Massage Chronicals Prostate Milking

Being a relative newbie at the time, erotic massage thrilled me. I was always on the lookout 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 time that I learned to jack off, I was aware of the wonderful sensations that came with anal stimulation. It was taboo. Not talked about, but it felt really good! Soon the stimulation grew to penetration with a finger while jacking off and more, so when I read about full-on prostate massage, I was intrigued. Could it get even better?

I read through the forum post to learn that this type of massage actually existed and not all but many men enjoyed it.

My semi-photographic memory recalled an advertisement I'd seen not-so-long-ago and right away I started surfing the massage ads.

There was an ad on back-page or craigslist that popped up every few weeks for a massage lady who provided a prostate massage as part of the "therapeutic treatment." My cock thickened when I found it.

That ad promised the ultimate in sensual experiences from a European Lady.

---

My mind immediately contrived a buxom Elvira-type lady except with blond hair, telling me to bend over in a thick easter European accent.

Shyness prevented me from calling her right away. I needed to know more. What would it be like? I surfed a few porn sites for images and videos. These ranged from gentle anal fingering to Femdom cock milking, and strap-on fucking.

If only it could be like that! Just thinking about it made my cock a veiny couple shades of purple.

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

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

I'd lube up and finger my ass while I jacked off. I suppose most guys don't have long enough arms so no matter what I did, I never really got very deep. Still, it was enough to make me cum gallons. I'm a big cummer so most of the time, I painted my chest, neck and sometimes face with streaks of sticky sperm.

I wasn't fully massaging my prostate no matter what I did. The thought of a girl or lady doing it for me, while I was under her control, sounded much more thrilling.

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

Her voice was calming but direct and so experienced but unfortunately, her location was right downtown. 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 transit locations on google maps.

Thanks to the subway location, I was able to plan an alternate way to get to her downtown high-rise.

With a route in mind and sexual energy amped-up, within the week, I made a late afternoon appointment. The appointment I made was late enough in the afternoon to permit me to sneak away from work and would have me arrive home in early enough, to dissuade any spousal suspicions. I could always feign an extended late afternoon work-related meeting.

I recollect my first visit was a late spring or early summer day. Weather was favourable and meant a ten to fifteen-minute quick walk from the subway station.

When I buzzed up to her apartment, and Betty opened the door, I was thrilled. Betty wasn't a blonde Elvira, but she ticked all of the boxes wonderfully. Betty had a round face with a striking jawline. There was little makeup on her eyebrows or lashes. Her light blue eyes sparkled with that milfy experience. She could have been Swedish or German. It didn't matter. This MILFy beauty was probably fifteen years older than me but had it together. I surmised that she could have been a model when she was younger, who had aged ever so gracefully. Her face was mature, but still very pretty. She smiled and so did her blue eyes when she let me in. I could tell she liked me, "You are so attractive." She touched my arm muscle ushering me inside her upper high-rise apartment, commenting on my muscles. "And very firm." Betty padded my ass reminding us both why I was there.

--

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

"You can undress here."

I guess she's going to watch me. I'd always been fit, but this was new. I have had very few women watch me undress before. I took a breath. Something about this was perfect and arousing. Having a clothed Milfy European woman who was going to be fingering my asshole, watching me, checking me out as I undressed in front of her. It was cock-hardening. Instead of tossing everything in the usual clump, I made certain to fold my clothes neatly and place them on the chair.

I was completely naked, standing there. I just stood there silently. I'd half imagined her to ask me to bend over and touch my toes! Instead, Betty handed me a large terry cloth towel and directed me to the apartment shower. I cleaned extra thoroughly spending the appropriate amount of time washing the nether regions before heading back to the massage table, already sporting a flagging 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 and was wearing a black lace corset, with a very sheer beige-coloured wrap when I entered the massage area. It was easy to see the corset stopped below her breasts and above her pussy. I had a nice view of her fine light bush and nipples through the sheer cover. My cock erected like someone twenty years younger. So far this was everything I could have wished for. The perfect experienced pretty woman to massage me and teach me all about prostate massage.

"Let's get you on your tummy." Betty directed me face down.

I positioned my body face down shuffled around until my head stared through the face-hole at the 80's style Berber carpet and awaited her touch. Where would she start? Would she just poke me in the butt and get probing? It took a moment, but she came to the head of the table doing a light grazing massage of my neck muscles and back. With my head peeking through the hole in the table, I raised my eyes catching a look at her bare legs and the fact that the sheer cover she had been wearing was now removed.

When she leaned over to massage the small of my back, I accidentally, casually let my hands drift up and touch her legs. Betty didn't object verbally or stiffen, so when she massaged my bare butt cheeks, I let my hands go up higher until they were right up by her pussy. Her bare breasts and firm nipples grazed my head and upper back. The more she massaged and rubbed against me, the more pronounced her nipples got. She was stimulating herself on me!

I liked that! My cock hardened trapped between the massage table and my stomach when she let me touch her pussy lips with my fingers. Her hands made circular movements symmetrically over my glutes, kind of massaging them apart in firm circles. My ass-crack was being spread open each time.

"You have a well-muscled ass," Betty's alluring accent was so stimulating. Betty spilled some more oil on my butt cheeks. I took that as a green light and slipped my fingers between her labia. She stood astride allowing my fingers to dance in her moist pussy lips. All the time I was doing this, and letting my fingers slip closer and closer to her vagina, Betty continued the erotic circular massage of my butt cheeks.

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

I curved a finger up into Betty's pussy. It was silky and snug, like that of a much younger woman.

"Oh, you are a bad boy!" She said with a hint of humour.

Then I felt it, a trickle of oil being poured down my ass crack. My finger fucked into her vagina tentatively as she began to play my body. Betty rolled the pad of her fingertip around my hole relaxing it. Over and over, round and round, not yet entering me. God, it was such an arousing sensation. I wanted her inside and pushed my rosebud against her finger.

Slowly skillfully Betty slid a finger up then down my ass-crack teasing my sphincter once more holding the pressure. I tried to push up against her making her finger enter my ass, but she didn't let me. Not yet. It was such a slow and skilful tease better than I'd ever imagined. Her finger circled my bud teasing it until I was practically begging Betty to fuck it in.

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

Then she pushed it in, rotating her finger. "Oh, you are nice and tight, aren't you?"

"Mmm, fuck yeah" I moaned while Betty slowly finger fucked my ass. Too slow.

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

"Ready for a little more?" She asked moving from the head of the table down to the other end where I could not see her. Her oily hand traced all the way along my body as she walked. Over my back, ass and down the back of my leg.

"Have you had someone give you a prostate massage before?"

"No, this is my first time." This slow build was killing me erotically. Are you kidding, finger fuck my ass already! Please!

"Wonderful, let me get you to lift your hips higher." Betty pushed my heels apart and I lifted.

I was surprised when she grasped my hard cock and pulled it down south between my legs. I was equally surprised that in my erect state, that it would stay there. She means business!

Betty placed a fairly large pillow under my hips so that they would be raised "Okay lay back down."

I let my hips fall back onto the pillow causing my back to be arched and lifting my ass slightly up while keeping my cock pointed down between my legs. "Are you comfortable?" She asked caringly.

"Yes." I was comfortable and horny as hell. Ready for more butt play. Having my cock pointed backwards was unusual but not too bad. I didn't understand why that was necessary until with a single finger she tickled my frenulum. Utilizing the same tormenting skill used on my asshole that single finger swirled a small circle over the cleft in my glans, and frenulum causing my penis to solidify completely.

"Oh wow, mmm." my whole body shivered. Betty was unquestionably the most sexually skilled and experienced lady I'd ever had the pleasure of and at that moment I was about to surrender to her completely. Whatever she wanted to do to me, with me, I'd let her!

----

"Let's try to get a little bit of prostate fluid. Have you ever had a prostate cum before?"

"Um no." I had enjoyed prostate stimulation but had never cum that way. I didn't even know that was possible. Not at that time.

I didn't understand why, Betty then pushed my feet together, kind of burying my cock from view. "Knees apart." She directed in that lovely voice again. Very direct like she was bossing me around. Yes! I loved it so much, she was in control.

In this unusual position with my knees apart and feet together my cock down south, I was succumbing to a most unusual and arousing sensual experience. With my knees widely apart, it was oddly comfortable and made my ass a perfect target. Betty dropped what felt like a bottle of massage oil between my thighs when she climbed up on the back of the massage table, straddling my calf muscles and lower legs. I could feel her bare thighs against my skin. Then she lowered her lovely warm moist pussy over one of my heels.

"A girl should have fun too, yes?" When she rotated her pelvis, I could feel her warm moist pussy lips humping my heel.

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

I felt the oil spilt liberally on my ass crack again. God yes, she was going to pleasure herself while pleasuring me. Why not?

Her finger slid into my oily asshole easily, and as before she gently fucked, this time deeper and deeper.

"That's it, relax, you have a beautiful ass." She plunged her finger deeper until I felt a tingle. Then moved her finger in what felt like a side-to-side movement in my asshole.

"You have a healthy prostate, "Betty said skillfully teasing unusual sensations from deep inside.

The weight of her pussy fell on my heel. I could feel her wetness, the shape of her open pussy over me and her hard clit. She used my foot to make her clit hard while fingering my ass.

"Let's see if we can get prostate cum." She started applying pressure to me inside.

It felt strange at first, then nice. Then her finger would flip around inside me, and she'd repeat.

My body shook.

"Feeling nice there?" She asked enthusiastically, guessing she found a sensitive target spot on my gland.

"Yeah, that feels nice there." I wanted more of this, how good could it get?

"Wonderful." Betty moved her finger up and down, pressing and flicking at that same spot.

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

"Oh, you like it deeper there." She sunk her finger to the knuckle and hit a spot that I cannot describe.

"MMM," I moaned loudly into the massage table. I grunted like an animal and arched my back as much as I could.

Betty fucked deeper and moved her finger from side to side across my gland.

Very soon I felt wetness by the tip of my cock. At first, I panicked and thought I was dribbling pee.

"Oh, good I see some prostate cum!" Betty was equally excited to have stimulated me for the first time this way. Her cunt was gyrating on my heel while I pushed back against her hand.

"Good... good... it feels nice yes!"

Although, I could not see anything I was getting a distinct wet spot by my cock, and all from Betty's ass fingering.

"Ugh" I groaned unintelligibly. Whatever was coming out, she was in control of it.

Betty humped my foot faster and fingered me faster.

Then I felt it, this strange feeling. Like an orgasm only beginning somewhere different. Inside my ass! She must have sensed my body tension because the finger movement became much more purposeful. Slow circles over my prostate. I imagined its shape by her finger movements. She snapped her fingertip side to side quickly then touched a spot. The tip of her finger rubbed slowly at first. Then faster and faster. Faster!

-----

"Oh yeah, faster, just like THAT! My body shook uncontrollably. I panted like an excited dog.

"That's it good, you are going to orgasm, just relax."

"I'll make it cum, you will see." Betty placed her other hand on the small of my back pinning me under her body weight. My heel felt wet when she lifted her pussy off of me.

Betty's finger strummed my prostate like she was working an electric guitar on a high note! There was a lightning charge as she brought me to my first prostate climax. I could feel my cock oozing as my body convulsed face down on the table.

"Nnnnmmmm." I groaned like a wounded animal. I was her willing pleasure prisoner. Dampness gathered beneath the head of my cock as the orgasm crested then waned.

She rubbed my head and massaged my back after my breathing normalized. "How was that?"

"Amazing!" I turned my head and smiled, already completely satisfied assuming this had been the conclusion of the prostate massage.

------

"Wonderful, let's have you turn over on your back." It was then I noticed Betty's bare breasts held up by the corset, and light brown pussy hair. I'd never wanted to fuck a mature lady, but I would have loved to fuck Betty at that moment. She was the sexiest middle-aged lady I had ever met.

I also saw the silver dollar-sized wet spot on the center of the table between where my cock had been pointing. My cock curled like a thick angry snake on my stomach when I rolled over. Sadly, I was not fully erect anymore. There must be a refractory period when you have a prostate climax too?

"When you cum from the prostate, it's sometimes like a woman, for a man." Betty recited into my puzzled face. "Sometimes you can climax one or two more times." She rolled my loose balls in her palm then gently massaged my cock.

"Two times?" I wasn't a teenager. Supported by the corset, I stared at her lovely breasts.

"Would you like to have another prostate orgasm?" She smiled at me. Her smile gave me a sense that this was not something she offered to every man.

"Um sure, yes." I did not see how this was possible. My eyes zeroed in on her pussy.

"You like this!" Betty directed my upward-facing palm to her moist pussy lips. "You will like it you'll see." With her hand against mine, she guided two fingers into her warm pussy.

"Nice?" Betty asked for my approval.

I nodded.

"Mmm-hmm." Her clitoris was firm like a hot grape in the palm of my hand while Betty fucked my fingers for a couple of minutes.

After placing a couple of pillows under my head, Betty headed back to the foot of the massage table again.

This time she spread my legs wide and climbed up on the foot of the table. "Lift your legs, please." I raised my legs up and Betty spread and slipped hers underneath. "Lift- lift- lift."

Each time I raised my hips and legs Betty shuffled forward until her thighs were supporting my hamstrings. I understood. My ass was now elevated again, giving her easier access.

"Ready?"

"I think so." I was still tentative not believing it possible to cum again. I didn't know everything about prostate orgasms. My teenage years were long past. That and my cock was not hard anymore either.

"Just relax, breath deep, I will take care of it." Betty used both of her hands to gently massage my cock and balls, to illicit an erection or response.

To be honest, my mind didn't seem to be into it, nor my cock. Though, I did not want to disappoint her.

-------

"Relax, just relax, just breathe" Betty leaned forward and massaged my chest and nipples. That was nice, relaxing and sensual. There didn't seem to be any rush, Betty was taking her time, circling my pectoral muscles then touching my nipples. Outward circles then inwards. With each circle, my nipples wanted more. I pushed my chest up. Betty pinched them making my groin tingle.

She smiled at me. I smiled back, taking in her breasts and her pretty milfy body. She was sexy. I felt another tingle when she tweaked a nipple. Betty was intimately aware of the reaction and leaned forward touching her mouth to my chest. She sucked and bit my nipple hard then switched to the other side. I flinched and so did my penis, throbbing awake.

"You like it here?" Betty grasped my somewhat thickened cock and pointed it down to her pussy. She used my cock head to rub her clit and pussy lips.

"God" The submissive aspect of this aroused me. She was using my cock as a personal masturbation toy. Rubbing it between her labia and making it harden her clit.

She was in control and also using my body and this time my cock head to pleasure herself!

"So nice!" I smiled. Pulling my cock south again, she rubbed it firmly up and down her wet slit. Humping and grinding at the same time. By the time she stopped, I don't know who was more stimulated, me or her.