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).

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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 (some of it).  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 could be.

Now it’s been ten months.  I couldn’t help but peek at her Facebook and I saw she’s been with the same guy for the past eight months.  Oh really.  So what happened to all that jazz about not wanting to date or be exclusive?  How come she didn’t push him away and sabotage things like she did with me?

Well, let that be a lesson to me.  And I’m leaving her in the past where she belongs.  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.

Icebreaker

So… I went on my first date in five months.

In my last post I was indiscriminately swiping right on Bumble (and then Tinder) just to see who I matched with.  Then I starting swiping just for girls I was actually interested in.  This time I engaged them in conversation – or tried to.  Talking to most of them was like talking to the wall.  One word/one sentence answers, and nothing asked about myself in return.  I deleted each one and moved onto the next.

I finally managed to get something of a rapport going with this one girl, and we set up a game of chess for a first date.  All right, something different.  However, I had a funny feeling so I started the countdown.  Right on cue, she canceled the day before saying she forgot she was supposed to help her sister move.  I just said “no problem, let me know when is good for you.”  I didn’t expect to hear back (since I never do) and I was right.  And I don’t even care anymore when they flake out.  Losing my virginity has enhanced my IDGAF abilities.

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Then I chatted up another girl.  We went on yet another goddamn coffee date.  I’d sworn those off, but this time I thought it was a good idea to start small before investing in something more involved.    Good call.  Things got off to a slow start and ended up feeling forced and awkward.  It seemed like we were both just prodding the conversation along, and after an hour she called it a night.  She was actually yawning prior to that.  Either she was really tired or I was really boring, or both.

Outside I gave her a hug and kiss on the cheek and said it was nice to meet her.  Then we said good night and parted ways. I said nothing about getting together again, nor did I follow up with her afterwards.  I already knew what I would hear – the usual “oh I had a nice time and you’re a funny/interesting guy but I just don’t feel any sort of connection etc etc.”  So that was that.  But it was nice to get back in the game, even if I’m feeling a bit rusty.  I’m not really putting effort into online dating anymore, nor am I taking it very seriously.

Some of you have asked me “what are you looking for?” and I’d always struggled to answer that question.  How was I supposed to know when I had so little experience to draw upon?  And I’d always thought it unfair for some girls to reject me when they’d barely gotten to know me.  But now I get it.  The way things felt and flowed with Rebecca is my new benchmark going forward.  So if I do go on another online date, it won’t be unless I’m really feeling things.

Otherwise I’m busy doing my own thing and getting out in the real world.  I recently spent an hour on Meetup joining a slew of new groups and I went on my second outing last weekend.  It was another hike and we had over 20 people, but the vast majority were in their 40s and 50s. There were a couple of girls around my age in attendance, but one of them showed up with her boyfriend and another guy had already swooped in on the other by the time I arrived.

I watched with the tiniest tinge of jealousy as they exchanged phone numbers afterwards.  Not because I was attracted to her, but it was just the very idea.  I’ve always marveled at how dating and relating comes so easy to some people.  Some can date a different person every week, or every night of the week if they wanted, and they have no shortage of options.  They go from one to relationship to the next as easy as breathing.  How do they do it?  And how can I get there?   Not that I want to go through a revolving door of girls, but how do I achieve that same ease of attraction?  It’s something I’m still figuring out as I go along.

Some of you are frustrated virgins as I once was, trying to figure out your own way forward.  The best thing for you to do right now is to just work on yourself.  That can be as simple as picking up a new hobby or cultivating an existing one.  Good skills give you social currency.  Girls like confidence… except maybe you don’t feel confident.  But if you can find confidence simply in doing something well – whatever it may be – then that’s just as beneficial.  It’s why I devote so much time to my music and dancing and other pursuits.  At the very least, your hobbies will give you shit to talk about, especially if you find someone who shares your passions.  So if you don’t know where to start, that’s a good place.

A good analogy for me is this: say you want to develop your abs…  Now, you can spend an inordinate amount of time concentrating on your midsection, doing hundreds of crunches trying to spot reduce your belly fat.  Or you can work your whole body, targeting the major muscle groups with compound exercises.  If you do that and concentrate on your diet, then your abs will almost take care of themselves.  So if you’re struggling on dates or to even get dates, take a step back and date yourself for a while.  It’s an indirect way of achieving the same end.

Apart from my renewed Meetup activities I’ve also started volunteering at the animal sanctuary, the one my old friend is at.  We started super early at 7:30 AM.  On Sunday.  Ugh.  Kill me.  But we were the first two there and I was glad for the chance to talk to her alone as we fed and watered the alpacas and turkeys.  Then our conversation was interrupted by a father/daughter duo who showed up to volunteer as well, and will be joining us every weekend.  Of course.  Not that it really matters, because I’m pretty sure she’s still with the boyfriend.  And even if she’s not, she’s militantly vegan and our lifestyles would clash horribly.  But I’m there to spend time with the animals more than anything else.

Later that same day Vegan Girl posted some animal pics to my Facebook, and as always my friend Don was right there commenting on her post and asking her questions.  Every time a girl leaves me a comment, or vice versa, he sees it in his news feed and he jumps right in with his two cents, stepping all over my dick in the process.  It’s annoying as shit.  I’m afraid the time has come to block him, especially now that he’s mining my friend list for more girls to add. He already has a thousand as it is.

In a way, I almost have to give him credit – even if he did hit on my sister Mary (who’s ten years older and looked at him as if he were a bug).  He leaves absolutely no stone unturned, but I guess he has to when he’s the weirdest and most socially awkward person ever.  I stopped dining out with him because last time he was staring creepily at random girls and blowing straw wrappers at them.  He actually thought he was being flirty.  *facepalm*  (Another bit of advice for you virgins: don’t be like Don.)  Yet somehow he finally managed to lose his virginity too.  And get this – he did it a full two years before I did.  How in the fuck.  I’m still trying to process that.

So that’s the round up.  I’ve also made up a list of things to do and places to see, which has now grown to two pages.  So far I’ve crossed off a good number of items.  Most of it is just fun silly shit, but I consider them accomplishments nonetheless.  I’ll detail them all when I do my end of year post.

Success

Sorry for the delay, folks.  June is a notoriously busy month for me and I’ve been busy… *ahem* in other ways as well.

Picking up where I left off…

As I said, Rebecca and I continued talking throughout the week, and the following weekend she came to my place.  I took her for another nature walk, we made out in the bamboo forest, went to dinner (Italian) and then it was back to my place to watch a movie and play a board game… but you all know how that usually turns out.

Sitting on my couch talking led to sitting on my couch making out, then to sitting on my bed making out.  Some clothes were shed.  I sat her up so I could pull her shirt off, and she laughed and went, “what are you doing?”

“What do you think?” I said slyly.

“You can’t take off my shirt when you still have all these clothes on!” she said.

“Well, then, you’d better do something about that,” I said cheekily.  So she grabbed my shirt and pulled it off, and didn’t offer any more resistance as I pulled hers over her head and flung it aside.  Now she was in her bra and pants, and I removed those shortly afterwards.  And then we were both in our underwear in no time at all.  I knew this was it.  It was going to happen.  Our hands roamed all over each other’s bodies for the longest time, just taking it all in.

Her breasts looked like they were straining to be free of her bra, so I decided to help out. I knew she wouldn’t stop me.  One of the hooks came undone easily, but the other was stuck and I was having  a hard time with it.  We both laughed about it, but I finally got it off and there they were… big, magnificent breasts hanging right in front of me.  Mmm.  Oh yeah.  I kissed and caressed them and sucked on her nipples and basically went to town.

Then she pulled my shorts off and started to blow me.  It wasn’t at all what I expected it to feel like.  It felt warm and wet and really good but weirdly different at the same time.  I wasn’t used to that kind of stimulation and it wasn’t doing a whole lot for me, but I still enjoyed the sensation.   After a minute or two of that I couldn’t wait any longer.  I told her I wanted to be inside her.  She grinned at me and said, “finally… I’ve wanted you inside me all night!”

She dropped her panties, I deftly rolled on a condom, and then she mounted me.  I couldn’t feel much with the condom on, which kinda sucked, but I was inside her!  I did it!  We went at it like rabbits, trying out a few different positions.  We ended with missionary and I nearly pounded her into the wall.  I was making a bit of a racket, making the headboard thump and rattle.  Then we just lay there until 3AM, naked in each other arms and keeping our breathing in sync.  Eventually we drifted off to sleep.  The next morning she told me her vagina was a little sore but very happy.  Good deal.  I had gotten her off at least a couple of times during the night.

The next night she wanted to see me again.  We went out to eat, sat on the beach in the darkness, and then headed back to her place.  We tried watching another movie but we were only five minutes into it before she said, “Let’s go to my bedroom.”  This time the clothes came off even faster and I made it all about her.  I kissed her, caressed her, fingered her, licked her, pinned her down and flipped her around, and massaged and grinded her until she had orgasm after orgasm. The best part was when I spanked her.  I went from grabbing her ass cheeks to lightly swatting each one in turn.  Then I started smacking her harder and harder until her flesh rippled, gently massaging with my hand in between each slap. She bit and scratched me and made a great deal of noise and completely soaked me when all was said and done.  Afterwards she basically passed out and we slept until 6 AM.

A week later I told her I was a virgin.

I had to.  The thing was, I was having performance problems during all the aforementioned.  Trouble cumming or just staying hard.  I couldn’t get off that first night with her, so things actually didn’t last very long.  After a lifetime of porn and masturbation, I was struggling to adapt to new stimuli.  I was so used to my own hand. Not to mention my dick was suffering from a bit of stage fright.  I didn’t want her to think there was something wrong with her, so I finally fessed up.  I had to.  On a scale of 1-10, 10 being the most shocked, she registered a 7 at the news.

Things became much easier after that.  Even though I had lost my virginity by that point, I was still stressed out that I hadn’t told her and that in itself was just making things worse.  I also ditched the porn and masturbation and saved myself for her.  It was almost a couple of weeks before we saw each other again, due to work schedules and then both of us going out of town at the same time.  Finally we were back in each other arms again.  She came back to my place.  We started watching yet another movie but we both fell asleep.

Sexy time came in the morning.  Touching led to caressing which led to articles of clothing dropping off one by one.  She climbed on top of me and started rocking back and forth, rubbing her pussy against me.  We had prior discussions about safety and this time we went condom free since the proper precautions were in place.  It was unbelievably hot and wet inside her.  So THAT was what it felt like… I lasted only five minutes before I exploded. No wank can ever prepare you for that feeling.  It was amazing.  And messy.  I didn’t realize how messy sex was.  When you cum inside someone it all just kinda runs back out.  She had to wrap herself in a towel before she got back into bed with me.  I was in a blissful daze.  And I’d finally broken the wall so there were no more performance problems or anxiety after that point.

We went for round two later in the day, and that was all I could manage.  She had to get going, and I didn’t have any strength left.  It took me until midway through the next day before I fully recovered.  But ever since we’ve been having sex any chance we can, and by that I mean during whatever time we have free on weekends.  Although, we did manage one mid-week rendezvous during our lunch breaks.  I came three times in an hour and I was barely able to stand after that.  Of course, I always make sure she’s satisfied as well.  And then the following weekend we went at it until I was physically drained.  The last orgasm I had with her was the most intense yet and I was shaky afterwards.

Anyway.  So that’s how I lost my virginity.  I got off to a slow start with mixed results, but now I’m on a roll.  It wasn’t as big a deal as I thought it would be.  It wasn’t life-changing and I didn’t feel like a brand-new person afterwards.  The first time wasn’t nerve-wracking or awkward.  Maybe a tiny bit awkward, but that went away with practice.  If anything it was a bit surreal.  A sense of, “Wow, am I really/finally doing this…?”

One change I’ve noticed is that my libido has calmed down quite a bit.  Ironic.  I thought finally having sex would send me into overdrive, but finally understanding the mystery has taken the edge off for me.  Perhaps it’ll go crazy again over time, but for now I’m experiencing a new-found and much welcomed peace and calmness.

In the meantime we appear to be an item.  We talk every day and see each other whenever our schedules permit.  I don’t know how this will all end, but so far so good.  I’m very happy being with her and it’s such a pleasure waking up next to her in the morning.

In the end, it was worth all the struggle, frustration and heartbreak.  I feel like it happened at the right time and with the right person, and I’m glad I didn’t do it “just to get it over with.”  Sometimes the old cliche is true – it really does happen when you least expect it or when you’re not looking.  I just had to date three dozen girls before I found her.  I know some of you are struggling with your own virginity and/or just trying to find that someone special.  I urge you not to give up, no matter your age or circumstances.  Maybe take a little break and spend some time finding yourself first will help, like it did with me.  You can find success too.

Now the question is what to do with this blog.  I’m going to leave it up for all past, present and future readers.  I’ll continue to check in and post the occasional update, but for the most part my journey is over.

THE FINAL TALLY:

First dates:  37
Second dates:  5
Third dates:  3
Cancellations:  9
Stood up:  2
First kisses: 3

Her

This is the story of how I met her.

I’ve been on Meetup.com for a couple of years.  I joined a bunch of groups and received regular email updates, but I’ve scarcely put in more effort than that.  But as I’ve said, I’m determined to get out and do more things and meet new people this year.  So I took a second, more serious look.  There was a hiking group that intrigued me and I went to one of their excursions a few weeks ago.

It was my first ever Meetup.

There were half a dozen of us and I was the only guy who happened to show at this particular hike.  The odds were in my favor, but looking for a girlfriend was the furthest thing from my mind that day.  As a result, I was totally and unabashedly myself.  I kept the group entertained with my wisecracks and anecdotes.

Rebecca liked my jokes.  I thought she was cute when I first met her, but at some point during the hike we  clicked.  It was just one of those things.  Now I know what people mean when they say that.  When we came to a grove of dogwoods I plucked a flower off one of the trees and gave it to her.

“Here, this is for you,” I said, presenting it to her like the cornball I am.  She couldn’t stop grinning and stuck it into the strap of her backpack, where it remained for the rest of the hike.  We stuck together for the last mile, asking each other questions and sharing stories.

Later that day she sent me a message through Meetup telling me how much she enjoyed meeting me on the hike.  I had noticed she had posted a couple of pics on the Meetup page, so I asked if she had taken any more?  I was fishing for contact information.  Turns out  I didn’t have to try too hard.  She said she took a bunch of pictures, and if I gave her my number then she would send them to me.

I was in.

By the next day we were Facebook friends.  By the next night we were swapping flirty and sexy messages.  By the next weekend we were going on our first date.

We live some distance apart, so I drove out to her area and we went to the wildlife preserve.  Once we checked out the birds we set off on one of the trails. I took her by the hand.  We found a bench by the water and I suggested we sit.   After a few minutes of talking I pulled her in for a kiss.  We made out for a while.  It was perfect.  I remembered her saying she liked ass grabs, and she nearly straddled me after I grabbed both cheeks.  Unfortunately we had to stop when we heard other people approaching.

It started to rain right after that and we had to hustle out of the park.  We went out for burgers (my kind of girl).  Then we went to see The Jungle Book, but we saw very little of the movie as we were too busy groping and fondling each other. That was the first time I ever did dinner and a movie for a date.  It was also the first time I gave a girl an orgasm.

When we started watching the movie, she had her legs crossed and my hand was resting on her thigh.  As the lights went down I pried her legs apart.  I ran my hand along the inside of her leg, back and forth, going further and further until I was brushing against her crotch.  Eventually my hand made its way down the front of her pants and I started massaging her.  I’d rub for a little bit, then stop and just rest my hand there as she writhed about in her seat trying to muffle her cries.  Finally I kept going without stopping, going harder and faster until she came.

“Oh, fuck…” she whispered, nearly rolling over the armrest into my lap.  She grabbed my arm and bit down on my shoulder, nearly putting a hole in my shirt in the process.

After the movie we drove down and parked by the inlet.  We sat there watching the water and talking for about two hours before  calling it a night.  We’d been together for over eight hours and neither one of us wanted the day to end.  But she wanted to take it slow and not rush things.  She wanted to try, at least.

I was really attracted to her.  She was a no-frills, no makeup, what-you-see-is-what-you-get kind of girl.  Simple tastes and easily amused like myself.  We both valued nature, fitness, and keeping it real.  We had the same kind of spirit, energy and sense of humor.  We just got and understood each other.  Things were comfortable from the start.  Everything felt right and natural.  Maybe it was because we were both the same sign (our birthdays are ten days apart).  I don’t really set stock by that sort of thing, but it’s always fun to think about.

We kept talking throughout the week and we went out again the following weekend.  This time she came to my area.

And things got a little steamier.

 

First dates:  37
Second dates:  4
Third dates:  2
Cancellations:  9
Stood up:  2
First kisses: 3

Beginnings

True to my word, I’ve been taking a break and focusing on other things for the time being.  First up was the local traditional music orchestra.  They meet once a month to rehearse.  I didn’t get in touch with the contact person until after the February practice.   I couldn’t make March because it conflicted with my St. Patrick’s Day commitments.  Then April was canceled.  And then I couldn’t make May because it was the same day as my nephew’s First Communion.  Now I can’t make June because I’ll be out of town visiting my brother that weekend.  Always something.  But I’ll make it there eventually.  In the meantime I’ve obtained the book of music and I’ve been familiarizing mysef with the tunes.  I’m also planning on hitting the open mic circuit again over the summer.

Next up was the gym.  I’d been considering joining one for some time.  While my job and my dancing keep me in relatively good shape and I’ve been doing some workouts at home, I wanted to get serious with it and one of my friends volunteered to be my gym buddy.  It took us a couple of weeks before we finally got started, but we’re now going three times a week and both of us already feel a huge difference in our lives.  He says it’s even helped him drastically cut down on his smoking and drinking.  I’ve also noticed a nice change in my body.  Turns out I respond well to serious weightlifting.

Work is in full swing now and I’m busy prospecting to expand my customer base.  I dumped my far-flung (and most annoying) customers this year, and not only am I working to replace them but to add more on top of that.  So far I’ve picked up two new ones.  Good stuff.  I still have more leisure time than I had planned on so I’ve been using it to go on hikes and explore parks and preserves that have been on my to-do list for a long time.

In the middle of all of this I actually landed another first date.  I had left my OKC profile up just in case, and sure enough some girl came across it and sent me a message.  She found me interesting and I was intrigued by her as well.  If she wanted to meet me then I wasn’t going to turn her down.  However I met her for brunch and found I just wasn’t that into her.  I didn’t feel we had much in common after all.  When she asked me afterwards if I wanted to go somewhere else, I said I had to meet up with a friend who was visiting from out of town (which I did).  We made tentative plans for the next weekend, but I never followed up and neither did she.

And there’s another reason why I didn’t get back to her…

Because without planning on it, without expecting it, without trying to…

I met someone.

First dates:  36
Second dates:  4
Third dates:  2
Cancellations:  9
Stood up:  2
First kisses: 3

Kiss

It’s been ages since I’ve had a second date, but I went on one tonight with The Singer and I dare say it went pretty well.  The original plan was to go to the carnival, but the shitty weather put the kibosh on that.  We ended up going bowling instead.  There was an hour-long wait for a lane so we went into the bar area and had a couple of beers in the meantime.

We found a relatively quiet corner and had a nice conversation.  I found out that not only does she like Harry Potter, but she’s a Star Wars and Titanic buff too.  Score!  She’s very easy to talk to, and the huge mug of beer I had helped as well.  We also delved a little deeper this time, broaching the subjects of religion and politics and the cosmos.  We were pretty much on the same wavelength there too.  She took a lively interest in what I was saying and I was eager to learn more about her in return.

They finally called our names and we went out and bowled a couple of games.  She picked up the tab for those since I bought beers this time and dinner last time.  I appreciated the gesture.  After a couple of good frames I did a spin and a moonwalk, much to her amusement.  When we were done bowling we sat there chit-chatting for a bit before calling it a night.  She had choir practice in the morning and it was getting late.  I also didn’t want to overdo things.

I walked her to her car.  At this point my heart was throwing itself against my ribs.  We’d been texting all week and things got a little flirty the day before.  I was determined to kiss her before we parted ways.  I think she might have wanted me to kiss her after our first date, and I wasn’t going to make the mistake of not doing so this time.  Second date – shit or get off the pot.

We stood by her car making idle chit chat and it was clear she was lingering, so it was now or never.  I said good night and we hugged.  We pulled back a bit, and then I lowered my arms to around her waist and pulled her back in.  She realized I was going in for the kiss and she closed her eyes and tilted her face to meet mine.

As soon as I saw her do that I mentally shouted YES! YES! YES!  Then we connected.  It felt great.  Totally natural and not awkward in the slightest.  I let my hands roam around a bit, running them up and down her back, along her sides, and then reaching up and grabbing the back of her neck.  She pulled me closer against her, and when I put my hand on her neck she grabbed the back of my head and pulled me even closer.  We made out like that for at least a couple of minutes before finally coming up for air.  She opened her eyes slowly and let out a little giggle as she looked me, and then she put her head on my shoulder and just held onto me for a bit.

I said good night again and told her what a nice time I had, and she told me I’m a lot of fun to be with.  Then I said I’d be in touch very soon, gave her one last peck and floated over to my car.  I drove home in a happy little daze.  And now the big question is how to proceed from here.  I’m quickly approaching uncharted territory.  I have to figure out my next move and not screw this up.  I seem to be doing pretty well so far, though.  I’ve been cool and chill and patient, and I haven’t done or said anything weird or stupid.

Oh yeah – and I think she likes me.

 

First dates:  34
Second dates:  4
Third dates:  2
Cancellations:  9
Stood up:  2
First kisses: 3