Ms. J used me for things that were private and personal but not intimate. You don’t consider the feelings of a buttplug. You lube it up, use it, clean it, and toss it back in the drawer. Does a buttplug enjoy its work?
The lobby and stairs were empty at 8 AM, so I texted her and quietly slipped in her door on the dot. The coffee seemed to meet her expectations. As she sipped it, she told me some of her story.
“I’m a writer. I have a project that is due in six months. I cannot allow this,” gesturing to her boot, “to delay me.”
“You will continue to call me ‘Ms. J’ because I do not want people to know either my real name or my pen name,” she explained. “You might find out or be able to guess one or both. If you do, never mention either of them to me or anyone else.”
“By birth, I am related to powerful people. Because of them, my father died when I was young,” her eyes stared in the distance, “which gave my mother and me a choice. She took me to live where no one would find us, where no one has heard of those people. When I was old enough to make my own decisions, I chose to live here, but not to be involved.”
“Yesterday, you forced me to reach out to them,” she tried to contain her anger. “Now I owe them, and I don’t want to owe them anything more.” I guess the restaurant doctor doesn’t send bills.
Ms. J swallowed the last of the cappuccino and licked the foam from her upper lip. I’m sure she has to shave it, the one part of her body she couldn’t keep natural and covered.
“My writing is my life and my way to stay away from them. I can’t let your …” she struggled for a word, then went with the vernacular. “your fuckup fuck me up!”
She continued instructing, “I don’t want people thinking I have anything to do with you. Don’t be seen coming up here or leaving.” I had noticed a video screen by the door that showed the hallway outside. “When you get the mail, don’t let people see you’re getting mine, and don’t look at any of it. Bring the mail and any shopping you do when there’s no one around, late at night or early in the morning if necessary. Unless I give you permission, if you aren’t out doing something for me, you will be in your apartment. You can work or whatever, but when I text, you drop whatever you are doing.”
Grabbing her phone, she sent me a long text, a shopping list: a walker, reusable ice pads and ibuprofen were obviously for her injury, plus miscellaneous food and household items.
“That’s today’s list,” she said. “Go.”
I headed out. She didn’t say anything about money, so I guessed I was paying. When I returned, she was busy at her computer and didn’t acknowledge me as I set things on her table. Not wanting to distract her, I was about to leave when she stopped me. “Wait! Once you’re here, you stay until I dismiss you.”
My usual inclination to explain or excuse myself melted away in her presence.
She continued working for a few minutes before turning her attention to me.
“You need to adjust the walker,” she said, standing up with her crutches. The four-legged device would be easier for her to use in the apartment and it had a tray for carrying things. I set it to the height she wanted and she took a few steps with it.
“Push the couch that way,” she said, as she walked around her apartment, judging the clearances she needed. I moved furniture and rolled up throw rugs so it was safe for her. When she was satisfied with the arrangement, she sat on the couch with her leg up.
“It’s throbbing,” she moaned.
“An ice pad should help,” I offered. The ones she told me to buy were, of course, still room temperature, but I had anticipated the situation and bought some instant ones as well.
“Would you like me to apply it?” I asked. She nodded.
She winced as I opened the boot so I could get to her leg. Squeezing two packs to activate them, I placed them around the tender area. As the cold penetrated her pants, she sighed with some relief.
“I’ll put the reusable ones in your freezer,” I said. She nodded.
When I returned to see what else she wanted me to do, she held her head in her hand with her eyes closed. She shook her head from time to time—in pain, frustration, aggravation, all of the above? Finally, she looked up at me.
“Here,” she said, pulling a bottle of pills from her pocket and holding it out to me. “Take this,” her eyes were intense. “Keep those safe; I know exactly how many there are. Now go.”
I slipped it into my shirt pocket and made an undetected return to my apartment. The bottle looked like a normal prescription for a widely used painkiller. It was dated yesterday, so I assumed she got it from the restaurant doctor. I locked it in the safe I have for computer backups. Had she removed some and given me the rest to avoid an accidental overdose?
The rest of the day passed without incident. I was wondering how Ms. J was doing as I ate my dinner when I heard someone buzz the outside door. Taking a peek, I saw a restaurant delivery boy take something up the stairs. The sound of her door opening and closing right above me said she wasn’t going hungry.
The next day, I wasn’t summoned until 10 AM for her cappuccino. She looked a little haggard, but gave me a list of errands and sent me off. When I went to bed that night, I began to think this scheme might just work out. I had been able to spend some time on my job that day as well as keep Ms. J happy.
My phone yelped at 1 AM. “Come now,” she texted. Remembering the other night, I flashed on Ms. J’s hairy asshole as I took a two-minute shower. Uncertain what she would want at this hour, I silently climbed the steps and entered her apartment.
I had not yet seen her bedroom, but it was the only room with a light on. She was on her back, wearing a knee-length flannel nightshirt. I stood at the foot of the bed. She looked upset, her eyes red and wet, her brow and face strained.
“I’m an addict,” she said quietly. “I was, but I don’t think you can ever leave that behind you. They made me take some the first day, but I gave you the rest. I can’t take any more of those.”
“I have to sleep,” she said with emotion. “I need to think. I need to write. I can’t get to sleep. I tried,” she looked at the vibrator and dildo on the sheet next to her pillow. I was not her first choice to solve this problem.
“I need a good orgasm,” she said with a tinge of desperation. “Lick me. Finger me. You keep your clothes on.” Ms. J pulled her nightshirt up above her breasts, giving me access to her body.
It was a plea as well as a command. I carefully climbed on the bed between her legs, being sure not to disturb her boot. Her pussy was in full bloom, the dampness of her masturbation soaked her patch of fur and curled the dark hair on her groin. I gently lapped at her pubes, reducing her wetness as I massaged her belly and upper legs.
Taking it slowly, I tried to relax her. Nuzzling her bush, I siphoned the excess pungent liquid. Delving deeper in her folds, I heard a sharp intake of breath when my tongue touched the naked skin of her inner flesh. Planting rows of kisses seemed to reduce the tension in her body. I tried to show her I could do things those plastic devices could not.
Reaching up to her breasts, I fingered her flattened globes, squishing the soft tissue. Whether caused by the upper or lower stimulation, her nipples began to respond. I would normally have taken my time, getting acquainted with her genitals, but I think the head start she got from the sex toys made her closer to fruition. She put her hands on my head to focus me on her most sensitive spot.
Drawing it between my lips, I felt it retract and knew it was showtime. A thumb and finger clasped each nipple as I flicked my tongue across her clit. She climaxed with a moan that could have been heard in my bedroom. I gave her a flat warm tongue to wiggle against until the spasms faded. Backing off a little, I moved lower to slurp up what she had produced. My hands on her breasts were relieved of duty by hers, so I massaged my way down her body.
She gave me no sign to stop, and I sensed that my post-orgasm care was starting to interest her in another one. I wet my fingers with her lubrication, then played with her still swollen pussy. Spreading her hairy vulva, my slippery lips and tongue worked her smooth inner lips. A slick finger teased her opening, and the airy “Yes” she sighed encouraged me in. Soon a second and a third joined, giving her the girth of a cock.
Lacking the depth, but having more agility than a penis, my fingers probed upward in her tunnel, seeking her G-spot. As I gently explored, I thought I detected the location and it began to respond as I slowly stroked it. She tensed a bit at first but then relaxed to accept the caress. My tongue was still active around her clitoris, and my fingers still stretched her vagina, so the G-spot was a bonus in any case.
“Yes, faster,” her voice was breathy. I gradually accelerated and applied more pressure. After a few minutes, it paid off with a multisyllabic moan and a long series of contractions.
They had hardly stopped when, without a word, Ms. J crossed her right leg over my head and rolled on her side, forcing me to extract my fingers. She pulled down her nightshirt, indicating the session was over,
“Turn off the light and lock the door on your way out,” she sighed.
I quietly went back to my apartment.
Looking in the mirror in the bathroom, I saw some black curly hairs stuck to my chin. My nose and mouth were full of the smell and taste of Ms. J, not the same as but not so different from other women I had known. Despite the source and circumstances, my tongue savored it on my lips. As I washed my face, I could not recall if I had even gotten hard while I was in bed with her, something that would have been a certainty in any similar situation.
At nine in the morning, she texted for her cappuccino, and I reported ready for duty. She had a list of errands and things to buy.
“There is something else before you start,” she said. I was expecting that she might mention something about last night, but it wasn’t what I had imagined.
“You must not think that the way I used you last night changes our relationship in any way. What are you?” she asked.
I replied almost reflexively, “I am your slave, Ms. J.”
“To be sure you remember that, before you start today’s tasks, you are to buy a buttplug and put it in your asshole, wearing it the rest of the day. You will send me a picture of you in your car inserting it,” she said. “Obviously, it will still be in when you get back here. Now go.”
The fact that I had a buttplug or three in my apartment was probably irrelevant to Ms. J. As I walked to my car, I tried to think where I could get one. The internet had put a lot of local sex shops out of business. I remembered there was a feminist bookstore a dozen blocks away that had a section for sex toys and paraphernalia and found what I needed there. I resisted the temptation to open it in their parking lot, figuring there might be cameras or people watching.
Finding an alley where I was pretty sure no one could see, I was grateful that they had slipped a sample of lube in the bag. Unwrapping the four by two-inch glass model, I snapped a picture of it, then one with it partially, then fully inserted. Zipping my pants up, I sent the pictures off. I waited a minute but received no response. Scared for a moment that I might have sent them to someone else I know, I verified they went to the right number, then started the errand list.
Aside from the full feeling in my rectum, I was self-conscious, wondering if anyone could tell. I thought I was walking normally, but I know I was clenched tight, worried that it could somehow slip out and slide down my pants onto the floor.
In a drug store about an hour later, I received a message. “Show me,” it said. Asking where their restroom was, I suspect the discomfort on my face convinced them I really needed it. I looked for surveillance cameras but didn’t see any as I slid down my pants in the stall and snapped a picture.
Almost back to the apartment, I got a text. “Learn how to give a pedicure. Come at 1:00.”
I hadn’t paid attention, but the shopping list did include what you need to give one. Nail clippers, polish remover, clear and red polish, callus remover, plastic basin, towels, etc. I only vaguely knew the process, but I’m a quick learner. I had a little over an hour to educate myself using the internet.
She sat reading in a leather chair waiting for me. Setting up on the floor in front of her, I filled the basin with warm water and began. Although I removed the boot, I planned to work on her other foot first. I rolled up her pants a little and pulled off her white cotton socks, revealing that her toenails were painted bright red. Interesting that she would do that, given she would probably never wear open-toed shoes. The reason was plain: wisps of fine, dark hair decorated the tops of her feet and toes.
In any case, whatever her regular pedicure regime was, I had upset it, and she was making me pay for it. On my knees in front of her, I did my best not to disturb her reading as I worked, trying to remember everything I had watched over the last hour. She admonished me a few times, once because I was being too gentle with the footstone on her right foot, once because I was too rough on her left, making her cry out in pain. She stopped me from moving on to the next coat of polish, saying it wasn’t dry yet.
I idly massaged her foot as I waited for it to dry, eliciting a relaxed sigh. With her guidance, she let me proceed with the second, third and fourth coats. I’m sure it took three times as long as a professional and didn’t look half as good.
“Do you want me to put on your socks? Or the boot?” I asked as I was finishing up.
“Just the boot,” she said. “I want to admire your handiwork.” The last remark was tinged with sarcasm, but I knew she was right. I was cleaning up, wondering what to do with the various equipment.
“You can keep all that at your place,” she anticipated my query. I put everything in the basin and placed it near the door.
“Let me see the plug,” she ordered. I stood in front of her, turned and lowered my pants and boxers. “Does it turn you on to have that in you?”
“Yes,” I admitted, twisting my upper body and head to face her. “Sometimes it is uncomfortable. Sometimes I worry it will pop out and embarrass me. Sometimes I feel a tingle when it rubs against my prostate.” I paused, unsure if I should confess the thought that only now rose to the surface. “It reminds me that I am your slave, Ms. J.” I hesitated again, but her eyes drew the truth out of me, “That turns me on.”
“Have you had any orgasms since you broke my leg?” she asked, matter-of-factly.
“No,” I replied. It seemed strange to admit that I hadn’t, but the stress and other distractions left me without the urge.
“Even after you licked my ass, and licked and fingered my pussy?” she sounded skeptical.
“No, Ms. J,” I protested, “I wouldn’t …” I couldn’t complete the thought. Why wouldn’t I?
“You have the proper attitude without even knowing it,” she smiled. “You are my slave. As long as you are, I decide when or if you can experience pleasure. I expected that you might have jerked off after your service to me; if you had, I would be punishing you right now.”
“Since you won’t have that lesson, you will have another. Turn around, get yourself hard,” she instructed. My limp dick awoke with her words before I touched it. Sitting in the chair wearing her usual oversized shirt and her rolled-up pants, only her red-toenailed feet offered any suggestion of femininity. Whatever it was that inspired me, my organ began to fill my hand.
“Show me how you like to jack off,” she said. I pumped with my left hand until my cock reached full length. At that point, my right hand roamed around, tickling my balls, teasing the head, taking over for the left for a few strokes.
“You don’t cum unless and until I tell you to,” she stated the obvious. “You cannot ask permission to cum, so you had best learn control.”
“If I do tell you to ejaculate, you will capture all of it and consume it. I don’t want any of your fluids,” she said with revulsion, “on anything, even the floor.”
After idly watching me for a minute or so, she asked: “Are you enjoying stroking yourself?”.
I hesitated, unsure how to respond. Obviously, my penis was getting stimulated, but the situation was—unusual.
“It’s okay to admit it. In fact, I don’t like that you didn’t answer straight away honestly. Are you enjoying stroking yourself?” she repeated.
“Yes, Ms. J,” I blushed. How did she know me so well?
“How long would it take you to reach orgasm, if I told you to do so?” she asked.
I was unsure, given the situation and the absence of lube. “Three minutes?” I guessed.
“Let’s see,” her eyes focusing on my crotch seemed to provide additional motivation. “Keep going and see how close you can be in three minutes.” She started a timer on her smartphone.
Jerking with my dry hands was not the best stimulation, but my cock was overdue for an eruption, and it would take what it could get. As my internal muscles got into the spirit, my anus squeezed the buttplug, teasing my prostate.
“Two minutes,” she announced.
I had not progressed much in that first minute, so I began jerking faster, my off hand trying to contribute. I wished I could lick my palm, jiggle the butt plug, pinch my nipples, and any of a dozen other things that would help get me going. I focused on her feet and her face, imagining myself falling to my knees to suck her toes, daring to imagine her O-face, which I so far had not been able to see.
“One minute,” she tolled.
My climax seemed to be within reach. I took a deep breath, and my left hand found a consistent rhythm. My nuts tightened as my right fingers stroked warmth into them. I smeared the leaking drops of fluid around the head.
“Thirty seconds,” she said, “I want you ready to cum.”
I felt a little proud of myself, that I was on the edge. I slowed and loosened my grip, positioning my right hand to collect my emissions, ready for the command to ejaculate.
“Ten seconds,” she said.
I felt like my heart beat fifty times before her timer beeped.
Ms. J said nothing. She watched as my hands froze when I realized she had not told me to cum. Staring down at my raw, throbbing cock, I squeezed the base hard with one hand, suppressing the impulse while keeping the other in position in case my efforts to contain myself failed.
“That’s enough for now,” she said conclusively. “You can go.”
I slowly pulled up my pants and fastened my belt.
“When you get home, take out the plug. Focus on what I gave you, not on what I denied you,” she said, then added “I enjoyed it. Think about that.”
Back in my apartment, I spent some time reviewing and looking at other web sites about pedicures and made some notes. The next time I had the chance, I would do better.
While I cleaned the anal toy, I reflected on what she said. I did enjoy masturbating in front of her, the excitement of racing to get close, teetering on the edge. As much as I missed the ultimate explosion, there was no reason to discount everything that led up to that point.
I did feel good about the idea that she got something out of it, whether it was watching me perform or seeing my frustration at the end or both.
