Jeff Explores His Fantasies

It has now been nine years and I never thought things would turn out the way it did. At first, I was skeptical because this was a whole new experience that I've never heard of. However, the more knowledge I received about it, the more excited I got. It brought out of me a desire and a passion hidden inside that was begging to come out. It all started with a game of words with friends against an opponent that opened my eyes to a whole new level of sexual experiences that brought me out of my shell. My name is Jeff. I am now 30 and I live alone; which allows me to explore these fantasies without being caught. This is my story.

I love playing word games and words with friends caught my eye. Ever since I was a kid, it has been hard for me to make friends. I thought to myself that this would be a great way to make friends and feel less lonely. At first, it wasn't bad. There was a couple of people that I've been talking to but nothing really came out of it. After about four months of playing, I started losing interest because of how easily I was beating my opponents. The messages started to diminish also and I saw no point in continuing; until I received a message from Jenny, who I was beating by well over a hundred points.

"I am going to punish you for what you are doing to me in this game."

"Do not tempt me with a good time" I replied.

Those words forever changed my life. She proceeded by giving me the link of a website where people explore their fetishes. We became more and more comfortable with each other. For about a month, we talked about several fetishes and she asked if there were any particular ones I was interested in. I didn't respond for nearly two days.

"Hi Jenny. How are you?"

"I am good. I was worried about you"

"Awe. There's no need to worry. I am still your little baby."

"Mommy is gonna take good care of you, sweetheart."

Jenny is twenty years older than me. I've always been interested in older women. At the time of our initial conversation, she was 41 and I was only 21.

"Did you find anything that peeked your interest?" she asked after a few minutes of silence.

"Yes I did. I get excited every time I see those guys submitting to their mistresses."

This is when she dropped the bombshell that changed my life.

"Well, I am a dominant and I want you to be my submissive."

As I previously mentioned, I was skeptical so I was hesitant at first. I told her about it and I was relieved when she said she understood.

"We will ease into it."

"Ok. Thank you."

"I want you to create a profile on the website and under relationship, add me as your Mistress."

Once I made the profile, I followed her instructions and I was now her submissive. Her first message on the website was quite shocking. One message I didn't expect.

"This is your first punishment for beating me in the game: Go to Victoria secret and buy a pair of thongs. Go to the dressing room, put them on, take pictures and send them to me as proof."

"Ok I'm a bit scared. But I'll send the pictures once I take them."

"From now on, every sentence must include the word 'Mistress', you worthless little slut."

"Yes, Mistress."

"Good boy. Now go!"

20 minutes later, I got to Victoria Secret and I went to the sales associate in order for her to help me. I told her about what I had to do and she smirked. I took a quick look at her name tag, which read Mia. I must say, Mia is very beautiful. She had piercing light blue eyes with matching eye shadows. Standing at 5'7, her long black hair was curly and landed on her lower back. I was so mesmerized by her beauty that I didn't notice the slight raspiness in her voice.

"Wow. You're really beautiful."

"Thank you 😊. Follow me. I have just what you need."

She grabbed my hand and pulled me over to the thongs section. After looking for ten minutes or so, we agreed on a pair of pink laced and a pair of lacy black thongs. She headed to the dressing room with me, walked in and locked the door behind her.

"What are you doing?" I asked with a bit of shock.

"Thinking about you wearing those panties got me excited."

I turned around, my back to her. Slightly shy, I took off my shorts and my underwear. I put the black one on first and she took the pictures with my phone. Then came the pink one. As I was looking at myself in the mirror, I noticed that she was only in her underwear. Her breasts were round and firm. I felt the bulge growing in the panties.

In one quick and swift motion, she turned me around to face her, grabbed my shoulder and had me on my knees. I started to freak out when she took off her panties and I was staring at a 12-inch cock. As I opened my mouth to protest, she grabbed my head and shoved her cock in and started face fucking me.

"It is not even fully erect, bitch. Open your throat and take all of it."

A wave of emotions engulfed my body: shock, confusion, and surprisingly a bit of excitement. I've always wondered what it would be like to be with a transgender but never pursued it. Without knowing, I started playing with her balls as I voluntarily sucked her nice cock. I felt it slowly growing in my mouth as I went up and down her shaft, using my tongue every time I went back up.

"Oh my God. This feels so good. I'm about to cu..."

Before she could finish her sentence, she started shaking. She then grabbed my head and pushed it down her cock as she started to flood my throat with loads and loads of cum.

"This is the best I've had in a while."

With her cock in my mouth, a mouthful of cum, I was unable to respond. I swallowed as much as I could but there was still a bit in the corner of my mouth. She leaned down and kissed me, licking the cum off my face. She walked out of the dressing room with a big smile on her face, leaving me on the floor speechless.

I got dressed as quickly as I could. I left the black panties on the seat and grabbed the pink ones. I went over to the cashier and I paid for them. As I was walking out, Mia looked extremely happy.

"Thank you for your shopping. Please come again." she said as she winked at me, smiling.

"I will." I replied with a big grin.

As I walked out, I realized that I found out exactly what I was missing in my life. Mia!! I will definitely come back for more. I cannot wait to experience more of this lifestyle.