Q&A: Caught

Just a quick note before we get started: I’d still love some more input about the girls mentioned in the sticky post on the front page of this blog. I’d really like everyone’s help on this!

JackM wanted to know: Ever been caught or nearly caught masturbating?

Assuming that this does not include times that I’ve deliberately been “caught,” then… no. At least, I can’t think of any situation like that. I’m sure that’s not the answer you’re looking/hoping for, but it will have to do.

On the other hand, I can think of two times that I’ve been on the other end of this question: I’ve caught someone masturbating. The first was about a year after I moved out of my parents’ house. On a visit back, I accidentally walked in on my younger brother hard at work in the bathroom. Now, I’ve often thought about my brother fucking me, and seeing him stroking his hard cock just fueled my imagination. The situation was awkward, though, and definitely wasn’t an opportunity to act on it. I quickly apologized and closed the door.

Q&A: Wearing Him Out

PatrickOF wants to know: Have you ever worn out a guy during sex before?

It’s not uncommon for me to be wanting more sex after the guy has cum and he’s unable to continue for at least a bit. Some guys can go again right away. Some need a short break before they’re ready to go again. Sometimes I can shorten this break by whispering dirty thoughts in his ear, or talking about how much I love being fucked by him, or sucking his cock until he’s nice and hard again. But I don’t think that counts as wearing a guy out, even if I don’t arouse him back again. But there was this one time…

This was a guy that I’d fucked several times. A few times, when still wanting more, I’d managed to arouse him to give me some more. This particular night, he’d fucked me doggie style until he came over my ass. We relaxed for a bit, laying down on the bed as my fingers gently caressed his cock and his played with my tits. As soon as I felt him start to harden up again, I started working faster and harder, until he was rock hard again and I climbed on top of him and lowered my pussy over his cock and began to ride.

Q&A: Girth

ShylyAnonymous sent me this: I apologize if this is a silly question or one that isn’t relevant, but in your FAQ I noticed you talked about your ideal penis length, but does thickness matter to you? If so, how? I’m a bit embarrassed to admit this (though perhaps I shouldn’t be given the relative anonymity of the Internet, and your very welcoming and supportive atmosphere here), but I’m a virgin long after most of western society would probably say is “normal” for a guy. I guess I just figured getting a little more knowledge might help me feel a little more prepared or less anxious. Thanks for the time and the compelling content you create. It seems pretty rare to find someone as articulate, open, and thoughtful as you.

First off, thanks for all the compliments! I’m very glad you enjoy reading what I write, and very happy that I can pass on something that people might find useful.

I’m going to skirt around the main question for a moment and address something else you mentioned. Getting more knowledge about sex can definitely enhance your enjoyment, but you’re never going to really be prepared for your first time, and you’ll definitely be anxious or nervous. The best thing you can do to perform better and with more confidence is really just start doing it. You’ll learn more from experience than I can ever shed light on, and the more you do it, the better you’ll get.

Alright, the reason I don’t talk about my ideal thickness or girth is that, while it matters, it’s difficult for me to judge. People sometimes ask me about the size of cocks of the guys I fuck as if I pull out a tape measure just before he enters me. I don’t. Mostly what I judge on is rough comparisons of how the guy feels compared to some of my toys. I know how long each of my toys is, because, well, that’s how they’re advertised. If girth was mentioned on the packaging, I don’t remember. Thickness is important, because it’s not just how deep the dick can press, it’s also about how well it fills the space inside. For both guys and girls, the tighter the fit, the better. Or at least, that’s my view. Really what it all comes down to for girth is much the same as what it comes down to for length. There’s too big and there’s too small… but there’s a wide range in between that’s good to great. And, in both cases, I’ve very rarely come across anyone outside of that margin.

So relax, and go find yourself a girl!

Q&A: Sexual Disappointment

Got a question from Lexy, who wants to know: When was the last time you were disappointed by a guy. Meaning you went on a date, he was very hot. But then ended up having a small penis and/or was bad in bed?

I guess the last time would be about 5 months ago. This guy was hot and a great flirt. I had a great time with him on the date. We went to a show, then a late dinner, then he asked me back to his place. There was no reason on my radar to say no.

At his place, he continued with the flirting, and we both continued drinking, and things got intimate. He obviously had a thing for my tits. He wouldn’t leave them alone! Normally, my tits love attention, but this guy was a little too focused on them. It felt good, but I really wanted him to explore the rest of my body. A couple of times, I took his hand an slid it between my legs, but he quickly found his way back to my tits.

When our clothes came off, he got on top of me in a missionary position. Nothing wrong with that! He stuck his cock into my pussy and began fucking away. His cock was probably a little smaller than average, but still a fine size. The problem was that he quickly got into a rhythm and never changed it. It was fairly fast, definitely more fucking than making love. He came fairly quickly. Not early or anything, just not particularly long lasting.

All in all, there wasn’t anything particularly bad about this guy, but there definitely wasn’t anything particularly good, either. It was very humdrum and dull. It felt good, but it wasn’t really fun. After the fun I had talking and flirting with him, it was a pretty big disappointment. I haven’t gone out with him since.

Anyone else have any tales to share?

Q&A: Slutty Realization

Frank asked me a question that I’m not going to answer here. Why? Because the answer is in my FAQ. If you’re reading this, Frank, please check that out. Instead, I’m answering a question from Ben: At what point did you realise you were a slut/whore?

Here’s a fairly short version: In high school, I fell in love with my first boyfriend. Well, my first serious boyfriend, at any rate. And boy, did I fall hard for him! I think your first love is always a significant event. Not only was he my first love, he’s also the guy who took my virginity. At any rate, he dumped me for another girl. I was hurt, I was angry, I was embarrassed, I was jealous.

To try to make him feel something similar, I sought out revenge. I went out with the first guy to ask me out and gave him a blowjob on the first date. I was hoping my ex would hear about it, get upset, realize he was wrong, and take me back. He didn’t. So I fucked this new guy. Someone else asked me out, and I fucked him. I was horribly insecure at this point, especially since my ex didn’t seem to care. I’d fuck any guy who asked me out. 

Q&A: Sex Life Title

Sorry there was no entry this last Saturday. I just didn’t get around to it with the holiday. Today, I’m responding to Ryan D, who offered this: Describe your sex life with a film title.

I had to look at all the movies I own a few times, the ones currently in theaters, and several others as well. I tried to disassociate from the content of the films as much as I could, and just focus on the title. There were several that I seriously considered, but in the end, I had to choose just one. Ultimately, I’ve settled on Heat, which conveys a hot and steamy time, which is pretty close to how I view my sex life.

I’d love to hear any other suggestions for titles, as well as which you would choose for your own sex life! Anyone care to share?

Q&A: Thinking of Sex

Joey has a good question: Do you think males think about sex more than females, or females are better at hiding the fact that they are?

I think girls think about sex as much as, or more, than guys. I don’t think they’re necessarily better at hiding it; I just think that the societal expectation is for guys to be sex-crazed and girls to far too innocent for that. It comes down to the same reasoning for sexually active guys to be considered studs, while sexually active women are sluts.

Labels and expectations do not reflect reality. If girls hides how much they have sex, or even how much she thinks about it, it has more to do with worries about the social repercussions of being a slut than it does with anything else. There are some girls who enjoy being a slut while maintaining an innocent little princess look because they use this dichotomy to manipulate guys, but I think most girls who hide their sexual drive are mostly worried about losing social standing or some such.

Guys, on the other hand, have the freedom of an expectation to openly ogle girls and brag about their sex life. Well, maybe “freedom” is the wrong word. I know many guys who feel they have to exaggerate or lie for much the same reason as many girls hide or downplay.

I’ll wrap up with a pretty simple comment, though. In my experience, while the amount of sexual thinking may be pretty equal between guys and girls, girls have a far dirtier mind than guys!