2024-04-25 - Session with Tim

Posted on April 25, 2024
Word Count: 4642

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The evening started before we’d even left my house. Sam was laying down in the bedroom so we had the living room to ourselves while I grabbed the last of what I would need for the evening. He put his hands up my shirt in such a way that I was knocked forward and I ended up slightly bent over a nearby table, using it as support while he fondled me. I was surprised, but enjoyed the feeling of his hands running over my skin while I held onto the table to keep from falling. It was a pretty solid start to the evening.

We ran a quick errand and bought some fast food for dinner, chatting in the car. Every once in a while we returned to the topic of the evening’s plans. I enjoy discussing upcoming plans; it builds anticipation and, if the plans are evil/exciting enough, a delicious dread. We brought the food back to the apartment and started to settle in for the evening.

He had turned on the heater but before the living room was warm enough for my taste, he had me stand up for him. He fully stripped me while I murmured small complaints. He had me wait, standing there, cold, naked, and exposed for what felt like forever but was likely just a few seconds while he did … something. I just remember standing and waiting. I was cold and it was uncomfortable, and that made it really hot. When I was starting to really wonder how long he was going to have me exposed, he finally gave me my robe and we sat for the evening’s dinner and TV, and then we went upstairs to start the rest of the evening.

–

I sat on the edge of the bed, waiting. When he came to me he had me stand, as he always does. I expected him to remove my robe and put me on the bed, but instead he carefully lifted my glasses off my face. I felt the familiar and constant weight of them disappear, and with a tone so gentle and tender that it surprised me, he told me he was taking them and setting them aside for me.

My glasses are a regular minor detail that we often forget. I’ll be trying to lay my face on the bed and realize my glasses are in the way. I’ll remove them and set them wherever I can reach, which is usually a nearby pillow, and from there he’ll move them someplace safer. It’s usually just an afterthought. But his action this time brought this simple detail into the moment and electrified it. It was, in itself, a beautiful moment of him taking care of me. Also an interesting dichotomy: such softness and care, immediately preceding torment… hurting me and laughing at my pain.

After removing my robe, he positioned me how he wanted me on the bed. He always covers the bed with a towel and I was laying face down on it, but a little lower on the bed than usual. I watched him sit back and review my placement with a pensive look on his face. He then told me no, he wanted me higher, and to get up on my knees. No real thoughts to bratting this time, although I knew that that would have been a great moment for it. I lifted myself up and sat on my feet while he adjusted the towel placement.

He was being very particular this evening about how he wanted me positioned. He pulled me back down to where he wanted me by my collar then attached the collar to the rope tie point at the top center of the bed. After another moment of thought he adjusted the rope tighter so there was a constant mild tension against the collar. I knew the tension wouldn’t last but it was still nice to feel that added restriction.

He tied my feet to a spreader bar that was attached to the foot of bed, then my left hand to the left corner, and like last time, he attached the right cuff to a spot near my elbow so I could bend my arm and use my right hand to keep my head above the smothering bed. He wanted me as secure as possible for the evening.

The main plan for the evening was to try out some new floggers. I had a couple of rope floggers that I’d just finished the handles on, and some WIP kangaroo-hide floggers that were still missing their handle-covers but were otherwise usable. Additionally, I’d bought a new anal toy recently and this was going to be our first opportunity to try it. He teased me with it all evening. We both knew I couldn’t take the whole thing; it was quite a bit longer, and a little wider than anything I’d used before. He set it where I could see it and would tell me just how much he thought I’d be able to take. Every time he brought it up he would receive a bit of a shudder out of me from a combination of fear and excitement. Each time I saw it, all I could think was that it’s so big. Why is it so big… was it a mistake buying that? It’s just so big. It did not look that big in the picture on the website.

As I’d said in a previous report, I’m not really using large plugs, picking the smallest and squishiest things I could buy. The set of three I own are sizes 1-3 out of 9 available: XS, S, and M. This new toy was still the smallest one of its kind available, and still had a larger circumference than my “M” plug. But it started small and tapered slowly so I knew it would be fine to play with, and since neither of us were expecting me to fully take it, we were both ready to stop when I needed to without any missed expectations. No big deal.

No big deal but still… it was so big.

I’m just going to state now that he plugged me with the XS plug, because I don’t know when it happened. I believe we started with the floggers, and at some point he paused and inserted the plug, and then went back to the floggers, but it’s all so fuzzy it just seems easier to state this up front. It was a minor detail compared to the rest of the evening.

He started with the blue rope flogger: 50 ft of beautiful blue ¼” MFP rope, with the ends cut and allowed to fray. It was a relatively easy flogger – mostly an easy thud with a little bit of sting from the frayed tips, but not harsh. It was soft enough that it could be used on my back, which has been having trouble with harder thuddier floggers lately.

After that he moved on to the red rope flogger: another 50 ft of vibrant red ¼” MFP rope, with the ends looped back into the flogger. The loops allow it to have a thuddier hit, without knots or ties that would add bulky impact points on the ends (my back really does not like floggers with knots). This prevents it from being too harsh, while still being more intense than the blue one with the frayed ends. The looped ends still carried a surprising sting to them, especially when he threw it faster.

These weren’t new floggers. We had tried them when they were still in process, but this was the first time they were complete with a final handle cover – finally ready to join the collection and regular rotation!

When he was satisfied with the rope floggers, he moved on to the kangaroo hide floggers. I’d made a tiny one, and technically that was the easiest of the three, but it wasn’t really meant for this sort of play. It would have been more useful for small targets like breasts, face, or genitals which he didn’t try, so going forward in this text we’ll just ignore its existence and when I talk about the “smaller” one I’ll always mean the middle one out of the three.

From my own tests, I expected the largest one to be the easiest of the two floggers. The smaller one has a surprisingly nasty bite to it. It has fewer falls which are all different lengths, and its smaller size in general allows it to be thrown fast and mean with little effort. The larger one requires at least a little bit of intent to be anything similar to as mean. The large one has 108 falls, and in spite of its thin-cut strands, they are not nearly as nasty. The larger quantity of falls spread the impact around, and allow it to hit deeper, adding juuuuust enough “thud” to the strike that doesn’t really make it feel thuddy but pushes the sting a little deeper. This gives the type of hit that I like to describe as “lighting up” the skin.

We started with the larger of the two floggers but switched back and forth a bit. What I noticed immediately is that there were strikes that sent what felt like a wave of goosebumps down my arms. It was actually really nice, although a little difficult. It certainly wasn’t pain-free, but I definitely liked the experience.

I didn’t like the smaller one that much, though. I expected it to be nasty and it lived up to it. It was intense and had me trying to crawl up the bed to get away from every strike. Which of course, I couldn’t. I’d been secured well enough that I could only move a couple of inches, tightening the bindings around my ankles and loosening the rope attached to my collar.

At a point when he was using the larger kangaroo flogger on me I had a moment that really intensified the session for me. As he works me over with a toy he will generally move from one side of the bed to the other. At this point in the scene he had been to my right. Most of the sessions I keep my head to the left, and my eyes mostly closed, but not this time. I was looking to the right and I could just see him at the edge of my vision. Blurry because I had no glasses, but I could see how he stood, how he held the flogger, and I got a vague impression of a look of concentration as I watched him bring the flogger down onto me. It was such a familiar movement; one I’ve done myself so many times before. Nothing special in the movement itself, but something in seeing it was just so damn hot.

Days later, thinking back on it, remembering the blurry motion at the edge of my vision, blurry but so familiar…it’s still quite a turn on. I really need to make more of an effort to try to watch what he’s doing when I can. It’s one thing to get lost in my own head but seeing him handle the tools, seeing him hurting me, seeing him concentrate or grin… it really adds to the experience.

Finally at some point he decided it was time to try the new anal toy. I was anxious, eager, and a little scared, but most importantly, I was very turned on. I felt him sit behind me and he pulled out the small plug. He was telling me again how much he thought I’d be able to take while he lubed it up. The one-sided conversation was both embarrassing and exciting.

The toy has a much stiffer tip to it than my normal plugs and that seemed to make sliding it in must faster and easier. He added more lube as we went, and my mind spared a moment to wonder if something other than water-based lube would be more appropriate because insertion wasn’t as smooth as it felt like it should have been. The thought fell away though as he kept thrusting it inside me. It felt smooth and easy. It was long enough that I could feel it inside me which was a new experience. He thrust it in and out, slowly. He had started shallowly on the toy, slowly adding more depth as he went. He kept commenting on how much more I was taking than he had expected, and just kept thrusting it in me, slowly, a little deeper a bit at a time until I could feel resistance inside me. The resistance was uncomfortable but not painful at all. Otherwise, the thrusting felt impressively good.

When I finally said that it was starting to hurt (and it was only just barely starting to hurt), he had inserted almost the whole length into me, leaving only the last couple inches still un-inserted. He was surprised at how much of the toy I had taken and I could hardly believe it myself, it was just so big. But it felt great. It was so smooth and easy and I was enjoying the feeling quite a bit. Until suddenly I wasn’t. The pain was sudden and concerning. I don’t know what happened, but the image my brain came up with was that it was going sideways inside me. Tim said I had been moving quite a bit and thought that it was something in how I moved.

We took a break for a bit. I didn’t really want to take a break. The pain was gone, it was instant and gone just as fast. But I didn’t have enough brain to argue so we took a break. I was surprised at how unhappy I was with how empty I suddenly felt.

I don’t entirely remember the conversation or quite what we did when the break was over, but he did put the second size plug (“S”) in me and it was so easy he pulled it out and tried the largest of my three plugs (“M”) and it went in and came out with little effort. The first/last time we tried that one I had to carefully remove it myself because it hurt too much to let him do it. This time it came out with no real trouble. The smooth long cone had opened me up so easily that my largest and most difficult (again: “medium,” not really that large at all) plug was easy.

This seemed like a perfect opportunity for anal sex, of course.

At some point around here he hit me with the smaller/eviler kangaroo flogger. I remember him hitting me fast with it and I think I knew it hurt but it didn’t really phase me; I just relaxed into it. I was so ridiculously turned on that the pain from it was . . . somewhere else. It felt just fine.

He perched behind me again and I felt him lube up and slide in with some trouble. My legs were tied open, while last time we tried they’d been tied closed. He had more difficulty getting a position he was happy with. He was able to slide in though. I was a little worried about pain again after last time but no- nothing. Absolutely no pain whatsoever. It was just fucking awesome.

Shortly after he started though, he took a quick break to untie my legs. He had decided that leaving them open wasn’t what he liked for this activity. Once he had me how he wanted he reinserted himself. He got really into it, pressing his hands hard onto my back as he thrust into me.

Every thrust brought out some sound, a moan, a gasp, whatever. I don’t know how to describe my noises, only that I make them. Feeling him thrust into me was much more intense and intimate than the toy. His hands were heavy on my back, pressing me down hard into the mattress. If I hadn’t been tied in place, I was certainly pinned now. It was a really amazing moment, being held down hard into the bed, unable to move, unable to do much more than moan, while he fucked my ass as hard as he felt like.

At one point he pushed my head down and my face was so squished into the bed I remember doing a quick self-check. Okay, still can breathe… that’s good…. some pain in the face though. The way he was pushing my head was smashing my nose firmly into the bed and it hurt! I made an attempt but couldn’t get my face free with so much force pinning me down. It felt like forever, but it probably wasn’t very long until he finally released my head, freeing my aching nose. I was fine but it was definitely not a kink-related pain I’d ever expected.

He eventually collapsed on me, breathing hard and shining with sweat. He had not cum but needed a break. He had definitely been going at it for a while! And I was great. There hadn’t been any pain this time and I wasn’t sore at all. We discussed things, ideas, and possibilities. Maybe next time, he should require a blow job before anal to help him get farther so it wouldn’t be so much work. He agreed and said he had been thinking about something like that, too.

I was really turned on and up for more if he was. I suggested we could try vaginal if he was willing to go clean up and turn me over. He liked the idea and disappeared into the bathroom. This would be our first time trying that and I was hopeful that it would go well. It often is painful, and in a rather unfun way. But not always. And I really wanted him to be able to take me any way he wanted me.

I don’t remember him releasing my arms but when he left for the bathroom I was completely untied except for my collar which was still tied to the top center of the bed. As little as that was, that one tie still kept me in place. I wanted my water, but couldn’t reach it. I made a few half-hearted attempts at reaching it on the nightstand and then collapsed and waited. I could have undone the tie but it was much better to wait.

When he returned I requested my water. He sat next to me and handed it to me, ever patient. The restraint prevented me from lifting myself too far, so I only took one sip to wet my dry throat. I really only wanted the one sip anyway. I had been breathing so hard and fast that my throat and mouth were uncomfortably dry but I wasn’t exactly thirsty. When I was ready, he set the water back and got back to it.

I expected him to turn me over and fuck me. Instead, he presented his cock and indicated that I should suck it. I was surprised, but I don’t believe I even hesitated. Although my brain did go immediately to: wait this was just in my ass moments ago. But he cleaned it, and it seemed clean and I trusted him so I gave it no further thought as I did my best to pleasure him. I was laying on my left side and had a limited ability to use my hands in that position. I brought my left arm up to assist with the blowjob. I couldn’t really use my right to help at the angle I was at, but I used it to steady myself instead. He likes his balls played with, so I did my best to fondle them as my mouth did its work it knows so well.

I’m very good at blow jobs. Like, very good at blowjobs. I suspect a lot of women say they’re good but really have no idea because a common response is “oh you are good at that.” Guys always expect to have to direct me or move me but no, please give me whatever feedback you have (if you have any) and just let me go at it.

Over the years, I’ve gotten a lot of practice and developed my skill. I genuinely enjoy what I do. I’m always paying attention to what’s working for someone and what’s not, learning the individual, and remembering preferences from one time to the next. And always with one or two hands involved to provide additional stimulation and prevent me from going too hard and gagging. I can’t do anything too deep, but I’m very, very good with my mouth.

When I’m topping, blowjobs can be a form of control and torment, and as a sub, a form of service. I even know tricks to supposedly prevent orgasm until I’m ready for the guy to cum. I never do that anymore though. I no longer have the patience for it, although it has been super fun to have a guy question why the BJ session lasted so long because he really thought he was close but was close for what was a surprisingly long time for him.

It didn’t feel like we’d been at it very long at all before he pulled away from me, moving to more what I had originally expected. It’s always a little disappointing when I’m enjoying a blowjob and he just pulls away, but he had other plans. As we were getting into position I noticed that I could feel the wall against my hair as we moved. My earlier crawling up the bed had put me just a couple inches away from the wall. He grabbed a pillow for me so no matter what we did he wouldn’t start banging my head into the wall – something neither of us was particularly interested in. Thinking back on it, he also could have pulled me down some. Getting dragged down by my ankles does sound fun, but I guess the pillow was easier.

We took it slow because vaginal sex can go very poorly for me. He sat upright between my legs, pushing himself into me. I don’t know when he had grabbed my feet but I soon realized he was holding my feet up. It felt so easy and natural that I could tell it was something he was used to doing. But him pressing into me hurt. It really hurt. It felt like he was hitting a wall inside me and the pressure on that wall was all pain. No this wouldn’t work like this.

My thoughts ran over what might be going wrong. This wasn’t even the usual pain I’d expected, this was different. I first had him release my feet because that was something different so potentially a problem, but pressing into me still hurt. I thought harder, forcing the groggy subspace-clogged wheels to turn, and managed an idea. I asked him to “come here,” to get him to lean over me, and suddenly the pain was gone and it felt like he slid into me easily. Bingo.

I remember looking up as him he fucked me. His face was surprisingly blank. I remember reviewing his expression and being unsure of how to react to that. But his thrusting made my focus quickly shift. It didn’t hurt this time; not at all. Every thrust again pulled a moan from me, a gasp… whatever sound forced its way through my vocal cords.

This is normally where you’d expect a description of how great the sex was. Sadly, I just don’t enjoy vaginal sex all that much. It was good though; I enjoyed it well enough. What was really hot though was while he was thrusting into me he made a comment about “using all three holes” that night and it really hit me hard in an awesome way. Yes, please take whatever you want from me; use me how you see fit. ❤️

I have heard people say things like that in porn, read dialog like that in erotic stories, but hearing him actually say that to me, reminding me that he had actually just used me in every way he wanted, it hit so different. He had said that before, already, during the blowjob. It hit me then, too, but I don’t believe quite as much as this moment, feeling him thrust into me and knowing the truth of it.

He came inside me and as he did I began to tighten my vaginal muscles in sync with his shudders. He seemed to enjoy it so I kept at it until he seemed done. He glistened with sweat and looked really satisfied. I was happy to have been used for his pleasure.

Before this moment I’d never had vaginal sex without a condom. This was the first time a guy had ever cum inside me during vaginal sex with no condom to catch it. It felt almost no different to me although as we talked after, I felt increasingly slimy and did my best not to dwell on what was oozing out of me because it turned my stomach a little. I do not do well with body fluids.

It feels worth mentioning that he is, to use his words, “fixed.” If there was any chance of pregnancy I never would have been okay with that, and neither would he.

After another small pause where we talked a bit, we moved onto the last part of the session – my orgasm. I’m very much in this for the orgasm. Especially after an evening of being ridiculously turned on while he would rub at my clit randomly and pull away, keeping me aroused but never letting me finish.

He told me to masturbate for him and he sat back and watched. While I obeyed, he continued to mess with me a bit more. He slapped my breasts back and forth which hurt quite a bit, even through my arousal. I don’t remember if he did anything else; my brain was kind of fried by this point. The memory feels so fuzzy that I just remember the pain of his hand swinging back and forth, knocking my breasts to one side then the other while I rubbed at my clit until the orgasm I was reaching for finally arrived. It didn’t take long to get there, I had been so turned on all evening, and the extra pain he was so generously providing assisted in the process, too.

When all was said and done there was some mild vaginal soreness that I knew would be there the next day, but otherwise there was no lingering pain. That was about as good as I could have expected sex to go and was one of my better experiences with it.

After a rest and some more chatting, I eventually retreated to the bathroom to clean myself up and get dressed.

–

• the living room, stripping me and making me stand and wait for him was a delicious show of his control over me;
• the glasses, that tender moment of him showing such care for me before tying me down to hurt me;
• seeing him flogging me, I don’t know what it was about that but seeing him doing it gives me that electric butterfly feeling every time I picture it; and
• him reminding me that he used “all three holes” that evening, a deep reminder that I’ve given and encouraged full access to use me for his pleasure.

The rest is great, of course. I loved the whole evening. I love our sessions overall. But those are the moments that I just couldn’t get out of my head, enough that I felt like finally recording and sharing them.