My Special Matchmaker, Part 3 When I was following Cindy to her apartment, I was happy that a woman was willing to have a conversation with me even though I liked dominate women and was willing to be spanked by them. We both parked in the apartment parking lot, and then Cindy led me up to her apartment. "Go ahead and sit on the couch while I change into something more casual and comfortable." Cindy seemed to have a large apartment, and it was furnished with some fairly new, up to date furniture. Also, the apartment smelled like Cindy, which was in contrast to the sterile smell of the doctor's office. When Cindy entered the living room, I was pleasantly surprised. Instead of a white nurse's uniform, she was wearing a colorful thin summer dress. She sat down very close to me and said, "I have seen what you look like physically, and by your initial test results, you are a healthy male. So what has influenced you where you want to meet a dominant woman who spanks you?" I told Cindy about growing up in a family where my mom spanked me, my older sister spanked me, and my sister's friends spanked me. I also told her about finding my dad's stash of porn that also had to do with spanking and dominate women. In college I had seen some pros, but now I wanted a long-term relationship with a dominant woman, that I could marry someday. "I have to admit," Cindy said, "that spanking you and feeling your prostate was a little turn on for me, too. That is why I invited you to my apartment." "I am happy to hear that. One of the things that make me feel really close to a woman is when I am given and over the knee spanking. My penis and balls dangle down between the woman's legs, and I can feel the force of her thighs, as they hold me in place. Then I am aware of the woman's unique scent, I can feel her body heat, and I hear her soothing voice. As I am spanked, the lower part of my body warms up and I get a big erection. Also, I do feel that women are dominant in their thinking and being capable of handling many things at once. So now you know a lot more about me." "Since I liked spanking you during your exam, would you like me to try giving you an over the knee spanking?" "You could try it. The only thing is it will not feel the same because my penis is in this chastity device." "Don't let Jane or the matchmaker know this, but I noticed that there were many identical keys in the box. So I took one. I could actually free you during your spanking, but I would need to put you back in it before you leave." "Okay. Let me take off my clothes, and then you can take off the chastity device. After that, I can feel what it is like to have you spank me while over your knees." Although Cindy had seen me naked during the exam and had spanked me, it still felt different and exciting standing before her. "I have never worked with a men's chastity device before, so it may take a little bit of time." Soon she had the lock off, followed by the whole metal device that was around my penis. I couldn't help myself, but my penis instantly sprang into a hard erection. "Now I can see why they wanted you in that device until after you get back the lab results." Cindy hiked up her thin dress and said, "Now go over my knees so I can spank you." Before I went over her lap, I noticed that she was wearing some pink panties. Cindy had spanked me before while I was bent over the exam table. But this felt a lot more intimate, with my penis and balls hanging between her thighs. I knew from being spanked by the pros that they always liked my legs spread apart, so I did that for Cindy. Then my spanking began. Compared to my other spankings, I could barely feel anything. "You can spank me harder. Don't be afraid about hurting me." "Maybe I should use my wooden hairbrushes on you. Stand up so I can get them from my bedroom." Cindy came back with two large, wooden hairbrushes. "You should be able to feel your spanking now! So get back over my knees." Now I could feel her spanking me and I could feel that wonderful warm feeling in my lower body. I was also aware that my erection was growing harder and bigger, and my penis was dangling between Cindy's upper thighs. This is what I haven't felt in a long time and what I was hoping to find in a woman who cared about me. The more Cindy spanked me, the better I felt. "Your poor bottom is getting really red and feels really hot. Stand up for me and put your hands behind your back." I did so and then Cindy put a condom on my erect penis. "I don't want you to make a mess." Then she started to stroke my penis and feel my balls. In a short time, I felt a warm sensation fill my whole body and I exploded into the condom. "Stay there and don't move. Let me get a towel and washrag and clean you up." Next Cindy returned and took the condom off and cleaned me up. The warm washrag felt so good on my now very sensitive penis. After Cindy dried me off she said, "Keep you hands behind your back." Then to my surprise, she started to put back on the chastity device. "Please, can't you leave it off for a while? I really want to feel myself again." "I think Jane and your matchmaker wanted it this way. Besides, I would like you to come over to my apartment tomorrow. Then I could spank you again. Would that work for you?" "Yes, I'll be here around seven o'clock. Thanks for everything." I put on my clothes and we hugged each other. I thought I was only getting a medical exam, but I met Cindy and received a spanking as well. What a day! *** *** It was different sleeping that night. I am used to touching myself and thinking about what happened to me the previous day. I also found out that it was easier to pee if I sat down on the toilet, because I was now wearing the chastity device. When I went to work the next day, I was very aware that I was wearing it, but even my female co-workers didn't seem to notice. So I was glad of that. As the day went on, I was very grateful that Cindy had the key and I would be released from it, even if it were for a short time. After work, I ate and showered again before going to Cindy's apartment. I arrived right at seven o'clock and Cindy greeted me wearing another thin, summer dress. But instead of inviting me in, she said, "I want you to take me someplace where we can have desert and talk." I said, "Okay. That seems okay with me." Then I drove Cindy to a restaurant that I knew had great deserts and was open later. We started out talking about the weather but then went into a deeper conversation about my seeing her. I told Cindy that I was starting to like her and I couldn't see any reason why we couldn't date. I was glad we were seated away from others because Cindy asked, "I was wondering if the only reason you were seeing me was because I have the key to the chastity device you are wearing?" "I do have to admit that you having the key does make me want to see you again, but I also like your personality and that you are a strong woman," I said. "Well, I do intend on spanking you once we get back to my place, but for now I want to hear more about you and I want to tell you what I would like to see in a relationship." So we had a long talk about both of our likes and dislikes. Cindy had heard that there were some submissive men out there, but had never met one until I entered her life. Also, if we disagreed on something, I felt that we were still compatible with our main ideas in life. We talked so long that I soon noticed it was 9:30 PM. "I know that both of us need to work tomorrow, so I better get you home. I didn't realize it was so late." So I left a big tip and I took Cindy back to her house. When we arrived at Cindy's house, she said, "Come inside with me. I know it's late but I still want to give you a quick spanking." I was so happy that Cindy was going to give me another over the knee spanking. When I entered her living room I quickly took off all of my clothes, folded them and placed them neatly on a nearby chair. Once Cindy walked into the room carrying a large wooden hairbrush and seated herself on the couch. "Can you please take off my chastity device?" I asked. "There you go again talking about your chastity device", she scolded. "I thought you cared more about me and being spanked. Just for that, I am going to give you a longer spanking." "Sorry about that", I said as I laid across her knees. It felt different this time because since I was still wearing the chastity device, I couldn't feel my penis between her thighs. It did feel good that Cindy was spanking me again. Soon I felt my bottom getting warm and now my penis really felt trapped in the chastity device. "You better stand up, get dressed and leave now," Cindy said. "But can't you release me? I feel so horny," I pleaded. "Sorry, but that is what chastity devices are for," Cindy said. "See you tomorrow night at seven again." So I got dressed and Cindy lead me to the door and gave me a quick kiss on my cheek as she grabbed my bottom. I felt good that Cindy and I had that talk and she spanked me but now I really felt trapped with the chastity device.