How I [23M] got into a sexual relationship with my roommate [28F] [MF]

Before we get into the story, a little bit about myself – I am 23 and recently moved to Chicago from New York.
Now since i just moved to Chicago, I found this okay-ish apartment in my budget . But the reason i chose this was because of the people that lived in it . I met them and we felt connected vibe instantly. I live with one girl, who is 28 year old and she has a boyfriend who comes over regularly and another 23 year old guy.
So this story starts a month and a half into after I moved in.
The girl, lets call her Amber, and her boyfriend – lets call him Sam – they both share an open relationship. But its different from the actual open relationship, and by different i mean they only sleep with someone else when one of them is out of town or is going to be busy for a few days or weeks. A fact which i learned in a very awakening moment. In the most literal sense.
So one night I wake up to take a piss and i come out of the room to go to the washroom which comes after the living room – while my room opens directly into a part of the living room. And as i open, i see Amber naked on the coffee table with a guy on top of her , who is not fully naked, he is though only wearing a T-shirt. Since our house is out on the main street, the street lights come in through the window and just lit up enough of the room to be partially visible.
Amber has always been a moaner, and someone who talks a lot of dirty while moaning. I could always hear her demanding Sam to fuck her harder and demanding him to fuck her pussy in a sentence such as “fuck that pussy hard. Make that pussy squirt”
She is also loud during that, and unapologetic about it. During the first day we met, while i was still prospecting about it , she said,
“Before we go forward, i should tell you me and Sam have a lot of sex – and by lot of sex i mean pretty much every night. And i am a moaner . So hope that not disturbing for you.”
I thought how loud or how much sex would they have honestly. But spending the first night itself, i was proven wrong. Now probably my other roommate probably doesn’t get her moans that much, cause his room is farther away from her, but for me she is right next to me – sharing a wall.
The first night I unpacked and slept on the bed thinking I’ll finally catch on some sleep with a full day of moving, and as i lie down on my bed, i start hearing the dirty talk of how she wants to suck the life out of his dick and the slurping noises begin followed by loud gag reflexes and his moans.
Now i wont lie, the fact that i am so near to someone having sex, with every sound being very audible, it made me feel as if I was part of a threesome where i am only watching them get down and dirty.
But i am still prioritising on my sleep even though at this point my dick is slowly getting hard. But then i reach the point of no return. And that is when he starts going down on her and she starts moaning.
Now i have heard my fair share of girls moaning . But this was something different. It was almost like i was listening to a porn movie . The moans were amazing. It only took me a second after the first moan i heard to get rock hard.
She kept saying “lick that pussy lick that pussy good. Put all your tongue in it”
And before i knew it , i was holding my 8 inch rock hard dick in my hands. Hearing her moans put me into a place where i did not realise when i had started jacking off. But she wasn’t done, this moaning went on for another solid 15 minutes before she exclaimed, “i am gonna fucking cum!! Open your mouth!! drink that fucking cum”
At this point even I noticed my pre-cum to ooze out now. I was really turned on. I wanted to cum. And i did pretty quickly once he started fucking her. And her moans and dirty talk reached to another level.
Now they must have had a good solid 40 mins of fucking before he came on her boobs (she kept repeating that for the last 5 mins when he exclaimed ‘i am gonna cum’)
And it got really hardcore in those 40 mins .. the bed was shaking she was moaning a lot- the pace never got slow, he only kept going faster and only stopping (i am guessing) to change positions.
I remember i came twice that night . Once when they were having sex and one after they were done and they slept but i was still very hard as i w take out to moans from my head . So i jacked off again – and that was the first time I fantasised of how her body would be . I did notice the hourglass figure when i came the house first time , and i also noticed the noticeably bigger than average boobs she had and the tight round ass she walked with. And this night was first of many (and by many i mean every night) that i jacked off her moaning first and then second time fantasising that i was the one fucking her.
Before moving here, i hardly masturbated once or twice a week, but now a month into living here, i was masturbating twice every night.
So now when i saw her on that coffee table with her legs wide open and her hands holding her boobs and playing her nipples with one hand while rubbing her clit with the other while the guy fucked her as hard as he can, i got an instant boner. While i am a guy who loves to sleep naked, i wore a pair of boxers when i got out of the room to take a leak. And as i saw her boobs, and her hard nipples, there was a huge tent formed on my crotch and as she noticed me and my tent, while i noticed her big , 34D full boobs jiggle up and down with the motion of the thrusts, i quickly noticed she saw me enjoying the view, so i quickly went to take a leak and once i took a leak i noticed to hear the moans again. Till now she wasnt moaning, which cleared a confusion that i had over the month that maybe she is faking it with her boyfriend of how big he was and how hard he was all the time, and that how much cum he was shoot. But now i realised that she was faking it in this moment and not before .
And now that i had seen her boobs and she was moaning, i was rock hard again, and i felt that i had to jack off . So did, i couldn’t hold my cum too much this time, the image of her boobs moving up and down and the fact that she was looking at my boner was too much for me.
While i walked back, i noticed he was done and he was lying on top of her and she moved her to see me as i was walking back to my room. I noticed her eyes went down to my half hard boner as i walked to my room and gave her a smile before going in, and she did the same.

For the next couple of days things changed, but we never addressed what had happened and that she saw my boner and i saw her boobs. But she had become more open to me about sexual topics and she had started walking just in lingerie around the house. She had also one day asked opinions on what sexy lingerie she should wear for her hookup date as her boyfriend was again out.
She first showed the ones she had, and i said i would need to see how she looked in each one of them as she has said, “which one would be hot enough to make someone like really hard? Like which one would make you hard since you are a guy too” and i did end up choosing a lingerie for her that night.
And she saw my crotch every time she asked “is it hot enough to make you hard?”
And she kept laughing at the fact that i just hard constantly from first pair of the lingerie to the fourth- the last one. I said the 3rd was the best as that was a little see through.
And then later that night, i noticed she was back pretty early at 10 and that she was in the shower. I got out of the room to shower in my boxers and tshirt.
While she was in the shower she just exclaimed that i could just use the john while she was in shower. So i did. And i as i was done and i put my penis inside my boxers again, she came out of the shower and she saw my flaccid penis and she exclaimed, “oh i never knew you were uncircumcised.”
“Yeah. I live in New York but still Indian so we dont do that in out culture”
“Interesting. Good to know”
And then i noticed she was naked in front of me and i saw seeing her boobs for the first time in proper light. And they were mesmerising. Full, wet big boobs with small nipples erect.
She noticed me staring at her boobs and she quickly wore a bathrobe and said,
“Well, thats all the time you get to see them”
Laughed and left the bathroom.
She them went and wore her panties, and a T-shirt and came out to the living room. Her small nipples were still erect, and were poking out from her T-shirt.
She sat down next to me on the couch on the living room as i was randomly browsing through the channels. As she sat down next to me, put up my legs on the coffee table, the same coffee table she had sex on.
“I hope you guys didnt break this table that night” i said and smiled as i looked at her.
“Oh no, that guy couldn’t break the table if the table was already broken. He didn’t know what he was doing down there. He thought going fast is all there is to fucking. You know I had to masturbate after.”
“Damn that sucks”
“I didn’t even suck his dick, usually i like sucking dicks”
“Yes i know” i blurted out. I wanted to just think that, not say it.
“Oh . How do you know?”
“You know our walls exactly aren’t sound proof. I can pretty much hear everything, down to even the slurping.”
She laughed, and said, “i guess thats a live treat for you everyday. But you know that is actually my favourite thing, slurping and deep throating”
“Mine too”
“I miss Sam’s dick. He loves it too when i deepthroat him.”
“How long is he going to be gone?”
“2 more weeks. And its already 5 days and I haven’t had a proper fuck you know. Even the guy today i met with actually fucked me in the bathroom stall in the club but he came in like 10 mins. I mean he was fucking nicely even though he wasn’t that big , must have been 6-7 inches but like he came too early.”
“Thats too bad. How long do you usually like it to last?”
“I think atleast 30-40 mins is the perfect duration for me. If longer then even better. Sam usually lasts 40
Mins to an hour.”
“Yes i am aware of that happening”
“Haha .. do you listen to us having sex every night?”
“Yeah. It kinda is the same time i go to sleep. So its like first hour i am listening to your guys having sex.”
“Does it disturb you?”
“Can i be honest? I dont want to weird you out.”
“I have seen your flaccid penis today, so i guess we are pretty close now”
“Haha, that is true. To be honest then, it kinda turns me on. After the first night, i kinda look forward to it. I even masturbate to you guys having sex.”
“Really?”
“Yeah! Like before moving here, i used to masturbate once or twice a week, and now I literally masturbate twice every night.”
“Haha. That is amazing. You are getting a free live show every night. Btw did you also jack off the other night you saw me having sex on the table?”
“Yeah. . I woke up to pee but then seeing you like that just made me hard. So i had to”
“Seeing me like that?”
“Like i mean naked. I mean you cannot deny, you got a hot bod.”
“Hahaha thanks! I saw your boner that night too, and even today. Do you mind if i ask how many inches is that?”
She pointed on my now growing penis as it was making a clear outline on my boxers.
“I have never proper measured it but i think..”
“Then lets measure it.”
She interrupted and sprung up and went towards her room and came back with a ruler.
The excitement with which she had got up to go to her room and the excitement that rushed in me with the fact that she wanted to measure my cock mixed in with her bare ass shaking through the panties she was wearing gave me a boner.
“Okay. I got the ruler”
She walked up towards me and all i could do is look at her boobs and her nipples and they were hard and poking through.
“Okay lets see it. Lets get this boxers off”
She said while standing in front of me.
“Okay”
I took off my boxers but i was still sitting on the sofa.
“Wow. Even before i measure it, i have to say, its a big one”
“Hah. Thanks”
She sits down on to level the boner and took my boner in hand.
“Okay lets measure this monster.”
She places the wooden ruler next to my dick as she holds up my dick and the ruler next to each other.
“Ummm.. it sayyyysss.. its around 8 inches and 47cms. So you are almost 8 and a half inches. so that means you are half an inch bigger than Sam.”
“Really?”
“Yep.. he is like almost 8 inches. And you are half a cm bigger than him.”
She still sat there with holding my dick in his hand.
“Do you have a big penis head?”
For skin only pulled back a little when fully hard so you couldn’t see the full head until you pulled the foreskin back.
“I dont know if you’ll think if i have a big head.”
“I guess we’ll just have to see.”
She said that and smiled and then slowly pulled my foreskin back fully.
I am someone who has a bigger head than the shaft.
“You do have a big head! I like a big head. And i like how your head is much broader than the shaft.”
She moved another hand and took one of her fingers to see how hard was my head. She just moved her fingers around the head. And as she started to move around her fingers, i had some precum ooze out.
She smiled and started to spread the precum around the head with her fingers.
And when she was done spreading it around the head, she licked her finger.
“I like the taste of your precum.”
“You should taste my cum then.”
I smiled meaning it as joke but she just moved her tongue around her lips.
“How do you jack off with the skin? Just move the skin up and down like this?”
She started to move her hand up and down and started to jack me off quickly.
“Yepp. Thats how you do it”
“You know i have never been with a guy who is uncircumcised.”
“Really? I would love to change that.”
She looked at me, while jacking me off and then suddenly left my dick and stood up, and then took off her tshirt and then took of her panties too. Her vagina was fully shaved and from the looks of it, it looked really tight even after the fact that how many times she had been fucked and how many times i have had heard her getting fucked.
She then pushes me to lie down on the sofa and gets on top of me puts her pussy on my face and starts jacking my dick again before putting it in her mouth. She did not even take a moment to adjust, she had the whole dick deepthroating as soon as she started sucking me off while i was trying to lick her pussy which was getting harder cause her throat was constantly fucking me.
But the scent of her wet pussy kept calling me .. i buried my face on her pussy and started to lick her clitoris moving my tongue constantly on her clitoris while i put my fingers inside her. She then started to move her hips moving her pussy lips on my lips while still deepthroating me.
She then suddenly stops sucking me and gets up as she was now actually sitting on my and moving her hips much faster now and moaning loudly. After moving vigorously for another 10 minute she exclaimed, “i am fucking going to cum!”
“Cum in my mouth!”
I said and she started moving even faster and then just stopped suddenly and shot all of her squirt on my face while a lot of it getting into my mouth.
That was the first time i had been with a girl who could squirt. And squirt so much!

“You taste salty” i said, and continued “now get that wet pussy down to my dick and fuck me”
She first bent down and licked her own cum off my face till she had gotten all of it and then started to kiss me as she started to move her pussy down to my dick.
And the took my dick in her hand and slowly started to go down but before she could take her time adjusting, i pushed all of it in at once, and left a big gasp and just sat there with her hand on the public region.
I could feel her walls stretching. I could feel that she has never had a dick as thick as me. Even after bding fucked so hard everyday i felt like i was fucking her fir the first time.
It was like she skipped a breath. And then suddenly she slapped me. I slapped her back and then i held her neck and chocked and just started to fuck her as hard and fast as I could going in and out fully. I could go as fast as i could because she was getting more and more wet with every thrust . I could i was hitting the ends of her pussy slowly as her pussy opened up more and more.
For the first 10 mins of fucking she had not closed her mouth and as she was still gasping for air .. not because i was choking too tight, i wasn’t . But because her pussy hadn’t adjusted to the extra 50 cms yet.
She begged me to stop a couple of times but i didn’t. She then put her hand on my abdomen pushing me to stop but i wasnt going to stop . This is what i had dreamt of doing for the last month, destroying her pussy.
But after 15 mins of non stop fucking i wanted to change the position .
I could see she took a big breath of air in as i pushed her on to the coffee table.
“Dont you fucking stop me. I has been wanting to do this for a month. I am going to destroy your pussy”
I slapped her again . And then i spanked her ass and told her to lie down on her stomach and i spread her legs as wide as she could.
I spanked her ass more and said, “This ass has been teasing me for a month .. i have been wanting to spank you ever since i saw you”
I spank her a couple of times more and i pull her ass up a little so it a little higher than the body and its sticking it out . And then without telling her or giving her a heads up i stick my whole dick inside her again. She again lets out a gasp but with a little moan and sticks her ass out a little bit more. I took this as the acceptance of the roughness that had built up in me. I didn’t want there to be a moment of slow fucking, this was pure sexual exertion and fulfilling my sexual desires of fucking her apart.
I put both my hands on each of her ass buns and pulled them apart and took out my dick till the head and put my whole dick back in, in one go. She exhaled again and turned back and looked at me as i started to slam her ass from behind and spanking while i trash her pussy from behind. She had now started to talk dirty and start to moan loudly. The same loudness and dirtiness that had made me so hard for so long. My balls were slamming her pussy hard.
Her pussy was still tight and very very wet. I could now feel the ends of her pussy on head every time i slammed into her.
I wanted to go even faster so i decided to pull her hair and i got hold of her hair and i was now holding them with both my hands and now i was much more comfortable and i started to go even faster.
“Fuck fuck fuck fuck fuck fuck fuck fuck FUUUUUUCCCCKKK MEEE!!!”
She kept repeating the word fuck everything i thrusted in her. I could feel her walls tightening even more ..
“Dont stop dont stop dont stop! Faster faster faster! Harder harder harder”
Thats all i wanted to hear – Her begging me to go faster and harder. And i did.. i slammed her face on the coffee table and kept my hand on her face and kept it slammed on the table not letting her move inch and then gotten on top of the table with my legs on either side of body with my dick still inside her and now i was on an angle. But this was even more comfortable than before and i could put more force into thrusting her than before , and so i did. On ever thrust, she was physically getting pressed into the table with my hand pushing her face down and my thrusts pushing her ass.
“Fuck fuck fuck!!!! You…. AREEE… MAAKKIIINNGGG…. MEEE… CUUUMMMM!!!!”
And as she said cum, she let go suddenly and her legs slammed on the table and her hands were move dangling from the sides of the table and her legs started to shake and i could feel her squirt hitting the head of my penis. But i did not stop. I was no where close to be satisfied. And as i kept thrusting her hard as i was before and all her squirt was shooting everywhere. The couch, the table , my tshirt and everywhere .
And as i kept thrusting her nonstop, after a couple of minutes, she seemed to regain her senses and then she open her eyes and she tried to look at me as i was still going strong and still pushing her face info the table.
After a point the table started to move on my thrusts. And she tried to tell me to stop but i pushed her face into the table more. And kept fucking her the same way, not lowering the force or the speed. After a couple of more minutes, she started to get into it again, started moaning and talking dirty again.
“Fuck me harderrr.. fuck fuck fuck fuckkk fuck me harder!!! And break this fucking table now!! Do what sam or the other guys couldn’t do! TEAR ME APART! BREAK THIS FUCKING TABLE!!!”
She really got me going again and i kept going and kept fucking her good and hard and after a while suddenly the front two legs, where her head was broke apart and the table from the front fell down but the back two legs were still there. I started thrusting harder now just to break the table. As i took off the speed and just concentrated on breaking the table, my thrusts got harder and harder without of my notice and she lost the balance of her hands which were supporting her on the table , she slides forward and as i thrusted at the same moment, she slammed her face on the floor with my one hand still on her face keeping her there
And she kept moaning
“Slam that pussy harder!!!!”
And i did. And after some good amount of hard thrusts, the back two legs broke too and now we were flat on the floor on the table head.
“Turn fucking around. We are not done yet!”
“Good cause i wanna fucking cum again”
She turned around and we started fucking missionary.
There is something about missionary that i always have loved. It has always been my favourite position to climax in. And now i could see that i was about to reach mine. Fucking in missionary always makes me reach my speed limit, maybe because i am always most comfortable in that. And so i did. I went max on the speed i could reach. She was moaning but now her moans have out a sense like she was vibrating. Before it was opposite. It felt natural to stop moaning on every thrust . But now she was stopping too but now it felt like the pauses were too short.
Our sweats had now mixed so much now that we didnt know who’s sweat was making out bodies so wet.
I looked into her eyes while fucking her. I could see the same amount of lust that i had inside my dick. She wanted to cum again – i could see she wanted to squirt again on my hard dick.
“You are so fucking wet. Do you want to cum again?”
“Yes. Fuck me . Make me cum again”
“Yes what?”
I slapped her when i said that.
“Yes what?”
“Yes daddy”
I was now slapping her on every word I spoke.
“Yes you fucking call me daddy or you dont talk to me ever. Do you fucking understand?”
“Yes daddy. Fuck me daddyy. Make me cum daddy”
“Do you fucking want my cum?”
“Yes daddy”
“Say it then.” I was still slapping her again and again.
“Tell me you want my cum in you. say you want me to fill your wet pussy up.”
She didnt say anything for a couple of minutes.
“Say it!”
I slapped her again.
Sh still just kept looking at me
I stopped fucking her.
“You dont want my cum? I guess then you wont cum again either”
I started to get up and take out my dick when she wrapped her legs around my ass and pushed me in.
“Yes daddy. I want your cum daddy. I want you cum to fill me up.”
I grabbed her neck again from my left hand and slapped her again couple of times.
“ then fucking say it! Shout it!”
I again started fucking her . I made my thrusts harder than faster when she started shouting.
“Cum in me daddy ! Cum in me daddyyy!!!! I want your cum to fill me up daddyyy!!!”
I held started squeezing her boobs hard while fucking her hard- taking all of my dick out and put it in all at once.
I started pinching her nipples while I squeezed and slapped her other boob making it red.
I could feel her pussy tightening more and more so i could see she was going to cum.
I picked up my speed and went as fast as i could do which made her gasp for air a little bit and started to moan loudly
“Ohh i am gonna cum daaddyyy!!! I am gonna cum on that daddyyy dick!!! Make me cum daddyyy”
She couldnt hold it for anymore . She started squirting earlier than i or her expected. And her thighs started to shake as she started to bite her own fingers as her eyes closed.
Her squirt started to shoot all over the room , on me, on her, on the sofa . Everywhere.
I did not stop fucking her . I did not slow down. I kept fucking her . The jets of her squirt and tightened pussy all of that together made me want to cum to. But i had some more minutes of fucking still left.
Thats when we heard the house door opening.
“Wait wait”
She said trying to push me away.
I wasn’t going to move. I put my hand on her neck and moved her hand away and kept fucking her without slowing down.
“I am not fucking stopping till i cum”

It was our other roomate. He came in and just stood there looking at me in my tshirt and amber naked on a broken table and room filled with the aroma of squirt and sex and sweat.
I looked at him once and looked back at Amber and held and squeezed her boobs and kept fucking her. I was really close now.
She had also ignored the fact that there was someone watching us continuously, she had again started to get into it.
And the fact that someone was watching us turned me on too.. and without even realising much, i shooting ropes and ropes of cum inside her. As the first stream came out of my penis, i lost my control in my hand and i fell on her as she hugged me and i started to kiss her as i kept still fucking her slowly as i kept cumming inside her. She kept moaning into my mouth as we kept kissing and moaning each time she felt a nee stream of cum hit her walls.
This is was by far the most I had cum in my life.
After what felt like eternity , i finally stopped cumming and lied on top of her for couple of seconds and then got up a on my knees and i saw a big smile on Amber’s face.
“Thats a shit load of cum”
“Haha yeah.”
I said as i was breathing heavily. And i finally took out my still hard dick from her pussy and started to get up. And as i took out my dick , a lot of cum started to drip out on to the floor .
I ignored that and went and sat on the sofa with my dick still erect and it fell on my abdomen.
“You fucked the shit out of me man”
“There is going to be more where that came from” i said that and looked at our roommate, lets call him John.
“Hey man.”
He kept looking at us for couple of seconds and just sat on the other couch that was perpendicular to the couch i was sitting on.
“Heeyyyy.. guysss what is this?”
“This was the best fuck in my life so far” she got up and sat on the the broke table.
“Haha mine too” i said holding my hard dick again.
“Are you still hard?” She said looking at my dick.
“Yeah. I told you there is more where that came from”
She kept looking at my dick constantly and said, “can you fuck again?”
“Yep.”
She immediately got up and came and sat on top of me and started to kiss me.
“Then fuck me again daddy.”
She said while sitting on my hard dick.
She started fucking me as we both looked at each other and then at John. We liked the fact that he could was watching us fuck like bunnies.
We both didn’t last that long this time, we both came in like 20 minutes as we were really turned on by the fact that John was watching us have sex.
But this was the only he saw the whole act, from now on he would still walk in on us fucking but he never looked at us more than once. And we fucked a lot from then on!
She would pretty much get fucked by me and her boyfriend every night. Her boyfriend was pretty cool with me fucking her , we even had a threesome once. But that story for some other time.

Source: reddit.com/r/gonewildstories/comments/a1mlpg/how_i_23m_got_into_a_sexual_relationship_with_my