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Chapter 7

For many years my dressing was a secret, how could you share such a thing with anyone. But if you dress in ladies sexy lingerie then you are likely to be caught out, as I have written in previous chapters.

Initially getting caught was a terrifying experience. The shame of it, the being caught wearing ladies underwear. How can I ever be considered a man again.

But time cures everything and you look back on experiences of being caught and smile. It was actually very exciting. The time I was bent down in front of my cousin and she suddenly asks what I am wearing her eyes transfixed down my shirt. I stood up and said a vest, to which she replied “what a lacy one?” I wonder what she really thought.

The time I was wearing a bra and watching my sexy next door neighbour through the blinds, knowing I was hidden. Only when she looked up and burst out laughing I realised that I wasn’t hidden. I really couldn’t believe she saw me. I later checked the view from where she had been and I could not see in. So I convinced myself I had imagined it.

So when she was out the front cleaning the inside of her windscreen I happily stood behind the blinds watching her. I saw her look up and look away. I thought she had seen me again, but she carried on cleaning, but she looked as though she was discreetly trying to get someone’s attention. I stood back because I felt that she had seen me. Her boyfriend appeared and she talked to him and they were both laughing. When he looked up I knew I had been seen.

I was really terrified now. She was the local gossip, very attractive and popular. They both spoke to me in the same friendly way. He showed me holiday photos and talked about all the gay bars, so I realised that he had thought I was gay because I wore ladies sexy lingerie.

One day I was looking out the back across the gardens and wow I saw her washing. She had sexy black lingerie on the washing line. Bra, panties, camisole, suspender belt and stockings. I had never seen her hang out underwear before and this wasn’t exactly ordinary sexy lingerie. I was so excited I wanted to lean over the garden fence and touch it.

I wondered if it had been related to her seeing me wearing a ladies bra, that she was showing me what she wears. Or maybe it was a tease, I couldn’t help thinking that this is what her lucky boyfriend gets to see.

If the sexy lingerie on the washing line wasn’t enough to excite a little sissy, then I saw her out in the back garden sunbathing. Normally she sat out the front of the house because there was no sun out the back. But there she was literally outside my bedroom window sunbathing in her bra.

Now I simply couldn’t understand why she would be sunbathing there because it was in the shade. I really did think she was teasing me. I was so envious of her and wished that I could be a woman like her. I wondered if it was all in innocence but I didn’t think it was.

I decided to test the situation and dropped some coins onto the windowsill making a loud noise, she opened her eyes and looked up. I was behind net curtains but now she knew I was there. She closed her eyes and continued sunbathing. My mind was in turmoil, what was going on. We had been neigbours for several years. Now she was hanging out sexy lingerie and sunbathing in her bra.

I had experienced being caught and now rewarded. I wanted to get seen more and I did!

To get caught all you have to do is wear ladies underwear and carry on your normal activities. From time to time you will show off something or something will happen that will expose you. This has happend on many occasions. The following are two incidents.

I was trying on trousers in a shop. I removed my trousers and was standing there in my knickers, which I was admiring in the mirror. Suddenly the curtain opened, I looked and saw a lady looking at me. She quickly closed the curtain, my heart pounded, before I could even worry about whether she had noticed I was wearing knickers the curtain opened again and she looked straight down at my knickers. She closed the curtain and I heard her laughing, I could hear mumbled talking broken up with laughter, then there were two people laughing or was it three.

This was just awful. I hurriedly got dressed and was too scared to leave the changing room. When I left the shop was full of people all of them looking at me and laughing. There must have been a dozen or so people there. As I walked to the door I heard one lady say he is a transvestite. I looked around and everyone was laughing at me.

It was an awful experience at the time. The lady was rude to open the curtain as she did. If the curtain was closed then she must have realised that someone was in there. Then to look a second time almost as if to double check what she saw the first time was unbelievable.

If this had been a man walking in in a lady then what? As it was a lady did this to me and then told everyone around that I was wearing ladies knickers.

Of course when I look back on this I love it! She is a lady and I am a sissy, she had every right to look in and then tell others.

A second occasion you just can’t imagine. People say you have to be careful in case you have an accident. This is true but it would mean never going out wearing girly things again.

Unfortunately for me I did have an accident.. I stood on a broken bottle which went though my shoe and into my foot. It was a large cut and bleeding very badly. The result was that I had to go to hospital to have it tended to. Now so far I was not worried. My foot was injured so no risk of getting caught.

Everything went well until I required a tetanus injection. The nurse told me that I required one and told me what she had to do. I was asked to lower my trousers. This was absolute horror, I had on bright burgundy knickers, lace sides, bow on the front. I undid my trousers and stood with my back to her, I slightly lowered my trousers.

She came up behind me and lifted my shirt up and pulled my trousers down below my bottom. The cold air on my bottom indicated all was on show. She lowered my knickers half way down my bottom and gave me my injection.

I quickly pulled my trousers up and didn’t know where to look. She spoke to me and seemed completely normal as though what had happened was normal. To this day I can’t help wondering is it possible she hadn’t noticed I was wearing ladies knickers?

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.