Midwest Maiden

A 20something playing the game called life

Round Two April 30, 2009

Filed under: Uncategorized — maidenchessa @ 2:48 pm
Tags: , , ,

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!

 

Wild thing, I think I love you April 27, 2008

Filed under: Uncategorized — maidenchessa @ 2:25 pm
Tags: , , , , , ,

A quick little update about my last post…

The pms faded a lot sooner than I thought it would.  I moped around until my sister got home and when she made dinner I went upstairs to get some and then was going to retreat back to my hole in the basement (that’s where my couch & tv and everything are).  But, she said she was going to join me.  I can’t be miserable with her around (she has the ability to cheer me up unlike anyone else) so I caved and just had dinner upstairs with her.  In no time I was back to being myself and spent much of the evening scrapbooking.  I knew it would fade and eventually everything would be fine again but that just doesn’t make help ease the pain at the time. 

Anyway…onto the good stuff!

Hunter and I had a delightful night together last night.  When I’m with him, everything with the world feels perfect.  I don’t worry about us, our future, or the other women in his life.  It’s just the two of us – simply savoring every moment together. 

There was a lot of pain for him last night.  Granted, I think I say that after almost every night we spend togehter.  There is defnitely a lot of pain in his future.  Anyway, last night the pain started with clothespins on his nipples.  That just can’t get old, I swear.  My favorite part was when he was sitting on the couch and I straddled him, all seductive-like and when I’d lean down to kiss him it’d smash his clamped nipples – the pain making it almost impossible for him to kiss me back. Pretty much the whole time I was tormenting his nipples, his cock was rock hard. Mmmmm…..

The first time we fucked last night we went at it for quite a while (well, by my standards anyway).  When I counted down from 10, Hunter wasn’t able to cum so I made him pull out.  While I do enjoy when he cums, I also enjoy the painful look he gets on his face when he has to pull out without cumming.  Every time he looks like he could cry.  I love it!  He did eventually get to cum – twice (I know, I spoil him, don’t I?  hehe).  The first time I made him eat it out of me.  He gagged a few times – I guess it tasted worse than normal.  I got quite a kick out of that.  Later as we lay naked together on the couch (gosh how I love those moments!), like a pouty little boy he asked, “Will I always have to eat my cum?”  I told him that no, he wouldn’t always have to – but usually. 

I think he kind of doubted me when I said that though.  But, I proved him wrong!  The second time he came last night, I didn’t make him eat it.  Why you ask?  Because I’m just nice like that.  Okay, maybe that wasn’t totally it.  You see, I’m an idiot.  Earlier in the evening I’d grabed a magic marker (it was the closest thing!) to write the list of punishments I have or will use (I know, I’m 23 and have to write shit like that down in order to remember it….I’m so screwed!)  Then, I thought I’d just write a little on his body.  I wrote “Man Whore” (which he definitely was before he met me) near his cock, my name on his cock, and various other scribble type things on his stomach.  Then I remembered the marker was a washable one.  So, as soon as our naked bodies were once again laying together on the couch I too was all blue.  After we fucked my name was rubbed off of his cock but the area around my pussy was blue.  Granted, I know they’re “non-toxic” but I didn’t want to intentionally have my boy ingest ink & dye.  Plus, I’m sure there would have been transfer from my pussy to his face…don’t know how I would have explained that one to my sister!

~*~*

Normally I don’t get to spank Hunter all that much because most of the time we spend together is spent with my sister in the house also.  But, last night she decided to vaccum while he was here!!  I went to town on his ass with my hand for a bit and then the vacuum stopped.  There was a huge sigh of relief from Hunter, which just made me smile to myself.  See, I knew she wasn’t done.  Sure enough, the vacuum started up again and I went back to town on his ass.  I also laid into his balls.  I rather like slapping his balls – it gets a far more dramatic reaction than when I spank his ass.  He’d pull away as far as he could then try to close his legs as much as possible.  When both of those things failed to prevent my hand from wailing on his balls, he’d move back and try to sit on me!  I got quite a chuckle out of it.  I’d instruct him to get off of me and in his totally adorable whinny voice he’d say, “But it hurts!”  Too cute and oh so hot!

~*~*

Hunter got a really great internship in his hometown for the summer – which is 3ish hours away.  I’m happy that he has such a wonderful opportunity but I’m not happy that he’ll be so far away for 3 months.  It worries me quite a lot.  I *need* time with him, and I know he needs time with me also.  We’ve been seeing each other about once a week the past few weeks – usually on Saturday or Sunday.  By the time Wednesday or Thursday roll around, I’m a mess.  It’s usually one of those days that I start having doubts about something or another and things like that.  How am I going to make it only seeing him every 2-3 weeks!? 

He asked me last night if it would be okay if he took a second job over the summer as a cook at the same restaurant where Sarah – his ex-domme – works.  I gave it some thought and eventually said yes, but he was *never* to be alone with her.  But, I’ve given it more thought and have changed my mind.  That’s a lot of time that they would be spending together – even if they’re in a group with their co-workers, it’s still time.  If I lived in the area and was able to see him frequently, it wouldn’t phase me a bit.  But considering we won’t be able to see each other very often, I don’t want him spending that much time with the only other domme he’s ever had.  Like I’ve said before, I’m not afraid of him physically cheating on me, but of him developing feelings for her once again.  I’ve had the argument with myself – if you don’t trust him enough with her then really what does that say about your relationship?  But, why create a situation for that to happen?  If someone is tempted by something, they take efforts to avoid that thing – they wouldn’t take a job where they’re with that thing every day.  I’m not saying he is actually tempted by her at the moment, but who’s to say that couldn’t develop after seeing her day after day after day?  Plus, if he wants to make a little extra money (which he claims is the reason he wants this job), then I’m sure he’ll have no problem finding another job in his area as a short-order cook.

~*~*

Tentatively, we’re planning that I will meet Hunter’s friends this coming Saturday.  They’re having a party at his place on Saturday night.  It should be rather interesting.  I wasn’t nervous before about meeting his friends but now that this thing with Alicia has come to light, I am a little more nervous about it.  I asked him how he thought she would react and he said he hadn’t thought about it (what a guy!)  He wasn’t sure if she’d do anything, though he did say she can be pretty unpredictable when she’s drunk.  He did think there may be some caddy comments from some of the other girls in the group.  Seriously?  Aren’t we supposed to be adults – have some level of maturity?  It feels like fucking high school all over again.

~*~*

I want to end on a positive note – things are really going well and I am genuinely happy.  We were watching “Wild Things” last night and when the cheesy 3-some scene was about to come on I told him to watch ’cause there would be some girl-on-girl action going on.  It didn’t even phase him – he said he wanted was me.  At another point during the movie they had a cool shot of a house and he said, “That’s what our house should have!”  He said OUR :)

 

 

To cum or not to cum…that is the question April 14, 2008

Filed under: Uncategorized — maidenchessa @ 2:03 pm
Tags: , , , ,

Hunter ended up not getting to my place until almost 9 o’clock last night.  We got into it a little on the phone while he was driving here.  It was the closest thing we’ve had to a fight.  Usually when he does something I wasn’t pleased about, I tell him and that’s that.  Last night he gave it right back to me.  We threw arguments back and forth for a bit before there was an awkward period of silence.  I cut the conversation off abruptly because I had to go shower and everything before he got there. When he got there everything was just fine – like nothing had ever been wrong.  At some point we talked about the situation but we didn’t really argue about it or anything along those lines. 

Quite a while ago I asked Hunter to buy a pink thong.  I kept forgetting about it though so it wasn’t until last night that he wore it for me.  I’ve also been wanting him to do a strip tease for me.  He swore he wouldn’t do a strip tease.  He claimed he didn’t know what to do.  I tried to explain that it’s like what strippers do.  His comeback to that was, “They already have their clothes off!”  He eventually did it though.  It was among the most adorable things I’ve ever seen.  I can’t say he had many moves but what he did do was so cute.  He basically just moved his hips back and forth – kind of like how a 2 or 3 year old would dance.  I absolutely loved it though! He did something he felt was completely humiliating for me, to please me. 

Originally, he was going to get to cum.  It had been two weeks since he had last cum (he didn’t get to cum last time we were together since he’d stood me up the night before).  But, I was quite upset about our plans getting postponed last night, so I decided he wouldn’t be allowed to cum again last night.  He did spend a fair amount of time inside me though! :)

I had him go down on me for a while – both before he did and after he had begged me to allow him to fuck me and cum.  After he’d pleasured me a little while I told him he could fuck me.  He got so excited…until I brought out my secret weapon.  I got a condom out of our stash (normally we don’t wear them) and his face just fell.  He put it on and went to try to fuck me, but I stopped him and pulled out another condom for him to put on.  It looked like he could have cried!  It was one of the best fucks I’ve had though!  Normally he has to back off a little so he can last longer but he didn’t have to worry about that because the condoms deprived him of almost all feeling. 

I, of course, didn’t let him cum.  Then I played with his ass a little bit – with a plug and vibrator.  I am quite surprised by how much his ass can take.  I am rather looking forward to fucking his ass myself.  Mmmmm….

We spent a large chunk of the evening just laying naked in each others arms talking.  It was so nice.  Of course there was some teasing going on also.  At one point I did let him fuck me for 30 seconds.  You’d have thought I just offered him a thousand bucks, he was so excited to get even that little bit of time!  When there were 10 seconds left, I started counting down.  He got excited that he was going to get to cum but I told him no, that was just how long he had left inside of me.  I promptly pushed him out of me when I got down to one. Also at various points throughout the evening, I would let him just lay inside of me.  He was so grateful for even that.

At the end of the night, I told him he could fuck me for 1 minute.  I wanted to get him all riled up and horny right before he left.  After a minute I started counting down.  He asked if he got to cum at 1.  I asked if he thought he could and he said no (he’s no minuteman – he takes quite a while usually).  At 6 I told him that yes, he could cum.  When I got to 1 he came!  He said he didn’t feel at all like he could at all, until I said one and put my hands on hips to push him out of me.  All of a sudden he started cumming.  He was as surprised as I was! 

Yeah, so I messed up and totally underestimated him.  But, it was amusing nonetheless and we both left very happy people. 

I love him!

 

 

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

Filed under: Uncategorized — maidenchessa @ 2:11 pm
Tags: , , , ,

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.

 

It doesn’t taste as good as you do March 6, 2008

Filed under: Uncategorized — maidenchessa @ 1:44 pm
Tags: , ,

Hunter came over again last night – third time this week.  The one day we’ve spent apart since we met – Tuesday, was rough for both of us.  I didn’t know if I was going to be able to make it to Wednesday!  But, it did arrive….FINALLY!

Keep in mind Hunter is my first experience as a domme – my first experience causing another individual intentional pain.  Let me tell ya, Hunter has a high pain tolerance!  I was playing with his balls, trying out some of the pain techniques I’d read up on.  Yeah, they were causing him pure pleasure, there was no pain involved.  I was so scared to do anything more though because I didn’t want to actually hurt him; I just wanted to cause him pain.  So, he actually had to show me how to hurt him! 

I quickly got the hang of it though!  I clipped three clothespins to his balls and commenced rubbing his cock so he could cum, as I had promised.  He said it usually takes him around an hour to cum when he’s whacking it.  I’m a slam, bam kind of girl.  I get annoyed and give up if it takes me longer than 10 minutes to cum.  I don’t have patience, I get bored easily.  I’ve read on a couple websites where the doms have trained their subs to cum by counting down from 10.  That’s definitely something I’m going to look into for Hunter. 

One thing I appreciate the most about Hunter is that he’s not turned off by my inexperience.  I was so careful and almost scared the first time I put clothespins on his balls.  I asked him if he minded being my “guinea pig” and of course he said he didn’t, and I could tell by his reactions to things that he was sincere in saying that.  He is so into submitting and pleasing me that no matter how scared I am about trying some new pain thing or if I do something “wrong,” he definitely doesn’t allow it to kill the mood. 

Back to the juicy stuff!  It didn’t take him *too* unbelievably long to cum.  When he did, I was quick to scoop the cum from his stomach and feed it to him.  Oh, how I love that!  Every time I brought a little more to his mouth, his face winced in disgust.  It was obvious he wasn’t a big fan of it…which made me love it all the more.  I asked him about it later and he said, “Well, it doesn’t taste as good as you.”

Later he told me that his favorite part of the evening was right before he came – me stroking his cock, us kissing, and the movement of me stroking his cock making the clothespins bounce, creating a combination of pain & pleasure.  He called it “feeling overload.” 

Towards the end of the evening I again applied 3 clothespins to his balls. We were watching a show - during commercials I’d play with his balls, during the show I’d just cuddle up against him.  At the end of the show (which had the LONGEST concluding segment EVER!) we began making out while I played with the clothespins.  I loved taking them off.  I tried to make it so he wouldn’t know exactly when one was going to be removed (if it worked out that way, I don’t actually know).  It was so hot – we’d be kissing, I’d take one off and instantly he’d stop kissing me and pull away, wincing in pain.  I just could not get enough of that.  And oh boy did that make me wet as hell.  I could feel my panties getting all squishy.  I could have pulled clothespins off his balls all night long! 

Hunter has started writing reflections for me.  He was fairly nervous about it I think.   He wasn’t sure what to write about and that he would even be able to write about his thoughts/feelings were in-depth.  I was very impressed with his first one though, which he sent after he got home last night.  I think it’s already having the desired effect.  He told me in detail about his favorite part of the evening, about how he’d felt self-concious when he was standing almost naked in front of me, and about his ex-girlfriend – none of which I think he would have thought too much about or told me about, had he not been expected to write a reflection of sorts. 

As I said, Hunter talked about his ex-girlfriend in his reflection.  I’m glad he opened up with me about it some.  I knew they had been together quite a while and that she was the one who had introduced him to D/s.  To be completely honest, I do worry a little about them/her.  I know she is still in his life.  I also know that he’s told her all about me and how excited he is that he met me.  He did admit though that he does still have some feelings for her.  On a concious level, I know there is nothing to worry about – he is totally head-over-heels crazy about me.  But, considering the last relationship I was in ended because the guy got back with his ex-girlfriend, can you really blame me for having dobuts?  Hunter has done absolutely nothing to make me doubt him – quite the opposite really.  So, I’m just going to continue to focus on the fact that I’m happy and hell and so is he.  Hopefully those stupid little tiny voices of doubt in the back of my mind will shut up soon.