SISSY CUCKOLD HISTORY 729.
As a budding feminized sissy cuckold we all had our own unique experience in having out tight little sissy hole being violated!
And I would suspect to a sissy we all had a wave of fear terror and shame as whatever it was invaded that place?
The thing is from the moment you started sneaking into women's hosiery, lingerie and clothes your back passage the sissy pussy was going to be filled as the sissies in built knowledge that it's not a real man and because women have things put in them so must the sissy!
I started with a bit of self exploration with fingers but nothing more than that and it was with the second woman that played with me Fran that so the saying goes bust my anal cherry.
As already related Fran was a friend of my Mothers who after Pamela got into making me serve her in some very unusual ways and we were laying on her bed both lingerie and hosiery clad, me in make up which Fran had applied and I had already done things to her under her orders that were sexually mind blowing from worshipping her silky stocking clad feet and toes, licking her bottom that she had left very dirty making the anal pleasuring of her a shocking experience that I no less carried out getting shamefully aroused licking her dirty butt clean to eating her unwashed pussy till she had taken herself two massive orgasms.
Now as you might recall from previous posts Fran had been the first woman to feel my little erection (Apart from the night I erected against my Mothers nylon clad foot as I massaged her feet and she had laughed seeing my pathetic sight and had run her stocking clad sole up it telling me that I was to get on with massaging her foot as that was the only important thing happening in the room at that moment?)
Fran was the one that after kissing me at the fancy dress party where I was dressed as a woman and she as a French Prostitute that I was so small that she would not fuck me? and went on to spread the word to everyone at the party that I was a dud down there (you know how women love to gossip)
Anyway back on the bed I watched with bulging eyes as Fran took up from her bedside cabinet a vibrating dildo and proceeded to fuck her pussy with it and after letting me see how she was doing it she got me to take over doing her very wet and gaping pussy in a fucking motion as she went for another climax telling me that I would never be able to pleasure a woman with my tiny penis and women needed cocks that were substantial something I did not possess along with a pile of other humiliating missives over my lack of size that to me were shamefully exciting.
After using the dildo on Fran it lay in the bed wet and glistening with her sludge as we cuddled with Fran scooting up behind me our stocking clad legs hissing and sliding together when suddenly I gasped as she started to caress my bottom and eventually eased first one finger then a second into my tight little virgin sissy pussy making me gasp in first surprise, then a little pain and finally an uneasy comfortable feeling? as she did a fucking motion with her long fingers in my back passage as she whispered to me that this was how girls liked it?
I was as erect as hell and leaking and moaned when she took her fingers away as I had started to feel some very odd emotions with Fran's fingers in me only to become frightened and scared when suddenly she got quite physical with me and Fran was of a size that she could overwhelm me then and she forced my stocking clad legs open and I squealed with surprise when she then roughly pressed something very much larger against my terror twitching sphincter as Fran had taken up the used dildo in her hand and was determined to put it inside of me.
The pain was indescribable as Fran pressing me down with her weight and applying harder pressure kept talking to me saying I needed it dressed as a woman and suddenly I screamed a bit and the head of the dildo popped open my anal ring and entered me!
I remember I was panting "Please!" for her to stop but I think Fran took that as a "Please!" for more and in seconds she had forced the entire thing up my ass making me wail as she told me to relax and it would be ok?
Well it did end up ok as after a bit of her fucking my bottom like I had fucked her pussy with the dildo to pain did ease as I relaxed my emotions in turmoil of shame and humiliation being violated in a gay way even if it was by a woman because not only had there been pain of allowing what no real man would let happen but it was not feeling rather nice a strange all engulfing heat stirring in me and my little penis was harder than I had ever known it painfully so and leaking.
With her other hand as Fran screwed my sissy pussy with the dildo she reached round and started to caress my little penis making me melt and it took mere seconds till I smashed into a violent sissy squirt stuff shooting out all over Fran's bed as she nailed the dildo into me at a furious pace till I was drained and empty!
The first of a life long use of my sissy hole for others pleasure!