Chapter 36: Sweet Tightness

We rested, but Li kept track of my erection, it’s state and the state of my balls. She liked us resting in bed together, cuddling romantically after the strenuous violation we had done, but she really wanted her body to be violated and used for my release one more fucking way before we slept for the night. So she wrapped her hand around my shaft, giving it a pump now and then, as we rested.

We both knew there would be pain, her body was tiny and even relaxed her muscle was so tight, she had a much rougher time taking my cock up her tight ass than Resha or Cynthia. But she insisted on the anal fuck as part of what she was born to do. She knew the same tightness that was her pain was also a unique pleasure to me, her tightness was something nobody could match. Plus, the emotional payoff for her was much greater and more lasting than the moment of pain. She was very emphatic about getting that emotional payoff.

Two factors in getting anal sex to work are lube and position. Li had worked alternatives for both that made a significant difference.

Spreading lube with fingers never did the job for her. She wanted a lube that was natural, did the job, could be cleaned, and was not vile. So she came up with her own mix that involved coconut oil, olive oil, a hint of rum, and some other natural ingredients. Since it went up her ass I did not stress too much about the specifics.

Her real genius was getting the lube where it belonged. She started with a plain straight acrylic toy, something that was wider than a test tube but narrower than my cock, a size she was comfortable putting in herself, but it also opened her up a little and spread the lube. The genius part was that she drilled the thing with holes. She drilled a bunch of small cross-holes in the shaft, holes smaller than a nail, with a greater concentration in the front. Then she drilled a larger hole down the center of the shaft, intersecting all the small holes while leaving enough material so the basic shape - the walls and the nose - was still solid. She called it the “holey test tube.” A plunger went in the base, so it acted like a hypodermic needle. She filled the hollow inside of the toy with lube, stuck it in her ass, and pushed the plunger. Just like that her tight hole was really oozing lube without the hassles of messy fingers, missing a spot, or taking too long to get ready.

I did ask her about using something larger, something more like my cock in size, maybe a tapered shape to go in easy and stretch her out. But she said that if she was lubed enough, a little stretching pain wasn’t that bad, and she really needed something she could use “for fun, when my guy is not around.”

Well, I could hardly argue with that.

When picking anal sex positions, we do it all, including anal sex in missionary, she is very flexible so it works for us. But at the end of the day, we both like her on her belly underneath me, with my weight pinning her down while taking my cock up her butt. She is not completely flat, it helps if her cute butt is slightly elevated. We have a relatively stiff foam pillow, it goes from her pussy to her ribs. This lifts her so I have plenty of room for my balls to kiss her pussy on each stroke - that is an thrilling extra she likes. A second softer down pillow is used under her upper chest and head. In between the two? That is where her small breasts with their insolent nipple hang free and accessible, for the entertainment of both of us.

While “flat on her belly” is where we would wind up, we knew that getting my cock into her butt really needed some other position. If she is on top it starts good, but the transition is a bummer. Eventually we started by putting part “P” into hole “A” at the edge of the bed, with her scrunched down on all fours and me standing. She needs to have some control of position as she pushes out to take my cock. Standing next to the bed, with my hands on her hips, makes a good start.

Once she was lubed, in position and ready for fun, Li’s available bottom was a wonderful sight. On my bed her bottom was positioned at the perfect height, inviting my cock in. Her hole was distended, just a bit open, relaxed, glistening with lube like it was her own eager juices. Very inviting to the eye and the cock. Her pussy was peeking out, not quite lined up but it was always seductively beckoning my cock. We both knew that was not on the menu today. Tomorrow Abril and I would both play with that pussy for some threesome wedding night fun.

(We would invite Abril’s lover Cynthia, but space in the bed was an issue, and we had a specific plan that might be a surprise for Cynthia on some future day, if the Patron’s idea worked for my little baby-mamma.)

I stepped up so the tip of my cock kissed the center of Li backdoor. Her nerves were tuned up because of the oral play. She started to push out, inviting the tip in. I pressed inward, which put more of my cockhead in contact. This was easy, my cockhead was embraced by her body. But the last little bit, the top of the ridge, is always a trial.

I pushed a little more with my cock, working to get more in. She allowed it with her muscle ... but just so far. Then we reached the point where my ridge needed to be forced into her tight muscle.

“Go ahead ... do it,” Li said, her voice was steady. She was ready, even eager for what came next. I would not mind hurting the Five, but hurting Li was not the same thing. I hesitated. “Take my hips and push in. Don’t stop, it just takes a second, then we both get the good feelings. Push it ... Please, push...”

I did what she asked for, I held her hips while she strained to push out a little more. One shove and her slick hole swallowed. Suddenly I was in. I heard one whimper of pain from Li as my ridge forced the way past the barrier and into her body.

“Oh master ... hurt me ... so good. Fuck me like your anal slut. Fuck my tight hole!”

She felt real good on my cock. Looking down, my shaft seemed huge in the hole that was stretched entirely too much. But it felt so good, so tight on my shaft. Her ass was like a well lubed vice squeezing my shaft as I moved in and out. She was super lubed, there was no friction, no binding, only the tight embrace of her muscle around my cock. I pistoned in and out of that tightness all around my cock.

I fucked her like that for a bit, it felt good, but it wasn’t what we wanted. She wanted to feel my body on her’s, my weight pressing on her body while I rammed into her, really giving it to her butt. She started to stretch forward, moving her body towards the pillows. To keep us joined together I got my knees on the bed and knee-walked following her butt. When we were in position I let my weight force her down on the pillows, on her belly, with her bottom propped up perfectly for me to use. There I could really start to hammer her butt.

I looked down her body under me, taking in her short hair, her slim body which widened so sweet below the waist, my cock embraced in her ass as she moaned under me, reveling in my movements.

For a moment my imagination went to the stories I read in my teen years, of the ancient Greek city-states and their academies, where young men wrestled naked in the sand under the eyes of their philosopher-instructors. It was not hard to imagine that the victors might enjoy their victory to the fullest, taking relief as their reward. Some might choose, in brotherhood, to reverse things in their dorms at night ... or not. I recalled a story of Alexander the Great, who lost such a match and in the harsh lesson that followed found the spirit and the fire to turn things around, so the next time he enjoyed the sweet fruits of victory and tight release. He took that determination to the battlefield time and time again, never losing a battle, conquering huge swathes of the world.

I have never been into boys, I like to run my hands over what the front of a woman offers. But I could not deny where the sight of Li’s back took me.

Once I was inside Li was feeling no pain, her body had forgotten the moment of insult when my cock’s ridge violated her oh-so tight opening. Now her muscle held me tight as I moved in and out. The reason the pillow arrangement is perfect for us, for this, is that it puts her just so where my cock moves in her body at a very beneficial angle for her. With just the thin layer of her internal flesh between her ass and the pleasure nerves that rest in her vaginal tunnel, my cock pushes against her, inside.

The tip of my cock rubs against the inside of her pussy, massaging the very good spot. It is like my cock is in her pussy, only better because it is the tip that rubs her so good, hard and direct, not the shaft. It focuses the pleasure. She gets the anal sensation at the entrance and her vaginal sensations inside, like being with two guys doing a DP but without the extra stretching and awkward fucking plus the awkward conversation before and after that a real DP encounter always requires.

Li had her head turned on the pillow, so her ear was right in front of me, tempting me to do something indecent. I took that as an invitation to take the whole ear in my mouth and do some loving with my tongue.

“Oh ... GROSS ... Master, you know I think that is gross.” (This from the woman I traded analingus with?) “Why do you do it to me?” By asking a question my skinny Chinese fox knew I would have to let go of her ear to answer her. Then she could turn her head and I would not be so tempted.

But instead of answering I licked the contours some more, continuing my oral play getting her protests - but no movement - for a few moments before I finally answered. “My darling, you have the cutest, sweetest little ears. Plus, I know nobody else gets the wonderful treats. How can I resist them ... both.”

As expected, she turned her head as soon as I let go. Turning her head 90 degrees stuck her face in the pillow, so naturally she turned 180 degrees instead. She recognized the mistake - to late - when I said the word “both” just before I slithered my tongue into the other ear.

“Nasty man ... tricky man. Picks on poor skinny whore ... while you fuck my ass sooo goood.” (sigh) “Go ahead, have your gross way with my innocent ear. Stick your tongue in another hole.” With that she gave her ass a tight squeeze around my shaft, followed by using her pussy muscles to spark me to some action inside.

The ear thing was really sort of a game with us, after a few moments I gave it a rest and began to plant kisses on her soft cheek. She turned her head and strained till our lips met. I knew she did not like the ear thing, but it was more an objection based on pride, by a woman who always says she is unworthy. Plus, she knew I really liked it, I did not do it with anybody else, it was special for Li. After all, we gleefully stick our tongues in each other’s ass, so the concept of “personal borders” does not really apply to us.

I was still going slow and easy enough that I could do all the work with my hips and legs. My hands were free so I reached under her and cupped her little tits, hanging so sweet. I let them fill my hands, weighing them, treating them like they were spectacular treasures of flesh, which they were. I used my thumbs to stroke and pinch her nipples to fullness.