Every summer, I told myself that I was going to do it, and every summer I failed. This was the year it was going to happen. So help me God, I was going to visit Carissa.
Way back in middle school, Carissa and I were inseparable. We were those kinds of neighbors that made parents joke about how we would always end up as boyfriend and girlfriend. Some of the adults around us even asked Carissa point-blank if I was her boyfriend. It was a weird thing to ask a nine-year-old, but Carissa was Carissa and, even back then, smiled and told them a solid “no,” then smiled back at me and didn’t treat me any differently.
That’s how we were. Carissa was the kind of girl that never got embarrassed, never treated me weirdly, and never judged. As we grew up, she went to a different high school and we naturally drifted apart, but whenever she messaged me online, it was like old times again. I heard from her even less when I went off to college and she elected to stay home to watch over her bestie’s family business. She seemed happy – why wouldn’t she be, who else gets an opportunity right out of high school to run a company with your two closest friends? – and I was happy for her, but… I also missed her.
I think the first year I was back from college, I was too… scared to go back. Carissa never talked to me differently over text, but at that point, even though we were neighbors, we still hadn’t seen each other in over a year. It felt weirdly embarrassing to just strut into the shop and act like nothing changed. So, the summer flittered by, slipping through my fingers like sand. The second summer, I told myself that if I wasn’t going to do it the first year, it would have been weird to do it the next year. But after we stopped even messaging this year… I realized that if I didn’t do something, my friend and I could drift apart forever.
I didn’t like like her or anything, but Carissa was still a treasured friend, and… I didn’t exactly have a lot of female friends. Hell, I was turning 21 soon and I still never had a girlfriend… or at least a girlfriend that lasted more than two weeks. I needed to hang on to what (and who) I had.
Besides, it was summer. It was a time for relaxing, doing as little schoolwork as possible (a universal truth even when you were in college) and enjoying life, complete with beach trips and cold treats. Conveniently, the business Carissa helped run was a freaking ice cream store. It really didn’t get any more cut-and-dry than that. Sure, the store was a little out of the way… Okay, it was very out of the way. It wasn’t anywhere near where I lived in downtown Guelph… in fact, it was in Old Guelph. It used to be this charmingly old part of town, but as the jobs dried up and buildings dilapidated, it lost the ‘charming’ part. I was almost surprised to hear the old ice cream shop was still standing after three years of running it in such an abandoned part of town.
And “abandoned” was really the word. I had to take two buses to even get there, and when I’d reached the place, it looked like one of maybe three stores that were still operational. The other two were a payday loans place and a cannabis store – the telltale signs of a down-on-its-luck neighborhood. The store popped out to anyone looking at it as the sole source of color on the street, which was definitely thanks to the girls putting in as much effort as they could. As I reached the place, one of them was even putting the finishing touches on one of the walls, doing some repainting.
I gave her a friendly smile as I walked up to the place. She was kind of cute – late twenties, mayyybe thirty, with the kind of delicate tan and long curly blond hair that told me she was going to be one hell of a MILF one day.
She returned my smile with a polite “Hey there!”, and her voice confirmed it for me. Definitely MILF material someday. She already had a bit of the “mom bod” thing going on – a pretty nice ass filling out her jeans, even a slight “puppy fat” pudge filling out the front of her stomach. Heck, maybe I was misreading and she was expecting or something. I didn’t know.
When I walked inside, I was greeted by the feeling of cool air washing over my body. God bless air conditioning. I reveled in the feeling for a bit, especially since I couldn’t revel in the feeling of reuniting – Carissa was nowhere in sight. Instead, a second girl was at the counter. This girl was around Carissa’s age, though she had skin more like mine – I wonder if she was mixed-race too, or just naturally tanned. I couldn’t see much of her body behind the counter, but she had brown hair that fell to her shoulders and a smile that – despite a frankly average face – seemed to light up the room. “Hi! Welcome to The Divine Creamery!” she opened peppily. “What can I get you?”
I chuckled, looking around the store. “I can’t remember the last time I walked into a store and someone said, ‘hi, welcome to Insert Store Name Here!’” I remarked. “You girls are big on the marketing, huh?”
The girl shrugged, the smile still on her face. “We do what we can,” she replied, then looked at me expectantly.
I hesitated. I wasn’t even sure if I was going to buy anything – I was frankly just here for Carissa. “Um, actually, I was hoping that I could see someone here, if she isn’t too busy,” I replied, looking behind the counter. “Uh, Carissa?”
The girl looked at me for a bit. I don’t know why, but I started to feel a touch nervous, especially when her smile took on this weirdly different look. “Ah,” she replied slowly. “Did you order something from our secret menu?”
That was a curveball. “Huh?”
“No?” she continued innocently, then went to the door behind her, knocking on it gently. A few seconds passed, then it opened to reveal the face of who I’d been looking for.
Carissa was such a sweet girl. Like the woman outside, Carissa was blond too, but her face was decidedly “untanned” and pale. She had this cute “girl next door” look – average height, modest but visible bust, cute smaller butt, shoulder-length haircut, and the most excitable face you’d ever see. I had older cat energy, but Carissa definitely had dog energy. As soon as she saw me, the dog energy came through, with her tail practically wagging as she ran out of the doorway and past the counter to give me a hug.
“Oh my God, Dante!” she sang. “I haven’t seen you in for-fuckin-ever!!” She clung to me in a friendly hug and I chuckled as I hugged her back. “I didn’t know you were back home!” She broke off the hug and looked at me, expecting an answer.
“Well, uh… tada!” I lamely replied, and looked around. “This is a cute place.”
Carissa shrugged, her mood slightly dropping. “Fixer-upper,” she admitted, “but we’re making it work. This is Michelle; me and her take turns running the front and back of the store.”
“Oh, nice to meet you,” I told Michelle almost nervously. I didn’t know why I felt guilty for not introducing myself to the store clerk, but I did. “I assume she’s not the owner, right? The woman outside-”
“Yup, that’s Lauren,” Carissa said with a nod. “She’s always been like a, uh…”
“Sister to you?” I guessed. Oddly, Michelle laughed at that.
“Nah, nope. Not a sister,” Carissa laughed alongside her. I guess it was some inside joke I couldn’t understand. “But she has helped me a lot. She – mentor! That’s the word. She’s always been like a mentor to me. She’s taught me practically everything I know about business and customer service.” She smiled at me, pausing for a bit before shrugging – as if I should have talked but didn’t – and continued. “So! What have you been up to?” She reached forward and ruffled my short black hair with her hand. “Aside from going short now. Y’know, I preferred the hair long.”
There really wasn’t much to tell, but I tried to make it work. I wanted to catch up with Carissa, and it didn’t seem like there were people exactly lining up in front of the store, so I made myself comfy and enjoyed this moment of friends reuniting.
***
“And we had to wait, get this, four more weeks until it would be in stock again,” Carissa finished the story.
“No way!” I blurted out.
“Yup, I was there, it sucked,” Michelle added as the front door opened. “Running a business is hard! Without Lauren, this place would have sunk a long time ago.”
“And without you two,” Lauren added, walking past them with a full box, “I would have stopped trying years ago.”
“Dante, Lauren. Lauren, Dante,” Carissa added in a friendly tone. “Lauren, this is the childhood friend I was talking to you about.”
Lauren looked at me… in a strange way. If I felt egotistical, I might have thought she looked me up and down, like she was checking me out. “Ah! I thought maybe-”
Carissa coughed loudly. “Dante has been a good friend to me for a long time,” she repeated to Lauren. “Isn’t it sweet he decided to visit me? We haven’t even seen each other in years!”
Lauren smiled in understanding, then turned to me. “Well, Dante, any friend of hers is a friend of mine. Were you thinking of ordering anything?”
I looked at the menu and thought out loud. “These all seem good, although I think I heard Michelle say something about a secret menu…?”
All three women paused. I looked from the menu at Carissa to see her staring at Michelle, trying to communicate something. “And what would that mean, Michelle?” she asked.
Michelle scratched the back of her neck. “Sorry Dante, it was a dumb inside joke,” she clarified. “Sometimes guys come here just to say hi to her. She’s, y’know, popular like that. So we have our own little lingo to-”
“You get the idea,” Carissa cut in, then pointed to the menu. “But, if you want anything there on our actual menu… my treat?”
***
It turns out that when you finally go and man up to do something, it gets a lot easier to do it again. So, after the first day, it was way easier to visit Carissa again. And again. Eventually, I felt like a regular, despite the fact that I actually ordered once or twice.
I would have thought the girls would chase me outside for not bothering to buy anything, but luckily, they seemed bigger on the community than just making a profit. In fact, whenever Lauren, the owner, saw me, she just smiled. “Well, I’ll be! Dante!” she greeted me on the third day, smiling as she walked past with a bucket of paint in one hand, and a paint roller in the other. “You’re becoming something of a fixture around here, aren’cha?”
“Hey, L-Lauren,” I replied, in a less smooth way than I wanted. “Hope it’s okay I’m here again…”
“Why wouldn’t it be?” She stopped and gestured around her. “It’s not like you’re holding up a line or anything.”
“Still,” I mumbled, then looked at the paint bucket. “I mean… hey, if I’m here, I can always make myself useful, if you want. It seems like you can use a fourth set of hands around here.”
Lauren’s eyes darted to the door to the back, and her face clouded with an unsure look. “Uh, that’s very kind of you, but I think the three of us got a handle on it.”
“I’m not even looking for a job. If you just need a few favors done, I can-”
“All good! You just sit there and look handsome. Think you can do that?” With that, Lauren winked at me, turned her back, and walked away. It was weird… She was definitely being dismissive, but in a friendly way. It didn’t feel fake, or like they didn’t want me around. It was more like… I didn’t even know what it was more like. Still, more often than not I was just kind of… standing around. Sometimes Carissa or Michelle would be around to work the front, but sometimes all three were gone, with literally just me to stand in the store part of the store. A part of me wondered what would happen if a customer came in, but I guessed Lauren would notice and come in with them or something. I felt a little silly, just standing around doing nothing when I was here to see Carissa, but to her credit, she’d notice that and try to be out front and have a small conversation with me every so often.
Today wasn’t like that though. It was kind of odd – the two were constantly in the back to complete orders, but I rarely ever saw people at the front actually making orders. Plus, it was an ice cream shop. There wasn’t a whole lot of prep needed for ice cream, was there?
A part of me felt dejected – maybe even silly; silly for thinking Carissa wanted to see me as much as I wanted to see her. Sure, I may not have had a crush on her or anything, but still, I liked spending time around her! There wasn’t anything wrong with that. Despite being told to “sit there and look handsome,” I couldn’t just sit around and wait for Carissa. She was obviously the type of girl to get up and make a move for what she wanted, and I bet she would have respected it if I did that right back. So, with my mind made up and no one around to tell me it was a bad idea, I got up and moved behind the counter, then made my way to the door to the back room, and peered in through the little window.
The window was small, so I could only properly see into the back room when my nose was practically pressed up against the glass. I looked in… and my breath caught in my throat. It felt unreal. It felt like my eyes were deceiving me. I had to, somehow, be wrong about what I was seeing.
Even with Carissa’s back to me, it was unmistakable what she was doing. My face flushed – she was fingering herself on the job. You’d think she would just excuse herself to the bathroom to do that or something, and maybe that’s what made me get closer to the window to get a better look. I couldn’t stop the gasp from escaping my throat when I saw the carefully prepared treat below her. Carissa was squatting over it, clearly concentrated, and began to raise her hanging head, slowly lifting it up to look at the ceiling. At once, her juices squirted out, and a viscous string began to decorate the ice cream. She moved her hips around, clearly intentionally decorating the dessert… in a way that screamed, “this isn’t even my fiftieth time doing this.” She was… a seasoned pro at whatever the fuck was going on.
The front door’s bell took me out of my concentration. On instinct, I whipped my body around, letting my back rest against the wall next to the door in the least inconspicuous way possible. I saw Lauren coming into the store with a stepladder in her hand – she looked me over and chuckled. “You look lie you’ve seen a ghost,” she mused, then her eyes drifted to the door next to me. “…Or something else.”
I didn’t say anything. Lauren walked slowly up to me, then peered into the window beside me. I couldn’t see what she saw, but she slowly looked back at me. I looked into her eyes and said nothing, not knowing what was going on in her head. “And now just what have you been up to, hmm?” she asked with more serious a tone than one would normally use while asking someone that.
“I, uh, well, I was just… here,” I feebly managed to stutter.
She gave me a small smile. “Ah, well then, my mistake,” she told me, her tone friendly but still serious. “I tell you what: you seem mighty lonely out here. I’ll ask Michelle to find the time to keep you company as soon as she’s able. Sound good?”
“Well… I-” I didn’t manage to get another word out before Lauren disappeared into the back room. Did Carissa manage to get cleaned up…? God, it would have been embarrassing if I got Carissa caught. I couldn’t resist peeking again into the back room, only to see the blinds had been drawn on the window. It was wild Carissa didn’t think to do that herself before…
I realized only then how weak my knees were, so I found one of the few stools at the front of the store and sat down, putting my head on the counter. What the fuck was all that? Did Lauren see? If she did, was she pissed at Carissa? Did she know? Did Michelle see? What the fuck was going on?!
“Hey,” a voice took me out of my thoughts. I lifted my head to see Michelle standing there, cleaning a glass. “You good?”
“Um…” I replied. I didn’t know whether Michelle was instructed to calm me down, or what she knew, or… “Yeah, why wouldn’t I be?” I played it safe.
She chuckled. “Because you just saw an OSHA violation?” she joked.
I felt myself turn pink. I didn’t know what to say. “I’m sorry,” I immediately blurted, looking down. “I wasn’t being nosy. I didn’t mean to see such a, um, such a private momen-”
“Weird, sure. Private? Enh, I dunno,” Michelle replied, cool as a cucumber. “I kept telling her that if you were going to be hanging out here, you at least deserved to know. At least then, you wouldn’t have had – you probably had a heart attack when you saw.”
Speak of the devil: my heart started beating faster. “It’s, um, not exactly getting any better,” I admitted.
She gave a throaty, musical laugh. “You’re funny,” she replied calmly. “But I promised I’d let Carissa be the one to tell you the full thing.” She looked off towards the back room. “She’s, uh, busy right now.”
“So this place is… a front?” I asked gingerly. I never thought in my wildest dreams my childhood best friend would become a… Was this prostitution? Clearly the other women were aware of it.
“A front? Nah, we sell what we say we sell,” Michelle replied. “Just depends on what you’re buying. As I said, I promised I’d let Carissa tell you.”
“So I just have to wait for her to… do whatever she’s doing to the ice cream?” I asked, feeling my face flush again and my voice get quieter as I finished my sentence.
Michelle smirked. “She was right about you. You’re cute,” she said, as if that was the most totally normal thing to say in this circumstance. “Can you keep quiet?”
I nodded. “Tell me.”
“Not what I meant, Dante,” she replied confidently. “Keep quiet, as in, no noises.” She set the glass down and motioned with two fingers for me to follow her. I got up from my stool and followed her as she opened the door to the back room. She once again motioned for me to follow her, but put a finger to her lips after. Wordlessly, I followed her.
The back room was a lot bigger than I expected it to be. There was a lot of storage – both racks and freezers, which made sense – and even what looked like some kind of defunct conveyer belt. In the corner was some kind of indent in the wall – another room. It had a door sticking out, and I had to guess it was some kind of office. Michelle looked inside the door’s window and smirked in a satisfied way. She walked over to me and gently put a hand on my shoulder. “Brace yourself,” she warned me, then guided me by the shoulder towards the office. I followed, my legs feeling light and weightless, and peered into the window. I could see why Michelle told me to brace myself.
I don’t know what was more shocking: the fact that Carissa was on all fours getting the dicking of her life doggy-style by some guy possibly old enough to be her grandfather, or the fact that I freaking knew the old guy giving it to her. It was unmistakeably Mr. Fitzgerald – Guelph’s resident “jolly old man.” He went to every community event he could, he remembered everyone’s names, and thanks to his white beard (I’d say “white hair” but there was precious little of it left) and beer gut, he was a shoo-in to play Santa at the local mall for the past few years. If you were anyone in Guelph, you knew Mr. Fitzgerald, though maybe not as biblically as Carissa was getting to know him in that moment.
Although it quickly dawned on me that she wasn’t getting to know him for the first time. I stood there watching Mr. Fitzgerald’s hefty stomach clapping against Carissa… and watching her meet and match his movements at every turn like a pro. Pretty quickly, Mr. Fitzgerald’s face twisted in enraptured concentration and, like dominoes falling, a satisfied grin appeared on Carissa’s sweaty face as he began to unmistakeably cum inside a woman easily forty years his junior.
“Holy fucking shit,” I mumbled out loud, tearing my eyes away from them. Michelle was behind me, staring at the pairing.
“Yuuuup,” she acknowledged. “For the record, no one is gonna believe you if you blab. We cover our tracks well, and our customers understand why secrecy matters to them too. Besides, you wouldn’t want to get poor Carissa in trouble, wouldja?”
“Of course not,” I found myself saying.
“Good boy,” Michelle sang. “Give her a bit to clean up. If you want some fresh air, I can tell her you’ll meet her outside.”
“Um… yeah, I’d appreciate that,” I admitted. We didn’t say anything more to each other, so I found my way back out of the back room, and eventually, outside the store altogether. As the door closed behind me, I saw Lauren whistling to herself, cleaning the windows from the outside. She made eye contact with me without stopping her cleaning motions, and I merely blushed and looked away. She didn’t say anything.
I have no clue how many more minutes went by before a slightly flushed Carissa came to meet me outside. I turned to see her when I heard the door bell jingling, and for once, she looked about as nervous as I did. I don’t think I saw that kind of look from her… ever.
“Oooookayyyyy,” she announced, leaning against the storefront. “So, it’s come to my attention that you saw me, uh, in the midst of preparing a special order.”
She stared at me long enough for me to understand that she wanted me to say something before she kept talking. “Um, I think I saw more than that,” I informed her.
“How much more?” she asked, her nervousness growing.
“Mr. Fitzgerald?” I offered quietly.
“Wh- how the- did you just waltz into the backroom?!” she demanded, clearly caught off guard.
“Well, I- I was invited to,” I admitted.
Carissa glared back towards the store. “Michelle,” she grumbled, then looked back at me. “Okay then, explanation time, I guess. So, take a look around the neighborhood.”
She waited for me to physically look around, so, look around I did. I saw closed building after closed building, with cracked pavement and the occasional worn-down bench flanking the buildings. “What do you see?” she asked.
“A run-down neighborhood,” I murmured quietly, not understanding what this had to do with anything.
“Exactly,” she confirmed. “Owning a business around here is hard. Owning a business selling treats, something people don’t exactly need? Even harder. The business was in Lauren’s family for generations, and Lauren wanted to keep it going at all costs, but as the city started to go to hell, things looked… inevitable for a while. Shortly after she inherited the place from her grandfather, she had to start asking some tough questions.”
“Sell or keep the place?” I guessed. It was weird talking about her while she was close by, and odds are, could hear the whole conversation.
Carissa shook her head. “What she had to do to keep the place,” she corrected me. “Selling was never an option. She knew she had to keep the place afloat, but the question was ‘how.’ So, she started offering… special deals for special clients. At first it was a her thing, and she kept me and Michelle in the dark, but-”
“Michelle is a snoop,” Lauren interrupted dryly.
I had to chuckle. “I think I got that vibe, yeah,” I admitted.
“Michelle found out first, and Lauren kinda had to tell all. We held a lil’ team meeting, and we kinda sorta decided… why not?”
“S-so… you…”
“Everything from kinky services to full-on fucking, yup,” Carissa replied with an innocent smile. It was odd… getting caught was clearly embarrassing for her, but admitting she had sex for money was something she admitted as casually as telling a friend she skipped doing her homework.
“The secret menu,” I inferred.
“The secret menu,” she acknowledged. “Yup. Each flavor on the secret menu is a clever lil’ innuendo of ours. If I understand correctly, you watched me preparing a Peaches n’ Cream.”
I couldn’t help but stare open-mouthed at her. My childhood friend. Acknowledging I witnessed her… cumming on the ice cream. No anger, not even an apology for ‘having to see that’ or anything… no shame whatsoever.
She started to laugh. “Hey, Michelle had to do an Ultimate Banana Split earlier, be glad you didn’t have to see that,” she joked.
“Do I even wanna-”
“One girl, two ‘bananas.’ You get the idea,” she chortled.
“I didn’t even see two guys walk i-”
“There’s a special backdoor for the repeat customers,” Carissa explained as casually as one would talk about the weather. “Not that kind of special backdoor though. That’s the Rocky Road special, and lemme tell you, I am glad only Lauren handles those. I could never-”
“It’s better than you think, Carissa, as long as you prep for it,” Lauren pointed out, moving from one window to another.
“The prep is the worst part!” Carissa argued, then turned back to me and shrugged.
“I’m still hung up on the ‘two dicks’ thing,” I replied honestly. “Did you ever-”
“Only twice,” Carissa replied.
“So, you’re like… really experienced,” I realized, mumbling it both to her and myself.
“Sorry if this is weird hearing it from an old friend, but I started a long time ago,” she laughed bashfully.
“You’re just so… open about it,” I continued, feeling like this wasn’t even real. “The special services, the experience, the fact I just fucking saw you naked…” I waited for her to say something and she just maintained eye contact and smiled, shrugging after a bit. “Is it… degrading?”
Carissa sucked in her full lips in thought, puffing them back out as she thought about my question. “I mean, no,” she replied, with a voice that told me that was the only part of her answer she was sure of upfront. “I like helping people out, and I’ve known these people all my life. Take old Mr. Fitzgerald, for instance.”
“I’m pretty sure you’re the one that took him,” I joked.
Carissa smirked at me, but continued. “Ever since his wife died, the guy hasn’t really been the same. I bet you knew that as much as I did. This shit stays with people, and once he found out about our services, he admitted he liked them but nothing – even his own, uh, hand – had been able to make him cum since. Can you imagine? Blue balls even from masturbating? Especially when you’re old and people just look at you all, ‘ew, creep, no thanks’? How degrading, right?” She waited for me to reply.
“Uh, right.”
“Right! So, I offer him something no fancy-pants kink could ever truly replace…” She gestured down to her crotch. “Basically, like, ‘hey, let’s see if I can get you to finish.’ We had so many secret menu items, but no just straight-up ‘I’ll let you fuck me until you cum,’ actually. We had to create a new secret menu item for it.”
“Vanilla Frosting,” Lauren laughed.
“I thought it was a cute name,” Carissa huffed. “And the first time he came, he almost, like, cried out of pure joy. It was actually kind of sweet. So like, how can you say what we’re doing is wrong when it helps so many people feel so good? You see that, right Dante?”
I knew Carissa liked helping people, but good God, this was next level. Still, it was clear from the look in her eyes there was the slightest fear of her being judged or something, and in a weird way… maybe it was because she was so accepting of it, but I felt like it was all perfectly understandable. “Of course I see that,” I replied, trying to inject enough confidence into my voice to fully reassure her.
“Ugh, thank God,” Carissa laughed nervously to the sky. “And, uh, by the way, I did mean that whole thing about the people I’ve known all my life. I can’t offer you anything for free – even for friends, it’s against our lil’ policy – but, I mean, you’re a guy, and a cute guy to boot. If you ever did want anything…” She touched my hand and folded it in on itself. I started to blush, and looked at the hand. “…Think about it. ‘Kay?”
“You… me? You would… want to…”
She shrugged. “Yeah, why not? I get regularly tested, you’re clearly trustworthy, you’re around here all the time anyways, and besides… I mean zero offense by this, but you’ve vented to me before about your whole-”
“Okay!” I replied, the blush deepening. It was true, I had vented to Carissa once or twice about wishing I had a girlfriend for more… carnal purposes, once or twice, even if that was years ago. “I’ll definitely think about it.”
“Actually? Or are you just saying that?” Carissa playfully challenged.
“Well, since you only give the offer to people you trust-”
“Oh, you can bring a friend if you want,” Carissa added mischievously. “I know that shit is super hot to guys, and besides, I gotta hustle to keep the place afloat too. Could be you, could be you and a friend, and our prices are better than actual prostitutes. The services are, heh, sweeter too.” She leaned in and, out of nowhere, gave me a kiss on the cheek. Her full, juicy lips implanted onto my cheek, spreading a warmth I didn’t know lips could make. She retracted her lips, leaving the faintest impression of her saliva, and giggled. “Enjoy the free sample. I gotta go back inside and prepare the next order, ‘kay?”
She didn’t wait for me to reply as she practically bounced back inside. Lauren didn’t even look at me as I remained against the storefront wall, my head spinning.
***
I may have been shy, but there were still a few people I trusted with my secrets, including my sexual secrets, and James was absolutely my best friend in that regard. James and I began in late high school admitting to each other our secret fantasies, and the both of us came to soon find out we’d be cool having a two-guy threesome sometime, or have fun with the same girl one after another or something. I never told anybody but James, so… who could I possibly tell but him?
We talked about more than sex, of course – we literally played Valorant the night before when I messaged him about the Divine Creamery. We ended up having an hour-long Discord call about what I saw, what they were offering, and whether we wanted to fulfill a fantasy we’d been talking about for literally years. I mean, the opportunity was literally presenting itself to us. Did we truly want it badly enough?
James sure did. He was often our “point man” – liked making plans, called the shots, approached people with confidence. I was happy to be The Guy in the Background when that happened, and if anything, it was crazy that I was coming to him with a crazy opportunity. To solidify why he was usually the point man, one of his first questions was “How much did she say it cost?” and I had to tell him I forgot to ask. I caught some flack for that, even if James was laughing as he chided me.
James made the arrangements: we go, close to closing time. James brings as much as “regular prostitutes cost,” in cash, for two people, and would ask then and there how much the services were. If it was more than he had and they aren’t open to negotiation, the deal is a bust. I would give him my half later, via eTransfer or something.
Still, planning it was one thing. Actually walking up to the building was something else entirely. I don’t even know why I was so nervous – James and I talked about it for years and agreed we’d do it; I’d seen James naked before while changing for swimming; Carissa point-blank offered it to me after I saw her freaking naked – but still, my heart was pounding away.
It was less than an hour to closing when James and I were outside the doors of the Divine Creamery. James breathed in and out a few times, readjusted his glasses, pushed his shaggy brown hair out of his face, then offered me a fist to bump. “Moment of truth, bro,” he announced to me. “You ready to fucking do this?”
My breath came out shaky, but I bumped his fist, and that was good enough for him. With confidence I at times wish I had, he sauntered into the store and put his arms down on the counter in front of him.
Lauren was handling the counter, and gave him a polite smile. “Welcome to the Divine Creamery!” she sang warmly.
“Ahoy there,” James replied confidently. “Got enough time to squeeze in two specials?” He turned back to me. “This is Carissa, right?”
I practically tiptoed in like a disciplined puppy by comparison. “N-no, this is L-”
“Lauren,” Lauren finished, smiling even as she looked James over up and down, sizing him up. “You’re here to see Carissa?”
“He is,” James offered, gesturing back to me, “if she’s free for her shift.” He turned back to her. “But, uh, we’re not here for no Banana Split.” It was his turn to look her over. “Is it only her that’s on the menu?”
Lauren’s eyebrows nearly raised to meet her hairline, and her smile broadened. “Well, aren’t you my type of charmer,” she practically purred. “I like a guy who’s forward. But if you’re ordering the two of us, that means you’re paying the two of us.”
“Bet, then let’s talk prices,” James practically challenged her. As the two talked, Carissa came out of the back room and saw me. Instantly, her smile grew and she practically bounced over to me.
“Oh my God!” she sang, taking my hands in hers. “I totally thought I scared you off or something!” she ruffled her hand through my hair again. “No offense. So, did you give any thought to my offer? If you want, once…” She lowered her voice. “This other customer is gone, we can talk about-”
James turned to her. “I came here with Dante, and your whispering game sucks,” he laughed.
“Oh wow,” she laughed back. “Uh, duly noted. Wait…” Her look turned deadly serious. “You… brought a friend…? So, you actually wanted… to…”
“More than reasonable,” James announced to Lauren, taking his wallet out and handing her an amount of money. He turned to me, practically lazily. “Yo, Dante. It’s only $50 extra to switch halfway through. You wanna try out Lauren too?”
So everyone was just going to be nonchalant about this shit but me, huh? I barely suppressed a cough of sheer surprise and could barely choke out, “Um… yeah…”
I honestly never thought I’d get so lucky. Carissa was deadly attractive in her own way, with her bubbly demeanor and her full, juicy lips, but Lauren was attractive in a way that younger adults just couldn’t pull off. Not only her bigger bust and cute little pudge that came with graceful aging, but also the smouldering look that just made you want to drop to your knees and submit. It was any guy’s dream… or at least my dream, I knew that for damn sure.
And Lauren just reacted to my shy agreement with a smile of her own. No hesitation, no weirded-out look… if anything, she narrowed her eyes as she smiled, and just looked me up and down like she did with James only moments before. “I can only presume James wants me first, just so you know,” she lightly joked, smiling at me.
Carissa was once again smiling as well, only this time in an “I can’t believe this shit” way. “Oh my God,” she marveled. “Wait, what did you two actually order…?”
“Haven’t gotten to that part yet, but we’ll see,” James once again tossed over his shoulder, then looked over some set of rules Lauren handed him. “We’re good here, we’re both virgins so the STD fine doesn’t scare me…” he mumbled, almost to himself.
“Wait, you paid before even deciding what you wanted to order? Damn…” Carissa’s marvelling continued. “‘James,’ right? You’re reckless, aren’t ya?”
James turned his head and smirked at her. “Promises promises,” he teased. God, I wish I had that guy’s confidence. Part of me wondered why the charming bastard was inexperienced and even had to pay for sex, but I was glad he did, otherwise I probably wouldn’t even be here right now. He turned back to Lauren. “So, you own the place. Got any recommendations?”
“Well,” Lauren mused, handing James her phone with some kind of note-taking app open. “You can take a look at the full menu if you want, but I’m happy to make suggestions if y’all want…”
James whistled as he looked over the phone. He may have kept up his confident demeanor, but something tells me if he wasn’t already pale as a ghost, he might have gone white reading that menu. “Got any allergies, Dante?” he teased me as he read.
“I want Carissa,” I almost mumbled. “I r-really want Carissa.” I blushed, looking at her, for some reason still nervously picturing her getting weirded out and slapping me or never speaking to me again or something.
Instead, she looked at me the way a sappy girl looks at a new puppy. “awww, Dante~!” she sang, putting her hand on my shoulder. “That is so sweet! I would love to show you… I mean… I gotta imagine this would be your first time…”
I couldn’t even look her in the eye. I just looked down at the floor, nodding.
She chuckled. “James already paid, right?” she asked Lauren, and I have to imagine Lauren nodded, because only a second later, Carissa’s finger brought my chin back up. “This is normally not part of the deal, but since you’re a friend,” she told me in this deliciously quiet, sensual voice, before kissing me right on the lips.
I knew it was only sexual, but good God did so many feelings come out when her full lips pressed against mine. It was like her lips carried a magic spell that coursed throughout my entire body. My cock absorbed all of the tingling feelings her lips gave my body like a lightning rod. I could feel my entire body melt into her kiss – it truly felt like magic. I couldn’t help but moan into her mouth, which only caused Carissa to giggle as she pulled away, nothing but excitement and anticipation in her eyes.
While, uh, that was happening, I guess James had a chance to finalize his thoughts with Lauren. “Well in that case,” he finished his thought to her, “a Caked Vanilla sounds great.”
“Sounds like a treat to me too, darlin’,” Lauren told him with a smirk. “And if I may make a suggestion, partially thanks to what I just saw, how’s about a nice Strawberry Bubblegum from Carissa? It is a best-seller, after all…”
I looked back at Carissa and to my surprise, it was her turn to blush. “Hey, c’mon,” she managed.
Lauren gave a mature, throaty laugh, but noted, “that’s not a no. Dante, what do you think?”
“I have no idea what it is but I’m in,” I told her honestly. In a weird way, knowing what was going to happen may have actually made me less comfortable. In a weird way, being told what was going to happen might have made me bolt. But knowing Carissa knew what to do and was in control, and all I had to do was go along with it… it was exciting.
“You’re my kind of customer,” Lauren happily accepted.
“I’m going to make this the best day of your life,” Carissa quietly but determinedly told me.
My heart was trying to beat out of my chest as the four of us made our way to the same office where I saw Carissa on all fours only yesterday. Clearly the group were a fan of cleaning the place until it was spotless after every… satisfied customer left, which I definitely appreciated. I practically felt my vision blur and my hearing go when I realized, this was it. My first actual sexual encounter. It was going to happen, it was going to happen like this, and it was going to be with Carissa there, while James was there to witness it. What a fucking world.
I thought there would be this awkward moment of, “uh, so who does what first? Haha!” Of course, I forget that I was dealing with professionals. Lauren was the first to move, telling James, “alright, big boy, let’s get this party started!” while sensually taking off her pants for him.
I knew that James was pretty much the same size as me – a good six inches – so “big boy” was perhaps high praise, although when he took off his pants (finally showing some human nervousness for the first time since he walked into the store), Lauren gave a happy little gasp.
“Ooh, wow, what a large mushroom tip you have,” she marveled, kicking off her pants, her eyes glued to his cock. “Mmm, I bet that’s going to feel soooo good going inside of me…” She took off her underwear and turned around, bending over against the wall, arching her back to show her surprisingly firm ass to him. With her little stomach pudge, she must have worked out to get an ass like that. James may have been confident in the store, but all the inexperienced lump could do now was grunt happily, his cock twitching in anticipation.
“She has such a nice ass, doesn’t she?” I heard a hot sensual breath whisper into my ear. I turned back to Carissa to see her open a stick of… bubblegum strawberry chapstick, of all things. She must have caught my confused expression because she just winked at me and simply said, “You’ll see,” before pressing her lips together in the way girls do after applying chapstick. With her eyes, she told me to look back at Lauren and James, and my curious eyes followed.
I looked back just in time to see James, fully lubed up from a bottle placed strategically on a nearby shelf, inserting himself slowly into Lauren’s mature, tight, no-doubt incredible pussy. The two of them moaned in tandem as he slowly, centimeter by centimeter, sank inside her. “Ooh, fuck,” Lauren moaned musically. “God, I loved feeling a big tip like yours filling me up. Oh fuck, James, I’m gonna like this, I’m gonna like this a lot.”
James was a lot less wordy but still couldn’t help moaning as well, taking Lauren’s firm ass in his hands and relishing the moment. I would have watched for longer but an unfamiliar sensation took my attention back to my own situation, which was rapidly unfolding. I turned my attention down to seeCarissa, on her knees, unzipping my fly expertly with her hands. “You don’t mind, do you Dante?” she teased, smirking with her puffy, pink, gloss-coated lips.
The smell permeated through my mind. I could smell nothing but strawberry bubblegum bliss and could barely even process thoughts, let alone speak. I ended up just staring dumbly at her while she freed my own shaft and bit her lip. “Mmm, uncut. Nice,” she noted happily, beginning to jack me off with her hand.
Before I could even react, Carissa parted her full glossy lips and gleefully, with zero hesitation, took in my shaft. For the first time, I felt the sensation of a pair of lips on me, and realized then and there why some guys need to make sure not to cum immediately. I braced myself against the wall, unable to stop the desperate little noises that came from my mouth as my first ever blowjob began. I was wondering how the chapstick could possibly enhance the experience, and what a fool I was to lack the imagination. The sticky, gooey, velvety smooth sensation of the lubed-up lips, coupled with the smell of strawberry bubblegum, overwhelmed my senses.
No shit this was a fucking best-seller – it was like Carissa was made to do this. My own childhood best friend, with her glossed-up lips on my cock, blowing me like she’d been hungry for it all day… shit. “Oh my God, Carissa, you’re such a fuckin’ slut!” I practically panted.
Before I even had the chance to internally cringe at what I just told her on autopilot, I heard her moan, “mhmmmm~” on my cock, slowly but heartily using her mouth and throat muscles to milk every inch of me. Both of my hands flew to the back of her head and my jaw went slack with no hopes of recovery. Holy shit, her blowjobs were clearly a cut above. Even though she was my first, it was beyond apparently hers were next-level. It wasn’t just her warm mouth, her big juicy lips, and the chapstick… it was her doctorate-level skill at sucking cock, and her clear love of it as well.
Even with the sensations overwhelming me, the noise the other pair were making at the other end of the room drew my attention. I couldn’t help but watch in awe as Lauren’s hips bucked back to meet James’ thrusts. Her juices were similar to Carissa’s – thick strings of girlcum, making James’ slides no doubt enticingly wet and sloppy. Lauren was wetter than even the few wetness porn videos I had seen – was she always like that or was she particularly wet for us? Either way, it was hotter than anything I had seen on the Internet, and I got to see it while I was getting my cock sucked by a literal pro!
James caught me looking and smirked at me, even as he made no move to stop. “Crazy shit… huh Dante?” he nearly wheezed, pumping back and forth, in an inexperienced yet eager way. It almost looked silly in a way contrasted with Lauren’s expert rhythms. “Almost… surreal. I can’t fucking believe… this is happening…” He steeled himself, sighing and adopting a goofy grin on his face, focusing back on Lauren. Lauren could only moan, her breasts swinging under her shirt with every thrust.
I didn’t even need to look back at Carissa to know she was deepthroating me now. “Oh my fucking God,” I moaned, caressing her hair. “I think I’m gonna… soon…”
James overheard me and slowed his rhythm, laughing, “Ay-ay-ay, Dante! Slow down there, I paid for you to fuck Lauren too! Don’t blow your load too early on us!”
Lauren chuckled, even while moaning. “Maybe we… should switch now…?” she offered, even between moans. To be honest, after getting to feel Carissa’s mouth, I never wanted to leave it (ever), but James did pay for us to both get access to both… Fuck, would it have been a dick move to back out and go exclusive now…?
Clearly, James had opinions on the matter, seeing as he was already making his way over, leaving Lauren panting and recovering against the wall. “You heard the lady,” James laughed, his glasses a little fogged up and his shaggy hair beginning to matte against his forehead. “Don’t leave her waiting!”
There was no way I could articulate my case now. I gave my best apologetic look to Carissa as I retreated from her mouth – maybe I was imagining it, but I swear I saw her return the apologetic look as my cock emerged from her mouth, inch by inch, until it fully left with a loud “pop.” Carissa didn’t say anything but started to reapply her chapstick, while I begrudgingly yet excitedly headed towards Lauren.
Lauren was looking back at me as I approached, biting her lip sensually. “Been wonderin’ about you for a while, you know~” she told me coquettishly, grabbing behind her and shamelessly pulling her cheeks open for me. Thanks to her still arching her back, I was able to see not only the wetness of her pussy on full display, but her cute smooth asshole too, slightly twitching with apparent need. Fuck… Lauren was barely old enough to qualify for the title of a MILF, but even still, she clearly had the hormones and eagerness everyone else in the room shared.
I couldn’t help but spare a glimpse at James and Carissa, and felt a pang of jealousy as I saw Carissa’s mouth and lips stretching, accommodating to take the engorged head of James’ cock. I knew she was doing this near-daily, but still, getting to watch her lips part… knowing my friend’s cock was slowly sliding between them… The guy had better be appreciating what he got.
“No need to be jealous,” Lauren warmly told me with a kind yet non-condescending tone. “Why don’t we give him something to watch too?”
I chuckled nervously, but my cock throbbed, thinking of getting to be inside a woman’s vagina for the first time. This was it. Finally, I was going to get to fuck a woman… and not just any woman. I was going to get to fuck Lauren.
I took hold of my shaft and pointed it right at Lauren’s pussy, and shimmied forward, pushing my cock in… or at least, trying. The angle was off. God, why did porn have to make this look so easy and effortless? Lauren laughed and gently told me, “Happens to us all. Let me.” She reached behind her, grabbing hold of me, and lined herself up with the tip of my cock. “Go ahead, Dante,” she throatily told me, her voice full of anticipation and need.
I pushed forward, feeling her flesh envelope mine. I couldn’t help but exhale sharply, feeling a pussy from the inside, for the first time ever. Inch by inch, I sank inside, rewarded by a sigh of satisfaction from Lauren. “Ooh, fuck yessss…” Lauren sluttily moaned, letting her head hang for a second. “God, I love cute virgin boys like you. Two in a day is like heaven for me. Congrats on becoming a stud in an hour, Dante – ready to keep going?”
Fuck, Lauren knew how to turn a guy on. I wanted to savor the first-time feeling (and make sure I didn’t blow too early) so I started with slow, gentle, almost teasing strokes, watching the back of Lauren’s head with interest to make sure she felt good too. I looked down, watching my shaft slowly get coated in Lauren’s juices, sliding in and out more and more effortlessly, and most of all, watching the normally composed Lauren get more impatient and move her hips back until she was fucking me more than I was fucking her. I took the hint and began going faster and deeper, learning our best rhythm and using it well, beginning our sex in earnest.
As if I should have even been surprised, James had no taste for such a leisurely pace. I looked back at the pair to see Carissa deepthroating James’ cock – and couldn’t help but be transfixed on the way Carissa’s throat bulged with each stroke. It was like I could make out where James’ mushroom tip was with each thrust, and from the expression on Carissa’s face, something told me she could make out exactly where it was in her throat too. Even while inside Lauren, I throbbed at just how much Carissa was owning and enjoying her sluttiness. Just like Lauren, she clearly enjoyed being the experienced one in the room, and it showed.
I had barely gotten back to thrusting inside Lauren when the consequences of James’ speediness caught up with him. With a struggled gasp, James gripped Carissa’s head and held on as best as he could. Carissa barely reacted, taking the developments like a pro, sealing her lips around his shaft. I lazily thrust my hips back and forth, using Lauren’s pussy to lazily jack off, watching Carissa’s throat bob as she all-too-easily swallowed what must have been rope after rope of my friend’s load. Her eyes slightly rolled back, relishing the experience, and her hand even disappeared into her pants – even though she wasn’t rubbing frantically, this was clearly her treat for doing such a good job. It was crazy watching my childhood friend swallow it all so effortlessly, shamelessly enjoying herself in such a way, and seeing everyone around me accept it so readily. It somehow made Carissa even sexier.
“Congrats on not coming in first,” Lauren teasingly told me, taking me out of my thoughts and starting to throw her ass back against me. “But from here on in, there’s no prize for lasting long. What do ya say, stud, ready to finish? And no pulling out, by the by.” She turned her head around to grin at me, her backward thrusts picking up speed. “I wanna feel the full load inside me.”
Watching Carissa and being told to cum inside Lauren made something snap within me. Before I could even form conscious thoughts, I grabbed Lauren’s curvy frame and held on for dear life as I began thrusting into her with strength I didn’t know I had. “There we go,” Lauren sighed happily, “that’s the stud I knew was in there! Keep going, baby – wanna grab my hair? You can totally grab my hair, sugar!”
Well, if she was offering, why not? I grabbed her hair and watched as her thrusts went from back-and-forth to this complex motion where she kept arching and un-arching her back, milking my cock in multiple dimensions while somehow keeping up the pace. Fuck, she was a complete professional. The sensations on my cock felt almost alien in how full they were – they were compounding, they were overwhelming, and there was no way in hell I was going to last any longer than a few seconds.
“L-Lauren-!” I choked out.
“Fuck yes!” Lauren moaned heartily, abandoning her soft voice in favor of a hefty, carnal, desperate tone. “Give me your fucking load, baby! Coat my insides! Claim me, handsome! I want it allllll~!”
I now know why they call it “exploding” inside someone. It was like someone shot a bomb off inside her. From the moment I began, it felt like I shot a gallon of cum inside her. I slammed her hips against mine, panting, feeling the sweat on both our bodies as my first shot, then my second, then my third, shoot with the force of a bomb. The shots kept firing off inside her, and with every rope I shot in Lauren’s pussy, she gave back another appreciative moan of “Oh…” descending in tone.
She didn’t stop milking me, not for a moment. The entire time I shot my load into her, she was grinding her ass against me, milking and coaxing every last drop out of me. Eventually, I collapsed against her, accidentally pushing her into the wall. Lauren gave a clam, throaty laugh, gently pushing herself back off of the wall, but waiting for me to regain my strength and slowly retract from her pussy before standing back up fully.
Carissa was already fully decent by this point, as was James. In fact, Carissa reacted to me detaching myself from Lauren by walking over to her with some kind of towel, wiping the sweat off of her friend’s back and ass before squatting down.
Lauren braced herself against the wall and lowered a hand down to her pussy as Carissa started to lightly massage the area with her towel. I couldn’t quite see what was happening, but I heard a perverted yet satisfied “nnnh!” from Lauren as Carissa gasped, no doubt accumulating my load in her towel.
“Wow, Dante,” she laughed, cleaning up her friend intimately. “Very impressive.”
I could only chuckle nervously, quickly doing my pants back up and freshening up. I didn’t know who to look at – not Carissa, not James, not Lauren – so I just looked at the floor.
“I trust you two have – nnh – had a satisfying trip to the Divine Creamery?” Lauren asked, standing back up and putting her own pants back on.
“Ohhhhhhhh yes,” James laughed, nodding thoroughly. “Dante?”
I was still panting, and could only nod, causing the other three to chuckle.
“Good,” Carissa beamed. “Don’t forget, if you leave us a Google review, don’t even make an innuendo. Don’t get us shut down, even if you think it’s only us who are in on the joke.” She winked at me. “Aside from that, we’re glad we could service you today!”
With that, Lauren began to usher us out of the office and back to the front of the store, where Michelle was waiting next to the door. The ‘Come in, we’re open’ sign was facing us – the store had evidently officially closed a while ago. “Oh, sorry, did we take too long?” I asked.
“Nah,” Carissa waved me off. “Besides, who cares? I was happy to make you a satisfied customer today.” She gave me a warm smile, like she was just helping me with my homework or something.
I chuckled, blushed, and looked down at the floor. “I mean…” I began shyly. “If I had more money, you would have made a repeat customer today. Like, daily.”
“Oh yeah?” she challenged me with one eyebrow lowered and a confident smirk plastered on her face. “Hmmm… Well then, I’m sure we can arrange for the odd… free sample every now and then.”
Despite everything, I couldn’t help the shock from painting my face. “Wh- like, how?”
“Like how you’re thinking, Dante,” she told me sincerely. “I mean, I’m the reason you’re here, and it’s not fair to both of us when you think about it that you got to finish in Lauren but not me.” She bit her lip and started playing with the hem of my shirt. “You know what I mean?” She playfully released the hem of my shirt and said one more thing to me before walking off: “Think about it.”
With her trademark confidence, she began walking back into the back room, not even waiting for my response. As I watched my friend’s ass swaying back and forth, I knew that I would be doing a lot more than just thinking about it.
This piece’s premise, plot, and characters are all credited to the commissioner, ZeRoBotz. If you enjoyed this story, bear in mind it would not have been possible without his ideas and words of inspiration.
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