#openmouth4cock.blogspot.com

[openmouth4cock]

First time dressed as a woman

By then I probably would have been around 22 years young and still together with my second love. She always wanted an experience with a woman and I wanted to dress up as a woman ever since watching shemale porn. A threesome was out of question as she was way to conservative to let a third person intrude our private sexual life. Hence, I mentioned that I would like to dress up like a woman once. She was open to the idea and we decided on a date. 

To my personal surprise and certainly also to her surprise, I took it very seriously. I shaved my whole body so I was completely smooth. Then I asked her to withdraw in the TV room so I can prepare myself. I am only 172cm and she was just about the same height. Given I was also thin, I decided on sexy clothes from her wardrobe. And they surprisingly fitted me very well. A pair of her high heels fitted my feet too. It was incredible to feel the smooth silk of the pantyhose on my shaved legs. I would never forget how hard my penis got. I wished I could be shaved all the time.

I put on a bra (stuffed it with socks), a sexy black mini skirt and top. I even painted my toe and finger nails. I had long hair at the time and tied it back to a pony. Then I put foundation on my face, lipstick, eye liners and eye make-up of course. 

Once I was finished, I was truly stunned how hot I looked. I genuinely can say I would have passed as a very sexy woman. When opening the door to the TV room I could immediately tell that my girlfriend was also stunned. She even complimented me on my make-up skills and asked me whether I had done that before. I lied and said "no".

After a bit of an adjustment period given the unknown situation we started kissing and having sex. 

I would never forget how good it felt to be dressed up as and act and behave as a woman. The sex was okay. 

[openmouth4cock]

1st time living alone - sissy life

After the relationship with my second love fell apart I moved to a new city and finally lived the first time in my life just by myself in a small apartment. It was exactly what I always wanted. I could finally live out my bondage and dress up fantasies. 

I started shaving my entire body and would walk around in my home dressed up as sexy woman. I'd be wearing stockings and high heels, a nice negligee and a bra stuffed with socks. And, of course, my penis would always be neatly tucked away in a rubber penis prison or tied back to my arse while waring sexy panties. 

This was also around the time when I started a little bit of anal play. I remember clearly the first dildo I bought. It was 24cm in length and 4cm in diameter. To this point, I had never been really that much into anal play, neither receiving or giving. And to be honest, whilst I had some enjoyable moments, I could not really include it into my bondage play. The simple truth was that after a while wearing a 24cm dildo up my arse, the urge to go to the bathroom for a shit would become so intense that it was simply not enjoyable anymore. 

What was enjoyable though, was being tied up whilst dressed up as sexy woman and waiting for the ice in a little bottle to melt. That's where the keys were inaccessibly stored away; the keys that ultimately would allow me to regain my freedom again - after many hours that easily could last a whole night. 

Mostly I tied myself up whilst lying on my mattress so I could also fall into a broken sleep if needed to be. However. in this particular apartment there was also a hook drilled into the ceiling. On inspection day, I knew exactly what this hook could be used for. That was the key reason why I chose this apartment over any others I visited. 

Most of the time, I played with the hook living out bondage fantasies. However, I always ensured I could get free anytime I wanted. Over time I got more and more familiar with the hook in the ceiling and decided to freeze the keys safely in that little bottle. And then I prepared myself the usual way.

I got dressed as a woman, wearing high heels and stockings. I wore my sexy panties and tied my penis to my arse. I put make up on and a wig. I wore a nice negligee over my shaved smooth body, painted my toe and finger nails and secured a mouth gag harness over may head. My torso was also tied up. 

I tied my ankles together and my knees as well and attached the frozen bottle to the rope around my ankles. Then I tightened a belt around my neck. I further limited my movements via a stiff stick along my spine that I would attach to the belt around my neck and secure it with two further belts around my belly and hips. This was keeping my spine straight. My whole body was stiff whilst carefully balancing on the high heels.

A string attached to the hook on the ceiling was pre-prepared. I tied the string with a double knot to the back of the belt around my neck. This would keep me standing straight with no chance to free myself. In a last step, I slid the handcuffs under the rope around my torso and closed them around both of my wrists. Now I was truly shackled with no choice other then waiting for the water in the bottle to melt so I could undo everything. 

I was standing like this for a very, very long time...

And the pain that I felt after a an hour or so, the desperation and helplessness that became more and more as time went past... all of it was incredibly joyful ... and challenging too, of course. 

I don't know how many hours I stood like this. Time went very, very slow... and I wished someone had tortured me with a whip. 

[openmouth4cock]

Hogtied for real

Another key moment I clearly remember with my second love was the first and only time that I got hogtied by someone for real. We had two handcuffs that we occasionally used for sex play. These were made from proper metal. Once they were around your wrist you could not get them off and if they were too tight they cut into your skin. 

I asked her whether she would want to tie my ankles and wrists to the back with the chains of both handcuffs going over cross - a simple hogtie with 2 handcuffs. She was a bit hesitant but finally I could convince her that I really would like to do this. I told her she did not have to do anything and that I would try it myself and that I may needed some help (which I knew that I would not need it).

I put the first handcuff around my ankles. Then I lied on my side with my hands on my back. The second handcuff klicked around my left wrist. I pulled my legs closer to my hands. I wrapped the chain around the other handcuff's chain. I put my right wrist into the handcuff and .... klick. 

This was the first time I felt complete helplessness. This was the first time only one other person would be able to untie my. I was hogtied for real. The handcuffs cut into my skin. It was painful and I loved every single second of it. My penis was rock hard. 

She wasn't quite sure what to do next so I asked her to roll me on my belly as I could not do it myself. Then I asked her to position her vagina right in front of my face so I could lick her. She did as I told her and I licked her pussy. It was so good. I could have done that for hours if it hadn't been that tough on my neck. I would have loved her to simply grab my hair and fuck my face with her pussy really hard. However, I did not dare to ask. 

Instead she wanted to fuck me. Given the position I was in, that did not work well and proved pretty much impossible. Instead she gave me a blow job and I shot a massive load down her throat. That orgasm was ecstatic. One of the best in my entire life.

Unfortunately, we would never do it again. However, I also would never forget the helplessness and the pure joy I felt licking her pussy.