2025-10-17 Session with Tim

Posted on October 18, 2025
Word Count: 7072

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This session was very difficult, but it left me feeling happy and floaty.

We started with the usual Friday ritual: light discussion while he shaved me, a rinse in the shower, then back to the bedroom. It was nice; I do love the ritual, but it’s not where I really want to start writing in detail. It’s a lovely slow romantic lead-in that I enjoy, but what I consider the actual start for the session came after.

He planned temperature play and general sensation play. He also said it was going to be a difficult session, although it was difficult in ways he didn’t plan. He planned on using hot wax on me and had purchased a plastic shower curtain to use as a top sheet over the bed. The wax does like to get everywhere. For my comfort he put a towel on top, but it was perpendicular to how he likes me to lie. Honestly, that’s how he normally lays the towel, so I wasn’t surprised, but I still didn’t want to lie on the plastic.

When he was ready to start, he told me to lie face-down on the bed. Welp, he didn’t say how, and I didn’t want to lie on the plastic, so I laid across the towel knowing perfectly well he wanted me perpendicular to it. I grinned; he laughed. He made a comment about how I say I don’t brat. No, I don’t say that! I say I’m not a brat. Different thing. I absolutely brat when it’s funny and the loophole is there. Especially if I think he’ll find it funny. Which he did. I do enjoy being able to make him laugh.

As a consequence, though, he bit down on my arm. The pain was unexpected and harsh and I cried out a lot more than he expected. He told me to get in position, with more direction this time. I hesitated for a few seconds, then nodded with a small “yes” as I realized tears were starting to form. Genuinely unhappy.

I had spiraled. Instantly.

He recognized something was wrong when I hesitated. I wasn’t acting how he expected. He asked me if I needed a moment, and I… don’t know what I did, but I do think I managed to signal that I did, indeed, need a moment while I continued to sink into unhappiness. He got in position to cuddle me and figure out what had just happened. I didn’t quite cry, but I felt my body wanting to very hard.

So what had happened? Well… Two days earlier, I had received the COVID vaccination and my arm was still sore, right where he bit. I have some serious issues with needles. The extra pain, given its source, and the fact that it was in response to bratting, made me drop incredibly fast.

My emotions told me he’d done it intentionally to hurt me… to be overly harsh for what I had done. I knew that was bullshit. I told him what my feelings were telling me, and I told him I knew they were wrong, and he just held me tight in a cuddle and talked to me. He had meant it as a playful bite and didn’t realize he was anywhere near the sore spot. He had me show him the sore spot on my arm, and he showed me his sore spot was in a different place.

We talked for several minutes and I slowly leveled out again. It was only a few minutes, but that experience set me up for additional difficulties, on top of the already difficult evening he had been planning.

Once I was back in a neutral headspace and chatting again, he had me position myself on the bed where he had originally wanted me. He attached my cuffs to my wrists and ankles and secured me, spread-eagle and face-down on the bed.

I didn’t like his decision to move straight from that headspace to an anal toy, but I suppose for a difficult evening, it continued the trend. As he lubed up the plug, he mused about the plug sizes. He was going with the XS to start and might increase later. “Anything that’s going to be thicker than I am is really just there to show off. At that point, you’re ready to please me, right? As long as I fit in you? Not that there’s anything wrong with making you take more than that for the fun of it.”

Fucking god damn. Yes. Of course. Whatever you want.

I was too tense, though. I tried… I tried so hard to relax and largely couldn’t. He made slow attempts, adding more lube every little bit. I mentioned that I wasn’t sure if it was the angle on the plug (with the squishy neck it has, sometimes the angle is tricky), or if I was just tense from what had just happened. He told me, “It’s going in either way.”

I… fuck. Kay.

He was gentle and slow, adding lube frequently. The plug continued to have trouble so he switched to fingers. I don’t like the feel of fingers, the texture is uncomfortably rough, but they slide in easier than some toys, being thinner and easier to adjust by feel. Regardless, he likes being able to “feel around” inside me. He moved his finger in different directions inside me to emphasize that point. It’s such a weird, uncomfortable feeling… A weird, uncomfortable feeling that I have no choice but to lie there and accept from my owner. It did slide in easily, though, with no real resistance or pain.

He continued to work the plug into me, and talk to me, calmly, reassuringly, while I did my best to communicate what was going on. Something continued to not feel right when he pushed the plug into me. I couldn’t tell what, but I had a strong fear that, if forced, it would cause damage. Of course he would never force anything in any way that would damage me. Anal play is one of the areas I’m not allowed to push to the point of pain. If I feel pain I’m supposed to communicate it immediately so he can adjust what he’s doing. So I communicated as best I could while he adjusted and took his time, letting me relax as much as I was able, until finally my body gave in just enough and the XS plug—which I normally take with little effort—finally slid in.

It really hits all the lovely submissive buttons—his calm, gentle reassurance, coupled with the assertion that this is happening, and he’s patient enough to wait until the end of time for it, but it is happening. And it’s okay—he’ll take all the time he needs. All I have to do is let it happen and communicate. Doesn’t matter if I like it. Doesn’t matter if I want it to stop. What I want is important, but only as another data point in his decision. It doesn’t carry as much weight as what he wants. And I love that so much.

After he had the plug in, he moved on to rubbing coconut oil into my skin on my back, butt, and thighs. His plan was hot wax and it helps the wax removal later. Also it’s a relaxing massage. Why couldn’t he have started with the coconut oil massage?! A calm relaxing massage where he tells me all the hot things he plans to do to me while I squirm, whine, and melt into the bed would have given me a much better chance of relaxing for the plug a moment ago.

He really did tell me, too. He outlined his whole plan for me while he rubbed my clit, talking softly near my ear… all the things he planned to do that I would have no choice over. Slow, sensual, and a bit intimidating, especially when he said we would be doing sounding again.

I don’t know why I’m still surprised. Sounding is something we’ve been doing almost every session now. It’s hot and intimate, and intimidating.

He also said he was going to force me to have two orgasms that night. While it’s possible with enough space between them, I’m largely a one-orgasm gal. I have my one orgasm at the end of the night and I’m happy. It takes a minimum of 45 minutes to build back up to where I even have the chance of hitting a second one.

The list though: Wax. Cold. Slink. Spanking. Sounding. Forced orgasms.
Scared.

Not fearful scared, though. Nervous scared. Anticipatory anxiety scared. Complete trust, but still scared of what I was about to go through.

He pushed the magic wand vibrator right up against my clit and said we were going to go for that first orgasm today and turned it on.

We do not normally do early-session orgasms. Teasing, sure, but it’s really rare and usually unintentional to give me an orgasm so early in a session.

With the vibrator pressed firmly against me, and all the priming he’d just given by telling me all the things he was going to do to me tonight, an orgasm nearly immediately surfaced. After the orgasm was done, he continued to press it against me for a short time while I squirmed. When he finally turned it off, he said the next orgasm would be longer. I was just hopeful there would be a next one since my body sometimes doesn’t always like to agree to that sort of thing.

He dropped more cold oil onto my back and I jumped, but relaxed into it as he worked it into my skin. I love the feeling of a partner’s fingers gliding over my skin like that, slow pressure sliding around my muscles. After a few more minutes of letting me relax into the bed he said it was time to light the candles and start torturing me. I told him I was scared and he just went “mm-hm” in this completely “of course you are” tone while he kept rubbing my back. God, I could have sunk through the floor, I was so relaxed… and also anxious. His reaction to my concern was almost dismissive, but in a really hot way. Like he accepted that I was scared but it really didn’t matter. It wasn’t going to change what he was about to do.

“So you’re scared? Ask me to do it to you anyway.”

Welp. If I didn’t want to sink through the bed and floor and down into the earth before, I certainly did in that moment. I asked for clarification, unsure what exactly he wanted from me.

“I’m letting you collectively refer to the whole thing instead of making you be specific.” Holy shit he could have made me be specific. “Of the things you’re scared of, in general, ask me to do it to you anyway.”

Fuuuuuuuuck. Hot. Awful. Hate. But hot.

I did manage to get out “please do what you’d like to me, anyway”

Words are hard.

He accepted that though. I always worry that if I don’t say things perfectly that he’ll make me correct it, even though he so far never has. Maybe I am too much of a perfectionist, so if it’s not verbatim I worry it’s not going to count. But he accepted it and kissed me and told me it was going to be fun. I never find that reassuring, but I think I like when he tells me that, anyway.

He left me briefly and returned with a bowl of ice and a spoon. I fucking hate ice.

As he lit the candles, he mused, “Relaxing back massage… candlelight… I don’t know what you could be so nervous about. It sounds like a lovely evening, doesn’t it?”

I whined back at him. I do adore the power play in the lighthearted comments. It really drives home exactly how much power he has over me in these moments. Of course that’s intentional. But also, it fucking works. All I can do is take it.

He came in close, talking in a softer, more sensual tone, about how he was going to decorate me… make me all sorts of pretty colors. Teasing and drawing out the tension before he went for the wax.

He started with our soy-wax candle. Soy wax has an incredibly low melting point, so it’s warm, not hot, and when it hits it’s mostly just surprising. Dropped very close to the skin, the soy wax feels about as hot as paraffin wax poured from much farther away. It’s a good opener, but he doesn’t like to use it much. It doesn’t like to fully resolidify when in contact with my skin.

I actually like the feel of it quite a lot. It hits and it’s a surprise, but it’s not much more than the temperature of a hot shower. Then it cools and it’s just a pleasant warm.

Then I heard the ice clink as he picked up the now-chilled spoon to scrape the wax off of my back.

Hate.

I cried out at its touch. I fucking hate the feel of ice-cold on my skin like that. Unfortunately, he does love to get that reaction out of me. He scraped the wax off slowly and let the cold run over my back.

Misery.

Except… no really—actual misery. This wasn’t just “don’t like,” it was a problem. A real problem. I thought about him using a cold spoon on my back, over and over, and I felt the prickle of tears. Shit. Gathering all the words I could muster, I told him that there was a good chance that if he used cold on me too much I would cry.

He took a moment to talk to me and checked what I meant. He confirmed with me that I meant like a “spiraling” cry, which he didn’t want me to do. He carefully tested the spoon again, without it being ice-cold this time, and I still reacted strongly, so he decided that the room-temperature spoon was cold enough for what he was going for with me. All he wanted was the reaction; he didn’t need to push any harder. Apparently, I was extra sensitive that night.

I was rather relieved. Although I was fairly certain if I told him I was having a problem that he’d change the plan, there’s always a chance he’ll decide to push forward anyway. He can do what he wants with me, and he does have the power here to push me up against my limits with the expectation of more serious aftercare, and I’d just have to go with it. I trust him not to break me, but that doesn’t mean he won’t bend me a whole lot. However, he usually isn’t interested in pushing me that hard, and wasn’t that night, either. Yay! Nothing ice-cold! Crying risk (#2) averted.

Sam had been out for the evening and we noticed (through dog barking) that he had come home. Tim asked me if I’d gotten to say goodnight to him, and I hadn’t, not knowing how late the evening would run. Tim went and brought him back into the room for me. I was still naked and tied up, but Sam was not particularly bothered.

Sam crouched down by the bed on my right side. He stroked at my skin. We chatted lightly while he touched my skin, stroking everywhere, which was really nice. I like him touching me and he likes touching me. Perfect partnership. After a while, he went to leave and I managed to grab his shirt, because I could just reach it before he got out of range. I couldn’t do anything else because my hand was tied to the bed, but I held on. He sat back down and continued to stroke at my skin. Tim chatted with him over me.

I have a fantasy of two doms working me over and talking about me, one a dom who knows me well, and one who doesn’t so much, so there’s a lot of explanation and discussion while I suffer for it. While not quite the same situation, this really did touch on that fantasy; Tim talked about what he does to me, and then he would do it to illustrate, while I suffered.

He talked about the wax as he poured it over me. He talked about how the room-temperature spoon would still be very intense when used against skin that had just had hot wax on or near it, and then demonstrated while I screamed. He talked about the Wartenberg wheel, what it’s used for, and how it feels different to different people. He specifically talked about how it barely feels like anything to him except a little pokey and then dragged it along my skin to get me to cry out.

I really did enjoy being shown off, and I loved having Sam there.

Tim dropped something cold on the bed and I felt an unpleasant persistent cold along my left side. I wasn’t sure what it was, although after a moment or two I realized it was the slink toy. Large and cold. He laughed at my unhappy noises and told me that he figured he’d let it warm up against me instead of inside me. Ugh. Point. Although it’s actually easier inside.

Tim pulled the XS plug out of me carefully. Something hurt. I told Tim there was some pain on removal, and I could hear genuine surprise in his voice. We generally didn’t get pain on removal of toys. I thought about it later, and I think the orgasm while it was inserted actually may have had something to do with that pain. No idea though.

I was still fine to continue and Tim had been cautioned about the pain, so he did go forward carefully. With Sam still there, he slowly worked the toy into me. He continued to talk about me to Sam, explaining what we were doing. He asked me questions as we went to ensure that he wasn’t pushing me too hard. I had a lot of trouble. I was still very tense, and wasn’t able to take nearly as much as usual before it began to hurt. Ultimately, Tim decided to keep me with the XS plug this evening, even though I probably could have taken more, just to avoid potential damage.

After a while, Sam said he was getting tired, so we said goodnight and he disappeared to bed. It was so nice that he joined us for a little while though. I love my Sam. <3

Tim continued to decorate my back with the wax for a while. I think he started going harder on me without Sam around. More wax, closer to my skin, I don’t know. It felt way more intense. However, it had been a while since my orgasm and that was also making things harder. I finally requested some extra attention to get me turned on again and he was happy to oblige.

Thinking back, I wonder if being less turned on contributed to how cold I felt for most of the evening. I always heat up when he gets me worked up. The orgasm at the start definitely led to a drop in arousal as its effects faded away. It made everything so much harder, which in a way, did enhance the evening overall. But I wasn’t ready for what it would actually mean for me, and I’m definitely thinking now that that overall cold was one of the consequences.

He played with my clit, making comments about the wax, me, and the plug. Keeping me constantly aware of what he was doing to me.

Hot.

I mean. Still cold, but like. Hot.

After he decided I was worked up enough, he climbed up on the bed and sat in front of me, then made me suck on his cock for a while. I have my limitations on what my body will tolerate, but I fucking love sucking cock. I love the feel of the soft smooth skin in my mouth, on my tongue, and feeling him get harder as I play with it. It’s a favorite activity. It’s also hard as hell to do when tied spread-eagle, face-down on a bed. Extra challenge mode. He helped me by holding my head for me. I remember when I couldn’t handle someone trying to guide my head, but it is actually easier to just let him move me as long as I can relax into it.

After a few minutes of sucking on him and him moving my head how he wanted, he warned me—he was going to hold my head down.

Crap.

This is one of our forms of breath play. If he pushes my head down onto his cock, it pushes into the back of my mouth and prevents me being able to breathe. It’s not even in my throat, and I’m not sure if it’s physical or something else, but when he holds my head down, I can’t breathe.

He warned me. I gave a quick whine, steeled myself as best I could, and took a breath right before he let my head slide down and he filled my mouth. The moment of no sound other than him enjoying it dragged on. I couldn’t whine, moan, or anything. I was fully bound and completely at his mercy. Soon my body started to cry out for release—for air. I couldn’t stand it anymore and I pulled up… but I went nowhere. He held me tight in place and gave a soft negative “mm-mm” noise that I swear jolted straight to my clit. Just a second later he released me and as I was gasping for air he said “It wasn’t quite time yet. You get to come up for air when I want you to.”

Ugggghhhhhh so good. I know he counts in his head. He keeps very close track of me and time when we do any sort of breath play. But struggling and being told, very gently, that I’m basically stuck there, is such a trip. The moment drips with his power over me. He doesn’t need to be harsh, he doesn’t need to be loud… just soft, quiet power. Complete confidence, with a soft laugh.

He moved back to the wax, decorating me how he wanted. The wax was intense. He again had me crying out quite a bit. “It’s okay. It just hurts.”
Fuuuck.

Then he told me he was taking a picture.

I don’t do well with pictures in normal circumstances, but did put them on the table a long time ago as an additional way to submit to him. All I ask is that he protect them. It took him a long time to start to do anything with it, knowing how hard I find pictures (this was only the second or third one, actually). I actually find it surprisingly hot. I originally handed him that power as part of just handing him anything I thought I could handle, but when he tells me he’s going to take a picture I do get a chemical rush. One more way I’ve given up power. But also there’s something there knowing that he loves to have them. It does boost my confidence a bit that he wants them in the first place.

I don’t know that I could realistically look at any pictures he’s taken. Maybe someday. Maybe someday he’ll make me. But right now they’re for him alone and knowing that he has them and enjoys them is exciting.

After the wax and picture, he decided to use the speculum next. I had a hell of a time with that. Normally it’s fine, but the angle was off due to how I was lying. Normally I’m face-up; this time I was face-down. Every time he attempted to insert it, it hurt in an unfun way.
“Don’t like it.” To which he responded with a casual “Mm-hm.”
Dammit.

After a few attempts he did finally let me have a break.

He reassured, cuddled, and kissed me. “You’re okay. Difficult session, huh?”
“Yeah…” I agreed.

The break helped me settle down and relax into him again. After a few minutes of cuddling, he placed the vibrator up against my clit and turned it to low, letting me relax into that, instead, while he cleaned a few things up and prepped for the next part of the evening.

Then, more wax.

My body kind of does what it wants. The pleasure from the vibrator was intense enough I couldn’t tell what would happen and I started getting a little anxious about it taking me to orgasm, unplanned.

“I’m a little worried I’m going to orgasm again.”
“Well, then you might have to do it three times.”
“Oh fuck.”
And he laughed.
… What could I even say to that?
“Just relax, pet. If you come from being used, then you come. If I didn’t want you to, I’d command you not to.”
Fuck. My body doesn’t work like that, but that still sent a jolt through me.

Again, more wax.

He told me he was going to make me orgasm again. He paused to tell me very, very clearly that if I didn’t orgasm that that was okay. I appreciated the reassurance that if my body didn’t cooperate that I wouldn’t be doing anything wrong. All I had to do was relax into it as best I could and let him play with me how he wanted. Which was good, because I did not orgasm that time.

The vibrator buzzed away against me while he removed the wax from my back. He used the spoon to scrape up bits, or pulled strips off. The strips catch hairs uncomfortably, even with the coconut oil all over my back. The spoon scraping is a little uncomfortable, but isn’t too bad overall. Especially not with a vibrator pressed against my clit.

Finally he decided to stop and turn me face-up. We had a short break and check-in. Before we got going again, he said we would still be using the speculum and the sound. Just trying—and succeeding—to keep me nervous for the evening.

He climbed up onto the bed and sat above me. I remember him smiling down at me. Then he made me suck on him again. It’s always a struggle to breathe when he does that. I never know how much of that is intentional or not, but depending on how he positions, his skin loves to block my nose. Additionally, I focus so much on what I’m doing with my mouth and tongue around his cock that half the time I forget that I can just open my mouth for air.

The moment that really stands out in my memory from him sitting above me, is when he was smacking my breasts back and forth. It hurt, but I could look up and see his smile, see how much fun he was having while he hit me and it was just so hot, but also nice. It definitely turned me on, and the pain from having my breasts smacked around like that wasn’t terrible. But also, it was so great to be able to actually see how much he was genuinely enjoying hurting me.

He went back and forth between making me suck on him and striking me. Then he told me he was going to try the speculum again to stretch me out for fucking me, then after that, sounding and vibrator for the final orgasm of the night.

I told him I was worried. The speculum had hurt at the previous angle, and he’d tried it a few times and I was sore. I didn’t think I’d be able to handle it well. He acknowledged and dismissed the concern with a “we’ll see.”

It’s really interesting to have concerns and be able to express them, but they don’t mean full stop. I’m worried. I’m scared. I could even tell him I don’t want to, or ask him to stop (although I didn’t). None of that actually stops what he’s doing. He will take the input and may adjust what he’s doing, take it slower, watch me more closely… but he’s not stopping what he wants to do to me as long as he feels I’m safe. And I am safe.

And that’s hot as hell. Just submit, and trust, and experience. I suppose, what’s most important is that I agreed to that, and continue to agree to it every moment of our dynamic. Without any actual fear or regret.

It’s also really nice to know that he trusts me to tell him when anything goes wrong. He knows that I know what is supposed to hurt or not, and if the pain is wrong I tell him immediately. He can go as hard as he wants, try all the things that scare me, and let me experience it, because when something isn’t right, I’ll tell him without hesitation. (Although sometimes it’s just a scream when he didn’t expect one, or a more urgent-sounding whine than it should have been… I still do what I can to communicate however I can. We’ve been playing together long enough he can read me and my noises.)

Most nights, the speculum is easy for me. I might not take it fully opening right away, but it almost never hurts very much and I’m able to relax with it fairly easily. It helps open me, so when he does fuck me, it doesn’t hurt. Most of the time he can put it in, slowly open it most of the way, take it out and put it in another way and open it again. After just a few iterations he’s opening it fully and I’m fine. The stretching feeling inside is kind of hot, too. Not the most pleasant feeling, but not painful either, and the discomfort is still arousing when it’s him doing it to me.

Tonight? Well the speculum was okay but…

He talked to me as we did it. He checked in with me and went slow. He did it a few times and it was fine. In, open, slide out. No more problems than usual.

Then he switched to the one internal toy I had, and the way it pressed this time was pain.
It hurt. Wrong hurt. Bad!

He didn’t expect me to cry out and he stopped immediately. I told him it hurt. I said I didn’t want to do that again. I said “please.”

My “please” was small and my voice wavered. I could hear the tears behind it (third time this evening for anyone counting), although I couldn’t yet feel them. Difficult session, indeed.

I was scared but he remained in control. After a pause, he checked me over. He told me to tell him if anything hurt and he slowly and carefully pressed his fingers around inside me to try to find what was hurting. His voice was soft and calm, keeping me anchored.

Press, pause, nothing. Press, pause, nothing. After a little bit he seemed a little confused at what had caused my pain. Then pain!! I gasped and he stopped. He tried again to find the painful spot and wasn’t able to repeat it. Rather than risk causing pain he didn’t intend, he decided to forgo fucking me this evening.

I was both relieved and disappointed.

He assured me that he was still going to use me to get off, and afterward would be doing sounding and then using the vibrator on me. I was definitely nervous about the sounding in particular, and leaving it so close to the end of the session while constantly reminding me of it, kept me nervous and aroused.

We’ve been trying out sounding for a few months now. I’ve been wanting to write about the experience but haven’t had the spoons to really get into it. It’s been kind of hit-and-miss. Sometimes it’s hot as fucking hell and intense and I love every second of it but beg for him to stop because it’s too intense. Sometimes it’s kinda neutral but not bad at all. Many attempts end because it’s started to hurt. My body is still getting used to it.

Sounding is one of the things we do that isn’t supposed to hurt; when it hurts he stops. But the fact that it’s hurt multiple times, but also could be amazing pleasure… the whole thing is attractive but definitely makes me nervous.

So reminding me over and over that it was going to happen continued to keep me nervous for him. I both loved and hated it. Especially since this sort of mental play is exactly what I’ve asked for and crave.

He released me and told me he was going to set me up at the end of the bed and I was going to suck him off. He had originally planned to fuck me, but with where he thought the pain was, he didn’t want to risk hurting me that way. He said it was partially because it would be less fun for him, but also because he figured it would ruin his chances of forcing another orgasm out of me. Can’t argue with that, I suppose. Not that I would have tried.

I was still a little disappointed. Even though I really didn’t want that pain, sometimes it’s still hot to be sore and in pain and have him use me anyway. I considered asking him to do it anyway, but he already had his plan and the session had already been difficult enough. He had already reassured me that he was getting what he wanted, and if he fucked me like that, he would have less fun. Of course I want him to have more fun and use me however he wants. If that meant my mouth, well then that’s fun, too. At least I could still be of use.

While he laid out a mat on the floor for me to kneel on, I noticed that the plug was starting to bother me. I think the recent unfun pain had let some of the arousal fade. I let him know that it was bothering me. He had me come over to the end of the bed and he positioned me how he wanted me, facing the bed. He said, “I’m gonna force you down,” and he pushed me down quickly, leaving me bent over the edge of the bed.

He loves to do that. He’ll tell me flat out that he’s going to shove me down, and then down I go. It’s technically never a surprise, but I always gasp anyway because it’s fast and jarring. He enjoys it. And, to be honest, I enjoy it too. I don’t mind being told he’s about to shove me somewhere because: yay he’s going to shove me somewhere! It’s always fun. I wouldn’t mind the surprise either. Both good.

He removed the plug and helped me back up. He took a few minutes to talk to me and tell me how he could tell I’ve been struggling and how good I was being for him. Kisses and hugs and standing cuddles. It was really nice. And then he had me suck him off.

He had me kneeling on the floor in front of the bed while he sat at the edge. It’s one of the positions that my back and neck handle the best for long periods. He laid back and enjoyed my work. Occasionally musing at me about whatever crossed his mind, such as having me crawl across the living room back and forth between sucking off him and Sam. Telling me that at this point in my training I’d still be allowed clothes.

Fuck.

When he says that, I have no doubt that that’s what’s going to happen. He has all the patience in the world to take things slow with me until he gets what he wants, eventually.

And then he slipped his foot up between my legs and pressed his toes against my clit. Too much. I shifted trying to relieve the pressure and he commanded “keep sucking.” Fuuck. I wiggled away a bit but did my best to keep my mouth around his cock and my rhythm consistent. He continued to mess with me and although I’m sure my technique suffered, I know what mattered was that I was struggling for him. Soon he grabbed my head again and helped my rhythm for me. All I had to do was go with it and keep my tongue working. He pushed my head too far a couple times and I struggled against gagging. He did get me to actually gag on his cock one time, which I don’t believe was his intention, but he probably loved me struggling for him anyway.

He finally removed my head from his cock and came—very, very much not in my mouth. I slid down a little and licked at his balls and the base of his cock while he continued to have after-waves and shudders.

He’s not making me handle him coming in my mouth, yet. Thankfully. He’s talked about it in the past so it’s something he’ll start working on eventually. I’m very, very much not looking forward to that. I have a lot of problems with body fluids. So. Yeah. Going to hate that and right now he’s being exceptionally nice, and it seems it will be a very long way off since he’s only rarely talking about it.

The crawling between him and Sam giving blowjobs though. That feels like much more immediate talk. Also hot.

I felt nauseous when we were done. He definitely pushed me up against my gag reflex multiple times. Not enough to cause real problems, but enough to feel a little queasy for a few minutes.

After he recovered and cleaned up, we talked a bit. He again laid out what he was planning on doing to me. Back on the bed. Sounding. Vibrator.

Nervous. And we discussed why. The sounding had hurt the last couple times. He sounded completely unconcerned about my worries. Told me I could let him know when it hurts.

It’s an intense feeling to put all this in someone else’s control. He has so much power over me it’s intoxicating being able to just hand it over and go with it. He knows my fears, he knows my worries. He knows what I want. What I don’t want. What I can and can’t handle.

And he knows what he can push me into even when I’m nervous. And knows how disappointed I’d be if he didn’t.

And most importantly, he fucking loves doing it to me.

As he set up for the next portion of the evening, I told him “I’m nervous because this hurt the last few times, and a lot of things have hurt tonight.”
He kissed me and reassured me. “Communicate. We’re gonna try it. Just communicate. It isn’t important that it works, it’s just important that we try.”
Gahh… so good. I love how he talks to me.

He had me lie on the bed. We continued to talk while he set up for sounding. A mini-debrief mid-session. I figured out that part of my nervousness was how tense I’ve been all evening. Can’t exactly control that tenseness for the sounding. When he was ready to start I made an attempt to keep relaxed anyway.

As he inserted it, I felt a very light sliding sensation. It’s good, to be honest. I really do like the sensation. It’s somehow both soft and intense. Then pinching. Damn. It wasn’t too much, so he added a little more lube and reinserted. Checking constantly on how I was doing. Floaty and breathless, I told him I was okay. He moved it around carefully and I felt the movement and moaned softly at his adjustments. All I could say was that it felt weird. It didn’t hurt, it was largely positive, but weird and kind of intense.

And then pain. Enough that I cried out. In a moment he was up on the bed with me, kissing me, holding me, and telling me how good I did. I was fine, it wasn’t a spiraling pain, just a quick strong pinch that was really unpleasant in a bad way. But we were done with that for the evening. He was happy with me and I was happy for that.

Somewhere in the cuddles, he positioned the vibrator on my clit, then had me hold it while he continued to mess with me. The kissing transitioned into him biting me. He bit down on my neck and the suction was painful but also delightful. I fucking love marks and he was definitely going for one.

He sat up against me with lots of wonderful body contact and watched me and messed with me. Fingers, teeth, I don’t remember what he did while I concentrated on keeping the vibrator in the best possible position and enjoying the ride. Then the orgasm came. As he’d promised at the beginning, it did last longer, and was more intense. Then he had me keep the vibrator in place well after I was done while he continued to talk to me, amused, until he finally decided to give my body a break and he turned down the vibrator, then off.

We cuddled and did a little debrief. He had certainly succeeded in giving me a difficult session.

It was an awesome night.

And my night wasn’t over for once. Most of the time I get to drift off in aftercare cuddles, and then sleep. This night, however, was the start of Con Book Hell. So from this I would be getting up and doing my first all-nighter of the weekend—of the con.

I was happy and floaty as hell for hours after. It was such a great feeling. Really started my night off wonderfully.

And even though I’ve had to struggle to get this written down, I really, really wanted to. Because it was wonderful and difficult and I felt so connected to him after. I spiraled, more than once, and he handled me perfectly. I had issues and he handled them. I was scared and nervous and he guided me gently but firmly through it all anyway.

The best part about difficult sessions is coming out the other side of them. Safe, happy, and satisfied. And full of lovely brain chemicals.

Lovely session. Best owner. <3