the reminder, playful spankings.  I had never asked you about or told you that I would also tell her about our sexual relationship.  I did that without your knowledge or ok.  I know, I don’t think that I needed your ok but I absolutely should have told you that I was going to discuss this with Klara.  I should have asked for your advice.  I did not and that was wrong of me.”

I looked at my friend and replied.  “I agree that you did not let me know you were going to do that.  But Khrys, the punishment that Klara gave you is also sufficient to absolve you of not telling me in advance.  I have told you more than once that if there is an action that deserves a real spanking then a spanking should be given.  The severity of that spanking should depend on how serious the infraction was.  You have been spanked and spanked well by Klara for your actions.  You do not deserve to be spanked a second time for that.  I honestly do not think that we need to go there.”

“In this case, Uncle Chuck, we are going to have to agree to disagree.  We do need to go there.  During this whole mess I was thinking only of me.  I did not think of Klara.  I did not think of you.  You will never believe how upset I am about this whole mess.  I am no longer concerned about Klara.  That issue is very well taken care of.”

I had to grin as Khrys, while saying that, leaned forward and rubbed her bottom some.

“However, the issue of my ignoring you in this whole situation is not.  What we are talking about are two totally different things.  On the one hand, I hurt Klara very much and I have been punished for that.  Rightfully so.  On the other hand, I was not open and honest with you.  I should have been.  I consider myself very lucky that I did not upset you to the point that you decided this would affect our trust.  You need to punish me.  You need to spank me.   Knowing you like I do, I know that the reason you are saying that my punishment was sufficient is because you do not like to give punishment spankings.  I know that you do not.  I do not like receiving them.  But I think that I have to ask you to do this.  You have every reason to say no to me and tell me that Klara’s spanking was sufficient.  I will accept that.  However, I am going to carry this guilt with me for a very long time.  I would much rather have that cathartic release we have talked about.   I need to have this guilty feeling eliminated.  I know of only one way that will happen.”

I looked at Khrystiana and actually felt some tears forming in my eyes. 

“You are really going to make me do this, Khrys?”

“Uncle Chuck, let me ask you three simple questions.  The first of which is can you understand why, based on my actions, my sister felt that I needed to be punished?”

“Yes, Khrys, I do.”

“The second one is this.  Did I to some extent break our trust by not discussing with you before hand that I intended to talk to my sister about our sexual relationship?  And, Uncle Chuck, that is a yes or no answer.  I do not want to hear a ‘yes, but….’”

“Yes, Khrys, only to a small extent you did.”

“Uncle Chuck, I told you that was a yes or no question and no buts.  That means your answer is yes.  My last question is this.  Is not our ‘uncle/niece’ relationship built on our commitment to each other that if I do something that in either your opinion or mine deserves punishment, then you will give me a proper spanking?”

“Yes, Khrys, it is.  I think that you also just gave me an answer to the question I asked.  You really are going to make me do this.  If that is the case, I know you have to pack tonight but do you want to take care of this tonight.  I would much prefer that than to putting it off.”

“Uncle Chuck, I would much prefer to getting it over with tonight.  But I cannot.  I have too much to do tonight.  I get back from San Francisco Wednesday.  Can you come over for dinner next Thursday?”

“Of course I can, Khrys.  But you are going to have a very busy schedule next week and will be traveling almost all of Wednesday.  Would you not rather come to my place and let me plan the dinner?”

Khrys grinned at me as she answered.  “Of course, I would much prefer coming to your place.  But in realizing how our evening is going to end I really do not want to have to come back home afterwards.  I would much prefer that after we are done you tuck me into bed and then you return to your place.  You and I both know that there will not be any ‘fun’ after this spanking.”

At that point, I asked Khrys if she had told Klara that she was going to ask me to punish her.  Khrys told me that she had come to this decision Sunday night after Klara had left to go back to Milwaukee.  Klara had called Khrys yesterday, Tuesday, and Khrys had told her then. 

“What was Klara’s reaction, Khrys?”

“She told me, Uncle Chuck, that she did not feel that I needed to be spanked for it.  But she also told me that I was the only one who could decide that.  She told me that if I really did feel guilty about it then I should go ahead and ask.”

We both had sort of sad expressions as I agreed that we would have dinner at her place one week from tonight.  We changed the subject and finished our drinks.  It was a couple of minutes after 8:00 when I paid the check and we walked out of the lounge.  Before I headed to my car, Khrys gave me a kiss on both cheeks and a hug. 

“I am sorry that I had to ask you to meet with me tonight so that I could make this request.  I know that you believe me when I tell you that I did not want to ask.  I know I hated to ask and I know that you hated to hear it.  But let’s not worry about it until after dinner next Thursday.  I am certainly going to try to keep it out of my mind until then.  Thanks, Uncle Chuck.  I do love you.”

Over the next few days, I tried not to think about what the next Thursday was going to bring.  Khrys and I both knew very well that we each really enjoyed the ‘reminder’ or ‘playful’ spankings that I gave her.  I even enjoyed them that much more the few times that sexual play had been involved.  Khrys was an extremely sensuous woman and was constantly amazed at how spankings could get her so aroused.  At the same time, both Khrystiana and I knew  that we really disliked the punishment spankings.  I had been hoping that the one I gave her a few months ago for her drinking and driving would be the last real punishment spanking I had to give her.  Obviously that hope had gone out the window.   I myself was amazed at how much I could enjoy an act so much but actually hate it when the only difference was a mental one.  I would have been ecstatic if after drinks the previous Thursday we had arranged for a playful spanking date once she got back from her trip.  However, it was just the opposite.  I was not looking forward to what was going to happen after our next Thursday dinner.

I got an email note from Khrys Monday morning that she had sent the night before.  She told me how much she enjoyed San Francisco and had a lot of fun with her friends.  She promised to give me all the details at dinner on Thursday.  She had spent the evening in her hotel getting ready for her meetings and presentations for today and tomorrow.  She commented on the fact that she had been so busy that she had not really been able to spend much time thinking about Thursday night.  She told me that as she had gotten into bed she did start thinking about it and also started thinking of me.  She had decided to drop me the email.  With a smiley face emoji she said that she was looking forward to seeing me for dinner but, with a frown face emoji,  was not looking forward to desert.

On Wednesday evening there were a bunch of us guys in the smoking section on the patio by the pool enjoying a game of poker, some drinks and some cigars.  My cell rang and when I saw it was Khrys I answered and asked her to hold for a minute.  I finished the hand and excused myself.  All of the guys there had met Khrys at some point or another (as had a number of their wives).  When I mentioned that it was Khrys and she had just gotten back from the west coast the comments started flying.  I laughed and headed off to talk privately with my friend. 

She told me that she just wanted to let me know that she had gotten back that afternoon and had gone to her office for a couple of hours.  She had, on the way home, decided to pick up some items for our dinner for tomorrow night.  I could see her smiling as she told me that she wanted me to know we were having steaks for dinner so that I could bring an appropriate wine.  I knew right away that this meant she was hinting for a very hearty Malbec she preferred.  She also wanted to tell me that she would be home by 6:00 and wanted to know if I could get to her place between 7:00 and 7:30.  I agreed that would be perfect and told her that I was looking forward to seeing her.  She ended the call with a “Thanks, Uncle Chuck.  I will see you tomorrow.”

After hanging up I sat there for a few minutes before returning to the game.  I was very much looking forward to seeing and spending time with this young lady whom I had become so fond of.  But I was depressed over the fact that our evening was going to have to end with a punishment spanking.  It would have been so much better if we could have ended up in a different way.  There were times when I had wondered whether this idea of being a ‘strict uncle’ was really a good one.  Tonight I felt that it definitely was not.  But I also realized that there was nothing I could do about it.  I had made an agreement with Khrys that we both felt was positive for her.  But it was an agreement that at times we both hated.  We had discussed that a couple of times and each time we did came to the same conclusion.  This relationship fit us perfectly.   Khrys also felt that this type of relationship might be ideal for her sister if Klara did take the job in Milwaukee.  I had told Khrys that I did not know if I could handle two ‘nieces’.  Also that was so far in the future I did not want to even think about it.

I took the L to Khrys’ place the next evening.  It was early August and I could not believe the weather.  It was much more like an October evening.  The humidity was very low and the temperature was in the mid sixties.  I knew that I would not want the hassle with the other folks in the L later tonight as I knew that I would not be in a very good mood.  I had already planned on calling for an Uber driver.

Khrystiana greeted me at her door with a very enthusiastic hug and a lingering kiss.  She looked great.  She was wearing loose silken cream colored slacks with bright blue sandals.  She had on a  blousy bright blue buttoned shirt.  Her hair was in pig tails (which I always thought looked adorable) and just about zero make-up.  I think that a little lip gloss was about it.  I walked in and immediately opened the two bottles of a Malbec that I knew she loved so that they could start breathing.  I then decided on basically, what the hell, and poured us each a glass.  As I handed Khrys her glass she told a sip and then put the glass down.  She put her arms around my neck and pulled me towards her for a very lingering kiss.  She whispered to me.  “I know how tonight will be ending.  But between now and then I need affection.  I don’t need sex.  I need affection.  There are going to be a few more of these and some cuddling before we finish dinner.”

I hugged her back and returned the kiss.

Khryswent to the grill and started it up.  She had been marinating the meat since the night before and had it on the counter to come to room temperature.  She put me in charge of fixing the Cesar salad while she worked on the broccoli and rolls.  As we were working Khrys started chatting about her trip to the West Coast.  She told me that they had spent all day Saturday in Napa Valley and all day Sunday in the city.  They had taken a tour of Alcatraz which she described to me in detail after we had sat down and started our meal.

During dinner she started telling me of a couple of her customer visits.  I was surprised to hear that she had actually met with a couple of folks I had worked with before my retirement.  I told her about some of my funny experiences with them as we finished and then, as we had gotten use to, cleaned up the dishes and the kitchen.  The first time that Khrys had dinner at my place she had told me that she wanted to help to clean up so that I would not be faced with a mess the next day.  I had appreciated that and told her that same night that we would make that a practice every time we had dinner at each other’s place.

“Uncle Chuck, that was a very enjoyable dinner.  Usually we finish our dinners here with another drink or two on my balcony.  But tonight is not a usual evening.  We have an unpleasant task to get to and I don’t think we can delay it any longer.  Instead of heading to the balcony, we need to move to my living room.”

We headed to the living room and sat down on the couch together.  I looked at my friend and suggested that she get ready for her spanking and then we would talk.  Khrys had told me once she thought it was amazing at how much she disliked having to get undressed in front of me for a punishment spanking given how much she enjoyed putting her body on display otherwise.  I knew that having to get undressed for a punishment spanking was very embarrassing for her.  She knew exactly what I meant by getting ready for her spanking.  She leaned over and removed her sandals.  She stood up and undid her belt and then unbuttoned and unzipped her pants.  She let the slacks fall and then sat back down beside me to remove them.  She stood up and moved away from the couch as she started unbuttoning her blouse.  Wth her back to me she removed the blouse and laid it with the slacks.  She was now wearing only a cream colored, matching lacy bra and panty set.  She unsnapped the bra and shrugged out of it, turned slightly so she could lay the bra down.  I asked her to stop and come over to me.  I knew that it was more embarrassing to her for me to remove her panties for a punishment spanking, I hooked my fingers and slowly pulled them down and had her step out of them.  Khrys headed into her bedroom and came back with a wide belt, her hairbrush and one of her slippers.  I took her hand and patted the couch so she would sit next to me.

“Khrystiana, I usually spend this time scolding you on your behavior and talking about why you are going to be punished.  I am not going to do that tonight.  Last Thursday, I told you that in my opinion you had already been properly punished for both hurting your sister and not asking me about what you were going to do.  You disagreed with me and told me that on this we were going to have to agree to disagree.  I still do not agree with you.  However, you have basically told me that this is what I need to do and, based on our relationship, must do.  The one reason why I am willing to do this is based on what you finally told me last Thursday.  You told me that if I did not then you were going to carry a guilty feeling about this for a long time.  I know that will bother you a lot more than a very sore bottom.  I do promise you that you are going to be very sore in the morning.”

“I just told you that I felt you had been punished already, but you disagreed with me.  That is fine.  But because of that, I am going to try to mentally link the spanking I am going to give you with the one that Klara gave you two weeks ago.  When Klara gave you the second portion of your spanking, she used the belt on you.  What did you think about the ‘diaper’ position she had you take.  She asked that you lay on your back and raise your legs up and spread them.”

As I thought that she might with that question, Khrys blushed.

 “I hated it.  I could not believe that Klara asked me to do that.”

“And why, Khrystiana, was that?”

“Chuck, the answer to that is so obvious.  I am fully aware of the fact that when you are spanking me, both playful and real, nothing is really hidden from you.  But that is so different than me just opening myself up and keeping myself as open as can be.  I was so embarrassed I wanted to cry.”

As we talked I had taken Khrys over my lap and, while having this discussion, was rubbing her bottom and legs. 

“After Klara had spanked you, she and I had a long discussion.  One of the things she asked about was how a playful spanking could actually be fun.  We talked about the issue of mind set.  I told her that there were playful spankings I had given that actually were more intense than some punishment ones.  However the playful ones basically hurt less.  It was all the mental side of it.  Klara put you in that position because she realized that the embarrassment would add tremendously to the punishment you were receiving.  And she was right.  I am going to start your spanking now.  Before we move to the second phase we will pause as we always do.  But tonight you are not going to be in the corner or facing the wall.  Tonight we are going into your bedroom and you will take the same position as you did two weeks ago.  You are going to be on full display, 100%, for me tonight.”

Khrys turned her head to look back at me.  I could see the tears forming in her eyes and I just about decided to say to hell with this whole thing tonight.  But I knew that if I did that, Khrys would feel guilty for a long time.  I hated it but tonight Khrys needed for me to treat her this way. 

I brought my hand down hard.  This was the opposite of how our playful spankings start.  They start with light spanks to allow the endorphins to start to flow.  But not tonight.  I came down hard on one cheek and then the other.  Khrystiana jumped and then started moving around to avoid my fast landing hand.  Her bottom was quickly turning pink and showing hand imprints as I continued.  I had decided that even though I did not want this to be a proper spanking that it had to be. I had decided to deliver the spanking Khrys had told me she needed.  I had landed about a hundred hard spanks to my best friend’s bottom and upper thighs when I stopped.  I gave her a few minutes to come back to earth and then told her that we needed to move into her bedroom.  With my help, Khrys stood up and then looked at me silently begging  that I not have her do this. My response  was simply, “To your bedroom, young lady!”

She shook her head slightly while also saying “Yes sir.”  Almost any other time I would be delighted to be following a beautiful naked young lady with a bright pink bottom into her bedroom.  But not tonight.  I actually wanted to tuck her into bed, soothe her bottom and thighs and kiss her good-night.  But I knew that I could not.  I sat her on the end of her bed and retrieved her dressing table chair.  I put it facing her and sat down. 

“Khrystiana, you need to lay back and raise your legs.  I want you to put your hands behind your knees and raise your bottom up.  I then want you to spread your legs.”

I think that Khrys’ face got almost as pink as parts of her bottom was.   I had her hold that position for about three to four minutes.  I then stood up and walked up to her bed so that I was immediately over her looking down directly into her open vagina.  Khrys’ eyes were focused on mine for a few seconds until she simply shut them as she saw my eyes shift so that I had a clear view of her anus. 

“Khrystiana, I need for you to open your eyes and look at me.  I want you to be aware of exactly what I am doing.”

Khrys opened her eyes and focused on mine once again.   I probed her anal opening a bit and then moved to her labia.  Unlike her reminder spankings, Khrys was  not aroused.  It was perfectly clear that she was taking this spanking as she had wanted it to be, a real punishment.  I moved to her side and put my right hand on one of her hands holding the back of her knee.  I pushed her back a bit more to raise her bottom more off the mattress.  I then continued her spanking.  I decided that we were almost done, almost but not quite.  I told Khrys to hold her position as I moved to the living room to retrieve the slipper Khrys had carried out there before her spanking had started.  As I returned to her room, Khrys was looking at me with tears running down her cheeks.  I had decided that about a dozen more with the slipper would be the way to end this spanking. 

Once again I pushed her knee back slightly and then slowly and methodically started.  I landed the first slap with the slipper and Khrys let out a loud Ow.  The second landed on her other cheek and another loud cry from Khrys.  The third and fourth landed on her sit spot with an even louder cry.  This pattern continued until the tenth spank.  I then told my ‘niece” that we had two more to go.  I then landed two very hard smacks with the slipper across the fullest part of her bottom.

“It’s over, Khrys.  It’s over.

I helped Khrys lower her legs and helped her to her feet.  Immediately her hands went to her bottom and to the top of the back of her legs and she started rubbing.  As she rubbed her bright red bottom she was sort of jumping from one foot to the other.  I pulled her to me and held her as she put her head onto my shoulder and started crying even more. 

“Oh God, Uncle Chuck, it hurts, it hurts so bad.  I never seem to remember how bad a proper spanking can be.  I think that I am crying more,” she said in between sobs, “because it is over.  Oh wow.  Wow!”

After holding her for a few more minutes I laid her face down on her bed again and went to the kitchen.  I returned with the icy towels and very gently tried to soothe her bright fanny.  I then put aloe on her cheeks and soon my phenomenal lady was almost purring.  I returned the things to the kitchen after putting the aloe on her nightstand.  When I came back in Khrys was laying on her side.

“The last couple of times you punished me, Uncle Chuck, you put me to bed.  You told me that this one is over, correct?”

I nodded and smiled.

“Good because tonight I don’t feel like going to sleep quite yet.  After all, it is not 11:00 yet.  I want for us to go to the balcony so that you can have a cigar and we can have a drink.  And I do not want wine even though the Malbec you brought was great.  I think I want to have a couple of cognacs with you while you enjoy your cigar.  Fair?”

I could not help but laugh as I told her of course it was fair.  Now that the real reason for my visit was over I was happy to spend some casual time with my young lady friend.  We headed to the balcony, and I laughed as I noticed that Khrys, after slipping on a tee shirt, grabbed an extra pillow to sit on.   Khrys and I spent the next couple of hours talking about her trip to the Bay.  When I was ready to leave, I took Khrys to her bedroom to check out her still red, warm bottom.  I smoothed more aloe on her.  Khrys walked me to the door and gave me a lingering kiss.  As she hugged me she told me that even though she had dreaded the wait, had hated the anticipation and also hated the actual spanking, she was glad it was over.  She did feel that she was forgiven. 

I pinged for an Uber as I was heading out thinking again how fortunate I was.