Cute guys & boys crossdressing (gallery)

[Betty]

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[Angela M...]

Thanks Betty, I always love these pics, they bring back some memories of when I got caught in panties and other girls clothes. Those times were by accident as I was not paying attention to my surroundings. The other time I was out in public in my sisters clothes was one Halloween and I wore her red tights, a short dress, my mothers wig and my sisters Mary Jane shoes. I loved every minute of it but was scared somebody from the area would know it was me.  I guess that never happened as nobody ever said anything later on. My sister was good about it too and never told my parents about it.
There was one other time I was caught off guard by my doctor. I had worn new white girls boy shorts underwear with a shiny elastic waistband when the doc said I needed  a shot. I started to roll up my sleeve when she said bend over and drop your pants. I am sure she saw the shocked look on my face as she said don't worry I won't hurt you. I dropped my pants and undies at the same time so as to hide the girls panties but she smiled as she helped me pull them up so I am guessing she noticed. She was always very friendly with me on our visits for several years and gave me shots on other visits too but I was always careful not to wear panties again. I have a new doctor now and see her next week. I wonder how she would feel about seeing me in panties? Has anybody else been caught off guard like that?

[BillieJo]

Why Angela, just yesterday I was caught off guard. I had to see an orthopedic doctor for some hip problems I have been having. He put up on his computer some x-rays that were taken about five months ago. I was surprised back then that I would be having x-rays taken that day. When I went to radiology I asked if I needed to take my pants off and the technician said "no, leave your pants on". I most definitely would have to have taken my pants off years ago. That gave me a great sense of relief at that time because I was wearing panties that day. White, cotton panties to be exact.

Fast forward to yesterday. When we looked at the X-rays of my hips you could see the outlines of my panties. Only the leg bands and the waist band showed but it was unmistakable that what we were looking at were panties. The doctor gave me a sideways glance but otherwise did not say anything. Seems the waist band and leg bands were just dense enough to absorb some of the x-rays but they could be seen quite clearly. Yes, I as quite embarrassed because I'm sure my ortho knew what was on the screen.

[Angela M...]

Hey BillieJo, you just reminded me of another time that I was caught off guard. I was sent to the hospital for a scan by my doctor when I hurt my back. He said go over first thing in the morning and they will scan your upper back and neck so off I went for an early appointment but I was not sure how long it would take and if I would be a long time so I wore a diaper and plastic pants with four snaps down each side at the front. They were new from Suprima and I loved the soft feel and the way they looked with the shiny metal snaps and thought as I was only going to have my upper back and neck done it would be fine. Well the girl doing the scan told me to take everything off but my underwear and put a gown on. The doctor had called and ordered a full body scan. I was nervous but figured in a gown I would be OK and I was careful to make sure the back was closed as I got on the table. As the scan slowly progressed down to my waist she stopped at my hips and said "If you need to go to the bathroom I can stop for a bit". I said I was OK and she said alright I guess your protected enough. I was taken by surprise until I looked over at her monitor to see that the shiny metal snaps were quite obvious to anyone and she knew what I was wearing. I lay still until done and then she smiled as I went into the change room. I never even thought about the snaps being so visible on screen. As I was leaving I asked if they would send the report to both my doctors and she said they would view the whole scan on their computers. Later when I got the results neither doctor said a word about what I was wearing but my family doctor asked if I was still seeing my urologist so he might have thought I was in need of protection.   

[Betty]

Never been "caught". But there we many close calls & near misses, were I missed getting caught by only mere seconds. As a kid that was terrifying because getting caught would have meant getting the crap beaten out of me along with lots of other punishment for a very long time.

Our new background image brings back memories. The only times I was able to wear girls stuff outside was in back of Buffalo's old huge Central Terminal railway building... a massive structure the size of city hall, but abandoned for years back then. It was only a mile away, so within walking distance.

Most of my crossdressing as a kid was inside the abandoned building. It was so huge, one could get lost in it, & there almost never was anybody else around. For years I'd hide my sissy stuff in a room on the upper floors, & nobody ever found them. Outside in back, there was nobody around most of the time except an occasional passing freight train.

As a kid, I have struck that pose in the background, a few times on the railroad tracks in a dress & tights. At home with 6 kids & 2 adults under the same roof there was no privacy at all. All of us shared a small room with at least one other sibling. Mom also had an interesting hobby of thoroughly searching all the kids room & stuff almost every time we were at school or not around. She left no corner, object, or hiding place unsuspected almost daily.

BTW, if you are visiting on a mobile device, you don't see the same background we are. Our mobile feed is a separate site & view with a different background, but just shares the same database. If you see a "Mobile Home" button near the top instead of a "Home" button, you're viewing our mobile site. We automatically detect if you're using a mobile device, mobile OS, mobile browser, or a mobile data connection, then automatically send you the version of our site that is specially designed for small mobile touch screens (I made that).

So every Betty's site is currently really 3 separate sites online. The regular site, the mobile site, & a backup site.

[Betty]

Full sized tablet & big phone mobile feed view:

[Angela M...]

Hey Betty, I like this background. When I was younger about age 10 or 11 if my memory is still good, I would stash my girl stuff in a box in the basement workshop. I didn't have much stuff then but I was hooked on plastic panties and had a few pairs and some tights of my sisters. Like you my mom would be all over the bedroom most times and I did not dare stash things there. I would mostly try on my girls panties tights and leotard down there along with a skirt borrowed from my sisters room and would pose and dance around for quite awhile if nobody was home. I did make one mistake though having worn some plastic panties, the leotard and tights to bed one night and as I got up late for school I stashed the clothes under the mattress. Big mistake as mom changed the beds that day and those things of mine were waiting on the bed for me when I got home. I got a stern lecture and mom took away my things. All night I was waiting for dad to nail me about it but after going to bed that night and waiting again, nothing was said and I was so relieved. Mom said nothing either but I never saw those clothes again and the skirt was back in my sisters closet next day. I was careful after that but some time later I did the same thing and then it hit the fan. My mother took my all panties and tights and burned holes in them with her cigarette and hung them on the basement clothes line for dad and my sister to see and of course I got a visit from dad. I will never forget that as long as I live. I was so mad and betrayed as she had said nothing the first time. Of course that did not stop me from wearing my things and she would know because the tights ran where there were holes in them. I just hung them back up when I was done until they were gone one day.
I just remembered one other time I came so close to being caught when I was 10. I had a crush on a neighbor girl who was the cousin of my friend and while at his house I spotted the red tights she had been wearing the day before just lying on the bedroom floor. I got excited and scooped them up and went to the bathroom where I put them on. I was already wearing pink plastic panties and the feeling of both just was electric. Suddenly my friend was banging on the door to hurry up they were leaving so I figured I would leave them on and put the tights back later. We all ran outside to play games like hide & seek and chase and over the next hour I was getting wet and excited until the girl I had a crush on tackled me to the ground and sat on top of me. I think she also had a crush and she was tickling me and trying to kiss me, then somebody got the idea to strip me. I was horrified as they pulled my shirt up and started to undo my pants and I started bucking and swearing and trying my hardest to get away. I did not want to hurt her but I did not want her to see what I was wearing either so I tossed her off and got up and ran with everybody chasing me. When I got to my house I was in the door like a shot and locked it behind me. I was panting away and my face was red and sweating. They all went away when they figured I was not coming out and I was up to my room to change before anybody saw me. Now I had to figure out how to return the tights without getting caught but I figured as his mom was not a fussy housekeeper like mine, I could just drop them on the floor the next day. I got some flack from my friend for leaving and swearing but when I went into his house the next day, I asked where his cousin was. He said they left in the morning because her dad got an apartment for them so now I had a pair of tights under my clothes again that I could not return. As his sisters room was still a mess I took them of in the bathroom and dropped them on her floor behind the door. They would think she had forgotten them so it was Ok. A day or two later I wished I had kept them as I bet they would not be missed.

[Angela M...]

Would love to hear anybody's stories of almost getting caught or just what they first started wearing when they were younger as I am sure we all started at a younger age trying on things we found or borrowed. I got hooked on plastic panties because my friend who was a bully, told one of our younger friends that if he wanted to play with us he had to try on some plastic panties that were his baby brothers. There were always some hanging in the bathroom and he eventually went in and got a pair and came back in the bedroom. He said he was only going to wear them over his underwear and after he got them on my friend said he had to keep them on while we played. I liked the look and went into the bathroom for a pair but they did not fit me. He then put the boy over his knee and started to spank him with his hand. He was not being light either and I told him stop or your mom will come up and throw us out. The younger boy jumped up and took of the panties and put his shorts back on and left crying. This just started my friend laughing and I told him he was a bully and I went home too. We lived next door so he came over later and asked if I was going to be a suck or was I going to play with him and as he had all the cool toys and a huge tree house, I said I would. We were often together even though I did not like him very much but our parents were good friends and we vacationed together so we were pushed together often and he did have all the cool things. His mother never checked on us when we were playing in his basement but warned us never to touch his dads tools and for the most part we did not. He had a sadistic streak though as you read in the previous post and often I would end up being tied up and teased. As I kind of liked being bound up, I did not stop him too often unless he got real rough. Sometimes he would tie me spreadeagled under his dads massive pool table with my arms & legs bound to each table leg and he would really stretch me out good. He would pile all the couch cushions under the table with me on top so I was almost touching the underside of the table. Then he would tie my arms tight and move down to my legs where he would pull the ropes as tight as he could stretching me out till I was begging for him to stop.  Then he would pull all the cushions out from under me which left me hanging inches from the floor. The table had a long cover over it so nobody could see I was there and he would go up to the bathroom or get drinks and just leave me there for what seemed like hours. Then when he came back and I was begging him to untie me he would pull my pants down and pinch my butt till I was almost in tears. I don't really know why I would let him do these things but his mother was so nice to me and must have known what he was like because she often said she was glad he had me as a friend as not many other boys would play with him. I knew why but never said anything. When we got older we grew apart but his parents and mine were lifelong friends and I took care of her as well as my own mother when they were older.

[Betty]

Found some more cool stuff to post/repost.

Enjoy!

[Betty]

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