My step-mom is fairly mature at 47-years-old. But nonetheless she is a very sexy blond who I am very attracted to. This of course made me very nosey and want to sneak into her room and take a look at her stuff. To my surprise it did not take long until i found her stash of sexy underwear and lingerie. My first instinct was to smell it all and it sure did smell good, the smell immediately made me pretty horny, so i began to masturbate. After i came i quickly put everything back where i found it and left it for a few days until i had the urge to go again. This time i stripped fully naked to masturbate and in the heat of the moment i slipped on a gorgeous black piece with pink frills. It felt so nice, tight, soft on my skin and i was satisfied straight away. Just knowing my sexy step-mom had worn this made me want to cum. Whenever i was home alone i would be straight in there to try on something else and have a tug. In total there are 3 all-in-one lingerie pieces, a set of stockings and a corset, (I am yet to wear the corset as it is difficult to put on alone). After a few weeks of this i just wanted more. I wanted something different. So i went searching again. This time i had hit the jackpot. The toys. In her bedside cabinet is a 10 inch dildo, a butt plug, a vibrator, lots of lube and what i later found out was an anal speculum. Who knew my step-mom was this much of a sex freak! So i used her lube, sucked her dildo and used her vibrator on my balls. It was unbelievable, total sexual satisfaction. I was yet to try anal and i thought that with what i had found i may as well give it a go. So i slipped a condom over the dildo, so she wouldn’t find out, whacked on a load of lube to the dildo and to my asshole and managed to squeeze it up there. At first it hurt like a bitch but it was worth it as it feels amazing. Now it slips up there with ease and i often use it whilst wearing the lingerie on omegle. I must stress that i am a straight 18-year-old boy but this is my fetish and i love it. 6 months ago
It first started for me when I was 11 years old, and home alone sick from school. I was snooping around in my mom’s room and I came across this really cute little pair of silky bright red satin string bikini panties. I loved how the smooth red silky material felt on my hands, so I just had to try them on. In a matter of seconds I was stripping off all of my boy clothes and sliding my mom’s little silky red panties up my legs. They felt so amazing and they fit me just as good as they fit my mom. She was quite a small, fit, and attractive woman (5.5”, 110 lbs, 34B bra, size 5 panties). She was also fairly young (only 19 years older than me, so she would have been about 30 at that time). This began a longtime love affair with her panties, lingerie, and eventually all of her clothes. She had lots of sexy, silky panties and hot lingerie, which the panties and lingerie were always my favorite part. She was also more of the miniskirt and high heels type, so she had lots of sexy outfits to try on too. She caught me in her lingerie and panties on many occasions, and eventually told me that I did not have to sneak around and that I could wear her things if I wanted to do so. It continued on until I was about 15 years old, and by then I was growing up and getting bigger, and her small clothes would not fit me any more. I gave it a break for a bit, but then started to buy my own lingerie and panties several years later. I am currently and have always been a straight man, but I guess indulging a bit in crossdressing is the way that I get in touch with my feminine side. 16 months ago
It was my tenth birthday and no one was in the house. I wanted to try something new, so I went into my parents room and straight to my Moms dresser. Opening it then undressing I picked out a bra and while I was digging around I found some silicon breast forms. I also pulled out a thong and garter belt. Slipping the thong up my legs I waslooking at the clock to see how much time I had left. After a few minutes of struggling I got the bra on and fit the breast forms in. I looked at myself in the mirror It looked like I actaly had breast and some very sexy cleavage. I rapped the garter beltaround my waist and put on some black fishnet leggings. Digging around some more I found a corset and tried to get it on. After a few minutes I gave up and set it on the bed. As I looked through the dresses I found a little black dress. After I slipped that over my head I spoted some thigh-high,5-inch heel, sitleto boots. I zipped them up my legs and walked up to a full body mirror. I looked super sexy, other than the bulge known as my stomach. began posing and I lost track of time. I Hadn’t heared the front door open, or seen my Mom walk up the hallway. I did a spin and saw her standing in the door way with a mischevies smile on her face. I stoodthere in horror as she stepped into the room, closed and locked the door with a key, and face me.
She said, “There’s three things wrong with this look, one you dont have any acsesories, two no make up, and three that bulge. I can fix that.”
She ordered me to take the dress off. Which I did. She picked up the corset and wraped it around me. Securing each notch, she began to pull the ribbons tighter and tighter. Before it was tightened it was realy tight, but after it was almost unbearable. She then proceeded to doll me up with make up and jewlery.
That night my friends were suposed to come over and spend the night, and with a few calls, she cancled. Instead she called all the girls I knew including the girl I liked. She then took me to the salon, still wearing the outfit above, to get my already neck length hair pink highligths. 3 years ago
How I did it: I simply sneaked into Mom's bedroom. As soon as I put on her bra, panties, pantyhose, high heels, and makeup all my nervousness went away. I really enjoyed the comfort and excitement of being dressed that way.
I was walking on air as I walked around the basement. It was heavenly. Iwas on cloud nine until I walked out into the laundry room right in front of my mom.
Read how I did it… 4 years ago
I am a male. One day I came home from high school, my mom usually got home 90 minutes later after picking up my sister at the bus stop.
I went to my room and undressed. I walked into my mom’s bedroom. I opened her dresser and retrieved a white lacy bra, and matching panties. I put them on. I grabbed a pair of my mom’s tan colored pantyhose. I slid them onto my legs. They felt heavenly. I then got a pair of my mom’s high heeled sandals. I put them on. I put on my mom’s makeup including lipstick, eyeshadow, eyeliner, blusher. I put on one of Mom’s pearl necklaces and bracelets. I admired myself in the mirror. I liked what I saw.
I decide to walk to the basement to see how my high heels clicked on the cement floor. I walked around. I went to the phone in the hallway by the outside door. I walked back and forth pretending I was on the phone. I apparently lost track of time. I was still holding the phone pretending to talk as I walked out of the hallway area around the corner into the laundry room. As I did this I walked smack into my mom who was only 4 feet away coming toward me.
She was startled as was I. Then she was shocked at seeing me wearing her bra, panties, pantyhose, high heels, and makeup. She said “Ted, what the heck are you up to?”. Needless to say I had lots of explaining to do. She went upstairs. I waited 10 minutes then I went up. Mom said “Ted come here and explain what you were doing wearing my clothes, NOW”. I told her I was going to talk to her after I changed. She said “No, you wanted to be dressed like that earlier, you can stay dressed like that while you sit here and talk to me.” I had to sit there wearing my mom’s clothes while I answered all here hundreds of questions, what, why, how long, how often, etc.
To add to the embarassment, shortly after we began talking, my sister walked into the livingroom to see what all the fuss was about. Mom told her all about it, then told sis to sit down and listen while I talked to my mom all about it.
What could I say, the obvious already was known. I am a crossdresser. After that my family knew it too! 4 years ago