Dating Roulette

by D. Kelly

  “I’ll keep that in mind.” I move to step inside my room, and he reaches for my hand.

  “Two things—tonight was the best second date I’ve ever had.”

  My heart flutters in my chest. Tristan has always been a good guy, and I’ve always envied his girlfriends for being with someone as incredible as him. But having him turn those charms on me is a bit exhilarating.

  “Also, in a little while, if you hear me call out your name, know that I’m reliving the sensation of your pussy clenching my finger and imagining it was my cock instead. Now go make your list from tonight’s date while I take care of business.”

  Holy shit. He did not just say that.

  I close my eyes and take a deep breath.

  “Keep your eyes closed and tell me what you’re thinking right now.”

  “You’re cruel for telling me that because all I want to do is make myself comfortable at the foot of your bed and watch.”

  His lips are against my head, and when I inhale, his cologne seeps into my lungs and settles around my heart. He’s starting to imprint himself on each one of my senses in a new and enlightening way. I hope it never stops.

  “Bexley, I’m pretty sure that’s at least a fifth date opportunity. Imagine it now, and when it happens, you can let me know what’s better: the fantasy or the reality. Good night, angel.”

  “Night, Tris.” After closing the door, I lean against it. I was so close to telling him that so far, the reality is beyond any fantasy I’ve ever had, but I’m not quite ready to put those cards on the table yet.

  Once I’ve grabbed my pajamas, I take a quick shower so I can clean myself off. My nipples are slightly bruised, but knowing Tris is the one who marked me sends a fresh wave of desire coursing through my body. I’m buzzing with excitement as I wrap the towel around myself and step into the hall to go back to my room.

  The sound of Tristan moaning stops me in my tracks. He’s louder tonight, and when I turn toward his room, I see why. The door is cracked open. Normally, I’d duck into my room, but he never leaves his door ajar. He’s not playing fair.

  “You enjoy that, don’t you?” His words travel into the hall, and I bite my lip to keep from answering.

  The combination of his grunts, his breathless moans, and echo of his hand as it glides through the lube as he works himself up has me crossing my legs, hoping I don’t spontaneously combust.

  “Fuck, Bex, just like that . . . fuck me harder . . . yes, yes, your pussy is so hot, so wet, and so fucking tight.”

  I’m pretty sure I need another shower now, but as the sound of flesh working flesh intensifies, so do his groans.

  “Bexley!” he cries out, and my clit pulses with need. My name on his lips is the sexiest thing I’ve ever heard. I take a step away from his door because I’m now in desperate need of my vibrator.

  “Good night, Bex. Sweet dreams.”

  “Oh my God,” I mumble as my face heats with embarrassment. Tristan only laughs, and I realize it’s the happiest he’s sounded in a really long time.

  I decide to skip getting myself off. Maybe I’ll become so needy I’ll sleepwalk straight onto his dick instead. After I’m comfortable in bed, I reach for the journal and review what I have for today before adding to it.

  Under the good column, I’ve got the following:

  Turned me on in a way I’ve never been before. I don’t know where this version of Tristan has been hiding, but damn . . . I can’t wait to get to know him.

  Bought me donuts this morning, my favorite ones.

  I make the following additions:

  Let me listen as he fucked his hand to thoughts of me.

  Treated the date as a real official date and paid for everything

  Told me I’m the best part of his day. (This one would veto a thousand fuckups)

  Bad part of the date:

  He wouldn’t let me watch him as he got himself off—letting me listen earned some brownie points back.

  On Sunday, Tristan and I were like ships passing in the night. We were both up early but for vastly different reasons. He got called into work, and I made myself go to the gym.

  I spent the remainder of the day running errands and catching up on laundry. I tried staying awake until he got home but ended up falling asleep on the couch.

  Being the gentleman Tristan is, he did wake me so I could have a good night’s sleep in my own bed. Or maybe it was so he could kiss me senseless at my bedroom door—either way, I’m not complaining. After an incredible night’s sleep, I woke up this morning well-rested and ready for my breakfast date.

  Rita passes me the syrup for my pancakes and groans appreciatively as she takes a bite of her own.

  “Why don’t we start every day with breakfast at Rudy’s?” she asks when she swallows.

  “Because we’d never be able to leave the gym, and my body can’t handle that kind of torture. I’m still aching everywhere after going yesterday.”

  Her brow arches. “You sure you’re only sore from the gym, and you’re not holding out on me about Tristan? I mean it’s been a while since you’ve gotten laid. Maybe your body is getting used to being used again.”

  “Don’t I wish.” With a sigh, I take a bite of the chocolatey goodness on my plate.

  “Would you go there, Bex? Risk everything for a roll in the sack?”

  “After the seventh date, yes. Before then, even though it would be incredibly hard to turn down, no.”

  Rita sips her coffee and flashes me a sympathetic gaze. “Honey, have you ever considered that you could make it past the first seven dates with anyone and the relationship still might not work out?”

  “Sure, in the abstract, but it’s not something I need to worry about until I can actually make it through all seven dates.”

  The waitress drops off more cream for my coffee and hands me a note. “Some guy dropped that off and asked me to give it to you. You’re a lucky girl; he was a cutie.”

  “Thanks.” Rita watches with rapt attention as I open the note.

  Bexley,

  One of the perks of being your own boss is making your own hours. For date number three, I’d like to take you to a picnic on the beach. I know I told you to pick the dates, but since this is one of your favorite things, I figured it would be okay to take control. Let me know if there is a day this week you can get off an hour or two early. I’ll handle the rest.

  Tristan

  “Wow . . .” I pass the note to Rita.

  She looks up at me and smirks. “That smile on your face is going to be a permanent fixture soon, isn’t it?”

  “One can only hope.”

  “Tristan is one of the good ones. I hope this works out for both your sakes.”

  She’s not the only one. “Me too, but enough about me. How was your dinner with Adam last night?”

  Rita points at her eyes. “See these bags? They’re from the all-night fuck fest we had after he bought me an amazing meal. Did you know he likes basketball?”

  “Yup, he and Tristan were on the team in high school. They still play pick-up games on the weekends with some friends.”

  “You should show me your old yearbooks sometime. You’re lucky you’re still friends with people you went to high school with. We moved around so much I never really lived anywhere long enough to make friends I wanted to keep in touch with.”

  Poor Rita. That had to be difficult. “Considering I could have killed their friendship, I did get lucky. Adam is one of the few who made it to date seven, and then I found out he kissed his ex, and that was that. Stupid high school shit. I met Tristan the day I called it off and decided we should be friends. Best decision of my life.”

  Rita tosses some money on the table, and I look at the time. I shovel in a few more bites while she nurses her coffee. “They got past it, though, obviously.”

  I down the rest of my coffee and put my part of the bill and tip on the table as well. “Sure, they fought about i
t for a brief period — bros before hos and all that. Adam ended up going back to his ex a few days later. She’s the one he was kissing—everything was fine after that.”

  “When did the three of you become friends?” she asks as we walk to our cars.

  “The following year, we had some classes together. Tristan and I were like two peas in a pod at that point. Adam spent most of his time with his girlfriend and realized it was easier to bury the hatchet with me so we could all hang out than it was trying to get Tris to ditch me when Adam could squeeze him into his schedule. It was easy to love Adam as a friend. We just weren’t compatible as a couple.”

  I pause as we reach our cars. “Well, that was an early-morning monologue. Sorry for the history lesson—you know I get carried away sometimes. Do you guys have another date set up?”

  Rita digs through her purse for her keys. “Yup, he’s taking me out Friday night, but I’m hoping for a midweek booty call.”

  Adam will probably marry Rita. She’s literally the female equivalent of himself.

  “I’m sure you’ll get your wish. We should go before we’re late. Have lunch in my office?”

  “You know it.” She waves, and I pull out my phone. Before pulling into traffic, I sync to the Bluetooth and call Tristan.

  “Bexley.” His voice is smooth as silk.

  “Tristan, should we add stalker to your resume?”

  The sound of his laughter greets my ears. I’ve always loved his laugh. “It’s hardly stalking when you run out the door screaming your goodbyes and that you’re late to meet Rita at Rudy’s.”

  “That’s a very good point.”

  “You know what would have been better?”

  I have a few ideas, but I’ll keep those to myself for now. “If I’d invited you?”

  “God, no. The last way I want to start my morning is with Rita recapping her all-night sex-a-thon with Adam. However, a good start to my day would have been a kiss goodbye.” His words are the best kind of foreplay.

  “Is that so? I didn’t realize we’d graduated to morning kisses.”

  “Bexley, after last night, I think we’ve graduated to at least that, don’t you?”

  Damn, I hope so. “Okay, we can do that. I mean, you know . . . add morning kisses to our approved activities.”

  “I take it you got my note?”

  Bless him for changing the subject before I completely soak my underwear before I even get to work. “Yes, and I love the idea of a beach picnic. Unfortunately, I have meetings tonight, dinner with the parents tomorrow, and I’m out of town for that conference on Wednesday and Thursday, but I have Friday off since I’ll be traveling most of the morning.”

  He groans, and it reminds me of the audio performance I got last night. “All right, Friday it is, but it’s going to be a long week. Can we schedule dates four and five for Saturday and Sunday now since we’re losing the entire week?”

  “I’ll pencil you in.”

  “Good and think about what you want to do. I like being able to give you things you haven’t had, Bex. Believe it or not, it makes me happy.”

  I’m pretty sure my heart just grew three sizes bigger. Or maybe I’m suddenly developing an arrhythmia. Whatever the case may be, Tristan Xavier Jacobs is becoming hazardous to my health. “I’ll let you know. Have a good day, Tris.”

  “You too, angel.”

  “Let me get this straight. Bexley is out of town, and you guys haven’t made plans for phone sex? Video sex? Nothing?” Adam opens our beers and passes me one.

  “We haven’t even had our third date yet.”

  “Neither have Rita and I, but that hasn’t stopped us from screwing each other senseless.”

  My head whips around at his words. He didn’t say fuck. “You really like her!”

  Adam picks at the label on his bottle and avoids eye contact. “So what?”

  “Nothing. It’s cool. I like Rita, and she’s a good friend to Bex. What’s your plan?”

  He finally looks at me. “No plan, just keep dating and having sex. If it’s meant to last, it will. What’s your plan?”

  “Spend the week working, go to the gym, and take Bex out on Friday.”

  Adam kicks his feet up on the coffee table. “You know that isn’t what I was asking. Are you going to marry her or what?”

  “It’s a little soon for that, don’t you think?”

  He downs his beer and slams it on the table. “Stop being a dick, Tris. You’re dating Bexley, your best friend. This can go quite a few ways, and most of them are bad. I’m trying to be a friend. Talk to me.”

  “What do you want me to say? I’m scared shitless this is going to kill our friendship?”

  “For starters,” he answers with a smug grin.

  “You’re right; this could go to hell fast. I don’t know what concerns me more—not making it through the seven dates, or actually making it through and figuring out what’s next.”

  Adam grabs us two more beers and sits back down.

  “For what it’s worth, I thought you two would have figured out you were in love with each other before we graduated college. Whatever this is between you has been a long time coming.”

  I’m in a shit mood, and I know it’s because Bex is out of town. I usually miss her when she’s gone, but this time, I ache for her. “I would, you know . . .”

  Adam watches me in silence while I try to figure out how to put my thoughts into words.

  I finish off my first beer and hope I don’t regret this. “I’d marry her. In a fucking heartbeat.”

  “Like I didn’t already know that.”

  “What the hell? Why did you ask then?”

  “I wanted to know if you knew it yet.”

  “Asshole,” I mutter, but he only shrugs. “It’s not like I want to drop down on one knee and propose right fucking now. When I used to think about the future, I imagined our spouses getting along, our families vacationing together, and our kids growing up to be best friends. It’s different now. The future I see has easily shifted to one where she and I are together. It’s next to impossible to imagine her with anyone else—and that’s how I know I’m fucked.”

  “Nah, Bex adores you, and she has since she met you. Maybe that’s why I’m surprised it took you so long to date. That girl saw you and pulled you straight into her orbit before anyone else had the opportunity.”

  I toss him a controller so we can play and get past this conversation. “Fifteen-year-old Bex did not have an ulterior motive to get me into bed with her ten years later.”

  He flashes me a disbelieving gaze before turning his attention to the game. “Maybe not, but she knew she wanted you to be her friend. You’ve got to admit it’s worked well at keeping a large number of women out of your life.”

  While we play, I think about what he said. I’ve dated more than my fair share but never as much as him and some of our other friends. In part, it was because I enjoyed my time with Bexley, and I missed her when we spent too much time apart. But there is no way she somehow intentionally created that scenario to have me to herself.

  I’ve taken Friday off as a much-needed vacation day. It also gives me the opportunity to be ready for the beach whenever Bex is home and ready to go. She always hates these conferences, so I’ve made sure to get some extra wine and her favorite comfort foods.

  On the way home from the gym, I picked up her favorite cupcakes. I’m tucking them into the picnic basket when the front door opens.

  “I’m in the kitchen!” I don’t want her to be scared since I’m home in the middle of the day.

  “Hey, what are you doing here?” she greets me with a killer smile.

  “Mental health day. How was your trip?”

  She stalks toward me and wraps her arms around me. “Much better now.”

  “Did you miss me?”

  Her arms go around my neck, but she’s on her tiptoes. I scoop my hands under her ass and lift her as she wraps her l
egs around my waist. I could get used to this.

  “Maybe,” she offers, and her lips meet mine. Bexley takes control of the kiss, and I tighten my arms around her while carrying her to the kitchen counter. She keeps her legs around my waist when I set her down, and I pull her hips flush against me. “Tristan.” She gasps, breaking the kiss and throwing her head back. She grinds against me as I lick a path from the column of her neck back to her lips.

  “I missed you, too,” I reply, before crushing my mouth to hers. We’ve missed ten years of this, and there’s no way I want to miss another second of time together. She slides her fingers through my hair as our lascivious kiss deepens. Every whimper of hers fills me with hope for our future.

  I hate that she needs these dates to accept what I already know – we’re meant to be. But for whatever reason, that validation is important to Bex, and if it brings her to the same page as me, I’m in.

  The two of us kiss for what seems like forever before she finally pulls away. “I missed our good morning kisses,” she confesses quietly.

  “I missed kissing you good night at your door.”

  She leans forward and catches my earlobe between her teeth. “I really missed the sound of my name falling from your lips as you come.”

  With a groan, I steady myself against the counter. “I missed taking you out on dates so we could be closer to date eight. I’m looking forward to calling out your name when your sweet pussy clenches around my cock.”

  “Holy fuck, Tris. Tonight, can we pretend we’re on date eight?”

  I pop a quick kiss on her lips and grab us both some water from the fridge. “No way. You have a process, and there’s not a chance in hell we’re going to skip dates, no matter how much I want to.”

  “Fine.” She’s pouting, but she’s cute as hell when she pouts. “Then I need a nap because no matter how nice the hotel is, I don’t sleep well alone.”