Keeping My Sissy Secret

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Jacob pulled up his trackpants and got up, walking to what I presumed was the bathroom. The coughing had mostly stopped, but I still had to spit out a bit of saliva now and then. I let myself drop down on the floor, lying on my side. This initiation had drained my energy and judging by daddies words there still was a lot to come...

Wait, had I just referred to him as daddy?

To be continued...

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AnonymousAnonymousover 3 years ago
Sissy One

I have been dressing for years now and taking female hormones.I now have the female body i wanted for a long time.38d breast wide hips tight ass hairless body.I have long blonde hair long eye lashes red nails and bright lips.The older couple have caught me going out for walks at night.Now i am made to dress and visit them weekly .I had never had sex with a man or women dressed before them.Now they take turns doing what ever they want to do to me.He fucks me and deep throat his cock.She in joys tieing me up collar leash ring gag hands cuffed behind my back ankles cuffed.She loves to use monster strap on dildos in my ass.All the while he films her fucking me hard.He has from time to time makes me suck his cock while she fucks me.They have taken to bring friends over for group sex both men and women to use me.

AnonymousAnonymousover 4 years ago
broken in

My next door neighbour has been fucking me for several years now. It all started when our wives went out together to the city for a long shop and we drank beer and swapped Bull for a while before agreeing that Catherine Willows in the original CSI was the sexiest woman on the idiot box. Soon we were looking at pics of her on my laptop, which led to various sexy fakes of her which had us both playing with ourselves, then getting our cocks out. Mike, who had an above average sized cock talked about fucking her, while I who haven't been blessed that way found myself thinking of BEING her, and grew careless. Mike suddenly asked if I was wearing any of my wifes knickers, and when I blushingly admitted that I was, and often did, he "asked" in a very masterly voice for me to show him. I dropped all my outer clothes to show him suspender belt, stockings and a tiny g-string. He walked over to me, put his hands on my shoulders and pushed me to my knees. Then rubbed his cock on my lips and said " I AM gonna FUCK you, but first suck me till I'm super hard!

I had, as a boy sucked several other lads, so I at least knew the basics, and found that dressed, on my knees with a cock in my mouth to be very exciting to me, even if I was gagging as he held the back of my head and forced entry to my throat. I suppose this lasted about ten minutes before he blew his load into me. Most travelling to my stomach, with some blowback spillage onto his pubes and my chest, face and hair. Obviously we both needed a rest, but shortly after, and basically having cleaned up the mess on us and the room, we left a note for my wife, saying we had gone to his place to watch a match. His wife was going to visit her sister for the night, straight from the city, so we could have some more FUN by ourselves.

Using his wifes old clothing from the loft, and she had obviously dressed like a whore in her younger days, I was soon in a purple, six suspender basque, with her old (and large) false tits stitched in, black stockings with purple tops, toes and seams, see-through french knickers and very tight and strappy "Fuck Me" heeled shoes. And, of course Mikes cock in my mouth again. This time however, as soon as he was rigid, I was kneeling on the bed edge with my mouth chewing on a pillow as he forced my knees apart for the right hight for him to stand behind me and painfully force my anal pucker open to ride me a pussy for future use. Unless a lot of work is done over some time (i.e. days, if not weeks) don't let anyone fool you that being broken in for buggery is anything but painful. Where most of the stories are correct however is that after a few, "loosening" fucks the pleasure someone who knows how to fuck men can then give as they ride against your prostate can be cum inducing and immence. Mike had me twice that night and several times the next day, when we went "fishing" together at a Motel some distance away. Now I'm mainly fucking or sucking in a group of six tops, Mike included, and me and two other bottoms. All of us pay into a clothes fund, so us bottoms can start a session sexily dressed, but the wear and tear on our sexy gear is hard, like the cocks that roughly screw us.

AnonymousAnonymousabout 5 years ago
I lived it, I loved it.

As a young teen I was dressed and used like this. More please

cdCindy1cdCindy1about 5 years ago
please continue

I can't wait to read the next chapters. I too am a sissy CD cocksucker and I love reading about sucking older daddy cocks. Please continue and tell us how the sissy gets fucked. I can't wait !!!

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