#590) True Tales from My Trip #2

When I’ve flown by plane with Robert, I’m scared that we’re going to crash, and my ears get blocked from the pressure so we can’t really communicate, and we’re surrounded by strangers. I was encouraged to join the mile high club by a past lover, so we rendezvoused in the lavatory and he fucked me in cramped quarters where people had just pooped and peed. It is all a hassle, and it’s rushed, and it stinks!
On this train trip with Robert, we talk about unusual things that have never come up before, we lounge around in a state of undress, he spanks me quite often and we make love; both have an other-worldly quality, as if we are defying time and space. I look at the scenery, or look at him when he doesn’t see me staring. It is a cocoon of enchantment, I am falling head over heels in love, it is leisurely, it is sublime!
As a treat, Robert spent his own money to upgrade our hotel accommodations to the Ritz-Carlton in several of our destination cities. We got to the first one, and I was stunned by the sumptuous beauty of it all. As we unpacked from our suitcases what we wanted to keep wrinkle-free, Robert told me that he had a gift for me.
“I think you’re gonna want to play with this gift right away, so why don’t you take your clothes off first?” he suggested.
Intrigued to the max, I shucked off my clothes, fetched a thick terrycloth towel from the bathroom and spread it across the chair seat cushion, and sat down to unwrap my present. It was a series of stainless-steel butt plugs in ever larger sizes, four of them in total. (I’d shared with Robert a while ago that this anal-queen had never had a butt plug inserted up my own bottom, and he’d remembered, followed-up.) I tried not to let tears get in the way as I spoke from the heart.
“I love them! I do want to play with them right away! Can we?”
He smiled, so I dove across his lap. He’d included in the gift box an extra tube of KY lube, which was prescient because it was clear that we’d be using a ton of the stuff. Robert warmed the most slender plug in his large hands. He fingered lots of the cool, slick, clear stuff up my tooter and started to slowly, gently insert the first plug. Even for someone who has long been anal-erotic and experiential, it was a revelation. The bulb portion of the plug stretched my butt hole in a wholly pleasurable way, much like a bowel movement in reverse. Then my anal sphincter ring closed around it and gripped down on the shaft portion, Finally, the flange end, each one with a different colored cut-glass jewel inserted into it rested against my opening, giving me a satisfying sense of security. I felt possessed up my ass in a way I never had before. I felt full, but not like you do when you need to go to the bathroom. I felt turned-on (big surprise). My rectum had long been both a functional eliminatory canal and a fun fuck-entrance, but now it suddenly had a third role, a place to be quietly fulfilled, a spot to be filled and plugged giving me a strong sense of contentment and bliss.
Robert started to tell me about how each of the four were a gradation larger than the one previous when I interrupted him with, “I want to try that one!” pointing to the biggest, one with a big, fat bulbous end and a thick shaft.
“This is a training exercise for your rectum. You’re not supposed to jump ahead to the most challenging one right aw…”
I cut him off with, “I want to try that one!” like a little girl who spied a huge candy sucker at the confection counter, pointing to that big, fat butt plug with single-minded determination.
“No, you are going to be trained one at time in order…”
We know each other well. He knew that I was thinking about throwing a childish tantrum to get my way. I knew that he prized my tight anus, and wouldn’t risk hurting it by spanking me with a butt plug in place. It was a frozen tableau, a sort of Mexican standoff. Then Robert surprised me. Instead of a sound spank, as my childish behavior warranted, he pinched my right butt cheek hard and twisted his fingers as he released the flesh.
“Ow! That really hurts!”
“Exactly. Instead of twenty or thirty swats, you’ll get twenty-five pinches! Count each one aloud…”
“Ow! Please don’t!”
“Woops, you didn’t count that one, so it doesn’t count toward your total…”
“Ow! One! Please stop, Robert, that really stings!”
Robert heard the tremulousness in my voice, he knows that I sometimes don’t have a high pain threshold, particularly when confronted with something new. To keep me from saying the safe word, Robert countered with something ingenious.
“I bet it’ll leave you with some fantastic bruises…” he off-handedly mentioned as he continued to pinch and twist.
“We’ll see…”
He got his way. I wore that small butt plug only for the next few days at various intervals, and only when he thought it best did he insert the next larger one. And the next morning I woke up to find an awe-inspiring set of bruises on my butt. My hind-end’s hide looked like a jaguar’s with broken rosettes all over it. I was in heaven!
(Before the end of our trip, I’d worked my way up to being ready for the fattest of the plugs. I found it too much to hold for any length of time. I’m most happy wearing the third of the four. I guess that Daddy really does know best, at least sometimes.)
As a side note, we found vaginal sex in the doggy position while I’m wearing one of the butt plugs particularly stimulating. It seems that the plug fills that rear void well, so that the vaginal avenue next door is somewhat compressed, and more pressure is then put on my clitoris by Robert’s cock. Try it, we think you’ll like it!
It became a ritual. Before Robert left for his work to inspect that city’s facilities owned by his company, he’d insert a butt plug in me and pat my tush lovingly. I’d wear that butt plug all day as I visited museums or shopped. At day’s end, he’d return to the hotel to find me on my knees waiting for him. He’d take me over his lap, play with the butt plug, twisting it, pulling it part way out only to reinsert it again. This made my near-numb rectum glow with renewed life, so by the time he finally did take it out, I was horny as hell and ready to fuck his eyes out.
I LOVE being plugged! The only drawback is that I found I need to wear a Tampax panty-liner because my pussy leaks arousal all day, as my butt hole puckers up and kisses the plug’s shaft, and my rectum has something to bite down on and chew on all day.

2 responses to “#590) True Tales from My Trip #2”

  1. What a wonderful time you had here. I dream of undergoing a period of anal training. I have purchased numerous butt plugs, but use them on myself. My wife is not interested in using them on me.

    Liked by 1 person

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