Learning More About Henry and Making Plans

I met Carol for coffee several days after we had spanked ‘the boys’.   I couldn’t wait to ask her about Henry wearing a chastity cage, because she had not previously shared anything about that with me.  I was surprised by it when we exposed the boys for their spanking.  I had been a bit worried about Barry wearing one, and also the fact that he would be wearing panties.  However, neither became an issue.

Carol smiled at my question about his cage and shared that Henry is a masturbator … just like Barry.  She explained that she recently learned about his habit and has taken a little different approach than what I took with Barry.  She didn’t spank him severely for it.  However, she immediately required him to wear a cage; and the only time he gets to masturbate is when she removes the cage and gets to watch him do it.  She explained that she finds it exciting to watch a man masturbate.

She also explained that she learned a lot more about Henry after our little play session the other night.  He was quite excited about the joint spanking session.  Henry has never been married because he couldn’t find someone with whom he felt he could share the depth of his interest in spanking and other fetish activities.  After our little session the other night, he opened up more with Carol because he felt he could trust her and share with her more than anyone else he has ever met.   She learned a lot in the last 36 hours and is still digesting it.

Following is a summary of the information Carol shared with me.  There was a lot, so I am trying to remember and capture it as best I can.·        

• Henry’s most important fetish is spanking.  He enjoys being spanked and disciplined; and also being able to administer spankings to his female partner.  From what he has recently shared with Carol, it seems like he enjoys receiving pretty hard spankings from a disciplinary standpoint (he shared with her that what she gave him at our play date was a warm-up spanking).  He also indicated that he doesn’t expect to spank his female partner in a disciplinary way.  He likes to make it erotic and stimulating.
• ·        Henry shared with Carol that he has an extensive amount equipment and toys relating to spanking other fetishes in his home.  It seems like he got very nervous about visiting professional dominatrixes and decided to arrange for the one he trusted most to come to his home.  Consequently, he acquired and provided the equipment he loves most.  This apparently includes a spanking bench and a significant collection of paddles, straps, and hairbrushes, as well as anal play items (enema equipment, butt plugs, and strap-on dildos).
• ·        Henry is also has a panty and lingerie fetish.  He likes to be required to ‘dress up’ and he likes his partner to wear girdles, garter belts, stockings, etc.
• ·        Henry is also interested in public play as long as it is conducted away from where he lives, so there is no chance of him being recognized.  One of his strong fantasies is to be taken into a Victoria Secrets store to have lingerie picked out for him with the assistance of a sales woman.
• ·        Henry loves to be placed in situations where his female partner controls his sexual pleasure, such as tease and denial, ruined orgasms, forced/directed masturbation, post orgasm stimulation/torture,  multiple forced orgasms over a short period of time, etc.

I was amazed at how much detailed information Henry had shared with Carol.  However, I was also aware how open and non-judgmental she would have been … making it easy for him to share.

The similarities of Henry’s and Barry’s fantasies and fetishes were very striking to me, a fact that was definitely not lost on Carol.

After sharing all this with me, Carol turned the conversation in the direction of my comfort level with getting involved in some of these fetish areas as a foursome.  Given the comfort level we experienced a few nights earlier, and the similarity of the things that Henry and Barry enjoy, I shared that I would be willing to consider exploring some things as a foursome.  I suggested that we talk about and plan some specific role-play situations and evaluate them as we go along.  I didn’t want to give her carte blanche approval, but I was definitely interested in carefully proceeding.

I asked Carol what areas she is most interested in pursuing with Henry and Barry.  After thinking about it for a few moments, she replied that she is currently fascinated with the idea of making them masturbate in front of us.  She has watched Henry masturbate several times and loves the way he gets embarrassed about having her watch.  She would love to see how he reacts to being required to masturbate in front of another woman and a man.  She also admitted that she would find it exciting to watch Barry masturbate.  She still remembers the time that I made him masturbate in her presence before I administered a punishment spanking to him.

When I asked her if she has been thinking of how to script this type of play session, she smiled coyly and admitted that she has been giving it considerable thought.  “What would you think of requiring them to have a masturbation contest?”,  she asked.  She then told me a story that Henry had shared with her about his college years.  He said that he and his college buddies arranged to hold a “Circle Jerk”, which is a ‘supposed’ competition to see who can masturbate the quickest.  However, everyone involved except for the poor guy who is going to be the butt of the joke knows that there really isn’t a competition.  So, the victim of the prank ends up being the only one trying to masturbate in a dark room full of guys.  When the victim succeeds, the lights are turned on, only to realize that everyone else is fully dressed  and is staring at him; and that he has just jerked off in front of them.  She then asked “What if we had a ‘real’ competition between Barry and Henry?”.

As we explored this idea, she suggested that the two men be required to be naked and to attempt to be the first to masturbate to a climax as we watched and cheered them on.  The ‘winner’ would earn the right to give her a bare bottom spanking over his knee.  It seems that Henry has been bugging her to let him do so.  Consequently, she felt that he would accept the competition.  She also admitted that she suspects that, given Barry’s ED issues, Henry should easily win the competition.  She must have been reading my mind, because my only concern about this plan was that I really didn’t like the thought of Barry spanking Carol’s bare bottom.  She is eight years younger than me and has always had a much more attractive figure than me, especially with respect to her derrierre.

I began to warm up to the idea, especially if Barry didn’t get to spank her.  I also suggested that there should be a consequence for the loser.  I suggested that the winner gets to spank Carol, but I get to provide the loser (who we expect to be Barry) with a bare bottomed disciplinary hairbrush spanking.  Carol loved it.  She explained that she really likes the idea of Henry getting to see the type of spankings that I am capable of administering.  She has told him a bit about them and he seems fascinated by the fact that I administer real life disciplinary spankings to Barry.  I also confessed to her that it has been quite a while since I have needed to administer a disciplinary spanking to Barry.  In this case I would be doing it to punish him for accepting the masturbation challenge in order to earn the right to give Carol a spanking.  It really would be a disciplinary spanking for him.

We decided to sleep on it a few nights and to meet again to figure out if and how we wanted to proceed.  We have since met several times and have finally decided to set our plans for this little competition into motion.  We’re going to have dinner together at Carol’s home.  During dinner, we will present the competition idea to the boys.  If they each accept the challenge, Barry and Henry will have to stand in front of us and masturbate.  The first one to achieve a climax will earn the right to turn Carol over his knee and give her a hand spanking on her bare bottom.  There will be limitations on that spanking as far as length and severity.  The intent is for it to be a friendly and fun type of spanking for her.  The loser will have to stop masturbating as soon as the winner has been declared.  Hence, the loser will not get to have an orgasm that night.  The loser will also receive a disciplinary spanking with a hairbrush on his bare bottom from me.

We both feel pleased with these plans.  This feels like a fun ‘next step’ for Carol and me (and we hope for the boys).  Now, we just need to arrange a date and make it happen.

Susan