#ShadyShenanigans: A story about OKcupid and losing my virginity to an escort

<editorsnote> Soooooooo, I asked you guys the other day to reach out with your stories, that I'd love to hear 'em, and boy oh boy have you ever. So much so that I'm actually going to give it a section on the site called #ShadyShenanigans. HAHAHAHA you all make my life. Alrite, now here's a dude who quit OKC and opted instead for another type of professional service .... the uber, uber, professional. cough cough. Enjoy nerdlings!!! PS. Everything is always. always. always. kept anonymous. <editorsnote>

Hi Jen,

I emailed you a couple weeks ago to comment on your story about love that wasn't a love story, and how I had just gotten out of something and that your experience made me learn some things about myself.  Well I would like to share that story, however, I would like to ask that if you decide to share this if you could please keep me anonymous.  If that isn't cool I understand, in which case I ask that you don't publish this.  There are just some aspects that I find incredibly embarrassing, being a guy and all.  And with things like this I don't have your courage.

So here goes:

I am twenty six years old, and up until the cusp of my twenty-sixth birthday I was a virgin.  According to statistics, I was part of the exclusive 5% male population (in my age bracket) that had yet to know what vagina felt like.  This was something only known to my closest of close friends, and a fact that most wouldn't have guessed.  I'm decently attractive, personable, and on occasion really funny.  Being a virgin was mostly due to a couple reasons: 1. my parents aren't super religious or anything like that, but they are conservative on a level close to Mormon-ism.  Dating in high school wasn't really possible, and made me shy around the girls who showed interest. College was a disappointment in that the social skills I feel that should've been learned in high school weren't in my arsenal to help me woo any ladies.  I went on dates here and there, and made out with who knows how many girls, but if there were a Man Olympics I would've been considered a spectacular disappointment.  2.  I never tried hard enough initially, and after a few years I was insecure about it.  People often say that you meet someone when you least expect it, when you stop trying.  But what they don't say that is that you have to have you recognize your opportunity and capitalize.  Life will put you on the court, but you've got to make that dunk yourself.  I never took the chance to dunk.

Flash forward to a few years living in Los Angeles, and same story.  I met girls here and there, but nothing really clicked.  The ones that did I failed at following through.  So after a night of skyping with a friend who had found her recent love via OKcupid, I thought "why the hell not?"  Within a month of being on the site, I had gone on two dates in three weeks.  The first date was with a girl I had a 94% rating with.  We shared a few messages and had lots in common, and I thought we could get along really great.  While I was impressed with her forwardness (she basically asked ME out), I was slightly concerned by her screen name, which combined with her age seemed as if she was in the hunt for a ring.  No bueno, I'm down with finding something special if it happens, but settling down isn't really part of my immediate future.  I'm also always down for new experiences, and online dating was something totally new to me.  So we met up, and I was kinda put off by how she didn't really look like her pictures.  She was still kinda cute, so it was whatever I thought I'd feel it out.  And here is where I learned a valuable lesson - dates where you can't really talk will go nowhere.  We watched a comedy show on the west side, and afterwards it was late and since we both had to work the next day, we chatted, hugged and parted ways.  We exchanged a couple emails but I didn't see it moving forward.  The end of that story.

On to date number two!  This girl was really cute, we had a 90% match rating, and kinda young.  I was interested to see what going out with a nineteen year old girl would be like, especially since the previous date was twenty-eight.  After a handful of messages about books and Mad Men, we agreed to meet for sushi in the valley.  She was still really cute.  She was personable and open.  I'm liking where this goes.  After sushi we got coffee and talked more.  It was more her talking and me listening, so it occurred to me that she might be of the selfish type.  I would come to realize to what extent later.  She was brought up the idea of a second date, which took me off guard, but I was having fun with her and this was exciting.

So there was a second date, and third, and a fourth.  Being a virgin, I didn't really know how to be sexually aggressive.  I felt in a way it would be kinda like over-promising and under-delivering.  It was maybe the fourth date I had her at my place for dinner, and where I would finally follow through.  So after dinner, funny stories, and more laughs courtesy of Curb your Enthusiasm, we were making out on my couch.  Just before my hands could start exploring she says to me, "I have to actually have to leave a little early."  "Why?," I asked.  "My dad is away and I have to take care of our dog."  She still lived at home with her family.  And apparently only he and her could put the dog to sleep at night.  I could tell she clearly saw the disappointment on my face.

Flash forward a month, more dates and making out, more lost opportunities b/c of her familial obligations. The cherry on top was a text from her one night saying "I feel like family only exists to cock-block you."  She had no idea.  One night after dinner, she wasn't feeling well so before I dropped her off we sat in my car and talked.  It was a solid conversation about various things, but then I decided to open up.  I told her that I was still a card carrying member.  It was such an idiot move.  I thought it would be better to be open about something like that.  Lesson learned.  She said it was and wasn't a big deal.  She had issues being the one to take it as she thought I would fall in love with her.  - I should clarify that we both knew that this relationship wasn't built for the long run.  Despite our OKcupid match rating and the fun times we had together, we were two very different people heading in very different directions in life.  We both were aware and comfortable with this fact.  It wasn't an "exclusive" relationship, per say.  The thought that she might be seeing other guys didn't bother me.  I had a feeling she'd gone on other dates, but the way her demeanor slightly changed over time made me pretty sure that up until this point, I was the only guy she had stuck with. -  So we discussed this a little bit.  Being a stubborn person, aren't we all at nineteen, she was convinced that my first time might lead to infatuation.  She mentioned her own experience, and interestingly said, "and I don't want to get hurt again."  Well I knew that losing my virginity would only bring lust, not love.  Life isn't the movies, and I don't think boys are designed to think that love and sex are related.  I couldn't really convince her otherwise.

So we continued to see each other on and off for another couple months.  She actually got really sick at one point and we didn't see each other for a month or so. And then she got super busy with school. There were dates where she was content to sit and read a magazine rather than talk about anything, and there were dates where we had a lot of fun.  These dates in particular always led to making out in my living room until she had to go home around midnight.  It was like she was a chastity belted Cinderella.  I continued to see this girl only because I kept thinking that I could get it done.  It's like "chasing the river" in a poker game, 9 times out of ten you end up losing.

So as my birthday approaches, I kept thinking to myself that I didn't want to be a twenty six year old virgin. No way.  I had no idea what was happening with this girl, and by now I was pretty sure she was getting it on with other dudes.  I was trying to meet other girls, but nothing really got off the ground.  I have the worst luck with these things.  At some point I had heard about the Moonlight Bunny Ranch, a real live legal brothel in the outskirts of Reno where one could simply pay for sex.  I googled.  I found a website.  I found a girl who had great reviews in the forum and I booked a weekend appointment.  It was all professional and business, and was awkward breeze to deal with.  A flight and hotel were booked and I counted down the days.

I landed in Reno on a Saturday afternoon and found a car and hotel.  I lounged and watched the Real World on MTV.  I drove around explored the city.  On a cool and drizzly Sunday night I made the drive to the Ranch. I couldn't stop thinking of how crazy this was.  That I was actually doing this.  That years of incompetence with women had brought me here.  To a big neon sign at the end of a dark dirt road in the middle of the beautiful desert, surrounded by mountains.  Seriously?

I parked and walked to the gated entrance.  The moon was full and I felt like I was in some X-rated version of Hanson and Gretel.  There was Elvis music softly playing from somewhere.  I buzzed, I entered.  There were attractive girls in robes and skimpy outfits chatting at the bar.  I looked at them, they looked at me. Awkward city.  A woman in jeans and a black sweater approached, asked me if it was my first time.  "Totally," I replied.  She explained that there would be a line-up and I would pick.  Just like the movies?  I told her I already had an appointment and she left to go find my girl.  I sat and took it all in.  Still in disbelief.  I kept telling myself I didn't want to be a virgin anymore.  This was worth it.

A blonde woman with green eyes and blonde hair and platform heels steps into the lobby in blue lingerie.  I look up, and up, and up.  

"Wow.  This is like if Frodo banged Cate Blanchett," I thought.  

We sat at the bar and chatted.  She was very friendly, and made me feel comfortable.  After a quick tour of the place it was down to business.  I handed over a credit card and signed some receipts, she laid this thin paper stuff over the bed... kinda like that stuff that in on the doctor office chair.  We get naked.  Awkward city.  We talk and she gives a massage.  Her hands explore.  And I, for the life of me, cannot GET IT UP.  It wasn't that she wasn't attractive, or for lack of trying because she was very pretty and she was very... umm, talented with what she did.  I just couldn't get into it.  Maybe it was the larger than expected amount I had to fork over, or maybe the whole scenario just put me off.  But I couldn't follow through.  In every which position we tried, I had a weak half mast that was worthless.  After our hour was up, she told me it was okay and that it happened sometimes.  I didn't really believe her, but I appreciated her kindness.  She tried to make me feel better by saying, "hey, you're not a virgin anymore!"  I did penetrate.  But it didn't make me feel any better.  As I left, I noticed one of the girls who was at the bar when I came in was now in the lobby in a robe.  We made eye contact and the confused look on her face made me think she knew it was a disappointing lay.

So was it worth it?  I kept asking myself that on the drive back through the night.  I thought about it on the plane ride home.  I got back into town just in time to get to work.  I don't think it was.  And to top it all off, that girl I dated, spent money on, and did thoughtful things for from time to time just dropped off the face of the earth.  No last coffees or bye hugs.  Not even a text to say something like, "sorry, we shouldn't see each other anymore."  Nothing.  Back to square one.  But hey, there were valuable lessons learned in this experience.  It's true what they say, "life has to meet your expectations of it."  I'm keeping my head up that the next girl I meet rocks my socks.

Wow. That's an intense story. Here are my two cents ... because of course you asked for them ... dude, you've definitely got some emotional issues you need to address. I understand being awkward, but physically speaking, the way your body is reacting in scenarios like this are showing that there is something that is buried pretty deep inside of you that is preventing you from performing. You can't wait for a chick to come along and rock your socks off, because you're not even letting her get close to your feet. I would definitely start exploring some options. I'm personally not the biggest fan of therapy, but you can also try cuddle parties (which engages people in touch but having boundaries), or even learning more about the pick up artist community, which is less about just "picking women up" and more about social dynamics. Pretty fascinating stuff. Either way, lemme know if you want me to connect you with anyone. Wish you the best of luck dude. Please do keep us posted, and hang in there!! Sexuality is a HUGGEEEEE part of life, and something you should never deny yourself. Stay strong! xoxox

Got a story? I wanna hear it!!! Email me: JenFriel at TalkNerdyToMeLover dot com

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