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Sissies in Prison

horny, well endowed and good looking 32 year old black guy from London looking for fun with feminine CDs and sissies
I'm 28 an just interested on a little play on me I don't go down on woman it's just not me I'm not single I'm engaged but my fiance is in prison so need some play time for the time being
Mature, Masculine, hairy-chested, stocky and 101% Top Daddy Bull that LOVES smooth sexy and sensual T-girls that love to please a real man. I am VERY experienced. I have met and enjoy many of you girlies and sissies in my kinky past both in person and on cam. I know what I want and what I like. I seek exceptionally sexy femmes for long, kinky and repeat c2c sessions - I will treat you like the living sex doll you are and you will please me. I am also open to very, very, VERY exceptional young Tgirls for meeting - this will only be if you are fully femme in dressing and fit certain criteria for me
I am a chubby, small-dicked sissy. I like to wear slutty high heels and lingerie, and put on Goth makeup -- lots of eyeshadow, lots of eyeliner, lots of lipstick. I feel so sexy when I dress up, my little clitty won't stop leaking. I mainly want to meet men who like boys like me who want their cocks sucked and who want to fuck sissies in their boy-pussies! I adore women, my focus now is on horny men, I doubt I would kick anyone out of bed, but my little dick can't satisfy a woman. I'd love to help you take care of your man tho! I'm just a crossdresser -- I can't transition yet b/c of work and family situations. So for now, I wear a wig when I dress, I try to keep my weight down. Someday I plan to transition, take hormones, get implants, remove my useless nuts, become the woman that waits inside me.
Old Age
is Not for
Sissies !

Be Happy
D i c k
it all depends on the man. some enjoy sissies some dont.
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 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
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 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,

i love undies too and sissies for sex,love to chat
on a public beach in Florida got them both prison time last year.
I have wayyyyyyyyyyy to many to list here. So, i'll just list a few at a time. here's the first one:
Movies and TV which are mostly run by men. So how are lesbians or bisexual girls portrayed vs bisexual or gay men?

Women: Attractive, sexy, perfect bodied women who are more than willing to let a guy watch or join in

Men: e flaming sissies to be laughed at or lecherous losers who want to sleep with any guy no matter what they look like.
Im Stevie, an i truly enjoy bein sissy, luv playin naughty in panties an slippery baby oil.luv dressing fem an playing on cam
Lookin for a naughty hung perv who's really into naughty lil fem submissive sissies. So if your lookin to have a naughty time i could always use another good friend- playmate luv to model new sissy lingerie on cam or pics and share with others
During a prison sentence, many straight criminals shag men, despite having wives and girlfriends back home.
We shouldn't judge them, just let Bi cons be Bi cons.

i was given my 1st bj by an older man that had recently gotten out of prison for being homosexual, this was in the late 50's and early 60's. at the time i was 11 yrs old and couldn't cum as yet. but what he did is give me my first orgasm and it felt so good but i didn't know at that time what i was experiencing. i had no less than 4 orgasms that night and he ate me like a piece of candy. i had experimented with friends but nothing like this. it wasn't till i was about 55 till i met a man in a motel and we were cock pumpers at that time and met online. we pumped then started to play with each other. after a few minutes i really had the urge to suck him, so i put his cock in my mouth and thought, this is nice i like it. i had never tasted another man's cum, just my own at that time, but i was determined i was going to swallow him. i did and it was great. i had a couple of men after that, but not until i met a neighbor about 4 yrs ago did i start to suck and be sucked on a regular basis. i can say now i still love oral with a woman, but i love to suck a man and take his load.....very pleasuring for me.......doubleguy
I had several encounters with 2 family members when I was very young (a male and female at the same time) they would be in prison today if it happened today. But anyway I never liked the part of the male penetrating me but I liked the act of me finishing him off after and during his sex act with the female. I also liked eating her after he finished in her or on her. For all my life I kept this time secret from my wife's. I finally married a woman who I am totally honest and happy with. (been together 12 years now) we are completely honest in everything and no secrets between us. I told her about the encounters when I was younger and about me liking the oral part and that I was curious about doing it again. She was turned on about seeing me be oral with another man and so we began looking, we have had 2 encounters and it was great, the one did not want me doing anything to him but he did the wife while I watched and when he was done I got to have the cream pie, the wife loved it. But I do not want the make to be oral with me nor do I want to kiss or hold hands. I am interested in the oral part only. Does that make me bi? In my book it does but I find being honest and open with my wife we have both found pleasure in it together. Nothing better than going down on a guy with your spouse.
... My 2 cents:
There are laws on the books today in the US that are supposed to limit access to firearms. You need an two expensive federal permits to purchase any firearm that is capable of discharging more than one round per trigger pull, one to own them and one to purchase.
Ever hear of someone being charged with possession of automatic weapons without a permit?
A state permit is required to carry a hand gun. The permit process includes criminal and mental health background checks. A felony conviction (possibility of 365+ days in prison), or a domestic violence conviction, and certain mental health disorders will cause the permit application to be rejected.
Have you heard of somebody being charged with carrying a handgun without a permit?
Now look at the violent crime rates in Washington D.C. and New York City, two cities with very strict gun control laws, and compare it with Dallas Texas where it is much easier to get a pistol permit. In research I did in 1996 for a collage course, there was a striking correlation between legal gun access and the violent crime rate. The stricter the gun control laws in the area the higher the crime rate. I also found a survey done with convicted felons concerning their preferred victims and "hunting" areas. This survey showed that they preferred weak looking targets in areas where there was little chance of armed resistance from either the victim or a casual by-passer.

Shadow Knows
I've learned in life one just shouldn't judge another by assuming, We all judge ourselves every time we look into a mirror.Isn't that enough?! I find each person on this sight to be unique individuals with their own unique lives and situations. One assumes,then judges,by that. Really,what do we have to judge by other then ourselves,or lack of self ! My man is straight yet open minded.I've been Curious all my life. Yet too afraid or too conformed to society to do anything about it. Now with my man I can explore without fear,for I have his support and security to back me up.I find this normal in our 50's.Perfect for him,just now coming into midlife crisis,and, what man doesn't have a fantasy of seeing two ladies together getting it on?! For our situation this sight just fits our purpose perfectly! I don't feel age has anything to do with this.I don't feel exploited,hypocritical,nor manipulated. I'm not phobic of bisexual men,it just so happens that my man is straight-yet I would love him just the same if he wasn't. I love him for himself,as he does me. I'm not claiming to be Bisexual,I claim to be Bi curious,as many others claim to be. I have to start somewhere and I see nothing wrong with this either. I believe that everyone is born bisexual and that Thur centuries society has brained washed and conformed us into being straight for either religious or political reasons. I believe this is a crime that has to be rendered somehow. I see that this sight is one of the ways on which if one seeks a way out of this prison of conformity, then they can break out of the bondage to experiment and decide from there what their truth is. If one chooses to stay straight that is their freedom of choice as well. doesn't always gives us a choice when it happens,love just is...We're lucky when that love is open minded enough to love us for ourselves and allows it to be so. I'm sure there maybe a few cases were one wishes just to show how much one really loves the other, unselfishly,enough to share the other with another lady or man.They may claim to be bisexual just to share. I find this special person to be very rare and would have to be capable of unconditional love on this persons part,rare indeed! If any of you out there have such a person then Cherish them as a rare jewel.
1. The roundest knight at King Arthur's round table was Sir Cumference. He acquired his size from too much pi.

2. I thought I saw an eye doctor on an Alaskan island, but it turned out to be an optical Aleutian.

3. She was only a whiskey maker, but he loved her still.

4. A rubber band pistol was confiscated from algebra class because it was a
weapon of math disruption.

5. The butcher backed into the meat grinder and got a little behind in his work.

6. No matter how much you push the envelope, it'll still be stationery.

7. A dog gave birth to puppies near the road and was cited for littering.

8. A grenade thrown into a kitchen in France would result in Linoleum Blownapart.

9. Two silk worms had a race. They ended up in a tie.

10. Time flies like an arrow. Fruit flies like a banana.

11. A hole has been found in the nudist camp wall. The police are looking into it.

12. Atheism is a non-prophet organization.

13. Two hats were hanging on a hat rack in the hallway. One hat said to the other, 'You stay here; I'll go on a head.'

14. I wondered why the baseball kept getting bigger. Then it hit me.

15. A sign on the lawn at a drug rehab center said: 'Keep off the Grass.'

16. A small boy swallowed some coins and was taken to a hospital. When his grandmother telephoned to ask how he was, a nurse said, 'No change yet.'

17. A chicken crossing the road is poultry in motion.

19. The short fortune-teller who escaped from prison was a small medium at large.

20. The man who survived mustard gas and pepper spray is now a seasoned veteran.

21. A backward poet writes inverse.

22. In democracy it's your vote that counts. In feudalism it's your count that votes.

23. When cannibals ate a missionary, they got a taste of religion.

24. Don't join dangerous cults: Practice safe sects!
Dear Members,

The Department of Justice has enacted new rules and regulations known as 28 C.F.R. Part 75. The new rules derive their authority from 18 U.S.C. §2257 and are meant to provide the government with a set of rules they can use to help eliminate child pornography. Bisexual Playground has always and will always advocate the elimination of child pornography and child pornographers.

The new rules dictate record-keeping requirements for producers of sexually explicit content which depicts "Actual ually Explicit Conduct." Basically, what this means is that producers of certain types of explicit photographs need to keep records about the people in the photos (the models). The new rules are very broad, and could be interpreted to include us as producers because we, as webmasters, publish this site,, and because the site contains photos that are sexually explicit.

We have never and will never maintain the types of records this rule is requiring (copy of driver's license, etc.) for every one of our members. So, our only other option if we wish to comply with these new rules is to remove the images that would fall under this rule from the site.

The Free Speech Coalition filed a motion seeking a Temporary Restraining Order enjoining enforcement of the recently re-issued federal record-keeping and labeling requirements, 18 U.S.C. § 2257. What this means for us is that there is some hope that these rules will end up being thrown out, or changed in such a way as to exempt us altogether. For this reason, your photos are not being 'deleted' however they will not be visible on the internet. Should we find that these new rules do not apply to us, we will surely put all the photos back.

To be clear, they types of photos we are removing from the site (temporarily) are the following:
(A) sexual intercourse, including genital-genital, oral-genital, anal-genital, or oral-anal, whether between persons of the same or opposite sex;
(B) bestiality;
(C) masturbation; or
(D) sadistic or masochistic abuse;

This is not a change in policy on our part, but rather an update to a law that causes us to make changes in order to remain law-abiding.

In order to only remove the offending photos, we need to sift through hundreds of thousands of photos. Even with the extreme help of our team of Moderators, Assistants and helping members, this may take days or weeks. To ensure that only compliant photos are visible, all photos are being assumed to contain actual sexually explicit conduct until they can be reviewed by one of our team. This means photos will filter back in as time passes.

The punishment for our site not complying with this rule is the immediate shutdown of the site, and years in prison.

We know and understand your frustrations about photos being removed, and we sympathize. Our hopes are that sites such as ours will be found not to apply to the new rule by precedent, or by amendment to the rules themselves. Until then, the photos with actual sexually explicit conduct will be removed from view, but not deleted. You may upload as many nude photos that don't contain explicit sexual conduct (as described above) as you like, in fact, we encourage you to!

We thank you all for your support, and your understanding of our situation. We will try to reply to any messages here in the forum, or to our mailbox as always, but please understand we must also review all the photos to get them back on the site.

Rest assured we are going to stay as informed as we can on this and will update members as best and truthfully as we can.

Thank you all again.



Prison Pen Pals
I have several friends that are in prison and know web sites that have inmate listings.
Hello all!

I would love to meet other Sissies and Sissy lovers near so cal!

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You guys are doing an awesome job with this site.  What a great concept!  Hope to chat sometime!