Wednesday, August 31, 2011
Tuesday, August 30, 2011
Monday, August 29, 2011
Sunday, August 28, 2011
Any hetero guy wrestling with the idea of experiencing an encounter with a Shemale must go through the same things I was. Did this mean I had gay tendencies? Was there things seriously fucked up with where my desires were taking me? Why was I so curious? Was I going to be disappointed the same way I sort of was when I had my first BDSM experience? Would the feelings of letdown if I went through with it, be even worse, knowing that I would be with someone who also had a cock? Those things and so much more went through my head for weeks and perhaps months. The biggest question however was, what did Diamond look like facial wise? Was she "a guy in a dress" or was she like the Shemales I had seen in magazines and videos, someone who was passable? As I've stated before, I have had zero attraction to 'males' whatsoever and the idea of seeing a guy in a dress was a massive turnoff.
Finding a place to park near her condo, I was a nervous wreck. This was different than seeing Mistress Morganna. This was a point of no return for me. I felt light headed and a bit queasy as I rang the buzzer and she let me up. In the elevator ride to the 11th floor I remember telling myself that if she wasn't what I was expecting looks wise, that I should appoligize and leave. That would be the right thing to do, wouldn't it? Yes.
The elevator door opened and I found Diamond's suite. Palms sweating, queasy, nervous, heart pounding through my chest, and light headed, I knocked on the door..... I could hear someone on the other side come to the door and look through the peep hole. Then the door opened and in a dimly lit hallway, partially behind the open door stood Diamond. She was tall (5.10-6.0) with blonde natural hair, fair skinned, and was wearing a light colored dress. I was surprised at how completely passable she looked. I was in no way expecting her to be so fully transitioned.
I entered her nicely furnished condo, feeling more at ease with each step, but still very light headed and heart racing. We exchanged pleasantries and asking my name, she asked me to remove my coat and shoes and to come into the living room. She asked me to sit down on the sofa beside her and sensing my nervousness she asked,
" Have you ever been with a girl like me before?"
"Uhh....no... no I haven't." I stammered.
"Well please be assured you have nothing to worry about, I'm very understanding with first timers. Tell me, why did you want to see me?" She asked with a relaxing tone and pleasant smile.
" Well....I've been curious for a little while, and after I had seen my first video with a transsexual in it, I found it quite....stimulating" I nervously laughed.
She joined in my laugh and explained that she wouldn't do anything with me tht I wasn't comfortable doing and if I didn't want to continue at any point to just politely request that we stop and things would be ok. I was feeling much more comfortable upon hearing how she was concerned that I wouldn't be uncomfortable at any time.
"Would you like a drink, and I can put on a video for you? " She asked
I agreed and she went to the kitchen to get each of us a glass of wine. Upon returning she went over to her TV and picked out a shemale porn video and as it played she sat down beside me and we toasted our glasses and she said softly, " Just relax and enjoy yourself hun..."
Not being needed to be told twice I lowered myself to my knees and with both hands slowly peeled down her panties and was suddenly face to face with her silky smooth shaven cock as it popped out. I felt as if I was stoned at that moment as the endorphins from who knows where flooded my brain. Instinctively I opened my mouth and she moved forward ever so slightly just to place the tip of her cock on my lips. The feeling was incredible. Never had anything so smooth passed my lips.I kissed the head over and over and ran my tongue all around the head as she ran her fingers through my hair drawing me insticntivey ever so closer as I took her cock into my mouth, like a young calf who feeds on it's mother for the first time.
Upon leaving and getting back to my car, I was swirling with the thoughts of what had just taken place and all over the map menatlly and emaotionally as to what it all meant. it would take me some time to come to terms with this experience and what it would all mean, but the one thing I knew was there was no way to turn back now... I was now a cocksucker and I liked it!
Saturday, August 27, 2011
Friday, August 26, 2011
Thursday, August 25, 2011
Wednesday, August 24, 2011
Tuesday, August 23, 2011
Monday, August 22, 2011
Sunday, August 21, 2011
Saturday, August 20, 2011
Like any young man moving to the big city, I had some wild oats to sow, and that certainly happened just like any other young guy. However, now that I had a place completely to myself, I suddenly had the freedom to allow those desires and fantasies, born years earlier to rise to the surface without any real fear of being discovered, at least in a home sense.
As the session drew to a close She proceeded to introduce my cock to the world of CBT and tied my cock and balls up while blindfolded and re-tied to the room chair and slowly began tugging and pulling on the head of my erect cock, seeing how I was reacting.
" You know I could yank your pathetic cock right off in this way, but that wouldn't be much fun." But to re-enforce her point she pulled it hard to the ground, causing a lot of discomfort. Seeing me squirm brought laughter to Her and in one swell move jerked the rope in such a way that the way She had tied my cock up in a spiral unravelled in quite a stimulating way and I coudn't help but smile in delight.
"Oh, you like that! Well you're going to do something for Me that you will like."
She ordered me to begin stroking my cock slowly while She placed Her shoe into my balls and cautioned me not to cum until I asked permission and was given. Being told at what pace to stroke, the limitations of a 19 yr old body couldn't comply and I quickly wasked for permission to come, to which I was denied, but it was too late! I shot an enormous load straight into the air, to which Mistress Morganna laughed.
" Oh my little boy! You almost hit the ceiling!" Mistress Morganna laughed.
"Sadly you didn't get my permission so we will have to work on your training next time"
With that, I was untied, allowed to compose myself and clean up. After a short discussion as to how I enjoyed myself, I was given permission to contact Her again and I would be allowed next time to serve Her in Her dungeon. I thinked Her profusely for such a unique experience and when She left, She asked me to repeat back what I was.
" I'm an arrogant male chauvinist pig, who needs Your control and guidance, and You are going to give it to me"
" Good boy" She smiled and walked out.
I reflected on the experience. While it was truly unlike anything I ever experienced before, I was left asking if it was worth it, and wondering if I would ever go through it again? What I didn't know at the time is that I had built up so many mental expectations fueled by fantasy, that there was no way a hotel session could possibly live up to the unknown. For now, I was happy that I went through it, but thought, " This isn't for me"
How little did I know then.....
Friday, August 19, 2011
Thursday, August 18, 2011
Still living in a smaller community and at home, there was no opportunities for a young man to really gain much of an education in those areas. It probably was an ad in the back of the local metropolis newspaper that gave me an avenue to take the first wobly steps as a baby deer would in encountering my first Domme.
On a side note, I would like to take this opportunity to finally appoligize to Mistress Morganna for the foolishness of my youth, and for the dumb questions I was asking and for wasting Her time. Better late than never I hope...