So I feel compelled to give a bit of history, lest you think that I perhaps am all talk and maybe have never had sex before at all.
A bit o’ background on the Duchess:
– I lost my virginity when I was 17. I was in a relationship with the guy, but he definitely was pressuring me for sex. I was actually OK with the experience on the whole. The boy wasn’t a virgin and did his best to please me. I do find it hilarious though that all my friends immediately asked me: “how was it?!” How the fuck should I know? At the time I was just relieved to have gotten it over with.
– I didn’t even know what a blow job was until I was 16 and the thought of such a thing existing had never even occurred to me before. I remember being in high school gym class and a girl telling us about how she gave a guy a blowjob as a thank you for driving her home. “What else was I supposed to do? He drove me home!” (no euphemism or pun intended there) (And as an aside, uhh maybe just say thanks?). The way she describe the whole thing, I suddenly understood what she had done, and felt like a lightbulb had just been turned on in my head. Sexuality was a much more vast universe than I ever knew.
– 18 was pretty uneventful- then I turned 19. I went to University and kind of grew into myself. I was an unintentional flirt and had more attention than I knew what to do with. A few well-meaning people warned me that I was going to get myself into trouble if I didn’t watch it. Nothing ever came of there warnings, and to this day I still can’t quite sort out what it was that caused such alarm.
– I had a few boyfriends and did the regular sex thing. A blowjob here and there. Making out with random men in bars and such. Naked showers and the occasional bed of roses.
– Then I got the first offer. At age 21 I discovered the world of “friends with benefits.” Yet again, I had never heard of such a thing before. The way in which it was introduced is still both ingenious and hilarious to me. He offered me a “business arrangement.” There were to be no mergers, but frequent business meetings. He expected that we would have several business contracts – a non-exclusivity clause. I never did have sex with this little entrepreneur, but we did fool around a bit. He didn’t like kissing and wanted to go right from the bench to either third, or straight to home. Call me old-fashioned, but there are a reason the first two bases exist…
– At age 24 I actually accepted my first fwb offer full on. He was a few years younger than me but with oceans more experience. His favourite position seemed to be with us on our sides facing each other. My leg slung over his, with him impaling me deep. Either that or with me on top of him – me riding him hard while he fingered my clit. He was the first person that actually made me enjoy being on top. For the most part I prefer men to pin me down and fuck me hard and fast…
– Then there was one of my only real accidental seductions (sorta). Me being aggressive(ish) and fully expecting to be rejected, but having had a few too many drinks to think through the consequences. I went on a trip with a male friend, and he booked a hotel room with once king-size bed. He was giving me a massage (yes, yes…I know…)when I found myself a bit too teetery to sit up. I fell over and started kissing him. And he responded. (OMG! A man and woman sharing a bed, and the man responds when the girl comes on to him! This is the most amazing blog ever! Shut up.)
– Anyhow. I was a bit reluctant since we didn’t have any condoms. I mean I REALLY wanted to fuck him. But I felt like I had to make the token expressions of concern. Which he interpreted as a rejection and proceeded to roll over to sleep. With a huge sigh, and exasperation that I had to spell it out, I made him sit up, grabbed his face and said “you CAN convince me to do this. PERSUADE me. Put some effort into it!”
– At least he got it. In a hurry. Without further ado, his finger was in my panties massaging my clit. Within about 30 seconds of him finger fucking me, I had both of our clothes off and was in no way giving him the impression that I wasn’t anything other than a sure thing. We had been friends for about 4 years and I was more than anxious to have sex with him by then. He came through like a trooper. I don’t know if it was his natural style, or if he’d actually been paying attention to all the not-so-subtle clues I’d been dropping, but he did it right. He grabbed my hair, pulled me down and fucked me as hard (although unfortunately briefly) as I like. Yeah. too bad for the brief part. We tried it again a few times over the past 3 years, and that was always the issue. Honey? Condoms? Kind of serve more than one purpose…especially if that’s an issue…
– Anyhow, he was the last person I had sex with. So needless to say- I’m quite anxious and have been more than a little unsatisfied with my last few encounters.
– I find that martinis are generally a sure way to get some decent sex. The last couple of times I’ve had martini nights, the sex I’ve had on those evenings have gone remarkably well. There’s media boy- who was able to go more than once. And massage boy who could go for hours.
– Perhaps I should just be hitting the martini bars more often. Why do I need this online dating shit?