So… I Had a Girlfriend

It’s been a while.  The last time I was here, I had a handful of Hinge matches that weren’t really doing anything for me.  I decided to junk the app.  However, one of the girls I was talking to noticed I was gone and panicked.  She messaged me on Instagram (slid into my DMs, as the kids say) and was suddenly a lot more conversational.  Well, this was more like it!  We went on our first date a few days later.

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Dawn, 28, a teacher and a local!  She lived only a few miles away, and coincidentally on a road I frequently traverse.  We met a local pub halfway between our houses.  I normally detest meeting in bars and such, but it was a Monday and mercifully quiet.  We got on pretty well, and as I walked her to her car afterwards I saw it was conveniently parked right next to mine.  I took that as a good sign.

We stood there for a moment looking at each other before she giggled and said, “I always get awkward at this part, I never know what to do!”

“I do,” I said and I took her in my arms and kissed her.  We made out for several minutes, ignoring the soft light rain that had developed.  She told me I was good kisser, and she wasn’t afraid to use her teeth and bite my lips a little.  Ooh, a biter!  Does that mean she liked it rough?  The thought got me super hard.  There was definitely going to be a second date.

We went to a mac and cheese place for our second date, and across the street for brews and board games afterwards.  However it was chilly inside and rainy and damp outside – much like our first date – so I suggested going back to my place where it was warmer.  I worried she might take it the wrong way and question my intentions.  Fortunately she was down for it, and we watched a movie and had a makeout session afterwards.  But we didn’t go further than second base.  It was only the second date and she didn’t want to rush things.

Third date was lunch and a hike, fourth date was dinner, and fifth date was dinner at my place.  I’d always wanted to cook dinner for someone and I finally got  my chance.  I thought she might stay the night but she left at 11:30.  Before she left there was some making out, some clothes came off, and my dick went into her mouth.  I couldn’t cum though.  I very nearly did, but I got some weird mental block and just couldn’t bring myself to do it.  What the hell.  And still no sex because now she was on her period.  Didn’t bother me but apparently some women are icky about that sort of thing.

Sixth date was pizza and board games, again at my place. She brought her Chrome firestick and we watched the Zac Efron Ted Bundy movie on Netflix. It was very good. Afterwards we cuddled and kissed a little bit, but I held back because I didn’t want to get too worked up and develop blue balls. She was still spotting from her epically long period (her gyno said it was due to her switching birth control pills), but eventually I said “fuck it” and starting making out with her for real.

Eventually she kissed her way down and gave me a blowjob. This time I came in her mouth, and she swallowed.   Holy fucking shit.  It felt amazing and took me a while to recover from that.  She was the second girl to ever go down on me and the first to go all the way with it.  Definitely worth the 34-year wait.  This girl was definitely a keeper. Even better, I awoke to the good news that her period seemed to be over!  Did I want to try having sex?  Pfft.  You don’t have to ask  me twice.  I grabbed a condom and when it was over I had filled that thing to near bursting.  Phew.

Over the next few months we had some great sex.  I lost count of the number of times we did it, but it was certainly in the dozens.  She had the most voracious appetite of anyone yet. One night she came over to my place wearing nothing but a trenchcoat over some sexy lingerie.  That was one of my hottest encounters ever.  We even experimented with paddles, handcuffs and blindfolds – more bucket list items for me.  There was good orgasm equality and we often climaxed simultaneously or close to it.  I scored some more blowjobs and happily returned the favor.  Dawn was only the second chick to ever let me go down on her, so it was nice to get some more practice.

Dawn helped me cross a lot of firsts off my list.  I finally had someone to introduce to family and friends.  I went on my first ever double date.  I updated my Facebook to “in a relationship.”  She joined me in the gym and we worked out together.  We watched a fireworks display.  I posted my first ever #wcw.  And then just regular couples stuff I’ve long relished the chance to do.  It was so nice to have someone to talk and text with all the time, sharing every weird or random thought.  Sometimes I’d wake up and just watch her sleeping next to me, scarcely daring to believe my luck.

So what happened?  Everything was going great as we approached the five-month mark, until I got the dreaded “we have to talk.”  Turns out… she did want kids after all. In the beginning she said she didn’t want kids, but ended up changing her mind.  I was afraid that was going to happen.  She was a Pre-K teacher, and anyone who teaches kids likes kids, and anyone who likes kids usually wants kids.  And if they want kids, then they have no future with me.  Dawn was looking towards the future, so that put the kibosh on things.  At least that was the reason she gave. I have no reason not to believe her, so I’ll accept that.

In the end I was dumped but at least we parted ways amicably and I have nothing but happy memories.  I gave the relationship everything I had.  Nothing was left undone or unsaid and I have no regrets.  Disappointing to say the least, when she checked off so many boxes for me. And five months – that’s a new record for me. 

All the girls I’ve had success with were fellow Sagittarius.  I don’t put much stock in that sort of thing, but it’s funny how it’s happened that way.  We certainly had a lot in common. Dawn was a brunette, which is also in keeping with the pattern…even if she did go blonde for the summer.  They’ve also been trending younger: 39, 37, then 34, and now 28.  Younger seems to be better in my experience.  More fun and spontaneity, less baggage, and greater sexual energy and openness.

While I’m sad that my time with Dawn has come to an end, I’m also kind of excited to see what’s next.  But I don’t know if I could go back to online dating.  (Of course, I keep saying that…) Even with that as a tool, it takes an average of 1-2 years to find someone interested in me in return, expending a great deal of time and energy in the process.  We’ll see.

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.

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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.”

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“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.

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. 

bad santa

Hair

“Hey, Tommy, there’s a girl giving blow jobs under the bleachers… you want one?” Joe asked as we stood in our high school parking lot.  His friends hovered behind him, shoving their fists into their mouths and elbowing each other waiting for my response.  Joe was one of my many childhood bullies, and based upon their reactions I knew he was up to no good.

Not to mention that I was fourteen years old and I still had no idea what a blow job was.  I did know that it sounded like something I’d seen on the board at the barbershop: “Wash cut and blow job.”  I scratched my head, trying to figure this out.  So… was Joe saying there was a girl under the bleachers with a hair dryer?  Where did she have it plugged in?  And why was he asking me this?  Why did his friends think this was so funny?  Did my hair look wet? Was somebody sneaking up behind me to dump a pail of water on my head?

I decided to bow out gracefully:  “No thanks,” I told him.  “I’ll just get one the next time I get a haircut.”

There was a riotous explosion of laughter.  “HOLY SHIT, DID YOU HEAR WHAT HE JUST SAID!?”  Joe yelled.  Some of his friends were literally rolling on the ground, unable to contain their mirth.  Confused, I turned and walked away, doing my best to ignore the words they were calling me.

I was pretty upset when I got home, and when my mother saw me she asked what had happened.  “This guy at school told me there was a girl giving blow jobs under the bleachers and asked if I wanted one, and I didn’t know what to say!”  I shared this story with her hoping she’d pick up the hint and dispel my confusion as to what a “blow job” was without me having to ask.  No such luck.  Her response, though?

“You should have asked them, ‘how much?'” she said.

Now I was really confused.   But that was the reality of school life for me.  On a daily basis the guys would approach me with a new question:

“Hey Tommy, do you like Korn?”

“Yeah, it’s okay.  We have corn every night for dinner.”

“HOLY SHIT, THIS KID IS A RETARD.  YO, GUYS, COME OVER HERE, YOU GOTTA HEAR THIS!  Tommy, say it again.  Tell them what you just told me.”

Everybody in school called me a retard for the rest of the day.  Or they asked me if I wanted some corn. Or they asked me if my family was poor and whether corn was all we could afford to eat.

Next day:

“Hey Tommy, are you a fudgepacker?”

“What’s a fudgepacker?

“It means you eat a lot of candy.”

I didn’t eat a lot of candy – or any candy at all – but I didn’t want them to think I was even more of a weirdo.  I was desperately  trying to fit in, so I told them, “Yeah, I’m a fudgepacker…”

“HOLY SHIT, DID YOU HEAR WHAT THIS KID JUST SAID!?  HE’S A FAGGOT!  YO – Chris!  Nick!  Joe!  Get over here, you gotta hear what this kid said, he likes to take it up the ass!  He’s fucking gay, I knew it!”

Everybody in school called me a fag for the rest of the day.  Then again, they called me a fag every single day, so that wasn’t exactly anything new.  But this time they peppered me with extras:

“So what does penis taste like?”

“I know this guy in my third period class you’ll like.  He’s a faggot too.  You can fuck each other in the ass in the locker rooms.  I’ll stand guard outside the door so nobody bothers you two.  Would you like that?”

“No wonder you don’t have a girlfriend.”

“When did you take it up the ass for the first time?”

“Are you really a fudgepacker?”

“Yo, we were talking about AIDS in health class today, and I thought of you.”

“You know everybody knows you’re queer now… right?”

“You’re so skinny you probably weren’t in the closet all this time, you probably hid where your mom keeps the ironing board instead.”

“Joe told me your barber blows you.  Is that true?”

When I went to my last period class there was a pile of pencils on my desk:  “Hey Tommy, me and some of the other guys took up a collection for you.  We thought you could use these because you’re so tiny that your ass probably couldn’t take a real dick…”  (In case you missed it, I was a skinny little nothing back then.)

Multiply that by twelve years and you get the idea…

***

I went for a haircut today to ensure that I looked fresh for the holidays and my fast-approaching birthday.  I love getting a haircut – I always feel fresh and sexy afterwards.  Anyway.  I decided to pamper myself this time.  For an additional cost, my haircut also included a hot towel face and scalp massage, and then an upper back and shoulder massage.  Well worth the extra money.  And I specifically went to this place because it’s men-only clientele, and the staff are all very lovely young ladies.  They are very nice and friendly and talkative, but then again I’m sure they’re paid to be.

I got Kaitlyn. Very pretty blonde with a very nice ass.   And normally I hate it when girls wear perfume (because they usually overdo it with shit that’s WAY too strong), but whatever she had on was very light and pleasant. and as she worked I closed my eyes and inhaled her intoxicating scent.  Thankfully I was sitting down, because I was getting weak-kneed every time she ran her fingers through my hair.  I silently mused about how nice it would be to have someone run her fingers on my hair on a regular basis.  I’m actually considering going back there for my next hair cut just so I can experience the pleasure again, even though I never go to the same place twice.

Damn, I need to get laid.

We talked the entire time, exchanging chit-chat and pleasant conversation.  I like to think she was so taken with me that that’s why she forgot to dry my hair.  So when we came to the end and she asked if I’d like anything else, I said, “Yeah, can you give me a blow job?”

Whoops.  My eyes bulged and I gaped at her, horror-struck.  I covered my face with my hands and started laughing.  “I’m sorry!  Oh God… I meant can you blow dry my hair!” I babbled, pointing at my wet head.  Fortunately she took it in stride and laughed too, as she realized she had forgotten all about that step.  But I couldn’t recover from my embarrassment.

When we were finally finished I followed her up to the register, enjoying the view as she walked in front of me.  After I paid she handed me a business card, and for one wild second I thought she was giving me her number.  My heart hammered in my chest as I took it from her.  Was she actually thinking of…?  No.  It was just one of those get-five-cuts-get-the-sixth-one-free punch cards.  Oh well.

I really need to get laid though.

Tarnished

For the longest time I’ve been seeking a serious, long-term relationship.  But I’ve grown so accustomed to being single and I relish my freedom and independence.  Not to mention that I’m so busy with work and extra-curricular activities that a relationship would just suck up my remaining time.  So I’m thinking… maybe it would be nice simply to have someone to occasionally do fun things with.  And stick my penis into.

In other words, I’m considering looking for a friend with benefits.

Friends With Benefits: Mila Kunis and Justin Timberlake

Considering my situation this seems like a good starting point.  In any case it’s a possibility I’d like to investigate.

These feelings began their distant rumblings several months ago, intensifying when I came across this post by fellow blogger Tarnished Sophia.  She has a long-term monogamous FWB, and the more I read about their relationship, the more such an arrangement attracted me.  What’s more, she was considering finding a second FWB.

Her lover is the only person she’s ever had sex with.  Tarnished has a history of abuse at the hands of her stepfather, so many walls needed to come down first.  And after eight years together, her lover thought she was finally ready to take on a second partner.  While they’d always been monogamous, they have an open relationship.  He was going to be out of the picture for a while, and thought it would be a good idea for her to have someone on hand to help feed her insatiable appetite.

This is where I entered the picture.  I half-jokingly left a comment that I might be able to help her out if she were truly looking for “male or female disease-free virgins that don’t want children, marriage, commitment, or to live together…”  We exchanged emails for a few weeks, talked on the phone a couple of times, and finally set a date.  Even if we didn’t hit it off, she said she could still give me a blowjob so I’d have at least that much experience.  That sounded good to me, especially if she was as good at it as she said she was.  That alone had always been one of my biggest fantasies, but I’d long ago given up hope of it ever happening to me.

The day came and Tarnished and I finally met.  I was quite pleased with her appearance.  Assets like whoa.  I went in for a handshake but she went in for a hug instead, which surprised me considering how touch-averse she is with strangers.  She was also a lot more bubbly and talkative than I was expecting. We spent an hour eating a late breakfast at the diner (her treat) and then walked around town for a while.

“So what do you want to do now?” she finally asked.  I chuckled to myself.  Oh, you know what I want to do now… I felt like saying.

“I don’t know, that’s as far as I’ve planned,” I responded.  She laughed.  Then she informed me that she only had a little while left before she had to meet up with her family.  Oh.  We hadn’t set plans apart from what we’d already done, but I’d assumed I was going to have her to myself for the whole day.  My hopes crumbled under me as I looked at my watch and realized there wasn’t really enough time left for sex, especially since we still had yet to address that particular elephant and I didn’t want to do things in a rush.  It seemed apparent that this was just going to be the initial “interview” rather than a sex date. So I devoted our remaining time to talking about sex.  We drove to the outskirts of town to walk along a popular hiking trail, and it was here that I finally broached the subject (once the coast was clear of children or anybody else – we kept looking over our shoulders to make sure).

“So… I was wondering if you’ve decided whether to take me on as a partner?”  Tarnished hemmed and hawed, and started saying things like, “I’m probably not what you’re looking for,” and “I don’t think I could give you what you want”  Finally I sussed out the reason for her hesitation, and it turned out she was not really on board with the idea of taking on a second FWB.  It was more something that her lover wanted her to do, rather than something she wanted to do.

That settled it for me.  I wasn’t going to have her do anything she didn’t really want to do.  Had she taken my hand with a sly smile and said “are we going to do this or what?” or “let’s get out of here,” I would have been all-in.  But she’s also demisexual, so in any case she’s not attracted to me the way she’d need to be in order for us to do anything sexual past a one-time encounter.  She said she could still give me a blowjob if I wanted one, and that it would be really good, but I turned her down.  Yes, I turned down a blowjob, heavily aware that another opportunity may never arise.  No pun.  But I could tell she wasn’t keen on that idea either.  (She later told me that my declination was both a major relief and a huge letdown – she’d spent a lot of time pumping herself up mentally to do it.)

To be perfectly honest, at the time I wasn’t 100 percent sure about entering a FWB relationship but was willing to explore the possibility, but I knew that I wanted my first time to be with someone I felt comfortable with and trusted completely.  Tarnished fit the bill.  She’s amazingly caring and accepting and non-judgmental, and her lover is incredibly lucky to have someone like her in his life.  However, we were just not meant to be.  But I was grateful for the chance to meet her and we still had a fun time together.  And she considers our meeting a date so I will update the counter accordingly.

***

In other news, I have one last update on Shorty.  She would not stop bitching at me, so I finally I composed a lengthy message telling her to get fucked.  Those weren’t the words I used – in fact, in contrast to the way she’d been talking to me lately, I used no swear words at all – but that was the jist of it.  I detailed exactly what my problems with her were, concluding my essay with “if this is how you act towards people, then maybe that’s why you’re having such a miserable time on the dating scene.  Just a thought.  So goodbye and good luck to you.”

Within the next hour I received seven missed calls, four voicemails, and two texts.  I deleted them all without looking or listening.  And that was that.  All has been silent ever since, and what a goddamned relief that is…

First dates:  21
Second dates:  2
Third dates:  2
Cancellations:  3
Stood up:  2
First kisses: 1
Sexual experiences:  0.6