First time with a trans woman

Young, dumb and full of cum! 

I suppose that I better start from the beginning,…

It was an icy cool evening, in my Mother’s home, the wind was blowing loud and hard, it had already knocked over the bins, leaving a scattered pile of debris, the lighter items flapping about in the brewing storm. It was just a couple of days after my eighteenth birthday. My mind started to wander and to explore and learn about all the curiosity running rampant about my own head,  the desires I had towards the opposite sex. But most of all. When I first got to discover the unspoken, hidden world of what aroused, single men. Most of all though, what we got up to, when nobody was watching.

The anticipation surging through my body in electrifying jolts of excitement at the thrill of what I had planned. The minutes slowly ticked by, then suddenly there was a knock on my bedroom door. “Good night” slurred my mother,  as she drunkenly made her way up to bed. 
“Night mum” I replied.
As soon as I heard my mother close her bedroom door, I snuck out to the living room,  creeping through the hallway, lightly stepping forward,  I slowly made my way until I was in front of our pc, I waited there for about five minutes in the quiet. My young, thick cock was starting to get hard. I couldn’t pause any longer, so I reached forward and switched the pc on. It took a few minutes to load up, as I waited I slowly ran my hands over my young, smooth body. I let my hands gently caress my soft, pink nipples. Slowly I traced my finger around the points of my nipples until they were erect,  I then started to pull and twist, getting a little rougher with each pull and twist, until my nipples started to burn with pleasure, sending jolts of ecstasy down my spine. My young, hard cock started to ache and throb from the sensations travelling around my body. Just as I started to grip the base of my cock, the computer’s monitor flashed on too the desktop screen. 

After about twenty minutes surfing the web, I found a chat site where gay men all over the country were chatting to each other and arranging meet ups, I quickly created a profile as my curiosity peaked. I signed in with my new username; Young dumb and full of cum. Seconds later windows were popping up with guys asking how old I was?, asking how I was doing? I responded to a few to get my bearings of how this site worked, nobody seemed to want to meet,  everyone that had messaged me, had only wanted to ask if I’d be interested in phone sex. Phone sex was the last thing on my agenda for the evening.

After what seemed like an eternity. . 
I got a message from a cross dresser in my area,  she was looking to meet,  my cock ached so much it was beginning to hurt at this stage, we messaged back and forth for a few minutes until I told her how much my cock was aching. She asked for my address, which I gave instantly but informing her that I still lived in my Mother’s house, to which she responded that she would be outside my house in 15 minutes and that she wanted me dressed and ready, and to be standing on the road just outside my house. My body was trembling with so much anticipation it took my three clicks of the mouse to actually hit the shutdown option. Stealthily I rose up from the chair and tiptoed my way back to my bedroom.  Quickly and quietly I pulled off my underwear and tshirt. I then gingerly made my way to my chest of drawers,  I pulled out a loose fitting jumper and tracksuit bottoms,  the shape of my semi hard cock showing against the fabric of my tracksuit bottoms.  I gently rubbed the shaft causing it to twitch and get slightly harder. I stopped myself from going further by walking around my double bed until I was at the window,  I reached forward and pulled up the handle,  pushing the window open I climbed up and out the window,  when I was outside I closed over the window,  leaving only the tiniest crack open so I could get back in after my escapade.  Slowly I crept along the gravel path, careful not to make the slightest bit of noise,  my heart was racing with the anticipation of my first meet with this cross dresser,  my heart was also racing with the fear of being caught.  Every time the gravel ground together with each step forward I’d freeze for a few seconds,  just to listen for any other disturbances of sound in the cool night’s air. As I finally reached the end of my Mother’s driveway,  I could hear the faint hum of an engine approaching. Turning my head to the right,  I could see the whole way up the road as the full moon lit up the entire countryside in a beautiful night time glow, then in an instant two headlights came around the corner completely illuminating the road, I had to look away as the car came towards me, I started to rub my eyes as I felt as though I’d been blinded by the headlights. 

The car was beside me, the engine purred into the night, I felt like I had left my body as I climbed into the dark interior of the car. As soon as the car door was closed, we started moving again. Out of the darkness this seductive husky almost feminine voice purred over the hum of the engine. “Hey honey, I’m Amanda”. She said
As she elegantly reached across to shake my ever trembling hand. Her hand was bigger than mine but it was warm and soft, as if freshly moisturised. Her nails were painted bright green and her fingers and wrist were adorned in an assortment bracelets and rings. “Hey honey, you have no reason to nervous, I’m going to look after you tonight”. She purred.
 I looked at her and smiled. As we drove further down the road before she started to slow down. We pulled into the entrance of a field. Amanda quickly jumped out of the car and quickly walked over to the gate that was blocking our access to the field, as she opened the gate,  the goddess that was Amanda came into sight.

She stood six foot two inches in height,  on her feet she had on a pair of scuffed up converse shoes, her beautiful, smooth legs were clad in pink fishnet tights.  Around her waist she was wearing a green micro mini skirt.  As she pushed the gate open her skirt rode up revealing her curvy bubble butt, just for a second the head of her eight inch, circumcised cock came into view between her long legs. Just as soon as her beautiful cock came into view,  it disappeared as Amanda turned around.  My jaw felt like it had dropped to the ground, hungrily my eyes devoured Amanda in all her beauty,  she was incredible, her shoulders were broad in her green halter top. But her c-cup breasts were what really caught my eye. As I tried to process everything that was going on.  Amanda quickly jumped back into the car and looked at me, seductively she smiled as she drove us forward.  
“Do you like what you see?”. Amanda asked me.
“ye.. yes” I nervously mumbled. 
“oh honey, is that tent in your pants for me?”. She giggled as she stopped the car and switched off the ignition,  the car was warm, Amanda reached across me to lower my seat back, she smelled divine,  all of a sudden her hands were on the waist of my tracksuit bottoms,  with ease she roughly pulled them off. My throbbing seven inch uncircumcised cock bouncing off of her chin. With a pleasant moan Amanda began to run her tongue up and down the length of my throbbing cock, all of a sudden her mouth had engulfed my smoothly shaven balls,  I leaned back and moaned in pleasure as my hand explored Amanda’s back until my fingers got low enough to run my hand across her ass, gently caressing her soft smooth checks, my fingertips rubbing small circles around her tight smooth rose bud, slowly I worked my middle finger deep inside. Amanda moaned in pleasure as she ran her tongue around the circumference of my  balls, before I knew it Amanda had the head of my cock in her warm,  wet,  soft mouth. I groaned in ecstasy as Amanda flicked her tongue around the head of my cock. Slowly she swallowed my cock until the head was resting against the back of her throat. I slipped a second finger deep inside Amanda’s tight, lubricated asshole, Amanda’s head started to bob up and down,  picking up speed with every her lips hit the base of my ever swelling, young cock. I lay back in the reclined car seat, my body was is spasms of ecstasy as Amanda’s  velvety mouth continued to suck my cock hungrily,  her saliva dripping down my balls as her tongue flicked across the head of my cock, the pressure building as I started hump and buck, as I was moaning and squirming in pleasure,  Amanda reached between my legs and slipped her middle finger deep inside me. Instantly Amanda found my g spot.  As she pressed my magic button she used the positioning of her hand meant she could hungrily fuck my cock with her mouth,  in seconds I was crying out in ecstasy,  “Fuck, I’m going to,  CUM!!”. 
With a groan and a final thrust, my cock exploded in the back of Amanda’s throat. Amanda quickly clamped her lips around my cock as to not lose a single drop. “Mmmmmmm”. Amanda purred,
 as she hungrily swallowed every last drop.  Running her tongue around the head of my cock, she gently began to suck, after about thirty seconds Amanda brought her head up from my cock with a little pop as my cock slipped out of her mouth.  “Did you enjoy that honey? “. Amanda asked
 As she leaned in close to me so she could kiss my neck. 

More to cum ;) 

Source: reddit.com/r/eroticliterature/comments/htpes2/first_time_with_a_trans_woman