The Wager Chapter 8 - My Birthday

[LOST BOY]

Chapter 1 http://www.milovana.com/forum/viewtopic ... 18&t=10069
Chapter 2 http://www.milovana.com/forum/viewtopic ... 18&t=10070
Chapter 3 & 4 http://www.milovana.com/forum/viewtopic ... 18&t=10071
Chapter 5 http://www.milovana.com/forum/viewtopic ... 18&t=10090
Chapter 6 http://www.milovana.com/forum/viewtopic ... 18&t=10129.
Chapter 7 http://www.milovana.com/forum/viewtopic ... 18&t=10580

Chapter 8 – My Birthday
Donna had been telling me that we will have sex like never before on my birthday until now I thought that was when she would be letting me have my orgasm that was overdue, particularly with the teasing & denial she has put me through these last few days. She has made sure my balls ached every night and my cock leaked every day, to the point that I have started to poke tissues into the cage to prevent wet spots.
The thought of going another month before being allowed to empty my balls was almost as unbearable as the thought of her wanting a strap on. Over the course of our marriage I have brought up anal sex a few times generally after hoisting a few too many drinks. Her reply as always been "You first". That was always enough for me to change my mind. Not that I am seriously opposed to the idea but it does scare me just a lot.
I opted out of stopping to buy the "HUGE strap on" because Ally had not actually told me to she had pointed it out in the letter but she didn’t actually tell me to. I know it is a technicality but I just could not bring myself to do it.
I headed for work and got changed before going home. I looked ridicules although the bra was barely noticeable if someone were taking anything more than a glance in my direction they would be able to tell that something was not quite right. The fact that I was wearing shorts that came to just above my knees and BRIGHT red leggings guaranteed they would take more than a glance.
I pulled onto my street hoping and praying that none of our neighbors would be out on the street. Lucky for me no one was out and I found a parking spot close to our house.
Once inside I modeled all the new garments for Donna, who just nodded her approval, smiling when I modeled the maids’ uniform. When I was done she looked me up and down. "Where are the yellow panties I told you to buy?" I explained that they did not have any yellow panties of any style in the store, and I had bought the uniform to make up for the lack of them. I could tell by the look on her face she was not pleased and I began begging for her forgiveness. "You mean to stand there and tell me that no store in that whole mall had yellow panties" I had no choice but tell her I had not looked in any other stores. "Ok pet get naked and bring me a shoe lace." I did as I was told; I stood naked in front of her as she sat on the sofa fondling my balls until my cock was trying to swell out of its cage. She had me tell her in detail about my trip to the mall, as she tightly bound my balls, squeezing them tighter & tighter against the skin of my scrotum. They were rapidly turning purple as she quizzed me about what Ally did or did not do. She then got a marker and wrote just above the cage "Do not open til X-mas." That is how I had hoped you would be when you got home... But I guess Ally just was not up to the task" Donna continued to quiz me about my experience while shopping for underwear. Taking her time and always fondling my balls caressing, stroking, rubbing, and gently squeezing them causing my cock to strain even harder. I had started to sweat and my knees were starting to feel a bit like jello by the time she figured I could use a break. She untied my balls and pulled the shoelace off, gave them a like swat with her hand and told me to get her a glass of ice water then clean the kitchen & master bathroom.
It was nearing midnight by the time I was done cleaning. I was looking forward to climbing into bed but knew I had at least one more job to do before I could get some sleep. Donna was already in bed her knees lifted and spread making the covers look like a pup tent and the buzzing coming from under the covers told me she was getting warmed up already.
I lifted the covers at the foot of the bed to crawl up between her thighs but she stopped me "get your butt plug & lube" I retrieved them "don’t take too long pet I am very horny tonight"
I went to the bathroom to put the plug in, it took a couple of minutes to get in place and somewhat comfortable. I came back to find Donna in mid orgasm. "Now get your blind fold pet" she managed to tell me between gasps. Once I was blind folded I heard her toss the covers to the side, "now get to work pet" as I got between her knees Donna grabbed my ears and guided my head between her legs, pinched my ears hard and twisted them causing me to let out a loud "Ouch" only I never got to the ch part as she pulled my open mouth down onto what I would later discover was a nine inch strap on dildo "Happy birthday Pet" as she lifted & lowered my mouth on it for several strokes, before moving her hands into the hair on the back of my head. I knew better than to fight it or protest as it would only get worse for me if I did. She continued to fuck my mouth for a few minutes. I was gagging on about every fourth or fifth stroke the blindfold was getting quite wet from my eyes watering. Donna was never at a loss for words the whole time, always giving me words of encouragement. "oh yeah pet suck my cock" "Deeper faster take my cock pet" "oh God pet I wish I could cum in your mouth" "take it all I want your chin slapping my balls" "you suck cock like a pro." She made me gag on about five consecutive thrust by pushing my head down and thrusting her hips up just as I have done to her on several occasions when the roles were reversed. The only differences are A) The dildo is longer and thicker than my cock B) She has had a lot more practice C) she can deep throat me without gagging.
I had to stop I forced my head up and finally let the head of her cock slip out of my mouth. "if you’re not sucking my cock you better be at least stroking it ..."BITCH!" Without thinking I gave my head a shake in disbelief did she really just call me BITCH? I did reach up and stroke her cock though while I regained my composure the whole thing was soaked in spit and drool. I eventually began sucking it again this time I stroked it as well giving her the best blow job I could.
My first cock sucking experience lasted much longer than I would have liked, Donna had slipped a bullet vibrator beneath the harness and she had at least three orgasms while I spent at least 45 minutes sucking and stroking her cock before the inevitable came "Ok you cock suckin BITCH I want you bent over the bed with your legs spread wide" I did this very reluctantly but I did it. she pulled the butt plug out and reinserted it several times adding more lube as she went after a couple minutes of this she tossed the plug aside "beg me to fuck you like never before bitch... beg me to fuck your ass!"
I took a deep breath lowered my face into the pillow top mattress "Goddess nothing would make me happier than if you fucked my ass."
She wiggled the head of the massive thick dildo against my ass "beg for it” "Please goddess let me feel you enter me... fill my ass Goddess... take me now PLEASE!!!"
Donna began pressing into me, it felt like she was using a Louisville slugger. She had only pushed a couple of inches up my ass but I thought it was going to rip me apart. She added more and more lube until it was running down my legs. She kept working that massive dildo in and out going deeper and deeper. Five minutes later she was giving it to me in full long deep thrusts that rocked me back and forth with every stroke.
Donna began to breathe heavily and her strokes slowed and faded in intensity, realizing that thrusting a cock back and forth is harder than it looks, gave me three or four hard thrusts and stopped. She stood there for a moment with her cock buried deep in my ass. I was glad for the break but it was short lived, with a smack to my right ass cheek "I did not say stop, get moving!" She guided me with her hands as I rocked back and forth, impaling myself on her cock, I was taking it all the balls of her dildo slapping my own balls more often than not.
Once she had rested for a while she again began thrusting and she was not being gentle, it wasn't a fast pace but it was rough. She would pull back slowly until only the head remained in my ass and then she would thrust into me as hard and fast as she possibly could, stopping only when she was convinced there was no more dildo to push in. I was grunting and or groaning with every thrust.
It was almost 3:00 AM before we stopped and so far it was a birthday to remember. Donna kept her promise we did indeed "have sex like never before" She fucked me into exhaustion and then some. My ass was gaping and I thought it may never be the same.
My alarm clock went off way to soon but I had to get to work. My ass was still feeling the effects of the pounding it took the night before. My balls ached a little despite not being edged at all and most surprising at least to me my jaw hurt from sucking her cock or at least that’s what I blamed it on, I cannot think of anything else it could have been from.
Wednesday November 21 my birthday, we were both off work for a few days now with Thanksgiving and we both had scheduled a vacation day for Friday. I knew the next couple days were not going to be a vacation at least not for me. The work day went by quick enough but I was tired from the night before after work I came home and Donna greeted me at the door with a hug and kiss. "Happy Birthday Bitch" I sighed and nodded my head acknowledging her new name for me. "Not too bad Goddess my ass and jaw hurt this morning but they feel better now, but I am beat and need a nap." she smiled "You can lay down for 45 minutes but we are going out for your birthday Dinner then to a club for drinks and dancing"
I was asleep before my head hit my pillow and it seemed like I had just climbed into bed when Donna woke me. "It's almost 6, its time to get up we have a big night...make sure to shave very well tonight."
I was showered and shaved and looking through my closet for something to wear before 7:00. Donna came in just as I had pulled out a pair of dress pants. "I have your clothes already picked out... but first we need just a bit of makeup, sit down and I will do it for you."
I began to protest profusely “I am NOT going out with makeup on and there is no way in hell you can make me!” Donna actually giggled “wanna bet Bitch” she left the room and a few seconds later called me into the bathroom. “You ARE going to get makeup on and go out in the clothes I have chosen for you or I will do this” and dangled the key, the only key to the cage on my cock above the toilet bowl with her other hand on the handle.
My first instinct was to say go ahead I can get some bolt cutters and be rid of this damn thing, but I bit my tongue and thought better of it I instead bowed my head turned and sat at her makeup area. Approximately fifteen minutes later she had a light coating of makeup applied. Next came the outfit she had prepared for me and Donna had been busy.
First she handed me my new red thong & bra then came a very pale blue top with spaghetti straps. No matter how I adjusted things it was impossible to hide the bra straps and half the time the cups were visible as I moved. Donna then handed me a pair of cut off jean shorts, now when I say cut off I mean they are basically blue jean bikini bottoms. The front pockets had been cut out because they hung down below the bottom of the leg. They were cut off right at the bottom of the back pockets and there was little more than the seam itself running between my legs. She added a pair of sandals that had about a two inch heel.
Once completely dressed I glanced at myself in the mirror and shook my head, I looked like a very cheap transvestite hooker, and there was no way I was leaving the house looking like this.
We argued a bit about my outfit and leaving in it, I knew we were not likely to meet anyone we knew at dinner or any club Donna planned on going to with me dressed like this, but we still had to get from the house to the car and out of our neighborhood, and back again. She finally relented and let me put a pair of old grey sweat pants and jacket on but I had to take them off as soon as we hit the interstate. That settled we headed out.
Once we were on the interstate I stripped off the jacket and sweats, and by the direction she was driving I knew we were headed for center city. I peppered Donna with questions about her plans for the evening. The more I asked the less she told me. Finally in center city we found a parking lot close enough to where ever we were going.
We got out of the car and Donna handed me her small clutch purse to hold while she opened the trunk. She rummaged through a few bags collecting a few things. She closed the trunk and I held out the purse for her to take “oh no” she giggled “That one is yours for the evening” as she hefted a large shoulder bag onto her shoulder “unless you want to carry this one.”
We walked for a couple of blocks holding hands. I avoided eye contact with everyone we passed it was bad enough knowing they were all staring I did not want to see them do it. Donna seemed to notice I was staring at our feet “head up bitch… from now on whenever I catch you looking down you will get a hard slap to those swollen balls when we get home.” I did my best as we kept walking we were on a side street now not very busy at all. About half a block ahead of us a couple came out of their house as we got closer it became obvious it was two guys and they were holding hands that’s when it hit me like a ton of bricks. We were in an area known as the gayborhood, now it was starting to make a little sense she dressed me like this brought me to a part of town with a lot of gay bars and restaurants. Finally we stopped in a little sidewalk eatery and yes the person waiting on us was obviously a guy dressed as a woman. The food was outstanding and I honestly can’t wait to go back. After we ate we walked for a bit just watching the streets come to life for the night. Donna dragged me into the shadows hugged me and whispered in my ear “when we go into this club I am not going to sit with you and if someone asks to dance or “whatever” you will be very agreeable” patting me in the crotch. “If things go too far or get out of hand I will step in and save you … I promise.”
At about 9:45 pm we were standing outside a bar “ok Bitch you go in and get yourself a drink, I will be in shortly. I don’t want you looking at me or acknowledging me at all, I just want to watch you and any admirers you may have.” I took several deep breathes and walked through the door, it was not very crowded thank god. I sat at a stool at the bar and ordered a crown royal; I thought I may as well get a buzz going and pounded it. A couple drinks later I seen Donna come in out of the corner of my eye. I resisted the urge to watch where she sat, but I slowed my drinking pace though.
I had been sitting at the bar feeling very self-conscious every other guy in the place was dressed very nice not a pair of jeans or a T-shirt to be seen and there I sat in cutoff jeans that were way to short a very feminine top with a very red bra that refused to stay hidden. I was standing out like a sore thumb. After about 45 minutes Donna finally tapped me on the shoulder and asked if I wanted to leave. I couldn’t get out of there fast enough. She told me that I was to go to any other bar in the area that she would find me in a little while.
I found another bar just a block away “Woodys” this bar was considerably more crowded and had a more comfortable atmosphere. The band was rockin’ and I was almost enjoying myself when a younger guy with a three day beard asked me if I would like to dance. I almost said no instinctively, but caught myself remembering Donna’s instructions to be “very agreeable”. I took a quick glance around and did not see her anywhere but it was crowded and it would be hard to pick her out especially if she did not want to be seen by me. I took a deep breath and said yes to this young guy.
I am not much of a dancer but I tried to shake my ass best I could, laughing at myself as I did. I must have done ok. After a few songs Jason asked if he could buy me a drink. Hmm free drinks I had not thought of this aspect of being dressed in like I was. “Yeah sure why not I’ll have a crown and coke… actually make it a double” and sat down. While Jason was getting our drinks I took a serious look around for Donna, she was nowhere to be seen and I was about to text her when Jason slid his chair beside mine and slid his hand up my thigh as he sat down. It happened so fast and shocked me to the core I sat bolt upright with a stunned look on my face as his hand slid ever closer to my caged cock. I did not think he was going to stop, so I stopped him, slapping his hand much harder than intended. I just sat there staring straight ahead like a deer in headlights. Catching my breath and sipping my drink I decided to slow him down with some questions.
I found out he was an accountant, working at a large firm in center city, he is 26 and he wanted to take me home. I needed to be rescued and I needed it fast. I excused myself to the bathroom and texted Donna. “I am in Woody’s and need help NOW!!!” by the time I returned to the table Jason had bought another round and Donna texted me “I will be there in 15 minutes” I sat down and Jason dropped his hand into my lap again. Thinking quickly I jumped up and headed for the dance floor with Jason close behind. I did my best to keep him at arm’s length but he was all hands. At one point when I had spun my back to him he grabbed me and started to grind himself into my ass. I damn near hit him the only thing that stopped me from slugging him right there on the dance floor was the sight of Donna standing there watching us dance. I continued attempting to keep my distance until the end of the song. When it finally ended I turned to see Donna had moved. I returned to the table but stood rather than sat and pounded my drink. I was searching for Donna she promised to help me. I decided to get myself a drink I thought about buying one for Jason but didn’t, I returned to the table to see Jason had also bout me another, damn he was not giving up. I picked up my purse and got my phone, I had a text message from Donna, “he’s cute, what’s his name?” I replied “help me get away from Jason PLEASE”
Jason kept trying to see what I was texting, when he wasn’t trying to molest me. Donna finally replied “why not take him to the bathroom and show him your cage lol” I had had enough of this game I just told Jason “look dude I gotta go my wife put me up to this” and headed for the door not looking back to see what his reaction was. As soon as I was outside, I texted Donna that I was outside waiting for her. I waited about 15 minutes before I texted her again. I was getting cold standing outside it was nearing midnight and I was very scantily dressed in November. Still no reply I went back in and to my surprise Donna and Jason were sitting together talking and laughing. I had not been seen by them yet I set Donna another text saying I was getting cold and wanted to go home. I seen her look at it but put her phone down again without responding to it. I stayed behind them for a few more minutes before texting her again “are you coming out or not” again she looked but did not respond. I waited a couple minutes before approaching them I wanted to see if I could hear them but in this noisy atmosphere there was little to no chance, at least not without being seen. I finally just tapped Donna on the shoulder and asked her if she was coming or not. Donna replied yeah I will but first sit down for a few minutes and moved over freeing a stool between her and Jason. Donna as sitting on my right her left arm slid around my back and her right began rubbing my thigh as she told me that Jason was a colleague at work and she had told him all about the situation she had me in and had asked him to come onto me as strong as he could. Yes he is actually gay and yes he loved tormenting me as his hand began sliding up my thigh again as if on cue. I jumped a little and went to stop him but Donna had me by the balls figuratively and literally at this point told me to sit still and that if I did not try to stop them for ten minutes that we could leave and she had a very special surprise for me, however if I did not let them do whatever for ten minutes that she had a very special surprise for me too I just would not like it as much.
I sat there as they both stroked my thighs under the table, as much as I hated it my cock was straining against its cage trying to stiffen. I had only been sitting for about three minutes when I felt Jason’s hand slip inside the bottom of my shorts and his fingers grazed my nut sack and the cage.
I could not take it and stood up. Donna slid a twenty across the table to Jason “well I guess that settles that. I know a little bitch that won’t be getting out of his cage any time soon, and I was so looking forward to letting you give me a pearl necklace tonight.” I shrugged my shoulders not really believing that she would have let me fuck her boobs anyway.
As we were about to walk away from the table Donna handed Jason an envelope and said “Thank you so much for everything tonight “and we finally left.
Donna was walking deliberately slowly on the way back to the car. The sidewalks were quite busy considering that it was now almost midnight. I was getting all sorts of looks and leers. I lowered my head so I would not have to see them. Donna began counting in time to our steps. 1…2…3…21…22…30 she was up to 47 when I remembered her earlier instructions not to look down, and snapped my head up. “Wow I thought you were never going to lift your head, 47 hard slaps to those poor balls.”
We got to the car and climbed in I grabbed the sweats and started to put them on before Donna stopped me “uh uh bitch not until we are in our neighborhood” We were almost there when she said “you have a rather long night ahead of you, do you want to stop for at McDonalds?” “Yeah might as well, I will have a number one combo with a coke.” We pulled into McDonalds but instead of going to the drive through she parked the car about as far as she could from the building. “Well go get your number one combo” “fine would you like anything while I am in there” “no I am fine thanks”
At this point I did not care anymore I walked right in ordered waited for it and left not giving a shit that the entire staff were poking their heads around corners to look at the cheap cross dressing hooker standing at the counter.
We drove on we were very close to home and I put on the jacket Donna stopped me from putting on the sweats. “You can keep the jacket on but don’t do it up when you go in to get my food” as she pulled into a Wendy’s.
We were much closer to home now actually only about six minutes away from our house, too close for comfort really. But I opened my door “fuck it” and took my jacket off and marched up to the door. I damn near dislocated my shoulder pulling on the door, it was locked, “perfect just fucking perfect” and marched back to the car. I climbed in and told Donna the obvious, as if she wasn’t watching. And we went through the drive through. A few minutes later we were pulling onto our street, while I was fighting to pull up the sweat pants.
Once inside Donna sat in her favorite chair, turned on some dance music “shake your ass for me pet, shake it like you shook it for Jason.”
I really wasn’t in the mood for dancing but I did it anyway, during the third song she instructed me to slowly strip while I danced, two songs later I was down to only the thong. Once that was off she lunged at me kissing me deep and hard her hands rubbing my body finally finding my balls. She rubbed and caressed them making my cock strain against its cage. “Come with me I am VERY horny and you’re going to get lucky tonight.” She attacked me again in the bedroom we fell onto the bed her tongue driving deep into mine as she continued to make my penis swell within its confines. By the time we got her out of her clothes I was in considerable pain my cock swelling though the bars of the CB2000, I was very horny and my balls ached already.
“I want to sit on your face before you fuck me.” She straddled my face and using my hair pulled my face into her core. I have no idea how long she rode my face or haw many orgasms she had, but I was soaked, the bed under my head was soaked and she wanted more.
She rolled off me “I need a cock and I need it now!” I smiled and started to tap my cage. “You are in luck I happen to have a cock and it wants out VERY badly” I smirked, knowing I was getting out of my cage. “I would love to let you out and for that reason I am so glad I gave the key to Jason” I went ballistic I completely lost it and the argument ensued.
Once we had calmed down a bit she explained her reasoning. She knew she would cave in and let me out and probably let me finally unload my swollen balls so she put the key in a stamped envelope and give it to someone to mail back to her. She had picked Jason a co-worker and that is why she had told him about my current situation. It was in fact his idea for her to take me to the gayborhood. I was still pissed but was getting passed it.
Donna called me over to her after she sensed that I had calmed down sufficiently and told me to get the strap on that she had used on me the night before. She still wanted a cock in her and as I was learning quickly what Goddess Donna wants Goddess Donna gets. Especially since she surprised me with the snap of the lock four days ago.
We spent the next couple of hours sending her to heaven in sexual bliss we fucked in every position we could think of and a few that we had never thought of before. The sun was up and the day was bright and sunny before she had enough. .

Coming soon Chapter 9 - Thanksgiving and beyond

[Juliette]

Absolutely outrageous to say the least
Poor devil just wants to be released
Locked in and dominated
Humiliated and frustrated
Limited to only licking the furry beast.