We met years ago on one of those silly adult dating sites (don't use those by the way, they are mostly BS and the successes I've had were all flukes). I used to live in an area with a much smaller population, so I took notice pretty much any time a new profile popped up, and one day I saw a new face pop up. She was over 50, but still looked great in every conceivable way. Caucasian brunette with tan skin and hazel eyes. She was also a lesbian, but had curiously indicated in her profile that she was seeking Men and Women. She also wasn't that far away, so I introduced myself. I was in my early 20's at the time, so she was rightfully skeptical, but I'm easy to talk to and was mature for my age, so we hit it off.

After just a few emails she invited me over to her house. She as sweet, and greeted me with a BIG hug. She also didn't have much experience with men, so there were some fun quirks. First, she asked me if I understood why I was there. Although I am SUCH a fuckboy, I didn't want to be crass and just say, 'Well, I was hoping we'd have sex', so in my nervously gentleman-like manner, I tried to say something like, 'I'm here to hang out and get to know each other, and, you know, if there's um, like a connection or-' She politely cut me off. 'Oh, well, if you just want to talk, I'm not sure I'm interested in that, I mean, we can chat, but I really just wanted to have sex. Is that OK?'. I blinked. "Yes, that's entirely ok'.

She smiled at me and said, 'Great'. The she invited me to take a shower with her. I had literally JUST taken a shower, but I like being naked with attractive women under almost any circumstances, so I followed her to the shower. Besides, I think guys smell bad, so I can sympathize with why she would want to scrub one down the fist time she fucked one.

When we got to the shower she disrobed with no hint of self consciousness, and when I saw her body, I understood why. She was built like a classic Pornstar, huge perfect tits, hourglass figure and a nice round ass, full bush. I was hard before I even got my pants off. Then I got maybe the best compliment of my life: She turned around to see my erect penis and literally exclaimed, 'NICE TOOL!'. I nearly blushed and laughed at the same time. My cock isn't gigantic, but I'd been told it looks nice, and to have a Lesbian say so just gave me the best self esteem you can imagine, lol.

We didn't do much foreplay in the shower, mostly rubbing our wet, naked bodies against each other while she held onto my cock. At one point she gently washed it with soap, then rinsed it off, then took it in her mouth and sucked on it gently a few times. She stood up and looked me in the eye, hand still on my dick, and said, "You look like you're ready". I said, "I am" and she turned off the shower and led me to the bedroom.

Very sweetly, she asked me to take it easy on her since I was so much younger, but when I actually penetrated her and our hips started moving, she had no trouble keeping up with me. I was surprised at how turned on she was by the experience, which in turn, made it even hotter for me. Every time I wanted to cum I'd slow down because it was just to much fun watching her react to my dick. I still did my best to be gentle, but it was hard not to get carried away and start manhandling her tits while I drove her into the mattress. After about a half hour she asked me if I wanted to fuck her tits, to which I said, 'of course'. I'd only known one girl before this that was actually into titty fucking, and this woman had amazing tits, so I immediately straddled her chest while she held her tits together and I pushed my cock into her soft cleavage. It felt amazing. I pumped her slowly for a few minutes, but it was so hot I was ready to pop almost right away. 'Is it OK if I cum?'.

The she said the best thing ever, "Oh, I was hoping you would...".

This was real fantasy--become-reality stuff for me, so I relaxed and ejaculated all over her big, sexy light brown tits...and a bit on her chin and lower lip too. I normally only shoot a pretty modest load, but she had me really turned on, she she got a good spray. She looked up at me, and with my cum still on her lip, she smiled and said, 'You just came to Kelly Clarkson'. Kelly Clarkson was indeed playing in the background, apparently a favorite artist of this woman. If you knew me, you'd know that I'd never willingly listen to Kelly Clarkson unless I were distracted by fucking a hot lesbian, so this was actually quite funny and she knew it. After she wiped my cum off her face and tits, we both got dressed and I left, but she invited me back several more times.

We never dated, and we didn't hang out outside of having sex, it was always just a fuck-buddy type situation. Funnily enough, after we'd been at it for a few months I could tell she was getting lonely, so I played matchmaker and hooked her up with a woman I knew who was also a lesbian. They started dating and got into a very happy relationship for as long as I knew them (I eventually moved out of state and lost contact). We never told my lesbian lover's girlfriend that she and I had fucked, I just introduced her as a friend from work or something.

I'd had many lesbian friends before this in my life, but I'd never had sex with one before. I was honestly expecting it to be a lot more awkward, but no, it was pretty organic and awesome and I'm glad I reached out. We were different ages, had different interests, and virtually nothing common, but we were both respectful of each other and looking for the same thing, and it totally worked out. In a perfect world we'd all be able to easily find someone we could secretly experiment with, to play outside our normal comfort zone without any negative consequences. But this isn't a perfect world, so be careful out here!

This is a true story. I don't send photos or personally identifiable information about any of the participants, so please don't ask. I do not kiss and tell. I've been on reddit awhile, but I created this accountant specifically to document some of my more entertaining encounters, both old and new alike.