The Massage Date : Age Gap Romance

I liked her profile on the dating app and assumed I wouldn’t hear back from her. There was a significant age difference between us, and I figured she wouldn’t be interested. At 46, she looked incredible—judging solely by her pictures. Her profile mentioned she was into fitness and running; “runner” was even part of her username, and her physique definitely reflected that. A cute blonde with shoulder-length hair and three kids probably wouldn’t go for a younger guy like me, or so I thought.

Later that night, I was lounging on the couch after the gym when my phone buzzed. I got up, walked over to where it was charging, and saw the dating app icon glowing in my notifications. My heart and stomach did a little flip as I nervously swiped to see who had responded. To my complete shock, it was Runner Girl. I don’t know why it hit me so hard. I’d always been drawn to older women, but they usually seemed too shy to engage with me. This woman, apparently, was different. Her message thanked me for the compliments I’d sent and tossed a few my way. I was even more surprised when she ended it with her phone number—talking would be so much easier without the app’s clunky messaging system.

I glanced at the time: a little after nine. Part of me didn’t want to seem too eager by texting her right away. My heart was racing, but I didn’t want to come off as a pathetic dork. So, naturally, I did the dorkiest thing possible—I logged back into the dating app to stare at her pictures again. It didn’t take many flips through her gorgeous eyes and radiant smile before I felt compelled to send that first text. After the third scroll through her photos, my fingers instinctively drifted to the texting app. Heart pounding, I typed her number and a simple “Hey you.”

Not exactly Shakespeare, I know, but I was too nervous for poetry. Minutes dragged by as I waited, each one feeling like an hour. I put the phone down, trying not to obsess over it. My anticipation was driving me crazy. Was this normal? Why was this woman I didn’t even know getting me so worked up? She could be a jerk, or her pictures might be fake. I told myself to relax. Then—buzz buzz. A text notification. All that self-talk flew out the window as I leapt up, grabbed my phone, and saw it was her. Relief washed over me, followed by another surge of excitement. Her reply was as simple as mine, but soon we were texting back and forth, exchanging the usual “get to know you” chit-chat that kicks off every new dating conversation.

About 20 minutes in, I heard a distinct notification—a media message. I opened it to find a stunning selfie of her in a sundress, likely taken in her front yard. The dress hugged her figure perfectly, her smile showcased flawless teeth, and her kissable lips drew me in. The hemline was short but tasteful, revealing toned legs that screamed “runner.” I stared so long I nearly forgot to reply. Finally, I texted that the picture was incredible. She thanked me and followed with a playful “Well…,” hinting I should send one back. I jumped up, fixed my hair, and tried to look presentable. I’ll admit it—I took at least ten photos to get one decent enough to send. It must’ve taken a while because she texted again, asking if I was still there. I picked the best shot and hit send.

When she didn’t reply right away, I worried she didn’t find me attractive. I’d built this up so much in my head that the thought of her losing interest stung. Just as I started to feel down, she texted an apology—her dogs needed to go out—followed by a message saying I looked cute. My face flushed; I was blushing hard. I thanked her and joked that, since we’d gotten the photo exchange out of the way, maybe I should give her my name. We laughed, realizing we hadn’t even introduced ourselves properly after all that texting. “I’m Aly, by the way,” she wrote. We kept trading questions, and I felt surprisingly at ease with her. I asked what she thought her best feature was. After a moment, she replied, “My eyes… and maybe I shouldn’t say this, but my ass.”

The second I read that, my stomach flipped—a mix of nerves and something else. My heart raced, and I felt myself getting hard. It wasn’t even a particularly risqué answer, but my body went into overdrive. I replied carefully, trying to hide the effect her words had on me. Almost instantly, she followed up with, “We should meet.” I agreed, and we tossed around ideas—movies, coffee, drinks—before settling on coffee at 1 p.m. the next day. She said it was getting late and she needed sleep. I wished her good night, telling her how much I’d enjoyed our chat. I’d love to say I slept too, but I spent hours rereading our texts and scrolling through her pics again. I finally passed out around 3 a.m.

The next morning, I woke up buzzing with excitement about meeting Aly. I made breakfast and was checking my phone when I glanced at my calendar app. “Oh shit!” I yelled. I’d booked a massage for the same time as our coffee date. How do I never check my schedule? I’m such an idiot. Maybe she’d be okay switching times—or maybe not. Not the best first impression. I texted her, asking if we could adjust the time, explaining my mix-up. “Did you change your mind?” she replied. I assured her I hadn’t, just forgotten about the massage. To my surprise, she wrote, “Oh, that sounds amazing.” On impulse, I texted, “Would you wanna get a couples massage with me?” Panic hit as I realized how bold that was for a first date. It felt like forever before her reply: “Actually, that would be nice.” I couldn’t tell if I was more excited or terrified. I sent her the address, and she confirmed she’d meet me there.

Driving to the spa, my hands trembled on the steering wheel. I was so distracted I passed the place twice before pulling into the right lot. After a few deep breaths in the car, I went inside, checked in, and asked if Aly had arrived. The receptionist said I was the first and directed me to the lobby. I sat down, texting Aly that I was there. “Almost there,” she replied. My knee bounced nervously as I waited, every second stretching endlessly. Then I saw an SUV pull into the lot. A woman stepped out and headed toward the entrance. I looked down to avoid staring as the door chimed.

I glanced up, and there she was—a breathtaking blonde in dark sunglasses, a calf-length coat, and heels that accentuated her toned legs. My heart skipped as she removed her glasses and said, “Hi, I’m Aly. It’s nice to finally meet you.” I managed to stammer a response and gave her a hug. Her body felt perfect against mine, a testament to her fitness. I was far from cool, stumbling over my words. Our small talk was cut short when two massage therapists approached, saying our room was ready.

They led us down a hall to a small room with two massage tables and a chair in the corner. They told us to undress to our comfort level and left us to prepare. Aly and I exchanged shy smiles. Seeing her in person made me blush uncontrollably. Trying to play it off, I pulled off my shirt and tossed it onto the chair. I caught her checking me out as she began undressing, though she quickly looked away. I couldn’t help but sneak a glance too. As she stripped to her bra and panties, she angled herself modestly, but for a split second, her hand dropped, revealing a hard nipple pressing against her bra. A rush of arousal hit me, and my cock stirred. I turned away to hide the bulge forming in my boxer briefs, sliding under the table’s covers as fast as possible. Once covered, I slipped off my briefs and tossed them aside. Aly laughed as they flew across the room. “Are you naked under there?” she asked, giggling. “You’re supposed to be for a massage,” I teased back. She slid under her sheet, then tossed her bra and panties to the corner with a mischievous grin. As she adjusted, the sheet slipped, briefly exposing her perfect ass. She hadn’t exaggerated—it was flawless. My cock went rock-hard, its outline embarrassingly visible through the thin sheet. I flipped onto my stomach just as the therapists knocked and entered.

They began the session, and I tried to focus on anything non-sexual to calm my arousal. The last thing I needed was an awkward moment with the staff. As my therapist worked my scalp and neck, I relaxed, and my erection subsided—mostly. But every time Aly gasped or moaned softly during her massage, it threw me off again. I’d refocus, only to feel my cock stir when I imagined her hands on me instead. The session flew by; I’d have sworn it was shorter if not for the clock. The therapists told us we could get dressed and meet them in the lobby. “How was yours?” I asked Aly. “Absolutely amazing,” she sighed, sounding refreshed. I propped up on my elbow and looked at her. She met my gaze, and we sat in silence for a moment. Finally, I said, “You look absolutely gorgeous.” She paused, then replied, “You’re not so bad yourself.”

I couldn’t help myself anymore, I leaned over and kissed her softly. She kissed me back, her tongue tracing my lips. The sensation sent a jolt through me, my cock swelling again. I deepened the kiss, my hand sliding behind her head. She gasped and pulled me closer. Shifting to her table, I settled between her legs, my hard cock brushing my stomach as I moved. I kissed her neck, feeling her arms tighten around me. Her heat from her now turned on vagina pressed against me as I thrust my hips, grinding against her swollen clit. My lips trailed to her chest, where her nipples stood stiff and begging. I sucked each one, teasing with light bites. Her hips bucked harder with every touch. Lifting her hips, I ground my throbbing shaft against her soaking pussy. After one final savoring suck, I moved up to my knees and hiked her hips up even higher, exposing her absurdly swollen vagina. I couldn’t look away. It was absolutely fucking gorgeous. Her lips were so swollen and full, absolutely glistening with her juices. Her clit flared out and looked absolutely stunning, her swollen lips glistening. It was perfect—absolutely fucking perfect. I teased her slit with my fat cock tip, coating it in her juices.  I began running my shaft back and forth over those wanting lips.  I couldn’t even begin to describe how amazing it felt. Seeing her body shake with each pass was making me delirious. I helplessly positioned my cock to thrust inside of her.  Completely drunk with lust and want, my cock head pressed into her soft wet opening.  All of the sudden, she stopped me. “I can’t fuck you,” she gasped. “I just met you.” I ground against her again, and she moaned, hooping I'd change her mind. “I want to, but I can’t. I really like you.” She was right—I liked her too. I slid up and gave her a deep kiss again. I didn't want to spoil this incredible experience we had just because I wanted her so badly.  I knew at that moment that we would be seeing a lot of each other in the future. Did I want to fuck her? Absolutely! But more than that, I felt a deep connection.  One that couldn't be denied.  We laughed about the wildness of our first date, wondering if the staff had overheard. The clock showed we’d overstayed, so we hurriedly dressed.

Definitely the most unforgettable first date I’ve ever had.