quizzical pussy

When I think of things I’ve wanted my entire life, the word “adventure” seems to come up a lot. I think deep down I’ve always wanted to captain a pirate ship in a sea populated by mermaids and monsters.

I used to define the perfect partner as someone who wanted to have adventures with me, and who made them better just being a part of them.

Now, generally, having a small fraction of the energy a healthy person has, it’s hard for me to get too ambitious and exotic. I have to carefully ration energy for everything I do. But trying something new is pretty much always, always worth the drain.

It does not hurt if there are orgasms involved.

I spent last night making out with and tickle-fighting my gay best friend and a mutual female friend (who, like me, IDs as straight). It was my first threeway play and my first time kissing another woman, and it was awesome! Not horny or romantic, just all friendsy and fun and biting and tickling and kissing. His housemates had to have heard us shrieking.

This is exactly how I imagine mermaids behaving. Yar.

My boyfriend loves my ass. I’ve never delved much into anal play before him, but I’m enjoying it… or maybe it’s the multiple orgasms he gives me before the anal play, which certainly eliminate any chance of tensing up.

Sometimes, while he’s got me bent over, he’ll reach into the Fun Drawer for some lube and start playing while he’s fucking me.

Last night, after a session of that, he turned to me and said ”It was just there, and it looked so good….”

I of course responded with ”So, you’re saying that my ass is like Everest?”

I think I love you. Because you’re awesome.

So I am a 21-year-old, relatively good-looking, frighteningly-intelligent, incredibly boring male, to the extent that I’ve never managed to keep a girlfriend interested for more than 3 months. Nor have I managed to get laid with a girlfriend, girl at a party, etc.

(It’s not that I can’t converse for hours on end about almost any subject. I’m just quite apathetic about almost everything.)

Instead, my entire sexual history consists of 2 visits to a bordello in Berlin.

The first time was… okay. While the prostitute was really nice (and gorgeous), I had no clue what I was doing. In addition, being significantly larger than the average male, the normal-size condom was cutting off my circulation something fierce, and I just couldn’t stay hard. All in all, I exhausted myself pounding away for an hour and a half.

Yesterday, I visited again. Much better. I specifically asked for a magnum condom right off the bat–she waffled around a bit, the whole ”you’ll be fine with a normal,” at which point I mentioned that I’m 8.5”. She got one.

Also, she was REALLY horny. As in, soaking when she stripped her panties off. We started off with mutual oral, and she stopped several times because I was somehow actually getting her off! She kindly thanked me for my consideration.

We did the typical missionary, doggy, and her-on-top missionary, and during the lattermost I managed to bring her off twice more (NOTHING feels better than a woman cumming around your penis), and ended up with a lake on my stomach from her enthusiasm! Sadly, my staying power–who’s heard of a noob who doesn’t shoot off at the drop of a hat?–meant that I didn’t cum before the hour and a half was up. I played it off as ”yeah, I usually go for hours on end. No worries!”

I found that interesting. Maybe if you choose to date in future you could lead with that? On second thought, that might be more of a third date conversation…

She spontaneously put her finger in my ass, and I liked it some, despite my faint inate phobias. But it rubbed it raw. To do this again, I’m going to have to ask her to use lube or even a device or gloves. And that’s just planning out anal exploration a bit more than I think that I can openly do, and still be a straight man.

Yes, I’m completely aware of how stupid this sounds.

You don’t sound stupid. You sound scared. And with the tons of shame piled on guys if they don’t adhere to demoralizingly rigid standards, it’s not surprising.

But pretty near every man alive has a prostate. So don’t think for a second that you’re alone.

Have adventures to brag about? You know I want them.

I had a dream that I started working at a brothel. Not as a janitor. I think there might have been a murder mystery somewhere in the plot, but brothel. That’s the part that stuck with me.

It was a rather low-rent, dismal establishment: one of those seedy brothels rather than, you know, the mind-blowingly classy ones you generally picture. In my dream, I wasn’t anxious about embarking on a life of harlotry, but rather the fact that this wasn’t one of the nicer cathouses in town. “If I start out here is that going to hurt my chances of getting into a better house?” I remember asking one of the girls turning me out. She assured me I could move on to bigger and better operations once I’d learned the game. I like to think we both knew she was lying, but I’ll never know for sure.

Strangely, this was all fairly realistic. The sketchiness of the brothel really is what I’d worry about, to the exclusion of loftier moral issues. If I’m getting paid to fuck, I damn well want to be a hetaera, not a pornai.

(image source)

Have you ever played “I’ve Never…”? If not, you have to take a drink now because that’s how the game works.

And oh, here are some anonymous internet confessions that may be related…

I’m a 25-year-old male virgin, and I’ve seriously considered hiring a prostitute to change that. The strange thing is that I know that it would not be particularly difficult for me to put myself out there and get laid the way everyone else does, but hiring a professional is oddly appealing to me. Perhaps because there is much less risk of rejection? I think it’s more complicated than that, but I may be rationalizing. The decision has been a source of some anxiety for me lately.

I’ve never received oral sex. I’ve been in one relationship and my gf just was never into the idea of it enough to give it a try. She’s my ex now and after we split, I started testosterone to make a gender transition. I love what testosterone has done for my genitals. They feel and act like my brain says they’re supposed to. It makes me want oral more than ever. But I don’t know how to explain my anatomy and I worry that I’ll never get someone to go down on me b/c what I’ve got is unusual. I think it’s quite sexy myself, but I’m aware there’s a lot of myth and prejudice floating around about trans bodies, and orientation and kinkiness (or lack thereof) don’t seem to make a difference in the level of transphobic BS. Worse than that, I’m afraid that getting a blowjob is somehow going to make me dissatisfied with my cock, either because my size will compromise the experience or because my partner says or does something interpetable as dislike or pity. I don’t want pity. I want someone who’s as into my cock as I am. I don’t know how to find that and I sorta think that admitting how good I feel about myself will come off as crass because it’s cliche that men are all about their dicks, right? And no one wants to hear about that. But I really, really, really want a blowjob!

Sounds like you’re proud of your body without being a narcissist, which is sexy. And chicks like me abound, and we love giving blowjobs to sexy guys. Thus, I find it hard to believe this story isn’t going to have a happy ending. Please let me know how your first blowjob goes!

I haven’t had sex in five years and I’ve never dated. I’m almost thirty and I have no idea what I’m doing! I thought this was only supposed to happen to religious fundamentalists.

I frequently lie about my sexual experience (pointedly the lack there of). To myself I count the times I had sex as one, but he didn’t get his dick all the way in before he came so I’m even lying to me about it kind of. The real confession is that I read sex blogs and pretend I have the bloggers sex lives when I’m talking to my friends.

Calling all firsts, lasts, fantasies, lusts, fables, and laments: send me your secrets here.

I have a confession to make. I totally watch the British ITV2 show Secret Diary of a Call Girl. I consider it kind of a guilty pleasure. It’s the type of TV critics seem to like to call a frothy confection: a half-hour drama following a high-class (“upscale”) London call girl (played by Billie Piper) as she juggles her secret career as prostitute Belle De Jour and her personal life as Hannah Baxter. Yeah, I watch it and like it. Now what?

I appreciate shows and movies that portray sex workers as real people who aren’t predators, victims, or addicts. I do understand and acknowledge anyone who feels compunction about glamorizing something that can go so terribly wrong, especially when that glamor might threaten to blot out the stories that need to get told. The tragic injustices exist: hell, they abound. Prostitutes can and do encounter violence and exploitation, and please let’s not forget the nauseous abundance of women, children, and men forced into sexual slavery to fulfill the global demand for sex workers. There are major problems with the sex-based sector of the economy, some of which of arise partly because so much of it has to operate underground, accountable to very little, and even less that’s ever concerned with the health, independence, and well-being of the participants. Misplaced moral outrage and criminalization chase sex work into the shadows, and we know all too well what happens in a darkness like that: that’s how Sméagols become Gollums.

I believe it’s time to make a clear distinction between sex crime and sex business. These horrible infringements on human rights shouldn’t find it so easy to ape a harmless transaction between consenting adults any longer.

But how about people who are drawn to prostitution and other sex work because it’s fun, because they enjoy both money and sex? Why the hell that should present a problem to anyone is beyond me. The self-created happy hooker who makes a deliberate career choice and executes it with responsibility deserves more play. That’s the kind of sex worker we should encourage. Secret Diary portrays a call girl’s vocation as difficult and complicated, but also rewarding and sexy. Plus, there are times I feel sure I could compose a panegyric to Billie Piper’s ass.

The show is loosely based on the real experiences chronicled by the real owner of the really fake pseudonym Belle De Jour, who maintains a blog and wrote bestselling books, remaining completely anonymous until early this week. Turns out (via sexoteric), she’s 34-year-old scientist Dr. Brooke Magnanti, a respected specialist in developmental neurotoxicology and cancer epidemiology. These days she’s spending her time researching children’s cancer. Yep, she’s a science geek who’s trying to keep kids healthy: your move, naysayers. She spent 14 months selling sex to support herself while she worked on finishing her thesis, and she doesn’t regret it at all. In fact, she enjoyed it.

Good on you, doctor, for coming out and proving that a whip-smart woman (who is not, as it turns out, some man’s wishful invention or a writer’s fantastical thought experiment) can choose to participate in prostitution, have a great time, and walk away when she’s good and ready.

Now, to wait for season 3 to start…