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Sissy Prison Stories


Here mainly for friendships. Not looking to hook up. Just looking for good friends and people to talk to and discuss life and stories.
I'm married, but I fantasize sometimes...I write erotic stories, many of which are explorations of my sexuality. I can't hook up realtime, but I like to meet new people, male, female or couples, it doesn't matter to me.
bi - enjoy pics, vids and stories of m/m oral. Have now started acting on these urges and enjoy oral
Very happily and securely married. Wife knows all and approves but doesn't join. She prefers to hear about the stories I bring home to share with her about my adventures with others. I don't smoke or drink (but not against those that do), am drug and disease free, so this is the only vice I have left. I am not into head games or competitions and have nothing to prove to anyone. I just enjoy all aspects of sensual and erotic play with like-minded, fun adults. Very open minded, versatile, and flexible. I have been surgically safe for many years and have no kids to prove it. I'm not into children, blood, or real pain (mine or anyone else's...but erotic discomfort can be AMAZING!)...other than that, am open to just about any and all positions and combinations. I am always very oral and very happy to help clean up before, during, and after. Prefer couples or moresomes but can meet with select singles. Not into role playing but can be happily submissive to serve and please. I am happiest when I can give pleasure to others, help them explore and live out their fantasies. Care to share a few with me? I'll do whatever I can to make them real.


That is some story!

It reminded me of when my ex-hubby played a sissy prison bitch in the film "The System Within" He flew up to New York first for auditions and then later flew back to film his scene..it was based on a true story where the protagonist was a pro football player who also owned a club, had introduced a guy from Miami to a guy from New York and unbeknownst to him they set up a drug deal in his club. He went to prison and his life was nearly ruined. The guy who was behind the movie later went on to be a model and entrepreneur. "The System Within" was shot both here in North Carolina and in and around the New York City area.

s and es,

THIS Sissy would like to know also so please if anyone knows let us know,SISSY,aka(MissSucker) is in chico cal.area.COCK SUCKING SISSY CUM DUMPSTER
Hello, I'm a 33 yo panty wearing bi male sissy total fem bottom that loves to be used like a little sissy bitch and told what to do. However, right now my main concern is finding a room to rent in the HEB/ARLINGTON/FORTWORTH area around the first of April.

I would be willing to trade rent and utilities for personal services. If you are open minded and would like a live in sissy cocksucker at your disposal the situation could be perfect. I would dress fem 100% of the time in the home (no matter who comes over, unless directed otherwise) and will willingly satisfy your needs as your little sissy sex/toy wifey.

Have been wanting a situation where I could openly stay dressed and feel good about being used like a sissy fem daily. So.....let me know if there is a spot at your place for me to get on my knees.

sissy Danni
This sissy would like making you go through the hoops! SISSY would love playing with you & USING YOU!! We could have FUN together,you COCK HUNGRY SISSY SLUT,SUCK COCK BITCH & EAT ALL THE HOT THICK CUM,SLUT!!!COCK SUCKING SISSY CUM DUMPSTER
i`m looking to be turned purely sissy and suck cock,eat cum and get cock in my sissy pussy, i want to learn about living as a sissy for ever and worshiping big cocks ,to become a woman
hi everyone, 47yo closet cd with smooth lil clitty fetish would luv to hook up and play sissy with women or other cd/tgirls the week of October 9th. not into anything forced or not mutually desired. enjoy dressing with, seeing others dressing and being seen dressing in sexy or sissy lingerie. ultimate fantasy would be to dress n play with another sissy and her wife/ gf. email if possibly interested.
I keep my sissy shaved head to toes as a good sissy should be.... isn't she just so cute.....
Don, check your email......I think I'm the panty wearing little sissy slut you have been looking for baby.

your devoted little sissy cocksucker,
I am also from Erie, PA. I am a submissive Bi sissy crossdresser, late 50's (NOT PASSAABLE) but with breasts. I am strictly a BOTTOM. If interested, please get back to me..

Be sure to tell me all about yourself, and what you like to do.

Sissy Kelli
i have been the wife of a federal inmate since 1992.. i met my leo in 91....and your right...there are so many things that we outside the walls are not prevliged to know.
gaurds play games with inmates heads and are cruel with no feelings...my boy earned a name for himself behind the walls of some of the worst hell holes in the prison system......prison gaurds forget one thing........INMATES DO GET OUT AND ARE HUMAN BEINGS!!!!!!!! Prison tears apart families, destroyes marriages and effects the kids the most...they need nurturing from the imate parent as well....yet the system is fucked and kids suffer the worst....the system doesnt get it...keep the family intact, make more pleasent settings for visits, no matter what level prison it is..
childeren dont understand bars on windows, gaurds tellin papa he cant play normal with the kids, no running or playing tag ect.....just cold visiting room minimal toys,worst yet being told i cant nurse my daughter descreatly under my coat at the time..having to nurse her in the bathroom where is was freezin cold
so called xmass party at prison yet still being told what to do ......for 15yrs i endured many things while my leo was gone........whats important is we are together again and very happy.....Prison sucks for those left behind to pick up the pieces, nights crying myself to sleep with just a blanket to hold and call his name
having phone sex to maintain....wanting to be true to him yet still being human and needing affection...i chose a woman with his concent. for me there is no other man but him....he made it out alive and we found eachother together again let no one put asunder.......sweets i truely understand that other world so empty and so cruel......if society would open their eyes to the inhumane treatment of prisoners maybe just maybe things will change....Change comes with an idea.....there are more rapes in the prison system than out on the streets........
sweets my heart reaches out to you.......I DO UNDERSTAND.......put that world behind you now and look at the wonders of FREEDOM.......i pray you find peace and god bless
Hi, I'm a 48 year old CD. No, wifey doesn't know, lol. Been dreamin about being on my knees before a "real" man. Anyone interested? Really want to see just how a sissy feels at that first moment... knowing what a sissy does... {giggle}.
my name is sissybritney(mark). 56 yr old sissy/sub white weak pervert. I would love to be trained to be a SUPERIORS bitch/slut/whore/faggot. i have some experience serving Mistresses as a sub/sissy. Im looking to finally take the next logical step into becoming what i was meant to be. A PATHETIC SISSY FAGGOT. I will serve MASTER, MISTRESS OR DOMINANT COUPLE. i also have a MAJOR weakness for HUMILIATION. i think my 56 yrs as a beta bitch, becoming addicted to FORCED BI & all the HUMILIATION from that has taken over my dreams & fantasies. Would love to discuss what started me down this path........TO BE A SISSYFAGGOT
will gladly let you suck me as long as I can suck you and have you give it to me up my tight little sissy ass first. Want to suck, swallow and bend over for you while she watches, then you can do whatever you want with me.

your devoted little sissy cocksucker,
i have read a few of your stories now. very good stuff! very creative. i really hope that you keep writing these stories.
First off id lile to say i am a very easy going guy anyone from this site thats met me will surly agree. I am a CD male when i do dress up im a hot tall fit sexy blond and im super horny for cock i love women but having found the joy of being a sissy cock slut i cant help it i crave cum and cock so much so i actually want a biyfriend a sexy man that uses me the i was intended and hopfuly thats at least once a day if not more ............so my question is why is it so hard to find a man who wants to fuck me not on cam or text but actually fuck me cum on me in me as much as u wantb....i remember when all i wanted was to fuck someone when i was top but now that im cd its a pain in my ass so so many flakie men comon fellas i may be a sissy but no shiws and excusses are so week u might as well not even have a cock bitches so were are all the horny men at now that im a sissy ????? hoplessly craving .....
Nice stories, I get aroused reading first time same sex stories.


Prison Pen Pals
I have several friends that are in prison and know web sites that have inmate listings.
Couples Searching For Bi Males
Hello , I am looking for couples to dominate me to help me learn how to wear make up , to dress and be a sissy for them , I enjoy sucking a cock tho I eat my own cum , I have yet to taste another males cum in my mouth , I would enjoy a couple who would let me be and become a sissy , cd , cum craving , cock worshiping ( strap on too ) sissy girl
Submissive Men
submissive bi male , ready to be feminized into a sissy slut for dominate couple and or dominate female , longing to be in chastity , to learn how to apply and use make ups , to dress and live as your sissy , to suck cocks and take cocks in my pussy , to eat cum off your body , to eat cum from your pussy and ass , to desire your strap on and a cock taking turns in me , letting your friends come over and letting your sissy try her skills and learn how to be a true sissy cock lover
Sissy Slut Training
looking for female dominate or dominate couple be a great sissy for , to dress , to think , to live as and be a pure sissy , cd , cum craving slut
Men Sucking Dick While Woman Watch
I want to be feminized and to live and dress and wear make up like a good little sissy slut , to suck and fuck a cock and have a strap on at same time , to be dominated and used by a couple , learning to be and live as the couples sissy
Sissy Slut Training
looking for couple or single female in North Georgia area to serve as a permanent cd , sissy for casual sex or for long term relation ship , I have always wanted to have a woman dominate me , to strap on fuck me and let me taste myself on her cock , to shave my legs and wear chastity to learn my place as your sissy and pleasure men for you and with you
Story Writing
I've even written stories about people I've met online...
I love hearing stories of girls who let their dog lick their pussy
Cum In My Ass
I'm surprised there isn't already a discussion in progress. Some of the hottest porn scenes I have ever seen ended with a cum kiss. Do you have any stories to tell?
Story Writing
I've written some stories, and have several of them on various erotica websites out there. If you're interested, I can tell you where to find them, and which ones you may be particularly interested in...
Black Couples Dominating White Men
I would love to be a little white sissy for a dominate black couple ,
2 Cocks In 1 Ass
I would love to try it. The very thought of two guys fucking my sissy arse together makes me feel so horny.
I am so turned on when I think about learning how to walk and dress , to wear make up and be the true sissy I was meant to be either for a female dominate or to a couple
69 With A Strap On
hello I live in North Georgia and I am looking for dominate couple or dominate female to help me be the sissy I was ment to be
Dick In The Mouth With A Dick In The Ass
Would love to be in my sexy lingerie,and getting a big cock in my ass and mouth. being the sissy slut
Sex Toys Used On Men
hi I`d like to find a dominate woman and or dominate couple to help me in being the best little feminized sissy i was born to be
Dominant Women
I am lusting for my sub/slave owner ship marks, anyone need a sissy boy for long term training, will take time to work this trusting relationship out, contact me.

I live to serve and obey.


I'm going to post something in the place where I found success stories. We had a meeting last night, and I was quite satisfied. Wow! In less than 36 hours.

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