Daisy and Me
Copyright© 2025 by TheDarkKnight
Chapter 4: Daisy and Me ... and Cindy
Coming of Age Sex Story: Chapter 4: Daisy and Me ... and Cindy - Growing up in a small town in southeastern Georgia in the 1960’s wasn’t quite as idyllic as Mayberry, but my time there was made a lot better by having Daisy Taylor in my life. She was a pugnacious, kind of bratty tomboy who became my first love. Together, we explored the blooming sexuality of our teen years.
Caution: This Coming of Age Sex Story contains strong sexual content, including Teenagers Consensual Reluctant Romantic Heterosexual Fiction Anal Sex First Masturbation Oral Sex Petting Voyeurism Clergy
You probably expect me to tell you that Daisy and I devirginized each other shortly after our awful anal experiment. I know that’s what I expected, but that’s not quite what happened. We still messed around a lot, making out, mutual masturbation, more oral experimenting, and other stuff, like the time I ... well, that episode deserves a more detailed description.
A couple of weeks after our anal misadventure, or the time I raped her butt, as Daisy liked to describe it, we were lying on Daisy’s bed one afternoon, just reading and talking about things going on in our corner of the world. I was about to doze off, something that happened frequently in her cool room on those hot afternoons. Daisy was curled up next to me, and I thought she was almost asleep, too. Times like that made me picture what the rest of our lives might be like: making sweet love at night and waking up in the morning next to each other. I was naive enough to think that we would never drift apart.
Dreaming of that perfect life was making me feel very peaceful, then suddenly, Daisy sat up, poked me in the ribs, and said, “Get up and take your pants off.” Yeah, just like that. I did mention that she could be a bit bossy, didn’t I? I wondered if my pants were on fire, but they weren’t. I hesitated for a moment, wondering if it was just another one of her jokes, then she became insistent, “Come on, your shorts and your boxers. You can leave your shirt on if you want.”
“What goin’ on, Magnolia?” I asked. I was hoping this was going to lead to some goofy new sex game she had come up with. “Ain’t you gonna take your clothes off too?”
She didn’t answer me. Instead, she got up and headed for the bathroom. I wasn’t sure what to do; you know, like when a nurse tells you to take off your clothes and the doctor will see you in a minute, you’re never quite sure what that means. So I took off my shorts but kept my boxers on.
When Daisy came back, she was holding one of her hairbrushes and a jar of something I couldn’t see. I was really confused, but the love of my life quickly straightened me out. “Take your underwear off, and lie down on your stomach.”
“What are you gonna do with that brush, Daisy?” I thought maybe she wanted to give me a spanking, something that we had never tried, but I wasn’t opposed to the idea.
“I’ve been thinking about what I told you about never wanting to try anal again,” she explained. “But I want to make sure that you understand why. Now come on, just take ‘em off and let’s get this over with.”
I wanted to remind her again that the whole thing had been her idea, inspired by her nasty cousin Caroline, and that I hadn’t even hinted about trying it again, but she had that look in her eye that told me I would be wasting my breath. At least now I had an idea what she intended to do with the brush, and I was worried.
She saw me staring at it and explained why she had selected it. She held it up and gave me a short lecture. “The handle has a nice, round end, and these things,” she told me, pointing at the ribs circling the handle, “are a good way for me to see how far in it is. If you can take it to the third one without crying like a baby, I’ll know you are a real man, and you’ll understand why I never want your dick in my ass again. Don’t worry, I’ll use lots of this,” she added, as she opened the jar she had brought with her. It was Vaseline. I wasn’t sure if that was better than shortening or if she just didn’t want to waste more of her mom’s Crisco. She coated the end of the brush and even dared to spread some of the slippery stuff around my anus. I hoped I had wiped well that morning.
I decided the best thing for me to do was cooperate and get the whole crazy act over as quickly as I could. My boxers came off, and I stretched out on my stomach, feeling very vulnerable. Even though we had lots of experience seeing each other naked, it was still embarrassing to have her messing around with my back door.
Daisy got on her knees behind me, straddling my thighs, and pressed the blunt end of the brush against my tightly clenched opening. “Just relax,” she said, giggling, as if she knew how impossible that was.
She pushed a little harder, and I felt my sphincter being stretched a little. It wasn’t painful or uncomfortable at that point, just weird. “Are you done?” I asked, hoping that she had accomplished her goal.
“That’s just the first ring, J.C.,” she told me, “two more to go.” She paused for a moment to apply more Vaseline to the brush handle, then pushed it again. Now it was beginning to hurt a little. “That’s two,” she announced.
I tried taking some deep breaths and not think about the object stuck in my butt. That seemed to help, because a few seconds later, after she gave the brush one more firm, steady push, I felt it going deeper. Now it was definitely painful. Those circles around the handle were starting to feel like knife blades, and I had a flashback to Daisy showing me the bloody tissue after our disastrous experiment. I was hoping she was about done when I heard her say, “Yeah, there we go, that’s the third one in,” she said. “Good on ya, sweetie. You didn’t cry or scream.”
“Okay, but be careful taking it out,” I warned her.
She laughed and said, “I know, I know, but I’m not taking it out yet. When you did me, it wasn’t too bad until you started really fucking me. So, hang on, Superman, I’m gonna give you something to remember.” I had no idea she had been storing up that much resentment for something that had been her idea.
I clenched my teeth as Daisy started moving the brush handle in and out. She wasn’t pushing it any deeper in, but her strokes were getting faster and faster. I couldn’t remember if I had lost control like that when it had been my dick in her ass, but it didn’t matter. Finally, I’d had enough. I reached behind me and grabbed her hand to stop the torment. That did the job. She stopped moving the handle, but didn’t take it out.
“Not yet,” she told me. “There’s one more thing I want to check out. Roll over on your side for a sec.”
I was really confused now, but I did what she wanted. “There it is!” she declared. “That’s some woody you got goin’ on, J.C. Caroline told me that sometimes guys get really turned on when their prostates are massaged. I didn’t know what a prostate was, or where it was, but she told me all about it.” Of course, it had to have been Caroline, Daisy’s sex guru.
Then, suddenly, the Good Daisy was back. “Let me help you,” she said, as she started stroking my cock, which was, as she said, about as hard as it ever gets. She proceeded to give me a very special Daisy hand job, something that she had become very proficient at that summer. When I came, it was like an eruption of semen. The effect of that damned brush on my prostate had created a very happy ending. It left me drained, in every sense of the word.
“Damn,” Daisy said, “You got your stuff all over my blanket. Caroline said that might happen. How did it feel?”
“Kinda shook me up a little,” I told her, “but could you take the brush out now, slowly, Sweetpea?”
Once she got it out, she said, “Looks like I need a new brush. I might not be able to clean this one, and it smells. Good thing Mom got me a new one last week.” So, this hadn’t been some spur-of-the-moment thing. Daisy had been planning it for a while. I was just glad that she had gotten it out of her system. As amazing as it was, I’ve never been tempted to try it again. Anal was a dead end (sorry for the pun) for both of us.
We both knew, without talking about it, that at some point we would grow apart and turn our attention to other people. Changes are a natural part of life. We would lead boring existences without them, and there were a few more of them ahead of us that summer.
One of those changes was that Daisy got a job bagging groceries at our local Piggly-Wiggly grocery store, the closest thing to a supermarket we had. Her parents had promised they would get her a car when she was sixteen, if she kept her grades up and got a job. Even though that momentous birthday was almost a year away, Daisy thought it would be a good idea to get started on the whole job thing. She liked working there. It gave her a chance to talk to lots of people, which she was always good at, and she picked up on all the local gossip, something else she enjoyed. She usually worked afternoons, and since I worked mornings at the library, it meant we couldn’t hang out together as much. Sometimes I think that was a good thing, part of that growing apart I mentioned.
The other change in our lives was Cindy Walker, my coworker at the library. She was a year ahead of Daisy and me in school, and I didn’t know her very well until we began working together. At first, I didn’t really like her. Getting along with her was just part of the job I had to get used to. She was a bit stuck up, but I guess when you make all ‘A’s, and are president of the Honor Society, even as small as it was at our school, you can have your nose pointed up in the air sometimes.
After working with her for a few weeks, I found out she was fun to be around and wasn’t as conceited as I had thought. She had a wicked sense of humor, and much to my surprise, knew almost as many dirty jokes as Daisy. Cindy wasn’t much to look at. She was a couple of inches taller than I was, but really skinny. I heard one of the librarians describe her legs as “looking like pipe cleaners”, and her knees reminded me of doorknobs. Her hair was a ginger-colored mass of curls that never seemed to look the same from day to day. It was almost like she had given up on taming it and just let it rest wherever it settled. She wore thick, nerdy glasses, and snorted when she laughed. The one positive attribute she had, based on teenage boy standards, were her breasts. They weren’t Dolly Parton big, but they looked too big to be stuck on her skinny chest. I was still immature enough to find my attention drawn to those mounds whenever I talked to her. That got me the “my eyes are up here” speech a few times, but I honestly think she enjoyed my attention.
It took me a while to catch on that Daisy was actually a little jealous of the time I spent with Cindy. That was made clear to me one day when Daisy was waiting for me as I left work. We were going to hang out together before she had to go to her job. When Cindy and I were leaving the library, she was still laughing, snorts and all, about something I had said, which caught my girl’s attention. She was nice enough to my Cindy as she said goodbye, but as soon as Cindy was out of earshot, Daisy got on my case.
“So, you really like her?” Daisy asked. The tone of her voice left me no doubt what the correct answer to that should be.
“I like working with her, if that’s what you mean.”
“She laughs at your stupid jokes?”
Now I started to feel like I was being attacked for something innocent, and it riled me. “My jokes aren’t stupid,” I told her, “besides, most of them I got from you.”
“Oh, sorry, I meant silly.”
“I can live with that,” I smiled.
“Doesn’t that snorting get on your nerves?” Daisy asked.
“I got used to it,” I told her. “Actually, it’s kind of cute.” Sometimes I just couldn’t stop my mouth from getting me into trouble.