I Fly Away

Story Info
A fantasy of a brief encounter.
1.9k words
22.7k
17
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

AUTHOR'S NOTE: This encounter is purely one of fantasy fiction. It was inspired by a conversation with a friend and a "what if" moment...enjoy.

I flew out of town the other day for a business meeting with a publishing company. Much to my surprise as I walked down the airport concourse, a beautiful woman met me at the airport. She was standing outside of the security area holding a sign with my name on it. She was tall, which was accentuated by her five-inch stilettos. I followed her slender legs up until they ended in a lovely little round ass. Her breasts were full and shapely. I wasn't sure if she was wearing a bra because I could see her nipples straining to burst through the silky black dress that she wore. Her jet-black hair cascaded in lush curls to fall gracefully around her shoulders. It framed a gorgeous face with high arched eyebrows and piercing blue-green eyes.

She told me that she was sent by a mutual friend to make sure that my stay in the city was pleasant. She offered to take me to my hotel as we walked out of baggage claim. Her car was parked just across the street from the airport. As she opened the trunk with her remote I glanced up surprised to see a sporty 525i BMW flashing its lights at me.

I offered to take her to lunch as recompense for her generosity to which she agreed. We had a lovely meal followed by a stroll through a nearby park and pleasant conversation. She told me that she'd read all my stories and how much she liked them. She told me about herself, her life, and her dreams. Then I shared some of my own. I told her that I wished that I could help her toward her goals but we both knew that it would never happen.

After our walk in the park she took me to my hotel and helped me carry my baggage into the lobby and reception. While checking in, the hotel clerk mistook us for a couple and gave us two keycards. I'm was too shy to refuse and I handed one to her rather than cause a scene.

She used her card to open the door and I pulled my luggage into the room to deposit it on a single king-sized bed. She smiled and sat in one of the chairs while I unpacked. We continued our conversation, discussing little things of insignificance.

Finally, unpacked, I sat on the edge of the bed and relaxed. She walked over seductively and sat beside me taking off her heels. She paused a moment then leaned forward and kissed me. She tasted sweet and soft, my heart was beating rapidly. She slowly unbuttoned my shirt and removed it. Then she massaged my breasts and used her long nails to pinch my nipples lightly, more to tease than to give pain. Her hand moved down to my belt and she unbuckled it. Then she unfastened the button at my waist, unzipped my pants, and slowly released my cock.

She smelt of sandalwood and rose, exotic, sensual. My heart was racing.

She looked up and gazed into my eyes a moment. Her eyes were smoldering and sultry. She leaned forward and took me into her mouth, slowly licking the tip and down the shaft then enveloping me until my cock touched the back of her throat. She gagged a little then she pulled back to suck me hard in and out of her mouth. I was so excited I barely made it a few strokes before I felt an urge deep in my balls to come.

She felt me tense up and she brought her taloned hand up to squeeze the base of my cock and stop the flow of my come. "Too soon," she whispered.

She sat up a moment and pulled my pants completely off of me then urged me to move up onto the bed further. While I reposition myself she pulled on a zipper and her dress fell around her ankles revealing what I suspected, she wasn't wearing a bra. Her nipples stood erect and I look down to see her cock emerging from its confinement in her lace thong. It looked big, bigger than mine. And it looked beautiful. The thought surprised me, as I have never thought of a cock as beautiful. But hers was.

She knelt back onto the bed and slipped her hand down between my butt cheeks to massage my rosebud. It is now when I realize that one of her fingers doesn't have a long sharp nail attached.

She reached for her purse. Inside it she pulled out a small tube of lube. She covered the middle finger of her left hand and then she slipped that finger into my ass. I clinched at first, feeling the cold of the lube inside my rectum but she shushed me, smothering my protests with her luscious lips.

She resumed her attention on my cock while she moved her finger in and out of my rectum like a little piston. Then she worked her finger around in search of my prostate. When she found it she began to massage it vigorously. My body arched off the bed. Between her invasion of my ass and her wonderful assault of my cock the sensations were overwhelming.

Suddenly I came, for the first time in a very long while I really came, a lot. The woman was a magician. I haven't come like that in decades. Eventually my breathing returned to normal, well sort of normal considering a beautiful goddess was still stroking my cock and pushing her finger in and out of my ass. She lifted her head up to me and smiled then she pulled her finger out of my ass and slowly moved up to kiss me again. I could taste my seed on her tongue.

She whispered, "I want you," and I looked a bit frightened. She smiled reassuringly and moved back to her purse to pull out a condom, which she handed to me. She moved forward and presented her cock to me so that I could slip the condom on her beautiful shaft. Then she coated her condom-covered cock with lots of lube before she positioned several pillows beneath my ass.

I started to turn over but she stopped me. "I want to watch you while I take your cherry," she whispered sweetly and I watched her position her cock at my entrance. Slowly she pushed into me, past my sphincter, and deep inside my bowels. My body expanded to accept her girth. There was pain but mostly it was discomfort. I felt so incredibly full. She paused a moment waiting for me to adjust then she began to move inside of me, slowly at first but then she picked up speed until she was driving into me furiously.

My god how she commanded my mind and body, not a word was spoken but our eyes are locked on to each other. Our bodies were synced in a rhythm of passion as she pounded her rod into me.

At first I didn't notice it but suddenly I became aware that my cock had sprung back to attention, it was throbbing with each of her thrusts. She picked up even more speed, even more intensity as she continued to thrust into me. She paused a moment, I could feel her swell in size. I know she's close. A moment later, in a single thrust, deeper than ever before, she arched her back filling the condom with her come. She dug her claws into my shoulders as she collapsed on my chest, her breasts pressing against mine. Her breath was heaving and rapid.

We stayed like that for a moment while she slowly softened and slipped from my ass. She shifted sideways and fell off my chest but she kept her leg across my thighs and her arm across my breasts, as if still possessing me. Her eyes were closed at the moment but eventually she opened them to smile at me.

"I was told that you wanted to experience that," she whispered and I nodded with a sheepish smile. "I was told that I should leave after we are done and never speak of it again. If that's what you want I'll do it but honestly, I'd like to stay with you a while longer."

"For the weekend?" I ask, my voice quavering. She nodded briefly. "You're so incredibly beautiful," I said, "wouldn't you rather be with your boyfriend than an old guy like me?"

"I know it's just for the weekend but I really want to be with you," she said smiling demurely. "I feel so safe here with you and it felt so good to be inside you." She gazed up into my eyes, cupped my face with her beautiful hands, and my heart melted. "Would you make love to me?"

We came together several more times that night. With this beautiful woman making love to me I felt like I was twenty again. I knew it could never last. That it was a brief moment in our lives never to be repeated, but it felt like nirvana as I laid enveloped in her sweet embrace.

Saturday morning, she drove me back to the airport, her hair all disheveled, wearing jeans and a t-shirt. She was stunning in her simplicity. It seemed so natural to be with her, sitting next to her. If I had had a daughter I would love for it to have been someone like her. I know that sounds incestuous but that's not how I thought of her. She was such a beautiful person, inside and out.

As she parked her car in the airport parking lot she slipped on her five-inch heels again. God how I loved to watch her butt sashay in those heels as she walked around her car. She opened the trunk so that I could retrieve my luggage.

"I'm so glad I got to meet you," she said running her nails seductively across my chin so that I kissed each finger as she slipped them past my lips.

"You'll be in my next story, your name will be Anna and you will be amazing."

"What will I be? Magical?"

"Yes, you'll be a goddess."

She kissed me passionately and slipped a small card in my shirt pocket. Then she stepped back and smiled as I sadly turned to walk towards the check-in counter.

A week later as I started to do my laundry I noticed a small card in one of my shirt-pockets. I pulled it out and read it.

"Dream of me my sweet, for I will be dreaming of you."

A NOTE TO THE READER:

This story is a work of fiction. All of the characters, their names and the places that they visit, are purely from the imagination of the author. Any resemblance to persons, places, or things is not intentional and purely coincidental.

If you believe in coincidence I'm happy for you. However, if you read my other works you know that I do not, but the lawyers like to see that word in there anyway.

Thank you for reading my work, I hope you enjoyed it. If this is the first time you've read one of my stories, welcome. I hope you take a look at the rest of the work that I've published her on Literotica.com. If you are a returning reader, welcome back, it's nice to see old friends.

  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
AnonymousAnonymousover 1 year ago

Beautiful!!!

AnonymousAnonymousover 6 years ago
Dressed for a man

I remember the first time I dressed up for another man . We had conversed on line in a chat room and I had told him I was a crossdresser- that really excited him as it does me !!.. to cut a long story short, on Monday I invited him over to my house ( I live alone in a remote country cottage) for dinner at 7 pm on Friday

All day I spent preparing food .. and myself ( long hot bath, total body shave and 2 enemas )

By 6pm I was getting ready for my guest .. dressed in my new panties, bra , suspender belt and stockings , I applied my make up carefully before slipping into my black dress and donning my long blonde wig ...I looked sexy .. grabbing my new 5 inch heels I went through to he lounge and waited, sipping a drink as I did ....

At 6:55 the bell rang and before answering , I put on my heels and walked confidently to the door ( takes a LOT of practice to walk in them )...

Ben was stood at the door with a bottle of wine as I opened it wide and ushered him in ...

“ Wow!!.. you look fantastic Barbara( my sissy name ) “ he breathed .. my heart and COCK lurched at the compliment

“ You look handsome too Ben “ I said pecking him on the cheek before leading him into the lounge

“ Drink?” I asked in a sultry voice .. he didn’t reply , just pulled down beside him and kissed me passionately ( we had discussed kissing and both of us liked it )

His hands wandered under my dress and he murmured ‘lovely’ as he encountered my stockings and suspenders .. dinner was forgotten until later as I led him into my bedroom ..

“ I need fucking now “ I moaned like a whore ( I felt like one too )

Ben took me straight away , my dress round my waist as his lovely cock ploughed my twitching hole .. we both came .. him inside me , me on my tummy !!

Dinner was eaten at 9pm after which we went to bed and fucked the whole night long

I woke him at 7 am , sucking his cock - he just ‘ manfully’ flipped me onto my back and fucked me again .. and again

Fly_paraFly_paraover 8 years ago
stars

somehow the star rating is gone but l give it 4 stars, reads well and l enjoyed it, thx for sharing

cliptoecliptoeabout 10 years ago
Once again a hit!

Wonderful fantasy, it makes one wonder how many times a 'what if' situation passes us by, fearing that step across the fantasy threshold.

Thank you for yet another exciting read!

Joscelyn2tgJoscelyn2tgabout 10 years ago
Once Again A Beautiful Gem...

...Of a story is polished to a fine luster. Its a lovely fantasy that delights the senses and excites the mind to an erotic vision within an everyday scenario. Thanks once again for sharing such romantic stories, and I will be hoping for more just like it!

Share this Story

Similar Stories

Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
What A Man Needs? A guy, a porn shop, and a surprise.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
The Roommates Ch. 01 Brad moves in with a couple of girls who hide secrets.in Transgender & Crossdressers
Finding My Dream Wo(man) Never knew I wanted a tranny till I found one.in Transgender & Crossdressers
More Stories