Jolene's Momma Pt. 01

(The names and locations in this story are completely fictional and have no connection with any person living or dead.)

My name's Chris. Wife Jolene and I have been married six years now. Live in the small city of Centertown, Ohio. It probably got that name because it's about half way between Columbus and Cincinnati. Being from a midwestern small town, the residents' views are conservative, religion is big, and everyone eats corn on the cob and watermelon in the summer.

I work as a junior planner in the city's engineering department and my wife works as the city clerk (she earns more than I do). Naturally, we met at work. We eventually plan to have children, but want to save up some money first.

People often remark that we could be brother and sister. We're both of slim build, about five-foot-six, and we don't tan easily. After four years of marriage, we finally realized our dream of owning a home, an older, two-story midwestern home with some gingerbread and a big front porch. I love it.

Early on, during our courting days we had some hot and heavy dates, and it wasn't long before we jumped into bed. Jolene was a little shy at first, not having dated much, but once we hit our stride, she was enjoying sex as much as me, taking care not to get pregnant.

There was one little thing that I introduced her to after two years of marriage: I gradually made her aware that I liked to wear her lingerie. I say, gradually, because growing up in a small town, she knew practically nothing about crossdressing (except what she'd seen in movies like "Some Like it Hot" and "Tootsie").

So, one time I said, "You know, it really turns me on to see you in a bra and panties."

To which she replied, "Well, that's sweet. So which of my bras and panties turn you on the most?"

And I responded by rating her various pieces of lingerie on a one-to-ten basis.

"Really," she responded, "I didn't know you noticed them so much." And then, after more thought, she added, "Do I turn you on as much when I'm not wearing them?"

"Yes, really," I replied. "But you know, when you have them on it's like the gift wrapping on a terrific package."

She laughed.

This sort of banter went on and on over many days, until the day I asked to wear one of her panties while we were making love. There was a slight hesitation, but I had more or less prepped her for this moment, and she laughed and handed over her frilly red and black stretch undies. I wasn't embarrassed putting them on, and she immediately noticed my erection underneath. She touched it, saying, "My, my, bowser obviously loves feminine things!"

This went further in the ensuing months, until we always made love with me wearing lingerie, and sometimes I even wore a nightgown when I slept with her. She, being the generous person she was, bought me nice stuff.

When I eventually suggested dressing all the way as a woman sometimes, she drew the line, saying she didn't want crossdressing to define our relationship. I didn't press the issue.

After about five years of marriage, we hit a speed bump in our marriage. Jolene caught me staying up late one night looking at crossdressing and sissy porn on my laptop while she was ostensibly deep in sleep. She had thought I was going over our household finances! I tried to talk my way out of it and smooth things out. I said I'd come across the pictures accidentally.

After that, there was some distance between us. Sex between us seemed to become more perfunctory, and it was without lingerie. Nonetheless, I still managed to indulge in viewing porn when she was out of the house (sometimes when wearing her things). I especially loved to see pictures of women with nice tits and feminine faces and beautiful erect dicks.

Then there was the time her mom, Brandi, came to visit. Brandi lived in Texas, so we didn't see her often. Jolene convinced me to have Brandi come for a week while we took vacation time from work.

Brandi needs some explanation. She divorced her alcoholic husband soon after their two children were born. She took the reins of the family easily, becoming the well-paid bookkeeper for a large trucking company. Meanwhile she indulged her passion for bodybuilding, winning several competitions. I had seen the photos of her very-well-muscled body, glistening with the oil bodybuilders use for photos and competitions. Over the years, she'd stopped entering competitions, but had maintained her physique.

Jolene was quite the opposite, not being into exercise beyond a little jogging with friends.

When Brandi drove up, we greeted her effusively. Not surprisingly, she turned down my offer to help her with her two suitcases, saying, "I've got it, Chris. I'm in better shape than you ...."

I couldn't argue with that.

Following her down the hallway to her room, I noted her short hair and muscled butt, pushing against her tight jeans.

We had dinner together that evening, with Jolene and her mom trading stories. Brandi really doted on her daughter, but engaged me hardly at all. When she did, she's say things like, "Chris, why are you still a junior planner? You need to take some more college courses so you can move up in the department."

And, "Chris, I noticed the house needs a painting job. Have you given some thought to that?"

To which Jolene added, "We've talked about it, but it never seems to get done."

So, after a day or two, the overbearing mother-in-law treatment was getting old. For the first time, I truly understood that jokes about mothers-in-law were on the mark.

I encouraged them to go out and do things together, so I could stay home and indulge into a more rewarding enterprise: trans porn. After four days, they decided they were going to spend an entire day at a nearby large casino and invited me along. I said I had some paperwork from city hall to look at and declined. But the morning of the trip, Brandi said she didn't feel well and got Jolene to go by herself. I cringed. Now I had to do something with her mom -- entertain her, take her out to eat ..... something.

She turned down all my suggestions, implying I was a poor host. After Jolene left, Brandi and I were sitting side by side on our sofa, watching the local news. Her large presence (she was five foot ten and weighed 170) intimidated me a little. I could virtually feel the heat of her muscled body. Her movements were so deliberate and confident, and her boobs were big and impressive. Her shirt was unbuttoned down to the point where I could see the beginning of a black bra.

At one point during a commercial she turned around to face me, saying, "Chris, you and I need to have some time."

"You mean, to talk?"

"Yes, and more."

With that she reached over and grasped my wrist in a powerful, viselike grip which I was powerless to remove. Actually, I didn't even try.

In reality, I wasn't surprised. Unconsciously I'd seen this coming. The undercurrents of her visit were culminating in this. Here was a woman much stronger than me, exerting her will. I was cowed and confused. I even had a vision of her hurting me physically.

Then she did something that really took me by surprise: She dropped my wrist and latched on to my ear, pulling me down the hall and into her bedroom. I was speechless, feeling like an eight-year-old boy being disciplined by a mother for having said the F-word.

"What the ....?" I protested.

"Quiet," she commanded. "Don't speak unless spoken to. Got that?"

I nodded yes.

It was then that I noticed the feminine apparel carefully laid out on her dresser; mostly Jolene's lingerie. I had worn all of the items at one time or another.

Brandi looked at me sternly. "I understand that you took a liking to my daughter's underwear."

Embarrassed, I didn't respond, but she read my answer in my face.

So, Jolene had spilled the beans to her mom. I was getting the feeling I'd been set up.

"Well, isn't that something?" said Brandi in a mocking tone. "So, I want to see for myself, Chris, or Kristi. Give me the pleasure of dressing up for me; put on a little show for me."

"You're kidding, right?" Where I'd never been shy about dressing around Jolene, doing it for her mother was another thing entirely.

"Don't mouth off to me," she said with anger, as she twisted my ear. Hard.

I glumly began to undress under her piercing gaze. When I got down to my jockey shorts, I hesitated. My dick felt completely wilted underneath. She brought me one of Jolene's better bras and a lacey pair of panties.

Gingerly stepping out of my skivvies, I clumsily slipped into the panties. My instant erection gave me away.

Brandi stood there, imperiously tapping her foot, impatient.

I followed by strapping myself into the sexy bra. Now I had an even bigger erection pushing against the panties.

Brandi snickered a little, then stuffed some socks into the bra cups. "So this is who my daughter married. A sissy who gets off wearing her underwear. How pathetic. You made her put up with this?"

"It's something we both liked to do."

"No, she was just being nice, giving in to your perverted ways. You pressured her to go along, didn't you?"

"I don't think so."

She went to one of her suitcases, pulling out a slim cane with a curved end. And then, surprise upon surprise, she pulled off her tight jeans and close-fitting shirt, revealing a tight-fitting black corselette with impressively large, jutting cups. At the corselette's open bottom, multiple garters held up black nylons. The erotic sight took away my breath.

Walking to my side (I could again feel her body heat), she struck an unrestrained whap to my backside with the cane. It was painful enough that for an instant, I buckled up.

"I don't think so?" she imitated my answer. "No, you pressured her."

"Yes," I said with a weak voice. Now, my penis had shrunk even further down to a nubbin.

"Look at your little weenie now," Brandi triumphed, putting the cane up against my balls. "You are such a pathetic sissy boy. Unworthy of my daughter."

Brandi had only just begun. She produced a pair of police handcuffs and slapped them on my wrists behind my back before I could even protest, and sat me down on her bed. She then indelicately applied lipstick and some sort of makeup and found a blonde wig to complete the facial effect. I was getting an erection again, but one swat of the cane in that area brought that to a halt.

"Ha," she crowed, "look at you. You don't know whether to be turned on, or to be scared of Jolene's momma, do you?"

I just looked at her, half with anger, and half with an appreciation for her powerful presence.

She lifted my leg up and powerfully swatted the bottom of my foot a number of times. The pain was considerable.

"Answer me, sissy."

"You're right." After the caning, my voice had become high-pitched, almost pleading.

So there I was, ensconced in the wonderful bra and panties, and with a feminine-looking face -- in the company of a sadist. Where was this all headed?

I soon found out. Brandi stood me up handily, removed the handcuffs, and bent me over the back of a chair, securing my ankles to its legs and my wrists to the arms with some Velcro ties. I was beginning to realize that she had some experience in this area; that she was thoroughly enjoying putting me through her paces.

Pulling down my panties to expose my bare ass, she caned me four or five hard strokes. She had stood back so she could generate a powerful swing -- I could hear the swish of her switch before it contacted my virginal ass.

"This is what you get for disrespecting Jolene," she said. "This is what you get for betraying your manhood and dressing like a sissy. Next time you get the impulse to wear her things, remember this ....." -- and she swatted me three more times, as hard as she could. My ass stung with the pain of 20 bee stings.

"I'm going to tell Jolene, Kristi, that if you ever approach her again wanting to be a girl, that she cane you herself."

Then came the piece de resistance of our little get-together. I watched with fascination and trepidation as she found and strapped on a big black dildo. She walked over jauntily as it swung from side to side, magnificently arched upward. She drew it along my face and lips, getting a little smear of my lipstick on it.

"Now, my little sissy, I'm going to show you what it's really like to be a girl, or g-u-r-l in your case. I let my good-for-nothing husband fuck me, but that's long gone. Now I'll return the favor. I just love wearing a cock, and wielding it. Don't you just know?"

With that, she lubed her big member copiously and contacted my little asshole with its head. Taking a glance back, I could only see her nyloned muscular thighs!

I was afraid she intended to tear me up, to rend my back door.

She reached under and felt the precum wetting my panties.

"Just as I thought," she chuckled knowingly. I realized I was under the control of a skilled dominatrix, just like I'd seen in some porn.

"Oh, Kristi, do you want me to fuck you now? Do you want my cock inside you? Inside your sissy vagina?"

It was like I was separating from the Chris part of me, and feeling a female side of me taking over, like the slow-motion film of a flower opening up.

"OK."

She gently and deftly pushed her dick into me and then wiggled it around by maneuvering it with her hand. That doubled the sensations.

I involuntarily pushed backward a little, bringing more of her inside me. I wanted to feel totally occupied by her shaft.

"So, the sissy likes cock."

She proceeded to fuck me, as I allowed myself not fight the penetration and relax into it. As she thrusted, she started slapping my buttocks hard, provoking the spots where she'd caned me. I began dripping even more copiously, and started matching her motions with some of my own. I closed my eyes, as the feeling of being restrained and dominated and slapped and fucked (while wearing a bra) brought me close to orgasm.

I realized she was getting off script, like she'd forgotten my transgressions against her daughter -- and our little scene was more about what Brandi the domme wanted. She released me, forcing me to kneel under her spread legs while she was standing up, in order to kiss and tongue her fragrant and wet cunt with its tuft of hair. There was something exciting about servicing such a muscled woman, with hardly an ounce of fat to be seen. While doing so, I hand-jobbed myself. First she came and then I did, dripping sperm all over the floor.

Afterwards, Brandi said, "So, sissy, you were my bitch. I gave you the taste of being at a woman's mercy. Now you can make a choice. I've talked this over with Jolene. You will either go back to being Chris, and forget all this sissy stuff, and being fucked will be a distant memory. Or, you can go the other way entirely -- and after I leave, you would be Jolene's sissy slave. Her sissy bitch. You would sign a contract to do so, and you would always dress as a woman at home. She would not hesitate to inflict pain if you got out of line. You would be at her beck and call.

"And most importantly, she would totally control your sexuality. You know what a male chastity device is, right? You would wear one 24-7, and she would have the key.

"If you got tired of this arrangement and gave Jolene a problem, I'd drive up here in a flash and set things right. And you know I'd be much harder on you than she would."

I had no hesitation about my choice of my lifestyle. So, before Brandi left, we had a little ceremony where Jolene and her mom cheerfully brought out a little gift package wrapped with ribbons, and inside was the cutest and yet most ingenious chastity device, with the name "Kristi" engraved on it. They laughingly fitted it onto my genitals, and locked it with a tiny padlock.

Next, I examined my contract. It read:

"Chris (also known as Kristi) Zalenska, on this date _____, in full possession of his senses and without coercion, agrees to the following:

1. To obey without hesitation and questioning -- the requests, commands and desires of Jolene Zalenska and to execute them to her complete satisfaction.

2. To completely stop the watching of pornographic pictures and videos of any kind.

3. To submit to punishment by caning in restraint if upon a second chance, the requests, commands and desires of Jolene Zalenska (and the terms of this contract) are not met satisfactorily. There will be a minimum of seven full-strength strokes, followed by ten more if any insubordination is observed.

4. To also submit, if necessary, to a paddle, whip or other punishment device as desired by Jolene. Full-body bondage may also be used for punishment.

5. To allow the further punishment of chastity lockdown without release, for as long as necessary to obtain complete subservience. Any attempt at masturbation will be met with punishment and further lockdown. For extremely good behavior, the chastity device may be removed for several hours once per week. Jolene owns Chris' penis and determines the level of his sexual satisfaction.

6. To swear fealty to the female race, to honor their superiority, and to support every feminine inclination of Jolene's.

7. To further honor womanhood, when at home, to wear the lingerie and clothing of a woman, including jewelry and shoes, and light cosmetics. An appropriate and attractive female wardrobe will be created, as approved by Jolene. If found to be wearing or using any of Jolene's clothing or items, punishment will be given. Hair will be grown to a woman's length.

8. To wear woman's lingerie under work clothes as directed.

9. To go out with male friends no more than once per month.

10. To insert a tampon within the male vagina to be retained for two days every month.

11. To not attempt to initiate foreplay or sexual touching. All sex of any kind will be initiated by Jolene and will be directed toward her satisfaction.

12. To reinforce subservience, wear a collar and leash to bed each evening which will be attached to the bed, to ensure distance from Jolene unless released by her. A nightgown will be worn.

13. To submit to penetration by strap-on dildo, if desired by Jolene.

14. To prepare, cook and serve meals and clean up afterward when directed to do so.

15. To give Jolene full power over the household finances. All financial decisions will be made by her.

16. To generally be of good spirits with the goal of dropping masculine aggressiveness and moodiness while promoting Chris' (Kristi's) passive femininity and the worship of, and service to, Jolene.

With her experience as city clerk, Jolene had had no problem writing the contract. I wasn't sure it was legally binding, but after experiencing Brandi, I was thoroughly ready and willing to submit and be dominated and become a part-time Kristi.

I dated the document and signed my name. Jolene smiled knowingly as she signed, and Brandi signed as a witness. The following day, Brandi returned to Texas.

Could Jolene impose her will on me like her mother did? That remained to be seen.

(To be continued.)