“It’s not going to fit.” I wish I had been joking. Just fluffing his ego or something; but I wasn’t. “There’s not way; I’m sorry.”
“Oh, it will fit, maybe not today. But by the time I get back down for a visit, mark my words. I’ll fit.”
* * * *
That was two weeks ago. Two days after he left I got a package from a lovely sex shop in London he had taken me to once or twice before. In it were three progressively larger butt plugs. Each was a plain, stainless steel tear drop shape. The smallest had a red ‘X’ on the end of the stopper, the next a black ‘X’, and the largest has a pretty emerald colored jewel. There was a note with them:
X = 3 days, at least 2 total hours/day
X = 4 days, at least 2 total hours/day
Gemstone = 7 days, at least 2 total hours/day, work up to 1 hour blocks of time
See you in two weeks cunt. xoxo
The first day was rough. Even the smallest plug was larger than any I currently owned. I found if I came once, and put my clit vibrator to high, I could relax enough to get it in. I tried to wear it as long as I could, but I ended up with several short spurts to equal my two hours.
The next few days weren’t so bad. Even moving up to the black ‘X’ size wasn’t as difficult as I had feared. Sir texted and told me to take a picture. He has colored the ends so he could tell which one I was wearing; I had wondered why they all didn’t look the same. He was happy with my progress, but warned me that the last size jump would be hard. His vote of confidence that I would be good to go when he saw me was not longer reassuring.
The day I first put the largest plug in I cried. And considering that I didn’t cry when I broke three fingers slamming my hand in the car door, that’s saying something. Even post-orgasm with the vibrator on it’s highest setting, it took me nearly ten minutes to put it in. I only wore it for another ten. There was blood. I called Sir bawling.
“I told you this was going to be difficult, but I wouldn’t ask you to do anything you weren’t capable of. Relax and give yourself an hour or so and try again.”
“That’s what I like to hear.”
An hour and a half later it still hurt, a lot. But after getting it in place I was able to leave it for an hour. My body adjusted quickly after the initial pain.
The next few days didn’t help as I continued to struggled, but once in I could leave it with little pain as I went about my chores and regular work. I could feel it, but only insertion and removal were painful. My anxiety grew, however, as it was not his intention to very slowly put his cock in me and then stay perfectly still. I was worried how anything rough or even just regular movement would feel. The last thing I wanted was to safeword after all the work I had done.
* * * *
I wore the plug as he arrived on Friday evening. I had dinner prepared and his drink waiting for him. He had me bend over and present myself to him before we ate.
“I am happy you are wearing the plug to dinner, cunt. I appreciate your commitment to my pleasure.”
He snapped his fingers and I sat down on the floor next to him. All that I laid out for myself was a napkin. Tonight he decided to feed me rather than give me a plate. It was a welcome gesture as I’m sure he could feel my nervousness.
He decided to wait on dessert, so I put the cheesecake in the fridge and we went upstairs. He told me to remove the plug. When I reentered the bedroom his dress shirt and tie were on the chaise and he was throwing his socks in my hamper. I would wash them in the morning.
He pulled the large bottle of lube from the drawer in my bedside table. I was ordered to grab a vibrator and get into position on the bed. With a mixture of excitement and dread I just wanted it over. I wanted to be everything he wanted. My mind was racing so much I opened the wrong drawer twice trying to get my vibrator.
When I climbed on the bed I shaking. He rubbed my breasts and arms as he turned me around and pushed me out into the bed. He pulled me arms around my back and told me to hold myself open for him. The lube was cold and it felt like he was using half the bottle. I was going to make a snarky comment, but then I felt the pressure of his cock against my skin. I knew there wouldn’t be the slow entries that I had given myself with the plugs. All I could do was relax as much as possible as he grabbed my hips. I took a sharp intake of breath as he pushed his tip in an squeezed my hips with both hands.
“There’s a good girl. See, what did I tell you? If there’s no way, create one.”