I hired her and got extra services as a friends and family bonus
Ive never been super close with my little sister Jess, 10+ year age gap, but we would regularly talked about life, school and boys when I was away at college. I recently moved back to town after graduating and when I tried to spend time with her she would just blow me off for friends and stuff so I thought whatever.
I had a ton of fun in college, and had a few FWB i could call when i was in the mood to fuck, but after graduating and leaving all the college sluts behind it became harder to find something to fuck. I tried dating apps but they are shit show with bots and girls over the hill with a 4+ kids no thanks. So one particularly “hard” night i decided fuck it and looked on local sights for young escorts(i love tight pussy).
I was browing looking for girls 18-21 when i saw a pic of a girls ass in a thong that caught my eye. It was a great ass with an anal plug that looked like a flower in her asshole, but the room behind it was what caught my attention, the posters looked just like the one’s in my little sisters room. I immediately thought some catfisher/scammer must be using my sisters pics to make money but then i thought where would they get these pics of her in her underwear with toys in her ass? None of the pics had her face so i still wasnt 100% sure it was her but either was she had a great body and nice tits.
They had a snapchat username to contact her for her services and I added the snapchat under an alt i had(Jess knew my main account). Not long after i got the notification they added me back and a message asking if i wanted her rates, i responded asking if i can get a verification pic to prove she was real, and sure enough a pic of her titties with the verification but still no face. She sent the rates and said she was available now and can travel to me, so I agreed to 1 hour and gave her 50 bucks as a down payments and sent my address.
Now Jess doesnt know where i live she has a general idea but she blew off helping me move in so doesnt know my exact address. So like 20 minutes go by until i get a message on snapchat saying she’s here and i go to my door and look through the peep holes and it was a mixture of dread and excitement because it was Jess!
I open the door but stand behind it so she cant see me and run, i want her at least inside before i confront her. Once she’s inside i close the door and just say “hey jess” she screams and is getting ready to cry. But i calm her down and ask her to sit down on the couch so we can talk and I ask what she is doing she is only 15 and fucking strangers for money?
She told me she’s been sexually active since middle school where apparently she got her first bf and one day she was at her Bfs house and somehow she ended up in his olders brothers room and her Bfs older brother forced her to give him a bj while her bf watched and started to love it and it wasnt long until the older brother took her virginity a few weeks later.
Then the older brother told all his friends about Jess the middle school slut and they started to ask for Bjs too but Jess had the bright idea to charge them and was making 20 dollars a bj. She continued this into high school until one of the rich kids wanted to pay her for sex so Jess charged him 200 and she said he lasted like 30 seconds and had a small dick so it was easy money. Soon she was basically fucking this guy every day and getting paid for it each time. So all this time she was blowing me off she was making money blowing someone from school.
Ever since she lost her virginity she had a thing for older guys so she joined the site posing as an 18 year old to get paid for older guys to fuck. But she hasnt had any luck since it seems they either pussy out meeting or they dont give her the down payment and I was the first person she was going to meet with. She looked like she was about to cry and begged me not to tell mom and dad, i pulled her in for a hug and told her its ok i wont tell im here to protect her.
She calmed down and we hung out a bit and she asked what i was doing on the site i told her im horny and was looking for someone to fuck but I saw your pic and thought the room looked familiar, i guess thats when she realized all the pics she posted and sent me and freaked out that i saw her naked. I laughed and said if it makes you feel any better you have grown into a beautiful women with an amazing body she laughed and said thanks and well since youre helping me keep this secret i bet some of my friends would be down to suck you off, they always talk about how cute you are and are pretty slutty.
I laughed and said well maybe another night since i already have you for tonight, she looked at me confused before realizing what i meant. “We cant have sex youre my brother” Jess if you think about it we barely know each other ive been away at college a good chunk of your life and when you were little i was always busy with sports and friends. Plus im an older guy who you can trust and you know I’ll always protect you. Plus i already paid you the deposit. She contemplated a bit before agreeing and asked what i wanted to do, “well you just told me all the practice you have show me how well you suck dick” with out a second of hesitation she kneeled down in front of me on the couch reached in my shorts and pulled out my dick and started sucking it.
My word she was better than most of the college sluts, she could deep throat, knew how to use her hands, had a magical tongue, and sucked on my balls, soon enough I was about to cum and before i could tell her to stop she was deepthroating me and i shot my cum down her throat while she made eye contact with me. After she swallowed my cum she stood up asking if i can give her give her a ride home, i told her what do you mean i payed for an hour and grabbed her hand and led her to the bedroom.
I started to undress her, and look at her flawless teen body and then told her to sit on the bed, after she sat on the bed i put my hand between her legs to finger her pussy and she was already soaking wet, while i played with her tits and sucked on her nipples. She started to moan a bit and soon enough i was hard again and i laid her down and spread her legs as I was lining up my cock she asked if i put on a condom, i told her not to worry she can trust me remember as i slide my cock in her wet teen pussy and god damn she was tight, she let out a loud moan as i started to fuck her slowly, then i started to pick up my pace and fuck her a bit faster watching her tits bounce with each thrust. I pulled out and told her to turn around and she obeyed sticking her ass up and seeing she had that same toy in her ass, i slid back in her pussy and fucked her doggy, before playing with her plug.
I took it out and asked if she liked toys in her ass she gasped yes, put it back in! Instead i started to finger her ass while fucking her which lead to even louder moans and her shuddering as she came with my cock in her pussy and my thumb in her ass. I picked up the pace fucking her harder dead set on cuming in her pussy, as i felt myself getting close she was just moaning into a pillow until i felt the first burst of cum so i went in balls deep and held there as i filled her pussy with cum. She snaped out of her trance and asked if i came in her i said yeah i know youre on the pill relax, she got upset saying we need to wear a condom! The pill isnt 100% you cant get me pregnant and blah blah blah.
I showed her i still had her plug and asked how long she has been playing with her ass and she said her friend told her about it and how good it feels to finger her ass while masterbating. I asked how about i pay for another hour and we try out some anal sex. She instantly said no and how I was way too big and the small dick guy tried and it hurt! It took some more convincing but i eventually got her to say yes and started to play with her ass to the point i got 3 fingers in her ass and her nearly cumming again. I got behind her spit on my cock and her asshole and slowly pushing the head in with her gasping and saying go slow! Soon enough i got the head in and Jess was moaning super loud into my pillow as i slowly pumped my cock and then her phone rang and it was our mom!
She got up and answered and said yeah she is on her way home now sorry lost track of time before hanging up and getting dressed and looking at me saying your 2 hours are up and I’ll need a ride home! Im still sitting on the bed with a hard cock saying well you need to make me cum first and she tells me she’ll suck my dick in the car and lets go! I grumbled ok before throwing on some shorts and a shirt and headed out.
True to her word as soon as we were on the road she unbuckled and leaned over to give me road head. I had to stop down the road from our parents house to let her finish sucking, and just like last time she swallowed every drop and asked for her money. I didnt have the full amount so i gave her all the cash i had and said I’ll get you the rest later, she said you better if you ever want to fit the rest of your dick in my ass, before getting out and running down the street home.
I headed back home thinking about how good my sisters pussy and ass felt, nearly getting hard again. After getting home i saw a text from Jess it was a screenshot of a conversation with her friend Amanda.
A: How was your night making money;)
J: Another flake but i got to hang with my brother and he seems really lonely after leaving all those college girls, you should go suck his dick like you did with Travis!
A:I would let your brother make me his sex slave hes so hot! Do you know how big his dick is????
J:GROSSSSS!!!!!! why would i know that weirdo!!!
A: oh please youre a total perv i know you would peak on him naked! And i am a virgin so i dont want him scretching and ruining me out with a monster dick! Lol
Jess then sent a link to her insta and damn she was a cute, but very chubby, but she had massive tits and a phat ass and still a virgin with a super tight pussy…
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