Road Trip 02: Off the Mat

"About what?"

"Your first time. Us, that night." She said it without eye contact, as though she was a little wary of it.

"What is there to talk about?"

"Dunno, I guess.... I guess I wonder sometimes how you remember it now, after everything since. I was only ever two people's first, and one of those I never see anymore. I'm curious." Now she looked at me, with interest.

"I remember being nervous. I remember you doing a pretty good job of easing that."

"How, by letting you play with these?" She looked down at her chest.

"Yeah, it worked like a charm."

"They always do," she said, cupping them in her hands and laughing. "What else?"

I looked at her, and she looked at me, I willed my mind back four years, and we started to remember together.

October 9, 2014

She'd told me for weeks that she wanted to take it slow, but I wanted it to be tonight. My roommate Todd was gone for the weekend, and I'd cleaned the place, opened the windows to push out some of the stale air of a freshman boys dorm room. I had new sheets on my little twin bed, and a pack of condoms my mom had given me before I left home, a fact that had deeply embarrassed me then, but which I now appreciated. My laptop was charged, ready for the DVD Katie was bringing with her, and I'd gotten hold of some wine, courtesy of a junior I knew who was willing to make a liquor run for me. I had candles. I had planned and prepped and overthought it fifteen times, and I was going to lose my virginity tonight.

Katie knocked, and I opened the door. She smiled up at me as I took in her favorite denim jacket, the blue tank top she wore under it, and the tight, low rise jeans she knew I loved. Her midriff was showing, as was the hem of her black lace panties - just a bit, at her hips, letting me know they were there. Those were my favorite of hers.

We'd gotten together only a week or so into school, but during our first real hookup she found out I was a virgin and slowed things way down. I hadn't wanted to: I wanted on the train fast, I was done waiting on the platform. But she insisted. We'd take it slow, we'd make sure I was ready, we'd go step by step. I hated it and I appreciated it all at once.

We'd finally seen each other completely naked for the first time last week, in her room. We spent all day there. She got me off with her hands, with her tits. Not her mouth yet, though that would come. She touched herself for me as I watched, masturbating with her. That was a strange feeling, taking this thing that I'd done in secret for so long and sharing it. She showed me how to touch her, guiding my fingers over her clit, showing me everywhere she wanted me, taking the training wheels off and letting me ride solo until she moaned and shook and came.

All of those were firsts for me. My high school girlfriend was from a religious family, and the furthest we'd ever gotten was topless. I walked home from her house ready to burst so many times, racing to my room to placate the throbbing in my pants with visions of her in positions I'd only seen in porn, knowing she wasn't going to do any of it with me, at least not any time soon. We finally split up when I left for school, and though I loved her in a certain way, I didn't spend a lot of time mourning that transition. I was ready for other things now.

"Hey, beautiful." I leaned down to kiss Katie as she came through the door. After spending a little while on that, she finally looked around at the candles, the made bed, the wine. The conspicuously clean room.

"Oh my, Danny... hoping for something special tonight?" She had a glimmer in her eye. We'd talked about things already, and she knew what I wanted.

"I'm hoping for you, and you're special," I replied, closing the door behind us.

"Sweet talker. It might just get you someplace."

"So what are we watching tonight?" I asked, as she put a bag down on the bed. I noticed with anticipation that there was a change of clothes in it. She reached in and pulled out two DVDs.

"Your choice - we've got the raunchy sex comedy, or..." she held up two DVDs - Don Jon, a movie about a porn addict featuring almost naked Scarlett Johansson, and Pitch Perfect, her favorite movie.

"This feel like a trap." I said, after a moment. She raised an eyebrow.

"Could be... better choose wisely."

I reached out and grabbed Don Jon, holding it just long enough to see her eyes narrow, and then... dropped it back in her bag. She laughed.

"Smart man right here." She gave me the DVD and moved over to the wine. "Want a cup?"

I gave her a nod and a thanks as I loaded the DVD into my laptop, then went over to hit the lights. The candles took over. She stepped out of her shoes and took off the jacket, draping it over a chair. I admired her chest, pushing at the tank top; with the jacket off I could see the black lace straps of her bra as well, under the spaghetti straps of her top. She saw me looking and did a little turn.

"You don't have to stop with the jacket." I said, walking over to her and collecting her in my arms again.

"Mmm... slow down, baby, we have all night." She kissed me, her hand on my chest. "And all morning." I felt a little flutter, a combination of nervousness and excitement, in my stomach.

We climbed into bed, careful with our cups of wine, and started the movie. I made fun of her for it, but Pitch Perfect was a pretty excellent film - smart, funny. She'd made me watch it three times now, and it still landed. We agreed Anna Kendrick was hot, and the bus scene with the Miley Cyrus song rocked. But this time, we turned it on but didn't talk. As we watched, I became hyperconscious of her, knowing what we were moving toward. Her head on my chest, my arm around her, her breathing. Her hand on my leg, fingers moving around slowly. I was hyperconscious of myself, too. Heat seemed like it radiated off me, and every time she moved my dick twitched. I'd had a semi basically since she curled into me. My heart was pounding under her head, she must have felt it.

After a few minutes of that, she looked up at me.

"You okay?" She asked. And I was, despite the nervousness of anticipation. My kiss served as my answer, and she returned it, reaching a hand up to my face and leaning her head back. But as I started to move my hand over her breasts she stopped me, sitting up to face me.

"Seriously, Danny... I want you tonight, but I don't want you to be uncomfortable. Talk to me."

"I'm not uncomfortable. I want this. I'm just... nervous is the wrong word, but I can't think of a better one."

"I know that feeling. And..." she leaned down to me, "I know how to fix it."

Without breaking eye contact, she lifted her tank top over her head and dropped it to the floor. Her chest was level with my face and only inches away, so I stared into her cleavage, held up by the lace black bra she'd been wearing the first time we hooked up. She brought my face to her, burying it in her breasts, as I kissed her. I felt the bra loosen and fall away then, and I reached a hand up to squeeze and fondle and pinch those big, luscious orbs that hung in front of my eyes. She stroked my hair as I kissed her and took a nipple into my mouth, then the other.

I suddenly became aware of my cock, painfully hard, pushing against my jeans, begging for escape. The jitters had gone, replaced by an urgency as the hormones took over. She seemed to feel it too, pulling my shirt off and then standing, working off her jeans. She stood there, naked but for the lace panties, and there was no turning back even if I wanted to. And I really, really didn't want to.

The movements that came next were a blur. Closing the laptop, moving it off the bed. Her hands undoing my pants, pulling them from me. Mine on her ass, sliding the underwear off her, touching her the way she taught me, guiding her to the bed with me. Her hand sliding into my boxers, up the leg, up my thick, throbbing cock, pulling the fabric from me until we were both naked.

She somehow knew already where I'd put the condoms, sliding her hand into the middle drawer of my desk next to the bed and emerging with one. She lowered a breast to my mouth as she massaged my balls with one hand, and used the other to bring the condom wrapper to her teeth, ripping it open. She removed it and rolled it down me slowly, sensually. I'd tried them on before, even jerked off into them, practicing, but to have her put it on me was a completely different experience.

"I'm going to make this last as long as I can," she told me, gently pushing me down to the bed, "but I want to make you feel so good right now, Danny. Don't hold back." and she slid a leg over me, kneeling above me rock hard virgin cock, then lowered herself onto me.

I'd imagined what it would be like so many times - the warmth, the wetness, the movement - but even with the condom between us it felt better than I'd ever dreamed. Feeling her move on me, even slightly, sent shockwaves through me. She sat straight up on me, letting me look her over as she gyrated slowly, grinding.

"You're so big... you have an amazing dick, baby." I knew she was lying, I knew I was slightly above average at best in that department, but I loved hearing it anyway. I strained up into her, lifting her a little, feeling the sensation of a thrust for the first time. My hands found her legs, her hips. I held her to me as she moved. Her breasts swayed above me and I reached a hand up to one, but immediately wanted the pressure against me back.

"Can we turn over?" I asked, wanting to be on top, wanting to thrust into her.

"We can do anything you want, baby." She said, kissing me as we rolled, nearly falling from the twin bed. Laughing, we righted ourselves, and I started moving in her. I was tentative at first, exploring this new angle and sensation, but I picked up speed fast.

"Fuck me hard, you feel so fucking good, Danny..." she moaned, as I started to hammer her. I felt that familiar warm radiation start to build, first in the head of my cock and then down, down, toward my balls, which tightened as I lost any semblance of control.

"Katie, oh god, Katie, I'm-" I didn't finish the sentence, as I blasted into her, completely unable to control it, like every bit of matter in my body shot through my dick and into her, accompanied by the longest most intense orgasm of my life, a different sensation altogether from masturbating, or even getting a hand job. I fell on top of her, and I could feel the smile on her face as she stroked my hair, knowing I would fall asleep on her, and letting me.

Present

"You snored, too. Almost immediately. I don't think I told you that at the time." She laughed at me once I was done describing my memory of the night.

"You didn't, no. And thanks for that."

"I thought it was cute. And hot, honestly, feeling you fall asleep in me and on me."

"I didn't get you off, though, some gentleman I am."

"Aw. It was your first time, consider it a gift." I laughed, and watched Melky Cabrera drift back on a routine fly to right to end the 9th and send the game to extras. Bonus baseball.

"Did you know then that you were more into women?" We'd talked about this before, but somehow she'd always found ways to not answer it. I didn't expect this time to be different, and didn't really know why I wanted it to be, but I asked anyway.

"God, Danny, I don't know. I was 18, what the fuck did I know about anything. I knew I liked you, and I knew we both thought Anna Kendrick was hot."

"She was. Is."

"True fact. But... I was a college freshman, I was away from home for the first time, everything was kind of new and sexy and scary together. And you had a nice butt."

"You mean 'have.' I have a nice butt."

"I said what I said." She paused. "Why do you care, anyway?"

"I was afraid you'd ask that. I don't know. Some weird kind of latent jealousy? Some man card thing?"

"Yeah, so, both of those are dumb reasons."

"They are." I looked back at the field. "Still wanna know, though." She punched my arm.

We watched the rest of the game without much deep conversation; the other stuff had worn us out. And it was a good end - after a tense but ultimately scoreless tenth, the Phillies pushed a run across on a double, a stolen base, and a sacrifice fly before turning it over to the bottom of the inning. The Pirates threatened, with a man on second and two down, but Hector Neris blew a fastball by Josh Bell to end it, I cheered along with half the stadium, while Katie glowered.

With much of the rest of the crowd, we walked back over the bridge in the cool air. We caught an Uber on the other side for the quick ride back to her place in the Polish Hill neighborhood, a little two bedroom decorated very much to Del's taste - she'd lived here before Katie had moved in, and the default had held in most places. They set me up in the spare room, and I changed out of my hoodie and jeans into a t-shirt and a pair of shorts. Katie and I had a beer and reminisced a bit more, not going too deep - a couple funny stories we both knew, I couple "what's so and so up to now?" talks. But I was fading fast, and after a bit she prompted me to go to bed.

"We've got a busy day tomorrow, you and me, so get some beauty sleep, bucko." I nodded, and said goodnight.

Five minutes later, I was fast asleep, dreams of the past floating past my eyes.

Day 3 - Tuesday, September 26, 2019

We all slept in, but I was the last one up, around 10. I stumbled out of their second bedroom in my shorts, and noticed a nice aroma from the kitchen area. Del was reading on the couch, fully dressed. She barely looked up. Katie was hovering near pancakes on the stove, wearing a t-shirt and either panties or nothing - the t-shirt was long enough that I couldn't tell.

"Damn, Danny, have you been working out?"

I had a little bloom of pride that she noticed. After the breakup, I spent a couple solid weeks shuttling between going to work and eating chips on the couch in my parents' basement. But though I needed to wallow, none of it felt good, so I recommitted myself to working out: more frequent running, daily trps to the gym before work. After a few months, I'd seen a real effect, losing about ten pounds and getting a lot more definition in my abs, chest, arms. I hadn't really bulked up, but I'd gotten leaner, more toned.

"Yeah, some. Helps me deal with the general rage at the universe."

Del looked over at me. "Get inked, you'd look pretty hot." Katie gave her a weird look. "What, just because I'm gay I don't get opinions?"

"Thanks, Del." I said, as Katie rolled her eyes.

"Want some pancakes?" she said, turning back to the pan.

"As long as they come with coffee." I yawned.

"That you can get yourself. Mugs," she pointed to a cabinet behind her, "and coffee." Her finger dropped to the coffeemaker under the cabinets, next to the fridge. I helped myself, pouring it into a mug with our alma mater's logo on it.

"So what are we doing today?"

"Del's doing some work, but you and me, we're seeing sights."

"Like what? I've been here before."

"You've never been to my museum, have you?"

"Actually no."

"So, there, and a few other places. A little Katie-tour of Pittsburgh. Mostly other museums."

"Didn't you take today off? And you're taking me to your job?"

"I promise you'll be the only person on my tour, and I'll spare the backwards walking."

"I'm in," I said, taking my first sip of coffee and feeling my body welcome the promise of caffeination.

We ate, showered, dressed, and headed out, leaving Del alone for a couple hours before she had to go in to try to replace a bartender who was moving on.

It was a long day, but a fun one, and despite the fact that I'd been here with her before she managed to avoid spots I'd seen. Her museum was cool - I was not an art museum regular, but I appreciated it, and Katie's depth of knowledge and professionalism was pretty cool to see. She introduced me to a couple of co-workers, and we got to peek back into the restoration area, though not where any real work was getting done.

Lunch was at a little taqueria near the museum, where Katie seemed to be a regular, waving at several of the staff as we ordered. Then it was off to another museum of a sort, this one a little less high-class than Katie's - Randyland, an outdoor public art installation that was a community centerpiece. Then, a baseball museum dedicated to Roberto Clemente, the late great Pirates star, which we capped off with a visit to the old Forbes Field site.

By then, it was closing in on 5pm, and we made our way back to the apartment. It was a warmer day, and we'd both worked up a sweat from walking a bunch, so we took showers again, then hung out waiting for Del to get home. That happened around 7, and we headed to dinner.

The place Del's friend ran was outstanding, a little dive bar that happened to serve perfect burgers to go along with some live music and craft beer. We spent a couple hours there, eating, drinking, talking, listening.

Our waitress was Talia, and she was cute - blond, good smile, nice eyes, great ass. She knew Del and Katie, at least in passing, and chatted a bit with me in between songs as we sat at the table - nothing of much substance, but enough to let me know there might be interest there. I felt that same double helix of excitement and guilt I had that night in Niagara.

"I can get her number for you, if you want to stick around another day or two," Del said, noting the direction of my gaze. I was staring over at Talia, with a particular focus on the aforementioned great ass. I looked back at Del, then Katie.

"Nah. Thanks. It's been awesome seeing you both today, but I've got a long drive to Chicago tomorrow and I've already booked a hotel downtown."

"Seriously Danny," Katie said, "she's cute, and I bet we could make something happen here. She seemed like she was into you."

"I doubt it, she's just making conversation. Seriously, I appreciate it, both of you. I'm good."

Katie looked like she was about to argue, but Del gave her a look and the moment passed.

We spent a little while longer there, and tipped Talia well on our way out. Katie and I sang a Vampire Weekend song as we wandered, moderately buzzed, back to their place, while Del judged us silently, but kindly.

Once in the apartment, Katie poured another glass of wine, and I had a beer. Del declined, as she had to do dome work in the morning. As we sat around I remembered Katie had mentioned her recent art to me the night before.

"Hey, Katie, didn't you say you had some artwork you wanted to show me or something?" She smiled, and Del's eyes widened in a weird way.

"Yes! I've been taking this portraiture class and have been sketching me and Del a bunch, want to see?"

"Absolutely, I haven't seen anything of yours in a while." She got up and went over into their room. I looked at Del. "What's wrong?"

"Nothing, really. They're good. Some nudes, just so you're prepared for that."

"Of..."

"Either of us, both of us. She took some photos to model off of."

"Well okay then." She laughed.

"Hey, you've already seen her business, and as for me..." she shrugged. "just bodies."

Katie came back in with a large sketchbook and settled onto the couch next to me, then started to flip through. The first several were straight up portraits of both of their faces, with beautiful detail, including one closeup of Del that was really lovely, intimate, clearly done by someone who had studied her face in more than just one session.

"These are all great, Katie, but this one is really stunning. You should hang it up."

"I keep telling her that," Del said, from the other side of the room.

"I will, I will! I just need to get my act together and get a frame or get it mounted or something." She said it as she turned the page, and there was Del, nude. Del saw my face.