Sign up now to join the fun!

Caught Crossdressed by Boy Across the Road

I am a 50yo bi male into crossdressing, role playing, kissing, just having fun. Like both sexes, can be both a top or a bottom for right person. Love to please, and would love a threesome while crossdressed, with a couple, or if the chemistry is right, two males. Would also like to find a female who is OK with a crossdressed male to have fun with, and play dress up with. My motto is, if it feels good, just do it.
I am an outgoing person who try's to not get caught up in any stereotypes. I like to let people feel and act the way they want to, and I wish the same for my self. I do get caught up feeling shy but I try to always just do what feels right and not be reserved.
50 yr. old was married for 30 years . One nite my wife didn't take her sleeping pills,caught me crossdressed looking like a slut, short short black dress,make up,nails,8 inch heelsand a 10 inch dildo in my mouth. She was gone the next morning. I'm single now. I would like to be dominated and humiliated , forced to suck cock, made to try on womens cloths at the store or forced to show people my sissy panties and little tiny clit. I'm 5' 10'' 185 lbs. grey hair and balding. I haven't done anything like this before but I want to try it and see how it goes
Widowed (25 years) male getting knowledge of what mat be out there. Older I get seems the hornier, I play almost daily as I live by myself, but on the road I tend not to, fear of getting caught from family members, just avoid drama. One day to hold another cut cock, no matter length, just a preference, and jerk it off, seeing it cum for me, a fantasy, then suck it off. Always hot for women that will never change.
Well i am 49 and iam in retirement from the USMC I retired at the age of 29 to chase my child hood dream I caught it or it caught me cause it's got out of so I am now a pro puller for the NTPA TRUCK AND TRACTOR PULL association...and have been for 19 years now and on road a lot is takeing a lot to get use to me being aMan with veryhigh sex drive with a over sized cock why he blessed me with all this dick I well never no but it's got it's good and it's bad like everything else in life ..,SO JUST IN YOU ARE WONDER IT IS 13 AND A HALF INCHS LONG AND AS BIG AS A COKE CAN AROUND ALMOST..... So if you thank you may be interested in having the time of your life..... And don't mine the big mess I leave behind when I finish up... Yes wipe the smile off now it's not funny yes it's a trun on very hot if you like to be covered in it if so............ Anytime day or night ... Email....... . yes it's a real email address......... Text me on hangout if you like very fast response back no waiting....... Pictures and video available Stright to you just request.......... Looking forward to give you the time of your life......PS.. I love older lady's they know how to handle something of that size......
i am fun loving guy that likes to be accepted for who he is.i wore my moms things and sisters panties young.i got married was caught dressed.i was also caught playing in diaper at 10 by mom in bathroom,punished.
I've only crossdressed in private, going back to my early teen years when I'd dress in my mom's panties and bra when no one was home. I'd walk around the house acting out a scene. I still dress in my wife's clothes once in a rare while. They hardly fit... Not at all. I've never told anyone.

I've been with others crossdressed a few times. I love it.
hi, Eydie here from the Poconos...did you ever party at Rainbow Mountain resort on Mount Nebo road past Marshals Creek?'s a gay owned resturant/club...when I go there crossdressed everybody treats me nice....anyway, the Halloween party there is always fun,(look 4 me ina french maids outfit *giggle* Fri. nite) should check it out....seeyalata
got caught 69n with my best buddy at 12 yo in his pup tent by his mom.funny she never said anything about it to either of us.when i was about 25 yo i got caught getting a bj from a gay guy in a campground bath house at 2 am but it was just by another ex girlfriend caught me licking her best friends pussy in a hallway and i guess thats why she is an ex,she just couldnt understand.was caught many other times and caught quit a few others myself but ill never tell !!!
me too ! it has always been my fav fantasy to be caught sucking a man and then made to finish or be helped . Anyone interested ? I'm on the road alot
Luv to feel feminine. I dress feminine as often as possible. Even when not theres usually a 95 percent possibilty that I have panties on. I've gone on several road trips lately 100 dressed. Panties skirt long knee high socks bra tank top of some sort wig. Lipstick eye liner plus lil more I need more practice with the make up but I still wore it. 2 inch heels. Not sure if it's just the rush that I could be seen in public by someone who knows me or chance I could get pulled over and obv wouldnt be caught dressed maybe I want to be caught so I can stop hiding it?
I never got caught masturbating when younger or even now and never got caught having sex with a girl or my wife but in the past years I have been caught several times having sex with other guys,, my wife caught me under a guy in the bed so did my daughter and been caught by a friend as a mutual friend of ours was taking me outside in a park on the picnic table..


Being Tied Up
Love the thought of being crossdressed and tied up fully love to tie a woman up bent over a chair or the bed her to wear what i want and me to be crossdressed ...i would make sure she cums multiple times b4 she begs me to fuck woman wanna love this or wanna try Charles healthy 42 yo crossdresser here!
love to be crossdressed for your use
Public Masturbation
I love public sex and masturbation, and love being caught. just not by the police. :) every job I have had since being a teen I always let myself be caught my last week before I quit. turned me on coming to work the rest of the week with the rumors flying. I have sucked guy off andbeen caught too, that fun too.
Demolition Derbys
There is nothing like seeing a car crashing into another car. I would Love to do this. I think someone should make a program for the road rage peopleof the world where they can go take their road rage to and get it out of their system afely. IconU4DragonnIconLRWolf
Blowjobs While Driving
Mmm if your near saugus, ma come pick me up lol i will suck your cock while you drive may drive off onto an abbandond road and want to do more. .But i do love blowing guys while they drive..had my ex gf eat me while i drove..and yes i did pull off the road lol...
Caught By Family Member
Both my kids live with me. One of ea. Ive been caught jerking off by both a few times and lets just say they were curious about it. I've been caught with my daughters panties too.


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