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Sissies in Prison

I'm a former Marine and Retired Prison Guard. I love all sports , dinning out etc. I'm very open to sexual desires
Sissy who loves others sissies, and the ovassional man inside me
I'm a little bit older kind of very submissive sissy Boi who would like to e-mail and chat with a dominant couple who would like to ' own ' a sissy by e-mail or texting. I like to dress up in sexy lingerie but don't really fully dress in women's clothes as I think I look a bit silly and not so pretty. I'm shy but once I get to know a couple - who knows, where things might go from there. The only thing besides the way I look dressed up is I want to make sure the man of the couple understands and sympathizes with sissies. I DON'T want a guy who is too dominant or aggressive, one who is mean to sissies, one who would smack me around all the time, slam his cock roughly into me ( not at first ), Slam his cock down my throat making me choke or vomit , or who would treat me like shit !!! I need the man to be loving and gentle and treat me like a soft, feminine girl like I dress up to be - not like a worthless street whore or a piece of trash. Dirty talk and everything is fine, but no physicial abuse is what I'm asking. That's all I'm worried about. I don't mind being their sissy bitch, I just don't want to be hurt or abused physically.
Straight but curious eager to Explorer only had little experience with oral. Would love to spend time with sissies CD and transsexuals bi couples as well
I'm a horny male looking to fuck a male's holes and fill them up with cum. I'm into sissies, trannies and cross dressers, but I do like females too. I would carry a condom just in case of safe sex.
passable and sexy transsexual that loves bi guys, sexually liberated and open minded. love 3sum and groups with multiple guys. i also have a thing for young sexy panty bois sissies cds fem bois and twinks. love to party and explore all night
Top Pantyman seeks other panty lovers (and bottoms looking to receive a cock "gift-wrapped" in panties)! I'm a SWM 48, 5'10", 240 lbs, short brown hair (with some grey, of course!), hazel/brown eyes, average looking, clean-shaven (no facial hair), thin built (but have a belly) intellectual-type. Average 6" shaven cut cock, smooth chest and back, and looking for other smooth bodies to play with. Drug, disease, and smoke free, and looking for the same. Tender-hearted with a lot of unfulfilled desires - nice guys need sex too! I prefer quiet intimate times and don't care for big crowds. In addition to the usual interest in females (straight, bi, and lesbian), I'm a long-time admirer of cross-dressers/transvestites, male-to-female transgendered (pre-and post-op), she-males, and so on (you get the idea!). I'd like to try fucking a girly-guy's smooth-shaven asshole (especially when it's framed with pretty things, and would like to wear pretty things while doing it)! I have a love affair with panties and the people who wear them, female or male! I like seeing panties on almost anyone (shaven), and I love wearing them myself (which I do almost every day)! I have a pretty big collection of panties which keeps on growing! I've begun to dabble in camisoles recently, too. That fine fabric brushing against my sensitive nipples does the same kind of good things for me as having my cock wrapped in the fine fabric of a pair of panties! My nipples are very sensitive and are a definite focus in my sexuality. Two "hot spots" second only to my cock! I often think that despite their small size, they might be as sensitive as a woman's nipples. Despite my love of feminine undergarments, my pleasure would come from fucking and not from being fucked. My orientation would be best stated as "top". Not into the extreme or hardcore fetishes (pain, violence, scat, watersports) or , just interested in safe, sane, gentle fun like fucking a girly-guy (is that you?) in her smooth, velvet hole! Pull your pretty panties aside, down, or off and slide right in! Things I've been thinking about for a long time... I'm located about an hour and half east of Edmonton, and would travel to you. I'd be happy to do a road trip that promised this kind of fun! I have no experience in this and am both excited and frightened by it, so I'll depend on your patience and understanding. I can't deny the kinds of feelings and desires I have and it's definitely something I want to try with the right person (or people!). And if we click, a long-term friends-with-benefits relationship (with "sleepovers") would be great! I'm attracted to femininity and those who express femininity. Looking for feminine people (crossdressers, sissies, trans females, bisexuals who like crossdressers, or straight ladies who just happen to like a guy in panties!) and fellow panty and lingerie fetishists for fun and friendship.
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.

Hugs and Kisses,

i love undies too and sissies for sex,love to chat
Sex 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: Huge 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.
Male... 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.Love 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 Sexually 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.
Any she-males, lady boys, fem boys or sissies that want to fuck and suck and be fucked and sucked near Los Angeles?
Hit me up!
Some nights I dream of having a line of Black Men just waiting for their turn at this sissies white ass. Going deeper than any white man has ever been. Stretching my ass to the limit and making me scream for more. It's too bad it's only a dream. I'd love to have it happen for real. Lindawantabe

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