The Penthouse Ch. 06: John in Charge

Next came a lesson in oral sex. I thought I knew how to eat out a woman. Sharon showed me quickly how much I had to learn. We went through spelling out the alphabet with your tongue, where and when to suck, where and when to lick, and where and when to curl your tongue and tongue fuck. When to include the ass with the cunt and when to concentrate on just the ass.

Sharon finally felt comfortable with my skills, so we laid in bed kissing and caressing until it was time to get ready. We showered together, I bathed her, and she bathed me both with a lot of groping, finger in cunts and asses, and kissing. We finally finished, toweled off and did our make up and put our heels and collars back on.

John and Mistress Umbra came in together. Sharon ran over and fell prostrate at the feet of her Mistress, kissing her boots. John came over and gave me a kiss.

John asked, "How did the training go."

Before I could answer, Mistress Umbra in a rather cold tone said, "That is what we are going to find out in a bit"

Mistress snapped a leash onto Sharon's collar and led her crawling over to one of the chairs. Mistress sat, and Sharon knelt at her feet. John asked if she would like something to drink. "Sparkling water for me, and a water bowl for her." John got the sparkling water out of the refrigerator and poured a glass while I got a suitable bowl and filled it with water and set it by Mistress's chair.

John told me that the dinner would be delivered soon and reminded me that I still owed the delivery man a better apology. Mistress asked what that was, John explained what I had done and how I was making it up to him.

Mistress laughed and said, "Wonderful, Sharon you are to help slut apologize. Like you practiced at the party."

The doorbell rang and Sharon and I crawled over to the door. John opened the door, took the food and told Bill that he considered my apology last time poorly done and was I was being given a chance to do it right. It took Bill a moment to grasp what he was being told but then he undid his belt, and I lowered his pants and shorts again showing that Bill was well equipped. I licked up his shaft and took it into my mouth about halfway, before pulling it out and giving it to Sharon. Bill was a bit surprised at that action, but quickly realized what was being done. Sharon really went to town taking it full depth and cradling his balls with her free hand. I took him back and immediately down my throat, I held him there until I needed air, popped him out and handed him back to Sharon. Sharon finished him off and took the mouthful of cum like a champ. She immediately leaned over and shared it with me, as we tongue kissed the cum back and forth, before swallowing. I licked and sucked Bill's cock clean and helped put it back into his shorts. I again apologized and hoped that my service in some small way made up for my inappropriate actions.

We both crawled back to our respective Masters. John told me to set the table, and serve the dinner to the table, only two place settings and two extra bowls. Once that was done John escorted Mistress Umbra to one of the place settings before seating himself at the other. Sharon crawled over next to her Mistress and knelt up allowing her Mistress to attach her leash to her collar. John motioned for me to do the same by him and attached my leash.

Mistress took portions of each item on the table and placed them in the extra bowl, stirred it all together and placed it on the floor by her feet. John watched and did the same before setting the bowl down by his feet.

John then served Mistress's plate and then his own. Mistress then looked down to Sharon and said, "Eat" Sharon pulled her hair to one side, placed both hands in the small of her back, bent over and started to nibble at the food in her bowl. I took her lead and did the same.

While the two of us were eating from our bowls John and Mistress, enjoyed their food, wine and conversation. The conversation seemed to center around the proper way to train a submissive. John seemed quite interested in Mistresses strict ways.

When Mistress placed her utensils on her plate indicating she was done, she reached down and picked up Sharon's bowl. Sharon was done whether she was satisfied or not. John reached down and did the same with my half empty bowl. Mistress wiped her mouth and hands on her napkin then reached down and cleaned the food off Sharon's face. Again, John followed suit and did the same with his napkin and my face.

Our leashes were picked up and we followed our respective Masters over to the couch. Mistress and John sat together on the couch.

Mistress turned and said to me, "It is time for you to demonstrate what you have learned today, I hope for both of your sakes, you learned well." "First you will show me how you scissor together."

Sharon and I moved to the middle of the room, intertwined our legs and started rubbing our cunts against each other's. It took a short time to get the alignment right, but once we did it felt incredible. I quickly started climbing towards my orgasm and from the looks of Sharon she was close too.

"Very good slut, you may stop." was not what we wanted to hear form Mistress but we immediately complied. Both of our cunts were soaked.

Mistress next directed Sharon to lie on her back between Mistress's feet with her head by the couch. I was then told to sit on Sharon's face. Mistress moved forward so that my face was right in her cunt.

"Now slut, Sharon knows how to serve my cunt. She will tongue that pattern in your cunt, you are to immediately recognize what she is doing and repeat it in mine. We will see how well she taught, and how well you learned."

I buried my nose in her cunt. What was Sharon doing? Alphabet, tongue the alphabet around the clit, got it. What now, flat tongue from ass to clit, got it. Now curl the tongue and fuck the hole, got it. Mistress is moaning, good sign. Suck on the clit, got it. Mistress squeezed my head between her thighs and came all over my face.

Once Mistress released my head from between her thighs, I heard, "Very good slut" "As a reward Sharon will fuck you with the Feldoe until I tell you that you may cum. Get off her face. Kneel, chest on the floor ass up."

I got the Feldoe and helped Sharon get her end in place and the vibrator inside turned on before assuming the requested position. To say it slipped up my cunt easily would be an understatement, after scissoring and sitting on Sharon's face while she ate me out, I was a faucet. Sharon started slowly fucking me with the Feldoe.

All we heard from Mistress was "Faster Sharon!" "Harder Sharon" "Make that slut cum"

Sharon did her best and I felt my orgasm build. Sharon didn't let up but kept up the pace. Soon I was about to cum with or without permission. Then I heard, "Cum hard slut" Strong orgasms rolled through and shook me until my body failed and fell flat on the floor with Sharon on top of me and the Feldoe still vibrating deep in my cunt.

Mistress leaned forward, smiled and said, "Very good sluts. As a reward you are spending the night together in slut's room. We will be in Master's bed and expect the usual wake up in the morning.

It took a moment for that to sink in. I got Sharon for the night, and John and Mistress Umbra were sharing Master's bed! First, I found out John was bi, and now Mistress Umbra is too!

Sharon got to her knees, removing the Feldoe from my cunt. I helped her remove it from hers and turned the vibration off. I licked and sucked her end clean, and she did the same for mine.

I kissed John good night while Sharon crawled to her Mistress and kissed her feet. Our leashes were removed, and we crawled up the stairs to my room. As soon as we were in my room we grabbed each other, kissing, hugging and rolling together on the floor. We made it to the bathroom, removed our make-up and showered together with lots of kissing, hugging, groping and fingers finding various holes. It would be nice to say that we spent the night with glorious sex, but instead we talked and giggled and fell fast asleep in each other's arms.

I woke up as usual at 5:30 AM and did my first edging of the day watching Sharon sleep. I did my bathroom routine: used the toilet, brushed my teeth, brushed the tangles out of my hair, did my makeup, inserted my day plug, and put on my four-inch heel "house shoes." After making coffee I checked my business email, fortunately no crisis had come in overnight. At 6:30 I crawled back into bed and used the oral skills she had taught me yesterday to wake up Sharon. When she woke up, she pulled me up to her for a morning kiss. I explained how we were to wake up John and her Mistress. She got up and did her bathroom routine, very similar to mine.

At 7:15 we went to the kitchen and got two hot cups of coffee and carried them to Master's room and placed them on the nightstand. Apparently there had been a lot of action in Master's bed the night before, the blankets and top sheet were in a tangle on the floor. I started licking and sucking John's cock and balls while Sharon started to serve her Mistress. When my efforts woke John up he smiled, and pulled me off his cock. Reached over and grabbed the now awake Mistress Umbra and pulled her up onto his cock.

As she started to ride him, she looked back at Sharon, "You and slut practice what you learned yesterday, 69 and whoever comes first is going to feel my crop." Sharon swung around and offered me her cunt as her head disappeared between my thighs.

There is nothing like being eaten by a lesbian who knows what to do. She Licked from my ass to my clit, tongue fucked my cunt, sucked my clit, rimmed my ass, doing Lord knows what with her tongue did to my clit. I tried returning the service with everything she had taught me yesterday. But between what Sharon was did to me and the cries in my ear of her Mistress as she rode John, my attempts to hold off my orgasm failed. I muffled my cries into Sharon's cunt as the orgasm ripped and then rippled through my body. I moaned again as Sharon brought me off a second time. As the ripples from the second orgasm started to fade, Mistress moaned loudly, and John bucked up hard into her, with a loud grunt as they came together.

Mistress slapped me on the ass, said "You came without permission, get off and crawl to the playroom and wait for me."

As I rolled off Sharon onto the floor, mistress slid off John onto Sharon's face. I could see the large flow of John's cum out of Mistress's cunt onto Sharon's eager tongue and mouth. As I crawled out the bedroom door, I heard Mistress tell Sharon to clean John and do what he says.

Mistress caught up to me as I entered the playroom and directed me onto the same horse that John had used when he disciplined me for making him cum too early. As I mounted the horse, I briefly saw Mistress go over to her bag in the corner. I didn't see why or what she took out.

As she came up behind me, she said "slut, you seem to have a problem cumming without permission. I'm going to punish you for cumming with Sharon and then we are going to work on your problem." She punctuated the word "problem" with a stinging smack on my right ass with her crop. She then proceeded to work my ass and thighs over with that vicious crop with occasional swats square on my cunt. I never understood how beating pain, turns to heat, and the heat moves to my cunt, but that is the way my body works. My cunt, already wet from Sharon's attention was overflowing down my thighs.

I felt the crop laid on top of my back, and moments later felt something pushing on my cunt. I heard Mistress, "slut, that is enough foreplay, now we are going to work on your orgasm control."

Whatever she was trying to introduce into my cunt was large and firm. It moved up and down my labia then became insistent on the entrance to my cunt. As it started to enter, it just kept feeling larger and larger. It hurt. Then Mistress stopped pushing and let my cunt stretch and adjust. Then the pressure increased again, and I felt it stretch my cunt inch by inch as it was pushed in deeper, the pain had dropped to just discomfort. While not painful it was stretching me like I had never felt before. Then again it stopped.

Mistress spoke softly, but quite clearly, "Welcome to the world of my strap-on slut. Yes, I am larger than your Master or even John and as you can probably tell, I'm firmer too. I'm going to start fucking you, and you will not cum until I tell you too, or the cropping you just got will feel like it was just a warmup." With that I felt her slowly withdraw, and then slowly push again deep into my cunt. It was still stretching my cunt as it went back in. Mistress then started a steady pace.

My cunt was still adjusting to the size of Mistress. As it adjusted the pleasure started to flow. My cunt had never been fucked like this. It was at the same time familiar and yet completely different. It lacked the warmth of a cock and it felt more rigid, but at the same time it was stimulating my G-spot and all the familiar nerves in and around my cunt more firmly than I was used to. I finally realized what was missing, there were no balls slapping my clit as I was being fucked doggie style.

Mistress started slapping my ass every time she pulled back. I could feel my arousal starting to peak. Mistress started to speed up the rhythm and added some side to side and up and down to her stroke. She could tell that I was approaching an orgasm and warned me again that my ass would pay dearly if I came without permission. I bit my lip and dug my nails into my palm hoping the pain would help me control. I tried counting backwards, to get my mind somewhere other than the feeling in my cunt. It helped but my body was still climbing.

I finally begged, "Please Mistress may this slut cum for you."

"Not yet slut, control it until I give you permission. That cunt is mine not yours and will cum when I tell it to."

Mistress kept up the pace, occasionally slowing down a little bit, then picking it up even faster and harder. I concentrated, I willed it, then I felt Mistress pull almost all the way out and then slam it back hard into me as she almost screamed, "Cum for me slut, cum hard."

I may have cum harder in my life, but I don't remember if I had." My cunt convulsed, as did my gut. I screamed. I saw a light show in my head, and then nothing. As I came back from the dead, Mistress was gently stroking my hair and caressing my cheek. She took a handful of my hair lifted, my chest off the horse and kissed me deep and long.

I saw her smile. "Good slut, I knew you could behave." She reached back and pulled the strap-on out of my cunt and gave it to me to clean. Not nearly as rewarding as cleaning a cock, but on the other hand I realized that I was doing it not only because it is my duty, but to please Mistress Umbra, which somehow had become very important to me. She told me to get down from the horse, attached a leash to my collar and led me crawling from the playroom.

We checked Master's room and John and Sharon were no longer there. Mistress led me downstairs to find John and Sharon preparing some fresh fruit and yogurt for breakfast. As we sat around the table on the terrace, Mistress told John how well I had responded to my orgasm control training. John seemed amused and said that he would pass that on to my Master and perhaps he would arrange more training in the future. I got a wink from Mistress that I'm not sure I liked.

John then turned to Sharon, "Tell slut what you learned this morning."

Sharon blushed as red as the strawberries. Looked at the table and spoke very softly, "John fucked my ass. It was incredible. It hurt so bad, then suddenly like someone flipped a switch, it wasn't pain any more. It was just incredible." John took Sharon's hand and they exchanged warm smiles.

John then turned to me and asked how I liked my training this morning. I told him my experience had been much like Sharon's, it was painful at first, but became amazing.

John asked, "Are you sure?"

I looked at Mistress and said, "Yes, it was something I needed. Thank you, Ma'am."

John looked at Mistress smiled and proceeded, "I talked to her Master this morning, If you will have her, and she agrees, Master would like her to stay at your house this weekend under your rules."

Mistress looked at me and asked, "Do you agree, would you like to experience that. You would follow the same rules and duties as my girls."

Sharon chimed in, "Oh please say yes."

I looked at John, I looked at Mistress, and then I looked at Sharon's eyes. I saw the same pleading look I had seen at the party before I helped introduce her to male cocks. Now she wanted to help introduce me to Mistress's rule. I swallowed hard, looked at Mistress and said, "I would be honored to spend time in your house under your guidance and rules." I had sealed my fate.

The Penthouse 07 - Mistress Umbra Weekend