It has been awhile since I posted about “Sir.” We haven’t seen him in person since our September hotel date, but he texts every few days to check in, and sometimes we find the opportunity for sexting play.
If I’m honest, I find him to be ridiculously charming. I suspect that if we had met some other way, we would be friends (without sex benefits). We both have eclectic tastes in books and tv and like to talk about it. We both enjoy a nice glass of red wine (and he enjoys prompting me for details about my fantasies once the truth serum has been ingested). And we have similar senses of humor. All of which is to say that I really enjoy chatting with him.
When the timing works out, we’ve also played virtually. I confess that I don’t totally understand what Sir gets out of our relationship (other than the friendship I described above). I think he just genuinely enjoys helping women push their sexual limits. I’m not complaining because I benefit from the experience.
Recently, we had a play time that is worthy of sharing here. It took me a bit to process, and I had to go to my VHW friends for help putting it into perspective. For that reason, sharing it more publicly might help others to know that it is totally normal. Or maybe you’ll all judge me and think I’m weird

Either way, here it is.
The play time began in a typical way. I was in my bedroom and Sir instructed me to get naked, and attach a leather collar as well as wrist and ankle cuffs. This time, he also told me to attach two sets of clamps to my nipples. We’ve been working on nipple play lately, and I am getting quite good at wearing clamps for a prolonged period of time. I’ve never worn two sets at once though!
I attached my gentler pair just above my nipples and the more intense pair below. I’m not going to lie. It hurt. After a minute or so, however, the pain dulled and the result was a very heightened sensation in my whole body.
Sir asked me to get out several of my toys (because we play via text, he had asked early on for a complete inventory of all of our sex toys. Sometimes he also suggests non-typical things to have on hand such as clothes pins, chop sticks, or rubber bands). I let him know when everything was assembled.
We started fairly easily. He had me lay down and hold a magic wand against my clit.
We own two of these wands. One is old-school and plugs into an electrical outlet. The other runs on a rechargeable battery. The electric one is much more powerful, and that’s the one that he wanted me to start with.
I used it on low and gave my pussy a bit of time to warm up. Since I was already aroused by chatting with Sir, it didn’t take long before I orgasmed.
Sir asked me to check on my wetness levels. I inserted a couple of fingers and pulled them out. I let him know that not only was I audibly wet when fingering myself, my fingers were coming out very creamy.
“Excellent, then let’s work on getting that wand inserted in your pussy,” he instructed.
If you have a magic wand, you may understand the magnitude of this request. The head is very large. It wasn’t going to slide inside very easily. I added some lube and began to work it in gently, teasing myself with it and letting myself open up a little bit at a time.
Sir was happy to keep me entertained while I worked. He texted me with all his ideas for our next in-person play time. Some made me laugh. Some made me institute a strict veto. Many made me aroused to think about.
After several minutes and a very solid push, I was able to report that the head was fully inside. It wasn’t painful in any way, but I felt stretched and very full. Sir instructed me to turn the wand on.
“No,” I responded. Then I added a follow up, “I don’t think I’m ready for that yet.”
“Not a problem, Wench,” he said. “Use your fingers on your clit and let me know when you feel ready.”
I did as instructed and soon could feel my arousal building. I was less focused on my stretched pussy or my clamped nipples, and was instead noticing that my whole body was turned on and eager to cum. I told Sir that I was going to turn the wand on.
“Use the low setting, Wench” he cautioned.
I did, and the feeling was intense. I could feel vibrations deep inside - against my cervix and my g-spot. Sir asked me to describe how it felt. Then he had me take the second magic wand and hold it against my clit.
I was not to turn it off without permission. He wanted to see how many times I could orgasm.
I did as instructed. When I turned the second wand on and held it against my clit, I came very quickly.
Keeping the wand on my clit after an orgasm is really difficult for me. My clit gets very sensitive and the vibration feels too intense. Sir and D have been working with me on this lately though. If I can breathe through the initial discomfort, it eventually turns back into pleasure and another orgasm builds.
This time, with the wand also on inside of me, the feeling was super intense. I had an orgasm, and then another would build within two or three minutes. That happened three times.
I turned the wands off, and noticed that while the wands were on I no longer noticed the clamps on my nipples. With the wands off, my nipple sensation was once again prominent. I texted sir to report my orgasms and ask if I could take a break. Could the clamps come off? Could the wand come out?
“No,” was his reply.
I turned the wands back on. My nipple pain went away, and the sensation in the rest of my body built again. This time, the break between orgasms lessened. There was maybe only a minute between them. My face and chest were flushed. My heart was racing. I had to work to catch my breath.
After my seventh orgasm of the session, I turned the wands off again and asked if maybe I could remove the inserted wand. I was once again denied.
“I want you to turn the inserted wand on high and then hold the other on your clit. I want you to cum five times with no turning them off in between. After that, you may remove it,” he said.
It is important to note here that I do have safe words with Sir. I also have the complete ability to not follow instructions if I don’t want to. In this case, I really did want to push myself. I didn’t want to let him down (and I knew D was following along with our text conversation while he was in a meeting at work). So I replied, "Yes Sir."
I turned the wands back on. It was amazing. I can’t accurately describe the sensation. There was a full body intensity that just grew until my orgasms were flowing in waves one after the other.
It was extremely pleasurable, but for some reason I also started crying. I wasn’t in pain, and I wasn’t in a bad head space, my body was just having an emotional reaction for some reason. That’s the part that took me a bit to figure out.
After many orgasms, I turned the wands off and removed the one from inside me. I texted sir to let him know about the waves of orgasm and how they felt. I didn’t immediately tell him about the tears.
He told me how well I had done. He asked if I wanted to make myself squirt before we finished our play time. I said I didn’t.
He told me again how well I had done. I thanked him but said that I was a bit disappointed in myself. I didn’t like how often I had asked to take breaks or to remove the nipple clamps.
“Don’t be silly,” he wrote back. “You had the clamps on for 90 minutes. That’s a new record. And rolling waves of orgasms with two wands is very intense. You did very, very well. You are a treasure. Truly.”
I thanked him but said I still wasn’t sure. I removed the clamps, cleaned my toys and got dressed as I tried to get my emotions under control. Sir continued to chat with me and I think he could tell something was up. Eventually, I confessed.
“I don’t know why, but sometimes when engaged in submissive play, something hits an emotional nerve for me. I can’t explain it or why it happens, it just does. That happened today. I just started crying, but I wasn’t having a bad time or anything. Anyway, I’m just trying to recover from that,” I told him.
“Oh, Wench. That is totally normal. Sounds like you experienced a bit of sub space maybe. I wish I was there to give you a big hug," he answered.
I assured him I was fine, I just needed to ground myself a bit. I’m not sure he totally believed me because he continued to text a bit as I went downstairs and started making dinner.
We chatted about work and our plans for the evening. I also chatted with a few of the VHWs to get their perspective on my emotions. Like Sir, they assured me that this was totally normal. BDSM play can be emotional and even cathartic.
Sir stopped chatting with me once I told him that D was finished work and had come to the kitchen to hang out with me.
D had been following the conversation and gave me a hug. The kids were around so we couldn’t really talk. He just asked if I was ok and I told him that I was.
That evening, when we went to bed, he held me in his arms as I described what had happened. He stroked my hair and kissed my forehead and I felt much better.
Sir checked in with me again the next morning. He really is very sweet. And I assured him that I’m eager to continue playing. We even have another in-person session planned for next month.
The moral of this story, however, is to be careful when you play alone. Lol. Aftercare is so important.