I can't say for sure when it started. I had always had dreams of showering with mom, looking at her, hugging her, ever since I was a kid. It wasn't until I was 18 that it became more of a sexual desire, wanting her naked body against mine. Kissing her neck, feeling her breasts press against my chest as she whispered in my ear. That was the dominant fantasy through my early adult life (though certainly not the only one).
I have tried to leave hints in the past- hugging a little longer than usual, kissing her cheek, putting my hand over my crotch whenever I saw her- but they seemed to have been missed. Maybe my mom was incredibly naive, or maybe my mom knew exactly what I was doing. The latter is the reason I hadn't acted on anything, despite how hard I've tried.
My first attempt was in senior year of high school, when my mom would wake me up every morning. I thought that one method would be to fall asleep masturbating, and when she came into my room, she'd see my cock, dripping with cum, something I thought would at least really turn me on, if not her. But the night that I had masturbated, I got that post-ejaculatory guilt- guys, you know the one. The one that made you say you'd never jerk off thinking about your mom again. That is, until you did it again.
My second method would be to walk in on her while she was changing. My mom had a habit of leaving her bedroom door cracked while she was in there, even when she was changing (something I mistook as a hint, but dismissed out of paranoia). One day I had walked in and, fortunately for me, she was changing. She had her back turned towards me, so all I saw was her bare back and her beautiful ass- I have skirted descriptions of my mom for a reason, and that was to describe to you how absolutely gorgeous she was when I finally saw her naked, but, we'll get there. When I had opened the door, I realized the door didn't make any sound, and in my typical fearful and pessimistic mind I immediately thought the worst would come of the situation, so I just left back to my room before she noticed. Some days I wondered, perhaps she saw the door was opened slightly more than before. Maybe she liked that it was. I know I did.
My final method was to take a shower and walk around with just a towel, until I accidentally drop it in front of my mom. This plan was almost executed, my cock semi-hardened for maximum impressiveness (not that there was that much, but it was the biggest I could make it while giving it some sense of candid flaccidness) until I was looking in the mirror after my shower and realized I wasn't exactly in the best shape. It was kind of a depressing sight, and I thought, even if my mom did have the inclination to fuck her son, she probably wouldn't want to fuck someone like this. So, with a sigh, I just got dressed as usual.
After that, I hadn't really made any effort to do anything. Instead I would just masturbate twice a day or so, once when I got back from school and once at night, after I could see my mom. This largely occupied my senior year of high school, into the beginning of the summer.
I mark that as the end of the period because something happened at the beginning of the summer. It was late June, and I was turning 19 (I wasn't held back a year, it's just that the school district I entered in kindergarten was weird). My mom was a single woman, working an office job, so understandably cash was a little tight. She was talking to me over dinner a week before my birthday.
"So, the big 1-9 is next week, you excited?" She said, cutting into her piece of chicken.
"It's not really a big year. 18 and 21 are the biggies, everything in between is kind of a wasteland."
"Well you can buy alcohol in Canada, right?"
"Mom, we live in Virginia. I don't even have a passport. When am I gonna find the time to go to Canada?"
"Well," she said, "at least you aren't reaching my age. Once you blow though the 41s, 42s, 43s, the only milestones are the ones that remind you your ten years closer to death than the last time you celebrated anything."
"Huh, that's weird mom, I thought you were 33."
"Oh stop it. This isn't about flattering me. This is about your birthday and what you want for it."
"Mom, you don't have to-"
"Uh uh, zip it. You aren't grown up enough yet to turn down birthday gifts. Now I do hope you realize that money is a little tight, so the cheaper the better. Well, the cheaper, the more likely I am to get it for you."
"So, a car?"
"Not a chance."
"A Rubik's cube," I say jokingly.
"Now we're talking."
"What if I wanted something free?"
"Tell you what, I will get you anything you want that's free. I'll even get you two of them."
"Big spender." "
"Anything for the birthday boy."
"Now when you say anything, you mean anything?"
"I'd pinky promise on that mister."
"...Alright, I'll think about it."
In reality, I didn't have to think about it. I knew exactly what I wanted.
But asking her for it would prove a little more difficult. I don't think she had the same 'anything' in mind as I did. In fact, I was very iffy on the idea that she would even be okay with it if I just told her my fantasies, let alone if I asked her to act it out for me.
So I came up with the perfect plan.
About four days later, three days before my birthday, I decided to tell her what I wanted for my birthday.
"Well, I want to have sex. I'm a virgin, and I don't think it's alright for me to be going into college without this kind of experience."
"I mean, I think you know about the birds and the bees. How to put on condoms, all that."
"It's not the technicalities mom, it's the confidence. I'm afraid I'll be in that position and, well, not do so great."
My mom mulled over for a second.
"And," I interjected, "it doesn't have to be like a prostitute or some hot young girl. It could be one of your friends. One of your more attractive friends, preferably, but not necessary."
"Do you have an age limit in mind?"
"Let's say 50 is pushing it," I said, still surprised my mom is even considering it. I very easily could've jumped ship and taken the Rubik's cube at this point.
"I'll see what I can do. But you might not l be able to be picky. Beggars can't be choosers."
"I totally understand. Just, please, not Nikki."
"Ooh, lemme text her now, see what she's doing this weekend."
"Please mom. Don't."
I planned it perfectly. My birthday was on the Monday, three days from now, so my mom wouldn't be able to see most of her friends she works with this weekend, and wouldn't be able to ask them. Not to mention it was a three day weekend, so I'm sure a lot of her friends were out of town. Even if they weren't, knowing my mom, she'd probably be too embarrassed to ask them herself, maybe even rather doing it herself than asking.
Sunday, I asked her how her search was.
"Well, it's not going great," she said, taking a bite of her Chinese takeout, "but I do have one possibility in mind."
I swallowed, realizing my plan had been foiled. Well, at least I'll have sex.
"It's a surprise. But you have to realize I've been pulling out all the stops. You better appreciate your old lady and everything she's doing for you."
"Oh, I do mom."
"Good. Remember how much you appreciate me tomorrow. It'll be needed."
That night I couldn't sleep. Who had my mom picked? I was still in awe at the thought of my mom picking out who I was going to have sex with, at some point imagining me having sex. It made me want to rub my cock, thinking of her, maybe even masturbating, imagining me fucking some other woman while she was in the other room. I didn't though- I was saving my cum for the next day, my birthday.
At some point I fell asleep, and had a very vivid sex dream involving my mother (that I won't describe- saving the juicy details), ultimately leading to me cumming in my underwear. So much for saving it.
My mom woke me up that morning around 9. She was sitting in my bed while I was half under the covers. When I realized she was there, I covered myself more to hide my very apparent cum stain I had noticed.
"Happy birthday baby."
"Thanks mom. What's for breakfast?"
"I wanted to talk to you a little bit first, about your present."
"Oh right. When are they coming over?"
"Well... I couldn't find anyone. To be honest, I didn't even ask anyone. It felt weird to even talk to them about it."
"Oh... That's alright, you didn't have to."
"Well now, I said I'd get you anything that was free, and technically, this was a free request. So, I thought, just this one time... Maybe I could help you out."
I was stunned. I couldn't even get the words 'fucking yes, please' out of my mouth.
"You don't have to say anything dear, just let your mom take care of you."
She lifted the blanket, and started rubbing my crotch, feeling the wet stain on my underwear.
"How about we take these off?"
I quickly took them off- a little too quickly, showing my gusto for her advances. My cock was already pretty much hard, only becoming fully erect when she gripped her fingers around my cock. Instantly, feeling her warm hand on my cock made me close to cumming, despite the fact that my last load was still wet in my underwear.
She continued to stroke my cock, running her thumb over my head as I dripped pre-cum, smoothing it over. She leaned in and planted a kiss on my cheeks, which instantly sent a wave of pleasure over me. I hadn't realized I had cum until I opened my eyes, and I saw my mom licking her fingers. Fuck, I thought. My one chance. And I came too early.
"Damn it mom, I'm so sorry."
"It's totally fine. And technically, it wasn't sex. It was just a handjob. So, maybe we can do this later, when you're up for it."
"Alright, thanks mom."
"And don't curse. It isn't as sexy as you think it is."
"So, how about some waffles and bacon?"
I threw on a pair of shorts and a shirt, and walked downstairs. I sat at the table as my mom poured some batter on the waffle maker. She put some bacon on the plate, still a little warm, and put a dollop of whipped cream and some strawberries on the side. She waited a little for the waffle to be ready, and while she leaned against the counter, I was looking at my mom's body, for once not worrying about getting caught.
This is the part, before I continue with the sexual descriptions, where I describe how inexplicably gorgeous my mom is. She has the beautiful wavy brown hair down to her shoulder, and piercing blue eyes. She has incredibly plump lips, and beautiful freckled skin, especially on her chest. She has wonderfully round breasts, not too large, not too small, and a beautiful ass, certainly something to grab. (If you're trying to cast the image in your mind, imagine Vera Farmiga.)
The green light on the waffle maker turned on, and my mom opened it up and put it on my plate. She put the plate in front of me as I poured a glass of milk.
"Eat up," she said, "you have a long day ahead."
"Is that so?"
"Well, you might as well make the most of this one gift that I owe you. If you don't count oral as sex, like I don't-" in this moment I feign thanking God, which she responds to with a 'pfft'- then we could do breakfast, some oral, lunch, then your choice of taking a break and watching a movie or something before dinner, then fucking after, or fucking before and having after dinner as a cool down."
"Swearing isn't sexy mom."
"Really? It isn't sexy when I say I'm going to fuck you, baby?"
"Well, maybe a little."
"So it's up to you whatever you want to do."
"Could we, maybe, at some point shower together?"
I scarf down the waffle, and as I eat the other one, I talk to my mom more.
"Since we'll be, you know, having sex, could I see your breasts?"
"Well, first of all, thanks for not calling them 'tits'. And I don't see why not. How about I show you one now, and you can see them both later when we shower."
My mom then, with no hesitation, pulled one of her breasts out of her blouse and let it hang in front. Thankfully, she didn't mind that I stared. Her breast was perfect; perfect round areola, the nipple hard and pointing out, the skin around it so smooth. I would've touched it if I didn't have a fork in my hand.
"I'm glad you enjoy it. I thought I was losing my perkiness."
My mom smiled and turned her head, but I could tell she was blushing.
After breakfast, I suggested we took a shower together. We walked into the upstairs bathroom and undressed in front of each other. I watched as my mom pull down her skirt, revealing a pair of black underwear, then unbuttoning her blouse, to reveal a matching black bra.
"Someone wanted to impress."
"I wanted to look sexy for my son," she said with a smile. She does look very sexy- especially in black.
As she stripped those, I looked at my mom in her entirety. Her beautiful body was so close to mine that, had I not given myself some room for my incredibly hard cock, we would've just been a few inches apart.
She got in the shower first after letting the heat warm up, and I followed her in. Her back was to me as she faced the water and I wrapped my arms around her waist and kissed her neck. My cock dug into her ass as I held her tight.
"Thank you mom."
I ran my hands over her breasts, finally, feeling their weight in my hand. I rolled her nipples between my fingers as she rolled her head back and kissed my cheek.
I moved my hands down her stomach, over her small patch of pubic hair, and I felt her lips parting at her clit. I slowly rubbed it while warm water ran over my hand. She put her hand over mine-initially, I thought she was going to stop me, but instead, her hand moved with mine, and she pushed me to rub her harder.
I slowly rubbed her clit, deep, hard, as I kissed her neck, until I alternated to fast, light rubbing. I felt my mom squirming with pleasure in my arms, with each one running her hands over herself, her neck, her chest, until I could feel her coming close. I gave a fast, hard movement on her clit as she grabbed my forearm and opened her mouth in pleasure as my mom's knees weakened and an orgasm flushed over her. She turned towards me and kissed me, deep, harder than the kids from this morning, and turned me around in the shower so that my back was to the water.
My mom dropped to her knees and held my cock in her hand. She kissed up and down the length of the shaft until taking the head in her mouth and licking it. She took it out, looked up at me, stroked my cock, then put in her mouth slowly again. As she sucked it, I ran my hand through her hair, grabbing the back of her neck as her tongue ran up and down the length of my cock. She moved her head in and out slowly with her hand on the base of my shaft, moving it back and forth. With her other hand, I could see she was playing with her clit, and with her next orgasm I came in her mouth, shooting my cum down her throat. She sucked on my cock, running her hand up it to tease all the cum out of it. She swallowed, looked up at me, and stood up. I turned around as she stepped out and turned off the water.
"Do you wanna lie down for a little bit?" I asked my mom.
"Sure. I wouldn't mind a little downtime."
We walked into her room and got under her sheets.
"Do you like sleeping with your mom?"
"It's really nice. I like feeling you against me."
I spooned my mom, my cock against her back, as I slowly fell asleep.
When I woke up, my mom wasn't in bed. I got out and walked downstairs to find her in the kitchen in nothing but an apron.
"Finally," she said, "I was wondering when you wake up."
"What did you make?"
"Thanks for the nap too."
"Oh yeah, right, I'm sorry. Thanks for the nap mom. It was really nice."
"Clearly, since you slept so long," she said with a smile. "I made you a bagel and a smoothie."
She placed the smoothie in front of me right as the bagel popped. I watched her as she took out the bagel from the toaster, then bent over into the fridge to get the cream cheese. She took it out, smeared it on the bagel, and placed the plate in front of me.
"So have you figured out what you want to do?"
"For what?" I said, after swallowing a bite of bagel.
"For our schedule. Before or after dinner?"
I paused for a second with a long drink of smoothie. "Well," I said, "why not both?"
"Come on now. I said once. One time."
"Fine. How about before dinner?"
"Works for me."
"Can you do me a favor mom?"
"Could you put a foot up on your chair?"
"Like this?" She said, giving me a full view of her pussy.
"Yeah, then could you just, um, play with it? A little bit?"
Without a word, she looked at me and moved her hand down her thigh and started rubbing her clit. I watched as her fingers moved up and down the lips of her vagina, as she massages her clit with her thumb. She then slides two fingers into her pussy, deep down, keeping eye contact with me. She starts rubbing her clit harder, angling her fingers upwards. She starts breathing harder, running her hand over her body, down her breasts, squeezing her nipples, until she comes, breaking eye contact to close her eyes, feeling the orgasm fill her body.
"I think we should head upstairs now," I said. My mom nodded her head, and we got up to go upstairs, my bagel and smoothie unfinished.
We opened the door to her bedroom and instantly we fall in the bed, kissing. I immediately spread her legs and run my cock over the folds of her pussy.
"Are you ready for this baby?" My mom whispered to me. I nodded my head as my cock slid inside her slowly. I felt her warm pussy over my cock as I slid in and out of her, feeling her push back into my pelvis with each thrust.
"I've wanted to fuck you for so long, mom," I said, telling her my feelings for her, something I've been wanting to do for so long.
"Fuck me baby, fuck your mom like you've always wanted to fuck her."
I wrapped my arms behind her and fucked her fast as she moaned so loud. She wrapped her hands around my back and dug into my skin with her nails, grabbing me as hard as she could. I moved my arms to her lower back and pushed harder into her with each thrust, faster and faster. I felt my mom come on my cock, her pussy quivering as she sighed deeply.
"Let you mom take care of you," she whispered into my ear. I turned over and my mom was in top, poised over my cock. She slowly lowered herself onto it, feeling it fill her, as she looked down at me and ran her hands up my chest. She grinds her hips and I feel my cock moving, pushing against her. She leans down, and kisses me, grabbing my torso, and bouncing her pussy on my cock while looking into my eyes. I could feel my cock going in and out of my mom's pussy as she fucks me hard, and she comes again, angling my cock upwards into her pussy.
"Are you going to come for mommy?"
"Yes," I said, "I want to fill you up mom."
"Fill me with your cum."
She got off of me and I turned over. I pushed her face down onto the bed, climbing on top of her, mounting her behind her ass as she kept her legs straight. I guided my cock into her pussy again as she moaned. I wrapped my arms across her chest as I kissed my mom's neck, face, shoulders. I thrusted deep into her, feeling her ass bounce back with each push.
"I'm going to come mom. Fuck, I'm gonna come."
"Fill your mommy's pussy, sweetheart. I want you to come deep inside me."
With some more final thrusts, I fill her pussy, as she shakes from the times she came. I collapsed on top of her and hold onto her as we slipped into a half daze, just feeling each other's body. I felt like this was natural, feeling my mom's body against me. I felt like it would be right to always feel this.
I fell asleep again, tired from the sex, and this time woke up to my mom in bed with me.
"Dinner's ready, do you wanna come down and get some?"
"Yeah, I'm actually kinda hungry for some reason."
"Well, you broke a sweat."
"Now that we had sex, do we have to wear clothes again?"
"I'll let it pass until tomorrow."
"Thanks. What's for dinner?"
"I ordered some pizza."
"Mm. My favorite."
"You should've seen the delivery boy when I answered the door."
We walked downstairs. The Pagliacci's boxes were stacked on the counter, and I grabbed a plate and a slice from the top box.
We sat down at the table, and I asked what this would mean for us.
"Well," mom said, covering her mouth while chewing, then taking a second to swallow, "I'm still your mother. That's not gonna change no matter how hard you try. If you want to use your birthday and Christmas wishes on these things from here on out, feel free to."
"And, of course, you'll always cheat a little bit on that."
"I will clearly say I won't ever do this outside of birthdays or Christmases."
"But is that the truth?"
"That's besides the point."
I smiled at my mom as we kept eating the pizza. As we say on the couch, watching TV, she leaned against me and I wrapped my arm around her shoulders.
"So that's it for today?"
"That's all you get. We can touch each other, but no sex. Oral is still a little iffy."
"You know," I said, "when you told me I could have anything that's free, you specifically said I could have two of it if I wanted."
She looked at me and smiled, then said, "do you want to go upstairs?"