The Successful Woman Pt. 01

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Double Penetration

She is successful, smart, fit and glamorous. Everything most men would want in a woman. Little did he know he was in for a life of humiliation and financial sacrifice.

*Beep Beep* Johnny’s email notification alerted him. I reached over to check the phone. One new message it said, appears to be from an online ad. How exciting i thought I would try my luck, however i didn’t expect much in the way of real women replying.

Her email introduced herself as Sharon. Said the ad was what most girls wanted, and couldn’t pass up replying. Couldn’t believe I had an actual response seeking worship. I calmly replied asking about her weekend, and whether it was enjoyable. She responded quite promptly, to my surprise. This time more direct and seeing no reason for small talk. Still a little shocked it wasn’t a spam reply with grammar and spelling errors. I wasted no time, and got right back to thinking what I should say.

A few moments passed, and i decided to tell her I love the idea to serve a woman.

She replied that is great, but what man wouldn’t?

Then asked me what could I offer that would be any different another other man, that she should give me a shot.

My mind raced. What could i offer? I wasn’t successful in my work field yet, having just moved to a new city. And was slim but not toned in the body. And it seemed to obvious to just offer a mouth. I could tell Sharon was hinting at something more. My mind raced. And thought well there was that *one thing.* But surely she wouldn’t know what that was. And maybe I would even frighten her at mentioning it. Then i thought what the hell, it is just a bit of online chat that mostly likely wouldn’t lead anywhere, anyway.

I had recently discovered some kinky porn browsing the web. Some sexy empowered women taking charge in the videos. Was interesting from the standard run of the mill stuff. Some had restraints, some floggers, and other gear. One particular video though had a male on his knees licking away with his cock locked in a chastity cage. The woman was moaning deeply with enjoyment. It was unique. Hard one not to forget.

I gulped and sent in my reply. Some time passed. And thought to myself that definitely would have scared her off. So went to have a shower. Upon returning to my room I noticed a notification on my phone. Surely it wasn’t Sharon.

Much to my surprise i opened her message to read simply as “Now you’re talking.” My heart raced. How could it be true? How did she know what I was talking about?

I politely replied asking how çukurambar escort she knew. She said “fantasies.” I had to know more.

Sharon explained “Men had it easier than women. More money, better job status, more opportunity because they simply where male.”

Her response seemed reasonable. I was never the arrogant alpha male type who felt entitled to the world. And I was still in shock the conversation had lasted this long. I thought I should ask her what else I could offer.

She replied “money for the privilege.”

Quite shocked and confused, I didn’t really grasp that paying was something that got people off.

Not sure what to think. Was it wrong to pay? Was it ok? One thing is for sure I didn’t understand Sharon’s interest in the matter. I decided to ask her if she could elaborate.

She promptly replied “You’ll learn.”

Without thinking much of it I decided to try keep the so far good conversation going. And switched subject to asking about her status, or an available picture to get an idea of whom I was chatting with. She said she was around my age, Toned, liked to hit the gym, and blonde. Worked in an office by day for a successful firm. This all sounded appealing to a guy like me. How had I got so lucky to be chatting to such a woman?

After a few days of banter Sharon messaged “How about we meet at yours 6pm Tomorrow?”

I was shocked and excited at the same time. I promptly replied with a “Sure thing.” Trying to play it cool. Surely she wanted me to orally please her. She must have been impressed with the hints I dropped in our banter.

It was a long day at work clock watching, waiting for 5pm to roll around. I had to contain my excitement around my work mates all day. But they could kind of sense it anyway. Staring at me on occasion, catching me grinning while I was at my desk. But it was my little secret that I decided not to tell them. Despite being rather excited that i wanted to boast.

Finally the work day was over. I hurried home and checked that the house was neat and tidy. Then suddenly my phone beeped.

It was Sharon “Be there in 10.” she wrote.

I replied “Number 10, door is unlocked let yourself in.” What was i thinking? What was I doing? Inviting a stranger in like that? Never mind I thought, this was exciting and the closest to any action in some time. I couldn’t spoilt it now!

Next thing I know the door swings open. Sharon entered the room. Black shiny heels. They looked immaculate and expensive. Kind demetevler escort that reminded me of some of the women in the videos I had seen. Her legs where long, fit, yet slender. Covered in nylon stockings. She was wearing a tight black dress, with a cut to display her cleavage. Which she clearly didn’t mind showing off. Her breasts looked firm and and soft peeking out of the top of her dress. Her hair was long and golden blonde, shining in the light. I was mesmerized. Pretty face and blue eyes. How did I get so lucky?

She broke the silence with “I brought you a surprise or two.” Handing me a small green bag.

I opened it to find some handcuffs. “What are these for?” I nervously stuttered.

“Well you said you where up for some fun didn’t you? Or should I go?”

I replied with the only thing I could. I wasn’t going to blow this. “Stay, I am up for some fun.”

She grinned. “Ok put them on, hands behind your back.”

Hastily i fumbled with the cuffs but managed to get them, on hands now restrained behind my back.

“Great” She said, right before her shiny black heel met my chest and knocked me back on the couch. “Want my other surprise too?”

Boy did i ever. Surely she was talking about that amazing body of hers. “Yes Sharon i’d love that.”

She responded with “Good boy, that’s what I like to hear.” As she started undoing my belt on my pants and wasted no time unzipping me. And lowered my pants to my knees. “So you like surprises is that right?”

Shocked and amazed at what was happening I nervously replied with a “Yes.”

“Great! So I want you to close your eyes while I get your surprise ready.”

Without a seconds hesitation I complied.

“I really liked that in our messages that you said you like to please a woman Johnny. And so I felt I should do something special for you.”

I couldn’t believe it, how did i get so lucky! Then i felt my underwear being slid down. I nervously thought about my size. Would it impress her? Did she have a preference? Sharon didn’t say anything as I then felt some cold steel being put around my balls and shaft. My eyes where firmly closed as she requested. I didn’t want to ruin anything. However I was extremely curious about what she was doing.

“All done! You can open your eyes now.” I saw her grinning confidently.

I looked down and saw a small metal device now covering where my cock would usually be visible. I had seen them in the videos so I wasn’t completely unaware. But never had I worn demirtepe escort one. I tried to act cool and not freak out but had to ask the obvious. “What is this?” I stuttered.

“A chastity device silly, You said you liked to please women didn’t you?”

She then stood up and turned to walk away. Stopping after a few steps, before I notice a pair of lace panties sliding down her legs. Her shiny black heels stepped out of them as she walked closer to the door.

“Key is in the cuff you are wearing. Thanks for today you’ve made me very happy Johnny. I’ll message you soon.”

And with that she was gone out the door. I was left on the couch pants around my knees with my penis now in a steel cage as I struggled to unlock the cuff.

“What just happened?” My mind was racing as i removed the cuffs. “Message me? What the hell I thought”. I was both scared and excited. But surely it was just a trick to scare me. I looked out the door. No sight of Sharon. Not knowing what to do I went and sat back down and tried to distract myself with some TV.

Next thing I know my phone beeped.

“Thanks for today Johnny. Really got me going. You where great! How does the cage feel?”

I replied that I wasn’t sure. Sharon said she was so horny on the drive home. That she texted a friend to meet her back at her place.

“I get extremely turned on when I lock a new boy up. I usually cum multiple times. So I messaged a stud I know who has a lot of stamina. He can last long enough for me to cum several times.”

I thought what on earth was happening? I was shocked and aroused and confused all at once.

My phone beeped again.

“He is here. I am already in bed waiting. Now how about you pick up those panties off the floor. And think about how I am getting pleasured and pleased”.

I picked up Sharon’s panties and noticed a wet smear on the inside of them. instantly I felt a strain in my crotch. My penis was attempting to get erect. But the cage was very small and tight and it completely stopped any growth. The scent of her panties was now in my nostrils. Aromatic and sweet. Again my crotch twitched. I wanted to look away but couldn’t. A whole half hour must have passed.

Suddenly my phone beeped. It was Sharon. I nervously opened the message.

“Panties cause a bit of a stir? 😉 I thought so. My stud just fucked me so hard I came 3 times. I feel amazing, aren’t you happy you helped please me?”

Gobsmacked and shocked. I sat there straining wondering what happened. I thought I was at least going to get to lick some pussy tonight. Instead my cock is now in steel, and Sharon went and had sex with another man.

Still shocked and confused, I looked down at Sharon’s message again. I had so many questions but my spinning head couldn’t muster any conscience ideas.

So I simply replied “Yes Miss.”

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