Tuesday, May 12, 2015

A new man, let's call him Aaron

After things have kind of cooled off with Ryan, I started talking to a new guy, who we'll call Aaron.

Aaron and I talked online for a bit, then through texts, and when he didn't respond to one of my texts for hours, he called me.

We chatted for 20 minutes, and it was in this conversation that I told him of my widowness. And that I found a story about how he lost his brother less than a year ago.

So we have this instant connection. And I'm waiting to see if we have more of a connection than that, but so far it's sweet.

And we have a date in Chicago in a little bit, and I'm hoping it goes well. He is a little younger, but already seems more mature than both Scott and Ryan.

Monday, May 11, 2015

Sexting with Scott - Part 2

- I don't understand tossable...is where I left the last post about sexting with Scott. I was going to include the text here..... but I think it's better to leave it up to your imagination.

He started here:

-Well, hypothetically, imagine you are on top ......

And it got raunchy.
And ended here:

- Glad I could explain to you the meaning of tossable. You're lucky if you're tossable. Doubly if you are tossable with big firm breasts. It creates various opportunities.

And after a few days passed, we decided to put a pin in our communication until we're closer to being in the same city.

He is smart. Articulate. A little emotional, but I told him I wanted to see me as more than just a potential lay. We started talking, in theory, because we have at least one quality that the other is looking for in a life mate.

So pin in Scott. Until further notice.

Friday, May 8, 2015

Sexting with Scott - part 1

Not long ago, both Scott and I had work commitments, and we both had consumed a few drinks....it started in a somewhat innocent text flirtation, that ended in a full-on sexting session, that I thought I'd share here.

It was only after I shared it with my friends that they informed me he was probably getting himself off while writing, especially, since I was pretty unresponsive. I didn't really know that men do that. I'm pretty sure that husband #1 never did that.... how do you even text while holding your shlong? Despite me not really understanding the logistics, I think they're probably right....

Instead of using my name, whenever he says it, I'll refer to myself as Wanting Widow.
Without further ado...

-Ugh Scott, I'm just the right about of tipsy that if we lived in the same city right now...

- Me too, Wanting Widow
- Fuck

-Please
-one day

-And I do admire your cleavage. You also have a really shapely face, when you're not SCOWLING

-I'm not scowling, I'm trying to be sexy. I guess it comes more naturally to some

-sexy ->nipples
- or a cobalt blue suit in my case

- not sure if we're there yet, but if they made an appearance in person, what might you do to them?

-that's a very good question, Wanting Widow, I have a few crude thoughts that I'll keep to myself.

-Why keep them to yourself?

-Because they are crude. And rude.

-I'm a big girl. I think I can handle it.

-And I'm a dude.

-And you rhyme. Some of the time.

-You are a little girl.

-With big boobs. That happen to have nipples on them.

-I think you might even be described as "tossable"

-What does that mean? You can throw me away? :-(

-What a sad thought! No! Like, bounce you on my...lap. Flip you over.. For a...

-Keep talking

-No no. Not a crude dude. Keep those thoughts to myself.

-But I don't know how it ends. I don't understand tossable....

Monday, May 4, 2015

Date #2 with Ryan

I'm pretty sure that date #2 with Ryan will be the last date with Ryan. He is a nice guy. Understanding. Smart. Not altogether unattractive, but I'm pretty confident that he's not the new guy for me.

We made plans for me to go to his apartment to watch Curb Your Enthusiasm, and for him to make me dinner. We talked all week about the tentative menu, and he seemed really excited to cook for me. Let's be honest, a meal where I can watch TV, that costs me nothing, I was looking forward to it too.

So I get to his apartment in Lincoln Square, that he shares with two other 20something year old boys. He opens the door, and I am smacked in the face with the smell of boy.

And not like boy's cologne, but full on boy living, breathing, sweating in the apartment boy.

Strike 1. But I can look past it. I can. They are nose blind to it, and soon I will be too.

We sit on the old, grimy couches, in front of the coffee table that is a slab of glass on top of two plastic hampers. One is pink and one is blue. The table is littered with papers, remotes, cups, paper towels......  He mentions that he has nice stuff. That none of this stuff is his. His stuff is in storage, and costs $100 a month to store. He's doing that instead of having his stuff in this apartment. Okay, so strike 2, but I can look past it. He wants me to believe that he's adult enough......and I almost do.

I came over for dinner, and after watching TV for half an hour or so, I said I was getting hungry. He asked if I wanted to help chop up stuff for the fondue that he was going to make. I didn't really want to.....but of course said I would help. I'm a good chopper, but it was our second date....he should still be trying to impress me...and maybe he was, but it just sort of felt like he didn't quite have his shit together. Like he isn't a good enough planner.

So we ate the apples, carrots, bread and broccoli in the fondue, and the next course he had planned was steak, but at this point it was 9pm, and the steak was still wrapped in plastic. I didn't really feel like waiting half an hour and eating such a heavy thing, so I asked him if he would be offended if I didn't eat steak. He kind of seemed like he would be, but I told him it would be a waste, that sometimes I don't like to eat large amounts all at once...

We keep watching TV for a bit; HBOGo keeps on stalling. His arm is around me, I'm kind of nuzzled into him. It's not terrible, really. Except for that my neck starts to hurt after a little bit. But I find myself getting bored, and while he is nice and all, I found myself really wondering about my physical attraction to him.

So I ask him, point blank, if he wants to fool around for a little bit.

We go into his bedroom....bed unmade, and I gesture for him to take off his shirt. And he does. And it's really hairy. Front and back. Something I'm not used to at all. I used to tell husband #1 that he had the perfect amount of hair...everywhere really. Ryan and I are kissing, his shirt is off, and he unzips my dress, so I'm standing there in my bra and panties, and I dunno....it's fine and all, but not great....

We climb into bed - me, with the knowledge that there's no way I'll be sleeping with him, but also with a curiosity as to what I'm working with.... I find my way to his zipper, after swatting his hand away from my panties... and telling him that whatever he was doing to my nipple wasn't really doing anything for me.

I unzip his pants and find my way in.......to disappointment. I'm sure it's average. But I was used to above average. And I loved every minute of it. I offered to play with it for a bit, without actually seeing it, but he said he's never gotten off with manual stimulation from a girl.

This is where I know something's up. "Are you on antidepressants?" I ask. Sure enough, he is. And blood pressure medication. There's no way I want to fight against the meds. There's also no real chance that I want to watch him jerk off while he looks at me. And yes, he did ask if I'd be okay with that. And then asks if it was weird. I said, "yes, that's weird." In 9 years with husband #1 I don't think he ever jerked off in front of me. And that was okay by me.

So I tell Ryan that I'm not even going to try if it's not going to happen, and then went to put my bra back on. I just felt like everything was too dirty that I didn't really want his hands wandering in my nether regions, and there wasn't much else to do.

I told him shortly after that I wanted to leave. And I left, after a few more kisses. And I got in the car and drove to my friend's house....and I cried for husband #1 most of the way there.




Wednesday, April 29, 2015

Going out with Ryan...thinking about Scott

It still feels a little weird to be thinking about/talking to two different men, neither of whom are husband#1....but my friends are encouraging me to cast a wide net. To play the field. To have a little fun.

Even though I had the most fun with husband #1, I think they're right. I shouldn't get too into any one man at this point. It's unlikely that the first or second guy I date or hook up with will become husband #2. Not impossible, but unlikely.

So I'm seeing Ryan, who is really nice. Who texts with me all the time. Who told me he likes me......but I can't help but think about how sexy Scott was in the video I saw of him lecturing...to an empty room.

Scott and I decided to put in pin in whatever we were developing since we aren't going to be in the same place for several weeks yet. I kind of get it.....it is really just a fantasy right now, even if we did FaceTime....but in the meantime, it's nice to have Ryan as a distraction.

And I may have bought a sexy new bra and panties to have in my back pocket...just in case.....

Sunday, April 26, 2015

Real messages - Part 1

Because sometimes, you just can't make this stuff up, I decided to intersperse my posts with ACTUAL verbatim messages that I have received on dating sites. So far, I'm only on "OkeeDokee" and "HeyDate"....

I just don't think I can ever understand what goes through some of these people's heads.
There are a few different types of men out there, I'm learning. Slowly.

The over-sharer/one who tries to tell you everything he thinks you'll want to know in the hopes that you'll feel an instant connection/want to blow him:

"Got two older brothers, two step brothers and one baby sister. I like to go shopping, watch movies, go out to dinner, listen to music, watch NFL, watch NBA, love to cuddle, love to text, I'm respectful. I'm a nice and honest person. Love video games. Looking for a relationship. I live at my own house. I will never cheat on u. like movies and music. Love Sex. Want to text babe:)"

I want to add my own judgments and comments here, but I'll just leave it with this: So basically, he's telling me he's a person. Who exists. And doesn't adhere to traditional grammar rules. I know I don't always either, but it's usually for emphasis or to make a point. Also, this "man" is 24. Doesn't warrant a response.

Then there's the....let's call him bold/unconventional...and not really in a good way:

"Hey there! Let me start by saying I am aware of how forward and inappropriate this might be if you're not that open. I'm a (relatively) normal (slightly geeky) professional with the unfortunate juxtaposition of having absolutely no time for dating or getting to know people and an insatiably high sex drive. Since I also have a thing for hooking up with people I don't really know, and because you miss 100% of the shots you don't take, I saw your profile and wanted to see if you'd like to get together today or soon to let loose and have some fun without judgment or strings attached. If you're not, thank you for reading and have a nice day. If you're open minded and don't think it's too socially unacceptable I'd love to get together with you today. What do you think?"

"shot in the dark, have any interest in a submissive guy new in town?"

"hii, would you like to slice me up with a scalpel?"

And then there are the ones who try to start with flattery....not sure what to call this type yet:

"Woaaaaaaah, what a profile and what a figure. I totally don't expect a reply from you, because that can only happen in my dreams!"

"Okay, I'm hooked with the photos, I guess now I'd like to hear(see) her speak :-)" --- Okay I can admit this one isn't TERRIBLE, but he's 10 years my senior (dealbreaker) and not my physical type.

"So I don't want to come across as disrespectful, but honestly you're too beautiful for your own good lol. But straight up no bullshit, I'd love to get to know you sometime. Over coffee, drinks, a pool game or planting a tree I don't care I thought it'd be worth coming by to see if we could get to know each other so...here I am. But before I become your new best black friend, find out your favorite color, ice cream flavor, I wanted to know something. If a guy really wants to be in your life, what's something he should know about you before hand? Like you aren't some kind of crazy cat lady are you? Also where would you travel to if money wasn't an option? - This novel is brought to you by the Reading Rainbow. *que song*"

.....
.....

Open to hearing your comments, if there are any readers out there.



Wednesday, April 22, 2015

My first first date in 9 years

Ryan and I exchanged long messages on OkeeDokee online dating site, and soon those long messages turned into long emails, and dozens of texts throughout the work day.

He is also a lawyer, but already lives in Chicago, and after having enough to talk about with each other for weeks, I asked if he wanted to grab drinks.

He also asked at some point how I ended up in the city I currently live, and what was bringing me to Chicago. I told him it was wrapped up in a sad story, but that I would share it with him if he wanted. Through mutual friends, he was able to figure it out, and apologized...both for finding out, and for the fact that this was my story...and he also said this was new for him. But he decided to keep talking to me. Score 2 for men in their 20s/30s not being scared off by the baggage that automatically comes with a 20something year old widow.

So Ryan and I talk a lot about the possibility of making out. He assures me that his experience with the French horn makes him a very good kisser. I tell him husband #1 played an instrument too. Maybe I shouldn't have. And maybe I also shouldn't have said that I miss having sex with husband #1. But I did.

Ryan and I decide to meet for drinks at a place near Lincoln Square, but I decide to bring two girlfriends. I tell him beforehand, so he doesn't feel ambushed, but I also tell him that it's what I need. That this is my first first "date" in 9 years, and I don't know what to do. How to be. What to say....

So my girlfriends come, and it's the three girls and Ryan. And he talks to them almost more than he talks to me. He tells us a story about some unfortunate boss he had. And after they text me that they think he's nice, and after drink number 2.5 for me, they excuse themselves to go on a quest for pizza. Or chocolate. I don't really remember. I don't really care.

So here we are, Ryan and I sitting at a table. His sweat from riding his bike to the bar has dried. He's not exactly my type physically, but I'm getting more drunk by the minute, and he keeps touching my arm. My hand. My shoulder. It's obvious this "making out" that we've been talking about might happen soon.

I take another sip. "I don't know what I'm doing. My life is so complicated"
He moves his chair closer, and grazes my hand.
"It's not so complicated. It's okay"
He leans in.

We kiss for a minute.

.....

<<WHAT AM I DOING. KISSING A MAN OTHER THAN HUSBAND #1. WHAT AM I DOING KISSING A MAN AT A TABLE IN A BAR??!!>>

.....
I finish my second gin & tonic and order another.
He told me about a time he ingested pot on a trip to India, and I asked him to tell me his story, and then I shared with him the time that I made pot brownies in college. (I did it wrong. Got super high. Threw up. A lot.)
......

We kiss some more.
.....
It's midnight and the stupid Chicago ordinance that outdoor 'beer garden' spaces close goes into effect. We have to go back downstairs. We finish our drinks. We get ready to go on a quest for pizza. <<Need food to avoid hangover tomorrow>>

On our way out, we wander back upstairs, which is closed to the public, and yet there are people up there. The door is closed, so there's this sort of secluded alcove at the top of the stairwell. We make out some more......and then I tell him that I want to show him my boobs.

I don't know why.
I don't know why I want to show him. Or why I chose to do this. I was pretty drunk, but Ryan had mentioned that he is a boob man. And I thought he'd appreciate my 36Ds, and I wanted to have them appreciated. It'd been months since they'd been appreciated in person.

"Wow. those are pretty fantastic."

"Thanks, Ryan. I think so too. Do what you will with them."
So we're making out in this not really private alcove at the top of the stairwell in this bar, when he moves his mouth to my breasts and puts a nipple in his mouth. And nibbles just a little bit.

We make out a little more. I put the boobs away. And we go look for pizza.
...
It's Chicago, so we find pizza in approximately 3 minutes. He buys (which he totally doesn't have to, but I appreciate it).

We finish our pizza, and he shows me where the single person bathroom is on the side of the restaurant that's closed. I bring him in the bathroom with me. And we make out some more. And my dress somehow comes down, again. And his mouth finds both of my nipples this time.
"a little more gentle" I suggest.

My hand was able to tell that he was enjoying himself very much. I bent over as I let him have his way with my ta-tas.

We kiss some more. I apologize for maybe giving him blue balls, but I also don't really care. I don't think I'm being a tease, or am leading him on, that's just all I was ready for. And he seems like a nice enough guy that he understands.

He held my hand while I waited for my Uber.

<<My first first date in 9 years. Overall, a success, I'd say...">>