Tonight I’mma Let You be the Captain/ Tonight I’mma Let You Take Me Higher

Sir. That’s what he told me to call him. Fine with me since I only planned on indulging his desire for the next few hours anyways, and to be honest, I had been expecting something along those lines from the start.

I had met Sir through a dating app when he messaged me asking if I was interested in BDSM. And yes, I was/am, but had never found someone who was willing to do some of the things that turned me on. So, even though Sir was in his late 50’s and not someone I usually found attractive (he was white, and much older then I was used too) I figured it was something that I wanted badly enough, so I’d try it this once.
After a few messages back and forth discussing what might transpire if we were to meet, He gave me his address and we planned a time for our rendezvous. I wasn’t nervous until I had rung his doorbell. That’s when it hit me, I’m about to experience sex like never before… at least I hoped so. Sir invited me in and we sat on the couch for less then 10 minutes and got the small talk over with. We both knew why I had come and we didn’t need to waste time on pleasantries. It wasn’t your normal first meet up where you feel like you should “get to know someone” before you can fuck. I hate that bullshit. I don’t care, you don’t care, let’s just get on with it. Sir understood that. Our couch time had no “where are you from” questions. It was more like, how was your day? Would you like some water? Do you need to use the washroom? Ok let’s head upstairs.

“Oh” Sir exclaimed, take your hair down and leave your glasses down here. Because once we head upstairs, I’m the boss. You don’t do anything until/unless I say so. Do you understand…. HOLY HELL. Yea I understood. I understood it made me super horny.

This is what I’d been looking for! A man to take control! I wanted to feel like someone else was going to do everything in their power to make me orgasim, even when it seems like I’d had enough… they would push me further, to my extreme.  I was wet like nobody’s business as I followed him up the stairs. But then as I was led into his room the anticipation was ridiculous. I saw an open closet full of all his “apparatuses” and I was so excited for whatever was to come. And trust me, by the look of that closet, ANYTHING was possible.

Sir asked me if I squirted, which of course I said no to, since at that point I never had. I had barely even heard of it let alone ever done it personally. So he said ok, and something about using plastic sheets if I did. Like this man was prepared for EVERYTHING. Anyways, he told me to undress and lie on my back which I did. He then proceeded to blindfold me, which was the best part, not knowing what was coming next, or even what tools he was using, it totally heighten the experience. I would highly recommend everyone try sex with a blindfold at least once. Then he gagged me with a ball gag, which I’ll be honest was my least favourite part, but like I said, I’ll try everything once.  Ohhh I should mention since I just remembered, our couch conversation also included a quick discussion about a safe word, as well as a ‘grunt’ of sorts to use if I was gagged… which I currently was.

After I was blindfolded and gagged, Sir began the painstakingly slow process of tying me up to the four corners of the bed. I swear he did it slowly just to mess with me, and he definitely knew that it would work. Because the anticipation was killing me. By the time he was satisfied with my position, I was 100% helpless, and 100% horny. I could barely twist my arms, I could slightly move my legs but not enough to close them that’s for sure. I couldn’t speak and I couldn’t see, and I was so excited. I was thankful for the blindfold because I didn’t have to have the image of an older white guy doing his thing, I could imagine anything I wanted, which I did, and it was hot.

Sir rustled around in his closet a little, and I’ll be real, I can’t describe this in much detail because I have no clue even to this day what he used to make me feel so great, but I’ll do my best. First, some sort of light whip was used all over my body. Then a few light clamps/pins were put on my nipples and varying other places. Then the vibrator came out… and teased so much. So close and then pulled away, repeatedly. Then right on the spot on full speed until I was squirming on the bed and trying to move away and feeling so good. And I got to the point where I thought I had had enough, I thought I had orgasimed, and I thought I couldn’t handle anymore, and I considered using my safe “grunt”, but then I thought to myself, I’ve come this far,  I want this, I want to see how far I can push myself, I wanted to be taken past my limits.  So I just let him keep going… and Sir did. And that’s when I came. Everywhere. I squirted so hard and so much it was amazing.

It was my first time and I honestly didn’t know what was happening. Yes it felt SOO good, but I was embarrassed. Especially since he was worried about getting his bed all wet (totally understandable). So he made me come/squirt a couple more times, since I was on a roll now, but then he put the vibrator away and started to untie me so we could change the sheets to presumably continue. But once I was untied, and standing there, with the blindfold off, I was like, nope. I’m done. I got enough of what I came for, I’m not getting back on the bed. I was seriously so embarrassed about squirting and the reality of this old man up in my pussy was just too much, that I just started getting dressed and was like thanks, but I’m gonna peace out now.

Sir was very kind about it, saying that it wasn’t a big deal and next time we would just start out with the plastic sheets etc. I’m thinking to myself dude, there isn’t going to be a next time, but thanks anyway, as I tried to dress as quickly as possible while my body is still shaking from coming so fiercely. Once dressed, I hurried down the stairs and for the door ASAP. I thanked Sir for the night and was out like a flash.

Once I got to my car, I finally had a chance to think through everything that had happened. I truly enjoyed the night and everything my body had experienced, I would definitely want to do something like that again, but I just wished it was with someone I felt more comfortable around. As well as someone I was attracted to.

Although, lol I would still want the blindfold.


-Rihanna/Rude Boy-


7 thoughts on “Tonight I’mma Let You be the Captain/ Tonight I’mma Let You Take Me Higher”

  1. I definitely feel you on the walking away, “I’m done” mentality. Sometimes, you just done haha. I did that the other night and the guy hasn’t stopped texting me.

    Liked by 1 person

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