What Might Have Been

This story is a cross between reality and fantasy. I hope you enjoy the format. For the typical disclaimer, all players are over the age of 18 and the story contains loving sex between a mother and her son. If that bothers you, clicking your Back button would be a good idea. Otherwise, read on. I look forward to polite feedback.

A huge thank you to barefootgirl69 for cleaning up my mistakes.

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Looking back on my younger years and remembering some interactions with my mom, I'm pretty sure I missed some hints, some teasing, maybe even some straight up seduction. I was clueless back then when it came to girls (and women) and probably needed a smack to the head to see what was right in front of my eyes. Someone could flirt with me but I was too shy and lacked self-confidence to recognize it. Following are some short stories about "what might have been". There is not much build up in each individual story. I will say that now so that it doesn't seem like one little thing resulted in hot and passionate love-making all of a sudden.

My dad worked out of town quite often and, even when he was home he was, well, let's just say he was less than pleasant to be around. I'm pretty sure their love life was near nonexistent based on several things, such as him always going to bed much later than my mom, no affection between them, etc.

I've always recognized that my mom is very pretty. She worked out so is pretty fit, but I never really looked at her as "hot" or had thoughts of a sexual nature about her.

I was always closer to my mom and my dad often referred to me as "momma's boy" in a very derogatory manner. After I graduated high school, she seemed to elevate that closeness. She would hug me more, come out of her room in her nightgown in the morning and at night (not quite lingerie but definitely more revealing than before), often not wear a bra, and make little risqué comments. This increased over the course of a couple of months but, again, I was clueless.

In our looking-back fantasy scenario, however, I DID notice these things and I started seeing my mom as a sexy woman. At first I thought I was imagining it but soon realized mom was flirting with me! We were a very conservative family and I didn't really know how to respond. I did look when I thought I could get away with it and even got caught a few times. But she would just respond with a little smile and sometimes a comment. "Is this shirt a little tight?" or "I'm sorry, I didn't know you were up already."

As my mother got bolder and bolder, I would see cleavage where before I don't think I had seen much below her neckline. Then, there were the times I would see her in the hallway or even through her open door when she was wearing only a bra and panties. She certainly didn't have a young perky body, but I thought she was hotter because of it.

I was a walking erection half the time and Mom didn't seem to mind. The boldest thing I had dared was to deliberately adjust my cock in my shorts one day when I knew she would see me. Her eyes lingered on my crotch for a few seconds before she breathed heavily, smiled and walked by me, her fingers grazing my arm.

As my desire built, my guilt over looking at my mother with sexual thoughts decreased. I started fantasizing about her and her body invaded my mind during my masturbation sessions. Her teasing seemed to be constant after some time and I was going crazy. But what should I do? How do I respond?

The events below are all real but taken to a level that didn't really happen. They are somewhat short and fast, but remember that the sexual tension between us had been building day by day for a few months. Each short is how I wish I had responded to each event at the time. Label each of them as "What Might Have Been - How It Started".

----- Wrestling Match

POP! "What the heck, Mom!" My butt stung. I was about to go for a run so I had on shorts and a t-shirt. The shorts are pretty thin and Mom is pretty deadly with a dish towel. I should have known not to walk so close when she had one in her hand. She jumped out of my reach giggling. Grabbing my own towel, I started stalking her around the dinner table. Back and forth we moved, staying out of each other's reach.

I snapped my towel at her a couple of times but she was always a step ahead.

"You move pretty fast for an older lady," I taunted.

She froze and looked at me, eyebrows up. Oh, crap! The Mom Look. "You're going to regret that, BOY," and she charged.

I did what any self-respecting young man would do. I ran! Through the living room door and right over the arm of the couch. I never said I was the most graceful person. I landed on my back and Mom was on me in an instant. Straddling my waist and pinning my shoulders, it was her turn to taunt. "What are you gonna do now?"

My mother is pretty fit for a woman of 40. She works out and eats well. I'm quite a bit bigger, though, and could have easily flipped her off of me but, suddenly, I realized that she wasn't wearing a bra under her t-shirt. I could see the sway of her breasts and just make out the hint of her nipples.

Now I'm 18. I'm sure you can imagine my involuntary response. I made some token moves as if struggling but was afraid that, if I moved too much, Mom would feel my hardness.

"What's wrong, baby? No more tough talk?" she asked.

"Don't think I can't get away," I responded. "I just don't want to hurt you."

"I don't think you're in a position to hurt anyone." And then she made use of my Achilles' Heel. I'm about as ticklish as anyone can be and she knows this well, so she goosed me in the side. Her movements caused her breasts to sway even more and I was mesmerized until that point. I jerked and said "Stop!"

"Why? You deserve that and much more for calling me old," and poked me again with a huge grin on her pretty face.

This time I arched my back and felt her butt graze my cock through my shorts. Mom's eyes got just a little bigger for a second. And then I saw a gleam. She put both of her hands on my ribs and I started thrashing. This caused her to slide down a little lower so she was now just resting on my crotch.

"What are you going to do about it?" she asked as I felt her move her hips slightly.

"Two can play that game," I responded and grabbed her sides. Nothing! Mom isn't very ticklish and that didn't faze her at all. She just laughed and wiggled some more.

"Nice try, Buster, but you're gonna have to do better than that," she laughed. I moved my hands just a little and was under her shirt just above her shorts, hoping her bare skin would be a little more sensitive, fingers on her side and thumbs on her tummy.

"Nope," she said and ran her finger across my chest. Not so much a tickle this time as a tease. And still with that mischievous smile. So I moved my hands a little higher under her shirt. "Don't think I won't keep going," I warned.

"Won't do any good. You're still trapped."

So up I went, my eyes locked with hers. The only reaction was a little more grinding. I was rock hard at this point and there is no doubt that she could feel it. Both of our shorts were pretty thin. Nervous almost to the point of shaking, I decided to risk it and moved up a little more until I could just feel the swell of the underside of her breasts. She closed her eyes and I saw her nipples harden through her shirt. That increased my boldness so I cupped them just a little.

"Give up yet?" I asked quietly. She just shook her head, bit her lip slightly and pushed her hips down further on me.

Throwing caution to the wind, I encircled her breasts with my hands and placed my thumbs on her nipples. They were as hard as pebbles. A little moan escaped her throat and my mom began to slowly slide up and down my cock.

"Take that," I whispered.

My mind was reeling! I couldn't believe it had gone so far so fast! But not one to waste an opportunity, I started moving my thumbs in slow circles. Mom arched her back, pushing her breasts out, silently begging for more. I so wanted to see them, to break the confines of her t-shirt, to rip our shorts off, but I was afraid to ruin the moment so I just kept circling.

Mom's hips sped up and her grinding increased. I massaged her breasts and thumbed her nipples with earnest. The look on her face as she sat above me riding my cock was amazing! I thrust my hips up to meet hers and we abandoned any pretense, only enjoying the pleasure.

I could feel the tension building from what seemed like from my toes to my head. Mom's grinding was almost frantic as she groaned and thrashed her head. I adjusted my hands and pinched both nipples between my thumbs and fingers, kneading them firmly but trying not to cause pain. That pushed my mom over the edge. She pressed against my cock and moaned loudly, her body taut and shaking. She was cumming! It was too much for me and I felt my cock explode in my shorts. I have never cum so hard in my life!

We ground slowly against each other for at least another minute or two as we came down off of the incredible high. Slowly my mom opened her eyes and stared into mine, a look of horror on her face as if she just realized how far we had taken things. I just smiled, too breathless to say anything and her shock turned to a smile as well.

Mom leaned down and gently kissed my lips. "Wow!" she breathed. She slid up and down a little and said "I think we made a bit of a mess."

"Yeah, but it was worth it," was all I could come up with. She smiled, kissed me again, and said "You should go get cleaned up." She then stood, looked down at our cum-soaked shorts smiled again and went to her bedroom.

I laid there for about a minute, processing what just happened. Never had I imagined something like this would actually happen. The mess in my shorts pulled me out of my reverie so I got up to take a shower, wondering if this was a one-time thing or if there was more to come.

"Baby, can you bring me a towel?" Mom yelled from her bathroom. I brought two.

----- Storeroom Cleanup

What was that awful noise brutally dragging me from my sleep? "Wake up, lazy bones. We have work to do!" I heard Mom say. Ugh. I agreed to help her clean out our storage building today. Throwing open my curtains, my loving mother yanked the covers off of me. Fortunately, I sleep in shorts but my cock had some morning swell to it. Not fully hard but definitely noticeable in my thin jogging shorts.

"You promised to help me," she pouted. Women know how to use that, don't they?

"OK, Mom, I'm up now," I said, shielding my eyes from the harsh light.

"Mmm, so I see," she smirked looking at my shorts. "Get a move on before it gets too hot."

Those little remarks were more and more frequent. I wish she knew what they did to me, where my mind wandered when she said them. Or did she?

Walking downstairs like a zombie, I grabbed some orange juice and a banana and headed out to the small building in the back of our yard. About once a year we clean it completely out, throw away half of its contents and put what's left back neatly. Each time we swear we will keep it organized and junk-free throughout the year but that lasts about two months.

Mom had already started so we had a little bit of working room, but it was still going to be tight quarters in there. As she turned to chide me for my slow start, I saw immediately that she was in a light shirt and shorts. And no bra. I raised my eyes and apparently she picked up on it. "What? It's going to be warm in here," she said, defending her wardrobe choice.

I just shrugged my shoulders. "Good point," I replied. It was going to be a long morning and would take a lot of willpower to keep myself from getting an erection.

Due to the limited space there was a good deal of body contact over the next hour. And I started to think that much of it was intentional. My willpower was crumbling. I tried to think of everything but my mom's body against mine. She would bend over to pick something up and I would see her breasts swinging under her t-shirt or her shorts pulled tightly over her ass.

At one point, I placed my hand on her back to move around her. Knowing I felt no bra strap caused an involuntary groan. And she heard it. "Something wrong, sweetie?"

"Nothing, Mom," I said, and after a pause, "Just thinking that, if you didn't wear a bra around Dad, you would probably give him a heart attack."

"Like he would notice," she mumbled. I could hear both sadness and bitterness in her voice.

As I moved around her again, I put my hand on her back again and paused. "I don't see how he could not noticed." My mom stood up straight and leaned back into me. I wrapped my arms around her from behind to hug her for comfort. "I'm sorry," I said quietly. She leaned her head back against my chest.

It was at that point that I realized my arms were under her breasts. I could feel their warmth and weight through Mom's t-shirt. No amount of thoughts about football or Algebra could prevent my involuntary reaction. My cock was hard in a matter of seconds and pressing against my Mom's butt. I couldn't back away without her feeling rejected and I knew she didn't need that right now. Maybe she wouldn't notice, I tried to tell myself.

She raised an arm behind her and put it on the back of my head. "You noticed them, though, didn't you?" I was too nervous to answer. She pressed back against me and said "Yes, I see you did. Do you like them?"

I moaned and said "Oh, God, yes." Slowly I moved my hands to caress up her sides and under her breasts, lifting them slightly. "They're perfect!" Mom put her other hand on the back of my neck which caused her breasts to push out prominently. I could see them clearly over her shoulder. But I wanted to feel them.

I lowered my hands to the bottom of her shirt on her belly and waited. "Go ahead, baby," she purred, so I slid my hands under her shirt to gently cup her breasts again. Oh, my gosh, it was incredible! I could feel her hard nipples in the palms of my hands. "Mmmmm," she moaned. "It's been far too long."

As I caressed my mother's breasts, I began to kiss her neck. Her moans grew louder, encouraging me. I massaged her breasts, playing my fingers over her hard nipples. Suddenly she turned, pulled her shirt over her head, and kissed me like crazy, thrusting her tongue in my mouth while holding the back of my head and grinding her hips into me. I could only feel the sides of her breasts as they pressed out from between us.

After about two minutes of the most passionate kissing I've ever experienced, Mom took a small step back. "Are you sure about this?" she asked. I saw, for the first time, my mother's gorgeous breasts. I was not experienced enough to know their size but they had a beautiful drop and were capped by small hard nipples. I could only nod.

She reached down to stroke my cock through my shorts. "I've wanted this for some time now," she said and reached inside. It was amazing to feel my mother's hand on my cock. She pulled on it a couple of times and then removed her hand.

"No!" I groaned.

"I have something better in mind, baby." She pulled my shorts down and then hers. I pulled my shirt off and stepped forward to kiss Mom. Our totally naked bodies melted together.

Breaking the kiss, Mom hopped on a table behind her and spread her legs. My eyes were, of course, drawn to her pussy. It was neatly trimmed and glistening with her juices, revealing her excitement. As I stepped forward, Mom grasped my cock and guided it to her. Looking in my eyes, she said "Last chance to back out, baby."

"Nothing could change my mind," I replied. I pushed forward, entering her moist warmth. I had to go slow or I would explode. When I was all the way in, I paused to regain some control.

"Please, baby," she pleaded. I could not deny my mother's lust or my own. I slid almost all the way out and then back in, slowly for several strokes and then increasing speed as my mom thrust up to meet me. I couldn't believe my cock was in my mother's pussy!

She wrapped her arms around my neck and her legs around my waist. "There's time for lovemaking later. I need you to fuck me, baby," she growled. I almost came right then and there. The lust in her voice was intoxicating. I began to thrust my cock inside her, almost lifting her off of the table. She met each thrust hungrily. "Oh, yes, like that. So good," she encouraged. I knew I couldn't last much longer.

Digging her heels into my back, Mom went wild. I have limited sexual experience but it was like nothing I've ever seen. She bucked against my cock and almost screamed as she came. I'm not sure how I lasted this long but I followed right behind her, filling her gripping pussy with my cum. We came together, holding each other tightly. After several minutes we separated. I kissed Mom gently but passionately.

"You have no idea how much I needed you," she said. "That was better than I've fantasized."

"I couldn't have imagined this would really happened," I replied. "I think I'm dreaming."

"It's was real, baby, and it's going to happen many more times if you're willing."

I was!

----- Good Night

The last few weeks have been insane. My mom seems to be flaunting her body more and more. It makes one's imagination race. Well, it does mine. Shirts without bras, a little cleavage here and there. But nights are the worst. Mom has been getting ready for bed earlier than normal and then will read or watch TV in the living room in her nightgown, something she never did before. Nothing Victoria's Secret or anything, but still wow!

They are thin, not quite transparent, but close. I can see the bumps of her nipples and a flash of panties if she sits just right. Makes it hard to concentrate on whatever is on TV.

This night was no different, and when I got caught peeking a couple of times, Mom would just smile and turn back to her book. This went on for probably an hour.

Rising and stretching, she announced it was her bedtime. Breasts pushed out, panties showing. I know where I was headed as soon as she went to bed.

Mom leaned over as I lay on the couch to hug me good night, giving me an unbelievable view of her breasts. Definitely odd as I haven't hugged my parents good night in years. "Get over it. A mom can hug her son whenever she wants," she said when I hesitated.

The following night had the same routine. I couldn't keep my eyes off of her and I think she knew it. When it was time for bed, she leaned over for her hug and I put my hand on her side, accidently grazing the side of her breast. Really, it was accidental. I didn't have the guts to try something like that yet. Mom jumped a little and I thought I might get smacked, but she just laughed as she straightened up. Blushing profusely, I apologized. "I'm sorry, Mom. That was not intentional at all."

"It's ok, sweetie. Sometimes a woman likes to get felt up a bit." She winked and went to bed, leaving me stunned at her comment. My dreams last night were of Mom. No surprise there.

The next morning, as I sat at the kitchen table eating my cereal, Mom came down ready for work. "How are you feeling this morning?" she asked with a definite emphasis on the word "feeling". She kissed the top of my head and there was no mistaking her breasts pushing against my arm. Thoughts of my mother's breasts swirled in my mind all day.

I have no idea what was on TV that night. I could only think about Mom as she sat at the end of the couch in a nightgown with buttons, the top few undone. As she shifted I could see almost to her nipple, and she shifted often. Her feet were tucked under her with her butt facing me. I swear I could see the bulge of her pussy once or twice. I hoped she wouldn't suspect why I had a pillow in my lap.

The moment I was waiting for finally came. Standing, stretching, flashing, oh my! I had been psyching myself up for this all night. Did I dare? Mom leaned in for her nightly hug and I placed my hand directly on the side of her breast, feeling it's weight. She stayed there a moment and the said "You can hug your mom with both hands, you know."