This is based on something that happened to me but I've added a lot so you can't tell what's true and what's not. Everyone was over 18 at the time this took place.
When I entered college, my roommates were Cindy and Carol. They talked about sex a lot. Each had a boyfriend, and they'd go on and on about letting the boys feel up their titties in the library stacks and about stroking dicks behind the soccer fields. They especially would get into details about the boy's spurting, how much, how far, how often. It got to the point that they started competing with each other. I first noticed they tried to outdo each other when Carol said she went to a nude beach to sunbathe. She liked how the guys walked by and eyed her. Then Cindy went to a nude beach with two boys. She said they were semi-hard the whole time sitting next to her. She said she couldn't blame them since she was giving them uncensored views of her pussy. Cindy was the first to talk about sucking her boyfriend's balls while giving him a slow blow job, before he came all over her face. Then Carol began talking about rimming her boyfriend's anus when she gave him oral sex. It wasn't long before Cindy said she rimmed her boyfriend's anus and let him rim hers. The next night Carol talked at length how good her boyfriend's tongue felt at her rear hole and how he put a finger in her ass when he licked her pussy, making her cum harder than she'd ever had.
I listened to all of this and laughed with them, but I didn't have a boyfriend and I didn't dare go to the nude beach. What if someone I knew saw me? I wasn't a complete virgin, but I had a very slow start with boys in college. Maybe I was a little intimidated, too. Cindy and Carol seemed so sure of themselves. They weren't drop-dead gorgeous but they were pretty and had attractive physiques. I was skinny then, with small breasts. With my long straight hair, I looked like a bookworm.
Their conversations made me horny. At night, I would lie in my bed and quietly finger my clit, imagining what they had talked about, until I came. Cindy and Carol continued to talk about having sex with their boyfriends, and it wasn't long before I overheard Carol telling Cindy that she had been fucked in the ass.
"Oh, my, god, it was so good, after I got used to it."
"Did it hurt?"
"Oh, god, I was too drunk to notice. All I know is that my ass is still tingling."
So, naturally, Cindy went out that night to get fucked in the ass.
"Oh, you should have seen his face. He had the biggest smile. I remember watching him go in me. My legs were open wide, and I told him 'fuck me in the ass, baby.'"
"Oh, my boyfriend loved to hear that, too."
"And I let him come inside my butt. It didn't take him long. I was just getting used to it."
"He didn't pull out first?"
"Why should he? It's not like I'm going to get pregnant up the ass."
"Oh, now I need to try that."
"I want to try taking it up my butt from on top."
"Oh, my, god, can you imagine that?"
I thought about what they said for many days. I'm not sure why, I never thought about it before, but it made me very horny to think about it now. Maybe it was the way they talked about it. Somehow they made it sound dreamy. Whenever I thought about it, it made my ass feel squirmy. I could feel my sphincter muscles react. I wanted to know how it would feel to have a dick inside me like that.
I found a book in the library by a woman about being fucked in the ass. She was a classy, independent sort of a woman and to look at her you wouldn't think she'd be the kind that would like it or even talk about it in a book. I wasn't sure what kind liked it, but it sounded sort of slutty to me. Cindy and Carol weren't in love with these boyfriends of theirs. They never talked about love or making love. They said they were just having fun. The sex they talked about did sound fun.
This lady in the book talked about how it was difficult for her to even think about being fucked in the ass. She had all sorts of reasons that made her think how wrong it was. She said that her biggest fear was that she might like it, and in fact she did like it. The reason she liked it surprised her. She said she did not like being fucked in the ass until she finally let the man take her without any reservation on her part. She just let him fuck her in the ass. If it was dirty or taboo, well, then so be it. She had to learn to become completely passive as he stuck his dick insider her butthole, letting the man take control, or at least allowing him passage, and that sort of pissed her off at first. Once she figured it out, there was no going back. She got into this new experience so much that she thought it was a transcendent experience, beyond anything she felt before.
I started playing around a little in the shower, first with my finger and then with a small dildo. I often played with my clitty as I played with my little hole. I got used to my finger inside, or the dildo, but it didn't seem that exciting doing it to myself. I forgot about it after a few months.
By my second year in college, I still didn't have a boyfriend. I still saw Cindy and Carol a lot, but we didn't room together. I was still in the dorm. Instead of sharing with two roommates, I had a room to myself. They were living together in a condo one of their daddies bought. They hadn't quit competing with each other, and from their talk I gathered they each had graduated to fucking two guys at a time and giving blow jobs to guys they hardly knew in bathrooms. Well, at least they talked about doing those things one time. One time they mentioned they fucked one of their boyfriends together. They kept laughing about tasting each other's pussy on his dick and how they even kissed when they were both licking his cock.
One day I was sitting in my dorm during school break. Cindy called me and said she and her boyfriend were going to fuck on the internet and let anyone watch. She said they did it once already, and it was an incredible turn on. So many people, both men and women, complimented her body. She said what was really great was how her boyfriend couldn't cum on camera with people watching him and she said he must have fucked her hard for almost a half hour, making her cum many times, before they had to turn the camera off so he could squirt all over her. She said they were going to do it again that evening around 11 o'clock.
My brother happened to be in town during school break. He's a couple years older than me, and I'm sure he's had many girlfriends. He asked if he could stay with me. When he came over that afternoon, I was so glad to see him, and I gave up any idea that I would watch Cindy on the internet. We had dinner at a pizza place next to campus and back in the dorm I showed him where he could sleep and said I was tired and needed to go to bed. But I couldn't get to sleep, thinking about how close it was to 11 o'clock. Something made me really want to see Cindy on the internet. The minutes went by. Soon it was ten past eleven. My brother was asleep. So I propped the laptop on my bed, and booted it up.
I did find the site and found Cindy's broadcast. She and her boyfriend were still clothed. You could see they had been drinking. They were staring at their laptop, laughing and giggling. This went on for several minutes until the boyfriend left the frame.
My brother woke up from the glow of the screen. "What are you doing?"
I was mortified. "Nothing," I said.
"It must be something."
"I just couldn't sleep. Just watching some video."
"I'll join you."
"No."
"Why not?"
"It's just a friend of mine. I don't think she'd like it."
"Why not?" he asked and crawled over to my bed.
"It's just...."
I tried to close the laptop, but my brother snatched it before I could.
"Oh, it's a sex site," he said. "Tsk, tsk, little sis, but it doesn't look like there's much sex."
As fate would have it, Cindy flashed one of her boobs on the camera.
"Wasn't she one of your roommates last year? She's kinda pretty, and kinda drunk it looks like."
"I'm sure she is." On the screen, Cindy was now flashing both of her boobs.
"Oo-hoo. Hey, let's watch it for a bit," my brother said. "Do you mind? I've never actually seen someone I sorta know on one of these."
On the screen, Cindy stood up, pulled her pants down, and mooned the camera. I gasped. My brother gave a little cheer. You could barely see the slit of her pussy. I was embarrassed. And then she reached back and spread her ass cheeks. It was a pretty clear view. Cindy left the frame, thank goodness, but she was replaced by her boyfriend, who was now buck naked and stroking a hard boner. I was riveted for a moment until I realized my brother was sitting next to me.
"We should turn this off," I said.
"Are you embarrassed?"
"Absolutely!"
"Don't be. Let's just watch a couple more minutes and then we'll turn it off. It's not that big of a deal, is it?"
"Yes, it is!"
"You've seen this before, haven't you?"
"Not with my brother sitting next to me. It's weird."
"Well, I'll grant you that. Okay, better turn it off."
The screen flashed to black.
"That sure was something," my brother said. He got back on the mattress on the floor. He lay on his back, his hands behind his head.
"That sure was something," he repeated.
A few seconds went by in complete silence. It was apparent that both of us were awake and thinking about what we'd just seen. I was imagining more, and I wondered what my brother might be imagining.
"Remember when you came home from school last year?" he finally asked.
What made him think about that? It seemed so disconnected. I couldn't imagine where he was going with this.
"Yeah?"
"I could hear you in your room at night."
"No!" Now I knew what this was about.
"Yes, I'm sorry. I didn't want to hear it, but I couldn't help it."
"What did you hear?" Did I really want to know?
"Well, I could hear the rustle of your sheets, and the bed creaking, and these soft moans."
"How dare you!"
"Sis, I couldn't help it. It's not like I was spying on you."
"Oh, god, you must have thought I was a pervert."
"Hell, no. "
"Well, it's supposed to be private."
"We all do it, don't we?"
"We don't talk about it."