Age Gap

The ball shot down the middle and I gave the table a good shake. Fuck. Happy Thursday. I had been trying to distract myself from my long work day, but to no avail. Usually pinball helped me relax, but tonight I was just playing like shit. I had had one or two good games earlier tonight but things had just been getting worse for a while. I was frustrated as hell and just wanted to stop thinking about life for a bit. Suddenly, there was a tap on my shoulder. I turned around to see who was bothering me, maybe the bar was closing and I would have to be on my way.

What I wasn't expecting was somebody closely leaning in trying to get my attention. Occasionally when I play pinball, somebody a little tipsy might wander over my way and start asking for tips or just strike up a conversation, but I am rarely in the mood. Either they are far too drunk for me to flirt with or are just looking for the bathroom or something. Look I am all for making new friends and I have this way many times, but usually I approached them.

So here was this woman, her hand on her hip, looking at me as if she had never seen somebody play pinball before.

"You mind if I cut in?"

It's rare to meet somebody who isn't actively playing pinball know that you can play the game with more than one person. I grew up way past the heyday of pinball so a lot of this is just stuff people don't know anymore.

"Of course, 2 player or you want the table for yourself?"

That got a look. A long approving look.

"How old are you?"

I wasn't expecting that kind of question from her, but I obliged anyway.

"I'm 24. What about you?"

"Old enough for you to not get any ideas about."

Well. I mean I hadn't even thought those ideas yet, but now that she mentioned it, she was absolutely stunning. Her long blonde hair, flecked with grey, trailed down her back. She wore a bright red dress shirt, with the sleeves rolled up, and a grey pencil skirt that was both professional and short enough to make me think about her legs. She had pumps as well, but I don't remember what color if I am being honest, the main thing I remembered was the way she carried herself, complete confidence. It was driving me wild already, even though she had said not to get ideas.

We started playing back and forth, talking about all manner of things. She was well read and had been playing pinball since before I was born. I took a couple games off her, she took a couple off me and the night kept going. We were laughing and taught each other all sorts of tricks of how to hustle random dudes at bars out of drinks over pinball. We talked about sobriety, she had been sober for about 7 years, our careers, she was an old school tech woman who had climbed the ranks through sheer tenacity and competence but still had a sense of humor about her. We felt like old friends, but there was definitely something in the back of my mind that was nagging at me. An uncontrollable desire for her.

The bartender came up to us and let us know that we were nearing the end of the night and to play our last game. We both dropped our quarters in and began to play the game. It all came down to the last ball where, to my surprise, she swept up behind me and pressed herself against my body, wrapping her hands around my shoulders as I tried to play my last ball.

"You know I have been waiting for you to make a move all night."

I gulped trying to focus on my game. She continued in a quiet sultry tone.

"Truth be told I would have rejected you, far too... dominant for my normal type. Unless..."

She paused as I saw a smile creep over her face.

"Oh my."

She slid her hands down my sides as I furiously struggled to focus on my last ball. My cheeks flushed, knowing the realization she had just come to.

"How precious."

I sighed as she traced along my spine with her finger. My eyes went out of focus as my ball drained. I looked up at the scores, I was 100 points short. She laughed.

"Awww. I'm so sorry you lost focus there, sweetie. I didn't mean to distract you."

Her smooth mocking voice caused me to double over on the machine. She followed me down, leaning right next to my ear.

"I think I might be able to help you, with some of your problems. You should come home with me, I need to show you something."

I stayed there frozen, not sure how to respond. Her body pressed against mine. There was nothing better in the world than a woman who knew what she wanted.

"I can help you, but I know this is sudden. I don't want to pressure you into this, but I feel like I can help you sweetheart. Just nod if you want to come with me."

I stayed motionless, not sure what to do. I wanted this woman, she wanted me, was there anything more to it?

I nodded very softly.

"Good boy."

She gathered me up and lead me by her arm to a parking garage where she had parked. She rubbed my shoulder.

"Are you sure you want to come with me? I promise I won't be angry if you say no."

I grabbed onto her arm tightly nodding much more certain now. She held my head against her body and laughed.

"I think this will be good for both of us."

We got into her car, which might I add, was very nice. I guess that is what old tech money will do for you. She gave me a few minutes of silence as we drove out of the parking garage and onto the highway. After what was probably 10 minutes, she turned to me and started a completely normal conversation.

"I have always found your generation fascinating. You are all so wildly weird and enthusiastic about everything. I love that about you."

"Pick up a lot of men my age?"

She smiled.

"I have, though honestly none as young as you. I just got tired of the people my age. They are all just too similar to me. When you get to be my age, novelty is hard to find. I take it where I can get it."

I sat on that, taking in what she was saying to me. Was there subtext here or was she just being polite? As I thought about this, we pulled into a very nice apartment complex downtown. I looked up at the tall building in admiration.

"You live here."

"Mhmmm."

I had nothing more to say, we pulled into the garage, parked, and got out of the car. It was a cold night and she pulled me towards her as we walked to the elevator. I loved feeling her against me.

The elevator shot up the building to one of the top floors and she lead me through a maze of hallways that were, in hindsight, a little more confusing than needed to be.

"Any reason why you live in a labyrinth?"

"Sweetie, a labyrinth has no exit. Just one way in and out."

She paused for my reaction, I shuddered briefly and kept walking.

"I'm only kidding, I think it was some weird architectural dick stroking contest. It is truly maddening when I have guests over."

I relaxed. She had been joking. I think.

We got to her door and she unlocked it. What was behind the door was incredible. She had quite possibly the best view of the city I had ever seen in her living room. I walked over to the window and peered out, taking it all in. She strode up beside me.

"I sometimes forget how magnificent this place truly is. I always love bringing impressionable minds up here to remind me how spectacular it all is. But the night is late and we have so much to get to."

She motioned to a recliner in the corner of the room.

"Be a doll and sit in that chair for me. I need a few minutes to prepare for you, but I promise this is going to be a very good night."

I sat down. and tapped my foot, she walked out of my sight and into another room, only to return a few moments later with a piece of white silk in her hand.

"Now. As much as I admire your generation, there are so many things about them that need to be corrected. I am here to ensure that you are set on the right path."

She walked over slowly, looking me up and down as she did so.

"You may all have such great enthusiasm and energy, but it is undirected. Undisciplined. I happen to be an expert at fixing impressionable men like yourself in my 'Clinic'."

She smirked at that last word, clearly she had advanced knowledge that I did not on this subject.

"Tonight. We are going to begin fixing you. To be more disciplined."

She wrapped the silk around my eyes and tied it tightly.

"More controlled."

She slid her hands across my chest and circled my nipples underneath my thin shirt.

"And far less..."

Her hand drifted down my body to my bulge.

"Sensitive."

She retreated from me and I was left to sit there idly, my head spinning with her words, my body twitching with the lust that she knew she had imparted onto me.

Several minutes later I heard her reenter the room. The quality of her footsteps sounded different. Harsher, louder, more in my face somehow. I didn't know how to react, so I sat still.

"Are you ready to begin?"

I nodded shallowly, not really knowing what was coming next. I felt cold steel against my collar as she slid a pair of shears down my shirt, cutting it away from my skin. I stayed as still as possible, trying to make her job as easy as possible.

"Good boy. Stay still for me. I need to take a look at you first before I can do my job. Breathe nice and deep for me."

I let her cut it all away. She was methodical about the entire operation. She had my shirt off in less than a minute and began to rub my shoulders.

"I like what I am seeing here."

I remained silent. She kissed my nipples and they hardened instantly. She continued to play with them with one of her hands, the other still on my shoulder, holding me firmly in place. Her hands felt different, but I couldn't place it. Softer. Smoother. I let out a moan and pressed forward. She reaffirmed her grip on my shoulder.

"Far too sensitive. I am worried about you. Your case is quite severe."

As she said these words, she came around behind me and sat, once again pressing her chest against my back.

The cold of her latex outfit made me jump forward and she pulled me tight against her once again. I now knew where I had recognized the sensation her hands.

"So helpless."

She began to twine her legs around mine, they had a weight to them that could only mean one thing. She was wearing ballet boots of some kind. I shuddered again and she held me tighter.

"Are you going to let me conduct my evaluation or are you going to keep squirming?"

I shook my head, hoping she would understand my meaning. Thankfully she did.

"Good. Now let me conduct my test."

She began to unzip my pants and pulled out my cock, already hard and slick with precum. She laughed, her diaphragm bouncing against my back, making me feel every rising and falling of her body. My heart was racing. So was hers. She began to stroke me very quickly without any pretense.

"I am worried about another thing with this level of sensitivity. That I need to test."

I began to moan wildly as she worked me up and down. She quickly covered my mouth and hissed at me to be quiet, but I was beyond control. The smooth latex gloves pressed against my mouth tighter. I continued to groan as she sped up and played with my scrotum, her fingers searching for every inch of sensitivity they could find out of me, glossily sliding over my entire body searching.

"You aren't even going to last two minutes, you are quite the disappointment."

I came all over the floor, a rather large load, just exploded across the room, her laughing in my ear as it happened.

"Oh you poor thing. Is this what it is like all the time with you? Just so eager to please and full of need? I don't know if I have ever seen anybody quite as excitable as you."

She kept pumping me after I finished, my body twitching wildly, trying to get away from her. My volume of moaning rose.

"Sweet child, I think your case is going to need more attention, don't you?"

She kept pumping. I screamed.

She subsided a moment later and began rubbing my body with her now slick gloves, my body started to get covered in my own sticky residue. She reached for the blindfold and took it off. She held me tight and just let me sit there for a few moments, no longer touching my cock, just holding me.

"I'm so proud of you for being brave for me."

I stayed quiet, melting into her. I noticed her boots, bright red and shiny, idly playing with the pool of my own cum on the floor.

"You really are the most excitable man I have ever been with. I really liked that."

I nodded at her, appreciating the praise.

"How is your energy level? I know some boys need time after they cum to collect themselves."

I sat motionless, resetting my brain.

"Sit with me a moment. Just let me hold you. I promise I am going to help you. Just relax, let your doctor take care of you."

I fell against her body and she held me tight. She had plans and she knew how to take care of me. I knew it on an instinctual level.

"Are you ready to continue, love?"

I nodded.

She pushed me to the floor, my body crumbling into what remained of my own filth. She looked down at me with amusement and lust in equal parts. Her outfit had completely changed. The red over the knee glossy boots were just the beginning. A tight white and red latex nurse's dress stretched across her body in such an appealing way. The gloves she was wearing matched the color of her boots, long opera style latex. She had done her hair back and looked like one of those old pinup girls from the 40s, and had a small nurse's cap to complete the look. I couldn't quite place it but holy shit she drove me wild.

"Now, in order to get better, you need to follow my directions. Do you think you can do that sweetie?"

I looked up at her, apprehension in my eyes.

"You can do it darling, just listen to the sound of my voice."

She extended her boots towards my mouth on the ground.

"Clean this with your mouth, I just shined them and I want to keep them looking nice."

I began to lick them clean, my own semen, running across them in streaks. She looked on with admiration. I gagged over the taste. I continued, cleaning all parts of the boot, the bottom, the sides, even sliding my tongue in between the laces to clean my filth out.

"So eager to please. Don't stop now. You came far too quickly and need to know what that sort of eagerness tastes like."

As she did she idly licked her gloves, also covered in my cum.

"The first time you cum in the night is always the worst tasting. I normally love the taste but the first batch is always disappointing, especially after such a short performance."

I continued to clean her boots, lapping up my mess with diligence, she continued to look on with satisfaction. At some point she swapped the boot for the other and I had to taste more of my filth. After some time she nodded.

"Good work. I think you have cleaned me enough and hopefully will remember why I never taste a boy's load the first time he cums."

She stood up and grabbed my hand.

"Follow me. It's time to fix you."

---

She half dragged, half walked me down the hall, my mind still in a haze. I was shocked at how strong she was, clearly she was used to pushing people around and wasn't at all conscious of how strong she really was. My feet splayed behind me as her pace was brisk. She pushed open a door to a room that had bee setup like a full exam room, decked out with a gyno table, all sorts of kink gear, and loads of cabinets. I noted the tile floor and drain in the center of the room. She pushed me up into the table, removed all the clothes I had remaining, and adjusted me to fit into the stirrups before beginning to strap me down.

"I know you are fidgety and the next phase of your treatment is very delicate. I promise I'm going to make you all better."

She walked over to the cabinet and grabbed a small tub with a sponge in it and began to fill it with hot water in a sink against the wall.

"You are currently covered in your own filth, and though that's probably good for you, it isn't really what I want to be touching right now, even with gloves. It's time to clean you up. A filthy boy like you needs so much help."

She shook her head and began wiping down my skin, head to toe, spending extra time on the delicate areas. My arousal already returning. Something she appeared to make a mental not of approvingly.

"To be that full of life and need. I knew I picked correctly."

She finished cleaning me up and returned to the sink and tossed the sponge in. She turned back to me and put her hands on her hips.

"I was planning on using clean ice water for this next part, but it just occurred to me. You probably aren't ready for that. Something we can work up to. For now this dirty cum water will have to do."

She crossed the room again, this time to the wall where all the kink gear was and grabbed an enema bag. I quivered. Now I understood why there was a drain in the center of the room and began to dread the next few minutes. She selected a nozzle, thankfully it was smaller and returned to me, gently touching my knees and then sliding her hands up my thighs.

"Are you nervous?"

I nodded.

"Good. I want you uncomfortable. Don't worry too much though, I'll be very gentle and only give you as much as you can take."

She continued to rub my lower body, calming me and gently reassuring me. Gently hushing me at any whimpers I let out.

"It's going to be okay, you are in my hands sweetie. I know exactly what you need."

She snapped open a bottle of lube that had been sitting beside the gyno table and began to cover her gloves in lube, making eye contact with me the entire time.

"Deep breaths for me."

She began to rub my hole, slowly, gently, a look of desire on her eyes, moaning a little as I loosened for her.

"Just like that. Just stay calm, let me take care of you."

She gently slid a finger inside and she shuddered as she took me, sliding in and out in time with my breathing. She sighed as she retracted her finger one last time and began to slide the nozzle inside.

After she finished her work, she began to fill the bag with the dirty water and took her time as to not spill a drop until the bag was full. She hung it up on a hook above me and circled around to my side so she could be closer to my head.

"I'm going to turn the valve and you are going to begin to fill up with warm fluid. It shouldn't be painful, just a little uncomfortable, like being too full. Are you ready?"

I tried to not as much as I could in the restraints. She patted my head and turned the valve open. The warm liquid rushed inside of me and began to fill me up. I squirmed a little and she pressed me back against the table.

"Stay. It will only take a few moments."

I lay back, trying to enjoy the sensation, which was in reality, quite pleasant. She gazed at me with pride.

"I knew you could learn how to follow my directions. Just enjoy me filling you up. Before I am done here, every one of your holes is going to be full."

I was suddenly alarmed and it showed. I tensed up and clenched down on the nozzle. She laughed.

"Yes dear, all of them. Don't whine. You said you wanted to get better didn't you?"

I moaned as my body filled more, not sure I could take any more in the one hole, let alone the other holes. She cocked an eyebrow at me and returned to the wall of implements.

As she came back, she held a gag in her hands, what looked like a bulb on the inside of a leather strap and a tube leading off of it. She gently wrapped it around my mouth, the bulb snugly inside my mouth. As she finished her work she made intent eye contact with me as she squeezed something, slowly the bulb in my mouth grew as she pumped it full of air. My moans steadily being muffled by the now full bulb in my mouth. Unable to move or scream.

"No more noise out of you sweetheart. You are getting filled up. It's what you need."

As she spoke the filling sensation down below finished and she squeezed the last of the liquid out of the bag, before removing the nozzle. She gently tapped on my stomach.