A Very Embarrassing Evening for Barry

I will begin this post by admitting that I was quite hesitant about whether what I was doing was a good thing.  However, the comments provided to my last post convinced me to follow my instincts.  Thank you to everyone for your sharing and giving me confidence and suggestions.

I proceeded with my plans to punish Barry in front of Helen Wednesday night.  And, I also invited my sister, Carol.  Helen has previously met Carol,and Carol has previously observed and participated in spanking Barry, so I thought Carol might add a bit of a comfort level to both Barry and Helen.

Helen and Carol each arrived at the appointed time of 6:00PM. We relaxed in the living room with a class of wine, which I think helped relax each of us.  Carol was probably the most relaxed of all of us, which was very helpful.  It made me glad that I decided to include her.   Barry was the least relaxed, understandably.  He had two glasses of wine and I have never seen him so quiet.  Not surprisingly, no one broached the subject of why we were together.

We eventually moved into the dining room for a simple supper that I had prepared. Conversation still remained somewhat stilted, which made me nervous.  However, we still seemed to manage some good conversation about the current political situation ... what happened in Iowa on Monday, and what will happen in NH next week.  Since Barry and I have lived in NH, Carol and Helen were eager to hear our thoughts.  That also gave Barry a comfortable topic to talk about and he became a bit more engaged. I was very thankful for that.

As we finished our dinner, I suggested that we save dessert for after Barry receives his punishment.  This was the first time our reason for being together was mentioned.  And, it seemed to provide some relief to Helen to hear it vocalized.  I wasn't sure whether to delay dessert or not, but my gut told me that we needed to have something to bring us all together after the main event.  It turned out to be a good decision.

I asked Barry to clear the table, while I prepared the living room.  Helen followed Carol's lead in helping him.  While they were cleaning up, I took a dining room chair into the living room and placed it in the middle of the room facing the sofa.  Our coffee table was the only thing separating the chair and the sofa.  I then placed the implements that I planned to use on Barry's bottom (besides my hand) on the coffee table.

Returning to the kitchen, I asked Helen and Carol if they would like another glass of wine.  Carol took me up on it.  Looking quite nervous, Helen declined.  After Carol poured herself a glass of wine, I suggested that we all retire to the living room.  Carol and Helen seated themselves on the sofa and I sat on the dining room chair.  Barry wasn't quite sure what to do, so I called him over to stand by my right side facing the sofa.  I could see Barry and Helen nervously looking at the implements on the coffee table.

I then thanked Helen and Carol for being here to witness Barry's punishment and explained that Barry and I each agree that it is important for him to experience the embarrassment of being punished in front of someone.  I then instructed Barry to remove his shirt, shoes,and socks.  After he did so, I then made him turn to his left to face me and I unbuckled his belt and lowered his trousers.  I then instructed him to step out of them, fold them neatly, and place them on a nearby chair along with his other removed clothing.

When Barry finished, wearing only a pair of sheer white nylon panties through which it was clearly visible that he was shaved and wearing a chastity device, it was very evident that he was nervous and embarrassed.  I decided to add to his level of embarrassment by stating something like "Doesn't he look cute in these wonderful panties and his chastity device?"  I don't think Helen knew what to say, but Carol immediately commented about how perfectly submissive and cute he looked.  Looking up at Barry, I could see a blush appear in his cheeks.

I then lowered Barry's panties to mid thigh and asked him if he would like me to remove his device before he is spanked.  This caught him by surprise.  I had never done that before.  He eventually stammered that "Yes, that might be nice".  This let me make his penis the center of attraction as I removed the cage.  After slowly removing the cage and gently touching his penis while I explained to Helen how useful I have found this chastity device, Barry began to get an erection.

I was a bit surprised by this.  I began to apologize to Helen for putting her in an uncomfortable position of seeing my husband become sexually aroused.  Much to my surprise, she quickly replied with something like "Oh, don't be concerned Susan.  I have seen my share of 'willies' in my life, especially when I was younger.  However, I will admit that this is the first time that I have seen a cute little bald one that was locked up in a plastic box and wearing panties!.  I must also admit that I wish I knew about these things when my husband was alive."

I couldn't help but smile at her genuine response.  I eventually looked at Barry and he was crimson.  I was then taken completely by surprise with Carol's response. She quickly stated "I can take care of that" ... and she got up from the couch and used her first finger triggered by her thumb to thump against the underside of the shaft of Barry's penis.  She quickly repeated that action two more times.  To my surprise, his penis immediately began to wilt.  I guess I looked at her in surprise, so she quickly apologized and share that this was a technique that she had learned years ago in nursing school.

Barry now stood by my side, completely naked except for his panties that were lowered to mid thigh.  He started to place his hands in front of his penis, but I stopped him and directed him to explain to Helen and Carol why he was being punished.  He began to stammer and said that he thought they already knew.  I calmly explained that they have heard the reasons from me, but that it is important to me that he personally share with them what he has done wrong.  I added, "I want you to personally admit to them what you have been doing without my knowledge."

Barry then proceeded to stammer and slowly explain that during the past few months he had become obsessed with watching spanking porn on his computer and had been jerking off (his term).  I prompted him to go further by asking what was the result of this type of activity (which is something that Barry and I have discussed the past few days).  He became very obviously more embarrassed and became very quiet.  When I told him that I was waiting for his answer, he quietly shared that he developed some erectile dysfunction.  I then took on the role of a prosecuting attorney and asked him if a better characterization of his condition might be that he became impotent.  After a long pause, he whispered "yes".

I was watching Carol at this time, because this was something I had not even shared with her.  I could see the look of surprise and shock on her face.  And, when I looked at Barry, he was crimson faced.  I then thanked Barry for his honesty and asked him to explain what else he had done to deserve his punishment.

Barry slowly shared how he had visited a professional disciplinarian last fall to be spanked.  Again, my prosecuting attorney personality kicked in and I forced him to explain how many times he had done so; and to acknowledge that he did this without even telling me that he needed to be spanked or asking me to do so.  I also pushed him to admit that he agreed with me that his actions were equivalent to cheating on me.

I then explained to Helen and Carol (primarily for Helen's benefit) that I had already punished Barry last week for these actions, but that I felt it important to make sure he learns a lesson.  I also explained that a very important part of this punishment is to make Barry admit what he did to someone else besides me and to have this punishment witnessed by both of them.

I then asked Barry to pull up his panties and get over my lap.  I could tell that he was surprised at being allowed to keep his panties on.  For the benefit of Helen and Carol, I explained that I don't normally spank Barry with his panties on when the spanking is a punishment.  However, tonight I was going to start out easier than usual; and that I wanted them to see how cute his shaved bottom looks in nylon.  As he was pulling up his panties, I hiked up my skirt so that Barry would be lying over my stocking covered legs.

Once he was over my lap I began spanking and scolding him, as well as periodically pausing to rub his bottom and comment about how cute he looked.  I gradually spanked him quite hard with my hand and his bottom was becoming a nice pink color.  However, I could tell by the feel of his penis against my thigh that he was enjoying it.  Having him lie directly on my stockings was having the effect I desired.  When I allowed him to stand up, it was obvious that he was quite aroused.

I took this opportunity to embarrass him further.  Pulling down his panties, I made him step out of them and I then hung them on his erection.  I commented, "Since you are getting spanked for masturbating, why don't you show Helen and Carol how you like to stroke your penis with nylon panties when you masturbate?".  "No, please don't make me do that", he begged.  When I just stared at him, he took the panties and began to massage his penis.  After two or three minutes, I allowed him to stop.

After first making him hand me the wooden hairbrush that was on the coffee table, I positioned him over my lap with his legs spread open and his penis drawn back between his legs so that it was clearly visible and accessible to me.  I knew that this would further embarrass him in front of the ladies, plus I wanted to keep an eye on his level of arousal.  I expected to to go down very shortly, and it did.  It didn't take many swats with the hairbrush to have him squirming and begging me to stop.  I started out using it very methodically, working my way around his entire bottom and sit spot.  Near the end I just alternated from cheek to cheek while minimizing the time between swats.  Of course, I was scolding him about his masturbation problem the entire time and making him promise to never masturbate without my permission.  When I was finally done I allowed him to stand and rub his bottom for a moment while standing facing Helen and Carol.

When I was ready to continue I told Barry that the next stage of his punishment would address his cheating on me by visiting the disciplinarian.  After having him provide me with the Jokari paddle on the coffee table,  He looked at me with fear in his eyes.  He had never seen this paddle and he is very fearful of heavy wood.  I looked back at him with a look that said "deal with it cheater".  I then took him back over my lap.  This time I required him to lie over my left leg so that I could use my right leg to clamp him in place.  Once I had him in place, I suggested to him that he hang onto the chair rungs and be prepared for some pain.

I then went to work with the Jokari.. While scolding Barry, I started out by spanking his right cheek, then his left cheek, and finally right across the middle of his bottom.  I repeated this pattern about twenty times.  I then suggested that he hang on tight while I finished things up.  That meant multiple, rapid alternating swats with the Jokari between both of his cheeks.  It didn't take long to have Barry begging me to stop.

When I finally stopped, Barry was sobbing.

This post has become much too long.  I apologize.  Barry suggested that we need to add some photos to break it up.  So, I directed him to find some.  He found a couple.  I have also decided that I need to go ahead and post what I have.  My next post will talk about how the four of us dealt with what had happened.

We continue to grow,
Susan