My First Time With My Best Friend’s Mom

I came to a rolling stop on my bike, hopping off and pushing it around to the gate at the side of Lucas’ house, pulling off my helmet and hooking the straps over the handlebars, wiping the sweat from my forehead with my hand. I tried to think of it as just extra endurance conditioning for basketball season once school started again, but with the temperature in the mid hundreds it was hard to make myself believe it. I jiggled the latch until the stubborn thing finally agreed to open, nudging the gate closed behind me with my foot and leaving my bike leaning up against the fence like usual, making my way around to the pool-side patio doors. But what I saw as I turned the corner nearly had me tripping over my own feet, stopping me in my tracks.

“Oh, hey Mrs. C,” I managed to choke out, my eyes feeling like they were about to burst out of my head. Lucas’ mom was the quintessential milf, busty, blonde, and beautiful, but I’d never actually seen her in a bikini before, much less one that consisted of barely more than string and wishful thoughts, and the unexpected sight had caught me completely off guard. “Is Lucas up in his room?”

“Brian?” She pushed herself up onto her elbows on her lounge chair, twisting to look over at me in surprise. “Oh, sorry… Lucas must have forgotten to text you in all the excitement this morning. His father surprised him with tickets to the game this afternoon, I guess he got them from somebody at work last minute, so we decided to swap weekends.”

“Oh, uh… okay,” I said, fighting the instinct to curse. I was not looking forward to getting back on my bike right away for the ride home.

“Here, why don’t you come sit down for a minute, have a bit of a break,” she offered, leaning over and patting the seat of the lounger next to hers. “This weather is just about perfect for laying out by the pool, but it must be murder riding that bike of yours back and forth.”

“Uhh… sure. Thanks, Mrs. C,” I agreed, trying like hell not to let my eyes wander up and down that amazing body of hers, so petite and slender, but with an absolutely amazing pair of huge, firm breasts. I was no expert, but they had to be at least double-Ds, and they looked even bigger than that in contrast to her tiny little frame.

“Not at all. And please, I think you’re old enough you can start calling me Jenna now, don’t you?” she smiled.

“Really?” I asked, coming closer and lowering myself into the chair.

“Why not?” she giggled, just like a little girl not a third her age, and it was only then that I noticed the wine glass and bottle on the table next to her chair. “It is my name, you know… and whether I end up deciding to keep the ‘Carmichael’ part or not, the ‘Mrs.’ is definitely no longer appopiate. Apporpiate… Ugh!” She closed her eyes, forcing herself to speak slowly and deliberately. “Appropriate, I mean. Sorry… I may be just a little bit tipsy, this afternoon. Did Lucas tell you his father and I have decided to move forward with the divorce?”

“Uhh, no, I’m sorry to hear that,” I said.

“It is what it is,” she sighed sadly. “It was always heading this way… but somehow it still comes as a shock, you know? No, never mind. Of course you don’t… how would you know, at your age? Here, would you like a drink?” She sat up, reaching for her bottle.

“No, that’s okay,” I said as she upended the bottle over her glass, only to find the the bottle was empty, too.”

“Oops, all gone!” she giggled again, apparently not having registered my denial. “You know what? Thomas still has some of his beers left in the fridge in the garage. Why don’t I go get you one of those, instead?”

She pushed herself up out of her chair, but ‘tipsy’ wasn’t even the half of it. I lunged back up from my chair, barely getting there in time to catch her before she fell.

“Mmmm… so strong…” she murmured into my chest as I supported her in my arms, head tucked comfortably under my chin, her hand caressing my side.

“Here, how about we get you laying back down in your chair, okay Mrs. C.?” I tried.

“Jenna!” she pouted, petulantly shaking her head.

“Okay, Jenna, then,” I relented. “How about we just get you back down into your chair, Jenna, where you aren’t going to fall and hurt yourself, okay?”

“You’ll stay with me, Brian?” she asked, snuggling deeper against my chest. And my best friend’s mother or not, my God, did that ever feel good, with those huge, firm breasts I’d spent so much time fantasizing about pressed so tightly against me! “I think maybe I had a little more to drink than I realized.”

“Yeah, of course I will…” I said, giving her a reassuring squeeze in my arms. “Let’s just get you laying down again, okay?”

“In such a hurry to get me into bed?” she quipped, sexily biting her lip as those gorgeous, deep blue eyes of hers stared straight up into mine.

“What? No, I…” I gasped, at a loss for words, and she just giggled again.

“You can relax, I’m just teasing,” she smiled, stretching up onto her tiptoes to give me a soft, slow kiss on my cheek. “Mostly…”

“Jenna…” I chided gently.

“Did you know, out of all Lucas’ friends, you’ve always been my favorite?” she dropped back to her heels, nuzzling into my chest again. “You’ve always been so nice, and kind, and polite… and here you are, taking care of me like this. And you’ve grown up to be so tall, and strong… and so handsome, too!”

“Jenna, you’re drunk,” I told her, certain it must just have been the wine talking. My best attempts notwithstanding, none of the girls at school had ever been half as interested in me as she suddenly seemed to be.

“Yup!” she giggled again. “Doesn’t change facts! You’re hot!” she accompanied this pronouncement with a sudden grab of my ass, which made me gasp in surprise, and only made her giggle all the harder.

“You know…” she continued, suddenly serious as she looked up at me again. “If you’re going to stay out here in the sun with me, you have to put on sunscreen. Otherwise you’ll burn. You have to take off your shirt and let me put your sunscreen on.” You’d have thought she was negotiating a nuclear arms treaty, she was speaking so seriously.

“If I agree, does that mean you’ll let me sit you down in your chair again first, so you won’t fall?” I asked. She smiled and nodded eagerly, but made no move to let me go.

“You do realize you’re going to have to actually let me sit you down, then,” I told her. “I can’t take my shirt off while I’m still holding you up.”

That seemed to finally break through the alcohol-induced fuzz, and now that she was cooperating I was able to get her down onto her chair without much trouble. I’d always known and appreciated what a tiny, skinny little thing she was… I’d been taller than her since I was ten, for crying out loud, and even girls my age would have been jealous of that gorgeous, toned little waist and ass of hers, to say nothing of those incredible tits! But I’d never quite realized how that would translate to the feeling of holding her in my arms, so small and delicate, like a precious little porcelain doll. She sat staring up at me expectantly, knees spread to either side of her lounger, patting the spot right in front of her as she grabbed her sunscreen from her table. I was still feeling more than a little conflicted… but I told myself that I wasn’t actually doing anything wrong, just letting her put some sunscreen on me. And whatever doubts I may still have been feeling, they couldn’t hold out against the view down into that incredible cleavage of hers in her tiny little string bikini. I took a deep, steadying breath, then stripped off my shirt, spun around so my back was to her, and sat down where she wanted me. The sunscreen was cold at first, but it warmed quickly as her small, delicate hands travelled over my back, shoulders, and sides. I was expecting her to tell me to turn around next… but before I knew it she was snuggling right up behind me, those huge, firm tits of hers pressed tight against my back as she started caressing my chest, nuzzling and kissing the back of my neck as she did it. I was worried she might try for more than that… and I had no idea what I’d say, if I’d even have the strength to try to deny her, if she tried to take things further.

“Okay, my turn!” she finally announced, pulling away. And honestly, by that point I wasn’t even sure any more whether I was feeling relieved, or disappointed. But we both stood, me with a hand cautiously on her hip, ready to catch her if she started to fall again, as she shook out her big fluffy beach towel before retaking her place lying face-down this time. She carefully brushed her long, blonde hair out of my way for me as I knelt down beside her, warming a generous dollop of sunscreen between my hands before I started rubbing it into her back.

“Here, let me get these out of your way for you,” she said, reaching back to undo the strings of her bikini at her neck and the middle of her back. I don’t know why that made such a difference; I wasn’t able to see any more of her than I had a moment ago, but suddenly I noticed I was sweating again, and I didn’t think I could blame the sun. Her skin was so soft, and warm, and smooth under my fingers, and she started letting out the sexiest little moans of pleasure as I massaged her back. Thank goodness she had her eyes closed and wasn’t able to catch me looking, because there was no way on earth I could keep myself from staring at that perfect little ass, the strings of her thong not hiding a thing.

I’d have been quite happy to stay there with her for the rest of the afternoon, no matter that my knees were starting to complain about how hard the patio was, just for the pleasure of touching her back. But suddenly she was turning over, pulling her top out from behind her and tossing it aside.

“Time for you to do my front, now,” she said, biting her lip as she stared up into my eyes.

“Jenna…” I began, but I trailed off at a loss for words. She was incredible, even better than I’d imagined! Her nipples were swollen to a lovely, dusky red, thick and suckable, her areolas wide and girlishly pink.

“Do you realize it’s been nearly eighteen years since the last time I let anyone other than my husband touch my breasts?” she asked me. “But you can touch them, Brian. I want you to touch them!”

“You…you do?” I stammered, swallowing nervously as I tried to get my voice back under control, trying and failing to keep my eyes on her face.

“Please!” she purred up at me, sexily licking and biting her lip. But as if that weren’t already temptation enough, she grabbed her sunscreen again, spraying herself with a line winding back and forth across her tits, writhing slightly on her lounger as she met my gaze, silently daring me to act.

I was beyond even trying to resist, after an invitation like that! She gasped adorably as I took those magnificent globes fully into my hands, her long, sexy eyelashes fluttering closed at my touch. And to think, I’d thought that touching her back had been good!