It all started out as a normal Friday night, after a long week at work I was relaxing at home with a rum and coke, me, in my red lacy underwear browsing the internet dating sites hoping someone could fall in love with a sissy like me, yet again. Weeks of failed attempts had led me to believe I was a complete and utter loser until a girl called Samara jumped into my inbox with a casual “Hey, looking for some company?” Instantly my cock was interested, her profile looked hot, with many images of her in latex and thigh-high boots, I thought it was too good to be true, but she sent a quick video of herself, and I was in shock at my luck!
Curious to figure her out I asked a few questions about her images, whether she was into being a top when it came to the bedroom, based solely on her clothing of course, there was no point in beating around the bush, I thought to myself after one too many rums, those thigh high boots had certainly piqued my interest! Samara laughed at me and spoke,
“Why of course, isn’t it obvious? I like to make men my bitches, tell me Ben do you like to submit to powerful women like me?”
This could not seriously be happening I thought to myself, I had to re-read in case my alcohol-filled eyes were failing me. Deciding to go all in I laid my cards on the table, what did I have to lose?
“Well, since you asked so directly yes, yes I do like to submit” I replied excitedly at where this could lead. “I am a sissy boy” I blurted out. “I enjoy humiliation play, and well, I hope this isn’t too much information, but I enjoy anal play, strap-ons on a woman are so fucking hot” I hit send nervously eagerly awaiting her reply, my clitty dripping with its new-found luck!
After what felt like an eternity, I could see her starting to type, my slurry eyes eager to read her words.
“Benny boy, I would love nothing more than to fuck the shit out of you, in every single way possible” she purred. “Shall we arrange a date?” she asked. “I would have to book a room though, as my flatmates are always home. If you send some money through, I could book us a room for tomorrow night at the Beachside Hotel, how does that sound?” she said casually as if she was talking to me like I had known her for years.
Money, I knew this was too good to be true! But maybe it was just the hotel she wanted me to book, I should take a chance on it, I thought to myself, I mean really who has ever paid me attention like this before, let alone a hot dominant woman!
“Sure, let’s do it, how much do you need for a room” I said, with slight caution.
“$400 should cover it, I’ll get an early check-in so I can set a few things up and prepare the room special for you, shall I? I have so much kink gear to bring along with me” she said.
She seemed to know what she was doing by the sounds of it. “Ok, sure, where shall I send the money to?” I said, now feeling more at ease.
“Flick it to Samara666 on the Cashsender app” she stated.
Instantly I obeyed of course, and within 4 minutes of sending the $400 for the room a new message came through.
“All booked for noon but come at 3 pm so I have time to make it all perfect. Room 43 level 5, I CAN’T WAIT TO DRESS YOU UP” She pronounced this with great enthusiasm.
Again, my clitty moved at the thought of tomorrow night and at what was to be my fate under the feet of such a gorgeous woman!
“Sissy?” another message came through. “You won’t believe it, my best friend Ashley just messaged and said she wants to come up from the coast tomorrow, we could have such a good time together, the three of us, but she said she would need $500 to cover her trip. Could you imagine us spit-roasting you? It would take the whole experience to new heights” she said, with what sounded like genuine excitement. “So, if you want to go ahead and have an extra dominant to spice things up, flick the money through to the same account”.
My clitty dripped at the thought of a cock in my mouth and a big fat dick pounding me from behind, “fuck it” I said out loud I may as well go all in, I let my horniness lead me back to her Cashsender account where I flicked through the money without thinking.
“I have sent the funds, I can’t wait to meet you both, I look forward to playing tomorrow” I replied.
“See your sissy ass soon, we can’t wait either” she purred.
I signed off wanting to cum in my red lacy panties, but decided I would wait and let the anticipation build and slide into bed, hoping to get to sleep so the next day would arrive faster. I felt like a kid at Christmas waiting for Santa!
I woke up early and scrolled through the dating app again so I could look at Samara’s account again and goon for a while over her before we met later, then it hit me! I saw her face but linked to another profile stating, “SCAMMER ALERT AVOID TOOK MY MONEY AND LIED ABOUT A HOT FRIEND COMING INTO TOWN”. My heart sank and I sat up feeling sick to my stomach at the thought of having sent $900 to her already, I pondered wondering what to do when my phone pinged.
“Yay, today is the day we all get to play. We look forward to seeing you this afternoon, sissy xx” it read.
Thank fuck, I thought as an instant flood of relief ran through me that I hadn’t been duped out of my money, the other account must be some guy who is being petty, I thought boldly and full of triumph that I was going to see her and her friend, Ashley, later today.
TO BE CONTINUED……. WHAT WILL HAPPEN TO BENNY BOY? THE LIFE OF A SISSY!
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This is the picture she sent me of her and Ashley. SO HOT!!!
