My Cross-dressing Story

My Cross-dressing Story


I was about 13 when I was home alone during the day, I went into my (older) sister’s bedroom and saw her school dress on the floor. For some reason, I thought I would try it on, so I undressed, put it on, and paraded in front of the mirror (no underwear). My immature little penis got stiff, but I had yet to discover the delights of ejaculation.

I walked around upstairs for about 30 minutes, then took it off and put my boy clothes back on.

The next year we moved house, and I started to get an interest in the laundry basket! Every bath time, I would have a look through and discovered my mother’s nylon full slips. I still hadn’t discovered what my right hand was for, so just got stiff which was nice.

It was around this time that one of my (male) friends and I started to ‘play’ - just undressing each other and groping each others cock. One day he suggested I wear one of his mum’s old bras, I did, it was nice! He tried it on as well. We continued to play in this way, then one evening he came to stay over while my folks were away. We looked through my sister’s things (she was away at college), and found a nice blue full slip, and a lovely baby-doll, very sheer and tiny sheer panties. We undressed each other, then he put the slip on, and I put the baby-doll on. As I pulled the panties up, I all of a sudden ejaculated. We both thought this was funny, but didn’t do anything more.

I then discovered girls, and my dressing reduced (but didn’t stop). When I finished college I moved away from home, sharing a flat with a friend from college. I had a good stash of porn, including some tranny mags. On the return from one of my trips home, I walked into a Dorothy Perkins shop. I came out with my first items – a white lacy front fastening bra, matching tie-sided panties, and a long waist slip (floor length). I got back to the flat, and dressed in my own things for the first time – heaven! I can’t remember how many times I came that night, but it was great!

I then bought a house, had much more privacy so my collection increased. Several slips (full and waist), several bra/panty sets, a couple of suspender belts, stockings, a basque, a short nightie and a long nightie (both with negligees). This was way before digital cameras, but I processed my own B&W films, so had a few pics.

Girls came and went, but then I met ‘the one’. We were married just over a year later and I got rid of my collection (and the pics). I stopped dressing – or so I thought. I was travelling around the country a fair bit, and started wandering into stores when away and looking at the lingerie, then bought a few items. I had a small collection that I kept in my car for nights away.

Trips to the US were fun, I would always got to a J C Penney or similar and buy a slip, bra and panties to keep me happy away from home.

Towards the end of this time, digital cameras cam out, and I found I could use mine as a web-cam. I had my first cam 2 cam session, came 4 or 5 times during the night while playing with like-minded others.

The sexual side of the relations hip with my wife was on the wane, so masturbation was my primary relief. She threw out some of the undies I had bought for her (2 white teddies), and also a lovely Kayser full slip. I managed to acquire these before they reached the rubbish and still have them.

There were many changes at work and I ended up home based. I had quite a few conference calls with customers were I was wearing just the Kayser slip!
I gradually added to my collection, and started to dress more and more. My wife retired, and this put a stop to things.

Now, in retirement, I can only wear when she is out for long enough, but I do like to cam with others.

I consider myself straight, and wouldn’t do anything without lingerie (or at least nice man undies), but I do get aroused by a hard cock in lingerie, and I have made quite a few guys cum just by dressing on cam for them. I have no wish to be a ‘gurl’, I’m just a hairy guy that like lingerie (on women as well).

How long will I continue? As long as it still feels good!!!
发布者 arnold11195
3 年 前
评论
51
账户以发表评论
arnold11195
arnold11195 出版商 6 月 前
Bobblehat12 : Same for me, but it reignited when it became sexless (but had never gone away, just reduced slightly!)
回答 原始评论
Bobblehat12
Bobblehat12 6 月 前
Yes that is another thread. I speak from experience of a sexless marriage. I didn’t get into cross dressing because of that. It wasn’t a substitute for sex I wasn’t having, or never had. It was always there.
回答
arnold11195
arnold11195 出版商 6 月 前
Bobblehat12 : Very welcome. Marriage is now sexless (menopause), so I need to find an outlet. I dress in lingerie and dress with others who wear.....
回答 原始评论
Bobblehat12
Bobblehat12 6 月 前
I haven’t read all the comments, but I imagine they have a similar thread…starting young, wonder whether we are gay or straight, having to keep things quiet because of our relationship….but so wanting to share times with someone like minded. Thank you for sharing.
回答
Camisole123 7 月 前
Mine very  same story love cross-dressing  and masturbating  at home love camming with other crossdressers 
回答
alicesissylove
alicesissylove 8 月 前
Very nice history, very similar to mine. 
回答
Anfrield
Anfrield 1 年 前
Thanks for accepting the friendship Arnold. I masturbated from the age of 7, mostly with girls in mind. But I noticed I got erections too seeing a penis, but as not attracted to other parts of the male body. On my 18th I gave in to my bi-feelings to a house friend of our family, who touched me and played with my cock. The beginning of a decades-long secret intimate friendship it was. 
回答
Anfrield
Anfrield 1 年 前
Nice story, getting aroused seeing another man's cock in ladies' panties is a certain sign of bi-curiousness. I hope you can live out your secret dreams once in real. Friendly Greetings. Hans. 
回答
cdhubby3054
cdhubby3054 1 年 前
great story
回答
bimale49 1 年 前
lovely story 
回答
joelinger52
joelinger52 1 年 前
my story as a young boy is the same ! ... I was hooked ... For ever ... And I love it 
回答
Leomoore
Leomoore 1 年 前
Great post. Like you i love to dress when the opportunity allows, no way am i convincing though.  Best wishes.
回答
arnold11195
arnold11195 出版商 2 年 前
petering52 : I play on Skype.
回答 原始评论
arnold11195
arnold11195 出版商 2 年 前
petering52 : Skype. Don't get much chance, need wife to be out for long enough.
回答 原始评论
petering52
petering52 2 年 前
Your story has many similarities to me. And about same age, what system do you cam on?
回答
nylonslip1
nylonslip1 2 年 前
I like this statement very muchhave no wish to be a ‘gurl’, I’m just a hairy guy that like lingerie
回答
sarah_hot1
sarah_hot1 2 年 前
Sounds a familiar story. I started with rummaging through mums knicker drawer, my favourite being red see through knickers with black lace trim. Like you I and wife retired, so finding time to dress limited 
回答
arnold11195
arnold11195 出版商 2 年 前
sloggijohan : Hope we can make it happen.....
回答 原始评论
sloggijohan
sloggijohan 2 年 前
We are sort of in the same boat. Looking forard to camming via skype and cumming via skype :smile:
回答
meat13 2 年 前
I too love dressing in my wifes soiled knickers so the guys can smell them when we play. love 69 with them.
回答
ed689 2 年 前
It is a shame so many of the Pennies stores have closed up. I always love to browse thru their lingerie section. I now wear panties 24/7 and have dressed as a woman for costume parties. Never passable but it was fun and that was long before I found the joys of being with another man.
回答
nylonslip1
nylonslip1 3 年 前
Interesting and exciting at the same time
回答
katey08 3 年 前
Very similar to my experiences 
回答
arnold11195
arnold11195 出版商 3 年 前
So true - I have had a few purges, but can't stop!
回答
arnold11195
arnold11195 出版商 3 年 前
Loverosatin : Seems to be how most of us started!
回答 原始评论
Loverosatin
Love to read about another’s experiences that I can completely relate to. 
回答
kinkyoone
kinkyoone 3 年 前
your story has a great line. My cross dressing started after I got married and suggested to my wife I try on her panties. Well it went all the way to her buying some for me too. Like you dont want to be a boi/sissy, just enjoy the thrill and feel of quality lingerie. That doesn't mean I cannot appreciate cross dressing stories and film, even anal fucking, toys or cock. Your last line is the best, totally agree.
回答
darren134
darren134 3 年 前
prairieFreak13 : I'm glad you did to your beautiful and sexy and I will be there for the first time and I hope you feel like a like a real woman...that's how I see you ....
回答 原始评论
coltag1947
i started wearing my sister's panties when i was 13.  so similar tale to tell
回答
meintights
meintights 3 年 前
Send her out... You make me cum.... Mmmmmm
回答