Midwest Maiden

A 20something playing the game called life

Round Two April 30, 2009

Filed under: Uncategorized — maidenchessa @ 2:48 pm
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Hunter came over again last night.  I was/am extremely pleased about it.  After his visit the other night, I was afraid it would be a one time thing.  It was 6 months since the last time we’d gotten together, and had been 5 months before that.  While I would like it to become a semi-regular thing, I’m trying not to get my hopes up.  He’s done with school for the summer in a couple weeks and that changes things.  Plus, one just never knows with that kid.  Since I’m not sure when/if I’ll see him again, I was sure to savor every moment of it.

 

One of the things that had to be taken care of last night was that Hunter needed to atone for his “sins” from the previous Saturday night.  That night he’d gone to a strip club (with female strippers, mind you) and ended up hooking up with a guy!  How he managed that, I have no idea.   But, it made me insanely jealous.  Part of the reason was because the strip club was in my town so if he was going to be fucking anyone, it sure as hell should have been me!  The other part of me was worried it was going to make him realize he was gay and then he’d obviously be done with me completely.  I’ve always known he considered himself bi but he’d never acted on those feelings outside of a D/s setting (as in being forced by his former domme to suck her boyfriends dick or something along those lines).  No worries there though, it’s pretty obvious women (well, at least me) still do it for him. 

 

Our activities started with a good spanking with his belt.  I really liked the belt – I’d only used one once before.  I hadn’t been impressed the first time because my brush and a wooden spoon had gotten more reaction.  But, this was somewhat of a punishment spanking (less punishment, more me just wanting to take out a little anger on him about Saturday) so it actually worked better.  The belt allowed me to *really* wail on his ass, without pushing him too far too fast.  Plus, it made his ass much more red than the spoon which was a nice sight. 

 

Since he enjoyed sucking cock so much Saturday night, I gave him my dildo and made him demonstrate his skills.  I’d say it was one of the most difficult things I’ve made him do (as far as humiliation is concerned).  He did not want to do it all.  The first time he spoke after I told him what I wanted, his voice cracked.  It was hilarious.  Of course, I also had to taunt him with comments like “I’m sure you didn’t have such a scowl on your face Saturday night.  Suck it like you mean it.”  I wanted to take a picture so badly – that would have *really* humiliated him, but I couldn’t find my camera.  Damnit!

 

Eventually, I combined the spanking and dildo-sucking.  I started in on his ass with the belt again, while he sucked the dildo as instructed.  I also got in quite a few nice shots to his balls too.  Throughout that part, I reiterated to him that I was the only one who could use that ass and that the only “cock” he should be sucking is mine. 

 

After the last time we’d been together, I confessed that I had wanted to suck his cock.  I know, some think that isn’t a “dommely” act but occasionally I enjoy it.  Originally, I had told him I wouldn’t go down on him because of his actions Saturday night but as time had passed, my jealousy over it had eased and I figured he’d paid by sucking my dildo and taking the spanking.  But, I teased him relentlessly before I finally took it in my mouth.  I put my mouth right up to it, would blow on it a little, but wouldn’t take it.  The cock would totally react, involuntarily moving toward my mouth.  I did this over, and over, and over.  It just didn’t get old!  Eventually, I did take his balls in my mouth.  He really enjoyed that….until I bit them!  It took him totally off guard.  Hilarious.  Of course, I did give in when I was ready and sucked his cock for a bit.  I think it’s safe to say we both enjoyed it.

 

At this point I was still fully clothed, while Hunter had been completely naked for a while.  I really like that – the sub naked and domme clothed.  I think it highlights the difference in status.  Anyway, I let his hand wander a little and soon his fingers were inside of me.  That was probably only the second or third time we’ve done that.  Part of the reason is it’s something I feel awkward about asking for and he never takes initiative with things (understandably so considering he’s the sub, though he was a little more forward last night…which I enjoyed).  It was awesome though!  Getting fingered is something I’ve always enjoyed – as long as the guy knows what he’s doing (it seems like such an easy thing but you’d be surprised how many guys absolutely suck at it!)  It really helped with the pain factor when we did finally have sex.  I had been extremely nervous about sleeping with him again because of the pain – nervous to the point I almost cancelled our plans.  I had even considered going to my doctor about it, worried that something was wrong because the pain last time was not at all like I’d ever had before.  But, this time there was absolutely no pain!  Woohoo!

 

When we moved to doggie, he could hardly fuck me – he was so close.  I started moving my hips a little, not much at all, but it affected him immensely.  He said he’d cum if I kept doing that.  So, naturally, I kept doing it but refusing to grant him permission.  Soon he did cum and felt awful because I hadn’t granted permission.  I assured him it was fine, I’d wanted to push him to that point.  Some people might disagree with a mindfuck like that but he didn’t seem to mind after the fact. 

 

We actually went a second round, sorta.  He has a long rebound time so we’re pretty much always done after one time.  But, I put in a little effort and got it up again.  He didn’t cum again but the sex was good nonetheless.  I’d gone down on him again and he pulled me up onto his lap.  I’ve only ridden a guy sitting up once and it was as good then as it was last night!  That is definitely one of my new favorites.  One of the reasons I enjoyed it was because we were able to make a lot of eye contact.  Well, when his eyes weren’t rolled back in his head from pleasure.  His eyes would be mostly closed and all I could see were the whites of his eyes because they rolled back.  It was so hot. 

 

Despite how fucking great the evening was, it ended with a really awkward moment.  My sister was home and sitting in the living room (where the front door was).  So, we had to walk by her when he left.  She knows our relationship is purely sex at this point and doesn’t exactly approve.  I walked him to the door and said “see ya later.”  He said the same and walked out.  My sister didn’t acknowledge him and he didn’t acknowledge her.   Such an informal goodbye felt really weird considering what we’d just done together!

 

Eating pussy isn’t always enjoyable….for the boy March 14, 2008

Filed under: Uncategorized — maidenchessa @ 2:11 pm
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Last night was amazing.  I got to see Hunter!  First, we went out to eat.  I have to admit I was a little nervous about it.  Well, nervous seems to be too strong a word, as does worried.  On our first date we went out for ice cream and there were a couple moments of awkward silences – well, I thought they felt awkward.  I have no idea if he even noticed there was silence.  Perhaps I’m just super-sensitive about that kind of stuff. Anyway, since our first date most of our time together has been spent either watching movies or messing around.  I was unsure about how the conversation would flow when there was no external stimulation (such as our surroundings at the hockey game or events from the movie we’re watching).  I knew we connected on a vanilla level, but I wasn’t sure just how much.  I sure didn’t need to worry though!  Conversation flowed beautifully and it was just delightful.

When we got back to my place I had to work on something for my psycho boss.  We popped in the movie he’d brought but soon he shut it off because I was focusing more on the movie than getting my work done.  But, soon I was watching what was on tv instead of working on my work.  He would lean over, take hold of my chin, and move it back to the computer screen.  Some domme’s may have been upset by that because it could have been viewed as a dominant gesture but I appreciated it actually.  I have his best interest at heart always and I expect him to have mine in his also.  Even with the little things like watching tv while I should be working, I do expect him to do what he can to keep me focused.  In my opinion, sitting silent while I did something dumb would actually be a disservice to me.  It was really cute too – at one point he moved away from me a little and I started watching tv.  As soon as he made the littlest movement, my eyes jetted back to the computer screen because I knew I was going to be in “trouble.”  Yeah, we may not have a conventional D/s relationship but it works damn well for us!

After I was done with my work and we’d started watching the movie again, I mentioned a foot rub to him.  He paused and said okay, but I could tell by the look on his face that he wasn’t crazy about the idea.  He didn’t have a look of distaste or anything like that on his face, but the look of excitement was missing.  When it comes to pain I have no problem making him do something he doesn’t want to do but in other aspects, I want him to serve me because he wantsto, not because he hasto.  So, I didn’t push the foot rub thing.  But, about 10 minutes later he gets up and starts rubbing my feet anyway!  He’s so damn great!!

He’s been wanting to go down on me for quite a while but I’m not a big fan of it so had put it off.  I gave him his chance last night though.  I must say that I was pleasantly surprised.  It’s not that I doubted his abilities, being eaten out has just never done anything for me before.  But, it’s true – he’s good!  I didn’t cum, but I did very much enjoy it.  For the first time in a really long time (if ever), I actually have hope that I may cum from something besides my hand & bullet!  A lot of it comes down to allowing myself to sit back, really enjoy it, and let go.  I am able to do that with Hunter more than any other guy, and I think I will continue to do it more each time we’re together. He also fingered me just the way I like it!  Fingering seems like such a simple concept to me and yet there are SO many guys who have no clue what they’re doing.  Hunter definitely does not have that problem!

Soon we were fucking, and it was great! I was *so* wet and had no problem taking him this time.  He enters me so slowly, as if he’s savoring the feeling.  Both times that we’ve had sex, he’s whispered “Thank you” as soon as he’s all the way inside of me.  I absolutely love that.  He doesn’t even realize he does it.  He’s just that grateful to be in me, which I think affirms the fact that he knows it’s a privilege to have me – that sex with me is not something that can ever be assumed.

He came inside of me after I had counted down from 10.  As soon as he’d cum I told him to get down and clean me out.  He asked if he could just lay there for a little bit, inside of me.  Since I absolutely love the feeling of him inside of me, I allowed it.  He had a hard time eating his own cum out of me.  He doesn’t like the taste of it to begin with, plus being mixed with mine, just created a really bad taste for him.  But, he did it it.  He did a very good job of it actually.

We cuddled and watched pretty much none of what was left of the movie and soon we were going at it again.  Again, I started counting down from 10, telling him to cum onmy pussy when I got to one.  He wasn’t able to cum right at one, so I made him pull out of me.  The look on his face was priceless – I thought he may cry!  He began to apologize and I assured him that it was fine, he did his best and that’s all I ask of him.  I knew that it was a quick turn-around from the first time and that it would be challenging for him.  Making him pull out was not a punishment, simply a tool for helping me train him to cum on the count of 10.  What motivation does he have and what conditioning does it create if I let him just continue as he was even after I’ve already reached 1?  I hope he understands that I am in no way dissapointed when he doesn’t cum at the count of one, and that I’m crazy about him for trying.

I’ll get to see him again in a day.  I absolutely can’t wait!  We’re going to a hockey game and then taking a trip to the dive of a porn store here in town.  I looked up strap-ons online and they’re so damn expensive!  BDSM is an expensive lifestlye in general – even if one improvises!  So, I’m hoping to find some cheaper stuff at the store.  If not, Hunter and I will fork out the dough we don’t have for the shit we want.  I am a little nervous about fucking though.  What if I’m bad at it?!  Yeah, I’m still working on the self-esteem thing.  Believe it or not, I’ve actually come a long way! Hehe.