I’ve woken up on a saturday morning in my appartment after a quiet night of gaming. My roommates wouldn’t be home until mondaynight so i was planning for a party / night out with some friends.
in the past half year i didn’t really have all too much succes with my sex life ever since I broke up with my girlfriend Jamie. It felt quite weird as i’ve always had some kind of attraction to me wich saved me the embarresment of being rejected.regularly girls would approach me when going out, especially at the kind of EDM party’s i went to.This ultimately gave me a confidence boost and alot more bedpartners as i had been a virgin until age 18. (after the first time it occured alot more often)
i felt it was time to try out tinder, all the girls at party’s who used to seem into me didn’t really show the same interest after my relationship. Any guy has to try it out i guess, so there we go.
A few hours later and quite some failed conversations there was a match.Not just a girl, i had seen her before.. She’s the ex girlfriend of my ex’s little brother.
Her name is Anna, and quite honestly, i already fantasized about her while dating Jamie. She had the most sexy voice , a beautiful tan and a big C-D cup already at age 18. She surely had become older and with the years she looked like a thick goddess. She still had a bit of her old Skater look but overall looked more mature.
She immediately messaged me and asked me how it’s been since the break up with Jamie. After some catchup talks and some flirting inbetween I gather the courage to ask if she’s having any plans for the night.
” well, i was just gonna drown in some wine and netflix, unless something better pops up ”
“I happen to have the appartment to myself for the weekend being.”
“I know u and Jamie loved to get fucked up. u can expect me around 21:00.”
We end the conversation smoothly all while i’m jumping in the air from excitement. i’ve dated with some stunning girls before, but i had to pinch myself a few times to check reality. Anna was a true goddess.
The day went slow as i was so pumped for Anna to arrive. We live around 2 hours apart from each other so i already expected her to be late. After doing my workout routine and preparing / enjoying dinner, it was time to clean up, as she would arrive in about half an hour. My cock had been throbbing this whole day with all the thoughts in my head and the amount of time without a sexual partner. The thought of letting out a quick wank went through my mind. I hadn’t jerked off in a week or so and my hornyness was out of the roof. Just as i was considering i heard the bell rang. FUCK, it’s Anna already! I collect my thoughts and walk downstairs to let her in.
”Hii, good to see u again Sam, it feels like ages ago” Anna says, as she storms in and hugs me tight.
” likewise Anna. I can still remember u being in high school when me and Jamie were dating. I’ve underestimated how much hotter u’ve become since then” I say while being so mesmorized by her looks.
Anna’s wearing black leather skinny pants, a red crop top wich shows her amazing toned belly including her piercing. The crop top seems to barely be able to hold up her C / D cup breasts. As finishing touch she wears a pink jacket made of a soft plushy fabric.
Right as i’m thinking about how long my staring has been going on i notice her walking past me upstair while saying: ” U seem to like the way i look Sam, but let’s skip the drooling and go upstairs for a smoke. I’m dying for it”
As we get upstairs I guide her to our roof terrace. One of the biggest plus points of our appartment is being able to host small party’s on there if the weather is good.
It’s already getting dark outside as we smoke some weed, enjoy the music and fill ourselves with wine and laughter.
As we both get more intoxicated, the conversations slowly shows the increase in our libido’s. Anna starts to ask about my sex life with Jamie, wich she seems a bit too interested in. After a few spicy questions back and forth about embarasing bedroom stories, Anna walks up and sits on my lap to pass the joint.
At this point my cock is throbbing, actually from the moment she walked in i felt so intensely arroused by her already.
As she slowly starts grinding in my lap, i feel comfortable enough to grip my hands around her waist.
“Omg Anna, ur body is so amazing. U’d be surprised about how many times i’ve fantasized about you.” i stutter as i still can’t believe what’s happening
” Hihi, u think i couldn’t tell with u always staring at my curves. Even when u were dating Jamie.Wich makes me remember, Why did she cheat on you? From what i’ve heard she told all her friends that u had a small dick, so eventually she needed something better sexually. ”
” That fucking bitch. That’s why all our mutual female friends were not interested in me anymore! Well, fuck it. Anna u must know that it’s not true, esp after grinding on my lap for a good few minutes.
” Don’t be embarrassed Sam. That’s exactly what i’ve came for, I love to tease boys like u who can’t handle me, so after I’ve heard about your size i was convinced.” She says devilishly while continueing to grind on me.
I can’t handle the continuous teasing anymore. As i push her off me, I stand up and drop my pants and boxxers for her.
She looks very shocked, as my boxxers fall down and i expose my fairly big 7.8 inch cock. Anna walks up and grabs my meat as she mumbles something again.
“Omg i didn’t know Sam. I actually came here to tease u and leave u with blue balls, but this had made everything even more interesting. But that leaves a bigger question, why dit Jamie cheat on u!?It can’t be because of this fella down here, so what is ur problem? Do u have some weird fetish? I’m sure we will find out” As Anna says these last words i see her phone camera flash right at me while i’m still standing naked with my boxxers down.
“Wtf are u doing Anna?” i say shocked but angry.
” Just trying to make sure I will get what I want. Now give me your phone! Im sure there’s some dirty stuff on there to make me more informed about ur fetishes Sam.”
I pull up my boxxers and leave my pants off. I’m soo horny but at the same time it’s been getting a bit more scary with Anna. She came here for a reason and now she has a nude of me. As i act like reaching to my phone to give it to Anna, I quickly grab her and try to pull her into the kitchen.
This is the moment to take control, take the phone and make her realise u Can handle her before it’s too late.
As we’re struggling, i’ve grabbed her from behind and try to bend her over against the kitchen table while i’m holding on to her perfect tits.
” Get off me Sam, i will make u pay for this!” Anna moans as she struggling to get loose.
Slowly I make way for one hand to reach down her Tight leather pants while i struggle to hold her with the other arm. Once my hand slips down her panties, I immediately feel how wet all this teasing has made her. She let’s out a moan while i slip down her pants and slide my cock in.
” Aaah Sam, u don’t want to do this! I’ve send the picture to your ex and she sure as hell will keep it safe for me. Aaah Take it out of me.” She moans as i start thrusting in her perfect body. As i start pumping harder and harder, I notice she isn’t resisting too much anymore.
as I finally feel in control of the situation, i grab her tits again while maintaining a good tempo. Anna’s even thrusting in the rythm against me while talking really dirty and I feel like all the teasing has made me close to cumming already.
Anna notices this and starts moaning extra obvious. I’m not sure how much longer i can hold it in.
” OH Sam fuck me harder. Please i haven’t had a good fucking in so long, make me cum over and over and over!”
The pressure becomes too much and she knows it.
As i pump my heart out a few more times i start shooting my cum in multiple loads. Every load get’s welcomed by her pussy sqeeuzing me tighter and tighter. I hadn’t cum in way too long and it showed.
” DID U CUM ALREADY? ” Anna says shockingly as she is still shaking from my last thrusts.
” So that’s why she cheated on u? Because u can last for 5 minutes? What a waste on such a beautiful cock” Anna says. I feel how she got enjoyment from this, she knows I couldn’t handle her and now my power role feels vanished.
Anna pulls my cock out and grabs my arm. She pulls me on the sofa and right before I try to resist she sits right on my face with her leaking pussy.
“That”s what boys like u deserve. Eat your own cum Sam!”
I try to resist but her pussy is grinding all over my face and i start licking her out anyway.As i’m working my way through, i’m met with my own cum and a mix of the most lovely pussy juices i’ve ever tasted. Feeling humiliated and slightly turned on again, my cock starts throbbing at full size again.
” Oh dear Sam, u really like this, don’t u?. Is it still a punisment if u like to eat your cum out of me? What a dirty boy u are, does Jamie know about any of this?
I try to talk but there’s only some muffled sounds coming out. Finally once everything is cleaned out, she get’s off and starts kissing me with the remainder of all the bodily fluid mixes in my mouth.
” Hmm, i’m gonna have soo much fun with u Sam. U really don’t know what u’ve got yourself into. Now this time for real! Give your phone to me and get on your knees, or i will make sure every one of your friends know about this!”
Tinder date turns out to be a setup, Part 2.
It’s been a week ago since my tinder date with Anna, wich could also feel like multiple weeks at this point. I’ve always felt like i was more into the submissive side when it came to sex, but since my experience with Anna it became alot more real and scary. ( surprisingly this made me only more horny and aching for her)
To explain what happened, after Anna snapped a nude of me and made me eat my own cum out of her, i was forced to do what she said.
She went through my browsing history while i was on my knees, and unfortunately i had been watching some chastity / femdom / edging pornstars before she came over without deleting it.
“Edged into insanity, Step sisters chastity fuck toy? U really are as messed up as i hoped u are Sam!” she said while giggling
“it’s just some porn fantasy’s Anna, please give it back” I said while blushing, wich she obviously saw
She keeps on browsing for a bit before she throws my phone on the couch.
” Well Sam, ur fantasy is coming true tonight” she says as she reaches in her bag.
It’s a chastity device. I had never seen one in real life before and the thought of it scared me a bit.
“u already know what this is, so i don’t have to explain it right?” Anna says
I really do not want to get my dick locked up in that small Cage, but the look on her face says enough.
“As i don’t have another choice, could u put it on for me?”
She squats down with her amazing legs and her big tits are right in my face. She puts the device on me and: “CLICK”
Anna then attaches the key to a necklace and let’s it hang right in between the spot where i look at the most.
” How does it feel Sam? Knowing your dick belongs to me. No way of escaping without this little key.” Anna says as she smiles
“So what is the plan? U can’t just keep me locked up in this thing all night, it’s gonna hurt!” i say as everything sinks in
” Hihi, all night? U mean all week.
Now u get to choose, do u want to be the big spoon or the small spoon tonight?” Anna says
Her voice is so sensual and sexy, wich almost makes me hard again in the cage.
” Quick mention, if u chose to be the big spoon i will grind my ass against u all night while u are locked up. If u chose the small spoon, the chastity device can go off for the night. However, i will fuck u with a strapon and make u leak all night.” Anna says viciously
How much i would like my dick to be free for the night, i am in no need of being fucked by Anna.
“i’ll be the big spoon!” i quickly spurt out.
It was a horror night. I couldn’t get too horny all while she was doing her best to make me as sexually frustrated as possible. Moaning and grinding up against me all night. I didn’t think it was possible to leak this much pre cum without being able to get fully erect, but her whole butt was sticky halfway through the night.
Suddenly I get woken up by heavy moaning and feel someone thrusting against me. As i open my eyes i see Anna riding me intensely. But it’s not actually my dick, she’s riding a big black strapon around my waist.
” Mmhh, u’ve just woken up at the perfect time. I’m getting soo wet from this big fake dick. Does it hurt down there? My locked up fuckboy!” she moans as she get’s close to climaxing.
I’m shocked because of how horny this is making me. I’m leaking so much pre cum and my dick is testing the material of my chastity device. As Anna starts shaking and moaning she put’s her big juicy tits in my face while slowly pounding a few more times on the strapon before taking it off me.
” now as a treat u can suck it clean for me Sam” Anna says devilishly
I’ve become such a horny mess that I immediately long for her pussy juices, so i start sucking her whole strapon clean. I’ve become addicted to Anna and all of her body.
Anna get’s in bed with me again while starting to grind up against me like the rest of the night.
After a few more teasy moans and dirty talk from Anna I dwell asleep again.
As i finally woke up after she fucked me into waking up at night, Anna was gone. I noticed the chastity device still being attached and this is when the hornyness turned into being scared of the consequences.
As i reach to my phone i see Anna has send me a snapchat.
It’s a picture of me asleep, laying naked on bed with her panties in my mouth. (with the text: see u next week, my slut)
Then I suddenly see a snapchat from my ex Jamie. She must know about last night since we haven’t connected in over a few months.. It’s a picture of her in yogapants and a very revealing top. It’s making my dick want to move and grow but i immediately feel it aching.
This is gonna be a long week..
Anna has kept me locked up as her on demand friend with benefits for over 2 months.
She’d order me to come over every week or so to either tease, fuck, edge or deny me. At one point she even set up a night out for me and Jamie to go drinking and chatting up, however she made me go on the date with my chastity on.
After 2,5 months Anna got into a relationship and gave the key to my chastity device to my ex Jamie.
This was my first written story inspired by my experiences. Let me know what u think please!
Source: reddit.com/r/gonewildstories/comments/i2hbxn/tinder_date_turns_out_to_be_a_setup_fm