Massage Chronicles – prostate massage

 Massage Chronicles – prostate massage


Being a relative novice at the time, erotic massage delighted me. I was always looking for different variations, different experiences. How to take the sensual and intimate feeling of erotic touch to the next level.

On one of the local massage forums I frequented there was a thread about prostate massage.

From the moment I learned to masturbate, I was aware of the wonderful sensations that come with anal stimulation. It was taboo. It wasn’t talked about, but I felt really good! Soon the stimulation increased to finger penetration as I rubbed it, so when I read about the full prostate massage I was intrigued. Could it be even better?

My semi-photographic memory recalled an ad I had seen not too long ago and I immediately started browsing the massage ads.

An ad appeared on the page that appeared every few weeks for a massage lady offering prostate massage as part of “therapeutic treatment”. My penis got thicker when I found it.

That ad promised ultimate sensual experiences from a European lady.

My mind immediately conjured up a fat Elvira-type lady, except with blonde hair, telling me to lean into a heavy European accent.

Shyness prevented me from calling her immediately. I had to know more. what was it like I browsed a few porn sites for pictures and videos. These ranged from gentle anal stimulation to Femdom cock milking and strap on sex.

If only it could be so! Just thinking about it made my penis a few shades of purple.

I researched, even more, looking at online reviews fantasizing and daydreaming about what it would be like. To be honest, it wasn’t a big deal. Either there was very little of this type of massage going on, or everyone was keeping it a secret. I couldn’t find anything concrete about this lady online.

At the time, I was a newbie to erotic massage, it took me months to work up the courage to call Betty, let alone see her. Between that decision were a lot of long masturbation sessions.

I was lubricating and caressing my ass as I rubbed it. I guess most guys don’t have long enough arms, so no matter what I did, I never got very deep. Still, it was enough to make me ejaculate. I ejaculate a lot, so most of the time I painted my chest, neck and sometimes my face with streaks of sticky cum.

I didn’t fully massage my prostate no matter what I did. The thought of a girl or lady doing this for me while I was under her control sounded much more thrilling.

Finally, after weeks and weeks, I worked up enough courage to call her. Her kind, confident Austrian-inflected accent was so sexy, so perfect. Just as I fantasized. I had to do this!

Her voice was soothing yet direct and so experienced but unfortunately her location was right in the center of town. This place was a parking nightmare and far from my work. My mind was made up. I wasn’t going to let anything stop me and scrolled down the transport locations on google maps.

Due to the subway location, I was able to plan an alternate way to get to her salon downtown.

With a route in mind and sexual energy heightened during the week, I made an appointment for late afternoon. The appointment I made was late enough in the afternoon to allow me to sneak away from work and get home early enough to discourage any suspicion from the wife. I could always pretend to have an extended late afternoon work-related meeting.

I remember my first visit was on a late spring or early summer day. The weather was favorable and it was a quick ten to fifteen minute walk from the subway station.

When I called her apartment and Betty answered the door, I was delighted. Betty was no blonde Elvira, but she ticked all the boxes wonderfully. Betty had a round face with a striking jaw line. She had a little makeup on her eyebrows and eyelashes. Her light blue eyes sparkled with that milf experience. She could have been Swedish or German. It doesn’t matter. This MILF beauty was probably fifteen years older than me, but she looked good. I suspected she might have been a model when she was younger who had aged so gracefully. Her face was mature but still very beautiful. She smiled and so did her blue eyes as she let me in. I realized that he liked me.

– You are so attractive.

She touched my arm muscles, ushering me into her upstairs apartment, commenting on my muscles.

– And very firmly.

Betty touched my bottom reminding us both why we were there.

Betty moved to the corner of the massage area, which was decorated with tasteful artwork and open earth-toned curtains, framing a largely unobstructed view of downtown. It was a large, sturdy massage table covered in white linen. A small towel folded into a donut shape was placed around the face hole. I giggled. At least there were no whips, chains or strap-on dildos!

– You can undress here.

I guess he’s going to follow me. I’ve always been fit, but this was new. Very few women have watched me undress before. I breathed. Something about it was perfect and touching. I have a clothed European woman who would caress my ass, look at me, check me out while I undress in front of her. The penis was getting stronger. Instead of throwing everything in the usual bundle, I made sure to fold my clothes well and place them on the chair.

I was completely empty sitting there. I sat there in silence. I half imagined her asking me to bend over and touch my toes! Instead, Betty handed me a large cloth towel and directed me to the apartment shower. I cleaned myself up very well, spending the appropriate amount of time washing my nether regions before returning to the massage table, already having a weak erection. My mind and body were ready for this experience.


-You are bigger than the average bear!

Looking at my cock, she smiled, planning what she was going to do to me no doubt. Betty had changed into a black lace corset with very sheer beige panties when we entered the massage area. It was easy to see the corset stopped under her breasts and over her pussy. I had a nice view of her soft and light bush and nipples through the sheer material. My penis rose like someone twenty years younger. So far that was all I could have wished for. Lovely woman with perfect experience to massage me and teach me all about prostate massage.

– Let’s put you on your stomach.

Betty guided me face down.

I positioned my body face down until my head looked through the face hole at the 80’s style berber rug and waited for her touch. Where will it start? Would he shove me in the ass and probe? It took a moment but she came to the head of the table gently massaging my neck and back muscles. With my head peeking through the hole in the table, I looked up at her bare legs and the fact that the sheer material she had been wearing was now removed.

As she bent down to massage my lower back, I accidentally casually let my hands come up and touch her legs. Betty didn’t object verbally or stiffen, so when she massaged my bare bottom, I let my hands move up until they were right next to her pussy. Her bare breasts and firm nipples crushed my head and upper back. The more she ate and rubbed against me, the more pronounced her nipples became. She stimulates me!

I liked! My cock hardened between the massage table and her stomach as she let me touch her pussy lips with my fingers. Her hands were making symmetrical circular motions over my buttocks, massaging them separately in firm circles. It opened for me every time.

– You have a very muscular ass, Betty’s enticing accent was so stimulating.

Betty spilled some more oil on my bum. I took this as a green light and slipped my fingers between her labia. She sat astride, letting my fingers dance in her wet lips. All the while I did this and letting my fingers slide closer and closer to her vagina, Betty continued the erotic circular massage of my buttocks.

I rocked my ass from side to side over my trapped bulging cock and under her experienced hands. The nerves all over my bottom were so sensitized. She had prepared me greedily.

I curled a finger up into Betty’s pussy. It was silky and comfortable, like that of a much younger woman.

– Oh, you’re a bad boy! she said with a hint of humor.

Then I felt it, a trickle of oil pouring down my ass. My finger poked into her vagina as she began to rub my body. Betty rolled her fingertip around my hole, relaxing it. Again and again, circularly, it still doesn’t enter me. God, it was such an exciting feeling. I wanted her in and pushed my rosebud on her finger.

Slowly, skillfully, Betty slid a finger up, then down, teasing my sphincter once more while holding the pressure. I tried to push her up, making her finger enter my ass, but she wouldn’t let me. Not yet. It was such a slow and skilled tease, better than I ever imagined. Her finger circled my bud teasing it until I practically begged Betty to insert it.

My hands were frozen between her legs, I could only wait.

Then she pushed it in, twirling her finger.

– Oh, you’re nice and tight, aren’t you?

– Mmm, hell yes, I moaned as Betty slowly fingered my ass. Too slow.

It was crazy good. Perfect. I pushed my knees. I wanted this so bad!

– Are you ready for some more? She asked walking from the head of the table down to the other end where I couldn’t see her. Her oily hand traced my entire path as she walked. Over the back, bottom and back of the leg.

– Have you ever asked someone to massage your prostate?

– It’s not the first time. This slow teasing was killing me erotically. You’re kidding, stick your finger in my ass! Please!

– Great, let me make you lift your hips higher. Betty nudged my heels and I stood up.

I was surprised when she grabbed my cock hard and pulled it down between my legs. I was equally surprised that in my erect state it would stay there. She knew how!

Betty placed a fairly large pillow under my hips so they would be raised.

– Okay, lie back.

I let my hips fall back onto the pillow, arching my back and lifting my bottom slightly while keeping my cock pointing down between my legs.

– Are you comfortable? she asked carefully.

– Yes.

 I was comfortable and horny as hell. Ready for more bottom play. Having my penis pointing backwards was unusual, but not too bad. I didn’t understand why it was necessary until he tickled my brake with a single finger. Using the same excruciating skill used on my anus, that single finger spun a small circle over the cleft in my glans and the frenum made my cock harden completely.

– Oh wow, mmm, my whole body shook.

Betty was without a doubt the most skilled and sexually experienced lady I had ever had the pleasure of being around and at that moment I was about to surrender myself completely to her. Whatever she wanted to do to me, I would let her!


– Let’s try to get some prostate fluid. Have you ever had a prostate ejaculation before?

– Um, no.

I loved prostate stimulation, but I never ejaculated like this. I didn’t even know it was possible. Not at that time.

I didn’t understand why, Betty pushed my legs together.

– Knees apart.

He directed again with that wonderful voice. Very direct as if she possessed me. Yes! I loved it so much that she was in control.

In this unusual position, with knees apart and legs together, penis down, I succumbed to a most unusual and arousing sensual experience. With his knees wide apart, he was strangely comfortable and made my ass a perfect target. Betty dropped what felt like a bottle of massage oil between my thighs as she climbed onto the back of the massage table, straddling my calf muscles and legs. I could feel her bare thighs against my skin. Then she lowered her lovely warm wet pussy over one of my heels.

– And a girl should have fun, right? As she rotated her pelvis, I felt her warm wet pussy lips cupping my heel.

– Yes, I muttered into the hole of the massage table.

I felt the oil poured liberally on the crack of my ass again. God yes, he was going to pleasure himself while he was pleasing me. Why not?

Her finger slid easily into my oily ass, and like before, she entered gently, this time deeper and deeper.

– That’s it, relax, you have a nice ass.

He pushed his finger in deeper until I felt a tingle. Then he moved his finger in what felt like a side to side motion in my ass.

– You have a healthy prostate, Betty said skillfully teasing unusual sensations deep inside me.

The weight of her pussy fell on my heel. I could feel her wetness, the shape of her open pussy above me and her hard clit. She used my foot to make her clit hard as she rubbed my ass with her fingers.

– Let’s see if we can get a prostate ejaculation.

She started applying pressure on me inside.

I found it strange at first, then pleasant. Then her finger went back inside me and she repeated.

My body shook.

– Do you feel good there? she asked excitedly, suspecting that she had found a sensitive spot on my gland.

– Yes, it feels good there.

I wanted more of this, how good could it be?

– Wonderful.

 Betty moved her finger up and down, pressing and hitting the same spot.

The nerve endings centered on my prostate electrified. Betty was an expert and gave me my first experience of deep prostate pleasure. I lifted my hips and pushed back against her hand. I wanted more of this!

– Oh, you like it deeper there.

He stuck his finger in and hit a spot I can’t describe.

– MMM, I moaned loudly on the massage table.

I grunted like an animal and arched my back as far as I could.

Betty pulled deeper and moved her finger from side to side on my gland.

Very soon I felt wetness at the tip of my penis. At first I panicked and thought I was peeing.

– Oh, good to see some prostate sperm!

 Betty was equally delighted to stimulate me in this way for the first time. Her pussy was spinning on my heels as I pushed back on her hand.

– Good… good… it feels good yes!

Although I couldn’t see anything, I got a distinct wet spot from my cock and everything from Betty’s ass finger.

– Ugh, I moaned. Whatever came out, she controlled.

Betty rubbed my leg faster and fingered me faster.

Then I felt, this strange feeling. Like an orgasm just starting somewhere different. In my ass! I must have felt the tension in my body because the movement of my fingers became much more intentional. Slow circles over my prostate. I imagined the shape through the movements of her fingers. She quickly snapped her fingertips back and forth, then touched a spot. Her fingertip rubbed slowly at first. Then faster and faster. Faster!


– Oh, yes, faster, just like that! My body shook uncontrollably.

I was panting like an excited dog.

– That’s good, you will reach orgasm, relax.

Betty put her other hand on the small of my back, holding me under the weight of her body. My heel felt wet as she lifted her pussy off me.

Betty’s finger rubbed my prostate like she was working on an electric guitar with a high note! It was a lightning load as he brought me to my first prostate climax. I could feel my cock flowing as my body convulsed face down on the table.

I moaned like a wounded animal. I was her willing prisoner. Moisture pooled under the head of my cock as my orgasm rose, then receded.

He rubbed my head and massaged my back after my breathing returned to normal.

– How was it?

– Amazing!

I turned my head and smiled, already completely satisfied assuming this would be the conclusion of the prostate massage.