Cockblock-19

Just when I was getting into my stride, too.  However, nobody close to me is sick or dying or dead, so I can’t really complain.  And I’m lucky to say that, considering how close we are to the epicenter.   As of this writing there have been over 22,000 deaths in New York state alone.  The daily toll has gone down but we’re still losing 400 people on average.  Yet some people I know still think it’s much ado about nothing, a big hoax, a Democratic power grab, caused by 5G networks, or some other nonsense.

There’s no telling what effect this will have on dating once things get back to normal (whatever “normal” will mean).  Dating will either be freakishly easy because everyone will be horny and desperate after being cooped up for so long, or freakishly difficult because they’ll be more afraid of catching covid than an STD.  In the meantime I have to laugh because now everyone’s in the same boat:  can’t get a date, can’t meet anyone, can’t get laid… hey, welcome to what was my world for 30 years.

I was still swiping on Tinder and Bumble the whole time I was banging College Girl.  I felt slightly guilty but – knowing my luck – things could go sideways real fast and I wanted a backup plan.  Sure enough, things ended with College Girl, but due to unforeseen circumstances outside our control.  Maybe we’ll get a chance to hookup again, but I’m not counting on it.  However, I racked up a few more dates before the quarantine began and people started panic-buying toilet paper (for reasons still unclear to me).

#72
33 years old, from Bumble.  Another teacher.   We were supposed to meet at this indie coffee shop but they unexpectedly closed early, so we ended up at Starbucks instead.  It was an above average date.  We talked for two and a half hours and had a nice flow.  She’s one of the rare few who actually likes to compare dating stories and experiences.  But while she’s recently out of a relationship and supposedly on board with the idea of something casual, she wanted to take it slow and spend more time getting to know each other outside the bedroom first.

Yeah…that sounds more like traditional dating to me.  I don’t think that’s how this FWB stuff works.  I suspected she wasn’t fully on board after all.  She gave me her phone and told me to put my number in, but after texting a couple of times she went MIA.  Suspicions confirmed.   Although, during our conversation we’d found out I’d once gone on an OkCupid date with one of her friends (Melody, girl #23).  It’s a long story how that came up, but talk about a small world.  Maybe that had something to do with her ghosting on me.

#73
She was 46, from Tinder, and my oldest date yet.  I should have listened to my instincts and not wasted my time with this one, but I have this awful habit of giving people a chance.  The initial warning was when I opened Tinder and found two messages from her.  The first message was some general question, followed by “oh well, guess you’re not interested in meeting.  Good luck to you.”  I checked the timestamps and they were sent eight minutes apart.  Seriously?  “Geez, how about giving me a chance to respond?” I wrote back, and she sent me a facepalm emoji.

Then I suggested a place to meet.  “Are they open today?”  I answered that they should be and she came back with, “well, why don’t you put on your big boy pants and call and find out,” as if I hadn’t already intended to do so.  Normally I would have taken her passive-aggressive attitude and told her to pound sand, but I’m just looking for a sex partner right now so I’m not as fussy.   When we met she asked me lots of questions which I was happy to expound upon, but she was pretty tight-lipped when I turned the questioning around on her.

I grew irritated as we were in a noisy-as-fuck bar on a Saturday night, and I was losing my voice from having to talk louder and louder until I was almost shouting.  Meanwhile she was one of those people with no concept of traveling of sound and maintains the same speaking volume no matter the situation.  I was losing interest and the feeling was mutual.  She didn’t talk much and didn’t want to answer questions, so I turned my attention to the live music starting up – which she wrinkled her nose at.  What a stick in the mud.

Finally I called it a night and bid her adieu.  Waste of an hour and a half.  Earlier in the night I had broached the FWB topic and she was like, “this isn’t a date, it’s a meeting” and “I don’t like to put a label on things,” adding that she likes to be friends first and see what happens.   Once again… I don’t think that’s how this works.  I figure you match, meet up and see if you get along and find each other physically attractive, and move onto the fucking.  At least that’s how it works in my mind.  Am I oversimplifying it?  I don’t think so, because College Girl came right over to my place to have sex without preamble.  I struck gold with her, so I’m sure I can do it again.

#74
I had one last date (33yo, from Bumble) before quarantine started.  Once again it felt more like a traditional date, although it was a unique choice of venue – the beach in wintertime.  I never thought I’d find someone else into stuff like that.  However, everyone else in the world had the same idea because it was packed like the middle of July instead of March.  We walked six feet apart, doing the whole social distancing thing.  That lent itself to a weird dynamic, although she did venture close enough to sample the homemade cookies I’d brought for us to munch on.  We got off to a good start but by the end it seemed we were running out of things to talk about.  And that was that.  No contact afterwards.

***

That’s it for the foreseeable future.  I won’t be doing virtual or Zoom dates or any of that nonsense.  However I matched with someone on Tinder who possibly shed some light on my struggles.  First she admitted she hadn’t read my bio first, so she wasn’t interested in a FWB.  Then she psychoanalyzed me based on my pictures, telling me that I wanted kids, that I’m looking for something meaningful, and “you crave connections, bro.”  Dafuq?  Why, because I was holding an animal?  Then she went on to suggest that I retool my Tinder profile, because “anyone advertising FWB subconsciously wants something.”

Yeah.  I don’t know what to make of this – thoughts anyone?

And last but not least, I have something exciting to announce in my next post.  I’m expanding my social media presence onto Instagram.  Details coming soon…

The Virgin Mary

I gave it a month after my breakup before I re-downloaded Bumble.  I noticed a couple of changes.  First, they no longer show when someone’s read your message.  Second, they have swiping limits now.  I hit them during my first few days on the app, but haven’t since.  Anyway, I picked up a bunch of matches, albeit at a slightly slower pace than during my last few stints on Bumble.

 

#63
I thought I hit paydirt with this one.  31, Lived only a few miles away, didn’t want kids, cute as hell, and the conversation was fire.  She was willing to meet sooner rather than later, so we set a date at a craft brewery the following night.  Things seemed off from the get-go.  As soon as I showed up she was low-energy and a bit meh.  I did my best but things didn’t flow like they did online.  This has happened to me quite a few times and it’s frustrating as hell.  It’s even more frustrating when you feel like the only one making an effort.  I’ve literally made up index cards of questions and topics in the past and studied them beforehand in case things lagged.  I didn’t do that this time but – social media ninja that I am – I’d found her on Facebook and combed through her interests.  Even working some of those into the conversation didn’t breathe more life into the proceedings.  The last straw was when she picked up her phone for the tenth time and it looked like she was messaging someone on Bumble.  Okay.  I downed the rest of my drink and told her good night.

 

#64
This one definitely went better than the last.  29, also lived a few miles away, also didn’t want kids (woohoo!), but her pictures were a tiny bit suspect.  We met at a bar, and I warmed up to her over the course of the evening.  For once the in-person banter matched the online banter. We traded stories back and forth, compared dating experiences, talked about our crazy families.  We sat at the bar stools with our legs touching, and I was going to go in for the kiss afterwards but I got the cheek instead.  Oof.  Okay.   The next day I texted her to reiterate what a nice time I had, and she concurred.  I dithered about, wondering if I should ask for a second date.  In the end I took my indecision as a sign and just left it at that.

 

#65
Finally!  A great first date and an even better second date.  The two best dates I’ve had in a long, long time.  Unfortunately there won’t be a third…

She was 28, lived a little further away, cute as hell, but unfortunately wanted kids.  That came up pretty early in our online conversation, and I warned her that I didn’t and that wasn’t going to change.  So if that wasn’t going to work for her, I’d understand.  Nevertheless she persisted, but I knew this was going to have a short shelf life.  That’s okay, though – I’m open to short-term dating.

Our first date was at a board game cafe, which worked out perfectly because she loves board games and hosts regular game nights.  We were there for three and a half hours.  Afterwards we waited outside for her Uber and I put my arms around her to keep her warm.  “You know, we have time for one more thing…” I said.

“What’s that?” she asked, grinning up at me.  I leaned down to kiss her in response.  It was a bit awkward with the height difference, but it was still really nice.  We made out in the shelter of a doorway for a minute until her ride pulled up, and I skipped across the intersection as she pulled away.  Now that was more like it!  Finally, a great first date.  There was definitely going to be a second.  It was a week and a half before she had another free night, during which the anticipation was killing me.

This time we went to an Italian restaurant, putting away the food and wine for three hours.  Instead of calling another Uber, I offered to drive her home and she accepted.  Five minutes in and she brought up the whole not-having-kids issue again.  “I hate to be a debbie downer…” she began.  She’s looking to get married and have kids as soon as possible, and if I was dead-set on no kids… but she really liked me and was confused as to what do.  Maybe we could just date casually?  I said I was open to that, yet she was still uncertain.

By this time we were back at her house.  I pulled into the driveway and we sat there continuing our discussion.  She was all in a dither about things.  We interrupted our chat for another makeout sesh.  This one was pretty hot and heavy.  She tilted her seat back and pulled me over to her side so I could get on top of her.  I lost track of the time but we must have been at it for a half-hour.  She even let me feel her up and – after I confided being driven crazy by her low-cut shirt on our first date – she hiked her sweater up so I could pull her tits out of her bra for a better look.  They were awesome.

Then she dropped another bomb.  She was a virgin.  Well, I can relate to being a virgin at 29.  I even like the idea of being someone’s first.  But she told me she was a “good Catholic girl” and saving herself for marriage.   OMGWHAT?  So if we were to date casually, there wouldn’t even be sex.  Wtf would we be doing then?  I knew she was politically conservative (itself a potential issue down the road), but to be sexually conservative as well?   Yeah, this wasn’t going to work at all.  So long story short we parted ways.  Sucks because we got on so well and really liked each other.

So that’s the latest.  If nothing else I got some kissing and titty action. Now if I could just find someone like her who’s also a huge slut…

Just wondering – should I bring back the date counter?  What do y’all think?

Six years of blogging

Happy six year anniversary to my blog!  I can’t believe it’s been that long, and I’ve certainly come a long way.  I seemed to have caught the tail end of the craze though, because it’s a lot harder to find dating blogs on here nowadays.  It’s a shame that many of the ones I started with are no longer around.  One by one my favorite bloggers fell by the wayside as they found significant others, or at least better things to do with their time.

I’ve considered shuttering this blog too.   The month after I lost my virginity, my views went down by half and have continued their decline.  At my peak I received 3,000 to 4,000 views a month and an inquiry from a Washington Post reporter.  A slow day would garner 100 views, a new post would bring 200+.  Now a new post won’t even crack 100, even though I have more followers than ever.  I guess my journey is not as interesting ever since the climax.  However, I do enjoy writing and interacting with my fellow WordPressers, so I’m sticking around.

Bumble is sticking around too.  I’m on the verge of deleting it for the 20th time, though.  I don’t know why I keep trying, but until I have more luck meeting people the old-fashioned way it’s better than nothing.  I received a shit ton of matches from my recent trips into the city, but I’ve been eliminating them left and right:  Minimal and mediocre conversation?  Shitty availability?  Using the app to promote their Instagram or music and bartending gigs?  Undercover single mothers?  Goodbye.

Then I had another one of those 1 in 100 conversations.  Finally someone else that matched me in goofiness and witty banter, whom I really seemed to click with.  And then it all went to shit.  Everything was fine until she added me on Instagram and I scrolled through her old posts.   All I did was swipe with my finger for a minute or two to get to the end and texted her: “I see you were into fitness coaching back in the day?”

“Whoa, you went through my old posts??” she said.  Uh, yeah.  So what?  Who doesn’t do that when they add someone?  Was I using Instagram wrong?  It really weirded her out though.  I didn’t even like or comment on any posts, I simply asked a question.  What’s more, she had texted me a pic of her messy kitchen (due to party prep), and I had zoomed in on the background and commented on a wall decoration.   That didn’t sit right with her either – that I was looking in the background of her photos.

Add to that me playing the piano and not eating seafood, and it was too many red flags for her.  And just like that I was back to square one.  Just as well – if that’s her bar for weirdness then we were in for a rough ride.  But it amazes me sometimes – I hear so many women airing laundry lists of serious grievances about their men, yet they still date them.  Meanwhile, I’m put through the meat grinder for the silliest, nitpickiest little shit.

In some ways I feel like I’m still in the same spot as when I started this blog.  Yes, I’ve finally swiped the V-card.  However I’m still yearning to put at least one long-term adult relationship under my belt.   And I’m going be 35 this year.  Once again I wonder why it hasn’t happened yet and why it’s so frustratingly hard for me.  And I feel like I have a lot to offer the right person.

I have a job, a car, my own place.  I can cook and would love to do so for someone.  I’m cultivating hobbies and a social life.  I can communicate, as well as respond in a timely fashion.  I’m honest and open about my feelings.  I do my best to get to know the other person.  I’d be a supportive partner.  I’m not argumentative but I’m no pushover either.  When it comes to the bedroom not only do I have good stamina but I’m eager to please, ready to learn, and open to trying new things.  I know how to have a good time and plan fun activities.  I like to think I’m funny.  I even think I’m somewhat good looking.

Of course there’s always room for self-improvement and I’m always looking for ways to do so.  But I feel like there’s more working in my favor than against.  I just don’t seem to have that elusive “it” factor yet.  I don’t know.  In the meantime I’m going to do my best to meet people and keep putting my best foot forward.  We’ll see what happens.

My pants came off

For a hot minute I thought I was going to get laid again, I really did.

I made a snap decision to rejoin Bumble a few days before Christmas.  However I was tiring of the crap I was wading through and I remembered my hookup over the summer. I could do that again, I thought.  I definitely missed sex.  And while I’d ideally like to find something serious, if something like that came along I’d definitely consider it.  So I posted a picture of me in a holiday suit, declared I wasn’t looking for anything serious,  and joked about having a Red Room of Christmas, donning a Santa hat and engaging in elvish kinkery.

#56
I created my profile at 8 in the morning, and within a couple hours I already had an interested party.  She was 28 and lived a few miles away in my old hometown.  We met for coffee that afternoon.  Profile creation to first date in five hours.  That’s a new record.  She was cute as hell and even better looking in person.  We chatted for an hour before parting ways with a quick kiss.  Her lips felt amazing.  I actually got hard, not going to lie.  I would have kissed her longer but we were outside and it was pouring rain.

The plan was to meet for drinks the next night and then back to my place. She wanted to see this Red Room, or at least this kinkery of mine.  We would have done so later that day, except she was stuck with the kid for one more night.  That’s right, she was a single mother, which for me made her a candidate for something casual.  However it was not to be.  We messaged back and forth the rest of the day and then my last message went unread (Bumble now indicates when your messages are read).

A week went by with no further response from her, so I shrugged and unmatched with her.  Then I put my Bumble profile back to semi-normal, excising the lines about not wanting anything serious and engaging in elvish kinkery.  It was funny while it lasted.  A week later I came across her on Instagram (turns out we have a mutual friend) and noticed she’d updated her bio to include the handle of the guy she was now dating.  Well.  That was fast.

I took another trip into the city the weekend after Christmas, bouncing all around Midtown and the West Side before heading back home again.  It seemed like everybody in the world had the same idea to go into the city that day.  What a zoo.  But I had Bumble running the entire time I was in there and I returned home with 90 matches.  Within a couple of days I had whittled it down to a couple dozen and two or three hot prospects.  I set up another date later that week.

#57
This one was 28 and lived a bit of a distance from me.  We picked a halfway spot at Dave and Busters.  For those of you who don’t know, D&B’s is basically an adult arcade, along with a bar and restaurant and bowling alley.  I got there before she did and she messaged that she’d be there in a minute.  A minute later a girl walked through the doors, glanced in my direction and continued inside.  Her phone was in her hand and I noticed Bumble on the screen, and she was turning this way and that looking for someone.  Was that her?  She looked a little like my date.  I dithered about and finally went to ask her, and it wasn’t her.  Oops.

I got back to the front doors just in time for my real date to walk through.  Ah.  This was definitely her.  She looked a little different in person but it was definitely her, and she was definitely cute.  I liked, and I admired her assets as we sat at the bar and took off our jackets.  We had a drink before proceeding to the games.  I held my own but she whooped my ass at most of them, and as we waited for the basketball hoops to open up I put my arm around her and she immediately reciprocated.  Yes!  That was a good sign.  And I got hard again.  Seriously, that’s all it takes with me sometimes.

We bowled a couple of games, had something to eat in the restaurant, and then browsed the shop to see what we won with all the points we’d earned.  Not enough for anything good unfortunately.  But we’d been there for four hours so we called it a night.  Outside I gave her a hug good night and then I went in for a kiss.  Second first date in a row that I went in for a kiss.  I have no qualms or hesitation about doing so now.  However all I got was a quick peck.  Huh?  I went in for another.  Another quick peck.

I was so surprised that I very nearly said, “That’s it…?”  We had such a great time and she seemed to have really enjoyed herself, laughing and joking around with me and touching me in return.  I thought for sure she’d be into more than a lightning-fast smooch on the lips before doing the familiar trot across the parking lot to her car.  I said good night and drove home with a pit in my stomach, replaying the entire night in my head and second-guessing everything I had said or done.

Then I waited.  Sure enough I got the following message the next day, right on schedule:  ““Hey! So sorry it took so long to get back to you. I had a lot of fun, thank you for a nice evening. Unfortunately I don’t think we’re the right match. Best of luck!”  Dammit.  What the hell?  That stung.  Sigh.  Well, at least I still had a large pool of matches to draw from.  The next weekend I was back in the city, this time to meet one of my matches from the previous weekend.

#58
This one was a 27yo au pair from South America.  She worked for a family on the Upper West Side, so we met at this place called Mom’s Kitchen not far from Restaurant Row.  We met out front and she looked just like her pictures, but seemed a bit quiet and passive.  Hmm.  Things got off to a slow start but eventually warmed up to a semi-decent conversation.  But despite her proclaimed excitement about going to a place with all-day brunch, she ordered… a salad.  FFS, really?

There was an Irish pub down in Hell’s Kitchen called O’Neills with live Irish music, so I said I was going there and asked if she wanted to join me.  Basically I gave her an out, because I wasn’t sure what else to do with her and I wanted to ensure that I at least had a good time.  However she elected to come with me and I bought her a drink, and we took a seat near the back where it was quiet enough to talk but still able to hear the music.  Eventually I ran out of things to talk about with her, and she asked me very little in return.  Yet she stuck around.

We were there until midnight when the session ended, and before it did I jumped up and danced around with the rest of the group that was dancing to the music.  She seemed totally unimpressed and uninterested.  The hell with her.  I was still going to have fun.  It was another four hour date for me, and I walked her back to her subway stop.  Nice to meet you, hug good night, and away she went.  Then I took a seat in Times Square and started swiping, collecting 30 more matches before I started walking again.  (Full disclosure: I indiscriminately swipe right and filter them out later.)

The Nanny continued to text me for the next few days before things dropped off.  I was surprised she did, because I didn’t think she was really interested in me.  I’d decided I wasn’t.  Plus the whole time we were out she didn’t make one motion or suggestion to split the bill, or offer a round of drinks on her or anything.  Maybe it’s a cultural thing, but it left a really bad taste in my mouth, especially considering the distance I covered to meet her and the time it took me.

And finally, I come to the story behind the title of this post.  This past weekend I took part in Improv Everywhere’s No Pants Subway Ride.  It’s a public prank that is exactly as it sounds.  I’ve wanted to do it for a long time but missed it each year.  This year I finally made it.  There were six starting points around the city and I chose the Great Hill in Central Park.  Hundreds of people showed up, and were divided into groups and assigned subway cars.  Of course I was sorted into the group without any of the cute girls that had gathered.

From there we took the C train to Times Square, and switched trains to go to Union Square.  The looks people gave us were priceless, but since the event garners a good amount of media coverage it’s not such a surprise anymore. In fact we had a reporter from one of the major networks embedded with my group.  She didn’t take off her pants though.  I on the other hand relished the opportunity to show off my sexy legs.  The gym has been paying off.

There was an impromptu pantsless dance party in Union Square despite the cold, and I stuck around to watch before putting my pants back on and going down the street to gorge on junk food.  I spent the third weekend in a row swiping on Bumble and collected 80 matches.  This time, though, it was early enough to meet someone before heading back home.

#59
She was 39 and lived on the Upper East Side.  Coincidentally my sister and her boyfriend were also in town, over at a rooftop bar in the meatpacking district.  So I met them for a quick drink before meeting the latest Bumble chick.  When I told her I was gorging on junk food she was like, “you should have invited me!”  Well, I can always squeeze in more, I told her.  She said there was a Shake Shack near her so that’s where we met.  Man, I love me some burgers.  At least she didn’t order a salad, but all she had was a burger with a glass of water and no sides.  Women don’t like to eat on dates, do they?

We talked for an hour about our lives, families, politics and culture.  Stuff like that.  And only for an hour because she said she had to get up at 4:45 for work.  Hmm. Okay.  I know what that means when they call it a night after only an hour.  Sure enough, she unmatched with me on Bumble afterwards. Oh well.  Guess I failed to make a good impression.

So that’s all for now.  There’s more to write about, but this post is long enough as it is.  I’ll save it for the next one.

New and Improved

Your boy has been quite the social butterfly over the past few weeks.  First I went into the city to see an old friend perform with her band.  I hadn’t seen her in at least ten years and she looked the same as ever.  After the show we went out to eat at a soup and burger place just down the street.  It almost felt like we were on a date (except I’m not attracted to her like that).  Then we took a cab back to the train station.  My first ever NYC cab ride.  There’s an item that wasn’t on my bucket list.

Next up was a wine and cookie swap.  The guest list was mostly female and I didn’t want to miss out.  Plus it was an opportunity to wear my ugly Christmas sweater, and several others wore theirs too.  (Closest I’ve gotten yet to an ugly sweater party.)  Procuring wine was easy but we were required to bring homemade cookies.  Well, I’m a bit of a whiz in the kitchen so I had no trouble making my first batch ever.  They were a hit though, so now I can add baked goods to my list of talents.

We spent most of the night playing “Have You Ever?” type drinking games – all of a sexual nature.  In the past I would have excused myself to save face, but I was  happy and relieved to be able to take part now.  I’m no longer on the outside looking in.  However my cup sat mostly idle in my hand.  I watched the others – including the two other guys that came with their girlfriends – take drink after drink in response to the questions.  There are a LOT of things I haven’t done yet.

I recently turned 34, but sometimes I feel like I have the sexual and dating development of a 21 year old.  At the very least I wish I was in the place I am now at that age.  As the game unfolded I sized up the others, especially the guys.  They didn’t seem that different from myself, so how did I miss out on all this stuff?  Why am I still lagging behind?  And the girls… turns out they were pretty freaky, especially the one sitting closest to me.  She was cute as hell and caught my eye, but she barely acknowledged my presence.

The conversation later turned to astrology and her friend asked me if I was a Sagittarius.  Surprised, I answered in the affirmative and asked how she knew.  “I could tell by the way you walked in.  You were working the room.”  I thought I’d walked in normally, but I’ll take it.  Wasn’t sure how to respond to that.  The matter was forgotten entirely when Frosty the Snowman came on and I made a wisecrack about that being the next holiday song people take offense to: “Next year it’ll be Frosty the Snowperson.”

The guy next to me took the opportunity to chime in with his thoughts on sex and gender and rape culture.  Turns out that Astrology Girl is also a super-feminist sex therapist and women’s studies professor and she just went off on him.  Oh boy.  They went back and forth for ten minutes until she finally threw up her hands and stalked off to the kitchen in high dudgeon.  She later ditched out with her cute freaky friend to hit up another party.  Oh well.

Aside from that it was a rollicking good time, and I went to another party the next day.  This one was a White Elephant.  I’m learning about all new kinds of parties now.  It was also a potluck so I brought my garlic roasted potatoes.  They were a smash hit.  But with the exception of the co-host it was a total sausage fest. I still had a good time.  I went to another holiday party later in the week, spent Christmas Eve with the family, hosted a couple of people for New Year’s… and now I’m just about partied out.

In other news, I’m on vacation from now until April.  So I’m using the time off from work to cultivate my hobbies and get things in shape around here.  I’ve already fixed my car, bought my mother a new car, redid my kitchen (complete with new table and chairs), went to a jam session, restarted my gym program… all within the first week.  I’m kicking ass over here.  I’m even thinking about getting back into dancing once classes resume on the 29th.

But while I’m putting my place in order, I’m being mindful of things.  I once read that if you want someone in your life, make sure there’s space for someone in your life – literally.   Leave an empty drawer or closet space for her to put her things, make sure there’s room to get out on her side of the bed, etc.  While I’m not looking to live with anyone, I do want to make sure things are clean, comfortable and accessible should I have an overnight guest in the future.

I also read a Wall Street Journal piece on Peter O’Sullivan, a former Google exec who went to great lengths renovating his house to accommodate a future family.  “He asked for two kids’ bedrooms and lots of bins for toys. In his master bedroom closet he created spaces for high-heeled shoes; in the master bath he made velvet-lined makeup and jewelry drawers, going so far as to wonder whether his future wife would wear hoop earrings or bracelets. Realizing he tended to date women around 5-foot-7 in height, Mr. O’Sullivan asked that all the home’s furniture and cabinetry accommodate [that].”

“In early 2008, when everything was all planned out and designed and the house was under construction, Mr. O’Sullivan met Nava Gabbay, a cosmetic dentist. On an early date, Ms. Gabbay got a peek at Mr. O’Sullivan’s then-unfinished home and said she was impressed by his thoughtfulness in creating spaces for kids and a wife. ‘I thought he really had his act together,’ she said. They got married in 2009, just after the house was finished, and now live there with their 8-month-old baby.”  So while he may have taken this to an extreme, it did work out for him in the end.

And finally, I intended to break from Bumble at least until after the holidays, but I broke down a few days before Christmas and found myself back on the app.  That means I have some more dates to blog about.

Serial dating

Well, guess who was back on Bumble and scored a bunch more dates?  Yours truly.  Yup. I know, I know… I keep saying I’m done forever and never going back, yet I keep returning every few months like an Alzheimer’s patient.  I guess deep down I think a 3-6 month break to regroup will result in better luck next time, but (spoiler alert!) I still haven’t cracked online dating.

Of course, I wasn’t taking it seriously this time either.  I put up a joke profile in order to collect more funny screenshots of my conversations.  However I also collected dozens and dozens of matches along with my first hookup, so maybe I was onto something. People appreciated my sense of humor so I started screening them for first dates.  If they enjoyed a pic of me sitting on the toilet reading the bible, then maybe they were worth getting to know.

#51

First one up was a 36yo teacher from a few towns over.  We met at a bar/restaurant where I’d met a few other dates from the same area.  She came across way older and more mature than I expected.  I felt like I was having a sit-down with one of my teachers from high school.  It was a little off-putting.  We sat and drank and talked about a bunch of shit for two hours and… nothing.  Didn’t feel anything.  We called it a night and she told me to call her if I wanted to get together again.  I think she was just being polite, but I wasn’t interested.  However she did introduce me to Blue Moon.  Pretty tasty and went down very easily.  I put away two of them and ended up very giggly.  After the date I had to sit in my car for a while before I felt ready to drive home.

#52

Next one was a 29yo social worker.  She lived locally and we went to the nearby crepe place – another venue I’ve met a few dates at.  I approached this one with caution.  All of her pictures were from the neck/cleavage and up, so you know what that means.  She was waiting outside the place, and I parked a little bit away so I had to time to appraise her as I approached.  “Hmm… okay, I can work with that,”  I thought to myself.  Things got off to a strong start conversation-wise but dropped off after a while.  We were only there for an hour, hour and a half at most.  I was mildly interested in seeing her again and reached out afterwards, but no response.  Another girl down.

#53

34yo, worked in sales for some health product company.  And she was a former Mormon.  Very interesting.  We had similar strict religious upbringings, so we could relate to each other a lot.  She was even more sheltered than I was though.  She was a recent transplant from the city and lived in a town that I knew very well.  Unfortunately, I didn’t know it as well as I thought because the mac and cheese place I took her to was still under construction.  Whoops.  My internet research told me it was open.

Fortunately I knew a sports bar in the center of town.  In fact, it was yet another place I’d taken a few dates to.  Apparently I have regular date spots, but they’re good spots so why fix what’s not broken?  And they had a mac and cheese dish she really liked so… hero!  I was rather taken with her too.  She was the hottest girl out of this latest bunch.  But I was relaxed and comfortable with her and conversation flowed well.  Only at the very end of the two hours did things start to peter out.  I suggested another place just down the road, but she passed. Damn.

We walked to the parking lot, exchanged nice meeting yous, hugged good night and went our separate ways.  We stayed in touch for a couple days and then things fizzled. Oh well.  I thought she might have been fun to spend more time with.  But she also might have been a bit too conservative for my tastes.  I don’t mean politically, because we covered that topic on our date and we were mostly on the same page.  I just need someone with a bit more edge.

#54

29yo lawyer, and you know what lawyers use for birth control… their personalities.  Okay, it wasn’t that bad.  She looked just like her pictures and it was pleasant enough, but she was kinda “meh” to me.  Apparently the feeling was mutual because while I did my best to keep the conversation going, she hardly asked a single thing about myself.  At least she bought her own drink while I had myself another Blue Moon.  She called it a night at 9:30.  Then we walked to the parking lot, exchanged nice meeting yous, hugged good night and went our separate ways.

 #55

I seem to be see-sawing between 29yo and 34yo here.  This one was 34 and worked in the events and activities office at her college.  And she lived all the way in Brooklyn. Oof.  Apparently we matched due to one of my trips in and out of the city.  I normally wouldn’t consider someone that far in, but she was being all flirty and winky in our conversations so I thought it was worth investigating.

We met at a halfway point but the place we agreed upon was noisy as fuck.  Oh hell no.  I suggested a bar down the street which had live music but was marginally better.  This is why I don’t like to do bars for weekend dates.  I want to have a nice, relaxed, fun and flirty conversation – which is hard to do when you have to shout everything.  Not to mention I have to sit or lean in so close to hear that I feel like I’m invading personal space.

She looked great though.  She also had some of the spirit and energy I was looking for.  That was because she was a stereotypical Italian.  Yappity yappity yappity.  Never a quiet moment with her.  But she was a bit of a conversational steamroller, crushing all other words and sentences in her path.  Between that and the increasing volume of the place (I swear the guitarist was increasing it one notch after every song) I was getting aggravated and not feeling things anymore.  After two hours I also had a headache.

I called it a night.  Then we walked to the parking lot, exchanged nice meeting yous, hugged good night and went our separate ways.  The usual story.  I debated with myself on the way home, wondering if I was making a mistake casting this one aside.  I kinda liked her, but I didn’t think I could manage the distance.  I also wasn’t sure what else I could do with her.  I slept on it, and when I awoke in the morning I realized I was fine with not seeing her again.

***

I got along really well with the next girl I talked to.  Twice I tried to set up a first date but she kept sidestepping my attempts.  Finally she confessed that she connected with someone else and wanted to explore things.  Okay.  Goodbye.

The next one lived even further away than Brooklyn Girl, but she was the first one in ages to match me in silly and witty banter.  We talked for two weeks and set up a date for a Sunday, but she developed cold feet a few hours beforehand.  First she made noises about rescheduling, then asked if I didn’t prefer to meet someone closer?  She went on and on about how she doesn’t typically meet guys from my area, this isn’t going to work in reality, etc. etc.  Jesus.  This didn’t occur to her at any time before during the past two weeks?  The whole thing collapsed like a house of cards, but on the bright side I ended up with a Sunday all to myself.

And lastly, I had a really hot prospect that I was talking to for the past three weeks.  We even graduated to the phone and had hours-long conversations, something I’d never done before.   I was really excited to meet her and we were supposed to meet this past Saturday, but she went cold turkey on me come Thanksgiving.  I texted her a couple of times over the weekend and got no response.  So I have no idea what happened, but I figure someone more interesting came along.

That’s all for now, folks.

Hookup

I’ve read so many blog posts about them over the years, but never did I think I would have a hookup of my own to write about.

It all started a couple of months ago.  My niece and I were talking about dating and swapping stories… hard to believe sometimes that she’s 21 now.   Even harder to believe she’s on Tinder.  She even pulled out her phone and swiped left and right through a bunch of guys.  Very, very interesting watching the process on the female side.  She showed me some of her conversations too.  Not to be outdone, I showed her screenshots of my old conversations.  She really got a kick out of them – so much so that I decided to go back on Bumble with a joke profile and collect more funny screenshots.

This went on for a couple of weeks when one day I got a message at 4AM:

“Hey Tommy, seems like you got low enough standards for my liking :)”

“And apparently we’re both night owls,” I wrote back.

“I think I should say that I have jet lag.  But the truth is…”

“You’re horny…?” I suggested.

“A bit.  Fancying some good old fashion missionary.  Ok… or maybe I will be on top for a little.”

Okay… this had to be a joke.  Someone read my profile and was clearly fucking with me in return.  I even suspected it was someone I knew in real life.  Plus she only had one picture, which is usually a red flag.  But we chatted until the sun rose, and during the day she sent me photos of herself in various states of undress.  After less than 24 hours of sexting and steamy conversation, I met her in a bar in Brooklyn.

#50

Right up until I walked through the door, I kept thinking it was too good to be true.  I half-expected to see one of my friends sitting there, although I doubted any of them would travel all that way just to play a prank.  And the more I talked to her online, the more confident I was that I wouldn’t end up meeting some 40yo hairy fat dude.  But sure enough, she was a real person, sitting right at the corner of the bar in blue jeans and a black top just like the said she would be.

Phew.  And wow.  She looked better in person than I imagined.  Except when I tapped her on the shoulder and said her name, she didn’t look entirely enthused to see me.  Uh oh.  I greeted her and told her I had to use the bathroom and I’d be right back.  After the long drive into the city I was fit to burst, and I went downstairs and pissed a bucket.   When I came back upstairs I wondered if she was going to give me the “you seem like a nice guy” speech and nix the rest of the evening.

She didn’t.  I ordered myself a drink and we took a seat in a booth away from the noise.  She had a beer of her own but didn’t seem very interested in it.  We made chit-chat about nothing in particular, and I was surprised to detect an English accent despite her being Chinese.  But she grew up in Hong Kong, and studied and worked in the UK, so apparently that was why.

After about 10-15 minutes I asked, “Do you want to get out of here?”  She did and we got up to leave.  I knew she had a hotel a block away, but I insisted on meeting somewhere neutral in public first.  As we walked outside I was waiting her to change her mind and wish me good night (as is my luck), but instead she hooked her arm around mine, eventually hugging it with both of hers.  Oh!  Looks like she was interested after all.  She warned me beforehand that – despite her online sluttiness – she was likely to be awkward and shy in person.

To be sure, as we walked down the sidewalk she kept stopping to stare at me with a weird grin.  I kept asking her “What…?” and she kept asking me why I was giving her weird looks.  Uh, because YOU are.  After the third time I turned and put my hands on her waist, and she continued looking up at me with that weird grin.  This seemed like the moment.  I moved my hands up to cup her face and went in for the kiss, but at the last second she turned her head and I got her on the cheek.

Oof.  More awkward.  She wrapped her arms around me and buried her face in my shoulder.  Okay.  What’s the deal?  Well,  apparently she doesn’t kiss on the lips.  Okay there, Pretty Woman.  I didn’t get much more out of her than that, although she later confessed that kissing doesn’t do anything for her.  I didn’t know that was possible, but there are all types I guess.  Maybe the other guys she’s been with were bad kissers? Who knows.  And before we resumed our walk back to the hotel, she blurted, “I might even like you as a person.”

pw
“I don’t kiss on the mouth.”

“Well, I’d hope that you’d like me as a person.  I’m not just a piece of meat, you know.”  She let out a loud giggle and quickened her step until we were almost race-walking.  We went right into the elevator and up to her room.  She swiped her card and in we went, with me in a bit of a daze.  This was totally surreal.  Was this really happening?  Never in my wildest fantasies did I imagine something like this could be a reality.  And from my ridiculous online dating profile!

She was still a bit awkward, which was making me awkward.  I’d vaguely pictured myself making out with her and slowly removing her clothes piece by piece.  That kind of foreplay is important in helping me determine what someone likes.  But with kissing off the table, there went one of the tools in my toolbox, and it was a bit of a buzzkill as well.  Plus when I looked up from taking my shoes off she was already pants-less.  Somebody was eager to start, apparently.

There was a bit of fumbling about and then we were lying on the bed, first side by side and then me on top of her.  There was more awkward fumbling about as I tried touching her lady parts, but couldn’t seem to get that right.  First she told me to be more gentle, but then she was pressing my hand into her indicating I should use more force.  Then she put one of my fingers inside her, but after a minute of that she wanted my fingers on the outside again.  Finally I hit pay dirt when I started sucking and kissing on her neck and tits.  All girls seem to like that, but she was practically orgasming from it.

We were a bit limited in what we could do.  In addition to no kissing, there was no oral either – for her or for me.  So that basically left condom-only P-in-V sex.  She couldn’t wait any longer and wanted my dick inside her, but she didn’t think she was wet enough.  After leaking pussy juice profusely for an entire day, she was running a bit dry.  But I put on a condom and she slathered lube everywhere, and then we started fucking.  Finally, an area I seem to excel at.  At least, I’ve never gotten any complaints in that department.

She got really wet before long, and it felt so good being inside her.  (Skyn condoms are great, btw).  I’d already jerked off twice that day looking at the pics she sent me, so I lasted a decent amount of time before I unloaded in her.  It was really intense.  I don’t remember it feeling that intense with my ex Rebecca, but it’s been so long that it’s hard to remember exactly.  She came too – loudly – and it was funny because even though she sounded British she would orgasm in Chinese.   It was like I fucked her into another continent.

Afterwards we lay there for the longest time, just talking about stuff. She asked me a million questions, including, “Am I asking too many questions?”  She dropped a bomb about being divorced. She also claimed I’m the first person she’s had sex with in two and a half years.  Wow.  So she’s had a longer dry spell than I’ve had.  Who would’ve thought?

All the while we played with each other’s hands, stroked each other’s arms, and touched each other all over. I gave her a back and shoulder massage because I love doing that.  The entire time I did my best to relish every moment, telling myself that it might be a long time before I get to touch anyone like that again. Sure enough, I remember thinking that exact thing when I was with my ex, and then two years went by.

Eventually she started jerking me off, but it wasn’t doing anything for me. She didn’t have the right touch, even after I gave her some instruction. Then she was telling me to cum even though I was nowhere close, and her telling me that had the opposite effect.  It’s like when the doctor asks you to pee in a cup, and the more you try the more you can’t do it.  Then you start feeling pressure, and in this case I was starting to go soft.  She noticed and started making efforts to get me hard again, which also had the opposite effect.

Shit.  I went back to work on her neck and chest and soon I was almost rock hard again.  We had sex a second time, we both came again (her at least twice) and we managed to snag a couple hours of sleep before morning.  We tried some other positions but they weren’t really comfortable for either of us, so it was mostly missionary. There was one more round of equally satisfying sex before I had to hit the road.  It felt a bit weird waking up in the city, and I drove home in a bit of a daze.  That might have been more due to exhaustion, as I had to pull over and take a nap for an hour in order to make it the rest of the way.

I didn’t jerk off for the rest of the week.  We met for Round 2 the following weekend, and I wanted to save up an especially big load for her.  This time I met her right at the hotel.  She left a key at the front desk for me so I went upstairs and let myself in.

She was waiting in bed in a black lace negligee.  “John McCain died,” were her first words to me as I entered the room.  Wow, you really know how to turn a guy on.  But I did enter a celebrity death pool at the beginning of the year and he was on my list, so he earned me 24 points.  Yay for that, at least.

We got down to business right away.  I was more than ready for her.  I attacked her neck and chest and played with her pussy.  “How did you get so much better at this in only a week?” she gasped.  Easy – I simply remembered what she liked and didn’t like from last time.

Things went a lot smoother this time, and there was no need for lube whatsoever.  She was positively dripping downstairs.  She wasn’t kidding about that. I’d never seen anyone get wet like that – not that I have much experience to judge, though.

Finally she couldn’t take it anymore.  “Get a condom,” she gasped.  I did, and ten minutes later I filled that bad boy to near bursting after not jerking off for an entire week.  But truth be told, I didn’t need to jerk off.   After the previous weekend I found myself feeling fully sated and satisfied.  I didn’t even look at porn or anything.  However, I was ready and raring to go now.  She came many times, and after the third round of sex she took the baby oil I brought with me and dumped it everywhere.  She proceeded to massage my body with hers.  It was amazing, and she ended by jerking me off until I spurted a fourth time. Practically repainted the ceiling.

She wanted to keep going.  Unfortunately, the spirit was willing but the flesh was weak.  I was surprised and disappointed I couldn’t go more than four times.  Apparently sex is more intense and draining than regular ol’ masturbating.  We’d also been at it for five hours by that point.  And we were getting pretty hungry, so we got dressed and headed out to the diner.  She watched in amazement as I downed a plate of pancakes, a bowl of home fries, ham and eggs, and a bagel.  Apparently sex also whips up quite the appetite.

We held hands on the way there and back, which was really nice.  Honestly, I was almost as happy holding hands as I was to have sex again.  I miss that kind of touch and intimacy. We learned more about each other as we walked and talked, and I also learned that a lot of people leave books outside their homes in Brooklyn.  Apparently this is a thing they do there.  I suppose it’s a take-a-book, leave-a-book kind of thing.  Heh – maybe they should call it Booklyn.

We got frisky when we were back at the hotel again.  I was ready to go a fifth time, but exhaustion overpowered us and we fell asleep.  We did have one last glorious round of sex in the morning.  I woke up with her hands on my penis.  In fact, she could barely keep her hands off it all night – even on the way back from the diner.  She said she couldn’t resist squeezing it and that I had a really nice one.  Why thank you.  I think it’s rather swell too, if I may so myself.

And thus ends the best two weekends I’ve had in a long time, and certainly among the best ones I’ve ever had.  She was only in town for ten days and we made the most of her time here.  Now she’s back home.  There’s a possibility she may return in the future, but when that will be I have no idea.  In any case, my scratch has been itched and I’m feeling exceptional nowadays.

Fish

I had the best Fourth of July in a long time.  My sister’s boyfriend has a place at the beach and we went there for a barbecue.  There was a professional fireworks show at dusk, but the neighbors up and down the beach lit huge bonfires and set off their own fireworks.  It was like being at a tennis match; I didn’t know which way to look.

Actually I knew which way I wanted to look.  It was everything I could do to not stare at the brunette beauty by my side.  My cousin is dating this chick, and this chick has a daughter.  Well, the daughter and her friends unexpectedly showed up at the party.  Turns out she’s close with my sister’s boyfriend’s family.  Talk about a small world.  Maybe it’s fate.

She and her friend and her friend’s boyfriend spread a blanket out on the sand when the fireworks started.  I brought down a plastic lawn chair from the deck for myself but she said, “You can sit with us if you want, there’s room right here.”  She patted the spot on the blanket next to her.  Well, I Frisbeed that chair into the sand dunes.  I don’t shy away from opportunities anymore.

Her friends cuddled and canoodled in front of us, and I was seized with a strange urge to put my arm around her.  It almost felt like we were two couples on a double date.   I hadn’t seen her in a long time and she is quite a knockout.  But I kept my composure.  Stay cool, don’t say or do any dumb shit…  I just leaned back on my hands, and as soon as I did another crazy thought entered my head:  How much do you wanna bet she touches my hand?  I waited in that pose to see if my hunch was correct.

Sure enough, a few minutes later it happened.  She shifted her weight on the blanket and put her hand down right on top on mine for a moment. “Oh, sorry,” she said.  “That’s okay,” I grinned to myself in the darkness, wondering if that was an accident-on-purpose or what.  And now my brain was going into overdrive.  Would she or could she be interested in me?  We’re potentially step-cousins, or something.  I might not just get friend-zoned but family-zoned.  There’s also an age difference (which doesn’t bother me).

Still, I chatted with her trying to feel things out, until my sister came along and interrupted and wrecked my flow.  Thanks a lot.  We rubbed shoulders a couple more times that night.  Afterwards we started following each other on social media.  I’d like to get another conversation going but she’s rarely online.  A bit unusual for someone her age.  Damn.  This girl is intriguing.

***

In other news, I was looking forward to attending a friend’s pool party but it was canceled.  Shame, because according to the Facebook guest list there would have been a number of attractive single ladies there.  Figures.  Just my luck as always.  I was working out like crazy in preparation, but getting in better shape never goes to waste.

And in other news,  I ran into a spot of bother with the girl who cuts my hair.  I’ve had her as my stylist three times in a row now.  I like the familiarity, and it turns out we went to the same high school.  I couldn’t find her in my yearbook (would have helped if she remembered what year she graduated – how do you forget that?), so this time I asked what her last name was.  When she told me I suddenly realized: “Oh, you’re Deborah’s sister!” I exclaimed.

She put her hands on her hips and gave me a look.  “Okay, first of all, I have a name.  It’s Mandy, it’s not ‘Deborah’s sister,'” she said.  I just stared back at her in the mirror. Didn’t seem like she was trying to be funny.  I said nothing, partly because I was trying to figure out if I was somehow being an asshole, and partly because I didn’t want to get a shitty haircut.  Still… my brothers are well-known in certain music circles, and when people find out I’m related they go, “Oh, you’re Johnny/Patrick’s brother!”  I just say “yeah” and that’s that.  I don’t get snooty about it because I don’t see a reason to.

I dunno, maybe it had something to do with her being a “strong, independent woman.”  She gave a speech about that during one of my haircuts.  Maybe it’s me, but I feel like if you’re such a strong, independent woman, then you don’t need to tell everyone about it.  But she had ranted how men suck and “can’t handle strong independent women.”  I’ve heard quite a few women make that claim.  While I’m sure it’s true in some cases, it’s more likely your confrontational or bitchy attitude that sends men running.

Anyway, I promised a post on the subject of having kids.  That’s still coming up next, I just got a little sidetracked.

Downtown

So, my next post was supposed to be about politics and dating, and indeed I have several pages of rambling notes I’ve been agonizing over. I’ll get to that post eventually, but I have to write about something else first.

I met someone new.  Here’s how it happened:

It all begins with Winery Girl.  We still talk on occasion even though she’s had a boyfriend for the past two years.  Funnily enough, she actually took his virginity.  He had to wait six months to have sex with her though because – as she put it – she’s not a whore.  Uh… okay.  I wasn’t sure what to say to that.

She’s not too crazy about her boyfriend.  He’s basically a seat-filler because she can’t stand the thought of being single again.  She’s also been using the BFF function on Bumble to find new female friends.  She’s having a hard time of it, since all she sees are girls with nose rings and that’s a huge turn-off. I know that because she’s been griping to me and sending screenshots.

Winery Girl dared me to go back on Bumble to see how many nose ring girls I could find.  Ok, why the hell not?  I thought it might be funny.  And since I was treating the whole thing as a joke, I put in next to no effort.  I only posted one (albeit unique) picture and put one sentence in my profile.  Within a couple of hours I had nearly 40 matches from my careless swiping.  I hid my profile before things got crazier.

I spent the new few days culling the herd.   I decided that if I was going to entertain anyone on the app, then they’d better stand out.  A good portion expired without a message.  Many messaged with nothing more than “hi” or “hey” or “what’s up” so I deleted those.  Several messaged me and I responded, only to hear nothing further.  I deleted them as well.  The remainder matched me in goofiness and witty banter, and Jane was the finalist (no nose ring, btw).

#43
We got on so well that I asked her out, despite my original intention not to ask anyone out.  (Yeah yeah, I know…. so much for swearing off online dating.)  Our first date was a few days later at a wine and cheese place, and we were as fun and flirty in person as in text.  However she had a few more extra pounds than were evident in her photos.  Hmm… well, okay.  Not enough to be a deal breaker.

It was light and easy and comfortable with her.  I could relax and be myself.  Still missing that spark from meeting the old-fashioned way, but still better than most other online dates.  We spent a good chunk of our first date planning future dates, and we were at the place until closing.  I walked her back to her car, which happened to be a few spaces from mine.  We stood there talking until the well ran dry and then there was a slightly awkward silence.  “I don’t know what happens now,” Jane giggled nervously.

I did.  I wrapped her in my arms and kissed her. I didn’t hesitate or wonder if I could or should, I just went for it.  I wasn’t even nervous.  Big change from when I was going on dates three years ago.  She really got into it, too.  Almost immediately she was frenching me and running her fingers through my hair, and almost immediately I was super hard.

Our second date was that Saturday.  Jane needed help stringing Christmas lights on her tree so I gallantly offered my services.  She proclaimed that there would be no sex until at least Date 5 or 6.  No problem, I assured her.  However, I remembered Rebecca wanting to wait, yet we fucked on Date 2 when we couldn’t control ourselves any longer.  So with that in mind I came packing a box of condoms.  Just in case.

When I got to Jane’s place I couldn’t help notice the lavish furnishings.  She seemed a bit materialistic, which she confirmed by telling me how much she liked to shop.  She also told me she liked being spoiled.  Fortunately I’d brought a bottle of wine along, but I frowned to myself.   I wasn’t going to overthink things, but I couldn’t help imagine our lifestyles clashing down the road.  No matter.  I decided to not worry about the future and just enjoy the present.

I also couldn’t help but wonder whether Jane wanted kids…?  It never came up in conversation, and she was already 38.  In fact she was a year younger than Rebecca was.  Hmm.  39, 38… for some reason older women seem to be the only ones I’ve been having any real success with.  Interesting.  I do seem to connect better with those a few years older.  And I do find them appealing in a way.  That is, as long as they’re child-free.

We ate take-out and then I helped her put the lights on the tree.  Unfortunately, while the boxes were labeled the same, the two strings of lights didn’t match.  Dammit.  We sat on the couch gazing upon her half-and-half tree.  Then we snuggled together to watch the rest of The Santa Clause on TV.  That didn’t last long.  I’d been there for over an hour, and I was running out of self-control.

I reached over, cupped her chin in my hand, and tilted her face up to meet mine.  A heavy make-out session ensued.  God, it felt so good to do that again.  First time in a year and a half.  Before long I was sprawled on top of her.  After a while of grabbing at the hem she finally pulled my shirt over my head.  Yes!  This was happening!  Once it was off I asked whether she wanted to move things to the bedroom.  At the very least it would be more comfortable than the couch.

“We’re not having sex, but we can do other stuff,” she said.  I assumed “other stuff” meant oral.  Who’s the lucky boy? I thought to myself.  I’d never gotten a BJ to completion before, so it sounded like it might be a good night!  We resumed making out with some ferocity, and eventually my hands made their way to her chest.  I hesitated a bit, wondering whether she’d let me cup her breasts through her shirt.  She did.  Yes!  Her shirt came off shortly afterwards, followed by her bra.

I’ve fantasized about it many times, but actually removing a girl’s shirt and bra is truly a magical experience.  I don’t think it’ll ever lose its luster.  I relished the skin-to-skin contact, spending eons with my mouth on her neck and tits.  I started inching my way down, sucking and kissing and licking and nibbling as I went.  As I approached her belly button, I wondered how much further I could go.  No girl had ever let me go down on her before.

One time with Rebecca, I’d barely started on her when she pulled the blankets around her and proclaimed she was cold.  I guess that meant we were done?  After that, anytime my face ventured too far south she’d stop me and tell me she wanted me inside her.  Wasn’t going to argue with that.  Plus, I figured that like a lot of women she was self-conscious about how she looked or smelled or tasted down there, although she looked tantalizingly perfect.

After a period of time Rebecca told me she wanted me to go down on her, and I said I’d be happy to oblige.  I sent her descriptive texts about how I wanted to put my head between her legs.  Unfortunately that was also around the time she started getting weird and told me she was feeling overwhelmed and needed space.  Whether my texts contributed to that, I don’t know, but in any case I approached Jane’s nether regions with caution.

I hooked my fingers in the hem of her pants and pulled them down. Her panties came with them, and she assisted me in pushing them off.  Then I started to tease her.  I worked my mouth along her inner thighs, first one leg and then the other as her breathing intensified.  I kept teasing her until finally I was face-to-vagina.  My mouth hovered over her lips as I waited for the red light, but she didn’t seem like she was going to stop me.  She was naked and waiting.

So I took the plunge.  I went all-out, working my tongue in and out and all around.  I kept that up for a while, occasionally coming up for air and another mini-makeout session before going downtown again.  This time I stuck my tongue in even deeper, sucking on her clit while working my fingers inside her, trying to remember everything I’d ever seen or read.  Her moans and cries grew louder and louder and I smiled at her reactions.

Suddenly I felt a wave of heat as her body shuddered, and she wrapped her legs around my head and nearly yanked my hair out as she came.  Wow.  That was intense.  I made her cum two more times like that before I stopped.  I’d been at it for at least a half-hour and I needed a break.  My mouth was parched.  She held me tight to her chest and I enjoyed being suffocated by her 36Ds (I’d peeked at the label when I took her bra off).

“You’re bad,” she said.  “You’re not as innocent as you look.”

I gave her an evil grin.  “Definitely not,” I said.

“I didn’t think we were going to do all that…”

“I didn’t so either,” I said, laughing a little.

“What’s so funny?”

“Can I tell you a secret?” I asked, then immediately debated whether I should.  Ah, why the fuck not.  I wanted to see her reaction.

“Sure!”

“You’re actually the first person I’ve gone down on…”

There was a pause.  “What do you mean??”

I told her I meant just that.  She actually sat up and made me look her in the face as I said it again, because she wanted to make sure I wasn’t lying.  Then she goggled at me.

“But… like… how did you know how to do all that?” she sputtered, astonished.  “YouTube?”

“Google,” I grinned.  “Was it really that good?”

“Yeah,” she said, sinking back into the couch again.  “I’m still trying to catch my breath.”

“Well, I’m sure there’s room for improvement.”

“Well, you can practice as much as you want on me,” she said with a kiss.  And then I revealed a little more of my history to her, which further shocked her.  She couldn’t believe that not only was she the first I’d given head to, but only the second I’d been intimate with.  “So I’m your first vagina…” she said dreamily.

However, I was getting the sense that she wasn’t going to reciprocate, and I was right.  Dammit.  While disappointed, I didn’t whine or complain or make her do anything she didn’t want to.  Instead I was just glad I’d had my first opportunity to give oral and I did my best to make it count.  And I quite liked it.  I wanted to do it again.  And I would have gone down on her again had my tongue not felt like sandpaper at that point.

By then we were halfway through The Santa Clause 2 (a sequel which did NOT need to be made).  We cuddled on the couch for a while before moving to the bedroom, but only to sleep.  I’d already figured on staying the night, especially since it was snowing and the roads were treacherous.  She put on her PJs and I stripped to my boxers.  It didn’t take long before we were fooling around again.  We were spooning when she told me I could hold onto her breasts.  No problem!

Her shirt came off once more and I went to town, especially after she told me she likes her nipples pinched and sucked, which I was more than happy to do.  Then I sat against the headboard and told her to lean back against me.  That way I had a great view and easy access to her tits, and I fondled them to my heart’s content. Finally I ended up lying on top, grinding myself against her.  She bucked her hips against me in return, and went harder and faster until she came one last time.

Jane assumed I came too after I rolled off her, and was astonished to hear I hadn’t. Yeah… dry humping doesn’t do it for me.  And her hands never ventured past my waist, true to her word that she wasn’t going to touch me.  Which was a shame, because I had the biggest erection ever and would have loved to have shown it off.  But getting so worked up for so long was a mistake.  I went into the bathroom to whack off, but it was too late.  Wham.  Blue balls.  Jesus that shit is painful.

But I had to relieve myself or else I was going to be wired all night. After that I was able to sleep, and as I drifted off I mused how surreal it was.  If somebody had told me two weeks earlier that I’d be in a new girl’s bed, I’d have said that was crazy.  Yet there I was, and her bed was comfortable as shit.  I didn’t stay for breakfast as I had to get going, but we made plans to meet again during the week.

The following Tuesday we had a bonafide movie night.  And I take movie nights very seriously.  I actually watch the movie, and I even have my own popcorn machine.  She was surprised, but even more so at my choice of movie: Bad Santa.  Not only is that one of my annual holiday flicks, but I chose it specifically to test her sense of humor.  That is critical to me, and I was having doubts.

Well, she did not find it funny.  While I was roaring with laughter, she was going “awww!” every time the kid was onscreen.  When it was over I wiped tears from my eyes and relayed the tale of when I saw it in the theater with my mom and brother, and how people kept turning to stare at us wondering why we were laughing.  “Yeah, I was wondering the same thing,” she said.  Um, because it’s a comedy?  Yup, as I’d suspected we were definitely a mismatch.

After that we had a quiet time snuggling and chatting.  No fooling around, no groping, no making out… I wasn’t getting all worked up again for nothing.  If she wanted to wait to get physical, then we were going to wait.  Until then I was content with running my fingers through her hair, massaging her head and neck and shoulders… all the while marveling at how amazing it was simply to touch another human being.

Eventually we called it a night and I took her home.

We had a fourth date lined up – a Paint Nite – but there was more goddamn snow and it wrecked our plans.  She said she was feeling sick anyway, so that put the kibosh on the next few days too.  During that period I noticed our communication dropping off.  I was holding up my end but she was getting quieter.  Sigh.  My gut told me what was coming.  I’ve been down this road a million times.  So I waited.  Finally the word came down the pike:

“I’m sorry for the late response I have been running non-stop and can’t seem to catch up! I am an idiot for taking up a second job- I have to be at work at 6 am. This is just such a busy time of year etc.. plus holiday, plus my trip, I’m not sure if this is really a great time for me to start a relationship. It’s not fair to you. You are a really nice, sweet, kind of guy and you deserve a girl that has time to give you. And unfortunately I can’t be that girl. I realized all of this today as I finally have a chance to catch my breath and think…”

My suspicions were correct.  And it sounded like a polite way of saying, “I’m just not that into you after all.”  Which would have been fine, because I was starting to feel that way about her.  But I gave her a chance and it was fun while it lasted.  So I told her “no worries” and that I understood.  Thus concludes my latest dating experience.   So while 2017 won’t go out with a bang, at least I got to eat pussy for half an hour and play with tits for another hour.  It was a good thing I went down on her when I had the chance, because who knows when I’ll get another one.

I’m still convinced that Bad Santa was the beginning of the end for her. 

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Feelings

I’ve kept a positive, upbeat outlook over the course of this blog, but I was in the doldrums a while ago.  Just a little bit.  It’s passed now.  Part of it was standard winter blues, but another part was my perpetual singleness.  Don’t get me wrong – I’m happy with myself and my life.  I don’t need “my other half” or someone to complete me. But I want more.  I want someone to share the good things in life with.  Food.  Drink.  Laughter.  Music.  Travel.  Sex.  Just to name a few.

For a short while – nearly two glorious months – I got a taste of what that was like.  I had sex.  I lost my virginity.  I finally felt like I was in the know, part of the club, part of the world, “normal.”  I stopped feeling those pangs when I saw couples.  I did things that come so easily to most people:  hugging, kissing, cuddling, massaging, holding hands, or just sitting on beach watching the sunset – things other people take for granted.  Until I slept with Rebecca a few times, I had no idea just how warm another human body was.

Now it’s been ten months.  I’m doing my best to leave her in the past where she belongs.  I blocked her on Facebook to resist the urge to snoop or message.  I’m doing my best to not to dwell on negative thoughts and remain forward-looking.  Therefore I’ve been filling up my time with hobbies and activities to keep my mind on other things.

I’ve been hitting the gym hardcore for the past three months.  It’s a great outlet for my pent up sexual energy and frustrations.  I continue to set personal records in deadlifts, squats, and bench presses.  I’ve stacked three, four, or even five 45lb plates on the weight sled and pushed it back and forth across the floor until my legs gave out and my arms shook.  My buddy and I tried a class last weekend that nearly wiped us out.  But my body is responding and I’m tipping the scales at 187 pounds – a number I dreamed about for years.

The gym is not my only arena of success these days.  I’ve been out there marketing myself and I gained ten new clients, so this should be my best year financially.  I had a great parade season and a triumphant return to solo performing.  I’m practicing several instruments a week and I sound better than ever. (I find playing music as cathartic as going to the gym.) My passport arrived and I’m planning some more travel.  And I’m giving my life a complete overhaul – new car, clothes, furniture, appliances – everything.

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Throughout all of this I’ve had Bumble running in the background.  The last app standing.  There was that one awkward date a couple months ago, and since then I canceled on two more because I’d decided I’d rather go to the gym instead.  I just used the always popular, vague line of “something came up.”  I felt a bit shitty doing it, but deep down I felt those dates would have ended up like all the others, so why bother?

But there was one final Bumble date.  I tried to keep the online chatter light and flirty and save all the getting-to-know-you questions for in-person.  As Matthew Hussey says, “if you’re using texting to ask, ‘How many brothers and sisters do you have?’… you’re doing it wrong.”  So I gave that a shot, but it didn’t matter.  Once again I met a girl who checked out of the conversation after five minutes and I was the only one left making an effort.

I’d talk, I’d ask questions, she’d respond… and I’d wait.  Nothing.  Nothing asked about myself in return.  Scratch that – she asked literally two questions, almost as afterthoughts:  what was my job, and did I live alone?  When I realized she kept glancing at her phone on top of her purse on the chair next to her, I bade her farewell.  I know a lost cause when I see one.  And thus concludes my online dating efforts.  Permanently.

After so many years, I’ve come to conclusion that it’s a supreme waste of time.  There’s always the anecdotal success story, but I could never get it to work for me.  It never felt right – always forced and awkward and unnatural.  Personal experience and informal polling of friends and fellow bloggers tells me that meeting people in real life is the way to go.  Not to mention that I had more success with Rebecca than all the girls I met online put together.

Now that spring is finally here I’m compiling a bucket list, which includes several upcoming Meetups.  I’m trying to get to that same sweet spot I was in last year, where I found the perfect balance of doing my own thing and not worrying about finding someone.  Then BAM, it literally happened when I least expected it.  In the meantime I feel I’ve grown content with the status quo again.

I also continue to work on myself.  It’s almost comical… I’ve had thirty years to work on myself – how much more time do I need?  There’s always room for improvement, I guess, like with my conversation skills.  That’s partly why I’ve been filling up my calendar with things to do – gives me shit to talk about.  I’m doing my best to be more social and to fight reverting back to my natural introverted state.

So I guess that’s all I have to say for the time being.  I’ve had this blog post drafted for weeks and weeks and I kept revisiting and revising as my thoughts and feelings ebbed and flowed.  Now I’m finally ready to publish, and we’ll see what happens next in life.

Stay tuned.