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

It don’t mean a thing…

‘Twas time for swing dancing!  It’s been a while since I’d gone, and a while since I’d been out of the house, so I killed two birds with one stone tonight.  This time I arrived early and derived the benefits of the half-hour lesson that starts the evening (I missed it last time).  I learned some new steps and brushed up on the old ones.  I wasn’t worried about losing anything during my long absence; I spend most nights sliding around my house in my socks and underwear like Tom Cruise in Risky Business.  You know – practice.

Swing dancing is great  I finally get to dance with girls, and they actually seem to enjoy dancing with me!  Awesome.  Not only that, but the people there are all so friendly and outgoing and approachable.  It’s almost unnerving.  I’m not used to that.  Maybe I’ve unwittingly stumbled across a cult…  But what’s nice about swing dancing is that you can ask pretty much anyone there to dance and nobody turns you down.  You get a turn with everybody in the room.

Once again were a few young lovelies in attendance, some I recognized from last time and some new faces as well.  I took a few spins around the dance floor with each of them, which was great.  I was really getting into the “swing” of things.  They also play an occasional non-swing dance tune throughout the night, which mixes things up nicely.  I was in the middle of dancing with this real pretty girl when a waltz came on.  Ho, boy!  I may not know how to really swing yet, but I sure as hell know how to waltz.  However, the girl I was with didn’t.

“It’s easy,” I told her, putting one arm around her and holding up her other arm.  “Just follow my lead…” And away we went!  In fact, all the couples formed up into one ring encircling the entire dance floor.  It was awesome.  Probably the closest I’ll get to being in a Viennese Ball.  But what I wouldn’t give to find someone I could do this with all the time.

The girl in my arms sighed contentedly at the end of the dance.  “You’ll have to show me how to waltz sometime,” she said.  “I just wish my boyfriend could dance like that…”

Boyfriend.  Of course.

But whatever.  Tonight was easily the most fun I’ve had in some time.

Swingers

The long wait was finally over.  I’d wanted to try this for eons.  It wasn’t until tonight that I finally took the plunge and experienced it for the first time.

I approached the venue with trepidation, worried about the possibility of spending an evening cooped up with a crowd more akin to Bingo Night.  But alas!  Upon my entrance I immediately noticed a number of lovely young ladies.  I eyed them hungrily from opposite the room.  I was a lion on the hunt, a tiger lying in wait, a tomcat on the prowl.

Meow.

They held this shindig every week, devoting the first thirty minutes to acquainting everyone with their limbs and different positions to try. I paired up with one of the older, more seasoned ladies.  She grinned at me.

“So.  Did your friends drag you here or what?”  No.  I assured her I came of my own volition.  She nodded, apparently satisfied.  She took hold of me and told me where to place my feet.  I obeyed, not willing to quarrel with a more experienced woman.

Before long we settled into a routine and found each other’s rhythm.

“You’re really good at this!” she gasped at one point, clearly impressed with my abilities.

“What can I say?” I sighed, adopting my best aw-shucks persona.  “I guess I’m a fast learner.”

“Well, keep it up!  The better you are at this, the more girls will like you.”  I barely stopped myself from rolling my eyes.  I had been doing this by myself ever since I was a teenager, but I’d never seen firsthand proof that girls liked it too.  I supposed it was true.

After a short while the organizers called out for everyone to stop.  It was time for the real party to begin!  They dimmed the lights, put on some music and served drinks to help us get in the mood.  We were encouraged to switch partners constantly – regardless of whether we were finished – with the ultimate goal of taking turns with everybody in the room.

This is it, I told myself.  Time for my big debut.  Don’t be nervous…

I spent the first part of the night with a few more older women until I finally relaxed enough to take a turn with some of the girls around my age.  The first girl was okay looking, but she exhaled a scent like moldy cheese.  Ugh.  I didn’t last long with her; I couldn’t take her heavy breathing in my face any more.  The second one was really pretty, but she was there with someone and I felt really self-conscious with him watching.

Then I saw the next girl and my eyes nearly fell out of my head.  Wowshe’s really fit.  What a body!  I took a deep breath, put an arm around her and pulled her into me, and then we started to move.  Oh my God, this feels so good!  This is what I’ve been missing out on?  Why didn’t I try this sooner!?

I wasn’t expecting much conversation, but she wanted to talk.  I did the best I could, as I was trying to stay focused and concentrated on what I was doing.

“Is this your first time?” she asked.  Ha.  There was obviously no fooling her.

“Yeah… definitely my first time,” I said.  No worries, though.  She was very supportive and encouraging, and before I knew it I had found my mojo and we were really going at it.  It was even better than before!  I was positively bursting with excitement.  I heard singing in my head:  “Heaven… I’m in heaven… and my heart beats so that I can hardly speak… and I seem to find the happiness I seek…”

Then she went and burst my bubble.  “I usually come here with my boyfriend but he couldn’t make it this week…”  Ugh.  Way to spoil the moment.  But I got over it.  There were other ladies during the night, but none were as fine as she.  No matter.  I’m definitely going back there again.  This is just the kind of thing I’ve been looking for.

I really like swing dancing.