{"loaderData":{"4":{"story":{"id":"682a7e05-5c86-422c-8000-c878992f674a","seriesId":null,"seriesName":null,"currentUserId":"00000000-0000-0000-0000-000000000000","added":"2025-08-04T21:58:35.679Z","title":"It Isn’t Always So Easy","slug":"it-isnt-always-so-easy","shortId":"ShdWxYf7","authorNote":null,"disclaimer":null,"type":"Short","paidUrl":null,"synopsis":"Being with mom for the first time has its difficulties.","partCount":1,"parts":[{"partId":"fe0b7b8b-8ae5-4bb8-8d62-1f441bc02761","title":null,"summary":"I maybe shouldn't have told mom I was still a virgin at nineteen, but I'd had a weak moment after ye","wordCount":2868,"readTime":14,"number":1,"state":"Published"}],"currentPart":1,"contentTitle":"Chapter 1","content":"

I maybe shouldn't have told mom I was still a virgin at nineteen, but I'd had a weak moment after yet another unsuccessful date. This revelation led to one of the most important moments of my life.

\"You'll find the right one some day,\" mom said.

\"That's what everyone says,\" I retorted, and they did, especially the sweet girls who liked to keep me safely in the friend zone.

Mom came to my room that night. I didn't understand what that was all about. She never did that, and she was only wearing a disturbingly thin nightgown which left the bumps of her dark nipples clearly visible through the fabric at the point where her saggy breasts were hanging down near her stomach. My gaze quickly blinked away and I made sure it stayed there. Mom said she wanted to talk and that she couldn't sleep because she was worried about me.

\"You seemed more depressed than usual and that left me thinking,\" she said, touching my arm. I twitched a bit because she didn't really touch me very often.

\"I'm fine, mom. Nothing new about this,\" I assured her, as if I hadn't been crying into my pillow just moments earlier. She sighed and I let her hold and caress my hand for a while before she left after she understood I didn't want to tell her anything more.

I didn't think much about that until she was there again a few weeks later. At least she knocked this time and avoided surprising me. I had not fallen asleep yet anyway, I was just reading on my Kindle. Mom kneeled next to the bed and lightly brushed my cheek with her fingers. I twitched away nervously, dropping the Kindle. Luckily it only fell on the mattress and not the floor. Those things were overpriced and broke easily. I guess I shouldn't have reacted so nervously, but my mother really wasn't a touchy-feely type, or at least hadn't been since I'd been a baby.

\"Mom, what are...?\" I asked, since she hadn't said anything, but I fell silent when I saw how her hand moved to the hem of the nightgown and raised it. My eyes widened and my jaw dropped when I saw a bush of bristly dark hairs. I was completely frozen, unable to turn my gaze until she let the hem fall back down. Then I quickly turned away from her and realized my heart was pounding vigorously.

\"Sorry...\" mom sighed when she saw how my reaction, and lightly kissed my cheek before she left.

I was thinking about that disturbing yet somehow entrancing sight for the rest of the night, rolling nervously on the bed before I finally fell asleep. When I woke up, I was completely rock hard and well aware of what I had been dreaming about even though I didn't want to admit it.

\"Goddamn it,\" I groaned, knowing I had to meet the family in the kitchen. Mom didn't say anything, and neither did I. It seemed like this was one of those things which would be forgotten and not talked about. Not that it left my mind even as weeks went by.

I tried to remember to clear the cache of my computer whenever I was done surfing for mature women with dark bushes. That was an entirely new interest for me after all the \"barely legal\" sites I had been browsing for lookalikes of the girls next door I had been missing while they dated stupid jocks.

I did find one older woman with her legs open who looked slightly like mom and that immediately made me so damn hard I thought I was going to faint. Worse yet, I knew I had been thinking about mom and not a random woman on the internet.

\"I need a fucking date,\" I mumbled, shaking my head. I closed the page and membered to clear the cache before switching to CollegeDates. There were plenty of sweet smiling cuties there, but they steadfastly refused to answer any of my messages whenever I dared to even send them in the first place.

I read all the interesting girls' bios carefully so I could send them long and thoughtful responses. No dick pic spamming from me, I'm an artist at heart. I'm sure that's a part of the problem, but it's not I can do anything about it. I finally shut down the computer after sending more messages than ever before. Waiting for the answers made me very nervous.

It turned out there wasn't much reason to feel jittery. Weeks passed and I didn't get a single damn answer from any of the girls. I was starting to wish mom would come hold my hand again, but that caused certain other images come flashing to my mind and I tried to make them go away until I finally decided to do something about this obsession.

\"Could we talk again, mom. Tonight, just the two of us,\" I said to her one evening, wanting to clear the air between us. \"I've been having hard time.\"

\"Oh, I'm sorry, honey,\" she said with a soft voice. \"I wasn't sure if you wanted to, as depressed as you have seemed. I should have understood...\"

\"It's all right, mom...\"

\"Yes, tonight,\" she said, before one of the younger kids dropped something in the kitchen and that caught her attention.

\"Oh dear, what did mommy's little rascal get up to now,\" she said and got up.

Later in the evening I was trying to read in bed again, but it was hard to concentrate for a variety of reasons. Mom knocked and entered, wearing the same nightgown. I had assumed she wouldn't wear that. This must have been a sign of something. What, that was yet to be seen.

Mom held my hand again. \"You've been having hard time. I can see it. Sorry that I haven't been much help lately.\"

\"I've been thinking... um... about the last time,\" I blurted out, avoiding her eyes.

Mom sounded embarrassed: \"I'm really sorry about that, I don't know what I...\"

I did my best to explain my thoughts: \"No, mom. I mean... I'm the one who should be sorry. I want to do it, mom. I just... got scared.\"

\"Really?\" Mom frowned, and her hand was moving towards the hem of her nightgown again.

\"Yes,\" I said when her fingers touched the lacy hem. She was hesitant and I bit my lip as I looked her in the eyes. \"Yes, I really do.\"

Mom gave me one more silently affirming gaze before she slowly started pulling the nightgown up and over her head. Seeing my mother naked wasn't as appealing as I had imagined. Her saggy tits hung almost down to her stretch-marked belly, and right under that the bristly dark hairs started and formed a bushy thicket between her thighs. I almost wished she had left the gown on, but I was polite enough not to show that in any way as she sat on the bed.

We tried an awkward kiss during which I was nervously aware of my mother's naked nipples touching me and the twitching and hardening which was happening in my groin area. Mom was holding my hand and looking me in the eyes as she lay her head down on the pillow. I couldn't help my gaze being locked on the dark thicket between her thighs.

My eyes widened when my mother opened her legs wide. The vagina was a loose wide opening between her cellulite-marked thighs and surrounded by bristly dark hairs. It was nothing like I had imagined, the bush spread all the way to the noticeable stretch marks on her stomach.

\"How do I...?\" I mumbled, barely audibly, overcome with shyness as I moved closer.

\"Just guide... it... in with your hand. Don't worry, I'll help you.\"

\"Okay, mom,\" I said, knowing this was a bad time to start having second thoughts. After a few fumbling tries I managed to slip in with the helping guidance of my mother's fingers. It was very warm in there and I could feel the bristly pubic hairs on my shaft. My hands were on either side of mom, I was still afraid to lean close for some reason. I started awkwardly thrusting my hips, not feeling much more than the warmth.

\"Try to get it deeper,\" mom instructed, her hand touching my hip. I moved my weight to my elbows and tried to do a longer thrust. The natural ribbed feeling of the vagina caught me by surprise, which mom could see on my face.

\"Just like that,\" she said, and I let my hips move, doing the same long thrusts.

\"Hh. Hh. Hh.\" Minutes passed awkwardly as we both started to realize this wasn't working. Mom quickly took the situation under control like a responsible parent should.

\"Let's try something else, okay? Or do you mind if I'm on top?\" she asked.

\"N-no, that's fine,\" I tried to sound confident despite how the situation was going and how embarrassed I felt as I pulled out.

\"All right. So you lie down instead,\" mom suggested and I did so. I tried to think positively, at least I had stayed hard, so things could have been worse.

Mom moved on top of me and brushed her hair over her shoulders, which made her saggy breasts rise and fall. I was completely rigid as she directed me in. She tried to smile as she started moving, and I tried to caress her thighs and hips when she started bouncing faster, even though I didn't really like how her saggy tits were flapping around when she did that.

Mom tried grinding her hips and alternating the pace for a while, but eventually she was just riding me at a rapid, desperate pace. She wanted to make it happen despite the problems we had encountered during the evening so far. My eyes were locked on her dark bush because I didn't want to see her looking at me and watch her saggy breasts bouncing and slapping around. It wasn't much better, the bristly hairs which I could distinctly feel on my shaft were an unappealing sight in how spread onto her lower stomach and thighs. The stretch marks on her belly were also constantly making me all too aware of who was on top of me.

Mom spoke in a husky and breathy voice: \"Come on now! Shoot it in me! Shoot...! It...!\" She was trying to sound nice and sweet rather than demanding while she was reminding me about the goal of the intercourse, but it wasn't working out so she had to start slowing down when she got tired.

\"Sorry...\" I said, biting my lip.

\"What am I going to do with you?\" Mom shook her head in frustration. I knew she wasn't going to give up, she could be quite persistent when she got in that kind of mood, and she knew nature would always find a way. I later understood that for a mother and son it was easier than for some because the natural ribbing of a mother's vagina was especially compatible with her son and would get the results sooner or later regardless of how loose and hairy her vagina was.

Unfortunately I only learned that later, so right now the situation seemed hopeless to me. I barely dared to look at mom as she started riding again. She quickly reached the same pace as before and kept it going. Despite the abrasive pubic hairs and the fact that the vagina was my own mother's and not as tight as I had imagined it would be, I was getting sweaty and twitchy because of the warmth and the motherly ribbing.

\"I - I can't do it, mom,\" I whimpered when physics and biology were starting to get the better of me, bringing my hands to her hips and patting them until she slowed down. \"I'm sorry,\" I apologized the best I could. I was aching all over, but I was just too scared to release into my own mother.

\"It was going fine now!\" mom said and frowned in exasperation because I had stopped her. Her thin lips had turned into a line and I could see from her gaze that she was frustrated with me. I looked away as she lay down beside me. I kept staring at a corner, away from her. Eventually I felt mom's hand slide into mine, but I almost wanted to twitch away even from that.

When the awkward silence became too uncomfortable for both of us, mom finally spoke: \"Do you want to try again? Or should I just go...?\"

I was breathing deep. I knew I had to think about my mother's emotions too, and not just about my own inhibitions. I mean, the ribbed nature of my mother's vagina had been doing what it was intended for, it was just that I had gotten nervous and scared so I had made her stop. I was afraid she would be left feeling like a bad mother if I didn't successfully shoot inside her on my first time, and I didn't want that to happen. Now was the last chance of getting my feelings under control.

After a long pause I finally said: \"I really want it to happen, mom,\", more out of politeness than anything, but I really didn't want to fail on my first time. Especially not with mom. It wouldn't be nice for her.

\"All right. Let's try it this way,\" mom said as she climbed on top of me, with her back towards me this time.

I could feel the vagina's natural ribbing better in this position, especially when mom leaned backwards and supported herself with her arms. That must have been her intention, although I have to admit not having to look her in the eyes helped too. I could still watch her saggy tits bouncing and flopping on the mirror to the right if I really wanted to. I wouldn't say I did, but I still snatched a glance at them occasionally just to see how big and tall her nipples were.

My mother's hips started riding me again, occasionally twisting a little which helped because it felt good and natural in this position. The vagina being loose from several births didn't matter so much when mom was in control of her hips. She could make them twist and rotate in ways which overcame any possible issues. Deep penetration allowed the ribbing to work on the whole length of the shaft, especially when mom started increasing the pace. The bristly pubic hair opened into the warmth and I could even feel my mother's clitoris against my balls as she rode hard. That was a very tender moment which along with the deep naturally ribbed penetration and the motions of experienced birth-giving hips finally brought the act to its natural finish.

\"Nn-n!\" We both flinched in surprise as we heard the squirt. It had finally succeeded. My hips had thrust instinctively when I was holding onto mom's, and that final motion had sent the sperm in at long last. It was a deep ejaculation, straight into the womb, and my mother threw her head back and shuddered when it happened. The spurts would have been flying high if they hadn't been beautifully sent into their most natural place, filling it completely with the warmth from my balls. The mom-ribbing pulsated on my throbbing shaft and the movements of experienced hips helped to keep the drive going as long as the spurts kept on firing into the womb.

\"Nng-nh!\" the feeling made me groan as my entire body tensed so hard my toes curled. Despite our difficulties I saw and felt how my mother's hips shuddered when it happened, and I knew I would never forget that memory. It was worth all the trouble, and when comparing experiences with other people it made me later understand my first time had been better than many other's. I still remember it as one of the best orgasms of my entire life and I doubt that is going to change.

\"Finally!\" mom sighed in exasperation and surprised me by offering a slight compliment, \"But at least the finish was proper and good even if it took its time.\"

I couldn't really disagree with that. Although the orgasm's end had brought along an instant feeling of regret, I felt like I had shot at least twice as much as ever before, completely emptying my balls into the womb.

We had succeeded at last, but I wasn't sure how I was feeling about that. I was distinctly aware that I had come inside my own mother, and I doubted that awareness would easily go away if ever. I correctly thought this would become one of those things which would never be talked about. Except for one quip I managed to slip into a conversation much later, thanks to the singer Shakira.

\"Your hips don't lie, mom,\" I said when song's video was playing on TV. That made mom flash a quick smile at me during a brief moment when we were alone during the day.

\"What, am I like Shakira now? Silly boy,\" she said and pecked a kiss on my cheek.

I still like that song and think about mom every time I hear it. We haven't done it again and I have a girlfriend now, but who ever knows what will happen in the future?

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