Chapter 4

“Oh, gratitude? I like that,” Anna purred in response. She reacted to my pleasure by getting turned on, which made me want to perform for her. As she fingered my pussy she knew exactly how to touch me, but it was not like when she touched herself at all.

She was rough with herself, pinched herself, and yet with me, she was gentle, sensual, and seemed all about trying to get me off. I craved my friend’s attention. When Anna explored my body, she was so hyper-focused on me that I felt like the only thing in the universe – a treasure.

I forgot that I was dripping wet, and all the warm and musky smells of my pussy were probably disgusting to her. She had four fingers inside my pussy, and her thumb was hooked onto my clit, holding it like a trigger she was pressing but not pinching or crushing.

I did not even realize that the plug was inside of my ass until she removed her hand from it. It didn’t immediately drop. She moved that hand to my nipples and began to caress my tits and alternate between rubbing my neck.

I felt no pain. I did feel a little “full,” but in a good way. In fact, I barely noticed the plug was in my ass. It felt heavy but not uncomfortable. I didn’t feel a wave of pleasurable stimulation either. Instead, I got a kinky feeling from being naughty and doing something sexual, and that was intoxicating.

What surprised me was that it did not vibrate or move around inside me, and I liked that. Even though I loved my friend’s fingers expanding and playing with my pussy, it felt like an octopus was invading my pussy and trying to seek out all the open folds and spaces to caress and tickle them. The sensation was driving me wild but not giving me an orgasm. I was on the EDGE of an orgasm. I had no idea at the time that my friend was intentionally holding me there.

The anticipation of that earthquake at the start was driving me wild. I felt one was building – an earthquake of a much greater magnitude that would rock my entire body and send me into spasms. Yet, I couldn’t quite get there.

However, the plug was not a part of that experience. The plug was simply present in my anal cavity like it was locking that disgusting part of my body off and that it was closed for exploration.

It felt deeply shameful to enjoy it, but I liked it.

I did not like it the way Anna had. She had a big old smile like someone who was doing something she loved and couldn’t wait to get more of it packed up her ass. That wasn’t how I felt. I felt like this plug was just enough, and at the same time that I shouldn’t have put it in my ass.

I didn’t want it to come out, though. I was afraid it would stretch my bottom hole and Anna would think I was disgusting if she saw what was in my bowels.

“Do you want to cum, Susan?”

“Yes,” I responded flatly in a whisper.

“Show me then. Show me how you get off,” she withdrew her hands from my body. My pussy instantly felt empty, and I longed for her to plunge her fingers inside of me again. I had never had more than one finger inside of myself, and she had inserted almost her entire hand.

I clearly had no idea what I was doing.

“You can cum, Susan. Don’t waste the opportunity. Do you want to cum for me?”

Oh god, what a question. Did I want to cum for her? I hadn’t thought I did, but now I wanted nothing more than to show her how much I could cum. I needed to orgasm.

“Can I lay on my back,” I begged as I brought my fingers to my pussy. It felt odd to be in this position – foreign and alien. I felt like I was raining little dribblets of pussy juice hanging from my pussy like the sticky strands of a banana peel.

I expected Anna to tell me that I could lay how I wanted.

“No, I like you like this,” she whispered in my ear, and my leg began to spasm. I had that restless leg syndrome instantly kick in as if I was ready to sprint out of the bed and through the window into the backyard.

I had two fingers probing my slicked-up pussy, but it was not enough to fill me now. I wanted more, but the only reason I did not try was two was double what I would normally have done, and I was afraid that my friend would think I was disgusting.

“Show me, is that how you get off?” Anna clearly wasn’t impressed as my breath started to return to normal, and my tummy stopped heaving. I was sobering up from an orgasm-induced drunken stupor. Except I hadn’t quite reached the point of satisfaction.

“I do not know. Can you do it again? The way you were doing?” I begged.

“No, fist your cunt for me. You know you liked that,” she said.

FIST? As in, punch my pussy? Why did she have to call it a cunt? Oh god. I felt so humiliated, like a dumb but obedient dog, as I reached behind myself, and with my dominant hand, I plunged my fingers into my pussy. I did not stop with just four fingers, either. I pushed my thumb into the side and managed to get my pussy wide enough that I had my hand inside of me to my wrist.

“Like that?”

“Can you take more?”

“I don’t know,” I whispered. I really didn’t know. I pushed my hand in further and was shocked to discover how pliant my pussy was and how freaky it all felt. “Please, please,” I was about to start begging for something – anything. It wasn’t a negotiation. I would have agreed to any condition if only Anna would tell me how to orgasm or touch me like she did earlier.

I began to twist my fist inside my pussy, and as I did, I fell face forward so that my tits and face were in the sheets, but my ass and pussy were still facing up. I knew I was sliding out of the position as I buried my head in my friend’s pillows, bit and sucked on the pillowcases, and orgasmed myself to glory.

It didn’t last long, and when I finished reaching a state of ecstasy, I felt dirty- gross and sweaty. I felt slimy, but I imagined that I was covered in that shiny oil that Rachel had when she came out of her bedroom earlier.

“Can I stop?” I asked.

Anna was already on her back, playing with her own pussy. She giggled and said that I could take a break if I wanted, but she wasn’t ready to quit. We touched ourselves together, which only made the experience much more intense. I felt the warmth of my friend’s skin as we played with each other together.

I adjusted myself so that I was back up on all fours after I finally had a proper orgasm and switched hands. I kept waiting for my friend to tell me that I could lay on my back, but she didn’t. I eventually removed my hand from my pussy and laid down flat on my tummy. My hand was sticky, and now I could feel the plug in my asshole – like a lead weight pushing down on a button that told me I had to poop.

“I need to use the bathroom. May I take this out?” I asked.

“Yeah, after about an hour or so, it always feels like that. You get used to it,” she giggled without giving me permission. It wasn’t that I needed permission. I had free will. I just WANTED her permission. I told myself it was her house and her sex toy – but it was really her mom’s house and her mom’s sex toy.

I had already removed my hand, and I could smell the smell of a girl on it – it embarrassed me. I wouldn’t say tuna fish, but stinky enough that I knew Anna could smell my body.

“How long do you usually wear this?”

“This? This what?” she asked. I knew she knew what I was talking about. I whispered through gritted teeth that I was asking about how long she wore the butt plug at home.

“I never wear the butt plug around the house. Mom would probably freak out if she knew I had it,” she giggled her confession playfully. I felt she was probably telling the truth, though, that her mom wouldn’t allow her to have it though. “At school, I go all day.”

“You wear this all day?”

“Where this.this ... this ... this ... what?” Anna wanted me to say it again. I felt so ashamed. The word sounded absurd to me.

“You wear a butt plug all the time at school?”

“Not when I take a crap, but yeah. I’ve had it every day at school. I took it off when I got home.”

“But I saw you change,” I said.

She slapped my butt lightly and told me that she clenched and waited for me to leave to take it out.

“There is no way,” I replied incredulously. The plug had peeked out of my friend’s butt cheeks when she was wearing it.

“Are you calling me a liar?” Anna’s tone changed drastically like she was angry with me. I assured her that I was not. I was not thinking clearly. All that pent-up sexual energy had drained from me after I satiated my lusts, and I was in a relaxed state where I wasn’t thinking.

I was thinking.

I just wasn’t OVER-THINKING – which is what frequently made me paralyzed to try anything new or take risks.

“Take it out, and I’ll show you,” Anna insisted. She patted my bottom like she was patronizing a good puppy.

I didn’t want to take it out – not in her bedroom and not in front of her. I wasn’t sure how stretched out my asshole was, and I wasn’t sure what might be ON the plug.

“Let me go to the bathroom to do that,” I said. When I noticed Anna’s reluctance, I added, “I’ll even go there naked.”

“Oh, big risk-taker! Two steps out of my bedroom at 2 in the morning?”

“It’s two AM?” I had not ever stayed up that late. I was gobstruck by that news.

I almost didn’t realize that Anna was not smiling when she insisted I return the plug to her. “Take out the plug, clean it, and give it back to me.”

“Clean it? With my mouth?” I was already pinching the plug with my fingers and trying to lift it out. It was a lot easier going in than it was coming out. I had been so far in the throes of passion that I did not even notice the plug getting seated in my ass.

“What? You expect me to clean it with mine after it’s been in your tootsie roll maker?”

I giggled when she called my asshole a tootsie roll maker. That was so degrading – the very audacity of her saying that to me. “It’s not coming out.”

“Here, it’s easy; just poop it out,” she coaxed me by suggesting I use the muscles in the walls of my ass to push like I was taking a crap. I was afraid that I’d actually poop, though. Anna was delicate, and it popped out with a woosh sound, followed by a stale farty smell that I knew had come from my backside. I remained on my tummy.

“Turn over and wash it for me,” Anna said very seriously. There was not a trace of malice on her face, but it was obvious she wasn’t kidding.

I felt strangely comfortable lying on my belly now that I had gotten used to it. Flipping over and exposing my engorged nipples, and facing the ceiling felt like a new humiliation.

“Oh, you have such nice little boobies,” she kissed my tits, alternating between nipples while waiting for me to lick the plug. I did not look at it or sniff it. I put it in my mouth. It was earthy but tasted more like a ball bearing than anything else. I didn’t taste anything or feel anything on my lips that felt like poopy.

“Good girl,” she said as she admired it. Then she put it in her own mouth and sucked it clean one more time – sucking my fresh spit from the object into her own mouth. We hadn’t kissed, but suddenly, I realized she might want to do that if she was willing to taste something I had just placed in my mouth and slobbered all over.

Anna turned around to face away from me and spread her legs nice and wide. Her pussy was red and puffy from all the touching, and it looked sore and worn out – coated in a creamy thin layer of her own pussy drippings. She pushed the plug deeply into her anus with a satisfying “thump” while exposing herself like a dog to me.

I felt flattered – I had done it when she told me to do it. I felt flattered that she assumed the same position for me. I could see her entire body from this angle. I was placing my friend Anna on a pedestal above me. I felt like it was not dignified and slutty – something she didn’t have to do but did it anyway. It proved she would do something she asked me to do, and I respected that. I do not think that was Anna’s intention, but that’s what I took away from it.

She stood up, clenched her cheeks, and then looked over her shoulder at me with an innocent expression. In the dark, her cupie doll face and bald head made me think of Betty Boop saying, “Poop-Poop-Pee-Doo!”

in a cute but sexy way.

Then she walked back and forth, and her cheeks bounced a little as she walked, but I couldn’t see the plug. Anna walked proudly and tall like a cat wiggling their tail slowly to seduce you into petting her. It was so hot!

“So, if you can hide the BUTT PLUG,” I enunciated the word a little too loudly and then stopped myself and brought my voice back to a whisper. “If you can hide it when you are naked, then why do you have to take it out when you get home?”

Anna’s facial expression reminded me of a traffic light that transitions from red to yellow to green. The first expression was “no way,” and it quickly changed to an inquisitive face that seemed to be wondering if she could get away with it. A moment later, Anna had a devil-may-care expression that took it as a dare.

I almost wanted to retract my question because I hadn’t intended to dare her to do it and possibly get in trouble.

“I have never tried to wear the butt plug for more than eight hours. I take it out a little to go poop during the day, but I guess one reason I don’t wear it at home is I have to bend over to pick stuff up. I like to do cartwheels and lay on the carpet. I would totally get busted if I tried it,” she said.

I nodded and accepted the wisdom of that answer. If you can’t do it – then you can’t do it. No point in getting in trouble, right?

“Tell you what, though,” she looked at me like she was about to make me a clever bargain. “Tomorrow, I’ll wear the plug as long as you stay naked.”

“I can’t be naked!” I insisted. Anna gave me a look that suggested that I definitely could. “I mean, not when my mom or brother come to pick me up!”

“Mom will take you home, and you can wear clothes in the car. She won’t let you ride buck naked, trust me. I asked.”

“Really?”

“No,” Anna grinned playfully. She was just having a laugh to see what I’d believe. “At our last house, though, we could go out in the front yard nude, though because we lived in the boonies. I did that all the time.”

“Weren’t you afraid someone would see you?” I whispered. I realized that was a dumb question and retracted it. “Obviously, a dumb question. You don’t mind if your mom’s customers see you naked; why would you care? Your beautiful.”

“Awww, you think so?” Anna was elated that I had said that. “Actually, I was afraid you’d freak out if you saw me naked. My mom thinks that I stripped because I forgot and didn’t care what you thought. I was afraid you’d flip out. I thought it was better to just go ahead and get it out there in the open and see what your reaction would be. I was afraid, though,” She admitted in a moment of total honesty and vulnerability.

“I was shocked, but I kind of expected you to be different. You do not conform to the norms,” I quoted her.

Anna liked what I said and smiled at me.

“I meant, aren’t you afraid of what other people think though? The neighbors? Your brother? Your mom’s clients?” I clarified my question.

“Oh, what MEN think?” Anna frowned when I clarified my question and suggested that she didn’t give a crap what they thought.

I told her I hadn’t meant only men. “There could be female neighbors or customers,” I explained. I had actually been thinking of guys, but I didn’t want her to think that I was a misogynist or something. “My opinion really isn’t all that important,” I said.

“I hate it when you do that. You always put yourself down and make it sound like everyone else in the world is more important than you,” Anna sounded really disappointed by my response.

“I just don’t have an ego and look down on everyone else,” I countered.

“You go the opposite extreme and look up to everyone else. I saw how in awe you were of that weirdo that was staring at my butt today. It was like you were so desperate for him to look at you.”

“No,” I replied. However, at that moment, I realized that my friend had been observing me, and she was correct. I hadn’t realized it at the time, but I felt that, of course, he was looking at Rachel and Anna – they were beautiful, and I was just ordinary.

I did not know how to respond to that.

“Tomorrow, you are going to walk around the house like you were born naked, live naked, party naked, and are going to die naked. It doesn’t matter who comes over, and if you want to act like you are beneath everyone, then I am going to make you do the dishes, clean the house and cater to my every whim.”

I did my fair share of housework and chores at my house. I never complained about it, but it wasn’t something I volunteered for (not usually). I wasn’t lazy, but I wasn’t a neat freak, either. However, I wasn’t afraid of her threat. In fact, I was intrigued when she said I could cater to her every whim.

“I can’t tell your brother to eat a dick and flip him the bird,” I warned her.

Anna snickered when I said that. “I could tell that blew your mind. My brother and I have that kind of relationship. He knows I love him more than the earth and everything in it, and that’s why we can tear each other down. We protect each other, but we fight like cats and dogs at times. You don’t have to tell him to eat a dick, but how about starting slow and tell him to nibble on a pecker?”

She was being facetious.

“I like you, Anna. You are fun. So do we have a deal?”

“I will have to think about it,” I said as I rolled over on the bed and tried to contain my excitement about this wild idea. I didn’t want my friend to see how eager I was to do it.

“No, you do not,” Anna insisted.

“Okay, I’ll do it,” I instantly agreed to her deal but added that she didn’t really have to wear the plug all day. “It might hurt, and I do not want you to get in trouble.”

“It hurts, but it’s a hurt that feels good,” Anna smiled. I assumed she was being facetious and saying something that was an oxymoron because pain and discomfort don’t feel good. “It’s going to be a fun test, and while you are naked, it’s a bigger distraction.”

“May I go to the bathroom now?” I had been holding it for so long. Anna giggled and told me to go but not to take any clothes with me. I can’t really express to you how surreal that feels.

It’s one thing to streak nude when you are carrying your clothes. You can sort of explain when you get caught and change. However, when you dash through the house naked without any backup plan or contingency – it’s kind of like you are committed to the deal.

If Brodie or Rachel had been in the hallway, I would have been busted and had to explain myself. I’d have to do that in the morning anyway – but I had time until that inevitable moment to think of what I’d say. It was in the future – and less scary that way.

Once I was in the bathroom, I kept looking at Red Willy in the shower. It was huge – at least nine inches in length and in the dark, it reminded me of a giant hot dog. I was tempted to play with it. Instead, I fingered myself, but this time, I pinched my clit while I sat on the toilet. I did it half as intensely as Anna had done to herself and squeezing and pinching STUNG, and I did not feel good.

I did not understand that.

However, when I dashed back to her room (completely naked), Anna was lying on her back with her legs spread, finger fucking herself on top of the blanket. I could see the sparkle of the cherry red plug in her ass reflecting the moonlight through the window.

I joined her on my back and finger fucked myself without telling her what I had tried in the bathroom. I felt ashamed I hadn’t enjoyed it. It looked like she did – at times, it seemed like Anna was trying to pull her clit off or stretch it out like taffy.

“What do I tell your mom and brother is the reason I decided to go naked?” I asked after we started finger fucking ourselves for a few minutes. I was overthinking again, and it was probably the wrong time to ask clarifying questions.