Part 2: Ari’s story
I had always thought of my friend Lin as being hopelessly prudish and conventional. When I discovered that she had a live-in boy who dressed like a maid and cooked and cleaned for her, I felt like she was usurping my place as the wild-child of the friend group. Still, there was nothing she could do that I couldn’t take over and take too far.
I considered online searches, but after a few sessions, I decided that the kind of experience I was looking for was going to need to start in-person. That wasn’t going to be easy. There were certainly men in the city I could twist around my finger, but that was the point. It would only be fun if he started out not wanting me to tame him.
So, on my various trips, I visited clubs, bars, and other promising venues. But I never really found a spark. The boys that approached me might have great bodies and good dance moves, but they really wanted a no-strings hookup. Which was fun a few times, but didn’t advance the cause. And then, I found someone without even trying. Tyler handed me a cappuccino with his phone number on it–“For the stunning boss-lady.”
Ordinarily, a man who cold-approaches a woman wouldn’t be the best prospect to recruit to a live-in servant. But two dates with Tyler convinced me I had a winner. First off, he breathed a noticeable sigh when I paid for dinner unprompted. Baristas aren’t exactly swimming in funds. And then he got to talking about traveling, asking where I lived and what it was like.
But obviously a cold invite to come and stay with me in the penthouse was going to put the shoe entirely on the wrong foot for where I wanted to go. I needed some indirection.
We hooked up a couple of times when I was visiting his town. He took direction well and knew how to warm me up with foot rubs, massage and some nice tongue action. I bought him a hideous gold bracelet that must have cost two months of his salary, and was delighted to find him wearing it when I surprised him at his shop one day. The material was there–I was just waiting for an opening.
It came when he took a second job as fitness trainer to supplement the barista income–did I mention he was 10 inches taller than I was and completely ripped?
About three weeks after I got home, I sent him a message:
“Hey–I know this is going to sound crazy, but I’ve been really busy with work and haven’t been taking care of my body. I’ve interviewed a dozen so-called personal trainers, but they all creep me out. What would you think if I flew you over here for a month to help me get back in shape? I bet I pay better than ‘The Coffee Bean.'”
He arrived four days later.
I only had a month to complete my plan, so I had to work fast.
The first day was just a normal workout. But I made sure I had on my smoothest pale blue leggings and matching sports bra. Before going down to meet him, I just checked that my ass popped perfectly, with the two sides each neatly framed by the leggings.
It was a hard workout, and I was plenty sweaty at the end. I made him show me the various movements and weights, and was sure to press my damp body against his. He gently wiped a bead of sweat off of my forehead. I let him finish with a shoulder massage before giving him a hug that was just long enough for me to feel him grow against my hips.
Then I began to go a bit further. I started with matching workout clothes for the two of us–leggings and something I told him was a tank-top, though it was clearly a sports bra. He was so cute–the next day his body was completely hairless without my saying a word.
He was a great trainer, but I was better. Bringing me water after workouts became a gentle wipe down became me standing in the shower while he washed and rubbed every part of me. I found him looking at my bare breasts during one of these sessions.
“Good boys need to ask permission before looking.”
I winked.
In two weeks, I had him kneeling down when I walked into the room. About the same time, he started doing little chores around the house. When I laid the maid’s outfit out for him, I told him was a joke. But it wasn’t a joke when he put it on again the next day.
By the third week, I knew he wasn’t going to leave after a month, but I waited for him to raise the idea.
“Of course, I’d love to have you stay more. But you know, as busy as I am, we won’t have much time together.”
And so, to give us more time together, he volunteered to take care of the house. The outfits I bought for him to do so were getting steadily more scandalous, but there was one accessory I really wanted but could not figure out how to broach with him. And then, one day, he solved the problem for me.
I was climbing out of the shower when he came in. His skirt that day was extremely short, and I had forgotten to offer him panties to go with it. (The question of why he accepted a completely feminine wardrobe from me despite his well-chiseled body was one I didn’t ask).
The skirt grew a very noticeable tent.
“You’ll want to smooth that skirt down…”
He turned bright red.
The next day, his minidress was skin-tight and again without panties. I decided it was a good day for me to try on my new leather harness. With nothing else.
The tent was back.
“Pet: I don’t really think it is appropriate for you to walk about my house like that…”
“But, miss…”
(We were still settling on a title he could call me…)
“Can’t you control it somehow?”
“Umm, well, I, I did find something, but I mean…”
And three days later, he was wearing the perfectly fit chastity cage I had ordered for him. I found myself omitting the skirts in his outfits, and the tops too. Fishnet stockings, perspex heels, and crotchless thong panties, all serving to draw my eyes to his perfect, aching, locked cock. His eyes, meanwhile fell between my breasts, where the cage key nestled.
Of course, I hadn’t forgotten Lin: But I hadn’t introduced her to Tyler (or, as we’d agreed the other day, Ty) yet. Instead, the two of us went drinking one night. Once I was sure Lin was tipsy enough, I took her home. (I had secretly been drinking virgins–I wanted to be alert for this.)
Ty was in on my plan and was waiting to open the door for us. When Lin saw him standing in the door welcoming us wearing only stockings and crotchless panties, she almost tripped over.
Ty brought us drinks, handing Lin’s to her in such a way that his caged cock was only inches from her eyes.
“It’s ok–we know you want to look.”
Lin’s hand ran gently over the chastity cage, hesitatingly, almost lovingly.
“How, how long have you kept, kept him this way?”
“Ask Ty, silly–I make him keep track in his diary.”
Ty blushed–of course.
“Goddess released me last month so she could ride me.”
“He was such a good boy–he held himself until I came and gave him his permission. He’s so sweet I might even let him out again this month.”
Lin didn’t say anything.
