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.

Susan                                          

CAROL'S TURN: Role of a Female Mentor

In a comment to my most recent post, Kate asked:

• Do you consider yourself a naturally dominant woman who simply acted on your own instincts or is this something you have learned from watching and observing Susan? I have mentored several women entering DD relationships including both of my adult daughters. Personally I believe a female mentor and role-model is the missing link for many women trying to make this work. Bit I would appreciate your own view of it. 

I am definitely not a naturally dominant woman.  However, I have come to enjoy using whatever dominant traits I possess.  During my first marriage, which ended with my husband's much too early death, we never played in this way at all.  I think it is safe to say that female domination never entered either one of our heads.

However, after my husbands death I had the opportunity to observe my sister Susan as she explored domination and spanking with her husband.  I found myself very interested in her actions and their results.  I was especially amazed by the impact it had on her husband Barry and the new life it brought to their marriage.

When I decided to explore the possibility of a new partner, Susan was very helpful to me in her willingness to open up more about her new lifestyle with Barry.  She continues to be willing to share openly and that is extremely helpful.  I could not do what I am currently doing without her support and guidance.

So, in answer to Kate's questions:  Yes, I believe a female mentor and role model is invaluable to anyone who wants to explore this area with her partner.

Carol

CAROL'S TURN: Taking control of Henry - continued

When we arrived back at Henry's home we immediately went to his basement playroom.  I quickly reminded him that he had earned a good paddling for not having shaved himself as I had directed.  He actually acted like he was looking forward to it and asked me if I'd like him to be on the spanking bench for it.  I said that I would very much like that, and I directed him to completely strip.  I then secured him to the bench.  I then selected a medium sized wooden paddle and began to apply it to his backside.  I started out rather lightly, but continued a crescendo until it was really popping of his red bottom.  By the time I finished, it was clear that he was feeling it, although he was still semi-rigid.  I decided to pause at that point and move on to my next planned task --- shaving him.  After asking Henry if he had a beard trimmer and learning its location, I assembled the tools needed to shave everything accessible from the position he was now secured.  It allowed excellent access to his bottom, scrotum, and inner thighs. It took a while, but once the task was completed, I liberally applied an alcohol based after shave that I found with his shaving gear and then returned to using the paddle again.  This time I really got his attention and his erection quickly disappeared.

I then advised Henry that I wanted to move him to the gynecological exam table.  After securing him with his legs spread, I proceeded to shave his front side.  It took a while, but I thoroughly enjoyed having such complete control over him and watch his discomfort as removed the hair from his waist to mid thigh.  He really looked quite cute and I made sure to tease him about how smooth and clean he was going to be.  He must have enjoyed it because he remained hard the entire time, which made the shaving of his penis much easier.  When I was finished I advised him that I expected him to continue shaving this area at least once a week for me.  I also warned him that if he failed to do so, I would use more than just a paddle on him.

I decided it was then an appropriate time to introduce Henry to his new chastity cage.  Somehow I think he thought it was going to be a bit of a joke.  However, I now clearly let him now that if he wanted to have a serious relationship with me he had to turn over control of his manhood and stop getting all of his sexual pleasure from his hand pussy.  I explained how effective it had been for Susan and Barry and that this was not negotiable to me.  He decided to agree and I proceeded to install his new device for the first time.  It was a challenge at first due to his erection.  But, thump to the underside of his erection from my fore finger snapped from my thumb (a trick I learned many years ago from a fellow nursing student) quickly reduced the problem.

I then asked Henry if he had ever orally pleasured a woman to orgasm and learned that this was not a skill he possessed.  So, we moved to the sofa in his downstairs office for his first lesson.  I was pleased to realize that Henry was a very quick study.  He was also pleased to learn that pleasuring a woman provides similar returns.  He experienced the first removal of his chastity device to be pleasured (and, of course, having it re-installed afterwards).

We decided to meet again in two or three days.  I thought that was an appropriate first length of time for Henry to be locked up.  I also reminded Henry that we had one more new toy that we haven't explored.

As we cuddled in each other's arms at the end, we both agreed that it had been a wonderful day together.  It was very clear to me that I needed to take charge of Henry and I was also very pleased at how he accepted this new control in his life.  As I look back on this now, months later, I realize how critical that day was in the development of our relationship.  I firmly believe that if I had not taken charge we would not currently be planning for our upcoming wedding.  We would also not be enjoying the deep relationship we have with Susan and Barry as a foursome.

Susan has purposely not been posting while I have been sharing these beginning stages of my relationship with Henry.  I now hope we can get back to sharing more about all of us.

I also want to express my appreciation to all of you who have warmly welcomed and appreciated my sharing.  This has been a new experience for me.  It is not easy to share so much about a very private part of my life.  Thank you everyone.

Carol

CAROL'S TURN: Taking control of Henry

In my last post, I didn't share everything that happened at the end of our play session.  Henry showed me another room in his basement.  It was the room designed to be the bedroom for the in-law apartment.  However, it now contains some very interesting furniture, which Susan has already written about in a previous post (Henry's Playroom).  Seeing this playroom for the first time made me realize how kinky and submissive Henry must be.  At the end of this play session, Henry also asked me why I didn't make him masturbate this time.  That made me realize that Henry had yet to make any effort to provide me with sexual pleasure.  This previously unshared information is what made me tell Henry that our next session would have to be "real" and would be completely controlled by me.  I realized that unless I took control of Henry, our relationship would always be one-sided to provide him with sexual pleasure.

During the following week I spoke with Susan several times and made plans for my next 'date' with Henry.  Susan was very supportive and helpful, as she always is.  She also shared some good ideas that I hadn't thought of.  On Friday evening I called Henry and asked him if he'd like to play on Saturday morning.  He said that would be nice, so I told him that I would pick him up at 10 AM for us to go shopping together.  He sounded disappointed, so I shared with him that it would be a shopping trip for new toys we could play with.  That got him very interested, so I dropped my first real surprise on him.  I told him that I expected him to shave his genitals and butt before I picked him up.  He started to object until I reminded him that this was going to be a 'real' play session, not a role-play.  And, that what we do the next day was going to be completely up to me.  He hesitantly agreed.

I arrived at Henry's home at 10 AM sharp the next morning.  He invited me in for coffee.  I said I'd come in for a minute, but I didn't need any coffee.  Once in the house, I directed Henry to show me his 'pecker' (that is a word he likes to use).  When he asked why?, I told him that I wanted to see if he had followed my directions.  I quickly saw that he had not shaved and informed him that his failure was going to cost him a very sore butt.  He tried to make excuses about not having time, but I told him that I never want to hear excuses from him or his punishment will be worse.

When we left the house, I drove, and Henry wanted to know where we were going.  I simply shared with him that he would find out when we arrived.  Our destination was an up-scale adult novelty and lingerie store about a half hour drive away.  I suspected that Henry knows it, but didn't know for sure.  I had visited it during the previous week as I was planning this date.  I wanted to see if they carried the types of toys I had in mind.  They did and I also had chance to have a candid talk with the woman who owns the store with her husband.  I let her know what I was looking for and what I hoped would happen to embarrass Henry as we shopped.    She loved my ideas and was willing to help me.  She also agreed with my thought that Saturday morning would be a busy time with many customers present to help add to Henry's embarrassment.

Henry seemed surprised when I pulled into the parking lot.  When I asked him if he had ever been here he claimed that he had not.  However, when we walked in the door, the owner with whom I had met greeted him by name!  I could tell by the look on her face that she had not idea that it was Henry that I was planning to bring.

I started the conversation by letting her know that Henry and I were newly dating and hoped to find some appropriate sexual aide and play things to make our dates more exciting.  I also expressed surprise that she new Henry by name.  She quietly shared with me that Henry has been a frequent customer for many years.  She also openly shared with both of us that she would be happy to help us find whatever is appropriate.

I looked around the store and realized that there were four other customers in the store.  Two individual men and a couple.   I didn't make any attempt to keep my voice low when I began to share with the owner what we were looking for.  I started out by sharing that I was interested in buying some sexy panties for Henry to wear.  I couldn't help by add that Henry seems to be fascinated with panties, so I want him to wear them 24/7 after we shave his pecker and ass.  Henry began to shrink into the woodwork!  And I couldn't help but see the other customers react to what they heard.

The owner then ushered us into the lingerie section and made several recommendations.  I also found some options that I liked and asked Henry what he found to be sexy.  I also asked the owner if she had a dressing room where Henry could try things on.  She assured me that they did, but they Henry must keep his own underpants on when he tries things on.  She also shared that their dressing rooms were very private and that I was welcome to join him there.  I then directed Henry to pick out six items to try on.  As we proceeded to the dressing room, I could feel the eyes of the other customers watching us.   When we got into the dressing room, Henry asked me what I thought I was doing.  I shared with him that I was providing a real life experience of the things that I think he fantasizes and masturbates about.  When I pressed him, he admitted that I was right.  I then told him that he can call it quits anytime he wants.  However, I added that if he does so, our relationship would be over.

When we returned to the store front I noticed that more customers had arrived.  I took that opportunity to hold up the six pair of panties and advise the owner that Henry will take all of them.  I then added that I couldn't wait to throw out all of his tighty whitey jockey shorts.  That quickly got the attention of the newly arrived customers.

After leaving the panties on the front counter, I asked the owner if she carries any chastity devices.  I added, loud enough for some of the other customers to hear, that I need to find a way to control Henry's need to masturbate.  Henry immediately pulled me aside and whispered in my ear "What are you doing?".   I simply responded that we had just had this conversation in the dressing room.  I reminded him that he can call it quits any time.  I also reminded him that if he continues we will return home with a number of new toys and ways to explore our relationship.  We continued.

The owner took us to an area where she had multiple options of chastity cages.  She initially showed us one that was obviously designed for a small penis.  Henry seemed quite pleased when I immediately shared in a loud voice that it was much too small for Henry's pecker.  We then worked to pick out something that was more appropriate size-wise for Henry.  But, I also couldn't help sharing loudly enough for most customers to hear that I was concerned about "comfort", because Henry would be wearing it 24/7.  After reviewing the various options, I let Henry pick the one he wanted to wear.  Of course, his choice would have been nothing :-).

After the chastity device was added to the panties on the front counter, I shared with the owner that "we" would like to purchase a quality strap-on belt and dildo.  I could see several customers' heads turn as I made this request and I'm sure that Henry saw them as well.  He turned to me and mouthed the word "please".  However, I continued.  The owner suggested that we first look at dildos and we had a lengthy discussion about size.  We settled on buying two dildos, one about the size of Henry's penis and one a reasonable bit larger.  We then worked on a belt to hold them, focusing on my comfort and how securely the belt would hold the dildo as I used it on Henry.  He continued to be mortified about what other customers were hearing.  I'm sure he was also mortified for the owner to be learning all of this information about him.  I couldn't help bu share with Henry how excited I was to look forward to using these dildos after seeing his collection of photos on his PC about pegging.  I was so happy that it would excite him.  I have to admit that I was also aware of the reaction of the growing number of customers in the store.  No one was leaving and everyone seemed to be staying close to us in the store in order to hear what we were saying.

At this point, I asked Henry if there was anything else he would like to look for in the store.  He quickly replied that there was not.  As the owner began to check us out, I left Henry at the register alone to pay for the items we had selected.  I returned just as he signed the credit card slip.  I thanked the owner for being so helpful and let her know that we would be back.  She returned a very big and kind smile as she shared that she loves to be of service.

When we got back to the car, I asked Henry how he felt about our little shopping trip.  I was very pleased to hear him say he loved it, but it was extremely embarrassing.  Further conversation confirmed that the embarrassment was OK and loved, as well.  When we discussed what to do next, it was very clear that we were both ready to head to Henry's home and play - even when I reminded him that he was still going to be punished for not having shaved.  I also let him know that I now planned to shave him myself.  I heard no argument from Henry.

So --- I will pick up here with my next sharing.

Carol

CAROL'S TURN: Getting to Know Henry - continued

Several days after that first play time, Henry and I met for coffee again.  It didn't take him long to ask if I'd like to play again.  When I agreed, he invited me to his home, if I was comfortable with coming there.  By that time I was feeling OK about it, and I agreed.

Henry suggested we do another role play, this time using an office setting.  He explained that he has a large home office with a large desk and sitting area that would provide a good setting.  He also suggested that I be his boss who has discovered that he has a large amount of pornography on his work computer and has been masturbating in his office.  Finally, she said that I could bring whatever toys and implements I'd like, but that he has a large collection from which I can pick things to use on him.  It was at this time that I began to realize how deeply Henry was involved with spanking and kinky sexual activities.

When I arrived at Henry's home on the designated evening, we first sat in his sun room and had a cup of tea.  I think he was trying to make sure I was comfortable being in his home.  He then took me to his home office, which is located in the basement.  He explained that the basement was designed as an in-law's apartment and contains a living area (which is now his office with a sitting area as part of it), a bedroom with attached bathroom and a small kitchenette.

I suggested that the setting for the role play be that I have called Henry into my office to discuss a serious matter.  He would arrive, not knowing what issue was to be discussed.  He was agreeable to this plan.  I then asked him to show me where the pornography is located on his computer and where he keeps his spanking toys.  After he dis so, I then asked Henry to leave the room and return in 15 minutes for his appointment with me.  I thought that would give me sufficient time to review the type of pornography contained on his computer and make some decisions about spanking implements.  Before he left, Henry shared with me that I could spank him harder than what I previously did.  He told me that he actually enjoys quite a hard spanking.  I thanked him for sharing that.  I then asked him how he felt about being completely submissive to a woman.  He provided the answer that I expected, which confirmed my preliminary plan to step things up a bit during this play time with Henry.  My brief review of the porn folders on his PC also confirmed the extent of his kinky interests, especially spanking.

When Henry returned, I put on my stern and serious face and directed him to take a seat in the chair to the side of my desk.  I then calmly, but sternly advised him that our IT office had discovered a serious amount of pornography on his computer and a history of him visiting pornographic websites while he was working.  He first tried to deny everything, but quickly realized it wasn't working.  I then told him that we have security cameras in everyone's office and asked him if he had been doing anything in his office that he wouldn't want anyone to see.  He played the role quite well.  He stammered and hemmed and hawed and eventually said "no".  But he then asked why I brought that up.  I just said "I think you know" and added that it was interesting to watch a man masturbate.

I then suggested to Henry that we needed to talk seriously about his situation.    I explained that I should fire him.  I quickly added that I really didn't want to do that because he was such a productive employee.  I also added that I was willing to find an alternative solution.  He was very open to that, so I explained that I also enjoy the kinky sexual aspects of life.  I offered that, based upon the porn on his computer, he would like to be spanked by a woman.  I suggested that I would not fire him if he was willing to submit to corporal punishment from me for this situation and any future work related performance issues.  Henry quickly agreed.

I then informed Henry that I would start out with a prolonged spanking and asked him to tell me his favorite position.  Since he had a folder labeled "spanking positions" on his PC, I suggested that he show me his favorite.  This is what he selected.  He then showed me a video of the same gentleman being spanked in this position.  It was quite interesting.  He bottom was thoroughly spanked, but so was the head of his penis and the tender areas around his anus and lower bottom.  It was quite a spanking.

After making Henry strip, I placed him in this very position and thoroughly spanked him in the same way.  I was amazed to see that he remained hard through out the entire spanking.  That made me decide to give him a very hard spanking with an implement.  I suggested that he provide me with his favorite spanking implement.  I was a bit surprised when asked me to use a leather sandal that I was wearing (this was back in warmer weather).  I quickly agreed.  After turning him back over my knee, I proceeded to apply the heavy soled sandal quite vigorously to his bottom.  This time his erection disappeared and he did a lot of squirming and begging me to stop.

We eventually retreated back to his sunroom for a glass of wine, which gave us time to discuss what had taken place and our budding relationship.  We each agreed that we would like to continue.  However, I suggested that our next play time should be a bit different.  I shared with Henry that it should not be a role play, but something real.  And I added that it should be completely controlled by me. (I wanted to see just how far he was willing to go with giving me control).  Henry quickly agreed and we decided that I would get in touch with him when I had made some plans.

If Susan wants me to do so, I'll continue to share how our relationship developed.

Carol