Midwest Maiden

A 20something playing the game called life

It’s in His Kiss October 12, 2008

Filed under: Uncategorized — maidenchessa @ 12:06 pm
Tags: ,

I had a date last night.  Well, I don’t know if “date” is really the right word.  It wasn’t a play session either.  It just was.  I’d talked to the guy for a few months; we met on CM.  I’d been kind of putting off meeting him though.  When we talked on the phone or online (which wasn’t regularly) we only talked about lifestyle related stuff, which made me think we wouldn’t connect beyond something physical, and I wasn’t even sure about that.  He is the most adorable thing ever – why would he want me?  And, he lives almost 2 hours away – that’s a long ways to drive for something I’m unsure about. 

 

But, last night I made the drive to his place and I am so glad I did.  In so many ways, he’s the guy I never thought existed.  He is funny, smart, artistic, kinky, AND a farm boy!  There was never a lack for conversation.  When we went to bed, my cheeks hurt so bad from smiling and laughing so much.  He really put himself out there for me too.  He did everything I asked of him (not that I asked anything too drastic) which was a big deal for him.  He’s been interested in the lifestyle for years but has only had one previous opportunity to explore it in real life. 

 

After I’d been there a little while he told me what his one real limit was – kissing.  I was shocked.  It took me a few minutes to wrap my head around the idea.  Everything (including sex!) was on the table – but no kissing.  He said he never kisses on the first date – it’s something he saves for girls he’s semi-serious about.  He acknowledged that there was logic missing from his theory but that’s the way it was.  To a certain degree I guess I get where he’s coming from; Julia Roberts in “Pretty Woman” would do anything her clients wanted, except kiss on the lips.  While I respected his decision (and in some ways it made me want him so much more because it really is sweet!) it was frustrating!  I wanted him; I wanted to kiss him *so* badly.  More than that, even though we’d just met, I wanted to be someone he was semi-serious about!

 

Even though sex was an option, I couldn’t sleep with him without kissing him.  I don’t do casual sex [anymore] and even though we’d probably see each other again, sex without kissing felt very casual – despite the fact sex with kissing can be casual so I know the two are not exclusive.  And, by him not kissing me it implied the verdict was still very much out about me; I didn’t want to put myself out there sexually if he wasn’t sure about me. 

 

The whole kissing thing wasn’t all of why we didn’t sleep together though.  It wasn’t until our 4th date that I slept with Hunter – which was also the first time he’d gotten near my tits or any other part of my body.  I feel like I’ve grown a lot in the past year and a half where sex is concerned.  I *really* want a guy to want me for me, not for the sex.  Not that waiting only a few dates ensures that, but it’s better than jumping in the sack right away.  Another thing is that I have to build up confidence with each guy.  I didn’t feel extremely dominant last night, despite the fact he was extremely submissive.  Even though I wasn’t really nervous at all around him, I didn’t really put myself out there either.  I was too shy to try a strap-on, or a whole lot of anything else.  With Hunter it took probably around two months before I had the courage to take his ass that way.  I don’t foresee myself ever being the type of person who can just do scenes.  For me to feel & be truly dominant, it has to be within the context of a D/s relationship. 

 

He said he wants to see me again but for my own sake I’m trying not to get my hopes up too much.  If he’s not interested in pursuing something beyond just sex, then I won’t see him again – that really isn’t what I want.  Even if I don’t see him again, now I know there are guys like him out there so I guess that’s something.

 

The Good Stuff September 7, 2008

Filed under: Uncategorized — maidenchessa @ 5:12 pm
Tags: , ,

I fully intended to have this post done on Wednesday night but I’ve been swamped with work!  Anyway, here goes…

 

The good stuff started when I, out of nowhere, reached over and grabbed his balls through his jeans.  Just rubbing him through his pants got him going like no other.  He’s used to cumming on a semi-daily basis and he hasn’t been allowed to for a week or so.  Needless to say he was horny before I even started rubbing him.  He made the most amazing noises while I was rubbing him – much like the ones he makes when he’s in pain.  And, as I’ve written many times before, that makes me *so* wet.  It was odd to be so aroused from teasing him.  While teasing has always turned me on, it was the pain that really got me going.  In a lot of ways, it was actually the opposite with Dayton. 

 

I’ll really challenge that theory next time we’re together though, hehe.  We didn’t get too much into pain.  I eventually took his cock out and worked it both with my hand and mouth.  When my mouth wasn’t around his cock, I was teasing him relentlessly about how easy he was to turn on.  A few times he put his hands up to his face and literally hung his head in shame and embarrassment.  I’ve never *seen* the fruits of my labor in regards to humiliation as well as I did with him.  When I pursued humiliation with Hunter, he kept it inside and I had to be satisfied knowing/hoping it was humiliating to him.  Actually *seeing* the humiliation is almost intoxicating. 

 

I told him while I was teasing him that I wasn’t going to let him cum that night.  He’d already waited over a week because I’d ordered him not to before we met.  He took it in stride – didn’t really complain or anything.  It was thoroughly entertaining to me though because as I told him that, I had every intention of letting him cum later that night.  When he called some 2.5ish hours later to tell me he got home safely, I told him he could cum.  I don’t totally remember the conversation because I’d been sleeping a couple hours at that point and had taken my sleeping pill, but I definitely remember the excitement in his voice when I told him.  Too freaking adorable!

 

~*~*~

Not a lot has happened since that night.  He and I have both been ridiculously busy with our jobs and he’s actually 4 hours away for work this week so not a lot will be happening any time soon.  He is good with me though.  You know me, I worry like no other when I haven’t heard from a guy but that doesn’t seem to bother him.  He always patiently answers, “Yes, I’m still interested in you” (or something along those lines) whenever I ask if he really is just busy or if he’s no longer interested in me.  I greatly appreciate the fact that I can be completely honest with him about my insecurities and he doesn’t judge me for it or run in the other direction.

 

Dayton September 3, 2008

Filed under: Uncategorized — maidenchessa @ 5:20 am
Tags: ,

I had a date last night with Dayton.  We were supposed to get together over the weekend but something related to his work came up.  Because I’ve been screwed over in the past with guys not following through on their word (*cough* Hunter) I thought for sure he was just playing me.  But, he ended up coming to see me (a 2 hour drive) last night, which I know was a sacrifice for him because he’s a lot like me in that there’s *always* something that needs to be done for work. 

 

He was 35 minutes late though and to say the least, I was not happy.  The thing that bothered me was that he didn’t call to say he was going to be late.   I arrived at the restaurant at the time we were scheduled to meet and called him from my car to see where he was.  Imagine if I would have just gone in to wait for him!  I would have been sitting there looking like an idiot (I know, it wouldn’t have been *that* bad but I do have some social anxiety so it would have been traumatizing for me!)  I know I was a total bitch when we were talking on-and-off for those 35 minutes.  I’m lucky he still showed up and didn’t just turn around and say screw you. 

 

We chatted a lot over dinner – there weren’t really any of those awkward moments of silence.  At the end of dinner I asked if he wanted to come back to my place and hang out for a bit.  He recommended that we instead find someplace to just sit and chat or go for a walk.  I took that to mean he wasn’t interested in anything more than friendship.  Come on, if he really wanted to get in my pants, a walk would not provide adequate opportunities.

 

We settled on going back to my place though because it was getting dark.  We chilled and watched the Republican Convention, despite the fact we’re both passionate democrats.  An hour or so later he said he should probably get going.  That’s when he *finally* made a move!  Up to that point we’d been sitting on separate ends of the couch.  He reached for my hand or something like that so we ended up holding hands for a bit.  There were moments that took me back to high school as I kept thinking, “What do I do next?  How do I tactfully take another step?” blah, blah, blah.  We did eventually get to the good stuff though.  :D

 

Two new friends June 25, 2008

Filed under: Uncategorized — maidenchessa @ 8:51 pm
Tags: , , ,

I had a date-ish type thing last night.  I *though* it went well but I haven’t heard from him since so I can’t really say for sure. 

 

I met the guy at Coldstone.  We had ice cream then headed back to my place.  When we got to my place we watched Top Gun and chatted.  We *really* clicked on a vanilla level.  At one point I turned to him and said, “So, you gonna kiss me or what?”  I’m forward like that with guys.  Even as a domme I’m not a big fan of making the first move so by saying that I’m technically making the first move but they actually have to make the first physical move.   We kissed a little but the mood was abruptly killed when he started kissing my neck.  See, I work with kids and that day we’d gone to the pool.  The pool requires putting sunscreen on.  Sunscreen does not taste yummy.  After we got done laughing our asses off we went back to watching the movie.  When the movie was over we watched a little TV (an hours worth actually) until I finally said something AGAIN about him making a move.  We made out a little more and then I had him take off his pants.  I caused him a lil pain, teased him A LOT and we made out a little more and he went down on me.  I had told him previously that he could cum that night so I had him masturbate until he came.  Then he left.

 

I understand why he had to leave so abruptly – it was 11, he had an hour drive home and had to be up for work at 3:30 a.m. the next morning.  I hadn’t realized that he had to get up so early until that point.  Even though it makes complete sense that he would leave then, it still made me wonder about his interest in me (I know, I worry too damn much!)  And, he was supposed to text me when he got home so I knew he’d made it safely.  He didn’t and I didn’t hear from him at all today either. 

 

I’d be pretty disappointed if he isn’t interested.  Like I said, we totally hit it off on a vanilla level.  We have a lot in common but enough minor differences to keep things interesting.  We talked a lot about sports and politics and life in general.  Hunter and I rarely talked about things like that at length.  But, sexually Hunter is hard to beat.  I didn’t click sexually with this guy the way I do/did with Hunter.  I did get turned on but not like with Hunter.  I think that could improve if more feelings develop though.  But who knows if he even wants that to happen.

 

I called Hunter last night after my date left.  I told him I’d had a date and that I did like the guy.  He didn’t have a whole lot to say.  He just said he can’t ask me to wait around for him.  He had to go abruptly though because he had friends over but I stressed that I wanted to talk about it with him some more.  I know he has more thoughts on it than what he said I just wish he would tell me!  But, he’s never been good at expressing his thoughts/feelings so I don’t know why this time would be any different. 

 

~*~*~

A few weeks ago a girl (we’ll call her Lisa) from my area who is my age and a sub contacted me on the fetlife website.  I think I’d mentioned her previously.  Well, we met tonight for coffee.  We chatted for a little over two hours!  The time just flew!  I can’t even begin to put into words how great it is to actually hang out with someone who “gets” you – someone you can be pretty much totally open with.  I was totally comfortable with her right off the bat.  I talked a lot – too much probably!  But, I was totally myself and even shared a story or two that didn’t portray me in the best light.  It’s so refreshing to know right off the bat that someone is going to accept you for who you are.  Plus, it is cool to have a friend who’s actually in a 24/7 D/s relationship.  The only 24/7’s I’ve been exposed to are from blogs I’ve read which isn’t quite the same.  She and her fiance were vanilla for a year or so before she brought up her interest in D/s.  He wasn’t really a dominant person at all before she brought it up but he’s really embraced it.  How cool is that?  Perhaps I shouldn’t totally rule out vanilla relationships…

 

~*~*~

Also, I got a promotion of sorts at work today!  Right now I’m working in the two 4 year old rooms as kind of a floater.  But, next week one of the room leaders is going to have her baby so I’m taking over her room while she’s out on maternity leave!  I’ll have my “own” room again and they’ll be school-aged kids!  I’ll get to plan art lessons and go on super cool field trips (last week they went on a riverboat ride down the river!).  And, in the fall I’m officially going to be a pre-school teacher!  They’re re-doing their system and starting the team-teaching approach.  I’ll be team teaching with the woman who’s going to be on maternity leave (she’ll be back by then).  I’m SO relieved to have a set-in-stone job for the fall!  And, since I know I’m staying in the area, I think I’m going to apply for grad school in the fall.  YAY!

 

First D/s-ish date March 3, 2008

Filed under: Life — maidenchessa @ 12:35 am
Tags: , , ,

I had a date tonight with a guy (Hunter) I met on collarme.  I had originally contacted him about a week ago.  I was a little hesitant to contact him, as he is 2 years younger than me.  I’ve normally dated older guys – part of the maturity thing I think.  But, this guys profile caught my eye – it wasn’t the typical collarme profile.  But, he is a typical 21 year old. lol.

While I’m only two years older than him, it does feel like a significant difference.  He’s still in college and living with 5 other people in a campus house.  He goes to “keggers” on the weekends and has homework during the week.  We just live in two different worlds.  I’m sure part of it is a difference in personalities too – I’m just not into the party/drinking thing. 

So, we met for ice cream.  He scored points with me when he recommended that.  I cannot believe how many guys still fall back on the movie thing for a first date.  Seriously, there is no point to that!  That’s two hours you just spent with a new person and learned absolutely nothing about them.  What a waste of time.  Anyway, we talked a lot about basic stuff over ice cream – our families, school, typical surface stuff.

We popped a move in and started cuddling on the couch.  Right away he put his arm around me.  I loved that even though there’s the D/s dynamic, he’s still not afraid to take initiative.  We talked for the first 1/3 of the movie – this conversation more in-depth.  We watched a little of the movie and then I kissed him, which lead to making out.  It was so odd though. There were times I couldn’t breathe while we were making out! I’ve never ever experienced that.  I tried to move my head certain ways so my nose wouldn’t be covered when kissing but it didn’t seem to work.  We’ll have to work on that.

After making out quite a bit of making out and some time of me rubbing his cock through his jeans, I told him to take “it” out.  I began rubbing it while we continued making out.  Eventually I pulled away and said I wanted to watch the movie.  I continued to rub his cock though.  A couple times he tried to run his hand down my pants or up my shirt, but I was always quick to move it back to my hip where it had been.  At one point I said my hand was getting tired and moved his hand to his cock.  For a while he rubbed his cock while we sat there just watching the movie.  Then I continued doing it again until the movie ended. 

Doesn’t it seem odd that the domme was rubbing cock all night while the sub just sat back and enjoyed the ride?  I’m odd, what can I say?  I sent him home with directions not to touch himself/cum for the rest of the night.  Knowing that he was so horny when he was with him me for the rest of the night and there was nothing he could do about it, totally does it for me.  Teasing is so hot.  Plus, I think it shows the difference in status – I’m sitting there fully clothed while he has his cock out for me to play with.  And, not letting him touch me in too intimate of ways was a discreet way for me to show that his body is mine while mine is not his.  He has to earn access to my body – it is a privilege. 

I was a little nervous about not being domme-like enough.  I felt like since we met on collarme there were these expectations for some kink.  I realized tonight that I have all these ideas of what I want to do to a sub but I don’t know how to get there!  I just wanna jump right to being comfortable with each other and doing lots of fun stuff.  But alas, that’s not how life is.  So, I will continue to improvise incorporating some aspect of D/s into our dates.  We talked about that – about how there may be a fair amount of vanilla-ness because of our living situations and my newness to the lifestyle.  He’s totally cool with it.

On a semi-unrelated note….

A few days ago this guy added me on yahoo.  Tonight he immed me and said, “evening miss chessa.”  Totally forgetting who this guy was I asked, “What is your screen name on collarme again? I forgot.”  To that he replied, “I have no idea what collarme is.  We were matched on eharmony.”  Ooops!!

 

Depression & Dating February 21, 2008

Filed under: Uncategorized — maidenchessa @ 9:53 pm
Tags: , ,

I really don’t know where Paden and I are right now.  The past two days we’ve exchanged texts, but that’s about it.  I know some more stuff is going down with his roommate but it’s bothering me that I don’t know.

A little background about me, I have depression.  It pretty much bites ass.  It’s been under control for about 6 months now but a couple weeks ago I went out of town for two days and didn’t take my medication – haven’t quite been the same since.  Two days shouldn’t have made a big difference, but obviously it did. 

Anyway, I have a semi-stressful job.  I’m a private tutor (I know, sounds way stressful, doesn’t it?).  I love the kid I tutor but her parents are those over-protective, expect absolute perfection, PSYCHO parents.  Last night I left their house, almost in tears.  I got home and the first thing I did was run to the computer, hoping to talk to Paden.  He wasn’t there.  Almost instantly I lost it.  I started bawling, went to my room and just lay in my bed crying for a solid half hour.  Yesterday I went and worked out and felt GREAT.  Until I went to tutor, then the life got sucked out of me.  It’s been not so great ever since.  All day today I’ve been numb.  Since tutoring tonight I’ve been on the verge of tears – the place where you’re totally sad, but you can’t really pinpoint why (and if you can, the reasons are bogus – as in my case this time), and you can’t cry – no matter how hard you try. 

I have a date on Saturday with another sub I’ve been talking to.  He sounds really great and we get along decently.  We’ve taken things A LOT slower than I did with Paden though.  I think that’s definitely best for me emotionally, but I’m incapable of doing it without the guy initiating that path (ironic considering I’m a domme, eh?) So, I’m not extremely excited about the date Saturday.  You’d think I would be – this guy is only an hour and a half away, while Paden is 1,200 miles away.  And, like I said, his location isn’t the only thing he has going for him – he’s an all around great guy.  But I’m just not excited.