#3: Carlito’s Way – My first date…

Now 2 months on 2 apps, 1 date scheduled, 0 dates had

Then there was this… Let’s call him Carlito.

I was desperate for physical contact so I decided to get bold on Bumble. I matched with this super cute 33 year-old and was really excited because he was actually in town.

This was his profile:

“All I want is a relationship that will make all our friends jealous.”


At 6pm on Friday night I sent this:

Hi Carlito! I don’t swipe right often so I thought I’d tell you why I matched with you…

You have a cute smile.

You can pull off a sports coat with sneakers – very rare.

You’re musical.

Your profile or bio (whatever it’s called) is adorable.

You make bald look sexy.


You’re not presenting a fish to me.

Ball is in your court now.

His response:

A female welder!! You win the badass award. And congratulations on looking super cute in glasses and looking like you belong next to a campfire. I’m up for the weekend with some friends. Are you skiing this weekend?

It was on! We texted and made a plan to meet up at a bar each bringing a friend. On our way over, I texted our good friend Captain America, telling him that I was on my way to meet my first guy from the internet but deep down I was wishing it was him. He replied ‘damn’. NUMBERS GAME!

My friend was the best wing-woman ever. His friend wasn’t as cute as he was and was possibly gay. They worked on her Bumble profile together while Carlito and I got to know each other. He was cute, affectionate, smart and interesting. We went to the bathroom at the same time, his idea, where he waited for me to come out and brought me in for a kiss. It was SO HOT, my whole body was on fire. I knew at that moment that I was definitely going home with him. We shut the bar down, went across the street and got doughnuts with chocolate sauce.

A side note to the doughnuts and chocolate sauce:

We got into my car to drive back to their rental house and our friends were in the backseat with the pastries. They put the container on the middle console (my arm rest) and without me knowing it, I put my elbow right in it. I had a thick layer of chocolate on my jacket, which looked like a professors elbow patch. Our two friends saw this happen and decided not to say anything at that juncture. I didn’t realize until I got home the next morning. There was chocolate everywhere in the car including the drivers side window. (That one is still a mystery.)

So we get back to their place at 2 am (very late for me) and they bring out a bottle of champagne. They were much fancier than we were. They were a bunch of guys from the city vacationing in a very expensive resort town. Whereas we were locals in said resort town, both artists, who spend 75% of our days in dirty studio clothes. I am in a CLAY COVERED APRON at this very moment.

My wing-woman was up for anything and when I asked her if she wanted to go home, she insisted she didn’t care, so I just announced to the group that I wanted to stay and make out for a bit, and she was game. So Carlito took me into his room and before I could blink he had all my clothes off. It happened so fast. I didn’t even shave my legs because my expectations were so low and forgot that I HAD MY PERIOD. Once he got me naked I was like – OH SHIT! WAIT! And I had to tell him that I had my period, and he tugged on my tampon string like he was going to take it out! It was such a surreal feeling, someone else trying to take your tampon out! So I succumbed and went to the bathroom and took it out. It was my last day, so things were pretty clear down there, but really? I honestly couldn’t believe he still wanted to be down there knowing that. But if he didn’t care, I didn’t care. I was ready to go.

I have lived a very SHELTERED SEX LIFE. The man I married was not adventurous or interested in trying new things at all, which partially lead to our demise. He was the majority of my sex life, so when a guy asks me what I like in bed, I literally have no idea. So, I am taking this time in my life to figure it out. Something new I experienced that night was HAIR PULLING. I liked it. It wasn’t painful, a little aggressive but non-threatening. It was hot. He was hot. He thought I was hot, which made him hotter. He would compliment my body and tell me that he liked me. I talked dirty back and kissed him hard, but I never felt comfortable telling him that I liked him back.

He could not keep an erection with a condom on and I was adamant about the condom. After a couple tries, he said ‘I think I’m going to cry’. I laughed and kept kissing him. It was so nice just to be naked with someone and to be touched. After we decided that he wasn’t going to get off, he concentrated on me and it was nice, but he didn’t make me cum. He accidentally put his FINGER IN MY ASS – first time for that too – my eyes got wide and I jumped, he apologized and we laughed. Then we both passed out for a couple hours.

It was 5:30am, I didn’t know where my friend was and it was time to SNEAK THE FUCK OUT. Instead of being smart about it and crawling out the far side of the bed I climbed over him on the near side of the bed, and he grabbed me and we started fooling around again which led to sex. UNPROTECTED SEX. I was not ready. It felt like I was losing my virginity all over again. He was a big boy. I am petite to begin with and I had been celibate for 2.5 years, I was really, really tight. And I wasn’t ready. There was no foreplay, he went straight to penetration and it hurt like a MOTHER FUCKER. I was into it, it was not assault of any kind, I just really wished we had some lube. I, at least had the wherewithal to tell him that he absolutely cannot cum inside me and he didn’t. I got up and washed off in the bathroom as soon as I could, put my clothes on kissed him goodbye and got the fuck out.

I assumed I would find my friend on the couch, but she wasn’t there. I texted her and she texted back right away. “Are we leaving?!” BEST WING-WOMAN EVER. She met me, we made sure we had her purse and left. I recounted every graphic detail on the way home and we both laughed our asses off. It was really great to have a partner in crime on this adventure and the sunrise was absolutely gorgeous.

I had never felt so sore in my life. My whole body hurt, inside and out. I could hardly sit down. I had no intention of seeing this guy ever again. And we were so smart about it, making sure we had my friend’s purse before we left. On our way home (6am) I got a text message and we thought it was going to be him, but it was Captain America! And it went something like this:

Captain America: How did it go?

Me: I’m on my way home now. The sunrise is amazing.

Captain America: You fuck him?

Me: I’m a lady so I never kiss and tell.

Captain America: Damn, I thought we were going to be honest with one another.

Me: It was just meh.

So I guess I’ll be fantasizing about you for the foreseeable future.

Captain America: Fuck. Come to New York.

Me: I might have to.

I bet you know what to do with a woman’s body.

Captain America: I think so.

I bet you know how to please a real man.

Me: I think so. 😉

Does that mean that you’re a real man?

Captain America: Yes mam

Me: Mmmm We don’t have a lot of those around here.

I passed out, for three hours. Woke up to a text from Carlito. He asked how I was feeling and told me that HE HAS HAD A SMILE ON HIS FACE ALL DAY. Charming as hell. When he got home from boarding that day he sent me an image of my purse slung on the back of a chair in the kitchen – “did one of you girls forget something?” “fuck”. I had to see him again. I left my fucking purse at his place. I mean what the shit?! AMATUER MOVE! I was mortified. I never use a purse so I didn’t remember that I even brought one. We made a plan for me to pick it up, I asked him if he would be the best guy on the planet and meet me outside, so I didn’t have to perform the return of shame, he of course did. We chatted for a while, then we started making out, full on ass-grabbing, it was hot. He was going out with his friends, I was going to the hot tub for some much needed R&R and he seriously thought about blowing his friends off to come with me, which I would have been fine with, but I didn’t want to be that girl and he didn’t want to be that guy. So we parted ways. He texted me on his way out of town Sunday evening and asked me to be in touch if I was going to be in his neck of the woods. I told him that I would be in about a month and I would let him know.

At the end of the day:

I FINALLY MET SOMEONE FROM ONLINE. It took me 2.5 months. He wasn’t the mind blowing sexual experience I was looking for, but he was sexy, sweet and so communicative. I really liked how he stayed in touch. My wing-woman gave me advice that night before we went out. She told me to BE THE CAT. I am very dog-like, I give my love and admiration out freely, sometimes it is returned, sometimes it is not. I hate games and refuse to play them, much to my detriment. But with this guy, it was easy to be the cat, and he ate it up. I was me, but I didn’t develop feelings for him, so I could be detached, unlike with Tinder Ken. I had a goal, to have sex and I accomplished said goal. He was cute enough that I decided I would see him a month later. I texted him and gave him the date well in advance and asked him not to meet his dream girl before then, he said yes mam! We saw each other again, more on that later…

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