Serving the bisexual community for over 24 years

Crossdressing Stories Caught by Neighbor

BisexualPlayground ›
Topics ›
Crossdressing Stories Caught by Neighbor

Stories on Bisexual Playground

bicyclerider	I really like the outdoors. Enjoy bike riding, camping, hiking, and sex in the woods is a great time...well if ya watch out for the poision ivy. I am sort of new to this. The last 3~some i had was back with my ex and a neighbor. I enjoyed watching, joining in and when we both played with the neighbor. Send Mail IM
cd_debbie	I first got into crossdressing in my late teens. For a few years my 'kink' was confined to strictly wearing women's lingerie and clothes to get my thrills. I was closeted, it was my big secret, and I had no thoughts or desires pertaining to bisexual or submissive situations. I discovered crossdressing to be a "progressive" fetish, where I was seeking that "next higher level" to maintain the thrill I got from dressing as a girl. This progressed to self-induced "dares" that eventually led to me going outside dressed, usually under cover of darkness. Soon it was day-time dares in remote, rarely travelled areas, where I eventually got caught. I experienced my first submissive and bisexaul encounter that day, and thoroughly enjoyed it. I haven't looked back since. Send Mail IM
SissyMacy4u	I've been crossdressing and wanting to be a real girl since I was born. I got one of my Moms pantyliners when I was like 6 or 7 and put it inside my underwear and wore it all day. Feeling excited and girly all day. But I forgot to take it off and at bath time, Mom caught me with it in my underwear and she knew I was wearing it like a girl even if I didn't understand everything. But I did know I was embarrassed then, and for watever reasons, I knew it excited me to get caught by my Mom, and that was the start of me desperately wanting and needing to be humiliated, degraded, used, and laughed at. I've been a true cuckold to my wife, Ms Brenda, for years. I told her everything after one year married, and it's worked out great. Send Mail IM
Alabama360	Ok looking, love email exchanges, love to write hot stories about crossdressing and wild bisex, sissy love. Send Mail IM
Mickey3	Hi, I am a white male, 5' 6" 170lbs, I am a outdoors men. Retired US Army. I am here for 1 thing, I found out by having a gay next door neighbor, that I enjoy sucking dick. My neighbor moved away about 3 years ago, and believe it or not I miss it. Send Mail IM
ShipTastic	I’m 37yrs old. And ever since this one time way back when I was 15yrs when the neighbor was letting me drink at his house and then all the sudden he took me in his mouth, it was great. But when I barely had his head in my mouth and he moaned and I started to cum, while he was in my mouth. And we got caught. Since that day, I’ve wanted to finish what I started. I want to take someone into my mouth and if I had my way, my first time would be with at least 3 men, while I try to please them, bringing them to climax one after the other, feeling them squirting down the back of my throat. Send Mail IM

Blugrassbi	I was caught the masturbating first time I can remember about age 5 by my Mom. She beat me pretty good over that so was more careful. Was caught by a neighbor girl and I were caught by her Mom at 14. Those were the ones I remember most. Send Mail IM
sadie1208	I got caught by my neighbor. I was drinking pool side with a friend when my nipples got hard she started to pinch them trying to convince me to be with her. Well my top came off and while she was sucking my titties she took her hand and played with my pussy. Well I have never cum hard and when we looked up my neighbor was standing in his backyard with cum shooting everywhere. Send Mail IM
Join To View Likenewstuff	First time was when I was 13. Me and my friend started playing with each others cocks and I leaned down and started sucking his cock. He blew a small load. We got caught playing with each other in my garage by my neighbor. He saw us through the back window of my garage. He was about 50. He told me to come into his house. I did. He told me to get undressed, I didn't want to but he said he would tell my grandma what he saw. So I stripped. Then he said he'd give me $5 if I'd jack off into a Dixie cup. I did, I jacked off while he watched and he took the cup into the kitchen. My Grandma and him were friends. She had to go away for a week. She asked my neighbor if I could stay with him. Well... Let's put it this way. There was a big difference between the taste of my friends cum who was 13, and my neighbors cum who was 40. My neighbor and me had fun about once or twice a week until he moved about a year later. Send Mail IM
Billy4fun2	OMG!! I have been caught countless times masturbating, by a stepsister or 2, Stepmom a couple of them, neighbor boy has caught me numerous times, neighborhood girls have caught me, on an average I masturbate at least once a day except on those days I am super horny then 2 maybe 3 times a day. I have been caught by strangers, friends. Been caught having sex in a mall, at a carwash, in a restaurant, Oh and on an elevator once. Send Mail IM
Join To View mommysissy	I enjoy laying naked out by the pool The pool boy caught me masturbating and joined me Now we fuck and suck each other every week. I hav also been caught by the neighbor masturbating she just smiled and watched until I shot a big load. Love being watched or caught naked. Send Mail IM
WiganDave	Hi JB, Just posted a story on crossdressing (see above) In doing so, your photo caught my eye, so I looked at your profile - I think that you are very sexy xxx Send Mail IM

Interests:

SchoolGirl06	Men Sucking Dick With Women Participating I'm new to the site but I'm very experienced. A couple of these stories made me so horny. I started crossdressing because I wanted to know what it was like to be a woman on the other end of sex. I am looking for almost the same thing but to a different degree. Having a woman direct or control me while I serviced as many men as I could. Of course, taking all the cum wherever I was told by our female director. ;) If anyone knows where I could find something like that, let me know. Hugs---Erica Send Mail IM
4nickate	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. Send Mail IM
slaveboy7777	Getting Caught Yeah I got caught too, my sister in law walked in on me and another guy, he was sucking me and doing a gr8 job. she freaked, then told me she would either tell everyone or i could buy her silence with my ass. i agreed to that and she had me take his cock up my ass, after he shot his load she spanked me and made me blow him (second load takes a while, my jaw got very sore) after he unloaded into my mouth she made me show her he load, then swallow it. Then she layered my balls with icy-hot and they both watched me dance around in pain while i jerked off, of course when i did it was into a condum and i had to swallow every drop while they laughed. The best part is she took pictures all through this ordeal and has keeps bringing them up, she just made me sit and participate as she showed them to her female lesbian neighbor and her lover. They both laughed, called me a sissy whore and we have a date for this weekend for them to strap a dildo onto my sis i law and have her shove it up my asshole. I hope this comes true, she enjoys it, decides I should be her slut slave, and she fucks me on a regular basis. Send Mail IM
carleegurl	2 Black Men 1 White Sissy Two men at not planned. My "neighbor" text me, said he was horny and so is one of his friends. I know, pornos start out like this... I reply - "Okay so ... sounds like a personal problem". A couple of replies, a preview pic of his friend's BBC to entice me and... OMG!!! A Jaw dropping moment later - left my door unlocked. Nervous, quivering & lubed up fingers in my asshole to get it ready knowing how my neighbor is - it's going to hurt good later. My "Neighbor" lived just down the street. My two BBC Pipes in a box, delivered, will be here shortly. Only way I can rationalize this. my neighbor's friend is very big - six foot seven big. I joked with him for a minute and ask him if you have any experience with TS girls. " Bitch, I breed fucking TS bitch asses!" They both unzip and next thing you now I have each one of these monster fucking BBC's in each hand. Ohhh.. My neighbor always brings over this really good lubrication oil, don't know what it's called but it makes penis' really glistening and really slimy and really shiny and really pumpy veiny. His friends BBC was OMG!!! A what seemed to be an 11 inch baby arm attached to two ! I can barely get in my mouth but it felt really good across my lips. He had the have the right amount of pubes. I'm starting to get into this. My neighbor takes me in the other room, gives me something to get me really nasty and horny and makes me lie on the bed - Ass up! His friend starts caressing and slapping my ass and starts running his tongue all over my ass pussy while I have my neighbor's growing cock in my mouth. I'm led to my knees on the floor to further service their BBC's with my mouth. "find dick just find dick" Alternating their dicks in and out of my mouth, damn these dicks got hard fast. Wait! Let me go get some condoms... His friend "we're not going to need them". But wait... The friend tells my neighbor he should go first "I love it all bred & buttery" My neighbor fucks my ass really good. "I'm gonna breed you deep" protested a little - "no no no" His friend is "oh yes yes yes" My neighbor came deep ( balls deep) In Me - My guts farting and dripping the whole way. I had two incredible anal orgasms. He had to prop me up on the second orgasm. I was like a limp rag doll as my neighbor's semen drips down my leg. I'm such a nasty fucking whore. Neighbors friends Saddles up and.. Oh Man!!! The stretching and the pressure of the length really deep inside me was kind of hard to take. It felt weird and out of place. " this ass is so buttery smooth I'm going to tear up and rip on this tender ass" My Neighbors friend had me pinned down on my back - he was thrusting so deep. It hurt too much it was just not right. Screaming as he let loose his babies really deep in my guts it was really slimy and nasty. It burned everytime I could feel his balls pumping on each squirt. Cleaned up, left soon after leaving my asshole leaking and numb. How nasty am I to allow this? Neighbor's friend left me his number. Send Mail IM
carleegurl	BBC Anal Creampie Two men at not planned. My "neighbor" text me, said he was horny and so is one of his friends. I know, pornos start out like this... I reply - "Okay so ... sounds like a personal problem". A couple of replies, a preview pic of his friend's BBC to entice me and... OMG!!! A Jaw dropping moment later - left my door unlocked. Nervous, quivering & lubed up fingers in my asshole to get it ready knowing how my neighbor is - it's going to hurt good later. My "Neighbor" lived just down the street. My two BBC Pipes in a box, delivered, will be here shortly. Only way I can rationalize this. my neighbor's friend is very big - six foot seven big. I joked with him for a minute and ask him if you have any experience with TS girls. " Bitch, I breed fucking TS bitch asses!" They both unzip and next thing you now I have each one of these monster fucking BBC's in each hand. Ohhh.. My neighbor always brings over this really good lubrication oil, don't know what it's called but it makes penis' really glistening and really slimy and really shiny and really pumpy veiny. His friends BBC was OMG!!! A what seemed to be an 11 inch baby arm attached to two ! I can barely get in my mouth but it felt really good across my lips. He had the have the right amount of pubes. I'm starting to get into this. My neighbor takes me in the other room, gives me something to get me really nasty and horny and makes me lie on the bed - Ass up! His friend starts caressing and slapping my ass and starts running his tongue all over my ass pussy while I have my neighbor's growing cock in my mouth. I'm led to my knees on the floor to further service their BBC's with my mouth. "find dick just find dick" Alternating their dicks in and out of my mouth, damn these dicks got hard fast. Wait! Let me go get some condoms... His friend "we're not going to need them". But wait... The friend tells my neighbor he should go first "I love it all bred & buttery" My neighbor fucks my ass really good. "I'm gonna breed you deep" protested a little - "no no no" His friend is "oh yes yes yes" My neighbor came deep ( balls deep) In Me - My guts farting and dripping the whole way. I had two incredible anal orgasms. He had to prop me up on the second orgasm. I was like a limp rag doll as my neighbor's semen drips down my leg. I'm such a nasty fucking whore. Neighbors friends Saddles up and.. Oh Man!!! The stretching and the pressure of the length really deep inside me was kind of hard to take. It felt weird and out of place. " this ass is so buttery smooth I'm going to tear up and rip on this tender ass" My Neighbors friend had me pinned down on my back - he was thrusting so deep. It hurt too much it was just not right. Screaming as he let loose his babies really deep in my guts it was really slimy and nasty. It burned everytime I could feel his balls pumping on each squirt. Cleaned up, left soon after leaving my asshole leaking and numb. How nasty am I to allow this? Neighbor's friend left me his number. Send Mail IM
MrTrucker	Sex With Neighbors Anybody wanna be my neighbor? Send Mail IM

Testimonials

deepthroatswallower

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.

Other Topics

Interests