“We only have one room left,” the attendant said, glancing back and forth between Steve and I, nervously. “Is that going to be ok?”
I rolled my eyes as obviously as I could. “I’ll try to restrain myself.” I heard Steve chuckle behind me. “Is there 2 beds, or can we get a cot…?”
The attendant agreed to send up a cot. I signed the necessary documents, grabbed the keys and we headed upstairs. “I’m glad you came.” Steve sighed as we got in the elevator. He said that every time. If ever there was a person that needed an assistant, it was Steve. He couldn’t book a hotel or flight to save his life, and God forbid a storm delay his flight – I could imagine him sitting in the airport forlornly trying to decide what to do.
Steve was a sweet man who was a friend of my older brother’s. I had known him for years, and though I was 15 years his junior, he had always been kind and friendly to me. He had married and had children young, so now he was barely in his 50s with 2 grown children and the freedom to pursue his dream of lecturing across the country. His wife had been his assistant for years, but she had died a few years ago after a long illness. When Steve wanted to get back on the road, he asked if I’d be interested in helping him.
Of course I said yes. I never really liked the 9-5 scene and enjoyed my freedom, so this gig was perfect. It was basically an all expenses paid vacation for a several weeks twice or three times a year. Sometimes the destination sucked, but there was always a spa or mall I could entertain myself at while Steve did his thing. And sure, I had to make sure he got to where he needed to be on time, but that was actually a pretty easy job. And to be honest, I had a crush on Steve. I had for a long time. Not that I thought it would turn into anything, but I liked hanging around him.
Today had been a bit stressful, but by the time room service arrived with a late dinner and our cot, I had called ahead to the venues and organized everything. We scrolled through the movies and settled in on the bed to eat and relax.
“So are we flipping a coin for the cot, or…” I joked. Steve laughed but didn’t answer.
“Thanks again for working this all out.” He gushed.
“No problem.” I shrugged. “It is my job.”
“I know. But you really are great at it. I thought when Mindy… well, I didn’t think I’d be able to do this again without her, you know?”
I nodded, my mouth full of pasta.
“You remind me a lot of her.” Steve continued between bites. “She never took anyone’s crap either. But you’re different, too.” He waved his fork at my tattooed arms.
“Are you alright?” I joked, downing the last of my wine having finished my dinner. “You’re not usually this sentimental.”
“Oh, I’m fine.” Steve sighed. “Just…glad you’re here.”
I suddenly became aware of how close we were sitting to each other on the bed. His arm was brushing mine, and when I glanced over at him, our eyes met. He definitely showed his age. He had bright blue eyes that were framed with laugh lines and his face was classically masculine, with his usually smooth skin showing a dark five o’clock shadow, betraying the hour. His dark hair was shot through with silver and his once athletic body (I’d seen pictures of his college days with my brother) was now a certified dad bod. But he was still good looking. I breathed deeply, taking it in, smelling his cologne, like I did often, appreciating the view. But before I could turn away, his face leaned in and his lips were on mine.
His kiss was strong and sure, and passionate. I was taken completely aback. I had no idea he saw me as anything but his friend’s baby sister. But it ignited a fire in me and I wrapped my arms around his neck and as his hands found my waist. He pulled back momentarily, mumbling some apology, but I pulled him closer without a word, locking in to another kiss.
There was no turning back now. He rolled halfway on top of me and kissed my lips, neck and ear as his hands wandered over my clothes. My own wandering hands found his button and fly, and he caressed my skin under my shirt until he came to my bra. As I pushed his pants down over his still decent ass, he expertly unclipped my bra and fondled my breasts under the material. Before long, he pulled my shirt and bra over my head and I sighed as he sucked and massaged my bare breasts. He hooked his thumbs into the waist of my yoga pants and with one smooth movement he yanked them down, caressing my ass on the way back up.
His mouth came back to mine as he ran a hand over my aching pussy, sliding a finger through my wetness and giving my clit a little rub. I breathed out his name and he stopped kissing me just long enough to ask if he should stop. I said no, and before I knew it I felt his hard cock slip into me. I gasped as he pushed himself in as deep as he could, letting out a moan. I wasn’t sure what I was expecting, but I was pleasantly surprised to find he stretched my pussy deliciously, and I moaned as he filled up every corner of my hole.
His strokes were steady and not fast, but deep and urgent, like he hadn’t fucked anyone in a while and just needed to DO it. But I am not a woman to be left unsatisfied, so after a minute or two I pushed up from under him and he let up just long enough so I could turn the tables on him. With him reclining on the pillows, I straddling him and brought my dripping pussy down onto his cock. I let him pull me forward to kiss me passionately as I grinded myself on top of him before sitting up so I could massage my clit. He interrupted me, taking my hand and sucking my juices off each finger, before taking over, one hand tending to my clit and the other gently pinching my nipples. I felt my orgasm building so I filled myself up with as much of his cock as I could as the dam broke and wave after wave of pleasure washed over me.
He pulled me to him again and, with my pussy still pulsing on his cock, he rolled me back over. He pinned my hands to the bed, fingers interlocked with mine, and stroked in and out, over and over, making the most of my orgasm. I relished in this attention, moaning softly as he kissed me, sucked on my neck, and nibbled my ear. No one had ever fucked me with such passion. Finally, with one last thrust to the hilt, he let out a moan and I felt his cock spasm inside me, his warm cum filling me. He stayed inside me as his erection subsided, kissing me and running his hands over my skin one last time.
After he rolled off, still holding me in his embrace, and fell into a peaceful sleep, I lay drifting off myself. The last thing I thought before my eyes closed was “what the fuck was that!?”
Source: reddit.com/r/eroticliterature/comments/p4ltoh/delayed_flight_female_pov_romantic_older_man
Beautifully written….amazingly told…vibrantly detailed.
And as an older man (kinda) myself, very much appreciated.
Well done, thank you for sharing!