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

Our First Play Date with Carol and Henry

I probably shouldn’t call this event a play date.  Barry and Henry didn’t know anything about it in advance, but Carol and I did.  A couple of weeks ago, Carol and I decided that it was an appropriate time to experiment and see how things would go if we tried to have some fun with Barry and Henry together.  We talked about it and felt that a joint spanking would be a good way to break the ice.  So, Carol and I made plans for us to get together for dinner at her house and to create a situation where they both deserved to be spanked.

During dessert Carol purposely raised a topic that she knew Henry had some strong feelings about … that were somewhat different than hers (a local political situation).  Henry took the bait and began to argue with her, albeit in a very gentle and kind way.  Carol took offense at his arguing and Barry quickly came to his defense (it really was a fabricated reason for Carol to be upset).  That gave me the opportunity to intervene and declare that both gentlemen were acting a bit childish and each deserved a good spanking.  I suggested to Carol that we take care of it right now.  Barry quickly caught on to what was happening and played along.  He apologized profusely and begged me not to spank him in front of Carol and Henry.  However, Henry continued to argue and declare that he didn’t deserve to be spanked for merely expressing a different view point.  At this point, Barry really stepped up to the plate .   He turned to Henry and said something like “Let it go Henry.  Let’s just take our punishment like the men we are.  How bad can it be, especially since I understand that you and I each seem to enjoy being turned over the knee of a beautiful woman.”  With that, our first play date began….

Two dining room chairs were placed facing each other in the living room. Carol and I sat down on them.  Since Carol and I each spank with a different hand (right vs left), the two men found themselves standing side by side in their underwear after we instructed them to remove their shirts, trousers, shoes, and socks.  Barry was wearing is usual panties and Henry a pair of colored low-rise men’s jockey shorts.  They both couldn’t hide the fact that they were wearing a chastity cage.  I couldn’t resist teasing them a bit about how sexy they looked and how much I was going to enjoy seeing each of their bare bottoms turned to a rosy red color.

As we lowered their underwear, I was surprised to see that Henry was also wearing a chastity cage.  I commented to Carol that perhaps we should remove their cages so that we can better assess how they are reacting to their spankings.  Carol quickly agreed  and we did.

As the cages were removed, both of our men began to show signs of arousal.  I couldn’t resist toying with Barry’s penis while offering loving comments about how nice it was to see him being excited about getting a spanking.  Carol chimed in as well and we each agreed that we were sure that they would not seem so excited once they were being seriously spanked.

As we turned our two little boys over our laps, their heads were side by side, so they would obviously be aware of each others’ reactions to the spanking.  Carol and I had earlier agreed that we would play it by ear, but that we would try to keep the level of discomfort for each of our little boys about the same.  Carol warned me that she planned to give Henry a fairly hard spanking.  We also agreed that we would start with a prolonged hand spanking to warm them up and see how things were going.  We could then decide whether it was appropriate to proceed to a serious spanking.

It turned out to be a lot of fun.  Carol and I could reach each man’s bottom, so we occasionally spanked the other mate.  At one point, when he was whining and complaining to Carol about being spanked, I reached over and gave Henry a few hard swats with my hand and told him to stop his whining.  Immediately afterwards, Carol gave Barry several unexpected really hard spanks that caught him by surprise and created a reaction from him.

After each bottom was nicely warmed up, I suggested that we needed to drive our point home to our naughty little boys and suggested that we employ something more severe than our hands.  Carol agreed and sent Henry to the bedroom to get their bag of implements.  While he was gone, I warned Barry to be prepared for a tough spanking.  I let him know that he was going to get it worse than Henry.  I couldn’t help but smile when he replied “Give it to me darling.  I’ll take it.”  It was clear that he was willing to show Henry how much he could take.

When Henry returned with the bag of implements, Carol suggested that we let each little boy select an implement to be used.  She asked Henry to pick first.  He picked a 24” ruler, but I knew that it could provide a lot of sting, should Carol decide to use it hard.  Much to my delight, Barry picked a heavy wooden hairbrush.  Henry looked at him like he was crazy.  Barry picked up on that and commented to Henry that he knows I will only use it as hard as is appropriate.

So, back over our knees the two naughty boys went.  They both received an appropriately hard spanking.  Side by side they moaned and begged.  I took my cue from Carol concerning how hard she wanted to spank Henry.  I initially matched her level.   However, as we finished up, I gave Barry a rapid series of ten swats with the hairbrush that had him begging me to stop.   In the end, they each received a tough spanking.  I’m sure they each wanted to demonstrate their pain endurance to the other.

When we were done, we settled in for a cup of coffee with each other and discussed what had happened.  I was pleased to hear from each of them that it was an exciting experience.  Carol and I just looked at each other and smiled.  It appeared that the boys were comfortable with each other.  We each knew that we had opened up an interesting door.

Susan

“Where’ve You Been Susan?”

"Where've you been?" is a question I get asked a lot these days.  I’ve been on hiatus from more than just this blog.  I’ve taken time off from a number of other activities and connections as well; and it has been good.  However, I’m now ready to re-enter the wider world again.  At some point I may share what prompted my absence, but I’m not ready to do so yet.  Please bear with me.

First, let me assure everyone that Barry and I are fine.  We have never been better, both health-wise and relationship-wise.  However, we have been busy, so it was good to slow some things down a bit.

My sister, Carol, is also doing great and we have been seeing a lot of her.  Since I last blogged, a new man has come into her life and she is thoroughly enjoying it.  His name is Henry, and he is a wonderful and kind gentleman about her age.  He is also quite kinky with a naturally submissive side similar to Barry’s.  Carol actually met him through FetLife, so that is not surprising.  They’ve been seeing each other for about four months now and seem to be developing a very close relationship.  During the last two weeks, we have actually started to play together a little bit, so there may be some interesting stories for me to tell (with Carol’s permission, of course).

I hope my small band of loyal readers are well and have not forgotten me.  I apologize for disappearing, but it did me a lot of good; and my absence has made me realize that I miss having this outlet to share some things in my life that can’t be shared with most other people.

It feels good to start typing again.

Susan