Milked by My Fiancée’s Mother Ch. 03

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Authors note: All characters depicted in this story are to be considered over eighteen years of age.

Milked by my Fiancée’s Mother CH. 3

The restaurant was dark and I could make out very little detail. I picked my way through the dining room all the way to the back as directed by the Hostess.

As I got closer, I recognized two familiar faces, it was Andria and her mother Edith. I walked over to them trying to make it seem like I wasn’t having any issues with the anal plug I was wearing. I stood before them, waiting for their direction.

Edith was the first to speak,

“Benjamin, you may sit…..if you can!” She seemed to be enjoying my predicament, but with her lifestyle, why wouldn’t she?

I sat in the chair across from them and squirmed to get comfortable. Andria reached over and warmly touched my hand and looked deeply into my eyes. It was an unspoken ‘I love you, and thanks for doing all this for me!’

“Look over the menu and order what you want,” said Edith in a calm friendly voice. I was puzzled by her demeanor, it was defiantly out of character for her. Edith must have read my face,

“We are out to eat here as mother, daughter, and perspective son in law. Your training so far is going so good that Andria and I thought we’d have a nice dinner so I could get to know you.”

“Can I ask a question?” I said with a strained voice.

“I’ll bet you’re wondering how long the plug is required to stay in, right.”

I nodded my head in the affirmative.

“Two hours a night, and you will be required to insert it before you leave work on Thursday when you come to get your next milking.”

“And after that?” I asked.

“After that we start increasing the size of the plug, Andria will have the plugs and help you with them.”

“The time-frame is up to how quickly your rectum stretches to our desired size.”

“Desired size?”

I heard myself ask it, but I couldn’t believe that I was talking about my rectum being trained, but I’m getting to the point where not much surprises me anymore.

“Now, no more shop talk, let’s have dinner!”

As the evening went on I actually found Edith to be very warm and pleasant. The three of us had a nice dinner and I learned that there were two sides to the CFNM lifestyle; the normal social life, and the persona that is their tribe-like family unit.

Andria and I both drove our separate cars home and as is my now usual routine, I stripped once I entered the front door. I looked at my watch and saw that the two hours were up, but I didn’t dare take the plug out myself. I waited for Andria to do it. I just stood naked at the door as kind of a hint to remove the plug.

Andria saw me there and walked over to me,

“Looks like someone is ready for the plug to be removed,” she said in a teasing voice.

“How does it feel?”

“Like I’m constipated,” I said with a strained-pleading voice.

“Ah, don’t worry, once you are stretched you’ll hardly know it’s in there!”

“Bend over, grab your ankles, and take a deep breath!”

“This may hurt a little when the bulb clears your sphincter.”

I bent over and exposed my ass to her waiting hands. She wrapped her fingers around the protruding knob and gave it a swift, steady tug. I had put my hands over my mouth to muffle the involuntary shriek I knew I was about to release. With a loud ‘Pop’ the plug was removed, the resulting pain was far less than I had expected, but that didn’t stop me from yelling out.

“Oh, poor darling, it always hurts at first, but before long you’ll learn to relax and get used to it.

“Now, just keep this position a little longer!”

She reached into her purse and took out a different type of salve.

She squeezed some out on her finger and fingered it into my aching rectum,

“This is what women use on stretch marks during pregnancy, we found it works as well on anal stretching as well!”

I stood up and walked into our apartment, somehow it felt as if the plug was still there, but I knew that I’d best get used to it like all the other recent changes in my life, because Andria was definitely worth it.

I had to re-learn how to sit in a chair and not squirm while I was in public, I knew work would be more difficult now. Not only would I have to work at hiding my stiffy on milking days, but now I had to re-learn how to walk.

Tuesday and Wednesday morning were the same routine as the other days almanbahis adresi of my new life, the alarm would go off, Andria would sit on my face, I’d service her, and she’d apply the salve to my cock. The difference now was that the ointment was applied to my anal opening as well. I had to take the regiment of vitamins before getting dressed at the door then leaving.

On Thursday it was the same routine, but this time Andria gave me a little box and said not to open it until two o’clock that afternoon.

I fidgeted all day in my chair, looking at the box from time to time. But my orders were to not open it until two o’clock.

I wasn’t exactly sure what the contents of the package were, but I was sure I wouldn’t like it!

Again today, as I found on last milking day, Andria had put something extra in the pills she had set out for me, just minutes down the road I had developed another strong erection.

This time I kept my apron in my car so I was able to wear it past the other bakery employees to my office. No one seemed to notice the huge bulge in my pants or the way I walked with a slight limp.

There was no doubt to me that the family females now controlled my cock and the sooner I learned that the faster my training would advance.

The hours slowly clicked by, as I got closer to the set time, my erection was still rock hard, but now I shuttered with anticipation of what was in store for me that night.

It got to the point that it became impossible for me to walk. I dare not even try to go to the bakery main floor, my stiffy would certainly give itself away and I couldn’t wear my apron forever.

I found it impossible to focus on my work but I knew that I had to. This will be my new way of life so I had best get used to it.

By noon, my bladder had become full and that three cups of morning coffee were screaming for release. When the crew went to the break room for lunch I had to try to make my move. The men’s room was a hundred twenty steps away, yes after several days with an almost constant stiffy I knew exactly how far it was. I took a clipboard and covered my crotch hoping that I wouldn’t run into anyone.

When I made it to the rest room I didn’t dare use the urinal so I had to get in the stall and urinate. The human male’s body was designed with a phenomena that prevented urination during arousal so I had to fight to force out a healthy piss. This was another task I had to re-learn, how to piss while fighting against a persistent hard-on.

I heard the employees return from lunch so I sat there and waited until my erection had diminished enough so I was able to get back to my office and waited for my day to end. One employee tried to flag me down, but I acted like I didn’t see her. If anyone wanted to talk to me it had to be when I was at my desk with my stiffy out of sight.

At two, when I was sure that nobody was looking, with my hands shaking, I opened the box.

Inside was another anal plug with a note telling me to insert it before leaving for Edith’s house. It was larger than the one I had been wearing and I didn’t know how it could possibly fit in my rectum. At least Andria had filled a small vile with her saliva that I could use as lube. I was told that the family never used conventional lube because female spit was a symbol of feminine power and male submission.

I drove to Edith’s house and entered as instructed by the note on the door. I stripped, put my clothes into my designated locker, and waited. Then I heard an unfamiliar woman’s voice directing me over to the couch,

“I’m Emma,” said a thirties something lady in tight latex leggings, curve hugging leather corset and a black and white striped blouse. Her knee-high laced patented leather high heeled boots covered the ankles and calves of her shapely legs catching my eye. Her long brunet hair flowed over her shoulders.

She was stunning and my male anatomy quickly responded.

I stood in front of her and she took my now pulsating boner in her warm hands.

“I’m Edith’s sister, you’ll be with me tonight!”

She worked her hands up and down my shaft, analyzing its length and girth with her fingers. Then she did the same while cupping my balls.

My compliments to my niece, she sure got us a live one here.

“Turn around and kneel, put your head on the floor, and present that virgin ass to me!”

I instantly did as she instructed, a normal man would almanbahis adres have hesitated before showing that type of vulnerability to a woman he just met, but this was now MY new normal.

I heard a ‘pop’ followed by intense relief as she removed the anal plug and spit into my rectum, then she inserted a gloved index finger.

“Have you ever had your prostate milked?” She asked in a direct voice!

“Ah, no,” I said, not believing that I was in that position with a finger up my ass of a women I just met thirty seconds ago. Really though, at this point nothing surprises me anymore. I understood that it was all part of my training. When acting out the CFNM lifestyle I was to have no privacy and be available for fondling, poking, and prodding by any female family member. That was the true definition of a ‘Freeuse’ Society.

She knew right where my prostrate was and I jumped when she hit it. A mix of pleasure and a little pain surged over my body.

“Ah, good, you have a well-developed Prostatic gland, we’ll make good use of that.

She probed my ass with one finger, spit on my rectum again, then inserted two, then three.

“When was the last time you had a bowel movement Lover boy?”

“Yesterday,” was my grunted answer.

“Ok, we’ll have to cleanse you first then. She removed her fingers and reached into a carrying case that was on the couch next to her. She took out a different looking anal plug with a pump bulb attached to a short hose on it. She inserted it in my anal orifice, then she pumped up what felt like an air bladder in my rectum. I instantly felt very full.

“You can stand now!”

I gingerly stood up and she led me down the steps by my erection.

In the center of the milking room was a bench with a five inch notch on one end and next to it was an IV stand with a large rubber bladder hanging from it. The bench was at a thirty degree angle to the floor with a donut pillow on the low end.

“Lay face down on the bench Lover Boy, and slide your junk into the slot!”

I did as instructed. In that position, my plugged ass was on display to her and about two and a half feet in the air. My head was about a foot and a half off the floor. She strapped me down so I couldn’t move.

She grabbed my balls and inspected them.

“First, let’s get you cleaned out, then I’ll collect that sperm of yours. Looks like the supplements you’re taking are working, these balls are nice and full, so we’re going to have some fun aren’t we?”

I didn’t bother to answer, it was a rhetorical question, but I did notice that she said ‘these balls,’ not ‘you’re balls’ which I felt was a sign that my genitals were now community property.

She unscrewed a cap in the middle of the plug in my rectum and connected a tube from the hanging bladder.

She removed a clamp in the tube and squeezed the contents of the hanging bag into my bowels, filling them with a lukewarm soapy liquid. She left me like that for about ten minutes before she cranked up the front of the bench to get my head about a foot higher than my full gut.

She took a bucket and held it under me and removed the tube. The brownish soapy liquid expelled from my bowels.

Then she repeated the process with a second bag.

Once I had expelled the contents of the second enema, she removed the plug.

“Alright, that done, now let’s get to work.”

“I’m going to milk your prostrate!”

“There’s no need for a button on this one, your sphincter will let me know when I need to get the container ready.”

I heard her snap on latex gloves and without further ado, she stuck her finger in my ass and started massaging my prostrate while stroking my cock.

She’d only stop when she needed drip more saliva on my ass and cock for lube.

Emma was right, on my first climax my rectum clamped down on her fingers singling that an eruption was imminent.

I let out a deep grunt and Emma kept steady pressure on my gland and waited, her finger trapped in my anal cavity by my steady clamping down on her appendage. I heard her move the glass beaker into position.

It only took a few seconds until I shot a massive load into the waiting container. My climax was so powerful that I could actually hear it splatter as it was collected. I shuddered in relief.

“Oh my, a few more like that and we’ll make my quota today.”

The word quota was interesting, then Emma further explained,

“Edith, almanbahis adresi Emily, Ashly and I have a competition. Whichever of us drains you of the most wins.

She emptied the collection vessel and went right back to it without giving me a rest bit like the others had.

“I always get a quick second one right away, give it to me lover boy, show me how much you love your milking’s! GIVE IT TO ME!”

I immediately shot my next powerful load and it splattered as it was captured, making a sound similar to a cow being milked into a bucket. She worked to squeeze every drop from my pulsating cock.

She added that load to the first one,

“I have to make a phone call Lover, stay here and I’ll be back in a jiff!”

She chuckled as she spoke, I was tightly bound, with my exposed ass in the air, just where the hell was I going to go! She obviously was amused over my predicament.

So, I waited…

I could hear her talking on her phone in the next room, I think she was talking to Andria, bragging about the volume I had just secreted for her. It sounded like she was congratulating my future wife for choosing me.

That got me to thinking, the term ‘choosing me’ sounded interesting, it had me thinking as to how we first met.

It all started some time ago when I went in for my annual physical. I had been going to the same Doctor for years, but I found out he had retired. I was assigned to a Physician’s Assistant named Jorden.

The nurse led me to a room, took my pulse and blood pressure and went over my medical history with me and asked if there were any updates. Everything seemed up to date. I was handed a gown and she told me to disrobe and dress myself in the flimsy, tied in the back, garment. Then she left the room.

I got naked and put on the gown, then I sat down of the paper covered table and waited.

Soon I heard a slight knock on the door,

“Come in,” I semi-shouted.

The door opened and a young lady in a smock entered and introduced herself to me.

“Hi, I’m Jorden, I’ll be doing your physical today,” Then her and I made eye contact. In an instant the two of us recognized each other.

I had seen her many times at the local bar I frequented, but I never knew her name, I may have even bought her a drink or two.

We started reminiscing about our favorite bar experiences, and sort of did some ‘Catching-up.”

The conversation quickly put me at ease.

We talked as she continued her examination. She reached under my gown and had me turn and cough, her hand just inches from my balls. I found this very erotic and fought off the urge to get an erection. I did get semi-hard, but she acted like she hadn’t noticed, I figured that this happens all the time with male patients.

Next she had me bend over and checked my prostrate with her gloved index finger.

By that time I was sporting a full erection, but she still acted like she didn’t notice. The exam ended without event.

After that, I noticed that she had a new friend with her when she frequented the bar. That friend was Andria.

As I was bound there waiting for my next milking I kept my flashback as how to Andria and I met.

The bar tender set a drink in front of me and said it was from the lady in black on the other side of the bar, and that’s when it all started. Andria bought me a drink as an icebreaker, she was the first to ask the other out, she was the first to initiate a kiss, and she was the first to seduce the other.

In retrospect, I hadn’t realized it before, but she was always the aggressor.

It all became clear to me, Jorden must have told her about my Physical. She knew how endowed I was, how my penis responded to her touch, and other facts of my health History. Now I knew she would be violating the law by sharing confidential medical information with someone else, but I didn’t really care.

I WAS chosen by Andria and I had worked right into her plan!

The strange thing is how I felt about it, I was actually flattered. I didn’t really care that everything had been pre-arraigned as long as I ended up with Andria as my wife, it all seemed right.

Emma hung up her phone and returned to her task of milking me. Now that everything seemed clear to me that I had been selected by Andria, I had mixed emotions, but mostly I was flattered and I knew that I had achieved my destiny and I was looking forward to married life in Andria’s family.

My next ejaculations were a blur and before I knew it I was drained.

Emma held up the vessel with today’s ‘Catch”.

It was a total of six ejaculations and Emma seemed pleased with herself.

“I think you just put me in first place!”

To be continued….

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