Real-life meeting with Sir

A little background: I've been a member 11 years and a mod about 9. Some issues in real life and on the site made me back off of posting here, and in the last year as my dad needed more care (dementia), I was rarely even on the site.

I met my Dominant here 10 years ago through the chat room. We hit it off almost immediately, and built a long-distance relationship. That's often not successful for D/s relationships, but in our case it has been good. In person would have been better, but because of His skill in many areas, it has worked. We started with chatting online and went to phone calls and some videos in chat. We have done lots of play, with Him supervising enemas and orgasms--including being able to trigger one with just a word--along with occasional punishments. And He was a steady force in my life as I dealt with an abusive husband who blindsided me with a divorce and restarting my life and healing. In fact, if not for Him, I probably wouldn't still be around. I still have a ways to go in some areas, but I've made great progress, and a deep friendship developed. We usually talk several times a day and share tons of vanilla interests.

We wanted to get together and discussed it regularly. But He was caring for his mom, and I became more involved in helping my mom care for my dad, so meeting wasn't possible. As both family situations got worse, D/s got set aside. He still gave me instructions and made sure I was staying out of trouble (those of you who know me: QUIT LAUGHING), and we did enemas, but we quit playing.

Along came the pandemic. Among the many things it messed up was His going on a cruise. Twice. So when the second one was cancelled this spring, I said, “Why don't You come here?”

He did!

We had about 10 days together, and it was incredible (except for having to say goodbye). There is so much to tell, and I'll break it into separate posts. Won't surprise me if He weighs in occasionally too.

This is awesome, Chester! I'm so happy for you and Fencer!

@chester89 Amazing account and great to read. At first I did not realize you were a woman, your ID sounded masculine, but quickly realized as I read what you wrote that you are a woman (not that it matters)… So wow - you finally did meet! Hope your relationship continues - and it goes to show that people do actually find someone here (a question that is asked in other threads). So best of health and happiness to you both!

Sir allowed extra time driving, but He was able to drive farther two of the days than He had expected, so i got extra time with Him--an additional evening and full day. I wondered what He was going to have us do, and i fully expected Him to spank me as soon as He could. Wouldn't have been surprised if He had before we went to get dinner because a warm tush is always a good thing. But He didn't.

We found a spot to eat that didn't have a long wait time and went back to His hotel. Still nothing. Not even a swat from His hand. Part of me was wondering what was up, but most of me knew that He was giving me time to get to know Him face-to-face, and figured He was assessing me as well. Sometimes things work great online or on the phone but not so well in person. He cares deeply and wasn't about to push me too much too soon.

I went over late the next morning so we could run some errands and have a late lunch at a restaurant He was interested in. A pleasant greeting when I arrived. He was genuinely glad to see me. Still nothing kinky. I discovered as we walked at several stores that He liked following a few steps behind me, however. Couldn't decide if it was the view or if He was positioning Himself for an occasional swat when i wasn't expecting it. I know how much Doms like mind games. I finally said something, and He just grinned.

Never a good sign.

We went back to my house to take some groceries we had picked up and for Him to meet my mom. I moved in with her a few weeks after my dad died last fall to help us both financially and so I could help her with stuff around the house she can't do any more. Thanks to my ever-helpful ex, she knew Sir and I had been in a kinky relationship, but she also knew that He had become a close friend, so she welcomed Him, and before long they were laughing together. We would be limited at the house, but i was thrilled they got along.

When we went back to the hotel, Sir got out an odd-shaped bag. And grinned. “Let's try a few things.” I raised an eyebrow but said nothing. He pulled out one implement after another and swatted my backside with my pants still up. Another surprise as a covered tush is never acceptable, but again, He was giving me time to adjust. I gave moderate feedback on each one. In these situations, there's never a good option for what to say. Loud “OUCH” or the equivalent = more because He knows it hurts. Not much response = try harder to get a response.

He finished, and i commented on the pants up. “Tomorrow.”

What a lovely thought for the night.

Wonderful stories of luck and primal connection.

@reddevil I know my name has caused confusion. When I joined looking for information about enemas, I didn't expect to stay and become involved like I did. I knew I liked spankings but didn't know other kinks, and I didn't get creative with a name. I just used the nickname I'd had since high school that my best friend gave me. I had hurt my knee again, and our band director commented that I was walking like Chester on “Gunsmoke.” When she heard that, the name stuck. She rarely called me anything but Chester, even to others. In fact, when I would meet her friends at college, she would say, “This is [real name],” and her friends would look at me funny. She'd say, “Chester,” and they'd be all excited to finally meet me. I lost her to breast cancer that metastasized to her lungs about a dozen years ago, but the nickname lives on. (I'm chester on Sir's phone, even.)

@chester89 Great account about your nickname - yes, when I saw it I thought of Chester from Gunsmoke having watched the series.. Hope all is going well for you and with Sir.. Please keep us updated - he's a lucky guy!

Those first couple of days, as we were getting accustomed to each other's presence, Sir kept a promise He that had made on the phone. He gave me an incredible non-erotic back massage. I was sitting in the chair at the desk, and He came behind me, and without a word started rubbing my neck. He had told me before that He was good. … He is. He has smaller hands, but oh my, they are so strong, and He turned me to mush as He worked my shoulders and up and down my back. Several times when we had talked on the phone about His R-L play He mentioned how the subs wondered how He could spank so hard.

I didn't find out how He did it, but i did find out He could.

On one of Monday's trips to the hotel, I asked Sir, “Now what would You like to do?” He looked at me and told me to lose pants and panties and lie face down on the bed. No explanation, but He doesn't have to give one, and I had a good guess at what was coming. I got comfy on the bed with my face turned from Him. Part of that was because it was comfortable. Part of it was although He hadn't said I couldn't look, I didn't want to. I just wanted to experience.

I felt a hand rub my backside for a few moments, and then the swats started--more of a pat, really, initially, but within a few, they were stinging. He worked side to side and up and down, including pulling my tush upward to swat at its merger with the top of my thighs. I'd told Him that i mark and bruise easily, and He was concerned with how fast i reddened under His hand. After some rubbing to confirm the heat, He stopped. We had a brief discussion about doing too much since we had so many days ahead of us, but i asked Him to keep going.

I heard rustling, and then I played “Guess which implement He was using.” Crops, paddles, canes, a carpet beater. It was starting to hurt--the point, of course--but He was careful. So careful and measured. Some of the items i could guess. I couldn't tell which cane was which, just knew that He was using one. He liked delivering those low. I knew for sure one of the paddles. About 16-18 inches long, several inches wide, and flat on one side and convex on the other. Thuddy and stingy. Even though I knew He was holding back, damn that thing hurt.

It is evil.

He laughed and said i wasn't the first to say that and the friend who made it would be happy to have my confirmation

i wondered how much trouble i would be in if it disappeared.

Cutlass would probably recreate it just as evil or even improved!!

Cutlass would probably recreate it just as evil or even improved!!

Oh yeah, that's all we need.

i mean, yes Sir, what a lovely idea, Sir. 🙄

When the mind wanders, or, how to stop a spanking …

As we were chatting about spanking, Sir mentioned that a RL sub He had commented on how He gets fixated on one spot. She was right. Not so much with the hand spanking but with the implements.

We had started another round with me on the bed and Him using His hand to warm me up. Again, i was facing away from Him. A quick rub to check on the heat, and He turned to the implements. Several strikes with one, then another. They all hurt to some degree. Some made me grunt—a little “uh.” Some made me squeak. And some brought a squealy “ouch.” I tried not to wiggle since that can bring on more, but sometimes it was necessary.

And then He found His sweet spot for the moment. While part of me was going from the uh to squeak to ouch, part of my brain was thinking how His former sub had been right. Then i thought how it was like a record player that gets stuck in a groove and just keeps repeating, and you need to bump the player to make it stop. And i wondered how i could think all that while He was still spanking me … and it REALLY was hurting.

I have a high pain tolerance, but i was reaching my limit for that spot, and i was worried i'd bruise, which would keep Him from spanking again. It was too early in His visit for that. I could have used “yellow,” and He would have respected that, and we’d have talked about what was happening. He might have stopped for the time being, or He might have moved to another spot to spank.

Instead, for some reason, what came out of my mouth was “Stop the Victrola!” Now those machines are not only way before my time, but His too. No idea why that’s what i thought of, but it was effective.

He stopped.

I didn’t look back, but i heard Him start laughing. So i did. And the more we laughed, the harder we laughed. We cried. He made some comment about my comment, and we started all over again. I turned and looked at Him as we stopped, and we started again. He made some squeaky-ish noises that let me know He was starting to hurt from so much laughter, and i managed to swallow “Serves You right.” (For the uninitiated, that’s one of the phrases you NEVER say to your Dom, especially when you’re already in a spanking position, and there are so many options available to Him.) Apparently, i didn’t think it too loudly, either, because He just sat down on the bed next to me, and we finally settled down.

That became one of our catch phrases for the week. It was a bit dangerous because when He got fixated on one spot, it ran through my head again, and rather than maintaining the proper submissive “ouch” and “uh” and squeaks with each spank, i’d giggle. Fortunately for me, His sense of humor won out, and while He’d continue the spanking, usually with a few laughs, He never increased it as punishment.

It is called marksmanship, not getting stuck!!!

It is called marksmanship, not getting stuck!!!

Poe-tay-toe, poh-tah-toe

I met her here about 10 years ago. We started chatting online, and it started developing into a D/s relationship. After some time, we started talking on the phone, and although we wanted to meet, it never happened until 04/10/2021. The first couple of days I kept it quite vanilla as I got to study her expressions and learned how to read her. When I finally spanked her, I found out that she reddens quite easily, so I was concerned that she would bruise just as easily. So I kept the spanking short and at medium strength, but I did use a paddle made by BadAss Designs, and I was happy to see a positive reaction from her. (She wiggled just a bit, but it was enough for me to know that the paddle had made its mark!)

This a great thread. Thanks for sharing!

You pair have a new follower. 🌹

You pair have a new follower. 🌹

Me too. Keep it coming.

(Work got in the way of having fun writing today …)

When Sir was sharing (ha) the various implements with my backside, He also pulled out a pair of gloves. Soft black leather. With needle-like points all over the palm and fingers. Vampire gloves. He put them on and ran a finger lightly up and down my forearm. It kind of tickled, but it felt good, especially with a little pressure. They would be wickedly dangerous in a spanking—unless you’re into drawing blood—but i could see the possibilities when applied gently.

i was right. Sir paused the spanking, which had so far meant He was getting something else to get more squeaks or ouches. But He took a longer time coming back. i still wasn’t watching Him, as much as i wanted to, so i took time to wiggle a little at the rather pleasant pain i was experiencing. Rubbing was tempting, but although He hadn’t said i couldn’t, He also hadn’t said i could. So i was safer not. i knew that much. He’s never been vindictive or unfair, but you just don’t take chances with Dominants. Especially while in that kind of position.

i heard Him approach again, and i felt a pokey gloved finger run up my left calf. It gave me goosebumps on my scalp. Not running up to the scalp. Just there. A flash for a few seconds. That was one of the coolest sensations i’ve ever felt. Up and down the calf, up the thigh, my tush. Back down the other side. Up again onto my back. Down around the tush and to my thighs. Lingering here and there. Moving quickly. More pressure. Less.

Never a word from either of us. i kept my eyes closed and enjoyed the sensations, occasionally shivering when He hit a particularly sensitive spot, or feeling the crawl of goosebumps on my scalp again. But everything felt good.

Then on one of the passes on my thigh, His fingers dipped lower to the inside on one and went along the inside of the other. First time a partner had done that to me—not even my ex had—but my legs parted a little on their own, and my breathing changed. Wow! More passes up and down, inside again, and this time i provided more space on purpose. i had no idea what the vampire gloves would be like on more delicate tissues, but my body was quite willing to find out.

Part of my brain was still enjoying the sensations. Part was wondering what Sir would do. Accept the invitation? Ignore it? Tease some? Had i gone too far? Not far enough? i was pretty sure He knew full well what i was offering and wanted. But just more passes. Try a little wiggling? Open more? GAH! There’s a delicate balance for me in the D/s relationship, probably for many subs: ask, tease, push a little, but don’t try to top from the bottom. Trying to force a Dom like Sir to do what you want is never successful and always has negative results beyond not getting what you want. It’s true even if whatever you were wanting is something the Dom would enjoy and want under other conditions (i.e., no pushy sub).

Anyway, i so wanted more, but we had just started playing and were still figuring each other out in real life. I had no idea how far to go, so i didn’t do more or say anything. He ran His fingers on their circuit a couple more times. Still felt so good. And He stopped.

Sigh.

Disappointing, but it was what Sir wanted.

“Thank you, Sir.” i did mean it. He had given me so much already that i hadn’t experienced. It had been fantastic.

“You’re welcome.” … A rub on my back and pat on my tush. … “Turn over.”

On the second full day I decided it was time to give her tush some color!

I told her to take off everything but her bra and lay on the bed, she followed and made her derriere available to me.

I started by caressing her tush to wake up her senses, and then I started with a bare hand spanking, I struck each cheek once and was rewarded with nice hand imprints. I commented that she reddened easily, and she said she did.

I proceeded to redden the tush evenly before switching to my toys: three canes, three crops and one paddle. (It has been called evil in the past; she confirmed that moniker.)

I had to keep the toy play light since I was concerned that she would bruise and ruin future fun. I managed to get satisfactory results, though, and have more fun in the next days.

I am so happy that the two of you finally got together in real life.. Continue to be with each other as much as you can in real and on the phone and oh line. Continue Loving and Living showing the rest of us that no matter what happens Love still Rules.

This is a great thread and its good to read that you two were able to meet in person. Thanks for sharing and please continue.

Chester behaving for once… LOL. I missed seeing you around and I'm glad there is calm period in life for you to come back on occasion.

I simply adore the relationship you both have and had when I first met you. I can say that over the years I knew you, you helped me grow and learn a lot. I can never thank you both enough for being such amazing friends to me. I can't wait to hear more!

When Sir told me to turn over and sat on the edge of the bed, i wasn’t 100% sure what He wanted, but i had a good idea. i was right. i scooched over a little to make more room for Him to sit (but stay plenty close!), and He reached between my legs and started exploring.

Oh. My.

The few times my ex and i had sex, he would reach there, finger me a few minutes, and then about the time i was starting to aroused say something like “I guess that’s enough” and then try to get inside me. Talk about frustrating.

Sir knows what to do. That hand that left red prints on my tush was still so strong but so careful. He worked on my clit, making my eyes close and head push back. Wiggling to increase His fingers’ pressure produced an arched back and curled toes. He shifted a little and tried for my g-spot. That was a first for me too. It felt good, but He couldn’t get it exactly, and as much as I enjoyed the sensations, i wasn’t getting over the top like we both wanted. i’ve always had problems climaxing from finger stimulation alone, and i was mentally distracted with it being our first time. So i told Him as good as it felt, i didn’t think He was going to get me over that way right then because it rarely worked.

He wasn’t bothered. He said He had something that would work and got His magic wand. i had been using one under His direction for several years, and i knew that even with our first time in person, it would work.

He lubed it, put it in place and turned it on.

Yeah, cumming wasn’t going to be a problem.

Except we hadn’t discussed if i had to have permission to cum. From the first time He directed me, i had to wait for Him to give me the trigger word before i could. (Oh, that was feeling good.) What was i supposed to do? (Uh-huh, over there a little.) Do i say something? (Mmmm. Push up against it.) What happens if He is waiting to see if i wait on Him? (Back the other way. Just a smidge.) What if i don’t wait? (Yeah, that’s it.) Another spanking? (Would you please focus on what is important, brain?) Is that a negative? (Ohhhhhhhhhhh, that’s great.) And by then nothing really mattered because even if He had turned off the wand and commanded i stop, there was no way i could—or would even if i could.

Right then He flipped it to high.

And i was gone. Wave after wave.

It probably wasn’t long, but i had zero sense of time. i knew only that the waves were continuing, i was starting to have trouble catching my breath, and i was finding muscles i'd forgotten i had. my right hand grabbed His wrist almost involuntarily, and He understood.

i laid there, eyes closed, gasping like i'd been in a race, still holding Him. Then i hit subspace, and my hand let go.

It wasn’t too deep, but i was floating there with the endorphins carrying me in a semi-out-of-body experience. Sir took my hand. i was with it enough i could respond a little, but not really anything coherent. He did at one point say something about subspace, and by then, i was able to respond that i was definitely there. It’s a happy place. i hadn’t been in a long time. i wanted to stay, but my brain and body reconnected, and i managed a “Thank you, Sir.” I could hear His smile in His “You’re welcome.”

*Note: This is actually from the second time with the wand. More to come from chester on that round.

I decided to see if I could work the Magic Wand on her. I had her turn over on her back, and plugged the wand into the lamp on the nightstand next to her. Her eyes were closed, but she could hear me moving around. I lubricated the head and proceeded to separate her labia to allow me to place the wand on her.

When she felt the head of the wand she tensed up. I started on low, but making sure that full contact was maintained, sure enough, she started to wiggle. I kept her at low power for a bit.

The wiggling intensified, and that was my clue to turn it up a notch!

I turned the wand to high, and the "magic" started.

When she orgasmed, I kept the wand going. She had another, and then they came fairly quick

.

When I stopped the wand, I could tell she had drifted into subspace, so I sat by her and held her hand so she would know I was there, I did not keep track of time, but when she finally started coming around, she told me: "I am here, but my body refuses to move."

When she was able to move, she dressed, and I took her home. As I was driving, she commented that she was glad I was driving since she did not believe she would have been able to.

For my part: Job well done!!!

“When she felt the head of the wand she tensed up.”

Perhaps because Someone used cold lube?

“When she felt the head of the wand she tensed up.”

Perhaps because Someone used cold lube?

That’s probably deserving of a spanking. 😀 Nice to hear both sides of a dom/sub relationship and the respect on both sides.

Glad that the two of you finally got to meet and be together. It has taken way too long!

Vampire gloves

I wondered if they would come along for some fun. 😉

(This is the night Sir referred to in post 24.)

Sir came equipped with several new toys. His level of excitement was about that of a little kid on Christmas morning, particularly with the violet wand. For those unfamiliar with it, as i was, the quick summary is it gathers current and zaps you, the intensity of which depends on which glass electrode is used and a few other variables, including where it zaps you. The second night we were together and Sir was demonstrating his toys, He got out the box and put the wand together. The glass lights up with a little stream—in this case, purple. He put it along my arm and zzap. That was cool. He tried it at different distances and time applied, and then tried out the other electrodes. i didn’t quite share His level of excitement, but i thought it had potential.

The second time we played, Sir again started with warming my backside with His hand and then the variety of implements. Yes, He found a spot He liked again. No, i didn’t say anything. But i thought it.

This time when He told me to turn over, i knew what was coming. i was right, but there was a little delay. He had the violet wand again. And that same look on His face. i will give Him credit for showing restraint in the electrode He chose since it was not going on my arm this time. He also was careful where and how much He zapped me. i do recommend the violet wand.

Next came the magic wand again. Sir started it on low, which is plenty powerful, and as i was starting to hit orgasm level, He flipped to high. i flipped too. Back to low. More waves. Up to high. i have no idea how long or how many times i came. What i do know is about the time i couldn’t take it anymore, He stopped.

my body sort of did. i went into deep, deep subspace. i knew it was happening. Was aware of Sir sitting there and taking my hand. Could feel my breathing getting back to normal. And when subspace and i collided, my right ear was smooshed uncomfortably weird against the pillow. i couldn’t do one thing about it. Or anything else that might have happened.

my brain was functioning, floating between the nothingness of subspace, wondering how long it would last, and was there any way i could move my head to make my ear feel better. Nope. i tried to move my hand. A couple of fingers sort of twitched. The other hand didn’t work any better.

i had learned on my first trip into subspace to just let it all happen and ride it out without fighting. That time probably 10 years ago i had read about subspace. Sir and i were still working online, and i had cum hard. i didn’t understand the sensations, was trying to type what was happening, and Sir was trying to explain. my fighting resulted in aftershocks of orgasms. Some would like that, and i might now, but then it freaked me out.

So i laid there aware of Sir’s hand holding mine. The gentle waves. Fingers still only able to twitch. And my dang ear. i think i drifted into actually sleep for a minute or two. Finally i came up enough to move my hands, and then yes, my head moved too. I managed a thank you, which is important, although Sir would have understood more delay. Finally turned to my side and then stomach. Everything was slow motion. But that was OK. Fine, in fact. So fine.

What a wonderful Sir. i think i will keep Him.

(OK, technically, that's “i hope He will keep me,” but you get it …)

Sir will have to add details about the violet wand He got, but here's a link to some info about them: https://www.violetwands.com/about-violet-wands/

Great thread