Cast of Characters: Shyness

I’m no stranger to online dating.  Having been a computer nerd since high school, and now with a career in a tech/entertainment industry, the interwebs are a second home.  After divorcing #1, I started a profile on Match.com.  It had been 8 years since I was on the market, and as #1 was my first serious girlfriend (actually my first with just about everything sex related) I had absolutely no skill or knowledge when it came to meeting women.

This was 6 years ago, when online dating still had a negative image, as it was considered to be the refuge of molesters and the last resort of desperate women.  Nevertheless, it was perfect for me.  I could sit in the comfort of my home and browse women like I was at the supermarket, pulling the interesting ones off the shelf and dropping them in my basket.  I was a quick study and soon learned the proper procedures and etiquette to get dates and even had sex with a few of them.

Now days, I still have my Match.com profile which I check in on occasionally.  After my divorce with #2, I discovered okCupid.com, which has turned out to be significantly better than match, plus it’s free, so you know, it has that going for it...which is nice.

I emailed Shyness because she was a 97% match or something ridiculous like that, she had mentioned one of my favorite restaurants in her profile...and she was surreptitiously flipping the bird in her profile pic.  BTW, as soon as I accepted how absurd online dating is, I had a lot more fun.  I mean, potential dates can and do accept/reject you on utterly unimportant things like the position on your middle in a photo, despite all the time and effort you put into shit you thought was really important...but is in fact not.

To reinforce the point, the first 6 emails exchanged with Shyness were about Saag Paneer: a disgusting looking, but incredibly delicious Indian dish, which she had never tried.

I developed a crush on Shyness from the first time we met.  She has a fantastic smile, is really cute, and is just the right amount of nerdy.  Sushi Night was date number three, and it worked as it always does. (I’ll have to explain Sushi Night later, as it deserves it’s own post)  I discovered that Shyness has several tattoos, is soft in all the right places, and is shy about all things sex related, except giving blowjobs, which she unabashedly loves.

We have seen each other several times now, and our m.o. has been drinking and cuddling on the couch while watching nerdy TV shows, then chatting and making out till we make it to the bedroom.  I must admit I really, really enjoy my time with her, and the only thing I would change is that she is nervous/shy about smoking up with me.  Luckily, I think with the right prodding and some fantastic high sex, she will come around.

Cast of Characters: Delight

...as in Afternoon.

In the course of meeting couples with Rebound, about a third of the dates never made it past drinks.  It was usually that they weren’t what we had expected or hoped:  One or both weren’t as hot as they looked online, there wasn’t any chemistry, or one of us just wasn’t feeling it, it didn’t really matter.  If either one of us wasn’t into them, we would call it a night after the drink.  

It was on one of these one-drink dates I met Delight.  Taller, with nice curves, great natural tits and a naughty twinkle in her eye, Delight and her hubby had a _very_ open relationship.  They were both seriously dating at least one person each, on the side, but would swing together on occasion.  Rebound wasn’t in to the hubby from the get-go.  He was shy, nerdy, not particularly attractive, and Rebound gave me the no-go sign before the first round of expensive martinis had even arrived.  

I was surprised the next morning by a flirty txt from Delight.  I responded in kind, as I LOVE txt flirting; especially the witty exchanges rife with sexual undertones that are more verbal foreplay than conversation.  Delight knew how to play the game well, and by lunch we were both so incredibly horny she agreed to meet at my house in 30 minutes.

She was able to play it cool until I had closed the front door behind her, but immediately had me pressed up against it, her tongue in my mouth and her hands groping my ass.  The sex was fast and furious as she had no patience for foreplay and demanded I fuck her as hard as possible.  It turned out that was pretty hard indeed, and we literally exhausted ourselves and rubbed our sexy bits raw in the effort.

I quickly learned Delight had an olympic libido.  That despite having a husband and TWO boyfriends who all fucked her regularly, she was booty-txting me twice a week for a lunch hour of very vigorous sexing.

I found this nicely ego-inflating as I reasoned I must be a pretty spectacular lover for a woman, who has unfettered access to three other cocks, to demand repeat performances on a semiweekly basis.

Except for a week-long stretch where Delight and her hubby were being monogamous, (they needed to “put some time into their relationship”) we have been having lunch at least weekly...and by “having lunch”, I mean fucking...

...if that wasn’t obvious.

Musings on (bi)Sexuality

I have had a fair amount of experience with female bi-sexuality.

For example, both of my ex-wives were/are bi-sexual.  (a fact unbeknownst to me before getting married)  Indeed, every woman I have dated for any duration of time, except one, has been bi.
In the case of both ex-wives, it was spontaneously revealed during pillow talk that she would like to gain carnal knowledge of another woman, and had been fantasizing about it for quite some time (since puberty in the case of ex #2)

Of course, I was more than willing to facilitate the gaining of such knowledge, and turned to my trusted friend, the interwebs, for help.  I quickly found one of the largest sex personals sites on the web and we were off.
What followed, in both cases, was a brief and mostly unsuccessful foray into "the lifestyle", as swingers like to call it.  Bi-sexual sex was had, but the relationship gymnastics required to accomplish it made it too difficult to continue.

Shortly after divorce number 2, while still in my "slaying the bitches" phase, I started seeing a fantastically sexual woman, The Rebound, who also soon confessed to being bi-curious but completely inexperienced in the subject.  The next 3 weeks were filled with an amazing array of bi-sexual debauchery, as The Rebound turned out to be absolutely voracious when it came to the ladies.  We would arrange to meet a couple for drinks, then back to my house if they were a likely conquest.  Inside 10 minutes after entering the hot tub, Rebound would be naked and pouncing on the chosen prey of the evening.
I must admit, watching Rebound go at it with such gusto was one of the most fantastically sexy things I have ever watched, even compared to all the naked fun we would have with each couple once Rebound decided it was time to move the party from the tub to the bedroom.

Before this point, I had never honestly considered where I fit on the straight-gay spectrum.  I was previously a member of a particular brand of christianity which considered homosexuality a grave sin, so the thought was never entertained.  It was only after my recent conversion to agnosticism that I began to re-evaluate my self-identification as straight.

Free from religious guilt and encouraged by the ever receding social stigma, I started considering if I could be bi-sexual.  I was certain I was not gay, as I would never forsake the vagina, but I was open to testing my sexual boundaries.
Bi guys and girls have a distinct advantage over the rest of us: ie. double the opportunities.  Should I discover I was bi, I would have more sex than I could want (because guys are sluts).
I spent a couple hours perusing gay guys on okCupid, watched some gay pron, I even replaced my regular lesbian dominated masturbatory fantasies with focused thoughts of performing fellatio.  Not surprisingly, I developed a mild Pavlovian response to thoughts of male genitalia, but I was never able to respond to the male physique the way I do to the female.  The most desire I was able to muster was a strong curiosity about both performing and receiving fellatio, and an acknowledged openness to participating in either, should the opportunity arise.
To be honest, I was a bit disappointed by this conclusion.  However, I gave it a true effort and don't feel like I need to force myself to be something i'm not, just for the sake of pushing boundaries.  That said, I am proud of myself, that I could lay my male ego aside and approach such a life-changing possibility.  Who knows, I may run into someone or something that may cause me to reconsider the subject again.  In the meantime, i'll identify myself as straight, with a hint of bi-curiosity thrown in.

The Wedding Announcment

Not mine...obviously.
Bunny is a girl I have been seeing for a few months.  Well, "seeing" isn't the right word, as all we do is get high and fuck.  I met Bunny on okCupid, where she sent me an email, which led to txting, facebook stalking, and then chatting, where the conversation quickly turned to sex and getting high, and how those were both of our favorite things to do.
We met a couple days later at a bar near my place, and after a drink and some pleasant conversation I invited her back to my house.  A 5 minute drive later and we were hitting my bong and fucking...crazy amazing drug-addled fucking.
Bunny is 23, short, cute, curvy, and absolutely insatiable.  She entertains herself abusing me for the next three hours before announcing she needs to leave, as she has an hour drive home and needs to work in the morning.  After quickly gathering her strewn clothing, she gives me a peck on this lips and says "that was fun, lets do it again", then lets herself out.
We have been repeating the preceding scenario once a week since then.  She arrives around 7pm.  We smoke, head straight to the bedroom till 10, and she's off.  No talk of anything except which position she wants me in.  No chit-chat, no relationship talk, just getting high and fucking each others brains out.
I have to say, it's definitely the easiest relationship with a woman I have ever had.

Oh yes, the wedding announcement!
I was perusing facebook, as I am want to do 20 times a day, and I see a post from Bunny, how she's "so glad she can tell people that she's engaged! Moving to the NE next month!" followed by a pic of her and a boy...
A quick txt confirms that yes, she is engaged and moving away in a month, but can she see me a few more times before she moves?
I may be a slut, and though i'll never make that mistake again, I have some respect for marriage.  Luckily, she explained that they have an open relationship, he knows about me, they have an understanding about her needs, and am I busy thursday night?

kink

I recently received an email on okCupid from a not-unattractive girl in which she included a link to her fetlife.com profile.  It turns out the "fet" in "fetlife" is fetish, and the site is for the BDSM community, of which this girl is an active member.  I quickly started a profile, entering the minimum required, so I could get a peek under the curtain.
Three hours later, i'm officially interested in being tied up and spanked by this girl.  Literally two days later, I found this blog (without even looking for it, mind you) by a nice young woman chronicling her adventures in spanking.  For some reason, I had never considered myself into kink.  If I believed in karma, I might think the Universe wants me to get a good spanking.
I have since emailed and facebook friended GothGirl and have made plans to get a drink.  Maybe i'll end up tied to her bed and blindfolded...one can always hope!

My brother the man-whore

I've been out on the town wing-manning my brother twice.

The first time he successfully chatted up the two hottest girls in the bar and we spent the evening dirty dancing, later discovering they were both married.

The second time was last weekend.  Bars 1 and 2 were short on single ladies, but bar 3 was packed.  Within 15 seconds he had made eye contact with two gorgeous girls.  2 minutes in, we were behind them at the bar ordering drinks and he was chatting them up.  10 minutes in, he's grinding with the hotter girl on the dance floor.  An hour later, he has them both back at my place and is getting a strip-tease.

It turned out my girl's divorce was final three days ago, so we commiserated platonically while trying to ignore what was going on in the other room.

What is the take-home lesson here?  I'll let you know when I figure it out.

lesson learned

I had the following IM conversation on okCupid last night:

me: hey there

her:hey

me:how are you?

her:doing well, u

me:good! had a nice night out

her:good.

me:you had a nice trip?

her:amazing!

me:did you take a lot of photos?

her:im not really interested

me:in photos, or me?

her: (logged off)

This may have something to do with the previous IM conversation we had in which I encouraged her to come over and hang out...at 11:30pm on a Tuesday night...

I was stoned at the time and thought it was a great idea.  Sober me realizes that's crazy rapist talk.

No more okCupid when i'm high. 

Got to Start Somewhere

I must admit, i'm not very good at dating.  Being in relationships for 9 of the past 10 years hasn't given me much experience, so here I am in my early thirties with only rudimentary knowledge of the dating game.   I figure I might as well share my failures with the interwebs.  Wish me luck!