I said this before all my stories are real and actual encounters So it all…
Sexed up in mom’s underwear.
Sexed up in mom’s underwear.
I am a 26-year old smooth skinned, wheatish complexioned guy and love to dress up in my mother’s bra and panties on a daily basis, especially her “After Eden” panties, which are lacy and designed with little flowers and have a sexy trimming. I generally wear her bras stuffed with balls of wool, which give them a nice rounded look. Then I wear her panties and walk around the house with my hard on coming through the top band of the panties. Most of the times I also wear a tight blouse on top, which gives me a whorish look. I then masturbate as I fantasize about having sex with a bunch of cute looking, effeminate guys with smooth brown cocks and hairless bodies. I always use a thick candle, which I insert into my ass and pump in and out till I cum all over my mom’s panties. I have melted a rim around the tip of the candle so that it does not slip out if my ass. I use anything that is cylindrical for stuffing up my ass; screwdriver handles, toothpaste tubes, skipping rope handles, carrots, cucumbers, brinjals and bananas too. One of my favorite pastimes is to walk on the roof in bras and panties with a 6″ long cucumber up my ass, tempting the kids next door (they are twins) to see me. They must think I am weird but the thought that 14-year-old kids might be seeing me in this state really turns me on. I have even masturbated in their full view and then rubbed cum on my face and neck, all the time acting as if I don’t know they are there. It really turns me on.
One day I decided to carry out my ultimate fantasy of displaying my urge to dress in my mom’s underwear to someone who would be a complete stranger. I planned to drive down to the beach one evening and try to pick up a kid or two who I could convince to click my snaps while I was in the drag. I wore my mom’s cotton panties and lacy bra (which I stuffed with two condoms full of water) under a pair of loose Bermudas and tee shirt and took my digital camera and dumped two six packs of beer in the back seat. I also kept one black lace bra and a yellow thong for change. I was cruising down the road parallel to the beach, hoping that a cop would not stop me, when I saw a young teenaged boy looking for a hitch. I drew up next to him and was floored by his soft looks and the smooth legs coming out of his shorts. I opened the other door to let him into the front seat. As I bent over I made sure he saw my bra through the top of the tee. He started but then controlled his reactions and got in, all the time looking at my “breasts”.
I offered him a beer, which he accepted slightly doubtfully, it being his first time. Things were looking brighter because I knew that one beer for a first timer was good enough to drive away all inhibitions. The very thought that I was going to “come out of the closet” in front of a kid was so erotic that I could not help massaging my crotch in plain view of Roger (his name). He studiously avoided looking at my crotch but could not control the reactions of his cock to all this stimulation. Roger drank up his beer like a pro and had uncapped the second one before I could even finish half of mine. After making a lot of small talk, during which Roger was continuously staring at my “boobs”, I decided to go for bust and strip down to bra and panties. Complaining about the heat, I slipped out of my Bermudas and pulled of my tee. Roger was literally zonked out of his mind as he saw my hard on out lined against my mom’s cotton panties and the beautiful lacy bra, but the beer made him braver: he blurted out the first thing that came to his mind, “Ooh! They look so sexy! Can I feel them?” I nearly fainted with pleasure as he moved his soft hands over my mom’s bra and onto my panty encased hard on. I moved my hand to his groin and took hold of his cock, which was rock hard. I had to stop the car and blow Roger; I felt the desire to behave like a slut. All this while Roger was trying to smell the panties. I knew that I had touched a nerve in him seeing his reaction to the women’s underwear. I handed him the black bra and thong and two balls of wool; in a jiffy Roger had become Regina and was on top of me looking like a cute girl with a bob cut. I told him that I wanted him to take some pictures of me and he agreed without taking his tongue out of my mouth and his hands off my “tits” and cock. I wanted this moment to last forever, with our breasts rubbing each other and our cocks straining to get out of my mom’s panties. We went home, got onto the roof, changed into all the panties and bras available at home one by one, clicked away to glory and brought ourselves off to amazing orgasms. My ass was already adjusted to penetration so it was not difficult to take Roger’s 5 inches in side me, but Roger was no sissy; one look at my 7 inch rod and he was drooling all over it. He straddled me and slowly settled down onto my rod and started riding me like he wanted me to cum all the way into his throat. We slept in each other’s arms and woke up wanting more, but I had to wash all my mom’s underwear because she always smelt them before wearing. If they ALL did not have the freshly washed fragrance, she would surely know. So that was all for the day.