A Midlife Awakening

One

I dropped my clutch bag on the ridiculously large divan and looked over the room. It was much like any other city hotel accommodation, I'd seen so many. A square room dominated by the bed. En-suite in the corner and built-in wardrobes that matched the dark rich mahogany of the floor-to-ceiling board at the head of where I would be sleeping.

A small table sat at its base and there was a further solid-looking bench against the wall. Both in the same deeply coloured wood. There were also two small comfy chairs for lounging around.

"It'll do fine.

Thank you."

I tipped the young bellboy who'd stood waiting patiently after placing my suitcase carefully next to the wardrobes.

"Will there be anything else?"

I saw his eyes flit down the length of me and imagined what my answer could have been had I twenty years less on the clock.

"No.

That'll be all thank you." I replied smiling.

He pocketed the note and nodded before turning away, closing the door softly behind him.

"Fuck."

Sometimes I thought about throwing caution to the wind and filling the empty space in all these hotel room beds. But that was just fantasy.

I glanced around again, this time turning my attention to the one significant feature this hotel had over so many others I'd frequented. The floor-to-ceiling full glass frontage. High up, I had an unobstructed look at the city below.

I felt queasy just standing close. My knees literally shook. Only what seemed a thin delicate sheet of glass separated me from a fall of twenty-odd floors back to ground level. Of course, with my background, I understood the strength of heat-strengthened glass. Two six-millimetre panes separated by a twelve mil air space, or perhaps argon filled. It was designed to withstand the torsional strains and the punishing wind speeds of a high-rise building. If I leant against it my tiny frame would be insignificant. That was the engineer talking. The primitive instinct of survival said not to trust anything so flimsy looking.

I raised my eyes and gazed towards the horizon and the knots in my stomach eased. Lights shone back from street lamps and other high-rise buildings. A tapestry of colour and light against the backdrop of a fast-darkening sky. It was still only evening but the encroaching winter and the rain that'd hampered my journey shortened the day.

Kicking off my shoes I checked the bathroom. Large, with a walk-in shower that looked inviting and designer-style fittings.

"Very nice."

I turned the taps and stripped off my clothing, hanging my suit neatly in the wardrobe before returning to the en-suite with just an uneasy glance at the bare window. Twenty-four floors up, I reminded myself. And no nearby buildings. No one could see me. It still made me tingle with excitement as though I was doing something very naughty by walking about naked. I enjoyed the buzz.

The shower was powerful, making me take a step back in shock as tiny beads of water pelted my bare skin with stinging hot strikes. Becoming more accustomed I stepped back under and let it flow over me, taking with it the stress of my journey.

I smelt lavender as I spread the soapy lather over myself, washing away the day's sweat and grime. Natural oils instantly calmed me and relaxed my taut muscles.

I remembered the bellboy as my hands glided over my tits and I gave them extra attention, caressing and squeezing them. I had to admit the sight of a smart young man and my abstinence from real sex for so long had left me horny. I wouldn't sleep unless I did something about the fire beginning to smoulder away deep in my groin.

Fingers slid down to my thighs and drew lines around my vulva.

"Mmm."

For five years I'd been single and only my fingers and a few well-used toys had explored this territory in all that time.

So what if I fantasised about the bellboy? The idea of a lad nearly half my age was quite exciting. The fact that he'd be more at home with my daughter than her forty-four-year-old mother was unimportant. In my head, he could be anything I wanted.

And to my shame, he wasn't the first I'd had thoughts about. Chrissy had supplied a long string of young men coming to the house that'd sent my imagination wild. Especially recently as they'd become young men rather than boys.

While I smiled and offered coffee and they called me Mrs or Mum my head had often been filled with thoughts of how they looked naked. How it would be to know the feel of their hands on my body or their cock filling my pussy. It was true, I was jealous of my daughter's rather overly-filled love life.

I stroked my slit back and forth slowly, picturing the smooth, athletic body of the young bellboy rubbing against me under the cascading water. Imagining that I'd asked him to join me when he'd asked 'Is there anything else'.

How nice would it be to feel a real man again after so long? I was wasting the last few good years I had remaining. Perhaps I could pay for it? A hot young guy just for a night. Were there male prostitutes? I supposed there were.

My tender lips parted on a soapy finger and I found the natural silky lubrication secretly hiding just beneath.

"Uhh."

I began a slow methodical finger fuck of myself, delighting in the euphoria that filled my head. A dreamy half-existence that carried away the worries of work and life, leaving me only with the concentration of enjoying my pleasure.

"Mmm."

I turned and leant back onto the wet tiles, just out of the waterfall.

"Ooh."

I turned to firm circular motions using the tips of my fingers over my clit, increasing speed as my mind's eye envisioned the bellboy's hands on my body, caressing and stroking me with the attention of a devoted lover. Kissing me, my neck and shoulders, sucking my nipples. I squeezed one and stretched it.

"Uhhh."

The fresh environment of the hotel room and its stylish shower heightened my mood, pushing me faster than usual towards my end.

I imagined his cock inside me, sliding in and out as the fingers of my other hand imitated the action.

"Uhh. Fuck."

It wasn't mind-blowing when it came. But it was pleasant. And probably better than anything that hopeless ex-husband of mine had managed in our last few years. If ever, to be honest.

I rinsed again to remove the evidence of my relief and turned the taps off.

I felt good, and happier, as I stepped from the shower. But disappointed that I was alone and no one would hold me or whisper sweet nothings in that big bed as I drifted into sleep. However, in the world of reality, I was as satisfied as ever.

Masturbation for me was a release of tension. A necessary bodily function like peeing. Little more. And once done I could function again without my head being bombarded with distracting images and thoughts.

I dried myself with the towel and wrapped it around my damp hair before going back into the room, glancing at the window again. It felt so risqué walking about naked with the curtains open. I retrieved my glasses and went back to the window.

No one could see me up here but I still felt the thrill of exposure. A thrill I excited even further by standing and looking out again.

It was black now. The darkness of night. The pinpricks of light seemed homeless, just shining out of the nothingness, apart from the reflection of the room behind. And me.

I stood up straight. The mirror image of me was kind, hiding the beginnings of lines around the eyes. My body wasn't bad at all. Good legs and nice tits. I rocked my hips from side to side admiring the small patch of dark hair I maintained above my pussy. I circled a finger through it proudly.

I knew I still looked okay, but Mike banging his little plump Secretary for two years before I found out hadn't done much for my self-esteem. It was only recently I'd begun to see myself as attractive again.

"You're wasting yourself, Anna." I muttered.

I was. I knew that. Time wouldn't hold back forever and I was denying myself a chance for fun by avoiding every man that showed an interest in me. But then they all seemed to be attached or carrying baggage. Perhaps growing old and spending my twilight years with a house full of cats wouldn't be so bad.

"Oh well." I sighed.

I looked outwards again, into the blackness and suddenly imagined all the eyes out there looking my way. In the brightly lit room, I would be as clear as day to any onlooker. The flush of excitement turned to fear and embarrassment, even knowing they'd have to be Superman to see me. I closed the curtains and became normal again.

I was up early. Fresh and ready for my first meeting. They were sending a car to pick me up at nine which gave me plenty of time for breakfast.

I hated sitting alone in hotel restaurants. I'd had enough experience but it still didn't get any easier. Others read newspapers or fiddled with their cell phones to distract themselves. I couldn't do that and remained wallowing in my loneliness while trying to portray the confidence and control of a business executive. Sometimes I felt as though I was a fraud.

And of course, somewhere there would probably be a set of eyes on me. There usually was. Some bloke hoping to get lucky. Sometimes I considered it. I missed the company of a man after so long divorced. But I always looked away.

"Thank you."

I looked up and smiled as the waiter brought me my drink. An Asian immigrant as so many in the hospitality industry were.

"Your breakfast will be along shortly madam." He said perfectly.

Orange juice. I sipped it and glanced about. No eyes this morning. That was one thing. Everyone here seemed to be in groups. Business people like me, and the occasional couple, wealthy enough to pay the horrendous prices out of their own pocket.

"Good morning Mrs Cross."

I looked up shocked at hearing my name to find the bell boy smiling at me.

"Sorry. I was passing and recognised you from last night.

When you checked in."

He looked a little nervous. As if I'd be annoyed he'd spoken.

"Yes. I remember." I smiled back pushing my glasses higher on my nose.

He did look good.

"And it's Miss."

Not sure why I felt the need to correct a complete stranger on that. I didn't usually.

"Sorry."

He hovered, looking lost and I found myself quietly amused.

"Do you remember all your guests?"

"No. Just... Er. No

Just the ones that tip well."

He grinned. Looking a little more comfortable having come up with a suitable answer. I didn't think it was his first thought. I looked down to avoid his gaze as a smile forced itself on my face. I was flattered.

"It's company money. Can't say I can afford to be so generous with my own."

I liked him. What was he twenty-two? Twenty-three? Couldn't be any more. The sort of lad I would be happy to see Chrissy with.

"What's your name?"

"It's Christopher. Chris." He said.

He was smiling. The kind of genuine smile that subtly filled his eyes. One he didn't even realise populated his face.

I held my hand up for him to take.

"Well, pleased to meet you, Chris.

And forget the Miss. It's Anna if we bump into each other again."

"Anna. Nice name."

The waiter arrived with my breakfast and saved me from any more of this boy's apparent infatuation with me.

"I'd better get back to work. Enjoy your breakfast.

Again. Nice to know you. Anna."

I watched him walk away. He was fit as fuck under that uniform. I'd chosen my shower fantasy well I decided. Now I had a little more to think about when I was feeling lonely later. And there, that little glance back. I felt good about myself.

A silly infatuation I knew, but it did no harm. Thinking about celebrities or work colleagues was becoming boring and unsatisfying. Chris the Bell Boy was a fresh target for my mind when I needed to perform that necessary bodily function again.

I turned my attention to the breakfast. Poached eggs on white toast. There were fancier meals but I always kept things simple. And of course, I needed to focus on the reason I was here. A few hours from now I had to present a pitch to a room full of executives and convince them why they should invest money in my employers and our company's future. A long day ahead with a lot riding on it.

By the time I got back to the hotel, I was shattered. Dinner was serving in the restaurant but I couldn't face that. Instead, I showered and wrapped myself in a fluffy dressing gown before ringing down to room service. I checked my messages while I waited.

No loving messages from a husband who missed me. Just emails from work and one from Chrissy asking where I'd put her favourite top.

"Chris."

I was surprised to see my new best friend as I answered the knock at my door.

"I can't seem to get away from you."

I stepped aside letting him in.

"Sorry. Just my turn on room service tonight. Short staffed since covid."

I smiled before averting my gaze to the platter. It looked stylish.

"I wouldn't have thought it was possible to make a cheese sandwich look so... fancy." I said.

"I can't claim responsibility for that. I just carried it up."

"Shall I place it on the side?"

"Please. Yes."

I looked back up at him. His face was kind. Alert eyes. Smooth youthful skin not yet hardened by maturity and the elements. I smirked, realising I was staring.

"You must work long hours. Eight this morning. And it's nearly nine now."

"Spilt shifts. I was off this afternoon. So not that long. But I need the money. I'm at college."

"Really?"

God, he was young.

"What are you studying?"

"Business.

I'm hoping for a management position. In hospitality. Somewhere like here." He said emphasising the hotel with open hands.

"That's why this job is handy. Real experience."

I picked my bag up and found my purse.

"Here. Let me give you some more company money to help pay for college expenses."

I doubled it from last time.

"Thank you.

But that's way too much."

"No, it isn't.

My bosses are about to gain a rather large investment if I do my job properly. They can afford it."

"Thank you.

Can I ask? What is it you do?"

"Green energy. We build wind turbines.

I may not look it but I'm an engineer. Though I haven't done much more than look at drawings, negotiate sales and beg for investment in an awfully long time."

"Wow.

No. You don't look like an engineer. All the ones I've met are middle-aged men working on gas boilers in student accommodations.

Certainly not... well..."

I saw his eyes on my tits as the gown gapped, then a flit to my legs before coming back to my face. God, it made me feel good. A quiver raced over my skin and I fought the urge to pull the garment tighter. I liked being looked at as a sexual object.

"Female?

We exist you know."

"Yeah, but I doubt many look as good as you."

I started to colour up.

"You got the middle-aged bit right though. I must have twenty years on you."

"That doesn't show either."

I was struggling to hide my delight at his flattery and turned away. Now I did straighten the gown.

"Well. Thank you for that. And thank you for bringing my sandwiches."

"No problem.

Thank you for the tip, Anna."

I literally trembled at hearing him use my name and turned to see the door closing.

Alone, I let the grin I'd been stifling spread across my face.

"Fuck me, Anna. A twenty-something fancies you." I said out loud.

"How amazing is that."

I opened my arms and fell face down on the bed in a childish act, almost wishing Chris was still there, ready to tear away the dressing gown and take me from behind.

Alas, not.

But he'd left me needing relief and my hand went under me, pushing the gown away to find my pussy.

"Aw fuck."

I spread my legs. For the second time with Chris in my head, I rubbed my hot little frustrated clit towards orgasm.

"Fuck."

I pulled the dressing gown up to my waist, feeling cooler air on a bare arse that I rocked up and down on my fingers, letting them enter my wet passage. My other hand took over clit duties, fingers circling and rubbing it."

"Uhh."

I pulled a knee up to open myself wider and pressed my face into the bed.

"Fuck."

How good would it be to have that hot young man fuck me from behind?

"Uh."

This time I came harder. Jerking and bouncing against the mattress as I imagined Chris fucking me hard.

"Uh... uhhh."

A wave of euphoria raced over my skin and I relaxed. Just tiny after-shocks occasionally twitching my muscles.

"Fuck." I gasped as my breathing settled back.

I sat up and stared out of the window at the city again feeling pleased with myself.

Wow. If there was anyone out there with a telescope I'd just given them a show worthy of any porn site.

Two

The next day I was back early. Business concluded. Another shower and this time I decided I should spend my evening downstairs. That little part of me that was needy wanted to see if I could garner attention. Telling me to find someone and get myself banged while I still could. Before everything turned crinkly and headed south. A challenge that I knew I wouldn't rise to even if the opportunity presented itself.

What I didn't expect was to find a friendly face at the bar the very second I walked in.

"Well if it isn't the bellboy again."

I smiled with genuine warmth.

"No home?"

"Hi, Anna."

He shifted around in his seat and I felt invited to join him. I didn't have a problem with that. Better than drinking alone.

"Student accommodation. I share and sometimes you just... have to be out."

His smile turned into a grin and I laughed as I got his meaning.

"I'm sure he does the same for you."

"Not so often as you might think. Can I get you a drink?"

"No." I protested.

"I'll get you one. Company money remember.

And I won the investment I was looking for so there's plenty of it."

I felt good about that. A successful trip meant the company had a secure future. A me a job I could rely on.

"Well done you.

Perhaps you should get us a bottle to celebrate."

"Yeah. You know what? That's actually a good idea."

I ordered a bottle of champagne and finally took the seat next to him.

"So how come your roommate gets all the action and not you? I mean, look at you. You look... Fantastic."

Oh my God. He did. In his civies, he looked hotter than ever and I felt myself reddening up."

He pulled a face.

"Girls like the bad boys. I'm too... nice."

"Yeah, that's true. I get mad at Chrissy all the time for some of the boys she brings home. That's my daughter by the way. She's twenty-one.

Her latest beau seems nice though, so perhaps she's maturing."

"Hard to believe you can have a daughter that old."

Now I did blush.

"Yeah. Well, I'm a lot older than you might think."

"Not so old that you can't still bring home a few conquests of your own. And which do you prefer Anna? The bad boys? Or the nice?"

I hesitated. When I answered I'd be telling him I liked him. But wasn't that what I was supposed to do when someone showed an interest? It'd been so long that it seemed I'd forgotten the rules.

"Hmm."

I poured our drinks from the expensive bottle.

"The nice." I finally answered, smiling at him.

"With maturity comes wisdom."

"Well here's to maturity.

He raised his glass.

"Cheers."

I never was a drinker and two glasses in I was beginning to let my guard down. Almost fishing for the compliments.

"I must be as old as your mum?"

"Probably. But trust me. You look better than my mum.

I mean she's okay and all. And her boyfriend's besotted. But she isn't.

Hot."

I think I nearly wet myself at being called hot.

"Ha. You haven't seen me naked. I'm not some twenty-year-old bimbo with tits that defy gravity anymore."

"No. You're not."

He spoke much more softly. More serious.

"You're much more interesting than that."