My mind is a jumble of naughty and heartache

I’m sitting in my vacation spot, outdoors, where it’s a bit chilly. I’m warming myself by a firepit. Listening to what I’m sure is a wedding party, and debating how uncouth it would be to crash. I’m also not wearing a bra, but am sporting a white shirt and realize that I’m a bit nipply.

As I think about what to write, there are many things going through my head right now.

The first (not foremost) is that my masturbation is getting naughtier. I find myself on occasion DP’ing myself. Is that odd?

Sheesh. Okay, here I am asking the internet if DP masturbation is weird. I guarantee that for every kink or idiosyncrasy, there is a community here.

The second is that I’m alone, for eight nights. When I went on vacation by myself back in January, it was for four nights. So I’ve doubled it. I happen to be in a land of couples. No party crowd here. Last night it worried me a bit, but today I’m feeling better.

I spent the entire day by the ocean. I had my e-reader and my iPhone for music. In a bathing suit, armed with sunscreen, baseball cap, some snacks, water bottle, and a sarong, I was set. It was bliss, actually.

I was alone most of the day but met three guys while swimming. They were in their late twenties and we chatted in and out of the water for a couple of hours. It was fun. While I TOTALLY would have fucked the cute one with the interesting tattoos (with a military history – like a few of the other men who have graced these pages), it was just nice to chat.

The third is that last night while masturbating, for the first time ever, I thought about a woman.


I’m not going to read too much into this, but it surprised me. I’m tentatively open to being in a threesome with another woman, but I can’t see myself being a giver. Perhaps I could be a receiver. But there are so few women I’m attracted to.

This is a women I know, and I will be seeing her soon. So I’m a bit weirded out about this. For now, I’m going to chalk it up to horny creativity. But we’ll see.

(and by the way, although Andrew is creative and flexible, his preferred threesomes are two men and one woman. So I’m super good with that).

The last, but definitely not least, is about Johnny. It was his birthday recently and I debated whether to send him an email to wish him a happy birthday. I was conflicted because to be perfectly honest, I didn’t want him to think I’m more of an asshole game-player than he seems to already. And I feared if I didn’t reach out, he would be even more hurt.

A post of his alluded to the fact he’d found a woman to spend time with and that his birthday plans were looking promising. I thought this was a good sign that he was healing. I hadn’t communicated with him since I wrote the post about some of the irrational things that went through my head when I read his writing. It’s been a few weeks.

I decided to send him an email – it was short and said simply that I wanted to wish him a happy birthday. I didn’t think I would hear back at all and I was okay with that.

Well, I did hear back, and it was unfortunate. I promised him I wouldn’t quote him, so I won’t. I have no intention of speaking for him or trying to ascribe motives. This blog is about me, not him. But suffice it to say, I caused him pain. It wasn’t my intention. He’s angry and hurt, as I was supposed to be with him on his birthday.

I made the decision not because I don’t care about him, but because I do. I knew that things would be great and fun and intense between us. It would make things all the more painful to then continue on the current path. We had already come to the conclusion that the timing was wrong for us.

So by reaching out, I ended up hurting him again. It was the last thing I wanted to do. It makes me sad; there is nothing I can do to make it better. It is an odd place to be to not regret the decision, as I know it was the right thing for me, but to very much regret the impact.

I have to come to terms with the fact that it’s unlikely I will ever talk to him again. That there is nil chance of there ever being something between us again. That history is being rewritten and I have to just suck it up.

Now, you can guess which of these four things is prominent in my brain right now. I’d love to say it’s not the last, but I try not to lie in my journal.

0 thoughts on “My mind is a jumble of naughty and heartache

  1. I like the phrase “horny creativity”. There was an online test somewhere about where a person falls in the “spectrum” of sexuality but I can’t remember where it is. It would be interesting to see your results (in a non-creepy way, I mean).

    I wish you would stop reading his site, but I get why you did and that it’s still not easy. ((hugs))

    As for the pool guys…Sometimes it’s hotter to leave them wanting more πŸ˜‰

    • I took that test…and can’t remember where I found it either. I forget where I was on the spectrum but if you find it let me know and I will absolutely take it again and share (I’m such a giver!!).

      It is hard not to read, and I have failed at that. But I’m not getting hurt by reading about him with other women or anything like that. I want him to be happy. The stuff that bothers me is the stuff that ascribes motives to my behavior that is untrue, or that seems to be written from a place of anger.

  2. Do our minds ever stop thinking/wondering/worrying/surprising us? Haha its insane.

    I think the ereader, music, and relaxing is exactly what you need right now. Enjoy your holiday sunshine! Don’t stress or worry, just go with the flow. Whatever happens happens. Xo

    Ps. With your glorious bosom out to show, I’m sure there will be some ladies having dreams about you too πŸ˜› Its nice to stop and appreciate the female form sometimes, nothing wrong with that πŸ™‚

    I’m shocked you haven’t ticked it off your sex bucket list yet though! Ann the raging sex goddess with things still left to tick off, tut tut! Jason found you a pretty good male unicorn, maybe he knows a good female one, and you can see if you like it or not πŸ™‚

    • Oh man this comment made me laugh and smile and laugh again. To be told I have a “glorious bosom”. Wow, thank you. I may have blushed.

      And then to be considered a “raging sex goddess”? Even better. And nope, there are a lot of things I haven’t done. I haven’t written a sex bucket list, but perhaps I should.

      I think Andrew can introduce me to a few things that I haven’t done before. It’s titillating and nerve wracking at the same time!!

      • Hahaha its the truth! A couple of the many reasons why we’re all addicted to you Ann πŸ˜›

        I’m excited for your adventurous future, have fun with it!! And YES you definitely need a sex bucket list. I’ve done quite a few things for the sake of the sex bucket list/fetish list/blog and its been quite fun actually! I’ve found out a lot more things I enjoy. Even today I learnt a new bj position to try out: wooo so excited!

        • I guess I’m okay with being an addiction πŸ˜‰

          I will try to do you proud!!

          And there are a few more things that I will add to my non-list…after having a conversation with Andrew last night again. Sheesh. He’s taking me to whole new places.

  3. Congratulations on embracing your alone time. You are doing all the right things. My suggestion is not to overthink any of this – just be in the moment and give your mind some space and time to process. My gravitar is from a trip similar to yours. It reminds me everyday to live my life my way – no compromise for now.

    • I’m never that good at living in the moment…but I’m trying πŸ™‚

      I think I’m still winding down so perhaps by day 3 or 4 I will be all super chill. One can hope!!

      And I’m glad you were able to take a similar trip. I love the avatar you use!

  4. You’ve done all you can with Jonny, Ann. Move forward and concentrate on your own happiness.

    And speaking of which, I’m sorry to hear you’re lonely. I am glad you decided to go someplace where it’s warmer tham my home base. (Niagara is a wet sticky mess right now – and not in a good way!) Think warm, sexy thoughts and you’ll be good.

    Do WHATEVER it takes to get back to form.
    Be well.

    We’ll talk soon.

  5. You’ve stuck a cat laser toy in you hoo haw before, so DPing yourself is not odd at all and quite frankly whether you’ve been with another woman or not thinking about it isn’t odd either. Of course your thoughts on giving and receiving might change once you find the “right” woman and I’ll attest that, that is a feat in of itself. But once you do…. well watch out. πŸ˜‰

    I’m guessing that you are going to experience a full range of emotions and at levels that might be unexpected considering this is really the first time you have had to yourself without interruptions to begin processing all that you’ve been through in the past several weeks. Allow yourself to feel, absorb, acknowledge then release them.

    Hugs to you Ann and I hope you are enjoying your vacation.


    • Thank you ‘Tis. It’s so true…this is the first time I’ve had space to really think. So lots of processing is being done πŸ™‚

      I’m glad I also have time to write about it too!!


      • I think it would be wonderful if everyone could take solo vacations if for nothing else but to decompress and process.

        I see I have some catching up to do in the reader. lol


        • I hung out with a female blogger on Sunday and when I made a comment that I posted every day she said – yes, sheesh, I know…it’s hard to keep up πŸ™‚

          I am honoured, truly, that you do.

  6. I am sorry that this last interaction transpired like this Ann. I am also sorry that it leaves you with some fresh pain from this emotional scraping of the scab that was only starting to form on your heart. I suppose that you needed to experience this last bit of hurt to confirm that puttying JiD decidedly into the past. I hope that this doesn’t jade your time in this wonderfully relaxing locale.

    I admit that I haven’t read your blog from beginning through to today, but I don’t recall military men gracing your pages (which could be the result of memory issues or my spotty reading habits). I guess that I have a bias towards and cheer for these guys (for some reason)! But, I caveat that thought with things that I have mentioned in previous (email) conversations. πŸ˜‰

    • Thank you so much for your concern. I am not jaded in the least. It was a disappointing outcome but I suppose not entirely unexpected.

      And no, I don’t explicitly mention military men, because generally a man’s profession isn’t relevant to the posts I am writing, but suffice it to say a few I have written about have that background.

  7. Sounds like a few days alone is just what the doctor ordered so you can sort some things out upstairs. Enjoy the rest of your vacation. I have a feeling you’ll feel much more ready to take life on by the time you get back.

  8. I think a break on your own will do you and that brain of yours a world of good.

    Healing is a hard beast. Some days are good some days not so good.

    Be kind to yourself as always. I’m sending you squishy hugs.

    Ps. There’s nothing wrong with having a girl surprise bomb your masturbation fantasy! It happens to me allllll the time. But then, I think sometimes I prefer women over men. But that’s just me and my queer ways.

    Just go with it. It may transpire into something or it may not. But I do love the masturbation crashers πŸ˜‰

    And enjoy that time off! More nipples. There should be more nipples in the world…

  9. You mentioned that you liked to DP yourself while practicing self-abuse, here’s a trick for you. The next time you’re getting laid for real, stick that finger back in your ass at the same time. From a guy’s standpoint it feels really good and you can feel her rubbing your dick through the thin membrane that separates the front door from the back. Not quite as good as when she’s really getting DP’d but a close second!

  10. Welcome to the warm sticky mess that is the south! And you get to play with that in your mind any way you like. I love your analogy of not regretting the decision but very much regretting the impact. That says it all. To have done what is right for you is a good thing. To cause more pain becomes painful for you too. How do you fix that? You don’t, I suppose.

    Hopefully your next 6 days will bring you peace and contentedness. And the odd orgasm. Well… not odd. I don’t know why you’d consider self DPing weird. It sounds pretty nice to me. And what you do in the privacy of your own beach doesn’t count anyway. It’s like eating whipped cream on an airplane. You’re so high up, you hips don’t even notice.

    Just enjoy yourself… for yourself. You’ve done enough self analyzing and criticizing for a while. You deserve some “me” time without trying to figure out if it’s weird on not. Male, female… if they make you feel good, does it really matter? Ya, actually it does. I know I couldn’t be with another man, so I guess that one doesn’t cut it for me.

    I’m on day 2 of a long trip away too. I’ll wave to you as I go by. Have a drink or two for me. A Singapore sling… I’m buying

  11. I think about women about 30% of the time. I think women are better in bed than men. And they actually give a shit about you getting off. Usually. You should do whatever it is that makes you feel best. Male, female, tentacle monster. Our fantasies are the one place we can be free

  12. There was probably no winning on the Happy Birthday thing….but if it was me, I would personally have accepted the gift of your thought politely without causing you the same distress I’m feeling. Johnny is being a bit selfish – and that’s not what love it about. You reached out with genuine love.

What do you think?