Painful Pleasures

First Date

Here I was again, at the airport, playing the role of the family chauffeur as I waited for Elijah’s plane to arrive. Thankfully, he wasn’t as uptight as dad, so I could simply sit in the car with the AC running and he’d find me. I was texting happily with Jamila when I saw him come out and wave to me. He tossed his suitcase in the trunk before climbing into the passenger seat.

“You look happy,” I said as I pulled out. Though he tried to hide it, I could tell he was trying to suppress a smile.

“I just had fun, I met a lot of cool people at school.” he said as he swiped through his phone. He held the phone up to me. “Look, I took a bunch of pictures. One of the guys even asked to be my roommate.” he gave me the goofiest smile and I chuckled. He was such a dork. For someone who stayed in the house way too often, it made sense he’s happiest when he’s out meeting people. I couldn’t help but be happy for him. 

“That’s cool Eli, I’m glad you had fun.” 

“What was your week like?” he asked. My expression clouded and he noticed. “Was it…mom and dad?” 

“Ha…you don’t even know half of it.” I hesitated, contemplating how open I wanted to be with him. He was my brother after all, not some stranger. I shouldn’t have to be guarded. “I…I was drugged two days ago.”

“What!” he screamed. It was so sudden, I jumped, accidentally jerking the car in the process. 

“Can you not? I’m trying to drive.” 

“Sorry, but what the hell? You can’t just say stuff like that and expect me not to react. What happened? Who the f**k was it?” I couldn’t help but smile as I watched him crack his knuckles with a fierce scowl on his face. Sometimes I forget men are normally protective. It was sweet in a way. 

“I was at a club. My friends were supposed to come, but they never showed up. I got drugged by some asshole that I met at my gym. He and his friend tried to take advantage of me, but-” 

“s**t, we can pull up on that son of a b***h right now. What time does he usually show?”

“But…” I continued as I fought back laughter. “They never got to do anything because I still kicked their asses. Though, I don’t remember much of it since I blacked out. I saw what happened on the hotel cameras.”

“That’s so messed up. What did mom and dad say?”

“I didn’t tell them.”

“Why not?” he asked. “We can easily press charges on that asshole.”

“I will, but I’d rather handle this on my own. I don’t trust mom or dad. I know they’d find some way to blame me for what happened.” 

“Noway, they’d never do that.” he sounded so sure. I laughed.

“Sure…your daughter goes MIA for the night and the first thing you do when she comes back is smack her.” he went silent. Though it’s been some time, everytime I think back on it, I get angry. The way everything escalated was so f****d up, it pissed me off. But I didn’t want Eli to see that, so I remained neutral. 

“Dad…he likely-”

“I really don’t want to hear any bullshit excuses Eli, please. What’s done is done, the why doesn’t really matter anymore…Look, I don’t want to talk about this anymore.”

Elijah sunk in his seat. “Sorry…” his phone buzzed and he looked at it. His brows furrowed as he read what was on the screen. I’d caught a glimpse of the caller ID; Bae. It must have been a text from his girlfriend. He looked concerned. I asked if everything was okay. He parted his lips, but refrained. “Yeah, everything’s fine.” 

I was finishing up my packing, listening to Mila ramble on the phone about all the things we should do this weekend when I got a text. It was from Nate, checking in to see if everything had been handled and if I was alright. I told him everything was fine and nothing serious had actually happened to me that night. I checked the time. I had to be up pretty early to make my flight, so I shouldn’t stay up too late. Since it was still early, I ended up asking him if I could treat him to dinner. It was almost 5, so as long as I was back before 10, I’d still manage to get a decent amount of sleep. Though I doubt I'll be out for five hours.

Nate: I’m surprised. I thought I’d be the first to ask you on a date.

Me: Don’t flatter yourself, it’s not like that. I simply want to do something nice to show my gratitude. If you’re going to make it weird, then we don’t have to. 

Nate: Ha, I was only teasing. I’d love to join you. Shall I pick you up in an hour?

Me: How many girls do you know that can get ready in an hour?

Nate: Not many, but assuming this isn’t a date, I didn’t think you’d go through the trouble of getting dolled up for me.

I huff. Cheeky bastard. I then texted him that I’d be ready in an hour and a half and that I’d meet him at Wuu’s Kitchen in Chinatown. I quickly took a shower and looked through my closet for an outfit. I wasn’t going to dress up for him, but that doesn’t mean I was going to become a water-down version of myself either. Despite what I said, I actually managed to finish getting ready in a little over an hour and called an uber to take me to Chinatown. Usually I’d prefer to be a few minutes late than to arrive early and wait for a man, but considering that this wasn’t a date and I was running on a time limit, I didn’t mind. When I walked into the restaurant, I was surprised to see that Nate was already there. I asked why he was there so early.

“I always show up early, a man shouldn’t keep a woman waiting.” he stood to pull out my seat. A part of me was feeling slightly embarrassed, but I sat down regardless. “You look lovely, by the way. Comfortable, yet classy.” I blushed. I had pulled on some high-waisted jeans, a white bralette covered by a wheat-colored jacket and matching boots. My dad had mocked me before saying my style was hoeish because I didn’t mind showing a bit of skin. It was…different hearing a man refer to me as classy. I took notice of his attire as well. From first glance, he too looked rather comfortable. His pants looked expensive, banana republic jeans maybe and a cozy brown sweatshirt. Despite being at opposite ends of the table, his cologne engulfed me. It was slightly different from the first time we met, but still light and fresh. He gave me a smile. “You’re staring, Ms. Kirkwood.” s**t, was I really? I could have sworn, I’d only glanced for a second. The waiter approached us, offering us water and asking if we’d like to start off with drinks and appetizers. I chose to stick with water, but before I could say anything more, Nate asked him to give us a few more minutes. “You were still looking at the menu, I didn’t want you to feel rushed to choose something.’

“I wasn’t really about to. I already know what I want, I just wasn’t sure if we should do an appetizer.” 

“What is it that you want?” he asked as he looked over at his own menu. I told him what I wanted and when the waiter came back, he ordered for the both of us, selecting an appetizer and a bottle of wine. “I’m sorry, I should have asked if you were okay with drinking.” Yeah, he should have, especially after the previous incident. However, considering they’d be giving us an unopened bottle, I shouldn’t have to worry. I noticed him staring at me very intensely, almost as if he were studying me. It made me a little intimidated. “I’m curious, what made you want to treat me to dinner?”

“Like I said, I simply wanted to thank you.” I said, “I had my suspicions about that night and though I still don’t 100% trust you, I do appreciate you looking out for me. Though I do find it weird you were so willing to allow a stranger to sleep in your room with all of your possessions.” he smiled. 

“Are you insinuating that you’d have stolen from me?”

“Of course not, but you don’t know me to know that. I could have been crazy or violent,” he chuckled.

“You’re right, you could have, but frankly, I’m not frightened by unhinged behavior. In fact, I actually find it rather exciting as I’d enjoy figuring out a way to tame that behavior.” So he’s either a therapist or f*****g toxic. “Maybe my actions were a bit reckless, but considering it was you of all people, I couldn’t bring myself to leave you there in your state.”

“Oh really? Tell me, what’s so special about me?”

“I’m interested in you. I found you stunning despite how you felt about your attire and I simply want to get to know you. Like a book with a blank cover, you have to open it to determine if it’s to your liking.” Was this guy serious? It seems like encounters like these really only happen in books. There had to be a catch with him. And the fact that I didn’t detect any red flags off the bat was concerning.  

“As flattering as that sounds, I don’t think I’m down for dating right now.”

“You still have priorities to focus on, I understand. I wasn’t asking for anything like that now, just the opportunity to observe and support if possible. We have all the time in the world, no need to rush anything.”

“Now that I think about it, you told me before that you were visiting, so you’re not even from here? Why even pursue me?”

“Do you not have friends outside of Illinois?”

“I mean, I do, but how would we go about dating, hypothetically?”

“It can be difficult considering I doubt either of us has the time to fly across the country too often.”

“Across the country? Where do you even-” we were interrupted as our waiter delivered our food. He opened the bottle of wine for us and poured each of us a small serving. I tasted it. I hadn’t really had wine before, but it was sweeter than I expected. I’m not a heavy drinker, but this was something I wouldn’t mind having ever so often. 

“I don’t only want to talk about myself, tell me more about you,” he said as placed a napkin in his lap.

“There’s not much to know about me.” I say, “Well, nothing all that interesting, I’m just a girl who works too much.”

“I don’t think that’s all that true.” 

“Excuse me, rude” I said. “You’re coming off as a real smart ass for someone I just met recently. What? You want me to dump out my bullshit and tell you all about my f****d up family and how I’m a useless disappointment to them? Looking for entertainment or something? Or are you just trying to figure out if I’m a red flag so you can move on and be done with this fascination you have with me?” for a moment he was silent, only staring. I’d said more than I wanted to and now I was feeling embarrassed. Why’d I lash out like that? Instead of saying anything more, I prepped myself to leave. This was a waste of time. 

“You don’t have to run away from me.” I looked over at him, confused. “I may have overstepped with my previous statement, but I wasn't trying to offend you. I’ve already seen how wounded you were from our first conversation. You stay guarded, eager to push away anyone who starts to remind you of the person who’s hurt you the most. But I’m not him, Ada. And you are not the person they’ve painted you to be. I’m sorry, but I care little about the family that has conditioned these insecurities on you. But I do know that most of the negative things you believe about yourself are not true and that you are far more interesting and enticing than you may think. You’re creative and smart and it shows through the things you create through passion.” I felt my cheeks blush.

“And how would you know any of that?”

“Well, that’s because I’ve read your writing.” he smiled. “I guess you could say I’m a big fan.” 

To say I was shocked is an understatement. I didn’t appreciate Nate holding that type of information from me for as long as he did. I hadn’t expected him to have been one of my subscribers. I was upset at first, maybe it was the wine, but as dinner progressed, I felt more at ease. Jamila was the first fan I’d met in person and to be speaking with someone else who enjoyed my work made me happy. He told me that he had recognized me at the airport from i********:, which had led him to approach me. He told me more about himself and that he was a lawyer who lived in Manhattan. We talked about our interests and hobbies and I was surprised to find that we shared some of the same tastes. We both must have had a bit too much wine as I started feeling slightly tipsy, so we decided to take a walk to sober up and work off some of the food. The air felt nice as the cool summer breeze brushed my face. I felt oddly giddy as I walked with a bit more of a spring in each step. At some point, we stopped to take in the city and I caught him staring at me. He gently took hold of my chin to tilt my head to the side. I realized he had been looking at the scratch on my cheek from when my father had struck me. I tried to cover it with makeup. He made a face full of concern. 

“Don’t make that face,” I say. “I’m tougher than I look. It didn’t hurt nearly as bad as it looks.” 

“How can he call himself a man, let alone a father, when he abuses his power and strikes you to relieve his own anger?” he rubs his thumb across the scratch. I smile and caress his forearm. 

“A man who doesn’t hit women, you’re really milking this perfect guy act, aren’t you?”

“Please, that’s the bare minimum,” he starts. “But I am not perfect, nor do I try to be.” His jaw tenses and he looks away as if he’s thinking hard about what he wants to say. His voice went low to a whisper. “I’m not so innocent either, but any striking that comes from me will come from pleasure and respect, not anger.” I felt my body grow warm as my heart skipped a beat. He continued caressing my cheek as I was now caressing his arm, nuzzling my face in his palm. 

“Like spankings?” I asked. 

“Only if you’re being bad,” he replies. I let out a giggle.

“And if I’m being a good girl?” 

“Obviously you'll get a reward…” he leans in and his breath tickles my ear. “And I'll do whatever it takes to please you.” a chill runs down my spine, I feel hot. His cologne smells amazing this close. I was quiet for god knows how long, until I heard him whisper my name and tilt my head up to look at him. His gaze was stern, yet comforting. “Are you alright?” I hesitated for a moment, still hazy from the wine, but my mind felt clear. 

“How far is your hotel from here?” I asked. 

“Maybe 10 or so minutes without traffic,” he answers. I bite my lip anxiously, a gentle vibration running through my body. His thumb runs across my lips. “Should I make it 5?” he whispers. I don’t answer, but I part my lips and bite his finger, never breaking eye contact. He takes a sharp inhale. “f**k it…” and pulls me closer, replacing his thumb with his mouth. His tongue forced its way into my mouth and god was it sweet. My body was shaking so much I felt I might fall, but he held me firmly, kissing me. I didn’t even remember arriving at his  hotel room. One moment, we’re making out in Chinatown, next he’s pinning me against the doorframe, attacking my neck. Whether he was leaving hickeys or a hundred kisses, I didn’t know, but it felt amazing either way. He was breathless when he pulled away, “I want you to submit to me.”

“Excuse me?” I ask also breathless, my hands entwined in his hair as I desperately wanted to pull him back into kissing me.

“Just for tonight…” he kissed my cheek. “Allow me to lead…”he kissed my collar bone and trailed his tongue up to my ear. “Let me take care of you.” Yes! Yes, whatever! I could feel his hard on pressing against me and I was aching to feel it without all the layering. I nodded. “I need to hear you.”

“Yes, please just take me.” I trailed my hands down and under his shirt to feel his tummy. It was so hard and muscular with soft hairs above his belly button. He slapped my ass. 

“These are gonna have to go.'' He unbuckles the buttons of my jeans and slides them down. Before he comes up, he hoists me up and carries me to bed. He lays me down gently, giving me one quick kiss. I watch as he hovers over me, pulling off his sweatshirt. Sexy couldn’t begin to describe him. “Like what you see?” I blushed and my eyes trailed down to his pants, unhappy to see a belt tightly wrapped around his waist. I want it off now. I crawled over to him, looking up at him with doe eyes, begging for more kisses. His lips meet mine as he runs his fingers through my hair. My hands trail down his tummy and start working on his belt. His hand catches me, moving mine away. “Not yet.” 

“But-” he shushes me.

“You’re not nearly ready enough. You’ll meet him soon, be patient.” I pout, but allowed him to lean me back on the bed. I ignore the belt and continue exploring his torso with my hands. I feel his back, it’s so broad and smooth. I couldn’t wait to leave scratches on it. He goes back to kissing my neck as he lifts my bralette, exposing my chest. “You really are stunning, my dear. I could admire you all day.” He takes hold of one of my n*****s and begins rubbing them between his fingers. I tense as another shiver runs through me. My breasts have always been a weak spot for me. I let out a whimper as he takes the other in his mouth and circles his tongue around it. Randomly, he nips and pinches them. I let out a yelp. He looks up at me and stops.

“Sorry, you surprised me.” I say shyly.

“What’s your safe word?” he asks. “I should have asked sooner. I won’t go any further until you tell me.” I learned from Jamila about safe words, random words you wouldn’t say unless you wanted to stop someone’s current actions or behavior. I hadn’t thought about it before and being on the spot, I randomly said the first thing that came to mind. 

“Um, Chalupa..” I felt embarrassed, that was probably dumb. He smiled, amused, but didn’t laugh.

“Alright then.” he went back to suckling my n*****s, this time without the nipping. I was kinda disappointed, it felt good in a way. Finally, his hand rubbed my c**t over my panties. I could feel it jumping at his touch. “Has this ever felt a man before?”

“Are you assuming I’m a virgin?”

“I don’t assume, I ask.”

“I’m not…but I’m clean in case you're wondering. The last man I was with was years ago and I’ve long been tested. ”

“That’s good to know. I was tested a month ago.” He began to pull my underwear off, and I lay back trying to calm my shivering. He kissed my tummy to my pelvis to my-

“Ah!” I yelped, jerking back. Most guys tend to trail their tongue slowly over the c**t, but I hadn’t been prepared for how fast he’d be flicking his. He pulled me back down and started again. I tried to relax, but it was so sensitive I ended up jerking back again. “Sorry, I can’t take it head on like that.”

“Then tell me how you like it.” 

“I guess…a little more on the side if that makes sense.” Was this going to annoy him if I couldn’t take it? This time he locked his arms around my legs to hold me in place and started again. I braced myself, but this time was better, less intense and more pleasurable. I would still tense from time to time, but I managed to relax more. The suction and flicking of his tongue was far better than any vibrator I’d ever had. He too began to relax as he allowed his hands to play with my n*****s again. “Mmmnn…Ahh..” I moaned, running my fingers through his hair. My body was on fire, I could melt. My mind was blank except for the feeling of his lips and beard on my skin. I wanted to feel this forever. I could feel my orgasm building and I started gripping his hair tighter. “Nate…” he didn’t stop even as my legs pressed against his head. “Nate….” Wait, hold on….this didn’t feel right. “Nate, wait…” My walls started to spasm and Nate gripped my legs even tighter to hold me in place. Unable to pull away, something gushed out of me and I let out a cry, trying to pull away from him. “C-Chalupa!” He then stopped and let me go. I had to press my legs tightly together to stop the stream of liquid. I felt my whole face flush. Did I just pee? Reluctantly, I looked up at him. His mouth and chin were wet. I expected him to be angry or disgusted, but he was smiling, almost laughing. “I-I’m sorry. I didn’t know that was going to happen.” 

“Sorry for what?” he asked as he wiped some of the liquid from his chin. “I didn’t take you for a squirter, but I’m delighted to see that you are.”

“No, I think I…I think that was.” he cupped my face and licked his lips. 

“You didn’t do anything wrong. Seeing as it doesn’t have a scent nor does it taste like much, I don’t think you did what you think you did. So relax…” he parted my legs and rubbed my c**t again. I jumped and twitched. I was far too sensitive. “I love seeing you enjoy yourself, hearing those sweet breathless moans… And the way you called my name, it just makes me want to f**k you just to see how much more I can get out of this little body of yours. So, by all means, squirt all over me as much as you like.”