Saturday, December 31, 2011

Last Caption of the Year - Daddy's Girl

I hope everyone has a Happy New Year and may all of your dreams and wishes come true in 2012.


xoxoxoxo Sidney



Sunday, December 18, 2011

A new Caption

Not sure if this one works or not.  But you never know until you try.  I do hope you enjoy.


xoxoxoxo Sidney



Friday, December 16, 2011

Saturday, November 5, 2011

A new caption. Tormenting Sissy

Not sure if this caption works or not, but I love the model so I just had to try.  I do hope you enjoy.


xoxoxox Sidney



Sunday, October 2, 2011

Something Different

Not sure if this works as a caption or not but I absolutely love the image so I had to give it try.

xoxoxox Sidney


Saturday, October 1, 2011

New Caption

Another try at a caption.  I do hope you enjoy. 

xoxoxo Sidney


Saturday, September 10, 2011

Sunday, July 17, 2011

The University Years Part 4 – Finally some dressing en femme

This is the last time I will mention Bill, after we broke up I went back to my routine of hanging out with Steve and his buddies; going on a few dates and concentrating on school.  It was very relaxed no pressure and at lot less intense.  The next bit of drama to unfold was that I needed to find a job for the summer or I was going to have to give up my apartment and move back in with my parents for the summer.  That would have been very bad because after exploring my sexuality so thoroughly during my second year of University there was no way I could go back to living with my parents and their rules.  Luckily my Gay bear angel Steve had a friend who would hire me for the summer working at his business doing office work, answering phones, filing and doing some basic accounting duties.  Luckily it paid enough to cover my rent and still let me save some money for school.  Steve also promised that in the fall I could pick up a shift or two a week at his bar to earn some extra money to help cover my expenses if I needed some extra money.  So all in all it was going to be a great summer.

One day after work I was in a bookstore checking out some novels when a gentleman started up a conversation with me.  You know basic stuff like he had read that book and thought it was excellent, or had I read any other books by that same author.  So we talk for about 10 minutes or so, and I am just about to say good-bye and he introduces himself as Mark and asks if I would like to go for a coffee and talk about books some more.  I say sure so we buy our books and head over to a coffee shop for a coffee.  I am thinking to myself well this guy certainly seems nice, and pretty smart, and it was nice of him to suggest we have a coffee so that we could continue our conversation. 

So we grab a coffee and sit down at a table and continue our conversation for about an hour.  Mark was a pretty good looking man, fiftyish, grey hair, wearing a suit and tie, clean shaven, and a nice smile.  We finished our coffee and as we standing outside of outside saying our goodbyes Mark asks if I might be interested in meeting him again tomorrow at about the same time, at the coffee shop and we could go back to his place for dinner and he would show me his collection of books.  Duh!!  Of course he was nice, he was hitting on me!  That was a first for me, getting hit on in a bookstore.  It was also the first time I had ever been hit on in a non-gay setting.  All the other times a man had made advances towards me; I had either been seduced or had been set up on a date.  I said sure and we agreed to meet up the next day after work which was a Friday night. 

So the next day we met up outside of the coffee shop and, we drove over to his place which was in a much nicer part of town than where I lived.  We went in to the house, Mark poured us a glass of wine and then he gave me a tour of his house.  It was very nice, with a great den/library that had lots of books and winged back chairs to sit and read in.  There were lots of photographs all around the house, including some nudes, which were of very high quality and I asked who the artists were he said that he was.  He said that he was a bit of a shutter bug, and when he was younger even thought about becoming a professional photographer, he even had his own darkroom in the basement.  In a lot of ways he reminded me of my first male lover Mr. P. in that he was obviously pretty well off, and had a bit of an artistic streak and dressed well.  So we hung in the kitchen while he prepared dinner, turned out that he was a lawyer, had been married in his early twenties, got divorced before he was thirty and had been single ever since.  Mark liked to travel when he had the chance and had actually just turned sixty.  I told him that he must be lying to me because he looked fifty at the most.  He gave me a little peck on the cheek and said that I was being very sweet but no he was really sixty.

When he gave me the peck on the cheek that was the first time he had touched me, I remember thinking to myself; that it was about time because I thought I might have been wrong about why I had been invited over. 


After dinner we retired to the living room with another glass of wine and continued talking.  Finally Mark brought up the topic of sex and very politely asked me if I would like to spend the night with him.  He told me that he realized that he was much older than me, but he thought that I was very attractive and wanted to fuck me.  That is what I have always liked about older men they at least tell you what they want without beating around the bush.  Lol

I told him that I loved the idea and had been hoping he would make a move all night.  So he told me to grab my wine glass and then he grabbed my hand and led me upstairs.  Once upstairs he undressed me and was delighted that I was smooth all over.  As he undressed he made a comment that he would love to fuck me while I was wearing a black garter belt and stockings because it would look great against my smooth white skin.  Well I just turned beet red because a man had never said that too me.  He looked at me and said “Are you into that?”  I sort of stammered and stuttered for a moment and then said “Wait here I will be right back.”  He left the room for a couple of minutes and then came back in with some stockings and a garter belt. 

I said “I really am not into that stuff.”  But Mark replied, “For someone who is not into this stuff you sure have a raging hard on.”  So he came over gave me a big kiss with lots of tongue and put the garter belt on me.  He then helped me on with the stocking and attached them to the garter.  I just stood there getting redder and redder.  Finally when he was done, he stood back and said I looked very beautiful.  He then led me to the bed and started making out with me.  Mark was very passionate and very tender and it was as much about me receiving pleasure as him.  I was really turned on but was feeling a little freaked out by wearing the stockings and garter belts and being with a man.  I know I had always dreamed of it happening but all I could hear was the disdain of Steve’s voice in my head making comments about Sissy faggots and not being real men for wearing lingerie.  Steve was all about masculinity although he too liked it that I was smooth all over but he claimed it was because he liked the person he was fucking to be smooth not that that they were in any way femme.

Mark reached into his bedside table and pulled out a small bottle and opened it up.  He then put it under my nose and said “Have a sniff of this it will help you relax.”  I asked what it was and he said that it was called poppers and after a couple of sniffs I would feel much more relaxed and passionate.  So I inhaled deeply a couple of times and wow did I feel horny.  I felt this how flash all over my body and a little light headed, but I could feel all of my inhibitions just melting away.   Mark then rolled me over onto my stomach lubed me up, slipped on a condom, then had me get up on all fours and started pumping.  He reached around every few minutes and told me to inhale the poppers again.  I just did as I was told and let him keep riding me until he finally exploded inside of me.  After he pulled out, he took off his condom and then went down on me and gave me an amazing blow job.  After I had blown my load Mark came up and gave me a deep French kiss, and still had some of my cum inside his mouth.  Which is a real turn on in my books, tasting your cum on someone’s else’s tongue.  Mmmmm

So after we finished and lay relaxing in bed drinking some wine I asked Mark why he had stocking and garter belts.  He laughed and said that he had a huge collection of lingerie because he liked bringing men home and having them dress up in the lingerie and then fucking them.  He said that he had lingerie in various sizes, styles and colors, plus shoes, wigs and even some dresses, skirts and blouses.  I asked him if he ever dressed up and said no, he did not dress up but he was attracted to men who did like to dress up.  He then asked me about my experiences and I explained to him that I only dressed up at home, except for the few times in high school that I went out late at night dressed driving around in a car.  I also told him that he was the first man who I had ever had sex with while wearing woman’s lingerie. 


After that we went to sleep the next morning Mark asked if I would like to go home or spend the day hanging out some more.  I said I would stay if he wanted me to.  So we grabbed a shower together and he asked if he could shave me.  I said I had shaved everywhere the previous day but he said that he wanted me silky smooth so he lathered me up and shaved me from my neck down completely; which was very erotic.  We then got out of the shower and I shaved my face while Mark towelled off and then went to get dressed.  Once I finished shaving my face I was smooth from top to bottom and ready to play.  Lol

When I got back to the bedroom Mark had a bunch of different outfits laid out for me.   I stood there stunned because everything looked gorgeous; he had great taste in lingerie and even had brought out a couple of dresses and lots of shoes for me to try on.  I asked what he wanted me to wear first, he said try to find some shoes that fit and then we will go from there.   I tried on all of the pairs of shoes and found two that fit, a pair of black pumps with 3 inch heels and a pair of red open toed pumps with similar size heels and then the dressing began.  I stayed with him all day Saturday until Sunday afternoon playing dress up.  I could not tell what got him more excited the woman’s clothing or me dressing up in them.  He certainly was the only gay man I ever met who got off on woman’s clothing.  After I had tried on some of the outfits he already had laid out for me, he took me to a small bedroom that had been converted into a closet and it was full of woman’s clothing.  He had dresses, skirts, blouses, shoes, and enough undergarments to stock a small store.  Whenever he would pull something out you could just see his eyes light up when he talked about the garment and you could see him get a hard on under his pants.  It was truly amazing.

He fucked me at least four times on Saturday and once before I left on Sunday and he gave me over a half a dozen blow jobs.  There was certainly a lot of sex and I was very tired when he took me home on Sunday afternoon.  He even gave me some lingerie, a couple of dresses and shoes to take home with me.


So Mark became my summer romance between second and third year of University and the relationship lasted about two months.  We would get together on weekends, meeting after work on Friday and then we would spend until Sunday afternoon together.  Every weekend he always surprised me with a new outfit and lots of new lingerie.  I kept telling him that was not necessary but he insisted because he wanted me to look good and have nice things.  I would dress for him all weekend long and we would have lots of sex.  Eventually he convinced me to allow him to take some photos of me some nude and some dressed up totally.  I wish I still had them because some of them were pretty good if I do say so myself, but I purged them in my mid-twenties when I was going through one of the periods when I was getting rid of all things that had to do with wearing woman’s clothing and all things gay, vowing to be a good heterosexual man, and never having sex with another man again.  Like that ever lasted for long.  Lol

Anyway, what finally broke us up was that I got bored.  Mark was a lovely man but I missed going out and doing stuff.  I hated being in the house all of the time and when I was with Mark all we ever did was stay in house so that I could be dressed up in female clothes because that is what he liked.  I liked it as well but offered to wear woman’s lingerie under my male clothes so we could at least go out; but that was not the same for Mark.    


As they say every relationship is a learning experience.  From my relationship with Mark I learned that there were men out there who liked guys who dressed in woman’s clothing and when I was dressed as a woman I could be considered sexually attractive, well at least to one guy.  I also learned that I needed more than just dressing up to make a relationship to work.  The fact that I was not comfortable going out dressed because I did not want to be found out was a problem.  But the fact that Mark only wanted me fully dressed all the time was also a problem that we could not overcome.

 





Saturday, July 16, 2011

Two captions for the price of one!

I do hope you enjoy.  Below are a couple of captions that I did today.

xoxo Sidney



















Thursday, July 14, 2011

The University Years Part 3 - More Bill

I promised more about Bill so here it goes.  Our first night together, was very vanilla.  We went back to his place; he put my clothes into the wash and had a shower together.  Afterwards we sat around having a couple more beers and talking.  He asked lots of questions about me, my sexual history, upbringing, and whether any of my family knew I was gay.  I protested that I was not gay; he laughed at the comment and said “Yes you are; you just will not admit it.”  After my laundry was done we went up to his bedroom and had sex.  He certainly was not tender when making love to me, but he was not overly rough either.  There was lots of whispering in my ear about the fact that I liked being fucked by older men.  That I liked grey hair, and wrinkles and that was why I was nothing but a gay boy looking for a Daddy to look after him.  I just went with it, because I was thoroughly enjoying myself.  After he finished fucking me, we went to sleep.  

That was the only time Bill ever had sex with me in a vanilla manner, and it is only vanilla if you discount the part about him having me pee my pants in front of four other men before he took me home and fucked me.  Well at least the fucking part was vanilla.  Lol

This was a true Dom/sub relationship, when we were together Bill was always in charge whether we were in his house or out in public for the approximately two months that we were together.  At home I always called him Sir; when we were out in a vanilla setting I called him Bill, but I always deferred to him, in restaurants and bars he ordered for me and spoke on my behalf.  If I spoke out of turn when we were out; there would be a punishment waiting for me when we got home.  He always referred to me as boy, or “my boy” in social settings or “pee boy” if wanted to embarrass me.  Thankfully he only called me “pee boy” when his friends were around.  Bill was big on humiliating me and did so any chance he had.  I always turned a bright shade of red whenever he humiliated me and it was always a great source of laughter for him.

The “pee boy” moniker came about because of the time I wet myself the first time we met, and the fact that Bill attempted to bathroom train me, which resulted in more than a few accidents when I could not hold my bladder as long as he required.  Bill also introduced me to golden showers so I was his “pee boy” in more than one way.

Bill was also into cum control and I was not allowed to masturbate and he never gave me a blow job or a hand job during the two months we were together.  He was into prostrate milking though and on weekends he would milk me two to three times a day.  I must admit the orgasms caused by prostrate milking can be very intense, it is the dribbling of cum that drives me crazy.  The little dribbles of cum that just seem to go on forever, when all I really wanted to do was blow a full load.  I have come to appreciate them now more that I am older, but when you are twenty years of age, you just want to get off.   Of course because I was only twenty sometimes I did blow a full load when I got too sexually excited during a full on training session, that of course led to a punishment but at least I got off.  Lol

I could probably write five blog posts about my experiences with Bill each in excess of 5,000 words each but I am not going too because that would be way too self-indulgent and I am pretty sure nobody would read them.  So I am going to try and be brief and wrap this relationship up in a few paragraphs.

It was a very intense relationship.  I would submit to anything Bill wanted me to do.  I would leave his place after spending all weekend with him from Friday night to Monday morning, covered in small welts and bruises from the spankings and floggings he gave me during our time together and I would be back the next Friday night for more.  There may even be a midweek session if our schedules allowed.  The one thing I was always adamant about was that school was very important to me and I would not do anything to screw that up.  So I was always allowed a few hours on the weekend to myself to do some studying maybe three or four hours a day.  The rest of the time would consist of training sessions as Bill called them, with maybe a social outing on the Saturday night.

A typical weekend was I would meet Bill at his place on Friday evening, we would have a two hour training session, then stop for hour or so and have something to eat, another training session and then I would be milked then it was off to bed.  On Saturday morning, we would be up early usually around 6 AM; and go right into a training session for at least two hours.  Then I would be milked and have something to eat and have a shower together.  Bill then usually drove me to the library at school where I would write papers, study or read for three or four hours.  Which meant that he usually picked me up again by 1 or 1:30 pm, it was then back to his place for some lunch then another training session in the afternoon.  There was then a break for dinner, then if we were staying in we would have a long training session that lasted to ten at night, then I would be milked and then off to bed.  If we went out, there would be a short training session, then we would get cleaned up and go out for the evening, come home I would be milked and then off to bed.  Sunday was the same as Saturday except that we never went out, so it was always a long training session after dinner.  Monday, Bill would drop me off at school on his way to work and then we would start all over again the following weekend.

Training sessions consisted of corporal punishment sessions (at least one per day), some sort of bondage session and or torture session, where I would be tied up and subjected to verbal abuse and or humiliation, some sort of sexual scene that would involve bondage and or S&M.  I was always pretty tired and sore by the time Monday morning rolled around, but I certainly learned a lot.  Bill never leant me out to another Master during our time together and did not subject me to being passed around as a sexual object to his friends.  A couple of times he did have people over to watch our sessions which kind of freaked me out and exhilarated me at the same time.  I guess I had a little closet exhibitionist in me that got off on being trained in front of people.  It certainly freaked me out because I was a little bit ashamed of myself and what I was doing and having one to me.  It is that little voice in the back of your head that keeps going you may not be able to admit it but you are a screaming homosexual.  Letting some guy fuck you then pee on you and then letting another man watch, you are nothing but a fag.   Lol!  Believe me I heard that voice often.

The relationship ended because Bill wanted me to come out to my parents that I was gay and move in with him.  His reasoning was if my parents freaked out and disowned me he would pay for my schooling so really there was nothing to hold me back from moving in with him and becoming his full time submissive and lover.  The thing was that was very sound logic, but I was not in love with Bill; I was in love with submitting to Bill.  I absolutely loved giving up control, being a true submissive and loved submitting to Bill, but I did not love him and he wanted me to both love him and submit to him.  I did things with Bill that I am still not proud of today and have never done again with anybody else, but that was because I was so turned on by being his submissive I would do anything for him.  I knew that living with him would mean that there would have to be some sort of domestic dynamic and I could not be what he wanted me to be.  So I did what every good person does and lied my pants off.  I told him that I was not ready to come out yet, because I was experimenting with my sexuality and it did not mean that I was gay, and at best I told him it meant I was bisexual.  He called me lots of nasty names and called me a liar, which of course I denied because I did consider myself bisexual, but it did save me from telling him that I did not love him.

So that was the end of my relationship with Bill, later on I learned he had ended up moving away a couple of months later because he got a better job in another city.  I am not sure if I was the cause of that; or if he was really looking for a new job, but I never saw him again after the day we broke up.

Sunday, July 10, 2011

The University Years Part 2 - The introduction of Bill

This blog had not developed the way I had imagined.  The retelling of my sexual history in University and of my first sexual encounter with Steve in a previous blog; brought back a tidal wave of memories and emotions that I needed to work through before I could continue.  In fact I developed a severe case of writer’s block, and no matter how long I stared at the computer nothing would come out, and if anything did it was certainly not good enough to publish.  I even tried to work through the writer’s block by doing some captions, but even though I posted them, most of them were not very good in my opinion, except for a few at the end which I think are pretty good.  I am going to leave the captions up though as a reminder to myself of the feelings I was going through at that time. 

So I am going to try and get this blog going again the way I envisioned it and hopefully by working through my emotions I can put some of the skeletons in my closet to rest.  I am not going to go through every sexual encounter I had during my time in University because for one thing it was many years ago and I do not remember them all.  LOL!  But I will retell a few adventures because they stand out to me and helped define who I am today. 

As I mentioned in a previous blog Steve became my first male fuck buddy, we were not exclusive with each other because he knew I was not ready for a relationship and that I needed to fully explore my sexuality.  Although Steve did like his sex rough he was not into S & M, he was more of a slap and tickle kind of guy, but he would tie me up on occasion when he wanted complete control over me.  Steve was my introduction into light bondage and light S & M, but there was never any Domination/submission aspect to our relationship.  Truth be told although things were supposed to be casual between us I was really true in love with Steve.  He was right in that I needed to explore my sexuality but I truly valued our time together and would do anything to please him.  I believe he had deep feelings for me as well but could not get over the age difference, he was in his 50’s and I was only 20 years old when he first fucked me. So although we had amazing sex, he never told me that he loved me even though he was my Gay Bear guardian angel for the rest of my university days.

Now as part of my Master class in all things gay Steve did introduce me to his gay friends and set me up on more than a few dates.  I used to kid him that he was like my pimp because every time I turned around he had me going out on a date with somebody.  He also gave me some grooming tips and told me that given my body type, and the fact that I preferred older men, it would be to my benefit if I tried to keep myself pretty much hairless, as that was a big turn on for a certain segment of men.  I had not shaved all of my body hair off since high school but after hearing this news I went home and shaved everything off and tried to shave a couple times a week to keep smooth in case something ever came up. Lol

During this time I had not even thought about dressing because I knew Steve’s feelings about guys who wore woman’s clothing.  He was not a big fan and I had heard him make a few disparaging remarks a couple times about femme leaning men.  But the being completely smooth did give me the itch again, so I bought some bras and panties to wear around my apartment, but that was my little secret.

Most of the guys Steve set me up with were around his age or older so they would have been fifty plus, although there were a few in their forties.  He kept trying to get me to find someone my own age, but I was so far in closet I could not even find the closet door.  At school no one knew about my penchant for sleeping with men.  All of my classmates just assumed I was heterosexual because I never gave them a reason not to and that was the way I wanted to keep it.  I went out on a few dates with some woman I met at school but nothing serious, but once I got back to my apartment, or my local bar, or Steve’s apartment, it was all men all the time.

Most Friday nights became date night, Steve would have my gentleman caller meet me at his bar, and if we got along, off we would go for dinner, or a movie, or drinks at another bar.  If we did not get along, it would just end there, no hard feelings.  Saturday nights I would usually hang out with Steve at his place, we would watch some sports and then get all hot and sweaty or he might have some buddies over to play poker so I would sit around and watch or we would go to a party or something.  It was a pretty good life. 

Whenever he had the chance Steve further tried to enlighten me about gay culture.  He explained that I was definitely a bottom, who was attracted to Daddies.  I had to agree with him because I was truly turned on by older men.  I also liked my men to be on the large size, not fat, but a little chubby with a bit of a tummy did not bother me at all.  He explained to me what he knew about the leather culture when we saw some leather guys in a gay bar in Toronto.  He also tried to explain the Dominant and submissive dynamic involved in the scene.  I was really intrigued by this and was determined to learn more.  I asked Steve if he knew any Dominant leather guys and he told me yes and I asked him to introduce me.

So a couple of weeks later Steve introduced me to a gentleman at a party whose name was Bill.  He was in his mid to late forties, around 6 feet tall, medium build had black hair and a beard and was holding a pipe.  Steve told Bill my name and said I was the guy he had told him about.  Steve then left us on our own and Bill turned to me and said “For the duration of this conversation you are to call me Sir, if you do not call me Sir at any time I will walk away from you and the conversation will be over.  There will be no second chances.”  I looked at him and said “yes Sir I understand”. 

Bill then launched into a long speech about his philosophy on bondage, Domination and submission, discipline and his training methods to get submissive males to submit to him.  I just stood there mesmerized.  He just oozed power and confidence and his eyes seemed to look right through me into my soul.  I was both scared and excited at the same time.  After he was finished he asked why I was interested.  I told him about my experiences with Steve and that some of our best sex in my opinion was when I was tied up and had given up complete control.  I told him that giving up control to another was an aphrodisiac to me, the more control I gave up, the greater the freedom I felt and more I enjoyed himself. 
Bill then explained to me that it was not always about sex, it was about the exchange of power, one person giving up their power to another individual, or even someone taking the power from another individual under the right circumstances to push the other person’s limits.  Furthermore, sex could be used as both a reward and a punishment depending upon the dynamic and the situation.

I just stood there dumbfounded and did not know what to say. There was this whole other world that I never knew existed but I knew I belonged.   Bill then asked me if this would be something that I would be interested in exploring.  I stammered “Yes Sir”.  He said “Excellent, let’s go grab a drink, then go outside so I can smoke my pipe, and continue our talk”.  So after grabbing a drink we headed out to the backyard so that Bill could smoke his pipe and we could continue talking.  As we stood in the back yard, he showed me how he loaded his pipe with tobacco and told me to pay close attention because that would be one my duties during our training sessions.  I paid close attention to the ritual and knew it would take me a few tries to get it right.  After a few minutes, I said “Excuse me Sir, I will be right back I have to go to the bathroom,” and handed him my glass and started off to the house.  Well that was a huge mistake.  He grabbed my arm, pulled me back and said “Did you ask permission to go to the bathroom and how dare you hand me your glass, do I look like your maid?”  Now I was taken aback because I thought I had been very polite, saying excuse me and even calling him Sir.  Obviously I was mistaken.  He then said to me, “You do not leave my presence unless I dismiss you, or you ask permission and I grant you permission to leave and you certainly never hand me your glass.” 

I said “Sorry Sir, may I please leave you alone for a few minutes, so that I may go to the washroom”.  Bill looked at me and replied “No”.  From the look in his eyes I could tell he was not kidding.  So I just stood there for a moment and tried again “Sir may I please go to the bathroom?”  He replied “What part of no did you not understand?  Are you stupid or something?” Now I was becoming somewhat flustered by the fact that I really had to pee, but I said nothing thinking that anything I said would only make matters worse.  Bill then said, “Here are your choices: your first choice is to leave and go to the bathroom, which if you choose; do not bother coming back because you are obviously not serious about being a submissive.  Your second choice is to stand here, carry on a conversation with me, and when you decide you can no longer hold your pee; you wet yourself like the little boy you are.” 

I stood there with my mouth open not knowing what to say when finally I just said “So it certainly is lovely weather we are having now isn’t it.”  Bill looked at me and said “Good boy, now wait here while I go get a couple more drinks.”  So I stood there waiting in the back yard and eventually Bill came back with two glasses of water and a couple of beers tucked under his arms and a big smile on his face.  “Sorry I took so long boy but I had to stop and go to the bathroom.  I thought you might have gotten thirsty since I was gone and brought you some water.”  He handed me a glass and said, “Drink up boy; all in one go now, no stopping.”  I took the glass and drained it and as soon as I was finished he said, “One more time boy, I know you are really thirsty.”  So I grabbed the second glass and downed that one as well.  Bill just smiled and said “Excellent work boy, here now I have a beer for you as well, but you do not have to drink that one all at once.”  I took the bottle of beer from him and said “Thank you Sir, you are very kind.”

After a few moments he said “Here is your final chance to leave.  I know you are new at this and you are trying to put on a good show, but if this is not for you, just leave now, go inside the house go to the washroom and then have Steve take you home.  Maybe when you are a little older, you can find someone like me and try this again.  But if you decide to stay, you will pee your pants and in front of an audience.  In fact within the next two minutes two of my friends who are also Dominant are coming to join us.  I told then I was breaking in a new boy outside and as punishment for not asking permission to go to the bathroom that the new boy was going to wet himself.  They thought that sounded like great fun and could not wait to join us.  So just tell me your decision boy and if you leave that is ok, this lifestyle is not for everyone.”

I stood and did not know what to say.  The one thing I did know was I was not leaving.  I felt very alive at the moment.  Finally I just said, “I am staying Sir.”  Bill looked at me with a bit of amazement and said, “Fine boy, this is your decision I hope you know what you are getting yourself into, I do not just play at this life style I live it.”

With that I heard a noise behind me, I looked around and there were four guys coming out of the back door.  One of the guys said “Hey Bill, I hope you do not mind but when we told a couple people what was going on, they wanted to come for the show as well.”  Bill just said “That is fine, the more the merrier.” 

Everybody sort of gathered around me waiting for me to start peeing.  Finally Bill leaned in to me and said, “Just do it, you know you have to pee badly.  Just close your eyes and let your bladder go.”  After a moment I started to concentrate and then I could start to feel pee come out of my dick, first slowly then in a big rushing flow.  Then I started to sob, I could not believe I was standing in front of 5 men peeing myself, I was so ashamed.  I just stood there blubbering and peeing myself for what seemed like hours but really was only a couple of minutes.  Finally, I stopped and looked down at my pants, they were soaking wet. Even my shoes and socks were wet from the pee running down my leg.

Bill looked at me and said “Don’t you feel better now!  And what lesson did we learn from this boy?”  “Always ask for permission to leave your presence Sir, or wait until given permission to leave.”  I replied.

“Excellent Boy, now gentleman if you will excuse us, I am going to take my new boy home and get him cleaned up.”  With that Bill lead me out of the back yard and down the street.  He told me that he did not live far away and that he had walked to the party.  He told me that once we got home, I could shower and then throw a load of laundry in so that my clothes would be clean for morning.  He also told me that he was going to fuck me hard, as a reward for accepting my punishment. 

I will tell you more about Bill another time, because he played a pretty important role in my life for a couple of months.  Whenever I have told anyone about this adventure, they ask why did I pee myself in front of those men?  Why did not just not leave?  The answer is kind of complicated but at first I did not believe Bill would make me do it, I was trying to call his bluff.  Then when I figured out that Bill was not bluffing, I did not want to appear like I could not take my punishment.  He kept challenging me to back down, and I became stubborn.  When I finally did pee in my pants I was really humiliated, you have no idea; that is why I started to cry.  But the thing was it was very cathartic. After I had done it, I realized that I could do anything; and I would certainly do anything Bill asked me to do because it felt right.  I was also extremely turned on, and I freely admit that it I am a humiliation slut.  I turn bright red, shake and cry, when going through the situation but afterwards I have the libido of a dog in heat.

That is it for now.  I am sorry that this is such a long posting.  I do promise to post more on a regular basis.

Caption - Becoming Sissy Sidney

This is a rather long caption, I probably should have made it a story.  I do hope you enjoy.


xoxox Sidney



Saturday, July 9, 2011

Feeling inspired today, here is another Sissy caption

I do hope you enjoy.

xoxoxo Sidney

Another try at a Sissy Caption

From the stats on my blog I can see that lots of people are looking at my posts but there are never any comments.  I do hope you enjoy what I am posting.


xoxox Sidney



Thursday, June 30, 2011

Sunday, June 26, 2011

Another try at a caption

I seem to be getting a quite a few views on some of my captions, but no comments.  I do hope you enjoy them.

Saturday, April 30, 2011

Magical Apron


Another attempt at captioning.  Please let me know if you enjoy it.




Saturday, March 19, 2011

Could be perfection

 I love her curly hair and her face.


Her perfect breasts


And her lovely ass.


She may be perfection.  



Tuesday, March 15, 2011

A beautiful back

Call me weird but I have a thing for woman's backs.  I think they are under appreciated and when I see a nice one I could stare at it for hours.  Below are some pictures of a model from met-art that I found today.  The model has a beautiful back.  Just the right amount of muscle tone/muscle separation and great shoulders to boot.  I would die to have a back that looked like this!!  Imagine how sexy it would look in a backless black gown!!  Men would be drooling and all of the women would be envious.  I have included a front shot as well so you can see the whole package.  Very nice athletic body.  


Anyway, time to hit the gym some more in the hope of achieving this type of back!!






Sunday, March 13, 2011

My first Caption

I thought I would try my hand at captioning.  Please be gentle.  


Saturday, March 12, 2011

A parade of butt's

Sorry since my last post I have been fascinated by woman's buttocks.  I just cannot seem to get enough of them.  Lol Below are a few that have tickled my fancy over the last week.  I will say one thing though, if my ass looked anything like any of the butt's displayed below, I am pretty sure I would be wearing nothing but short skirts everyday so I could flash my ass to people all day long.  :)








As a guy I find these woman absolutely stunning, but as as Sissy I would much prefer to be "them", than to be with them.