DareDone Date Step 2 and step 3 upcoming.

I'm going to be a little scatterbrained on this one, I have a bunch of work to catch up on, and not as much time as I'd like, so its going to have to be done piecemeal so... hopefully I make sense.

Anyway, first things first, here were the dares:

Two that were punishment based:

Try to get him to call you "Mama," "Mommy," or something similar during the date. If you can't, go buy a coloring book and some crayons (if you don't already have them) and finish coloring the entire coloring book within the week following the date. Be sure to stay inside the lines.

and

You must try to get him to drink three different beverages during the date. For each drink he doesn't have, you will have to drink a glass of water after the date and wait an hour for every drink he doesn't have before you may use the restroom.

Some that were rewarding ones:

Go to a clothing store, get him to try on a skirt or dress. If he does, he can pick out something for you to try on.

If he will masturbate in the car, you will too.

He has to kiss a boy. If he does, let him watch you kiss a girl.

Since you're going to be doing more dares in this series, tell him if he'll go out with you again, you'll wear something low cut.

and one less easily categorized one:

Wear a skirt and panties; what you wear on top is your choice. At some point during the evening, you must take your panties off (while he is there, no sneaking off to the toilet) and you must convince him to put them on.

I'm going to try and make sense now. Hope it works.

The plan was to go out for appetizers and desert, lighter than a full meal and more fun. I think he was a little weirded out by the whole asking/telling him out sort of thing, and didn't really know what to expect. When I met up with him he was kind of awkward. I don't know if that was normal or not for him. I tried to soothe it over by saying he seemed interesting and I was curious what he was like, and it was fun to meet new people. I did say I'd pay, which was only fair, since I was the one inviting him and all, and since then I could say "I'll be your sugar mama" and stuff until I finally got him to say "thanks, sugar mama" and first dare checked off!

The other punishment dare was easier, he drank water and a soda on his own, and I had him try some of my smoothie. 3 drinks, check!

Also, just a quick side note to all the boys reading this. If you're out on a date with someone, even if you have no idea if its a date or not, try to not be awkward, and if you are, at least try to be responsive and engaged. Thanks!

The conversation was a little one sided. He occasionally would talk a lot about something, but most of the time it was a little hard to keep the conversation going. That may have been because I was trying to gin him up by asking lots of weird questions like "whats your dark secret" and "come on, are you telling me you wouldn't go streaking right through this restaurant if you could get away with it?" I was trying to make it seem less weird when I tried to get him to do crazy stuff. One that kind of worked was the "make friends by doing stupid stuff drunk" because apparently he knows a couple people with some entertaining stories, even if he doesn't drink...

That led to the "masturbate in the parking lot" which kind of weirded him out, and then I think I really surprised him with the "if you will, I will" and he just kind of stared at me for a minute. He didn't go for it, but it did kind of look like the almost considered it.

I tried a couple other "Crazy things you've never tried that you should do" like for example "kissing a guy?" no way. He's sure, even though hes kind of artsy. Even if I kissed another girl to prove its safe. Although I can do that anyway, if I want to. haha.

He did ask why I was so interested in him doing weird things. I told him weird things are important. You gotta be weird sometimes, makes things more fun and interesting or something like that. I promised I'd think of something really weird for next time we went out. He was like "Next time?" I told him of course, we'd have to go out, I hadn't gotten him all the way out of his shell yet. I told him I'd wear something low cut to make it up to him.

The last two dares I managed with "a quick errand I wanted to do while we were out" I needed to pick up socks from the Target. I'd had this one mostly planned out, but it took a little bit of quick picking. I spotted an eyecatching skirt, different shades of pink with ruffles, while we were there. I wanted something stranger, but that would work. I did the whole "check this out, wacky!" thing and said "try it on!" he was totally not interested. I pleaded with him for a bit and eventually got him with the "come on, I'll try on anything you pick out." he was thinking about it so I was like "here, look around. Pick out anything. If you try on the skirt, I'll try on your choice."

So we looked around. This part was the exciting bit of all the dares, at least so far, since he kind of wimped out some of the others. I was kind of expecting something clever and creative, since he is artsy and all, but I guess boy comes before artsy. He picked out some skimpy little nightie. Totally unoriginal. But hey, whatever.

So I got him to try on the skirt. He was going to back out when he put it on but I talked him into letting me see. it wasn't half as funny as his facial expression, and he almost closed the door on me when I was laughing but I had to have him wait for the second dare. You could see his boxers under the skirt (I picked a shortish one on purpose) so I was like, you're ruining it, take off your boxers.

Note to boys again. When a girl says take off your underwear, your answer is yes, ma'am

He did not answer correctly. He was like "no way!" and tried to shut the door on me again. I needed him to not, because this was my opportunity and I had no plan B. So I just started taking mine off and was like "Here, its no big deal!" and he stared at me. Fortunately nobody was around. I had no idea what I would've done if someone was. thank god for target late at night.

He just stared at me and I was trying so hard to act cool about standing in the middle of the store holding my panties, but I think I was blushing like mad. So I was like here, put mine on if you need something. he turned my offer down. Seriously, this guy needed a clue. I was actually a little frustrated. Clueless. and I really wanted him to take them because I was standing there holding them awkwardly. And I really couldn't think of how to be like "please, wear my panties" without coming off weirder than I already did, so I gave up. I don't know if that means I failed that dare or not.

He changed back quickly after. He told me I didn't need to try on the nightie if I didn't want to. Sweet, but I wasn't in the mood for sweet at that point. I either wanted to kill him (in a nice way) or get him to actually take an initiative. I still did it, dare and all, and I wanted to see if that might jump start him.

I put my panties back on when I was changing, although I had to take the bra off for it. It was pretty skimpy, but it covered all the important bits, if it were a bit longer and slightly higher cut I probably could get away with wearing it out, but it was high enough and just low enough to be bedroom only. Also, pretty low quality material, so I wouldn't wear it anyway.

So I came out and showed it off, did a couple cheesy poses. He just stared some more, but he was definitely looking. I started to do a twirl in one of those spin around to show all sides but stopped pretty quickly once I realized I didnt need it riding up. I couldn't stop giggling after that, and he started laughing too, but he didn't know what was funny until I explained it to him, but it was a fun moment. He let me change back after that.

We poked around a bit more before I bought the socks and we went home. He walked me back to my dorm, which was nice of him, and he was, well not less awkward, but differently awkward. More like he didn't know what to say than he just didn't want to say anything. I told him to call me when he got back from break and we'd go out again. He said ok. Hopefully he means it.

This dare was fun, I liked the twist of getting someone else to try stuff, but it was hard when he refused. Also, he was frustrating, but that had nothing to do with the dare. Hopefully next time he'll be better. Maybe I'll have to get a pervy friend to give him a clue. Or maybe not.

So, next step: for the next date, this is what I need. I need a wacky thing to do, cause I promised, but I could pretend to forget and he probably wont call me on it.

As for the dares from Slick, there are two things. The next game is fantasies. I ideally need to get him to share some of his, but also share some of mine. Twist is, you get to pick my fantasies. it would be more fun if the ones you send in are actually yours, but you can make them up to. I'll take the top third or so of what comes in (we're trying a ratio winning thing). Ideally something plausible, since I also need to try and talk him into fulfilling one.

The second bit is that this is supposed to get more serious. So we're going to let you choose how far the next date goes. I'm going to get a range, minimum and maximum. I have to get him to, or go myself, to the minimum. Can't go past the maximum. Send in suggestions for either or both, we'll be picking by taking the highest and lowest of all the suggestions for minimum and flipping a coin, then doing the same for maximum.

Also, this is just a normal date, feel free to send in suggestions for other dares such unrelated to the game.

One other thing, sorry. Becky will do one dare for this date, if you have any ideas. She wont be coming along, so it would need to be at the start, finish, or she'll need to run into us halfway through or something, but one dare, she'll do. Also, I've picked out a dare for her to do when she gets back from break, so stay tuned!

PS, sorry this is so delayed, I'm still not entirely caught up.