Extension of First Role Play - "Corporate" Discipline

Our extended role play using our "Corporate" Discipline scenario took place Tuesday night.  I apologize for taking so long to create a post describing what happened.  Part of the delay was due to the fact that I decided that Barry needed to become more involved in this blog.  When I asked how he thought he would like to be involved, he suggested that he could add photos to my posts, and he has done so with this one.  I actually think that he quite enjoyed doing this.

I didn't tell Barry when it was going to happen until we sat down for lunch that day.  I wanted the timing to be somewhat of a surprise.  I announced to him that Carol was coming over for dinner.  He immediately perked up and said, "And ...?"  I then shared with him that after dinner we would continue our role play, with Carol playing the role of his previous secretary.  It quickly became obvious that he was pleased and very excited.

During the afternoon I laid out his best suit again and suggested that he should wear it.  I knew he would.  I also told him that he could choose what he would like to wear under it.  Knowing that he no longer owns any male underwear, I knew it would be panties, but I wanted him to have the freedom to decide how far to go (or not go) with respect to what type and whether or not to wear anything else.

Carol arrived around 5 PM and we enjoyed a light dinner together.  We were each dressed for the role play and it was clear that Barry and Carol were both anticipating what was to come.  I knew that Barry couldn't wait and that Carol would have loved to start asking him questions.  However, they each restrained themselves.  The level of anticipation was high, which was what I had hoped for.

When the kitchen was almost cleaned up, I suggested to Barry that he move into his office and prepare to be leaving for home at the end of the work day.  A short time later, I walked into his office and announced to him that I hoped he didn't mind staying a bit late tonight so that we could continue his discipline.  He acted appropriately unhappy and tried to weasel out of staying late, claiming that he and his wife had plans for the evening.  I immediately called him up short on that, explaining that his wife had joined me for lunch the previous day and that she knew about my plans for tonight.  I also shared with him that she and I had enjoyed each other very much, and that she now knew all about what he had been doing at work and supported how I was handling things.  I then asked him to look in the left hand pocket of his suit coat and give me whatever he found in it.  He reached in and pulled out a small white envelope, which he handed to me.  "Lovely", I said.  "She promised to send me this little gift when we talked yesterday".  I then opened the envelope and showed him its contents.  It was the spare key to the lock on his chastity device! "She and decided that we should each hold a key to your cage", I declared.  "Isn't that convenient for our meeting tonight? "

I could tell that this caught Barry by surprise.  And, I knew he would also be surprised by  what Carol and I had planned for him.  About that time there was a knock on the office door.  I suggested to Barry that he should see who is there.  When he opened the door, he acted appropriately surprised to see Carol.  He started to tell her she is no longer welcome in the building since she resigned.  However, I intervened and explained to Barry that I had invited Carol to join us for his disciplinary session tonight.  "After all", I said, "I think she has earned the right to be part of your discipline and it is appropriate that she achieve a little revenge for what you put her through."  Carol quickly agreed and walked into the office with an air of authority.

Carol and I each sat in a chair at a table in Barry's office and I directed
Barry to come stand in front of us.  I then ordered him to remove his coat, tie, shirt, and trousers.  After some feeble attempts to protest, he began to slowly comply.  I eventually became impatient with his progress and decided to add to his embarrassment by removing his pants for him.  Out of the corner of my eye,  I could see Carol's amusement at what was happening.  She was taking it all in.  When I dropped his trousers, Carol was surprised to see him dressed in garter belt, stockings, and panties; and even more surprised when she realized to see the outline of the chastity cage through his panties.  I had not shared that detail about our relationship with her.

"Doesn't he look darling in his female underthings?", I asked her.  "And, don't you just love the fact that he is locked up?", I added as I stood up and grabbed his crotch.  "Why don't you tell Carol and me why your wife has you locked up Barry?".  Barry began to stammer a bit and finally said something about her liking to control his orgasms.  At that point I chimed in and said "Don't you mean that she wants to control your addiction to masturbation?".  I then explained to Barry and Carol that I had lunch with his wife the previous, during which she shared with me how much Barry likes to masturbate and to wear feminine undergarments.  Barry immediately became embarrassed and began to blush.  "She has also provided me with the key to Barry's device", I added.  "Come over to me Barry and let's make sure this key works.  I then unlocked his device and slowly removed it.  As I did so, Barry immediately began to get hard as I handled his genitals.  "Why don't you go over and show Carol how nicely shaved you are Barry".   Sheepishly, he did so and Carol admired how clean and smooth he looked as she rubbed his bottom.  I was glad to see that she remembered the rule that she is not to touch his genitals.

In response, I commented "I learned quite a lot from Barry's wife yesterday."  I then explained to Carol that Barry's wife requires him to keep himself shaved from waist to upper thighs and that he does not own any traditional men's underwear.  All he owns are panties.  I also explained that Barry has a serious panty and spanking fetish.  He not only loves to administer spankings to women (as Carol and I already knew), but his wife shared with me that Barry loves to be spanked! .

I then decided to put my plans for this session into action.  I began by makingBarry stand in front of us.  I then began to lightly tease his penis.  He was so excited that it didn't take much to have him squirming in front of us. Carol was quite intrigued by what I did and added verbal comments to tease Barry as well.  It would have been easy to bring Barry to an orgasm, but that was clearly not going to happen.  Instead, I brought him to the edge of a climax several times and then left him hanging.

What happened next was a fulfillment of Barry's long desired fantasy ... being spanked over the laps of two women at the same time.  This would be the first of two sessions over both of our laps.  I am right handed and Carol is left.  So, we positioned ourselves in two chairs facing each other so that we could turn Barry over our laps and each spank with our dominant hands.  For this initial spanking, we each used our bare hands over his bare bottom.  We also took time to gently massage his cheeks as we warmed them up.  I also made sure that I took the opportunity to tease his testicles from time to time.  Since his penis was lying on my right thigh, I could easily tell that he was extremely aroused.  When we let him stand up, I couldn't resist teasing him about his erection and scolding him for allowing it to make a mess on my skirt from his precum.

We then took our time in making Barry assume different positions bending over the desk or kneeling on it as we spanked him with different implements.  It became a bit of a training session for me to help Carol learn how to spank at different levels of intensity that would keep him aroused, but keep adding redness to his cheeks.  Carol was also quite intrigued by how hard Barry stayed during most of the spankings.  At one point she called him a little spanking slut.  While Barry was kneeling on the desk for one of his spankings, I also brought out his collection of toys and panties from his desk drawer and showed them to Carol.  We made Barry explain why he the Hitachi vibrator and penis shaped butt plug in the drawer.

We then moved to the final stages of my plans.  I  informed Barry that since he loves to masturbate, he would now do so in front of Carol and me.  I also added that since he loves panties so much, he would do so using his panties. I then pulled out my smart phone and advised him that I was going to time him.  I explained that if he reached an orgasm within three minutes, his disciplinary session would be over.  I then added that if he was not successful I would use his Hitachi vibrator to finish the job for him and that he would then go back over Carol's and my laps together and we would take hairbrushes to him.

This took Barry quite by surprise.  He didn't come close to orgasm in three minutes, which didn't surprise me.  I knew he wouldn't be able to resist having me use the Hitachi on him or going back over our laps (even though it would be after an orgasm).  When the timer rang on my phone, I picked up the vibrator and plugged it in.  I made Barry continue to use the panties on this erection, but I added the vibrator.  In a matter of less than a minute he started to climax, at which time I immediately shut off the vibrator.  The look of surprise and disappointment on his face was priceless.  "You didn't think I was going provide you an enjoyable orgasm, did you?" I commented.  I could tell that Carol was also surprised by what I did.  I later learned that she was not familiar with the concept of a ruined orgasm.

After Barry cleaned himself up with the panties, Carol and I each took a hairbrush in hand, sat down facing each other, and turned Barry over our laps again.  We then administered a much harder spanking.   Sometimes Carol and I alternated spanks.  Sometimes we spanked both cheeks simultaneously.  And, for a short time I used my brush on Barry's upper thighs, while Carol worked on his cheeks.  When we finally stopped, I could tell that Barry was relieved to have it over.  This time there had been no erection pressing into my thigh.

The three of us then returned to the living room where we lit a fire in the fireplace and took some time to debrief with each other about what had happened.  Since this post is already quite lengthy, I'll save that information for my next post.  However, the bottom line was that all three of us enjoyed the evening.

Susan

PS  I would like to express my appreciation to all who offered comments and advice at the end of my last post.  Your caring and thoughts about making sure we would be OK with adding Carol to the role play was very kind and helpful.


PPS I think Barry did a wonderful job with the photos he inserted.  I hope you agree.