Mistress Valeria Pt. 03

This is part 3 of my Mistress Valeria series and I truly suggest reading parts 1 and 2 before this one if you have not done so. Thanks all for the support and feed back on the first 2. I believe this should be the best part. This is still around 90% accurate and I am looking to drag it out a little more by being more descriptive and let the story come to me instead of pushing it. Let me know what you think.

Chapter 6 Starting my Anal training for Mistress

Mistress Valeria had left town and now all I could do was replay the moments we had in my head, knowing it would be months before I saw her again. However, I knew that next time I wanted to not just be in complete sexual bliss but to give her the same. My goal was going to be to make her cum and leave her as exhausted and fully pleased as I had been and then maybe I would leave a lasting impression on her.

The following day, I went to work on figuring out how I was going to please my mistress by taking her full cock easily. It did not take much to find what I was looking for as after just a few blog sites I knew where I needed to start. To fit that perfect cock inside me I needed some butt plugs to get use to having something in my ass and there was no better way then to just hop on a popular sex toy site and buy their most popular and well reviewed anal training set. Anxious for my toys to arrive, I had picked 2 day shipping, I still kept looking into how I would be able to easily and safely stretch myself while not over doing it. I would need to just slowly build up the sizes over a week or 2 depending on how it felt. However, the day came when my toys would be at home after work and I got a little more then excited and impatient.

Rushing home early from work, I tore open my front door and tore open my package. Inside was the slim black anal training kit and the first time anal set with lube. There were 3 toys, starting at 1 inch wide and 3.5 inches deep and moved up a quarter inch wide and an inch longer on the next 2 toys so the largest was 1.5 inches wide but 5.5 inches long. I read some of the instructions for cleaning and the lube and just jumped right in. Rushing to my bathroom I stripped and pulled out the first toy and lube and got into my shower, just in case of a mess. My heart was racing as i had played with my ass many times before but this was very different, it was not just pleasure but a goal and I did not want to fail.

I breathe in slowly as I lubed the toy and my ass, only to sigh and say, "Here goes nothing."

I sucked in air as I slide the toy along my ass crack till I found my tight, tense asshole. I had goosebumps. I slowly slid the end of the toy into my ass and stretched slightly as I was still tense. Still nervous, I removed the toy and added a generous amount of lube. This time the toy surprised me, and as I went to slide it into my ass it just quickly slid half way inside me. I slightly moaned and stopped as the toy's widest part was now pressing into me. Taking another deep breathe, I just went for it and stuck the toy rest of the way until the base came flush with my tight hole.

"Oh shit!" I moaned. It felt so good to have this small teasing and filled feeling.

I left the bathroom and went to my computer to jerk off and edged some so I could get use to the feeling. Every stroke on my cock just felt better and more euphoric. I was in this fantastic mostly hard but not all the way hard place so I could easily stroke and watch even the hottest porn but I knew I could go at it for a while without cumming. In just 15 minutes it felt so normal and yet so hot. I had to go to the next size up. However, this is the part where I should have taken the blog advice a little better.

Hastily I went back to my bathroom, removed the first plug and cleaned it. Then I got back in my shower to stuff the next size up in my ass. Now .25 inches difference is almost nothing when it comes to anal play, except when you are first starting out. So, when I quickly lubed up and shoved the plug in, I got quite a surprise at the widest part.

"Ugh, oh god so tight," I moaned as I stopped midway to realize this felt quite a bit larger and tighter. My ass not quite just opening up and inviting it in. I stopped and breathed in a few times before forcing the plug in till it was flush on my now very tight and filled hole. I felt sore and stretched where before it was more just pressure and pleasure. I took a moment to feel it deep inside me before trying to walk and when I did walk it felt worse. However, I made it back out to my computer and sat down and just let the feeling continue to take over. The pain and stretching had made me go almost completely flaccid and it took time to regain my stiffness but once I did, I was back in euphoria.

The pain had been worth it as now the pleasure was more extreme. My body trembling with this new feeling of being full and touching erotic areas I had not felt before. Not to mention the extreme pleasure I was receiving for this fantasy of working to stretch myself for my mistress. I felt the urge to text her what I was doing for her. In detail I told her about the toys and training to fit her totally inside me. Mistress seemed distracted and almost unconvinced till I sent her a picture of the plug in my ass.

"Mmh so hot baby," was the next message I received across my screen.

I had now at least peeked her interest with the hot picture of my ass bent over showing off the toy inside of me. The idea I had now turned her on became too much for my fantasy to handle and I had to cum right away, I searched around for a big, hot cock girl fucking a guy and immediately found the right porn in about 3 video searches. This large 6 foot goddess was just plowing into this guy as he moaned loudly for her to take him fully. My cum built up in my balls and this pressure and pleasure felt huge and very new. I finally came as the goddess finished on the guy in the video and wow did I cum a lot. I covered my legs, stomach and the floor in cum and I knew, I would never want to cum again without something in my ass.

Chapter 7 More is Required

After the first night, I needed a few nights break since moving too fast made me sore but I knew I was hooked for sure into wanting to do this all the time and text my goddess while I did it. In just a few more tries I was able to build up to the largest of the 3 plugs, 1.5 inches at it's thickest and 5.5 inches long, and it felt even more amazing being that full when I would cum. However, something was missing from this whole experience, they were just plugs and hardly like the real thing.

I took a night to look further into making sure I could take my mistress' big, thick cock and found a blog written on the difference between training and the real deal. I found out it was best to practice with a larger and wider toy then the real cock to make sure you could stretch beyond that then settle in. Also to use a dildo and not just a plug so your ass didn't just stretch over the thick part of a plug and go back to the thinner base but instead got use to being stretched fully for a long time.

This research led me to my next toy purchase only 2 weeks after the first purchase. I bought some plugs that were more like a cock except narrowed at the bottom after having the cock head then the thick shaft. These plugs ranged from 1 inch thick and 3.5 inches long to .5 inches thicker and 1 inch longer per moved up plug. This meant by the third plug I was staring at a 2 inch thick plug that I could see no way would fit in me but I had to for my mistress. In this purchase I also bought a 5 inch long dildo that was an inch wide to practice riding and elongated stretching. However, it ended up being way to thin and didn't do much for me which will come to create my third purchase just 3 days later.

The new plugs felt much better, I could use them longer and comfortably. They were even good enough to allow me to practice riding some. After 3 days of straight use, of the 1.5 inch thick and 4.5 inch long plug, and it feeling fantastic, I knew I was close. I tried riding the dildo in this time to but out of my hour or 2 hour long sessions of jerking off it just never filled me enough to satisfy for more then a few minutes. At this point I knew I needed to buy just as close to a replica of her magnificent cock as I could so that for the month long build up, to her coming back to town, I could get something close to the ecstasy she gave me.

I went right on to an adult toy website and bought the best anal dildo they had that looked like a real cock and was thick enough and long enough with balls too. I even ordered it 2 day rush shipping. I rushed home when I got the email that it had arrived and I tore open to find the big hot blue dildo inside. (the one I am currently using while writing part of this story) It finally felt like I had my goddess with me. The long firm dildo, with large balls and thick shaft. I was so hard. I had to get this inside me now.

I fucked myself for 2 hours that night, just bouncing up and down then stopping to stroke to some porn before going back to practicing my riding. God bless, it felt so good deep inside me. I just was lost in the feeling of being filled and being able to control it. I was essentially edging myself the whole time as I wanted it never to end. After I realized how late it was then I knew it was time to cum. I found a hot big titty, big cock goddess and watched her just pound the shit out of this twink. I came so much so fast! It was just rope after rope after rope of cum. Somewhere around 9 i lost count and I just fell back completely used. I had found the perfect toy to tide me over and to practice for my mistress on.

I spent the next month or so every other day using the blue dildo to fuck myself and cum everywhere. It was amazing how much fuller my orgasms were while riding the dildo. I even got up the courage to try the 2 inch thick plug a week before I would see mistress again and I was able to fit it in with some coaxing. I knew I was finally ready to rock my mistress with this hot tight boy slut ass.

Chapter 8 I Drain Her Balls

Mistress was finally back in town and oh had I missed her so much. I needed that cock in all my holes and I needed to please that cock. I wanted to surprise her with how well my ass would take her and yet be so tight squeezing her shaft. Over the few waiting months I had been teasing Mistress with the information of me training my ass for her and it had her just as excited to see me, I just didn't know it. We had both built up anticipation that this would be one seriously hot fuck fest and we did not disappoint. I got to see Mistress the first day she was in town and I wanted to see her as long as possible so on Thursday right after work I was heading straight her way for the fucking of a lifetime.

I pulled into the hotel parking lot almost hyperventilating. I had built this moment up so much that not only was there a lot of anticipation but now I realized the pressure of if my ass would be able to cash that check I had been writing all month. However, I had to have this so nothing would stop me. I texted mistress that I was on my way up to her and got out of my car. I tried to walk casually but there was clearly speed in my step as I wanted to get up to her immediately. I got on the hotel elevator and it felt like an eternity for the elevator to get going. I even started slightly jumping up and down with impatience. Finally the doors open and I quickly rushed to her room and knocked on the door, it was time to completely drain my mistress.

Valeria opened the door looking hot as ever in a tight jean skirt and a lacy bra. She welcomed me in and as I past her she grabbed my ass. Oh how I loved her strong hand grabbing me. I could feel the anticipation that she was going to fuck me thoroughly. She closed the door then walked pasted me, while brushing my shoulder with her hand. She smiled, almost smirked, at me then sat on the edge of the bed. She reached down and pulled her semi hard cock out from beneath her skirt and said, "Okay baby, show me what you have learned!"

I dropped to my knees immediately and paused to watch Mistress stroke herself a few times before I brought my own hand down to grab her glorious cock. I always loved the first time I grabbed it, so warm and hard and pulsing. My mouth began to water so I did not hesitate past 2 strokes before placing her cock just past my lips to suck on the head and swirl my tongue on it. God her cock in my mouth had me instantly hard as a rock. I took one hand and fondled her balls as I kept going back and forth from sucking her to licking the sides of her cock. I tried deep-throating a few times just to makes sure I gagged and got her cock nice and wet with my saliva. I even then when and sucked her balls slowly but all the way into my mouth while slowly stroking up and down her shaft. Just when I was getting into the blowjob though mistress stopped me.

Mistress lifted my chin, looked into my eyes and said, "It's time to see that ass now, turn around for me and strip;"

I bit my lip and stood up as she stared at me with complete lust. All I could think of was taking her entire cock inside me and at the time I did not know but that was all she had thought for weeks as well while I had described to her all my training with the dildos. I turned my ass to Mistress and slowly pulled my pants down with my boxers while shaking my ass in her face. Mistress rubbed my ass while I was bent over and then gave it a firm slap. I was so completely turned on at this moment so I did the first thing I thought of and backed my ass up to rub it on her beautiful cock. I slowly started giving Mistress a lap dance as I bounced my ass up and down on her lap and rubbed her cock in my crack. Mistress was moaning and rubbing my ass as she got fully hard. I could tell I was finally about to get the full fucking I wanted and take that cock fully in my tight ass.

Mistress grabbed my ass lifted me lightly and then placed her cock head right at my asshole. She was about to enter me without any protection and that just mad it hotter. I breathed in sharply ready for the penetration. She slowly slide into me just the head and wow did it pop in nice and easy. At the moment I knew the sex was going to be hot, heavy and take at least an hour. Mistress moaned and pulled me towards her to sit down some on her cock. I did so taking about half of her inside me while I whimpered and moaned like a good little slut. Mistress motioned me up and down a few times and then I got the idea that she wanted me to ride her. I leaned back so her beautiful huge tits were on my back and started to slide down on her cock, groaning as it filled me completely up.

Riding mistress felt like heaven as I controlled her cock and made her moan and slap my ass with enthusiasm. Mistress clearly liked the changes I had made to be her perfect butt slut and was enjoying my hot tight hole gripping her cock up and down as at this point only my saliva was acting as a lubricant. Mistress reached around and stroked my cock and kissed my neck while I continued to let her get deep in my ass. After about 5 minutes of me riding her, I stood up to possibly re position and Mistress took it as the chance to finally get me face down and ass up.

Mistress commanded me to the foot of the bed where a small bench was. My knees on the soft bed, my face in the soft blanket and my ass bare in her face. It was time to truly test if I was perfectly prepped for her huge cock to take me for long periods of time with no pain. Mistress used the bench to get in a perfect position behind me while she shoved 2 fingers in and around my ass with lube. She spread a generous amount of lube as she prepared to pound my ass hard. Mistress gave me one more ass slap then slide her entire cock all the way into me till her balls touched mine then she just paused to feel my ass around her.

"Oh baby, you trained so well for me!" she moaned as she enjoyed my ass engulfing her fully.

":Of course Mistress, this was my dream to take it all. Now Just pound me senseless and cum inside of me!" I whimpered loudly as she started to slide out.

"My little butt slut we are definitely about to have some fun," she smirked as she pulled almost all the way out before pounding into me.

As Mistress began pounding into me from behind in doggy style, all I could think was god yes I had done it. I had worked my ass to perfectly fit her huge cock. Mistress effortless pounded me as our flesh slapped together loudly. The pleasure was so great I was stuffing my face in the mattress and moaning and whimpering like a good slut. Mistress was ecstatic and kept pounding away and slapping my ass. She even moved positions from doggy style to mounting me to get a higher deeper angle. It was pure ecstasy and my mind was blank with nothing but love for her cock inside me. This is exactly what I had dreamed of. Just effortlessly getting pounded at for her cocks pure pleasure.

After at least 10 minutes in this position, Mistress wanted to see my face as she fucked me so she flipped me over and put my legs on her shoulders. This angle almost always makes me cum as it just hits me a different way and god was I begging for it from Mistress.

"Mistress, is my ass how you wanted it?" I moaned aloud.

"Was I a good slut for you Mistress?" I whimpered in pleasure.

"I love your cock in me Mistress Valeria! Please fuck me so good, I love it!" I yelled.

I was delirious for her cock at this point as she pounded away so good. I could feel my load building deep in my balls and we weren't even stroking me yet. Mistress was starting to take breaks as she let me know I was getting her close to cumming but she didn't want that yet. However she pounded away a few strokes then stopped and a few more while stroking me till I cam all over my chest. It was easily the largest I had cum with a woman as it as rope after rope of thick cum all on me. Mistress pumped me a few more times then passed me a towel.

As I cleaned myself up Mistress lay on the bed half hard knowing I had worked her close, something client's rarely cared about but I knew why I was here and it was to get that load out of her and into me. I came back to the bed and laid my head on Mistress' thighs as I lightly ran my fingers over her cock and balls. Mistress pushed her hand through my hair to encourage me and so I licked the tip of her cock then slide it in my mouth. Never had I sucked cock after being in my ass but the excitement of it all made me not care and even think it was hot. I sat up and started bobbing on Mistress cock with my mouth getting it all sloppy as I gagged on her. I wanted Mistress fully hard again to try something we had not yet done.

I took one more long slow sloppy deep throat and gag on her cock then I turned around got on my toes and sat on Mistress' cock reverse cowgirl style. I buried her cock down to the hilt into my ass then shook my ass back and forth. Mistress was pleased and moaned, "Mmh oh naughty baby boy. Cant resist that cock?"

"No Mistress, I have to have it and I want that cum out of it and in my ass," I whimpered and moaned.

I bounced up and down slowly and Mistress gripped my ass while allowing me to just control the flow. I sped up the pace and Mistress slapped my ass to encourage me to keep going. At this rate I was taking her entire cock in long strokes as fast as I could to see if I could really pound myself out. It was not working anywhere near as well or hot as when she takes me doggy style. I realized at that point that Mistress completely controlling my ass from behind was my favorite position by far. I did however spin around while her cock was still inside me and did normal cowgirl while kissing Mistress' tits and neck some.

Finally Mistress was ready to go and knew she wanted to pump a load into me. Mistress pushed me off and ordered me back to doggy style.