I Know

I'd been stealing glances for over three hours. What else was I supposed to do in the Minneapolis airport as seven of us waited for a storm to pass over Southern Montana? I was struck by her Botoxed lips and high cheek bones. By her big, wide-spread brown eyes that occasionally glanced back at me from behind her over-sized glasses. At her long, slender fingers and fake nails on which she rested her prominent jawline for most of the wait. At her blonde hair with black roots tied and pulled upwards into a tight golden bun on the top of her head. And of course, at the outline of her perky nipples visible through the tight white ribbed tank top. The same U-shaped, low-neck top exposed her olive-toned long skinny neck, and compressed her fake, bra-less c-cups. Oh god, those tits, they poured out everywhere! Exposed cleavage on top as well as a good deal of side boob.

I watched her walk away a few times, to go to the bathroom or get something to eat back when the airport stores were still open. She must have been six feet and her high heels added a few more inches. She had really long legs, toned but not muscular, that dropped from her loose fitting pleated black skirt which just covered her curvy booty. I slumped down more than once that day to get lower in failed attempts to see her cheeky backside. Her hips and slim waist were not very curvy, rather more streamlined, but the whole package had left me half-to-fully hard the whole evening!

It was already one o'clock and we were the last remaining passengers in the entire terminal at the very large airport. I was so taken with her, I didn't mind the delay, that was entering it's sixth hour. She mostly read her phone and a fashion magazine, but she gave me a few looks and shot me a smile or two throughout the night, I think. I was obsessed, I couldn't believe this opportunity, only seven people would be on the flight!

Finally it was time to board. Even though there were only seven of us on the short 90-minute connection to Bozeman, the airline didn't skip any formalities and called all the boarding zones separately. Despite the ability to board first, a privilege of my first class ticket and frequent flier status, I let the other passengers go ahead and boarded with the last group that included the striking woman. I kept a little distance as I walked through tunnel to let her get ahead. The crux of the plan I hatched as I waited for the flight hinged on where she sat. It was nerve racking.

As I went through the door of the plane I explained, well lied, to the sole flight attendant that I slept better in the back of a plane, so I didn't want to sit in my spacious first row seat. With this few people on the plane, he would know where everyone was supposed to be seated, question me and threaten my plan. He had no objections and I began the journey through the aisle.

It was a regional jet, maybe 20 rows long, and had two seats on each side of the lone middle-aisle. I passed two people in first class and three more in the first few rows of economy, none of which was the woman of my obsession. I couldn't believe how well this was working out, maybe a connection was meant to be!

Butterflies fluttered in my stomach as I continued my journey to the back of the plane. After passing five people, I saw her settling into a seat in what I estimated to be row 16 or 17. "Holy shit!", I thought, "we have the last 10 rows to ourselves!" I quickly scanned the back of the plane to make sure, it was in fact empty! I continued walking towards her as she settled into an aisle seat on the right side of the plane. It was go time!

I approached her a bit hunched over at the neck. The plane was small and I was tall. The top of my baseball cap probably wouldn't have hit the roof of the plane, but it was close. When I arrived at the woman's row, I put my hand on the back of the seat in front of her and said:

"Can you believe this? An empty plane and that's my seat," pointing to the window seat next to her. "I'm sure they won't mind, I can sit here," indicating the aisle seat next to her.

I paused to let her respond. I'd be good from either seat, but it would be much better if we were directly next to each other. Luckily she was still getting settled when I approached her and I was able to add, "but I'm pretty wired, won't sleep. I wouldn't mind a little conversation if your up for it."

I'm pretty smooth at talking to the ladies. And I have a thick Boston accent that gets a lot of women to cream themselves. I'm in my mid-thirties now but look much younger, and although I'm married, I still get around. My wife and I have an alright marriage, but we're apart a lot. And frankly, I'd cheat on her even if that wasn't the case. I really just can't help it.

Our eyes were locked and my stare was intense as I awaited an answer. As I suspected, she couldn't resist my charms. She actually didn't answer, rather she stood up with a big smile, inviting me into her seat. Her smile seemed to say your full of shit but I do want you next to me at the same time. I didn't want to count my chickens, but there was a great chance this was on! Some type of mile-high intimacy was likely in the cards!

I sat down and let her get settled. "Eddie," I said holding out my hand.

"Lita," she replied in a heavy Latina accent, holding out her slightly bent long fingers to grab my hand softly. We gave each other a light shake and took our hands back, maintaining eye contact.

The plane quickly moved from the hangar to the runway as we continued on with the pleasantries. We covered the basics, she was Brazilian and on her way to Bozeman for the weekend from New York, I was from Boston. I left out the part about my wife and two kids. That subject tends to spoil the mood. Instead, I just told her that I was staying at my cabin about 40 minutes south of Bozeman to ski all week.

'My cabin' was actually a palatial skiing chalet on about 240 acres owned by my wealthy father-in-law. He was a former prosecutor turned high-powered defense attorney that owned seven luxurious properties, five of which were at our disposal. I wasn't his favorite son-in-law, I didn't work per se, rather I mooched off him via his daughter and grandkids. I typically traveled with my family but my wife didn't like to ski and particularly hated going to middle-of-nowhere Montana. So I usually went there by myself two or three times per winter.

I grew up a poor kid with no father from a rough neighborhood in South Boston. When I married my wife 15 years ago, we were 22. She was hot, but now she was just a fat pig. Sorry, I shouldn't say that, but it's true. She was over 200 lbs and made no effort to loose weight. She got out of shape after our oldest son was born and blew up like a balloon after the youngest. I was still a hot dark-Irish looking guy with a goatee and tattoos on my shoulders.

Like I said, I could charm the ladies. I'm not a total shithead, I spend a lot of time with my kids and I'm really nice to my wife. I even throw a fuck in her jiggly body here and there. But the way I figured it, I couldn't waste these years and my gift. I'm mean I'm hot, have a big dick and can charm well more than half of the people I want to fuck into bed. I can't waste all that on chubby spoiled homebody from a wealthy Boston suburb.

Back to the flight, our conversation took a pause as is customary during the actual take off and we settled into our seats. I knew the flight attendant would want to get the beverage service over quickly and get back to the front of the front of the plane. That's when I would make my move. I also knew when he came by that he would know exactly why I gave up my first class seat. But that being the only minor hole in my plan, and if so, that was totally acceptable.

While still ascending but comfortably in the air and through those first few turns every flight seems to make, I began to pry more into why Lita was going to Bozeman. Before take-off she said she had 'an engagement'. I figured it would be a good topic to kill a few minutes while the attendant gets the drink cart ready. I also thought it might be a sexy engagement that would stir up a conversation that would move things in the right direction. I'll get to why I thought that later.

"So tell me, what's this appointment or engagement you got going on this weekend in Bozeman of all places?," I inquired.

Lita smiled, "why is it so important to you?"

"I'm just curious. Seems like a good topic to discuss over a drink," I replied and nodded my head towards the man coming toward us with the cart.

As I awaited a response, I faced my gorgeous Latina flight mate with my shoulders square to her. As the man approached to serve us first, I turned back towards the seat in front of me and put down my tray. I wanted to keep our flirtatious interactions a little more private. The whole point of my plan was to be as clandestine as possible, if I didn't care I would have approached her in the airport. As I said, the attendant knew what I was up to, giving up a first class seat to sit next to someone on a near empty plane! A little obvious. Not to mention, Lita's gorgeous, I'm hot, but there was no need to totally confirm it!

"What can I get you both?", said the good looking flight attendant in a very effeminate voice.

I knew there was no alcohol on the short flight but I did ask for a gin and tonic. Maybe I do things like that because I'm an optimist, but more likely it's because I'm an entitled asshole. As expected though, I had to settle for a glass of water, as did Lita and the man pulled away. We were now in the clear. It was highly unlikely anyone would come back here for the rest of the flight. The bathrooms and flight attendant area were in the front of the plane and the attendant moved on to serve our fellow passengers. His back was turned to us, he was already 15 feet away, and the plane was dark except the aisle lighting and a few overhead lights. Our overhead lights were both on, and their soft yellow light created quite a romantic atmosphere. I again turned my shoulders towards Lita, this time with no intention of striking up a conversation. I placed three fingers every so gently on her inner thigh, leaned my head in a bit, and said in a loud whisper;

"Do you want me as bad as I want you?"

Lita was half shifted towards me, her head was turned and her mouth was half open, like she wanted me to kiss her. She looked at my lips and then down at the fingers I placed on her leg. I gently stroked the soft skin on her more-muscular-than-most-girl's inner thigh. She answered me with a smile, so I did it, I leaned in to kiss her while palming the inside of her leg. Lita pulled back however with a smile and placed her hand on mine to ensure it wouldn't travel upwards.

"Slow down lover," she said with a sexy smile. "You think I'm that easy?"

"I think you want to fool around a little," I responded with a smile. "You know, you're hot, I'm hot, I think you want me."

With a really big smile, Lita replied, "is that so?"

"That's so," I said confidently.

"I don't think you fully understand," she whispered with a coy smile.

"Understand what?"

Lita paused for a moment and answered, "let me show you something. Then we will see if you still want me."

My cock was already hard and pressing against my jeans. I got an incredible tingle through my shaft when she said that. I had a good idea what she meant. I was so fucking excited and nodded in agreement. Lita reached her hands under her tray, I couldn't see exactly what was going on, but again, I was pretty sure what she was up to! And I couldn't believe I was going to find out in such a sexy way!

I waited with great anticipation as she struggled with something under the tray. She shifted her hips back and forth once or twice and then shifted her butt upwards just off the seat. Her left hand re-surfaced, pulling the bottom of her skirt upwards. She then made one final shift and up sprung the biggest fucking cock I ever saw.

I beheld it for what seemed to be 10 minutes but likely was a few seconds. My breathing strained. I couldn't take my eyes off of it. Lita stared at me intently as I took it all in. She then leaned her lips towards my ear and whispered in the sexiest voice I ever heard, "so, do you want me?"

The question made me turn my eyes back towards her beautiful face. The intense look on my face slowly changed to a smile. I leaned in again, this time really close. I gently grabbed the side of her neck and pulled her ear towards my lips. "I knew," I whispered as I moved the hand on her neck to her jaw to turn her face, and planted a deep tongue kiss in her mouth.

I looked out of the side of my eye down at that massive pole emanating from Lita's lap. It was towering inches above the beverage tray. The olive-skinned head was swelled to capacity and pulsating as we made out. It was a little thinner right below the tip which, along with a well defined cock-head rim, made the throbbing bulbous tip that much more impressive. As my eyes perused down the veiny shaft I noticed how it began to get thicker as it moved down and the base was the widest point. I couldn't resist anymore. I wrapped my large masculine hand around it and my thumb and middle finger were still an inch away from each other.

As we made out and I dry stroked her huge girly cock, I thought to myself how I waited a lifetime for this. I was, no am, a masculine, straight pussy hound. When I was 19 however, I got a thing for chicks with dicks, discovered anal stimulation and have since loved she-cock as much as pussy. But they both have to be attached to a hot feminine human. My friends would never understand this, hence I kept my tranny obsession and occasional dalliances very private.

That was what was so amazing about this opportunity. In my early twenties, I hooked up with approximately 25-30 shemales and cross-dressers. Most we borderline passable, but not like Lita. The few I hooked up with like her were working girls, as opposed to my internet meetups which overwhelmingly were small-to-average dicked, no implants, kinda but not really passable Filipinos. Since I got married, I decided not to fuck with working girls due to the risks involved to my wife and family, as well as the 10-12 girls a year (or more) I fucked behind her back.

It's also why as confident as I am, I didn't approach Lita in the airport. If Lita was a bio-girl, which in the hangar I was 98% sure she wasn't, I would have been all over her and likely hooked up and figured out a place to fuck her before we got on the plane. But I don't allow anybody, not strangers, no one, to see me in any sort of intimate situation with someone rocking a cock. Lita was super passable, but as with most glamorous shemales, anyone with a trained eye would know she was packing.

We continued making out as I stroked her girl-tool. I tried to awkwardly reach down with my left hand to undo my pants because I didn't want to let go of her massive treasure stick. I eventually had to acquiesce and free my rock hard, sizable manhood with both hands. It was an inch or so smaller than hers, but quite impressive in its own right. I eventually got my balls above the band of my boxers and my erection was pointing upwards toward my face, resting on my flat stomach. Lita reached down with an open palm and began to rub the underside. Meanwhile, I reclaimed her big dick with my right hand and resumed stroking it.

Normally when I'm about to eat pussy or suck girl-cock, I work my way down slowly. You know, play with some titties, lick a soft belly and /or some inner thigh. But I couldn't wait any longer. I had never seen a lady stick like this before, I needed it in my mouth! Not to mention we were in airplane seats! I pulled my face away from Lita and looked over the seat to make sure everyone was still seated and likely sleeping. The coast was clear and when I moved my head back down I went right for her cock. Stabilizing it at the base with a clenched fist, I puckered my lips and took the tip and maybe two more inches right into my mouth. I moved up and down that real estate for a moment or two, circling my tongue to give her more pleasure. After getting into a good cock-sucking rhythm, I shifted to get comfortable and allow her access to play with my dick.

I bobbed my head up and down in Lita's lap as she stroked my hair with her left hand and my cock with the other. It got a bit easier as I gagged and drooled on that gigantic, stiff pole and worked my way farther and farther down. Lita unbuckled her seat belt and put the gray table up which was in both of our ways. She then shifted her hips a bit and took a firm hold of the back of my head. She began thrusting her pelvis upward as I came down her erection to drive her big dick deeper into my face. She got into a cadence of three upward thrusts and then the fourth upward movement was coupled with a downward push on my head to drive her she-cock as deep as possible into my throat.

I was gagging a bit but not loud enough for anyone to hear, at least I think, but the third time she tried to force her erect girly-cock as deep as it would go, I did gag loudly, coughed and pulled my head up while letting out a mouth full of drool. After I gained my composure, I looked up at her with teary eyes and we both let out a little laugh. I gave her a look indicating for her to see if she thought anyone heard or noticed. They didn't. Or at least we think they didn't!

I wanted to take my pants off and just straddle that beautiful she-cock. But I knew I couldn't. So I got back to work. Sucking that massive shaft was a little easier now as my saliva had lubed it up quite well. I didn't want to be gagged anymore, so I employed my hybrid stroke the bottom two-thirds with my hand/suck the tip and a little bit more with my pursed cock-sucking lips. I worked her impressive package this way until Lita grabbed both arm rests and arched her back, I knew she was close.

Taking her cue, I increased the speed and tightness of my grip around the base of her lady-stick. I began to rotate my head around in a twisting motion to tongue as much of the underside of her shaft and cockhead as possible. I always found stimulating this sensitive area worked well, and I was right. Lita let out a low, consistent moan and her body started that pre-orgasm quiver. Soon, I tasted salty pre-cum that began to ooze out of her cock hole. A few seconds later, a significant spurt of viscous cream shot into the back of my throat. I closed my lips tight to not lose a drop and waited for the rest. The first eruption was followed by one more major explosion of girly-boy goo, and a few after spurts. I made sure to hold her erection firmly, gripping and twisting the base while mouth-massaging the tip to ensure she fully enjoyed her climax.

The entire load was in my mouth and I carefully extracted her penis from my face, making sure not to lose any. I sat back up with cheeks drawn in and lips pursed. I nodded my head down, puffed out my cheeks and swallowed the gift she just deposited in my mouth in one gulp.

I leaned in to kiss her again and she accepted my cummy tongue. We kissed lightly as I continued to massage her now satisfied she-penis. We stopped kissing and I moved my head back to focus on her beautiful face illuminated by the overhead reading light. "Nice," she said as she stroked the side of my hair. "Your turn."

Lita scooted to get in position to suck my cock but I stopped her. "I want you to fuck it out of me when we land. I've never had a cock like yours. Can we do that?"

She laughed and responded, "mmm, you nasty little cockslut! Where?", she asked.

"We'll find a place, I'm not worried. We land in less than 30 minutes. Rest up and reload," I said as leaned in for a kiss.

With girls, I am a virile, alpha, mouth, pussy and ass fucking machine. But with ladyboys, I don't know, I'm a total bottom. I think that's the point, the cock right! It's what is unique. And it's my chance to take a break and be submissive.