Serving the bisexual community for over 24 years

Shemale Inmate Penpals

Whether you are transgender yourself, or looking for shemales to chat with or to hook up with, you will find plenty of shemales on BisexualPlayground. This is the place to chat with, meet, and hook up with real transgendered people. Inside you will find plenty of real shemales who want to chat.

Find Shemales

bamasnake	Just looking to see who is out there. Looking for e-penpals mostly. Anyone and everyone is invited. Love married men! Send Mail IM
candy968	i am bi-curious looking for penpals and friends who don't mind my questions and willing to teach me new tricks Send Mail IM
crazieone67	VERY EASY GOING AND EASY TO GET ALONG WITH AND NOT HARD TO PLEASE. I AM VERY UNDERSTANDING AND I AM WILLING TO LEARN NEW THINGS WITH NEW PEOPLE I WANT TO TRY SOME BEING INMATE WITH ANOTHER FEMALE CUZ I AM SO SO CURIOUS. NEED A WOMAN IN MY LIFE MEN HAS JUST MADE ME SICK OF THEM SO IF U LIKE WAT U C PLEASE FEEL FREE TO HMU..... Send Mail IM
Tuck9117	I like shemales and I'm looking for penpals Send Mail IM
Bigdr80	Stocky, chubby, tattooed(not a thug or former inmate or anything like that) 5’7” curious to know what it’s like to have a man in all ways. I need a teacher Send Mail IM
Mannick2000	Not looking for penpals Send Mail IM

WiserRanter	Looking for penpals to email with, bi males and bi females, if anything happens then it does. Hug Send Mail IM
Join To View blondenymph77	Hey ya'all...I'm currently on the search for some penpals...whether thru eMail or Snail Mail. Could be erotic letters or regular letters...I love to write letters and wondering if anyone else would like to also. Its a great way to learn new things about people's lives, where they live, how they live, and all that. And, if they are erotic...mmmmm Anyway, just thought I would check...if you're interested, either eMail me or leave a post on here. Happy Holidays, Kasey Hug Kiss Send Mail IM
Join To View blondenymph77	Hey everybody...I'm sooooo hoping that people that post replies to forums happen to double back and check them again. A few of you have emailed me privately on here about becoming penpals without replying to the forum post, which is fine! However, a couple of those few have me blocked due to age or couple...and I can't email you back...this is the only way I know to try to contact those people..and hope you figure out who you are! Hug Kasey Send Mail IM
Join To View MatureCurious101	I’ve been thinking again…. My first post was about my being bi-curious; particularly with regards to sucking a cock. My second one was about a mechanism that might get me to actually do that (persuasive woman). This one is about another mechanism; Shemales. My second post laid out the fact that I’ve been straight and have enjoyed that lifestyle for many, many decades now, so it invoked the use of something that I know pretty well; women - did I actually say that? Yup, I guess I did - as a catalyst to persuade me that sucking a cock would be a good thing for me. Furthest thinking leads me to question whether both of those things could simply be combined into one person; the persuasive woman and the interesting man. Enter the Shemale, perhaps(?) Shemales, at least to me embody both male and female characteristics. Frankly, from an emotional standpoint I’m really not sure if a Shemale is a male with a pretty face and boobs or whether she’s a female with a cock. Biologically I know the answer, but emotionally I’m not sure. Is there anyone on this forum who had their first bisexual experience with a Shemale? If yes, was it a good experience and would you recommend it as a good way to satisfy my bi-curiosity? Send Mail IM
Join To View mytpopsta	I am guessing you never reported it and I figure you would or have done it again. So did you ever force anyone else? Tell the true former inmate to former officer. Send Mail IM
Join To View Scottytohotty1970	Former inmate on sex charge looking for same share story's or anything on your minds Send Mail IM

Find More

Interests:

TransfemaleSandieQOS	Prison Pen Pals I have several friends that are in prison and know web sites that have inmate listings. Send Mail IM
truckchef01	Transsexuals Wanting to be sub for shemale(s) Send Mail IM
Biman22191	Transsexuals I love to be with a shemale. Send Mail IM
Swingcpl69	Transsexuals I would love to be a shemale one day. Send Mail IM
wolfee1171	Shemales With Big Cocks I would love to have some fun sex with a shemale Send Mail IM
Jeffsready	Men Sucking Transgender I want to suck a shemale so bad Send Mail IM

Testimonials

hissexybitch

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

Shemale Inmate Penpals

Interests:

Testimonials

Other Topics

Interests