A Lonely Mom, an Experimental Son

"Ye--yes, honey. That was just...very, unexpected." She took her hand from my arm, but otherwise she didn't pull away.

"Are we cool?" I asked.

"Uh, why yes, of course," my mom replied.

"Haha, well good. I mean, this is a date after all, and good practice for me--both of us, really--right, mom?" I smiled at her, and I could see her blush.

"Yes, I suppose so. I don't know what to say, son. I'm really enjoying myself."

"Good, because I am too, mom." She softly grinned, and finished the last sip of her wine. We both sat there in silence, staring at each other--and I not so subtly eyeing over her bust and hips.

"So, mom, I'm going to go get another bottle of wine. You wanna come with me, or stay here?"

"Oh, I'll join you, dear. I don't know how much more I can have, but I love your company." I gave her my arm, and my mom stood up, both of us pulling one another to the kitchen and giggling softly. Mom instantly eyed a good white wine, "ooh, get that one sweetheart," and I took it down. I uncorked it in front of my mom, and as I did so, she steadied herself by holding onto my waist. With a satisfying "pop," I opened the bottle, and both my mom and I looked happily at the fizzing foam.

"I think a toast is in order?" I asked musingly to my mom.

"What kind of toast, honey? What do you have in mind?"

"To trying new things, to moms, and to first dates!" I declared. I raised the bottle to my mom, making her smile.

"Mmhmm," my mom agreed.

"Cheers." I took a swig straight from the wine bottle, and offered my mom some. She held it up as I helped the bottle to her mouth, and she took a sloppy sip, getting some of the wine onto her chest.

"Sorry about that!" I said happily.

"It's okay, sweetheart. I don't mind a little bit of a challenge."

"Yeah, I'm sure you do. Oh! And here's to amazing first dates with amazing people." With that second toast, I bent down to my mom, and kissed her deeply on the cheek. She closed her eyes, and I could tell she was very excited.

I pulled back, and we both laughed. My mom had a big, goofy grin on her face.

"So, am I a good date, mom?" I asked.

"You're an excellent date, sweetheart. I love you, and I think you've done well."

"Well, I'm glad you like me, mom." I moved closer to her, my frame towering over such a tender and small woman.

In a spur of the moment, I asked, "can I see that really lovely necklace, mom?"

"Oh, this?" my mom replied, pulling at the pearl chain around her neck.

"Yes, mom. Please, let me take a closer look. "Can I touch it?" I asked, and she nodded, smiling at me.

"Of course, honey."

I moved in close to my mom I reached out, and I gently touched her necklace.

"I love the way you wear it, mom. It really compliments your eyes."

"Oh, thank you, son. I appreciate that. I know it looks good on me, but I never thought of it in those terms before."

As my mom talked, I carefully felt and tugged at her necklace, bending my mom ever so slightly closer to me. As I did so, I lightly caressed the top of her breasts, which were at once held snug inside her dress, and exposed from its low cut. I could feel the fabric of her bra underneath her blouse, and I was tempted to pull her shirt up and expose her chest to me, but I resisted. I wanted to be gentle.

"Oh, son, I'm sorry, I didn't mean to make you uncomfortable. I'm just not used to having a man hold me." She started to back away, but I pressed my hand against the small of her back, holding her still.

"You have nothing to be sorry for, mom. After all, you're my date tonight! Aren't we support to support each other?" I smiled, and my mom giggled.

"Yeah, and I'm grateful, sweetheart. I love that. I always have. I don't think I'd ever been so comfortable with a man in a long time. I hope you can see why I'm so nervous right now, though," she said.

"I think I do, mom. I love you, and I love you in that dress."

"I love you too, honey. I love you in everything. I'm so glad you're here, honey. I'm glad I'm not alone."

"Me too, mom. Me too." I took her by the shoulders and leaned down to hug her. We stood there, still, embracing, in silence. I slowly pulled away from my mom, and I looked her straight in the eyes.

"So, mom, what do you think about me? What's my type, mom?" I asked, and she grinned.

"Well, I'm going to say you are very much the mother's boy. You seem to be a sweet, caring, and thoughtful young man. I'm sure you'll find a wonderful woman to spend the rest of your life with."

"Haha, you know, I think you may be onto something. I've had a crush on my mom since I was a kid."

"Oh honey..."

"Don't think anything of it! It's just nice to spend some extra time with you, mom, that's all I'm saying. I'm really enjoying this date."

"Well, I'm glad, sweetheart. I'm glad you're enjoying yourself. I'm glad I'm not a burden to you."

"Oh, you'd never be, mom."

"You know, I've had a few drinks, and I'm feeling a little more relaxed, honey. I'm thinking maybe we should move somewhere more comfortable."

"The couch?"

"That sounds perfect."

"Sure thing, mom, let me help you there."

I held my mom onto my arm and walked her from the kitchen into the living room. As we moved near the couch, I sat her down on the leftmost side, taking up the right for myself. I then moved to the center of the sofa, and I helped her take off her shoes.

"What a gentleman," she mumbled sweetly.

"No, mom, you're a great lady, and I'm honored to have you as my date."

"Oh, you're so good to me, honey. I'm so lucky to have you."

"So, mom, after you've been wined and dined on your dates, what do you like to do with the guy next?" I asked, feigning a joking manner. In truth, I was curious what would happen next on this "date."

"Well, there are some things I wouldn't mind trying..."

"Mmhmm, like what?" I suggested.

"Like, kissing, hugging, and cuddling."

"And then? What happens if I get a little frisky, mom?"

"I'm not sure, honey. You seem to be pretty confident." Mom grinned at me, making my heart beat a little faster.

I leaned over, and kissed her softly on the lips. It felt warm and tender, but also naughty--taboo. My mom responded by kissing back, and I could feel her body moving against mine ever so slightly.

I caressed my mother's cheek with my hand as I slowly pulled away from our kiss.

"Is that the kind of stuff you had in mind, mom?" I asked, smiling.

"You--you're very bold, sweetheart, but I'm not sure--" Before doubt could cloud my mom's mind any further, I leaned over to my mom and kissed her on the lips again, this time with slightly added pressure. I grabbed her left hand in mind, and she squeezed it willingly, my other hand caressing her shoulder. Then I let go of my kiss, but held onto her.

"Don't think about it mom, this is practice, remember?" I said quietly. "Let me, and we'll both learn how much fun this can be. I want to give you a date you can remember."

My mother smiled at me, her eyes fluttering, and I could tell she was struggling internally.

"I'm not sure," my mom mumbled.

"It's okay, honey. Don't be afraid. Let's just enjoy the evening, mom," I said, staring at her chest and necklace. "You look so good tonight."

"You think so? Thank you, honey. You really like my dress?" my mom asked.

"Oh I love it mom, you look stunning. So attractive!" I began to rub my mom's leg with one hand, and I rubbed her shoulder with another. She began to squirm a bit, but I held her firm.

"So, mom, after the kissing and cuddling, if the date's still going well, what do you want to happen next?" My mom looked increasingly nervous.

"Oh, honey, I'm not sure, this is getting a little..."

I leaned down, and whispered to her, "shhhh, focus on the moment, mom." I began to play with her pearl necklace.

"Honey, son, what are you doing?"

"You're so beautiful tonight mom. I want to be the best date you've ever had. You deserve nothing less." With that, I tightly wound my left arm under my mom's chest with my right hand moving to her shoulder and partly grabbing onto her neck, holding her still. I then started kissing the left side of my mom's neck, giving her gentle pecks as I squeezed her.

"Are you alright?" I asked.

"This is wrong..." she groaned.

"Oh, mom, it's so right. So answer my question, after you're done messing around with a good date, what do you want to happen next?" I slowed my kisses and made them firmer, taking in my mom's scent as I did so.

Mom started to answer, but stopped herself. She gulped hard, and turned her head away from me for a moment.

"I'm sorry, honey. I really love you too much to think about sex with you. This isn't going to happen," mom answered. She struggled to break free from me, but I swung my left leg on top her waist, keeping her fixed on the couch. As I did so, I also grabbed both hands softly yet firmly onto her neck, showing her I meant business.

"Don't be shy mom, how do you like your good dates to end?" I stopped kissing my mom's neck, and I looked her in the eyes, momentarily glancing at her chest. My mom seemed partially repulsed, yet she didn't show absolute fear, and she didn't try with full effort to push me off, or raise her voice. A part of her looked desperate--for this to end, to make me happy, or perhaps both?

"Something--something we shouldn't do honey," my mom mumbled. She wiggled her hand towards my lower body, bot stopped and gave a gasp as her hand fumbled into my crotch, briefly feeling my hard erection.

"Oh my God," she whispered. I stopped grasping her, and went back to sitting next to her with my arm over her shoulder. I pressed my other hand to her stomach this time, rubbing it gently.

"Oh, I'm sorry mom, is something wrong?" I asked cheekily, I moved my crotch closer in her direction ever so slightly.

"I-it's okay. I should go," my mom said, her face turning red, and she started to stand up. I stood with her, and in an instant, I put my hands along her cheeks, and I gave her a deep, long, passionate kiss. She slowly put her hands to mine, at first trying to force them down, but then she held them there, her lips yielding ever so slightly to mine.

As our tongues met, I ran my left hand down her neck and grabbed her pearls. My mom gave a soft moan as my right fingers worked into her hair.

"Let's go ahead and give you the full girlfriend experience tonight," I said, pulling my arms down her sides and onto her hips, before moving my head in to kiss my mom again.

Mom moaned softly, and in the midst of our lip lock, her hands went back to grasp mine.

I kept kissing my mom as I moved both my hands from her hips to her back. I gripped tightly, and I pulled her towards me. When she was almost fully pressed against me, I leaned forward and my mom's breasts were nestled between us, I could feel them through our clothing.

My mom opened her eyes, and she gave a soft gasp as I took in her beauty. She had her eyes closed, and I brought my face closer to hers. As we kissed, I started to run my tongue across my mom's lips.

"Oooooh," mom sighed as my tongue reached her.

"Mmmmmm..." I moaned as I began to suck on my mom's neck again. Mom's chest fell against mine, and I felt her breasts press back into my body.

"Oh my God, honey, what are you doing?" my mom groaned.

I backed off, and I stood up, taking my mom by the hand. "Giving you what you need," I said. At that, I took my mom shoulders and push her back down to the couch, resuming our cuddling position.

"So, mom, let's play some truth or dare." She looked uneasy. "I'll go first, for a truth--how many guys have you slept with in your life?" My mom stopped squirming and her face reddened.

"S-seven, no eight," she stammered, trying not to look me in the eyes.

"Wow, you've really gotten around," I mused, smiling at her. "I love a woman who's confident about loving cock. Alright mom, you go." She gulped slightly at my comments, and I squeezed her arm tighter.

Mom took a deep breath before answering, "Okay, your turn to pick something. Truth, dare, or switch?"

"Mmmm, let's go with, dare." I smiled at her as I thought over my options. I leaned in close and kissed my mom softly on the lips. She didn't resist, but she remained still. Her hands rested on mine, but she did not hold them tightly.

"Alright, here goes," I whispered to her, and I gave her another quick kiss. "How do you like men to have sex with you?"

"Oh, no!" Mom exclaimed, breaking away from me.

"Aw, that was almost too easy, mom," I said as I pulled her back with both arms. "So come on, answer the question."

"Ummmm..." she moaned, looking up at me nervously. She bit her lip, her cheeks were bright red, and she seemed to be writhing under my touch.

I smiled at my mom and then lowered my face towards hers. As I did, I lifted her hair off of her neck, and then I began kissing her again. "Do you like to have sex, mom? Do you miss sex? I'm only asking." My mom groaned again, whether out of pleasure, despair, or both.

"Please, honey, no more, please stop! I shouldn't do this!" she begged.

"Just tell me the truth, mom. I'll listen. I won't judge you. I promise." I pressed my hardening erection against her waist, causing her to let out a soft, "oh, God."

"I-I've...yes, I guess, yes, I've thought about it before. But not with you. Not with my own son," she said, and I could see tears in her eyes.

"Are you serious? You're lying to me, mom. Why are you crying?" I asked, looking down into her eyes.

"No, I'm sorry, honey, I'm really trying to be honest."

"No one's going to know! This is just us having fun on our date, remember, mom?" I said, putting my hand under her chin and raising it, moving my face closer to hers.

I leaned forward, pressing my lips against hers, letting them meet softly. Her lips gave way, slightly.

"Please stop," mom pleaded as I continued to kiss her.

"I'm not stopping until you answer me, mom," I whispered firmly, then closed my mouth around her lower lip. I took my left arm from around her shoulders and slid it underneath her neck again.

Mom was still struggling, but I didn't let her get away. She gasped loudly, and she put her hands to my arms, yet she still didn't try to pull me away.

I pulled her head back to mine, and I moved in for another deep, passionate kiss.

My mom whimpered when I did this, and her lips parted slightly, as I wrapped both of my arms around her, holding tightly onto her body.

When our tongues met, I kept kissing her softly, and I ground my groin against her. I rubbed my erection along the top of her stomach, and I moved my fingers to her sides, feeling her soft, curvy figure through her dress.

I pulled my lips away from my mom and gave her a gentle smile, bringing ne hand back to toy with her pearl necklace, and one moving slowly up her front until I began to feel her left breast over her dress.

Mom's eyes rolled into her head, and she moaned as my hand squeezed her chevage.

My mother gasped, her breathing heavy, and her eyes were half-closed.

I felt my mom's body shift slightly, and her hands came to rest on my own.

I ran a finger under her chin, and lifted her head to bring our lips together again. We kissed briefly, but I broke off to look at her.

Mom gave me a surprised, shy smile as she brought her face close to mine.

She grabbed hold of my shoulders and pulled herself closer, until her cleavage pressed up against my chest.

We both felt pleasure when our chests touched each other for the first time.

Her breath was hot against my neck, and I could hear her moaning softly as we made out.

"Having fun now, huh mom?" I cheekily asked. She didn't respond.

I continued to rub my hands all over her stomach and sides, feeling her down before my right hand cupped her right breast through her shirt, and my left hand switched to tugging at her pearl necklace.

The sensation of her large breasts pressing into my chest caused my cock to stiffen even more. Could this go all the way?

Mom moaned louder as I teased her.

I moved my fingers from her neck to her hair. I leaned in, running my tongue along her lips, and then kissed her deeply. My mom's hands were resting on top of mine, squeezing and pulling them.

"Do you miss sex, mom? Are you thinking about having sex with me?" I asked as I continued kissing her.

"Oh...ohh..." she groaned. Her body started to shake, and her hips began to move as well.

"Answer the question," I repeated, and then I pulled my face away.

I looked into my mother's eyes, and saw that her hazel-brown orbs were still half-closed. She was panting heavily now, though, as her chest heaved. I could see sweat on her forehead, and I knew she must be really turned on by what we were doing.

I returned my lips to hers and pressed them firmly against hers. We kissed again, but my mom didn't respond at all; she remained silent.

"Okay, mom, you're not answering me. Tell me the truth."

My voice was stern as I spoke. My mom nodded slightly, and I kissed her again, pressing my tongue into her mouth.

"Do you miss sex, and are you thinking about having sex with me?" I asked again, pulling onto her back and kissing her neck.

"I...uhh..." my mom whimpered quietly.

Her eyes had opened completely now, and she was looking into mine as I began nipping and nibbling at her skin.

"Say the words, mom," I said gently.

She shook her head, but I pressed on.

"Please, mom, say the words. You know what I want to hear."

Mom bit her lip, and then looked down. Her eyes went from me, and I saw them glisten.

"I--I guess, maybe, yes, I am thinking about having sex with you, honey," my mom said while trembling.

"You guess? Are you sure, mom?"

"Yes, I am, honey. It's so embarrassing. I mean, I'm your mom!"

"Are you sure about that, mom?"

"It's true! Oh, God, please don't tell anyone, just please don't tell anyone, sweetheart" my mom begged.

I smiled, and brought a hand up to caress her cheek. Then I moved towards the couch, and I sat down.

"Come here, mom." I beckoned my mom over, and she sat by me on the couch, this time, gently draping one of her legs on top of my lap.

I leaned in close, moving our faces closer together, until we were practically kissing again.

My hands ran down the front of mom's dress, touching her breasts though the fabric, and I squeezed them lightly.

"How does that feel, mom?" I asked her.

Mom moaned softly, but didn't answer.

"Doesn't it feel good? Does it make you wet?"

She nodded.

I slid my fingers underneath her chin, and lifted it up to bring my lips against hers again. My mom closed her eyes and let out a long, soft moan.

"Say something," I whispered into her ear.

"Oh...ohhhh...honey, your tongue feels so good."

Her body was shaking, and her breathing had gotten heavier.

I took a hold of her other breast, and then kissed her again, both of my hands now fondling her boobs over her tight beige dress.

My mother gasped loudly, and her hips began to grind against me.

"What is going on here, mom?" I asked.

"Please honey, please don't tell anyone!" she said, in between moans.

"Tell who, mom?"

"The boys at school, okay? Please, please, you promised me! Ohhh, God, ohhhhh, God...ahhhh..." she moaned deeper as I pecked kisses all over the top of her chest.

"No one's going to know mom, don't worry, this thing is our little secret. I'm you're special and exclusive date for tonight," I said staring her in the eyes.

My mother's body trembled from my words.

I grabbed onto her breasts again, squeezing them and feeling her hard nipples pressing up against my palms through the fabric of her dress. I pulled away from her for a moment, and asked, "hey mom, do you want to feel my muscles without my shirt on?"

My mom nodded and whispered, "yes."