Jeff parked his car in the downtown parking deck and walked out to the street, checking the address in the email confirmation for the third time. He had expected something in the run-down warehouse district and instead he found himself in the nicest and most upscale part of the financial district. Still worried that he had made a mistake, he took the elevator to the 8th floor, found suite 816, knocked and then entered.
Once inside the office, Jeff saw a waiting area with wood paneling, a table with a receptionist, and a few chairs. There was a second door to an interior office that was open a few inches, but Jeff couldn’t see far into it. The receptionist was a pretty blonde woman with long hair and blue eyes. She wore a white blouse, and he could just barely see a green skirt and white stockings under the table.
“May I help you?” the receptionist asked.
“Oh, um, hi.” Jeff started. “I’m looking for Jessica at Exciting Encounters. I have an appointment.”
“Then you’ve got the right place.” The receptionist smiled brightly. “Let me just check her appointments so we can get you checked in.”
She paused and typed for a moment. “Yes, here you are. You’re the man who had some questions and wanted the short consultation before booking a full session. You know, she doesn’t usually do that, but she had a little time free today so she decided to fit you into her schedule. But listen to me!” She exclaimed. “I’m just little miss exposition, aren’t I?” she laughed.
“Anyway, I see you gave some information in your email, but we need you to fill out these details and sign a couple of releases.” She handed a tablet to Jeff for him to enter the information.
Jeff took the tablet and stared down at it. “I was hoping to keep this as private as possible.”
“Don’t worry about that, sir. We’re very discreet. But this is a business, and we do have to keep some records,” the receptionist told him.
“Of course, I understand.” Jeff answered. He sat down and went through several screens on the tablet, then finally returned it to the receptionist when he was finished. He sat back down and waited.
After a few minutes, the receptionist looked up from her computer and told him, “Sir, Mistress Jessica will see you now. Just go through that door and leave it open if you don’t mind.”
Upon entering, Jeff found that the interior office had a nice view of the city. It was on the corner of the building and two of the walls were floor to ceiling glass windows. The other two walls were covered with a mix of bookshelves, a few cabinets and a couple of landscape photographs, not at all what he was expecting. At the center of the office was a large wooden desk, bare except for a notebook, a few pencils, and a brass ring bolted to the top edge of the desk. Behind the desk sat Mistress Jessica.
Jessica stood up when he entered the room and greeted him. “Hello, Jeff, is it? I understand you wanted to ask some questions about our services.”
Jessica wore a dark blue long sleeved blouse, brown trousers, and brown heels. Her dark black hair was pulled back, and she wore red lipstick and brown tortoise shell glasses.
Jeff looked hesitant, and Jessica spoke again. “Do I surprise you? I’m sure Tiffany told you, we’re a business and we’re in a respectable part of town. I’m not going to show up for work in a corset or in a latex body suit. Now go ahead, let’s not waste time.”
“Well, of course.” Jeff started, looking for a place to sit down, then realizing the only furniture was the desk and the chair that Jessica occupied. “I’m very interested in your services, but I suppose I wanted to know what I was getting into. What to expect, that is…” Jeff trailed off, uncertain of how to proceed.
“Stop for a minute, Jeff.” Jessica spoke up. “I can see you’re nervous. You don’t want to ask anything inappropriate, but you don’t know what is and isn’t appropriate. Let’s try something.”
Jessica took a pair of padded leather bondage cuffs out of her desk drawer. “Put these on.”
Once Jeff had the cuffs on, Jessica locked the two cuffs together with a small padlock, then attached the cuffs to the brass ring on the desk. “Lean over with your chest on the desk and your back straight, so your butt sticks out toward the door where you came in. Yes, just like that. Perfect.”
When Jeff was cuffed to the desk and positioned as instructed, Jessica came around from behind the desk and stood next to him. She loosened his belt, unbuttoned and unzipped his trousers, and pulled his trousers and underwear down to his ankles. This left Jeff naked from waist to calves and bent over the desk.
“But, uh, mistress…” Jeff stammered.
“You may call me Mistress Jessica.” Jessica instructed him.
“But, Mistress Jessica, I had thought we were just going to chat today.” Jeff questioned, glancing over his shoulder at the door that was open to the waiting area.
“And now you can ask your questions, but you should have a better idea of what you can ask. Plus I can get a better idea of your reaction to my answers. For example, I can see you’re already getting an erection from being bound and exposed.” Jessica smiled. “Go ahead with your questions.”
“Um, yes, Mistress. I was going to ask if the sub or client is nude during the sessions.” Jeff asked.
“Let’s call you a client. And yes, you see you can be partially nude, or whatever I think you need.” Jessica answered.
“And, is the Domme, that is, are you nude during the sessions?”
“Certainly not!” Jessica answered. “This is a respectable business, not a brothel. What other questions do you have?”
“Yes, Mistress. Do you inflict a lot of pain on your clients?”
“Not more than you can take.” Jessica laughed while she paced the room answering his questions. “I’ll try to explain.” Jessica took a riding crop from behind her desk and struck Jeff’s exposed ass with it four times, hard. “Now, you’re red and stinging, but I can see that your cock is fully hard. So, yes, some pain, but clearly it’s a level of pain that you enjoy. What else?”
“Do you require chastity or orgasm control?” Jeff asked.
“Possibly, in rare cases, but it’s not something that I focus on. In general, you’re free to masturbate as much as you want when you’re not here. Of course, when you are here, you’ll do as you’re told to the best of your ability. What else?”
“Do you penetrate your clients? Anal penetration, I mean.” Jeff clarified.
“Do you like that, Jeff, you kinky boy,” Jessica teased. “But I’ve seen all kinds of things. Have you ever been pegged before?”
“Yes, Mistress, once by a woman that I met through a friend at work.” Jeff answered.
“Then you’re more experienced than many of my clients. You shouldn’t have so many questions.” Jessica cautioned. Jessica walked back behind the desk again and took out a pair of blue latex exam gloves and a small tube of lubricant.
“Is there any thing else you need to know?” Jessica asked Jeff.
“Do you do skin to skin contact?” Jeff asked, watching Jessica put on the gloves.
“We usually avoid skin to skin contact, but sometimes we make exceptions for special occasions.” Jessica answered. She walked behind Jeff and squeezed a little of the cool lubricant onto his asshole. She next slid one finger into his ass, then a second finger. Jeff started to lean back into her fingers, pushing back to help her fuck him.
“You do seem experienced at this, Jeff. Look at how hard you are now. Have you ever cum from having your ass fingered?” Jessica asked him.
“No, Mistress Jessica, I haven’t.” Jeff answered.
“Well, we’ll see if we can change that.” Jessica told him. “Tiffany, please come in and help me with this.”
“Yes, ma’am.” Tiffany answered, walking into Jessica’s office. She seemed unsurprised by Jeff’s condition, bent over the desk with his pants down and Jessica’s fingers in his ass. “I should tell you, ma’am, that your next appointment is in 10 minutes.”
“Thank you, Tiffany.” Jessica responded. “Please take off your shoes and sit cross legged on the desk. Lift up your skirt just enough so that Jeff can see your panties.”
“Yes, ma’am.” Tiffany answered and positioned herself on the desk. Jeff could see that Tiffany’s stockings ended at the tops of her thighs and that she wore white cotton panties under her green skirt.
“Jeff, do you like seeing Tiffany’s cute white panties?” Jessica asked.
“I like serving and pleasing you, Mistress,” Jeff answered.
At this answer, Jessica took her fingers out of Jeff’s ass and slapped his balls so that he jumped. “Don’t give me that bullshit, I know you want to serve me. Do you enjoy seeing Tiffany’s cute panties?,” Jessica asked again, sliding her fingers back into Jeff’s ass.
“Yes, Mistress Jessica, I do.” Jeff answered.
“Good answer. Tiffany’s panties are very cute, and I can tell from how your cock is throbbing that you like seeing her. I think you also like that she’s watching me fuck you with my fingers.” Jessica told Jeff.
“Tiffany, put your legs down over the edge of the desk and slide up so your crotch is right in Jeff’s face.”
“Yes, ma’am,” Tiffany answered, sliding closer to Jeff’s face.
“Jeff, put your nose right in Tiffany’s crotch and breath through her panties while I fuck your ass with my fingers. We’ll do this until you cum, but don’t keep Tiffany here too long, we’ll need someone to check in my next appointment in a few minutes.”
Tiffany slid closer to Jeff’s face and he put his nose against her crotch. Tiffany giggled, “That tickles, ma’am.”
“Shh, Tiffany, let him concentrate,” Jessica said indulgently.
Jeff kept his face buried in between Tiffany’s legs, smelling her panties while Jessica fucked his ass with two fingers. After a few minutes, his cock started to twitch and he ejaculated, the cum dribbling down his legs and shooting into his underwear on the floor between his ankles.
Jessica saw that Jeff had cum and sent Tiffany back to reception. “Thank you Tiffany, that will be all for now.”
“Yes ma’am.” Tiffany answered as if nothing unusual had happened. She climbed down from the desk, then put her shoes back on and walked back to the reception area.
Jessica removed the latex gloves and dropped them in the trash can next to her desk. She unlocked Jeff’s cuffs from the ring on the desk and had him pull up his trousers to cover his cum filled underwear and sticky legs.
“Goodbye, Jeff. You can book your next session with Tiffany on your way out.” Jessica told Jeff as she sat down behind her desk to prepare for her next appointment.
Source: reddit.com/r/sexystories/comments/4xupsz/interview_with_a_domme_mffdom
This is a more straightforward, self-contained Femdom story that leaves open the possibility of more from these characters in the future.
Really awesome. Hope you’ll think of writing more about mistress Jessica.