Was Bad Annie very bad? I relented and took ex-boy home last night.

updated november:
e.
yes, ex-boy

this year:
b-boy
ex-boy? can’t remember timing
new boy
J.
Creepy V.
J. & A.
G.

Just tryin’ to keep track.

Bad Annie was hung over today. Couldn’t bring myself to go to work — called in sick, but worked from home for the afternoon.

Why? I went to Bootcamp, dashed home to clean up, then straight out to my first date with G. Skipped dinner, drank three glasses of wine. Now three glasses normally wouldn’t do much, but after hard exercise, without any food, and very little sleep….

oh yeah, I fucked him. Really wasn’t sure I was going to at first but then it’s midnight and what the hell. He’s different than the boys I’ve been dating: older (51), stable, and oh yeah, rich. Has a 15 yr old son, a brand new 2br loft in Soho, a weekend home in CT. A little bitter about the divorce but trying very hard not to show it, so okay. Used to work for our mayor’s former company, now deals with private equity investments. Likes music, goes out a lot, good company.

no real sparks. but a gigantic cock, and ready to go twice last night and again upon waking. Bad Annie really likes morning sex.

so I’ll see him again on Tuesday (he has the kid for the weekend), and we’ll see what develops.

Where do I start? A. and J. and I just couldn’t wait. We made plans for Saturday, then moved it up to Friday, then what the hell, jumped on it Wednesday night. Met at a bar down the street from her place, just to be sure I guess. J. seemed a little nervous about whether we’d hit it off, but we’d already pretty much decided it was on, it would have taken a pretty big turnoff to call it quits.

The bar has booths with curtains, we sit at one in the back and when J. goes to pay the check, he closes the curtains and A. and I start to make out. lol.

So we all go up to her place, now affectionately referred to as the sex den, and she and I strip pretty much the moment we walk in. Sex all night in as many ways and forms as we can think of. I hadn’t gone down on a woman since the 80s, I was worried about technique, but it seems to have been okay enough. I do watch a lot of porn, so it’s not like I don’t know what to do, it’s just that I’m out of practice. She set up a ‘taste test’ for the two of them to see who was better at making me come. For the record, it’s him– wow he is seriously good at cunnilingus. And what a champ, it’s gotta be hard to keep up with two horny women and you’re the only cock in the room. She’s so excited about my virgin ass – made sure that he fucked hers so I could watch and get inspired. Oh, did I mention that she ejaculates? I’ve never actually seen a woman do that. Her poor couch. She finally kicked us out around 1am, it was a school night after all.

Later Thursday, J. texts to say he mentioned the night to another friend, who wants to join in, with her friend J. We set up a date for a Friday Fivesome.

But later on Friday, they back out, so it’s back to us three. Back to the sex den. J. brought his puppy dog to hang out with hers. More of the same, with some new twists — A. bought a double-sided dildo. Looking at it, it didn’t seem all that interesting to me, but turns out it was kinda fun. We mastered it right away. We fucked and fucked and fucked until around 4, when we decided we were spending the night. We fall asleep, J. in the middle so again I’m spooned by him and the puppy. That really does make me happy. At some point they switch and A. gets in the middle. J. sleeps through most of the night, but A. and I wake up every couple of hours and finger through another orgasm. I’m not certain how many orgasms I had earlier in the night – maybe three? but I had *another* three *after* we went to bed. Un-fucking-believable. Eventually it’s early afternoon and we get up, A. makes us coffee and we walk the pups. Then back up for round eleven. In the middle of J. fucking me, I turned around and asked for the lube. He’s pretty gentle with my virgin ass, A. tried to help me come while he’s in me but it kind of hurts, I can’t focus on coming. It does finally loosen up after a while, but overall, it’s not that pleasurable. I had higher hopes- maybe next time. We finally break up the party around 3 and go about our days.

Summary: not all that into her, but what a good time, she’s such a sweetheart slut. I will absolutely do them again.

First date with M., a bank CFO originally from Kosovo, raised in the Bronx. 6’4″, big guy but not entirely comfortable with it, especially in a crowded Spotted Pig. Nice enough guy but a) talked a lot about what he liked and needed in a woman, and b) kept talking about how spare my online profile is, which after a while made me uncomfortable. Am I really supposed to have some list of must-haves and dealbreakers?

He will only date women who are over 5’4″, with light colored eyes, with good hygiene. He can’t date Indian or Asian women because curry smells. Wow, did he really say that? He couldn’t stand the lack of hygiene when he went to visit cousins in Albania.

Maybe I’m being too harsh. But still, not making it to date two.

Update: just got email from him asking me out again. In spite of having absolutely no intention of accepting, it was still surprisingly important to me that he wanted to.

Jesus.

J. shared my profile with A., this sort of slutty looking girl he’s fucked before. So now we’re on. She’s not really my type, but I claimed not to have a type, so what the hell.

The three of us sexted all afternoon and most of the evening. I sent some relatively modest naked pics from the bathtub, she sent one with her finger up her ass. He sent repeated pics of his ever-increasing hard-on.

This should be fun. I am going in with an open mind and open legs. Probably an open ass by the end of it, too.

I worked from home on Monday and J. and I spent most of the day on IM sexting. Not all of it titillating but a great, explicit discussion of what we’ve done (where, what, whom) and what we want to do. He’s dying to pop my ass cherry. lol. couldn’t get that phrase out of my mind all night. Continued via phone text when we both went out but my party ran late, he went home to brooklyn. His directness and unabashed need makes me very hot. Woke up in the night thinking of his cock, had to rub one off to go back to sleep. He checked in again tonight but I had class til late. Gotta figure out this scheduling thing.

Another sex date from online… disappointing. And I knew it would be, but I just couldn’t stop myself from going through with it. He was so excited I looked like my picture, and actually showed up. But he was small — short and thin — and I’m pretty sure took a cialis or similar when he went to the lavatory at the bar. He came back and wanted to hang out for a bit more before going back to his apartment and then had a raging hard-on on the walk back. sex and even just touching just…. disappointing.

whatever.

I wake up in Bushwick and I’m totally spooned between this lovely boy and his puppy dog, one on each side. bliss.

Yes, that needed a headline. It was about fucking time. Met him online, kind of surprised to have escalated it right away, but I needed sex and there he was, looking for it. Looking for me. So not my type– kind of preppy looking, but smart and funny and very comfortable talking explicitly about sex. I’m never initiating that conversation, but I’ll participate; it was kind of fun. He thinks I’m sexy. He loved how I sucked his cock (though to be fair, I’m really very, very good at it.) He seemed surprised that I woke him up early for more. I’ve no idea where this is going, and I don’t think he’s boyfriend material, but he has really nice dimples and an adorable smile and wants to fuck me with another chick if we can find one. I’m not giving him a nickname yet. He’s just J., for now, and I’m trying really hard not to online stalk him, but I would like another piece of that. Soon.