Sunday, September 25, 2016

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.



  1. It's nice when an adventure like this works out well for everyone.

  2. No orgasms for the males?
    Not fair.

    Best wishes,


  3. So glad you're back!

    What a fun day for you and your sister.

    So did Carol put Henry in a belt?? That's how you start a great relationship!!

  4. Glad you're back!

    I hope you can keep in touch; it makes us think we are going to be ok if you all are.

    Peace out

  5. What a lovely way to return to blogging. I loved the joint paddling. How delicious--in my dreams. Interesting that your sister has also put her fellow in chastity. Thank for sharing with us. Penney

  6. That was wonderful. Oh to be in the company of another FLM couple, having to endure such a spanking.