Time flies when you are having fun, or so they say. In my case, it seemed to be standing still. It had been almost a month since Fiona allowed me to have an orgasm, the most extended denial period ever.
Several months before, she started keeping me nude at home, and now it felt odd to think of wearing clothes all the time. They almost felt uncomfortable on the occasions when I was allowed to put something on. All of her friends and mine were now fully aware of the situation. Most of them got over the initial awkwardness soon enough. My friends mostly thought it was funny and made lots of jokes at my expense, especially when Fiona declared that nude was now my “default state” and I was to ask her for permission if I had to put on clothes of any kind. The guys just laughed their asses off the first time they heard me do that. Several of Fiona’s friends wanted to know how they could get their husbands and boyfriends to be as accommodating as I was, and she never missed an opportunity to give them advice, often using me as a teaching aid. Fiona even invited my sister, Alicia, over for dinner on my birthday. I wasn’t sure how that was going to play out, but she just laughed after I explained why I was answering the door in my birthday suit.
“I shouldn’t be surprised,” Alicia said. “When you were a little kid, mom had the hardest time keeping clothes on you, do you remember that at all?”
Alicia was 5 years and a couple of months older than me, so she had plenty of stories to tell about me as a kid, and Fiona wanted to hear them all. I spent the night blushing profusely. Apparently, she had encouraged my exhibitionist behavior on many occasions when she was supposed to be taking care of her little brother, letting me roam the house, and even the backyard, completely bare. She had even had a couple of her friends over a few times to watch me as well. The stories did bring back some vague memories of running through the house naked, being chased by my mom or my sister. I definitely remembered some of the events after I was a little older, when I got into big trouble (like that time in the treehouse…), and only now did I realize how much she had been egging me on.
It wasn’t long before she spotted the plug in my ass. Wearing a butt plug 24/7 was another thing that Fiona had required even before she started keeping me nude. That was something that I didn’t think I would ever really get used to, and maybe that was the point, but it had gotten a little easier over time, and I felt empty when it wasn’t there.
Fiona had built up a small collection of different sizes, shapes, and materials for me to wear at different times. Still, the plug she preferred was pretty large and made of stainless steel, so it was heavy, making me feel very full, and had a flat ring-shaped handle that fit between my ass cheeks. That was the one I was wearing that evening. It was a constant reminder of the things I was willing to do for Fiona.
“Too bad we couldn’t have kept you plugged like that when you were little. I always hated wiping your ass,” my sister joked after telling us one of her more embarrassing stories that had me blushing.
The worst part about the evening was that I had a nearly perpetual erection. After going so long without an orgasm, the constant teasing in this conversation was keeping me hard, and my sister thought it was hilarious.
“Brian was always a little horndog when he was running around naked. Even at a young age, his little peepee was always poking out like that,” Alicia said, snickering, “At least it has gotten a little bigger.”
I knew my cock was pretty average, even when fully erect. Plus, I was a grower, not a shower, as they say. That meant most of the time, I looked like one of those Greek or Roman statues with their small packages. I had also been a late bloomer with my pubic hair, which got me teased a bit in the locker room at school when I was younger. Of course, Alicia had some comments on that as well.
“I do like that bare skin,” she said, “If you were just a little smaller, you’d look like you did when I was still babysitting you.”
“I have him use a cream to keep the hair off. It lasts longer than shaving, and when it does start to grow back, it’s softer, so rarely any bumps. Plus, I got him some good conditioning lotion,” Fiona said, stroking my pubic area above my shaft. “You should feel how smooth it is.”
I looked at Fiona and started to protest. This was my sister! But Fiona just nodded her head towards Alicia and moved her hand behind my back, giving me a nudge.
Alicia looked surprised as well, but then she smiled and said, “Come here, little brother.”
I slid to the edge of the couch where I was sitting next to Fiona, got up, took one step forward, and turned so Alicia was on my right and Fiona on my left, and my bouncing cock was pointing straight out between them at almost eye-level. I was blushing all the way down to my chest, but I was also as hard as I had ever been.
My sister barely hesitated as she reached out and brushed her fingers across the smooth skin above my penis, where Fiona had earlier. My cock twinged at her touch, making it bounce again.
“He’s a little ticklish there, I think,” Alicia said, giggling a little.
“Yes, I think keeping his body smooth all over like that makes him more sensitive to touch,” Fiona explained, as she reached out and tickled my balls with her fingernails.
I shivered and audibly moaned, making them both giggle again.
“I know it’s probably weird for me to ask,” Alicia paused for a second, then pressed on, “but I’ve never actually seen a butt plug except in pictures and stuff.”
“Would you like to get a better look?” Fiona prompted, “You can even take it out and put it back in if you want, and ask anything, we don’t mind.”
She didn’t mind, I thought, as I cringed. She seemed to enjoy giving everyone we knew the full show with my ass in the starring role.
“Really? Can I? How do I do it?” Alicia asked, thrilled at the opportunity.
“Bend over and let her get a good look,” Fiona ordered
I gave her a pleading look, but I already knew it was pointless. She knew this was totally humiliating me. The fact that it was my sister just made it that much better. This was bringing back memories of us playing doctor when we were younger, and it occurred to me that I was almost always the patient.
I turned my back towards my sister, spread my legs a little more than shoulder-width apart, and leaned forward at the waist, keeping my legs straight and pigeoning my feet inward to help open me up. Then I reached back and spread my cheeks so that my plugged asshole, cock, and balls were all on full display.
“Ohh, wow, you have him well trained,” Alicia laughed.
“Thanks. He’s usually a very good boy,” Fiona said, patting my head.
“He is so smooth back here, too,” my sister observed, “Most guys have a lot of nasty hair, especially along their crack.”
“Yes, it makes it much nicer, doesn’t it?” Fiona said.
“Mmm hmm,” my sister affirmed as I felt her touch the thin line running down my perineum from my anus to my scrotum.
“If you want to remove the plug, just get your fingers into the ring, and pull,” Fiona explained.
Alicia seemed to hesitate, but then I felt her fingers sliding between my ass cheeks to grasp the handle. She started pulling, and I let out a breath that I didn’t realize I had been holding, trying to relax.
“It’s stuck or something,” my sister said.
“That’s one of his larger plugs, you’ll have to pull firmly,” Fiona said.
“Push a little for your sister, baby,” Fiona said to me, making the girls giggle again.
I pushed as instructed, and Alicia pulled harder. I moaned as my anus began to stretch around the thick head. There was an audible sucking sound as it finally broke the seal, and the steel bulb popped out.
“Wow, that was amazing!” my sister exclaimed as she looked between my gaping hole and the plug dangling between her fingers. “Does it hurt?”
“No. It took a while to work him up to that size plug. The sphincter is designed to stretch; you just have to take your time,” Fiona explained. “He also had to learn when to push and when to relax those muscles. It takes some practice for your brain to isolate them so you can consciously control them.”
“So, you are trainable,” Alicia laughed, and swatted me on the ass playfully.
“Oh, yes, he’s the best pet I have ever trained,” Fiona said, patting me on the head again.
“It’s very clean. I was afraid there might be poo on it or something,” Alicia said
“He uses an anal douche when he showers so he is clean inside and out, but that’s something you just have to expect with anal play – shit happens,” Fiona laughed, and then Alicia laughed, getting the joke. I had heard her say this on many occasions.
I was starting to feel a little light-headed, whether from being in this position so long or from the extreme humiliation I was feeling, I wasn’t sure. I just hoped that I wasn’t going to have to give that demonstration to my sister as well.
“Ooh, that sounds like fun. Like when we used to get enemas when we were kids,” Alicia said, like it was a fond memory.
I didn’t remember those enemas being fun at all.
“Does his hole stay open like that all the time now?” Alicia asked.
“It will close after a while, though I do keep him plugged almost all the time,” Fiona told her.
“Wow, really. So do I just push it back in?” Alicia asked.
“You should put some fresh lube on it first. Lubrication is the key to almost any kind of anal play,” Fiona said, handing her a small bottle of lube that was on the table beside the couch.
I heard her squeeze the bottle to coat the plug.
“Is this enough?” Alicia asked, holding the shiny plug up for Fiona to see.
“Yes, that’s good. You should apply some to his anus, and work some inside as well,” Fiona instructed.
I prepared myself for what was coming next. I felt the squirt of cool lube on my asshole, followed by my sister’s fingers. She circled the ring a couple of times and then dipped one finger in and began to spread the lube into my hole. She pulled out and then pushed in again, adding a second finger. I was moaning, and that seemed to encourage her. She twisted the two fingers around and pressed them as deeply as she could.
“Oh god, this is so bad,” Alicia said, but continued reaming my hole. “I would never have thought I would be doing this when I came over to visit today.”
“I promise I won’t tell anyone,” Fiona said, and they laughed again.
After another minute or so, Fiona suggested, “You can use three fingers if you want,” as she slid her hand down to my chest and began pinching one of my nipples between her thumb and finger.
I was breathing heavily as Alicia pulled out, then forced three fingers into my hole, and slowly twisted them. I started to clench, but Fiona pinched my nipple again, and I let out a sigh and relaxed. The anal reaming felt good, but I was mortified that my sister was the one doing it. That didn’t stop a drop of precum from forming on the tip of my penis.
“He seems to be enjoying this,” Alicia giggled. “He is leaking a little.”
“That’s just precum,” Fiona said. “Let’s show your sister how we take care of that.”
So many people had seen me eat my precum, and even a few had watched me clean up my full load of cum, usually after I swallowed their full load. You might think I’d be used to it by now, but you’d be wrong. I was utterly humiliated again as my sister watched Fiona wipe the head of my straining cock with her fingers, then bring them to my mouth where I licked them clean.
“Good boy,” Fiona said, patting my head again.
“So he eats his own cum?” Alicia asked, sounding amazed.
“Yes, and not just his own,” Fiona added, winking.
Oh god! Did she really just out me to my own sister?
“What! Is my baby brother a little cock sucker?” Alicia laughed. “I have always suspected something was up with you ever since I caught you and Tommy Greyson naked in the garage.”
“You never told me about that,” Fiona said, pretending to be hurt.
“It wasn’t anything, you always made such a big deal about that,” I complained. “We had gotten into some nasty-smelling mud down by the old farm. We thought it was manure, so we put our clothes in the washer.”
“Sure, and that’s why you were holding your cocks and jerking off together?” Alicia asked coyly.
“We were not!” I countered. “You made that up so you could blackmail us.”
“I saw what I saw,” she retorted, laughing. “You really shouldn’t argue with a woman who has three fingers in your ass.”
“She has a point,” Fiona said, laughing as well. “One more and she might as well use her whole fist.”
“Have you done that?!” Alicia asked with a gasp.
“No, not yet,” Fiona replied.
Realizing the position I was in, and not wanting my sister to be the first person to fist me (I wasn’t sure I wanted anyone to be the first), I stopped arguing.
After playing with my ass a little longer, Alicia stopped her probing, and Fiona coached her on working the plug back in. I pushed and then relaxed, finally the large ball of steel reached that point where it was more in than out, and, with an audible sigh, I felt my sphincter muscles draw it in of their own accord. That feeling of relief when my anus can finally relax and settle in around the narrow shaft is almost indescribable unless you have felt it before.
“He just sucked it in at the end!” Alicia exclaimed, giggling again. “That was so fucking hot.”
“Yes, it’s a reflex, but I always like that part too,” Fiona said, handing her a tissue to wipe her fingers, while she used another to clean off the excess lube around the plug before finally allowing me to stand up.
“He really did enjoy you playing with his ass,” Fiona said, pointing to another little dollop of precum that had formed on the tip of my cock.
“So what if he cums in you?” Alicia asked as she watched me wipe it off and eat it myself.
“Oh, he loves creampies, don’t you, baby?” Fiona cooed, patting me on the ass.
“Yes,” I mumbled. Could this get any worse?
“Why don’t you go open some wine for us, sweetie,” Fiona suggested.
I trotted off to the kitchen, happy to be a little less on display, but still able to hear all the intimate questions Alicia was asking, and Fiona’s honest, but very embarrassing (for me), answers. The conversation continued after I brought three glasses and a bottle of wine, with my situation, sexual activities, and childhood antics still the main topics.
It was hours before my sister finally said she had to leave to meet someone for a dinner date.
“I would love to visit more often. You guys have a great relationship, but I am a little surprised you are on board with all of this,” Alicia said, showing a little sisterly concern as I walked with her to the door.
“I love Fiona, and we don’t do anything that I haven’t agreed to in advance,” I said.
“Even sucking cock? I never thought you were gay,” she said.
“Well, I guess I’m bi now, not gay. I had been bi-curious for a long time, and Fiona knew it. She just helped me explore that side of me.” I explained. “And it’s just a fun, sexual thing. I am not ‘into’ guys the way that I am women.”
“As long as you are happy, my nudie little brother,” she said, giving me a hug.
“I am,” I assured her, “and, for the record, Tommy and I were not jerking off together, but I did kinda set up that whole situation so we would have a reason to be naked together.”
I blushed at the admission.
“I knew something was going on with you two,” she said, punching me in the arm.
“Nothing ever happened,” I said defensively, then added, “but he did have a nice cock.”
“Yes, he did,” Alicia said, with a knowing smile.
“Wait, did you and Tommy…?” I asked, giving her a sideways glance.
“Only a couple of times,” she said. It was her turn to blush.
“You slut!” I exclaimed, mocking her. “He was 5 years younger than you, cradle robber!”
“Yeah, yeah, but he was well developed for his age,” she laughed.
After my sister was gone, I gathered up the wine glasses and the empty bottle and carried them to the kitchen area. Fiona came up behind me after I had set everything on the counter and wrapped her arms around me.
“That was a fun evening. I really like your sister,” she said, letting her hands roam over my chest.
“Fun for you, totally embarrassing for me,” I complained, “I can’t believe you told her all that stuff, or that she told you all those old stories about me, and the plug, and everything else.”
“I know, it’s hard sometimes, but admit it, you enjoyed it too,” Fiona said, her fingers finding my nipples and tweaking them.
“Okay, yes, maybe a little. I’m just glad she didn’t freak out or anything,” I said, enjoying the teasing as my nipples hardened.
“Quite the opposite, I think. And it’s nice to not have to hide things from your family,” she said, as her hands traveled down my abdomen to stroke my smooth, soft pubic area.
“Well, my sister is one thing. She was always pretty open-minded. Apparently more than I realized after hearing some of her stories from when we were kids,” I said, feeling my erection grow even though she hadn’t touched it yet.
“So, you’re saying we should have your parents over next?” she teased, moving her hands to my hips and turning me around to face her.
“No, I am definitely not saying that,” I said emphatically.
Fiona kissed me passionately. I could lose myself in her kisses. I placed my hands on her waist and started to pull her in, but she had other ideas. Breaking our kiss, she put her hands on my shoulders and pushed me down.
“I can’t believe you let your own sister finger your ass, you are such a slut,” Fiona teased as I settled on my knees in front of her, “but it was really hot to watch, I need to cum so badly.”
I lifted the hem of her short shirt and, as expected, she wasn’t wearing panties. I kissed my way down her pubic mound. The scent of her pussy was intoxicating, and I buried my tongue into the folds between her labia, seeking out that little button that would give her what she needed, knowing that I would not be allowed the same relief.