When Barry lowered his trousers, I was definitely surprised. I knew he would be wearing panties (since that is all he owns) and the fact he added a garter belt and stockings didn't surprise me. I was very prepared to incorporate his feminine underwear into the scenario. However, I never expected to see him wearing his chastity device locked in place! His goal was to create something unexpected and unusal for the scenario we were acting out. And, he succeeded.
Of course, I immediately reacted to how sweet he looked in his lingerie and pretended to not notice the outline of the cage inside his panties. As I grabbed his crotch and started to tell him that I own him now, I reacted to feeling the cage and said "Oh ... it looks like someone else owns you as well! Does your wife hold the key to this lovely little device?" He eventually admitted that she does and that she has kept him locked most of the time for several months now. I replied that I would like to meet this lovely women I also mused that I wondered what her reaction would be if I cut the lock off and replaced it with my own. Barry immediately began stammering that I can't do that, to which I replied that I certainly can ... and just might the next time we get together this way.
I then decided to begin with the spanking portion of my plans. I told Barry that his former secretary had shared with me that he has a special desk drawer where he keeps a variety of spanking implements and sexual toys, as well as his collection of panties that he has kept from the women he has spanked. To make this part of the role play, I had previously prepared one of his desk drawers with a variety of things. "Let's see what kind of toys you keep in your special drawer", I said as I opened it. I proceed to remove each item as ask Barry about them one by one. We found a nice variety of spanking implements, including a leather paddle, a wooden hairbrush, and a wooden ruler paddle, In addition to three pair of women's panties, I produced a Hitachi vibrator, a set of nipple clamps, a penis shaped butt plug, a rather larger dildo, a tube of lubricant, a blindfold, and a pair of padded wrist cuffs.. Barry acted quite humiliated during this entire process and I enjoyed asking him lots of probing questions about what he does with them. When he wasn't forthcoming, I would remind him that his last secretary and filled me in on lots of details.
We then moved into the first spanking phase of Barry's predicament. Taking him over my lap, I proceeded to give him a good warm up spanking with my hand and the leather paddle. It was apparent that he was enjoying it. When I let him stand up, it was also apparent that he was straining within the chastity cage and it didn't look like it was very comfortable. Of course I teased him about that.
I then directed Barry to remove his shirt and tie, leaving him in just his panties and stockings. I cleared the top of his desk while he was doing so. I then placed the blindfold and wrist cuffs on him and made him lie on his back on top of the desk. Reminding him that I had learned from his last secretary how he had sexually teased her, I told him that I thought it would only be fair for him to get a dose of his own medicine. I proceeded to use my finger tips to arouse him. I eventually installed the nipple clamps and then put the Hitachi to work on his cage. His reaction was priceless. After some uncomfortable moments and relentless use of the vibrator, I enjoyed watching him climax while still restricted in by the cage, making a sticky mess of his nylon panties.
It was then time for some more spanking. After having him turn over and lie on his stomach on his desk, I put the hairbrush and ruler paddle to good use. Knowing how hard it is to receive a spanking after an orgasm, I went somewhat easy. I reddened his bottom quite nicely, but I still wanted the role play to be fun and not punishment. When I was done, I let him up and removed the blindfold and wrist cuffs. His panties were now a complete mess from having climaxed in them earlier. I then directed him to get dressed.
While he did so, I told him that I would plan to see him again next Wednesday night at the end of the workday for our next little mentoring session. Once he was dressed and before I walked out the office, I went to him and whispered in his ear "This role play is not yet done. I suggest you clean up your office and then come upstairs. When you arrive in our bedroom, I will be playing the role of your wife." This was a surprise that Barry clearly didn't expect. His reaction was priceless.
To be continued in my next posting ....