Alright here's my story.
She was a
gold star lesbian (I actually had to look this term up originally) who I'll refer to as "Jessie":
A few months ago I was hosting a cookout at my place. Partly to celebrate my long-awaited freedom and release back into the wild... and partly because it was nearly summertime and I needed an excuse to throw a party. I invited a couple of friends and co-workers, but being short notice I did not expect more than a dozen people to show up.
I had also extended an invitation to the woman who lived downstairs, seeing as she had expressed interest the last time I'd brought the idea up in passing. She was a bit older, but attractive, passed the boner test, and as far as I knew (aside from her cats), available. I also gathered she had to be pretty lonely based on my limited interactions with her.
The event went off as expected with plenty of food, booze, music, drinking/board games, and good times all around. Towards the end of the afternoon a thunderstorm started and it was pouring down rain and a couple of people took off.
Finally I got a text from Jessie, "party still going on upstairs?".
One girl, a former co-worker, who was South American and already kind of a long shot, texted around the same time saying she probably wasn't going to make it. Granted this was an all afternoon event so it wasn't unexpected to have people canceling at the 11th hour. I told her not to worry about it, besides I figured having two girls there I wanted to bang could have ended up cockblocking me anyway.
I texted Jessie back, "yeah you should stop by" to which she replied, "give me 15 minutes."
I high-fived my buddy and we got back to drinking. Had she shown up immediately it might not have meant anything to her, but taking that much time to me meant she was at least making an effort to make herself presentable. My buddy knew to delay his taking off by a few minutes, which made my job all the easier.
Game on.
I prepared some don julio shots and rejoined the group on the couch engrossed in watching the daily show. There was a knock at the door and I let Jessie in. Now she was definitely older, but she could clean up well. Red hair, freckles, southern accent. Jeans and a halter top. Cute. She even brought a bottle of wine.
"Come on in."
Jessie settled in on the couch and I brought over the shots, sitting down in between her and the other two. "Tequila? Oh wow I haven't done tequila in so long."
Perfect.
The mood relaxed as we watched more comedy on tv until my buddy and his girl had to "take off." I started cleaning up in the kitchen and Jessie came in to assist. "Shall we try your wine?", I asked?
...Half a bottle later we'd shared the expedited versions of our life stories and she was telling me what a great person she thought I was.
And then the kicker,
"Just so you know, I'm a lesbian."
My sober self would've had it's heart drop, but I didn't even flinch, I swear. The alcohol probably had something to do with it.
"That's cool."
The conversation continued and we moved back to the couch with a second bottle of wine, television still going on in the background.
My memory is a bit hazy here but at one point she asked me (or I asked her, still not 100% certain), "So are you a good kisser?" I shrugged. "Only one way to find out." She was, but my scruff seemed surprisingly painful to her. It was clear she hadn't made out with many (if any) guys before me.
Things sloped off for a bit and then somehow we got on to the topic of sex. Out of the blue she told me she had an oral fetish. I thought for a split second.
Oh shit dude... that's a green light.
I wasted no time, stood up and whipped my dick out right then and there. She didn't even waste a second before going to town. Must have been close to 30 minutes and she was insatiable - I don't really get off via blow jobs which usually works to my advantage. I pushed my luck further and told her to turn around and take her pants off. She was submissive and I went on in and plowed her on the couch. I was pretty drunk and it wasn't long before I slipped into the wrong hole. "Whoops", I said. "What time is it?", she replied.
Fuck me.
Too late... that pretty much ended the ordeal for the night. We said our goodbyes and she went home. There were a few very delayed text exchanges nothing sexually related until it quickly died off.
I was not quite satisfied with the outcome and figured that was pretty much it.
Luckily for me I was wrong.
About a month later in between dry spells I happened to be contemplating another text invite, something along the lines of, "Going to watch GoT tonight, wanna join?"
Knowing how poorly the texting had been going I chickened out and decided against it that afternoon and instead saved it as a draft.
Pussy.
Later on I walked down to the local convenience store to pick up some random stuff and on my way out, who did I run into?
Yep, Jessie the "lesbian."
"Oh hey, small world." Her eyes lit up, we hadn't crossed paths in a while.
She gave me a lift (one block) back to the neighborhood and we talked for a few minutes outside the door to the building. Before I could invite her up later she said "Wanna share a bottle of wine later?"
Fast forward to that evening she came in again and we caught up further. For some funny reason she reminded me that she was lesbian. Plausible deniability maybe. Another couple of glasses of wine later I whipped out my dick again right there in the kitchen and like a good submissive girl she got on her knees and went at it.
At one point there was a short intermission and she complimented me on my member, saying she had seen a lot of gay guys with really ugly penises and that she had looked but never touched one. "Uh, thanks?"
Guess I should have been honored?
This time I managed to get her into the bedroom only to find out she was on the rag. No biggie for me. Grabbed a towel and banged her in every hole (including her ass this time) and in half a dozen positions. She was begging me for a hot steamy load inside of her (I kid you not). Knowing I had been where no man had ever gone before, of course I obliged her.
Not much else to say afterward. The niceties and texts slowly stopped and I moved out a few weeks later. I gathered that she had a girlfriend of some sort and knowing that I was moving out might have given her further plausible deniability.
Who knows.
I haven't spoken to her since.