Playing Pretend

by The Traveling Master

Tags: #dom:male #m/f #pov:bottom
“No way!!!” I exclaimed. “You hypnotized Jenny?”
“I did.”  he said with a smile. 
“And you managed to make her strip naked?”
“I did.”
“NO WAY!” I said with a huge smile. “I don’t believe you!”
“Here...” he said as he took out his phone and showed it to me.
“OH MY GOD!” I said as saw the picture. “That’s definitely Jenny! Wow... She looks so out of it!”
“She was pretty deeply hypnotized after all.” he said as he closed the screen.
“That was pretty bad of you to do you know!” I said. “Making her strip like that...”
“I know... But I just couldn’t help it! She’s so stunning. I just had to have a peak.”
“HA!” I said laughing. “I bet you wanted to do more than just peak! Especially once she was naked!”
“Guilty as charged! But... Since it was her first time being under, I couldn’t push things too much so I resigned myself to take a few nice pictures for later.”

“Geezz... I bet you had major blue balls after seeing such a stunning girl all hypnotized like that! Bet you jacked off to those pics right?”

“Of course I did! But it’s never the same as the real thing!”

I smiled as I thought of all the things he would have liked to have done to Jenny. Which got me curious...

“I bet...” I finally said. “What if you HAD hypnotized her plenty of times... What would you have made her do?”

“What?” he asked surprised. “Why would you want to know that?”

“Just curious...” I said with a smile.

“Nah... I bet you can imagine just fine! Besides... I would have known in the moment, it’s not like I planned to make her do more while she was under.”

That gave me an idea!

“The moment huh?” I said as I looked him dead in the eye. “Well why don’t we recreate that moment and I'll  pretend I’m her!”

“Really? You’d be game to let me hypnotize you?” he said as he lifted his eyebrow.

“No silly!” I said with a laugh. “I would never allow myself to be hypnotized! Especially since I know you would be dying to make me strip! Among other things...”

“Yeah... I guess you are right.” he said with a smile.

“BUT!” I said perking up. “I AM willing to play pretend! So... Let’s say you got me all trancy and under your hypnotic spell. Then what?”

He chuckled.

“Ok... Well you would strip naked of course.”

“Which I won’t do for real, but let’s say I’m already naked.” I said before taking on a very fake damsel in distress tone of voice. “Oh no! How ever did I get so undressed?”

We both laughed, but I could see he was getting in the mood of things.

“She wouldn’t say that... Hypnotized remember? She wouldn't even know she was naked unless I let her notice” he said. “Anyway... Then I would probably... Yeah... I would make her jack me off... You know... So it’s not too invading for her. If that went well... Then I guess... yeah... Things could possibly progress...”

“Ok... So...” I said thinking about it. “Let’s do that!”

“What? You want to jack me off? Sweet...” he said with a smooth smile.

“Of course not you idiot!” I said. “But if you wait a second... We can continue pretending and see what else you make Jenny do!”

I got up and raced towards my bedroom. I rummaged through my nightstand drawer and took out what I was looking for. I kept it hidden as I went back to the living room. 

“HERE!” I said as I revealed what I had gotten.

His eyes grew wide with the shock of seeing my private dildo in my hands.

“Woah...” he said as he took it. 

“Just use this! That way we can continue to pretend properly!”

“Right!” he said. “Just a sec...”

He got up from the sofa and turned his back to me. I watched as he seemed to fiddle with his pants for a moment before turning back around.

“Tada!” he exclaimed as he struck a pose.

I almost laughed as I saw how he had jammed the dildo inside his zipper! The effect was good! It ALMOST looked like it was his real cock.

“There you go!” I said pointing. “So where were we?”

“Right...” he said as he took a large breath. “Jenny... You are so deeply hypnotized... So calm... So relaxed... Nothing can reach you while you are this calm... This relaxed... Your mind is free to live out any dream or fantasy it desires...”

“Really?” I said as I tried not to laugh at his ‘hypnotic’ tone. “She would fall for that?”

“Well yes...” he said as he broke character. “She would if I had the chance to put her under a few times a week. Eventually, she would drop in a trance so easily and so deeply that she wouldn’t even realize what had happened. Her mind becoming completely open to my words.”

“Really? Intense...Anyway... Sorry! Please continue!”

“Right...” he said with a smile. “Jenny... You’ve often told me how you think of yourself as a conservative lover... I’ve thought about it and I believe that living out specific fantasies would help you become more comfortable with your lovers... So... As you relax and feel the truth of my words... I want you to act out a fantasy in which you pleasure your lover... No expectations... No worries... Just a chance to learn how to better please your lover...”

“Nice...” I said, truly admiring how he would go about it. “Yes... I would like that...” I added to get back into character.

“Very good Jenny...” he said in his low voice. “Let’s start with something simple... Imagine that you have your lover’s cock in front of you...”

He came up to me and presented the dildo to my face.

“You’ve known how much your lover enjoys being jacked off and you wish to be able to offer that to him. Now is the perfect time to see how you can best do that. Completely safe... Completely erotic... Completely within your mind’s fantasy...”

“Yes...” I found myself saying in character.

“Now let me guide you as you experience this fantasy... Learning from it... Enjoying it... First you must make sure your lover’s cock is properly lubricated... You can either use lotion, lubricant or even your own spit... For this fantasy, simply spit and drool all over your lovers cock as your hand slowly and tenderly spreads it all over his length...”

His words were so calm and inviting. I found myself thinking that if he really did hypnotize Jenny a few times, I could definitely see her falling into his soft guidance. Amazing really...

And admittedly... Slightly erotic...

I moved to the edge of the sofa and worked up a large globe of spit before letting it drool all over the dildo sticking out of his pants.

“Like this?” I asked seductively.

“Yeah...” he said. “Didn’t think you’d continue...” he commented softly.

“Of course... I want to see where you would lead her...” I said with a wink.

“Very good then...” he said before resuming his soft tone. “You are doing well Jenny... Now delicately use you hand to grasp the base... Stroke it slowly and make sure to spread the spit all over the shaft...”

I did exactly as he instructed and used very light pressure to stroke and spread the globe of drool I had spit on there. As I did, I noticed I couldn’t fully cover my dildo’s impressive girth so I spit again.

“Very good Jenny... You are a natural... Always make sure to add spit when ever you feel like your lover’s cock is getting too dry... Try to picture how he feels as your hand gently strokes him... Giving him immense pleasure...”

I was no stranger to giving hand jobs so I started to use my own experience to further the fantasy. I started to use my 2 hands in a myriad of ways and strokes to try and maximize the fake pleasure I was giving my dildo.

After all... Better to stick to the fantasy if I wanted to know what he planned for Jenny!

“Looks like you’ve done that before...” he commented.

I smiled as I continued to stroke.

“I take it that I’m close to what you would coach Jenny to do?” I said as I looked up at him seductively.

“Oh yeah...” he said, mimicking the pleasure he would feel. “Most definitely...”

I first thought he was pushing it by moaning softly, but it kind of went well with the fantasy so I let it slide. I even tried to adapt my strokes to his moans as to fully immerse myself in the role playing.

“So...” I said stroking him fast. “This is it? You would make her jack you off naked? Nothing more?”

“Ohh... No...” he said in a very convincing aroused tone. “I would also take pictures...”

He fished around in his pockets and pulled out his phone.

“I see... Kind of like the pictures you took before huh?”

“Exactly... But way hotter! Do you mind? If we are going to act it out as I would play it, then we really shouldn’t stop now right?”

“Right!” I said. “Besides... It’s not like I’m Jenny. All naked and stroking your cock.”

“Exactly!” he said as he took the first picture. “But... To get in the role, you should really try to fake a trance too... Eyes all vacant and all...”

“That’s right! Jenny WOULD be zoned out as she strokes you!”

I did my best to imitate the hypnotized people I had seen in the movies and had to admit that Jenny looked a lot like them in the pictures he showed me. I let my eyes lose focus as I pictured myself trying to see something off in the distance while I continued to spit and jack along the dildo in front of me.

I heard the tell tale clicks of his phone as he took pictures of me. I briefly thought I would look pretty hot in them, even if I was dressed up.

We didn’t talk for a while as he took his photos. It let my mind wander off as I let my hands continue to work their familiar magic. This whole thing was admittedly hot. I’m not sure why I wanted to know what he would do with a hypnotized Jenny, but I was definitely glad I had.

This whole thing was making me aroused in a deliciously mild way.

I even caught myself replacing Jenny with myself! How would I react if I suddenly found myself jacking him off? All naked and unable to resist his hypnotic command?

Part of me couldn’t deny that it turned me on...

So I stopped picturing my friend Jenny and let the fantasy consume me. How hot would it be to have his REAL cock in my hands? He was handsome enough... Would he make me jack him off until he came all over my naked body? Or would he switch things up?

When he faked moaned a little louder, I got pulled back to the present and looked up at him.

“I guess this would be pretty hot for you... Would you be able to last?” I asked seductively.

He chuckled.

“Well... The beauty of having Jenny all hypnotized and under my control is that I don’t need to last long... I could just cum all over her naked tits and enjoy the ride... Make her do it again later... As many times as I wanted!”

“Hot...” I whispered. “But come on... You would settle for a hand job?” I asked, pushing him to be creative.

“Another... hhmm... Fun fact about having her like this would be that I could cum... Enjoy the release... But have her nurture my cock until I’m hard again!”

“Nice...” I said as I tried to picture it. “And once you’re hard again... What would you do with her then?”

“Not sure... Want to continue to act it out? It will give me time to think about it.”

“Sure...” I said as a spike of pleasure went down my spine.

“Ok then...” he said before lowering his voice. “Very good Jenny... Your lover is almost there... Ready to experience his release... You want it... You want him to feel that intense stab of pleasure as you stroke him closer to it...”

“Yeess...” I breathed in a half hypnotized, half aroused voice.

“Your hands have a mind of their own as you stroke him faster and faster... Pumping more and more pleasure from his cock... Making him... Reach... Bliss...”

I pumped faster and faster as I listened to his words. I could almost feel the dildo swell with need in my hands as the heat from my strokes undoubtedly gave him more and more pleasure. Making him reach his release...

The fantasy was so intense! Even if I was fully clothed and only stroking a rubber cock, I felt like I could easily picture myself naked... Sitting on his sofa... Stroking his real shaft... About to be showered by his cum!

“YES!!” he suddenly exclaimed as he fake jerked his hips.

The sudden move brought me further in my own fantasy and it was almost like I could feel his real cock. It felt so real to me that I could easily imagine how his cum would feel as it shout out of his dick and splashed on my naked tits.

On my face...
On my hands...

Load after load would come pouring out as he felt his release. His fake grunts of pleasure only made the whole thing that much more real for me!

And oh so exciting...

If only it was real!

“That was... Very good Jenny...” he said in a fake exhausted tone. “And now that your lover has experienced... You talents... You must... Clean his cock... You must show him how tenderly... You care for his... Pleasure... A new fantasy to experience... One that will only help you become the lover you wish to be...”

I hadn’t realized that my eyes were closed as I ‘experienced’ his release. I opened my eyes and saw how pleased he looked. No doubt, he was actively picturing Jenny do all these things to him for real.

I wonder if he also pictured me...

I smiled at him.

“Jenny...” he said in his low voice. “In this fantasy... You will find yourself drawn to his shaft... A deep desire to clean it will inhabit your thoughts... No other thought will plague you as you take him in your mouth... Not the taste... Not the act... Only the tenderness in which you want to clean and stimulate him... You will find a deep pleasure at being able to do this for your lover...”

I smiled and licked my lips. In a way, it was a shame he wasn’t offering up his real cock to me. Not to brag, but I consider myself to be a pretty good cocksucker and if I WERE to really try and get him hard again, I’d know exactly how to accomplish that.

I’d be tender. I’d be slow. I’d lick and kiss every inch of his half erect cock as I slowly covered it with my spit before suckling the sensitive tip. Which I did to the dildo in front of me.

God it would be so hot if it were real...

I felt like it was... I could clearly picture how he would taste. Just a hint of saltiness as the left over cum covered parts of his shaft. The taste of his hot skin as I bobbed my head along his length.

The fantasy was so real I started to yearn to stop pretending.

I wonder... How would he react if I just pushed this dildo out of the way and took out his hard cock... I bet he is so hard right now... Looking down at me as I suck on his fake cock.

It would be so easy for him to imagine his real cock disappear past my lips...

The fantasy was so real for me that I could easily feel how soft his cock would be even if I was sucking a hard rubber dildo. He would be so easy to suck down... Lick... Kiss...

“That’s it Jenny...” he said, half fake moaning. “Just like that... You are doing very good... Feel how good you are... How talented... Feel how rewarding it is to pleasure your lover...”

I listened to his voice and pictured how it would affect me if I was as deeply hypnotized as Jenny would be. How his voice would guide my mind into believing anything he told me. How his voice would take control of my thoughts and actions until I was helplessly doing what ever he wanted.

Part of me was scared of imagining he could have such power over me. But... Another part couldn’t deny that it also made my pussy drip. Both thoughts made my mind giddy with possibilities.

“Feel how much your lover enjoys your ministrations... Feel how much you enjoy giving him oral pleasure... Feel how hard he is getting because of your talents...”

I could feel it so keenly... Picture how his cock would grow inside my mouth. Expand... Stretch... Harden... The fantasy of it was so real to me... I felt my own juices respond as his growing fantasy arousal triggered my own as I pictured myself sucking on him. Making him ready to fuck me...

God it would be pretty hot if he used his skills to fuck me...

“More and more... You feel how hard your lover is getting... A true testament to your skills... Your talents... Your ability to arouse him... To pleasure him...”

Of course I could... He was getting so hard... I... I could feel him in my mouth... Or I thought I could... 

“You love to feel him in your mouth... You enjoy it so much... It feels so good to please your lover in this way... Especially since you are discovering how good he tastes...”

Yes... God yes... He would taste so fucking good...

“His cock is the best thing you have ever tasted... Because it reminds you of how much you enjoy pleasing him... The feel of him... So hard for you... It makes you incredibly happy...”

Fuck yes... It... it did... God... His voice was so soothing... So right...

“You love to orally pleasure your lover... You always love to pleasure him... Always...”

Always... Yes... 

“You love to indulge his desires... It makes you so happy to feel his lust for you...”

Oh yes... So happy...

“You love obeying his desires...”

God yes... I love it... Fuck I’m so horny right now...

“You’ll do anything he desires...”

Yes... GOD yes...

“It’s time... Your lover is ready... Lean back on the sofa... Let him enjoy your body... Lift your legs in the air for him...”

FUCK yes!!! I sucked one last time on the divine cock in front of me and pushed myself until I was on my back. My legs spread wide and up as he grabbed both my thighs. Without a word he pushed my legs up and over me until my crotch was ready for him. He aimed the dildo perfectly and I threw my head back as I pictured him ramming his cock deep inside me.

A sharp spike of pleasure and heat erupted from my loins at the thought of him actually jamming his cock deep inside me. It would feel so intense... So fucking good...

Feeling his cock ramming again and again inside me. God... It would feel just like this... So intense that my mind would dissolve into a puddle of pure pleasure.

The reality of us fully clothed in my living room and the fantasy of our pretend play meshed together until I didn’t know what was real. The pleasure I felt now and the the one I imagined myself having under his control became one and the same.

I was dreaming of being fucked by him on my sofa just as much as he was bumping the dildo against my shorts...

Or was he?

I didn’t care! Real or imagined, the feel of a cock relentlessly pushing itself in and out of me was sending me towards one of the most powerful orgasms of my life!

Like a machine... He didn’t stop... The heat of his relentless assault was too much for me. I came...

So fucking hard...

The bliss of it all took me to a place where fantasy and reality didn’t matter. I had experienced pleasure and that was all that mattered to me. I lost track of my body as my mind tried to make sense of how I could cum so hard.

But as my senses slowly returned to me, I felt the unmistakable stretch of a cock slowly grinding itself deep in my pussy. The cold leather of my sofa had turned hot and sticky as my bare back moved with each thrust.

Wait... When... When did I get naked?

I opened my eyes and looked between my legs, completely confused about what I was seeing. I had to blink a few times as I saw that he not only DIDN’T have my dildo, but he also didn’t have any clothes on!

“Wh... What...” was all I managed to say before he smiled and decided to kick his thrusts into high gear.

My eyes rolled in the back of my head as the sudden renewal of pleasure burned away all the confusing thoughts I was having. Who cares about when or how we both got naked?

The shear amount of pleasure of overwhelming. It was like I hadn’t cum at all! His cock seemed impossible as it kept pumping more and more pleasure into me. My mind shut down as instincts took over while he rammed into me.

With his cock...

His REAL cock...

Fuck it felt so good...

I lost track of everything except the pleasure.
His hands...
His cock...
His words...
Our evolving positions...

Everything became a mindless blur as he fucked me without any semblance of mercy towards the moaning mess I had become. Even the fact that, despite the insane quantity of pleasure I was feeling, I didn’t cum.

My conscious thoughts were completely unhinged as I floated in the infinite sea of pleasure. Concepts... Words... Beliefs... Everything got knocked out and replaced as his cock kept pounding into me.

Searching for its pleasure...

Using me to reach it...

And once he did, my own orgasm came crashing through me with a vengeance! I saw stars as the heat suddenly erupted in time with his own intense jab of release. I screamed until my throat became soar with the effort before I lost sight behind the wall of my own inferno.

My body jerked and twisted with an ecstasy I had never known while my veins boiled with the power of my pleasure. The last thought I had before I lost myself to it was that even my fantasies could never be this good.

And that I would do absolutely anything to feel it again.


Even let him hypnotize me.

Show the comments section

Back to top

Register / Log In