Cherish Me 5 (Patreon)

Cherie led the girl that stumbled across us last week and her friend into the motel room. The two girls were looking at me with blushes on their faces (probably aided by the fact that I didn’t have a shirt on) and whispering softly to each other. As nice an ego boost as that was, I still felt pretty conflicted. I’d never been with anyone this young, the youngest my partner had ever been was eighteen. But despite my hesitance, a big part of me was looking forward to this. The Forbidden Fruit is the most tempting, after all.

“Missy, right?” I asked, getting their attention.

“Yeah?” she replied, her posture full of nervous tension.

“You want something to drink?” I asked as I stood up, Cherie stepping behind her and starting to rub at her shoulders.

“Um… sure. I’m not o… I’m fifteen.”

“Wasn’t planning on booze anyway,” I reassured her, filling a glass with a few cubes of ice and water.

“Thanks,” she muttered as she took the glass and started drinking.

“Straight laces, eh,” Cherie teased.

“Be nice, we’re here to make sure that everyone has a good time,” I chided her, even as my brain started to list all the soon to be broken taboos.

“Sorry, Missy. Why don’t you tell us a little about yourself?”

“Um… like what?” the girl asked as she set the glass on the side table, her posture no longer so tense.

“Hobbies, what sort of things you do in your free time, stuff like that.”

“Well, I’m part of an afterschool… gymnastics club.”

“Ooh, that sounds like fun, you should be able to try out a lot of interesting poses tonight. What about you Dinah?”

The now named Dinah started, pulling her eyes away from my washboard abs with a furious blush, and hesitated before answering, “W-well… I read? And sometimes draw? Missy’s done a lot more than me with her after school program though.”

Seeing as this could easily go on forever, I turned to Missy and asked, “Do you have any expectations for tonight? If you want, you can walk out that door right now. There’s no pressure to do anything you don’t want.”

“I just want to have a good time,” she answered, looking me in the eye. “I can tell you’re both experienced and, well… I’ve heard a lot of horror stories about the first time and I figure that if it’s with an experienced partner it’d be the best it could be.”

Well, she wasn’t wrong. I know I’d rather forget my first time because of how awkward it was. A glance at Cherie’s far too calm face told me she was having similar thoughts. Meeting my gaze, she gave me a nod while gently nudging Missy towards me.

“Alright,” I agreed, accepting that it was going to happen.

Missy gave a still-nervous smile, before reaching down to grab at the hem of her sundress (the same one she was wearing when she stumbled across us in the alley, I noted with a touch of amusement) and pulled it up over her head. Underneath the dress, she was fit. And had quite a few scars.

“Missy?” Cherie asked, both concern and surprise in her voice as the girl pulled her blue and white striped panties down her legs.

“I grew up in Brockton Bay, even in the okay neighborhoods if you’re at the wrong place at the wrong time you don’t walk away without some scars,” she said with a firm voice.

Kicking off her shoes, Missy stood there with her head held high and her arms at her sides. Missy’s body was odd in how little body fat it had, but it was also really hot. Even with her youth, she had a well toned and fit body, her scars adding character to her.

“Damn, you’re hot,” I whispered, making Missy’s faint blush darken, even as her nipples started to poke out from her chest.

“Th-thanks,” she said.

“C’mere,” I said, arms held out for her.

Taking a deep breath, and unintentionally pushing her chest out at the same time, she stepped over to me. Reaching down, I picked her up by her hips and lifted her up onto the bed. Gently maneuvering her so that her ass (which felt firm enough to bounce quarters off of) hung over the edge of the bed, I kneaded the muscles of her ass as I knelt in front of her puffy lips.

Leaning in, I gave her slit a long lick as I let my hands roam. Missy gave a pleasured moan as I ate her out and my fingers traced her scars and pinched her rapidly hardening nipples.

“Good, isn’t he?” Cherie cooed from her place next to Dinah. “Relax, let him take care of you. You’re in good hands.”

I don’t know if Missy was just already on edge, Cherie’s encouragement really got to her, or a combination of both. But whatever the reason, Missy let out a wail not five minutes after I started as she came. To my surprise, I got a much larger mouthful of her juices than I was expecting. It seems that our little vouyer was a squirter.

As her limbs collapsed onto and against the bed, I leaned back and said, “Well, that was a pleasant surprise.”

Missy didn’t respond, beyond staring at me with surprising coherence, all but begging me with her eyes to keep going. I guess that meant it was time, because with that kind of expression, who could resist? I certainly couldn’t. Much as I hated how they felt, I walked over to where my wallet was on the side table for a condom.

“Don’t bother,” Cherie said as I picked up the folded leather. Ignoring the look I was giving her (I was in no way interested in knocking up an elementary school girl), Cherie dug through her purse and pulled out a small box that had a cartoony picture of a sperm cell with googly ‘X’ eyes on its front.

“That image really doesn’t fill me with comfort,” I said dryly, making all three girls giggle.

“Nah, it’s the birth control I use. Based on the work of a chemical tinker out of Alabama, it’s a pill that makes it so that you can’t get pregnant for a month. Works both before and after.”

“I heard about that…” Dinah muttered, drawing all eyes on her. A fact that made her blush, “Um… my mom was talking about it.”

“Gimme one, I heard raw was better,” Missy said, lifting an arm with a bit of shaking. Cherie gave her a pill from the box and the glass of water from earlier and the younger girl gulped it down.

With the last of any credible objections gone, I dropped my pants and walked over to the cute, horny, and most importantly ready girl on the bed. Placing the head of my rock hard dick at her entrance, I leaned down and caught her lips in a kiss. Before pushing in. Missy moaned into my mouth, my tongue pushing past her lips at the same time as my cock pushed into her tight and wet pussy.

A part of my brain noted how smoothly my passage was, and while intellectually I knew it was likely due to the gymnastics she’d talked about, a dark part of me wondered about her home life and if I needed to “have words” with any parents. Pushing that aside, I instead focused on the tiny form beneath me. Gently pulling back, I gave Missy a moment to mourn how empty she was feeling, before pushing back in. Even without a hymen, it was best to start her slow.

“It… it almost looks romantic,” Dinah whispered from where she was watching us in a chair.

“My boyfriend can be caring like that,” Cherie answered. “Jealous?”

“Ye… no… I don’t know? I was expecting something crazy, like in that alley.”

“Oh there’ll be time for that later. But a girl’s first time should be special.”

There was something in the way that Cherie said that last line which made me want to stop and give her a hug, but that would be both rude to Missy and completely ruin what Cherie was saying. Instead I sped up, my hips moving faster as I fucked Missy, my hands moving to grab her hips as my dick all but reshaped the insides of her pussy.

“Ooooooooohhhhh!” Missy cried as I fucked her. She wasn’t a screamer, but she wasn’t quiet either, gasping and moaning as the pleasure of our coupling ran through her. Again and again, my length was buried into this young girl, filling her like she never had before. And she was absolutely loving it.

“Fuck that’s so hot to watch,” Cherie said with a groan as a hand came up to tease at her nipple poking through her dress.

“Yes,” Dinah whispered, just barely loud enough for me to hear over the sounds of my and Missy’s hips colliding.

“It feels sooo gooooooooooooo-aaahhhhhhhhh!” Missy cried out as she came a second time, and I pulled out so I could watch as she squirted out more of her juices and girlcum. It was fascinating to watch. I wasn't close to cumming, but seeing a girl react to you like this, especially this explosively, never gets boring. Especially as it's pretty rare. Missy took a few breaths, completely lost in lust. She stood up, with an eager, and expectant look. Yeah, this one was an eager keeper.

“You know, I think it's time to see those... gymnastics skills in action.” Cherie smiled, while gently pulling Dinah over to sit in her lap. With Missy’s permission, I raised her leg, while guiding her arm to the wall. This looks like it’ll lead to pretty deep penetration, something I was greatly looking forward to.

“Ready?” I asked, seeing Cherie’s fingers slip under Dinah’s dress.

“Do it, fuck me!” Missy cried as she pointed her leg to the ceiling, pulling off a standing split.

Yeah, no way I was resisting that. Wrapping my arm around her leg, I crouched down just a little and slid into the warm and wet depths waiting for me. Just as my base touched her lips, I felt my head touch something else much deeper inside her. From the way her pussy clamped down, to the point that it almost hurt, she felt how deep I was too.

“Ooh yes, she’s definitely a little gymnast, isn’t she? It’s so fun to watch when a girl can bend like that. I don’t think I could pull that off,” Cherie admitted, arousal, amusement, and exasperation in her voice. “Maybe I should take up yoga?”

“It took her… a while… to get this… good,” Dinah said between gasps, her hands covering Cherie’s as they teased at her. “But yeah… Missy’s really… gooooooooooood!”

I wasn’t going to be able to hold it in for much longer if this kept up, so I paused and leaned down to whisper to Missy, “Want to try something a bit different?”

“Yes! This is the best thing ever!” she agreed, her lustful grin practically splitting her face.

Letting go of her leg, I carefully guided her into the position I wanted even as Cherie and Dinah continued to talk.

“You’re so polite,” Cherie cooed, not stopping her ministrations even through the younger girl’s orgasm. “You don’t want to say that I can’t do it.”

“We… well,” Dinah said through her pants, trying to gulp down air and talk at the same time, “yeah?”

“Don’t worry. I’m not so insecure I can’t admit it. You’re still cute as a button,” Cherie reassured her. “Besides, I’m getting the feeling that you want a turn now, too. Don’t you, Cutie?”

“Yes… it looks… so good.”

“Trust me: it feels even better.”

By this point, Missy was in the position I’d been hoping she could pull off. If there were any way I could do so without getting thrown in jail with a man named Bubba and the key “lost”, I’d be thanking her gymnastics teacher. Though I really doubt that they had Missy getting fucked while bent over backwards and both hands and feet flat on the ground. This was the first time I’d seen anyone in the bridge position outside of particularly kinky sex books, let alone been with a partner that could pull it off.

No more waiting, I drove my dick into her. I was already amazed that she could even hold the position, I was all but flabbergasted that she was managing to hold it steady with my fucking her hard and fast. The whole evening had proved too hot for me to take it slow, so I just let loose on the girl before me. My hands on her hips pulled her tiny body into me, as I drove my hips forwards with all the strength I could muster.

“Yes, yes, yes, yes, yes, yes, yesyesyesyesyesyesyesyesyesyesyes!” Missy chanted as I fucked her, her pussy flexing and clamping down like crazy.

It was too much. The amount of fucking I’d been doing, the positions, Missy’s age, all of it came to a head as I mashed our hips together as close and tightly as I could and let loose. Missy moaned and came herself as she felt my cum flooding her womb, her arms and legs shaking as she struggled to maintain her pose. Finally, after what might have been the most explosive orgasm of my life, I pulled out and let Missy collapse onto her back.

“You did amazing, Missy,” I told her as I panted from the exertion. “I’m impressed. I know your friend and my girlfriend are too.”

As the words left my mouth, I paused. I… this was the first time I was able to call someone ‘my girlfriend’ so easily, without feeling like I was lying or acting. It was… I didn’t have words to describe how big a deal that was for me. All my life, every romantic relationship had this undertone of use, that they were using me to get what they wanted. And what they wanted wasn’t to enjoy time with me, it was always about what I could get for them. That realization, if nothing else, made everything about this night worth it.

It was only then that I snapped out of my self reflection and saw that Missy had turned over, and raised her ass up into the air, shaking her cute little butt. Well, I certainly wouldn’t pass up on an invitation like that.

“I thought guys had to wait?” Dinah asked as I began to fuck Missy into the bed.

“Trevor doesn’t,” Cherie answered, even as she teased another shuddering orgasm out of her. “It’s one of the things that makes him so wonderful.”

By the time I finished inside Missy a second time, I was in serious need of some water. But when I turned around to head to the kitchenette, I was treated to an unexpected sight. Dinah was still sitting in Cherie’s lap, but her dress had been pulled up and her panties were dangling from her left foot. The end result of this was that, combined with Cherie’s fingers holding them open, I could see that Dinah was absolutely soaked.

“Ready to finish the set?” Cherie asked with a cheeky grin, even as a furiously blushing Dinah pulled her dress up over her face.

I’m going to Hell, but fuck yes!