Chapter 3 - Where No Man Has Gone Before

“Bugger it!” Lia shouted from inside her room. It was Saturday, around half-two after a detour from the schedule for teas, and she was getting ready for her first catgirl costume rehearsal, the orchard photo shoot having been arranged for 5am the following Thursday.

“Problem?” I asked from inside her ‘studio’ where I was looking through the camera’s menus to see what the options were for shooting outside in possibly dim lighting. All I could see was that I was going to be hitting YouTube tutorials hard for the next few days.

“You could say that,” Lia said as she walked in, nude, wearing her ears so well they looked real ... and carrying her tail in her hand. She also seemed to have painted on some whiskers, coloured the tip of her nose a darker pink, and colour-matched her nipples to her nose.

“Nice details,” I said.

Lia smiled. “Thanks. Nude lipstick on my nips, same on my nose, eyeliner for whiskers, and good to go.”

“Neatly drawn.”

“I can draw in the lines,” Lia chuckled before her smile faded as she looked at the butt plug tail. “Jim. I, I just can’t!”

“No?” I asked carefully.

“I’ve never ... I mean I’ve not, er...”

Oh crap. You ever hate how you can solve someone else’s problem by going somewhere you never planned to? This was one of those times. That butt plug had to go where nothing or no-one had ever gone before it seemed. Curse you, other Jim.

“You know, it’s not so bad,” I said as I waved for her to sit down on the bed, waiting for her to get comfortable before joining her and hugging her gently to me. She was tense, all right.

“Not so bad? Ha!” Lia said bitterly. Ouch. “Oh I’ve heard that from guys–”

“Not what I meant,” I interrupted.

“Not ... it’s not!?” Lia asked, puzzled.

I smiled. “Time for a story?”

“Will it help with this?” Lia asked as she gave her tail a little shake. The plug end. It wobbled heavily.

“It might.”

“Then please, go for it,” Lia said, sounding hopeful but also unsure how a story could help.

“Okay, so this goes to a lot of places, the story I mean, but trust me, it’s not as bad as you maybe think it is if you’ve not done it before, at least once you get used to it a little. You see the thing is, back when I was a young man, no, I know I’m still young, but this is from the ‘before times’ when I was learning about things as things happened to me, and, well, let’s call him Jessie.”

“That’s his name?” Lia asked, suddenly interested in where this might lead. “His real name? Jessie?”

I smiled. “It is, but you’re unlikely to ever meet him so it doesn’t matter. Anyway, Jessie is my cousin, my step-cousin actually, and his family used to come down here once or twice a year on holiday, staying in one of the caravan parks nearby. As we got to a certain age, we grew curious about things the way we all do, and I suppose it was because he was on holiday away from home and I was spending time with him while he was here and not with my friends, but, er, we tried things. He was my first kiss, the first person to masturbate with, and one lovely afternoon I learned all about blowjobs with him. The following year we were a little older, a little more mature, a little more knowledgeable, and a little more confident to explore things. During that year I’d spent my time with a couple of girlfriends, but nothing serious and nothing that lasted more than a month or so. Jessie had been busy too, and he didn’t have a boyfriend but he had had more experience, so when we got together, he suggested we try and have sex. I wasn’t very confident, so, and this is where it might help you, he was so perfect with me I still have a little bit of a candle for him.

“You see what happened was we were alone at my house, the parents were out together, and we were supposed to have been playing football in the garden. In fact, I don’t think the cars had got to the end of the road before we were upstairs in my room, stripping, stopping to kiss, and stripping again, both of us as hard as we could be by the time we got into bed. We tossed a coin - sorry - we flipped a coin to see who was first, Jessie won, and so he got to fuck me. Thing was, I was really curious to try and really into him being the one who I tried it with, but I was also really nervous.

“Here comes the science part.

“What Jessie did was just get me to lie on the bed, face down, and he began to massage me. He rubbed the middle of my back, the bottom of my back, and then my arse. Once I was pretty relaxed - and he was telling me what he was doing before he do it so it was never a surprise - but he got some lube on his finger and gently rubbed it over my arsehole, just getting me used to the sensation of being lubed. Weird stuff. Cold and sticky but also sexy because you know what it’s there for. Anyway, after that he lubed up his cock - don’t worry, we used condoms - he then rubbed my arsehole with the tip of his cock, getting me relaxed so much that it felt ‘normal’, just rubbing my arsehole over and over and over it became normal now. He then asked me if I was okay for him to try, I said ‘yes’, and so he pushed into me, really slowly, stopping, letting me feel comfortable each step of the way and, er, then we fucked. The end.

“Well, not quite the end as after he’d fucked me I got to fuck him. The end. Again.”

“Jim that sounds so perfect. And you and he... ?”

I shook my head. “His parents moved a couple of years later, so we had one more summer where we had a lot of sex, but after that nothing more. Oh, I still get Christmas cards from him and his husband but that’s that.”

“Er... ?” Lia said as she tried to ask the question she wasn’t sure if she could or should ask.

I smiled. “No, Lia, no boyfriends since then. I think it was at that time and with him, but since then, no.”

Lia nodded. “You’re thinking that what Jessie did for you... ?”

I shrugged, puzzled how the boundaries between a model and her photographer were nothing like I imagined they would be. “Well I can at least give you a back massage, try and bliss you out a little?”

Lia took a deep breath. “Or ... or you could ‘Jessie’ me.”

“‘Jessie’ you?” I asked, wanting to be crystal that I was understanding what she was asking.

“If I lie down, can you, er, do what you said, massage, lube, then, er, in?”

“Isn’t that rather ... intimate?”

Lia grinned. “Well it’s not like I’m asking you to put your cock up my arse.”

“And that would be too intimate?”

“Fuck yeah!” Lia smiled. “Come on, let’s do it before we change our minds. I wanna role play as Miss Puzzle.”

“Miss Puzzle?”

Lia nodded. “I’m Mister Puzzle’s niece, a little shy, but also a little excited to do my first ever photo shoot.”

“Okay, that’s also not something I was expecting from today.”

Lia chuckled. “You, er, you wanna solve the last piece of the puzzle?” she asked as she waved the butt plug as bravely as she could.

I sighed. “For that pun I should not use lube.”

“Beast!” Lia complained. “Also, back in a moment,” she added as she dashed out of the room, returning seconds later with a couple of sachets of lube, handing them to me.

“Lia, I’ve really got to ask one more time–”

“Yes, Jim, that’s exactly what I want you to do. I really want to see if I can make furry photos or not, but when I, er, I clench, okay. But what you said, about getting all relaxed and taking it slow, if one of my old boyfriends had tried that then I wouldn’t still be an anal vir–”

Silence. Crashing, halting, silence which I rushed in to fill. “Happens to the best of us, doesn’t it,” I said.

Lia smiled as she shook her head. “Jim, exactly what does that mean? Happens to the best of us?”

I shrugged. “No idea. Just something to get the conversation started again.”

“Well ... it’s unconventional, I’ll grant you that, but it did work so marks for that I guess.”

“And while things are still a little awkward...”

“Hmm?” Lia asked curious to see where I was about to detour us.

“I’ll be careful not to–”

“Slip it up my fanny by mistake?”

I nodded. “I was going to say ‘touch’ but ‘missing the target’ counts too I guess.

Lia smiled. “I win.”

“You won?”

“I guessed you’d say something like that. Before. That’s why I trust you, because I know you’ll be super careful not to ... that.”

“I will!”

“I know. So, now we’ve got all of that out of the way,” Lia began as she handed me the butt plug end of the tail and lay down on the bed, wriggling and opening her legs as she got comfortable. “Would you kindly stick that gently up my arsehole?”

I chuckled. “That has to be absolutely the strangest request anyone has every made of me,” I said as I moved to sit at her side.

“I do love a challenge, and your challenge is to help me transform into Miss Puzzle, okay?”

“Okay, asks the girl with the cute arse who’s asking me to stick a plug up it.”

Lia giggled. “I never said working for me wouldn’t be hard... oh. I didn’t mean–”

“I know, Lia, it’s okay. Now, you think of whale song or whatever, and let’s just begin with a gentle back massage, okay?” I said, not waiting for her to answer as I lay my hands on her waist and began to softly rub the small of her back, more caressy than massagey.

“Mmm, feels nice.”

“Now I’ll move my hands a little lower,” I said.

“Please do,” Lia purred as I kept my hands where they were for a moment as I contemplated her arse. Maybe it was the running she claimed to do in the winter. Maybe it was her regime at the gym. Maybe it was good genes. Whatever it was, Lia had the best arse I’d ever seen. It wasn’t exactly a ‘bubble butt’ but God it looked firm and round and I really couldn’t quite believe I was being asked to get my hands all over it.

“I’ll, er, try not to enjoy myself too much,” I teased as I cupped her cheeks and began to do what I best imagined was a ‘relaxing caress’. I knew what had worked with Jessie, but Lia wasn’t him.

“No worries, no hurries, too,” Lia giggled as I felt her arse muscles unclench a little. I guess she’d been a bit more anxious about this than she’d said she was.

“You’re the Boss,” I joked as I spent a good amount of time caressing, massaging a little, and generally softening her arse as much as I could, judging ‘soft’ to equate with ‘relaxed’. “Everything okay?”

“Mmm, very,” Lia sighed as she seemed to stretch out, getting longer or taller or whatever, encouraging my hands to move around a little more as I massaged her upper arse, her side arse, and her under arse, her skin soft and smooth, her muscles relaxing with every action I took, and my own reaction growing more ‘insistent’ by the second.

“Now, first of all I’m just going to, er, spread things a little. Don’t worry, I’m not going to touch there yet, just get you used to having your arsehole, er, easier to get to...”

Lia giggled. “That’s the most romantic way I’ve ever heard that described,” she said as she wriggled about a little and opened her legs a little for me.

“Well, in the spirit of telling you new things, possibly, you know you’ve a really cute-looking arsehole,” I said as I eased her cheeks a little wider and then a little more as I caressed her, her arsehole a soft pink, still a little clenched-looking, and seemingly very clean.

“Why thank you. I used the bidet,” Lia giggled, seemingly reading my mind or at least guessing what I was thinking. “Twice.”

“Very considerate.”

Lia chuckled. “Can’t not, can I?”

“Quite,” I said. “Now, I’m just going to, er, massage it first, no lube, just, er, outside.”

“Okay...” Lia said, sounding a little more cautious now.

“Be brave,” I said as I put my thumb at the base of her spine, just below her coccyx, and slowly eased it down until it was just resting over her arsehole. I could feel her tension, still. “And a little more,” I said as I began to rub my thumb up’n’down, round’n’round, rinse’n’repeat until I could feel her beginning to untense.

“Ooh, that’s ... a feeling.”

“Good or bad?” I asked, pausing a moment.

“Actually, good. Naughty, weird, but kinda nice. You’re being really gentle.”

“Thanks, that’s kind of the whole idea,” I said as I began to press against her arsehole, not trying to push my thumb in or anything like that, and also not noticing, and I mean absolutely not noticing how her lips were a bit puffy. Small lips. Plump lips. Look away. “Okay, so, er, hold that thought a moment while I warm up the lube.”

“Warm it up?” Lia asked as I grabbed one of the lube sachets, ripped it open, and squirted it into the palm of my hand, rubbing my thumb through it for a minute or so until it felt like it hadn’t just come out of the fridge.

“We’ve got you about as relaxed as can be. If I was to use the lube cold from the packet, you might tense up again. Warm it will feel a bit odd, but it won’t feel as odd as if it was cold, too.”

“You really are trying to do everything you can, aren’t you?”

“Trying. Okay, so first I’m just going to put this around your arsehole, okay? I’m not going to push it in yet.”

“In... ?” Lia asked, her voice edged with anxiety.

“Yeah, it’s better if you’ve got some lube inside before, er, anything else goes into it.”

“Oh. I didn’t know.”

“No reason for you to,” I said, Lia having made clear this was all very new for her. “Here it comes,” I said, resting my hand on her cheek a moment before I opened her cheeks a little more and as gently as I could I put my thumb over her arsehole ... and waited. “Okay?”

“More weird. Warm goo on my arsehole? Definitely weird. And I think I can tell I’m glad it’s not cold.”

“Not my first rodeo,” I joked as I began to rub the lube around her arsehole, coating all the pale pink bits and even working the light hair she had there out of the way so that when the tail went in, it wouldn’t snag anything in with it.

“Haha, feels like I’ve had a little accident,” Lia said.

“But you’re okay, right?”

“I ... I am,” Lia said, sounding surprised at her own reaction.

“Okay. So now I’m going to ease my thumb, er, in. Slowly, I mean. Really slowly. If it’s too much...”

“I’ll be brave,” Lia interrupted.

Okay. This was it. Time to finger my neighbour’s virgin arsehole with a thumb covered in lube. Who needs Saturday afternoon football?

“I’ll just, er, no twisting or anything like that.”

“Twisting?” Lia asked.

“If you like this kind of thing it can be ... interesting.”

“Oh. Maybe not just now, thanks, haha. I’ll, er, I’ll try to relax.”

“Actually, there’s something you can do to help with that.”

“There is?”

“Breathe out. It’s harder to, er, clench, if you’re breathing out.”

“Wow, you really know your onions,” Lia joked.

I chuckled. “Never heard that described like that. Okay, so, er, here goes,” I said as I moved my thumb from resting lightly over her arsehole to gently pressing towards it, pausing a moment until I heard Lia theatrically breathe out, refocused myself on the task in hand, and increased the pressure on her arsehole a little ... a little more ... and then it started and my thumb began to enter into her arsehole.

“Ooh,” Lia sighed.

“Good ooh?”

“Keep going ooh.”

“Got it,” I said as I applied a little more force ... until the first knuckle of my thumb popped into her arsehole and I stopped.

“Okay?” I asked.

“Can I, er, have a moment?”

“Sure. Want me to pull it out?”

“No! No, I mean I need to get used to this don’t I?”

“Your call, Boss,” I teased, and so for a few seconds that’s what we did, Lia lying naked on her tummy on her bed, and me with my thumb a little way up her arsehole where I could feel her trying not to squeeze me back out.