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Financially Dominated and Cuckolded

This is a story about a woman cuckolding a man and taking all his money – don't read if that doesn't interest you!

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I first met Kristin on a Saturday night at a trendy bar in my city. She was cute, around 28 with dirty blonde hair, and a sexy blue dress on. I'm 33. We hit it off and I bought her several drinks throughout the night. I thought I might be getting lucky when this tall, muscular guy butted into our conversation. Kristin was obviously tipsy at this point and she didn't seem to mind. He introduced himself as Brad but quickly turned his attention to Kristin. He slowly rotated his body to edge me out of the picture. Pretty soon they were deep in conversation, touching each other, and totally ignoring me. The next thing I know they were full on making out in front of me. The girl I spent the night talking to and buying drinks for had rejected me for an athletic stud. Although I felt humiliated it was a pretty hot scene to watch. The next thing I knew they were walking out the door arm-in-arm, she didn't even say bye.

I went home and masturbated to the thought of Mr. Stud plowing Kristin. Why I didn't think of myself in that role I don't know, but I clearly felt inferior to him. The next day I gathered my courage and messaged her on Facebook that I had a great time with her. I didn't mention that she had brazenly chosen another man over me, I figured she was just drunk and it wasn't a big deal. To my delight she wrote back and said she had a great time too! I got the courage up to ask her to dinner and she said yes. We went out the following Friday – I took her to a nice seafood restaurant, got an expensive bottle of wine, and we had a great time. I noticed she was on her phone a decent amount but I didn't think much of it – chalking it up to millennials and their phones.

I was going to suggest we stop off for a nightcap somewhere but Kristin beat me to the punch. She said she had some friends meeting up at a bar near her apartment. Excited, I thought maybe she chose that location for close proximity to her apartment in case things continued to go well. We got to the bar – it was a generic Irish bar filled with 20 somethings. Not really my scene, but whatever, I was trying to get laid. We headed toward the back and my heart sank as I saw Brad from the bar the other night. Kristin made a beeline for him and gave him a big hug. I'm pretty sure he grabbed her ass too as he turned and looked at me. Brad gave me a big, shit-eating grin and said “hey buddy, long time no see.” It turns out Kristin's “friends” were Brad and his guy buddies. I was humiliated but couldn't really do much except grin and bear it and hope Kristin would choose me. Considering even I had jerked off to the vision of them fucking I knew that was pretty unlikely.

In an effort to fit in, I bought everybody a round of drinks. I then stood awkwardly off to the side while Brad and Kristin were engrossed in conversation. One thing led to another and they were full-on making out again. It was humiliating that I had dropped hundreds of dollars on this girl and she had me bring her to the guy that was fucking her. After a bit Brad and Kristin walked up to me hand-in-hand.

“Thanks for dinner and the drinks,” she said as she pecked me on the cheek and walked out the door with Brad.

“See ya round, buddy,” Brad said with a smirk.

Humiliated, I paid the tab and went home alone to jerk off to Brad and Kristin fucking.

The next morning I messaged her again.

“Hey Kristin, had a great time last night 🙂 Hope to see you soon.”

What was I doing? She had totally used and humiliated me. Why was I reaching out to her. It didn't take long for her to respond.

“Aww, I had fun too 🙂 Why don't you come bring me breakfast in bed? A bagel with cream cheese and an iced coffee.”

I eagerly obeyed and headed over. I pulled up to the complex carrying her request and buzzed her apartment to get in. As I headed up the stairs my heart sank – Brad was coming down the stairs with an arrogant grin on his face.

“Hey buddy,” He said as he walked past me.

I bowed my head and said nothing and continued on to Kristin's apartment.

Did Kristin coordinate the time of his exit and my arrival? I wondered.

I didn't care. I was becoming infatuated with her, and even though she used me and humiliated me at every opportunity I wanted more. Little did I know what would eventually be in store for me. I arrived at her apartment and rang the doorbell.

“Come in, it's unlocked,” Kristin said.

I stepped in her apartment and saw her bedroom door was ajar. Kristin was laying across her bed with a robe and panties on, no bra. The sheets were a tangled mess. Kristin had a glow about her face like she had been freshly fucked and the smell of sex filled the room. It was obvious she and Brad were having sex all night. But why did she want me to come over? I wondered. I handed her her food and coffee. She set them on the table next to her.

“Come here,” she said, beckoning me over to her.

Was I going to get sloppy seconds? I wondered. Hell, I didn't care I was infatuated with this girl and wanted to do anything to get near her.

I got on the bed and she pulled me close for what I thought was a kiss.

“I hate to ask, but could you lend me a little money for rent? I'm a month behind.”

On our date I had told her I make good money, well into six figures. I didn't want to come off as cheap so I told her of course I would help her, and she didn't need to worry about paying me back. She smiled and kissed me. After making out for a couple minutes she grabbed me by the back of the head and started pressing down. I made my way between her legs and started sucking on her thighs.

The smell of sex was intoxicating. She had clearly just had sex and her scent filled the room. Brad's too probably. I pulled off her panties and began licking. I tasted lot of fluid – a tangy, salty mixture. I was pretty sure I was tasting their combined juices but I wasn't one to argue, I was infatuated with her. Kristin ended up being quite rough with me – pulling my hair and talking dirty to me.

“That's right, suck the cum out of me,” I thought I heard. I wasn't certain so I still eagerly lapped at her pussy, hoping I would get to fuck her once I cleaned her out. After she came twice on my face she pushed me aside. I tried to mount her but she closed her legs.

“I'm too tired and I have a busy day, I need some rest. Before you go would you mind transferring me the money for my rent? Thanks.”

With that she got up and walked to the bathroom. I sat there dumbfounded. Not only had I spent hundreds of dollars on food and drinks for her, I was about to transfer her a thousand dollars for rent after sucking another man's cum from her pussy and getting nothing in return! I wanted to storm out of there but my raging hard-on won out. I transferred her the money and said goodbye. She kissed me on the cheek on my way out.

I thought about her the entire day, jerking off twice to the memory of her using me. I couldn't help myself – I messaged her the next day telling her what a great time I had. I didn't hear back from her for a few days. I spent the entire time going crazy, wondering if she fucking Brad or someone else. Wondering if she was done with me after getting her rent money. I vowed to go above and beyond to spoil her if I got another chance with her. I finally heard from her a few days later.

“Ugh, I have a date tonight and nothing to wear,” She texted me.

My heart pounded. A date? Didn't she know I wanted to date her myself? Why was she telling me this? I had to admit I was excited, though. I figured if I could showcase myself as a loyal, generous, non-jealous guy then maybe she would choose me.

“Well, why don't we go to the mall and get you something to wear? ;-)” I typed, fingers trembling. I was trying to play it cool, like it was no big deal to buy her a dress to wear on a date with another man.

“Great, there's a dress I picked out at the mall. We can get it and you can take me to lunch after.”

I eagerly agreed and pushed all the doubts I had out of my mind. I picked her up and she kissed me on the cheek. I was hoping for more but since she had a date tonight I didn't want to press. I was trying to play it cool.

We got to the store and the clerk recognized Kristin.

“Your dress is altered. Do you want to try it on before you buy?” The clerk asked.

“Sure,” Kristin said.

Kristin came out of the dressing room and looked absolutely stunning in a beautiful, low-cut, short cream-colored dress. For a moment I forgot she would be wearing it for someone else.

“You look great,” I said.

“Is this your boyfriend?” The clerk asked.

“Oh no, he's just a friend,” Kristin replied instantly. The speed in which she dismissed me as her lover definitely made my heart sink. But, she looked great and I was determined to win her over.

“You know.. I don't really have any shoes that match,” Kristin said. “Do you recommend a pair to go with them?”

“I have just the pair,” the clerk said, and came back with a pair of gold heels.

“Great, thanks,” Kristin said to me and kissed me on the cheek.

I hadn't even paid yet or agreed to the shoes but I knew I couldn't protest, I wanted her to think I was easy-going and it was no big deal. My eyes nearly bulged out of their sockets when the clerk rang up the purchases. The dress was $1699 and the shoes were $699. I grinned and handed her my card, totaling almost $2400 in purchases.

“Thanks, you're the best,” Kristin said beaming, as she handed me her bags to carry. “Now, let's get lunch.”

There was a Capital Grille in the mall so I took her there. We sat down and she ordered an expensive bottle of wine (of course). She then spent the meal how she and Brad didn't work out. He had a big dick and was great in bed but it was just a fling, nothing serious. Things took a turn for the worse when she made her next comment.

“I would never sleep with a guy less than 8 inches,” Kristin said.

I turned bright red, giving my 5″ away as if I had whipped it out on the table.

“Aww, I thought so,” Kristin said as she laughed. “Don't worry you make up for it with your tongue and your wallet though. Since you were a good boy today I'll let you taste me before my date.”

I simply nodded yes, humiliated that Kristin knew I had a small penis, and devastated that she made it clear I would never be fucking her. Still, I loved going down on her and had jerked off to the memory several times in the past few days so I was getting excited about licking her later. I paid the check and we walked to my car.

We got to her apartment and she dropped her bags and firmly grabbed me by the hand, leading me into her bedroom. She roughly forced me between her crotch and I went down on her for close to 2 hours. After she orgasmed several times she pushed me off.

“You should go,” she said. “I need to get ready for my date. Oh, do you have any cash I can borrow? I don't expect he'll ask me to pay but you never know.”

By this time I had a feeling I wouldn't be seeing any of the money Kristin was “borrowing” but I was so horny I didn't care. I gave her everything I had in my wallet – almost $400.

“Oh, one more thing. I don't want you jerking off tonight to the thought of me getting plowed by a bigger man. I have a surprise for you tomorrow and I want you good and horny for it.”

My face reddened. How did she know I had been fantasizing about her getting fucked by guys with bigger cocks than me? I simply nodded yes and slunk out.

I tossed and turned all night – my thoughts alternated between dreaming of Kristin getting fucked by someone else and going down on her afterwards. I awoke in the morning to a text message.

“OMG the sex was incredible. He stayed over all night and fucked me four times. Twice in the morning. Get over here with that tongue.”

I threw clothes on and rushed out the door, eager to obey. I arrived at her apartment and rang the doorbell. Kristin told me to come in. I walked to the bedroom and Kristin was lying naked in bed. The room stunk like sex. Her hair was a mess and the sheets were on the floor. I saw used condoms in the trash can by her bed. For some reason I was a little disappointed I wouldn't be tasting his cum but then I saw her tits were covered in a white gooey substance. Without waiting for her command I dove right in and started licking his cum off her tits.

“Good boy,” she cooed, as she pressed down on my head guiding me to her pussy.

I ate her to three violent orgasms before she pushed my head off.

“Now for your surprise,” she said.

I sat up on the bed, waiting to see what the surprise was. My 5″ dick was at full attention, poking out of my boxer shorts.

“Close your eyes,” she said.

I eagerly complied. After a minute or so Kristin fished my cock out of my boxers. I almost came in her hand right there! I was so turned on. The next thing I knew I was gasping out in surprise as my cock was plunged into what felt like a cup of ice. I opened my eyes and sure enough Kristin had dunked my penis and balls into a cup of ice. No longer hard, I retreated to my usual .5″ limp state. 'I'm a grower, not a shower,' I used to say. Although truth be told I wasn't much of a grower either.

“I said close your eyes,” Kristin said, as she slapped me across the face.

“Yes, Mistress,” I mumbled as I closed my eyes. Mistress! Why was I calling her Mistress? Although it was obvious she had incredible power over me.

The next thing I felt was cold steel around my cock and balls. It felt very snug and I heard a snap.

“You may open your eyes now,” she said.

I looked down and I was wearing a chastity device! I started to say something but Kristin put her finger on my lips.

“Shhh,” she said. “You are to wear this until I agree to release you. You are great at giving oral but it's important that you are constantly horny so you are eager and obedient. You will do whatever I say. You want this, don't you?”

I nodded yes.

“Good. Now we can begin. Log into your Amazon account on this iPad. I'm going to shop while you worship between my legs.”

“Yes Mistress,” I said as I dutifully obeyed.

I worshipped between her legs for hours. She would occasionally set the iPad down to firmly grip the back of my head as she orgasmed. It was exciting and terrifying knowing that the longer I was between her legs, the more of my hard-earned money she was spending. She finally came one last time – a violent, thunderous orgasm as she yanked on the back my head, and then pushed me away.

“Good boy. I have a busy day today so you can see yourself out but I'll expect you back here Saturday morning at 9am. Bye”

Trembling with excitement and nervousness, I made my way out of her apartment. I was crazy with lust and the uncertainty of not knowing how much Kristin had spent was incredibly erotic. Shaking, I pulled out my phone to check my bank balance – she had spent almost $10,000!! I would have cum on the spot if I wasn't in chastity. The mixture of lust and devastation was an intoxicating cocktail. She knew I had the money to spend because when I was trying to impress her on our first date I told her I made $250,000 a year and had about the same in savings. The money I had spent on Kristin wasn't going to change my life but I knew I was on a slippery slope and resolved to stop.

The week at work flew by. I couldn't help thinking that I was working in order to spoil Kristin, which was an incredibly hot feeling. I texted her a few times but didn't get a response, which made me even more turned on. I finally received a text back on Friday.

“Have a hot date tonight. Transfer me $1000 so I can look pretty for him.”

I transferred the money with little hesitation. What's another $1,000 after everything I've already spent, I thought. I'll just tell her tomorrow I can't keep doing this. My cock throbbed as it strained against the chastity device. Later that night I received another text.

“OMG he's so hot. I made sure that everything I'm wearing from my shoes to my panties to my jewelry came from your Amazon account. I'm gonna let him fuck me in the expensive dress you bought me. Thank you baby remember, 9am sharp, don't be late.”

I showed up right on time and rang the doorbell. As usual, Kristin beckoned me in from the bedroom. As usual, her hair and the sheets were a mess and the room smelled strongly of sex. She was naked and her pussy lips were swollen and glistening with her juices. Her face was glowing, it was clear she had been VERY sexually satisfied. I dove in to take my usual position between her legs but she pushed me off.

“Not now, I'm too sore from the fabulous fucking Ethan gave me. Here, let me show you pictures so you can see what a real man looks like,” she said.

I didn't really care to see what the guy who was fucking the girl of my dreams looked like but I reluctantly agreed. She showed me pictures on her phone, he was a very handsome black guy with an enormous cock. At least 9″ and thick. My cock strained against its cage and I felt embarrassed that I was getting turned on. Kristin gushed the entire time about his size, stamina, and skill in the bed. She was like a teenage girl. I tried going down on her again but she brushed me off.

“I'm not sure if you've earned it yet,” she said.

“Earned it?” I thought, “I'm in the hole almost fifteen grand to this woman, plus I allowed myself to be put in chastity. I think I've earned it.” I was too timid to voice these thoughts so instead I asked meekly, “What can I do to taste your pussy, Mistress?”

“For starters things are going to change. I want you to put all my bills in your name. You will pay each one on time, without fail. Once you have transferred the bills to your name I will let you taste my pussy.”

My previous thoughts about telling Kristin I was done being used for my money went out the window. I was so horny that I eagerly took over all her bills, totaling about $2500 / month, including rent. She let me eat her to two thunderous orgasms before pushing me off.

“Now, since you've been such a good boy, I will allow you to be released from chastity on one condition. I have almost $15,000 in credit card debt. You are to call off work Monday and bring a certified check for the full amount. Once the balance is paid off I will permit you one orgasm before locking you back up. Now leave, I'm seeing Ethan again tonight and I need to get ready,” she demanded.

Humiliated and trembling I left her apartment. What was I getting myself into? I was dipping into my savings and now greatly reducing my paychecks to help support her. When was this going to stop? I imagined my accounts hitting zero and felt a tremendous surge of excitement as my cock pressed against the cage. I was determined to bring her the money on Monday so I could finally cum, then I would put a stop to this.

Monday came and I made sure I was at the bank when it opened. The teller looked at me a little quizzically when she saw the amount, but I had the money so she gave it to me. I raced over to Kristin's and gave her the check.

“Good boy,” she said, as she patted me on the head and kisses me on the forehead.”

We went to the bank together and she deposited the check. On the way back I asked when I was going to get to be released.

“Soon,” she said, “I just want to make a quick stop first.”

We pulled up at a jewelry store.

“I want a nice necklace to put the keys to your chastity device on. Most people won't know what it means but those who do will get a good chuckle out of it. Besides, wouldn't you like to see a video of me sucking a real man's dick with your chastity keys bouncing around, tormenting you?” Kristin asked.

Humiliated, I simply nodded my head yes and we headed into the store.

Updated: December 19, 2016 — 5:54 am
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