Tuesday, January 24, 2017

Play Time with Carol and Henry

I am so glad that Carol took the time to share the details of the beginning period of her relationship with Henry.  I was very proud of the way she took charge of the relationship and it is wonderful to see the two of them enjoying life together.  I've held off on posting any details from our current activities until Carol finished telling her story.  However, now I'll get back to posting and I am hopeful that Carol will also post some current things from their relationship.

Since Christmas, Carol, Henry, Barry and I have been attempting to get together each weekend for some sort of kinky play time.  It usually involves some sort of role play, but sometimes it is just real life.  We decided that we would take turns coming up with an idea or theme.  The girls pick what we will do one week, and the boys pick the next week, etc.  So far, it has worked out quite well and all of our events have been enjoyed by all.

Last Saturday it Carol's and my turn to plan the activity.  We decided that it would be a real life event and the four of us would go shopping together before coming home to play.  We started out at Victoria's Secret with a goal of selecting some sexy lingerie for each man.  We each ended up selecting the bustier shown.  I picked black for Barry, with black stockings, and Carol selected Cherry Red with white stockings for Henry.  However, before we made our selections, we had great fun searching for and viewing various options.  Of course, we made no secret of what we were doing.  Upon entering the store Carol and I picked out the youngest and sweetest looking sales representative and told her that we were looking for something very sexy for our men.  We then took her to Barry and Henry and we began the search.  We received many stares from other customers as we held up different items and colors to our men as we tried to make a decision.  It was very amusing to see how embarrassed they were.

Afterwards we went to the adult novelty store that Carol had previously taken Henry.  Our goal there was to purchase some silicone breast forms for each man to use in his new bustier.  We made sure that the customers in that store were well aware of what we were doing, which was very easy to do because the store was quite busy on a late Saturday morning.  After selecting the breast forms we decided to look at some new paddle options and made the men bend over so we could test various options on them.  That brought some cheers and words of encouragement from a number of the customers.  We ended up purchasing a very nice, thin hardwood paddle that is very stingy.        

When we arrived home, we had fun dressing the boys up in their new lingerie.  When we removed their chastity cages it was very clear that they were enjoying it as much as we were.  After testing out our new paddle on the bottoms, Carol and I came up with the idea of having a little contest.  We would each tease their genitals with the intention of getting them to ejaculate.  They had to try to hold off as long as they could.  The first to ejaculate would lose the contest.  The prize to the winner would be a blow job.  The loser would be get a dose of the new paddle.  To make things as fair as possible, Carol and I agreed on some rules of engagement regarding how we would tease the men.  There would be no stroking of the penis.  Touching could only be with our finger tips, open palms, and their new panties.  Verbal teasing and tantalizing would be allowed.

They each did very well.  However, after a little over fifteen minutes, Henry finally succumbed and ejaculated.  Not surprisingly, Barry very much enjoyed accepting his prize from me (since it has been quite some time since I have offered him that treat) and Henry attested to the effectiveness of the new paddle.



  1. Wow. Although I don't like cross-dressing and the humiliation part, I guess it's ok if all the 4 of you have fun. The teasing part: awesome.
    Best wishes,

    Marco and Lindsay.

  2. Loved this Susan! What a fun adventure for all of you. I was wondering how your relationships were progressing. Now I know...cumming right along. :-)

    As a pantie wearer and sometime cross-dresser I think I likely would have been in the same situation as Henry. My wife "outed" me at Victoria Secrets one time, but not is such an overt and completely embearrising way.

    Thank you for sharing,