I Would Do Anything Ch. 04

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Young man finally pleases his Mistress.
4.7k words
4.61
28.4k
12

Part 4 of the 4 part series

Updated 09/22/2022
Created 12/11/2013
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I was more than half way through my latest test from Sue. I was to show both her and Claire twelve different positions to fuck me with and perform it for at least 5 minutes making it virtually an entire hour of being fucked by these two gorgeous women. Claire was wearing a thick double ended 7" strap-on, while Sue donned a massive 9" cock so thick I couldn't reach my fingers around it. I was also instructed to remain fully erect the entire time, even if it meant stroking myself from time to time. Oh yeah... and I was instructed NOT to cum.

Claire's latest effort was the 7th position and it was now Sue's turn once again. I looked deep into her eyes, gently stroking my hard cock, which the two women kept referring to as my clit. In fact, my ass was now my pussy and I was their little slut for the day. Sue was beautiful, and I wanted nothing more than to please her by passing her test. Thus far, I had failed miserably on every occasion and I was quite sure this was my last chance.

"Mistress, could I ask that we move to the guestroom for the remaining experiences?" I said with my hand outstretched to her.

"Of course you may, little one." And she reached out and took my hand. I turned and reached out to Claire, "Madame, would you be so kind as to join us in the guestroom?"

Still exhausted and breathing heavy, she too reached out and took my other hand as we walked into the room where I slept just last night, all three of our cocks bobbed this way and that as we did. I lead Claire to the oversized chair in the corner where she sat herself down and immediately began to slowly stroke her fake dick. I asked Sue to lie in the middle of the bed, and I propped an additional pillow behind her head. I wasn't real sure how this would work, but kept at it as if to appear I planned it all along. I then straddled her large hips and lowered myself onto her huge cock.

"I'm flattered pet, but I do believe we've already tried this position," Sue began. "Do not disappoint me now."

"I won't Mistress, please wait a moment." I then extended my right leg and then left to either side of her chest and then using my arms to support myself, I leaned back away from her, keeping my legs somewhat bent to support my other half. With my midsection now suspended, I began to raise my pelvis up, sliding along the length of her 9" cock.

"Please Mistress, could you possibly hold your beautiful thick cock in place for me, I'll take care of the rest." Sue took hold of its base and I slowly began to lower myself back down onto her shaft, and then back up again. "Mistress, I believe this is number eight, yes?"

Sue smiled, "Yes it is, my slut. Yes it is. I'm most impressed. How does it feel?"

"Wonderful Mistress, I love having you inside of me," I answered, followed by a loud moan. My hips were now steadily moving in an up & down motion as I rode her cock. I suppose it was due to the angle of penetration, because on my downward stroke, I felt her cock rub my prostrate and it truly did feel wonderful. I would be in trouble if I kept it up like that, so I once again concentrated on Mistress' pleasure, but it sure felt good. I would come into contact with hand each time I bottomed out. Sue used her left hand and reached for my balls, running her nails on the tight skin. I remained focused on her as she would occasionally tap on them or squeeze them.

Claire then noticed something and spoke up, "Sue darling, our little plaything is leaking." Sure enough, pre-cum was dribbling out from the attention my prostrate was receiving. A pool had developed just below my belly button.

"Claire, would you please take care of that dear?"

"Of course, Sue. I've got just the trick." Claire stood and scooped up what she could with her fingers and rubbed it all over her cock. Then she walked over and stood behind me as I continued to ride Sue's cock. She leaned over my head and told me to lean my head back. When I did, her cock was looking me in the face and she slid it into my mouth with one steady push while holding my head still. The taste of my sweet pre-cum excited me even more. Soon, Claire was face fucking me while I maintained a nice rhythm on Sue's beautiful cock.

After a few more minutes, Claire pulled out of my hungry mouth and asked Sue if she could have her turn now.

"I supposed it has been five minutes, are you ready for another round little one?" she asked me. I sat fully on her cock now and answered yes, but I wanted to keep riding her cock. I remembered though that I would still have two more turns with Sue before the test was over. Claire scooped up the remaining pre-cum on my stomach and brought it to my mouth while I sat up and brought my legs back under me so I could sit up. I moaned as I sucked her two fingers, rolling my tongue around them and then lifted myself off from Sue's cock.

Sue slowly swung her legs over and sat up and then took a seat in the corner chair. Claire withdrew her fingers from my mouth and asked me, "well, what will it be this time, slut?"

I lay down on the bed and then turned over onto my back. Since my high school days on the wrestling team, I have always been limber and I had an idea that should turn on the seemingly insatiable Claire.

I took hold of my ankles and pulled them back to my head and moved my elbows inside of my knees. I lay there with my gaping man pussy open to this sexy woman with the 7" strap on.

"Please Madame, I want you to use that big cock of yours and fuck me with everything you have. I want your cock deep in my pussy, fucking me until you shoot your hot cum deep inside of me!"

Claire certainly was enjoying my dirty talk and slutty behaviour. I felt her weight on the bed as she got on her knees between mine and pushed the head of her lovely cock into me, then placed her hands on either side of my head and drove the rest of it into me. In no time, she was nailing me in a piston-like fashion, driving her cock into my hungry ass/pussy balls and all, or so it seemed. She was so hot, fucking me with her fake cock like she had been doing it all her life. I couldn't help but wonder how close that was to the truth. All that could be heard was the slapping of her fake balls each time she maxed out, grunts and groans, moans of pleasure and me calling out to her to "Fuck me, Madame! Fuck me harder! Yes!! YES!!"

The picture in my head of what we must've looked like made me so hot. I looked to my right and saw Sue watching Claire's attack on my hungry hole. I was convinced that Claire did not have a five minute limit when we were at it; rather she was allowed to fuck me until she climaxed and sure enough it happened. She drove into me hard and held it there, deep inside of my ass/pussy, shortened breath and then a quick few strokes in & out with a quiet scream and her head thrown back. It was really something to see, a middle aged woman in the midst of orgasm brought on by her fucking my ass with a strap on dildo. I felt wickedly excited knowing that this was brought on by my participation.

When she pulled out of me, I again felt empty. I enjoyed presenting myself in the contorted position I had with Claire and wanted to do likewise for Sue. Claire rolled over onto her back in order to catch her breath and I looked over to Sue as I scooted to the end of the bed.

"Mistress, could I ask you to sit here at the foot of the bed?" I asked, standing up to make room for her, my cock/clit remaining as hard as ever knowing I was close to passing her test. Sue walked over with that huge cock of hers menacingly swaying from side to side as she did. When she sat down on the edge, I knelt down between her legs, put my hands on each knee and took her cock in my mouth. I began sucking it deep into my mouth, but still only able to take 7 of the nine inches, though that wasn't my goal to deep throat her entire length. I used my hands to spread her legs apart, then let go of the grip my mouth had on her cock and I briefly licked the underside of her strap on, as though it were real and she could feel it, even licking and kissing her fake balls. I then sat down and set my legs on the bed and scooted my bottom closer to her until it was against the bed. Then I flipped my legs over my head onto the floor on either side of my head, providing her immediate access and viewing of what must have been a gaping hole between my legs.

"Please Mistress, if you would please, dip your cock into my pussy and fill me with your beautiful meat!" I begged as seductively as I could.

While remaining on the edge of the bed, Sue took hold of her cock and was easily able to rest the head of her cock at my opening. She slapped it against my ass/pussy for a few moments, forcing me to want it even more.

"Oh Mistress, please fuck me with your beautiful cock! I really must have it! I need it deep inside of my pussy, spreading me open, stretching my cunt!" I really was begging for it now. I had to have it.

With the head of her cock resting at the opening of my hungry pussy, Mistress then slowly stood up and as doing so, her cock began to enter me. Ahhh, once again I was being filled with lovely cock!

This position wasn't straining on Sue, which is exactly what I wanted. By simply squatting a little and then standing again, she could easily fully fuck me in a slow and methodical pace. Looking up at her, my cock/clit looked back down at me, merely inches from my face. Eventually she and then Claire made notice of this.

While I was moaning in delight from the glorious feeling of Sue's entire nine inches once again burying itself deep into my pussy, or ass, Claire spoke out, "My dear Sue, I do believe with a bit of effort, the little slut could possibly suck on her own clit! That would certainly be something new!"

"Yes", Sue replied a little out of breath as she continued to plough into me deeper and deeper. "I've heard of that being done, OOH, but have never seen it... oh dear, this position is doing something special for me!" She looked down at me, directly in the eyes, "little one, this is putting pressure at just the right spot, I, uh... um, it feels, oh yes... it feels quite good!" Her breathing was heavy, her pace picked up, especially on the down stroke where she would grind her cock into me before pulling back out. I could only imagine that the base of the dildo was pressing against her clit.

Sue began to fuck me with earnest, in the same manner that Claire did. She began to squeeze her tits with full hands as she rose up and back down, sliding the entire length of her fake cock into my wanting pussy or cunt or ass, whatever, it felt fantastic! She began to moan and then drove it in as deep as it would go and ground herself hard onto the base of it.

"Uuuuuggghhhh!" she moaned aloud, "oh gaaaawwwwwd, ohhhhhhhhhh!" Then her body shook and convulsed. I was bringing her to orgasm! She continued to push her cock further into me, as though trying to push her balls in, too! It actually felt as though they would get pushed into me. The full weight of her was upon me, grinding her pussy against the giant strap on, which in turn was grinding against my pussy/ass and it felt wonderful to know I had brought her this much pleasure.

Claire came over and whilst kneeling over my head, her cock lying on my face, she ran her fingers up and down the backs of my thighs, pulling them down ever so slightly as she did. She traced her fingernail on my, oh so sensitive, perineum that made me shiver and pulled my leg down a little further with the other hand. Together with Sue's weight pushing down on me, I saw as the head of my cock inched closer to my face.

Claire looked down at me as Sue regained her composure, but remained with all of her weight on me and all of her cock in me.

"Lick it, slut!" said Claire. "Do it, we want to see it!"

I opened my mouth and stuck out my tongue reaching for the head of my cock/clit. As a young kid, I used to do tricks with my tongue, like roll it over one way and the other and even touch the tip of my nose with it, so it was long. Out it stretched and the head of my cock/clit felt, for the first time, my very own warm tongue against it. This excited both Claire and Sue. Sue began to bob up and down while her cock remained in me, causing my own to gently bounce against my tongue. Soon I was able to press my lips against it, but that was it. I wasn't flexible enough for anymore.

"That's definitely something I want you to work on, my pet," said Sue as she began to stand and then sit back down on the edge of the bed. Claire released my legs and they instinctively fell onto Sue's thighs. My cock was achingly hard and straining before her.

Sue reached out and took hold of my turgid member and with a couple of slow and deliberate strokes said to me, "That, my dear, was fantastic. You're nearly there. Can you succeed by performing two more times for us? Can you do that without cumming?" She knew I would blow if she continued to stroke me just a few more times, which would be unfair to me in this challenge.

She let go and padded my sac, "Such a lovely little play thing I have. Up you get, what do you have left for us?"

Sue stood up from the bed and both women, each donning their huge strap on cocks, stood on either side of me as I got to my knees and crawled onto the bed. I rolled onto my back with my neck hanging off the foot of the bed and my knees spread and bent.

"Mistress, I would like to try once again to take all of you into my mouth while Madame fucks me missionary style."

Each looked at the other and moved into position. Claire took a pillow and patted the side of my bottom. I reacted by lifting my butt up and she placed the pillow, folded in half, underneath me, providing her easier access to my pussy or ass, whatever she wanted to call it, I didn't care. I just needed it filled. When she got positioned between my legs, she guided her cock, once again, into my waiting hole and held it there just an inch or two inside of me. Sue then held her beast and after slapping my face with it two or three times, placed the head of it between my lips and held it there. In a concerted effort, each woman then slowly pushed into me a little more and then pulled back out. In a bit further and back out, in even more and back out, each in perfect rhythm with the other. Each pushing there cock further into me and then pulling back, each time a little deeper and a little more forceful. For my part, I just lay there and take it, and I was doing just that.

Soon, Claire was shoving her entire length into my man-pussy and Sue had a good 7 inches of her nine filling my mouth. I tilted my head further back, removing the angle of my throat altogether and soon I felt Sue's balls ever so lightly touch my nose. Then again, then harder against my nose and then... her beautiful fake balls were pressed against my upper lip. I had taken all of her magnificent 9". When both women saw that, they began to begin with a steady fucking of my, oh let's just say it, my pussy and my mouth. With Claire lying on top of me, supported by her elbows, she watched as Sue's cock could be seen in my throat with each stroke. I was choking, but loved the fact that I swallowed her whole.

Claire then sat up on her knees, remaining inside of me and grabbed my hips. Then she went for it, she knew this was number eleven and her last time (for now anyway) to fuck me to her own orgasm. And she was determined to do just that.

As Claire began to groan and grunt, bringing herself off at the mercy of my well fucked pussy, I looked up at Sue as she caressed my cheek, my cock filled cheek. Sue withdrew her cock and rubbed the saliva lubricant all over my face, stroking it as she did. Claire continued her assault and then just like that, she was over the edge and shook violently as she let out a long moan and took in a deep breath.

"Oh God!" she said as she looked down at me. "I do miss this. You, our dear little slut, are a pleasure to have around." She then looked to Sue, "You don't mind my forwardness, do you my dear?"

"Of course not." was her simple reply. "Now, let's see what we'll get for a finale from our little plaything."

Claire carefully pulled out of me, allowing me to enjoy the long, slow withdraw. She left only the head inside of me for a few moments, reached down and took a firm hold of my clit, then looked me deep in the eyes and smiled. I let out a gasp as I was incredibly sensitive after everything we've been doing all day. She squeezed harder and then let go as she simultaneously pulled the head of her cock out of me.

I took a few quick breaths through pursed lips as I even shook a little. "Are you alright my pet?" asked Sue.

"Yes Mistress, I'm just, well... this has been such an incredible experience for me today and I'm, well, at the peak of arousal, my face has pins and needles, my co... ahem, my clit is overly sensitive and my pussy feels empty."

"Is it all too much for you my pet?" asked Sue.

"No, no!" I answered quickly. "No, please... we're, I mean, I'm almost there. There's just one more position I want to show you Mistress. Can you please sit up here in the middle of the bed for me? Just sit and cross your legs, please Mistress?"

Sue reached out and cupped my chin as she walked around to the side of the bed and sat down. Then she elegantly swung her legs over so lady like, even though she was sporting such a huge appendage. She scooted into position and crossed her legs, never taking her eyes off of me. Facing each other, I got up on my knees and moved to her. Placed one leg around her and then took hold of her cock as I swung my other leg around, lowering myself onto her nine inch wonder, letting my full weight down onto it as it buried itself into me. I then wrapped my legs around her and wrapped my arms around her neck.

"Mistress, this is number twelve. Thank you." And with that, I began a slow to and froing of my hips as I rode her in sheer bliss.

"You have done well, little one... extremely well." Sue looked over my shoulder to Claire and nodded, "Claire can you also help me with mine please?"

I felt Claire's presence behind me. She was on her knees and reaching around me unbuttoning Sue's blouse. I raised my hands so she could peel it off Sue's shoulders. Then, remarkably, Claire reached around Sue fiddled with something I could only imagine was her bra. When the straps went limp and Claire slid them down Sue's shoulders, I knew I was correct. The only thing holding it in place were our bodies pressed together.

Claire's arms were under mine and she reached up to hold my shoulders and softly kissed the top of my head. I felt her bare breasts pressed against my back as she rose up onto her knees and I felt a breast on either side of my head. Her hands pulled me back a few inches allowing Sue's bra to fall between us and I couldn't look. I couldn't believe this was happening! My eyes must've been a big as saucers as I just kept eye to eye contact with Sue. Sue moved her hands under each breast and lifted those mighty and wondrous tits to my face and pushed them against me, taking my breath away. I swear, if I would have died right then and there, I would have died a very happy man.

"Keep rocking little one, don't stop," she whispered to me.

So I did just that, I rocked forward while the two of them held their tits up surrounding my head. I began moaning as I rocked and then Sue pulled away and pointed her right nipple to my mouth. The nipple was dark brown in colour, sticking out proudly ½"-3/4" and her areola was maybe 3" across. My mouth opens and I simply began to suckle it as I rode her cock. First one, then the other nipple. I turned my head further to my right and sucked on Claire's right nipple, slightly smaller and lighter in colour, it was nonetheless beautiful. I reached my hand around to my right and took hold of Claire's cock and began to stroke it, remembering that the other end of it was inserted in her pussy.

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