Sissy Exploration Pt. 02

I was so excited pulling up to Mark and Rachel's house the next afternoon. I was wearing a cute navy t-shirt bra, a matching string bikini, a white low-cut t-shirt, short, tight jean shorts, and some cute sneakers. I had made sure I was completely smooth and had painted my nails a hot pink color. Mark opened the door for me. "Welcome back sissy!" he said as he grabbed by ass.

"I am glad you wanted to come back!" Rachel said, emphasizing the double entendre.

We all sat in the living room with Mark and Rachel on the couch and me in a chair facing them. Rachel began, "Since you decided to come back and be our sissy we need to set some rules for you. First, you are submissive to both of us. Second is clothing. You will wear panties 24/7. When you are home, or here obviously, you are to dress as a woman; bra, panties, women's clothing etc. At night you may wear lingerie, women's sleepwear, or just a bra and panties. I will demand random photos to ensure you are following this rule. Third, you will be caged 24/7. Fourth, you will begin anal training with butt plugs until you can take Mark balls deep in your boi pussy. Fifth, you will practice applying your makeup and strive to be as passible as possible. There are a few other rules that will come up but we will discuss them later. Any questions?"

"No, it is all clear to me." I answered.

"Good," said Mark, "let's head to the bedroom to get you caged and plugged then I can fuck you both. I have been horny all day."

Rachel led the way and when we got to the bedroom Mark lounged on the bed with his hand in his shorts and Rachel ordered me to take off everything but my bra and panties. Rachel sat down in an armchair in the corner of the room and picked up a plastic pink chastity cage sitting on a table next to the chair. "Come over here, pull your panties down then put your hands on your head sissy." I did as I was told and she proceed to lock my clit in the fairly small cage. It took a little bit of work as I was starting to get hard watching Mark slowly rubbing his cock while he reclined in the bed. The cage fit snugly on my clit and did not give me any room to grow. Once the cage was locked and the key was around Rachel's neck and nestled between her breasts she told me to turn around and bend over. Rachel lubed up the butt plug which had a pink jewel at the end and started to slowly but firmly push it into me. It felt slightly cold going in but I liked the feeling so I pushed back into it as she continued to push it into me. Once it was all the way in I felt so full and the weight of it was a constant reminder it was there. "That is the smallest plug we have, once you progress through the medium one to the large one you will be ready to take Mark in your boi pussy. Pull your panties up and lay on the bed so I can ride your face. I hope you are as good at licking pussy as you are at sucking cock, as I need you to get me ready for Mark." Rachel said.

I laid down and Rachel immediately straddled my face and I started licking her pussy. Once she was wet, she had shifted position so I could lick her clit and Mark could take her doggy style. I watched mesmerized as Mark's hard cock impaled her pussy again and again. Then, he pulled out and immediately put his cock in front of my mouth.

"We are going to play a game," Mark said. "You and Rachel take turns with 15 thrusts each. The winner gets my cum!" Excited to play the game, I eagerly opened my mouth Mark thrust his cock down my throat 15 times then pounded Rachel's pussy 15 times, then went back to my throat. Mark's cock tasted so wonderful with a little bit of precum leaking out mixed with Rachel's pussy juices. I moaned with pleasure each time he thrust deep into my throat. After a few turns my mascara was running from gagging on his cock but I knew he was close as his cock twitched each time it entered my mouth. However, on the 5th thrust into Rachel's pussy I heard him grunt then I saw his cock spasm. Rachel had won.

"Consolation prize sissy, you can suck my cock clean," Mark said.

After I gently licked Mark's cock clean of cum and Rachel's juices and swallowed everything like a good sissy Rachel said "I still did not cum and I want you to clean me up as well. Get licking sissy." So, I started licking her dripping wet pussy, making sure my tongue got as deep inside of her as I could to clean her up. Soon, Rachel let out a moan and I could feel her pussy spam. Mark's cum mixed with her juices flowed out of her and into my mouth. I hungrily swallowed it all. "Good job sissy," Rachel said.

We all headed to the living room where we ordered out for dinner and watched a movie. When the food came to the door I was told to get it. Embarrassed yet very excited, I walked to the door in nothing but my bra and panties. I opened the door and the delivery guy's mouth opened and shut. He looked me over from head to toe once or twice before stammering, "Here is your order.

"Thank you," I said as I took the food from him. As I turned to put the food down I realized there was no table in the entryway so I had to place the bag on the floor. Since I was going to have to bend over anyway I decided to give the poor guy a show. I bent over in my best stripped imitation, feeling his eyes on my ass the whole time. I turned back to him, paid for the food, and give him a generous tip.

As he turned to go, he turned back to me and said in a rush, "I am sorry if I stared earlier, I was not expecting that when I opened the door and I just think you are so hot I could not take my eyes off of you!"

"Thank you so much!" I said graciously then he turned and walked back to his car.

Mark and Rachel had been watching the whole thing from the doorbell camera so they saw and heard the whole thing.

"Very nice Samantha!" said Rachel.

"Impressive show Sam! I bet he is going to be thinking about you when he jerks off tonight." said Mark.

I blushed furiously as I sat down on the floor in front of the couch to eat and watch the movie. Occasionally throughout the movie Rachel would order me to suck Mark's cock and Mark would order me to lick Rachel's pussy on and off during the movie to keep them horny. At the end of the movie Rachel said "Mark and I are going to head to bed, you can sleep here on the couch." With that they left and I curled up on the couch in my bra and panties; the butt plug and cage a constant reminder of my new status here. As I fell asleep I could hear Mark fucking Rachel loudly in their bedroom and I wished I was there too.

Rachel woke me up the next morning after I had spent the night on her and Mark's couch. She was dressed in a sports bra and running shorts and was clearly ready for a morning run. "Samantha, I want to get a run in before it gets too hot but Mark is still asleep. Mark usually wakes up with terrible morning wood," she continued "and I am afraid I will be out on my run when he wakes up and won't be able to take care of it. Go into our room and curl up next to Mark. If he wakes up you will know what to do I am sure!" With that she left.

I made my way to Mark and Rachel's room wearing nothing but my bra and panties from the night before. I crawled into the bed next to Mark and he soon rolled over and spooned me, pushing his cock against my ass and his hand holding my chest through my bra. Soon, his cock started to get aroused and i could feel it pushing against me between my cheeks. So, I started teasing him by wiggling my ass a bit and clenching my cheeks on his rapidly growing member. He began thrusting and fondling my chest and i knew it was time to get to work. I started by kissing his now rigid cock and licking the head but every time I touched his cock with my mouth he was trying to thrust inside of me so I quickly took him into my mouth. Mark grabbed a fistful of hair at the back of my head and proceeded to set a very rapid pace. Soon his cock and balls were slick with my drool and tears were running down my face since he was forcing me all the way down on his cock hard.

"Rachel was right," I thought, "Mark does get morning wood bad and wants it taken care of immediately."

With his other hand he would occasionally spank me as I gagged on him. Soon, Mark grunted and forced his cock all the way down my throat. Spurt after spurt of warm cum shot into my throat. After I gently cleaned his cock like Rachel taught me Mark got out of bed and said, "Good job Samantha, I am going to shower now, you can head back to your couch."

I was just drifting off when the door opened and Rachel came in from her run. She was breathing heavily and said "I was thinking of you sucking Mark's hard cock the whole time I was running." She started walking towards me with her breasts bouncing in her bra with each step I suddenly I wished my chest would bounce like that as I walked. When she was by the couch she seductively pulled her shorts down and gave me a view of her cleavage while revealing a tight thong with a noticeable wet spot over her pussy. "I was getting so wet thinking about it that now I need you to take care of it." With that she straddled my face and pulled her thong to one side revealing her dripping wet pussy. I licked her deeply while she rode my face. When she got close, she grabbed my hair and started grinding her pussy into my face and soon her body spasmed in orgasm as she came on my face. After she composed herself and rose up from my face she said, "Thanks Samantha, you are really helpful around the house in the morning!"