Midwest Maiden

A 20something playing the game called life

Hope & Despair September 21, 2009

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This is going to become an extremely boring blog (not to imply it’s all that exciting at this point!)  Hunter and I are done for the time being.  I fucked up big time and doubt he’ll ever forgive me (though I can’t bring myself to completely give up hope which some say is a good thing but it sure makes coping and moving on more difficult!).  I may write about it eventually, but am definitely not ready to yet.  I have also put things with Grant on hold for the time being.  It sounds so unbelievably cheesy but I want to “find myself”.   Even though I know I would hook up with Hunter again in a heartbeat, because of the inconsistent status of our relationship, I became someone I don’t want to be. 

 

It’s not only with guys that I’m disappointed in myself. I used to do service and was all about creating social change.  Yeah, I haven’t done any kind of service in over a year.  I feel like my decrease of TV and increase of NPR are improvements in this area (it makes me more of a global citizen than one of our ignorant, shallow society only) but beyond that, nothing.  I’m just not as happy as I used to be.  I totally notice it in my teaching.  I’m just not as enthusiastic as I was last year. 

 

In addition to taking a step away from relationships (well, except for the possibility of hooking up with a dom friend but he’s leaving in a month so it wouldn’t amount to more than a scene or two), I think I’m going to start going to church again.  I can’t say that my core beliefs have changed but there is something unbelievably comforting about church for me.  I don’t know if it’s the sense of community one oddly feels sitting among strangers or feeling closer to God (not to imply one actually *is* closer) or if it’s the passages and sermon. 

 

And, I sent an e-mail to a contact in Haiti about the possibility of working there.  I’ve mentioned a few times that I’ve felt pulled in that direction the past few months but just couldn’t take the steps to make it happen.  Whether or not anything will actually come of my inquiry, I do feel that it is a step in the right direction.  Hell, it’s a step!  That’s more than I’ve taken the past couple of years to improve my happiness.

 

Despite the fact that I have a lot of hope for my life (with the Haiti inquiry and rediscovering my faith and all) I am still very sad.  I cry daily.  Never sobs, just a few tears here and there.   If it was PMS, it would have passed by now.  Damnit.

 

Slump September 17, 2009

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I think I’ve hit some sort of slump/depression.  This whole last week I’ve been completely unproductive when I get home from work.  I’m getting at least 9 hrs. of sleep a night.  At my last therapy session I had set a goal to walk 4 times a week.  I haven’t gone on a walk since then.  I was at such a high then, only a couple of weeks ago.  It’s been a rough week in regards to Hunter and shit hit the fan last night so I know that isn’t going to help things.  I had plans with Grant for tomorrow night but I bailed because I just don’t want to be around anyone (well, except Hunter which isn’t gonna be happening anytime soon).  I just want to lay in bed and do nothing.  I’m hoping it’s just PMS but who the heck knows.

 

Your Signature is Ugly September 10, 2009

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That’s what Hunter told me at the conclusion of our lovely meal together on Monday night.  As I was paying for the damn meal, might I add!  He’s such a romantic.  It actually gave us quite a good laugh.  And, btw, I think my signature is cute! :)

 

Backing up a little bit – Grant and I got together a week ago.  We met up at a hotel.  It was definitely the least intense but most service oriented time we’ve had together thus far.  He gave me one of his amazing massages, which was a little more erotic than in the past.  I freaking love it.  Mmmmmm!  He also took some pictures of me.  I wasn’t too pleased with the ones I saw on his camera but I haven’t seen the normal versions yet (I can’t imagine I’d be more impressed with the larger ones!)  I don’t find bbw women to be unattractive by any means, but when it’s myself – uck!  Then, he fucked me with the dildo I use with my strap-on.  I didn’t make him wear the strap-on (seriously, what kind of bitch would do that to a guy?  Oh wait, I did…more on that later!), he just fucked me with it.  It is a big dildo and I wanted to make sure I could take it.  The night concluded with Grant fucking me doggie style.  It’s the first time we’ve really had sex.  It was freaking awesome!  Definitely the best doggie style sex I’ve ever had (which I was sure to text Hunter about while I was laying naked next to Grant, hehe).  I wasn’t expecting it to be as good as it was.  Not to imply I didn’t think Grant would be good, just that I had other plans in mind.  I had made Grant fetch my book (he was to bring it to me in his mouth, like a good little puppy).  I was going to read it while I allowed him to fuck me.  Yeah, that didn’t quite work out. lol.

 

~*Fast forward four days*~

 

As I referenced before, Hunter and I had a very enjoyable time together at dinner.  When we got back to my place, I pulled out my dildo and strap-on.  I had mentioned to him a couple of times that I wanted to take his ass, despite his pleas to the contrary.  I got a condom out, put it on the dildo and told him to put it on.  He was not at all happy about wearing it.  I told him that now I know how good doggie can really be and since he can’t last long enough to please me that way, he’d have to fuck me with a real cock.  He is well endowed but next to my dildo it was tiny.  I was sure to point that out to him multiple times.  I made him fuck me quite a while with the dildo, all the while taunting him about how much better it was than he is and how it’s so great to finally have a cock that can last longer than 30 seconds.  Between my comments there was a fair amount of begging to be in me.  The whole time he fucked me that way, I could feel his cock rubbing up against my pussy lips and clit – that was extremely hot to me!  Eventually I let him stop but laid it on thick how satisfied I was by it and that I didn’t need his cock anymore.  We laid naked together on the couch for quite awhile and eventually I let his cock get close to my pussy.  There was much teasing and begging of course.  I did relent (which was my plant all along, btw) and let him fuck me.  He got a few (literally, maybe three or four) thrusts in before he had to back off.  At that point, I started moving my hips like I do sometimes, and it made him cum in no time.  He begged me to stop (funny how minutes before he was begging to fuck me, now he wanted me to stop him from cumming, lol) but I didn’t. 

 

Afterward he admitted that he didn’t think I was going to let him fuck him.  That was so kick-ass to me!  I totally got to him.  There have been times before when I’ve *said* I wasn’t going to fuck him but then give in and want it.  He totally bought my act though.  And he said the taunting about his cock was so bad, he was actually beginning to doubt himself – which is kind of a big deal considering he’s got an ego the size of Texas.  It was a good scene, I have to admit!

 

Boring Update August 30, 2009

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I put in a little overtime at work this past week.  We worked on getting our rooms ready for the upcoming preschool year.  I’m really excited for this coming year.  This year the classroom is mine, whereas last year I was co-teaching with someone who’d already had the job for a couple years and had established her own system for things.  And, last year was my first year, which is always the hardest.  Last year I went through a variety of aides but this year I should have more consistent ones, and they will be able to help for a little while each day (as opposed to last year when my aides could only help during class and thus couldn’t put things up on walls, cut things out, etc).  So far I have the feeling that my stress level will be significantly lower than last year.  And, it helps that there’s an end in sight.  At this point, my plan is to quit my job at the end of this school year.  I can’t continue to work for someone who’s philosophy is so different than mine (basically, my employer doesn’t believe in discipline).  I’ll get a decent bonus at the end of the year that will last me the summer and then if worse comes to worse I can sub again in the fall.  It’ll be a pay cut but the decrease in stress would so be worth it. 

 

So far I’m doing well with the decrease in TV.  I watched around 6 hours of it throughout the week.  I watched a lot yesterday only because of the Ted Kennedy coverage.   Today I watched some but only after I’d been ridiculously productive for the majority of the day. 

 

This is my life…more work, less TV.  And I love it actually.  Hunter is right – I am weird!  :)

 

Weekend Randomness August 24, 2009

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I spent most of the day & night Saturday at Hunter’s.  We did a whole lotta nothing – watched a movie, took a nap, had dinner, played on our respective computers then hit the hay.  We had sex only a couple of times and the kinky aspect was minimal. 

 

While I know he enjoyed our time together, it didn’t live up to his expectations.  He was expecting sparks to fly and everything in his life that was bothering him to disappear (my words, not his).  Unrealistic, yet I know I’ve had similar expectations for various things in the past.  Even though it lived up to what I had expected (I wanted it to be comfortable and laid back, like a couple who’d been together for years – though I would have preferred more sex) I can see where he’s coming from.  I don’t think I made him laugh too much, and I feel that laughter is important so that kind of made me sad.  He said all he wanted to do was lay in bed all day, but I feel like I could have somehow made that more fun or motivated him more to get up and do something.  But, at the same time, I was completely 100% myself.  Not that I was ever trying to be someone I’m not with him (or anyone else for that matter), but I feel like I have to reach a certain comfort level to really let my guard down and just be me.  Reaching that point with a guy is *extremely* rare for me (btw, it sucks major monkey ass that I reached that point for nothing because we most likely don’t have a future!).  It hurts a little knowing that the real me doesn’t cheer him up (actually, he just assured me that he was much better because I was around so perhaps I’m reading into a comment he made). 

 

I’ve said for a while now that I don’t think I’m capable of having vanilla sex.  The idea of a “kinky” person having a vanilla partner or vanilla sex is foreign to me. I didn’t think I could get turned on by regular means.  But, what we had Sunday morning was darn close to it.  I tweaked his nipples a few times and that was about as kinky as it got.  It’s actually quite comforting to me.  The idea of being incapable of having enjoyable vanilla sex was quite unsettling. 

 

~*~*~

Lately I’ve been reading a parenting book (no, not because I’m going to be a parent! I can use a lot of the ideas/techniques in my classroom too).  The author writes a fair amount about TV.  He makes a lot of really good points about the effects TV (and he argues that it’s not the content, it’s the act of actually watching it that’s detrimental) has on children.  I have absolved to get rid of my TV when/if I ever have kids.  Considering how much TV I watch currently (it’s usually on from the time I get home until I go to bed – while I do homework, mess around online or do lesson planning) I decided maybe I should start weaning myself off of it.  Yesterday I didn’t turn it on at all!  I cranked up the radio and got to work on work stuff.  I accomplished a lot and found that I didn’t really miss it.  We’ll see how long it lasts though.

 

Hangin’ Out August 22, 2009

Filed under: Uncategorized — maidenchessa @ 5:35 pm

Right now Hunter is laying down playing World of Witchcraft and I’m sitting with my feet up, usuing his ass as my footrest.  It’s been a delightful day, just hanging out with him (with a little sex thrown in, of course!)  :)

 

BFF August 19, 2009

Filed under: Uncategorized — maidenchessa @ 5:04 am

Okay, so Hunter and I were never and will never be BFF but we’re good for now.  After I made my post, I texted him to express my appreciation that he was honest (I did appreciate it – in the past he would avoid things rather than discuss them) but added that while I acted nonchalant when he told me, it did hurt and that I did a post about it.

 

Soon after, he texted me back to say he was sorry, that it was inappropriate, and that he’s just been struggling lately.  I wrote back what I thought would be a “good bye” text for the time being.  I said I was sorry if I had pushed him but that it was hard for me to watch someone I care about struggling so.  I added that I would step away and give him whatever space he needed but that I was there if he ever needed anything.

 

A few hours later, he called.  I about died.  I was not expecting that at all.  The first words out of his mouth were an apology, and a very sincere one at that.   He said that I didn’t deserve to be talked to like that and without me prompting, explained that it wasn’t true.  I don’t think he has ever apologized so unselfishly (usually he apologizes because he wants to get in my pants!)  Then we talked about what’s been bothering him.  I offered my advice (something along the lines of a profound, “I know, it just sucks”)  and talked about how I handled it when I went through something similar.  We ended up talking for an hour.  I don’t think we have ever talked that long on the phone before.  Neither of us are phone talkers so we’ve never taken that route for communication.  And, of that hour only about 5 minutes were sex related!  He’s visiting his parents for a few days but when he gets back we might do a ‘movie night’ like we used to all the time.  His proposal was, “Let’s *just* hang out and have a movie night like we used to.  No clothespins or spanking.”  Quickly I responded, “But we can have sex, right?!”  I don’t think we have ever hung out without me touching his cock.  Our first date was spent watching a movie with me stroking his cock a large portion of the time, then sending him home frustrated.  Hehe.

 

So, everything is good again.  What he said did hurt a lot but in the end, I actually came out with a lot more respect for him.  He apologized and opened up – my little man is growing up.  *tear*   :)

 

Friends? Not so much August 18, 2009

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I had every intention of writing about my fun with Hunter on Saturday night.  But, I’ve totally lost the urge. 

 

Hunter was depressed yesterday and I got a 3:30 a.m. drunk booty call from him last night.  It bothers me when he’s down because he’s rarely down.  Or rather, he rarely talks about it.  I know that if he’s actually talking about it, it must be bad.  His “status” on messenger today also had a depressed tone so I immed him saying, “want some company?”  His reply: “not really.  to be honest i don’t really like hanging out with you.  besides sex we have nothing in common.”  Ouch.  I simply said “okay.”  He felt the need to add, “but i’ll let you know next time i want some.”  Double ouch.

 

At first I told myself it didn’t bother me.  Slowly the sadness set in and eventually a few tears fell.  I was quite surprised by that, as I haven’t cried over him in quite a while – I’d gotten rather used to disappointment where he was concerned (though it very well could be PMS).  It bothers me that it bothers me.  I’ve said those exact same things on this very blog – we don’t have a lot in common beyond sex, it’s true. He’s a social butterfly, I’m a homebody.  He drinks, I don’t.  He plays video games, I read.   But despite that, I do enjoy spending time with him.  Saturday night after the first round of sex, we laid naked together and watched football.  I loved it.  I could lay with him and do nothing all day long and enjoy every minute of it.  Even though it’s “just sex” obviously I still care(d) for him.  I guess I kind of imagined us as a “friends with benefits” arrangement but obviously I was wrong.  Maybe that’s why I’m sad; I’m mourning the end of a friendship that didn’t really exist.  And, I feel like an idiot.  While I was enjoying spending time with him Saturday night, he was probably laying there thinking, “Just fucking leave already!”  Ouch.

 

Boy 1 of 2 August 17, 2009

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Grant and I got together Friday.  I went down to his place and met his girlfriend, her husband, and their daughter.  For most of the evening the three of us just chilled (the husband was gone most of the time).  It was enjoyable.  I was really impressed with his girlfriend.  She’s totally the type I would want to grab a coffee with and just chat.  And, not gonna lie, I’m rather attracted to her.

 

We did have some play time that evening.  I had purchased a restraints set on my recent trip to Chicago* so I tried that out on him.  I was not impressed – they don’t hook up as well as in the picture and make beating a cock or ass difficult.  Or, maybe it’s user incompetence.

 

Our alone time was kicked off with another of his amazing massages.  We tried out the restraints I got but that was kind of a flop.  Then I inserted a vibrating butt plug.  He gets so turned on with ass play.  I’m not a fan of it generally but his reactions make it so worth it.  Of course, I beat his balls and his ass all the while too.  It wasn’t nearly as intense as our first time playing but was still enjoyable.

 

The next day we had the house to ourselves (well, plus the infant who was sound asleep).  We watched “The Pet.”  Again, I was not impressed.  I guess I was just expecting something different.  But, it did create a decent setting for playing with Grant. 

 

He laid naked next to me for quite a while, while I teased/tormented his nipples and cock.  Eventually I told him to go down on me.  He did for quite a while.  Then, he simply laid his face in my pussy while I laid back and “enjoyed” the movie.  Having him down there just for the sake of being down there turned me on immensely – and is making me wet as I type this.  After quite a while of savoring our positions, I told him I was ready to cum.  He took his position – humping my leg like the dog he is, as I applied my bullet to my pussy.  The poor puppy had to hump quite a while.  But my orgasm was freaking AMAZING!  I don’t know if I had two (which would have been a first!) or if I just rode one for a really, really long time (which would have also been a first!)  What would get me going the most was when he was humping me, I would thrust my knee up a little bit.  I don’t know if it hurt his balls when I did that or not, but I imagined it did and it drove me absolutely wild.  Once I was done, he was allowed to get himself off and eat it. 

 

You may have noticed that I made some “pet” references.  Grant and I have decided to explore pet play a little bit.  This is not something I *ever* thought I would try or be interested in.  But, the whole humping thing really lends itself to pet talk.   It will never become the *only* or even main part of our dynamic but I’m really looking forward to exploring it with him. 

 

Later that day I visited Hunter.  More details on that later!

 

~*~*~

*Last week I went to Chicago to see the Cubbies play!  They lost but it was in extra innings so it was fun.  And, my friend and I went to “Boystown.”  It freaking rocked.  They had some awesome fetish stores!

 

Happy to be a Hypocrite August 9, 2009

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After I up and write a post about how age matters, I go and find myself an older man.  Go figure!

His name is Grant.  He contacted me a couple weeks ago on fet and we’ve been chatting.  The meeting last night was pretty spur-of-the-moment (which I’m finding is the way I have to do it….if I plan too far in advance, I chicken out).  He’d brought up meeting a few times and I’d kind of put him off.  I don’t really know why.  Actually, I do know why.  He’s more experienced than I am (or rather, has had more intense experiences than I have) and he’s older by 8 years (read: wiser) .  Both of which intimidated me immensely.  I really had nothing to worry about, though it took me a few hours to finally figure that out.

 

We met at a hotel and chatted a little bit.  Eventually we played strip Uno and I won :)   After the game he gave me a full body, erotic massage.  To be honest, massages have never been that erotic for me.  I enjoy them very much but they don’t turn me on.  Um, his definitely turned me on.  It was long.  It was literally a full body massage and it was totally erotic.  Yummy. 

 

Then we layed on separate beds, naked, chatting for a couple hours.  Some of the chatter was of course bdsm related but some wasn’t (we discussed “spirit guides” for goodness sakes!).  I struggle with the initial step into domination.  I was self-conscious about my domme skills with him (his primary sub experience was with a very, very experienced domme), afraid that I wouldn’t be intense enough, that I wouldn’t turn him on.  But, as I said before, I had nothing to worry about.

 

Poor Grant had to be the one to finally break the ice.  He had developed a “Truth or Dare” game and told me to pick one of the dares.  I picked the one that said, “Give another person an orgasm, using any means, within 5 minutes.”  Yeah, it was a cop-out on my part, I admit.  I told him how no one had ever made me cum.  He did though.  I couldn’t believe it!  It was good but I enjoy the ones I give myself better, I think because I feel like I can let loose a little more when it’s just me.  I’m more relaxed.  The feelings when someone else does it are so intense – toeing the line of over-sensitivity and pleasure.  It’s almost too much.  But, I know that if I continue to have them with him, I’ll get more comfortable with it and they’ll get better.

 

That little activity got the ball rolling quite nicely.  Grant falls into subspace extremely easily.  He’s got three phases of subspace – moaning, talking jibberish, and twitching/talking like Elmer Fudd.  When he first told me that I just kind of thought, “Um, okay?”  But, his descriptions are pretty accurate.  I tweaked his nipples a little bit and he was gone.  It was a new experience for me – Hunter doesn’t do subspace, I don’t think. 

 

Most of the intense play time was spent with him on all fours.  I alternated stroking his cock/balls, whacking his cock/balls, spanking him and teasing his ass.  He is a total ass slut.  His reactions to things are super hot.  The only thing is that he gets so out of it that he can’t talk – literally.  I’m used to talking to my sub a lot and asking questions so that’s something I’ll have to adjust to.   When he’s coming down from subspace, he uses sign language to communicate.  It’s adorable.

 

Eventually we laid down next to each other, naked.  We kissed and touched and just simply savored being in each others presence.  I began stroking his cock and then would abruptly stop.  When I would stop, he would want to keep the motion going so he seemed to begin humping my leg.  I kindly (ha!) pointed out to him that he was humping my leg like a fucking dog.  I’ve never entertained the idea of pet/puppy play but that one offhand comment may have planted a seed for future play.  We’ll see.  At one point I ordered him to hump the arm of the chair next to the bed.  He immediately did it and did it with gusto! lol.  While he was humping the chair, his cock was the hardest it got throughout our night together.  Not only is he an ass slut, he’s also a humiliation whore. 

 

He wanted in me so badly, but I wouldn’t let him fuck me (well, until morning).  But, I’ve decided that genital fucking will no longer be part of our interactions.  Grant is very talented with his mouth and fingers and is very in-tune with a woman’s reactions and sexuality.   That alone can and will keep me very satisfied.  His cock is slightly below average (plus, Hunter is very well endowed so even average seems kinda small to me now) so it didn’t do as much for me as his other techniques did.  I broached the topic of small penis humiliation and it’s now something we will be incorporating into our play.  I’m really excited about it.  I’ve done some “play” related to that with a few guys online and I really enjoyed it. 

 

Yes, we do have plans to play again.  He is part of a poly household and I’ve given enough thought to that to know it’s not what I want for my life.  So,  while we know for sure it won’t turn into a lifelong, committed relationship, we also know that there is some chemistry there.  We’ll just enjoy it while it lasts.