Chapter 3

After dinner, I showered and changed into shorts and a tank top to study. When Mom didn’t show up at her usual time, I worried that the previous night’s events had affected her more than she admitted. Just as the thought lingered, I heard a light knock at my door.

“Come on in, Mom. I’m already studying,” I called, relieved by the familiar sound of her entering.

She walked to her chair and relief swept through me, seeing her cloaked in her negligee. Everything had returned to normal as I continued with my studies. After thirty minutes, she fidgeted in her seat before bringing her legs onto the cushion and folding them to the side. Her hemline slid upward, revealing a good portion of her upper legs.

While I frequently ogled her legs, her gaze centered on the bulge in my shorts. “Was she recalling the sight of my cock from the previous night?” I asked myself.

Finishing my work, I stretched and suggested, “Why don’t we finish the night watching some TV? I’ll put on my robe and meet you downstairs.”

“No need for that,” Mom replied. “It’s getting warmer and the robes are just too heavy.”

Rising off her chair, she headed to the living room, with me following close behind, my eyes glued onto the backs of her legs.

After watching a couple of sitcoms, Mom hugged me goodnight and we adjourned for the night. My prick, already hard from Mom’s teasing, greeted Mia when she called. “Looks like you started already,” she giggled, looking at her laptop. I glanced at mine, displaying her fingers running up and down her pussy lips. Before I could tell her about my conversation with Mom, she stated, “Let’s cum first, baby—talk later.”

“Fine by me,” I replied, stroking my painfully hard cock. We had phone sex down to a science and it wasn’t long before both of us neared our orgasms. Between gasps, Mia murmured, “I made something for us, baby. Watch your laptop.”

She had compiled clips from her phone and laptop into a video. It rotated from closeups of her tits to her pussy in the throes of an orgasm, ending with a scene of my prick exploding. It repeated, using shots from different nights. My prick was ready to spurt, when Mia said, “Last one, baby. Stay focused on the screen.”

When it came to the final scene, it was from the previous night. I watched the video as Mom opened my door and peeked in, before stepping inside. After staring at me for a minute, she clasped her arms around her. When my prick erupted on the screen my orgasm hit me in real time. I groaned, depositing my load of cum onto my stomach. The video ended when Mom left after my outburst, switching back to Mia’s pussy jerking and spewing out her juices.

My focus switched to Mia’s beautiful face, filled with joy from her climax.

“I smoothed it over with Mom this morning,” I said, adding, “even saving you from a tongue lashing, shifting the blame to me.”

“I heard,” she acknowledged.

“Why exactly did you arrange it to happen in the first place?” I asked.

“You don’t know, do you?” she asked, her playful expression lighting up with mischievous joy. “After all I’ve gone through, you still haven’t a clue. Sometimes, you’re so naive, little brother, but it’s endearing in a way.”

“My understanding is that we were supposed to prepare her for dating again. Am I mistaken?” I asked, my curiosity growing.

Mia’s eyes sparkled with mischief, a knowing smile curving her lips. “That’s part of it, sure. But don’t you think there’s more to this whole thing than just playing matchmaker?” she teased, leaning closer, her expression a mix of amusement and mystery.

I furrowed my brows, trying to piece together her cryptic response. “What are you getting at, Mia? What haven’t I figured out yet?”

She sighed, a playful exasperation in her tone. “I want you to fuck Mom, silly.”

“Wait. What? Are you nuts?” I asked, not entirely shocked, but putting on an act nonetheless.

She giggled and explained, “She needs a hard cock and you need a pussy wrapped around your big prick—simple as that. I love both of you and want to make both of your dreams come true.”

“Our dreams? I don’t think Mom really wants to make love to me and I haven’t had any thoughts of being with her,” I stuttered, feebly trying to refute her assertions.

She laughed and countered, “First thing, all boys want to fuck their mothers. Who did you whack off to when growing up? Be truthful—you’re talking to your future wife.”

I blushed, confirming her suspicions. “I guess I might have, but that’s pretty normal for all horny boys.”

“Your connection to her is very strong,” she continued. “The way you gawked at her legs and that kiss at her birthday was more than pretending. Both of you revealed your deepest desires during that brief moment. Don’t get me wrong—I’m not mad or jealous. I think it’s wonderful you love her as much as you do me and I want you to show her how much, by driving your big cock into her horny pussy.”

Her arguments hit home and it was time to admit my true feelings. “I can’t deny the thought hasn’t crossed my mind,” I confessed. “I’m not sure if it’s because I love her so much because she’s my mother or if it’s from her sexy body. You and her have a lot in common—both of you keep my cock hard most of the time.”

“I know, baby. I want to help you fulfill your fantasy—and mine,” she assured me. “I have a knack for convincing Mom to expand her boundaries, so we’ll have you between our mother’s legs in no time.”

“I don’t know,” I replied, questioning her assumption. “Talking a mother into role-playing for dating is far different from convincing her to make love to her son. I don’t think she’ll cross that line.”

“Are you kidding me?” she asked, rhetorically. “She’s jumped at every chance to be closer to you. Did you see her at the end of the video, when she stuck her head in your room and saw you masturbating? She could have left quietly, but she didn’t. She stepped inside and froze, her eyes locked onto your magnificent cock—her son’s. Did you notice the way she gripped herself with her arms? From experience, I know her nipples ached to be touched and she was trying to quell her urge to run over and gobble up your cock.”

“She did stand there for a long time without saying anything,” I agreed. “And earlier, she suggested we remain in our skimpy clothes for our couch time. You’ve excelled at bringing her out of her shell lately. What’s next?”

She smiled, knowing I was on board, and answered, “When Mom and I talked today, she asked me whether you’ve been seeing Denise again. I think she recognized your cock from the glory hole. If that’s the case, curiosity will gnaw at her until she confirms it. We’ll work on that angle. Meanwhile, I’ll guide her along. You just have to seize any opportunity that opens up and not be afraid of alienating her. At this point, she won’t allow anything to interfere with your relationship with her.”

After a lengthy discussion of freely discussing our innermost feelings, we signed off and went to bed.

On Friday, I arrived home to find several boxes from DHL on the front doorstep. They were overnight packages from Mia, addressed to Mom. I hauled them into her room before going to mine to change into my sweats.

Mom entered shortly after, greeting me, “Hi Steve. I’ll change and start dinner. If you can help, we can speed things up. I’m thinking of a nice dessert for our time on the couch tonight.”

“No problem, Mom. By the way, some packages were delivered today. I stowed them in your room,” I said.

She smiled and replied, “Oh good. Mia said she was sending more clothes for me. She’s spoiling me rotten.”

She didn’t mention what kind of outfits Mia had sent while we ate and afterward, lounging on the couch. I didn’t ask, not wanting to thwart any plans Mia had.

The next day, after our chores, we showered and dressed in preparation to dine out. When I joined Mom in the living room, my jaw dropped, laying eyes on her sexily dressed body. My eyes traveled up her long legs, mostly displayed due to her short, pleated dark blue skirt. A stylish, wide leather belt wrapped around her waist. Her light-blue, crop top was open at the bottom, leaving several inches of exposed stomach along with her belly button. The material was thick, but the outline of her nipples distinctly pressed against the fabric confirmed she wasn’t wearing a bra. Mia had outdone herself.

When my gaze met hers, she blushed from my leering stare. Extending her arm, she softly asked, “Shall we go, Steve?”

“You look lovely tonight, Lydia. I’d be honored to be your date, “I replied as her smile widened, seamlessly slipping into our familiar dating role-play.

Assisting her out of the car at the restaurant rewarded me with a glimpse of her blue panties when she swung her long legs out, her slick skirt sliding up her smooth legs.

It was a delightful meal with our relationship more at ease. Thoughts of cheating on Mia had all but vanished, as I flirted with Mom. She reciprocated with signs of affection, more than a mother would normally do with a son.

When we were about to enter the car, Mom turned to me and held my waist. I did the same, my hands gripping her bare flesh. “Thanks for the evening, Steve,” she murmured, her face inches away from mine, her lips beckoning me.

I kissed her and when I ran my tongue along her lips, she pulled back. A mischievous grin danced across her face before she faked a mock-serious expression and declared, “It’s not my birthday, young man.” Her giggles followed as I assisted her into the car.

“At least she didn’t slap me,” I thought to myself on the ride home. Once we entered the house, instead of retreating to her room, she turned to me again as before and held my waist.

My hands instinctively clasped her sides, my eyes locking onto hers. “It’s much more relaxing when we’re at home, don’t you think?” she asked, her voice laced with lust.

“Was that a hint, referring to her birthday dinner when she stated she preferred displaying her affection in a private setting,” I thought to myself, unsure of how to proceed.

Her eyes glistened with the same fiery lust as when we kissed that night. Before I could answer, she leaned closer and silently murmured, “It’s someone’s birthday tonight.”

If that wasn’t enough of a clue to her desires, her hands pulling me closer left no doubt in my mind. Once our lips connected, she opened her mouth, her tongue finding mine. While we French kissed, her eyes widened and her hands tightened on my sides. I slowly slid my hands up her stomach underneath her top, my heart racing as my fingers explored her hot flesh.

Recalling Mia’s advice to seize every opportunity, my hands ventured upward until the side of my fingers and thumb bumped against the soft, spongy underside of Mom’s breasts. Her eyes twinkled as our kissing grew more intense. Just as I was about to cup her bare breasts, Mom’s hands released my waist, grasped my arms, and pulled me away from her matronly mounds.

Her lips parted, her warm, rapid breaths washing across my face. “How about we change and snuggle on the couch before calling it a night?” she suggested, her voice tinged with a subtle sensuality.

“I’ll brew us a couple of cups of tea to enjoy, too,” I offered, earning a wide, approving smile as she turned and headed to her room.

The intimate tone of our dinner date faded, leaving the rest of the evening to pass without interaction.

Sunday night with Mia, our orgasms arrived quickly as I related my dinner date with Mom. The rest of the time we spent talking and before we signed off, she asked, “So, are you enjoying drooling over Mom in her nightie?”

“It’s pretty nice, but you could have at least bought her a see-through one,” I suggested, nervously giggling.

“I did, but I don’t want to convince her to wear it. Let her set the pace. Love you, baby,” she replied before ending the call.

The next Wednesday, I had just begun studying when Mom knocked and entered. I did a double-take at her sexy attire—a light blue, see-through, baby-doll nightie. My eyes soaked in her scantily-clad body ending on her smiling face. She smiled at my approving glare and asked, “I hope you don’t mind. Mia bought this for me and I’ve been dying to wear it. Is it too skimpy to wear around you?”

“Not at all, Mom. It’s a really nice piece of lingerie. Your pink undies are a nice match for your blushing face,” I replied, my grin turning to a wide smile.

“Watch it, young man. I’m still your mother,” she said, jokingly, nervously fidgeting while I stared at her body.

“Could have fooled me,” I said. “You look more like a sexy lingerie model, rather than a mother.”

She settled into her chair and replied, “Even though it’s a little inappropriate to think of your mother like that, thanks.” Her grin widened, seeing her son admire her sexy curves.

“Like I said—not a big deal. Mia used to wear a similar one when she visited me,” I lied, knowing Mia wore nothing under her robe.

“She what?” Mom gasped, her eyes widening in surprise as she processed the unexpected news about her daughter. “Don’t tell me she pranced in here wearing nighties every night. I would’ve noticed that.”

“For that reason, she wore a robe and removed it when she relaxed in here. It made her feel comfortable so I didn’t mind,” I explained.

“I’ll bet you didn’t,” Mom shot back. Her serious, motherly tone shifted to a more relaxed one after I turned my focus on my homework.

That night, while discussing the day’s events with Mia, I deliberately avoided mentioning Mom’s new outfit. Still, I couldn’t help but wish I could be a fly on the wall during their conversation the next day.

The next night, Mom entered my room wearing the same nightie, but with black undies. The evening flew by and by the time I stripped and waited for Mia, my heart raced, expecting the worst. As anticipated, my call with Mia started off tense. She attempted to appear upset, but her expression betrayed her amusement—I knew she was enjoying our little game.

“Bro, you have to give me a little heads-up about what you say to Mom. She says you told her I wore see-through nighties when I helped you study. Seriously?” she asked, her scornful expression turning to a grin.

“Better than telling her that you were nude most of the time, isn’t it?” I replied, causing her to giggle even harder.

“Fortunately, I ran with it and made some lame excuse,” she related. “It was touch and go for a bit, but she finally relented, especially since she’s wearing one now.”

“Okay, I promise to give you a hint from now on, but not much more. You do remember all the times you didn’t warn me with your little plots on bringing Mom and me closer, don’t you?” I asked.

“Fair enough. Love you,” she said, smiling widely, ending the call on a high note.

With exams the following week, I decided to study on Friday night to better prepare myself. Mom showed up as usual, back to wearing her pink undies, most likely another pair, since she waited until Saturdays to do laundry. She would often massage my neck and that night was no different. Her fingers felt good as they worked my shoulders and out of the blue she asked, “If I may ask, what color undies did Mia wear?”

This was an opening I had hoped would come up. Pausing for a few seconds, I replied, “Flesh-toned, with an accent of pink dots.”

Her fingers continued to caress me as she remarked, “Seems a little boring for a young woman. I’ve rarely seen her wear a bra.”

I paused, letting my answer sink in, before adding, “Mom, think about it. Flesh-toned, as in skin.”

Her hands squeezed my shoulders as her fingers dug into my soft tissue. “Braless? Your sister paraded in here without a bra? I can’t believe what’s been going on in my own house.”

“Relax, Mom. It’s not like I haven’t seen braless girls before. It’s quite common nowadays,” I argued, trying to calm her down.

“Maybe so, but it still seems inappropriate. She’s not just some other girl—she’s your sister,” Mom stated.

“She probably wouldn’t have done it under normal circumstances, but it was the result of a silly dare we came up with one night when we were bored with homework,” I explained.

Her brow creased in curiosity as she asked, “What kind of dare are we talking about?”

“It was really hot in here one evening and when she noticed me sweating, she suggested I take off my top,” I began, hesitating briefly before continuing, “That’s when the dare happened. I told her I would if she’d do the same. Naturally, she just blushed and dropped the idea, so I kind of forgot about it. The next night was even hotter and when she was late, I thought she wasn’t going to show so I shucked off my top. When she came in, her face turned white and falsely assuming I had thrown the dare out, she turned around and removed her bra.”

“She’s always hated losing a dare, so I guess that makes sense,” she said, her curiosity evident. “But did she stick with it afterward?”

“Since I hardly noticed, she stopped bothering with it altogether,” I explained casually. “Honestly, I think she’s just more comfortable that way. Plus, it made it easier for her to massage my shoulders without my shirt in the way, so I didn’t have any reason to object.”

She pulled her hands back from my shoulders, walked over to her chair, and eased into it, tucking her legs beneath her. “You’re right. I probably overreacted,” she admitted with a sigh. “Sometimes, I feel like such a dinosaur. What kind of man would ever want to go out with someone as old-fashioned as me?”

“Any man who values a mature, beautiful, and intelligent woman—that’s who, Mom,” I countered firmly. “Stop putting yourself down all the time—you’re a catch.” She blushed deeply, said nothing, and quietly returned her focus to her book.

Later that night, during my conversation with Mia, I asked, “Did you mention to Mom what to wear for our dinner tomorrow night?”

“No,” she replied curtly. “I don’t want to influence her anymore. She needs to start making her own smart decisions.”

Grinning, I said, “By the way, you’ve been a naughty girl, parading around your brother in a skimpy nightie with no bra.”

Her brows rose as she processed my comment. “What did you do now?”

“Not me, you. I think it has something to do with not being able to lose a bet. That’s all I’m saying.”

She sighed, bid me goodnight, and ended the call.

Mom surprised me by wearing her floral sundress for our dinner date the next day. Maybe she noticed the joy it brought to my face whenever she wore it. My smile widened when she suggested we dine at the restaurant by the river. After a delightful meal, we strolled along the boardwalk, just as we had in the past. At the end of the pier, she held me close, slowly drawing me into her embrace. Moonlight danced on her face, accentuating her beauty. I was utterly captivated by her natural elegance.

Her eyes glistened and filled with lust, bringing back memories of when we kissed before. In a low, sultry voice, she asked, “You have a birthday coming up, don’t you?”

“You know I do, Mom. In a couple of months,” I replied.

“Lydia,” she emphasized.

Her intention became crystal clear and my heart couldn’t have been beating faster. “Yes, Lydia. I may have misspoke before. I believe it’s today.”

“Happy birthday,” she murmured, leaning toward me to kiss me. Her arms rose and held my head steady as her mouth opened and searched mine with her tongue. Once again, I couldn’t believe I was French kissing my beautiful mother. I pulled her into me, pushing her breasts into my chest. They heaved as she inhaled deeply through her nose.

My hands ached to cup and squeeze her breasts again, but I feared of breaking the mood and ending the magical moment. After ten minutes of necking with my sexy mother, she stepped back and purred, “I guess I’ll have to revise my rule for showing affection privately. Would you mind escorting me home, Steve?”

“My pleasure, Lydia,” I replied.

Unfortunately, we didn’t repeat the kissing episode once we made it home as we had previously, but it turned out to be an enjoyable evening, nonetheless.

Sunday night, I bore down on my studies, when a thought crossed my mind. Before Mom entered, I shucked off my shirt, tossing it onto my bed. When she saw me, she asked, “Is this some sort of dare, like you and sister did?”

No, Mom,” I replied. “I know you don’t like to participate in that sort of thing. I’m just worried about my first exam tomorrow, and I guess all the nervous energy is making me feel overheated.”

Her face softened with regret, as though she felt guilty for her accusation. Moving behind me, she gently caressed my shoulders for a few moments before saying, “You’re right about the shirt being in the way. It’s much easier to massage your muscles now.”

“Thanks, Mom,” I said with a grateful smile. “I’ve printed some study sheets. Would you mind reading the questions to me and checking my answers?”

“Of course!” she replied enthusiastically. Taking the questionnaire, she settled into her chair and began quizzing me. She loved helping me study and had a knack for jumping between questions to keep me on my toes. Before we realized it, several hours had flown by, and it was time to call it a night.

After she left, I prepared myself for Mia’s call. A wide smile lit up her face as soon as the video connected, and the first thing she brought up was her conversation with Mom, concerning her going braless in front of her brother.

“She was actually very supportive and didn’t make a big deal out of it,” she said, her tone filled with relief and gratitude. “She did ask me what it felt like with my nipples rubbing against the silky fabric and whether they stiffened while I sat in your room.”

“Did you explain to her that when your nipples hardened, I was there to suck on them and make them all better?” I asked, both of us giggling at my frankness.

“No, but I did confide in her that it felt a little exciting and naughty at the same time,” she explained. “If I could put money on it, I’d bet that you’ll soon be seeing Mom without a bra.”

We chatted for another ten minutes before signing off.

I breezed through my set of exams on Monday, feeling confident about the results.

Over dinner, Mom was genuinely thrilled to hear about my success. Afterward, she took care of cleaning up while I headed to my room to prepare for the next day’s exam. Focused on the screen, I didn’t glance up when Mom entered the room. She gently caressed my neck for several minutes, offering a comforting presence, before I handed her another set of study sheets.

She took them without hesitation, settled into her chair, and immediately began reading off the first question.

When I looked up to answer, my eyes locked onto her large, brown nipples pressing against the silky, thin material. I chuckled to myself, knowing Mia would be gloating over her correct prediction. While she read off the questions, my eyes remained on her nipples.

Mom’s sexy smile greeted me when she looked up for my answer to her question. It wasn’t long before she stole glances at the growing bulge in my shorts. She crossed her legs to become more comfortable and continued reading from the sheet while her nipples puffed out due to my constant staring. Once again, we worked until it was time to retire.

Remembering Mom’s kiss from the weekend and her willingness to dress so sexily around me boosted my confidence, inspiring a plan. Before my call with my sister ended, I informed her of a change. “Mia, these exams are really exhausting. If you don’t mind, could we postpone our calls until they’re finished?”

“Perfectly understandable, Bro,” she agreed with a supportive smile.

“One last thing. Mom’s not wearing a bra anymore under her nightie,” I informed her with a grin.

“I knew it!” she exclaimed. “How do you get any studying done? With her sexy body on display, I’m sure your prick is hard most of the night.”

“Much of it, yeah,” I admitted. “Focusing on my studies helps though. I’ll keep you updated with texts every day. Love you.”

While falling asleep, a grin formed on my face, thinking of how my new plan would play out.

At breakfast the next morning, I put on my best act of looking exhausted, punctuating it with frequent yawns and stretches. Mom quickly noticed and asked, “Steve, didn’t you sleep well last night?”

“Not really,” I replied with a sigh. “Today’s exams have me really worried. I tossed and turned most of the night, barely getting any sleep.”

“I’m sorry to hear that,” Mom said sympathetically, even though it wasn’t her fault. “Hopefully, all your preparation will pay off. Good luck, dear.” She gave me a quick peck on the cheek before I headed off to school.

Tuesday evening, while Mom helped me study, I maintained my act of being tired.

Concerned, she asked, “How did your tests go today? You’re looking so worn out. I’m starting to worry about your well-being. Is there anything I can do to help you sleep better?”

“I’m not sure,” I replied, rubbing my eyes. “But I struggled to stay alert all day. In the past, Mia suggested something to help me sleep, and when we tried it, it actually worked,” I admitted, hesitating. “But I don’t think it’d work with you.”

“What is it?” Mom asked, her expression curious and intrigued. “I can’t imagine I wouldn’t be able to take her place.”

Holding her attention, I paused for effect before saying, “She slept with me.”

“What!” she exclaimed, her shocked expression revealing her surprise.

“Good grief, Mom!” I retorted, rolling my eyes. “Get your mind out of the gutter. It’s nothing like what you’re thinking. She remained dressed and just rested beside me. Honestly, just having someone near me, with her arm resting on my shoulder, was usually enough to put me out. Do you remember the day Mia left, and I fell asleep on the couch with you? You draped your arm across me, and it was so comforting that I woke up feeling completely refreshed.”

“I do remember that,” she said with a gentle smile. “If I recall, there were many times in the past when I’d help you rest by holding you close. Mothers are experts at nurturing their babies, and I suppose that instinct never really goes away. But I think we’ll need to find another way.”

“I understand, Mom,” I replied, nodding. “Like I said, I didn’t think it’d work with you. Let’s forget about it and focus on preparing for tomorrow’s exams.” I shifted the conversation, steering us back to the task at hand.

For the rest of the evening, her expression revealed her lingering concern for my well-being, my explanation about my sleeping arrangement with my sister clearly weighing on her mind.

After she retreated to her room, I tidied up, changed into a pair of underwear, and crawled into bed. Lying awake, I stared at the ceiling, waiting and hoping Mom might relent and come to my rescue.

After twenty minutes, a light tapping on the door jolted me out of my semi-sleep state. “I’m decent. Come in, Mom.”

She peeked inside, her gaze softening when she saw me awake. “Having trouble falling asleep?” she asked quietly.

“A little, yeah. Did you need something?”

“I felt bad about selfishly rejecting the idea of helping you,” she admitted softly. “I don’t think it would hurt to give it a try. Would you mind?”

“Not at all, Mom. At this point, I’ll try anything, or else I’m going to be sleeping through my exams,” I replied, my voice tinged with frustration.

She moved closer, my night light illuminating her nightie-clad body. When she leaned over to crawl under the sheets, her breasts dangled beneath her, swaying back and forth. While I remained flat on my back, she lay on her side and draped her arm across my bare chest.

“Thanks, Mom. I feel better already,” I admitted.

“Let Mommy take care of my baby. I’ll remain here until you’re asleep,” she assured me.

Other than my prick remaining hard, my body relaxed completely with Mom’s touch. Maybe fifteen minutes later, I began drifting off, my breathing slow and deep. Her hand began moving, exploring my body, running her fingers through my chest hair. She softly whispered, “Are you awake, baby?”

I ignored her, continuing to breathe deeply. After another minute, her hand rubbed my torso in a circular motion, caressing my body. She scooted closer until her breasts pressed against my side, her thinly covered nipples poking into my flesh. Her arm wrapped around me as she nestled her head into my neck, her natural scent enveloping me. It was so comforting that I soon fell asleep, not waking up until my alarm rang out.

Although Mom had left during the night, I smiled, knowing my plan was a complete success. Before joining Mom for breakfast, I texted Mia, “You’ve been naughty again, sleeping with your brother.”

I laughed to myself on my way to assist Mom. After planting a kiss on her neck, I greeted her, “Good morning, Mom. Thanks for helping me last night. I feel great this morning.” I moved to the other counter to do my part in preparing our breakfast.