A Risky Return to Sin City

As this is completed, he is gently rubbing my back, sides, butt and legs as if he was familiarizing himself with me. At the same time, he is having a conversation with DR. D which goes like this, “So fisting is on the ‘hard list’ but ‘anal play’ is on the acceptable list. Well, I guess I’ll just have to make sure when my hand goes all the way up that tight ass that I don’t fist up, I wouldn’t want to cross his silly rules. That’s what you want, right, my arm up his ass?” The question being directed to DR. D and not me. “I’ll just flex my wrist and fingers instead of making a fist while I play; his fullness will be the same. Probably worse, more uncomfortable, but the choice was his. He really has no idea what half of the ideas on his list really were all about, did he? Oh look, he’s tensed up and has goose bumps, precisely why I wanted him gagged. I can tell he wants to argue and object.” 

My mind is spinning over what I have just heard. One thought of many flooding in was that I recall that while he was tall, solid and masculine, his package was just average. If the old wives’ tale holds true, that means his hands are average size too. I hope so or this could be brutal. Other thoughts deal with my frustration that I am being exploited on a contract technicality. You can sense their enjoyment of having the upper hand with me, figuratively and soon to be literally. They have thoroughly formulated and planned out the details for this episode; the gag, bench, straps, my position, the loophole found are all circumstantial evidence. There is more to come.

I hear the sound of latex gloves being put on, followed by my crack being smeared with lube. A second glob is then inserted into my hole. Now anxious and tense, I am instructed to “Relax, you are going to enjoy this. It’s my sub’s favorite.” For my own benefit, I try to relax with minimal success.

He starts very slowly and gently with one gloved finger, sliding fully in and out. He slightly changes its orientation each time he enters, sometimes twisting, sometimes bending his digit. I find that I am holding my breath. He tells me again to “Relax, this is only my finger. I heard that last night you took on all kinds of cocks, each one of them are bigger than what is in you now. You need to do rhythmic breathing to get pain/pleasure from this. Otherwise, it will be a pain only experience.” I try harder to relax and focus on other thoughts.

The master moves onto two finger penetration and in time to three, telling me as he proceeds, not that I could stop him. I have had three fingers up my butt before, and this causes no special distress. He is also an expert at this, and he is stretching me gradually, so I don’t feel any over the top discomfort. Initially, it was the same when he moved onto four fingers, but as he pushed his fingers deeper, we reached the point where the knuckles at the base of his wrist expand and that is where my hole spasmed in pain. He backed off, added more lube and then pushed back in again. Nothing overly forced, he worked my butt with different hand flexes and twists. Finally with more pain and stress than I liked and even a little bucking against the bench, my hole took his upper knuckles. He only was able to push in a short distance further when his thumb, still outside, bottomed out at my crack.

He let his hand just rest for a few moments as my rectum came to terms with the intrusion and pains, which subsided after a few moments passed. I describe this as unpleasant, a bad but bearable feeling. Also, as being one of ‘total fullness’, of being internally stretched, an unwanted violation that you can’t expel but my rectal muscles try anyway. I could feel my body struggling to handle it, pushing at it like a hard bowel movement having no success. I get a little diversion first as he jiggles my caged cock with his other hand. Once more, I got the coaching to relax and to concentrate on visualizing what was happening. The graphic advice helped. This game is as mental as it is physical.

After a minute or two, he starts manipulating his fingers, spreading them, twisting them, usually individually, sometime in groups. It causes interesting sensations on the rectum walls, certainly a feeling I am not accustomed to. He concentrates on the area I guess where the prostate can be messaged. This causes some stirring in my loins, reminding me I am still caged as blood tries to expand my trapped penis.

This stimulation goes on for about five minutes, when he begins to carefully and slowly withdraw his hand from me. The passing of his knuckles causing as much grief coming out as going in. “Usually, on a first session I end there with my new subs. With you, though, we won’t have a second chance, so I’m going to give you a few minutes to recover and then you are going to take it all, don’t worry, Cunt, I won’t make a fist and violate your contract. I am surprised at how well you stretch, you’re nowhere close to tearing.”

His second assault is just as slow and careful as his first except he has switch from his right to his left hand. Different this time is when he starts with his thumb instead of using his finger. And with it he can do more acrobatic moves in my hole. The change is amusing and reenforces my own realization that I am now well stretched. As such, the working up to four fingers goes quicker. When we hit that point, I felt his thumb being added to the mix, which as he forces it forward with a new coating of lube expands my hole wider than ever before as it allows his entire cupped hand to move in. Easy at first as with all five digits grouped and pressed together, their girth is not excessive down at the tips. As he pushes forward the hand grows wide in girth regardless of how tightly closed he keeps it.

He uses his free hand to gently massage and rub the tight stretched surface muscles around my bulging anus containing his fingers and thumb.  Never becoming impatient with me, he takes the time. Using years of expertise, plenty of added lube, and a variety of hand movements and flexes to stretch my anatomy, he manipulates my rectum to the point where my hole finally expands enough to let his wrist pass by and his hand slip entirely within me and closes behind, just as a butt plug expands your rectum as it enters then closes around its neck. Initially sharp, harsh glaring pain follows that makes tears well up and me suck air rapidly in and out through my nose, making me nearly hyperventilate.  But it subsides in short order to simply a strong, hard ache, but none-the-less, an ache that I can handle. A little more than the pain/pleasure I enjoy, but we will get there. He lets me rest, giving my body time to adjust and accept. Then it’s back to playing with his fingers. Praise is given by both DR. D and my tormentor. And I more appreciate what my wife endured in childbirth. I hear “get some still shots to go along with the video, he’ll want them as keepsakes, maybe something to be framed on his office desk.”

He plays for a bit; it almost feels like he is drawing pictures with his fingers. There is also some thumb and finger manipulations and finger drumming in his repertoire. I admit it stimulates me, and I have that euphoria feeling I get when I am bound and abused against my will. I concentrate on the visual in my mind of what one would see from behind me. I’ll get to see it for myself later. I feel so full and stretched, it is like he is all the way up to his elbow. He is not.

All good things and thankfully bad things must eventually come to an end, he extracts himself, which ends up being nearly as painful coming out as going in. He had been pumping his arm in and out as part of his playing in me but had not pulled back far enough in any rotation that the widest part of his hand would stretch my entry excessively like it did going in the first time. It will now that he is exiting. He is not abrupt. With his loose hand adding more lube and again massaging the outer surface keeping the skin from tearing, he gently twists and flexes his forearm and hand easing the withdrawal.

He leaves me. The pain while substantial subsides quicker than I would have thought. While I know I am empty, I feel like my hole is still open. Almost like a breeze is coming in me. It must be because I hear, “Don’t worry it will close backup tight before long.”

BDSM Dominants are by nature aggressive abusers but are also considerate and loving to their submissives. Damp, warm towels are laid down my crack providing a needed calming sensation. My butt cheeks and anal rim are gently massaged. It feels good. A vibrator on a low setting is used as an aid. After a few minutes the warm towels are transitioned to cooler ones and then finally to ice wrapped in cloth, all applied to help shrink back down my stretched-out canal. They let me know, however, that this is for their benefit, not mine. They want me tight again for later fucking. None the less, I enjoy the comforting attention.

Another first. Fisted by another name. The photos prove Interesting, but I don’t see what the big turn on is for either participant. To each his own, I guess.