Jeff Explores His Fantasies Pt. 02

At the time, I was living with two of my cousins, who are brother and sister. Once I got back to the house, it was empty. I quickly went to my room and locked the door. I took the clothespins and the markers out of the bag. My Mistress had ordered me to buy them on the way home.

"Mistress, I am home now."

"Awesome. Take the clothespins and attach them to your nipples and balls. Then across your chest and stomach, I want you to write the following: Mistress Jenny's Property. Take the pictures and put them on your profile."

"Yes Mistress."

I promptly did the tasks with the clothespins because they were painful as I somehow have sensitive nipples. The pictures were posted on my profile and received a lot of comments. One of the comments was from Mistress Jenny's husband. I had no idea she was married. However, he was okay with it as he also enjoyed this lifestyle. His name is Mark and he was 35 at the time. He was bald like I was. He was very muscular and was 6'1. I also found out he was bisexual; which explains his comment: 'Looking very sexy in those panties'.

"Mistress, who is Mark?"

"You do not ask questions unless you ask permission first. Understood?"

"Yes Mistress. I'm sorry Mistress."

"Since you've already asked, he is my husband and we are going to have a lot of fun with you."

Wondering what she meant, I had several scenarios playing through my mind.

"Thank you Mistress. Mistress, may I ask a question?"

"Yes you may."

"When will we meet, Mistress?"

"In due time. If you behave like a good little slut."

"Yes Mistress. I will."

The following week, I was quite busy with work. I hardly went to the website and only talked to my Mistress once or twice. As I predicted, a punishment was due. She took things a little bit further this time. This punishment had set me up perfectly for my birthday, which was 4 days later, on July 15.

"Go to the supermarket and grab the biggest cucumber you can find. Once you get home, I'll explain in details what needs to be done."

"I am on my way to the supermarket as we speak, Mistress."

"Ok. Hurry up slut."

"Yes Mistress."

I got to the supermarket down the street from the house. As if it was meant to be, the biggest cucumber was right there at the top. A bit curvy, very green and firm. I took it, along with a few other items, and made my way home. Once I got home, she called me on Skype.

"Hello slut. I hope you had a good day."

"It wasn't bad. How was yours Mistress?"

"My day was good but it's about to get better" she replied with a wide smile.

"Mistress, I have the cucumber as you requested."

"Perfect. Now I want you to suck on it slowly."

"As you wish Mistress."

I placed the cucumber in my mouth. Using my left hand, I sucked it; very slowly sliding it in my mouth inch by inch. I didn't even make it to the middle. That's how long the cucumber was.

"I want you to strip for me, slut. Turn around and show me your ass as you do so" she ordered.

In the corner of my eye, I saw her massaging her breasts and masturbating. I kept the cucumber in my mouth as I slowly took my pants off. Unbeknownst to her, I was wearing the pink thongs. I leaned over, exposing my ass to the camera, while maintaining the cucumber in my mouth.

"That is a nice ass." said a male voice

I turned around to look at my computer to realize that Mark was also watching. He was naked and standing next to Mistress. His dick, which seemed to be about 10 and a half inches, was in her mouth. They were getting excited as they watched me.

"Don't stop slut. Keep going!"

"Yes Mistress"

I grabbed the thongs and proceeded to do the same and took them off. Meanwhile, she was swirling her tongue around his dick a little. Then, as she started massaging his balls, she took on his whole dick, deepthroating it. All this excitement was too much for him to bear. He exploded, shooting his load onto her face. Licking the cum off her face, she kissed Mark, sharing his cum with him. She then added that I should insert the cucumber in my ass. I had a feeling she was gonna have me do that. I grabbed the lubricant out of the bag and rubbed it on the cucumber.

Facing away from the computer, I leaned over as I started pushing the cucumber in. Mistress and her husband had a clear view of the penetration. I could hear Mistress moan as she fingered herself while Mark was licking her pussy slowly and eating her out passionately. She was on the verge of cumming. I sped up a bit, plunging the cucumber a bit faster now. I felt my dick growing and I was ready to cum.

I was lost in my own world, as I was listening to my Mistress moan while having the cucumber in my ass; completely oblivious of my surroundings. All of a sudden, the call ended. At first, I wondered why she ended it as we were so close to a mutual climax.

When I opened my eyes, there, in the doorway, was my cousin Raven, staring at me with her arms crossed. I now remembered that I had forgotten to lock the door. Shocked and embarrassed, I didn't know what to do at this point. I just stood there, cum leaking from my dick. What she did next was quite unexpected. Without saying a word, she approached me slowly, fell to her knees and started licking the cum off my dick. She started with the tip, swirling her tongue around it. Then she started deepthroating me. My dick grew in her mouth as I felt ready to cum again. She pulled her shirt up to expose her tits and entice me. That was the last draw. I exploded in her mouth uncontrollably. She swallowed every last drop, sucking me dry.

She then got up, winked at me and started walking out. She stopped at the doorway again and turned to face me.

"We're gonna have so much fun." she said, with a devilish smile.

As soon as she left, I grabbed a towel and rushed to the bathroom. I took a quick shower and went back to my room; making sure the door was locked this time. As I was laying down, I started wondering how my relationship will be with Raven from now on. I will figure it all out tomorrow I thought to myself. Exhausted and drained, I fell asleep.