Stefan's Adventures

[stefan]

Hi,

I have been around here for some time but not really contributed with any pictures of my boots.

My interest actually started with skirts and I have been a member on some other sites that is all about skirts on men and not heels at all. As a matter of fact some of thoose site actively discourage heels since they think it does not promote men wearing skirts.

Anyway, I have an interest in both and for years I have had a couple of heels and skirts. I have not really worn my heels outside of my home and the same goes for skirts. Lately I have changed that and during this summer I started to use some of my skirts and I even was dressed in skirts during a vacation this summer. No heels then.

Since then I have bought some new heels, both boots and pumps etc. I have been using some of them with my regular trousers on and off for very short time outside. Sometimes I have been at one of the local restaurants in heels and trousers and sometimes doing other things.

I have been rather daring I think in that I am doing this where I live and the risk of meeting someone I know is high. I have found a lot of courage and inpiration in posts etc from people like JeffB, Happyfeet etc.

Monday 2009-11-16

I went to a local restaurant dressed in short sleeve shirt, boots and a denim skirt. The restarant was not very crowded since it was about 45 minutes to closing time on a Monday but I had a beer and sat down reading a book. I have been to this restaurant many time and only once in skirts and not in heels. There was no comment at all from anybody. Could not se if anybody really looked at me since I was sitting reading my book.

Tuesday 2009-11-17

I had to go to a local grocery store. I did this using the same outfit as last night but I put on a t-shirt instead of a shirt. I did this in broad daylight around lunchtime. There were a lot of people around! In the grocery store I met a former neighbor and we said hi. He did not comment on my attire but he must have noticed becuase he was not very talkative at all. But i didn't bother about that. Below is the outfit in the grocery store.

Have a nice day

/Stefan

[stefan]

And here is one picture of me from the summer vacation, without heels at the time. /Stefan

[stefan]

2009-11-29

Today it was time for another adventure. This time to a chineese restarant that is about 1 kilometer from home. I was dressed in a white short sleeve shirt with blue stripes and a grey skirt going below the knee. On my feet I had a pair of new black boots with a 3,5" heel. They are really nice to walk in and on my way to and from the restaurant I had some double takes but no comments at all. The staff at the restaurant has now seen me many times in different combinations of normal menswear, normal menswear and heels, skirts and normal shoes and of course like now with both skirt and heels.

Even if I am sligtly nervous some days other days it does not bother me at all to be dressed in skirt and heels.

I hardly ever get eny comment out and about. This summer I did get a comment at anothter local restaurant when I was wearing a denim skirt. I turned out that the guy was homophobic. It is a strange thing that some people autoamtically beleive that you are gay if you step outside of the norme with clothes. Anyway I did not care.

Attached you will see todays outfit.

Until next time take care all of you.

/Stefan

[stefan]

Hi, Now it has been some time since I went out in heels. As you might have seen in earlier postings I quite regularly go to local restaurants mainly because I live alone and don't like to cook for myself. It's a lot more fun to cook when you have friends invited home. On Monday the 14'th of December I wen't to a local chinese restaurant dressed in a long sleeve shirt, trousers and high hell boots. The boots were under my trousers so not very visible. Today we had a lot of snow in Stockholm and for some time is was almost a snowstorm. Today I dressed in a short sleve shirt, a grey knee length skirt and my black kneehigh boots. This time both the boots and heels was clearly visible since I was wearing a skirt. As far as I could tell there was no reactions anywhere. I held my head high and acted like it was totally normal so I suspect a lot of people didnät even notice. It was a rewarding outing where I was walking with heels in snow for the first time. It was actually no problem at all.

[NH Heels]

Congrats on your outings stefan. It's always nice to read a positive posts about about an enjoyable outing. Keep it up!

[Dawn HH]

Stefan:-) I echo NH Heels sentiments on your outings. Your having fun in various outfits and wearing your heels out and about. There is nothing like it and good on you for doing it. Congrarts! Cheers--- Dawn HH

[stefan]

Congrats on your outings stefan. It's always nice to read a positive posts about about an enjoyable outing. Keep it up!

Stefan:-)

I echo NH Heels sentiments on your outings. Your having fun in various outfits and wearing your heels out and about. There is nothing like it and good on you for doing it. Congrarts!

Cheers---

Dawn HH

NH Heels and Dawn HH.

Thank you for the kind words. Kinds words from others as well as people sharing their outings with others is what keeps us all going and hopefully will inspire others. I hope in my small way that I can inspire oters here as well as in the real world. Even if I haven't seen any other men with heels, or heels and skirt, here in Stockholm I will continue my adventures and hope that it will eventually inspire others to also try it out.

Every adventure where you eihter have no comments or a positive comment will boost your own courage. I have so far not gotten any positive or negative comments on my adventures.

/Stefan

[johnieheel]

Thank you stefan for sharing your outings with us. Very encouraging.

[Thighboots2]

Stefan, Thanks for posting your adventures. Comments are meant to be constructive and are my own opinion of course. I do like the boots in your first pic not just because I like western styles but they look properly masculine and the heel does not look out of proportion to your build, but not the combination of the skirt and boots. The look would be so much better with bootflair jeans that show most of the heel. The holiday snap, the skirt look is great and don't change a thing there. When its hot the only comfortable thing to wear is a skirt whatever style it is (Kikoy is my preference). Keep having fun. Simon.

[stefan]

Stefan,

Thanks for posting your adventures. Comments are meant to be constructive and are my own opinion of course. I do like the boots in your first pic not just because I like western styles but they look properly masculine and the heel does not look out of proportion to your build, but not the combination of the skirt and boots. The look would be so much better with bootflair jeans that show most of the heel.

The holiday snap, the skirt look is great and don't change a thing there. When its hot the only comfortable thing to wear is a skirt whatever style it is (Kikoy is my preference).

Keep having fun.

Simon.

Simon,

I am glad for all comments I can get. I guess we all have a long way to walk before we find the optimal combinations together with or without skirts. I don't own any bootflair jeans but I can se your point.

Another thing that I forgot to mention yesterday was that a very good friend of mine that live in another aparment building about 100 meters from me passed the restaurant, were I were sitting down, and saw me sit down and eat when he passed the restaurant sitting on a bus. He gave me a call and was almost on his way to join me at the restaurant. He does not know of my interest in heels and skirts. Talk about a close call. Phuuuu.

I don't have a problem showing myself in heels and skirts or just heels with people I don't know, but I have yet to work up enough courage to do it when I meet my friends or at work. That might be a goal for 2010.

Cheers for now.

/Stefan

[Bubba136]

Had your friend joined you at lunch, the problem of letting your friends know of your crossdressing would have been solved.

[stefan]

Had your friend joined you at lunch, the problem of letting your friends know of your crossdressing would have been solved.

That is so true. Even if it is a slightly scary thought at this point in time. But I guess since I do streetheeling and skirting in the neighbourhood where I live my subconcious mind really wan't my friends to know while my concious mind is slightly scared what will happen.

I am pretty sure my friend will accept it, atleast when it comes to the heels, maybee not the skirt. My biggest worry, as it feels right know, is to get my 80 year old mother to accept it. But she does accept the fact that I wear earrings in both ears every day and has done so for about 15 years. So she might actually accept me heeling?!?

And then of course we have work. I am not ready for skirts at work that might be considered weird since I have some customer contacts. But maybee I could get away with heeling? I think some of the women at work might actually like it because the compliment me on my earrings and notice when I change between all the earrings I have.

Anyway I have a mission during 2010 to come out of the closet with my friends and family.

Thank you all for your support and morale boost.

[stefan]

Friday the 18th of December 2009

Today I wen't on a 30 minute walk in my immediate surroundings passing many people and some restaurants with a lot of people in them. Today I was wearing a black knee lenght pencilskirt, slightly on the formal side. With the skirt I had a longs leeve white mens shirt and black hose. Today I used my dress shoes with heels. You can see them in my album.

I really like the feeling of the pencil skirt in that it slightly limits the movement, it is simply not possible to take your normal long male steps. They have to be shorter and more elegant.

Most people did not react at all, but there was a couple I passed where it sounded like the guy was laughing after I passed them. It could have been something else that amused him but I doubt it.

All in all yet another fun adventure.

Have fun guys. You only live once.

/Stefan

[roniheels]

Congratulations on your outings. I like your attitude toward public healing and it sounds like you are having fun doing it. Continued success to you and keep us posted on your outings.

[stefan]

Monday 21st of December

We still have snow in Stockholm and today I was walking a couple of kilometers in the shoes I have in my avatar to have dinner at a local indian restaurant. Even though they were a little bit cold they were perfect with the heel piercing thru the snow making it easy to walk.

Besides the shoes I was dressed in khaki coloured pants and a short sleve shirt and of course a warm jacket since ot is cold. I passed a lot of people and none reacted at all. Yet another sucessful adventure.

/Stefan

[Thighbootguy]

Starting to sound like we have another person hooked on heeling. Thanks for sharing you experiences. The sharing helps a lot of new folks and brings back a lot of memories for some of the ole timers.

[stefan]

Wednesday 23rd of December

Today it's the day before christmas eve and I needed to withdraw some money from an ATM to buy some christmas presents tomorrow morning. The temperature is up slightly since the beginning of the week. Now it is -3 degrees Celsius (27 degrees Farenheit). For todays adventure I was dressed in my warm jacket and beneath it I had a short sleeve white and blue shirt. Below that I hade beige pantyhose and a beige cargo skirt. On my feet one of my knee high black boots.

http://www.hhplace.org/album.php?albumid=184&pictureid=2392

The skirt stops slightly above the knee and the boots slightly below the knee. That leaves about 10 cm (about 4 inches) between the skirt and the boots. I was fine since I had my pantyhose. Not cold at all. When I came home I was actually rather warm since I kept a fast pace.

The walk to the ATM and back took about 40 minutes. I started at around 10 pm, and I hoped to find one of the local restaurants open so I could have a beer on the way back. None of them were open tonight. I guess everybody is home making the final christmas preparations. It was also less people on the streets than normal. But I managed to get a couple of turned heads and one man that did not look at me, his eyes were focused on my skirt the whole time. It was like my skirt was a magnet. There were however no verbal comments.

I wish you all a Merry Christmas and a happy new year.

/Stefan

[Dawn HH]

Stefan:-) All of the boots were njce streetheeling material, but I especially liked the shoes in pics # 8, 10, and 12. I echoe TBG's comments about giving the newby's courage and reminding us older posters of things that we have done from years ago. Cheers--- Dawn HH

[stefan]

Tuesday the 29'th of December

I am currently replacing my old mother's PC. Since the old PC was totally dead I needed to get a way to get the data of the old harddrive. So I had to go to a computer shop and buy a IDE -> USB connector so I could connect the old harddrive to the new PC without opening up the new PC. Since I had to leave my apartment I thought, why not use my heels.

In Stockholm it is getting colder again. Yesterday it was above freezing and the snow was all wet and would mess up my boots. Today with the temperature at about -8 celsius (about 17,5 Farenheit) there was better conditions. So I headed for the tram in a long sleeve blue shirt, my beige pants and the black boots I have in my avatar. After the tram I swithced to the subway line to the computer store. For you US people we have a really good public transport system in Stockholm

The whole trip to and from the computerstore took about an hour, even if my heels made the usual noise, when I walked, I could not se anybody reacting to my heels at all. Atleast not to my knowledge.

So now it's off to the PC to continue the work. I hate PCs that brake down.

Keep you heels on and a happy new year.

/Stefan

[stefan]

Saturday te 16th of January

It has been some time since I had an adventure. Today I felt an urge to go out heeling again. Todays outfit was a normal male shirt with my black demin skirt that goes slightly below the knee. I also had black pantyhose which makes my legs look a lot better. I then had one of my knee high black boots.

I was going to a cafe to have some lunch so I was out in the broad daylight for everyone to see. This is, as almost always, in the area where I live. I met a lot of people on the way to the cafe and on the way back. Not many reactions at all but I think there might have been som turned heads behind my back.

Have a nice weekend.

Stefan

[Dawn HH]

Stefan:-) It sounds like you had a very enjoyable outing. You don't seem to care if you run into your friends or strangers as you are as you are to everyone whether you know them or they are new aquaintances. That is the way to be. Congrats! Cheers--- Dawn HH

[stefan]

Hi, I have not written much here lately. I have been very ocuppied with work the last 6 months, to the degree that it has been to much overtime and I am considering chaning jobs. Anyway, today I had an outing in heels. The first fr a long time. FIrst of all I went to a restaurant and had a nice dinner and met some nce people. I was dressed in dark blue trousers and heels. Besides that I also had my nails painted sparkling pink and also 2" hoop earrings. As long as I was on the restaurant I had only a few comments mostly on my nailpolish and earrings. Thoose comments were very positive. The said the earring gave me a carisma. After the restaurant I walked to a local gasstation to buy some bear and coke. I was approched by a man that asked about my earrings and heels. He asked the standard question, i.e. are you gay. I answered no, I just dress like this because I can and I like to. All in all a very successful and fun outing.

[Dawn HH]

Stefan:-) There are quite a few people in this country that would give a right arm to have a job today with much overtime. Maybe you should consider your decision to look for another job where you may not be as lucky to have constant employment much less overtime. Cheers--- Dawn HH

[stefan]

Hi, If you read back in this post you will find a reply were I last year was sitting at a local restaurant and one of my best friends calld me. At that time he did not stop by at the restaurant. A couple of days ago I was mentioning to him that I like to be dressed in a skirt and also like heels. He is the kind of friend you really like to have, he said that he support me whatever I like to do. This sure builds up courage. Today I have had a knee length denim skirt for the better part of the day. I was out for lunch at a local restaurant dressed in the skirt and the heels. For dinner I went to another restaurant, the as mentioned last year. Today my friend called me when I was at the restaurant, with the diffeence that he stopped by today. So now he does not only know that I like skirts and heels he has actually seen them. It felt rather good. Tomorrow I am going on vacation. I plan to spend most of the vacation in heels and skirts.

[stefan]

Hi, I have not written much here lately but now I am slowly getting back to write here again. I have come to understand that to feel well with myself I really need to express some more parts of my female side. For instance since about 6 months I have been much more bold with my earrings i.e. I don't use the subdued type of earrings mot males uses if they use earrings, and I were them for work. As a matter of fact there is not many reactions at all. I also have nailpolish on both my fingernals and toes every day, and yes I also have it at work. And every day that I come home from work I change into a skirt and some heels. Some days I change into a dress. One of my friends have seen me many times in booth heels and a skirt and he is very supportive of the whole deal with skirts, nailpolish, earrings etc. I go dressed in skirt and heels to some of the local restaurants were I live about 3-4 times a week. Currently my favourite skirts are below the knees and for heels I usually have kneehigh boots. The waiters at the restaurants always treets me with a smile and I have so far not had any comments from the other guests, even if they twisted their heads now and then. I have almost not had any bad comment at all fron anybody.