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Their pizza avoidance had other benefits as well. A few months ago, they definitely wouldn't have let themself be talked into the brief-style harness instead of the boxer-style harness, but Olivia had managed to convince them with just three words and a tiny smirk.
"I like these," Olivia had told Max when they asked her opinion about which pattern she liked. They'd been talking about the boxer briefs but she'd reached straight for the briefs. They were sky blue with bright white seams and a rubber ring on the front to hold the lime green and blue dildo they'd chosen. They'd opted for a more colorful dildo because they wanted it to match the area immediately around it, which would be a harness that did not leave them too exposed.
Katie had explained that this dildo was a pack and play, meaning that it could be worn as a packer or as a strap-on. She'd demonstrated how to pose it with the display model, which Max probably would have seen on the shelf just above eye-level if they'd looked up when they'd been wondering how the different models felt.
But Katie also cautioned that some customers had complained that the large base made it uncomfortable to wear for long periods of time as a packer. Though she emphasized that each complaint had been accompanied by a rave review of its performance in more intimate situations. She recommended that, if Max wanted to try it as a packer, they wear it around their apartment before committing to wearing it in a situation where it might not be easy to remove it if they got uncomfortable.
In addition to the sky blue pair that Olivia had picked out, Max had selected a rainbow pair of briefs and boxer briefs with a purple and white shark pattern. If they didn't want to have to do laundry twice a day for the rest of the weekend, they definitely needed more than one option.
Katie had been very generous with the new customer discount and had thrown in a bullet vibrator and the essentials - lube and toy cleaner - for free. But even with the freebies, Max spent enough on their first visit to earn a discount on their next trip, as long as they used it within the next thirty days. Which was great because they were confident they'd be back to pick up a couple of things they'd caught Olivia staring at while Katie was explaining the importance of lubricant.
"I'm a little hungry, how are you feeling?" Olivia asked as she stepped out of the car upon arriving back at Max's place.
"I could eat. But if I have a whole meal now, I won't want dinner until like nine," Max said, pushing their key into the deadbolt lock.
"Oh, I bet I can help you work up an appetite," Olivia said, waiting for Max to turn to look at her before glancing slowly at the bag in their hand. "It's quite the workout," she teased, arching an eyebrow.
--
After a light and very late lunch, Olivia suggested they take a bath together, seeming to have forgotten the whole shower fiasco earlier that day. That led to the conversation Max had been hoping to avoid, at least a little longer.
Max stumbled a bit trying to explain what had been going through their mind, but they managed to explain - out loud for the first time to anyone except Bailey - that they experienced bottom dysphoria. They weren't sure how to describe that they liked how it felt to touch themself, but they didn't feel comfortable with someone else touching them. Even though they really did want that.
Olivia didn't question what Max was sure came across as contradicting concerns, she just held their hand and listened. And when they were done rambling, she kissed their forehead and thanked them for telling her. It felt good to talk to someone other than Bailey about their gender dysphoria.
While it was great to have someone in their life that could relate to what they were going through, they were also finding it helpful to talk to someone who didn't really know what it was like. It wasn't that Max thought that Bailey intentionally led them on a path that mirrored his or intentionally put his feelings about his own experiences on Max when they were struggling with something similar. But it happened.
And it was becoming clear to Max that they needed both types of support in their life. They needed someone they could relate to and who could guide them, but they also needed someone who would just listen while Max worked it out. They needed someone who could give them a possible explanation for how they felt and someone who could look at it from a different perspective and ask them questions that might help them understand what was really going on.
For example, talking it out with Olivia a bit helped them understand why, despite feeling more comfortable with her than anyone else they'd ever been with, they had struggled with disrobing for a shower with her. It wasn't that they weren't comfortable enough with her, it was that they were more comfortable with her. So they didn't have to sacrifice their comfort to meet societal expectations.
"I'm sorry that our sexy weekend has to include these little freak outs. I'm simultaneously afraid that I'm coming off as being only interested in sex while also being worried that I'm steering us towards unsexy conversations," Max said, inhaling deeply and releasing it slowly.
"Selfishly," Olivia said after Max finished their breathing exercise, "I'm really excited to be the person who gets to be with you while you do all this. I wouldn't trust anyone else to support you the way I really hope I can. When you trust me with your deepest feelings, you make me feel like the most important person in your life. What's not sexy about that?"
Max couldn't have asked for a better person to have by their side at this very critical stage in their life. They needed to experience this with something they trusted with the most vulnerable parts of themself and they had no doubt that they could trust Olivia completely. They were anxious, of course, but with her enthusiastically along for the ride, they wanted to focus on all of the milestones ahead of them. This weekend would start them on a path towards the "understand how their gender identity influences their sexuality" milestone. Which was, without question, the milestones they had been looking forward to the most.
They had a really good reason to be more sexually adventurous than Max may have previously been confident being. If they were feeling timid, they could remind themself how important it was to push their boundaries a little. They needed to get out of their comfort zones in order to find their most comfortable zones. And the contents of the bag still sitting on the chair to their right were a great first step.
But after such an emotionally vulnerable conversation, they both agreed that some lounging time was in order. Max found a movie on Disney+ and stretched out on the couch with their head in Olivia's lap. They'd imagined being comforted after feeling dysphoric would have felt a lot like pity, but it didn't. She stroked their hair with one hand while her other held their side, keeping them safe and close to her.
Max only caught a few minutes of the movie before falling asleep.
--
When Max awoke almost an hour later, Olivia was still gently stroking their hair as a very naked Chris Hemsworth was being scolded on screen by Russell Crowe with a bad Greek accent.
"You're very cute when you're snoring," Olivia said quietly.
"I don't snore," Max scoffed, blatantly lying to their... girlfriend? That had been the conclusion the night before, right? They were giving this an actual shot?
"Oh wow, you're a terrible liar," Olivia laughed. "Or a great liar trying to throw me off with an obvious lie so you can lie to me later," she teased.
"Jesus, babe, what kind of people have you been dating?" Max asked.
"I like it when you call me babe," Olivia said, tracing her fingers down Max's tricep in slow, light circles while her fingernails scratched at their scalp.
"Speaking of..." Max said, turning onto their back and looking up at Olivia. "We agreed last night to give this a shot and you'd said that you couldn't be sure it wasn't just lust and I was just wondering... if things are any clearer now?"
Olivia trailed her fingertips down the inside of Max's forearm at an achingly slow speed before answering. "Well, it is definitely clear to me that I want to continue being with you physically. This morning was..." she trailed off, closing her eyes and taking a long breath in through her nose. "I really, really enjoyed this morning."
Max was glad to hear it, but worried there was a "but" coming. I really enjoyed this one time, but I don't think it's more than physical. That was usually the line they got after what they thought was a great date.
"But," Olivia continued, justifying Max's concern. They braced themself for the honesty that they shouldn't have asked for so soon. They should have waited - it hadn't even been twenty-four hours yet. Why did they always rush things?
"I don't think it's just that I'm sexually attracted to you," Olivia finished.
Max felt a rush of relief wash through them, followed by a rush of excitement. They'd wanted this from the beginning of their friendship and they were finally getting it. Things never worked out in their favor.
"I meant what I said earlier, before you passed out," Olivia continued, pausing to flash them a coy smirk. "I feel like the most important person in the most important world - your world. I'll be honest, the last eighteen hours or so have me questioning why I avoided this for so long. I had a lot of fun for a few years, but this feels really great."
"Feeling confident is kind of a rarity for me, so I'm going to lean in and take credit for being such a great partner that you had to admit that you actually like relationships," Max said without thinking. They still hadn't actually confirmed that a full commitment was what Olivia wanted. "I mean... potential partner. I guess we haven't really gotten to that part yet."
"Well, we both agreed that we wanted to explore this. And we can't do that individually, we have to do it together. So I think that makes us partners," Olivia said, brushing Max's hair off of their forehead. "I'm a little too old to be someone's girlfriend and definitely not ladylike enough to be a lady friend. So unless 'partner' means something, like, really serious, I'd like it if you thought of me as your partner."
Max nodded cautiously. Olivia had avoided commitment a bit too much in how she described that.
"Not that I'm not taking this seriously," Olivia said when Max opened their mouth and closed it again quickly. "I'm serious about you. About us. About this. I wouldn't insert myself into this really important time of your life if I weren't serious. I care about you and I want to be with you."
Max reached across their body to still Olivia's hand against their forearm, drawing her gaze up from where she'd been staring intently while she spoke. "I'm sorry that I keep making you convince me that you want to be with me. It's just hard. For a lot of reasons."
"I know," Olivia said, squeezing Max's arm and brushing their hair back again. "If you're into it, I'd love to spend the next several hours showing you how much I want to be with you," Olivia said, threading her fingers through Max's.
"I could be talked into that," Max teased, the mere suggestion sending a rush of heat between their legs.
Olivia released her grip on Max's hand and straightened her fingers, pressing them against the length of Max's. "The dryer buzzed while you were sleeping, so your new garments are ready to wear," she said with a crooked grin. "Do you want to go try them on and call me in to join you when you're ready?"
"I'd like it if you were there," Max told Olivia. "I mean, I'll put them on in the bathroom but I'd like to have you there to tell me if you like them." They knew if they were left to stare at themself in the mirror, their eyes would immediately focus on the spots they didn't like. Olivia could distract them from their insecurities and save them from themself.
"You mean how much I like them," Olivia said, tilting her head and waiting for Max to nod before continuing. "I would love to be the sole audience member in your fashion show."
--
A few minutes later, Max tentatively pushed the door to their bedroom open wearing the blue brief harness Olivia had selected for them. They figured they'd start with the one she picked because they knew she'd react positively to it and they needed the confidence boost. The night was sure to be full of nerve-wracking moments and they needed to pump themself up a little.
"I hope you don't mind," Olivia said as Max entered the room. She'd paired her phone to their bluetooth speaker and found Max's only candle, which she was lighting at the moment. The LED lights they'd mounted as uplighting behind their headboard were on, but the room was otherwise dark. "You'll have to come close so I can see you, but I don't really like the big light," she said, pointing to the light on the ceiling fan in the middle of the room.
Max laughed. "That light doesn't even have a bulb in it. The switch only controls the fan," they explained as they flicked the switch on and off. "The lamp on my nightstand and the one on my dresser are the only other lights in the room."
"I tried to turn that on," Olivia said, pointing to the lamp on the nightstand. "But it didn't turn on."
"Hey Google, turn on the lights," Max said with a proud smile as the room lit up. It wasn't like it was particularly hard to screw in a couple of wifi bulbs, but they liked to show it off. It was fun. "Hey Google, uplights only," they said a few moments later. They didn't want the lamps on either. The lighting that Olivia had picked was just right.
"Neat," Olivia said, scooting back on the bed to sit against the headboard. "Okay, come here and let me see how hot you look in what I picked out for you." Max took a few steps and stood next to the bed. They felt Olivia's eyes on them, examining them. It was equal parts stressful and exhilarating.
It was also a little chilly. All Max wore in addition to their new briefs was a t-shirt and sports bra. Their nipples hardened, pushing against the stretchy fabric and, while it was unclear if it was the temperature or the mood that had caused their reaction, the look in Olivia's eyes as they drifted up Max's body made her reaction easy to read. She looked at them as if she were hungry and they were a meal that she intended to savor.
"I have very good taste," Olivia said slowly, her eyes still scanning Max's body. She smirked as she playfully patted the mattress next to her. "Come up here so I can get a closer look, please."
Max climbed onto the bed, kneeling next to Olivia. She set her hands on their waist and gently pulled, guiding them to straddle her thighs. Her fingers teased along their underwear, occasionally sneaking up and under the hem of their shirt. Their body reacted to her without much input from their brain, their abdominal muscles jumping as her fingertips grazed slowly against their skin.
Olivia grabbed hold of Max's hips and leaned forward, pressing a kiss to their stomach through their shirt. Her warm breath permeated the fabric and felt hot against their skin. Her fingers flexed into their skin as she placed a second kiss to their stomach, a few inches from the first.
Heat snaked through Max's core and settled between their legs. If Olivia intended to inspect each pair this closely, they were going to need to do another load of laundry that night.
Olivia slid her hands up Max's sides, pushing their shirt higher and exposing their skin. They weren't thrilled with the remaining soft layer that hid the abs they'd been spending so much time working on. Sure, strengthening their abdominal muscles had other benefits. Namely, a significant reduction in the back pain that had plagued them most of their life - even after they'd corrected their posture a few years prior. But they were missing the one benefit they'd been seeking - visible abs.
However, Olivia didn't seem to mind and that's what was most important. Max braced their hands lightly on her shoulders while she covered their exposed skin with kisses. What started as gentle pecks escalated quickly to Olivia tracing her tongue along the smooth lines of their tattoo. And they'd be lying if they said that watching - and more importantly, feeling - someone kissing and nibbling along their hip bone wasn't a motivating factor in their decision to get the tattoo.
"Tell me about this," Olivia said, tilting her head back to look up at Max and scratching her nails down their side, then along their waistband.
"I'm a nerd," Max choked out, not realizing how dry their mouth had gone. They cleared their throat before continuing, "It's from Borderlands. It's a tattoo that one of the main characters has. Except hers cover her whole body and glow and are a representation of her identity as a siren," they said, starting to ramble a bit. "It's, uh, yeah. Like I said. Nerdy..."
"You are one sexy nerd, Max. Fuck," Olivia said, sliding her hands quickly around their body and pulling them forward. Her hands kneaded into their ass as she alternated between pulling at the elastic of their briefs with her teeth and dipping her tongue no more than a quarter of an inch under it. "Stop me if I get too close to doing anything you don't want."
Max nodded and rasped, "Okay," as Olivia ran her hands down the sides of their thighs, her fingertips slipping around to their inner thigh as she moved them back up to repeat the motion. With each pass, her fingers came closer and closer to their underwear but stayed at a comfortable distance, not pushing Max's boundaries.
"I, uh," Max stuttered. "I don't really know what I want, honestly. I've had plenty of sex in my life but this feels brand new, somehow," they admitted. It didn't feel like the first time but it certainly felt like a first time.
"Can I just say again how fucking excited I am to be the one who gets to go on this wild journey of sexual exploration with you? I can't wait to learn how to make you melt, Max," Olivia said before tugging at the hem of their shirt. "Can we get rid of this?"
Max didn't hesitate, shedding the tee in one swift motion, letting it slide off of their arm and onto the floor. Olivia held their gaze as she dragged her chin down their body, her open mouth following shortly behind and grazing their skin. She hesitated as her lips hit their waistband and Max nodded to assure her they wanted her to keep going.
As she reached her destination, Olivia's eyes fluttered closed, her tongue flattening against the fabric as she moaned into them. The subtle vibration against their clit made their breath catch in their throat.
Max swallowed hard. "That feels good," they breathed out as they clenched their core. Over the years, they'd learned a few tricks to increase their chances of having an orgasm. They found that if they squeezed their pelvic muscles tight early in their arousal, their clit usually felt more sensitive.
"Fuck, babe, I felt that," Olivia said as she pressed her tongue more firmly against Max. Between their own arousal and Olivia's mouth, their briefs were soaked through, the wet cotton providing just the right amount of friction.
"Oh my god," Max breathed out slowly. "Keep doing that," they said, closing their eyes and tilting their head slightly back. As Olivia found a steady rhythm, Max started to lose their balance, their legs wavering a bit as they tried to follow her tongue.
Olivia found Max's right wrist and lifted their hand from her shoulder. They looked down to find her staring straight back into their eyes. "Guide me where you want me," she said as she set their hand on the back of her head and nodded encouragingly before pressing her tongue hard against their clit through the fabric. She kept the pressure steady and flexed her grip on their ass, encouraging them to move their hips and grind against her tongue.
