“Absolutely perfect!” She beams. “Oh my gosh, you are way too handsome to be my son, I can’t even right now!” She let out a high-pitched squeal of pure excitement.
Admittedly, I blush a little. Hearing her gushing over how great I look isn’t something I normally hear in the day to day.
“Ah! And the last piece to tie it all together!” She reaches for my navy suit jacket hanging on a heavy wooden hanger off the door. She opens it, and I slide my arms through the light, slick material. Being a little shorter than I am, I squat down a little as she tugs it up over my shoulders.
I stand up straight, still looking at my handsome self in the mirror, my mom’s cute, smiling face peeking beside me while her hands reach around me to button up the top and middle buttons of the jacket.
“Ok, stand up straight, arms to the side…” she starts to smooth out the shoulders and sleeves, even bending down to smooth out the slacks. Not that I mind, I get to check out her cleavage, silently wishing that her tits might just pop out as she swipes down my pant legs with both arms.
She pops back up and looks back at the mirror.
“(Gasp), Oh my god! Baby! Look at you! Oh!” Her hands, clasped together, come up to her lips, eyes getting misty.
“Thank you, mom, for everything! You nailed it!” Before I finish my sentence, she clutches my arm and pulls me towards her in a tight, side hug, never minding that she just smoothed out the suit.
“If this suit doesn’t get you at least a fifth date with this girl, then she clearly has no taste.” She smiles widely, clutching my arm even tighter.
I start to chuckle, “Mom, c’mon! We’re just going to the dance as friends.”
“Don’t ‘mom’ me!” she chides, playfully smacking my chest. “I’m a proud mama at the moment, and she better be speechless when she opens her door. Jaw to floor, the whole nine!”
Our eyes meet in the mirror, matching smiles for each other. I reach up with my free hand and squeeze her arm in love and appreciation.
…
Downstairs, I pull out the small bouquet and corsage from the fridge. Mom standing right behind the island.
“Ok, kiddo, first things first before you go.” She slides over a box of condoms. “You better use ’em if you both get to that point in the night, and if it happens in my car, I want it thoroughly cleaned by Monday.” Emphasizing ‘thoroughly’ with pinched fingers.
She then holds out her other hand, clutching what I’m assuming are her keys.
“If you drink even a drop of alcohol, you do not drive! You call, understood?” Her eyes serious and steeled.
“Got it, mom. Thanks.” I reach out and she drops the keys in my hand, a smile returns to her lips.
“Knock ’em dead, sweety.” She closes the gap between us and exchange pecks on the cheek. Then surprising me with a quick kiss on the lips.
“Have a good time, and again, if you need me, you call!”
“I will, mom. I promise.” I smile back at her, trying my hardest to not make a big deal out of her kissing me.
It’s not that it’s never happened before, it’s just really rare. The last time she kissed me on the lips was when I turned thirteen.
Internally shaking it off, I gather the flowers, tuck the three pack of condoms in my inside pocket, and head out to pick up Sandra. She has a lot of unexpected work to do if she is going to replace my vivid thoughts of my mother right now.
…
On the way to Sandra’s, I reminisce about our four-month relationship those three long years ago. We were great friends, and always hanging out together. I don’t know why I asked, but I did and surprisingly, she said yes.
Our first date was a semi-old-school date: a walk around downtown, stopping at a food truck along the way, chit-chatting about everything, and then finishing with a movie at the theater. To cap it off, when I dropped her off at home, I walked her to her door and we both expressed that we had a really fun time. I was about to kiss her, but hesitated. She didn’t miss a beat and swooped right in, locking her soft lips on mine. We were no longer ‘just friends’ at this point. It was a long, hard kiss. Her hand cupping my face, pulling me into her.
After the initial shock, I leaned into it, pressing my body into hers, wrapping my arms around her. We made out right there on her front stoop for a few minutes before she finally broke away, sucking in her lips as if to savor the taste. Looking up at me, she smiled, “Goodnight, Grant.” I replied with a smitten smile, “Goodnight, Sandra.”
And with that, she closed the door, and I felt like I floated back to the bus stop on cloud nine. Our relationship only progressed from there. Less than a month in we were making out in her room with just our underwear on, dry humping each other. A week later, we snuck outside my house at night and skinny dipped in the pond. As we lay out on the bank to air dry, she gave me my first ever blowjob. To my surprise, when I came, she swallowed it all. Not one drop spilled.
I was in heaven at that point, and I thought that she would be ‘the one.’ We fooled around a lot more, but we never had sex. Three and a half months in, I started feeling like we were just in a rut. We hung out but didn’t say much. We went out on dates, but at the end of the night, it never went past oral. I think she was getting the same vibe I was feeling, but we just never acknowledged it. Then, after four wild months together, she came up to me after school with a serious look on her face and said the dreaded words nobody ever wants to hear from their significant other, “We need to talk.”
I was devastated. Crushed, and heartbroken. My first real relationship, and it just crashed and burned right before my eyes. My mom was my saving grace. She consoled me almost every night for a week, cuddling me, holding me close, stroking my hair as I sulked. That’s when I started snapping out of my heartache enough to notice that I was resting my head in my mom’s cleavage. Her soft, full breasts pressing into my cheek. At the realization, I noticed I wasn’t sad anymore. I also noticed my pants getting much tighter in the crotch area. When my head hit my pillow later that night, it wasn’t Sandra that I dreamt of…I dreamt of my mom.
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