Playing with Mom Ch. 03byalwayswantedto©
This is a continuation of a previous story in which my Mother and I started to play a game. This game allowed me great liberty, at Mother's whim, but still had firm rules, rules I dearly wanted to skirt. Please read Chapter 1 and 2. All characters are 18 or older.
Somehow, I had to get into her. She would tease me and let me play with her until she came. Last time, she got carried away and broke her unspoken rule, letting me touch her bare pussy, even put my fingers inside her. I wanted to break all the rules. I wanted to have her whenever I wanted, and I wanted her to let me take her, not trick her into it.
How could I find a way to make her want me that badly? She liked being appreciated, liked having an audience like she used to have. Playing into that had got me this far, but I sensed that I needed something more to get further. She had mentioned that Dad enjoyed displaying her in sexy dresses, and she liked to flirt with the younger executives torn between desire for her and fear of him.
I think Dad's proximity was crucial for both stimulus and safety. I don't think she'd ever cheated on Dad, but she may have been tempted. Could I set the stage to trigger such a memory to prompt her to cross the line with me? She liked to dress in sexy dresses, to dance, and to play in public. That had worked so far. Without a better plan, I'd go back and take it from there again.
I didn't give her the opportunity to slide back into her depressed routine. As soon as I saw her the next day, I reminded her of how good she had looked in her wool dresses.
"You know, Mom, you looked so good yesterday. We should go shopping and get you some new dresses."
"Oh, I have so many dresses already that I'll never wear again. Your Dad won't go anywhere now," she pined.
"You and I can go out, Mom. Anyway, I like to see you in your dresses right here at home. We could work our way through your closet, keep the ones we like, and give the rest to charity. C'mon, let's go shopping for new outfits. What do you think?"
"Well, I guess that could be fun."
"Definitely. Let's go."
"Jay, you don't want to go shopping with your old mom for house dresses."
"Not house dresses. We're looking for dresses for a good looking woman." I pulled on her hand, dragging her out of the kitchen to the bottom of the stairs.
"Come on. Go upstairs and get dressed."
I stood at the bottom of the stairs and watched her. Although she started slowly, her pace picked up and she was moving briskly by the time she reached the top.
Fifteen minutes later, she came down in a white blouse and a loose, pleated skirt, with a tentative smile on her face. "You're sure about this?"
"Absolutely. It's going to be a great day."
Once in the malls, Mom really got into it. She clearly loved to shop, and was quite particular. We looked at many, many dresses in lots of stores. As she tried them on, she would come out to show me. I took my time, admiring her body of course, and took the full license shopping gave me to run my eyes all over her. I knew she was aware that I was appreciating her figure, but she let me have my fun too. As the day went on, I was sure she was striking poses to increase my enjoyment.
She had only bought one dress when, as we were leaving, we passed by a store with slinky dresses oriented to a younger crowd. Hesitant to enter, I cajoled her until she relented and we went in. The young woman seemed to mistake our relationship as one between a younger man with a somewhat older woman, not a mother son thing. I called mom by her first name to facilitate the illusion.
"They're got some real cute little numbers here, Lorraine."
Mom gave me a funny look. "I don't think these dresses suit me, I'm too old for them."
"Nonsense," I retorted, "They're made for a body like yours," intentionally drawing attention to her figure in more graphic terms. "Aren't they?", I queried the saleswoman.
"Oh, totally, you should really try some on," she effused, turning to Mom to release her pitch.
Mom tried a few on. They were all very sexy and I was pleased with every one she tried. The saleswoman could tell I was interested in Mom, so how could she mistake her as my mother, especially the way Mom primped for me? As she modeled the dresses, I touched her often, turning her by pressing my hands against the sides of her rib cage, sliding my hands along her waist and out the swell of her hips as she moved away toward the mirror. Mom seemed to revel in it, cocking her hips as she studied herself in the mirror, turning her legs to see her behind, glancing up to watch me studying her, ruffling her dress up her sides, lifting the hem higher on her thighs, and so on.
She finally picked out two dresses to buy. As she walked them over to the counter, the saleswoman suggested she get new underwear as well. "You can't wear regular bra and panties with these dresses, they'd show," she explained, picking up a tiny bit of silk that was supposed to be panties, and a bra as well.
As we left, I suggested we look for a new pair of shoes as well.
"Ok, but then we have lunch," she said, I'm starved and I want to go home."
"When we get home, let's put on your new dress and dance while we listen to our CD," I said, trying to set up the afternoon for more games. "But first let's get something new for you to dangle on your toes."
Mom shot me a real curious look at that remark, but smiled and said, "Whatever you say, Jay".
In the shoe store, Mom kept her pleated skirt closed demurely around her knees as the salesman, a year or two younger than me, fitted the first of several pairs of open-toed shoes we'd picked out. I could tell he was looking at her legs when he thought no one would notice. How could he help it? Mom had great legs.
I decided to explore her affinity for flirting in public. Sitting next to her, I casually dropped my hand in her lap as he turned to pick up the second pair of shoes for her to try. Mom tensed but she didn't push my hand away. Leaning forward, I looked down her legs at the shoes, her feet resting in between the teenager's legs.
"I like these ones," I remarked, pulling her skirt back as I leaned forward, exposing about three inches of thigh before lifting my hand away. "What do you think?" I said to the clerk, forcing him to look up at me.
"Oh, yes, they're very nice," he replied, but he couldn't stop his eyes straying to her newly exposed thighs.
When he turned to get the third pair of shoes, I slipped my hand between her knees and gently pulled her legs apart a few inches. When he turned back, the clerk's eyes reached between her parted legs. Mom blushed, but didn't say a word. She kept her eyes on the shoes, not looking at me or the clerk.
As Mom rose to walk on the new shoes, I pointed to a pair of high boots and asked the salesman to fetch a pair of them to try. When Mom sat down, I pushed her skirt higher again, and parted her legs. She didn't acknowledge my action in any way except to turn her eyes away. The clerk returned just as I was lifting my hand away from her knee. He immediately noticed the more revealing position of her legs and kept his eyes between her thighs as he knelt down, taking her foot in his hand and feeding it into the boot.
He seemed to sense that it was OK for him to look, and look he did. As he pushed the boot up, her leg lifted from the chair seat, opening her legs even wider. From his position, he had to be able to see right up to her panties. Mom kept her eyes averted as he started to fasten the leggings. When he finished, he started with the next boot.
"Take your time," I said, "We're in no hurry. We really enjoy shopping."
I turned to Mom. "Sit back and close your eyes, Mom."
She visibly tensed as I uttered the last word. The clerk faltered, then continued pushing the boot up her leg, leading with his fingers sliding up her calf. Again, Mom's thigh lifted off the chair as he pushed the boot up. He seemed to push her leg up farther, opening her legs wider this time. As he started to fasten the leggings, much more slowly, I reached down to grasp the hem of Mom's skirt. He watched as I pulled it back to the top of her thighs, exposing her yellow panties. He never looked at me.
The poor guy was having trouble breathing and his fingers were fumbling with the snaps on the boot. I noticed that he had positioned Mom's foot so that it was resting on his thighs as he knelt before her. As he finished closing the last snap, Mom opened her eyes and turned to look directly at him. She moved her foot directly onto his crotch and gently twisted her toe on his noticeable bulge.
"Let me up, so I can try them," she said. She walked up and down the store a couple of times, then made her way straight to the counter. "I'll take these," she said, "and I'll wear them. My son can take them off when we get home. He likes to do little things like that for me."
I basked in the hero worship visible in the clerk's eyes as we left the store.
At lunch, Mom requested a booth at the rear of the restaurant and went to the ladies before joining me. She slid in, pushing me to the middle of the large U-shaped booth. As she read the large menu, she spoke quietly without turning to face me, "Aren't you going to pull my skirt up?"
Taken aback, I didn't move.
"Don't be obvious about it."
Discretely, I moved my hand down behind the menu and under the table, grasped her skirt and pulled it back, away from her knees.
"You liked that little game you were playing back there. Didn't you?"
I didn't answer.
"Are you trying to be like your father?"
I was caught. "I don't know."
"Yes you do. You want to be like your father, don't you?"
"I guess. If you say so."
"Look at my menu, like we're discussing it." I did.
"Look down." I did.
"What do you see?"
"Your open legs, your thighs."
She reached down and pulled her skirt back even more.
"Now what do you see?"
She was bare. I could see her pussy covered with just a hint of light brown hair.
"I don't know."
"Yes you do. You know what it is."
"Yours. Lorraine's pussy," I replied, thinking she wanted to continue the game I'd started in the shoe store.
"No. Not Lorraine's. Who's pussy can you see?"
"My Mom's. I'm looking at my Mom's pussy."
"That's right. Your Mom's pussy. Your Dad couldn't play games like that. You're not your Dad. You have to play your own games, Jay, and I can tell by that little number you did back there, calling me Mom while you were playing with my skirt in front of that boy, that you have a knack for it."
Just then, the waitress arrived. We ordered and had little discussion until our meal was done. Mom didn't cover herself up. She left her skirt up, her legs exposed, but the way we were seated only I could see.
After the plates were cleared away and we were finishing our coffees, Mom said, "Lean in to me and laugh like we're sharing a joke." I did as she instructed.
"Put your hand down and touch me," she whispered, "Quickly."
I pushed my left hand down between her thighs and cupped her pussy.
"Do you like that?", she asked.
"Yes," I gasped, stunned that she not only let me touch her, but told me to do it. I had thought this was against the rules.
"Well, you're not going to get into it. This is all I'll let you do, and if you expose us like that again, I won't let you do that either. Understand?"
"Maybe I'll let your little salesman friend have it. Would you like that?"
"Then keep our little games to ourselves. Let's go home now."
We left the restaurant, but as we passed by the shoe store, Mom suddenly spoke out, "Oh, I forgot to try on that cute little green pair," and she hurried into the store.
When he saw her, the salesman almost tripped trying to greet us. Mom pointed to some green shoes and sat down. She waited until he knelt in front of her with a pair her size. I sat next to her again.
"You know I like to take my time when I'm trying on shoes, don't you?", she queried our very excited sales assistant.
"That's no problem. We aim to please. Take all the time you want."
"Take my boot off slowly, then." As he started, she moved her hands to her blouse and slowly loosened two buttons until you could see the swell of her tits. "Are you good to your Mother?" she asked.
"Yes, I try to be."
"That's good. You should be. A mother will do a lot for her son, especially if he's a good boy."
He glanced at me, then back to her. Was she speaking to me, through him?
"Is your mother pretty?"
"Do you look at her when she isn't looking?"
Caught off guard by this direct query, he paused, flushing red in the face.
"You do, don't you?"
"Yes," barely audible.
"Would you like her to be like this with you?" As she said this, she dropped both hands to her sides and slowly pulled her skirt back but keeping her legs pressed tightly together. "You'd like it, wouldn't you, if she played little games like I do with Jay?"
"Yes. I would," he confessed, his voice hoarse. He slid the boot down her leg, leaving his left hand cupping her calf just below her knee, returning to hold her foot with the other after dropping the boot on the floor.
"She might, but you have to let her know you want it. If you don't take chances, you won't get what you want." She paused. "Put my foot where you want it."
A shocked look on his face, he nevertheless pulled her foot onto his crotch. "Watch the store, Jay," Mom whispered to me as she started rubbing her foot on his jeans. He was gasping, staring at her exposed but closed legs. She laughed softly. "If you want to look, you have to go for it. Nobody's going to do everything for you."
Haltingly, he leaned forward, tentatively placing his hands on her knees, then slowly spread them apart. He gasped as her bare pussy came into view. She started rubbing his cock vigorously. He responded by hunching into it.
"That's right, baby. This could be your mommy's. She'll do it if she loves you, and she's lonely. You just have to bring her around to it." She leaned forward as he started to come in his pants. "She might even let you kiss it."
He lost it, suddenly jerking wildly, fucking her foot, holding it down tightly against his cock, not caring that, if seen, he'd likely lose his job.
When he was done, Mom picked her boot up and pulled it on herself. She continued, "I don't want these shoes right now but I'd like to try on a few pairs at home. Can you do that?"
"Absolutely, no problem, absolutely," he gasped out, still recovering his breath.
"Great. Jay will give you a call when I'm ready. Would you like some advice to help you with your mother?"
"Yeah. That would be great."
"Be nice to her. Be thoughtful. Go out of your way to do extra things for her but don't mention it, she'll know. Compliment her and carefully, ... carefully ... let her know you're aware of her, as a woman. Just a few glances at first, then some lingering looks at her body, and her legs. Don't gawk. If she doesn't seem mad, start touching her. Not anywhere sexual, on her arm, give her hugs and little kisses, that sort of thing. If she gets tense and her pulse quickens but she doesn't object strongly, you're on your way. What's your mom's name, and yours?"
"My Mom's name is Dhelia, and I'm Greg."
"OK. Remember, take your time." She turned to me, "Come on Jay, let's go home, now," she said, huskily.
As we drove, she instructed me to take some sandwiches up to Dad when we got home and visit with him. She wanted to rest, and would join me downstairs later.
"I want you to contact that boy and help him if he needs it. Make sure he takes his time. If he rushes things, he may not get another chance. Anyway, he should learn to savor the good things in life."
Was she sending me a message as well?
Then she commented on how much she liked her new boots. "These boots hold a memory for us now, don't they, Jay?"
"Yes, Mom, they certainly do," I laughed.
"Always remember, if you take your time, you can make a memory. Memories last, they're worth the effort."
Mom went straight up to her room when we arrived. I dutifully made some sandwiches and took them up for Dad. While he ate, I hung around trying to talk to him but he was distracted, returning one word answers while continuing to read his book. I tried hard, for Mom's sake, but gave up after an hour and went to my own room. After a while, I changed into my PJ's and went downstairs, hoping to find Mom.
She wasn't anywhere to be seen. I poured myself a glass of wine, got comfortable on the couch, and started reading. Tiring after just a little while, I put my book down, and reached for my wine glass. There was a note written in my mother's hand leaning against the base of the lamp.
"Jay. Put on our CD when you're ready. I'll come down when I hear it. Love, Mom."
I put the CD on loud enough to be heard upstairs. Then I topped up my glass and settled in to wait for her. Twenty minutes later I had already refilled my glass but my cock hadn't subsided since reading the note. In between songs, I heard her voice, "Jay, turn the music down." Then, "And start it over."
I did as she asked. By the time I had reseated myself, she was halfway down the stairs. She was wearing the sexy blue, sleeveless dress made of a very flimsy material that almost let me see her body through the billowing fabric. My eyes were drawn to the boots that almost reached her knees. The black leather accentuated the supple strength of her thighs above, pulling my attention to the valley at the juncture of her legs. As my eyes traveled up her torso, I noticed her unrestrained breasts jostling as she walked slowly toward me. She stopped in front of me.
"I want to dance." I rose to take her in my arms.
"Give me a sip of your wine first, and don't spill it on my new dress." I tipped the glass to her lips, pulling back a little for her first swallow, then tipped it again. When she signaled me to back off again, I tipped it further into her instead. She tilted her head back and gulped the whole glass down. As I pulled the glass away from her lips she swirled her tongue around her lips. She pressed her hips forward against my cock until it was firmly lodged in her belly, "Been waiting long?" She laughed throatily, and raised her arms around my neck.
I tossed the glass onto the couch and steered her out into the room in a slow dance, shoving my prick into her as I worked her backward, pulling her waist in against me. I stopped and kissed her, forcing my tongue into her, exploring her mouth. I hunched my cock against her, rubbing it up and down against the mound I could feel between the thin material of her dress and my PJ's.
"Oh, you naughty boy," she exclaimed, breathlessly, when the kiss ended. But the glint in her eye wasn't an angry one. I tried to renew our kiss but she bent further backward to avoid my lips, pushing her belly harder against my stiff cock. "I'm going to have to put my foot down with you, young man," she admonished.
"Go ahead, Mom, put your foot on me," I countered, still trying to kiss her as she swayed to avoid me.
"Is that what you want, Jay? You want to walk a mile in the shoe salesman's shoes?", she laughed again. "Alright, I can't dance in these boots anyway. Pour me some more wine and take these boots off for me.
She pushed my arms away, walked past me and sat down on the couch. I grabbed some more wine and refilled the glass I had tossed on the couch. Then I positioned myself on my knees in front of her, lifting a booted leg, and starting undoing the snaps.