Does Sexting Count Towards My 2012 Dry Spell?

And lo, beloved Long Suffering Readers, it’s time that I come clean about some of the other activity that has gone on in 2012: the amusing and sometimes ridiculous story of my sexting experience on Twitter. It’s over now, but it still makes for an amusing tale. For a long time I did not want to write about this on the blog for a few of reasons. First, while it was going on, it seemed like it would be tacky to talk about it—the whole “kiss and tell” thing even if it was “type and tell.”  I’ll write more in a bit on why I’m not too worried about this now. Second: when I started writing the blog I’d done it with the intent of just venting about Catherine and I: as time has passed she has become less and less of a focus on the blog, and I have to start writing about the new experiences I’m going through or else put the blog into retirement for good. I figured if I’ve shared as much as I have up to this point, a story about sexting should not come as a shocker. Third: while it was going on, it was very fun and exciting (more on that in a bit as well) and I sure as hell didn’t want to do anything that would risk cutting that off too early; even if it was just sexting, it was the first “action” I’d received in close to 8 months so to say I was “eager” would be an understatement. Fourth: some of the reactions I’ve received from the few people I’ve already told about the experience are too funny not to share. And the final reason of why I decided to write about it now will be revealed at the end…

Meet “Victoria”

My relationship with “Victoria” started simply enough. She was at some point re-tweeted by someone I followed, I checked out her AVI and found her funny as well as attractive; clicking “follow” seemed like a no-brainer. At some point she followed back (no doubt when I tweeted something about the manscaping article… that one is always good for some self-humiliating laughs). At some point she made an open-ended tweet about something that was upsetting her. I DM’d her some sympathy, she DM’d back, and the small-talk went from there. What do you do? What do you do in your free time, etc. I started DM’ing her more frequently. At some point the conversation moved to Kik. It was flirty, but platonic. She was a sweet girl. We exchanged some pictures (G-rated head shots), stories, and were generally just having a fun and chaste time.

“Oh, you like my hair, do you?”

But I noticed that Victoria was also a bolder girl on her public timeline. She would willingly tweet about her urges, sexual frustration, desires, etc. Like several people I’ve befriended on Twitter she seemed brave on the outside, and a bit vulnerable “up close”. Our private chats contained some longing (on my part at least) but not erotic. I told her I much I enjoyed her company, and how pretty I found her. She called me handsome and funny. I was beginning to crush a bit on her. But I was 8 months into a divorce, and not been with anyone in a year, and not dated/flirted in over a decade. I was no prude, and her tweets told me she was not either, but I had no experience breaking the ice for something like this.

I went out one evening and sent her a pic. She kik’d one back of her long dark hair. I have a weakness for dark hair, I always have. “I love your hair” I texted her.

“Oh, you like my hair, do you? Do you want to run your fingers through it?” she replied.

Oh man. I looked at this message for a minute. If I’m going to go there, I thought, and let her know how I’m thinking now is the time. And if I am going to go there, it cannot be subtle: it should be a message that goes beyond suggestive. I started typing. I looked at the message before I hit send. This is either going to go really really well, I thought, or it will go horribly awry and I will be blocked almost immediately. This is what I wrote:

“Not only do I want to run my fingers through it, I want to grab that gorgeous hair, pull your head back and start kissing your neck. And as I do, my free hand is going to run up your thighs until I reach your wet panties.”

And then I sat and waited. Anxious and nervous, I could feel my heart pounding. Man, I hope I didn’t just fuck this up. My phone finally buzzed with her response:

“Oooooh… I like the dirty talk!”

And from there, my dearest long suffering readers, it was “on” as the kids like to say. I fancy myself a bit of a writer and not one to shy away from the graphic details so once I knew she was receptive I threw myself into my work. I wrote what I could to arouse and stimulate her. I told her about how this was my first sexting experience (true) and she was, effectively, the first person I’d had any sort of hot talk with since the divorce (also true). She was graphic and sexy and caring all at once. It… was… fabulous.

“Real Women Have Real Vaginas”

I have to admit, after being starved any sort of attention for so long it was addicting. If memory serves, that weekend we “got together” 4 times. I was feeling downright chafed. I asked her to send me suggestive pictures, and she did. I started seeing some bits of our “exchanges” show up as subtweets and it aroused me even more. As I did care for her, I didn’t want it to become just about sexting, but I’d be lying if I said I wasn’t looking forward to our exchanges. At one point I told Charles, as I was still living with him at this point, about how I’d been staying up late chatting with Victoria. “Dude,” he told me, “Real women have real vaginas.”

“I know,” I told him. “She’s hot and funny and sassy and she’s going to get a ‘Real Boyfriend’ in no time, but until then, I’m going to enjoy it.”

“If she asks for a Dick Pic, does that mean she likes me?”

At some point she asked me for a dick pic. While I’d given her a some PG-13 pix, I’d done nothing of this sort. I pinged another friend-girl I have on Twitter for advice. I’d had very limited DM’s with this person and nothing remotely sexual. It was a funny exchange that went something like this:

“Say, didn’t you tweet once that you wrote an article on the art of dick pix?”
“No, that was [ so and so].”

“Oh, sorry, I’ll give [so and so] a message.”

“Wait!? What’s going on, I know a thing or two about dick pix!”

I went onto explain what was happening, where I was with Victoria, how I was nervous about sending anything rated X.

“Look,” she said, “As long as you follow the safe pix sending rules, you’ll be fine. I’d be happy to send you a pic right now.”


“Um… I wasn’t fishing, but if you’re offering…” I mean, let’s be real, do you really expect me to turn that down?

“Look, I’ll tell you what, I’ll send you 3 of my favorite dick pix I’ve received so you know what a good one looks like, and then I’ll send you a picture of myself to cleanse your mind those images.”

“OK then.” She was good to her word: 3 pictures of members came into my kik inbox followed by lovely images of herself. It was fabulous and surreal.

For the record, here’s her advice on taking dick pix in a nutshell:

  • No headshots (seems obvious)
  • Hide any identifying marks, tattoos, or anything in the background (OK, makes sense)
  • Don’t forget to turn off the feature that inserts GPS from your phone. (Ooohhhh… I forgot about that)

Sage advice, my friends.

 “We’re not dating.”

But, it wasn’t all lust sexy talk. At my emotional core, even though I was WELL AWARE that this could never turn into a Real Relationship (for a variety of reasons I won’t go into here to maintain Victoria’s anonymity) it doesn’t mean that Real Feelings didn’t creep in. I tried to be careful about not saying anything that would make it seem that because we were enjoying Sexy Time it might infer some sort of commitment on her part. And yet, by just using the flattering language I would to try to make her feel special would make her nervous and skittish sometimes.

“We’re not dating, you know!” she would remind me.

“Yes, I know that…” I could tell it was soon going to come to an end. Our conversations started becoming less frequent, and when we did talk, it did not “go there.” There was one last hurrah as she sent me some fabulous photos and talk right before I went on a long vacation. When I returned it was mostly silent.

“So those girls are sending you pictures of them playing with themselves?”

Before I tell you how it ultimately ended I need to relate another funny story related to this subject. As I mentioned a while back, I was having some Man Issues, to which I finally went to an urologist to make sure nothing too weird was going on. Apparently, I choose the Most Chatty Urologist in the Bay Area. He was an older guy, probably in his early to mid 60s. I probably had the longest chat with him that I’ve had with any doctor.

“So, what are you here for?”

“Having urinary problems. Frequent urination. It sucks.”

“Uh huh. Are you married.”

“Technically yes, but I’m getting a divorce. I haven’t been with anyone in about 10 months.”

“I see. And did you have any problems getting an erection?”

“No. I don’t think so.”

“You don’t think so?”

“Well, I haven’t been with anyone, but I’ve had these online-chats with Twitter Girls.”

“What’s that?”

“Twitter is an online social network. You type at each other. You can send pictures.”

“And what are doing with these girls?”

“Basically it’s sexual stories combined with mutual masturbation.”



“So let me get this straight,” the doctor asked, “so these girls are playin’ with themselves and sending you pictures?”

“Yes… and sometimes they have video cameras. Although I haven’t done that myself.”

“Wow” he said. (He then went on to ask me more questions about my family and the divorce. He asked that as a man in my mid-40s with two daughters who seemed to be done with family had a I thought about getting a vasectomy.

“Hmmm… Are you suggesting I get a vasectomy?”

“It’s not my place to suggest it. I’m just wondering if you’ve thought about it.”

That,  my friends, is a tale for another blog.

Victoria: The Epilogue

I would ping Victoria about every 2 or 3 weeks (usually on a Friday as that’s when my work week is slowest) just to check in and say Hello. We were friends before the Sexy Talk and I wanted to be friends afterwards. She’d told me that she had met a Real Boy and that she’d given up sexting as that “just leads to someone getting hurt”. I totally understood. I asked if it would be OK if still texted her from time to time just to stay in touch and she agreed, and so we have. (P.S. I never did send her a dick pic…)

So why write about this now?

I actually had a longer chat with Victoria last week. It was a lovely chat and we both did lots of catching up. During the conversation I told her that I’d wanted to write about her and I “back in the day.” She admitted that while it was going on she kept reading the blog to see if I was writing about her. I asked her if it would be OK I wrote about it and she said it would (as long as I kept her anonymous). That pleased me as I always thought this would be a funny subject and in some way I think knowing that this post is coming has intrigued her a bit. And while it may not have ever gotten physical, Victoria will always hold a small place in my heart as my “first” after Catherine.


2 responses to “Does Sexting Count Towards My 2012 Dry Spell?

  1. “If she asks for a Dick Pic, does that mean she likes me?”

    lmao…. best line ever. I think I told you I don’t ever participate in sexting really of any variety (though wouldn’t be against it if I were in a truly committed longterm relationship), but if I did that sort of thing now being single, I would say no. For me, it would just be a game to see how far I could push someone to get him to do what I wanted. It would be about control for me. Sounds like you guys had a sense of closeness that went beyond just random sexting for fun. A lot of people just do it for attention and to see how far they can get you to do something. Sounds like she was fond of you and vice versa.

    Perhaps I’ll write about why I don’t sext and what my boundaries are now that I’m back on the dating scene. Stay tuned 😉

    • Hey Amy,

      Thanks for dropping by and checking out the blog.

      As for Victoria and I, yes, we had flirty fun but I think it was grounded in a mutual crush tempered with reality. I never felt like she was trying to control me or push my boundaries, nor I with her. She and I are still friends and in fact she told me several times (including just recently when she reviewed this article) that she was always just trying to be sensitive and not hurt me while also enjoying our time together. It was perfect for what it was.

      Looking forwardto reading about your boundaries and adventures on the dating scene 🙂


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