Jerking Off For My Co-worker.

 I used to travel a lot for work. I had several sexual adventures on these trips since I was single during the duration of my traveling. Several involve my coworker Kelsey, who I have a strange relationship with. We both accepted advancements in our job positions so found each other on our last trips at the same time. During this trip  I got a chance to do one of my favorite sexual activities: Masturbating in front of a woman.

I have a kink for masturbating with a female audience, but have done it relatively few times. My first time was in front of my cousin when I was 14, and that thrill got me addicted. I also did it for my sisters best friend, who I shared a brief but pretty intense series of encounters with, and the last time was (by accident) in front of my GF at the time’s mom. One day at a hotel in San Diego, I got the chance again.

Kelsey is a year older than me, 5’8 with red hair, glasses, and slightly overweight, but it gives her a large pair of breasts and she’s on her feet enough to have a pretty nice ass. She and I hooked up once, and it was honestly terrible. We had no sexual chemistry. After that, we never mentioned the encounter again, but it made us very open with each other. We would talk about our problems, relationships, sex, anxieties, etc. The openness was great. The best thing to come out of the awkward situation was finding a good confidant.  On our final trips for our company, we ended up staying in the same hotel, and things got wild.

One night I decided to go out on my balcony, read my book and have a nice drink. A few minutes after I started I heard movement on the balcony next to me. I look over and see my friend Kelsey. We exchanged pleasantries, and I invited her over for a drink to catch up.

She came over and I let her in, poured her her a drink, and we sat on the balcony catching up on life. She was engaged and about to somewhat down (she was in an ENM relationship, so they were open to some fun, nothing to wild though) and I had just gotten out of a 4 year relationship.

She had a fairly wild past, and was wondering what it would be like to be more reserved. My last relationship was pretty vanilla, and I was looking forward to the chance to try new things. At one point, we started talking about things on our bucket lists. She brought up wanting to be in some cfnm situations and being an exhibitionist that wanted to watch a man jack off, before getting bashful and saying she hopes that's not weird. I told her its not, that its a kink of mine and that I’d done it before. At that moment my drink was empty. Problem was I had an erection from all the sex talk, and with the thin pajama pants I was wearing their was no hiding it. I glanced over and she was nipping through her thin nightie. I told her that I wasn’t trying to be lewd, but I needed to get up and wasn’t blatantly bulge flashing her. She Looked at my bulge with fake exasperation as I walked by and I quipped that she was turned on too, its not cold out.

I poured myself a new drink, and she stood next to me, fixing herself another one while stealing glances at my bulge. I told her if she isn’t interested in it, its cool, but I was so turned on I needed a release and was willing to knock two items off her bucket list. She told me to prove it. I whipped off my T shirt and pajama pants standing in front of her, before starting to slowly stroke my cock. I stated that she’s clothed, I’m naked, and she’s more than welcome to watch until the finish. I then laid on my bed, continuing to stroke and play with my balls. She sat on the end of the bed, watching. I closed my eyes for a few moments, and when I re opened them I saw she was reaching under the nightie and fingering herself, and her lips trembled as she continued to stare. She locked eyes with me, reaching for one of her large breasts with her other hand, kneading it and letting out a little whimper.

I couldn’t last much longer. I aimed my cock towards her and grunted, shooting several ropes of cum over my legs. That pushed her over the edge and she had her own orgasm, squirting over her hand. We both laid back spent, no borders exchanged for a while, enjoying the afterglow of the moment. She was the first to speak, exclaiming “that was hot” before excusing herself to the bathroom. I got up, grabbing my drink, and not bothering to put clothes on. When she came out she smiled at my state, and we finished our drinks while chatting. Before leaving, we exchanged a hug, and surprisingly she gave me a peck on the lips and whispered into my ear that we had a week left and there was more fun to have. But that's a story for another day!