Coming off of a rather disappointing trip to Portland, I decided to learn from my experience and improve how this vagina operated. I still used craigslist; I didn’t post two weeks out, I posted about a week out. For the first time ever in a post, I included a picture of me. What was it? Your Daring Vagina, double fisting beer in sunglasses. This let the person responding to my ad hopefully catch on that I was A. real and B. I’m pretty fucking fun. I mean, if given the chance, wouldn’t you want to hang out with me? But I digress…
So, I had a LOT of good responses. As in, I had to actually take my post down there were too many responses. Not only were they good responses, I started wanting to move to San Diego for the plethora of attractive men that were into me sexually. Or maybe the idea of a one night stand made them jump at the idea–the possibility is endless! Within the multitude of replies, I found a handful that I was like, 10/10 would bang, and responded to their response. You might be thinking, why wouldn’t you just reply to one? Here is why you don’t limit yourself when you’re in town for a short time:
2. People have friends and family that live in that city and plans come up. Life happens for you like it happens for them.
4. They may start out awesome and then turn into a creep with some really out their fetishes that they think a one night stand is ok with. Spoilers! No, it’s not ok to tell me you want me to fist your ass because no one else will.
5. People get sick. Colds happen all the time.
6. If you have time to sleep with multiple people and want to, do it. Try to beat your 24 hour record!
7. And did I mention flakes?
Out of all the possible contenders, one went a bit too kinky for me (I will not fuck you with a strap on), one became ill, and the other I saw. See, if everyone was always this planned, we’d all get laid.
Good Guy Greg (GGG) was down to earth; our correspondence was fun, insightful, and while he wasn’t that sexually experienced (I apparently attract those that want to experience all the kinky things), he was more than into everything I liked. We moved to texting and that’s when I found out he really was the male version of me. While a few years younger and in school, he loved and also collected comic books, wasn’t that experienced (I wasn’t at his age either), a huge pale ale drinker, and physically we were the same height, eye color and hair color and type (super cute curls.) We sent some “classy” nudes as pre-game material and I wasn’t disappointed in GGG’s equipment; maybe not the biggest cock out there, but it had girth and if he somewhat knew how to use it, I’d be happy.
I told GGG my combo and he insisted I bring not only my toys, but my lingerie. Being inexperienced, he also shied at condoms, which confused me at first, but I then went on the best shopping experience ever with my gal pal a week before.
So, moving right along! GGG worked doing fishing tours and I happened to be in town during their peak season (who am I kidding, San Diego has perfect weather and probably has tours all year long), and he didn’t know exactly what time he’d be off that Saturday night. I told him I’d stay up for him even though I had to be up and out the door by 5 the next morning for my race. Armed with that knowledge, I played the Tinder swiping game. Big ol’ bust. The one guy I talked to wanted me to come see him at a bar and blow him…at the bar. I’m sorry, I don’t need another sex in public talk by a police officer before I’m 30.
Being somewhere new to me, I wanted to explore!…but I was also tired. I napped not only because I wanted to be awake for sex, but I had literally just finished my last trip the day before and wanted nothing more than to sleep. Is that too much to ask for? I woke up, had AMAZING Chinese food, came back to my hotel and waited until the time he said he’d be off (8.) I heard nothing. An hour later and I’m just passively watching the Spurs game while teaching myself how to toss playing cards into a hat. By 10 I had almost given up when GGG finally texted me! He said he would be right over, he couldn’t get off early, yada yada yada.
When he got there, I wasn’t surprised at all; I was at ease with him without the beer. Good Guy Greg was probably the sweetest guy I’ve ever met off of craigslist. He had brought a backpack with him; inside was my newly discovered and happy to chug Sierra Nevada, comics that he thought I’d like, and some random things. Like The Boy Scout, he was totally prepared for all that was the Daring Vagina.
We started off slow; he came clean he had only had sex with one other person. If he hadn’t told me, I would have maybe said no more than five. GGG was eager to please and also more flustered than I was about condoms. We wasted probably 3 condoms because he’d get soft because he couldn’t get it on. Ladies and gentlemen, this is when I learned how to put a condom on like a mom and not a lover. Just imagine someone putting a condom on you, very un-sexy and un-ladylike, and that was me.
It didn’t take long for him to cum the first time; we braked for him to catch his breath and get turned on again. It was almost like The Forty Year Old Virgin. Almost. The next time was better, he lasted longer and we even tried my combo! To help turn him on, I changed into one of my lingerie pieces. I had brought a few and had GGG pick one. It didn’t take long seeing me in my black and pink outfit before he was hard and ready to go. He came way too quickly and I was left wanting. Thanks for the muscle spasm game being too strong, Catherine.
As mentioned earlier, I brought toys. A toy I brought was my glass dildo. GGG decided he would love to help me cum by using it on me anally. At first I was skeptical, but honestly, it was fantastic. I wish anal was always that slow, and fabulous, and wonderful! The glass dildo may not have made me cum before, but when I came, it was an amazing feeling. After chatting for a bit again and trying to drink more of the beer, I noticed it was after 1am. I groaned a bit, but this was nothing new to me; sleep a little, run a lot, shower the sweat off, sleep until the maid wakes you up, get on a plane and fly home.
We decided to have one more round in the shower. Did I mention he was exactly my height? Being my height and skinnier than me, it didn’t really have the ability to help get me into any sort of sexual position in the shower. After 10 minutes of it not working, I suggested we try the floor. It would have worked, if it wasn’t for his rightfully paranoid brain of wanting to use a condom. He became too soft and that was that.
Sadly, he left after that. I showered for real, set my alarm and followed through with my plan. I didn’t set a new personal record in the morning, but I did finish and got a sexy ass farmer’s tan.
Good Guy Greg and I talked after that trip; we texted, sexted, and he told me to hit him up if I was ever close to San Diego. Over the following 6+ months, we stopped texting. And when I say we, I mean he stopped responding to my friendly “hey, how are you, how is that gorgeous weather?” texts. I left San Diego with two new comics, and confidence in my sex appeal and skills.
He was Good Guy Greg, for real.
Lesson learned: Being a teacher and helping someone is sometimes just as fun as having experienced sex.
The Daring Vagina