I'd known Amy for about 10 years. She had been through a divorce in another state, then moved back to my area and remarried a doctor. She and her new husband were into the soft swing lifestyle, but they never offered me any chance to join in.
Anyway, this started back on Valentine's Day. Amy, who loved inappropriate comedy as much as I do, put a meme on her social media that said "If you ever masturbated to me, you owe me chocolates." Jokingly, I asked if they should be sent to her house or work. She replied work so she could brag to her coworkers.
It just so happened that I was working a job close to her office that week. Always one to take it up a notch, I picked up a small box of chocolates and dropped them with the secretary at her work as a gag. About an hour later she called and we had a huge laugh about it. I figured that was the end.
About a month later she called and asked if I could come by and help move some furniture for her, as her husband was on a trip to some medical conference. While she was still single, I used to help her out with odd jobs and stuff when she needed help, so this wasn't odd to me at all. I went to her house, and after I was done moving a couple things (they were getting new carpet) she handed me a beer.
We hung out for a bit, and when she went to grab another pair of beers I hit the bathroom. When I came out she handed me the beer and said she wanted to ask me a question.
"You sent me those chocolates - have you ever actually masturbated to me?"
I about choked on my beer. She started laughing and I composed myself. "You really wanna know?" I asked. Her eyes got kinda wide. "You HAVE, haven't you!" she almost shouted. Sheepishly, I admitted that I had. She asked me to tell her about it.
I reminded her of a day that I ran into her and her new husband at a local brewery. They had been to some formal event prior and stopped off for a beer. She had worn a very short dress, and she was pretty drunk, so when she went to sit at the picnic table it rode up. With no panties on I got a great look at her smooth shaved pussy. Amy also loves to wear loose, low cut tops and I'd seen glimpses of her tits before. I said all that was my stroke fodder, and yeah, I jacked off a few times thinking about her. She told me she thought that was kinda hot, and she never suspected I'd thought of her.
I guess this is as good a time as any to describe Amy. She's roughly 5'6" tall with long blonde hair and blue eyes. She's very into fitness and runs half marathons for fun. On top of that, she sports D cup breasts complements of her ex husband and a good surgeon. So YEAH, I'd definitely thought of her!
At this point there is definitely some tension in the air. I figured I'd fucked up, so I polished off my beer and stood up, saying I should get going. Amy never moved, still sitting on the couch. "Wait" she said "do you have to go right now? I have another question." Then she blurted out "do you want to jerk it to the real thing?"
I stood there dumbfounded. Didn't say a word. I couldn't even process what she just asked me. Was she kidding? She likes to joke and flirt a lot. Probably kidding. I chuckled briefly and said "Yeah, right." "I'm serious" she said, and quickly slipped her t-shirt over her head. Never one to wear a bra, I was now starting at her tits in absolute awe. I was once again dumbfounded and stood like an idiot, not saying a word. My dick, however, definitely wasn't, and I could feel it hardening in my jeans.
Amy giggled a little when she saw the rise in my pants. "Come on, do it. I want to watch. I like turning men on." My brain was stuck right up until she said "please" and lightly caressed her breasts.
I reached forward to touch them, but she pushed my hand away. "Touch yourself, not me" she said. I broke out of my stupor and quickly dropped my pants. Amy looked and my cock and grinned. "I always wondered" she said, but didn't finish the thought.
I began slowly stroking my rock hard cock, marveling at her tits. She was pretty quiet, just giving me occasional comments like "you like them, huh" and "keep going" while caressing her breasts and pinching her hard nipples.
Pretty soon I was getting close. I had been quiet but was now breathing hard and moaning. Amy saw this, and she laid back on the couch. "Come on them" was all she said. Seconds later I threw three thick ropes across her chest. Amy just laid there a moment, then asked if I could get her a paper towel from the kitchen. I dashed off and brought her a few as well as one for myself. Just before she wiped herself clean, she took a bit of my cum on her finger and tasted it. She let out a very quiet "mmm" and cleaned up.
The post nut clarity kicked in and I felt panicked. What the fuck just happened?!? What did I do? I quickly dressed and bid Amy goodbye, hustling out to my car and heading home.
More to come if people are interested. Thanks for reading!