Wednesday, January 18, 2017

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.


Thursday, January 12, 2017

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.


Sunday, January 8, 2017

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.


When our decisions

Monday, January 2, 2017

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.


Tuesday, December 13, 2016

CAROL'S TURN: Getting to Know Henry

Hi Everyone,

Susan has recently suggested that I contribute to her blog to share a bit more about my relationship with Henry.  I have never tried to write in a journal or share things about myself, so this is a huge challenge to me.  But I thought I could give it a try and see how things go.  I realize Susan has shared some things about Henry and me, but I thought it might be best if I start from the beginning.

I have to thank Susan for introducing me the the kinky life she and Barry enjoy.  I would have never explored this area if were not for them.  And, I would have never met Henry.  I met him through a personal ad he placed in FetLife. It was totally unlike me to look or respond to something like this, but I'm very glad I did.  Henry is in his early fifties and has never been married.  But he has led a very interesting life and has a very kind and gentle spirit about him.  He is also very kinky and submissive, which are two traits I have come to appreciate in a man since my husband passed away at too early an age.

I ended up meeting Henry for coffee at a local Starbucks one afternoon.  We ended up spending three hours over coffee.  It was amazing how much we had in common.  After two vanilla dates, we were still enjoying each other, and Henry asked me if I would consider exploring his kinky side with him.  When I agreed, we decided that he would come to my home and explore a simple role play.  I asked him what he would like it to be.  Without hesitation he shared that he would like to play the role of an older teenage boy (17 or 18) and have me play the role of his new stepmother.  He suggested that our role play begin with his stepmother confronting him with evidence that he has been peeping on his teenage stepsister and has been borrowing her panties and using them to masturbate.  He indicated that I could punish him in anyway I thought appropriate, and even indicated that I could make him masturbate in front of me if I so desired.  (That was my first clue that Henry might be overly attracted to masturbation.)

We set up a date and time and I suggested to Henry that he could bring a long a few of his favorite spanking toys for me to consider using to punish him.  I also planned to borrow a few things from Susan.  Henry arrived on the designated evening dressed appropriately casually for a teenaged boy.  I was dressed appropriately maturely.    After some normal small talk, including Henry showing me the three spanking implements he brought along, I suggested that we start in the family room where Henry would be watching a sports event on TV.  Henry made himself comfortable with the TV turned on.  I shortly appeared and began to confront him about his behavior.  I informed him that his step-sister (Molly) had told me that he had walked in on her in the bathroom without knocking on two separate occasions and that several pair of her panties had recently gone missing.  Henry, of course denied everything, but didn't have much to say when I produced three pair of Molly's panties that I had found under his bed.  He also had no good answer when I asked him to explain what appeared to be cum stains on the panties.  His sole response was that he didn't understand what I was talking about.

I finally got to the point where I informed him that it was very clear to me what he had done and that I planned to punish him appropriately.  I then proceeded with requiring him to remove his shirt and trousers and come stand before me.  I then slowly lowered his underwear as I continued to scold him about his behavior.  I also talked about how I was going to spank him.  As I did this, Henry became quite aroused.  I used this as a reason to justify that he needed to be punished.

I ended up turning Henry over my knee and giving him a very prolonged spanking with the implements he brought (a ruler, hairbrush, and a small wooden paddle).  I decided not to use the items I had selected ... because by the time I used his selections at a moderate level, his bottom was nicely red.  I also wanted to keep this first meeting at a moderate level and made a conscious decision to not make him masturbate.  There will be time for that later.

I was also very much aware of the fact that Henry still had an erection when we finished.


Saturday, December 3, 2016

News Flash

I realize it has been  over a month since I last posted ... again.  Life has been busy, including some fun events together with Carol and Henry. However, I just haven't had the time and energy to appropriately share them.  I promise to do so soon.  I think the election results took a lot out of me.

However, this weekend I have some exciting news that must be shared.  Carol and Henry are going to get married.  I know it may seem a bit quick, but their relationship has developed very nicely and they both are extremely happy together.  The wedding won't take place until Spring and it will most likely be a very intimate affair for family and a few very close friends.  In the meantime, Carol is in the process of moving into Henry's house while she puts hers on the market.  I am extremely happy for both of them.

And, a second bit of exciting news:  I have convinced Carol to try her hand at sharing some of her thoughts about her relationship with Henry in this blog.  I suggested that she start her own blog, but she is not game for that.  However, she has expressed a willingness to periodically write and share along with me in this blog.  I think she will bring another perspective to how we deal with the needs of our subbie hubbies :-).

So ... stay tuned for a "Carol's Turn" posting in the near future.


Wednesday, October 26, 2016

Henry's Playroom

Henry was away last weekend, but suggested to Carol that she introduce Barry and me to his playroom while he would be gone.  He thought it might be easier for Barry if the three of us explored and tried out some of his toys without him being part of the process.  Barry and I thought that was very kind of him and liked to idea, so we accepted Carol's invitation to visit it Sunday afternoon.  We were each very amazed and the three of us had a fun time.

As I mentioned in a previous post, Henry had been seeing professional doms and disciplinarians prior to meeting Carol.  He got nervous about going to their facilities, so he decided to purchase the equipment he enjoyed most and set up his own playroom, with the understanding that the doms and disciplinarians would come to his home.

His playroom is part of an unused in-law apartment in his basement.  As you enter the apartment from the outside or a staircase in the home, you enter what would have been the living room.  Henry now uses that room as his home office and a sitting area.    The office area serves an office setting for appropriate role plays; and the sitting area provides a lovely domestic setting for OTK spanking, light domination, etc.  As we entered the room, my eyes were immediately drawn to a two foot heavy oak ruler on the top of the desk, as well as a crock sitting on the floor in the corner containing several canes.

What was originally designed to be the bedroom had been converted to an exercise room by the previous owner (complete with mirrors on the walls and a flat screen wall mounted TV)..  Henry has now converted this room to a very tasteful room containing his 'heavy' furniture.  This currently includes a wonderful spanking bench and an old gynecological exam chair that he purchased on eBay.    It also contains other serious equipment such as his collection of paddles and straps; as well as a Venus 2000 penis milking device and electrical stimulation toys.

Off the former bedroom is a larger bathroom, which contains a large walk-in shower and significant floor space.  The space allows for fairly large wicker bench (2 x 3') and a rolling medical stand that holds a medical grade two quart enema bag.  There is also a small cabinet containing significant equipment and toys that would most likely be used in the bathroom.

The facility is quite impressive.  After giving us a tour, Carol asked us if we'd like to play.  She explained that Henry has taught her how to use most of the equipment, including the Venus 2000 and electrical stimulation toys.  We quickly took her up on the offer.

Heavy Duty steel spanking benchWe started out with the spanking bench.  Henry didn't want us to take any photos in his home, which we respect.  However, Barry found his bench on line.  Carol didn't waste any time in getting Barry secured to it.   Once Barry was on it, I fell in love with it.  It presented his bottom in a wonderful position for spanking and his legs were spread quite wide, so it allowed options for many other types of play.  Carol was also very nice to make sure that his genitals were pulled back and fully exposed as she secured him to the bench.   I had toyed with buying a bench similar to this a couple of years ago, but was afraid to have it in our home. It is truly a fun piece of furniture.

I wanted to keep our play fun, but I also wanted to try some of Henry's toys that were new to me.  I started with a wonderful bamboo paddle.  It was over a foot long and less than a 1/4 inch thick. I suspected that it would provide a lot of sting ... and it did!  If anyone remembers the "SpankingMyHusband" blog by Deirdre, you may recall that she used to secure her husband, Evan, to a bench and then spank him for a predetermined period of time.  I decided to use that technique with Barry.  I announced that he would receive a five minute paddling with the bamboo paddle. It was then that Carol suggested we attach some electrodes to his penis and use the electrical stimulation device to keep him excited.  So, with his penis undergoing constant stimulation, I began to paddle him at a reasonable intensity for five minutes.  I managed to maintain a wonderful balance of making him feel the paddle, but never losing his erection.

I then selected what appeared to be a very old leather belt from Henry's collection of implements.  It was about two inches wide and very soft and supple.  However, it was clear that it had a different impact on Barry ... less sting, but definitely an impact.

It was then that Carol asked if I had ever used a cane on Barry.  I had not, and I heard Barry grown and softly say "Please, no".  Carol went out to the office and returned with a selection of canes.  She and I chose a relatively thin one and she asked if I would like her to demonstrate how to use it.  I agreed and she gave Barry several light strokes as she demonstrated proper technique to me. I took over and started out quite gradually. However, when I finished, I had left three very pronounce stripes across the lower portion of his bottom.  By this time, even with the electrical stimulation, Barry was quite soft.

We then discussed other possibilities with the spanking bench, especially how easy it would be to make a spit roast out of Barry with each of using strapons.    However, we decided to leave that for a later time.  I was much to anxious to get Barry on the exam chair.

Urological examination chair / gynecological / electric / height-adjustable Femi 1, Femi 2 FormedAgain, this is not a photo of the actual chair.  Henry had purchased his on ebay.  It was a bit older, but it was similar to this photo.  It had arm rests to which Barry's arms could be secured; and leg rests that spread his legs. It also left his genital area and anus completely exposed.  Once Barry was secured in it, I began play with him and tease him.  His erection came back to life. Carol then showed me how to use the electrical stimulation toy with a large butt plug that would then pulsate in his bottom.  Since the chair's height is adjustable, Carol also pointed out how easy it would be to peg him and be able to watch his facial expressions and play with his genitals ... all at the same time.  Again ... something for a future play time.

Carol then showed me how to use the Venus 2000 penis pump.  She installed the cylinder over his penis and set it to slowly pump him.  She then suggested that we go have a cup of tea and talk about Henry's play room.  I agreed; and we left Barry with a butt plug pulsating in his bum hole and his penis being slowly pumped.  We enjoyed the tea in the office, so we could be aware of Barry's sounds of arousal and frustration.  When we returned to him about a half hour later, Barry was clearly in need of relief.  Carol then showed me how to turn up the Venus 2000 to a rate that quickly brought him to orgasm.  However, Carol was not showing any interest in quickly turning it off.  Consequently, it continued to pump on Barry's spent organ, which caused him a deal of frustration.  It was then that my mind began thinking about all of the things we could do in this playroom  with both Barry and Henry.

We subsequently released Barry from his ordeal and we all enjoyed a glass of wine together as we debriefed and talked about Henry's wonderful playroom.


Thursday, October 6, 2016

The Rest of the Story

I met with Carol Monday afternoon and we had a good discussion about Sunday evening’s events.  I’ll share more about that meeting in a subsequent post.  However, I have decided to share what took place with Barry and me on Monday evening.  I initially didn’t think I would share this, but have subsequently decided that I should.

Even after my meeting with Carol, I was still dealing with my feelings of jealousy towards her because of Barry spanking her.  I was convinced that the reason he had such an erection while spanking her was because it was her bottom.  I was sure that spanking me would not have generated the same response.   Carol tried to reassure me that Barry will have the same reaction from spanking me as he did from spanking her.  She even challenged me to try it and see if I can prove her wrong.  It only made matters worse when I asked her about being shaved ‘down there’ and why she started doing it.  She told me about how sexy it makes her feel and how much Henry loves it.

So, I came home from Carol’s house feeling even worse than before.  Later Monday night, I ended up taking her advice.  When we were getting ready for bed, Barry kept asking me what was wrong, but I couldn’t tell him.  Finally, I turned to him and said, “Darling, would you spank me like you spanked Carol last night?”   He got an astonished look on his face and asked me if I was kidding.  When I said I was dead serious, he replied “You don’t know how much I would love to do just that.”

I told Barry that I would meet him in the family room in a few minutes.  I stayed in the bedroom and changed into the outfit I wore Sunday night.    When I entered the family room, Barry was sitting on a dining chair in the middle of the room, wearing only his pajama bottoms, waiting for me.  After calling me over to his side, he told me how much he loved the outfit I was wearing.  He then told me that I had been a very naughty girl lately and deserved a good spanking.  He then gently took me over his knee and started going through the same routine he did with Carol.  It didn’t take long for me to feel his tent pole poking my lower abdomen.   At that point I began to relax.  By the time my panties had been lowered, his tent pole felt huge and he also began to put his fingers between my legs and search for my clitoris.  It was then that I asked him if he would like me to shave ‘down there’ like Carol does.  His response was an enthusiastic “That would be very sexy and I would love it if you feel comfortable doing it.”

At this point I began to feel extremely emotional and upset with myself for having let jealousy take over my life.   I started to shed some tears of joy and frustration all mixed into one.  Barry immediately sensed that something was different and he asked me what was wrong.   I then shared with him about the jealousy I had been feeling and how guilty I felt about it.  And, I asked him to spank me much harder to remind me to never let jealousy take over again.  He then began to do just that.  Before long, I was lying over his lap, quietly sobbing, as he spanked much more firmly and deliberately.  It was a wonderful feeling.  When he finally finished, he sat me on his lap and hugged me and told me how much he loved me and how sexy I was.

After a few moments, I slid off his lap onto my knees in front of him and gently exposed his rock hard penis.  “Mmmm, no ED tonight”, I joked.  He smiled back as I lowered my head and began to lick his tent pole.   It wasn’t long before we returned to the bedroom.  Barry got on his back on the bed and guided my pelvis over his face where we could then offer each other mutual oral pleasure. 

I think that is more than enough details.  Suffice it to say that it was a wonderful evening which took away my feelings of jealousy and my guilt for having them.

Now you know "the rest of the story"!


Monday, October 3, 2016

The Masturbation Competition

Last night was the masturbation competition between Henry and Barry.  We decided to have dinner at our house.  When Carol and Henry arrived it was clear that Carol had dressed for the occasion.  She was wearing a very snug short dress that left nothing to the imagination about her shapely derrière.  I could also tell that she was wearing a garter belt and stockings underneath it.  I also dressed in what I thought would be appropriate to administer a disciplinary hairbrush spanking to Barry (since I expected him to lose, I thought I would dress in a way that he enjoys when being spanked).  I was wearing a snug black pencil skirt and a fitted white blouse.  I was also wearing my sexiest white bra that reveals significant cleavage along with a garter belt and stockings.  It is Barry’s favorite outfit

The Challenge
We enjoyed a relaxing informal dinner, after which we retired to the family room and lit a fire in the fireplace.  Carol said that she was sure both men were wondering why they had been allowed to not wear a chastity device tonight (Carol and I had agreed on that, as well as telling them only that we were planning a special surprise activity for them after dinner … and that they would not need their cages for it).   After we settled down by the fire, Carol then explained that we have planned a friendly competition between the men.  She relayed the story of Henry telling her about having participated in ‘Circle Jerks’ while in college.  I could see Barry’s eyes get wide and I was sure that he was thinking “No way do I want any part of this idea”.    However, he kept quiet and let Carol continue.  She explained that she and I would enjoy watching them masturbate; and she added that we had decided upon a way to make it interesting and fun.  She explained that the goal would be to be the first one to climax, and that the winner would earn the right to turn Carol over his knee for a friendly bare-bottomed hand spanking.  Much to my surprise, Barry was the first to say “I’m in”.   Carol stopped him from saying anything else by saying, “Wait, there is more”.  She then explained that the loser would stop masturbating as soon as the winner had been declared;  and would then go over Susan’s lap for a bare-bottomed hairbrush spanking.  Barry piped up again with “I’m still in”.  It was clear that he was thoroughly motivated by the possibility of getting to spank Carol.  I have to admit that I wasn’t pleased by that reaction and silently planned to make him a pay a special price for it with the hairbrush.

Henry was not so quick to accept the challenge, which concerned me a little bit.  I was sure that Carol must have mentioned Barry’s ED issues to him at some point.  However, he eventually agreed to be part of the competition.

The Rules
Carol then provided the following ground rules:
·        Each male will strip and be naked
·        Each male can use the lubricant of his choice
·        Each male will be given a small wine glass into which he will ejaculate
·        Each male must be completely flacid when the competition begins and can begin when Carol announces  that the competition has started
·        Neither male is allowed to use any form of pornography or any physical device while masturbating (just his mind and his hand)
·        The winner is the first one to expel semen from his penis into his wine glass
·        The loser must stop as soon as the winner is declared
·        The winner must then drink his semen from the wine glass
·        The winner will be permitted to turn Carol over his knee and spank her bare bottom with his hand.  Spanking is not to be so hard as to cause Carol significant pain.  If she says the word “yellow”, the spanker must reduce the intensity of the spanking.  If he does not, Carol can say the word “red”, which will signal the end of the spanking.
·        The loser will then receive a disciplinary hair brush spanking from Susan on his bare bottom.  This length and severity of this spanking will be determined solely by Susan.   The loser must endure whatever she chooses to dish out.

After Barry and Henry agreed to the above rules, Carol and I seated ourselves comfortably on the sofa and Carol directed them to remove all of their clothing.   I was surprised to see that Henry was now wearing panties.  As they became visible, I nudged Carol and smiled approvingly.  She smiled back.  I whispered to her that I will be anxious to learn more.

The Competition Begins
Once they were naked, we had the men position themselves in front of us.   Then Carol stood up.  Turning her bottom towards them she placed one hand on it and reminded them that the winner would get to spank her.  I then held up a heavy wooden hairbrush and reminded them that the loser would get to experience a heavy dose of it.   Carol then said “Gentleman, you may start to masturbate.  May the best man win.”

It was quite interesting and somewhat amusing to watch the two men start to masturbate.  I must admit that I hadn’t fully shared Carol’s fascination and desire to watch them masturbate.  However, this quickly became interesting.   Requiring them both to be flacid at the start was not an issue.  It was apparent that each of them was embarrassed by having to strip in front of each other and Carol and me.  As they began, I could tell that each was trying to mentally overcome that embarrassment and to achieve arousal.  It was also clear that each was also keeping an eye on the other one.  Henry achieved an erection first, which was no surprise.   What was a surprise was that he didn’t appear to be very ambitious in his attempt to masturbate once he was erect.  It took Barry a few more minutes to get hard.  Once he did, he started to work vigorously to bring himself to a climax.  Henry then began to work harder, but not as hard as Barry.  Carol and I both looked at each other and were quite puzzled.

We Have a Winner
After a number of minutes, Barry climaxed into his wine glass.  Henry wasn’t even close and didn’t seem to be trying very hard.  Carol and I looked at each other … and each quietly voiced, Henry didn’t try to win!  I recovered more quickly than Carol and directed Barry to drink his output.  I added, “After all, that is our house rule; whenever you get to cum you have to consume it”.  I immediately saw Henry’s look of surprise and Barry’s look of embarrassment.  Apparently, that was one secret that Carol had not shared with Henry.

As Barry performed his requirement to drink his semen, I announced, “I think it’s time for dessert”.  I needed some time to prepare myself for what was to follow.  I did not expect to have to watch Barry spank my sister.  And, I did not expect to have to provide a disciplinary spanking to Henry.  While Carol and I were alone in the kitchen preparing dessert, I asked her if she knew what was going on with Henry.   Why didn’t he even try to win?    She didn’t know either.  I asked her if I should try to sort it out when I gave him the disciplinary spanking.  She agreed that I should.

Carol Gets Spanked
After having dessert by the fire, I brought a dining room chair into the room and placed it facing the sofa, about four feet in front of it.  I announced that I thought the winner should go first, so Barry took his place on the chair and directed Carol to come stand by his side.  As she got up to join him, Henry joined me on the sofa and I reminded Barry of the rules that were established about spanking Carol.  I also told him that he had better follow them completely or he would find himself getting a disciplinary spanking along with Henry.

I could tell that Barry was enjoying this moment immensely.  He guided Carol into a position over his lap, using his right hand to grasp her bottom as he did so.  He then took his time shifting her a bit to get her into a comfortable position for him to spank. I noticed that Carol seemed to intentionally arch her back a bit, to elevate her bottom, which didn’t please me very much.  It only served to accentuate her already shapely behind.  Barry then asked Carol and me if it was OK if he began the spanking over her dress instead of starting out immediately on her bare bottom.  We each agreed.  I figured it was that much less time that he would have to observe and touch her bare bottom.

Barry then asked Carol if she was ready for him to begin.  When she applied affirmatively, he told her that he understood that she had been a very naughty girl, and asked her if she knew what happens to ‘very’ naughty girls vs. just naughty girls.   When she said that she didn’t, he then advised her that naughty girls get spanked, but ‘very’ naughty girls get spanked on their bare bottom.  He further explained that he was going to start spanking her on her dress, but since she had been ‘very’ naughty, he was going to eventually bare her bottom before he was done.  During this entire conversation I couldn’t help but focus on the fact that Barry’s right hand was cupped around her right bottom cheek.  He then began to spank her:  slowly and methodically over her dress.  After each spank, he allowed his hand to remain on her bottom for a second or two.  I’m embarrassed to admit that I was getting very jealous and upset.  I had to force myself not to make a comment to remind him to behave himself.  I also had trouble watching what was happening.  I wanted to watch Barry’s face to try to determine how much sexual pleasure he was deriving.  I also wanted to watch his right hand to see what he was doing.  You can probably guess that I was a mess!  However, I managed to keep myself together.

After several minutes of rhythmic spanking, Barry eventually announced to Carol that it was time to raise her dress and asked her if that was OK.  I had to admit that he was being the perfect gentleman that I know him to be.  Carol replied affirmatively.  Barry then slowly slid her dress up above her waist to reveal, what I am sure, she had worn to please Henry.  As he did so, he revealed stocking tops attached to a silver grey garter belt, and a bottom encased in sheer pink panties.  The panties had ridden up a bit to expose more cheek than they were designed to.  Barry carefully pulled them back into place to cover more of her bottom.  Again, a perfect gentleman.  I was focused on watching what was happening, but by the sound I heard emitted next to me by Henry, I was aware that it took his breath away. 

Resting his right hand on her bottom (I couldn’t stop my focus on how much his hand was in constant touch with her bottom) Barry immediately commented that her panties weren’t going to offer her much protection, but they would eventually also be removed.  (My mind was in overdrive at this point.  I couldn’t help but feel that Barry was creating a sexual experience for himself … and I didn’t like it.)
Barry then resumed the methodical spanking as before, usually alternating from cheek to cheek, but sometimes administering five or more spanks in a row to the same area.

After another period of time, Barry paused again and advised Carol that it was time to lower her panties and receive the spanking that ‘very’ naughty girls deserve.  He asked her if she objected.  When she said that she did not, he slipped his finger tips into the waist band of the panties.  As he did so, Carol raised her bottom slightly to allow him to lower them.  Barry slowly lowered them to her knees.  I couldn’t help but notice that Carol spread her legs slightly after the panties were lowered.  I could tell, even from where I was sitting, that she was providing Barry with a delightful view.  It also appeared that Carol was cleanly shaved in that exposed region.

Resting his hand on her bottom again, Barry announced to Carol that this is when a real spanking takes place.  He then resumed spanking, not any harder than before, but at an increased pace.  I could tell that Carol was feeling this more.  Barry also seemed to focus more on her lower bottom than he did before, which is much more tender.  I could see Carol’s face and it was clear that she was working to handle the faster spanking.  At one point Barry picked up the pace a little more, which caused Carol to utter “yellow”.  Barry immediately paused and asked her if she was OK.  When she replied affirmatively, he resumed the spanking at a similar pace, but with less force.  After another minute of causing Carol to squirm, he announced to her that he was going to administer ten hard spanks rather rapidly, which would be the end of her spanking.  He asked if she thought she could take that.  Hearing a ‘yes’, he then delivered the ten as promised.  Carol was very actively squirming and groaning after the first five, but she took them all.  When he finished, he patted her bottom again and told her it was a lovely shade of pink, which should nicely match her panties.

Barry then helped her to her feet.  She immediately reached down to pull up her panties.  Since her back was facing me, I could see that Barry was correct about the shade of pink.  I also glanced over at Barry’s eyes and it was very clear at what part of Carol’s anatomy he was watching.   His eyes were fixed on her crotch.

At this point, Barry thanked Carol for allowing him to spank her and told her that he thoroughly enjoyed the experience.  He added, “I hope you did, as well”.  Carol immediately responded that she did; and that it was obvious that he did.  She then directed Barry to stand up and show Henry and me his “tent pole”, adding for our benefit that she could tell he was enjoying it by the pressure his erection continually placed on her.  Barry hesitated to stand, and she reached out a hand to help him.  There was definitely a tent pole in his pants!  Carol then jokingly added that it looks like we have discovered a solution for Barry’s ED.   She then turned to me and said, “All you need to do is take a short trip over his lap for a sensual spanking … and he’ll be ready to go.”

A Surprise for Barry
Carol then stated that she thought Barry needs to get rid of his erection; and she proposed that he be required to masturbate for us again.  She also justified her request by stating that she helped him get that erection, so she should get to say how he relieved it.  Barry looked shocked.   I was embarrassed, but not surprised, by Barry’s  sexual reaction to spanking Carol.  Jealousy again reared its ugly head in me.  And, feeling a need to punish Barry, I quickly agreed.

We then took a break for a second cup of coffee before proceeding.  We also talked briefly about Carol’s spanking and she again thanked Barry for being such a gentleman about how he did it.

Time to Sort Things Out with Henry

I then stood up from the sofa and turned to Henry who was sitting next to me.  I grabbed him by his left ear and marched him over to the dining chair, telling him “We have a few things to discuss tonight about your behavior”.   I could tell that my abruptness took him by surprise, which was the effect I wanted.  As I did this, Carol and Barry moved to the sofa.

Sitting on the chair, I told Henry “The first thing I want to talk with you about concerns why you didn’t seem to try to win the contest earlier tonight.  It was obvious to Carol and me that you weren’t even trying.”  Henry initially claimed that he had tried but was embarrassed by the entire situation.  After being pressed further, he finally admitted that he had decided that he really wanted to experience being spanked by me, so he decided that by losing the contest, he would get what he considered to be the winning prize.  Carol piped up and asked what happened to his desire to spank her bottom.  Henry, unwisely, remarked that he thought he could talk her into that when they were alone, but getting spanked by me was harder to arrange.   Carol’s response was simply, “Don’t be so sure of yourself about either assumption you made”.  I commented that it sounds like Henry has made the common mistake of thinking with the wrong head.

Keeping Henry standing by my side while I sat in the chair, I asked him to remove his trousers and to fold them up neatly and put them on the floor.  He quickly complied.  I couldn’t resist commenting on the fact that he was wearing panties and that he had an erection.  I asked him if he was excited about being turned over my knee to be spanked.  He indicated that he was.  “Well, let’s see how long that lasts”,  I remarked.

I then asked him if he has ever received a disciplinary spanking.  He replied that he had.  When pressed for details, he admitted that he has received them from the dominatrix he used to see before he got serious with Carol.  I decided to probe further and asked him if she had ever spanked him to a point where he didn’t feel he could take anymore.  He replied that she had, so I asked “And what happened then?”  His reply was that he used his ‘yellow’ safe word and she lightened up.  I couldn’t resist asking “And you think that constitutes a real disciplinary spanking?” 

Henry Learns What to Expect
Not waiting for a response, I went on to explain to Barry what constitutes a true disciplinary spanking… and what he could expect from me in a few minutes.   I first explained that he would find himself turned over my knee with his bottom bared.  I would begin by using the hairbrush to thoroughly spank every inch of his bottom until it was very red and very sore.  I added that the intensity would be very tolerable, and perhaps even enjoyable to him.  However, I further explained that it would be a long spanking, and when I was done with that part of his spanking his bottom would be very sore for at least three days; and that the purpose of that was to make sure he thought about his punishment every day for that length of time.  I went on to explain that once I felt his bottom was sufficiently tender and sore, the real punishment would begin.  I would then spank with greater speed and intensity.  He would quickly come to the point where he felt he couldn’t handle anymore.  “However”, I added, “It will be different this time.  There will be no safe word.”  I went on to explain that when I sensed he could not handle any more, I would not ease up.  Instead, I would increase the intensity, while making sure I held him firmly in place.  He would have no choice but to take it.  “That”, I explained, “is when real discipline and real learning starts to happen.”

I then asked Henry if he was ready for that.  As he responded in a positive way, I looked again at his penis.  It seemed to be harder than before, and I could see that it was visibly twitching.  “You seem to be very aroused”, I commented.  “Would you like to experience a release from that?”  Not surprisingly, Henry said “yes”.   Barry immediately said “Don’t do it Henry”.   I gave him a look that told him to stay out of it.

A Surprise for Henry
I then turned to Carol and shared with her that it appears to me that Henry is still thinking with the wrong head.  I expressed my opinion that I thought we should grant his request and then I should administer an appropriate disciplinary spanking to him.   When she agreed, I asked her how she thought we should allow Henry to experience a release of his sexual tension.  I was not surprised when she suggested that he should masturbate for us and drink the result just like Barry did.

Henry quickly found himself standing in the middle of the room masturbating, with me holding a wine glass to catch his semen.  It took him less than a minute to achieve orgasm and express a significant amount of fluid into the wine glass.  “Wow”, I said to Carol.  “How long has it been since he’s had a release?”  The answer was a little over a week because Carol was trying to make sure he would win the original competition.  Henry didn’t appreciate it, but I quickly held the glass above his mouth and forced him to drink his semen.

Henry Receives a Disciplinary Spanking for the First Time
Henry then found himself standing by my side as I sat in the dining room chair.  He was naked from the waist down.  Using the bristles of the hairbrush to tease his flacid penis, I asked him if he was still excited about receiving the disciplinary spanking I previously described to him.  He clearly was not.  I then asked him if he knew why I was going to discipline him.  I was pleased to hear him say that it was because he made bad decisions, using his dick (his word), instead of his brain.  I acknowledged that he was correct and asked him to tell me the bad decisions he made.  He correctly mentioned his decision to not try to win the masturbation contest with Barry.  However, he didn’t come up with anything else.  So, I suggested to him that by the time we were done he would regret the decision to have a sexual release before the punishment.

I then turned Henry over my lap and made him spread his legs to better expose his lower cheeks and lower groove between them.  I spent a considerable amount of time methodically spanking his entire bottom and upper thighs with the hairbrush.  I made sure I paid attention to the lower slope of his cheeks and the area between them.  He actually seemed to enjoy it for a while.  However, before long, it was clear that it was no longer enjoyable, but not intolerable.  When his bottom was a uniform red color and he seemed to be squirming more, I paused to ask him how his bottom felt.  It was clear that he felt it was very sore.  I pushed some more and learned that it hurt more than he has ever felt before.  I told him that it should and that I expect that it will hurt for several days.  I reminded him that this is part of the disciplinary process.

I then told Henry that we were going to move to the next stage of his disciplinary spanking.  I used my right leg to clamp over Henry’s left leg. I then asked Henry why he was being disciplined.  This time he got it completely correct about the two bad decisions he had made.  I reminded him to keep both of those decisions in mind during the next few minutes.  I then began to spank him with the hairbrush much more intensely.  I still didn’t have to swing hard.  I let the hairbrush do the work.  However, I increased the frequency of the spanks and often spanked the same spot repeatedly.  Henry’s distress level increased significantly.  At one point I paused and asked him if we were at the point he had previously used his safe word.  Stupidly, he said “no”.  So I took his right wrist in my left hand and held it behind his back.  I then began to spank at the same frequency, but a bit harder.  It was not long before he was frantically trying to get away from me.  At this point, I reminded him that this is when things get learned and to think about his bad decisions.  I continued to use the hairbrush to punish his already sore bottom.  I was very intentional in what I was doing.  When I finished, it was all I could do to hold Henry in place as I spanked him.

When I finally stopped, Henry just slumped over my knee.  I asked him what he had learned.  It took him some time to respond, but I was very pleased to hear that he learned not to think with his ‘dick’ instead of his brain.  And, I was surprised to hear him add that he learned what a real disciplinary spanking was all about.  I decided not to push it any further than that.

I looked over at Carol and smiled; and she smiled back.  I looked at Barry.  It was clear that he had been relating to what Henry was experiencing.  His face was ashen.  He knew what Henry had just experienced and obviously had a lot of empathy.

I apologize for the length of this post.  It is much too long, and probably not well written.   However, I was anxious to share what happened last night while it was still fresh in my mind.  I will also get together with Carol later this afternoon. That will give us a chance to talk about what happened last night.  I look forward to learning more about her reaction and sharing mine with her.  There is much to talk about J!


Thursday, September 29, 2016

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.


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.