I had been with him twice before. While I didn’t really realize it, he comes to town around the same
time each year. Once I hosted at my house, a quick simple blowjob. The second time he had an Air BnB
close to my office. I took a longer lunch for a much more involved oral sex session. I got the feeling he
wasn’t into fucking, so I never quite perused it.
This time was different. WAY different.
Like the first time, I hosted. Like the first time, we used a bedroom. Unlike last time he had me strip
down. He did the same. While I started out sucking him, he gently, but insistently moved me over to the
bed. I lay back and he was between my legs. His hand reached out to my balls…..then moved over them
and below them. His fingers traced over my taint, which had me shudder. Done right, that is such a G-
spot for me. But then he went further.
Clearly, I’m not adverse to things near my ass. But he trailed those fingers over my hole, and around it.
The motion made me and my hole quiver. He looked right at me as he started to slide in his middle
finger. We never broke our gaze. The first knuckle, and then to the base of his finger. He held it there, I
squeezed my muscles around his finger, his one eyebrow raised. Then I felt the index finger start to slide
up there as well. Both fully in me, I know I put my head back as he moved them around. I was sure this
was the start of loosening me up for his fuck. Turns out, I was only half-right.
As I’m always prepped (well, usually), my ass was clean and there was poppers and Abolene on the
bedside table. And a towel, as I am always a gracious and neat host.
He now withdrew his fingers and reached over the lube. He put it on three fingers and went back to
work. He was methodical about it, and he was big on the eye contact. I think it was more than just the
eyes. He was looking at all my reactions – to see how I was liking it, or if I was. He was looking for the
ability to keep going. While I didn’t say ‘yes’, I didn’t say ‘no’ either. He moved the fingers around and in
and out….not all the way, but close to. He was truly opening that up.
By this point, with nothing said, I knew it was not fucking that was on today’s menu.
Once we established I was good with three, the pinky started to make its way toward my butthole. The
hole itself was already slick from the existing lubricant, so there was no reason to pull out the other
three. I’m guessing there was also a risk of if he took them out, he might not to be allowed to get them
back in. Just a guess though. As his last finger wasn’t large, it wasn’t a huge struggle to eventually get
that inserted.
With the four digits in place, he used them wisely. He’d curl the fingers, individually and in various
forms of multiples, up to and including all of them at the same time. I won’t lie, it was kind of good. I
liked when he’d pull back somehow…………and I think it might have been with one finger, how it would
take hold of my tissue and stretch it. It felt new and incredible. He stayed a seemingly long time with this situation. I didn’t encourage him to quit or go further. Honestly, little was said – none of it being
permission.
Since we are here, I should say, and you’d have to scan these 800+ posts, but I’ve only gotten this far
twice before when it came to fisting. It was never really on my to-do list. Up till this point, we’d never
proceeded past four fingers. If pushed on an answer if I wanted to be fisted, the answer would be ‘no’.
But that’s the funny thing about sex, should you be adventurous as I think I am, is that you don’t know
you truly don’t like it until you do it. On paper, lots of things sound bad. I mean, I don’t think I’d EVER be
down on sounding, but I’ve never tried. That said, I’ve never tried animals, and that is just off the table.
NEVER EVER happening.
So when guys ask me, ‘are you into kink?’, I roll my eyes and then I send them the eyeroll emoji. I
usually follow up with ‘kink is all relative’. I know guys who think having a guy shoot in their mouth is
kinky. I call it ‘sex’………..and ‘necessary’. I don’t think I’ll ever get to a point where I think fisting is
normal sex routine, but I know guys who do. To them, it’s not kink. To me, it is.
Anyway, the guy finally asks if I have a dildo. I answer in the affirmative. He slides his fingers out
carefully and asks me to retrieve it. I do. He slathers up the 8”x5” rubber phallus with lube and deftly
inserts it into my asshole. I should say, by this time, I have poppers at my side and not afraid to use them
sparingly. He uses that dildo well, fucking me with it, firmly but moderately paced. He’s making sure
that hole has been opened with those four fingers and that the lining is still pliable for more. This is my
assumption anyways.
Eventually he slides out the dildo and puts it right next to me. While looking right at me, he only asks
one thing, “ready?”. I nod. I don’t even verbalize. After relubing his hand, one by one, he gets the first
three in easily, then the fourth. It’s the last one, the thumb, that will be the challenge. And it was.
Mentally, I’m not sure I was there yet, and it manifested physically. You can’t say I was ‘tight’, because,
well………..four fingers up my ass………but for a fist, I was snug. As I know it is coming, I take a healthy
(well, you know what I mean) hit of poppers for both sides of my nostrils. It opens me up enough to
slide at least half of the thumb up me. Then all of it. I’m down to the bottom / side knuckle, but no
farther.
He bides his time, watching me intently, barely looking down at his now disappeared hand. He rests his
hand until I relax a bit more, then he moves….slightly, but surely. He’s not letting this moment go to
waste, for him or myself. There is a time I feel so incredibly full I tell him to just hold still. He does. I take
a HUGE hit of poppers and something happens. If you remember that very first time you tried them –
should you have had the opportunity to do the original real poppers – and how you kind of got
transported somewhere else, even for a minute? That was this. Times 10.
With the poppers hitting, he shifted his hand and moved it forward. He was at, or near, the wrist. At
this point, I went into completely other state. While I was staring right at him, I could not see him. There
was this total euphoric state that lasted a minute or two – which when writing does not seem long, but
when you’re there with a semi-stranger’s hand up your butt, it’s a long time. There were moments that
I wasn’t sure where I was, but somehow knew what was happening. My hole felt really good and it
wasn’t lost on me it was because there was a hand up it.
Mr. Fister moved the hand slightly pulling back and slightly moving forward. Spoiler alert, there was
fisting, but this was not fist FUCKED. There would be no movements so pendulous that it would imitate fist-to-ass intercourse. The movements to the eye were probably subtle. To my nerve endings – no so
much. Again, the tugging on the tissue on the pull back was somehow heaven.
He very slowly withdrew all fingers. As you’d imagine, it made me feel empty. But without a word, he
picked up the dildo and pushed it up my ass in one motion that took all of 1.9 second. He added no
additional lube, just replaced his hand with a big rubber dick. That, he did fuck me with. It was fucking
amazing.
As he slowed down on that, and I can’t confirm this, but I think he got exactly what he wanted when I
asked for him to put his hand back in me. There was no smile or smirk, not even a word, but a nod of the
head. And he did. And with another hit of poppers, I had the euphoric state again……even more intense
than the last time. I’d have another one a bit later on.
We tried me on my knees as well and he got his fist into me that way as well. I can’t say I liked it more
than with him just working between my legs, but it was fine. I didn’t have an out of body experience the
way I had.
At this point, we were well over 90 minutes into this session and I did have stuff to do, as did he. While
there were times I had a raging hard-on, at this point I was semi-flaccid. It was never about me getting
off and seemingly I don’t think so for him as well. I did get off – mentally. Often.
Before we completely finished, I asked him to shove that dildo up my ass again, and he did. Faster and
harder than the last time. We both knew I was open enough to take it like that. We discussed him
getting off, but he knew he couldn’t do it via sucking and he confirmed that he did not fuck….at least
me. But he agreed to jack off, so he did. As he got close, while on the bed, I got on my knees and spread
my cheeks. He stepped up behind me and shot on my hole and in my crack. With little urging, I asked
him to use his fingers to push the cum up there. He complied. It wasn’t a fist, but 2-3 fingers pushing his
warm load into my completely used ass.
He cleaned up and left. Before I resumed my day, I took the dildo and sat on it, taking it one more time.
Somehow it didn’t feel the same when you do it alone.
I’m not opposed to trying this again. He was from out of town, so that’s not on the docket for at least
10 months. And I’m not sure how to pick someone who’d go at my pace. But it’s no longer off the menu.
1 comment:
I kinda if the eye contact was both that he got off on it and that he was looking for subtle clues how fast to proceed. Sure, the body tells you the limits but so do the eyes.
As for guys that ask if you’re into kink, I know exactly what you mean. Internally I roll my eyes but now I just take it as a guy shy about telling me what he desires. And I take it as duty to pump him up and make him feel good about his hidden desires, whether that’s just raw sex or getting flogged until he’s marked. So I usually respond by telling them “there’s only a few things on the list I haven’t tried and what I’ve learned is that I REALLY enjoy pushing limits... so what are your limits?”
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