Diane was making progress. The young woman who was everyone’s overweight best friend, the nice girl who was going to be the maiden aunt with three cats had taken a radical turn. She wasn’t ashamed of her body any more. She no longer dressed like an off duty nun. She carried herself differently. Her friends and co-workers noticed the difference. A couple asked if she had lost weight- she hadn’t and wasn’t interested in trying. Of course none of them really knew the whole story, only the two of us knew.
The Diane who was more confident in her work and with her friends had become a greedy, lusty, at times almost pushy sub. With me enjoying every step of the journey. (See More I, II and III). I have to admit, she had one or two new doors up for me as well. One evening we were in the West Village perusing some of the sex shops looking for toys, maybe something for Diane to wear. Most of these places catered to gay men, but they were open to others and were much better places than anything in Times Square. We picked up a couple of items at one place then visited another store. We browsed for a bit then found ourselves looking a selection of butt plugs. I saw Diane’s breath change, deeper and slower. She was getting excited as she looked at the different plugs underneath a counter. The sales person came over to help us, wearing leather and was flamboyantly gay. He looked at me, then Diane to see if we were serious. He nodded as he recognized the dynamic.
Diane pointed to one of the plugs, “Could I see that one?” He opened the case and handed the sample to her. It was smooth, maybe four inches long, narrow at the top, then wider before narrowing at the bottom again.
The clerk handed it to Diane along with a tube of Astroglide, “that’s one of our more popular ones, great for starters.” Diane looked almost annoyed for a second even though the only thing that had ever been in her ass was one of my fingers, occasionally my thumb. She looked up at me, I nodded and we went to the register and paid. I turned to leave and Diane said, “Let me have a second.” I shrugged, not sure what she was up to. She took the bag we had just paid for and walked to the back of the store. There were several video booths at the back of the store. It was still early for the regular crowd, so none of them were actually in use. Diane disappeared into one of the booths and shut the door. The clerk looked quizzically at me, those booths were really for the gay clientele and I’m sure there were gloryholes cut in them.
Diane came out of her booth and as she got to the door, handed the clerk the bag with now empty plug box. I took her hand and we walked out. As we made our way down the street, I considered my next move. Diane must have been more than a bit annoyed by the “starter” crack from the clerk. But it also gave me the chance to punish her for getting ahead of herself. I kept us walking further and further west, getting closer to the Hudson. The neighborhood was getting slightly sketchier, but it wouldn’t get truly freaky until much later in the evening after midnight. Manhattan can be crazy like that, parts of it can seem like a ghost town at the right time.
By now it was fully dark, I pulled Diane into alley outside a dank little club, the lights weren’t on, that place wasn’t going to even open until at least 11, perfect. We were mostly hidden from the street, but if anyone had been walking by they would know we were there.
I moved Diane to face the wall, “put your hands against the wall,” she was bent over as if I were frisking her. I stood behind her to one side and began rubbing my hands against her ass over her skirt.
“What happened to the plug?”
“I used it” SMACK, I slapped her ass cheek, just enough to make a noise, not enough to sting.
“Did I tell you to go into the back and put that plug in your ass?”
“No, sir”
SMACK, then more gentle strokes, now I worked my hand under her skirt, on top of her panties.
“Why did you do that?”
“The guy at the store, he was making fun of me.” While I actually had some sympathy for that, after all Diane was proud of how far she had come, she still got another SMACK.
“I’ll tell you when and how to use the toys I pick for you. Is that understood?” Smack
“Yes sir”, now she was bending even further over, moving her ass back onto my hand. I reached down with my other hand, grabbed her panties and quickly ripped them apart. Diane whimpered, but stayed bent over against the wall. I could see the round end of the plug pushed flat against her asshole. I reached down and pushed two fingers inside her cunt, she was soaked. I pushed in and out for a bit.
“This pussy belongs to me, do you understand?”
“Yes, sir”
I moved my hand and grasped the plug, I knew how tight her ass was, the plug wasn’t huge, but it was stretching her that was certain. “This ass belongs to me, I’ll decide what goes in it.” I started to twist the plug slowly in and out, Diane started to make quiet yips, the plug was giving her just the right combination of pain and pleasure. Now I put my other hand on her clit and rubbed that while I kept the plug in and out, I stopped just as she was about to cum. She whined and pushed back.
“Be quiet.” I undid my pants, and in one quick motion buried myself in her cunt. She took a deep breath, I don’t think she expected me to actually fuck her in semi-public. I stroked for a while then took one hand off her hip and reached down to the plug. I started to work the plug in and out, opposite to my strokes, Diane was grunting now, loud enough to hear from the street if anyone walked by. As I emptied my balls into her cunt, I pushed the plug in to the hilt. They probably could have heard Diane all the way in Brooklyn.
I stayed like that for what felt like forever, post orgasm Diane’s cunt still gently gripping my cock. When I pulled out, a dollop of my cum leaked out onto the ground next to her ripped panties. I reached between her cheeks and slowly removed the plug, it was covered with frothy lube. I picked up her panties, wrapped the plug in them and put it in the bag with the rest of the things we had bought. Diane turned around and pushed her skirt back down. I reached out for her, gave her a gentle kiss, then we walked back toward the Village to get a cab.
More IV
Re: More IV
very hot