My Mistress, Better With Age

My Mistress simply grew better with age...

I was in my late 30's now and starting to finally get a decent income through mostly 2 of my own web based service companies, but I have also been working part time for Home Depot to help. We are now looking for houses on the web and our local open houses on Sundays. Some people may not agree with me when I tell them Allison is truly the reason for such a turnaround, but they are wrong. She was just an extremely beautiful girl with bleach blonde hair and the sexiest lips I have ever seen. I was at least 30 or 31 when we met and she was still bright eyed fresh from High school and no more than 19. I slowly turned her on to S & M which wasn't that hard to do for me, but my true fantasy or fetish was to find the perfect beautiful woman and after we had fallen madly in love get a steel chastity tube from Mistress Lori's website and live happily ever after.

The reality is always cooler in the movies...

The first year of my new life was a challenge. Mistress was extrememly careful with my, no, no, no..... that is her property now and helped me keep a very strict grooming routine that I have perfected with my eyes closed nowadays. I had to be smooth all over now, even my chest as Mistress wanted my appearance to make men comfortable. She told me she wouldn't do anything for the first 30 days, but after that she was going on some dates. I usually dressed normal and casual unless Mistress Allison had a date, or certain company that Allison enjoys showing me off to in special, often slutty outfits that she truly got got off on as she could dress me like a girl. One guy she dated for almost 6 months was somewhat bisexual and he would call ahead to just ask if I would also be there. Ally suspected he was more gay than bi but since he had an 8 inch cock that didn't seem to mind pounding the greedy pussy. Once we got comfortable together he was more open about finding certain boy things fascinating.

Eventually Allison was curious what her lover would do to me so she offered him 30 minutes alone with a gagged and tied up version of me, but he had to take a Viagra now and allow me to coat his cock in LMX 5% lidocaine numbing gel and put a condom on it and re fastened my wrists. Mistress set a timer for 15 minutes and told me "Slave when the timer goes of I want you to remove his condom and reapply another coating of the LMX cream, especially around the head of his big juicy cock" Mistress smiled at me, then winked and left me in a very vulnerable position.

He ended up taking me by the arm and layed me over a large wooden chair. He used some rope and fastened me down and I thought he was going to rape my ass just like that. He pulled his black leather belt through his jeans that were tossed on the floor and began to whip my behind. He was not messing around and each crack of that thick belt made me want to cry out. He would stop once I pretty much did begin crying and trying frantically to move me ass away to which he just laughed and said " I was going to stop and move on to tickling you but honestly every red stripe I put across that rosy red ass of yours is making me harder and more excited". He whipped me for what felt like an eternity but actually was about 5 minutes. He walked in front of me with his nice hard cock pointing at my mouth and put it in. I sucked his cock with a condom on and he began holding the back of my head, creating a good paced rhythm. Allison came in and it was time to put on more numbing cream.

"Wow time really flies when your having fun doesn't it Slave" she said. The buzzer sounded and Allison promptly unlocked my right wrist from its steel cuff to remove his condom. I pulled it off slowly and stared in admiration at the stretched out rubber. "Awwww poor Slave are you feeling a little jealous" she said and giggled at me making me feel so inadequate in such a way only she could do. "Now suck the cream off his cock Slave" she instructed and I opened up and swallowed his cock into my mouth for the first time. I then felt her hands on each side of my head working me up and down.

"Come on bitch you have work to finish" she said sternly pushing me up and down until the cream was completely gone. She pulled nim back several inches until his cock sprung out of my mouth, then gave him a final wash with a soapy small towel. "Oh my it seems you have a new fan" Mistress said to her lover. "He hasn't taken his eyes of your cock once since stopping 5 minutes ago" they both laughed and her lover came near me and slapped his thick cock in my face several times. "You know with the right makeup, a wig, and a 6 pack of beer......anythings possible" he smiled.

I was positioned on my back with my head towards the foot of the bed. My hands were both tied apart firmly by Allisons' big dicked lover. She had made it a point to not introduce us by name but tonight she changed that. " Mr. Gregory apparently is very curious about you slave" she told me as he was in the bathroom. "Apparently he wants to humiliate you and dominate you in ways I had never really considered" I got a little worried and asked "In what kind of ways Mistress?".

"Well to be honest that is between him and me but next month on your day of release I have allowed him to.....well....how do I say this?" She paused for a minute and finally said "Well we made a bet Slave, and to avoid giving up any clues he is betting he can convince you to go another 60 days with his offer and I am betting that you wont" she finished and he came out of the restroom and approached the bed.

Allison sat right down on my face in a sort of 69 while Mr. Gregory got behind her in a doggystyle position, his cock half erect. I just began licking on Mistress' yummy clit as her lover seemed to become instantly hard as steel and rubbed his cock against her pussy lips. He made sure to rub his swollen head down onto my lips several times before starting to push inside. "Allison this numbing shit is no joke" her lover said as he went in deeper. Allison just laughed and said "Thank Gawd for Viagra" and I smiled but kept licking. At least 5 minutes had passed and Mr. Gregory seemed to be getting frustrated. Allison said "Fuck me harder bitch, make me scream in ecstasy". He tried to do just that. He began ramming his cock harder and harder into her. His balls were slamming against my forehead with each thrust. Allison was moaning and saying things I couldn't understand. He took a break and pulled out his cock and fed it to me. I felt obligated so I licked his cock head over and over until he went back inside her. He pounded her harder, faster, so fast his balls and cock were just a blur to my strained eyesight. I felt Allison cumming.

"Oh FUCK!!! Awww GAWDDDD fuckcckckc FUCKKK!!!!" she cried out over and over. I thought something was wrong. Then she started gyrating, pulsing, almost crying in pure sexual ecstasy. He lover grunted like a wild boar and just held his cock deep with the bottom of his shaft pushing on my nose. I felt his cock throb, no more like pulsate with each squirt of ejaculate that traveled through his huge cock into my Mistress' lovely pussy.

I was exhausted, they must have needed an IV and shot of morphine after the fucking I was just witnessed to and part of. To think the entire time my poor chaste cock never growing an inch. It was more like a pee pee as a child would say since that's all it does is urinate. Fuck I wanted her pussy bad and after seeing what I was up against I knew the odds were against me. I licked up all his cum from her pussy as he got up and got dressed. When Ally was satisfied I was untied and allowed to go about my business. Right after she untied me my mouth kinda dropped open in shock as my Mistress' pussy was stretched wide open. Then my inner voice simply spoke to me and said "I don't think she could even feel your little dick inside her anymore".

Life during the week was pretty normal. Despite my being a chaste Slave I still did a lot of other things that were not sexual in anyway. Granted I usually began and ended my day licking Allison to orgasm, but the time in between was spent on my various hobbies. Allison had landed a very high paying job in hospital administration a few years ago and she decided it would be best for me to stay home and become her full time slave. I keep our 2 story 5 bedroom home in immaculate order. Dinner is ready at 5:30 every night for Ally. Allison also keeps me on an intense 1 1/2 hour daily workout routine with Sunday my only day off. I am generally allowed very little in clothing unless certain unaware guests stop by. I did a good job this week despite my perverted little boy mind fantasizing about getting my release this weekend. It had been 60 long days and my poor chaste cock and balls were crying out for relief.

Friday night rolled along and Mistress had yet to arrive home. It was my scheduled night for an orgasm and I was flushed and shaking with the anticipation. Allison arrived home 2 hours late and with a group of friends. I could tell from their scent that they had all been drinking.

"Bartender another round" Mistress Allison demanded of me so I did my best and poured some drinks. 20 minutes later Mr. Gregory showed up which was a surprise to me with 2 other guys. Everyone seemed to be having a good time, yet I felt suspiciously left out. At the same time I also felt as if all eyes were on me. I knew that something either very fun or very humiliating was about to go down tonight. The music was playing and the girls began dancing. I was sitting quietly when Allison and her friend Sunny approached me. "Can I see it" Sunny asked Allison without any hesitation. Of course Mistress obliged, in fact she ordered me to take my pants off.

Sunny just began laughing "Oh my Gawd I think he's starving or needs some sunlight Allison" she said with a buzz from the wine they all drank. Sunny dropped to her knees and began pulling on it and talking to it "Oh you poor poor wittle guy" she whispered and rubbed my balls. "Wow...it's smaller than my thumb" she said and started laughing. "His balls are huge though" she commented and squeezed them hard. "I heard you are the best pussy liker money can buy" she started and was cut off by Ally. "Just hold on Sunny Greg has a special treat in store for him". "Game-time everyone!" Allison shouted.

The men at the party came and handcuffed me behind my back. Greg I knew, the other two I did not. "Tonight is my poor little dicked chaste slaves one night to get unlocked and have an orgasm" Mistress informed her guests.

"Gregory and I wanted to make it interesting and figured why not make it a party". "This is Evan and this is Ted and they volunteered when I told them what we ere planning, and of course our contestant can opt out at any time and take his consolation prize of fucking a rubber pussy for 30 seconds, or he can compete for real pussy if he takes and wins the challenges" Greg said. "Okay I'll play" I said without hesitation. They had me pick a number between 1 and 6, I got 4. "Who is in seat # 4" Greg asked and it was of course Sunny again. He asked her how long on average it takes to suck her husband off, start to finish, no hands. She guessed she could do it in 5 minutes. "Okay the game s simple if Slave can suck each cock in under 5 minutes using only his mouth he wins and gets to fuck his Mistress Allison, if only one in under 5 then the rubber pussy, and if he fails at both he will be milked anally with his chastity tube on. Place any bets you would like now as we are about to begin" he finished holding Ally as she smiled and loved the perverted excitement.

The first guy got naked and layed down on the carpet. I with some help was positioned in he 69 over him. I was looking at his juicy but limp cock. Then I heard "Ready, set, go" and my 5 minutes had begun. All the girls sat around me and started giving me advice. "Suck it"....."get him hard"..... I was nervous and humiliated until I realized if I did not start sucking cock now I would never get to fuck my Mistress. I sucked his entire limp circumcised dick into my mouth. I massaged it with my cheeks and tongue. Finally he started to get hard. I heard Sunny shout out "3 minutes 43 seconds" and something just clicked in my mind I mashed my head up and down, faster and faster, occasionally letting the head pop out only to suck it right back in. faster and faster I went. I even started trying to deepthroat him, which to my surprise I could almost do. His cock was nice and I guessed around 7 inches long and decent girth. I was relentless and would not give up until I could taste cum. Sunny shouted out "30 seconds left Slut" and I just kept bobbing my head up and down over and over and at about 13 seconds left it happened. He moaned out load "I'm cumming" and I opened my mouth and kept licking for the girls to see and prove I had done it. "Swallow it Slut" Allison said to me and I did grasping for every drop.

"Wow what a lucky little whore, 13 seconds, damn" one f the girls said. The first guy got up and within 45-60 seconds the second dude was ready beneath me. Fuck I thought no break or anything. Then it happened " 4 minutes 59 seconds" and again I had to go right at it, unable to even enjoy sucking my first two cocks ever, no just frantically sucking in and out, up and down, desperate to get some pussy for a change. Time just kept ticking away and this guy seemed unresponsive. He was hard and all but maybe he had taken some drugs or some shit because when Sunny said 45 seconds to go I had already given up and just tried to enjoy what little time left I had with this cock and just licked around the head in circles. "Ahhh looks like that cock beat you" a girl said I didn't know. The timer went off and I was pulled off his erection, his unspent hard cock just laughing at me I thought inside. I looked at the solid S & M table and saw it was covered with a large white towel and of course my favorite sex toy, a rubber and very real looking pussy masturbation toy, sitting in the middle. Allison hugged me and whispered in my ear "I bet you loved sucking those cocks huh" and kissed me and lead me to the table.

"90 seconds is the cutoff ladies and gents" Ally spoke. "And in all fairness he hasn't made it past 33 seconds ever on this particular model of pussy" Allison said and broke into laughter. "My ex boyfriend Phil actually bought that for my Slut" Allison remarked. "He got way too jealous sometimes though of my Slave and despite catering to pretty much all his demands it still wasn't enough" Allison explained.

"I mean jealous of my Slave's little 4 inch erection going inside me for mere seconds every few months when he had an 8 inch long and super thick cock? So my loyal Slave went without his Mistress' pussy every 3 months as before and now had to suffer the indignity of fucking this rubber toy. That asshole Phil actually convinced me to not fuck my Slave at all, not even on his birthday, and I did just that for about 15 months. When that asshole tried to get in the way of my Slave's oral pleasuring of me it was the last draw and I told him to get the fuck out" Allison told all her friends who listened intently.

"You must admit if you had such a beautiful creature licking and sucking your pussy and clit for sometimes 3 or 4 hours a day, would you give that up? I found a new guy pretty fast and he was very open and accepting of my Slave. I did although realize I had to limit sex with my Slave for my boyfriend's feelings and have kept it to just once a year on his birthday and until he can last at least 90 seconds inside his rubber pussy there simply won't be any birthday fucks coming his way" Allison laughed, laughed at me, sh was obviously very drunk. "Can I unlock his chastity tube Ally" Sunny asked.

Allison handed her the key, grabbed a glass of wine and planted herself on the couch. Allison's good friend Sunny placed my hands in the steel cuffs on the side of the table. Then my ankles. I was fastened down but with some movement, especially up and down movement. "So how long has it been since that sad little cock has even been close to a real pussy huh slave? Sunny asked me while unlocking my PA post and then cockring. "My birthday 2 years ago Mam" I answered. She removed the steel tube, then ring, freeing my chaste cock to the cool breeze of the nights air. Ally's other friend Daisy I just realized was only a foot behind me also checking out my penis. "I sure hope you're a grower" she said behind me making Sunny also laugh and me blush.

"Allison is passed out" Daisy said as you could hear her snores. "You know this just wouldn't be right we should just lock him back up" Sunny said with n evil grin. "Maybe but I think he might get blue balls so bad they might have to be amputated" Daisy replied. "Well do we just let him fuck this pussy toy then" Sunny asked then laughed. Daisy also laughed and laughed. "Look he's starting to grow" Daisy noticed and touched my cock for a moment. "Awww look its so cute trying to throb for us.....go ahead little penis grow" they both laughed again "He throbbed it again, filthy little pervert" Sunny giggled and taunted me.

Daisy started massaging my balls from behind "Wow his balls are fucking huge...Oh and its growing some more". Sunny grabbed a ruler off the kitchen table and sat it beneath me. "Oh don't worry Slave dick I'm not going to beat you with it, nope I want to see how big this little guy can get". I could feel blood engorging in my penis and it felt excellent. She grabbed the ruler "Look Daisy he is at 3 and a half inches and wait, wait, he's growing". Daisy added " Oh does it excite your little dick that were measuring it...hmmmm Slave? I'm getting my camera to take some snapshots, just your little dick and me" Daisy added and got her purse. "Oh wow Daisy he's over 4 inches, how adorable" they both laughed again.

"You know Allison said he was 5 inches before she locked him up but over the past few years his erections just aren't as hard and full as they used to be so he really has lost an inch in about 3 years I am guessing" Sunny said. "Sunny take my pic back here" Daisy said as she held my boner downward with one finger and the ruler in her other hand. I could see the flash go off and off many times, each time my cock throbbed. They took at least 2 dozen pics of them posing with my hard little cock. "You know Slave" Sunny said " Your Mistress is a great woman, I mean she has found a purpose for you sexually despite your lack of manhood, and she has saved dozens of women from suffering the indignity of having your penis enter them by keeping you chaste". Daisy said "Damn girl that's so true, nothing like making out all night on a date and getting home and discovering that 4 inch hard-on". Sunny also said to Daisy "And Allison told me he had a serious premature ejaculation problem... didn't you Slave dick?" I said "Yes mam I did, and honestly chastity hasn't helped it very much, in fact I am usually boiling up with cum and an orgasm as soon as I stick it inside my toy or whatever Mistress lets me cum on". Sunny shook her head side to side and said "You must eat one mean pussy for her to keep you around" she laughed and then motioned to Daisy "Why don't we help Ally out and drain this little dicks balls and get him locked back up asap".

"Honestly Sunny I want to see him shoot his load, you know and not inside the toy pussy" Daisy said. "Well Allison might get pissed if you gave him a hand job, but... Slave you yell out before you cum so Daisy can pull your little dick out and stroke you over the pretty pussy ok?" I replied "Yes mam of course". Sunny warned me she would get Ally to keep me chaste for the next 5 years with some big lie if I did not. "Well time is ticking, get on that pussy Slave..." I mounted it and aimed my cock against the lubricated lips. "Now were not going to time you but I expect you to fuck her hard and as fast as you can from start to finish Slut, so if you start slowing down or playing games trying to hold back your orgasm its over and I will pull it out from under you and lock you back up without cumming so don't fuck around".

"Go ahead begin anytime now" One of them said as my heart rate was now pounding hard. "Pretend it's your Mistress, fuck it like you would fuck your Allison". I started pounding away. I went fast and hard and balls deep with every thrust. "Oh Gawd, fuckkkk....." I moaned aloud. I could hear them both counting out "1,2,3,4,5,6,7,8" with every thrust of my sexually deprived cock. "12, 13, 14, 15, 16, 17" Daisy kept up never missing a thrust. Sunny was now laughing at me "Whoa stud..... you're making......my pussy so jealous." Daisy now was at "25,26,27,28" and then I felt my balls boil over as my orgasm rose throughout my loins.

"I bet Daisy wishes you were pounding her pussy with that thick little juicy four inch cock Stud" Sunny said. "Oh fuckkkk I'm gonna CUMMM!!!!" I yelled out as I got ready to pull out. "Please jerk my cock Daisy" I begged in a deep and very serious tone as I popped my erection out and over the fake pussy lips. She didn't let me down as I felt her soft hand tug down once, then twice, and then a thick whitish stream of cum squirted on top of the pussy lips. Followed by another thick rope of semen. "OOOhhhh yesssss" I moaned as she continued to gently tug up and down on my ultra excited cock. "Oh my Gawd Stud, how much more could you possibly even have"

Daisy giggled while holding my cock in her hand. I pumped out about 4 more thick globs of whitish, yellowish semen as she just held my cock firmly, almost trying to squeeze it and make it stop. I shook all over from head to toes whispering to them both "Oh thank you, thank you so much ladies, I am forever in your debt" I squeezed my PC muscle again and another white droplet formed on the tip. The rubber pussy, that by the way looked almost real, was completely splattered from top to bottom in my hot man juice. "Who would have thought such a cute, nonthreatening little cock like that could have possibly made this mess" Sunny said smiling and now playing in my cum with her fingertips. "I knew it was going to be a big load" Daisy said and paused as in deep thought " But come on Stud, I mean what if I had decided to give you a blowjob.....I think I would have drowned in all that hot, thick cum."

Sunny and Daisy still both were talking about my load. "I remember Allison saying that after Greg fucked her sometimes she would let Slaveboy have sloppy seconds, after he cleaned her up first of course, and she would laugh and laugh asking him if he was inside her yet even though she knew he was balls deep just to fuck with him and because she truly could barely feel him after Greg's Mag-light sized cock stretched her out. She told me her favorite thing was to text and keep a straight face while he cried out and moaned her name in sexual ecstasy." Daisy then said "Allison is my new Idol, I want to learn everything I can from her and find my own slave. I just have that stuck in my mind now, Stud over here pounding her pussy with everything he's got, moaning and groaning, calling out her name while she just lays motionless texting some other guy, fuck humiliating a man like that just makes me feel so powerful and horny, I must try it Sunny".

Daisy got her stuff and was about to leave and came to me and slapped my ass several times. "I'm going to ask Allison if I can milk you next time you big Stud" Daisy said as she left and laughed in a very sinister way and shut the door. Sunny looked at me as she was preparing to lock me back up and said "I think we have created a monster" and also slapped my ass.

The End

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Page last updated 2012-Oct-20 by: Altairboy@aol.com