A BRIEF MOMENT OF BRAVERY

A BRIEF MOMENT OF BRAVERY

I had not a ton of luck with women. I mean, I got looks, and I did a lot of the things that guys are 

supposed to do. But no matter how likely it seemed that she would totally yes if I asked, I had a 

lot of trouble asking. To make matters worse, my Mom pointed this out to me when I was like, 12. 

In fairness, she was trying to be helpful; but it just seemed to make it extra embarrassing for me. 

Over the years, my anxiety at asking a girl out didn’t get much worse, but it didn’t get better 

either. Then, when I was 18, about to turn 19, Mom kind of cornered me one day while we were 

on vacation. She told me that before the week was out, she was going to cure me of my 

shyness, once and for all. 

It sounded more like a threat than an offer, but it wasn’t like I could stop her. She was my Mom. 

Even at 18, what she said kind of went. I mean, not because she was mean or anything. The 

opposite actually. Mom commanded respect by being a sweetheart. She was honest, and bold, 

and kind, and thoughtful. People WANTED to do things for her, and hated disappointing her; and 

as her Son I was no different. Hell, if anything I was even more in the dying to please her camp 

because, well, she was my Mom. 

Now, there Mayyyy have been a second reason too. See, the male brain is a wonder of science 

and stupidity. We have this habit to try to impress pretty women, even complete strangers, no 

matter what our or their social standings or circumstances are, and this instinct is both strongest 

and stupidest in a teenager. And Mom, Mom DEFINITELY qualified. She had long legs, pretty 

eyes, a knockout smile, and tits so large and lovely that they made people groan, out loud, in 

pleasure, at the mere sight of them! 

Anyway. All that week, Mom offered to pay for cool stuff; but I had to ask. It was like being teased 

about something, but then getting rewarded for going along with it. “Want to eat at that restaurant 

you’re always pining over but we can never afford? Well, ask me if we can… Good. Now ask me 

again, but prettier.”

Her tone was flirty, almost sultry, so it was hard to get mad. Like, on paper it would have looked 

so insulting, but when a busty goddess is purring it in your ear, and then buying you awesome 

stuff when you play along, “offended” isn’t on the list of reactions. 

She did it with ice cream, with expensive dinners, with cool rides, scuba lessons, jungle tours, 

and the list went on and on. Everything I’d ever wanted to do, if I worked up the courage to ask 

her, and then stood my ground and asked her again, but nicer (it didn’t matter how nice I asked 

the first time); then her answer was always yes. 

Then, four days into our five day vacation, Mom, who had a lip piercing that she sometimes 

used; was walking along this amazing little bit of secluded beach with me, as I tried to pay 

attention to what she was saying. It sure as hell wasn’t easy. Mom was wearing her piercing, a 

pair of tiny black shorts that gripped her amazing ass like nothing I’d ever seen, and a tiny 

swimsuit top that managed to show considerable levels of underboob, while also teasing the shit 

out of anyone who looked at it’s zip down front. I swear, you have never seen a zipper begging 

harder or louder to be tugged downward then the one that was holding my Mom’s breasts 

together that day.   

Then, out of nowhere, Mom told me that she had some new piercings, and asked if I wanted to 

see them. I started to say sure when, I realized exactly what I just told you. Teeny tiny shorts, 

teeny tiny top, and not a new piercing in sight… Then Mom told me that if I wanted to see them, I 

needed to ask her if I could. 

Right in that moment, I didn’t give a shit if she was my Mom. I’ve never wanted to see anyone's

pierced anything so bad in my whole life. So I worked through my anxiety, and asked her. When I 

did, she told me that it would be much nicer if I sat down in the sand, and asked her again, with a 

please. And, fuck yes I did. I parked my ass on that sand and I asked again, but nicer! 

When I did, Mom leaned over me, giving me an amazing view of, well, EVERYTHING. She was 

so fucking hot. Her eyes were gorgeous and seductive, her voice was doing this super seductive 

tone that was killing me, and when you add her legs, her ass, and those amazing tits… I was 

looking up at heaven. 

Then, the angel in front of me said that she couldn’t show them to me, unless I asked her 

something else. Then, before I could even ask what that might be, she told me to ask for 

permission to unzip her top.

My heart was in my throat, and the temperature inside my head had just jumped to 20 degrees 

warmer than the beach. I thought that she had to be kidding, but before I could ask if she was, I 

realized that I was more scared of her saying yes, than no. So, I risked it all, and, knowing that 

she might be fucking with me, I still went ahead and asked her if I could unzip her top. Then, 

without any more questions or teasing, she just looked me in the eye, and with a word so sexual 

it half sounded like a moan, she said “Yes”. 

I didn’t try to unzip it insanely slowly, but the teeth seemed to take forever parting. Slowly, the 

zipper crept downward, and more and more of her cleavage line appeared. More and more of 

her breasts opened themselves up to my eyes. Then, very suddenly, I hit the end, and after a 

second, the material just kind of popped away; like a sling being released. 

Mom reached up and ran a hand through her hair, smiling down at my reaction as I stared at the 

two biggest and most beautiful tits I had ever seen, both in and out of porn. “Do you like them?” 

She asked, obvious confidence in her voice. “The piercings I mean”. And, sure enough, she’d 

gotten her nipples pierced and yeah, I fucking liked them. I’d never wanted to play with anything 

so bad in my life, so maybe “liked” wasn’t a strong enough word. I managed to tell her yes, and 

then she said, “I don’t usually show these to people who haven’t asked me out yet.” 

I nodded, getting the reference and seeing where she was going, but not even caring. I just 

nodded, agreed, and said yes Mom. Frankly, whatever she wanted to hear, I would have said, 

just to keep that top unzipped. But then, she leaned into towards me and forced me back. Like, 

ALL the way back. As in, I fell on my back, and she was leaning over me with her hands in the 

sand, and her breasts so close to me that I could feel them rubbing against my chest!

Then she said, “Now… ask me if I give head on the first date.” I managed to stammer something 

resembling “what!?!”; but Mom didn’t waver. She leaned in even closer, the warmth of her body 

pressed into mine as she dragged her tits slowly up my chest and put her lips to my ear. Then 

she repeated herself, saying, “I said, ask Mommy if she Sucks her dates Cock, on the first date”. 

It uh, it took me a few tries to get enough air to say the words. But eventually, I managed to ask. 

When I did, she pulled back some, and with a smile, she replied, “Every. Time.”. 

Then she stood up, made a show of zipping her top back up, and started walking back the way 

we came. She called back after me, telling me to catch up, and informing me that she was 

hungry. So, I did. Then, I did the only thing that I possibly could. I asked my Mom if she would like 

me to take HER out to dinner tonight. She smiled at me then, like I’d done something very right, 

and she was proud of me. But then she turned her head, with a mischievous grin she asked, 

“Sweetie, are you asking your Mother out?” But for once, I didn’t hesitate. I nodded, said yes, and 

formally asked her if she would go out with me, and let me buy her dinner. 

In reply, she stopped, stepped in close, and reached her arms around behind me, placing her 

hands on my upper thighs and letting her fingers drift painfully close to erotic areas as she 

whispered into my ear. “It’s a date.”