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Jenny’s little Tryst goes horribly wrong for her – Part 1

2851 words | 0 |4.63

Jenny, bored with vanilla sex wants it rough, raw and hard. Thinking this was a one time thing. But she is blackmailed and becomes a full time whore

During the pandemic, I was really really bored so out of curiosity I joined AdultFriendFinder to see what it was about.

Well, as I figured most of the “women” were fake and probably guys from Nigeria trying to get my true identify to blackmail me. But one woman complained on the forum that she was finding the guys were fake. So I decided to contact her.

We commiserated about the fakes and eventually she gave me her phone number and asked me to text her back. Sensing that she was fake, I looked up the phone number on Google. To my absolute surprise the phone number was legit and took me to her business website. She had told me she was a real estate agent, her name is Jenny and business was really slow. The business website was a nearby real estate office with her name, Jenny and personal information.

Out of fear, I googled my phone number before responding and nothing came up. So I figured she had no way of identifying who I was.

While she texted me about how boring her husband was and she wanted rough/forced sex I looked up her name on facebook and found her real quick. She was married with two adult daughters. I looked up the husband, and got his facebook profile. Pretty much had everything I needed for blackmailing.

I texted her that I wanted a hotwife to fuck and wanted her to wear something sexy for me, like a garter belt with stockings, sexy dress, etc. She reluctantly agreed. I told her the sluttier she dressed the nastier the fucking would be. We did some more texting, her telling me all the naughty things she was to do and how she craves to be a fucktoy. These were great texts I could share with her husband of course.

I booked a motel room and in advance I went there and set up three spy cams. A while later she came up in her BMW wearing pants. I said “what the fuck is with the outfit?”

Jenny stated that she had to rush over to meet me at the agreed time and wasn’t able to change.

I told her then “go out to the nearby mall and buy yourself what I told you to wear.” “What!” Jenny shouted, “I don’t have time for this bullshit. Just give me a fucking break.” I instructed Jenny, “You have 60 minutes to do this or I leave.”

Jenny said “please, please, please forgive me. I need this bad and I don’t have time to shop.”

I said “ sorry baby but you need to learn to be obedient or forget it.” “Times ticking, you have 58 minutes now.”

Jenny, really pissed off slammed the car door and ran off quickly and sped off in her BMW.

Phase 2 of making Jenny my obedient slut was working as planned.

I was getting nervous. I really wanted to fuck this bitch, but had to stand my ground. 56 minutes, 57 minutes…. 60 minutes. Oh well, got to leave. I got into the car, but in a spot that I could see her legs when she got out of her car and waited a minute.

Just then Jenny flew into the parking lot, slammed on her brakes and came out the car, her new uniform hiked up to your waist. I took pictures from the car of her sexy look. Jenny quickly got out of the car, slammed the door in rage and started walking fast toward the motel with her dress still hiked up displaying her lovely legs. I took a few pictures to help with my plot.

Jenny frantically pounded on the door “let me in you asshole, come on!”

I came up behind Jenny “your late bitch. I was just leaving.” “Here’s the room key, open up the door.” Jenny rolled her eyes, but started to open the door, when I started spanking her hard. Jenny was shocked and dropped the key and shouted “fuck, people can see me!” I continued spanking her and told her “I’ll continue spanking your bare ass till you open the fucking door you slut.”

Jenny kept fumbling with the keys, trying to get in the keyhole while I continued spanking her hard. “Fuck!” Jenny said, “Oh my god, I can’t take this” when she finally got the door opened.

I said “do you accept that you need to be punished for disappointing me?”

Jenny was obviously angry and in a pissed tone said “yea, whatever shithead, just fuck me will ya!”

So I opened the door but didn’t let her in yet. She had on a very tight knit dress that was short along with 4 inch heels. Very sexy.

“I need to inspect you first before you come in.”

Jenny said “what?” “out here on the balcony?”

I said “I don’t trust you yet.” “lift up your dress and show me your panty and do it quickly.”

Jenny was very nervous but slid up her dress to show me her panty, garter belt and stockings.

Some teens were walking home from school eating something, and they dropped what they had and one said “holy shit did you just see that?”

“OK Jenny, you may come in.”

Jenny was pissed and blurted “I can’t believe how you’re treating me!” “Like some kind of bimbo slut!”

“Jenny, that’s what you are… a bimbo slut.” “Now do as your told or leave!”

Jenny said sarcastically “yes sir, I’m sorry and I’ll be obedient.” I don’t know what came over me.”

“Jenny, clasp your hands above your head.”

Jenny at first hesitated but she knew she had to be obedient and did as told. This made her dress rise up almost to her pussy.

I reached down, slid my hand along the inside of her thighs and felt her pussy. Sure enough she was very wet and swollen. Jenny tried to hold it in, but let out a little moan.

I then grabbed her by the hair, and pulled her over to a small table “now bend over and put your elbows on the table.”

Jenny complied quickly.

As I caressed her ass cheeks I told her “you were very disobedient and agreed to punishment, correct!”

Jenny meekly said “yes sir.”

I was starting to enjoy Jenny’s obedience. It was obvious that her need for sex was making her submissive.

I kept caressing her ask cheeks “you’re a slutty little disobedient whore aren’t you?”

“Yes, sir” Jenny stammered. Continuing to caress Jenny’s buns I yelled “tell me what you are Jenny, NOW!”

I could feel Jenny’s juices dripping down her leg betraying her.

Jenny yelled “I’m a disobedient little slut whore that doesn’t deserve your cock and deserves punishment sir!”

Jenny’s knees started buckling and shaking so I started spanking her hard.

With each syllable I spanked her: “DON’T, YOU,EV,ER, DIS, A,PPOINT, ME, A,GAIN, DO, YOU, UN,DER,STAND, YOU, SUB,MIS,SIVE, SLUT?”

Jenny was screaming and squealing “OH GOD YOUR HURTING ME, STOP!” Her juices almost flowing down her legs.

I grabbed her by the hair, dragged her to the bed and yanked off her dress. Then I took out a knife and cut off her panties.

Little did Jenny know that I had a few hidden cameras in the room. I wanted her to tell me she wanted to be fucked for the video.

“What do you want, slut?”

“OH GOD, please fuck me hard Sir!”

“Say it again… what do you want JENNY?”

“OH MY GOD, Please fuck my slutty whore pussy hard…. I need it so bad!”

I pulled Jenny closer to me so she was on her knees. I had a jar of Vasoline and started to finger her butt hole with the lubricant.


Jenny kept whimpering “oh please no, not there… please, please, please.”

“OK Jenny… I’ll give you a break, but you need to suck on my cock and get me hard.”

I yanked Jenny by the hair, dragged her face over to me cock “now start sucking slut!”

Jenny quickly starting sucking. Jenny didn’t realize it but I had every intention of fucking her butt hole. Just needed to get harder. While Jenny was sucking, I played with her clit and G spot to get her going again.

Jenny then said “oh for the love of god, will you please fuck me?”

“Sure Jenny” I said. “Turn around and stay on your knees.”

Jenny quickly complied and then I rammed my cock into her sweet butt hole.

“OH SHIT NO” Jenny screamed. Playing with her clit and Gspot I kept pumping my cock in her ass. Jenny kept screaming “oh god please not there, please.” But there was no stopping and Jenny started squirting and cumming.

I held onto Jenny tight as I kept ramming my cock deep into her butt hole, all the while playing with her clit and gspot. Jenny was screaming so high pitched I think only a dog could hear her.

When I finally shot my load into Jenny, I pulled out and spanked her again.

Jenny crumpled on the bed in a fetal position. Her body spasming, unable to talk. I walked over to the bathroom and cleaned up. When I came back into the room, Jenny was still moaning.

I figured she needed more. This slut was horny as all hell. Since Jenny had a thing for hair pulling, I pulled her by the hair out of the bed, dragged her to a small round table. I told Jenny “lay on the table now if you know whats good for you.”

Suprisingly Jenny was obedient and did as told. “Now grab your ankles and pull your knees up!” Jenny again complied. I then grabbed some ankle/wrist cuffs and cuffed each ankle to each wrist. Leaving her very vulnerable with her legs spread.

Jenny, obviously terrified of being helpless, kept silently saying “oh please, oh please, oh please.” I took off my belt, and smacked Jenny’s clit (SMACK SMACK SMACK). Jenny screamed “oh my fucking god!” I smacked Jenny’s clit again (SMACK SMACK SMACK). Jenny screamed again “oh god I can’t take this!“

I figured Jenny deserved it, so I walked around to her head, and stuck my cock in her mouth. Jenny immediately started sucking on my cock like a baby sucking a pacifier.

I said “when you get your Master nice and hard, I’ll fuck your slutty hole.”

Jenny proceeded to suck my cock like there was no tomorrow. I played with her clit and gspot, but not letting her orgasm. I was finally rock hard again.

I walked over facing Jenny and asked “so do you still want it slut.”

Jenny cried out, “oh my god how many times do I have to beg, please fuck me, I’ll do anything!”

With that I rammed my cock into Jenny three times, then withdrew, letting the bottom of my cock rub against her clit.

Jenny was squealing “ OH GOD, please fuck me, please fuck me.”

I entered Jenny again and this time I fucked her for good. Ramming my cock hard into her, over and over. Jenny once again was screaming in some high pitched scream that only dogs could here, as she squirted all of the place.

Then I spanked Jennys cunt calling her a dirty little whore. Jenny was spasming and squirming as I kept spanking her cunt. I finally uncuffed Jenny. She layed on the table still spasming.

I said “OK Jenny, your dismissed, get dressed and leave now.”

Jenny said “oh please, please cuddle me and hold me.”

“No Jenny, that’s what husbands do, not your Dom.” “Now get dressed in your slutty outfit and leave!”

“I’ll let you know when I want you again.”

Jenny looked puzzled but got dressed and walked out, obviously upset at my treatment of her.

A week later, I called Jenny and told her to meet me at the hotel in 2 hours and be dressed properly. She replied calmly that it was just a one-time hookup and as much as she loved the encounter she’d never do that again.

I told her I had videos and pictures of her and if she didn’t meet me I’d send the videos and pictures to her family via Facebook. Jenny laughed “yea right asshole.” I also let her know her home address, work address, name of husband and his phone number. I also told Jenny I friended all of her family on facebook with a fake Facebook account.

“If you don’t meet me in 2 hours I will hit the send button and send this and other videos to your husband and collegues.”

Jenny immediately started cussing every four letter word in the book and asked “how the hell did you get this information you bastard.” I said “simple…. You used your work phone number and I googled it which gave me your employment and personal phone number. With that I looked you up on Facebook and found your husband and relatives.” “I friended all of them and can post your videos to their facebook feeds.”

“Now, I don’t want to hear any more bitching, meet me at the hotel in 2 hours, dressed properly.”

Jenny said indignantly “FUCK YOU ASSHOLE, I’m calling the police!” I said, “go ahead you bimbo slut, Everything I’m doing is on the phone, no proof. Everything you did is on video, pictures and texts. You’re life will be destroyed and nothing will happen to me!”

Jenny whimpered “oh god please don’t do this to me… I have too much to lose.”

“To bad” I said. “Now an hour and 45 minutes.”

I went to the hotel and set up the spy cameras again.

I was really expecting Jenny to come with her husband armed with a gun. But surprisingly she arrived just in time in her BMW, wearing a short pleated skirt, nylons, heels and a very tight sweater top. I took some pictures of her getting out of the car with her stocking tops showing, and more pictures of her walking to the hotel with the wind blowing her skirt up exposing her sexy ass. I made sure the time stamp was turned on so I could show this was a second time for her.

At the front door, Jenny half heartedly hit me calling me a bastard and asshole. I blocked the punch and took he in the room, where I showed Jenny the edited videos (of her begging to be fucked) and photos in the parking lot.

“Jenny, do you understand that you must be obedient and do as your told so your family doesn’t find out that you’re a whore?”

Jenny replied “yes, I understand.” “I don’t understand why you’re doing this to me.”

I said “because you want this or else you wouldn’t have used your work number that I could trace.”

Jenny said “I just wasn’t thinking that’s all.”

“Yes Jenny” I said, “you were thinking with your pussy and not your brain.”

I then proceeded to kiss and make out with Jenny. Surprisingly she kissed back and we made out like high school students. I was so horny, knowing I just made this dominant woman my slave, and I think she was turned on by being forced into servitude. I then gave Jenny a good solid spanking.

I couldn’t believe she was dumb enough to fall for this. Making her my sex slave is going to be such fun!

I instructed Jenny that I will be sending her “Johns” to have sex with. She is to be obedient, do whatever they want, let them do whatever they want, and they will rate her from 1-5. I told Jenny “if any client gives you less than a 5 star rating, the videos and pictures go to your family.”

Jenny nodded, looking down.

I told Jenny “I will send the clients to your office with an hour notice to you. So you must always be dressed sexy for your clients every day as you have no idea when I’ll call.”

I could see Jenny’s heart sinking as she slumped a little.

Then Jenny asked “sir, could you at least not send them to my office? Please, I beg you!” So I figured that probably wasn’t a good idea. So I told Jenny I would pay for a room at the motel that day and tell the front desk to give you a key when you arrive.

I figured that would allow me to continue filming her. The dumb slut still hasn’t checked for cameras.

With that, I smacked Jenny on the ass and sent her on her way. Part 2, is Jenny becoming a whore and being used by various strangers.

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