Dressing With An Old Friend

by Malcolm (UK)

It was 1970s I was 18 and a bit of a loner. I had tried without success to find a girlfriend but always felt inhibited and awkward around girls, lived with my parents and had a secret, I was a closet crossdresser.

I had gotten into when messing about with my school friend Steven round at his place. We had tried on some of his sister’s bras and panties. It got as far as jerking off together.

We did it a couple of more times until he went to another school and we lost touch. I hadn't seen him since we were 13. I continued to sneak my sister's undies and even tried on dresses when everyone was out.

I was in town with nothing much to do when I bumped into my old friend. We went to a cafe and chatted about old times but neither of us mentioning 'that' subject. He now had his own place in town and I accepted his invitation to go see it.

It was a nice flat above some shops. As we chatted I wondered if I should say something. He hadn't so far, maybe he had forgotten about it.

'Do you still wear panties?' he suddenly blurted out.

'Yes' I answered relieved to have it out in the open.

'Me too' he smiled and we both giggled.

'Follow me' he said and led me into a bedroom.

It was decorated in reds pinks and lilacs rather over the top with drapes and cushions on a large bed. He opened a drawer full of panties bras and other lingerie. On a dressing table I saw makeup, powders, lipstick and so on.

I was agog at all this stuff, like I had entered another world.

He watched me smiling. 'Well what do you think Malcolm?'

'It's amazing' was all I kept saying.

He laughed 'So do you want to dress up with me?'

'Oh yes I'd love it'.

'Good, let’s get rid of our nasty male clothes' he said in an effeminate voice.

I followed suit 'Oh yes, horrid rough boy clothes, Yeuk.'

As we undressed I realised Steven had been wearing black panties stockings and suspenders all this time.

When offered I chose a bra panty suspender set in lilac. We giggled as he helped me dresss, both of us now had erections and we made jokes about it. Steven put on a shiny black cocktail dress.

He took out pink satin frock suggesting it would suit me. The time just flew past as 'Stephanie' as he liked to be called did our makeup. The crowning glory was when 'she' produced two wigs, a black bob for him, and blonde curls for me.

'I think your more the sissy type malcolm' he observed .

I had never thought about the different aspects of crossdressing before but I realised Stephanie was right.

'I used to have another sissy girlfriend but she moved on' Stephanie said as she took out a chain choker and fastened it around my neck. I stared at myself in the mirror and the word sissy now adorning my neck.

Stephanie kissed my neck and ran his hand down my front stroking my crotch.

'Wait here a while' he said and disappeared into the lounge. I thought I heard her on the phone. I was left to revel in the transformation I had undergone. I fingered the collar and the metal 'sissy' emblazoned on it.

'I need a coffee, come through' Stephanie's call snapped me out of it.

I went through stepping carefully in the pink heels she had chosen for me. I paraded about a bit and then we sat and talked as we finished our drinks. Stephanie moved in close and kissed me on the lips.

'You're so pretty my sissy, do you like it?'

'Yes thank you, I've never dressed fully before.'

'Feels natural, doesn’t it?'


I was startled by the sound of the doorbell.

'It's ok, I've just got someone who'd like to meet you'.................

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Jan 18, 2021
Wishing NEW
by: Anonymous

I loved wearing panties and lingerie from my early teens. One of biggest fantasies was to have a friend to dress & explore with (sigh).

Sep 15, 2020
just reminded me of school days !
by: Anonymous

And ?

Aug 14, 2020
sissy dress up
by: Anonymous

loved the story but want to kmnow who was at the door more more 313-720=4287 lmk

Aug 08, 2020
by: Mama's boy

The same thing happened to me. My mother knows about my "borrowing" her panties and pantyhose. Finally she just bought me my own personal pantyhose and panties because I often left them inundated with my sperm. Mom's wet panties were so deliciously sweet smelling and I frequently got off really good sniffing mom's soaking panties and wearing her pantyhose. Nothing satisfies like the scent of my mom's pussy. Also her taste in luxurious lingerie is excellent and I quickly developed a naughty fetish for wearing smooth silky lingerie that my mom buys me now. Everyone says I have a hot mom and I agree. My friend who shared a cross dressing hot fetish loves to get off on wearing and acting all girly like when we are together. Mom quickly found out about my hobbies and says it's fine to accept my feminine feelings and likes my friend. In fact she saw us dressing up and kissing and decided she wanted in.

"You two "girls" look so damn hot". Mom's panties were obviously wet. She smiled and spun around modeling her own lingerie and mentioned how big I was getting. Mom's not getting much attention from dad lately because my sister is occupying his time.

Mom's vibrator however is getting a lot of use. Mom and my sister both have been dressing me up and femininizing me since I was ten. I used to be able to fit into their sexy panties and pantyhose but now at 18 my legs are very long and mom and sis have been buying me little gifts of expensive silky smooth panties and pantyhose. Makeup kits and various items of feminine attire followed. It seems so natural and right to dress "en fem". My mother and sister think I look adorable. Dad doesn't dare say anything because of his relationship with my sister. However dad mentioned how sexy she looks in her bikini. Dad buys her expensive lingerie and likes her to look hot. I often borrow her things to wear and like my mom's panties sniff and inhale the smell of wet pussy.

My "girlfriend" and I get together for sleep overs and have slumber parties. We go into mom's room and sis and mom offer beauty advice and often offer to apply makeup to us. Mom's really cool about me dressing up as a sexy girl and hints about being intimate with my girlfriend.

One night late mom caught us in a sixty nine. I was sucking my girlfriends sissy clitty while she was sucking mine. My sister was with dad and mom was feeling horny and left out. I was wondering how I would feel about letting my girlfriend be with my hot mom would make me feel personally and after seeing my mom's mouth around her sissy clitty I knew soon how things would go. I grabbed mom's vibrator and quickly applied it to myself. Mom immediately saw me get erect and smiled coyly. "Only a matter of time son". Mom's mouth and tongue worked overtime on my girlfriends clitty. I was really getting hot and my mom asked me if I'd like some. I was reluctant and shy but mother knows about my fetish and started caressing my silky legs stating how pretty I looked in the shimmering pantyhose and mentioned how nice my panties looked as she rubbed my sissy clitty through my pretty panties. I was all excited about the thought of having a three way with my own mother. My girlfriend was obviously enjoying the action. I was thinking about how it would look being with my mom in lingerie but my mother just assured me it was the thing to do. "Mom what are you doing to me"? I was in heaven. Mom was using language I never heard before. "MOTHER FUCKER" and "incestuous needs" was her expressions. "Dad's with sis" my mom uttered. "Take care of your mom's needs"! She continued you use kinky expressions I found myself falling into the unholy perverted session of lust as my mom uttered "It feels so good doesn't it?" I couldn't lie.... It felt great as my mom's hands explored our sissy clittys and she unrelentingly worked on her new GIRLY-BOYS to help encourage us to let go of any inhibitions or guilt about this hot interaction between her son and his "girlfriend"

My mother was sucking like crazy and imploring me to taste her pussy. I told her I had been sniffing her panties and my mom immediately spread her legs. My mother now was soaking wet. I longed to taste her juicy pussy. My girlfriend was telling me to "go for it"! She was licking my sissy clitty as my tongued my mom's pussy through her pretty panties. "My baby loves her mommy"! My conscience was holding me back....I reluctantly tongued some juice from my mom's pussy. So delicious....Mom implored me to continue. "Be mommys good girl and make mommy yours"! I was not myself as my mom's hands felt my legs clad in shimmering smooth pantyhose. She continued to use nasty language and called me her "sissy mother fucker".... I felt like now it was time. Mom said "Put that sissy clitty in mommy's cunny"....

My girlfriend was jacking off watching as I positioned myself into a place where mommy could grasp my sissy clitty and put it where it truly belongs

My girlfriend was masturbating and encouraging me to be a hot little bitch. I asked my mom if this was what she wanted. My mom nodded in approval

Her nylon clad legs locked around my waist. Mom led me inside of her incestuous wet sex.....Her eyes widened as I slid deeply into her den of incestuous depravity... I was committing actual incest with my own mother and loving it!

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