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Chapter 6

The desire to dress getting stronger, to the point that I could no longer wear men’s underwear. This was actually a tough period for me.

I was completely hooked on wearing ladies underwear. I wanted to wear everything but knew this was impossible to do if I didn’t want to get caught.
I was wearing knickers at every opportunity, yet when I went to work I always wore male pants. I guess at work it is quite a competitive environment and I felt that I had to be manly.

I was very unhappy wearing men’s pants. I actually was envious of one lady. She had a very sexy bottom and it was made even better by her beautiful panty line. I just felt so jealous that she would have got up that morning slipped on a pretty pair of knickers and thought little of it. She was a lady and it was her right to do so. I wanted to be able to get up in the morning and slip on a pretty pair of knickers and come to work too.

Sometime soon afterwards I slipped on a pretty pair of knickers to wear to work. I felt so vulnerable, I felt that everyone would know I was wearing ladies knickers. Somehow wearing ladies knickers under my suit made me feel exposed.

It felt great at work, I loved being in an environment dominated by ladies. I was based at the head office and the staff was largely female. I used to sit with them and think if only you knew I was also wearing pretty panties.

I struggled a little wearing knickers under my suit. I was a network administrator in charge of the IT for the company in the UK. I was in charge of people and had responsibilities. How could I carry out my job wearing ladies knickers. I now had a conflict. I needed to wear ladies knickers as a minimum, yet they stopped me from being manly and this concerned me over my job.

The desire to wear ladies underwear won. Now there was only the doctors that I felt I needed to wear male pants to visit, not that I visit very often. So I had thrown away all of my male underpants including my silk boxers bar two pairs, which I kept for emergencies.

I looked online for ladies knickers that could pass as men’s, plain cotton ones seemed best and I bought Sloggi Sensual Thai briefs. These were so unlike anything I would normally buy, but I felt they could easily pass as men’s.

I no longer own any male underwear. I rarely wear my Sloggis, but they are there as my emergency backup! Even when I visited the gym I would wear satin plain knickers. Men tend not to look at each other and I always put on my top before my knickers so they were not exposed.

I was now wearing ladies underwear all of the time, it was great.

I do feel that we all have male and female qualities and the percentage isn’t always reflected in being a lady or a man. I am a man but inside I feel that I have a large amount of female qualities, not just because of my preference to wear ladies underwear, but how I look after my skin, nails etc. I look more towards ladies than men for inspiration.

By throwing away my male underwear and now only owning ladies underwear I felt that my feminine side had just destroyed my male side by 30%. I now dressed in ladies clothes as much as possible with the intention not to be noticed, so wearing trousers rather than skirts. I no longer dressed when I had time alone. I could no longer dress as a man.

5 Girls reactions

It has been impossible to hide that I wear ladies underwear, nor would I want to hide it. I did once upon a time, but once you are caught and have got over the shame of it, there is a great excitement to it.

When I was a young child, people thought it was funny that I would always be putting ladies underwear on. This included my aunties whose underwear I borrowed many times.

When I was a teenager one of my aunties didn’t find it quite as funny when she found out I was wearing her sexy lingerie.

We were in the kitchen together cooking, we often did this and I loved it, especially when I was wearing her knickers. This time it was a lot more exciting for me because I was wearing her bra and I was constantly aware of having it on.

Whilst we were cooking she suddenly twanged my bra strap (or should I say her bra strap?). She shrieked with laughter and asked if I was wearing a bra. I was stunned and blurted out no it was my vest.

She left the room and I knew I had to get her bra off as quickly as possible. My aunty came back into the kitchen and immediately grabbed my polo shirt and yanked it down exposing my bra and shrieked that I was wearing her bra. She told me to take it off, which I wanted to do very badly. But she was now pulling my shirt up over my head. She was furious and I was scared to resist her any longer.

I stood there in front of her with my shirt off, my face was burning bright red with humiliation as she laughed at me and asked what would my friends think of me wearing sexy lingerie. I couldn’t get the bra off I had literally lost control of my body. She undid the bra which was a feeling I will never forget.

She asked me if I was wearing anything else and I said no. She asked if I was sure because she would check. I was too scared to lie so I said in a very croaky voice that I was also wearing knickers. She burst out laughing again and told me to take them off. She frog marched me to the bathroom and pushed me inside.

She didn’t come inside with me! I removed her knickers and got dressed. My polo shirt was slightly ripped and creased where she had grabbed it. I handed the knickers to her and we went back to the kitchen. Conversation was difficult after that and I really wanted to leave.

It was a very humiliating experience, but I find it a turn on looking back and it sowed the seed of me liking exposure and humiliation.

Other experiences have been very tame compared to this. At the time I was turning from a boy into a man, so the dressing was confusing to me and now I had been found out.

I have been laughed at many times, girls who have appeared very understanding at the time and made me feel comfortable with myself have gone on to tell their friends about me.

I have learnt that if you let a girl know your secret about wearing sexy lingerie then it will become a secret between her and her friends and her friends friends!

I have opened the door to a courier lady wearing a ladies underskirt a number of times. She never seemed to notice when we spoke, but as soon as I turned around she would crack up laughing and have a good look.

I have been walked in on in changing rooms and seen. It is quite amazing when they take a second look at you and look you up and down. It is like because I am a guy wearing ladies underwear that they have a absolute right to stop and stare! Of course I love it.

I do like to wear knickers with lacy waistbands and take every opportunity to bend down and stretch. I have been seen many times doing this and not always by people I had expected to see me. I once did this and a girl who was with a large group of girls saw me and shouted out very loudly that I was wearing pink knickers! The sheer number of girls in the group made it a very intimidating experience. Everyone was staring at me and my face was a much brighter colour than my knickers!

La La Lingerie now have another  sexy lingerie blog that we’d like to share with you!

Coming Soon! A blog all about Sissy (the man who wears lingerie). This blog will feature Sissy himself embarking on some of his very own fantasy’s and putting himself at risk of exposure…because that’s what he loves the most! This blog will have plenty of pictures of Sissy in awkward situations and maybe even some video clips!

Every time I look at a lady I am checking out what she is wearing underneath. Occasionally I drop myself in it by asking a silly question about their sexy underwear.

One example was with a friend in Plymouth, we were chatting up two girls. The girl I was talking to had lace exposed at the top of her blouse. I was so excited by this and longed to be wearing such pretty underwear myself. Before I could catch myself I heard myself asking if she was wearing a teddy or a camisole underneath. The others just opened up laughing and she asked if I was kinky. Fortunately the others laughing meant I got away without having to give a reply.

I just love ladies underwear so much. I was young and always out on the town. I had a bedsit on the main strip where all the pubs and clubs where. It was very convenient for taking ladies back to.

As soon as we got back the heavy kissing would start. I always tried to get the ladies stripped down to their underwear and stay like that. Usually they would end up removing their underwear themselves because I wanted to look at them like that forever. I just love seeing ladies in their underwear, I can’t say it enough times to make my point. I just love love love it!

As I got bolder I started to wear items of ladies underwear when I went out, knowing it was very likely I would pick someone up. It was a huge thrill when I went back with a lady and we started taking each others clothes off.

It was very surprising that some didn’t even notice I was wearing ladies knickers. They were removed along with my trousers. of those who did notice, some thought it was hilarious but it didn’t stop them from what they wanted. I asked one girl if it put her off and she said no way they ain’t going to be on very long anyway.

One girl made me confess to being gay or she would leave. So I confessed to being gay and she stopped, but refused to have sex with me! I spent the whole night massaging her and trying to get her aroused. She said it was like being with another woman because I had a woman’s touch. Bitch I thought. I wasn’t ready for those complements back then. I was a stallion in girlie knickers!

I ended up the centre of attraction with one girl and her three friends, she obviously told them I wore ladies knickers and they were keen to find out for themselves. I went with all of them eventually and none hid their curiosity about what I was wearing under my trousers. Who would have thought wearing ladies knickers could get you laid!

It wasn’t always like that though. One girl popped over with me for a quickie, it was great, good fast sex and back to the club. Where she announced to everyone that I was a faggot and wearing girls knickers! Some unpleasant things were said, but the best comment was when a bloke said to her “and you still fucked him ya slag”!

I remember joining the Navy. I thought this is where I become a real man. One who would be confident and would gain respect from those around him. No more would I don on a pair of ladies soft silky knickers. I wanted boxer shorts, cotton ones at that!

I was only in the Navy for two weeks before going on Christmas leave, which I think was for two or maybe three weeks.

I wanted to spend some time in Plymouth and visit a girl called Belinda whom I had known for many years. We had spent summer holidays together when I would travel down to Plymouth and stay at my aunt’s who lived opposite her.

She was the same age as me, but sexually she was 10 years ahead. It may seem a boy’s dream but she really corrupted me! She was after a lot more than just a kiss and cuddle. She gave me sex education at a very young age. I only wanted to play kiss catch!

It was with the experience she had given me that made me decide to visit her whilst on leave. I was in the Navy and a virgin, not a good thing! I knew she was the girl to help me out.

I had arranged to stay at my aunty’s for a few days whilst on leave. I visited Belinda the first night and we spent the evening in her room. She told me about all the pubs and clubs she went to. She showed me her clothes that she wore out (Is this a usual thing for a girl to do with a boy?). I was really jealous.

She could go to pubs and clubs and get served and I couldn’t. I loved her clothes, the short dresses were really sexy and she put a couple on to show me. I think really she was just excited about her clothes that she wanted to show me. I loved it, especially seeing her in her sexy underwear.

I wanted sex with her and I think she knew that. She was very up for it and I think me still being a virgin made her feel special. So she was my first girl. I was in love with her and wanted to spend forever with her, well at least the night!

My aunty on the other hand wanted me back by 10:30. Here I was, a man who had had sex with a girl and serving in the Navy having to go home at 10:30. I was not very impressed with my aunty. With this in mind I took a pair of my aunty’s knickers when I got home, they were a bright green pair, soft and silky. I wore them to bed that night and relived my moment with Belinda many times.

I took this wearing of my aunty’s knickers as a little relapse. She had spoilt my night and that was the only reason why I was jerking off in her knickers.

That was to be the last time I wore ladies underwear for several months. By now I was really after girls for all the right reasons. I did always like their clothes and got excited by seeing girls in their underwear, but I no longer had the desire to dress in ladies underwear myself.

Several months later that all changed when I visited my aunty. I went to use the bathroom and the washing maiden which she kept in there was full of clothes, including ladies underwear, bras, panties, tights and a camisole.

Here I was alone in the bathroom, not even having to sneak around. I quickly fondled all of her underwear and before I knew it I was on the floor kicking of my trousers. I took a pair of white silky panties and put them on. I rubbed myself through them, it was heaven and I had to stop quickly before I spoilt the moment!

I pulled my trousers up over the panties, it just felt so good. I stuffed my pants into the dirty washing basket and went downstairs. I was aware of the panties, they felt so good against my skin. I felt very aroused to be in the company of my aunty whilst wearing her panties. I wanted to show her.

When she left the room I would take down my trousers and touch myself over her panties. When I heard her returning I would wait until the last possible moment before pulling my trousers back up.

On one occasion I didn’t get my trousers fully up, they were barely up to my bottom. The room was quite dark and I sat with my legs up on the sofa to try and hide my predicament! I loved the feel being so close to being discovered by my aunty wearing her panties!

One of the great things about the Navy was the run ashores, lots of beer and women. I had many one night stands, not always with Miss World either! I loved the getting undressed part, it was such fun, so exciting. To have a lady dressed in only her bra and panties really excited me. I guess I was supposed to remove those too? It was often the girl who got impatient and had to remove her own underwear! I never let it be known that I liked to wear ladies underwear but never got the opportunity to.

I did have a few longer term relationships. At the time I guess you would call them serious relationships. I was simply in love with them. These relationships could be hard because of the time apart. However when a relationship combined the friendship I had enjoyed with girls as a boy and now included sex, then the relationships were pure magic. I was still too embarrassed to mention my love of ladies lingerie.

I sometimes took off by myself and would go into town shopping. I would pass by lingerie departments and steal glances. I so wanted to buy lingerie and wear it, it was part of me. Yet it was also part of me to live and work in a manly environment.

I had pondered over meeting escorts and asking them to let me dress up, but I was always in a relationship with a girl and it seemed the wrong thing to do. I couldn’t open up to anyone so I stayed like this until I left the Navy.

2 Growing up, how wearing ladies underwear affected me. The desire to dress always remaining strong. More interested in what the girls wore rather than what they had underneath their underwear.

The seed for dressing up was planted at a very early age. It was not about sex, it was about preference, comfort, being like those around me.

At school I was always interested in girls and had many as my friends. I think perhaps because of my early years being spent in the company of females that I felt comfortable with girls, they made great friends. It wasn’t a conscious decision, it just happened that way.

My father was a ‘hard’ man. He joined the Navy at 14, traveled the world, was away for years at a time and was very into sport, including boxing. I call him a hard man, others might call him an animal, but that is not part of this story.

What I can say is that this hard man had less influence on his son than any of the female members of the family or any of my female friends!

When I fell down my mother was not allowed to pick me up, I had to pick myself up. When I came home from school with a black eye I was given another one for letting it happen. When I came home with a cut nose I was enrolled on Judo classes.

But running was my savior because when death was looking me in the face I could always out run him. I did cross country too, so I never bloody stopped running!

My father thought that my mother had made me soft. Maybe, but my aunties had helped too! If I fell down and got a bump on my head they put butter on it. No wonder why I preferred the company of ladies and of course I could secretly borrow their sexy underwear.

I had lots of male friends and loved football and all the games boys played. If I was ever with the girls and they had dolls, I would always lift up the dolls dress to see if it had sexy knickers on!

My childhood I say was typical in many ways, but I had a violent father and a fondness of wearing ladies underwear.

When I had girlfriends I was always excited by what might happen, seeing their sexy knickers and if I am lucky touching them. I loved life outside of the home environment. I had fun with boys and girls.

When I started secondary school I sneaked into the gymnasium with another boy. It was the girls turn to use the gymnasium, it was a new one and we took it in turns to use it. He stayed downstairs but I went up to the changing rooms.

There were two girls in there from the third year. They were big girls compared to me, I was only in the first year and a short ass anyway! One of the girls was standing there in her skirt and bra. This was very exciting, I just stared at her and blurted out “you’ve got a brown bra on”. They laughed and she turned around and told me it’s what’s inside I’m supposed to be interested in!

She looked like a giant Goddess and even now when I think back to this time I see her as being a giantess. That image stays with you forever, I wonder if she knows that?

I guess I couldn’t help myself falling in love with her in her bra. The love of ladies underwear was deeply entrenched and so deeply entwined that I would never change.

My parents divorced when I was around 12. My life was void of almost any female contact. There were a few ladies teaching at school, but I went to an ex grammar school and the teachers were predominantly male. We did woodwork and metal work whilst the girls did cookery! I never asked to do cookery, but if I had of done then I think I would have got a beating and then therapy!

I went through a period of time when my interest in girls was exactly that. I loved girls, I had lots of good times in learning about them. A bra was not an item of desire, it was an obstacle, something that required great skill in undoing and a very patient girl. It stopped me getting to where I wanted to go!

Then the girls started wearing pretty underwear as we got older and I just wanted to be one of them. I was not gay, no interest in boys. I just really loved girls and wanted to be the same as them. I had learnt from a young age that no one can make a boy happier than a girl, but somehow that made me want to be a girl.

I desired to wear pretty things.

I knew that I would stop being like this one day. I was joining the Navy and it was time to leave home. I was sixteen and I was now a man. No more would I want to wear ladies underwear.

And I didn’t! Well not for the first several months. I think the hard physical training designed to break and build you up really cured me. But after training, I was a confident man and I needed knickers!