I was 12 when I first wore my mothers underwear. I’d been born
In the 1950’s so it was the 60’s and she wore a lot of what were called foundation garments, corsets to you and me.
My dad had walked out on us when I was 5 and contrary to what you would expect my mother was not that close to me. Don’t get me wrong she was a good mum but not loving.
That’s why started the cross dressing I think I felt closer to her that way.
Fortunately my dad was rich and looked after us well so my mum had enough underwear that she didn’t miss the odd item that found it’s way into my room.
I started just wearing bras and panties or corselettes and panties and only for short times to begin with. My cock would get really hard and I would wank my self in front of a full length mirror and imagine I was fucking mum.
Then I got braver, I wore mums things under my own clothes. During the winter if I didn’t have pe or sports I would dress in corselette with suspenders and stockings and panties under my school uniform. No-one noticed but I had to wank at least twice during the day because my cock got so hard.
As the years passed I progressed to wearing mums dresses or skirts and blouses, again she didn’t miss them, she had loads. I would borrow her wigs and make-up and this being the 60’s I had long hair which I could make very feminine.
By the time I was 16, I dressed like a woman, looked like a woman but felt all man. I was very attracted to women but had only been out on dates and hadn’t progressed to any sex except my wanking sessions.
Then the most important day of my life. I was in my bedroom wearing a black wig, heavy make-up, black mini dress with black bra, black suspender belt and black stockings, no panties because I was wanking and had slipped them off.
I usually heard the front door go but today I was too far gone and had just shot my load when my bedroom door opened.
“who are yo…………. Oh peter is that you?”
I was speechless I didn’t know what to say. I eventually stuttered, “ yes, mum.”
“ oh well this is a surprise, are those my clothes?”
“yes mum sorry I’ve been borrowing them.”
“and more if my eyes are correct.”
She pointed to the obvious cum stains on the front of the dress.
I reddened, “yes, mum, sorry.”
“Oh don’t worry it’s nothing a wash won’t sort out. So how long have you been doing this?”
“ Since I was 12, only your underwear to start with then it got a bit addictive.”
She came over and sat on the bed next to me and put her arm round my shoulders.
“well love truth be known I’ve always wanted a daughter so now I have the best of both worlds.”
Mum had 44dd breasts and as she pushed against me I felt my cock rising again and with no panties on the dress rose too.
“Oh I see you like that,” said mum as she saw my erection.
I said nothing.
Then she really surprised me. She took off her blouse and skirt, slipped off her full length slip and undid her black full length bra releasing her majestic breasts.
My insides did summersaults and my cock grew another inch. She pushed my dress up to my waist exposing my rampant member and pushed her breasts down so my cock was between them. I’d never felt anything like this as she used her breasts to rub my cock. I shouted that I was going to cum and she lay on the bed and said, “ cum on my tits.”
I did, I came everywhere her tits, her face, the bed, the wall and the floor.
“oh goodness.” said mum, “ what a load, lets lick it up.”
Now I’d never even thought of tasting my own cum let alone eating it but soon we were lapping it up and swallowing it down. I loved the taste and when mum clamped her mouth over mine and our tongues entwined we swapped cum and swallowed more.
I was getting hard again and mum felt it.
“oh my.” she said, “ I’d forgotten how quickly you recover at your age. So have your ever had a blow job?”
“Well a girl at school said she would give me one but when she saw my cock she chickened out, so no.”
“well I won’t let you down, lie on the bed.”
I did as I was told and watched as mum removed the remainder of her clothes.
“ we’re going to do a 69.”
“what’s that I asked innocently?”
“I sit on your face so you can lick my cunt and I suck your cock.”
I was shocked to hear mum say cunt but knew what she meant.
She straddled me and I saw her juicy cunt descending onto my face. At the same time her lips sucked the end of my cock and she slid the whole length into her mouth, it was wonderful. I began to lick her cunt and found what I now know is her clitoris I sucked it and tasted her love juices as they poured into my mouth. She was moaning and writhing onto my face, she sped up the sucking of my cock and we both yelled that we were Cumming and I shot another load this time deep in her throat. She came and poured more thick love juices into my mouth and I swallowed them down. I kept licking and mum kept sucking until we were completely exhausted and collapsed onto the bed.
We slept and when I woke mum was not there. I went downstairs and found he in the kitchen.
“ so love have you been out dressed as a girl?”
“no.” I said, “I couldn’t do that someone might recognise me.”
“well I hardly recognised you and if I put your wig and make up on I can make you look like a different person then we can go shopping together.”
“why do we need to go shopping?”
“because we have to get you your own clothes. I don’t want any more cum stains on mine.”
“but mum I like wearing yours they smell of you.”
“well I’ll wear your new stuff for a couple of days then you have them, ok.”
I said ok but wasn’t sure but after I’d showered mum called my school and said I was sick. She then set about my transformation. First she put my make up on. Less heavy handed than when I did it and when I looked in the mirror a girl I’d never seen before, stared back.
Then clothes. The main problem was the size of my mums tits she’d told me that I would look better as a 38d so she blew 2 balloons up to fit in the cups of the bra I had put on. The bra was a bit loose and the balloons didn’t fill the cups but she said it would be better when we got clothes to fit me.
It was. We shopped all day I bought bras, suspender belts, panties, slips, corsets and corselettes, girdles and stockings and tights for wearing with extreme mini skirts.
Then blouses and skirts of all different lengths, tops, jumpers and dresses, for casual wear and some really nice formal dresses.
We also bought me 6 wigs and a huge amount of make up. Then we drove to a part of town I hadn’t been to before and pulled up outside a shop with no sign above the door.
Inside was a sex shop. I didn’t know such places existed but mum had obviously been here before. She picked up some dildos and a vibrator, then a pair of artificial breasts 38d, we went in the back and I removed the balloons and put the breasts in they were perfect. They fit the cups of my bra perfectly and the even bounced a little, I felt like a real woman.
So my new life with my mum began but that’s another story.