Friday, June 29, 2012



Timmy was required to visit his wife Rebecca in her office every day at lunch time.  She was a powerful executive for an international corporation, and Timmy was her sissy cuck husband.  While many of her fellow cuckolding wives believed in maintaining their husbands in strict chastity, Rebecca found it extremely comical to watch Timmy’s penis orgasm, so she allowed him to cum daily.  She did, however, insist that he only orgasm under her strict supervision.  So he would obediently arrive at her office, one of her assistants would show him into her office with a knowing giggle, and he would submissively approach his intimidating wife confidently seated behind her large desk.  Most of the time, she would be on the phone, usually participating in a conference call, so he would approach her silently, and once he was standing beside her, he would pull his pants down to his ankles.  His wife would quickly unlock his chastity cage, freeing his penis, which would immediately become erect. Rebecca also reached into her desk drawer and pushed a button on a small remote control, causing the butt-plug buried deep in his ass-cunt to begin vibrating powerfully.  His wife would pull up her short skirt, exposing her lush, nylon clad thigh, and place her hand on her thigh, forming a tunnel between her leg and hand.  Her husband would then excitedly insert his penis into the tunnel, and frantically hump his penis back and forth, eager to achieve his supervised orgasm.  He found the combination of sensations caused by both her stockings and her hand extremely stimulating, and would always cum in less than a minute of leg humping.  As he approached his premature, impotent orgasm Rebecca would touch the mute button on her phone, and begin laughing at his grimacing face and his frantic movements.  Rebecca’s favorite part of this tedious process was that Timmy screamed and wailed like a woman when he came.  Of course the intensity of his ejaculation was distinctly out of sync with the intensity of his verbal expression, and today like every day she made sure to cruelly make that observation just as his penis began twitching and spasming, struggling to expel his watery semen in slow, weak dribbles onto her thigh.  Timmy could barely hear her over his girlish squeals as the changing texture of her stocking as his cream covered it prolonged his orgasm.  The buzzing in his ass-cunt kept him in the throes of orgasm long after his little dribbles subsided, which meant he was still gasping and moaning as his wife firmly pushed him to his knees and he obediently lowered his tongue to the creamy mess on her thigh.  As he cleaned up his mess, his wife un-muted her phone and resumed her conversation.  Several minutes later, Timmy emerged into the outer office where his wife’s assistants worked, on unsteady legs and with his ass unconsciously jutting out, because the vibrations continued deep in his ass-pussy.  He was greeted with mock applause as he stepped out of his wife’s inner office, and even though that was no surprise to him, it still made his face burn.  Stephanie, one of his wife’s prettiest assistants, said to him as he walked by “that sounded like a really good one today Timmy!” which almost made him cry as he teetered to the elevator

Wednesday, June 27, 2012



You look adorable in your new swimsuit Sissy.  That 50's style, pink gingham will be a hit at my pool party.

Bedtime Fun

It started with a text...

Mistress.  Do you think that you can sleep in the hogtied position?  Maybe on your side?

My reaction to this out of the blue question was a bit shocked.  We had not planned on any playtime this week.  Also, when responding to Mistress it's best to choose your words carefully.  My response.

Me.  I don't think that I have the endurance to go the whole night.  Perhaps a simpler position to start off with.

Mistress.  How about legs tied together?

Me.  Absolutely.

Mistress.  Great! Get some of my ropes and leg cuffs and locks together for me.  I plan to mainly use rope.  Also boobies and the cage are required for bedtime.

Me.  As you wish Mistress.

My thoughts... This is going to be a long night...

That night I was well prepared with everything that she had asked for.  We went to bed a bit early.  She said that she needed to get me ready for the night.  I got into bed and she tied me up for the night.  To where I could barely move.  But with a bit of a struggle, I could change positions.  After tying me she proceeded to tease me for awhile.  Knowing that in my chastity it is torture.  My little puss started leaking all over the place.  She only teased me for a few minutes though.  Then she rolled over to get herself ready for bed.  Lights out.


I didn't get much sleep.  It was definitively uncomfortable at times.  But for some reason it also turned me on.  I kept having these really crazy dreams when I did sleep.  About women chasing me, and I had to hide from them.  I wonder now what would of happened if they would of caught me... So it was a very long night.  And I usually have a hard on all night long.  So being in the chastity at night is no fun at all.  Plus puss leaks, because I'm thinking how hot it is that I'm tied up for the whole night.  But I did sleep.

The next day.  This was her text to me...

I haven't decided yet when I'm going to allow your relief.

Maybe never ;)

Thank you for making my fantasies come true!  You looked beautiful last night and I love that you are all mine.

My thoughts... Gulp... I'm all hers... I love the idea of this fantasy.  And I keep giving her ideas...  Why is it that I feel that I'm sealing my own fate?  Oh well.  I guess I should embrace the pain.  I told her that my pain is her pleasure.  I guess we will see how much pain I can take...



Friday, June 22, 2012



Drink all your hormones Sissy.  They will make your boobs nice and full.  I'll be back to check on you in the morning.

Friday, June 15, 2012

Wednesday, June 13, 2012



“I do not consider your level of tit-induced stupidity to be sufficient, and I am taking personal offense at it.  I want drool running from both corners of your mouth, and I want pre-cum splattering all over the place NOW or you will lose your permission to worship my titties permanently.  Do I make myself clear?”

Monday, June 11, 2012

Just one more breath... please

I had a close call this weekend...  At the time I didn't think much about it.  But looking back, I should be more careful.

After my workout.   I ate lunch and took a shower.  It had been a hard workout so I was tired.  I decided to take a nap.  I had been wearing my double DD boobs.  Which make me feel very feminine.  And I had on my chastity and my pink crystal plug in my ass.  My girl had left a pair of her used panties, when she had left for work.  She had worn them for 24 hours and I new that they would be very juicy because I had given her oral in the morning and she never bothered to take them off.  I pulled them on over my head.  And I was right they had her strong smell on them.  The kind that makes my little puss tingle.  Over the panties I put on a pair of her pantyhose.  I tied them around my head.  I didn't want the panties to fall off my face while I slept.

I slept for quite some time.  I din't have any panties on.  Because I like to air out my chastity whenever I can.  But instead of my puss getting some air she had made a mess.  I hadn't realized while I was sleeping that my little puss was drooling like a faucet.  I reached down after my nap. To feel my thighs completely soaked in puss juice.  I was really horny at this point.  My girl was gone.  And I needed to do something about it.  

I was wearing my chastity so there is only one way to have that release.  It is to use my big huge fat dildo.  I love that thing sooooo much.  When it goes in, it just feels so good.  I had been wearing my pink crystal plug for hours before so the huge dildo slid right in.  It's so big that it still takes a few minutes before I'm ready to go all out on it.

So while I'm slowly sliding up and down.  Feeling every inch of the those fat ten inches.  I put on my latex hood with the inflatable penis gag.  It doesn't have any zippers or laces, it just slides on.  I have to get it just in the right place too.  When putting it on I have to get it over my head, then get the gag part in my mouth.  Then line up the to nose holes so that I can breathe.  It is quite an operation to do while bouncing up and down on a huge dildo that will make you gasp all on its own.  So once the hood is in place I put on a thick neck collar that has two buckles on it to hold it in place.  By the time I'm putting on the collar, I'm very distracted.  So I couldn't secure it very tightly.  That ended up being a very good thing.  So although the collar is not on super tight it is still very restrictive and doesn't let my head move much at all.

At this point I start to pump the penis gag.  Just a little at first... And my rhythm on my dildo picks up quite a bit.  And because I'm bouncing up and down so much, the giant boobs I'm wearing are bouncing pretty good.  So I have to hold on to them while I have the penis pump in my hand.  And I pump some more.  The penis gets rather large in my mouth.  And when it gets larger it becomes very difficult to breathe through the tiny holes of the hood.  I can actually pump it so big that it fills my mouth almost touching the back of my throat. And when that happens the nose holes move a bit and I'm not getting much air at all.  I actually love breath play so this isn't really a problem for me.  In fact it is a huge turn on for me.

I go back and forth on filling the pump gag so that I'm completely full in my mouth and barely breathing.  Then releasing the valve on the pump so I can get some air.  This happens many times.  Until one last time that I fill it so full I'm not breathing at all during my climax.  The problem is I try to pull the mask to get some air in my nose holes.  But I'm so low on air that it isn't doing anything for me.  It's at this point that I realize that I only have a few seconds left before I pass out.  And if I do, I probably won't wake up.  Because I won't have enough air getting to me.  If any at all.

And I know that I have this thick collar on with two buckles that are very difficult to get off.  So I start to fumble for the buckles.  And in my panic I can't even feel where my fingers need to be to start to unbuckle it.  Now several more precious seconds have passed and I'm really starting to panic.  My last resort is to just start pulling on the hood.  And hope that I can get it out of the collar.  A few tugs and all the latex seems to do is stretch.  Finally, I feel it start to move a bit.   I keep struggling.  I'm starting to suck in and out with no air at this point. Finally I get just enough of the latex out of the collar so I can get it up to my nose to breathe and spit out the gag.  AIR!

I don't think I would of been able to hold on much longer.  I pull off the latex mask the rest of the way.  And just collapse in a puddle of my own juices.  All of that and the dildo is still massaging my backside.  I look down at my chastity.  And see the huge mess of cum everywhere.  Even though I almost died.  It was one hell of an orgasm.  So lesson learned no more collar with that hood.

Saturday, June 9, 2012

I have to go get dolled up for my girl tonight.  She wants me all in pink to match my pink toe nails.  And hopefully we'll make up for lost time tonight.  Which hopefully means me dressed pretty in pink and my buns bright red.

Friday, June 8, 2012



New ballet shoes.  You'll need to get used to these Sissy.  You're going to be wearing them a lot. You'll look just like a ballerina.

Wednesday, June 6, 2012



When you are not compliant to my wishes it only fuels the sadist in me. Your tears are my joy, so please struggle some more.

Sunday, June 3, 2012

I get some playtime tonight.  I'm so excited!  Can't hardly wait.  I have 6 hours to kill.  I believe I will be bent over a bar, and tied down.  Ass held high.  Then some discipline.  Yum!  Then who knows...

Friday, June 1, 2012



Maybe next time you'll learn to complete your chores on time Sissy.   I doubt you'll get much sleep in that position.  But that's not really my problem now.  Is it?