Jolene's Momma Pt. 02

After Brandi left, after I had willingly signed my privileged life away, I also had some nagging fears. Like, would Jolene be able to carry out her role, since she was usually so sweet and caring, and she usually gave in to what I wanted? Or would she take after her mom and become a merciless taskmaster and sadist whom I would hardly recognize?

After we had two days of no change, where we were both rather silent and kept our distance, I returned home from work to see the "Sweet Sixteen" clauses of our contract blown up in large type and framed on the living room wall. Jolene, smiling, said, "Yes, Chris - Kristi - this is to tell you I DO take our contract seriously! Now that Brandi's no longer here and whipping your behind, do you still agree to everything you signed off on?"

"Yes," I said without hesitation.

"I have some background to pass on, then," said Jolene. "You already know that for the longest time Brandi worked for the trucking company. Then, not too long after we kids left home and she retired, she got bored just lifting weights and met this other musclewoman at a gym. The other woman introduced her to the world of dominatrixes. The woman was making a lot of money doing it professionally - without sex so it wasn't illegal - and she had so many customers she needed a partner.

Brandi thought she'd give it a try, and she learned the ropes quickly - she was a natural - and was so in demand that eventually she went off on her own. She's still doing it today. That's how she can afford her Mercedes and BMW. She calls herself Mistress Cara. So what you experienced was the work of a pro. She knows what guys and girls deep-down desire - she can read their minds. She knows how to take them to new places without scaring them too much."

"I could see she was no amateur."

"Well, Brandi and I had several really long talks about female domination - femdom."

"I'm familiar with the term."

"Yes, of course, due to your online porn." Jolene rolled her eyes. "She easily figured you out - your crossdressing and all - and really gave me some insightful tips about how to relate to you, so that both of us would feel rewarded, if you know what I mean. So I figure we can rebuild our marriage based on your serving me." She sighed, reflecting her new status. "Like a queen and one of her female retinue. And beyond that, to worship me."

"Yes," I agreed, "I like the idea of serving a queen." Meanwhile, I was wondering how Jolene would dress me.

"Well, then, Kristi, I think we should ease into the contract gradually, bit by bit, so everything goes smoothly and we're both comfortable in our roles. But remember, I do expect we'll follow the agreement very, very seriously! This is no game! I look forward to shedding my old skin, and showing you a new self you haven't seen before. To wield power."

"I do worship you." I leaned down and kissed her foot.

Now I'd said it! It wasn't an exaggeration or a lie. I really wanted her in this new role. I really wanted her cunt to overpower my penis. I wanted her breasts to trump my tiny man tits and nipples. I wanted her long hair to capture me.

"That does sound a bit melodramatic when you say it," she said knowingly, "but I'll accept it as heartfelt.

"Now, to move on. At first we will zero in on your obeying me completely, without reservation or argument, on every matter. I am going to add something - if you do have a disagreement with anything, you will write it on a note and leave it in little that box over there, which I will look into every week. But I don't count on me responding in any way."

Then she laughed half nervously and half derisively, saying, "You should know that Brandi left me her cane, which I'm perfectly willing to put to use, dear. Maybe it's what you want, maybe not, but if I need to use it, I will. In fact, I realized that I must have a bit of my mom's sadist streak in me, because I look forward to hurting you a little. Or, a lot!"

"I never would've suspected you had this in you," I responded. The prospect of her caning me aroused me instantly. "Did she also leave you her strap-on dildo?"

"You would like to know, wouldn't you? Well, I'll leave that to your imagination, Kristi."

"Due to that, I lost my virginity."

"So she told me! ... Well, this will be a journey won't it?"

"Yes."

"OK, Kristi ... Show me your chastity device, which by the way, I will now endearingly call your Susan. Don't ask me why. I just feel like calling it Susan."

I dropped my work trousers to show her the demure pink plastic containment, still locked in place. Due to the talk about caning, I had begun to drip pre-cum.

"Oh, look," she said, lifting up Susan, "you're just eating up this whole new relationship, aren't you? You dirty little girl. Apparently, part of your porn habit was loving femdom too."

"Well, yes."

"Oh, lovely. So, on to the details. Every weekday morning, I will lay out the lingerie I want to wear under your clothing to work. So you don't worry too much, I will choose things which don't leave a trace under your clothing. And you should probably wear loose clothing, you know. OK?"

"That's OK." I thought it unusual for her to ask my approval, but then she wasn't a Brandi.

"And every day after work, I'll lay out and choose the feminine apparel you will change into, to include a wig, until your hair grows out long enough.

"Now, as far as the housework goes," she added, "you will perform all the most work-intensive jobs, according to the task sheet I post every few days. Know that I have cancelled our maid service, because you will be the maid! I will do a few things around here as I wish - mostly cooking, because that's something I like to do, but you will do all the shopping, cleaning up, and all that. And you must do a perfect job, or I will absolutely have you do it all over again. No ifs or buts."

"Finally, sex for you will be a reward for fulfilling all my requests perfectly, and sex will not be a right. You will earn it. Every weekend, if you have behaved one hundred and fifty percent and have a cheerful and positive attitude - we will remove your Susan for a couple hours - I may allow you to pleasure me and then we could think about your pleasure. ... Sort of a surprise to have the tables turned, yes?"

I nodded my head yes.

"Or maybe midweek, you will just service me only, if you don't mind the allusion to a car."

"That's quite fine. You are a Ferrari."

"Easy to say that now," Jolene chuckled. "You better follow through, dear."

After a moment, she added, "We must both remember that if you misbehave in any way, in addition to a possible caning, your Susan can remain locked up for weeks on end if necessary. So just be a good and respectful and perfectly obedient Kristi, right?"

"Yes, mistress."

I could tell she liked that word.

I was thinking that if she fulfilled her role well, all would be fine. My imagination began working overtime. I wanted and needed to be doing all these things while ordered to become Kristi. ... I didn't want to be Jolene's slave for years, but for now I found my new role to be totally arousing.

Jolene and I went shopping for my new wardrobe the following Saturday. I enjoyed her picking my feminine attire, even though her choices weren't always sexy. Her picks didn't even reflect the styles that she herself wore, as though she wanted to create a unique "Kristi" that would make me her ever-more-obedient servant.

At one point, she even confessed that eventually, if and when I could attain her ideal, I could go out with her in public as a woman, which both scared me and turned me on. So part of the wardrobe consisted of outdoor clothing and boots.

There were dresses, pants, leggings, tops, shirts, sweaters, bras, panties, nylons, slips, a padded girdle, shoes, nightgowns, another wig, makeup, and much more. It was rather overwhelming, and I felt like a kid who'd been deprived of sweets suddenly left alone in a candy store.

What struck me as funny was when we stopped by a costume store and she purchased a stereotypical black-with-white-lace maid uniform, with a clever little lace headband to top it off.

I was pretty silent through all of this, but sometimes I felt my cock straining against my "Susan."

When we arrived home mid-afternoon, Jolene spread out all the purchases on our king-size bed, and ordered me to dress immediately in the maid outfit, which was rather saucy in design. First on was a B-cup strapless bra, with breast inserts she'd previously ordered, followed by the rather vintage-looking, waist-cinching girdle over my panties and my Susan. Jolene showed me how to properly slip into darkish nylons and how to attach them to the girdle's garters. I was so turned on, I was breathing heavily.

"Now, now," she said. "You're only getting ready to do the chores, Kristi."

Next on was a light brown, medium-length wig, followed by the fitted, tight and flirty black maid's dress (which she zipped up in back) and modest two-inch black heels.

Jolene and I strode to the mirror to admire her handiwork.

My tasks before dinner (posted on Jolene's list) included vacuuming, dusting, mopping, cleaning the entire bathroom (including of course the toilet), doing the laundry, getting rid of the week's junk mail and other debris, and straightening up stuff in our freezer. This was not work! Imagining myself as a maid, serving a superior woman, was the reward. I loved the tight bra and seeing my tits push against the dress's bodice, and feeling the silky nylons around my legs. Knowing that my cock was held captive and buried under the girdle - and knowing that Jolene owned my dick - was arousing.

I kept having fantasies of Jolene fucking me.

That evening, after I switched to a more usual dress and removed the headband, I sat down to quietly eat the dinner Jolene cooked. As two women, we talked more easily than before - about everything but our new arrangement. The new normal.

Finally preparing for bed, I donned one of my new nightgowns and slipped in with Jolene, who interestingly wasn't wearing one of her frilly gowns, but rather a very simple, slinky, unadorned one.

She didn't initiate the leash thing specified in the contract, but I knew better than to try to spoon her or touch her. I lay my hand on my hard-plastic Susan under my gown, and was so, so tempted to shake it and try to cum, but thought she could probably detect that, with dire consequences. Even when I went into the bathroom during the night, I was tempted to arouse myself, but let it go.

Come Monday morning, Jolene made sure I went off to work wearing control-top nylons and a simple, skimpy bra under my rather boring man-clothing. I was aware of my new underwear most of the day, making me even hornier. I actually looked forward to meetings, where my attention could be diverted from them. However, I kept looking at women in the office with more interest, observing how they dressed and adorned themselves. I imagined what sort of lingerie they wore, and noticed how they used makeup. If they only knew they were now working with a Kristi!

It was as though I had halfway joined their sorority, and was enjoying some of their secret pleasures. Of course I would occasionally run into Kristi, who would give me a knowing smile, as if to say, "Are you enjoying your lingerie? You know that at any time I could tell everyone about your new role ..."

When we arrived home that evening, Jolene began to put together a meal, pulling things from the freezer. When I returned all dolled up in my maid's outfit to check her list of things to do, she complained about the way I'd organized things in the freezer the previous day.

"Kristi, Kristi, you got it all wrong. What was your thinking, anyway?"

"Well, mistress, I was thinking I'd put all the boxes of stuff together, all the ziplock bags together, and all the Tupperware things together."

"No, no, NO," she retorted. "That's not the way it goes. I should've explained things better. The veggies go on one shelf, the meat goes on another, leftovers go on another, and fruit goes on the bottom shelf."

"Oh, geez, I'm so sorry. I'll redo it."

So I diligently worked to correct the arrangement, with my earrings delightfully dangling around my ears as I worked.

The next day after work, Jolene was looking for some frozen porkchops to thaw for the evening meal. "Kristi, Kristi, you didn't listen to me yesterday."

"What, mistress?"

"You put the fruit on the middle shelf, not the bottom shelf as I instructed you."

"I don't recall you saying that."

"Well, I did. This is your first failure as my maid."

I'm sure I looked downcast. I really had been trying so hard to please her, and I was very disappointed in myself.

"You know what we said in the contract: if you don't get something right after a second chance, there's a price to be paid."

Somehow in my crazy mind, the idea of an ice-cold freezer was combining with the thought of a red-hot caning. Ice-cold peas with red-hot chili peppers.

"Go to the bedroom, Kristi."

She ordered me to stand next to the bed, and bend over so my head rested on it, then she raised my dress up onto my back, detached my nylons and pulled down my girdle, making sure my ass was nice and high into the air. Walking over with her white cane, she smoothed one hand around my ass-cheeks as if to prep them for the inevitable.

I was beginning to sweat.

"I won't say this hurts me more than you," she said. "I have actually been waiting for a chance to hurt you. Maybe it all stems from a time in college, in my sorority, when some girls held me down and one of 'em spanked me really hard. I actually enjoyed it, and I secretly wanted to be the one spanking."

With that, she began to explore my ass with the cane's tip, adding touches to my my balls and asshole.

"Ready?"

I mumbled something.

"READY?"

"Yes, mistress. I deserve this."

"Seven strokes plus one more for luck."

"Yes, mistress."

She backed away to get proper distance. There was one very light stroke, as though for practice. Then, a frightening whoosh through the air before the cane contacted both cheeks. She hadn't held back. She wasn't fearful of hurting me in the least. My worries about her determination and role-playing ability were unfounded.

The stroke aroused me. I just plain loved the idea of her delivering pain. Of her being relentless and not holding back. Of her being a sadist.

Each new stroke added more pain to the previous stroke, until I had a reservoir of serious hurt to experience. Finally, the whooshes were over and she put the cane aside. I let a large breath of air.

Curiously, she exhaled as well. We both laughed.

We looked in the mirror at the damage her strokes had left. There were long red, raised welts where the wooden switch had landed. One of the welts was very slightly bleeding.

"Stay here," she instructed, and she came back with a tube of medicated Vaseline and a jar of what looked like water.

"Now, if you were REALLY into pain, I could use this on you, dear. She put a finger into the liquid and touched it to a welt - probably the bleeding one. I was hit with a sudden and very, very sharp pain that greatly exceeded the caning pain.

"Salt water," she pronounced. "You never want to get me so angry with you that I use this afterward."

"Right, mistress," I said weakly.

She kindly rubbed my wounds with the salve, which calmed down their heat somewhat. The rest of the evening, after dinner and my chores, the strong aftereffects of the caning constantly reminded me of Jolene's power over me and I was even more solicitous of serving her.

Maybe she had been turned on by caning me, because that evening when we went to bed she attached her leash and collar to my neck and positioned me, in my nightgown, between her legs. She had me lick the insides of her wonderful thighs, then gradually pulled my face closer and closer to her lovely cunt. I was approaching the most wonderful sanctum, her godly orifice.

Her cunt was shaved, which is just the way I like it: two pouty lips with curtains inside nearly hiding her pearl-like clit. I began by gently separating her lips with my hands, then licked all around her vaginal opening as she began to twist and convulse. I then ran my hands around under her butt, while my tongue began to flick at her precious and wet clit.

"Oh, my god," she gasped.

Then I began to gently suck on her clit, which instantly sent her over the edge. She literally exploded as her chest briefly lifted off the bed. "God, god, god," she yelled, as she repeatedly pushed her cunt fully into my mouth.

Afterward, when she returned from her bliss, she said, "Oh, dear, that's the best climax ever! I think this is the end of vanilla sex for me. Now, I know, dear, you would just love to fuck the shit out of me, but no. No, no, no! Remember, if you continue to obey and worship me, and don't get the freezer fucked up any more, Saturday's coming, when we release your Susan. Just think about that."

"I really enjoyed pleasuring you," I allowed. "I had a little bit of a mental climax at the same time you came. A new experience."

She kissed me on the forehead, released the leash, and I fell asleep after I pushed the folds of my nightgown between my legs. Susan was keeping me company down there.

The next day at work I could barely sit down on my sore butt. I wondered if anyone noticed.

When Saturday finally arrived, with no more canings or other discipline meted out, we slept in until 8 a.m., with strong shafts of sunlight pouring into our bedroom. There wasn't much pain remaining in my butt - it's amazing how fast the skin heals itself.

I woke first, and obediently waited until Jolene opened her eyes. "Oh, dear," she yawned. "So nice to relax in bed." Then, "We have to get ourselves organized ... First of all, you'll get the yard and garden work done in Chris' clothing, then by noon it's time for Kristi to make her appearance."

Kristi did make her appearance, and followed Jolene's housework instructions down to the last letter. I didn't want to jinx Susan's removal, after all. I was not wearing the maid's outfit this time, but rather a long summer dress that hugged my body. That allowed Susan to make a little bulge. When I reported to Jolene that I had completed my tasks, and she was satisfied after an inspection, she - wearing tight leggings and just a sports bra on top - smiled and said, "I suppose you think you deserve to be released from your Susan."

"I'm very ready for that, if it pleases you."

"Yes, that pleases me. But only for two hours."

"Yes, mistress."

We went to our bedroom, where I removed my dress while Jolene disappeared to her secret hiding place to get the key. Her removal of the Susan was the most intensely erotic thing. My poor little dick sprang loose and quickly began an erection.

"Well look at that," Jolene exclaimed as she lightly swatted my dick back and forth. "I'll bet you're just bursting at the semen, aren't you, Kristi?"

She ordered me to take a shower, which I did with relish since my privates hadn't seen soap and water in many days.

When I returned, she was wearing a leather skirt I'd never seen before - a very tight leather skirt that came down past her knees. And beyond that, a leather bra, and huge silver hoop earrings. I was totally taken with her sexiness.

She smiled. "Like it? Now that I control the finances, I can and will buy anything I want. Expensive, yes, but I'm worth it."

"Love it, mistress."

She then found, in a precious-looking little jewelry box that was also new, a small device that looked like two tweezers connected with a chain. I'd never seen such a thing - not even in my porn. She attached each of the two tweezers - actually clamps - to each of my nipples, watching my face to see how much pain I could stand as she tightened them. When I finally bent over, she backed them off a little. My nipples were really smarting. Jolene had played with my nipples a little during our past life, but she'd never pained them.