An Unexpected Friday

It was late on a Friday afternoon when the business meetings were finally over and I walked out of the office what to do with myself until the next morning, when I would be taking a flight back to my home city. I had flown in early this morning, hurriedly checked into the downtown hotel I had booked, and then caught an Uber the few miles to the offices. It was still summer, and the evening weather was gentle, so I thought I'd get some exercise and see an unfamiliar town along the way.

Taking my bearings I swung my laptop case over my arm and headed down the street, taking In the sights. I paused at a shop window here, glanced down a few side streets there, doing the usual things one does when enjoying a walk in unfamiliar territory. Seeing a park off to my left a few blocks, I turned down towards it, and soon found myself in a small bit of green surrounded by city. One of the streets that faced the park had a selection of small cafes and restaurants, so after a restful pause on a park bench I wandered over, selected an Italian restaurant, and had a meal on my own, at one of the tables that lined the street.

After a glass of wine with my meal I considered having something stiffer at the bar next door, but as the evening drew into darkness the scene on this little stretch of street had gotten louder with the sounds of people celebrating the weeks ending. I wanted someplace quiet to have a last drink before heading up to my room. Thinking that the bar at my hotel would probably be the sort of place I was looking for, I paid the check and headed out for the last few blocks. An early morning flight and the events of the day had really worn me out.

Arriving at the hotel and passing through the lobby to the bar I knew I had made the right decision. It was the usual anonymous place, with the kind of bartender who knew when to stand quietly in the shadows and when to engage in conversation. Scattered around the low lit room were a few tables, while the back wall was occupied by three booths. The bar itself wasn't long, and as I entered I saw the backs of a few patrons sitting there, while one of the booths held three people in business attire, seemingly engaged in the same pursuit as I, unwinding a bit from a day of meetings before heading up to the rooms.

Stepping up to the bar I caught a whiff of an unfamiliar floral perfume, and saw a mature woman sitting alone off to my right. Her hair shone with silver highlights in the low light, and I saw that she was well dressed and alone. Perhaps a fellow business traveler, I casually thought to myself as I caught the attention of the bartender and ordered myself a gin and tonic, planning to carry it over to a booth. As I spoke she glanced over at me, and I smiled and nodded as I made brief contact with her blue eyes. My glance took in that she was attractive, probably in her late fifties, with light makeup. Her hair was cut in a bob and framed her face, while earrings shone through the hair. A heavy necklace of silver and stone beads lay above the scoop neck of her conservative dress. The dress was of a heavy brocade fabric, and fit her middle aged figure well. Heavy breasts pulled the fabric tight across her chest. She returned my smile with a nod and turned to look at the wall behind the bartender.

I took my drink and turned away from the bar, walking over to ones of the booths. I sat back and tugged a bit on my tie, loosening it. I was ready to head up and get out of my suit And into something more comfortable. I looked forward to relaxing in the privacy of my room, maybe watching a movie. Thinking over the day's events, I sipped my drink and closed my eyes for a moment. Productive conversations, business connections and decisions, a brief lunch followed by meetings with another department, future moves planned.... Before I knew it my drink was gone. Catching the bartender's eye I lifted my finger, signaling for another.

As he walked towards the table I dug into my laptop bag for my wallet, preparing to give him my credit card. "No need, sir. The lady at the bar asked me to say that it looks like you've had a long day, and this one is on her."

I sat up a bit, and looked over at the woman. Her back was to me. I considered the situation for a moment, and then looked up at the bartender. A quiet chat that wasn't about work might be just the thing.

"Please extend my thanks and ask her if she needs a refill, on me" I said, this time opting to leave some cash on his tray.

As he walked away I again glanced over to where she was sitting. Profiled against the soft lights from behind the bar, I could see her pantyhose clad legs and the soft roundness of her shoulders. Her bobbed grey hair haloed around her head backlit by the lights of the bar. I saw the bartender speak to her and then watched as she nodded. He placed a fresh drink in front of her. She picked it up and turned, dismounting from the barstool as she did so, and looking in my direction. Sitting up a bit more I nodded and smiled welcomingly, inviting her over with a gesture. As she sat opposite me the faint fragrance of her perfume wafted across the table.

"Marc" I said as she sat, introducing myself. "Thanks for the evening's last drink."

"Diana. And perhaps I should say the same. Are you here on business?"

I confirmed that I was, and that she was right, it had been a long day - waking and catching the plane, and then a day of business. I had another flight to catch back home the following afternoon. She too was here on a business trip, though in her case she had flown in on Friday to have some personal time over the weekend before meeting with a potential customer on Monday. She was in sales for a large business software company.

"Though at my age, you are probably surprised I am in the tech business" she laughed.

"You are only as young as you feel," I said. "And you look to me like you feel pretty good." As I spoke I realized the drink may have loosened my tongue a bit more than I usually liked. I felt a bit of a flush to realize I was on the verge of flirting with this woman I had just met. Of course, she had sent over that last drink.

"Well thank you" she said, suddenly turning a bit serious and holding eye contact. "As a matter of fact, I am feeling pretty good right now. She dropped her hand onto the table, brushing it against mine, then moving it a bit to the side. I held her blue eyes for a moment with mine, and then turned to the conversation to what she planned to do with her weekend. There were some stores she wanted to shop at, and a museum that was holding an exhibit she hoped to see.

"Just a bit of freedom...a change of pace. One gets tired of the same places and faces in one's hometown. I find it fun to be in a different town...a different me, perhaps. I'm planning on sleeping in, room service breakfast, and seeing how the day unfolds."

Again I caught her perfume. Her hand still lay on the table where she had rested it. "The freedom of a new city, of no connections" I said with a smile, agreeing with her. As I did so I brought my hand over to rest against hers.

"Exactly" she smiled, as we touched. A moment passed. We sat in quiet, then began to chat again about this and that. Small talk with a new person. Our hands stayed touching.

"Well" I said, unable, as I looked at her eyes, framed by her grey bangs, to read her. "Thank you again for the drink, but it has been a long day and I'm mentally a bit fried. I think it's time I headed up to my room."

"Early to bed, early to rise?" She asked, raising an eyebrow. "I'll share the elevator with you, if I may."

She slid out of her side of the booth, glancing back at me as she walked towards the lobby entrance. As a followed her out into the light I saw that she wore a medium heel, and that the tailored waistline of her dress dropped to a hem that rode just below her knees. The curve of her hips was clear under the fabric of her dress. She had the softness of middle age, kept In check by exercise and diet. The pantyhose on her shapely calves caught the light as she strode towards the elevators. I caught up and stood next to her as we waited for the doors to open.

"I'm on the top floor" she said as we stepped inside. "There's a nice view of the city from up there- I pushed the travel allowance a bit but as I said, I'm taking a bit of 'me' time on this trip."

"Nice. I'm on nine please" I said, as she was standing at the elevator buttons. We began to rise.

"Perhaps you would like to see the view for yourself." She smiled over at me. "I could buy you another drink from the room bar."

I met her eyes again, and smiled. "That sounds nice, but I warn you, with another drink I may not be responsible for my actions. I'm generally a pretty light drinker."

"That sounds like it might get exciting, but consider me warned." She chuckled. The doors opened at my floor, and she pressed to button to close them. As the elevator rose, I wondered what I was getting into, but decided to let the evening flow. The light hearted conversation put me at ease.

The doors opened, and she again proceeded me down the hall, turning and opening a door about halfway down. As we stepped into the room she stopped short, turning to face me. We stood close. She was just below my height, and as her eyes tilted upward to meet mine, she placed her hand on my chest and looked at me for a long moment, a question in her eyes. I bent forward and brushed her lips with mine, feeling their movement as they took the shape of a smile. Her hand dropped slowly down, brushing against my stomach as she withdrew it.

"Allow me a moment to freshen up. The bar is over in the corner. Whiskey on the rocks for me please." She smiled slightly and turned away and entered the bathroom.

I walked further into the room. At the bar I mixed a couple of drinks, going light on the gin, and pouring a few fingers of whiskey over ice into a glass for Diana. Drink in hand I walked over and pulled open the sliding glass doors that lead onto the balcony. Before me the city lights spread out. I heard the bathroom door open behind me, and then felt her arms circle around me. On my back I could feel the pressure of her large breasts. We stood still for a minute, and then I turned to face her, still with her arms around me. I put my arms around her, touching her lower back. As I bent slightly down, our lips met. Eyes closed, I tasted her lipstick as our tongues touched. We kissed gently for a long time, gradually becoming more passionate. I could feel my cock rising, pressing against my pants and through them her tummy, as she pushed against me.

I dropped my hands down, feeling beneath the rough weave of her dress the silky smoothness of her panties on her ass. Pushing back against her I let her feel the pressure of my erection.

Suddenly she broke the kiss, backing from my arms and taking a breath.

"Marc" she said, looking at me. "Before we go much further, I need to tell you something."

I looked at her. Our eyes met. "Should I be sitting down? " I jokingly said, a smile playing on my lips.

"Perhaps. It depends on how you feel. You strike me as an open minded fellow. We've both seen much of the world...." she trailed off. "I never know how to put this, most men who follow me to a room seemed to know right away..." she was suddenly nervous.

"You mean-" I asked as I moved towards her quickly and reached my left arm around her, placing my free hand on her thigh and, still on the outside of her clothes, moving it upwards, "this?" I moved my hand firmly across her crotch, feeling the bulge of her cock. I stopped my hand on it, feeling it pulse faintly beneath my palm. Her eyes widened as she looked into mine.

"That just makes you even more exciting" I said as I once again felt her mouth beneath mine, and felt her melt beneath me. As she stepped backwards towards the bed, I stayed in contact, lost in the smell of her perfume, feeling her lips move with mine.

"Mmmmm oh Marc. How well you kept my secret..." Again I could feel her mouth formin a smile. I began to kiss her harder, our mouths moving in unison. The taste of her lipstick, the smell of her perfume, the feel of the fabric of her dress.

Conversation was lost as we explored our bodies. Her hand slipped down to the front of my pants. I felt the movement of her palm through my clothes. I moved my face down her neck, kissing her chest, as I too massaged her cock though her clothes, feeling the heavy fabric slide against her pantyhose.

She rolled away from me, and stood. I sat on the edge of the bed as she stood between my knees. Now she bent and kissed me, slowly taking my shirt and tie off as she did so. As she unbuckled my belt, I raised my ass slightly so that she could ease of my pants and my boxer shorts. Her hands reached down to caress my shaft as it stood at attention. She glanced down at it as her manicured hands moved gently up and down it. Her grey hair brushed my cheek as she bent to kiss me, then she began to kneel down, pausing to suck and kiss each of my nipples briefly as she did so. Her tongue and lips moved across my stomach, lightly kissing me as she moved her head downwards.

"Wait-" I whispered. She stopped, suddenly frozen. Suddenly nervous. "I want you naked too" I murmured.

"But..." Diana said.

"Stand" I commanded. She stood. I slowly reached up, finding the zipper on her dress. I pulled it down, and it fell away from her shoulders onto the floor. Beneath she was wearing a black silk underwire bra supporting her heavy breastforms. Her pantyhose gleamed in the light, covering black panties, flattening the bulge I could see there. With her still standing between my knees I began to caress her legs, rolling the pantyhose down them, exposing the soft skin of her shaved legs. They came off to join the dress on the floor. I reached back up and massaged her breasts in the bra, slipping my fingers briefly beneath the forms to pinch her nipples. She gasped and began to move beneath my hands. Brushing my hand across her panty clad cock I reached behind her, grasping the waistband of her panties and pulling them down.

As she stepped out of her underwear, her small shaved cock was at face level. She had left a landing strip of trimmed hair that lead from the curve of her belly down to the base of her cock; she was otherwise smooth.

I looked up past the bra she was still wearing and met her eyes as I leaned forward, opening my mouth. With one hand on her ass I pulled her toward me, using my other hand to guide her into my mouth. Sitting on the bed, I slowly moved her back and forth, the rhythm building as she slid in and out of my mouth. Now she moved on her own. I lightly caressed the crack of her buttocks as the movement continued. She gasped, and her knees began to shake. She put her hand on my head.

I stopped, just as I felt she was on the edge. She stood with her cock in my mouth. I smiled, feeling her fight for control of her oncoming orgasm. I could feel her twitching in my mouth, and listened as her breathing relaxed. Moving her body back and slipping out, she looked down at me and smiled. Keeping eye contact I lay back and moved up the bed. My own cock stood stiff, curving back on my belly.

Wearing only her bra, she moved towards me, straddling my legs as she bent over to kiss me. I slipped my hands under the straps of her bra, caressing her as we passionately kissed. Our cocks rubbed together, our skin touching. Her breast forms pressed against my chest. My hands explored her back, her ass, feeling the soft skin.

Soon she began to work her way down my body until her head was at my cock. She took me into her mouth at last, slowly engulfing me in her warmth as she moved her head up and down. I lay back with my eyes closed, just enjoying the feel of her as she moved her mouth up and down, while at the same time massaging my peritoneum with her long nails. I felt myself moving towards the edge.

She shifted on the bed, turning her body until she lifted one leg and came down over me in the sixty nine position.She continued to gently suck me off. I reached around and placed one hand on her cock. Opening my eyes her ass was just in front of me. It glistened. She had lubed herself as she sucked me off. Gently massaging her cock with one hand. I began to explore her ass with my fingers. I placed my index finger against her hole, and left it there, pushing slightly. Continuing to hold me in her mouth she began to push back against my finger. I could feel her moan gently. Slowly I penetrated her, as she pushed back and pulled forward. I began to move my hand more quickly up and down her cock, timing my movements with hers as she thrust against my finger.

Taking her mouth off my cock, her breathing began to quicken. She gasped, and small moans began to escape her as I jerked her off and played with her ass. Arching her back she rose up, riding on her knees, a slave to the rhythm of her body. Giving a great gasp, she shuddered and finally came, squirting down onto my chest and belly, thrusting back onto my finger as her orgasm spent itself. I felt her cum wet on my stomach and chest. Releasing her cock, I reached down and scooped some of it in my hand, lubricating my own erection with it, slowly jerking myself off using her cum as lube.

She eased herself off of my finger, and slowly lay down next to me, face to face. Looking into my eyes, she reached down and brushed my hand away from my cock, replacing it with hers. Her grey hair brushed her cheeks. Her blue eyes burned into mine. The forms in her bra pressed against my chest.

"My god...." she said. "I'm old, but I don't know that I have ever come that hard in my life."

"Mmmm" I said, focused on the rhythms of her hand. It moved up and down. We kissed.

"And how did you know?"

"Mmmm" I said.

Now she sat up, positioning herself next to me. One hand moved up and down my cock, the other slowly moved deeper between my legs. I opened my hips to allow it access. She began to massage my asshole. Pulling her hand out and reaching for the lube she she poured it onto her hand then replaced it between my legs, her finger slowly circling my ass, pushing on it, giving me time to decide if I wanted to be penetrated. The other hand continued to move up and down my shaft, still slippery from her cum.

"No really," I could hear the smile in her voice. "I know I pass. So....?"

"Mmmmm" I said, feeling myself close to the edge, Her hand kept moving, slowly increasing its rhythm. I relaxed, letting her finger penetrate me. She moved it gently in and out, in and out. The rhythm on my cock increased. I opened my eyes. I looked at her as she sat cross legged next to me, still with the bra and her forms, her grey hair framing her face. Her makeup was smudged, and I could still taste her lipstick on my lips. Her earrings glinted in the light. Her cock poked up, beginning to get hard again. One hand moved up and down me, the other with in and out of my ass.

"Birds of a feather" I whispered, looking in her eyes. "I dress too." As I spoke I reached the edge. I shuddered and came, spraying cum all over her and me. Again and again I felt the waves of my orgasm in rhythm with her hands. She slowly brought them to a stop, her finger still in me as my cock softened in her hand.

"Mmmm" she smiled, her blue eyes locked "Oh the possibilities."