I finally get my interview with Miss Wooldridge, and I think she is impressed.
Olivia led the way as we stepped into the atrium. There were now lots of people, mostly women, walking through the large lobby. I noticed that all the men in the lobby were naked, like me, but none of them were sporting a hardon. The thorough anal-cleaning that the girls had given me was so sexy, my cock was standing out rock-hard, and the cockring was making sure I stayed that way. I felt a little self-conscious as women stared at my bouncing boner while we crossed the busy lobby.
We reached the double elevator and waited for one to open. Two ladies walked up and didn't ask for permission .......... one grabbed my hard dick and gave it a squeeze. "Oohhh, that's a nice, big one. Try it ........" she said as she let go, and the other lady gave me the 'C.F.N.M. handshake'. "Oh, he's so hard. Maybe he's ready to squirt right here," she said as she pulled on my engorged penis. My mind flashed through the possibility of being jerked off in the lobby by two smartly-dressed women, eager to see my semen squirt out. The girls in the shower room had gotten me so worked up, I knew it wouldn't take much to make me cum.
Olivia interrupted their fun as they both felt my hardon. "Sorry ladies, he has an appointment upstairs. I'll bring him back down soon, if you really want a sample," she smiled as she brushed their hands away. They seemed to understand, and let their hands fall away.
The elevator opened and we stepped inside. I saw a bank of numbered buttons to eight, and one above them with a star on it. Just as Olivia pushed the 'star' button, a woman got into the elevator and said, "oh, can you hit three, if you don't min ................ mmm, that's a nice one. So big and strong. Do you mind sharing? Can I ....." she asked as she stared at my 10-inch erection.
Olivia smiled as the doors closed and said, "just a handshake. He's got an appointment upstairs." The woman nodded and reached her hand out to wrap around my swollen organ. She squeezed firmly and a bead of precum popped out of my peehole. "Oooh, nice and juicy," she commented as she used a finger to rub the precum over my bulging cockhead. She lifted her messy finger to her lips and gave it a taste just as the doors opened for floor number three. She smiled as she left the elevator.
The doors closed and we continued to the penthouse floor. Olivia looked at my shiny cockhead and said, "you look ready to burst. Just hold it a little longer ........ I know it will be worth it."
The doors opened and we walked into a grand hallway. I followed Olivia down the hall, and we walked into a lavishly decorated room with lots of fancy furniture. The centerpiece of the room was a large sofa with padded chairs grouped closeby. The chairs were filled with nicely-dressed girls, and on the sofa, a white-haired lady sat regally, dressed in a designer suit with diamonds accenting her neck and wrists. In front of the chairs was an elegant coffee table with a fancy tea service on it, and cakes and cookies on a platter.
Olivia brought me to stand in front of the table, opposite from the old lady. She said very formally, "Miss Wooldridge, may I present Mr. Moore?"
The old lady nodded like a queen and said, "thank you, Olivia. Girls, we have a Mr. Moore in our presence. He seems to have a large penis. Young man, do you always walk around with a full erection? It seems to be leaking."
I knew I had to say something, and I shouldn't offend this rich old lady and her beautiful, young companions. It felt very odd to be standing naked with an erection in such a fancy room with all these fully dressed women.
"Umm, No ma'am. It's hard because Miss Essex and I were just in the elevator and a woman was pulling on it. Should I have told her to stop?"
"Nonsense, my dear boy. You are a guest in my mansion, and you must allow any woman to experience your penis however she wants. That is the whole reason for C.F.N.M." Miss Wooldridge responded with a smile.
"He's been very popular .... lots of ladies in the lobby wanted a handshake, and he gave a very nice sample for some girls at a milking table. They were very impressed," Olivia jumped in, giving an informal 'penis resume'.
"Well, he certainly has a large one. Those balls look nice in that cockring. Can you come closer, please?" Miss Wooldridge asked as she motioned me toward her.
Olivia nudged my elbow, and I walked around the coffee table to stand directly in front of Miss Wooldridge, giving her a close-up view of my straining penis and bulging balls. She reached a wrinkled hand up and gently grasped my hard shaft, giving a small tug before letting go.
"Very impressive ...... long and thick. What is the length?" she asked as she stared at my leaking peehole.
"Ten inches, ma'am. We measured it this morning," Olivia quickly responded.
"Good, we can use one of those. We have a foot-long black one, but a ten-inch one would be nice. These balls seem nice and full. They look very smooth," Miss Wooldridge said as she reached her hand to my tightly held balls. She stroked across the skin and then dug her fingernails in as she squeezed. I held back a gasp as my scrotum suddenly felt pain. She dug in deeper and pulled, and I let out a soft groan, hoping I wasn't offending her.
"Hmm, you don't mind a little squeeze. Let's see what else you have ......... turn around, please. Girls, would you assist ........" Miss Wooldridge ordered as I dutifully turned to show my smooth butt. She ran her hand over my soft cheeks and then patted them, saying, "bend over."
As I leaned over, the girls moved in and held me in place. A girl on each side grabbed my butt-cheeks and pulled them wide open. Now Miss Wooldridge had a close-up view of my tender little anus.
"Well, that looks very nice. It's shaved and slippery, just like it should be. I'd better test it," she said as I felt a skinny finger poke at my exposed hole. I was glad that Krissy had lubed me up in the clean-up room ......... she must have known that Miss Wooldridge liked to 'test' her boys. I felt her finger press at my slippery pucker, and she got no resistance as her finger slid in all the way. She wiggled it around and explored my soft insides, pulling back and forth as if her bony finger was fucking me. She finally pulled out, and I felt her finger swirl around my shaved hole as she commented, "very satisfactory. He may need some loosening up. Girls, would you hand me the silver one?"
From my bent-over position, I saw a girl reach for something on the tea service, and I realized that there were several dildos and buttplugs next to the delicate teacups. She picked up a rather large silver buttplug, and I knew I would have to accept it into my hole. Now I was glad that the girls in the cleaning room had stretched me open earlier, getting my asshole used to being opened up.
I felt the cold metal press at my slippery hole, and I tried to push back gently as Miss Wooldridge pushed hard to get the buttplug inside. Ooooh ......... just think of the girls in the clean-up room pulling your anus open with their fingers ........... think of Krissy filling your butt with all that warm water .............push harder and let your sphincter open up for this buttplug to slip in...........
"Aaahhhh! Ohh, ooohhh ........." I murmured as the fat buttplug filled my anus. I was sure it was bigger than the one that the girls had used when they were milking me in the Sampling Lounge. I felt an ache in my asshole as my tender little hole got used to being stretched so wide. Is this what a rich old lady liked to do ............ fuck young men in the ass?"
"You did very well. It popped in pretty easily. You seem to like your anus played with," Miss Wooldridge commented, and two of the girls giggled as they looked at the precum dripping from my swollen penis.
"Should we milk him now? I think he's ready," a girl beside me asked, and I guessed that I would stay in this bent-over position for Miss Wooldridge to watch my milking.
"He's all yours, girls. Just get some of it on my cakes. He'd better have enough," Miss Wooldridge instructed, and two of the girls beside me reached down and grabbed my balls and penis. The hand on my balls started squeezing, and the hand on my penis started stroking.
"Oh, he's got plenty. The last time he squirted, it was at least three feet in the air, and it got all over my suit," Olivia offered. I was sure I could present a large ejaculation .........it had been over an hour since I had cum, and all the teasing in the shower room and the elevator had me ready to explode. Now I had four lovely girls feeling my body and jerking my cock while an old lady watched from behind. It seemed a little weird, but it was certainly exciting.
The girls holding my butt-cheeks open were now rubbing my soft skin and poking at the base of the buttplug, sending an extra surge of pleasure to my body. The girl stroking my penis was using all the precum that dripped from my hole to lube my entire shaft, and she even teased me by running her finger over my oozing peehole. I started moving my hips and my knees began to shake as my orgasm began welling up inside. I moaned and raised up slightly as my back stiffened.
"He's ready!" the stroking girl announced, and the other girl beside me reached down and grabbed the platter of cakes and cookies. She held it in front of my penis, and the 'milking' girl stroked faster on my excited penis. I felt the surge of orgasm rising, and I saw a small spurt of 'cream' fly out and fall on a cookie.
Oh, no! Had I been milked dry by the other girls? Did I not have any cum for this most-important interview? Was Miss Wooldridge going to be disappointed by my pathetic squirting ability, and I wouldn't get to move in? All this rushed through my head as I saw my penis release a tiny bit of semen.
"Let's see what this does," Miss Wooldridge said, and I felt a strong push at the base of the buttplug. It sent a shock up my whole body, and to my surprise, a huge gush of semen shot out of my dick! Three, four, five ....... six ....... seven ...........eight big squirts splashed onto the platterful of delicacies! My cum was covering the cakes and cookies with loads of hot cream. I was finally releasing my cum, and it felt so good!
"Look at it! He's cumming very nicely. Such a good volume, I'm sure he'll do quite well at C.F.N.M. Is he done, girls? I want a taste," Miss Wooldridge requested.
"I'm just getting the last little bit," the girl squeezing my cock informed her, and she milked long enough to get every drop out of my very-happy penis. When no more cum dripped from my peehole, the girl beside me took the platter away and brought it over to the old lady. From between my legs, I could see her pick up a cum-covered caked and take a big bite, giving a nod of appreciation as she tasted my fresh semen.
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