| Quick update on what I've been up to. If you've read some of my previous posts, one of the HB's I'm hooking up with is an ex-stripper/bartender/MILF. She works the bar on Wednesdays with an HB 8 who is my age (we'll get to her later). Because of this, Wednesdays have become one of my favorite days of the week as I now go to her bar by myself, chat her and the patrons up, drink for free all night, and laugh wholeheartedly as AFC after AFC tries to hit on her (since I'll be taking her home and fucking her all night). Anyways, after her bar closes she, the other bartender (HB 8), and I will typically head out to another bar for a nightcap. To the HB 8 I have phenomenal social status since I'm doing her friend and she's being told of my "prowess" on a daily basis (the MILF LOVES to fuck me and she's told me she's letting everybody know). Soon enough we became friends and now both of them give me free drinks at the bar.
So last night was going to be same as usual, but when I showed up I got a distinctly different vibe from the HB 8. She greeted me by saying, "Hey handsome" and leaning over the bar to give me a peck. "Hmm, she's friendly tonight," I thought. The IOI's didn't stop there. The HB 8 kept trying to make small talk with me throughout the night (folded her napkins near me while we chatted, etc.), and when I teased her about keeping her hair up in an old-woman bun instead of letting it flow "free and easy," down her hair came 10 minutes later. She told me she did this, "Just for me." Later that night I was teasing her about her accent, and she was trying to let me correct the pronunciation of certain words for her. I told her, "Hey, you don't need to change for me," and she coyly responded, "I'll do anything for you, though." Cocky-funny stepped as I answered, "I know that, but I'm saying you don't NEED to change. I'm nice like that."
Gears are turning in my head at this point. I'm trying to figure out how I can work dating both these bartenders at once. Would jealousy set in? Would I lose it all if I tried? I'll admit, these aren't problems you DON'T want to have. Anyways, for our nightcap me, the bartenders, and the owner of the bar (a rich dude but I would soon find out is a total AFC), went to a different bar for a nightcap. Now, I had learned from my MILF that this owner was trying to get the HB 8 bartender to come with him on a trip to Colorado (all her expenses paid). He and the HB 8 are not sleeping together, and she has trepidation because by going on this trip she would basically be signing an "I agree to fuck you this weekend" contract with him. As we were all sitting on the patio of another bar drinking, he was acting more and more AFC. When he wasn't on his cell phone and not engaged in the group (which was a lot), he was only paying attention to her and telling her ridiculously serious things like "I think you are tremendous" in order to convince her to come on the trip with him. All this after she just got off of a long day of work and was trying to unwind with friends! What a chump. Here's the funny thing, though. I was sitting across from the HB 8 in the circle of chairs while she was having this "serious" conversation with him, and I soon noticed her secretly rubbing my leg with hers...all while he's pouring his heart out. I was in another conversation entirely but I knew what was going on and couldn't help let a smug grin break through my calm exterior.
So the night ends, and we all go home...me with the MILF. As we're driving the MILF has a smirk on her face and says, "I have a secret." I finally get her to tell me what it is and she starts off by asking, "Have you ever been with two woman at once?" I doubt I hid my excitement well as I replied, "No, but its always intrigued me." She then tells me that earlier on in the night the HB 8 had asked her if she and I would be interested in a threesome. I told her, "Yea, that would be interesting." Then I go on to tell her about all the IOI's I was receiving all night. MILF told me that makes perfect sense.
I fantasized of threesomes as I fucked the MILF that night.
During a break in the sex, the MILF tells me she's never been with another woman but would love to try and that we should make this happen. Obviously, I agree wholeheartedly. We then figure out that my birthday, which is coming up shortly, falls on a Wednesday--the night of the week they work together at the bar. What a birthday present for Esperanto that could be! The idea of a threesome is consuming me.
I'll admit, a threesome now seems like a foregone conclusion. But I really, really want to do this, and I DO NOT WANT TO FUCK THIS UP. At the risk of overthinking it, I need to plan my next move and could use any advice anybody with experience can give. I know that I have to strike while the iron is hot because the HB 8 may not stay on the market for long. She's funny, cool, hot, laid-back, and gets hit on all day by guys. So if this is going to happen, its got to happen soon. My ace in the hole is my MILF...its amazing how sexually uninhibited and open she is. I need to tell her to start talking to the HB 8, but am not totally sure what to tell her to say. This is foreign territory for me, boys, I could use some help.
-Esperanto
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