I recently decided to try something other than Jdate since I’m open to meeting someone who isn’t Jewish. Match was a total bust a few months ago so I signed up for Eharmony….AGAIN!

Eharmony’s process just sucks….and this go around has been just as annoying and unsatisfying as it was when I first tried it years ago.

The first decent guy to contact me was Russ. He wasn’t great looking and he wasn’t very tall and he dressed like a 60-year-old man in his pictures….but fuck my life I’m 33 already!!!

We made plans for drinks after work and we exchanged numbers to keep in touch.

I’m a total stalker so once I got his cell # I started my search on Google. Within minutes I realized that I had just made a date with a millionaire – Cha-Ching!!!!

He owned a hugely successful business AND a winery in Napa! His face was plastered all over the Internet, articles celebrating his success for such a young guy…there were even YouTube videos of him analyzing the industry he worked in.

Ugly or not I was going on this fucking date.

I arrived at the bar and realized that my millionaire date was the missing member of Alvin and the Chipmunks. He had this very round face with pudgy cheeks and these two white front teeth that seemed to show even when his mouth was closed.

Disappointed yes, but my internal mantra that night was, “Napa, Napa, Napa, Napa.”

Drinks went surprisingly well. We had a lot to talk about and he seemed genuinely interested in me. I even stopped noticing how closely he resembled a chipmunk at exactly the same moment he started explaining his process for making wine…

He walked me home like a gentleman and although it wasn’t particularly romantic he stopped me on the street and kissed me.

We made out some more in front of my building and agreed to see each other when we both got back from our vacations. He was leaving in a few days for a 2-week vacation and before he returned I was leaving for a week in Mexico.

That night he texted me to tell me how much fun he had on the date and how awesome it was to make out with me. I told him I had a great time too and was looking forward to seeing him again in 3 weeks.

The following night he texted me that he was in the neighborhood and wanted to give me a goodnight/goodbye kiss. I should have said no, considering I was already in bed naked half-asleep (it was 9pm), but after my missed opportunity with the Turk (which I plan to regret for the rest of my life), I ran around my apartment like a chicken without a head, cleaning my apartment, my body, getting dressed and putting make-up on.

9:20pm he was in my apartment.

9:21pm he was dry humping me.

We were both fully clothed and he was humping me and grinding on me so hard and fast that he was going to cum.

With every hump and bump and grind that I felt, I just kept reminding myself, “Napa, Napa, Napa, Napa!”

9:40pm I finally stopped him mid hump, rubbed out the soreness in my thigh, told him I’d see him in 3 weeks and showed him the door.

10:26pm he texted me: “I’m lying in bed so horny right now thinking of you.”

10:27pm I texted back: “I’m trying to sleep, talk to you tomorrow.”

Believe it or not I never saw Russ again….he actually blew ME off!!!

I guess I wasn’t his Chipette after all!!!

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I hadn’t been laid since April 2012. I was drying up!!!!!! The cobwebs had appeared….

I was getting desperate!!!!

So when I received an instant message last Saturday from a 24 year old guy on Jdate I decided to ignore my gut reaction to ignore the kid. Cute pictures, 6’ tall, Jewish…I knew we probably had nothing in common (I recently turned 33), but I told myself what the hell!

I emailed him back, “Ur adorable….and very young!” Before I knew it we were talking non-stop.

7:30am “good morning” text messages.

Random texts throughout the day – “how is your day” “I can’t wait to see you!” “Ur so cute!” “Ur so sexy!” “I can’t stop thinking about u!” “Friday can’t come quick enough!”

Phone calls after work, before the gym, after the gym, before dinner, after dinner and before bed.

This kid was head over heels for me…and we hadn’t even met yet. The attention was nice…

I opened my apartment door on Friday night and felt a small pang of disappointment. He looked very young, he was cuter in his pictures (what else is new), he was balding (I know I know…not his fault), and he wasn’t 6’ tall.

But I brushed my disappointment aside when my vagina started to itch reminding me of our 14-month drought. When he kissed me I let him…

Dinner was nice…but I was kinda quiet (which is not the norm for me). I found it hard to find things in common to talk about. My brain kept telling me “he’s too young, this can’t go anywhere, you are wasting your time”….but my vagina kept whispering “Help! I’m lonley! I’m drying up! Take care of me!!!”

So although he enjoyed talking about his high school years while I’ve already been to my 10 year reunion, or that he still lived at home with his parents while I’ve been on my own for 10 years, or that his sister was headed off to college while my sister has been married for 10 years and has 2 children….we left dinner and headed back to my apartment to make-out some more.

We were lying in my bed barely dressed when he whispered in my ear that he had protection.

This was my moment to end it and send him packing on the LIRR back to his childhood bedroom.

OR….

I could have sex with him (hopefully good hot steamy sex) and then at least I could restart the clock on “the last time I had sex” because lets be honest…. my answer to that question was getting embarrassing.

Very quietly I answered him “OK.”

Now let me pause here for a minute to tell you all that I DO NOT sleep with men on the 1st date. Or the 2nd date. Or the 3rd date. This was the first time I had ever done this!!! I had only been with 6 men up to this point and I think this is a very respectable number of partners. I’d like to avoid hitting double digits if at all possible.

And then he entered me….

Me to Me: “Is he inside of me yet?”

Me to Me: “Wait…I think I feel something…”

Me to Me: “Shit, I think he lost his hard-on?”

Me to Him: “Everything ok?

Him to Me: “Yeah, I’m so turned on right now!”

Me to Me: “Oh my God, this is him turned on?”

Me to Me: “I don’t feel anything, how is this possible? He wasn’t that small.”

Him to Me: “Feel good?”

Me to Him: “Uh Huh….”

Me to Me: “Is he going to start moving? He’s just sitting inside of me like a wet noodle…”

Me to Him: ”Wanna flip me?”

Him to Me: “Yeah!”

Me to Me: “How is it that I still can’t feel him!!! Wait let me give it a squeeze….I can’t believe this!

Me to Him: “Everything OK?”

Him to Me: “Oh yeah baby, you like how this feels?”

Me to Him: “Uh huh…”

Me to Him: “You wanna try standing on the floor?”

Him to Me: “OK!”

Me to Me: “Why can’t I fucking feel his dick inside of me? Maybe its the condom???”

Me to Him: “You gonna finish soon?”

Him to Me: “Oh no babe…it takes me a while when I’m this turned on!”

Me to Me: “That makes no sense….this needs to end soon.”

Me to Him: “Maybe it’s a good time to tell you that I don’t come from sex so you should just try to finish.”

Him to Me: “OK, lets get back into bed.”

Me to Him: “You still hard?”

Him to Me: “Oh yeah baby, I’m so turned on right now.”

Me to Me: “My legs are on his shoulders and I STILL can’t fucking feel him inside of me…move your penis…move your hips…Thrust! Thrust! In then out….In then out…In then out…In then out!!!!“

Him to Me: “Oh you’re so hot! Feel good?”

Me to Him: “Uh huh…”

Me to Him: “You close?”

Him to Me: “Not yet…I wanna watch you masturbate…that will get me off!”

Me to Him: “OK.”

Me to Me: “Really?? God…do I know how to pick ‘em!”

And that’s how sex with my 7th partner ended. Me masturbating…him getting cum on my Pottery Barn duvet cover and me wondering….

If a penis enters your vagina, but you don’t feel it, does it count?