The $390 million weekend

Posted in: Ass Play | Sexual Blackmail | TvTs

“The $390 Million Weekend”

Everything began normally that day. I had a shower, ate breakfast and left for work. Everything was going fine until I called my fiancé around lunch. You see, I had given her $20.00 to buy me lottery tickets on her way home last Tuesday. It was the largest jackpot in history, $390 million, and I was hoping to get some of it. Today was now Thursday and the drawing had taken place last night. Since I had not seen her since she left my house on Tuesday she still had the tickets in her possession. So naturally I was anxious to contact her today to discover if I had any winning numbers on my tickets. So at exactly 12:00, when she goes to lunch, I made the call.
Even that began simple enough. “So, am I a millionaire?” I asked. “Not yet” she replied. Not knowing what she meant I asked her. She went on to explain that she had in her possession a ticket with not just winning numbers, but jackpot winning numbers. However I would never see a single penny if I didn’t do exactly as she said. Considering the ticket was in her possession and we were not yet married I knew that she could legally pull this off if I did not comply. So I began by asking her what she wanted me to do. “Come to my house tomorrow after you get off work.” She said. That didn’t sound so bad, so I agreed. At 5:00 on Friday evening I would leave work and go to Erin’s house.
As the day progressed on Friday I began to wonder more and more about what was in store for me. And when 5:00 came I could not wait to find out. Upon arriving at Erin’s house I knocked on the door and it was answered immediately. There stood my fiancé in the most incredible outfit I have ever seen her wear. It consisted of a black satin bra and panty set as well as a garter belt, thigh high fish net stockings, knee high black leather high-heeled boots and a metal chain choker necklace. She was stunning. And with the boots on and her already 5’5″ height she stood taller than I did at 5’8″. Upon seeing me she took my arm and pulled me inside, kissing me as she did so, almost forcing her tongue in my mouth. She then pulled away and told me the rules.
I was very confused when my “loving fiancé” told me that if I did not follow her every command for this one weekend that she would not hesitate to take my winnings and disappear forever. However, I felt a little better when she explained that if I did comply she would turn over the ticket, marry me and promise to love me unconditionally for the rest of our days. I am almost certain that she knew I would have no choice but to follow her lead. What else could I do? Lose all that money and the love of my life. No, I could not let that happen. So after a moment of indecision I gave in. Almost immediately I received my first command. “Take off all your clothes and lie down on the floor.” She said. I did so with no hesitation.
As I was lying down I looked up at Erin just in time to see her remove her satin panties. She slowly pulled them down her thighs and stepped out one foot at a time. But, what I really became focused on was the fact that her pubic area was completely bald. This was a first for Erin, or at least in the five years that I had been with her. I began to become incredibly aroused by this latest development. Then, Erin straddled my hips and in one swift motion impaled herself on my still hardening cock. Her pussy was dripping wet and hotter than it had ever been. In no time my dick was rock hard. Erin began to ride my cock up and down while working her hips back and forth. She was moaning and threw her head back as she fucked herself on my stick. Before long Erin began cumming. Her whole body tensed up and her pussy became a vise. As her orgasm subsided she put her hands on my chest to steady herself as she began riding me again. It quickly became apparent that her goal now was to get me off. Soon I felt that familiar sensation signaling my orgasm building. Just then Erin said, “I want you to cum in me. I want you to cum in me right now.” I began shooting a huge load into her pussy and she pulled herself off of me just as the last couple of shots flew, landing on her bare pussy lips, clit and even some running down to rest on her asshole. She then lay next to me on the floor and I thought to myself, a weekend of this certainly doesn’t seem be too bad. Then Erin said, “Aren’t you going to clean up your mess?” But, as I got up to get a towel she said, “where do you think you are going? I want you to clean it up the same way I clean you after sucking your dick.” I quickly replied, “You can’t be fucking serious!” Unfortunately, I could already tell from the look in her eyes that she was very serious. I again spoke up, “well, I’m not fucking doing it!” To which Erin replied, “you don’t have a fucking choice, remember!” And I knew she was absolutely right.
Erin spread her legs giving me a good look at the sticky remains of my own pleasure that I was about to have to lick off of her. She beckoned me with her curled finger and as I reluctantly began to lower my head to her usually sweet sex she grabbed me by the back of my head and forced my face into her crotch. Then she said, “now suck that cum out of my pussy!” I had no choice but to stick out my tongue and begin licking her glazed hole, but to my surprise my softened cock began to respond. I was becoming aroused. I could not imagine how this could be possible, but I was actually enjoying this. I started to lick the combined juices from our orgasms from Erin’s bald cunt with vigor. First the outermost lips with long even strokes. Then I moved on to her inner lips and clitoris and was promptly rewarded with more nectar as she came again, only this time my face was already between her thighs, ready to lap up her juices as they flowed from her. Then Erin instructed me to lick my cum from her asshole, so I lowered my head and licked her rosebud ferociously getting every trace off semen and licking her completely clean with my tongue. I also stuck my tongue out hard and tickled the rim of her ass with just the tip penetrating her rear opening. She moaned her approval as she pulled her bra down exposing her nipples so that she could pinch them, one in each hand. After I finished polishing her asshole with my tongue Erin told me to get on my back again. I quickly obliged and she straddled my face and said, “I expect you to suck every last drop of that cum from my cunt. Don’t let a single drop go to waste!” I immediately began sucking at her cum filled hole, which caused Erin to moan loudly. When I shoved my tongue into her to scoop out as much as I could Erin came again, covering my face with her fluid. I sucked it up as well and cleaned her entire pussy inside and out until there was no trace of our cum left. Erin stood up and put her panties back on as I tried to come to terms with what had just happened. As Erin was putting her bra back in place she told me, “get up and follow me, you’re not done yet.” My mind started to race as I wondered what else could possibly be in store for me this weekend.
I followed Erin into her large master bathroom. She reached over and began to run the bath water as she told me to get her lilac scented bath beads, shaving cream and razor, as well as some sort of soap she pointed to and said, “that will get rid of your rough skin and make you feel as soft as me and we have to get you ready before everyone else gets here.” Before I could even inquire about this latest statement I found myself soaking in hot lilac scented water and my fiancé was steadily working the rough soap all over my body. I later found out that this was an exfoliate and that it was used among many women to maintain their baby soft skin. Then, Erin handed the shaving cream can and razor to me and instructed me to remove every bit of hair from my body other than that on my head, which I kept buzzed short anyway. I was quite confused but figured what the hell, for $390 million I would paint myself blue. As I started to shave my body Erin produced a bottle of lotion and told me to apply it to myself when I
was done toweling off
. Erin then said, “meet me in my bedroom when you are finished. I have other things I need to prepare.” As I continued to shave Erin left the room and I wondered what I had gotten myself into.
As soon as I had finished applying the lotion to my body I did as instructed and reported to Erin’s bedroom. She was standing by the king size bed and I could see that there was an assortment of items placed on it. As I ventured closer I saw that the items consisted of an outfit matching the one Erin was wearing only it was pink and the boots that rested in front of the bed were white leather and appeared way to big for Erin. There was also a long strawberry blond wig positioned at the top of the ensemble. Just then Erin said, “Time to get you dressed.” I said, “what?!?” To which she replied, “well, a girl has to look her best when she is preparing for her date.” I thought fuck it, $390 million; let her have her fun. Besides, what harm could it possibly do? She started by handing me the pink satin panties, which I stepped into and slid up over my hairless thighs and over my bald crotch. Surprisingly they felt quite nice once they were in position. By the time she handed me the matching bra my cock was becoming firm and straining at the flimsy satin that presently covered it. I donned the bra, with a little help from Erin, and then she showed me how to roll on the thigh high white fishnet stockings. As Erin helped me get into the knee high boots and buckled the chain choker around my neck she told me, “after we fix your hair, (meaning, put on the curly, longhaired wig) we will need to do your makeup. Soon all of this will be second nature to you, but for now I will help you get ready.” I didn’t know what she meant by this second nature shit, I didn’t plan on doing this ever again, but I decided not to argue. Erin applied my makeup with a skillful and experienced hand. First a little powder, then eye shadow, mascara, and finally lipstick. It was a kind of metallic pink shade that matched my outfit, along with the eye shadow. Once that was complete she reached into a drawer and pulled out what appeared to be breasts. She explained that they were designed to give small breasted women a more enticing appearing chest, but considering I had no breast at all they would give me the appearance of having small but perky breasts. Once she had situated them in my bra she turned me to face the mirror. My god, I could not believe it, I was gorgeous. I looked like a beautiful young woman. My tits were small, but even still they looked great. And more surprisingly, they looked real. I stood up and admired my entire body in the mirror for at least 10 minutes. I looked amazing, and other than my now raging hard on, I looked like a lingerie model, the epitome of femininity. Then Erin told me it was time to learn to walk. She really wasn’t joking either; it took at least an hour for me to get it down pat. She made sure I knew, not only how to walk in the heels without falling down, but also how to shake my ass just right. I felt like a runway model as I sashayed back and forth in her bedroom. After we had that covered Erin told me it was time to have my reward, my first taste of womanhood. I asked her what she meant and she responded only, “you’ll see,” as she walked over to her dresser to retrieve something from the top drawer.
As Erin busied herself at her dresser she told me to go to the bed and lay face down. As I did this I thought to myself, maybe I am going to get a nice massage now. I heard Erin walking towards me and glanced up to see if she had massage lotion in her hands. What I saw was the single most shocking thing I had ever seen. She had a huge black penis protruding from her crotch. I jumped up and said, “What the fuck is that?” Erin replied, “It’s called a “Feeldo”. It doesn’t require any straps because it has a bulb on my end that holds it inside. I like it because it gives me better control by the sensations I feel in me, plus it gives the allusion of not being a “strap-on” but rather just being my very own cock. You want to suck it?” I said, “hell no I don’t want to suck it. I want to know what you plan to do with it.” “I plan to fuck you with it of course. Why else would I have it?” Erin countered. What was she thinking? There was no way I was going to let her do this. I had not even fucked her in the ass in the five years we had been together. Erin started again, “come on Kelly, you don’t want to back out now do you?” who the fuck is Kelly? My name is Kyle. When I reminded her of this she simply said, “not this weekend. If you can’t be Kelly than me and your money will split town before you can blink.” OK fine, I thought; I will be Kelly, but I’m not getting fucked in the ass. However, after some reassuring I agreed to let her try with the understanding that if it started to hurt she would stop. After all $390 million and her love was at stake. So, I layed back down and she crawled up my legs and pulled my satin panties to one side, exposing my very virgin asshole.
Erin began by using her finger to apply a bit of lube to my hole. She massaged the liquid only on the outside at first, taking her time. The feeling it caused came with mixed emotions. To say it simply, it felt great, which was not what I expected. Then I felt a slight bit of pressure as she began to work me open. After a few moments her finger slipped in to the first knuckle and she began to move it all around as well as in and out. Before long her finger was passing the second knuckle and I was panting with sexual excitement. Then Erin worked in a second finger, this one going in much easier than the first. As she worked her fingers in and out of my ass Erin asked, “do my fingers feel good in your pussy Kelly?” I could only let out a moan to affirm that they felt wonderful. Then Erin said, “your pussy is getting so wet baby, but we need to get three fingers in it before we try for my big cock.” Just then she started to push in the third finger and I thought I might pass out from sheer pleasure. My ass was getting fucked by three fingers and I loved it. Erin kept fucking me with her fingers until she was satisfied that I could take her eight-inch-long and an unbelievable three and a half-inch-thick dick. She then removed her fingers and sat beside me on the bed. Then she said, “Now suck my cock and get it nice and wet so it will slide right in that tight pussy of yours.” Without even thinking I immediately gripped it in my hand and began sucking away at it like I was some kind of deranged slut. I sucked so hard that Erin could feel the movements inside her and started to moan. Her cock glistened with my saliva as I started to really get the hang of being a girl and managed to deep throat Erin’s eight inches. My nose came to rest on her pelvic bone as Erin looked down and said, “Good girl; suck that fucking cock. You’re becoming a good little cocksucker, aren’t you.” I tried to reply but with my mouth full of Erin’s cock it just came out as yet another moan. That’s when I decided that I didn’t mind being Kelly. I didn’t mind being a girl, or even a cocksucker. I even decided that from here on out I would do exactly as Erin asked me to, no questions asked. Then Erin said, “OK that’s enough. I don’t want to come just yet; I want to come in your tight little pussy.” I stopped sucking her dick reluctantly and repositioned myself facedown on the bed again. Before Erin moved behind me she looked at my pretty face and said, “Are you ready for me to make you cum like a girl?” I could not even speak. I just nodded my head and watched as Erin crawled back off the bed, standing where my feet hung off the edge.
Erin stood between my spread thighs. She reached forward and tugged at my new panties, sliding them down and unhooking my garter belt from my stockings just long enough to get the pink satin panties over my high-heeled boots. Then she reconnected my garters and placed a hand on the underside of my thighs just below my waist. She then lifted up slightly as she pulled me back and positioned my ass up in the air and close to the edge of the bed. I closed my eyes and waited
for her
to take the next step. A few seconds later, she did. I could feel the head of her huge cock pushing at my hole. Erin leaned down and whispered in my ear, “Just relax baby and let my cock slide in. You can do it Kelly, just relax that pussy.” As I did, I felt the head slide in filling me to capacity. In fact, it felt as though it were ripping me in two. Erin just held it there giving me a moment to adjust to the thickness, and as she did the pain subsided and I began to relax even more. Soon Erin started to work her member in and out. Only slightly at first, but steadily increasing not only her speed but also how much of her cock she was fucking me with. The feelings she was creating were magnificent. I felt as though I was a teenage girl getting fucked for the first time. I could not believe how great it felt. I got so caught up in it that I completely lost track of what Erin was actually doing and before I knew it I could feel her hips resting completely on my ass. I had actually taken all eight inches. Erin leaned forward again and asked, “How does it feel to have my cock all the way in your virgin pussy?” All I could say in response was, “Please fuck me. Make me cum like a girl!” and Erin said, “Well now Kelly, you are a girl. And believe me I’m going to fuck you and you will cum soon enough.” With that, Erin began to saw her cock in and out of my ass.
I was moaning in complete ecstasy as Erin continued to fuck me in long, slow strokes. Then she leaned into me and asked, “Are you ready for me to really fuck that cunt of yours?” I yelled out immediately, “Yes, fuck my pussy.” With that Erin started to pound into me, slapping her thighs against my ass. “Yes! Fuck me, fuck me!” I screamed out. And she did for a few minutes until she said, “Now, you fuck yourself. Bang your little pussy on my big dick.” Upon hearing her say this I started to rock myself back and forth, fucking myself with her cock. Erin exclaimed, “If you keep that up you’re going to make me come all in your pussy.” I immediately picked up my pace and squeezed my anal muscles to provide as much movement for her as I could. She joined in and started to meet my thrusts, gripping my hips as she pulled me back onto her dick. Soon her pace increased so much I could not keep up and she yelled out, “Here it comes, I’m going to cum in your pussy.” As soon as she said this she began to orgasm. Her body again tensed and shook and I could imagine her shooting a load deep inside my pussy. Then I started too feel a rather strange feeling myself. It was not entirely unfamiliar, however it was like nothing I had ever felt. Suddenly I realized what it was. I was on the verge of cumming. Before Erin had finished her orgasm I started to cum. I never even touched my penis and yet I was definitely cumming. It was then that I realized when Erin came deep in my pussy she pushed me over the edge and for the first time, made me cum like the girl I had recently become. As soon as we finished riding out our orgasms, Erin pulled out of me and dipped her cock into the small puddle I had made on the bed. She made sure to get every bit of the seed onto the head of her penis before offering it to my eager mouth. Quickly I began to suck on her dick as she stroked my long curly hair and said, “That’s it Kelly, get all the cum off my cock. Suck it down like a good girl.” And I did just that, sucking it hard until there was nothing left on it but my own saliva. I even slid it back down the back of my throat again, loving the way it felt to deep throat her massive cock. Then Erin said, “That’s enough for now. We need to go to sleep, we have a big day tomorrow.” She then helped me remove my boots and undid my choker as I pulled my pink panties back up over my fishnets and into place around my slim waist. Then she gave me a see through silk teddy that was the same color pink as my bra and panties. As I was pulling it over my head Erin reached around from behind me and cupped my modest breasts giving each a much appreciated squeeze. Then she said, “This is only the beginning Kelly. I plan to use your body any way I see fit, to bring myself pleasure. I hope you are ready to get fucked like the little slut you really are.” I told her I would do anything she wanted me to in order to please her. With that we got into bed in the spoon position, her behind me with her dick firmly nestled in between my ass, right where it belonged.
To be continued….

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The $390 million weekend, 6.5 out of 10 based on 2 ratings

No Responses to “The $390 million weekend”

  1. Lee_mcgreggor

    God i wish i could find a woman to feminize me like that. Great story please continue

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  2. slutserfgurl

    That was sooooo hot! Can’t wait to read the rest.

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  3. Tree

    You had better continue this

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  4. Casey

    WOW, i wish i had a woman who would fuck me like that.

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  5. robin48

    nice story
    got my panties wet

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