Dear Diary
Copyright© 2026 by callmeQ67
Chapter 5: Heaven and Hell
Coming of Age Sex Story: Chapter 5: Heaven and Hell - 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 5, 2025
The first week of tenth grade was pretty much like a continuation of ninth grade. I was still a skinny nerd, ignored by most of the boys. I have a few guy friends who would probably like to be more than just friends, but they’re even more nerdy than me. Besides, now that DeWayne has spoiled me, I couldn’t imagine fooling around with a boy my own age.
My mom and I haven’t become regular lovers after our crazy weekend at the beach. In fact, she seems to be uncomfortable about the whole business. She’s come home from work late every night, and when she gets home she avoids me as much as possible.
I understand her, I guess. She probably thinks that she’s done the unspeakable with me and she’s feeling guilty. But I don’t feel that way at all. I love that we did that stuff together. It makes me feel closer to her.
I was worried at first about what Liz and Janice might do since I told them what had happened at the beach. They asked me a lot of questions, like, “Are you okay?” and, “Do you hate your mom now?”
But I told them I was fine and I wasn’t mad at anyone. They seemed to have trouble believing me, but after a few days I guess they accepted it. Or they just don’t talk about it with me.
I haven’t seen DeWayne since we got back from the beach. I suppose he’s busy with his job. But when my mom got home from work today, she said she wanted to talk. I thought she was going to scold me for not doing the dishes and sweeping the floor like she’d asked.
But that wasn’t it—she talked about DeWayne. She told me that what we did at the beach was fun, but that she and DeWayne could get in a lot of trouble if anyone found out. She stressed that I couldn’t tell anyone, even Janice and Liz. Oops! She would freak out if she knew I’d already told them.
She also said I shouldn’t get any ideas. DeWayne was still her boyfriend, not mine. Then she told me that he had plans for the two of us tomorrow night.
“I don’t know what he’s got in mind,” she said. “But you know how he is. It’s probably something kinky and fucked up.”
She never used to swear in front of me, but maybe she sees me in a different way now after all.
September 7, 2025
It’s three o’clock in the morning and I’m exhausted. But I’m still wound up from the crazy shit we did tonight so I want to get this down on paper before I forget anything. If I go to sleep now it might feel like just a dream by the time I wake up. But it wasn’t a dream. This really happened.
Let’s start at the beginning.
Mom said DeWayne was coming to pick us up at eight, and I should wear something cute and flirty. I spent some time pulling things out of my closet before deciding on a denim skirt paired with a cropped camisole top. On my feet I wore white ankle socks with my white Chuck Taylors.
Mom came into my room just as I’d finished dressing. She said my outfit was perfect, but after looking me up and down for a minute, she said, “Let me try something.”
Until then, she had always discouraged me from wearing makeup. But for whatever reason, tonight she decided to break her own rules. So she spent about ten minutes doing my eyes, and the results were amazing. The combination of dark eye shadow and mascara made my eyes look huge and very dramatic.
Even I thought I looked pretty, lol.
DeWayne was punctual as ever, but I was surprised when he pulled a bottle of champagne from his bag. “I feel like celebrating,” was all he said when my mom asked if this was a special occasion.
Knowing only too well my mom’s sensitivity to alcohol, I wondered if this was a good idea. He poured a glass for me too, which was another surprise. It was my first drink ever. I had declined the other two or three times when alcohol had been offered to me because I was afraid that I would behave like my mom. But omg! I felt so giddy by the time I’d finished half the glass that I kinda wished I’d tried it before.
After we’d each had one glass, DeWayne said it was time to get going. He poured the rest of the champagne into two insulated tumblers—one for my mom and one for me. He said he couldn’t have any more because he was driving.
A minute later we were in his Lexus heading towards the city.
Me and my mom both pestered him with questions about our destination, but he refused to tell us anything. I was getting pretty tipsy by the time we reached the exit for downtown, so I hardly noticed when we passed it and turned in another direction. Soon after that, I started to get a little worried when we entered a very questionable neighborhood.
My anxiety rose as we passed boarded-up store fronts, and we saw some guys on the corner who looked like they were selling drugs. I didn’t see any white people anywhere. Mom was kinda drunk by this point and she didn’t seem to notice.
But she had a moment of clarity when he finally stopped the car.
“DeWayne, really?” We were in front of a dilapidated building with bars covering the windows and a sign over the door which read, “Dirty Mike’s Adult Books.”
“Come on,” he said. “It’ll be fun.”
“But she’s only fifteen,” said my mom, jerking her thumb in my direction. “Is it even legal?”
“Don’t worry, I know the owner. Come on,” he said again, opening the car door. My mom looked at me and shrugged. I had no idea what we were going to do in there. I just hoped she wouldn’t make a fool of herself.
And I hoped that we would get out alive.
When we walked through the door we were struck by the powerful smell of weed—the air was thick with smoke. I was shocked when DeWayne was warmly greeted by several guys. He had always struck me as such a straight arrow. It seemed out of character for him to even come to such a place, much less actually know people there.
I looked around nervously. It was the first time in my life that I was surrounded by only black people, and it made me feel vulnerable. Maybe that’s not a cool thing to say, but I really don’t think I’m a racist. I mean, I’ve been having sex with DeWayne for a couple of months now, you know?
My champagne-addled brain made a passing note of the products on the shelves. What I saw were lots of sex toys and lots of porno movies. What really caught my attention were the men smoking weed. There were at least a dozen of them. I probably would have been really scared if I had been sober.
DeWayne led us to the register and greeted the white-haired man behind the counter. They reminisced for a minute or two and it dawned on me that DeWayne knew everyone because this was the neighborhood where he’d grown up.
“Mother and daughter, you say?” the man said when we were introduced, a huge grin on his wrinkled face. “Beautiful. Just beautiful.” DeWayne handed the old man a credit card and was given a key in exchange.
Behind the counter was a long hallway with several doors on either side. We followed DeWayne to a room about halfway down the hall, and he used the key to open it. He held the door for us and we entered a small room with a TV on one wall. A padded bench faced the TV, and there was a paper towel dispenser with a large wastebasket just below it. The room smelled weird and the floor was sticky.
Looking back, it’s hard to believe that I still didn’t understand what this room was for. My mom knew, though.
“DeWayne, you are one sick fuck,” she said, looking around. She didn’t seem angry so much as incredulous. “I can’t believe you brought my daughter to this place. She’s just a kid. Haven’t you corrupted her enough?”
“Your daughter is a little freak, as you know very well,” he said, taking something from his pocket. “She was corrupt when I met her. I just helped make her fantasies into reality.”
Even in my semi-drunken state I knew he was right—I had been gooning to porn for at least two years before meeting DeWayne. And since then, I’d done some things I hadn’t seen in any porn video.
I recognized the object in DeWayne’s hand. It was a vape pen. I’d seen some kids at school use them, but I’d never seen DeWayne use one before. Again, it seemed out of character for him. My mom didn’t seem surprised, though. She took a long inhale when he handed it to her. That’s when I recognized the odor. It wasn’t nicotine in that pen—it was cannabis.
“Holy shit, mom!” I said. “You smoke weed?”
She blew out a big cloud of smoke before answering. “Every once in a while,” she said. “It doesn’t mess me up like alcohol does.” Then she handed the pen back to DeWayne, who also took a long drag.
When he offered the pen to me, I looked at them both, incredulous. “Seriously? You think this is a good idea?”
They looked at each other and DeWayne grinned. “Your mom gets super turned on when she’s high. And I’d like to see if it has the same effect on you.”
He should know by now that I don’t need any kind of stimulant to get turned on, certainly not when I’m with him. But I took the pen from him and he showed me what to do. I took a deep drag just as my mom had done, and wow! I felt like I was going to float away, like my body was completely weightless. The world seemed to narrow into a small window in front of my eyes.
DeWayne must have thought I was about to collapse, because he led me to the bench and guided me down onto it. After the initial head rush, I just felt good. Amazing, in fact. It was like the time me and my friends had split that gummy, but magnified by about a hundred.
While I sat there more or less stupefied, DeWayne turned on the TV and a video started to play. Two cute girls dressed in private school uniforms entered a bedroom and sat on the bed. The room looked like a typical teenager’s bedroom with posters on the walls and stuffed animals everywhere. When the camera zoomed in on their faces, I saw that the girls looked very young. I mean, like my age or even younger.
One of the girls was blonde and the other brunette, and they were both really pretty. They just sat and talked for a minute or two until the brunette kissed the blonde. That began a serious make-out session. Closeups showed deep French kissing and tongue sucking. I thought it was hot as fuck.
I watched, spellbound, as one of the girls lay back on the bed, and the other knelt at her feet. Were they really going to ... yes! The kneeling girl lowered the other’s panties and began to kiss and lick her smooth pussy. My mom sat on the bench next to me. She was watching the video as closely as I was, her eyes wide and glassy-looking.
I got more and more aroused as I watched the girls until DeWayne’s voice reached my weed-fogged brain. “It’s okay if you touch yourself. I know you want to.” He was looking directly at me.
I glanced at mom to see if she had anything to say about that. But her eyes were still fixed on the screen, and her hand was already moving under her dress. I flipped up the front of my skirt and slid my fingers inside my panties. Oh god, it feels so good to touch myself when I’m high!
“You like that teenage pussy, don’t you?” This time, DeWayne was speaking to my mom.
“You know I do,” she said.
“It’s right next to you,” said her boyfriend. I was absolutely riveted to the action on the TV, to the point that his meaning didn’t sink in right away.
“Oh my goodness,” she said. “You’re a bad man.” But she was eyeing me hungrily even as she spoke the words. I knew then what DeWayne was suggesting.
Most people would think I’m sick for even considering it, but apparently I’m not like most people. Besides, I was so high and so horny from watching the girls on the screen that the notion of right and wrong didn’t even enter my mind. I took my panties off and stroked my pussy gently with two fingers.
“Do it, mom,” I said, looking directly into her eyes. “Suck my little pussy.”
My mother does not have a poker face. Quite the opposite. Her every emotion plays out clearly on her face, and at that moment I saw that she was conflicted. Part of her was trying to do what was expected of a good mother. But that part was losing.
“Oh god,” she murmured. “It’s so pretty.”
I slid a finger up and down my greasy little cleft. “Mmmmm, that feels so good...” I raised my finger to show her the strand of slippery girl goo that clung to it. “Please, mom ... eat my little teenage cunt.”
The last of her resistance was crushed.
“Fuck it,” she said, dropping to her knees in front of me. “I need to taste you.”
She dove straight in, her tongue parting my juicy inner labia. She was eating me just the way I like it, and I knew it wouldn’t take long to cum. I rocked my hips and moaned. “Oh god ... oh yeah, eat me ... yes ... yes...” Our eyes met just as she began to suck my clit, and that pushed me over the edge. My feet came up off the floor and I grabbed my mother’s head, holding her mouth hard up against my gushing pussy.
She kept on licking, and I wailed in ecstasy as she got me off a second time. “Fuck yeah, mommy, that’s so good ... yes ... yes ... suck my pussy...”
I finally had to push her head away when my clit got too sensitive. My legs were still shaking as I became aware of the world around me once more. The first thing I noticed was that DeWayne was pointing his phone at me, no doubt shooting video. I wasn’t surprised.
The next thing I noticed was that the girls on the TV had been joined by a tall black man. His hair was half gray, so I guessed he was at least fifty, maybe older. They freed his cock from his trousers, and holy shit! It was huge! Maybe even bigger than DeWayne’s. The two cuties got right to work licking sucking his veiny monster, slathering it with spit.
I was instantly turned on all over again.
“DeWayne?” my mom said. “Are you just going to watch, or are you going to take out your cock?”
His answer was completely unexpected.
“I’m just here to watch,” he said. “This night is for the two of you. But, if you want to suck some dick...” He didn’t finish the sentence, just turned his head toward one of the side walls. There was a big black dick poking through a small hole in the wall that I hadn’t noticed before.
At first I thought it wasn’t real. I thought there was a big dildo stuck to the wall. But then it sort of twitched, and a drop of pre-cum oozed from the tip.
“Oh my god!” my mom exclaimed. “A glory hole? I didn’t think they were real, just something they put in porno movies.”
Glory hole? I had never heard the term before, and had never seen one in a video. I guess that was one porn genre I hadn’t stumbled upon yet.
“Oh, they’re real all right,” DeWayne said, then pointed to the opposite wall, where another large black dick was sticking out. My mom looked dumbstruck. Like, in spite of everything she had done, she could still be shocked.
I was shocked too, but not for long. That first cock was fat, veiny and uncut, just the way I like them. I thought it looked delicious. Without a second thought, I got up from the bench and took it in my hand.
Disconnected from a body and a face, it seemed like its own being. The owner of the penis might have been young or old, thin or fat. He might have looked like a movie star, or had a face that would make a train take a dirt road. The only thing that mattered to me was his cock. It was hot and alive in my little hand, and I knew exactly what it wanted.
I stroked it softly as I dropped to my knees. It responded by oozing a little more pre-cum. I licked it up, then ran my tongue along its full length, starting at the base. I licked it all over, and stroked it with my hands. Finally, peeling back the foreskin, I popped the head in my mouth.
“Fuck yeah,” came a voice from the other side of the wall. I had learned a lot from DeWayne about how to suck a dick, and I put my knowledge to good use. “That’s right, little girl,” said the voice. “Suck it.”
I had also learned some dirty talk from DeWayne—and my mom. “Does that feel good, daddy?” I said to the penis, hoping its owner could hear me. I loved the way it felt in my hands, and I loved the way it filled my mouth. I pushed it in deeper until I choked and my eyes watered.
“Go ahead,” I heard DeWayne saying. “Your daughter seems to be enjoying herself.”