I’m 21 years old, and have not had much experience with sex, and most of it has not been very enjoyable. I would really like to explore my sexuality much further—I am a fairly shy and modest girl but get me in the sack and I can get pretty wild. I want to try and open that side more, you know, be ‘freer’ if you will.
Anyway, I was bored one night, so I decided to post an add in casual encounters on craigslist, basically explaining this need of mine—just for shits, to see what would come up. It was practically a joke, because really I just expected to get a bunch of iphone photos of dicks in response. Not to mention I’ve always been against the internet thing, because you never really know who they are, and it always seemed kind of stupid/desperate to me. Hell, I didn’t even plan on responding to any—it was kind of a spur of the moment, probably change my mind about it tomorrow, kind of deals.
Most responses were just creepy or dumb, (fun to laugh at though) all except for one. Didn’t see it coming. This guy seems genuinely alright, is in school for massage, has sent several pictures (of his face) and not to mention in all of the “hey what kind of interests do you have” he completely blew me away and ended up basically explaining my interests, dreams and goals back to me before I even got the chance to. We also seem to have a good understanding of each others needs and ground rules.
We’ve sent some emails back and forth for a couple months now, and he’s invited me to get coffee and the like recently (however I missed it, that’s what happens when your only form of contact is through email, which I don’t check too often anyway) and I would like to, but there’s also that part of me thinking “Oh hey, what if I get stabbed?”
So I guess there’s really a couple questions here I’m trying to get at. Is the internet thing somewhat legit? If so should we try and make an actual meet up plan through email, or should I just pass him along my phone number?
And like I said, I’m a pretty shy and modest girl. Cautious with strangers, not so much cautious with the rest of life. I’ve never done anything remotely like this before (part of the reason I want to, I suppose). Never met up with a stranger like this, and I’ve certainly never fucked a stranger. How do I meet up with this guy and (if it works out) turn him into a fuck buddy in a non-weird/awkward (or less-weird/awkward) way?
Don’t give him your number. Get his. Call him when you’re ready. If there’s still chemistry after a phone conversation, feel free to plan a meet.
Choose a very public place, and make sure a friend with discretion knows where you’re going. If you’re feeling particularly cautious, pick a place where he doesn’t see you park. I don’t know what kind of town you live in, so a generic recommendation would be a shopping mall or an outdoor restaurant.
If the meet goes well and you’re in the mood to fuck, get a room. Don’t go to his place. Don’t take him to yours. This shit only goes down in a hotel. A nice hotel. Get a fucking suite if he can afford it.
Since this is your first time, plan ahead and have a couple of hotels in mind that you know and trust. It’s fine if you want to chip in on the room, but it’s his name that goes on the room. It’s his drivers license and credit card that goes on file. No exceptions.
Make sure you get your own room key card. I suppose it’s an extra bit of safety, but personally, I like to keep them as a souvenirs. At this point, I could tile a bathroom with all those little fuckers.
Be safe and listen to your gut. If it ever starts to feel weird, just walk out the door. You may want to check in with your friend before the hours start slipping away, but other than that just do whatever hot nastiness you like.
(Oh, and if you make it this far, write me back and I’ll tell you how to turn him into a regular fuck buddy.)