Social distance and unrest, and a little bit of sex…

It’s been sad and disappointing seeing people posting and spouting the most unbelievable shit in response to current events this year.  No knowledge of civics, no critical thinking, outright dismissal of facts in favor of conspiracy theories and junk science, and a startling lack of empathy or understanding.  On that note – if you’re so tired of hearing about racism, just imagine how tired some people are of experiencing it.  If I wanted I could do a whole post (or a whole new blog) on these issues.  Maybe someday, but in the meantime I had to put my two cents in.

And now back to our regularly scheduled programming.  I had a few more dates recently.  I’d sworn off dating until things returned to “normal,” but as always I listen to my dick.

#75
This one was another waste of time – one I saw coming a mile away but proceeded anyway.  She sidestepped my flirty comments but still seemed keen on meeting me.  We ended up at the beach, and I made a joke that she was a little overdressed for the occasion.  Indeed she was – with her black pants, black leather jacket, and black heeled boots, but she got a little defensive about it.  She reminded me of my older sister, who’d go to the beach with a full face of makeup and would get equally as defensive if you ribbed her for it.

As soon as we got to the boardwalk she handed me her phone to take a picture of her.  Not just one, though, but a dozen.  She’d snatch the phone back after each one to make sure she looked good.  Once again, just like my oldest sister.  I rolled my eyes a bit, but it didn’t stop there.  We walked down to the big rocks at the water’s edge, and then it was picture time again.  And not just pictures of her in various model poses, but slo-mo and time lapse videos as well.  She showed me how she edits them all together into video montages of herself set to music.

I made another joke that I was starting to think I was only there to be her photographer, and she got defensive again.  Hoo boy.

We sat and made chit-chat and small talk while we waited for the sunset, but it was clear we were a total mismatch.  I learned she was an Aries.  Once again… just like my older sister.  Now, I don’t set much stock by that stuff, but it’s fun to think about and eerie how accurate it is sometimes.  But I find Aries women a bit high-maintenance, a bit flaky, and often a bit full of themselves.  (Teacher comes to mind; she was an Aries too.)  Then she dropped a bomb and disclosed that she was 40, not 30 as advertised.  She claimed that she didn’t know why it said that, nor how to change it.

As soon as the sun went down I called it a night and said goodbye.  She was making noises about wanting to see me again, suggesting I join her and her friends to go hiking upstate the following weekend.  I’m looking for a FWB, not a hiking buddy.  I don’t know if she didn’t see that in my profile, or just didn’t understand what it meant, but I was out.

#76
This one lived a bit of a distance away so we picked a halfway a spot – a scenic park on the lake.  We took a few laps around the water while we made conversation, but it wasn’t until we landed on the subject of her job as a financial planner that she became really animated.  She was really passionate about it… a little too much.  After what felt like a half-hour of her TED Talk, I called it a night.  It was getting dark anyway.  I suggested a movie night back at my place next time.  Hint hint.  She said she wasn’t interested in anything romantic with me, but maybe we could still hang out.  

Sigh.  Once again I was like… do these chicks not read my profile, or understand what I’m looking for?  I told her I wasn’t looking for anything romantic, nor am I looking for people to just hang out with.  So I wished her the best of luck finding what she was looking for and we parted ways.  Another one down.

#77
It’s funny how online dating activity ebbs and flows.  It was exceptionally quiet after that.  The next thing I knew, it looked like my theory was coming to pass – that girls would be so horny and desperate coming out of quarantine that getting laid would be ridiculously easy.  I was on track to get laid the next two nights by two different girls.  Was it possible?  Alas, no.  The first one crapped out, so I texted the other and asked, “are you still free tonight by any chance?”  Yes, she was.  I’ll call her Pharmacy Girl

Long story, it was some of the best sex either of us ever had.  The kissing was amazing by itself, so much better than College Girl.  (For the record, this one was 28).  My dick went in her mouth shortly afterward and I nearly burst right then and there.  Her oral skills surpassed anyone else I’ve been with.  She was also the first one to ride me cowgirl without it feeling uncomfortable.  PG obviously felt she same because gaped down at me and said “oh my God!  It’s like a perfect fit!”  She also appreciated that I assisted instead of just lying there like other guys.

I flipped her over and pounded her in missionary since she wanted to see what I could do.  Either she’s very orgasmic or I’ve become an exceptional lover, because she came hard with her heels digging into my back.  It was so intense for her that she was writhing and nearly bucking off the bed.  I came pretty hard myself; she felt amazing inside.  When she calmed down she said, “Well… THAT’S never happened before.”  I’d given her a full-body orgasm for the first time.  She tried sucking me off to repay me, but I knew it would take a long time after I’d just came.  I told her to get on her stomach and I fucked her from behind.  She absolutely loved that, and she got so wet that I kept sliding out.  “What’s the matter,” she giggled.  “Too wet to stay in?”  We switched back to missionary and we each came again.

PG previously told me that she’d never enjoyed receiving oral sex from any man (perks of always dating assholes), but I was determined to be the first.  I went to work, teasing my way down and working all around until she was going crazy with anticipation.  Then I buried my face in her.  I used all the techniques I’d studied and things I’d remembered from old girlfriends.  It took a while but I got her there.  She was in a daze afterwards, but I wasn’t done yet.  I used my fingers to get her off one more time.  She was on the verge of climaxing so hard I thought she was going to squirt.  No such luck, but I did give her another full body-orgasm and she left puddles all over my bed.

Afterwards she said she couldn’t believe how good I was with my fingers and tongue. “How did you learn to do all that?” YouTube, I joked.  From all accounts, I gave her the best sex and oral she’s ever had.  I asked if she was staying the night, but she had work in the morning and didn’t have a change of clothes.  Dammit.  But could we squeeze in one more round before she had to go?  I found that we could.  One last time in missionary, and we fucked so long and hard that the sweat built up between us and was dripping off my chin in the end.  And the eye contact we made… damn.  It was so hot.

We exchanged numbers a few days later so we could talk outside the app.  I asked about Friday.  She had to work.  Saturday?  Plans with friends.  I waited but she didn’t suggest a day in return, so I said I was ready for Round 2 the next time she was free.

I haven’t heard from her since.

I was flabbergasted.  How could she not want seconds when the sex was so good the first time?  She’d seemed excited at the prospect of regular sex again, but maybe she only intended it to be a one-time thing.  I guess I’ll never know.  She might still surprise me, but I’m moving on and already have another hot prospect lined up.  In fact, tonight is date night.  Stay tuned…

 

 

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

Tits

Shorty wasn’t inside for more than a minute before she launched herself at me and started kissing me.  I gladly reciprocated, grabbing her hips and mashing my crotch into hers to make sure she felt how hard I was.  I could taste the hunger on her lips.  That went on for about ten minutes before we finally broke for air.  “Now how about that movie?” she asked with a grin.

The only TV I have is in my bedroom, and the only way you can watch it is by sitting on  my bed.  I joked that I’d planned it that way as I led her to my room.

“So what are we watching?”  I showed her:  Fast and Furious 6.  She made a face.  “I stopped watching after the second one.”

I laughed.  I hadn’t even known there was a second one, let alone a sixth one, and the only reason I knew about it is because my 70yo mother had recommended it.  Besides, it didn’t really matter what I put on, because I knew neither of us was actually planning on watching anything.  Sure enough, no sooner did I perch on the end of the bed and take the DVD out of its case did she straddle me.  She was wearing an open button-down shirt over a tank top, so I took off the first item, pulled her hair out of the way, and went to work on her neck.  I swung her around so she was lying down and I climbed on top, my lips continuing their journey down her neck and across the top of her chest.

After another ten minutes had gone by, she took my hand and put it where she wanted it: on her breast.  I started massaging gently as I planted kisses all over her neck and shoulders..  Then she gasped, “okay, that’s enough.”  She sat up and put her shirt back on.  I put the movie on and we cuddled together and started watching.  I think we got as far as the DVD menu before we started up again.  This time she was on top of me running her hands through my hair and kissing me like her life depended on it.  We rolled around a few times and then she whispered, “I want to feel your hands on me…”

I started feeling her up again, but she took my hand and placed it inside her shirt and inside her bra.  I got the hint and started gently caressing her nipple.  Her head rolled back and forth on my pillow and she made all sorts of noises.  Earlier she had slapped my hand away when I put it up under her shirt, but this time she didn’t stop me.  But then she got skittish again and sat up and once again said that was enough.  I knew she was worried about having sex too soon, but as I propped myself up on my elbow and gave her my best come-hither glance, she came at me again.

This time it was her turn.  She ran her hands up and down my arms and under my shirt and over my chest.  “Do you like my hands on you?  Just imagine my body pressed against yours and my breasts would be where my hands are now…”  I was nearly convulsing at her touch and my breath came in ragged gasps.  She started teasing me as her fingertips kept delving inside the waistband of my shorts and running up the insides of my thighs.   Then she put her hand all the way down my shorts and touched me for the briefest moment and  I nearly lost all control.  I rolled her on her back and focused on her chest once more, but this time I put my hands anywhere but directly on her breasts.  I teased her for a good twenty minutes and she was going bonkers.  Finally she couldn’t take it any more and climbed on top of me and dry humped herself into an orgasm.  She collapsed against me afterwards in a quivering mess and muttering, “oh my God, what you do to me…” I simply grinned.

Unfortunately it was time for her to leave.  She had to go to work. Meanwhile, she couldn’t believe that the movie had been running for over 90 minutes and we’d barely watched more than a minute.  “I’m just impressed we made it as far as the DVD menu,” I said.  “Besides – car chases, explosions, guns going off… it’s not like we missed anything.  We live in NY so we already see that every day.”

Anyway.  Needless to say, there will be a third date.

PS – I never really knew what “blue balls” was, but after an hour and a half of fooling around with no release, I was in agony.  Actually doubled over in pain.  I had to jerk off and take a nap before I was able to walk again.  Ugh.

First dates:  19
Second dates:  2
Third dates:  1
Cancellations:  3
Stood up:  2
First kisses: 1
Sexual experiences:  0.6