I Know

I pecked her on the lips and rested my head on her shoulder. We didn't say much the remainder of the flight. We relaxed and gently played with each other's penis. I kept my cock out until we landed, except for the final landing check by the attendant, and it remained fully erect in her playful grasp. Meanwhile, I had my hand up her skirt, stroking and enjoying every inch of her womanhood. I tried to close my eyes and rest as it was now almost three o'clock, but I couldn't. I was infatuated with her flaccid penis. Her soft cock was almost as exciting as her erection. It was still large and so warm and soft.

When the plane landed, it quickly moved through the empty tarmac to the gate. Bozeman is a small airport and at 3:00 a.m. there is no one around. We kissed and talk quietly as the plane readied to unload. When we finally stopped, we put our dicks away and gathered our stuff. We were the last people off the plane and watched the other five travel through the boarding areas towards the baggage claim. I walked behind Lita and I was so fucking horny. Shortly after coming out of the tunnel, I took a few hurried steps to catch her and we walked side by side down the hallway.

When I was certain no one was behind us, everything was closed and we were around the corner from our gate which was manned by the only other human on this side of security, I grabbed Lita's arm and pushed her against the wall. We began to make-out and I ran my hands under the back of her skirt and got two handfuls of ass as I dry-humped her big dick with mine. I could tell she had some implants in that ass. I couldn't wait to see it! To the touch, beautiful shemales aren't soft and pleasing like bio-girls. But the look! Nothing like it! Perfect silicon tits and asses, Botox-filled fuck-me faces. And of course, the dick! But on a hot woman!

As we made out, I held her tight to the wall and pushed and grinded my pelvis into her massive she-bulge. I reached around from behind her and grabbed her thick cock over her skirt and skimpy white thong. I needed it! I needed to cum! I needed to cum from getting fucked in the ass by her near perfect organ! I had planned to offer her a ride to her hotel. I figured I could wait that long. We couldn't fuck in the airport. It appeared empty but it's a fucking airport and we were two of the last seven passengers. Way too risky!!

We were so into making out at that moment I lost track of time and my surroundings however. As I forced my tongue down her throat and dry-humped and squeezed her rock hard dick, the flight crew had de-planed and turned the corner. Lita saw them and pushed me away but I know the pilots and the flight attendant got a good look at me squeezing a handful of she-dick. Hopefully their eye was untrained and figured Lita had a pussy. But I didn't mind much, I would never see them again. We stopped momentarily and let them pass. I avoided eye-contact for the awkward few seconds as they walked by. We let them get a little ahead of us and then continued on to the baggage claim.

Luckily for us flight crews don't check their bags! On the walk over and the wait for our luggage I asked her if she would like me to drive her to her hotel. I really wanted her to come to my ski ranch but she had the "engagement" in the morning - I still didn't know what it was! And I don't know, I fucked women at my wife's families ranch, but if I got caught with you know, a dick up my ass there, even one on a chick, well, I wasn't ready for that risk. I mean all the trannies I sucked and fucked, well, technically that fucked me after I sucked them, this was already the first one where I wasn't behind closed doors.

I had a lot of luggage due to all my ski equipment, and pre-arranged for a large van to pick me up and drive me to our off-site parking garage where we kept two vehicles. The man was waiting right outside and helped us load our bags. We got in the van and I guided Lita towards the second row.

Lita sat near the window and as soon as her ass hit the seat my hand was under her dress freeing her large penis from her white thong. Blocked by the first row of seats, I shoved my hand under her panties and pulled it out. We kissed as I fondled it between my fingers, feeling it fill with blood and stiffen by the minute. The driver knew we were "busy" and remained silent. As we approached the parking garage I was so excited I was about to shoot a load in my pants. Before giving the driver directions to the car I whispered in Lita's ear, "I can't wait until your inside me."

I stopped kissing her as I guided the driver to our vehicle. It was a standard parking garage with your ramps and stone pillars, but it had a section with oversized spaces to accommodate six-figured vehicles! We pulled up behind my father-in-law's car and I begrudgingly pulled my hand away from Lita's rock hard dick. I stepped down out of the van and held my hand up to help her down.

The driver helped us unload our bags from the van and get them into the custom made Australian SUV. He unloaded them from the van and rolled them over to me to place them in the car. As he walked to the back of the van to take a second trip, Lita lifted up her skirt after he passed to flash her ready erection. It pointed slightly upwards and her cotton white thong was still pulled to the side, held in place by her she-balls. I almost came in my pants right there. As the driver arrived with the last of the luggage, I hurriedly grabbed it and got it in the car as fast as could. I tipped the driver, waved as he drove away and then turned back to my big-dicked lover.

Lita was walking to the passenger side and I said "Fuck me," as he drove away, "right here."

"Here?", she responded turning around.

"Yes, nobody is here, i need your dick, now! We will hear if anyone is coming."

I was still standing near the open tailgate, Lita was steps away. She walked towards me pulling off her tank top. I sat down on the tail gate in awe, it was the first time I saw those rock-hard, perky breasts. The line where they met her chest was perfectly defined and her small, dark-brown nipples actually pointed upwards. When She reached me, I put my hands on her sides and went straight for a lick and some nibbles on her right tit.

Although her boobs were beautiful to the eye, I was there for the dick. I only focused on her breasts for a minute or so before moving downward, kissing and lightly biting her tight stomach. As I worked my way down, I pulled her skirt down, which struggled to get over her feminine curves. As her skirt hit the ground, I pulled back to admire the whole package.

As beautiful as she was, I didn't take it in for very long though because that eight inch cock was fully erect and staring me in the eye. I couldn't resist anymore so I grabbed her by the hips, curved down a bit, opened wide and consumed as much of her she-cock as I could. I wanted to get it nice and wet and up my ass as soon as possible, but I started enjoying the blow job. An overwhelming urge to drop to my knees and suck her she-cock like a little bitch consumed me. I felt around behind me for my duffel bag and when I found it, struggled to open the zipper while keeping that delicious monster cock in my mouth. I got it open a few inches and pulled out the first soft thing I could find, a t-shirt. I dropped it on the concrete floor and knelt down in front of Lita.

Lita had one hand on my shoulder and had the other pressed against her belly holding up her skirt. She was lightly thrusting her eight-plus inch steel rod into my mouth. I had my hands on her hips and, in sync with her thrusts bobbed my head up and down her now saliva covered shaft. I gently pulled on her hips to work her she-cock further down my throat. I love kneeling in front of ladyboys and servicing their dicks with wet puckered lips and my wanting throat. It must be something about the reverse roles and the power dynamic. You know, the alpha-womanizing white male on his knees helplessly sucking a cock.

I sucked her dick for a good five minutes and then stood up and kicked off my shoes as I kissed her. We both began grabbing at my belt and the buttons on my jeans. I pulled them off with my boxer shorts and my large erection sprung from my pants. For a moment or two, we continued to kiss as we stroked each other's hard-ons. I had to pull mine away though as I was so worked up I could have cum just from her light touch. As I did so, she put her hands on my waist and spun me towards the tailgate. She was powerful! Another thing I loved about shemales, the beauty of a woman but the power of an in-shape man.

As turned on as I was that she took control and planned to bend me over and plow me, I wanted to get fucked in a different position. I wiggled my hips to loosen her grip, turned around. And whispered, "I need to watch you go deep inside me."

Lita nodded and I turned back around and pulled two bags out of the tailgate to make some room. I quickly turned back and using my fists, jumped up on the tailgate. The hatchback went up quite high so Lita would not have to duck to comfortably and forcefully fuck me. I wrapped my legs around her hips and ass and pulled her close. I threw my arms over her shoulders and resumed kissing her as our big dicks rubbed together. Our smooth, sizable shafts applied subtle pressure to each other, while my large sack bounced into her tight little scrotum that held her small-but-firm testicles. They had contracted over the years from estrogen treatments but the pills did not effect her blessed endowment.

Although I wanted to enjoy and prolong every moment, I was about to take a dick up my ass in public. Obviously, I did not want to get caught. So it was time to commence the pounding. I pulled my right hand back to spit in and lube my gaping hole. However, Lita put her hand on my wrist as my lips puckered and reached for her bag.

I quickly realized she had actual lubricant. As she reached for her bag, I lied back but kept myself propped up on my elbows and forearms. I unwrapped my legs and let them fall at the knees over the tailgate. Lita was leaning forward and I looked down at our two big rods pressed together and standing tall, pointing at the ceiling. As she searched for the lube with her left hand, she grabbed both our hard dicks with the other.

She worked her long slender fingers slowly, rubbing our penises together as I gently moaned at the site, and the feeling and the anticipation of getting plowed. I reached down with my hand to help her squeeze our dicks together. She quickly found the lube and attempted to release our erections, but I applied pressure to her hand stopping her and indicating that i wanted the cock-rub to last longer. We were in public but the two of us just gently grinding our shafts together was just to pleasurable.

After a few minutes of playfully rubbing, I released her hand and she opened the bottle. Lita squeezed out a glob of lubricant and I shifted a bit, laid flat on my back, put my feet up on the tailgate and spread my knees wide. My hand was though my legs stroking her thick shaft, and my lower back curved upwards to present my gaping, soon-to-be-penetrated fuck hole for lubrication.

Her hand dropped and I felt the cold sensation of the viscous liquid on my puckered entrance. I spread wider and pushed out to open up more and allow her fingers to get some gel inside me. She then rubbed the rest on her fuck stick and grabbed the back of my legs just under my knees. My lower legs were bent over her hands and I began to pull on her big lady-cock to guide it inside me. She took a step closer and bent her knees slightly until her throbbing mushroom head met my entrance.

Lita began to push slowly forward as I guided the tip of her penis into my wanting hole. With my hand wrapped around the biggest dick that ever fucked me, I exhaled deeply and spread my legs wider to open myself up even more. I accepted the tip ever so slowly and temporarily stopped her progress to get comfortable and let the slight pain of anal penetration subside. I then released her shaft, look her in the eye and nodded. She resumed entering and her monster erection began its journey through my boy hole. I let out frequent shallow breaths as I slowly took every inch of that cock until her pelvis reached the underside of my butt cheeks.

As a considerate lover should do, especially one with a dick as big as hers, she waited for my signal to continue. I took a few more breaths, closed my eyes and let the pleasurable sensation of tingling anal nerves take over my body. I then opened my eyes and nodded again. Lita started to pump me slow and deep, extracting her huge cock about half way before fully inserting it again. The feeling was indescribable. I knew I wasn't going to last long.

Lita slowly increased the pace of the big-dicked fucking she was giving my ass. She slid her hands down to my calf's and extended my legs straight up in the air as I laid on my back taking her she-cock. This was another super-subservient position I loved! She was also now fully pumping me, coming out almost to the tip and ramming me balls deep while pushing my legs by the back of my ankles. The thunderous clap of her thighs hitting my ass echoed through the parking garage every time she fully entered my body. Although I had no penile stimulation at all, my bouncing erection began to tingle. Pleasure then spread to my chest and I decided I was not going to hold anything in. The sensation ran down my legs. It was happening. A full body, no-hands, anal orgasm was upon me.

Throughout the fucking, I grunted with each stroke she buried inside me. As my climax neared, I began to moan steadily. The volume increased as my man juice traveled to the surface resulting in the first pre-eruption oozing out onto the tip of my penis. Lita began to furiously fuck me as she saw I was about to explode. As the clapping boomed and echoed through the parking garage, the first real shot of viscous goo shot from my cock-hole. My hard on was bouncing all around, pointing in the direction of my face. I came so hard that first shot hit my upper belly. The second sprung from body and passed my nipples! I remember the tickling sensation as it dribbled towards my neck. At this point as I was screaming, "fuck me" through my moans. I let out a few more less-impressive spurts before post-orgasm bliss sat in. As did another thought.

After cumming, I came to my senses. I'm not gonna lie, if she came first I would have taken it raw up the ass. But I was pretty certain that her 'engagement' was an escorting gig. Not that I'm proud of it, but I could spot a shemale escort. They traveled to different cities on request to reduce their chances of getting arrested. Lita seemed very clean, but still I am married. I would have, however, taken my chances with an actual ass-to-mouth finish, I'd done that before and enjoyed it, but I hadn't properly sanitized myself. I didn't want any remnants costing me a day of skiing with diarrhea! So I decided to request that she cum on my face.

Lita was still pummeling my ass full force when I blurted out "cum on my face, cum on my face!"

Slightly disappointed, she somehow increased the speed and power with which she was pummeling my body. When she was about to blow, Lita pulled out and I sprung forward to help. I jumped from the tailgate and quickly fell to my knees to catch her load. Unfortunately, I missed the t-shirt that was still on the ground and was bare-kneed on the concrete. She grabbed my hair like I had done to so many girls, pulled my head back and stroked her long ladyboy-cock right over my open mouth. As I waited, mouth agape, eyes open, tongue extended like a proper bitch about to accept a load of cum, the first substantial stream exploded from her erection. It missed the target and ricocheted off my cheek and across my eye, forcing them both shut. She then pulled my head forward by my hair, readjusted and shot three or four more streams right into my mouth. I dutifully accepted each one into the back of my throat as she bounced the tip of her cock on my tongue. My eyes still forced shut, I licked my lips, squinted my eyes tightly and swallowed the second gift of ladyboy juice bestowed upon me that night.

Lita let go of my hair and I wiped the cum out of my eye and shook it off on the floor. If I hadn't cum yet, I would have swallowed that too. Realizing I was naked from the waist down in a parking garage covered in cum and kneeling on concrete in front of a massive erect penis, I hastily stood up and grabbed the t-shirt on the ground. I wiped my jizz off my neck and torso and then wiped what was left of her load off my face. I got dressed and put the bags back in the car.

As we drove home, I had the feeling I often got after getting my balls drained by a shemale. I'm temporarily not horny and I want out of the situation. It's weird, when I'm about to get it on with a chick packing something extra, I couldn't be more excited. But after I finish? Well, I want out. I often want to leave right after dumping a load in a pussy, but it's exacerbated with a ladyboy. I guess that's the closet thing going on, I don't know. We didn't talk much on the short ride to her hotel, but it wasn't awkward or unpleasant. I mostly contemplated if I wanted to ask her for her number and if she wanted to hang out again before she left. I didn't want to at that point as the tank was empty, but I knew tomorrow I would be jonesing for that dick.

We got to her hotel and I pulled her bag out of the car. We began to kiss a bit, I didn't pull up in front of the door, as I didn't want anyone to see me kiss her, you know, and maybe recognize she wasn't exactly who she appeared to be! Maybe it was in my imagination, but I think she wanted me to ask her for her number. I decided not to, I just wanted to get to the family chalet and get to sleep. I figured I'd crank one out the next morning thinking about her fucking me, and then get a ski bunny with a pussy back home for the next few nights. So I said nothing. I just gave her one final peck and an over-the-skirt cock-squeeze.

Lita said good-bye in a matter-of-fact tone and walked away. I felt bad for a minute, I'm pretty sure she was disappointed. But I hopped back in the drivers seat and drove off. I got over it. It was best that way. She was by far the hottest shemale I'd ever been fucked by, but there are others. And I went on to fuck five different women over the next two weeks, including two 18 year-old sorority pledges at the same time who were in Bozeman for a ski trip with one of their fathers! Lita was incredible, but I made the right choice. How well do I know her anyway? She seemed nice, but do I really need a shemale escort getting my full name and phone number? And possibly seeing how wealthy I am? Well, how wealthy my family is. Nah, much better to crank one out here and there thinking of the memory. Wow, as I write this I'm thinking, maybe I am an asshole.