2024-04-10 - Session with Tim

Posted on April 10, 2024
Word Count: 4062

Comments 0

Well it finally happened after dating and playing for two and a half years. Of course, that makes perfect sense to me. I’m not very into penetrative sex overall. It takes a lot for me to want it, and most often it’s disappointing. I didn’t go into this session expecting penetrative sex at all.

Back in November, I had mentioned that I was putting both vaginal and anal sex on the table. It’s April now. November was five months ago. We had talked about it a bit at the time, mostly talking about anal since vaginal is even more hit-and-miss with me, and more often miss than hit. We’d also talked occasionally about it since that point, flirting around the idea, along with some planning, and I gave him all the information I could give regarding my experiences. It sounded like he was into it but a long string of sessions where he was too tired, or I was, and it had fallen out of discussion completely, but it definitely hadn’t fallen out of my mind.

I sent a reminder about it last week by hunting down a particularly spicy private message from December and replying to it. I didn’t expect anything to come of it any time soon. I just wanted to keep it very obviously on the table. My expectation was that by bringing it up again, we’d talk about it more, flirt around the idea more, and I’d probably get more warning than I actually got, which was nothing more than a heart-react on that reply-message.

I’m not complaining, though. It was a great session. He was delightfully rough with me right from the start, and kept it up.

We’d gotten sandwiches for dinner and since he was still running around getting things sorted around the house, I was waiting to eat mine. I generally prefer to eat together and think it’s kind of rude not to wait. So I waited, reading my book while he did what he was going to do. He came up to me and put my play collar on me, fast and a little rough, not bothering to move my hair out of the way, then pulled me to my feet. He removed my shirt and cami and replaced them with my robe. He bound my wrists together with my hemp rope (red <3) and told me that now I could eat and he handed me my sandwich. And we settled in to watch TV and eat dinner, with this added challenge for me.

He’s done stuff like this to me before. Last time it was handcuffs which were a little challenging but not really that difficult to work with. Well, having my hands tied tight together with rope was a completely different challenge. First, I couldn’t angle my hands very well and I couldn’t twist them in different directions either so I had to really think about how I was moving my arms together to be able to pick up the food next to me. Second, with the little bit of rope dangling down a few inches, I had to be careful not to get it in the food. I really did not want mayo/mustard-flavored rope!

I did manage to set down my sandwich, open the wrapping, pick up what I wanted to eat, and successfully eat it. I was even able to do all that without getting any rope in the food, but it was definitely a challenge. In the middle of working my way through the sandwich he pulled me up off the couch again and removed the rest of my clothes, leaving me only in the robe. It’s always a little jarring to get interrupted in the middle of eating. Like… but… food. Which of course is a lot of the point. Being able to interrupt me at any point is a fun display of control that I don’t always appreciate in the moment, but I definitely enjoy in the big picture.

After dinner and a short TV episode, he decided it was time to go upstairs. We had less time to spare and we were both very much in the mood for torment. He asked if I needed my hands to go upstairs. I didn’t think so, but I was concerned about how I would carry my things upstairs. It didn’t matter, though, he decided to undo my hands anyway for easier removal of the robe later. Temporarily free, I was able to grab my phone and water bottle and shove them in the robe pockets to head upstairs for the rest of the evening. I took a moment to admire the marks the rope left on my wrists. I do love marks.

The rest of the evening was kind of a fuzzy blur. I only have a rough idea of the order of things and I’m definitely missing bits here and there. A lot happened in just a few hours and I fell into subspace and let it all wash over me. I can’t help that some of it just floated away.

I vaguely remember him asking me to stand up, so I must have been sitting on the bed. Or maybe he pulled me up? What really sticks in my memory though is standing next to the bed, facing him. He made a swift and simple movement and tipped the robe easily off of my shoulders. It brushed lightly against my skin as gravity pulled it to the floor, leaving me standing naked in front of him. I could feel the individual points of pressure from each fingertip he pressed into my chest to push me down onto the bed, using one hand and just the right amount of force. I remember sitting on the bed and feeling the continued pressure guiding me down further so I was laying on the bed for him.

He had placed me perpendicular to where he actually wanted me. He put his hand on the bed and told me that’s where he wanted my head. As I moved to obey, I had a flash of thought: was there any way I could deliberately misinterpret the command? Obey but still get it wrong? I was in a playful enough mood to try, but I couldn’t come up with anything fun so I simply moved into the position I knew he wanted. As I brought my face down to his hand, I rubbed it lightly against him to show affection. He pulled away and got to work leaving me somewhat disappointed that I didn’t get any petting out of my gesture.

He tied my feet together while he told me his plans for tying me to the bed. He tied my ankles very tight and when he checked in I told him so; he adjusted it to be just barely loose enough. The rope still remained very tight, but now I could squirm a little to adjust my feet without it digging in much. Which didn’t matter much overall because he planned to have me struggling and pulling against that rope soon enough. At least the adjustment allowed me to rest my ankles in a comfortable position during breaks.

He tied my collar to the top of the bed, and with an unusual quickness, he secured my left arm into a velcro cuff, chatting casually “Did I tell you I cleaned out the velcro on this?” I didn’t answer him; my mind was lost, caught up in how fast and rough he’d just secured my wrist. I don’t remember most of his words from the evening, but for some reason I do remember that.

He left my right arm free at first; the bed is extremely squishy and when I’m face-down it tries to smother me. I normally get to keep one hand free which I use as a little platform to keep my face above the mattress as needed. While securing my feet to the bottom of the bed he came up with an idea of how to secure my remaining arm. He placed the other cuff just next to my elbow, which was odd, but worked surprisingly well. Both arms were secured, but I still had a hand available to hold my face up. The only disappointment was that I could easily have reached the tie for my collar to undo it. I thought about it briefly (did I really want to “brat” tonight?) and just decided I wouldn’t and didn’t think any further about it.

He had also considered tying my wrist directly to my collar but disregarded the idea when I told him that after about 30-40 minutes I would need to stretch my arm out. Keeping my arm bent tight for any length of time causes my hand to start going numb. He didn’t want to have to untie me for at least an hour or however long the session would last.

The order of some things is a little fuzzy overall, but I believe he started with the horsehair flogger. It was relaxing at first. The horsehair doesn’t really hurt when used normally. The tips have a mild prickly sting, but it’s not intense. Overall it’s mostly a relaxing sensation. At least until he decides to start getting mean with it.

My horsehair flogger is a striking piece (get it? Because it’s a flogger? No? Well it’s gorgeous anyway). I made it with about double the amount of hair typically used, hand-dyed in vivid red and blue, which I braided into about 20 individual braids. The braids extend roughly half-way down the length of the flogger, but end at varying lengths, leaving the bottom of the hair loose. The result is a relatively heavy flogger that stays together when swung so the tails hit precisely where they’re supposed to hit instead of spreading all over the place. I remember fuzzily thinking about the feel of the spread on my back, how it spreads but not a lot, and how it’s the braids that keep it grouped so well.

I remember one fleeting thought that maybe the braids had been a bad idea as he began to strike me hard and fast with just the tips of the flogger, going from relaxing to quite a bit of pain, especially after he hit the same spot multiple times, just to show me he could… just to get me to make the noise he wanted, or to get me to jump, writhe, and struggle how he wanted.

I remember opening my eyes during a short break and something red caught my attention, mixed in with my hair. As my eyes focused I saw that it was a bright red strand, about a half-inch long: the tip of a hair broken off from the flogger. The next day I also found an additional broken 2-inch blue strand from combing my hair. I could blame it on how hard he was striking, but there’s always a tiny bit of damage with use. But that’s okay; I crafted that flogger with so much horse hair that it will tolerate normal breakage from his hard use.

The broken flogger strands weren’t the only hair-related issue of the evening. My hair was a constant bother during the session. There was one point I was trying to pull a strand out of my mouth during a short break. I kept grasping at it with my nails but it slipped through every time. So I suffered not only from the flogging, but this random nagging hair. I eventually removed it, but quickly found it replaced with a small but substantial chunk of hair. The smooth feeling of larger amounts of hair against my tongue is generally nice so I let that bit stay, figuring that I’d rather have a chunk of hair in my mouth than spit it out and have wet hair plastered to my lips. Thankfully, he did notice during the next break and removed it for me. Another small hair lingered behind but I was actually able to remove that one. Finally, my mouth was hair-free! An unintended torment of the evening, but if my hair isn’t left free he can’t pull it as easily.

I believe he was still working me over with the horsehair flogger when he decided it was time to plug me. I can’t even describe how much that announcement always turns me on. The anticipation always gets me immediately wet, and sometimes I’ll let out an involuntary sound. I really don’t know how to describe the noises I make – it’s not a moan, but it’s probably related. And then I waited anxiously, for him to do what he just said he would do.

I felt him sit on the bed behind me. I heard him snap the lube container. I whined in annoyance when I felt the drop of cold lube find its mark. Sometimes he laughs at that but I can’t remember if he did that time. And then, focus. The inserting process is a moment of concentration, focusing on the feeling and trying to keep myself relaxed, or slightly adjust my angle, or whatever I need to do to help it slip in; help myself be open for it. Anal play is not a process I want to have go poorly. Then there’s the moment when the widest part pushes me open as much as it’s going to, then it tapers and slides quickly and smoothly the rest of the way in, secure. That moment always makes me … moan? I don’t think it’s a moan, but I definitely make noise. I don’t remember it, but I know I made the noise because I always do. Tim comments almost every time how much he loves to hear that noise. Then I can usually feel myself twitch a little because all I want in the world in that moment is to just rub my clit and get myself off immediately. Which, of course, I can’t, because that would ruin the fun, and at least this time, I physically couldn’t reach with my hands and feet tied in place. I’m always a little desperate for it until he distracts me.

He went back to his flogging after that, where I spared a brief worry about if he would be getting lube on the tips of the flogger tails if he struck too close to the plug. The thought was quickly drowned out by my own voice, crying out from pain or surprise. Or surprise pain. While he wasn’t pushing me to the edges of my pain tolerances that night, he wasn’t exactly going easy on me, either.

He continued to be very mean with the horsehair until he decided to change floggers. The instant it hit me I knew which one he’d picked and I relaxed again. He had chosen the heavy deer suede one, which I had made out of remnant deer suede lace. It is very heavy and very soft. He struck me several times, heavy but soft, and it was relaxing. But soon he got mean again. The strikes began to use less of the flogger until he was just using the tips again. A very different pain than the horse hair, but painful all the same!

Throughout the flogging he would also take breaks to use the Wartenberg pinwheel, a classic device that we’d only recently started playing with. As he rolled it across my skin he would comment on how little pressure he was using. Even with light pressure, it brings a smooth and sharp, but fleeting pain that always gets me to cry out. I don’t know if I like it, but I certainly don’t hate it. In this particular session, rather than simply painful, the sensation was also ticklish (I learned how to mostly turn off my being ticklish in my 20’s but for some reason I could not do it that night for this evil little pinwheel), causing me to strain my legs up hard against the rope. So hard in fact, that I managed to loosen the tie completely, bending my knees and bringing my still-bound feet up in a reflexive but useless attempt at protecting myself from the pinwheel. He told me that he hadn’t expected me to pull so hard as he paused to fix the rope. He cinched it swiftly, forcing my feet back into place with a delightfully quick, smooth motion. I did not manage to get loose again throughout the rest of the session.

At one point he paused, just running his hands over me. I love the feeling of his hands over sore skin. It’s lightly painful, but also extremely relaxing and pleasant. Then he wrapped his fingers around the plug and I knew it was coming out. Which sent my mind racing. Why? What’s the plan? Larger? Something else? We’re not done yet, are we?

He slipped it out quickly and announced that he was going to trade up to a larger plug. I melted and cringed at the same time. The larger one is effectively a more intense version of the smaller one. Let me be clear that when I say “smaller” and “larger” I’m talking about sizes “XS” and “S,” the smallest two out of a range of 9 sizes of this particular design. Out of the 9 sizes, I own and can take only the smallest three, and of those I can only barely take #3: “M”. “XS” has become easy-ish, and “S” manageable but intense.

More lube, and another round of concentration where I focused and tried to keep myself relaxed and open. He took his time, working slowly and carefully, pushing in just a tiny bit deeper with each soft thrust. Then finally there was a very light feeling of pain at the widest part, and then he pulled it out – damn. So close. And again, just the tiniest hint of pain at the widest part and then it tapered in, securing itself into place, and I heard myself make that noise again, but more this time, because the feeling was much more intense, and I was being held open a little wider now. The throbbing ache of wanting so much to urgently rub at my clit returned, more noticeable that time and harder to ignore. I believe I whimpered from frustration.

Again, I believe, he returned to flogging, and probably the pinwheel, but I must admit, my brain was so fuzzy by that point that I’m not entirely sure what happened. I just know it was a while before he took another pause, and told me what he wanted to do next. I wish I could remember the words. I can’t. I remember the feeling. The lightning of excitement mixed a tiny bit of panic, as he said that the next thing he wanted to do to me was fuck me in the ass.

Those are my words, by the way, but those are the words I have, because I simply cannot remember what he actually said to me. I remember “I cleaned out the velcro” but almost no other words for the evening. Moments like this make me want to record the audio of our sessions so I can refer back to it. The words are so important. Words mean everything to me; they keep me grounded and present, and they prevent me from spiraling. And yet they’re simply lost to the moment.

I felt his fingers wrap around the plug again, and that one came free, too. He inserted a finger into me, which I honestly found a little unpleasant; fingers are rough and bumpy. Thankfully he didn’t continue that, but moved on to what I was actually looking forward to.

He perched behind me, finding himself a position he was comfortable with, lubing himself up. I felt him press against me and slide into me, so easily I wasn’t able to tell how much he’d actually inserted. He went slowly, and it was easy, and it felt smooth and nice. There were a few false starts, but it was slow and we were in no hurry. I adjusted myself as I could to help him slide in easier.

And then he pushed in deeper and he got harder. There was some pain from that, but not an unreasonable amount. It wasn’t the “bright” pain of damage, it was not much more than an uncomfortableness and so I wasn’t concerned. He continued pushing and thrusting deeply into me and must have gotten harder still because suddenly the uncomfortableness ramped up a small amount. But with that pain was a companion pleasurable feeling. This wasn’t my masochism making the pain feel good to me, but an actual good feeling, and the pain was simply mild and unconcerning and so I paid attention in case it changed to concerning pain, but I otherwise ignored it.

He thrust into me for what seemed like a long while, and every thrust caused a moan to escape me. I remember him telling me how good I was. I was his good pet and it was amazing. However, with time the pain was slowly building and becoming harder to ignore. I remember trying to find words, lazily, in no rush, but still trying to call them up to say that I wasn’t sure I could take much more. But before I could say anything, he adjusted his stance and started pounding hard and fast and all the words were lost. The pain nearly disappeared and all I felt was a weird deep indescribable pleasure as he slammed into me.

Soon I felt him shuddering as he came inside me. I enjoyed feeling him convulse and hearing him moan. He collapsed onto the bed next to me and gave a couple last little twitches. I loved that I could give that to him. But I must admit, my next thought was “me next?”

After he had a moment to recover, he slipped his hands up between my legs. He had released my feet from the bed but I believe they were still tied together, so I had to pull my legs up awkwardly to open them enough to help him hit the right spot. He rubbed at my clit for a while and it was good, but I definitely found myself wanting more. I pulled words together enough to ask if he could also continue to hit me while he did that. He agreed and told me how much he loved how I ask when I ask for things like that.

And he did. He started smacking my ass with his other hand. I was turned on enough, and warmed up enough, that it didn’t matter how fast or hard he wanted to do it, it was all amazing. He grabbed large chunks of my hair and pulled my head back, causing me to cry out, but it was great. I love my hair pulled. And soon, between the pain and the stimulation, that familiar shudder came, forcing me to curl up, or at least try as my body pulled hard on the restraints. And as I felt myself curling and straining, he kept going, enough to make me cry out even more as he pushed me just a little, but not too far, into overstimulation.

He let me rest a moment before he untied me. I remember commenting that there were probably very good marks on my ankles from all the struggling. I had pulled quite a bit so the rope had ample opportunity to dig in and leave indentations. He confirmed that there were indeed good rope marks, but no bruising. I didn’t expect bruising; I don’t bruise that easily from something like that. I actually regret not looking at the marks but I was so worn out I didn’t have it in me to care enough at the time.

Afterwards, we cuddled and talked about the session. I could tell I was going to be sore the next day (I was actually sore for two), but I was really happy. He had been delightfully rough with me without pushing me too hard, I had been tied to the point of nearly no escape, we had anal sex for the first time and it was awesome, and I look forward to the next session where we’ll have a bit more time to play.

I wonder what he’ll have in store for me next time. ~~<3