Realtor Ruby. Interactive Story Pt2 free porn video

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Sitting in my house staring at the phone. My ass took 2 days to recover the brutal Ruby. But ever since then I been riding anything that was smooth enough to slide in my ass. I never had anal sex before Ruby. The closest thing I found to replicate her size was a cucumber. It’s like I need it, to be filled, I crave it.

I picked up the phone and called Ruby.
Oh hey Chris, hows it going she chuckled.
Well I still need a new house and I want you to be my realtor.
One sec. I hear a car door close.
Oh Chris so hows your asshole?
It’s really good
Mmmm I bet it is she giggled
So will you be my realtor again?
Yeah of course I will but I’m gonna make a few rules.
Ok what’s that?
So every house I show you that’s what I think you want. That you say no to...
Yes?
I get to cum in your ass!
Fine !I laughed
Really?
Yeah sure!

A long pause. Then a knock at my door. I opened it to see Ruby standing there. A knee length black skirt, black stockings and 6” heels. She had a light grey blouse on unbuttoned so everyone could see her massive tits . Her dark makeup and glossy lipstick. She stood there with a evil grin on her face.

You gonna invite me in Chris?
Oh yeah come in, sorry. She walked in and locked the door behind her. She had a small bag in her hand , and tossed it on the table, something hard hit.

So Chris do you really want a house or just my cock?
I need a house I smiled.
And my cock?
Ummmm.....
Don’t play hard to get Chris , you didn’t call the cops , you called me . You obviously missed my cock!

Ruby looks me up and down. She grabbed the bottom of my shirt and lifted it off. Then she shoved my pants to the floor.
I was a deer in headlights. I just stared at her.

I like your body, I really do but you need to shave it. All your hair completely off!
Ok... I will.
My cock was rock hard. She grabbed it and started stroking. Then she got down on her knees and started sucking . I tried putting my hand on her head but she smacked it away. Her mouth took me in and out with power. Her hands grabbed my ass cheeks, her long nails digging into my skin. One nail tracing my asshole. She pulled her hand back releasing my cock from her mouth, she drooling a large amount of saliva in her hand. Her mouth took my cock back in. Sucking furiously, her saliva soaked hand teasing my asshole.
My balls tightened , I was on the verge of orgasm and she knew it. Her finger slammed into my asshole. I moaned as my cock shot load after load down her swallowing throat. She kept sucking , clearing me of all cum. She pulled her finger from my ass.

My cock now flaccid, a mere 1.5” she reached up and grabbed the bag. I felt cold plastic surrounding my cock . I heard something click together and lock. She pulled something else from the bag , it was large and cold on my anus. She shoved it in and I gasped.

She stood up and stepped back wiping her mouth. I look down to see a pink chastity device around my tiny cock, with a lock.

It’s really a shame cause your cock is a good size and your cum is delicious. But that will be the last time you cum as a boy she smiled.
She went in the bag and pulled out a few pairs of panties. These are for you.

What? Why would I wear panties I’m a boy?
No honey not anymore, now your a sissy!
C’mon get dressed I have a house to show you.
I slipped into pink panties and pulled my sweatpants back on.

I’ll drive she smiled.
We drove out to the country, where I wanted to live. We walked into a house.
Well it’s very out dated but has plenty of potential .
This is a trap!
You know this isn’t what I wanted!

She slammed me against the wall. Her mouth kissing mine, her hands shoving my pants and panties to the floor.
Step out bitch!
I follow her instructions.
She hikes her skirt up and pulled her massive meat from her panties. Reaching down her large manicured hands grabbed my thighs. Pulling my thighs up to her hips. I wrapped my legs around her. She yanked my large ass plug from me and shoved her huge cock inside me, my eyes teared. My body trembling. My arm wrapped around her neck. Slowly her cock filled my ass.

You love my cock in you! Don’t you sissy?
My lips shudder from the intense pleasure her cock made me feel.
Yes I moaned.
That’s a good sissy. She moaned
Her cock pulled out and slammed back in, over and over. My tiny caged cock bouncing with every thrust. My asshole stretched so wide.
She stared into my eyes as her cock devoured my sissy pussy. After a half hour of pounding she blew her load deep inside my ass. I mean my sissy pussy.

She kissed me passionately, your my bitch now she smiled.
Dropping my feet to the floor she slipped my plug back in.
I reached down to pull my panties and pants back up. Her massive cock staring me in the face. I grabbed it and gave it a good sucking. Oh that’s a good sissy she moaned.
I stood up and she put her cock away lowering her skirt.

So you don’t like this one? Wanna see another?
Yes I do I smiled

We seen four houses that day. My ass or pussy used at each one. I went home that night with cum leaking out every where.

2 days went by and I haven’t heard from Ruby. My ass craving her cum, I had to call her.

Hey Chris I found your perfect house, I’ll be by later to take you there.

Ruby shows up, we drive to the house. It’s absolutely perfect. Just what I wanted. I put a offer in right there and it get excepted.

We drive back to my place, Ruby not saying much. You ok?
Yeah why?
Idk your quiet
I’m ok I’m happy you found your perfect house.
So I been thinking...
Yeah Chris she smiled
I want you to sell my house.
Oh ok sure I can do that.

We get to my house, she sits down and I hand her a glass of wine.
Oh what’s this for?
Well we gotta celebrate!
She threw a small key on the table. Your cock is free she softly smiled. She gets up and walks out.

I get naked sitting on my couch looking at my tiny caged cock. Holding the key. Sitting there missing Ruby already. Now I know why she’s sad, nobody to fuck. I tried calling her but it went to voicemail. I went in the bathroom and sat on the toilet to pee. I dropped the key in and flushed the toilet.

Sitting on the couch rubbing my nipples. Rocking on my plug. Fuck I need her big cock. I thought. I went online and ordered a big dildo. Went in the bathroom and shaved my entire body, went back online and ordered a bunch of female clothing.

The next day my package arrived. I pulled on black thigh high stockings, garter belt, bra and heels, a wig. Stuck my dildo to the table and bounced up and down till my tiny caged cock was leaking.

What am I doing? It’s not the same!

Should I :
1. Call Ruby
A. Confess my love for her cock
B. Send her a sissy video
C. Ask her to train me
D. Ask her to be my girlfriend

2. Buy bigger dildos
3. MAke a ad on sex website
4. Whore on the corner
5. Forget about everything and go back to my boy life
6. Stop story

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Fucking My Ruby Chachi

Hi friends m a regular reader of ISS n yaha mein ne kafi stories padhi h jiski wajha se mujhe gutts mille h yeh apni story yaha batane ke liye. Any aunties or girls wanna get satisfy who r not satisfied from their bfs or husbands can msg me on Pehle mein apne baare may bata ta hu mein 20 yrs ka hu m student hu n mera naam h rajan mera cock 7″ long n 3″ wide h n mein ek average looking guy hu from hyderabad. Yeh meri pehli story h toh zyada tym na barbad karte hu story pe aata hu Meri ek...

2 years ago
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Arajatta of the Ruby part 1

This is the first part of what I plan to be a long story line. If you have questions, comments or even complaints please email me at [email protected] This work is intended for a mature audience, it will contain big words, strong sexual themes, exploits and well, it will get rather explicit basically. If you are one to be offended by transgender themed erotica, don't read this basically. Gavin Mason looked around the bar. It wasn't a very good bar, it was a Casino Bar. And...

1 year ago
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Ruby My Chat Friend

Hi, Friends… My name is Hrishi I am an ISS fan for long. I enjoy reading the experiences. Today I thought let me try to share my experience with you all. Let me tell you about myself I am 26 years old, medium built and decent looking man. I am working in a MNC bank as a manager back in Kolkata. The story is my real experience which happened 6 months ego I chat a lot in yahoo and got some good friends from there one of them was Ruby. Our chatting started casually no sex of that sort of thing was...

4 years ago
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Akash Ruby and me

Hi! I read these stories regularly. Some of the stories are a real turn on. I am 28 yr experienced single Delhi male. I m 6ft 70kgs clean shaven with athletic body. I have lots of wild n erotic fantasies and true experience which I would like to share with like minded peoples you can email me main ab apko jo kahani sunane ja raha hu vo ak sachhi ghatna hai. Mera pahla sexual exp 6 saal pahle ak couple(cpl) ke sath hi hua tha. Main unke ghar main peing guest tha. Tabhi se mujhe sirf three some...

1 year ago
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The headmaster pt2

The headmaster pt2I am the Gardner/caretaker it may help to understand if you have read pt1.Victoria, the Head Girl is due any second at the Pavilion. I can see her crossing the rugby pitch in the moonless night. She has her short skirt swaying as she purposely strides my way. Her boobs bounce behind her crisp white shirt as she comes up the steps.We kiss and in doing so my hands grab her bum. Before our kiss parts I have manoeuvred her skirt up so that my palms cup her beautiful bum. The fact...

2 years ago
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431 After the passing pt2

431 After the passing pt2He stared hard at the images, flipping the pages, checking each image carefully Ann of Hull, Sarah of Liverpool, and Tina of kings-Lynn all leered at him as he turned the readers wives pages. That took about two minutes as laughing he picked her easily, her face more youthful and smiling but recognisably her, he then looked at the clothed body, now beside him, markedly more robust, but to him still most attractive. She was flattered that he recognised her so easily. “Do...

3 years ago
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416 A SUNDAY SHOP GIRL REMEMBERS PT2

416 A SUNDAY SHOP GIRL REMEMBERS (PT2)(See 196 Sunday shop girl 1)Sadly, this is a very true story. It was sent to me by a lass that is now, a nurse in north America, where she moved to too escape these folk as soon as she was able Anne-Marrie (as we know from part 1) had been coached from an innocent young virgin to a used young lady, still a virgin technically but no longer the innocent, unable though because of the trap she had fallen into to tell anyone and wrapped in the shame of the web...

2 years ago
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410 Daves reassuring hand holding pt2

410 Dave`s reassuring hand holding pt2They sat at the table she naked, he in PJ`s, coffee and a chip and egg meal, filling empty stomach`s, it was the Sunday evening and she had been sleeping all day after her overnight ordeal. He too had slept after masturbating a number of times watching the video and marvelling at her absorption of the pain she had endured. They were both wondering how to break the massive silence between them. In the end it was Gaye who spoke, “Well? Am I the biggest whore...

2 years ago
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MUM 1 PT2

MUM 1 PT2Well it has been 4 week sence life changed with my mum Jean on her birthday when we first moved into an i****tual relationship and most evening mum and I would email or skype each other the on skpe it would normally be with mum and I naked watching each other get off she would always know just when to talk filthy at me telling to shot my load in her slutty whore cunt or start pissing for me to watch and telling me she can't wait till I visit again so she can suck my cock or have me...

2 years ago
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Caught by Mom PT2

Caught by Mom PT2Following on from Caught by Mom- Just Fucked the Most Popular Girl in SchoolSuzy wasn’t in school today. The day after we lost out virginities and being caught by Mom. Although Mom enjoyed having me as a ‘companion’ in her bed last night and despite receiving a very nice blowjob, I’m desperate to get my hands on Suzy again. No Suzy at School! After a very long day at school I reluctantly wander home. Could I have misread Suzy’s intensions? Has she lost interest in me? Dragging...

4 years ago
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274 VISITING A YORKSHIRE LADY Pt2

274 Visiting a Yorkshire lady. Pt2 They sat talking most of the afternoon, filling in the inevitable gaps while they had the time together reinforced by sandwiches and her home-made cake. She pealed spuds, and prepared vegetables, for the main meal of the day, as they sat surrounded by the smell of a steak and k**ney pudding in the oven. He fetched a bottle of wine from the car, a present for Sharon, and some beer for Mark and himself, while he was away Mary slipped away and returned in a...

3 years ago
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But Im married PT2

But I'm married. PT2 I felt great on my walk home. It wasn't until I got to the front door of my house when I felt guilty.What have I done? I just fucked the masseuse and let a lady eat me out.Hi honey I'm home.Mmm that's nice.What an ass I thought.My massage went well.Mmm that's nice.With that all the guilt I felt quickly disappeared. When should I make my next appointment? Two weeks I thought. I too want my pussy to be on fire like the petite girl who bit me on my tit. I was sitting on the...

1 year ago
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But Im married PT2

But I'm married. PT2 I felt great on my walk home. It wasn't until I got to the front door of my house when I felt guilty.What have I done? I just fucked the masseuse and let a lady eat me out.Hi honey I'm home.Mmm that's nice.What an ass I thought.My massage went well.Mmm that's nice.With that all the guilt I felt quickly disappeared. When should I make my next appointment? Two weeks I thought. I too want my pussy to be on fire like the petite girl who bit me on my tit. I was sitting on the...

2 years ago
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Rachel pt2

.Rachel pt2Just after the summer of fun with Liz and Mark my father got transferred to the other side of the country which really pissed me off . So with heavy heart we packed up and left within a week. I was so depressed I really loved Mark and Liz and was going to miss them so much, for awhile I thought I might never have such fantastic sex again I will always remember Mark hammering my pussy from behind as I would eat out Liz's cunt it was perfect. It took almost three days to get to our new...

4 years ago
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The boys in the group Pt2

The boys in the group Pt2: The meeting...My first time was with my best friend, later known as my boyfriend named Mark. It happened by chance one day after scuool, back at his parents house and he told me to keep it a secret afterwards. Mark even made me promise not to tell any of the other boys in the group, afraid that they might over react so I didn't.We all started hanging out together as a group again during my last year in highh scuool. After a long while of Mark and me doing things in...

2 years ago
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173 Visiting aunt Fiona pt2

173 Visiting aunt Fiona. pt2We left Fiona bound of tits, and cuffed of wrist, laid on the carpet of the living room, Amy beside her had just returned from a multi climax induced faint and the two men were sat naked waiting Amy`s full return Phil just having had a BJ from the cuckolded Rob. The three were glad of the respite, Fiona though found the tender tits a trial, purple like balloons tied and bound, as they had been for near 30 long minutes now, they were causing her some discomforts, the...

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