Dear Diary
Copyright© 2026 by callmeQ67
Chapter 4: September First and Second
Coming of Age Sex Story: Chapter 4: September First and Second - On a girl's fifteenth birthday, one of her gifts is a journal which she uses to record her innermost thoughts. She’s ashamed of her body because she is developing more slowly than her friends and classmates. Little does she know that there’s at least one man who finds her attractive for the very features that make her feel deficient.
Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/ft ft/ft Consensual Mother Daughter Black Male White Female First Facial Masturbation Oral Sex Small Breasts
September 1, 2025
Saturday night was like a nightmare that turned into a freaky fantasy come true. And then it got a little too real.
Just as I’d hoped, my mom passed out after drinking several glasses of wine. While she was still conscious, though, she was awful. She was alternately silly and angry, and she pretty much threw herself at DeWayne. It was so embarrassing. She even took off her dress right in the living room while I was there! DeWayne was trying to get her into the bedroom, but before he could manage it her bra also came off.
It was pretty disturbing, but part of me couldn’t help noticing that she still has a great body. I envy her those big round tits.
At last they were behind closed doors, and I could hear my mom pleading still. DeWayne was being incredibly patient with her and I hoped she that she would pass out soon. I went out on the deck so I wouldn’t have to listen.
He found me out there like half an hour later. “Well, that wasn’t any fun.”
I wrapped my arms around him, and told how sorry I was that he had to deal with that.
“It’s my fault, really, for encouraging her to drink wine.” Then he grinned at me. “But now that she’s out, does my baby girl want to have some fun?”
I stretched on my tiptoes and he bent to kiss me. We sucked face for several delicious minutes and it was wonderful. DeWayne is a great kisser in a very different way than Liz or Janice. While they’re both soft and gentle, he’s strong and dominant. He shows me who’s boss as soon as his tongue enters my mouth.
You could say he kisses just like he eats pussy.
His hands were all over me while we kissed, and I was getting super aroused. I dropped to my knees and fished his cock out of his loose linen trousers. It was semi-hard already and I went to work on it, licking up and down the shaft and circling the head with my tongue. “I love sucking your big black cock, daddy,” I said, looking up at him as his cock slipped into my mouth.
It wasn’t long before his dick was fully erect. Like the rest of DeWayne’s body, his manhood is exceptionally big and exceptionally strong. It’s much thicker than my wrist and feels like gym-hardened muscle in my hands. The strength and power of it made me feel small and weak as I slathered spit all over it.
DeWayne had his back to the water which is why he didn’t see the boat right away. It was motoring slowly up the bay with seven or eight people aboard, probably returning to a marina after a day out on the ocean.
The boaters were most likely drunk, because as soon as one of them spotted us, they all started whooping and hollering. The boat slowed to a crawl just short of our deck. A female voice said, “Oh my god, that’s the biggest dick I’ve ever seen!”
“Fuck me, daddy,” I said. “Fuck me while they watch.” I looked up at DeWayne with pleading eyes.
“Tempting,” he said. “But not a good idea.” I suppose he was worried that they might take a photo of us together. He hauled me to my feet and pulled me towards the door.
“The show’s over, folks,” he said to the boaters as he led me through the French doors.
“Boo!” someone shouted, and there were chants of, “More! More!” But we ignored them and closed the door behind us. I understand DeWayne’s need for caution, but the notion of fucking him in front of those strangers made my pussy gush. I wanted his cock inside me so bad.
I was hoping that DeWayne would bend me over a piece of furniture and take me there in the living room. To show him how ready I was, I slipped my panties off and tossed them to him. “Can you tell how wet I am, daddy?”
“You’re such a naughty little girl,” he said, as he held them to his nose. “Now take off that dress and show me your gorgeous body.”
In spite of DeWayne’s compliments, I was still insecure about the way I looked. Especially after I pulled the dress over my head and stood before him stark naked. “I don’t understand what you like about my body,” I said. “I mean, my mom has an amazing body. I’m just a skinny kid.”
He looked me up and down, from my little bare feet to my smooth-shaven sex, and on up to my small pointy boobs. Finally, he looked at my face and grinned. “Believe me, your body is super sexy. But since you’ve mentioned her, let’s check on your mom to make sure she’s okay.”
We found my mom lying naked on the bed, her arms and legs flung out in all directions. DeWayne bent over her and listened to her breathing. “She sounds fine,” he said. Then he held her wrist, pressing two fingers to the artery. “Her pulse is strong.”
“Mom?” I said, laying a hand on her shoulder and giving her a shake. “Can you hear me?” No reaction.
I thought we’d go to my room then, but I was wrong.
“Get on the bed,” DeWayne ordered. “Right here.” He indicated a spot next to my mom. I did as he asked, and I was so close to her that my shoulder was pressed against hers. DeWayne looked at us and sort of growled low in his throat. “Fuck, yeah. What a beautiful sight.”
His eyes went back and forth, comparing us. It was kind of mortifying, you know? I mean, my mom is a very shapely woman, with nicely rounded hips, a narrow waist, and big round tits, though they were kind of flattened as she lay on her back. Our faces look very much alike, but my body is still only half developed. My legs are thin and I don’t really have any hips. I will say, though, that my pointy little breasts don’t sag at all even when I’m lying on my back. My fat gumdrop nipples pointed straight at the ceiling.
“Spread your legs,” said DeWayne as he undressed.
I gazed up at his body in awe. Just the sight of him made my pussy beg for attention. My mom was right in the middle of the bed, so the only way I could spread my legs was to rest my right leg on her left leg. “Like this, daddy?” I said, displaying my juicy little shaved snatch.
“That’s right, baby girl. Now show me how you touch yourself.”
I would probably feel awkward doing that in front of any other guy, but not DeWayne. I started by spreading my legs even wider and caressing my hairless little cunt with my fingers. Not really getting in there, just rubbing my plump lips slowly. Then I wet two fingers in my mouth and spread myself open with my other hand. I diddled the hood of my clit with those wet fingers and it felt wonderful.
DeWayne was stroking his cock as he watched and I wanted that hunk of beef inside me more than anything in the world. “Oh daddy,” I pleaded. “Won’t you fuck your little girl now? Pretty please, daddy?”
“Soon,” he said, and bent to kiss my mouth. “Very soon,” he repeated. When he knelt at the foot of the bed, I thought he was going to lick my pussy. But no, he spread my mom’s pussy open with his thumbs and began to lick her instead! She didn’t react at all—at first. I mean, she was pretty much catatonic. After a few minutes, though, she gasped and began to make a humming noise. Her head rolled from side to side.
“She waking up!” I chirped.
DeWayne raised his mouth from her wet, blood-engorged labes. We watched as my mom returned to her fully unconscious state. Her head stopped moving and her breathing became slow and steady again. When he was sure she was asleep, he slid over between my legs. I knew instantly what he was up to. Of course I didn’t mind that he was going to lick my pussy, but what the fuck? He’s comparing the taste of my pussy to my mom’s, like we’re two different wines or something?
But when he spread my pussy open and began to eat me, I forgave him pretty much right away. That man sure knows how to use his tongue! Maybe a small part of me resented his taste testing, but my pussy didn’t care one bit. When he sucked my clit into his mouth and tickled it with his tongue, fireworks exploded in my brain and all was right with the world.
While my legs were still trembling, he kissed me and shared my flavor with me. (I taste great, by the way.) The he flipped me over and lifted my hips until I was on my hands and knees. DeWayne stood by the bed and slowly worked his cock inside me. My face was just above my mom’s boobs—so close that my hair brushed against them.
It took at least a full minute of gentle in-and-out thrusts for DeWayne to get his oversized member all the way in me. I moaned when it hit bottom, and that sensation almost made me cum again. Once I’d adjusted to being filled with cock, he began to fuck me in earnest.
“Oh fuck, daddy,” I whimpered. “Your cock feels so good.”
His dick hit different at this angle, and I could feel it bumping up against something in there. It kind of hurt but felt good at the same time, if you know what I mean. He was taking long strokes, pulling his cock most of the way out and ramming it back in. It made the bed shake and I watched my mom’s boobs jiggling right in front of my eyes.
DeWayne seemed to read my mind. “Do you like your mom’s big tits?”
I watched them bounce gently as an orgasm began to build, like a train picking up speed. They’re not as perky as Janice’s boobs but even bigger and just as beautiful in a different way. “Yeah,” I said. “I sure do.”
“Play with them,” he said. “I know you want to.”
And it was true, I did.
I squeezed one of her boobs gently, noticing how small my hand looked by comparison. Her nipples are much longer than mine, and darker, like big fat pencil erasers. When I brushed my palm over one, the flesh of her aureole crinkled. The nipple itself grew harder and fatter. It was an involuntary reaction, I suppose, but it seemed like she was becoming aroused. Again.
“Suck them,” DeWayne said. “Suck your mom’s titties.”
He knows me so well, I thought. Because I wanted to do exactly that.
My mom had nursed me when I was a baby, and now here I was fifteen years later sucking her big squishy boobs, going from one nipple to the other and back again. And it did something to my brain because I started cumming again, over and over. My insides had adjusted to the size of DeWayne’s cock, and I felt all soft and wet and buttery in there. I was moaning and whimpering as I slobbered all over my mom’s big boobs, and nothing in the world mattered then except feeding my mouth and my needy pussy.
DeWayne fucked me like that for a good long time, all the while telling me how sexy I looked sucking my mom’s tits. I was having one earth-shattering climax after another, almost nonstop. I could tell he was getting close, too. His cock felt even bigger and he was fucking me hard and fast. “Cum inside me daddy,” I begged. “Fill my pussy with your hot cum.” I was beyond caring about the risk of getting pregnant, or anything else for that matter.
The man had other ideas.
He pulled out of me and knelt, straddling my mom’s waist. “Jerk me off,” he ordered. I stroked his slippery shaft with both hands as I sucked on the head. “Here it comes ... yeah ... yeah...”
I waited until the last possible moment to pull my mouth off. His cock swelled in my hands and he shot an enormous jet of cum up between her boobs and onto her neck. And as he continued to shoot six or seven more volleys of cum, I pointed his cock so that there were ropes of cum all over my mom’s big juicy tits.
When he’d shot most of his wad, I took his cock back in my mouth and sucked out the last drops. I was pretty sure what DeWayne wanted me to do, and that was fine because I wanted the same thing. I looked up at him and he nodded, so I began to lick DeWayne’s thick, gooey mess from my mom’s motionless body.
At the beginning of the summer, I’d never even been kissed properly. I was just another goonette, watching porn constantly and fantasizing about having real sex. Now I was doing something so outrageous that I’d never even dreamed about it. And it was turning me on all over again. I swung one leg over my mom’s thigh and began to rub my needy cunt on her leg. I was cumming again before long, and I came two or three more times before I finished licking up all the splooge from her body.
When I was all done, I rolled onto my side with one leg thrown across both of hers, and one arm around her middle. I’d cum at least a dozen times and I was tired, really tired. I remember feeling very comfortable, all snuggled up to my mom like that.
I must have slept like a baby, which is kind of funny since I was nursing on my mom’s boobs the night before. There were voices in the room with me as I slowly returned from dreamland, but they made no sense to me at first. The first voice I recognized was DeWayne’s. He was saying, “Your little girl has a pretty pussy, doesn’t she?” My brain was fuzzy with sleep but I couldn’t help noticing that someone was caressing my vulva. It felt so good I just lay there with my eyes closed and enjoyed it.
“Mmmm hmmm, she sure does.”
It was my mom’s voice, and hearing it made my heart stop beating for a second or two. When I realized she was the one caressing my little girl parts, I kept my eyes closed because I was afraid to look. Not to mention I was totally freaking out.
“I’m glad you made her shave it,” my mom said. “It looks so sexy like this, all smooth like a little girl.”
“Why don’t you taste her?” DeWayne suggested.
“Really? Don’t you think that would be a little weird? And, you know, just plain wrong?”
“Not at all. I think it would be hot as fuck, and I know that you want to.”
“You’re such a bad man,” she giggled, right before I felt her long hair brushing my thighs.