Photographer 40 (Patreon)

“W-wait—” Nancy stammered in fear, but it was too late, as Penny already slipped a finger inside, extracting a cry of pain.

“I can stop if you can’t handle it,” Penny said, her anger highlighting her cuteness even more. She was trying to look intimidating, but ultimately, she was as scary as a little kitten, her efforts only made her cuter. 

Of course, in our current situation, the cuteness was a relative term. I had no doubt that Nancy, whose face was scrunched in a surprise invasion of Penny’s lubricated fingers. Yet, her expression tightened despite the pain, her competitive spirit coming to the surface once more. “I can handle anything you can dish out,” she said proudly. 

Too proudly in my opinion, as I was never a fan of giving such categorical promises, though it was significantly different being on the receiving end — or in this case, a VIP seat to watch the show. 

“Good,” Penny said as she pushed her finger deeper. Nancy bit her lips, trying to hide her pain, but she was too close to me to even have a hope of hiding the sudden tightness of her expression. 

More importantly, it wasn’t the only part of her suddenly tightening. Her walls clamped around my shaft even tighter, making it much harder to prevent a premature explosion even when her hips were still, not rocking back and forth.  

Nancy seemed determined to tough it out, but it lasted only until Penny slipped another finger. Then, the pain overcame her desire to look superior, her mouth opening to let out a cry. 

Luckily for her, I was a nice guy, so I leaned forward, capturing her lips to suppress the loud cry that was about to let out. Penny glared at me, showing the closest emotion she could to anger with her cute features, no doubt frustrated that I had stolen her little victory. 

She wasn’t frustrated enough to pull back. 

I grabbed Nancy’s hips, guiding her to move once again, helping her enjoy the closest thing to a double penetration she could experience in the current party without involving toys, especially when Penny added a third finger, making her let out a string of beautiful yet suppressed moans. 

I had to gesture Penny to dissuade her from a fourth finger, as I could feel Nancy was already at her limit. Luckily, despite her sudden bravery, Penny was as obedient as ever, and a gesture was all I needed to stop her. No additional orders, no threats. Just a gesture. 

“Beautiful,” I murmured as I pulled back from the kiss, which put a beautiful smile on both of their faces. Penny because I made eye contact with her while saying it, and Nancy because her eyes were still closed as her hips rocked, enjoying the position despite the occasional pain as Penny’s fingers moved aggressively. 

I kept one of my hands on Nancy’s ass, enjoying her fit body while directing her pace, while the other sneaked toward Penny, landing one of her spectacular breasts, my fingers sinking into her inviting flesh, earning some beautiful cries as a reward.  

Thanks to the sensitiveness of her breasts, that had been enough to distract Penny properly, allowing me to focus most of my attention on Nancy, and not just to enjoy the way she was tightening around my shaft. I pulled and pushed her harder, making her pace even faster, which she rewarded by getting even tighter, clamping around my girth like a supernatural mixture of silk and steel. 

Soon, her earlier distaste about Penny’s sudden initiative had been forgotten completely, replaced by a beautiful string of moans, singing the song of pleasure. Our unintentional cooperation was working perfectly, each push inside her — whether from my rock-hard erection or Penny’s naughty fingers — making her moan louder. 

Soon, the pleasure hit her with all the subtlety of a truck, and she started trembling with an explosive climax I had never seen her experience before, the combination of surprise invasion and the frustration that stretched for a whole day working its magic. I wondered that, if we were in a bed at this moment, she would have collapsed unconsciously.

Maybe I should test that, I decided as I pushed Penny back a bit before grabbing Nancy’s waist, and standing up. Admittedly, with her weight pushing my shaft even deeper inside her, her feet dangling, it hardly helped her to process the tsunami of pleasure that followed her spectacular climax. 

While our ultimate destination might offer her comfort, the journey to that comfort had been rather grueling for her, each step pushing my shaft deep inside her. She tried to push herself up to limit the impact, but with her limbs trembling softly under the invasion of pleasure that immediately followed her climax, it was a challenge she had failed utterly. 

Although, while she had failed on that particular challenge, she didn’t look like her failure was the cause of great regret, if her cries of pleasure were to be believed. 

“She seems distressed,” Penny murmured, but rather than following us, she had dashed inside, only to return to the bathroom, carrying a small bundle in her hands, trying to keep it hidden. 

She failed on that particular task, but I deliberately neglected to ask about that, curious what little surprise she had for me. She had already surprised me with her performance today, and I was curious what she would reveal next. 

So, I left Penny behind in the bathroom while I did my gentlemanly duty of helping an exhausted Nancy to move to the bed to rest. 

Well, almost rest. 

At least she would be laying on her back on the bed. 

Nancy showed that she had appreciated the sudden change as her body hit on the bed, and that appreciation came in the form of a beautiful moan, soft, yet loud enough to echo against the walls. I pulled out, and let her rest for a few seconds to allow her to catch her breath before commenting. “Don’t tell me you’re already exhausted, and that’s all you can handle?” I asked. 

“O-of course not,” she answered, her beautiful green eyes flashing with anger at the question, too competitive to accept that even in her state. Yet, with exhaustion and pleasure battling in her delicate body, an angry glare was all she could manage. 

“Oh, really?” I said. “So, you’re saying that even with exhaustion, you can handle enough to actually compete with Penny?” I said, seeing no harm in a casual namedrop to fuel her competitiveness even further. 

Her reaction was so predictable that I wasn’t surprised the slightest as I felt her arms wrap around my neck and pull me a kiss — through the lack of surprise certainly didn’t mean a lack of enjoyment. I let her capture my lips in a searing kiss, even as I pushed my hips forward, ready to impale her again. 

Just not through the entrance she was expecting. 

“Are you—“ she started as her eyes widened, only to be replaced by a gasp as I pushed into her puckered hole, still slippery thanks to Penny’s earlier assistance. 

“It would be rude to waste Penny’s helpful efforts, don’t you think so?” I asked as I hit her with a big smirk. She didn’t say anything, because she was busy biting her lips as I slowly pushed deeper. “Of course, if you think you can’t handle…” 

At this point, her reaction was perfectly predictable, enough to make it actually boring if the reward I earned wasn’t so spectacular. She said nothing, nor did she need to as she wrapped her legs around my waist, and actually pulled me deeper despite the pained cry that left her beautiful lips. A rare feeling of mercy hit me, and I leaned forward to capture her lips. 

That didn’t stop me from pushing my hips steadily of course, though I made sure to keep my pacing manageable as I slowly pushed inside her until I reached her current limit, stayed there for a moment, pulled back, and pushed again with the objective of breaking my previous record. 

The progressive invasion of the last untouched part of her body challenged Nancy with a glorious mixture of pleasure and pain, each with its own challenge. The pleasure threatened to push her to the land of unconsciousness as it compounded with the joy of her previous pseudo-double-penetration, while the pain flared and disappeared based on the current progress of the invasion, forcing her to erase every sign from her face as she tried to sell her toughness. 

She failed spectacularly, of course, but that only made her cuter. I took several breaks from kissing her pouty lips just to enjoy her fiery beauty as she struggled against the overwhelming pleasure, her eyelids fluttering repeatedly. 

“It’s not too late to ask for mercy,” I whispered even as pushed even deeper, her puckered hole loosened just enough to allow me to assault from multiple angles, each bringing a completely new experience for her, her moans strong enough to eviscerate her determination to keep silent. Her moans exploded, filling the room even as I impaled her again and again, deeper and deeper, yet she took all of it like a true champion. 

I was impressed. Not everyone had handled their first anal experience that smoothly. 

I noticed a movement from the bathroom door, only to see Penny peeking as she tried to stay hidden, yet the door was still wide enough to reveal her jealous expression, underlined with impatience. Yet, despite her impatience, she didn’t enter the room, limiting herself to the show we were providing.

Maybe she didn’t want whatever she wanted to show to be overshadowed by Nancy’s amazing performance. And if that was the case, it would have been the correct call, because as my climax got closer, I was finding it rather difficult to pay attention to anything but the beautiful redhead moaning under me. 

And then, Nancy raised her head to take initiative in a kiss, her tongue doing her best to invade my mouth only to be rebuffed in a counter-attack. As our tongues locked in a beautiful dance, however, I had finally reached my limit, and started painting her tight entrance with my mark. 

Already on the limit, the endless throbbing of my thickness proved too much for her, and she started trembling under the endless flood of pleasure. Her moans started spectacular, but with each repeat, they lost power, exhaustion catching up with her, and when I pulled out of her, she was already unconscious, her weight buried in the soft bed. 

And then, I turned to Penny, who was still watching us from the cracked doorway…