Why Did Mom Have to Start Dating? - Cover

Why Did Mom Have to Start Dating?

by Ashley

Copyright© 2022 by Ashley

Erotica Sex Story: Fifteen-year-old Toby was very happy living alone with his mother after his dad left them. He felt conflicted, and even ashamed, when the raging hormones of youth made his feelings for her more... complicated. Then she announced that she was going on a date.

Caution: This Erotica Sex Story contains strong sexual content, including mt/Fa   Consensual   Romantic   Heterosexual   Fiction   Incest   Mother   Son   First   Masturbation   Oral Sex   Petting   .

I can’t say I was heartbroken when Dad left. I don’t think anyone, him included, would argue when I say that he drank too much, and when he did he didn’t get happy drunk. Oh no.

I was also pretty sure he’d been cheating on Mom, on and off, for ages and I had a horrible feeling that she’d put up with him, to a large extent anyway, for my sake.

Not too long after I hit puberty we started butting heads, mostly about the way he treated Mom, and I think that prompted her to push back at him as well. Long story short he left us about eight months ago.

To be fair to him he stuck with us for a long time when he clearly wasn’t very happy. He was also never violent and he was pretty good at sending Mom checks more or less when he was supposed to.

At one stage he even tried to patch things up with me. We spent a few weekends together and went to a couple of football games. We both tried to make it work but it just didn’t really happen.

I loved it with just the two of us though. More often than not in the evenings we’d cuddle up together on the sofa and watch TV or just chat about our days.

If a show was going to finish late we’d both get ready for bed before the start, her in a big, fluffy, toweling robe and me in my pajamas. Those nights were my favorites, so snuggly and lovely.

One very warm summer’s night Mom came down in a thin satin robe. As we cuddled I realized that I could see the curve of her breast where the top of her robe was partly open.

All of a sudden my dick started to get hard. I was ashamed of my reaction to Mom’s body and I fought to concentrate on the film, but my eyes kept being drawn back. Then she shifted slightly and I could see most of her breast and half of her nipple, all erect and pretty.

I was in serious danger of my dick rearing its ugly head and coming out of the fly of my pajamas. I had to put a stop to it.

“Mom ... you’re ... er...” I said to her, nodding towards her chest.

“Oh God, sorry Toby. I didn’t realize,” she said and covered herself up. I breathed a sigh of relief but I couldn’t get the image of her breast out of my head for ages.

I’d always thought that Mom was beautiful, I guess most boys think that way, but it was only on that day that I actually realized how sexy she was. At thirty-four she could easily pass for twenty-five and she was in amazingly good shape.

All of a sudden I found myself paying attention to the curve of a breast or the shape of her ass in the tight jeans she often wore. She had a habit of idly stroking her hand over her bottom as she was paying attention to some other task that got me almost instantly hard and I’d have to look away, embarrassed but excited nonetheless.

I tried hard not to be a degenerate about it but my eyes would invariably somehow just come to rest on her.

Two days later she dropped a bit of a bombshell.

“Carol’s fixed me up with a date.” She told me. “A man called Daniel Reynolds - a friend of a friend.”

I tried to be pleased for her but inside I was almost crying. I just couldn’t bear the idea of some man coming between us, and I silently cursed her friend Carol.

On the day of her big date she she came down to the lounge and did a twirl. She was wearing a pleated, mid-thigh, pink skirt with a white silk blouse.

“How do I look?”.

“Wonderful,” I said truthfully. She looked great but it hurt that it was all for him. Then I spotted something.

“You’ve got a thread hanging from your skirt,” I told her. She looked down but couldn’t see it.

“Get it for me will you darling,” she said.

I knelt at her feet and took hold of the thread and then tugged at it gently.

“No, don’t pull it, you might undo a seam,” she said and then walked away. When she came back she handed me a pair of scissors. “Cut it off as near the end as you can.”

I took them from her and, to start with, I craned my neck to try to see where it was coming from, but it disappeared up inside her skirt.

“I can’t see where it starts but it’s up inside somewhere,” I told Mom. “Maybe you should go and take the skirt off and do it that way?”

“I haven’t got much time. If you lie on your back you should be able to see it,” she suggested and moved her legs slightly apart. I gulped at the prospect of looking up Mom’s skirt like that and felt my cock begin to harden. Then I felt ashamed: here she was trusting me to do this, and all I could think about was perving on my own mother. I couldn’t think of a reasonable excuse why I shouldn’t do it so I lay down.

I slid between her feet and looked up her skirt. For a moment I forgot all about the thread as I gazed at the most beautiful pair of buttocks barely covered at all by a tiny pink thong.

I cursed my penis as it became fully erect and tried to drag my eyes away. I followed the course of the errant thread upwards and swallowed hard as I saw it heading straight toward her pussy. The tight cotton material of the gusset did almost nothing to hide the puffy shape of it or her enticing slit. It dawned on me that she must be bald down there and my mind conjured up a picture of how it would look if the panties weren’t there.

I tried to rationalize my way out of it: it’s your Mom, you came from in there. But it didn’t help at all. My erection was now so fierce it was being painfully constricted by my briefs.

“Can you see where the thread’s coming from?” she asked me.

“Yes.” I croaked, looking at it emerging from a seam just next to her pussy.

“Well cut it off then, and I can get going.”

I took the scissors in my right hand and started to slowly raise it. Oh my God, I thought, I’m putting my hand up Mom’s skirt! I really was trying not to brush against her inner thighs but it was very tight in there.

“Oh, that tickles.” She giggled as my hand touched her, and she wriggled making it even worse. I tried to ignore the soft, silky, warm skin grazing against my hand but it was just impossible.

“Careful,” I told her. “I have got a pair of scissors here.” The tip of the scissors was nearly at the end of the thread when I realized that I could feel the heat from her pussy on the back of my hand. It must have been less than an inch away, and knowing that made me tremble all over. I was mortified when my hand touched it, and I was expecting her to react in some way, probably badly, but for long seconds she said and did nothing.

“Did you get it?” I heard her say in a very quiet, almost husky tone. I steeled myself and managed to cut it off without touching her again.

“Got it!” I cried triumphantly and extracted my hand without further mishap. When I stood up Mom held me by the shoulders and gave me a peck on the lips.

“Thanks, Toby, you’re a dear,” she said fondly. I was still trembling from being so turned on, but I thought I could feel that Mom was doing the same. When I looked at her I could see that her face was flushed and her chest was rising and falling just as fast as mine.

“See you later, don’t wait up,” she said and picked up her stuff.

“Have a nice time,” I said, with an enthusiasm that I didn’t really feel.

When she’d gone I looked down at my crotch and my pants were tented right out. I gave it a few squeezes and then went to my room.

I opened my laptop and browsed straight to my favorite porn site. On the search bar, I toyed with the idea of putting in ‘mother and son’ before cursing myself as a deviant and typing in ‘teen lesbian’ instead.

I freed my dick and grabbed some tissues and was very quickly on the point of orgasm. As I came the vision in my mind though wasn’t the girls on the screen, it was Mom’s ass and pussy up that skirt and the feel of it on the back of my hand. I came so hard the first spurt hit me on the chin which surprised the hell out of me; I’d never done that before!

When I’d cooled off and cleaned up I was wracked with guilt for using my mom like some sort of porn star and resolved to keep myself under control in the future.

I was in the lounge when she got back.

“How did it go?” I asked her. She paused for a while before answering.

“Not bad,” she said, kind of unconvincingly. “We went to see a movie and then had a quick drink.” She seemed to ponder on it some more. “I think he was a bit nervous, he was quite quiet.”

Something in me was delighted that it hadn’t gone too well.

“That’s good.” Was the best I could come up with.

“We’re going on another date next Friday,” she added as she left the room.

Fuck! I thought.


On that day she’d been in her room for ages getting ready when I walked past the door.

“Ah Toby good, can you give me a hand please?” she called from inside.

She was wearing a shortish red dress and she was struggling with the zip. The cloth was all caught up in the zip and I struggled with it, trying to move it upwards but it was stuck fast.

“The material is all snagged up. I’m going to have to unzip it to free it.”

“OK. Go for it.”

It was a struggle but eventually, I managed to get it close to the bottom, then it jammed solid again.

At that point, I could see the top of her ass, with a little butt crack peeking out from some tiny shiny red panties. I got hard as hell, so much for self-control, I thought, and I was pretty ashamed of myself.

Holding the material with my hand meant that it kept brushing on the skin of her ass cheeks and it felt utterly gorgeous.

“Come on Toby, I’m going to be late.”

“I can’t budge it now Mom, I think you’ll have to take it off,” I told her, and I turned to leave.

“Wait,” she said. “I haven’t got time for that.” and she just pushed the shoulder straps off and let it drop to the floor.

I know my mouth dropped open at the sight of her. She looked fabulous in just those tiny panties and a matching half-cup bra which pushed her tits right up and gave her an incredible cleavage.

All thoughts of embarrassment had gone as I drank in the sight of her body. God, it was superb! The bright red underwear only seemed to accentuate her flawless alabaster white skin and she had a perfect hourglass shape.

She picked up the dress and handed it to me.

“Sort that out for me please Toby,” she said. “I’ve got to finish my makeup.”

Luckily for me, she sat down at her dressing table leaving me with just a view of her mostly bare back otherwise I think I’d have stared at her all night.

With shaking hands and constant peeks at her, I finally managed to get the zip sorted out.

I handed it to her over her shoulder and hurried from the room before she could see the state of my crotch.

After she was gone I wanked off to the vision in my head of her beautiful body. Afterwards, I couldn’t believe what I’d done but it was far, far too late by then.


When she came back she was a bit tiddly and sat on my bed while she told me all about her night: they’d been for an Italian meal.

“Are you going to see him again?” I asked when she was about done.

“I’m not sure, he still seems very ... uptight. Maybe I should take him to a bar and get a few drinks inside him, see if he loosens up a bit,” she said thoughtfully. “Thank you for your help earlier. You’re such a good boy,” she said as she stood up to go. She wouldn’t have thought that if she’d known what I did after she left, I thought a bit miserably.

It may have been my imagination but her goodnight kiss seemed to last a little longer than usual.


In the end, she decided to give him one last chance and again she called me into her room while she was getting ready.

“I need your help again please Toby. I can’t decide between these three outfits.”

She was wearing a black shortish skirt suit with a red blouse and she spun around.

“Nice,” I said

“Don’t look, I’ll change into the next one,” she said, looking hard at me. I turned away but not quite enough that I couldn’t see her out of the corner of my eye.

 
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