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...">>