Erry's Boy

Since my parents divorced I've moved around a lot with my Mom, so far I've lived in the houses of 4 of her "new" husbands until they became "ex" husbands too, and by the time I turned 19 I made her promise not to even bother introducing me to her boyfriends, if it wasn't going to last, and let's face it the odds were stacked that way, then I didn't need to even acknowledge his passing.

In the style of most reasonably well off divorcee single mothers, my Mom had a habit of giving me exactly what I wanted more often than not, and so it was that we had "our" house and she only ever visited her new men at theirs.

Without wanting to sound arrogant I need to let you know a little about the sexual history of our little family before I get into this one memory in particular. My Mom is a stunning woman, not tall, but thanks to her die-hard exercise regimes she has stayed as fit and toned as when she was a state representative in High School Tennis. Plus, the subtlety dressed cleavage from her generous bosom is a sure fire way of getting the attention of men the world over. Mom has always been very popular with guys, and she has the dazzling smile and self-assured sense of humour that comes with it, even when discussing sex openly with me. Growing up around her, the apple didn't fall far from the tree, and the open talks about sex still didn't come early enough as I lost my virginity to older girls within a month of beginning puberty.

The relationship that we have is a very close one, we have fought a lot in the past, and as a teenager I know I used fights to try to get my way wielding the divorce like a weapon against her, but it is safe to say that especially now that I've grown up into quite a solid guy, I am very protective of her and she still thinks I'm the most perfect person on the face of the earth. It's nice.

That relationship took a bizarre twist recently however, we were living in our house on the coast, Mom was visiting her current boyfriend most nights and I had a girl that I was sharing my own bed with regularly too. As much as Mom tried to hint that she was a lovely girl that I shouldn't risk losing, I wasn't even going to entertain the thought of a relationship beyond casual sex, and that subject usually led to me trying to find some way of teasing Mom in return.

Playing on her libido seemed like an effective way of doing just that, using the fact that I was getting sex in her house and she couldn't to really get under her skin and change the subject until she was the one needing to walk away.

I know, sometimes children can be cruel. But in our relationship, Mom loved me too much not to just take my cheekiness with a grain of salt and have a long hot "shower" to ease her discomfort.

I felt like king of the world those nights.

Two weeks ago I started taking it too far, enjoying the power of actually winning a verbal joust with Mom so much that I would persuade Lisa, my gorgeously leggy but none too intelligent blonde "lover", to give me blowjobs in the living room on nights that I knew Mom would be coming home. I don't know for sure, but seeing the look of silent shock and envy on my Mom's flushed face upon seeing me sitting there on the sofa facing her, my arms behind my head as Lisa's blonde ponytail slurped and bobbed on my throbbing cock probably tipped me to blow my load down Lisa's throat sooner than usual.

No doubt knowing that it was me being a brat, Mom never interrupted or made things awkward while Lisa was around, and so I continued, walking from the shower with my erection out in the cool air and giving Lisa loud orgasms (not that this particular girl had any other kind) with the door open just enough for the sound to carry down the hallway.

I was winning, and considering how sharp witted and confident my Mom had always been, this was a rare feeling that I wasn't just savouring, but relishing to excess.

Within three nights, although I only recognise it now, Mom started fighting back in her own way.

First of all she stopped showing any shock or jealousy of my overt sexual activity, instead smiling knowingly and giving me encouragement. This on its own disappointed me, but even without the victorious feeling of making her uncomfortable, the new sensation of having approval to get laid all over the house was thrilling of its own right.

Secondly I started to notice Mom as a woman more and more, her perfectly shaped ass raised in an inviting yoga position when I walked into the living room, her dark nipples hard against the thin material of her nightie as she came into my room to talk to me about seemingly irrelevant things, and even dropping her towel a split second before entering her bedroom giving me not enough of a look to see her entire body before the door closed.

Just because I was getting sex in the house didn't mean I wasn't frustratingly horny the rest of the time, and I didn't even know she was doing it on purpose yet.

The next turning point was a conversation I'll never forget over breakfast, and although I was every bit as self-assured going into it, I realise now that my confidence is only as strong as Mom wants it to be.

As usual Mom was up early, soft cotton mini-shorts and a nice blue tank top showing off both her fitness and her curves, 38D breasts with hips to match, as she prepared some muesli and yoghurt for breakfast. I staggered into the kitchen topless, just my boxer-briefs between my morning glory and the morning air and slid onto one of the stools at the kitchen counter.

"Good morning Matthew" she practically chirped, her energy making me feel lazy before I'd even said a word.

"Sure is, I'm a free man." I announced, and Mom immediately turned back to me for an explanation.

"No more Lisa, I told her last night that she was getting too attached, so I'm good to go again, starting today." Mom's obvious frustration at my "objectification" of women had long since ceased showing outwardly on her face, but she raised an eyebrow about some hidden thought and brushed past me to sit outside in the sun to eat.

I poured myself a glass of milk and followed her onto the balcony.

"You seem fine with the news, Mom. I thought you said you liked her?"

She just smiled knowingly up at me and gestured for me to sit.

"Yes Matt, she was a lovely girl, but I knew she wasn't the one for you, so there isn't much point getting upset over the inevitable is there."

This wasn't the reaction I had been looking for, so I pressed on,

"How do you know she wasn't the one for me?"

"Mother's know these things" she teased

"Oh ok then, Mother," I mocked, "What sort of girl is right for me then?"

Without a hesitation she smiled in a way that really annoyed me, and simply said something about leaving that for me to find out for myself.

"See! You don't know shit about it; you just don't want to admit that I'm more in control of my life than you are!" The words were a classic outburst, meant with complete sincerity but only because I was too annoyed to be thinking with any sort of sense.

Mom took it all with good grace and put down her spoon, turning in her chair to look me in the eyes with her baby blues, a gentle smile and a reassuring hand on my knee accompanying her 'wise words'.

"Darling, there is a reason that people say boys look for their mother in girls, and Lisa was practically the complete opposite of me, wasn't she. You need a strong woman with a brain."

It took me a while to think of anything to say to that, partially because at the moment of those words Mom caught my eyes flick towards her chest, but the words came out before my brain had any input.

"Oh, really? So I need a strong independent woman with brains, who isn't tall, who has brown hair and big tits? Or do you just think because every other man in the world wants to be with you that I do to?"

"I'm not saying you want to be with me personally, but you already know that." She countered rather pointedly, but then her cheeky smile returned and she followed it by saying,

"But according to Freud and most people with any power of observation, part of you probably does want to sleep with me personally."

I scoffed loudly and made a dramatic exit back inside, rummaging aimlessly through the cupboard in search of my thoughts more than breakfast. After a minute or two I heard the sliding door close, and Mom wandered back in, her cheek mixed with concern.

"I'm sorry sweetheart, I didn't mean to make you uncomfortable, I thought you could handle some teasing, isn't that what you're always telling me?"

I turned on her and fought to control my anger, rising to the obvious challenge

"Don't worry Mom, I'm the one that's sorry for making you so uncomfortable this past week, I thought you could handle being sexually open with me, isn't that what you're always telling me?" I spat back at her.

Breaking into a broad grin, Mom put her half-eaten bowl of muesli on the counter and looked me square in the eyes, her tongue moistening her lips in a way that I couldn't help but notice.

"Ok then Matthew, do you honestly believe you can handle being that sexually open with me? I'm willing to take it if you can." She was challenging me in the most obvious way she ever had, but I was too fired up to even consider turning her down.

"Of course I do! You're the one that got all weird about it, remember!" I practically laughed back at her.

"Ok then, being perfectly open with me, let's talk about why I'm wrong in saying you have a little crush on me."

My face must have fallen a little or something, because she was onto me and pressing home the advantage before I could even form a sentence that was decipherable from nervous gibberish.

"Since you're not uncomfortable talking to me about sex, I'd love to know what elements of the Oedipus complex you have and haven't explored... have you spied on me in the shower?"

My face threatened to burn up, but I was every bit as stubborn as her, so I held firm.

"Once or twice when I was 15, yeah."

"Ok, I know for a fact that you've listened to me having sex at my bedroom door."

"Sure, anything else then Dr. Kerry Freud" I tried to mock her in return, but it had no impact on her whatsoever.

"I hear that some boys try to sneak cum into their Mom's food so they can get off on the idea of her eating it, have you ever tried that?"

By this stage I was feeling pretty unshakeable, so I confidently told her that I'd never even thought about it, and as much as I see that she's a gorgeous woman, I'm obviously not Oedipus and I'm not uncomfortable.

As true as that statement was, it didn't stay true for long.

"I can see that Matthew, I'm very impressed, but if you haven't tried it how do you know you don't feel that way about it?" I didn't register what she was saying until she picked up the bowl of muesli again.

"Since we're so comfortable with one another being open like this, maybe you should top up the yoghurt content of this for me, and we'll find out if you like the sight of me swallowing it?"

I don't know what words I used to try to seem unfazed, I don't know how much I denied any interest in the idea, but the beginnings of a erection were obvious against the thin boxers shorts I was wearing, and to compensate for that I could only agree 'off-hand' to try it, even just because she wanted to know.

I reached for the bowl and headed for my room but Mom stopped me with a raised eye-brow.

"You didn't have a problem with me watching you last week?" she suggested, and I knew in the pit of my stomach I had to do it right there in front of her.

"I was just going to get some Porn..." I offered weakly, only to have Mom offer to show me her breasts to see if it would help.

Even the mention of it helped significantly, and soon my boxers were practically hanging from the end of my cock rather than covering it.

Stepping nervously out of the discarded underwear I positioned the bowl of muesli nearby and began to stroke my shaft, trying to seem casual even as my Mom rolled up her tank top to reveal her perfect breasts, the nipples growing hard in the cold morning air and the top pressing down slightly to enhance the roundness of the D cup beauties.

I don't know what was a stranger sensation, locking eyes briefly with her as she bit her lip and blushed slightly in sympathetic pleasure, or when her blue eyes lingered on the movement of my hand along the length of my throbbing cock, and the look in her eye that filled me with so much self-assurance.

Without a word one of her hands slipped down beneath the waistband of her shorts and as her finger entered her pussy her lips parted and a gentle gasp of pleasure reached my ears.

In that moment I shuddered, closed my eyes and thick globs of my cum shot out into the bowl, strands and drips of more watery semen following until I was panting heavily, my empty cock rapidly shrinking again as I reached for a tissue to wipe myself clean.

When I looked back up, Mom was dressed again, no sign of having continued to masturbate, and she was reaching for the bowl, seeming to admire the new topping with a practiced eye.

"You are a healthy young man, aren't you?" she smiled, and somehow it was a sincere complement.

"Are you going to eat that?" I asked, not sure whether she had already proved a point or not.

"Of course, anything my son puts so much effort into preparing for me, I will eat happily" She grinned, and as I watched she used her spoon to scoop a large amount of the cum off the top, taking barely any muesli with it.

As the spoon reached her mouth she closed her eyes and tipped it, letting the cum slide off the spoon and over her lip and tongue down her throat before sucking the rest off the spoon itself. With a murmur of enjoyment she swallowed it all down and began mixing the rest of the cum through the muesli before pausing to regard me again.

"You taste good, and I'll leave the discussion of whether you enjoyed watching me for another morning. I'm glad you're so comfortable being open with me Matthew."

Again, she was being sincere and I had nothing to say to her in reply.

"And sweetheart, if you ever have any other questions about sex, please do feel free to ask me." And with that she took the muesli back out into the sun to finish in peace.

For the next week and a half the feelings awakened by watching Mom gulp down that cum soaked muesli drove me back into the world of dimmed lights and internet pornography. Always thinking of her.

Porn of my had Mom given me the fright of my life once upon a time, browsing through the retro magazines of my Father's collection when holidaying at his house one summer I found a photoshack envelope with only three developed shots inside it, all of them the teen version of my Mom laid out on the bed with her nubile pink nipples bared on her then C cup breasts, pink underwear covering her thatch of pubic hair in one of the three photos, while she bent over the bed with her tight pussy showing in the last shot.

I may be exaggerating the quality of the photos of course, because all I really remember seeing was the familiar face of my Mom looking barely 18, and poses that strongly resembled those in the centrefolds nearby. At that point in my life, even the fantasy of incest was shocking and unappealing, and I didn't masturbate for a week and a half after that.

Years later when the secret urge to see her sexualised burned within me, I started searching the old photo albums and envelopes in my Mom's collection, book marking the page with her in a classic bikini and almost yelling for joy when I found the photo of her sunbathing topless in Cancun. Moving house and remarrying so many times will lead to a constant turnover of what other people might consider prized memories however, and within a year of my discoveries the photo albums and the young breasts of my Mom were gone, never to be seen by my horny eyes again.

Of course, all that was in the past.

Having seen the full 38D breasts of my more mature Mom only last week, not to mention the satisfied smirk that played across her lips as she casually ate my cum as if it were a rich and creamy yoghurt, the need to see her and have her was eating me alive.

Outwardly I was the same arrogant young man, teasing Mom with my muscled upper body as I swam in the pool, not hiding my morning glory before giving her a loving hug and a peck on the lips before breakfast. But inside it was all I could think about.

I tried spying on her in the shower, but there's no keyhole and the window is frosted.

I tried listening to her masturbate and have sex, but mostly she just went to her boyfriend's house for that, and otherwise she just had longer showers.

A few times I pumped more cum into her food or drink to serve her while we watched DVDs of an evening, but if she noticed the taste she didn't make anything of it.

Mom's ass in the air and her back arched during yoga became a spectator sport, but I still couldn't justify getting my cock out and jerking it while watching her there in the living room, so I just got horny and frustrated.

Her cleavage held tight by her bikini top as she emerged from the swimming pool, her tanned skin glistening with the water as she gently rubbed herself dry with a towel.

Again I was powerless to do anything but watch, and wait under the surface of the water for my raging erection to subside.

Which brings me back to porn.

In the absence of having any control over fucking my actual Mom, I stopped looking at tall blonde teens and started obsessively searching the internet for MILFs that looked like Mom. I searched by height and bra size, I only wanted brunettes and I needed the breasts to be natural so they would look the same as my painfully arousing memory.

I couldn't find anything like what I wanted.

I even spent two hours in photoshop attaching my Mom's face to the most similar pornstar body, and only after cumming all over a fistful of tissues did I realise how pathetic I had become.

It wasn't anyone's fault but my own, I still loved my Mom, she was more beautiful and fantastic than ever, smiling and laughing in that way that always made me feel better about myself, but with enough of a harsh ridicule that I didn't feel pitied.

Over dinner that night I was almost ready to take my plate into the cavern my bedroom had become, to delete the photoshop abomination and search the internet for a better alternative when Mom's small fingers grasped my wrist firmly and she fixed her kind blue eyes on mine sternly.

"What is it Matthew?" her tone suggested that she needed to know, right now. But there's no way in the world I would ever tell her the exact reason for that particular melancholy, so I made do with a forced smile and a brush-off, but it didn't work.

"It's a girl thing isn't it. I've noticed you haven't been bringing anyone home this last week or so, and you're certainly spending a lot of time on the computer in your room. Did some girl break your heart? Or have you suddenly decided that porn is better than sex?" The last part was delivered with a cheeky smile. She obviously knew that wasn't the case, but she also wanted me to know my activity of choice was obvious too.

"Nothing like that, just not feeling it at the moment is all." I managed to admit.

"Well, if you want to save the internet usage for more constructive downloads and you feel like a technological challenge to take your mind off the porn for a while, I'm sure the computer in the living room must have some porn hidden on it somewhere, you know what Geoff was like." The fact Mom was still so open and comfortable with talking about masturbation and porn with me was reassuring, and the mention of her ex didn't actually worry me as I realised she was right. What used to be the "family" computer had been used only by Mom for checking her e-mails since I got my own set-up in my bedroom, but the hours of porn the Geoff had downloaded wouldn't have gone anywhere. I smiled at her and couldn't help but laugh.