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 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 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.
