I've always been a closet cross dresser since as long as I can remember, when I first hit puberty like any other young boy my hormones were on a rampage but not in the typical way sure I enjoyed looking at women attracted to they're breast like a moth to a flame, the shape , the bounce I loved it all looking for hours at the lingerie pages of the Sears catalog was a favorite past time of mine and other pubescent teen males but my interest was different I envied women for being able to wear all those sexy bras and lingerie and I had an equal obsession with stockings and panty girdles as well.
So, one summer day my mom who I loved dearly a much kinder gentler nurturing soul than my asshole macho old man tasked me with an important job. I was more than willing to help her and asked what she wanted me to do. She said she wanted my help painting her bedroom and I would have to move all the furniture out and put it into the spare room, I agreed and told her I would take care of it. She suggested for me to take all the draws out first so everything would be easier to move made sense.
I started on my task and low and behold I came across her underwear draw. This was like hitting pay dirt for me, I had struck gold she had a collection of bras that I had no idea she ever wore and how would I. Long line bras, lace bras see thru bras my young cock was as had as a rock but when I came across her bullet bras I instantly could feel my cock pulsing and I now had a whole new image of my mom she was one hot sexy lady. Seeing pictures of her when she was growing up, I instinctively knew she had to be wearing some of these bras in those photos it was of course the style back then.
So, the overwhelming compulsion to try one on was more than I could handle, and I succumbed to my lust. I peeled off my white T-shirt and slipped one on and fought like hell trying to fasten the clasps behind my back, then I got the bright idea to slip my arms out of the straps and turn it around and fasten it in front then spin it around and slip my arms through. Something I see my own wife do as well as many of the women I've been with.
I admired myself in her full length mirror and the large mirror that was on her dresser, I looked hot in my book but my breast were somewhat lacking so I looked for something to stuff the cups with I rummaged through her draws and came up with some white cotton socks that I knew she wore when gardening and working outside. I succeed in filling out the cups of the bullet bra which by the way I still have to this day locked away. Well I looked good but not quite good enough, so I rummaged through some of her other draws until I came across her panty girdles.
My God! she must have had twenty or twenty five of them. I found a black one that looked like it matched the bra and removed my jeans and started to slip it on over my tighty whitey underwear and thought no this isn't how you look like a women stupid and slipped them off kicked them to one side of the room and stepped into the girdle and pulled it up wiggled my hips as I pulled until it was finally up just over my tummy just as I had seen in the pages of the lingerie section. I once again admired myself and I looked even better but still not complete. Stockings! I needed stockings I continued my search and instantly found them a pair of nude seamed stockings I slipped them on and the sensation of the nylon against my legs was indescribably euphoric.
I took care not to tear them and sat on the big wing backed chair my mom obviously used for dressing and slowly rolling them up until they were fully up my thighs and I clasp them to the garters hanging from the bottom of the girdle. It took me one attempt and I had them all hooked up, little did I realize back then but looking through the pages of the Sears catalog lady's lingerie section was in a way a cross dressing training manual for me. I went for the total look and tried on a pair of her heels which fit my feet way back then but when I tried to stand and walk, I almost killed myself. Looking back, I could just have imagined tripping hitting my head being knocked unconscious to be found that way funny now but a horrifying thought back then.
So, I decided to admire myself wearing the heels by laying on the bed striking different poses. I looked much better now I looked hot, being a kid of the 60's I had long hair just like everyone else, I grabbed mom's big silver brush and brushed my long auburn hair as close to her style as I could get it. My mom and my aunt often comment I had beautiful hair and that girls wished they had hair like mine, an added bonus. I took one look at myself in the mirror and could instantly feel my cock straining at my girdle. I lay back down striking a few more possess and almost as if on auto pilot my hand reached under my girdle and I found my now leaking precum cock.
I was amazingly hard truly something to be admired by both genders and sexual orientations. I began stroking and squeezing my balls and I increased my pace until I was feverishly pumping it and lifting my hips off the bed as if I was trying to meet an imaginary lovers' thrusts. I orgasmed for what seems like fifteen minutes continuously pumping cum from my balls until I collapsed in an unexplainable euphoric erotic state of completion. I knew right then and there I was destined to be as much of a woman as I could possibly be but living in that time period in the part of the country where I grew up I most likely would have been lynched or beaten to death by all the redneck asshole s who I wanted no part of anyway.
I was laying back fantasizing about being fucked by a man when all of a sudden, the phone rang, and it seemed it was even louder than ever as it was an alarm that I had committed a crime against nature and would be dammed all to hell. When I reached for the phone it was then I realized I had a right hand full of cum and fumbled for the phone with my left hand. When I answered it was my mom on the other end of the phone and I instantly felt guilty as hell and wanted to undress as fast as possible.
Why? I now ask myself but just a guilty teenage boy reaction, I guess. She asked how my job was going I said fine mom almost have the room empty total BS I was barely started. She said that good sweetie I'm not coming home the regular time I'm working overtime and then I'm going out with your aunt Martha, so I'll be home late. She told me to fix myself something for dinner there was always plenty in the frig. I told her id be fine and then I spotted the big wet stain on the comforter and thought oh fuck! Ah mom I spilled something on the comforter she asked what not paint I hope I said no something I was drinking (I only wished I was drinking cum).
She said that's ok take it off the bed and I'll wash it when I come home. I protested and said no I'll do it mom she said your such a good boy, (right now a bad girl maybe) She gave me instructions and I stripped if off the bed and went about washing it. The funny thing is I didn't even think about removing any of my garments and walked freely though the house and down to the laundry room and did the wash came back and finished cleaning out the room the entire time dressed in my sexy outfit. I made myself dinner dressed sat at the dining room table ate and then and went about finishing up everything I was tasked to do and figured it was time to get undressed but not before one well deserved wank.
This time I lay on the couch, closed my eyes and thought about my fantasy lover fucking my brains out like I had heard my older brother and cousins talk about to local floozies. I came in one gigantic explosive orgasm but this time I was prepared with a towel to clean up my mess. I reluctantly removed everything being careful to place things back where I remembered they came from so as not to be discovered. I gathered up my boy cloths and went and took a shower got dressed and sat down watching TV.
About an hour later I heard the door open and my mom called to me when she walked through the door. She kissed me and said well how'd you do, I just said check it out I had her bedroom totally cleaned out molding all taped floors covered ready to go. She smiled and said great job I'm off tomorrow would you mind helping me paint, without hesitation I responded sure mom no problem even though in the back of my mind I was supposed to go play ball with my friends but never being one to disappoint my mom I decided to forgo sandlot baseball for a chance to spend the day with mom. She said ok time for bed, then she laughed and said well now this might be a problem as her bedroom was empty and the spare room was full of her furniture.
She said oh well looks like the couch for me tonight. I blurted out why don't you sleep in my room mom, Chuck is away at school, she smiled and said sure why not. I went upstairs to get changed and hopped into bed. When my mom walked upstairs in stood in the doorway, she was wearing a white linen nightie that was backlit by the hall light and I could clearly see the entire outline of her perfect body especially her large pendulous breast being the tit man that I have become she was at least a 38DD or better and her nipples were poking at the thin material.
Her breast were my fixation for as long as I can remember and probably the reason for my love of large breasted women. She got in my brother bed and pulled the covers up and then said it's too hot for a blanket and just lay on top of the sheets she rested her head on her hand and said so pal whats new. I was holy crap mom had that infamous mom radar shit working how the hell did she know. I stammered a bit and said nothing mom. She said well we hardly ever get to be alone to talk about stuff you know like girls, cars, sports. I was relieved oh wait mom what about me wearing your underwear the voice in my head said. Ah not much you know I gave her a quick rundown about so and so's brother got a new Chevy and this and that.
What about girls I said what about them none are interested in me sometimes I think it would be easier to be a girl than a guy you know mom. She laughed and said it's never easy being a teenager, the entire time my perverted little mind had me staring at her breast imagining her wearing those pieces of lingerie I had come across. What I wouldn't give to see mom dressed like I was. She said ok bud time for bed we have a long day tomorrow, but we'll have fun.
Morning came and mom was gone downstairs making breakfast, she called to me form the bottom of the stairs, breakfast sweetie Ok mom be right there a few minutes later I headed down to the kitchen and sat down to eat with mom a treat I didn't get to do alone hardly at all anymore. After breakfast she said well you did a great job in the room, we're ready to go and you washed the comforter and hung it up to dry nice job, I said thanks mom.
Then she looked at me and smiled and held up the black panty girdle and said if you're going to wear my stuff you can at least wash it. I was dumbfounded one freaking time and I got caught. I hung my head and said I'm sorry mom I won't but before I could finish, she said its ok sweetie I understand. I looked up trying to fight my shame, she said no really its ok and came over and kissed me on the forehead. Look you're at a very confusing age right now and your mind has no idea what your body is doing so I'm ok with you experimenting as long as it's in the privacy of our home and you keep this our secrete. I said ok mom our secrete I swear.
She said ok now let me show you how to wash this. Ok mom and we headed for the laundry room I said wait and ran back to where her dresser draws were piled up and retrieved the bra and stockings. She smiled and said my, my! you must have looked sexy I just put my head down in embarrassment she said hey your my kid you had to have look like a million bucks.
We went downstairs to the laundry room and she held up the bra saying you have good taste like me, this was one of my favorites. I looked and said was? inquisitively she said I'm an old married lady I don't dress like that anymore. I said I bet you still look great mom. She said well your father doesn't seem to think so anymore. I wanted to say that's because he's an asshole but held my tongue as I was taught. She smiled and said thanks bud maybe we'll see one of these days.
She proceeded to teach me the proper way to was lingerie such as the bra and cum stained girdle I had worn. We then went back to our painting project, I was busy working when she said I'm going to make us lunch, it will be ready in a few minutes. After about fifteen minutes she called to me to come for lunch but make sure you go wash up first. I went into the bathroom there hanging on the towel rack was a blue shiny satiny top and shorts. She called did you find them, ah yes mom I think so, I answered back she laughed and said well put them on I want to see how you look. I did as my mom had requested and put on the outfit.
When I came out my mom had a big smile on her face said my you look cute, then she tugged at the top and adjusted it so it fit properly and when she adjusted the shorts, I could feel my member starting to grow. She said oh these will not do tugging at my white cotton briefs. She said follow me and we went to her pile of draws in the spare room and she rummaged through her panty draw and pulled out a pair of nylon bikini full back panties she said here put these on, she watched as I sat on the bed and slipped the shorts off and pulled off my underwear and I thought my now less than flaccid cock was going to spring to attention, so I quickly pulled up the panties and adjusted my manhood, she laughed and said that's something I never have to worry or be embarrassed about and handed me the shorts and I slipped them on. She smiled and said much better now let's go have lunch.
While we were eating, she asked me how I felt. I said good mom actually she said great, so you feel sexy I said yeah, I guess. She smiled and said it can be fun being a girl you'll see. I smiled and said yeah, I guess it can be. Mom said let's finish putting the room back together and then figure out what us girls want to do tonight. I worked tirelessly the rest of the day dressed as my mom had wanted. She was wearing a similar style pair of black shorts and a white top tied up, so her belly button was exposed.
As we put stuff back and hung up pictures etc. She said so you think your mom still looks good. I said heck yeah mom your gorgeous, all my friends think your pretty too. She smiled and said oh do they now I said yes mom they do. Hmm your making me feel really good sweetie. I said your welcome mom. Ok let's finish up so we can find something fun to do, how about I do your hair later. I said my hair she said yeah, it's something girlfriends do to each other. I said ok sure why not. Thinking to myself wow this is unbelievable. I worked as fast as I could to get everything finished in anticipation of what lay in store for me.