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.