The Long-Awaited Prostate Massage

Olivia became my favourite masseuse ever since I set foot in the parlour. She was exceptionally good at different types of massage, had a charming personality, and was strikingly beautiful. She satisfied my needs,  and I returned the favour by tipping her well.

We grew fond of each other, and I always looked forward to my weekly Swedish massage sessions. Therefore when she told me she would be leaving for 6 months of training in Thailand, I was happy for her but also visibly disappointed.

“Don’t be sad,” she said, “I’ll be back before you know it.”

I was holding onto my clothes and staring at her beautiful innocent face.

“Plus, I’m going to learn a few shaft massage tricks I’m sure you’d like,” she added and smiled cheekily.

“For that, you have a free prop to work with until you get better. It’s right here on this ‘thighland’,” I said, pointing at my bulging penis covered by the towel on my waist.

She stopped at the door and turned her neck to look at me. 

“Well, it will be the first one to get my prostate massage treat when I get back—for free,” she said and walked out, swaying her wide hips seductively.

She left the door open so I could watch the tease show, and it really turned me on. I’d fantasized about putting my hands on her hips and caressing her wobbly ass more times than I could count. She had a sexy and curvy body and dressed it sexily during our massage sessions, leaving very little to the imagination.

She returned and found I hadn’t moved an inch.

“Do you need help with that?” she joked.

“No, I was just thinking about your offer, and it sounds good. Let me dress up so I can activate a 6-month countdown timer on my phone,” I shot back.

She laughed loudly and continued until I finished dressing. 

“That’s fair but crazy,” she said as she calmed down.

I gave her a good tip and got out my phone. I counted 6 months from the day and set up a reminder titled “The Long-awaited Prostate Massage from masseuse extraordinaire Olivia.”

“I’ll miss your jokes,” she said when I showed her the reminder.

“My body will miss your soft hands, and my eyes will miss staring at your ass,” I said, and pulled her closer for a hug.

“What about your legs,” she whispered as we embraced.

“My third leg will keep longing,” I replied in her ear.

We hugged tightly, and I could feel her bra-less boobs poking at my chest. I didn’t want to release her from the embrace, and she didn’t seem in any hurry. I slowly started moving my hands down her back to her ass when we heard footsteps approaching. I let her go as a knock sounded on the door.

We walked towards the door, and I bid her goodbye. On the way home, I kept thinking about what my massage routine would be like without her. She’d recommended her friend Grace who was just as good. I said I’ll think about it and probably give her a try. 

I actually did, but settled for one monthly session. She was okay, but wasn’t Olivia.

After the 6 months were up, I waited another 2 weeks before showing up at the massage spa, eager and with lots of expectations. Sadly, Olivia wasn’t there, and nobody had heard from her. 

I was disappointed, but still went in for a massage from one of the girls, which helped to boost my mood.

After an hour, it was over, and I was on my way home. The time was a few minutes to five in the evening. I drove slowly while admiring the London suburbs. 

Halfway through my transit, my phone pinged with a message notification. I would’ve ignored it, but a second message followed a few moments later.

When I unlocked the phone, the message was from a new number, and it read, “Welcome to Oliv Spa; Your tantric prostate massage awaits you at the pinned location.” I checked the second message, and it was the pinned location.

I smiled, threw the phone on the co-driver seat and accelerated towards the location. It took 20 minutes for me to pull up at the private residence driveway. My biggest surprise was seeing Olivia walking towards my car smiling. I parked and got out to hug her heartily.

“I bet you’ve already warmed up, so come I’ll show you what I’ve learnt,” she whispered. I obediently followed her towards the lavish house. We passed the living area and headed straight to the last room in the hallway.

Everything was set up, so she asked me to undress and lie on the massage table. I did as asked.

Even though I’d already received a massage, Olivia started working on my back like she always did. The touch of her soft hands brought back amazing flashbacks, and my back muscles tingled with familiarity. She was more tactful, and it felt good. I quickly noticed how she paid more attention to my glutes and inner thighs, unlike before when she usually brushed over them.

She massaged each butt muscle keenly and even spread the cheeks to tease and massage the crack. I tried to stifle a groan, but it was all in vain. Olivia was all up in my erogenous area, and it was pure bliss. My balls ached with anticipation as I felt her fingers move down slowly.

She started with the inner thighs, and I instinctively spread my legs to ensure her hands had unrestricted access. My penis was fully erect and throbbed under my weight while my balls twitched nonstop. She brushed her fingers on the balls, then spanked my ass lightly and said, “Turn around now.”

I followed the order and immediately noticed she was fully naked. Looking at her perky breasts, wide hips, and well-shaven vaginal area awakened all my sensual senses. I was on the edge of climaxing when she poured oil on my chest and spread it out through my body.

Olivia took her time until she got to my aching manhood. The shaft had blood-filled veins all over, and I could literally feel my heartbeat on the tip. She took one hand and started massaging the balls while the other hand stroked the shaft slowly. Then, she released my balls and applied pressure on the space between my ass hole and balls.

I folded my knees, and she applied more pressure around my prostate area. I experienced mindblowing orgasmic sensations and wondered how she kept me on edge for so long.

She teased my butt hole to intensify the sensations. I felt an overwhelming out-of-body experience, and let out a loud groan. She continued for what seemed like forever, then eased up the intensity. I opened my eyes to find her staring at me.

She was leaning very close to the table, and her boobs were barely inches from my raised knees.

“Do you want me to finish you off?” she asked.

I nodded my head.

“Next time,” she said, and tapped the head of my erect shaft with her finger. She pushed my knees down and told me to relax.

“What do you think?” she asked after a while.

“Nothing! But I’m overwhelmed with sensations,” I said. 

“Do I have to leave? Because I don’t want to,” I added jokingly.

She continued looking at me, wearing a satisfied grin on her beautiful face. She knew she had me (read my prostate), and I would be coming back for more.

Picture of Olivia Hartley

Olivia Hartley

Olivia Hartley spent over a decade working as a high-end companion in London, offering discreet companionship to artists, entrepreneurs, and frequent flyers alike. With a background in modern languages and a love for the arts, Olivia brought charm, intelligence, and emotional depth to her work—qualities her clients valued just as much as her looks.Now in her late 30s and semi-retired, she writes full-time, drawing from her years in the industry to demystify the world of luxury escorting. Olivia believes in empowering women through self-awareness, financial independence, and thoughtful branding. Her writing combines honesty with elegance, offering insights to those new to the industry and guidance to those aiming for long-term success.

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