Chapter 3

Time flies when you are having fun, or so they say. In my case it seemed to be standing still. It has been almost a month since Fiona has allowed me to have an orgasm, the longest denial period ever.

It had been months since 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 me 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 babysitting her little brother, getting me to roam the house, and even the backyard, completely bare. She had even had a couple of her friends over a few times. That brought back some vague memories of running through the house naked being chased by my mom or my sister and I definitely remember 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 realized how much she had been there egging me on.

“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.

Wearing a butt plug 24/7 was the other 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. It had become more and more comfortable over time, and I now had a small collection of different sizes, shapes, and materials, but the plug she preferred was largish and made of stainless steel so it was heavy and made me feel very full. That was the one I was wearing that evening. It was a constant reminder of the things I was willing to do for Fiona.

The worst part about the evening was that I had a nearly perpetual erection. After going so long without an orgasm and the constant teasing conversation was keeping me hard and my sister thought it was hilarious.

“He was always a little horndog when he was running around naked, even from 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 almost never 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, and 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.”

“What would you like to know?” Fiona prompted, “You can ask us anything. You can even take it out and put it back in if you want.”

I’m not sure if it was me or my sister who gasped. Maybe both. Me from embarrassment, Alicia from excitement.

“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 enjoyed introducing people to butt plugs almost as much as she enjoyed humiliating me. The fact that it was my sister just made it that much better.

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.

“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 under the lip of the plug and pull,” Fiona explained.

Alicia worked a couple of her fingers under the plug as Fiona described. She started pulling, and I let out a breath that I didn’t realize I was holding.

“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 slimy steel bulb slipped 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?”