Vicki

Hey y’all, it’s been a while. What’s the best way to pass the time when your bored at work? Write stuff… I hope y’all enjoy my first endeavourinto trans stuff.

The room was dimly lit and a layer of cigarette smoke hovered a few feet below the ceiling that was only visible when the disco light bounced off of it. I was sitting at a table near the door with a few of my buddies talking about a couple of girls up at the bar.

“You should go buy her that drink!” I urged one of them. He had been talking about her for the last hour, how he wanted to “get with” her. He was the shy type so I thought he needed a little push. “Come on man, ya only live one! What’s the worst that could happen?”

He finally started to stand up at the same time she was walking away from the bar. I think it was his plan all along. “Damn, ya missed your chance!” I prodded at him as he sat back down in a huff of likely fake defeat.

“I’m empty” another friend said, “this ones on me? Who needs a fresh one?” Of course everyone at the table shouted and raised their hands as he started for the bar.

He was up making small talk when a group of people entered past security. They were dressed all flashy and were obviously not regulars. The folks that come here wear blue jeans and t shirts. This group was way over dressed for that establishment.

There was a mix of guys and girls, eight people in all and a few patrons watched them as they crossed the room to an empty table in the back.

They passed by our table and that’s when I noticed her. She was tall, blonde and had a tight red dress that seemed glued to her tight body. I wasn’t able to get a good look at her face, but that body! My jaw dropped and I felt a flash of anxiety run through me.

As the next round was being delivered to the table, the conversation had shifted to the new group of people that just passed by our table. One voice was heard suggesting that they probably came from that gay bar downtown.

“I don’t care! I gotta go talk to her!” And I nodded towards the blonde who was a few inches taller than the next tallest one in the group. She must have stood about five foot ten or more. She could have been a model, but tonight she was a goddess.

I stood up and headed to the bar. What woman doesn’t like Fireball? I heard the table laughing and joking about how I was going to crash and burn and that she was way out of my league.

I consider myself an attractive guy, I’ve had good luck with the ladies so far. I’ve probably had more than my share at the ripe old age of twenty-four. I got two shots of Fireball and I was about my mission. To be successful, I had to get her phone number I convinced myself walking over.

“Hey, I’m Aiden” I started out while reaching the shot in my hand towards her, “I haven’t seen you here before?”

She turned her head to face the stranger talking to her, she was drop dead gorgeous! “Hi, I’m Vicki.” she replied kind of shocked that she was being approached.

“Do you like Fireball? I inquired as she took the little plastic cup from my hand.

“Not usually, but I can make an exception tonight.” she joked as her group all laughed. And she raised her cup, tipped her head and it was gone just like that.

They were all, and I mean all seven of her friends, we’re all staring at me. I felt this awkward feeling run over me.

“I’m usually a whiskey girl.” She told me as I took my shot.

“Oh, we’ll can I buy you one of those?” I was nearly begging her. I suddenly felt a mix of small and accomplished when she grabbed my hand and guided me towards the bar.

Now, her table of friends and my table of friends were all watching us head up for another shot. Both groups in disbelief.

“Whatever the lady wants, bring two!” I told the bartender trying to let my confidence overshadow my insecurities.

She ordered us two shots of Devil’s Cut and looked at me and smiled. It should have been a sign, a red flag. Jump ship…now. But it wasn’t.

We got the shots, she made a toast to having fun tonight. I quickly agreed with a “hell yeah” and we took our shots. I’m grimacing and my mouth is watering from the liquor, not her. She set her cup down with an “ahhh”.

“Hey, wanna walk me outside?” She asks. “I need a smoke!”

Confused, looking around the smoky bar, “You can, ah smoke in here!” I obviously didn’t catch the hint.

“I know, but my pack is in the car.” Vickie responded innocently.

I agreed and we headed for the door with even more eyes watching us as we exited past the bouncer. Quietly we walked across the gravel parking lot towards the a dark corner and an old Chevy van. Totally not what I was expecting her to drive. It must have been one of the other’s car.

“Climb in” she motioned to the passenger side so I obeyed and got in the car.

Once the doors were closed and the dope light went out, she fumbled around to find her pack of Marlboro reds and a lighter. We were talking, I was trying to be funny whale she took in her nicotine. About half way through the cigarette she put her hand in my thigh and started rubbing small slow circles.

Her touch immediately stirred my cock. I could feel it pressing harder against my Levi’s, I could feel my heart speed up. I reached to reciprocate the touch and she blocked me. “Not yet Aiden!” she softy denied. “Keep your hands to yourself for now, ok?” Vicki requested.

I was intrigued and agreed to comply. I’ve never been with a woman so assertive. It was so sexy. Her pinky grazed the lump in my jeans and she smiled, I smiled back.

“Looks like someone is happy!” she noticed with a deviant grin.

Unable to speak, or a loss for word, I just nodded her affirmation as she gripped my cock through my jeans and leaned over and started nibbling on my ear lobe.

That’s my go button. How did she know? I was going crazy as she started trying to unfasten my pants. As impatient as I am, I helped her loosen their grip on my waist. She reached in and freed my raging hard on. It bounced in the cool night air.

She went down on me, slowly engulfing my cock into her mouth. My eyes rolled back in my head and I let out a long soft sigh. Oh my god it felt amazing. It was by far the best head I’ve ever had. She went about her business of blowing me while I went about my business of enjoying it for a few minutes. Then she stopped.

“You like that?” she needlessly asked me.

“Holy shit yeah!” I could barely force the words out of my mouth for her. I needed her to go back to what she was doing. I was going crazy with horny!

She grasped my hand and put it on her thigh. “You may touch me now.” She permitted. “But only if you want me to keep going.”

That’s all I wanted in the world at that moment. I excitedly rubbed her thigh for a few strokes until she went back down on me. That’s when it hit me.

Literally, I mean it hit me. As she leaned over to me, her body twisted and I felt her dick! She was a he!

I quickly pulled my hand back. I was shocked! I was uncomfortable and I was getting the best blow job of my life. She was beautiful. I would have never guessed she was trans. I’ve seen tranny porn and they didn’t look like her.

No one would know but us. And her friends. I didn’t care about her friends. I cared about this moment, this blow job and exploding this intense pressure I felt in my balls. Besides, lips are lips, right?

Like an expert, she worked my cock to peak and back down two or three times. The need to cum was tunneling my vision. On the fourth trip to climax and denied she raised off my cock and told me to hop into the back seat, take your pants off and lay down.

I was a lump of clay in the potters hand waiting to be shaped. I followed her command like a trained puppy and onto the bench seat, fumbling with my shoes and pants as I went.

She followed once I was settled in the most comfortable position I could find and got onto the floor next to me. Once she was comfortable, she licked her lips and went back to sucking my cock.

For the first time since I felt her dick, I put my hands on her. Expecting to find a wig, I gently put my hand on the back of her head as she bobbed on me. It felt real enough so I rubbed and locked my fingers in it. I could feel her groan of approval vibrating on my shaft.

She stopped again just before I reached that no stopping point and repositioned herself then started to rase my legs. I didn’t know what was going on, but at this point I didn’t give any fucks. I didn’t stop her.

She arched her neck over and licked my ball sack from between my raised legs and pulled my ass over towards her. I felt her tongue exploring my nuts and moving lower until she was no longer on them, but on that little place between them and my hole.

She fluttered her tongue down my unshaven place until I felt it hit my asshole. I let out a moan, I felt lightening shoot through my body and that moan was unstoppable.

With one leg propped on the front bucket seat and me holding the other up, I was in the most vulnerable position I had ever been in while my ass was being licked and sending me to the seventh level of heaven.

She was stroking my cock slowly and tonguing me when I felt a little more pressure against my ring and was thinking damn she’s got a strong tongue when I felt the first finger breach my virgin ass.

I jumped a little and clenched my butt, squeezing her finger. She never stopped moving her hand up and down my cock. I focused on that feeling and tried to relax again as she went back to eating me out and pushing her finger inside of me.

Softly, she spoke as she told me she wanted to fuck me so bad. That should have been a mood killer but I wanted to cum so badly.

“Uh, I don’t know about that?” I questioned, reasoned with myself as much as questioning the action. “I’m not fucking gay!”

“Trust me, no one will know. And if you let me, I’ll let you cum anywhere you want.” she petitioned for permission, while never missing a beat on my slightly less hard cock and her finger was now comfortably inside me and bushing my prostate.

The tunnel vision was blinding me, the build up of cum in my balls was blurring what little vision I had. Maybe I was gay or something, but I nodded my consent.

She hiked her red dress up and and lowered her panties. For the first time I could see her cock. It looked about the same as mine, seven inches and not super thick. Her cock was straight though where mine has a little bend to the left.

She reached into a bag and fumbled around for a second pulling out a tube of some kind of lube and squeezed a puddle into her hand. She grasped her own cock and coated it first. Then using her lubed up fingers, she applied to to my hole pushing her finger inside me again.

This time she had a purpose. She was working my hole to loosen it up some. A second finger impaled me and if not for a little pressure, it would have been complete pleasure.

She pulled her fingers out and got up below me, grasped my revived hard cock with her lubed hand and slowly stroked me. “Take a deep breath and try to relax. I’ll go slow.” she tried to calm my fear. I just looked at her. I noticed her blue eyes for the first time. I was focusing on them when I felt the head of her dick gently push against my ass.

With a short quick jab, she broke the plane. The pain was breath taking. My entire body screamed out in pain as she paused just inside of my ring. My dick convulsed at the same time as my breath was leaving my body. For a second all I could feel was fear and pain but slowly a new feeling was taking over. It felt good. Really good.

After a few seconds, she pushed herself in a little deeper, very slowly until I felt her body hit mine. She stopped again. “You alright?” she checked in on me. All I could give her in return was an “uh ha”.

She started moving back and forth, in and out of me. I could feel every inch of her filling me and leaving me empty and repeating. The pain was almost completely gone and all I could really feel was an earth shattering new kind of sexual ecstasy.

She had one hand on my chest for support, one hand holding my cock and she was pumping her cock into me. The pressure on my prostate was fantastic. She had me moaning and squirming. Her eyes never left mine, when mine were open.

She paused for a second to reposition her hands for better support as she continued to drill me. We were one now. Moving in tandem, together like we’ve done this a million times before. I was lost in a moment of pure bliss when the first volley of my own cum landed on my cheek. The second and third hit my chest and then my belly.

She never slowed down as my cock emptied itself onto my shirt. I reached between my legs and gripped her ass cheeks pulling her deep inside of me and I grounded my ass against her feeing her cock hit me in new places deep in my center.

She fought against me holding her inside of me to continue her assault on my now very hungry ass. “Fuck me!” I begged her. “Oh my god baby, fuck me harder!” I didn’t know where it came from but I wanted more, deeper and harder.

My cock began to stiffen again as she willingly pounded herself into me. God this woman was amazing. I could feel a second wave of orgasm building as I she slowed almost to a stop deep inside of me and let out a deep whispered moan. She told me she was going to cum and asked me where she should let it go.

“Wherever you want baby!”

She started jabbing inside me again and I could feel my own ecstasy build. The best feeing I think I’ve ever felt was when her cock throbbed inside of me, or maybe it was feeing the heat of her cum filling me. I don’t know. The were both fucking awesome.

She pumped into my cum filled ass until I could feel it pushing out. When I thought she was done, I grabbed her ass and pulled her deep into me again and started jacking off while grinding on her cock.

It didn’t take long before I was shooting my second load of my creamy juice onto my shirt. When I had milked all of the cum out of my cock I just dropped my hand to the side of the van bench and laid there trying to catch my breath, eyes closed.

I felt her move over top of me and put her lips to mine. We shared an exhausted kiss between hard breathing.

“You probably should have taken your shirt off too!” She joked pointing out the wet spots from my cum.

“Fuck!” I exclaimed pulling my shirt up to see what she was talking about. “It never crossed my mind! The bar is dark, I’ll just turn it inside out.” pulling it off over my head carefully so I didn’t get it in my hair. The wet spots were cold against my chest.

She reached under the seat and pulled out a box of baby wipes and motioned for me to take one to clean myself off.

“Can I see you again? she shyly asked.

I had a feeling of shame coming over me. Later I found out it was called post but clarity. Unsure if I’d really be willing, I said yeah.

She asked for my phone and put her number in the “To” line of a text message and told me to put my name in and hit send if I wanted too. I put the phone to sleep with it just like that and finished getting cleaned up and dressed. “Your friends are probably wondering where you are.” I said.

“Nah, they know. But your friends?” She replied with that devilish grin again.

We got out of the van and headed back across the bar parking lot. I felt conspicuous that I was walking funny as we entered the smoky dark room again. As we parted ways she reinforced her desire to see me again. I told her I’d call her, gave her a hug and headed towards the bathroom.

I opened up my phone, typed 5 letters and hit send.