I Would Do Anything Ch. 03

Claire was exhausted. She lay back in the padded chair breathing heavily. She was in her mid-fifties and just face fucked me with her 7" strap on dildo. No doubt she hadn't enjoyed much sexual activity recently.

"Oh my God, that was fantastic," she was able to get out.

I was breathing rather heavily myself. I wiped my mouth and lips with the back of my hand and sat back on the floor, remembering the existence of the tennis ball sized butt plug that stretched my opening. In a way, it felt delicious. Here I was, completely naked in front of two beautiful women in their fifties whom, in their day, were undoubtedly stunningly attractive and highly sexual, each donning strap on dildos, each that a short while ago was buried deep in my mouth. I knew what was coming next. This may have been new to me, but I was not that naive. Oh, I did want more.

"Little one", Sue began. "We're going to have to put you through another test, since you have yet to pass a single one. You do want to see my tits, look at their fleshy skin and suppleness, don't you? You said to me you would do ANYTHING for the chance to see them, but thus far, everything I have asked you to do has been met with failure. What say you, shall I give you yet another chance?"

"Yes Mistress", I immediately replied in earnest.

"Good girl." Again, I was referred to in a feminine tense. "Run off to the loo and remove your plug. When you return, you will need to present yourself to me as you did earlier this morning. Legs apart, hands behind your neck and your clit nice and hard."

"Yes Mistress", I answered.

"Run along then, little one."

I turned to my right and walked deliberately towards the bathroom, knowing what was about to happen to me. I noticed to my side was Claire, eyes half closed and a lustful look in her eyes. Her hand was gently stroking her 7" strap on cock. I wasn't going to have to worry about keeping my cock hard, what I was witnessing that day was something I had never even dreamt before. Here I was stark naked, clean shaven from neck to toes, sporting a raging hard on, masturbated in front of a beautiful woman in her fifties and then forced to lick it up, put over her knees and spanked until I was close to cumming, plugged and sucked on the strapped on cocks of these two gloriously sexy women... did I know what was next on the menu? I had a pretty good idea.

I entered the bath and squatted over the loo. Grasping the base of the oversized butt plug, I began to push as though I were going to the toilet. It didn't want to budge though; the flare from the base to the widest point was quite a lot. It burned as tried to pull the bugger out. Then, as I felt myself being stretched to the limit, the butt plug sort of shot out of me. I was able to keep ahold of it as my breath was obviously louder.

"Are you alright in there, little one?" I heard Sue call from the other room.

"Yes Mistress, won't be a minute."

I turned and looked at the monster that had been invading my backside for the past hour or so and saw that it was perfectly clean. The enemas I had been given earlier certainly did their job. My pussy, I mean my ass, was ready to be deflowered. I washed the plug and set it next to the sink, smiling at it as if it were a friend, knowing there was a gaping hole where it once was... a lonely hole that wanted to be filled again. Then I looked up into the mirror, stared myself in the face, and said "let's do it!"

I turned and walked into the lounge. My clit or cock or whatever was curved upward and hard as ever. The women were sitting on the sofa as I entered, each wearing their respective strap-ons; Claire with the 7 incher and Sue with her impressive 9 inch cock. Claire was idly stroking her's and I remembered that it was hers which was a double ender, so the other end of that prosthetic cock was buried up her pussy and she could feel it when she stroked it. That visualization made me hot. Both of these women, whom were both in their mid-fifties, were incredibly sexy. Sure, they might have been passed their prime, but were by no means beyond it.

I stood four feet before them, spread my legs and clasped my hands behind my neck, all the while keeping both eyes focused on my beautiful mistress.

"You've done well my dear, considering you've yet to correctly perform even one of the tasks I have asked of you. You have played along with us and given me your all, for that I respect you. That said, you still have not completed any of my desired tasks, and this will be the last. Although it has been fun to have a young plaything around again, God knows it's been a long time since I last had one, I feel it necessary to push you further in order for you to accomplish your goal." I was somewhat nervous now. Still completely aroused, hard as a rock, but wondering if what I thought was coming next had other things tagged to it.

"So you wish to see my tits? You long to see my tits, full and free of their confines. I'm quite sure you'd like to hold them, feel their weight, roll your fingers over my nipples, suckle them, what have you." She stood up. Her extra, long cock bobbled in front of her. "My dear, I need you to bend over and spread your pussy wide for me."

I did as I was told. I bent over slightly, reached around and grabbed my ass cheeks. I slowly pulled them apart when I felt Mistress place her left hand on my hip. Then I felt it. "It" being her massive cock pushing against my wanting pussy, I mean ass, I mean my stretched hole that craved to be filled again.

Mistress began to speak as she pushed her cock into me, "I know you want this. And you will learn to crave it." She continued to slowly enter me. "And I know you want to please me. This pleases me. You letting me violate you, letting me fuck you and fill you." Her cock continued to bury itself in me as she now placed her other hand on my hip. Then I felt her bottom out. Her body was pressed against my upturned ass. I had all nine inches of her magnificent cock lost in my ass. My eyes were closed and mouth agape as I moaned softly.

"Here's your test... do you enjoy this? Do you like this feeling of having a cock stuffed up your pussy?" she wiggled her hips to ensure that her cock was well and truly seated properly, she pushed against me even more to emphasize her presence there.

"I want to see just how badly you want to see my tits and how badly you want to be fucked." She began to slowly pull out of me. "I want to hear you beg for more, to want for more and scream for more." She was nearly out of me and then slowly pulled me by my hips and back onto her huge cock. This was the motion, she wasn't necessarily fucking me as much as with her pulling my hips to her and away from her, she was forcing me to be fucked.

The rhythm began to increase. My moans were becoming increasingly louder. Then, as I was beginning to really get into this whole feeling of being fucked by this woman, she paused while fully inside of me. "This is my task, my pet. I can already see you enjoy the feeling of a hot cock in your pussy, but I want to see how many different ways you want it. I want you to choose a position by which you will be fucked for, let's say at least 5 minutes, by Madame Claire here. You will then mount my cock in a different position for at least five minutes and so on. Remember, we're not young kids any longer like yourself, so that is why you'll be taking turns with us, so we can have a little rest. And besides, one of has to snap the photos."

If my head wasn't spinning earlier, it certainly was now. I couldn't believe what I was hearing.

"Now little one," Sue continued to say as she also continued to fuck me again in a slow, but deliberate rhythm, "you will show us twelve different positions in all. That should do nicely. It will mean you will have been fucked for a solid hour when it's all over. No cumming until I say so. And that clit of yours must remain hard at all times, even if it means you have to stroke it for us from time to time."

"If you're able to do this", she began to increase the tempo and force by which she was pulling my hips onto her cock, "if you're able to show us twelve different to be fucked by us, while keeping that clit hard and without cumming, then my pet, you will see these magnificent tits of mine. Claire?"

Then Claire spoke up, "yes little one, I will even show you mine, though they are not nearly the size as my dear Sue's are. I'm looking forward to this challenge."

"Yes, so am I." Sue then stopped mid-stroke, reached around and felt my hard cock. She giggled and asked me, "Are you up for it?"

What could I say? "Yes Mistress, I want you and Madame Claire to take me every way imaginable. I want to feel your cocks taking turns plowing into me. Please Mistress, let me show you how much I want to please you." As I pleaded, I began to move on back and forth on her strap-on, which remained buried inside my ass. "Please Mistress, fuck me. Fuck your little plaything. Give me your cock, I want all of it." Then, turning my head to see Claire stroking her 7" strap-on, I said, "I want your cock, as well, Madame. Please give it to me, let me have it. Use me, both of you, please!"

I was plunging my bottom onto Mistress' 9" cock and panting like a dog, moaning loudly. I wanted it so badly.

Then I felt it, SMACK! right across my bottom. "That's the good girl we want to see."

SMACK!

With each stroke, Mistress laid another on me and I was getting so fucking hot from it all!

"You will do just fine, I believe", she said as she stopped me from moving and slowly pulled out of me. "This position doesn't count and has now already been used. Show us what you got, my slut."

I didn't like the feeling of emptiness when she pulled her cock out of my ass. I needed to have something back in there and I knew the procedure. I was to now engage with Madame Claire in a new position. I straightened up and looked at her sitting on the lounge. I slowly and deliberately walked towards her and turned around, placing my feet on either side of hers. I then lowered myself onto her beautiful cock, knowing that it would easily find its way to my ass as it was so stretched from my first fucking. I felt it enter me and let out a gasp. "Ah, home", I thought to myself as I smiled. Claire took hold of my waist and I used her knees for support until I was now sitting on her cock with all my weight and wiggled some to make sure it was in all the way.

"Oh Madame, such a lovely cock you have. May I please?"

Claire replied, "Yes my little slut, you may."

And with that, I began to rise my ass up until I felt the head at my opening, then I would sit back down with a thud. I would let out a loud moan whenever I bottomed out on her lap. Up again and down, I could feel it sliding in and out of me and it was marvelous. So sexy, so dirty, so new and exciting... Mistress stood before me with a smile on her face. I reached out took hold of her cock and took it in my mouth. I was in heat. I was stroking Mistress's cock while sucking it into my mouth while moving my ass up and down riding Madame Claire's cock. Mistress lightly stroked my hair and smiled when I looked up at her. My own cock bobbed up and down with all my movement. Claire was now getting quite vocal and soon hit a crescendo.

"Oh, ride my cock you slut. Harder I say, take it all and love it!" I did love it. Claire was holding onto my waist and literally throwing me up and pulling me down, obviously close to orgasm. Sue pulled her cock from my mouth and watched as Claire reached her orgasm. She held tight against her lap, trying to push it in even deeper it seemed and then she let go and sighed. Her body went limp. I slowly stood and felt the strap-on plop from my ass. Actually, it felt like a pussy to me now!

"Mistress, could I ask you to sit in this chair for me?" I said motioning to one of the straight back dining chairs.

"Why of course my dear", was her reply. I then walked to her, my own cock/clit bouncing to and fro as I did. I pulled her knees together gently and then put my left hand on her shoulder and took hold of her 9" cock with my right. Straddling the chair I got on my tip toes and aimed the beast at my entrance.

"This makes two, does it not Mistress?" And I lowered myself down onto her cock.

"Yes it does, my pet." She reached around and kneaded my butt as I began to move down its length, filling me up with her meat. I shivered and she felt it. I moaned and she heard it. My breathing picked up as I neared the base and she noticed. When she was fully inside of me, I looked her in the eyes; we were face to face, just inches apart. My own hard cock was brushing up against her belly.

"Thank you Mistress." My face was tingling. I moved my hands around to her back, feeling her bra strap through her black top. I held onto her tight as I started to move back up her cock. As I did, my cock was rubbing the length of her torso. My cock was then pressed against Sue's tits. I moved away from her slightly and then it sprang up above them. I couldn't help but imagine that if she were topless, I could tit fuck her while she ass fucked me. When I picked up the pace, I think she had the same thoughts. I did all the work while she guided me to just the right distance from her that my fully erect cock was rubbing up between each bra cup. Essentially, I was tit fucking her, but while she still had her bra and top on.

Her nine inches were disappearing completely with every down stroke and I was moaning uncontrollably. My eyes would roll to the back of my head in ecstasy. Sue knew just what she was doing and it was working. I realized this and opened my eyes to her smiling face. My balls were beginning to boil as I would undoubtedly orgasm if I kept this up and hence, fail again. Not wanting that, I concentrated on her expression and my rhythm. Yes, it felt fantastic and yes I could've cum at any moment, but I didn't want to fail another test. Instead, I worked on her orgasm instead of mine, trying to get her fake cock to have a real orgasm. I kept my eyes focused on her face as I ground my ass/pussy onto her massive cock. I squeezed my ass like a woman would squeeze her pussy lips. I was starting to get good at this. Soon I was gyrating my pelvis like a pro.

"Very good my pet, I am impressed. Now relax, you have many more positions to show us. It's Claire's turn again."

I slowly stood up as her cock inched its way out of me. I looked down upon Sue's beautiful cleavage and noticed a hint of perspiration. I do believe she was pleased with my efforts. My cock deflated slightly when I began to focus on her pleasure instead of mine. When her cock plopped out of my hole, I gently took hold of my own and began to stroke it lightly back to full hardness.

"Thank you Mistress."

It was Claire's turn for some more attention. When my cock returned to it fully rigid state, I asked her if she was ready for me. To which she answered, "How do I get to screw that pussy of yours this time?"

I knelt on the lounge with my knees spread wide near the edge of the seat cushion and my hands took hold of the back. I turned my head around as she stood looking at me and said, "Please Madame, please use that big cock of yours and fuck my pussy with it!" and shook my ass.

The look on her face as she purposely came to me and in one smooth motion, grabbed one hip and then the other and aimed her cock right for the target and in no time bottomed out inside my turned up back side. I let out a cry as the forcefulness of her entry surprised me somewhat. Her cock was cool at first and I realized she had been stroking it with lube while I was with Sue. Immediately she began to saw away at my ass/pussy and all that could be heard were grunts and moans. She wasn't gentle at all, but it was actually kind of nice. The feeling of be taken by Claire was a direct contrast to being made love to by Sue.

Claire had yet another orgasm before her five minutes were up and I was thoroughly excited to have been used by her. When she pulled out of me, I merely rolled over grabbed my ankles and looked at Sue and said, "Are you ready for number four, Mistress?"

Sue had her way with me and soon the five minutes were over. The sight of her tits swaying back and forth while she fucked me was exciting enough, but again, I had to focus on her pleasure to keep from cumming.

I asked Claire to lie on her back on the floor. I placed a pillow under her head and told her to just relax and that I would do all the work. Turning to face her feet, I straddled her hips and lowered my ass/pussy onto her cock. Practicing with my hip movements and squeezing my sphincter muscles, I got into a pretty good rhythm. She couldn't help herself though grabbed my ass squeezed. SMACK! SMACK! SMACK!

"Let's go slut, I'm expecting another orgasm here!"

I got to work on her, forgetting that her strap-on was a double ender. The five minutes had passed, but she wasn't finished with me yet. So she took hold of my hips and threw me down on her cock, grinding it into my excited ass/pussy. That did it! She let out a scream and squeezed my ass for what seemed like forever before going limp. I leaned forward, remaining on my knees and she popped out of my very used hole.

"Mistress, I would very much like to do the same with you, but facing you. Would you mind?"

Sue laid down her big rubber cock resting on her stomach. I squatted above her and guided her lovely cock into my hole and then sat fully onto it. I got onto my hands and knees and lowered my face to hers, again, just inches away. I could feel the heat in her breath. I whispered in her ear, "this will be number six, Mistress."

For the next five minutes, I slowly rode her beautiful nine inch cock. My cock remained hard as it gently grazed her sheer black top. When I was told that it was Claire's turn, I stayed on my knees and slid forward towards Sue until just the head remained inside of me. My hard aching cock was saddled in between her two heavenly breasts. She took hold of me and pulled my nipple down to her mouth. She licked it and then sucked on it for a moment. Then she put my left nipple in her mouth and gently bit down on it. It felt delicious. I felt a charge run through my body.

"Go to Madame Claire, little one. It's her turn with you now."

And with that, I moved forward and the head of her mighty cock popped out of my ass/pussy. Immediately I felt emptiness down there. I know what I wanted and I wanted it hard. My cock/clit bounced as I walked just past where Claire was sitting, idly stroking her fake cock with the glistening presence of lubricant. I stood at the wall and spread my legs apart, hands at eye level and my bottom sticking out to her.

"Please Madame, please will you fuck my pussy nice and hard? Please Madame, I want it! I need it."

Claire smiled as she stood and strutted over to me, all the while stroking that 7" strap on she was wearing so well. Her finger traced down the spine of my back, between my cheeks and two wet fingers easily slipped into my ass/pussy.

"My, my... someone is going to be ready for a fist soon, I think!" And with that, she grabbed my hip, guided the head into me and then with both hands on me now, began the assault I was hoping for. The other end of her dildo must've been rubbing against her clit just right, as she became moaning and grunting like an animal... again! And I wasn't exactly biting my tongue. I bent forward a bit more to provide easier access for Claire who seemed to appreciate the move telling me I was taking it like the slut she thought I was.

"Ugh! Thank you Madame! Oh Madame... AHHHH!"

Her excitement built up rapidly the more she drove her cock into my very loose ass/pussy. Faster and harder, she was tightening her grip on me as she threw herself into me.

I couldn't explain how it felt. It was surreal. I was the only one of us there completely naked. I was with two grown, attractive women in their mid-fifties who were each still dressed and donning huge strap-on dildos and taking turns ass fucking me. I had masturbated in front of them, been given multiple enemas, stuffed with a butt plug of varying sizes, forced to suck on their cocks. All of which I had never experienced before today. At first I was tentative, unsure what to feel, think or do. I just followed instruction. Instruction from Sue, a woman I have known most of my life as a family friend through her husband. I had always admired her incredible bosom. It was huge. She had told me once when I was seen eavesdropping on one of her friends changing from out of their bikini that if I ever wanted to see a real pair of tits to just ask. That was ten years ago and everything that was happening today was because I finally asked to see them. My head was spinning from the chain of events occurring since this morning.