Miss Takes My Cherry!

Last night.....my sissy pussy...taken by Miss...with a strap-on.  i have now been fucked by my Superior Female and i love Her more than ever for it. 

 

It was always going to happen this weekend and Miss had set the agenda earlier in the day:

 

1. 'sissy, you will get changed'.

2. 'You will then dress me sissy'

3. 'You'll put the strap on on  me and then I'm going to fuck your sissy pussy'.

 

We had decided that it would be called my 'sissy pussy'.  i think that's a beautifully apt name for it. 

 

Miss and i had both had an energetic day and when finally able to relax, with a few drinks, the fun and pleasure began in earnest.  Following Her instructions i showered and dressed.  i felt that since my virginity was going to be taken then i should be dressed in some of my most sissy girly things.  Something to highlight and emphasise my full subservient sissiness.  My set comprised of a ridiculously short gorgeous pink lace and chiffon, baby doll, pink and white ribboned suspender belt, pink lace bra, my pink pair of 'cuckold' panties with suitable wording across the front and mink stockings. 

 

Miss took these pictures:

 

 

i love how She made me pose.  Revealing my 'cuckold' panties, my tiny cock getting very wet, my baby doll lifted submissively, my pretty bra showing nicely with my breast forms thrusting the bra cups out.  The gorgeous suspender straps holding my stockings taught. A pose i so enjoyed holding for Miss and would so enjoy holding for Her and a lover whilst they laughed and humiliated me. 

 

 

The wording on the front of my panties.  So, so true!  My tiny cock and the little wet patch of sissy excitement. 

 

 

Miss made me face the corner.  The rear of my pretty panties on display.  The delicate ruffles across my behind and on the legs.  The rear of my suspender belt visible through the sheer back of the baby doll.  Oh i felt so so girly and sissy.  Another pose which would be so appropriate in front of Miss and a Real Man.

 

i had by now dressed Miss.  i love doing this and have not done it nearly enough for Her.  i wish She would make me do it more often.  In the past when She had lovers it would be a ritual for me to dress Her and it would be wonderful to be able to do this again.  She had chosen a sexy navy blue six strap suspender belt, black seamed stockings and a gorgeously hot and sexy blue lace/satin body with stunning lace around the breasts.  She looked so fucking hot and i made sure i told Her so.  i wanted to include some pictures of Her but Miss was not having it, even though i would have not included Her face or anything compromising.  She did however take these and gave me permission to publish them:

 

 

Her gorgeous stocking clad feet. 

 

 

Her gorgeous stocking-clad foot, pressing down on my tiny cock through my baby doll and sissy panties.  A very symbolic picture! i also love my bra and tits in this shot. 

 

Miss told me to lube my sissy pussy and by that really lube it with my fingers inside me.  i made sure my pussy was very very wet.  She then adjusted the strap on around Herself and attached the smaller of the two 'cocks' to the harness.  Miss was giggling to Herself and i could tell by the look on Her face that She was really enjoying this.  Next She told me to get out a condom - 'we have to be safe sissy' and to sheath the cock.  God, that was sexy doing that.  i imagined sheathing a lover for Miss but instead this cock was for me!  Even though it was the smaller cock that was going to take my pussy it still looked ominous.  Miss made me kneel and then without warning forced the cock into my mouth and began vigorously fucking my face. 

 

This was the 'cock' for my 'sissy pussy'.

 

 

About 4.5 inches long, an inch wide.  My own little cock is not this long fully erect nor as wide. 

 

She literally made me gag with it and i absolutely loved it!  i grew into the role of a little sissy cocksucker and licked, dribbled and drooled.  i made soft sucking sounds and girlish moans as Miss continued thrusting it into my mouth - occasionally rubbing it across my cheeks and everywhere on my face.  She was really getting into it now as i gripped Her gorgeous arse, encouraging Her to give me more.  Miss though now felt it time to get on with the main event and forced me onto the sofa, with my knees on the floor and my pussy raised up to accept Her love.  More lube on the sheathed 'cock' and then the initial press onto and into my pussy.  Miss was gentle, She held my hips lightly and occasionally caressed my bra clad tits. 

 

Oh it felt so good!! So hot, everything on fire.  Pain, but not a pain i wanted to go away.  She eased Herself into me and waited until i asked for more - and more She gave!  Each press, each push feeling like a searing poker but i wanted more and pushed back onto Her.  Miss laughed at my girlish wiggling and absconded me for pushing back.  At one point i felt like i was going to pass substance and had to go and relieve myself.  All of that considered by Miss to be a very normal reaction!  Then more, more fucking by Miss and more moaning by me.  Miss regularly asking me if i was ok, if i liked it and me moaning my pleasure in confirmation.  Did i mention that when i dashed off to the toilet that the whole of the cock was plugged right up into me?? 

 

One thing that was noticeable to both Miss and myself was that my tiny cock hardly got hard.  It was certainly very wet with arousal but there was absolutely no significant erection at all.  Is that normal?  i don't know.  i was certainly turned on but my little cock was not hardening in the slightest.  Very strange.  Nerves? Eventually we decided that my pussy had had more than enough of a fucking and that we would definitely be doing this again.  i suggested that we try it bi-weekly and Miss agreed that as a good training schedule for my pussy.  i know that eventually i am going to be able to take it with Miss fucking me just as a Real Man would fuck a Woman.  Miss was wonderful.  Caring, considerate and compassionate.  She made it a wonderful experience for me and i am so grateful. 

 

But that's not the end of it.  As we sat on the sofa together, still in our lingerie, i noticed Miss fondling and seductively handling the larger of the two cocks. 

 

 

As you can see from the pictures it's considerably larger and thicker than the little one I took!  As She sat there playing with it in Her hands i wondered what She was thinking.  She had not asked me to pleasure Her in any way after fucking me.  i guessed She might be thinking that this bigger cock reminded Her of the cocks She had enjoyed previously with lovers?  i recall one of the black lovers She had a great session with  - was She thinking of that?  Whatever it was, Miss was getting turned on and with that monster in Her hands why would She want my pathetic little cock?  Oh no!  Miss had other plans.

 

'I'm going to play with this sissy and you can sit in the corner and play with yourself, watch me as i cum'.  Oh Miss!!  'Don't forget your condom sissy'!

So now Miss was going to pleasure Herself with this massive cock and i was to be humiliated with a condom on my little thing.  Miss knew the scenario She was creating.  Her with a lover.  A Real Man with a proper cock.  Someone who was going to satisfy Her. Me, humiliated, belittled, made to watch.  She lay there, the crotch of Her pretty body pulled aside and proceeded to 'condom' the big cock.  Oh Miss - to perfection!!  i wish She had made me do that.  'This is how a condom looks on a real cock sissy, they were made for real cocks like this one'. She was considerably wet by now and i knelt transfixed as the cock entered Her love petals to the accompaniment of Her moans and sighs of pleasure.

 

My own little cock was hard in the condom now as Miss commanded that i was not to cum until She had.  She told me 'keep your thoughts in your head sissy, just know that i'm being pleasured by something so much bigger and better than your little clit'.  i wanted to provide Her with verbal encouragement but Miss did not need it. It was quite clear that this cock was giving Her the pleasure She needed, deserved and that She has been missing for so long.  As Her cum approached i knew that i could take risks and edged closer to Her, running my hand along Her parted stockinged legs, urging Her to cum for Him to cum hard for Her lover.  'Oh I am sissy, I'm cumming for Him oh yes.....oh fuck yes...Ohhhhhhh!'

 

It was beautiful to watch.  To see Her pleasure Herself with something so substantial.  For Her to prefer this huge rubber cock over my own was wonderful for me.  Then, She began to verbally assault my sissy mind with a barrage of humiliating references to my small cock.  i was now sat next to Her on the sofa and knew that my cum would happen in seconds.  Just a few pumps into the rubber of my sissy juices, weakly dribbling.  Miss took me over the edge with Her teases. As a final act of dominance and to humiliate me Miss then made sure that i saw Her door to Her chambers close as She left me for a well-earned sleep. 

 

A truly memorable evening of hot loving between Miss and Her sissy.  My Superior Female has taken my virginity and i feel ever more closer to Her for it.  x