I met a new Tinderoni last Week Thursday. We’ll call him Brad. He was in town for the TriBeCa Film Festival and was staying at a hotel down in the financial district. We chatted, flirted, and teased each other. He told me he was a ‘pleaser’. I was interested in finding out more.

Apparently I’m more adventurous than I gave myself credit. I guess some might say promiscuous, some might say slutty even. I say bold.  I say, I know what I want, and I’m not hurting anyone by going for it. So there.

I agreed to meet him at the hotel bar for an assessment cocktail.

When I got out of the cab he was waiting out front. I was surprised that he greeted me with a full on kiss. It was pretty sexy. We got a seat at the bar. He was easy, and charming and funny. We had grapefruit margaritas that were pretty tasty. Talked movies and TV while we got buzzed and I felt like there was a good little connection there. I wasn’t about to go upstairs with him if my gut told me not to, I have pretty good intuition and while I’ll take some risks I’m not completely stupid.

The bartender asked if we wanted a second drink, we looked at each other, grinned and said no. We’re both light drinkers and that margarita had given us a pretty good little buzz. I used my usual line. “So, it’s safe to assume we aren’t mutually repulsed by each other?” That usually gets a at least a little laugh.

We headed upstairs.

The room was small, but nice, not much of a view to speak of being so far downtown. We started kissing before we got very far into the room and his hands started to roam, cupping my breasts and squeezing my ass. I slid a hand down the front of his jeans and he had a raging hard on.

We moved to the bed and started making out in earnest. I’ll give him this, he was a great kisser. Soft lips, passionate, tongue but not too much tongue. You know? Through the vent on the wall I could hear a woman softly moaning in a nearby room. It added a layer of erotica that turned me on further.

I sat up and quickly undid his belt, unzipped him and pulled his jeans off. Here’s where things started to go a bit funny.

What I had assumed was a curvature downwards because his boner was trapped in his pants continued to curve down. Even after I slid his briefs off. It wasn’t a turn off, I’m not the shallow sort. Everyone is different and we all have our quirks, lord knows I’m not a supermodel. But I was slightly concerned about the logistics. I had never seen one that curved so far south before.

I went down on him for a little bit, but he soon pulled me down and started eating me out instead. It was really hot. His good kissing really translated into good head. Before long he had me squirming and breathing hard. I grabbed a condom and slipped it over his cock. He was on his back and I straddled him, guiding that curved dick into me. It took me a few tries to get the angle right (leaning slightly back, hips tucked up) to be able to get a good rhythm going. Once I had it I started to go a bit harder, got up from my knees onto the balls of my feet for more traction and started really fucking him, but he stopped me. I think it hurt him a little bit, or he was afraid it would hurt him because of the curvature? Not sure. But I slowed down and started squeezing on my upstroke instead. Before long he was coming.  We took a little break. He wanted to continue to please me. I brought along a little bullet vibe so I took it out and he made me come a second time. This time so much harder. Good I love a good vibrator. He was laying on the bed, his head on the pillows and I straddled him with my head near his feet so he had good access to me. He fingered me and rubbed my clit. I really wanted his cock back inside me, but when I asked he said he wanted to finger me. I guess he had a hang up about his cock. Too bad because beside the curve, it was a pretty nice dick.

By this time it was close to 3:30 in the morning. He offered to let me sleep over, but I didn’t really feel comfortable doing that so he gave me money for a cab ride home.

Not a bad time for a one off hotel fling.


Jake is the guy I’ve been chatting on Kik with for, well, months now. He’s one of those guys who always seems to disappear when you try to pin them down to actually meet in person. <insert eye roll>

He sends me dick picts. Lots of them. It’s pretty amusing. He’s a really good photographer, too. Of subjects other than his groin I mean. lol He sends me pictures pretty regularly of the city. He has a very good eye.  He’s an architect.

It’s a pretty beautiful cock. Large, long, straight and pink. It’s really nice and fat too. I’ve always preferred fat cocks over long ones. I am very interested in meeting it in person. I know he’s just one of those ‘for fun’ guys. I’m ok with that. Because that dick looks like all kinds of fun. Initially I blew him off because things seemed to be going really well with another Tinderoni. Remember in my earlier post when I said I fell in love a little bit? Yeah. Another story for another time. But I told Jake that I wouldn’t meet him for sex because I didn’t want to screw up what was happening with Ben.

Flash forward seven months and the Ben situation fizzled, so I’m chatting with Jake and his big cock again. We have very sexual chats. It’s pretty erotic. I asked him to send me a masturbation video over Kik. lmao. Let’s see if he complies. I have a feeling that he won’t, but let’s hope he does! I’m amused, and I will let you all know the minute he does.


I had two dates with Tim a week ago. We had good text chats, made each other laugh. Made a date to go see a movie. We met at Bleecker Bar in Soho. I got there first, and got a booth. He arrived shortly after. I found him attractive, and the initial awkwardness wore off pretty quickly.  We had a beer and some laughs. We walked east on Houston over to Sunshine Cinema, got our tickets and continued our chatting a flirting as we waited for the movie to start.
We laughed. It was fun. Then we wandered back to the train and headed back to Astoria. He lives over by Ditmars. We got off at Broadway, my stop to have another beer. We went to Gilbey’s and had two more beers each. The flirting continued. We were talking about how old we were, and he said something, I don’t remember what and I said, “Are you trying to make me cry?” He very sweetly and seemingly sincerely replied, “I would never do anything to make you cry.” That took me by surprise, and made me smile. He walked me home and asked to kiss me. I said yes, and he did and it was a pretty good kiss. I started thinking that maybe he was boyfriend material. I had zero intention of asking him to come upstairs. I had intentionally left my room a mess (I had started going through some old boxes to throw things away earlier, and left a ton of things on the bed. Partly because I hadn’t finished, and partly to stop myself from jumping into bed again too fast). But I was tipsy, and and feeling frisky and the date had gone well and I’m the type to just do it I guess. I explained and apologized for the state of my apartment and up we went.

He used the bathroom while I quickly started clearing off the bed. He came back in and just then I noticed that I had left one of my vibrators out on the nightstand. I like to clean them before putting them away, and hadn’t intended to have anyone over so I had forgotten that it was out. I tried to be cool, and quickly put it into the box I have on my nightstand hoping against hope that he wouldn’t notice.  His voice was dry, deadpan. “Don’t worry, I didn’t see that.”

Well, shit.

Laughed it off, and we settled onto the bed and started kissing. He lay down on his back, and I straddled him, pulling off my dress. He seemed to be a bit passive, and that put me into an aggressive mood. “Is that one of those front closure bras?” “Let me show you how it works…” More kissing, hands everywhere. More clothes coming off. He was average sized, but with a little thickness to it. It was a nice cock. I put a condom on him and slid it in. And then it happened. About 30 seconds later he was done.  He mumbled something about it being a while since he had had sex and started cleaning up. I played it cool, but in my head wondering why he didn’t seem in the least bit concerned that I hadn’t come anywhere near orgasm. We said our goodbyes and I crashed out on the bed.

Well that was awkward.

So over the next few days we texted a bit, and made another date for Friday night. We went to eat some food over on 30th Avenue. Still good conversation, still had a good vibe, easy to be around. I was totally willing to give him another shot. Maybe it had been a while, and maybe he was really into being naked with me and got over excited.  We even joked about the vibrator, He said that it might have been different if he didn’t know what it was.  I said if he didn’t know what it was I would have shown him how it worked. Ha.

We had dinner, and drinks and wandered back over to my place. I had since tidied up and the place was looking more normal than it had that first night. We got on the bed, much like before. This time I pulled his pants off, and spent a few minutes with his cock in my mouth. He got really hard, liking what I was doing to him. Then again, after just a minute or two, started orgasming. Hmm. What is happening here? He cleaned himself up, and we were laying in bed. “Give me a few minutes, we’re not done yet.”

“Well,” I thought “At least maybe now he’ll be able to last when we fuck.” He reached for my clit, and rubbed it the way I like it. But just as I was really getting into the zone he switched it up and stopped. He had me on my back and in he went. On one hand – I didn’t like that he stopped what I was enjoying, but on the other hand – I wanted to see how he would handle me with a cock that was on its second go, so I didn’t protest.  But guess what. Two minutes later, there he was cleaning up again. “Wow, I’m finishing really fast lately.” No kidding, buddy. But out loud I said, “I take it as a compliment.” I didn’t want to hurt his feelings. I know this can happen, and I am totally willing to work through it. There are lots of things you can do to improve it. The thing that I had an issue with is that even after he had finished early, he once again made zero effort, or even asked if I had been satisfied. That’s not cool. He had gotten off three times already and me… not once. Harumph.

We watched some YouTube on my tv for a little while. Looked at some movie trailers, some funny videos. I was yawning a bit, so he started to get up and go. But then he did something funny. I was laying on my stomach and he rolled over on top of me – his chest on my back, legs on my legs. And then he just lay there, for about 30 seconds or so.  It was kind of nice. His weight and warmth was kind of comforting. Then he got up and went home. We seemed to part on good terms.

He text me the next afternoon asking about my sports team winning, I replied that it was a tie, but then he dropped off. I wasn’t really trying to play games, but I didn’t text him till Monday. I find texting is a pretty decent barometer of a man’s interest. If you don’t text him, and he texts you within a day or so that means he thinking about you, and is interested. If you don’t text him and he  doesn’t text you either… well then. He’s just not that into you. Right? So Monday I sent him a hi, and I got some half hearted answer. We talked about a movie he was interested in seeing, he’s a movie buff, and I said let me know if you want to go, I’d like to see it to. Bait-set. No bite. I’m not sure what to make of it. Maybe he’s embarrassed about his performance, or maybe he’s just not that into me. Should I stop texting him? I think I will. What do you think?


I met someone new. But I’m worried. He falls into the category of “we’ve already made this mistake, haven’t we?”.  He’s still married, and is only staying in the marriage right now because of two kids under five, the littlest on the road to recovery from a rough birth and some delays because of it. He’ll be fine, but it’s been hard. He told me that his wife has said that she hates him, and they barely interact but for the kids. It’s pretty complicated, but of all the men I have met lately, he’s pretty attractive. We went to a movie last night.  First, we had a drink, and great conversation. We make each other laugh, and he’s very easy to be around, I feel very comfortable.  I need to talk to him about this though, because what sort of relationship could we have? I don’t want to be ‘on the side’ woman again. That really sucks.  I didn’t like it before, and I’m sure it won’t improve the second time around.  I’m treading very lightly. I haven’t even kissed him. I’m not sure I should go there. He seems pretty emotionally defeated, and longing for affection. But I don’t want to be someone’s escape, or fantasy again.  It doesn’t seem like we could have anything more though.

I have two guys who continue to chat with me, one on Kik the other has my phone number and he texts me. I’ve been chatting with both for months, and we talk almost always about sex, but neither of them have agreed to meet me. I think they’re both chicken. Not sure why. I have teased, and argued, and even been mean (which they both seem to like) about meeting me and they never come through. It’s starting to get boring.  I need to break some of these bad habits.


Last night I found myself eating marshmallow fluff out of the tub, crying, in front of an episode of Felicity. It’s hard for me to admit this fact. I would never in a million years admit this to anyone who knew me personally. I mean, how pathetic can a person get? Felicity was graduating, everything in her life at that moment was hard, everything was changing and it was fraught with growing pains and angst. The love of her life was leaving her to be with another woman. She was leaving her beloved city of New York, and all of the close friends that she had made. Life was pretty shitty. In that moment of self-indulgence I was Felicity, I felt her pain and it brought me to tears. Ugh.

Don’t get me wrong. My life is pretty good. I’m gainfully employed. I have my health. I have no enemies (that I am aware of). But I identify with her, this TV character. She mirrors some of my hopes and some of my disappointments. Like a good cheesy tv show should.

All day I was chatting with a couple of guys, mostly from Tinder.  There’s Rodney. We’ve hung out and had sex a couple of times. At first I thought he might be boyfriend material… but no. I’ll explain why another time. He was sexting me this afternoon.

He’s pretty funny, good conversation. He turns me on, but I’m pretty certain that his interest in me is purely sexual. Which is fine, that’s kind of the point of a Mr. Right Now, and the feeling is mutual. It doesn’t hurt that he has a sexy British accent, and he’s a bit aggressive in bed.  Thing is- and I’m still having trouble reading him- that he tends to be a little bit flakey. Cancels on me sometimes. I know that probably means that he’s ‘just not that into me’ which is also fine. I’m not in love so I’m in no danger of getting my feelings hurt, but it can be a bit aggravating.  But he hasn’t stopped texting me.

He lives in the village, not too far from the West 4th train station. He used to play soccer professionally, so he has this muscular, sexy body. Very compact and powerful. He’s little on the short side. But I’m barely 5’1″ so it’s of no importance to me. Two words. Footballer’s Thighs.  Yum. And because he’s a Brit he’s uncut.You don’t come across many foreskins here in the states, and I like a man intact. Which I find erotic. I totally stole that from him. lol He tells me what he finds ‘erotic’ and just the fact that he uses the word erotic is erotic. I think it’s very sexy. I mean erotic.

The last time we hung out, we smoked a little joint, had some cheap beer and had some great sex. He liked it when I initiated our session by undoing his belt, unzipping his jeans, taking his cock out and spending quite a bit of time worshipping it.  Did I mention that I really enjoy sucking dick? Well I do.  He’s average sized, but I’m not sure I’ve ever come across a cock that got so HARD. Like an iron rod. I made him come three times that night.  At one point, he was rubbing my clit with his finger, and kissing my neck, and I was so close to coming. That’s when his neighbor came home, he heard them in the hallway, and had the nerve to shush me (why? I have no idea) and it threw me off. I was a little bit annoyed because it was a really good build up, ugh. But, gentle reader, no fear. He got me there later.

Am I being too graphic? Meh. Who cares. It balances out my sad Felicity-ness. 😉


I feel as though I’m floating through my life at times. There often are large chunks that I just don’t seem to recall until something jars a memory loose and then there I am. “Oh, yeah. That happened.”  Maybe it’s a good thing. Maybe it means that I’m living in the present, that I’m not dwelling on the past. Though that seems a little bit too rosy of an assessment,  it could just be that I have a mind like a sieve, or that I’m not paying proper attention.

Last week it was a year since Carl and I broke up.  Those first few days felt like I was floating through someone else’s life. There wasn’t a lot of drama. I knew it was coming. I had known it for the last couple of years.  It was mutual, calm, amicable even. I loved Carl, I still love him. But our relationship was an odd one. That’s a very long story for another time, which I will tell you at some point. Suffice it to say that he’s a continuation of a pattern for me.  This past year of kissing lots of boys has somewhat proven to me that I am attracted to relationships that are doomed to fail. Before you write me off as just being dramatic and self involved- hear me out.  Carl and I dated for 11 years. We saw each other two or three nights a week (he would sleep over)  and we never lived together. Never even discussed the possibility even though we started dating in our late 20’s and I had already turned 40 when we broke up. Prime living together/marriage/kids years, right?  I think part of the attraction, at least on my end was that I knew it was never going to be serious. It was low commitment. We ended up both cheating on each other in the end and it eventually imploded.

I have seen six men since last April, (April 4, 2014) and not one of them has stuck yet.  I fell in love once, because he was seriously NOT boyfriend material. I saw that coming. Ran in the opposite direction once. Was unimpressed more than once. Had a few once night stands. Will probably have a few more. I’m chatting with a handful of them currently, actively “seeing” or “dating” or “fucking” them as they reveal their characters to me.  I’m on a few dating sites, Tinder, Plenty of Fish, Hinge. I feel rather like a sexual anthropologist, at least that’s how I’m approaching it.

I really should have started writing about this more than a year ago. Much of it is fuzzy, but I hope that the process of journaling it will knock some of those memories loose for me, and hopefully entertain you in the process… that is… if anyone is reading.