Tuesday, August 31, 2010

I like this dress

I like this dress. Very simple, very colorful, nice pattern, short and sassy.  The woman wearing the dress is not too shabby either.  :)

Image from met-art.com

Sunday, August 29, 2010

The University Years

The first year of University was a disaster.  I made the mistake of living in residence and an all-male residence at that.  Not that I was tempted by any of the men in my residence, I was being a good boy, no dressing, no men, just behaving myself and studying.  The problem I had with an all-male residence that there was just way too much testosterone, it was like living in a locker room twenty-four hours a day.  Too much drinking, partying, and rabble rousing for my tastes; the only time I was really there was to sleep.  I spent most of my time in the library or hanging out off campus in coffee shops.  The first year also the point I broke up with my high school girlfriend.  I was the victim of the Turkey dump.  She went away to a different school from me and when we got together at home for Thanksgiving she broke it off with me.  So really nothing to report in year one.

Year two on the other hand was much better.  I got my own small apartment and enjoyed living on my own.  I started dating a few women, nothing serious; I was just hanging out enjoying life and studying.  At this time I also found my “local” as I liked to call it, a small bar near where I lived that I would stop in have something to eat and the occasional drink.  It was a perfect place to hang out in the afternoon when I had no classes.  It was quiet and I could hang out the bar, read text books and nobody would bother me. 

One of the co-owners of the bar was a guy named Steve who worked behind the bar during the day. He was a big bear of a man, early fifties, grey hair, over six feet tall and weighed I well over two hundred pounds.  Really nice guy, friendly, always had a smile for everybody and would give me a free beer or pop, every so often because he knew I was a student.  Anyway, one Friday afternoon he asks me why did I always leave once the after work crowd started to come in, he goes “there are lots of cute women and on Friday’s and it usually turns into a party atmosphere”.  I told him that I usually went home and studied some more, and once I knew it was going to get noisy at the bar, it was time for me to leave.  He goes “well you cannot study all of the time, what are you doing tomorrow.” I tell him study during the day and then probably watch the hockey game on Saturday night.  He goes great “why don’t you come over to my place, we can watch the game together and then I can take you out and show you some places, that you may not have been to before.”  I said sure, he gave me his address and off I went home.

The next day I studied and then got cleaned up and headed over to Steve’s place for the hockey game.  He lived a few miles away from me in an old converted warehouse.  When I got there he opened the door wearing shorts and muscle shirt.  He says “pardon my appearance but this is my hockey watching outfit.  I liked to be relaxed and comfortable when I am watching the game.”  So he invites me and gives me a tour of his place.  He hands me a beer, we head to the couch and starting watching the game.  We make the usual small talk about hockey; then he asks me how school is going, we have another beer and then of course he makes his move.  He was not subtle in any way shape or form, just reaches over grabs the back of my head, pulls it towards him and sticks his tongue down my throat.  I struggled just for a moment but then started getting into it. 

After a few minutes Steve stops and leans back and just starts laughing.  He says “I knew you would kiss me back.  My gaydar went off the first time you walked in the bar.  I have been dropping hints for weeks but you never took your head out of your books.”  Then he just kept laughing and grabbed me by the hand and took me to his bedroom. 

Now with Mr. P it was all nice and slow and tender, Steve on the other hand was lots of things, but slow and tender was definitely not in his top ten traits.  After he got me undressed he turned me around and checked me out and then gave me a couple of slaps on the ass and pulled me into bed.  I was really turned on; he got on top of me and started again with the French kissing.  I weighed only about one hundred and forty pounds at the time and he out-weighed me by over sixty pounds and I loved how his weight felt on me and the fact that I could not move, he was taking the lead and I had nothing to say about it.  Next he moved to my nipples, slowly licking them and then giving them little bites.  I happen to have rather large nipples for a male, and they had never been played with before and it really turned me on.  The harder he bit and sucked the harder I moaned, he took this as a sign of encouragement and kept working them, pulling, biting, twisting for at least thirty minutes and then I came.  No stimulation at all of my penis, just Steve working over my nipples and I was cumming.  He laughed and then after I was finished he licked it all up and then started with the French kissing again.  I could taste me own cum on his tongue and it just made me hard again.

Finally he pulls away and gets up and tells me to roll over on my stomach.  Next thing I know he is pulling on a condom and grabbing some lube.  I ask what he is doing and he says “I am going to fuck you.”  Now I had never been fucked before, I had seen pictures of it but Mr. P was all about the oral sex no anal.  I was scared to death and did not say anything more and he went to work putting lube on his fingers and then working them around in my ass.  I groaned and moaned every time he put his fingers in me; finally he says “raise your ass a little” and the next thing I feel is his cock going up my ass.  My ass felt like it was on fire, I wanted to scream but then he started pumping and I started to moan, really enjoying myself. 

After what seemed to be an eternity he finally came, pulled out, gave me a couple of more slaps on the ass and started taking his condom off.  While he was doing this he says “why is it that the quiet types are always the wildest in bed.  You were wild, if you do not mind me asking, how many times have you done this?”  I explained that he was only my second man I had ever been with and he was the first man who had fucked me.   He says “well I hope I did not scare you, but you seemed to be enjoying yourself; so I just was going with the flow.”  I told him I was fine and that whenever he was ready I wanted to go again. 

He laughed and said “OK, but first I need a beer and a smoke first.”  So off we went back to the living room and I noticed myself in a mirror and just had to stop and look.  My nipples were all red and raw and the skin around them was already starting to bruise from all of the rough play. I just smiled and went and had a beer, as I had never felt so alive in my life.

So Steve became my first male fuck buddy and good friend for my remaining years at University.  Neither of us was looking for a relationship, at the time but we had amazing sex together; so what he had worked for us.  Mr. P may have been my first teacher in all things gay, but Steve was providing me a Master’s class.  He introduced me to his circle of friends; he took me to Toronto; to my first gay bar and in general reminded me that sleeping with men was fine.  Also, Steve tried to drive it into my head that I needed to be myself, not what other people wanted me to be.

He also tried to explain gay culture to me.  I was fascinated by his gaydar (gay radar for those of you not familiar with the term).  He claimed that he could tell if somebody was gay or not in less than five minutes after meeting them.  I asked him how he knew I would sleep with men the first time he saw me.  He goes, “For you, you did not even have to say a word, I just knew from looking at you.”  I claimed he was lying and he just got lucky, but he swore it was true. 

Just a side note on gaydar, I have worked on mine over the years but unless I see somebody in a gay bar, or he is hitting on me, at best I am fifty/fifty in guessing somebody’s sexual orientation.  However, I know some people really have the gift.  I have been hit on by men in some of the strangest locations (and no I was not out dressed as a woman, which can be a dead give-away in my books.  Lol) and either they are a lot more confident than I am in approaching men, or they have exceptional gaydar.

I do not consider myself good looking, just average looking at best but I have been hit on by men while: i) standing in line for a beer at a ball game, ii) buying a sweater at Eddie Bauer while my girlfriend was standing right there oblivious to the whole thing (he wrote his name and number on the bill and a note that said “meet for coffee??”, no I did not take him up on the offer, nor did I tell her), iii) in coffee shops, iv) in a hotel bar in downtown Cincinnati (not known as a hot bed of gay activity as far as I know),v) in straight bars, vi) in restaurants, vii) standing on the subway platform waiting for a train, viii) in book stores (real book stores not porn shops, but I have been hit on there as well Lol) ix) at a wedding, x) on an airplane, and finally xi) by a person who interviewed me for a job.  He called me back after the interview and thought I was very nice just not qualified enough for the job, but he wanted to get too know me better.  Lol I did not take him up on his offer. 

Now the funny thing is in all of the case above, the person hitting on me looked at least fifty years of age or older.  All of them asked me out for coffee, a drink, or dinner after only a few minutes of conversation with me.  Some of the conversations were as little as a minute or two; such as the guy on the subway platform or the guy at the ball park; some were a little longer like on the airplane or at a straight bar.   The times in restaurants have been strange, for instance one time I was sitting alone and a man actually came up and asked if he could join me and offers to buy me lunch.  I declined the buying of lunch but said he was more than welcome to join me. 

I did not act on all of the above invitations because some of them freaked me out.  But as you can see most of them happened in everyday situations.  I was not at some gay bar; or even in a gay part of town when these things occurred.  I was living life.  Yet somehow these men either sensed I was open to their advances, or they were brave enough to take a chance that I was.  I actually believe some men do have very accurate gaydar and I am living proof. 
I have written far too much again.  I will give more details another time of my university years.  Do not worry; there is more of me dressing up in woman’s underwear coming up shortly.  I just need to get my sexual history with men told, so that I can move on to other things.  The sex with men thing is an important part of the story, because it is what makes me, me.

PS:  I know this blog may seem very self-indulgent but it is certainly helping me work through some stuff I needed to sort out.  The other thing I wanted to say is that I have read lots of blogs, lots of personal ads and had correspondence with lots of men all claiming they want to have sex with a man or fantasizing about having sex with a man.  All I have to say is it is out there, all you have to do is open your eyes to the possibility.  I am in my mid-forties and the subway guy in the proceeding examples, was a well-dressed man in a business suit who hit on me on the past Wednesday at five o’clock in the afternoon and he gave me his phone number.  That is a true to life example.  I can’t be the only guy in this world getting hit on. I am certainly not God’s gift to men, but maybe because I am open to the possibilities, they appear.

Just some parting words for you to ponder.

The High School Years – boys, girls and men – Part 2

We now come to the men part of the story, or more importantly my first relationship with a man.  Yes it was a man, not somebody my age I had my first man on man sex with. This was a very complicated relationship, so it will take me a while to lay everything out, so please bear with me.  The other thing I want to make perfectly clear is that I was 18 years of age when we first had sex; there was no inappropriate sexual conduct between this gentleman and myself while I was a minor.

Mr. P was my music teacher and I started taking lessons from him when I was eight or nine years old.  Although I had known him my whole life as he was friend of my parents.  He was a life-long bachelor, who was always very well dressed; he was a little eccentric, and also fairly rich.  Mr. P was also rumored to be gay, he had never been married, so people surmised rightly of course that he was gay, but he was always nice to me and my family, so that never bothered me.  He was also a pipe smoker, and even from a young age I was always fascinated by his pipe lighting ritual.  I would just sit and stare as he prepared his pipe to smoke it and then finally light it.  I can still remember how nice his tobacco smelled as he was smoking his pipe.  Anyway if he had not been my music teacher I would have never been able to take music lessons because my parents would not have been able to afford itHe charged us next to nothing, and gave me lots of free lessons if I was preparing for a music competition.  He did not really need the money and he wanted to help me and my parents out.  He basically charged what we could afford and not anymore. 

When I started taking lessons from him he would have been in his mid-fifties, he was semi-retired; he had maybe fifteen or twenty music students.  As I stated previously he was always very well dressed, and he cut quite the dashing figure in his well-tailored suits and was quite handsome.  Not that I thought that when I was eight or nine when I started taking music lessons, but he was still very handsome at least in my eyes when he was in his mid-sixties and we were having sex.

That is almost the entire back story.  The only other details that are needed is that I grew up about two hours east of Toronto, which for those of you who are not familiar with Canada, is not only the largest city in the country, but is also the cultural center of the country.  Yes Montreal and Vancouver are also great, but if you want to see top-notch theater, opera, ballet or symphony orchestra concerts, on any given night, Toronto is the place to be in Canada.  Also remember that my relationship with Mr. P was going on at the same time as everything else in life but I have kept this separate from part 1 so as not to make it any more confusing.  One last thing, in the part of Canada I grew up in, at the time high school lasted five years, it went from grade nine to grade thirteen.  So if you are wondering why I could still be in high school when I was 19 years of age, it was not because I was flunking out, it was because of when my birthday falls and five years of schooling. On that note here we go.

Around the time I turned 14 Mr. P thought it was a good idea for my cultural horizons to be expanded and suggested to my parents that it would not hurt me to attend some concerts and plays in Toronto with him on weekends.  My parents agreed and off we went to plays and concerts every month or so.  I always had a great time with him, as he would treat me as an adult, and we would go out for dinner or lunch, so it was always a good time.  Mr. P also made almost weekly trips to Toronto without me.  He was always going to concerts and plays, staying over-night and then coming back home the following day.   With me in tow though, there was never any over-night stays; it was always into the city for the day and home that night.

Unfortunately one day as Mr. P was driving home from Toronto, somebody rear ended him on the highway, luckily not at high speed so he was not hurt too badly, but he lost his nerve to drive on busy highways.  That put a damper on our trips together to Toronto of course until I got my license.  He was actually very sweet about it; he phoned my parents and asked if it was ok, if he could ask me, to drive him to Toronto to see a symphony concert.  My parents said sure and two months after I had received my license, Mr. P and I set off in his brand new Cadillac to Toronto.  Even though he did not drive on the highways anymore, he always had a nice car to run around town in.

Looking back I do realize that this was the beginning of the seduction.  Mr. P may not have intended it to be but it was.  He did not make any overt sexual advances; but there were lots of little gifts such as new clothes to wear on our outings, the day trips were a little longer, we spent more time together.  For example instead of just going to a concert and grabbing a bite to eat, we would leave early in the morning, grab a bite to eat, spend the afternoon visiting an art gallery, have dinner, attend some sort of play or concert and then I would drive us home.  We also started doing things with his “friends” in Toronto, like going over to somebody’s place and having lunch or dinner, or maybe just stopping by for a visit.
Now I know some of you may find this boring, a teenager hanging out with a bunch of older men, but I found it fascinating at the time.  They would talk about many different subjects and always treated me like an adult.  Some of them would tease me for hanging out with Mr. P all of the time and his group of old men.  I always told them that it was my choice to be there and I enjoyed everybody’s company.  Did I know they were all gay, of course I did, some of Mr. P’s friends were so flaming they could light a candle from three feet away without even using a match.  Lol   But these experiences taught me lots of things such as the world is made up of all kind of people, some straight, some gay, some, somewhere in between, but we are all just normal human beings who can laugh, cry and love.  That was pretty heady stuff for a teenager from small town Ontario.  That was also about the time that I knew I was developing some sort of attraction/crush towards Mr. P, other than our student/teacher/friend dynamic that we showed to the rest of the world.

Now of course when I was not going to Toronto with Mr. P, I was still going to high school, working part time, trying to have a relationship with my girlfriend, taking music lessons from Mr. P, competing in music festivals all around Ontario, and dressing up whenever I had the chance.  I was busy, it was complicated at times and it was about to get a whole lot more complicated.

How complicated you ask?  Well shortly after my eighteenth birthday me and Mr. P, consummated our relationship.  For my birthday Mr. P took me to Toronto for the whole weekend.  He actually asked my parents if it was fine with them before he asked me, they did not have any problems because hey it was just my music teacher taking me to an opera, on the Friday night, a play Saturday night and a piano recital on a Sunday afternoon.  They even let me take a half a day off school, so we could drive into Toronto before the rush hour traffic and get checked into our hotel. 

When we checked into the hotel Mr. P had a little surprise waiting for us upstairs in our hotel room.  He had ordered a bottle of champagne for our room to celebrate my birthday.  Now I am not much of a drinker and I certainly was not one at eighteen, but from the time I turned fourteen years of age I was allowed to have a small glass of wine with dinner, and I had drank champagne before.  I was very excited, I was having a very grown up start to my weekend and it was about to get a whole lot more grown up.

After we had unpacked and got settled, Mr. P and I settled down on the couch to drink a glass of champagne.  He then presented me with a small box and a card.  I opened the box first and it was a very expensive watch.  I thanked him very much and then he said read the card.  It was a fantastic card where he basically professed his attraction to me and how much he wanted to get the watch inscribed on the back “with love from Mr. P” but knew that would not be appropriate.  I was flabbergasted, shocked, overcome with emotion and more than a little scared about what would come next.  I just grabbed his hand and mumbled about being honored to be his friend, and he meant the world to me and yes I felt the same way towards him.  With that he lead me to one of the beds, helped me get undressed and we climbed into bed together and he introduced me to the joys of love making with another man.

I will not go into all of the gory details about what transpired, and no we did not have anal sex; for those who are wondering, but I will say it was very tender with lots of kissing and rubbing of bodies and learning how to pleasure a man and be pleasured by a man.  One of the best moments was after we were done, just laying against him while he sat up in bed smoking his pipe and drinking another glass of champagne.

We of course had sex throughout the weekend and many more times over the next few months.  Although that was our only weekend away together, let’s face it you can only get away with spending a weekend away from home because it is a birthday present once, not on an ongoing basis.  All in all our sexual relationship lasted a little over five months.  When we were together everything felt so right, when we were apart I was filled with doubt.  I knew I was not strong enough emotionally to come out as being gay and besides I knew I still attracted to women; or was it more that I liked to dress as a woman, either way I still had feelings towards women.

I guess my biggest fear was being found out.  Since we had begun sleeping together Mr. P had started to become affectionate in public which was totally freaking me out.  I did not mind it if we were hanging out with his friends in Toronto, but in the small town where we lived, people would talk and then my parents would have found out, I would have been outed at school, it was way more than I could handle.  I knew there was nothing wrong with two men caring for each other and having sex together.  I would even tell my parents to watch what they were saying if I felt they were making inappropriate comments about gays, but I was just not mature enough at the time to handle the consequences of being a gay teenager, not that there is anything wrong with that, with a much older lover in small town Ontario.

So I broke it off just before I went back to high school for my final year.  I broke off not just our sexual relationship but our music teacher/student relationship as well and our trips to Toronto for cultural events.  I said I needed to focus on my studies and was giving up music to ensure I could spend more time studying to increase my grade point average.  Mr. P was visibly upset and I was upset as well because I really did care for him and enjoyed our times together immensely.

That was not the only thing I gave up, I threw out my little collection of make-up that I had acquired and vowed to stop wearing my mother’s underwear.  I was going to be a good little straight boy for my last year of high school.  No more experimentation, just study hard so I could get the hell out that small town and on with my life.  I was successful, graduated with honors and went on to University.

Looking back I do not have any regrets about my relationship with Mr. P.  He taught me lots of valuable life lessons and with his help I developed my life long appreciation of the arts as well as my life long appreciation for older men.  Ha ha ha But more about the latter another time.

Friday, August 27, 2010

The High School Years – boys, girls and men

Even though I liked to wear my mother’s clothing I never considered myself anything but straight, during grade school.  I loved how girls smelled, I loved how they looked, I loved the way they felt when I touched them.  I loved girls!!  So the funny thing is I had a homosexual experience before, I lost my virginity to a girl.  I know if you read my previous you are going you had a homosexual experience before you slept with a girl?  There is a surprise.  You had been wearing your mother’s underwear since you were eleven.  Yeah, I know but I was never attracted to boys, so looking back it was a surprise to me.

Now it was not anything special and lots of guys have done the same thing.  My best friend and I were riding our bikes in the woods during the summer before we started high school.  We decided to stop and take a rest, so we get off the path, moved in behind some bushes and put our bikes down, sat down and relaxed.  We started talking about girls, sports, dreams normal guy stuff.  Somehow we got on the topic of pubic hair and he suggested we show each other what we had. 

Now we had seen each other nude before, we were best friends, had stayed over at each other’s homes, and had gone away for weekends together with our parents.  Anyway, we look around pull down our pants and start comparing what we got.  Thinking back he did have a wonderful big dick, but the one thing I did notice right away was that he had no pubic hair.  I on the other hand had quite the little bush growing.  When I teased him about his lack of hair, he just laughed and said the reason he wanted to show me, was that he had shaved it all off.  When I asked him why, he just said because he liked the smooth look.  He then started masturbating and I was mesmerized.  He was so confident standing there jerking off in the woods with his pants around his ankles, so I joined in and we stood there jerking ourselves off until we both came. 

That was my first homosexual experience, beating off in the woods with my best friend.  As I said pretty innocent and I bet you if you ran a poll, most guys will admit to doing that when they were growing up.  Now the interesting thing about this friend is that he ended up being the first person I knew to come out as being gay in high school.  The funny thing was that in the last two years of public school and the first two years of high school, he always had a string of girlfriends.  Girls would not leave him alone.  But when he came back for his third year at high school, he came out to everybody.  We had drifted apart by that time because we were running in different circles, but I felt for him because he was ostracized by just about everybody.  But he stood his ground and made it through high school and then excelled later on in University and then after that went to law school and became a lawyer.

Beside that one experience with my friend at that point in time I only had eyes for girls, girls, and girls.  I will admit I was not much of a lady’s man; I was and still am pretty shy.  But I kept trying and finally landed myself my first real girlfriend in grade 9.  Things moved along quite nicely and during the summer between the first and second year of high school, I lost my virginity to her.  It was nothing spectacular; it was the usual, lots of fumbling around, having trouble putting the condom on, but I was very proud of myself that I lasted more than five seconds.  Lol

We lasted a few more months then broke up during the first semester of our second year.  During this time, I was still wearing my mother’s clothes any chance I got.  But once my girlfriend and I broke up, I decided that I needed a change in my appearance and it was time to get rid of the hair around my penis, and go for the that nice smooth look.  A couple of weeks later my parents went out of town for the weekend, so I was able have the house to myself and the time necessary to complete the task.  I took my mother’s scissors that she kept in the bathroom and trimmed as much hair back as possible.  Still not satisfied, I found my Dad’s electric razor and used the side burn trimmer, to get rid of some more hair; finally I pulled out my mother’s electric razor and finished the deed.  I was bald as an eagle and loving it.  I spent the whole weekend wearing my mother’s sexy panties everywhere I went.  To the mall, to work, I had no pubic hair and nobody knew!!!

On the Sunday before they came home I spent the day doing laundry, and cleaning so that there was no evidence that I had worn my mother’s underwear or shaved myself bare. I was extremely happy.  I knew I could not get away with shaving my legs; or torso because my parents would be able to see it, but my pubic area no one could see.  It was brilliant and fool proof.

And then the girl of my dreams decides that I am not an idiot and she really did want to date me.  Yikes!!!!  Here I am smooth as a baby’s bottom, and a hot girl wants to date me??  I had to go into damage control.  I went on a few dates with her, and no matter how many times she suggested we take it to the next level, I kept demurring and claiming that I wanted to make sure that I really loved her before I had sex with her.  For whatever reason, she bought that, and after 6 weeks, I figured enough hair had grown back that it was safe and lo and behold she did not say anything, but I was extremely nervous the whole time because I thought for sure she would notice that my pubic hair was not very long.
Next big life event of course was turning sixteen and getting my driver’s license.  Now you may be wonder how could the ability to drive have anything to do with this story?  Well two things actually, with the car I was able to venture out dressed “en femme” and being able to drive lead to my first relationship with a man.

I will start with the going out dressed as a female.  Now I will be completely honest I was not able to go out fully dressed up because I did not have any woman’s shoes.  But what I did do was go out in full make-up and, t-shirt and jeans, with a bra and panties on underneath.  I also, used to stuff the bra a little because if you are trying to pull off make-up you better have some cleavage.  Lol

The first time I went out in full make up it was very late at night on a Friday night.  My parents were out of town visiting relatives, I got to stay home because I was working on Saturday.  I had been playing around with some make-up that I had bought for myself (yes, make-up counter ladies are very helpful when you tell them you want to buy your mother some make-up for her birthday lol) and finally got it exactly the way I wanted.  For whatever reason, I just had this urge to go out and show it off.  So I hopped in my mother’s car and went for a drive.  After a few minutes, I got really scared, you know all those things start growing through your mind, like what happens if somebody sees me, what happens if I get in an accident, what happens if a police officer pulls me over for a traffic violation.  I quickly lost my nerve and headed home vowing never to do that again.

The thing is of course was that I was hooked.  There was a real thrill to going out in full make-up, wearing a bra and panties under my t-shirt and jeans and not getting caught.  So each time thereafter, whenever my parents went out of town, I would venture out and go a little further and stay out a little longer.  The other thing I decided was to get drive out of the town where I lived, therefore decreasing the chance of running into anybody I knew.  After a while I even got up enough nerve to stop into convenience stores to buy a can of pop.  I never said a word when I would go into the store, always made sure I was the only one in the store and I never got caught. 

To be continued….

Wednesday, August 25, 2010


I know that this blog is about crossdressing, and other such matters.  But I came across this image this morning and I just had to share.  For whatever reason, this picture is one of the most beautiful I have seen in ages.  I can not stop looking at her.  The image is from met-art.com

Monday, August 23, 2010

How it all started

I started trying on my mother's panties when I was 11 years old. I would sneak into my parent’s room, when they were out and go through my mother's underwear drawer. I quickly found her secret stash of "sexy panties" that she kept at the bottom of her drawer. I loved the feel of them next to my body and how they looked on me. They looked so much better than the “tighty whities” that I had for underwear. Lol

I quickly graduated to trying on my mother's bra's, nylons, shoes and clothes. I even started putting on makeup when time allowed. That was always quite the experience because I tended to have a heavy hand when it came to applying makeup, so I looked like a badly made up trollop.

I was always very careful to put things back exactly as I found them, but I am sure my mother must have suspected I was messing with her stuff, especially after I broke her eyeliner pencil one time, but she never said a word.

Actually my mother was an unwilling participant (or was she really a willing accomplice??) in my desire to explore dressing as a woman. When I was in grade six I insisted that I go dressed up as a woman to school for Halloween. So she put an outfit together, a skirt with a jacket and a blouse, a pair of pumps, pantyhose, a bra and a pair of my own underwear. No sexy ones from her secret stash.  She fixed my hair up, and even put some make up on me and sent me off to school.

I was in heaven! I thought I looked amazing and secretly wished I could go to school dressed as a girly every day. I received lots of compliments on my costume, so many in fact that I decided to dress up as a woman for Halloween in grade seven and eight as well. Lol Don’t get the wrong idea, there was lots of clandestine dressing up sessions in between official Halloween outings. But I really looked forward to those sanctioned days when I could go out in public dressed as a girl, even though I was supposed to be in a Halloween costume.

By the time Halloween in grade eight rolled around when my mother asked me what I wanted to go to school and I said same as last year, she actually said “no”. When I asked why not, she said “that my feet were too big to wear her shoes, and that my legs were too hairy to wear nylons.” Damn puberty!!! Well she was right about the shoes, I knew they did not fit, but I still knew her clothes fit, they were a little shorter on me than her, but they still fit. Her suggestion was to dress up as a hobo and leave it at that.

I was heart-broken, devastated, I had already picked out the dress and jewellery I wanted to wear. Lol!! After much sulking and complaining, and you let me dress up last year comments, she finally relented. But she made me work for it and put up little challenges and roadblocks along the way in order to thwart me.

For instance she made me phone one of her friends to ask if I could borrow a pair of shoes to wear. Then there was the hair on the leg thing. Not that I had a lot of hair, it was just starting to grow, but she insisted that the hair had to go, or I had to go dressed up to school as a hobo.

So the night before Halloween, she had me put on a pair of gym shorts (they were much shorter than the ones the kids wear today) and she took me into the bathroom; pulled out her electric razor and showed me how to use it. She then rolled up the gym shorts slightly and said “I was to shave my legs up to the rolled up hem. That way when the hair started growing back it would look normal.” Kind of like my leg hair was growing in for the first time. I also had a little under arm hair she said had to go as well. I looked at her and said ‘OK” and went to work.

I had secretly wanted to shave my legs since the hair on my legs had started growing in. Now I had the blessing of my mother to get rid of it!! After about thirty minutes or so, she came back in and checked on my progress. I thought I was pretty much done, but she felt my legs, said “there was still hair on them”, grabbed the razor and finished up the job. She then rubbed baby oil on them and off to bed I went happy as a clam.

The next morning, she had a surprise for me; she had borrowed a wig, from a friend for me to wear, and she had laid out a full complement of woman’s undergarments for me, including panties!!! She said, “If you want to dress like a woman, you have to look like a woman, and that means from the top of your head, right down to your shoes, and underwear. Now go put your panties on and come back and I will help you get dressed.”

Anyway, I came back with my panties on, and she helped me get dressed. She even stuffed my bra for me, so that I had some cleavage. Next came the wig and make-up and of course pictures. I got lots of “doesn’t my little girl look pretty” comments from her, still trying to stop me. But I kept looking in the mirror saying to myself yes, I do look pretty. Lol. She gave me a purse to carry my keys and put some money in and off I walked to school.

If you have not figured it out yet, my mother kept trying to humiliate me into not going dressed as a girl. Whenever she did not want me to do something, she would use humiliation to bring me back in line. This time it back fired on her though, because everything she used to try and humiliate me, was what I wanted. So I won this round, but she would use this against me for years to come.

Also, for whatever reason me dressing up as a woman as a thirteen year old, was not as acceptable as when I was eleven or twelve. Maybe she thought I would get teased or maybe she knew I was wearing her stuff and she was not home, but could not bring it up. Who knows, but I certainly did not get teased that day at school for my costume, but I did get some weird looks the next day when I showed up in gym class with my shaved legs.

Actually that year, I kind of freaked out my teacher. I think me dressed up as a girl for the whole day was making him uncomfortable; he came over and quietly asked me if I wanted to change into something else. I said no I was perfectly fine. He then suggested that I take off the dress and wear my gym clothes that I had on underneath the dress, and then when it was time for the party I could put the dress back on. I politely said to him that I was not wearing gym shorts under my dress but was wearing a bra, a slip, panties and pantyhose. His face went beet red and he walked away.

He actually brought it up with my parents at a teacher parent interview a couple of weeks later. He said that he thought it was inappropriate for a 13 year old boy to be wearing woman’s undergarments to school, even if it was Halloween. He felt I should have been wearing shorts under the dress, not woman’s underwear. My mom just shrugged and said it was my decision and she had done everything she could think of to stop me.

The thing was that dressing up secretly behind my parents back, or dressing up as a woman for Halloween was never a sexual thing for me. Oh I will admit that as I hit puberty, putting on a pair of panties gave me an erection, and I became sexually aroused, but after a while the erection went away and I just enjoyed the feeling of clothes and looking at the transformation in the mirror.

Saturday, August 21, 2010

First post

Well here we go my first post on my brand new blog. I have never had a blog before so please bear with me while I go through the growing pains of getting this thing started.

First off my name is Sissy Sidney; i am a mid- forties male, sissy cross dresser.  I
 am sure most people would not consider me a "sissy" in a traditional sense, I am not even sure I am a "sissy", but through this blog I do hope to explore who I am. I do know that I am bisexual, not bi curious. I have sex with both men and Woman, and enjoy both sexes equally. I am also a submissive but have only had the opportunity to submit to Dominant Males.  At one point in my life i was also in a long term live in Master/slave relationship that lasted two years.  

In fact, until recently, I had not worn woman's clothing in almost fifteen years.  You might say that I got lost on my journey through life and am finally being true to myself again.

Anyway, this blog is going to contain postings about my past experiences, and things currently going on in my life.  The past experience postings are to help me work some things out, and hopefully provide some insight for others as they move through life. 

I hope you enjoy the blog.

Sissy Sidney