Business woman and cam girl on special vacation – part 5

I slipped into position behind her and reinserted my strapon.

“You want me to hit your g-spot, huh?” I said.

“Mmm, ideally.”

“So it has nothing to do with wanting spanks?”

I slapped Isabel’s ass as I spoke, emphasizing my question rather physically. She yelped in surprise.

“Unf, no, not about that,” she said.

I spanked her a few more times while moving in and out of her pussy.


“Well… maybe partly,” Isabel admitted. “You could, you know, give me a few more if you wanted.”

I grinned and smacked Isabel’s butt, alternately getting more yelps from her, and something that was very close to purring. She was so ridiculously into this, and it was actually really working for me.

I loved getting such positive reactions and feedback from Isabel. I got so into it, in fact, that I missed the significance of her mewling as it changed in intensity, and the way she worked harder to move her hips and find just the right angle.

“Mmm, yes, V. Right there. Keep doing it like that. Just like that.”

I blinked and stared at Isabel in brief incomprehension until I realized she’d positioned her hips right where she wanted them, where I was hitting just the right spot inside her. I continued thrusting as consistently as I could manage, giving her what she needed.

Isabel came hard while I was deep inside her, giving her pleasure. It was, for me, a fairly wondrous and unique sensation, giving me a weird sense of power.

I cradled her afterward, just holding her in my arms. She was all wiped out for a bit and let me comfort her while mostly just tracing her fingernails over my skin and occasionally playing with my tits.

“Might be too dangerous to let you do that to me on stream,” she said.

“Who are you kidding? You’re going to try it anyway.”

“Hehe, I might.” Isabel stretched out, sighed, then curled back up. “Do you need a cum?”

“Just rest.”

“You do, don’t you?”

I booped her nose. “Get me later. I just want to snuggle you right now.”

She nodded. “Ok. That’s a good deal.”


Isabel and I got something of a routine going, left to our own devices as we were. I tried to get most of my work done in the mornings, especially any virtual meetings I needed to attend. Isabel would often make me coffee and/or breakfast while I was working, and loved to play games like delivering a mug or a plate to me while I was on video and she was wearing very little or nothing at all. Of course, I wasn’t much better, oftentimes only being dressed from the waist up.

Lunch time was usually an excuse for something naughty. A little break before Isabel got into her shows. We’d eat, sure, but it was pretty usual for us to eat more pussy than food.

Afternoons and early evenings were Isabel’s cam show times.

“I changed my schedule a bit during the summer,” she told me. “Later times would actually be better for viewers, but it’s so nice taking advantage of summer sun.”

“Mmm, I don’t mind your work helping turn you into a tanned goddess.”

Isabel stuck her tongue out playfully and flounced away to set up.

We worked around each other’s schedules and needs pretty fluidly. Some days I had too much to get done and had to retreat to my cottage for privacy, mainly so as not to get distracted by my girlfriend’s camming. Some days I happily sacrificed some productivity for the privilege of sitting in the sun and watching Isabel work.

Some days, the really fun ones, I helped Isabel out with her shows. That usually meant on weekends when I didn’t have to work but Isabel did, or on the weekdays when I could get everything done that I needed sufficiently early in the day.

It took some adjustment and easing in on my part. Especially as Isabel got more and more naughty ideas she wanted to do on stream with me.

We started with making tipping for spanks a more common thing. Not every day, not when I was busy, but most days they were available. That went through phases of lots all at once, or not much in a given show. That was normal according to Isabel. It depended on people’s moods, and sometimes whether one person tipping for spanks led to more people wanting to do it too.

We graduated to some other ideas Isabel had that mostly involved my clothes staying on while I was on cam. Me wearing the strapon and doing things to Isabel with it was one such thing. It did leave me a little exposed below the waist, but everything was essentially covered. It did feel rather lewd swinging a fake dick around between my legs for our viewers’ titillation, regardless of my actual physical exposure.

Strapon play started out all oral. Isabel put her hair in pigtails for that show, because of course she did, and depending on tips would play with the dildo attached to me, or lick and suck on it, or her favourite, she’d guide my hands to her pigtails and have me face fuck her.

Admittedly, as I held on to her pigtails and shoved my strapon down her throat over and over until her eyes teared up and spit ran down her chin, I kind of enjoyed it too. I could call her a subby little perv all I wanted, but choking her on cock, such as it was, turned me on nearly as much as it did her.

“You make quite a mess of yourself sometimes,” I told her afterward as I helped wipe the worst of the mess off her face. After she’d given her cam audience a good close up of her spotty chin and streaky makeup, of course. There was no cleaning up before showing off.

“Can’t hardly take me anywhere,” she agreed.

“Did your throat take enough abuse yet?”

Isabel shrugged. “All depends if anyone tips for more, I guess.”

“Of course it does. Don’t think I don’t catch you loading the dice whichever way you want them to fall.”

Isabel just grinned innocently at me, as though she’d never encourage her audience to tip for whatever horny thing she wanted to do anyway.

We did some regular pegging at times too, but oral was more her thing on cam. She said it played better for the viewers, whatever that meant. I think it was really just a case of she preferred me fucking her face on cam, and her pussy in the bedroom, and that was all there was to it.

There was also some mild bondage play, which produced some quite good results for very little effort on my part. Once I figured out the basics of tying Isabel up so that she was restrained but comfortable, that was all I really had to do. It kept her and her audience amused, particularly with her tip-activated vibrator in her pussy so she had to squirm helplessly if she got a lot of action all at once.

Sometimes it meant gagging her for minutes at a time too, which I enjoyed and played my own game of pretending not to remember to ungag her. Her muffled complaints entertained me, and actually kind of turned me on if I was in the right mood.

The larger game Isabel was playing was luring me into being more and more comfortable with my role as her assistant, including quite a bit of nudity of my own.

One of her first ideas, and one that I really liked, involved a cheap, second-hand sundress and some scissors. Isabel had me lay out on my tummy with my laptop in front of me, then ‘sneakily’ brought her laptop over to get a good angle of me where she was theoretically out of my sightline.

Isabel then spent over an hour taking tips to cut strips off the bottom of my dress, slowly working up my body. It was another one of those ridiculous scenarios where I didn’t think anyone could possibly believe that I didn’t know what was going on, but she sold it so well that maybe that didn’t matter.

It was a scenario that involved very little of me for a while, and since I was pretending to be working anyway, I took the chance to get some actual work done. That only lasted until about when Isabel started cutting strips off my dress nearer and nearer to my ass, and especially as she slowly revealed it.

I practically felt the desire emanating from her to play with my butt in between tip notifications. That would have ruined the already flimsy facade, though, and Isabel made do with speaking quietly to her chat instead. I had earbuds in to try and give the illusion that I wouldn’t hear what she was saying, but I didn’t have anything playing on them so my hearing was, in fact, unimpeded.

“Guys I can’t believe she hasn’t noticed yet,” Isabel giggled in a hushed tone. She was all curled up next to my lounge, only half-dressed herself. “How far do you think I’m gonna get? I’m gonna get in so much trouble either way. She just got this dress.”

I rolled my eyes. It was technically a true statement, that the dress was newly acquired, but I just couldn’t take some of Isabel’s acting with a straight face, effectively though it may be for her purposes.

“No I can’t stick my finger up her butt,” Isabel said with a slight note of indignation. “First of all, she’d definitely notice that. Second of all, there’s tips if you want butt stuff, and it’s only for my bum.” I caught her wiggling her scissors out of the corner of my eye. “Ooo Rrr we could snip some more of her dress, see if we can’t expose that whole luscious booty.”

I tried not to squirm too much as Isabel cut up more of my dress. She got up to my lower back, then snipped my panties too. I’d only been wearing underwear for the look of the thing, but something about her cutting them and leaving my ass totally bare was that much more embarrassing and, rather perversely, thrilling.

“God I could just bury my face in that ass right now though,” Isabel said. “I mean look at it.”

She picked up her laptop and moved it closer for a better view of my bum. It was just as well I was facing totally away at that point, because I was sure I was beet red.

Isabel showed me off a bit, then went back to slowly progressing up the rest of my dress, cutting strips off of it until there was nothing left. She even cut my bra, which was unnecessary since she could have just unclipped it, but it was sexier her way. Both bra and panties had been purchased cheaply at the Isabele time as the dress, so it wasn’t like it mattered.

I spent a few more minutes after I was naked just lying there and letting Isabel show me off. I was embarrassed, anxious, horny, thrilled, and I’d really only idly been playing a game on my laptop for the last little bit anyway, since my concentration was nowhere to be found.

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