Short but Very Sweet

This happened a couple of years ago. I was flying From South Florida to Las Vegas for work.

i had settled in my window seat and a very cute guy sat next to me.

As the plane started to accelerate for take off he unexpectedly grabbed a hold of my arm, and i could see complete terror on his face. So I gently put my hand over his and rubbed it softly and whispered to him that "Everything was going to be OK."

He was holding on tightly until we were well up in the air then he started to relax a little bit.

He apologized profusely and said "This was his first time on a plane and he didn't realize how scared I would be."

I assured him that he had nothing to be embarrassed about and that i didn't mind at all.

He said "It's embarrassing, I'm a grown man clinging to a complete stranger like a little boy."

I assured him i was glad I could help and just then we hit turbulence.

He was scared so I took my sweater off, offered him my hand and when he gripped it tight i covered our hands and the arm rest with the sweater so no one would see he was holding my hand.

We held hands for most of the flight and whenever we hit turbulence i would lean over and whisper "Shhh its ok."

And in landing he squeezed so tight i joked with him that "I couldn't feel my hand."

Later while waiting for our Luggage he apologized about 25 times I again told him "it was a pleasure to help him through the flight."

That was Thursday.

On Saturday I was relaxing having a drink by the hotel pool (Guy watching) and I noticed him in the pool. When he looked up and saw me he swam to the steps and exited the pool.

As he emerged from the water i saw his absolutely beautiful body.

As he came all the way out of the water i noticed 2 things. He was only about 5'4". I'm not exactly sure why I hadn't noticed that before.

Also he was wearing a white Speedo that was almost transparent and he had a gorgeous bulge with a cock I estimated to be about 4" soft.

As he walked towards me i had to put a towel over my lap so he wouldn't know I was sporting a very hard cock myself.

He asked if he could sit next to me,and of course I said "absolutely ".

He mentioned it was a "Happy coincidence that we were staying at the same hotel."

Again he brought up how embarrassed he was about his behavior on the plane.

I told him not to worry about it and that "I never complain when a cute man holds my hand."

He had a look of minor surprise as he realized I just told him A. that I'm gay and B. I think he's cute.

Understanding the awkwardness, I apologized if those admissions were making him uncomfortable.

He assured me that he was fine with that and also "Flattered." And I thought I saw him blushing just a bit.

I told him, "That the way he held my hand I just assumed he was gay as well."

He said "I'm straight, but to be honest it kinda felt weird but kinda nice holding my hand."

He then mentioned he had a very limited experience with his roommate in college.

He told me that after a night of drinking they actually made out and masturbated together. "But that was the extent of it."

I told him "It's totally normal for young guys to have that kind of encounter."

Then he said he would stumble on gay porn every now and then on the internet and "Sometimes I continue watching it."

He said "I'm sorry I'm getting so deep with a stranger about my life choices."

I said "I held your hand for 4 hours so I think I'm hardly a stranger."

He laughed and said "I guess that's true."

He then invited me to share a pizza with him later that evening and i accepted.

So he gave me his room number and we agreed on 7:30 that evening.

As he stood up to return to the pool I couldn't keep my eyes off his crotch and he noticed and reached down and squeezed his package ever so gently and smiled and said "want to thank you properly for the other day."

As he walked away I know I groaned out loud at the sight of his perfect ass swaying so fucking perfectly.

At 6:30 I took a shower and shaved from my neck down. Douched very thoroughly did my makeup.

I put on a black satin push up bra matching panties a red garter belt, black seamed stockings, a black leather dress that came about 2" below my ass and 3" high over the knee patent leather boots. And topped it off with a shoulder length jet black wig.

It was now 7:20 so I threw my key card, lipstick and lube in my purse and headed to the elevator.

I was on the 4th floor he was on the 12th there were 4 or five people on the elevator and no one really gave me a second look. Although one man did say "have a good night Ma'am" as i got off the elevator.

Even though i never tuck so anyone can see I'm a Transvestite and not a woman. (I want people to know what I am in public) I thought it was very sweet of him.

I knocked on John's door and he opened and asked "Can I help you?"

I said "I thought we had a dinner date" that's when he realized it was me and invited me in.

I said "I hope you don't mind but this is what I like to wear after dark."

He said "No, not at all you look very nice, I think you're very pretty but very tall in those heels."

I told him "I'm worth the climb."

He laughed and replied "I bet you are."

With that I had him sit on the bed and dropped to my knees and pulled his sweat pants and underwear off in one shot.

His cock was hard and had grown to about 5 1/2-6" with a huge mushroom head as I leaned in to lick it he pushed me back and said I've never been with a man before and he was nervous.

So I joked this time and said I'd "never been with an elf before."He laughed and let go of my shoulders and I gave him the blowjob of his life.

I started by slowly licking his piss slit as it was producing a heavy amount of pre-cum. Then wrapping my tongue around the shaft and going sown its length. Then planting my lips on it and slowly going back up to his magnificent mushroom head. As I reached the top i took its whole length in my mouth.

I edged him several times until he just grabbed my head and shoved it down on his cock and held it there while he shot at least 6 shots of cum.

Which of course I swallowed every bit of.

When he regained his composure i removed the lube from my purse and applied a generous amount to his cock and my hole, climbed onto the bed and we kissed.

He was one of the most gentle and sensual kissers I'd ever kissed.

After about 15 minutes of pure necking he asked me to "stand up" and he removed my dress and said he loved my lingerie.

I noticed his cock was still rock hard so i went down on him again.

After a few minutes I had him roll onto his belly and there was that amazing ass. I couldn't help myself i spread his beautiful cheeks and tried to pierce his heart with my tongue he let out a big moan.

He told me "No one had ever eaten his ass before and please don't stop" so I ate his beautiful hole for about 10 minutes.

Then he grabbed me and flipped me on my back and ripped my panties off and mounted me Missionary Style. I lifted and held my legs up and as far apart as I could by grabbing ahold of my boot heels.

He managed to find my hole with his cock and applied enough pressure so the head popped in passed my ring.

He seemed to understand the process as he stopped pushing and let me get used to the gorgeous cock invading my Boi-cunt.

I started to kind of lift up into him giving him the green light and he got the message. And he pushed a couple inches in, pulled back and added a couple more. Soon enough he was buried balls deep.

He fucked me like that for about 5 minutes.

Then we fucked in every position we could think of. He fucked me for an hour. I came 3 times.

He then had me lie on my back with my head off the edge of the bed and he throat fucked me hard for about 5 minutes ( thank goodness for Strawberry flavored lube)until he backed out of my throat until just that big mushroom head was in my mouth and gave me another nice load which I again swallowed every bit of.

Later he told me he took "A little blue pill before I got there because he saw how I was looking at his cock by the pool."

We never did eat the pizza.

I slept in his arms that night and he fucked me in the morning and when we got back to South Florida we moved in together and stayed together for about a year.