My dirty secret is that I LOVE GWstories. You wouldn’t expect it. In no way do I present as someone who would be into erotica or reading in general (I kid, I kid). So every so often, I do my part by adding to the community. And today is the day I give thanks with another story from my past. The time I hooked up with my first masseuse. And first redhead. And first MILF. And...you get the idea. A redditor I met loved this story and thought it deserved to be posted, so I hope you enjoy it! Skip ahead to the ***** if you want the juicy stuff. But it’ll be better if you get the setup too. I promise.

I (dude, mid-20s) was living in a big city for the first time. East coast of the US. And it was glorious. Shake Shack like 5 times a week. Drunkenly stumbling home from the bars. Tons of new people to meet. Yep, as you can guess, I was in college. Grad school to be precise.

Thanks to a stint in the Army, I was going to school for free. But, also thanks to the Army, I had fucked up all of my joints. My body would routinely knot up, especially during the winter. My shoulders would get weird impingements so I couldn’t type without pain. My knees would feel like there were knives driving through them when I’d run. My hip flexors would get tight and force me to sleep curled up for a week...Moral of the story--wearing 50-something pounds of body armor for a year in a warzone will fuck you up. So, after exhausting all of the lacrosse ball stretches I could find on the internets, I went on the hunt for a massage therapist.

The first one tried to upsell me on an “annual massage subscription”. I didn’t take him up on it because I was in school and thus broke...and also because wtf is a massage subscription? I’m just trying to get the knots worked out, not sign my life away. The second guy was all about scented oils and relaxation which was nice, but felt more like a wellness retreat than a functional deep tissue massage. Despairing, I was ready to go back and sign away my future by joining the annual massage subscription plan when I came across Carol’s ad.

It seemed a bit sketchy at first. She worked out of the basement of her house. Didn’t have any reviews. Basically the setup to a slasher movie. But, she was professional on the phone. Carol was an older woman, in her late 40s, and explained that she used to work for a local pro sports team as one of their on-call masseuses, but had recently decided to pivot away and open her own practice. She was a single mom with two high schoolers and wanted to set her own hours and work from home, hence the basement studio. And she very kindly promised that she would totally not chop me up and store me in her freezer. Fuck it, I decided. It can’t be worse than the annual massage subscription.

I made my way to Carol’s row house. Knocked on the separate basement door. And entered an actually legit massage studio. There was the padded massage table. Stack of fresh towels. The soulful sounds of Enya playing on the speakers.

But my eyes were drawn to Carol. She was older. A few wrinkles. Grey streaking her red hair. About 5’5” tall and a little thicker, but you wouldn’t notice that. Because your eyes would instead be locked on her truly incredible rack. They were large. Probably 38DDD. Straining the thin fabric of her t-shirt. I felt my cock instantly hardening as she shook my hand. To give you a sense of what she looked like, she had a body kind of like these two women--just super top heavy: https://www.redgifs.com/watch/realachingiberiannase

https://old.reddit.com/r/gilf/comments/qri0hf/busty_granny/

But she was totally a pro. Stepped out so I could undress down to my boxer briefs. Draped me with multiple towels while I was on the table. And absolutely pulverized my back, to the point that I was almost in tears. But, the whole time, she swore that even though it was hell in the moment, I would thank her when we were done because the only way to break a knot was through directed, sustained pressure.

After I’d come out of the pain coma, I found that I could move for the first time without tension in weeks. And I was hooked. Carol gave me a hug on my way out, her massive breasts pressing into my chest, and my cock was also hooked.

I started seeing Carol once every 2-4 weeks when the pain would flare up. And we grew more relaxed. Started talking during the sessions. She’d tell me about how annoying it was working with pro athletes (shitty pay and entitled clients). I gave her a few war stories from Iraq. Then a few war stories about dating in the age of Tinder. We became friendly, but it was always professional. No hint of anything sexual.

But I couldn’t stop thinking about Carol’s deliciously thick body. Post-massage, I’d go home, close my eyes, and wrap my hands around my hard cock, moaning as I’d stroke myself to the thought of Carol’s massive breasts. Imagining her hard nipples in my mouth as I’d pump out a thunderous orgasm. Which was a mistake, because I started getting even more turned on whenever I’d see Carol, my cock twitching in anticipation of the post-massage jerking session.

I’d love to say I started laying the groundwork for a hookup but, at that time, I had terrible game. I was/am pretty good looking--6’ tall, athletic, attractive face. Can hold a conversation. But I was also a minority who’d grown up in a super-white area and was totally ignored growing up. In retrospect, there was definitely some latent racial stuff going on in that community but, back then, I’d just assumed I wasn’t that good looking. And while that experience gave me an awesome personality (as determined by me), I also assumed that Carol and I would only ever hook up in my mind. But, as in most things in life, my cock betrayed me.

I stepped into Carol’s studio for what must have been our 6th session. It had been a rough few weeks of final exams, and I’d been celibate for about two weeks. A lifetime for a 20-something guy to not think about sex. But Carol fixed that. She was wearing yoga pants. A tank top that hugged every inch of her tits. And I quickly grew stupidly hard, fantasizing about my post-massage wank session.

She excused herself so that I could get ready and I stripped down to my underwear. I wrapped a hand around my thickening cock, re-adjusting myself so that my erection was slightly less obvious, rubbing off the precum that was already starting to leak out.

Carol knocked on the door.

“Ready?”

“Just a minute,” I responded, scrambling onto the massage table, face down.

Carol swept in and carefully draped a towel over my back, exposing only the portion of skin she’d be working on. She softly touched my back and I spasmed slightly.

“You’re shivering. Let me turn up the heat” she responded, cranking up the space heater. She turned back to me, slathering tingling massage cream on my back to allow her hands glide more easily. I settled into the repetitive motions, my cock starting to relax.

“You’ve got a bad knot here,” she muttered, as she dug hard into my shoulder. She leaned into my back to get more leverage, her breasts pressing against me. And my cock sprang to life, getting rock hard as I felt her pillowy thick tits rubbing up and down into my back as she worked out the kinks.

I swallowed hard and shifted my hips, my cock pointing up to my head, parallel to the massage table, every one of her strokes causing my cock to rub against the soft fabric of the massage table. My face squinted in pain. It was agony. And ecstasy.

“Should I step it back?” she asked.

“No, no it’s good,” I gasped out, trying to pretend I didn’t have a raging hard-on.

“Good, I thought Army guys wouldn’t start crying about a little massage,” she said, driving her hands in deeper, chuckling as I groaned. But the groan was as much from the pain as from the indescribably raw feeling of my aching cock plowing into the massage table.

Focusing on the knot, she powered through, blasting it to pieces, basically forcing me to dry hump the massage table as she worked my back, my pent-up cock barely able to keep it together. After what seemed like ages, my knot finally disappeared and she told me to roll over so that she could work my legs.

I shifted under the towel and rolled over onto my back, surreptitiously arranging my cock so that it lay across my stomach (as opposed to creating a pretty fucking obvious tent). I really liked Carol as a masseuse. I didn’t want to fuck up the situation by coming across as a creep. And my plan worked, she was none the wiser as she moved the towel to expose my upper thighs, kneading my quads while I covertly eyed her heavy tits, softly jiggling with every one of her breaths.

“All right, let’s open up those hip flexors,” she cheerfully announced as she slid the towel up to expose the barest slice of my hips. For those who aren’t familiar, the hip flexor is a tendon that connects your hips to legs. It gets tight from running and sitting in a chair (aka, 90% of my waking hours), and to unlock a tight one, you need to literally dig a finger inside your hip bone, massaging the tendon until it relaxes. It was a release my broken-down body always seemed to need. But something that was also dangerously close to my throbbing penis.

Carol leaned over. Close enough that I could smell the rose scent of her body wash. And worked her thumb into my hip.

“How does that feel?” she asked.

“Not bad--mmmhph” my hips spasmed as she applied some directed pressure. It wasn’t an orgasm, I was safe, but the towel slipped off my hips, exposing my underwear.

“I think you needed that--oh…” Carol’s smile faded as she gazed at my boxer briefs. They weren’t tenting. My erection was hidden. But something much worse had happened.

I should probably mention here that I cum buckets. It’s like a geyser. I’ve met a few women off Reddit and the uniform reaction after I cum is “Damn, that’s a lot.” I’d post a pic but I’m not sure if I can if it’s not verified.

Anyway, cumming heavy is awesome. But the downside is that I also precum like a maniac, to the point where I will even get a visible wet spot on thick denim jeans if I’m really turned on. And, right now, on this massage table with Carol’s heavenly body at eye level, I was really fucking turned on. And Carol’s eyes were locked on the massive wet spot on my grey boxer briefs. Fuck.

Mortified, my face must’ve turned 17 different shades of red as I struggled to grab the towel.

“I’m sorry, I didn’t mean to--” I stammered, but Carol merely shook her head with a wry grin.

“It’s ok. You’re not the first guy who’s cum on the massage table.”

“I didn’t cum, I swear.”

“Oh,” she arched an eyebrow. “I guess that’s just sweat?”

“I mean, it’s pre-cum, but I didn’t ejaculate, I swear.” For some reason, I felt that I really needed to let her know that I wasn’t jerking off on her massage table.

“That’s just pre-cum?” Carol’s eyes widened. Then, blushing, she looked away, coughing to cover her sudden interest.

I awkwardly tried to put the towel back over my underwear. But Carol’s hands were already moving.

“Let me help you with that,” she said as she carefully rearranged the towel, again exposing the top of my hip. She started massaging me again, but something had changed. The sexual tension felt electric. Her strokes softer, more sensual.

“That was a lot,” she said with a forced laugh.

“It’s been a while. Finals and all.”

The back of her hand grazed my rock hard cock as she continued the massage.

“How long has it been since you’ve cum.”

Her breasts were at eye level, so achingly close. And, figuring I’d already fucked things up, I decided that I couldn’t embarrass myself any more than I already had.

“Two weeks. It’s been...hard.”

She slowly stretched out a finger under the towel, touching my engorged cock, chuckling. “I can tell.”

I laughed, feeling bolder now. “You touching it doesn’t help”

She arched an eyebrow. “Oh?”

She teasingly pulled her hand away. But I grabbed her hand and moved it onto my cock.

“Well, you touching it with one finger doesn’t help.”

Pursing her lips, Carol gripped my cock through the sticky fabric of my boxer briefs and I let out a soft moan.

“You’re young enough to be my son,” she remarked quietly. But she didn’t release my cock.

“I won’t tell if you won’t.”

She paused. For a long, awkward moment. And then she let go of my cock. Locked eyes with me. “Just this one time,” she said. And then she carefully removed the towel, moving it to a nearby chair, and pulled down my underwear.

My cock shot straight up, a trail of pre-cum dripping down to my belly. A soft sigh escaped her lips as she looked at my young cock. It’s average-sized, 6”, but has a huge mushroom head. She swirled her finger in the pre-cum and then traced the sticky liquid back around my shaft as I audibly moaned.

Carol gripped my cock in her hand and slowly, leisurely stroked it. Her grip tight. Firm. In control. She brought her hand up to her mouth and licked her palm, using her saliva as lubrication as she softly, sensually stroked me. My hand curved around her waist, gripping her hip tightly as she worked my cock. I was breathing hard, my entire body on fire as this fantastically built older woman sensually worked my cock.

I darted a glance at her face. And, to my surprise, she was just as transfixed as I was. Her face slightly flushed. Lips parted softly. Breaths shallow. She glanced at me and our eyes locked. Connecting. Both desperately wanting this.

She moved her second hand down to my balls and started massaging them. Pulling them further down so she could stroke further up and down my shaft. The pre-cum was just dripping out of my hard cock. Pooling in her hand. She brought her hand up to her mouth. Licked the pre-cum off her palm. And then wrapped her hand around my engorged cock. Stroking it faster. Faster. Her grip tight as I felt my body tensing, from my toes up to my quivering cock.

Carol could feel it too. She gripped my cock tightly. Looked me in the eye.

“Cum for me, baby.”

And I fucking exploded, moaning as I shot rope after rope of cum. All over my belly and her hand. At least 10 solid ropes of thick, white cum. As I came down from the high, she was still stroking my cock. And she leaned over and smashed her lips into mine. A hungry kiss as our tongues furiously explored each other while her hand continued jerking my cock, squeezing every last drop of cum out of my balls.

She broke off the kiss and I dropped my head back, totally fucking drained.

“Fuck,” I muttered, out of breath, in a post-orgasmic haze. Out of the corner of my eye, I noticed Carol was just as flushed as I was. She brought her hand up to her mouth. Discreetly licked my thick, sticky cum off her fingers.

Turning, she grabbed the towel and cleaned the cum off my chest and cock, thoroughly wiping down my shaft and balls.

She shook her head. “You do cum a lot.”

“I warned you.”

“That was just a one time thing, ok.”

But we both knew something had irrevocably changed in our relationship.

“See you next week.”