The Point of No Return: My First Cock

 

On the surface I was just like any other normal 22yr old guy. Working while going to school, dating, girlfriends, parties, etc. No one could ever imagine that at certain times, I would allow myself the guilty pleasures of learning about the world of kink, including still trying to understand BDSM more fully, and my newest desires; the idea of exploring what it would be like to be with a Shemale. 

Within the pages of Kinky Times magazine, and in the backpages of my local newspaper, I would see ads for a local Tgirl escort by the name of Diamond. It wasn't until I saw her more descriptive ads in Kinky Times did the idea of taking the plunge become something that was plausible. But could I get over that enormous hurdle?

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, complete turnoff. It was an early fall evening when out of the blue, I decided that I could not hold my curiosities at bay any longer. I worked up the nerve to call Diamond and was pleasantly surprised to hear that her voice was very feminine, which put me more at ease immediately. 

I asked her if she was available that night and she told me she was. We made arrangements for me to visit her condo downtown and when I hung up the phone and began to get ready, my heart was racing. Just like when I was prepping for my first encounter with Mistress Morganna. A million thoughts raced through my head, and I was unprepared for any of them so I just focused on getting ready. 

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 apologize 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 coloured dress. I was surprised at how completely passable and beautiful she looked. I was in no way expecting her to be so fully transitioned.

 

"Come on in." Diamond said softly.

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 that 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..." Diamond curled up beside me while we watched the video for a few moments and reached over to touch my hand which was cold with nervousness. She giggled and told me that it was good to be nervous and that she would warm my hands up. As she touched my hands, they felt completely feminine, and it eased my mind. By this time each of my senses were on extreme alert, knowing that this encounter was the point of no going back. I reminded myself that if I wanted to leave, I could at any time, but with each moment with Diamond, those fears were easing. She smelled great, her skin was soft and when she placed her hand on my upper thigh, my cock sprang to instant hardness. Sensing my growing comfort, she gently caressed my bulge in my jeans as we both watched the gurl on gurl action on the screen. 

 

A moment later Diamond took my now warming hand and brought to to the hem of her dress and ran my hand up her thigh. My heart began to race as I knew where she was heading. When my fingertips began to feel the silk of her panties, my senses were about to hit overload. Then for the first time in my life, I felt what was like no other, her cock slightly aroused behind her silk panties! She slowly removed my hand and allowed me the freedom to explore on my own. It was a combination of silk, soft and firmness, unlike anything my hands had felt before and her bulge was becoming more pronounced with each passing moment. 

She slowly leaned over and kissed my earlobe and as the tingling sensations overcame me, I moved aside her panties and for the first time, I felt a cock in my hand other than my own. It was incredibly silky smooth like velvet, as I took it in my hand and gently stroked it. The feeling of it getting hard in my hand was mind blowing as she continued nibbling at my ear. I turned my head and our lips met as I continued to stroke her growing cock as she unzipped my jeans and dove her hand into my pants to return the favour.

 

We kissed and stroked each other and all I could remember was thinking that there was no odd sensation that she wasn't anything other than a woman. She smelled like a woman, was soft like a woman, kissed like a woman, was gentle like one, sensual like one, everything. She just had this strange and exotically wonderful growing cock in her panties and with each passing second, my cares and fears were slipping away as we made out like any two people would. She then got up off the sofa and casting a silhouette in front of the TV, she slipped off her dress in front of me to reveal her almost perfect body to me. She undid her bra to reveal two perfect breasts and asked me to get up and come over to her. I did immediately as she began to take my clothes off and within moments we were both naked except for her bulging hardon straining against her silk white panties. 

"Would you like to remove them for me?" She asked coyly

 

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 shecock 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 instinctively 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.

 

This was so much more than I ever imagined and we had just gotten started! I slowly sucked on her cock, taking it in as far as I could without gagging, slowly taking it in a bit more each time as she softly moaned. I placed my hands on her hips and would bring her into my mouth which was dripping with saliva and anticipation as I indulged myself like a kid on a carnival lolly pop. I really have no idea how long I was on my knees sucking her cock for, when she pulled out and asked me to lie down on the carpet rug in the middle of the living room. I did as instructed and she straddled my head from above and I watched as she slowly worked her way down to straddle my body, never taking my eyes off her cock as it dangled. Now in a 69 position she slipped it into once again my awaiting mouth and for the first time I felt the sensation of her completely smooth balls as they came to rest on my face. OMG what a sensation!

As she took my rock hard cock in her mouth we both sucked each other off, with me now being somewhat less of a virgin cocksucker, and now was enthusiastically working my head to meet her cock and balls as she rocked them back and forth as they met my face. Diamond was now herself feasting on my cock as well and it didn't take very long to feel like I was going to explode in a mind shattering orgasm. I asked her to stop for a moment because I was going to cum and she backed off, while still sliding her cock in and out of my mouth and reaching for a condom at the same time. I was fully engaged on her dick non stop and when she resumed sucking mine, it didn't take more than a few short moments to test the tensile strength of the condom as I blew off  what felt like the biggest load of my life in a body twitching orgasm!

 

I kept sucking until I felt completely drained and when I let out an exasperated sigh and my body felt completely relaxed, Diamond turned to me and cuddled a bit on the rug with a big smile, asking me if I enjoyed myself. With a big grin I assured her I most certainly had and that I needed a moment to compose myself before even thinking about getting to my feet. She caressed my still twitching cock for a few minutes and ran her fingers through my hair until I felt my strength return. After cleaning up and gaining my composure somewhat, we hugged and I thanked her so much for what was an amazing first experience. She hoped that she would see me again, and I assured her I would.

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 mentally and emotionally 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!