Hashtag No Makeup

(Author's Note: All characters in this story at are least 18 years of age, and, even in role play, are "playing" characters at least 18 years of age.)

*****

It was a comment so unexpected, that I couldn't help but react unexpectedly. In hindsight, Mom was probably already a few steps ahead of me. But in the moment? In the moment I was just stunned into honesty. It was the last out of town sporting event of the year. I was traveling with my whole team, but because Mom was a chaperone for some of the attached events, she and I shared a room instead of me having to room with 5 other guys.

Anyways, the first night rolls around, and I am, as always with this trip, nursing a sore hand from having to smack so many guys for commenting on my Mother's amazing looks, her incredible tits, her long hair, her perfect ass, and just, on and on and on. The burdens of having a sexy Mom, I know, there are worse problems. But, I was mildly concerned myself, because there was a huge difference from going to my room at night to masturbate to whatever I wanted to, and going to my room at the end of the night where my Mom was going to change into her "nighttime wear" and be sleeping in the next bed.

So, that night, Mom, as always, was being flirty. It was just her personality. She never meant anything by it, but it was one of those things that made some women resent her and most men adore her. It didn't really bother me until I was about 14. But now... now I was doing my best to either not get hard in a room with my Mom that I couldn't flee from, or at least 'think the hard-ons away' as soon as I got them. Or hide them or... the whole thing was, er, hard on me.

Anyways, the comment. So, Mom and I have a good time, we talk, we laugh, we make fun of awful hotel T.V. channels, and then, out of flippin' nowhere, Mom warns me in a seriously self-defeating tone, that I had better prepare myself for how ugly she was going to be when I woke up, because she was, and I quote, "Hideous" without makeup on. Now, honest reaction? I was mad. Who the fuck made my Mom think something so fucking stupid?!? But then, of course, she answered it when she told me that, no joke, Dad told her the other day that he couldn't titfuck her in the morning unless she put some makeup on, because she just wasn't that pretty without it.

So, there we were, and I was high on anger, and horny, and horny, and also very supportive of my Mom, and somehow, that all culminated in (did I mention I was like, teased all night, stuck on a bus with no way to jerk off for the last 2 days, HORNY?) my saying that Dad was an idiot. That what he said was total bullshit, and that I would fuck her tits morning, noon, or night, makeup be damned!

...

Yeah. Try recovering from that... Mom was, understandably, shocked, but then, then she shocked me, a LOT, by rolling with it. After a long pause, she told me that it was very sweet of me to say so, but that defending Mommy and actually thinking something were not the same. Which put me in a weird place, because now my only options were: back down, or, double down. And, fuck it, I chose the second one! I told her that I knew what I was talking about. That she was sexy, and gorgeous, and beautiful, and her tits, hair, ass, just, just fucking EVERYTHING, was AMAZING!

But again, she pushed back. And this time, she was the one who doubled down. She said that I could say it, but it was easy to say something, and harder to prove it. Which, again, backed me into a weird place argument wise. I mean, the debate was escalating... and because of my idiot phrasing, the debate was about me having sex with own Mother's, admittedly gorgeous, breasts. Still, I wasn't about to back down and leaving her feeling down. So, and, I know how weird this is... but I doubled down. I told her that I would LOVE to show her that I was telling the truth.

She smiled, told me I was sweet again, and said I'd feel differently in the morning. Then, in that Mom way, she used her 'Mom powers' to end the conversation before I was done talking. She just told me that we'd talked enough for one night, and that it was rest time. Then she kissed me on the forehead, shooed me into bed, and turned out the lights.

Suffice to say, I was awake for hours thinking about it. And the next morning, I woke up an hour before the alarm went off, and thought about it some more. When Mom woke up the next day, she did so when I sat on the bed beside her. She greeted me, a little sleepily, and pulled her sheet up a bit (Mom always sleeps naked, even at a hotel). In reply, I told her that it was morning, she didn't have any makeup on, and she was still gorgeous. She smiled, and maybe even blushed, just a bit. But she told me, in shockingly blunt terms, that being a 'pretty mommy', and being beautiful enough to want to see her sucking a cock or tittfucking me were not the same thing. So... I actually stood up on the bed, and pointed to my erection. I was wearing just boxers, and I was more than a little hard. I asked her if she thought THAT was lying too. And, the faces Mom made while looking at my hard dick, well, I mean damn. They only made it harder. And when she told me that I'd, "certainly grown", and bit her lower lip like she was craving what she was staring at... that may have been the hardest I'd been up to that point in my life. But I could still hear her doubt, and see her preparing to give some kind of come back... So I escalated the situation.

I told her to pull down the sheet if she didn't believe me, and, after a moment, she bit her lip again, pensively this time. Then, she looked like she'd decided something, and, out loud, she said, "Okay then". And a moment later the sheets and blankets weren't even on the bed anymore. She was laid out naked beneath me, her sensuous curves, lovely skin, and incredible breasts all just laid out before me like some kind of heavenly banquet. So, sort of testing the waters, I reached for the waistband on my underwear, and when I paused, Mom just smiled and raised one eyebrow as if to say, "I'm waitinggggg". So I stopped making her wait.

I stripped down, and when she still looked expectant, I got down on my knees, and positioned my dick so that was where it needed to be in order to slide in between her cleavage. After a moment, I reached for her breasts, but Mom loveling moved my hands aside when I tried to touch her breasts. I thought, "well shit, that ends this". But then she said, "That parts my job sweetie." And then my Mother's large warm tits came up and wrapped my cock in a pure, soft, paradise of pleasure. I'm sure I moaned, but Mom just smiled, a sinful little smile, and began to gently stroke me off with her tits.

I told her how gorgeous she was, and how hot this was, and how incredible it felt. Mom, for her part, seemed genuinely surprised at first. "You really think I look pretty like this?" she asked. Her tone painfully sincere. So I told her exactly how 'pretty' she looked. I showered her with compliments. I told her everything that every guy friend of mine had every told me about her. I talked about all the parts of her that never used makeup and how they drove men wild, even me (especially me)! I told her how hot she was, and how many people lived for her casual flirting, and how I'd seen her without makeup for years and never thought she was less than Goddess levels of sexy. I told her the truth in an endless, honest, stream. And as I did, she got more confident, and more turned on, and more into it.

So eventually, I had to tell her that I was getting close. "Are you really?" she asked. Her tone going from shocked, to sultry a little too fast. "Are you getting close to cumming on my face and tits baby? Are you going to cum for me? Cum for Mommy? Think you could give me a pearl necklace when you do?"

And long before she was finished talking, I was screaming into my arm, and biting down, trying desperately to not be heard by any of my teammates in the rooms on any other side of us. I was muffling myself and yelling, and cumming all over my Mom, and she was looking up at me with a mix of delight and surprise as she kept saying that she couldn't believe I was cumming on her, while also telling me how good it felt, and how much she loved the feel of my hot cum on her skin.

When it was all said and done, Mom kissed me like nothing had happened. Then she thanked, me, told me I was, "SO sweet", and went to shower. The whole next day, Mom acted like nothing happened. We went to some events, toured the local tourist crap with the team, played a game (we won), and eventually everyone went back to their rooms. Honestly, I was afraid to say anything and starting to wonder if it even happened. Then, just before Mom turned out the light for the night, she kissed me goodnight, and said, "Hey honey... Maybe tomorrow you could let me know if you think I'm pretty enough to give you a blowjob first thing in the morning. What do ya say kiddo? Think Mommy's lips are good enough to suck your cock without any lipstick?" And before I could answer, Mom smiled at me, gave me a conspirators wink, and turned the light off.

The next morning, I knew words would be useless, so I decided to SHOW Mom my answer...