How I (29m) fucked my friend's ex (26f) in every hole and made her throw up

I am Turkish but I since I am writing in English I will use English fake names – and sorry if there are mistakes. Ages in the title are of the time this happened.

Some background, one of my close friends had a girlfriend for almost two years. Let’s call her Jess. Jess was a nice person at first but during the relationship her true colors came out. He was making my friend’s life unbearable and he eventually broke up with her. She got really upset about it and apologized many times but my friend was solid.

One more thing, she was a really big girl, weightwise. I genuinely have zero intention to offend anybody but this must be stated. She was seriously overweight.

The origin moment that shaped this story were two things my friend told me when we were having a boy talk some time after their break up.

First was, on two different occasions she tried to deepthroat him and ended up throwing up all over his cock. My friend didn’t like it very much but I disagree. I was a bit jealous because I didn’t experience a puker and he did.

Second was, he accidentally entered her asshole and didn’t realize, she didn’t say anything until the sex is over. And when he asked her why she didn’t stop him, she said and I quote “I thought my man took things in his hands and had his way with me.” Then since once it happened, they did anal from time to time.

My thought about this girl was that she was a really bad person and all of a sudden I found out that she was a submissive dirty talking puke whore who takes it in the ass. I was… Impressed!
Some months after their break up, I was to attend a birthday party of one of my friends. Since during relationships friend groups engage, Jess was also invited since her ex/my friend was out of town.
The party was at a tavern, so there were a lot of rakı (for those who do not know, it’s a strong Turkish drink) and snacks. One glass after another, everyone loosened and started chatting, causing seat changes around the table. At one point, I ended up next to Jess.

She immediately started to talk about the break up and how she was so upset and now she hates my friend. I realized she was never going to stop so I kept drinking and drinking, as did she. Drink after drink, she was talking about how she started talking to another one of her exes again, probably hoping me to tell my friend so he would get jealous. I couldn’t care less. With alcohol in my blood and anger caused by her fucking up my evening, I started imagining fucking her mouth to shut her up. This led me to remember those things about her. So shutting her up with my dick evolved into me fucking her ass hard in my mind.

This really helped me through, and the night was finally over. We were leaving and people who live close to each other shared taxis. Jess moved to a new home after the break up and the neighborhood was close to mine. So we ended up sharing.

On the way, I asked her many times about the exact location of her house but she was too drunk to remember. She didn’t have an address written anywhere in her phone or on some little notepad. I didn’t have any other option than hosting her for the night. No matter how annoying, I wasn’t going to let a drunk woman re-explore her way home in İstanbul in the middle of the night.

Also, even though I fantasized about shutting her up with a cock in her mouth, I wasn’t thinking about actually doing it so her coming to me was not exciting.

When we got home, I was too lazy to make a bed for her so I told her to sleep on mine, I was going to sleep on the couch in my living room. I was hoping this would happen really quick but when she got to the bedroom, she sat on the bed and started speaking again. I was trying to cut her off and leave but to no avail. Then my mind started to imagine the same things I imagined at the party. She was yapping again but I was holding her head and fucking her mouth. While this was happening in my mind, I realized the physical position we were in. She was in front of me sitting on my bed and I was standing up. Her mouth was leveled with my dick. My imagination, with the authority given by alcohol, stopped the action and turned into a commanding officer, telling me to do it. I felt very primitive and really wanted to fuck her face. Still, I knew I could not go full animal.

I don’t even remember what she was talking about at that moment, I interrupted her by saying “Do you know what you need?”

She looked surprised, probably because I finally said something. “What?”

“You need a good fuck.”

“Excuse me?”

This was the point I had to keep it very balanced, so that if it were to backfire I could jump to an overly honest friend advice attitude.

“Yeah” I said, “I really mean it. This helps every single time. My friends also do that, girls and boys no matter. It just works. You should find someone and do it. Maybe that ex of yours that you mentioned.”

“Well, I don’t know” she wasn’t suspicious, “How would that help me forget him?”

“I didn’t say it would help you forget him but it will definitely help you distract yourself. Bring your self esteem back and give you some relief trust me.”

“But how would I make love to someone else when he is still on my mind?”

“Well, I didn’t say make love. I said fuck. You need an emotionless physical thing, plain fuck.”

She laughed, good.

“I don’t know… Well I haven’t been with someone since the break up. So it has been a while actually.”

“Yeah.”

“Maybe… But you know, some random guy may distract me but won’t help with my anger.”

I saw the opening and took the shot, “Don’t do it with some random guy then.”

“Who then? One of his friends?”

“Yeah, that’s gonna feel like you’re taking your revenge.”

“Like who? You?”

Voila! I have specifically chosen my words as I answered “Me? Haha! No I mean some other friend! Can you imagine fucking with me?”

That was it. She didn’t answer, but she kept looking at me. Then I knew at that moment that I exactly made her imagine fucking with me.

“Jess stop looking at me like that!” I faked another smirk. She realized then what she was doing and literally turned her eyes away, blushing.

“Well sorry! You told me to fuck one of his friends!”

“I know I did, sorry, but I didn’t mean me! I would never fuck you!”

Say “never” to a girl and you have planted the seed, and if she is not in total control of herself she will ask the first thing that comes to her mind, just as drunk Jess did: “Why not?”

She was caged.

“I mean, I don’t know, it’s just… I just would not!”

“Is it because I’m fat?”

“Wow wow wow! What? Why would you say that?”

“Then why not?”

“I mean, you were my friend’s girlfriend!”

She laughed. “You are the one who told me to do it with one of his friends!”

“I know but not me!”

“So just that? Because I was his girlfriend?”

“Yeah!”

“What if I wasn’t?”

“What do you mean?”

“You know what I mean! Would you do it then?”

“I mean… I don’t know… I probably would…”

“Probably?”

“Oh my God Jess yeah! I would make love to you!”

“You said not to make love?”

It’s time to gear up now, “Do you want me to say that I would fuck you?”

She paused, then said “Yes.”

“Okay Jess. I would fuck you.”

Awkward silence followed. Then I said “But you were his girlfriend. So you wouldn’t want me to fuck you either.”

Another silence. I said “Jess?”

“I am not his girlfriend now.”

“What do you mean?”

“I was his girlfriend. Now I am not. I’m convinced we are not coming back together. So I’m basically a single woman now.”

“I’m not sure I understand.”

“You do.” Well fuck yeah I did. I was just trying to make her say it without me asking her to.

“Jess, I really…”

“You really what?”

“I mean, how did this conversation even came here?”

“I want you to fuck me.”

“What!?”

I was acting like I was in a shock. As if I was turned on at that moment, not before this conversation started.

“You heard me” she said.

“You… Wow… Don’t say that!”

“Why not?”

“Because it… Turns me on?”

“When I tell you that I want you to fuck me?”

“Oh my God! Stop!”

“Fuck me.”

“Jess!”

“Fuck me.”

“Jess please, we cannot do that!”

She looked at the bulge in my pants, finally! “This one disagrees” she said, pointing at it.

“Well don’t worry about it.”

“How so? It says that you do wanna fuck me.”

“Oh fuck yeah I do wanna fuck you.”

“Then fuck me.”

“Jess we can’t do it.”

“Okay shut up! I don’t want to talk to you. I want to talk to him” she grabbed it, the slut awakens.

I knew it was her final shot, if I moved her hand away she could stop insisting. So I have weakened my resistance. I made her make the first move, so if she would wake up regretting tomorrow, it would not be on me.

She started rubbing and squeezing my dick over my pants, making eye contact. She then unbuckled my belt, unbuttoned my pants, and grabbed the zipper. I said “Jess, please” almost moaning.

“Shh!” she said, “it’s between him and me.”

She unzipped, stuck her hand in my underwear and let it out. She let out an “Uuuh!” while she did that, as if it was an accident. My half erected dick was right in front of her face now. She wrapped her hand around it and started rubbing, very gently. As my precum was flowing, she squeezed my dick as it was a tube of toothpaste and milked more of it. Then used it to lube my dick and made it rock hard. I could feel her breath on the tip of my dick.

She stopped rubbing, looked up at me and opened her mouth. She got a little closer then I delivered my last line before stopping the act.

“Jess, if you do that there’s no coming back. If you do that will fuck you like there’s no tomorrow.”

She inhaled my dick. She basically grabbed half of it with her mouth. Then she started sucking it slowly, still looking at me. “Jess…” I whispered, “you are so good.”

She moaned after hearing that and got faster. I was biting my lips. I put my right hand on her head but still didn’t take control. I was definitely going to make her puke, but not on my bed. I pulled her hair back, taking my dick out of her mouth. I pulled her up by her hair, “Stand up bitch.”

She smirked as she obeyed, “Am I your bitch now?”

“I warned you before you put my dick in your mouth, didn’t I?”

“Yes though man, you did. I guess I am your bitch.”

Blowjobs and dirty talk are my two favorite things and she gave me both of it up to that point. Without letting her hair go, I grabbed her chin with my other hand and stuck my tongue in her mouth. We were not making out, we were devouring each others tongues. I pulled her back again and started aggressively undressing her. I wanted her fully naked, defenseless. When I undid her bra her HUGE tits spread out. I commanded her to continue after that and she undid her pants and underwear. Then she took off my shirt, and I got rid of my pants by shaking my legs. Then I pushed her to the bed on her back. It was my first time with an overweight person so I kinda didn’t know what’s next. I usually go for putting my arms behind my partners knees and my hands on the bed, kinda folding them thrusting myself hard, a painful position for the receiver. This is to see if they could take it. If they can’t and stop me I switch to a less painful position, but if they can I enjoy their loud screams. However, this was clearly not going to be the case with Jess.

Thankfully, she helped me. She pulled her legs up, her feet on the bed and spread them. I laid on her and placed my dick on the entrance of her vagina, but didn’t penetrate. “Come on!” she said, growing impatient. I said, “Say it again bitch, ask for it.”

She looked at me for couple of seconds with fuck me eyes and made it verbal afterwards, “Fuck me.”

I pushed in balls deep, making her gasp. I waited, then I pulled it out slowly and pushed all the way in again. Then again. Then again. Then again.

She started giving an uninterrupted long moan and I got faster and faster. As I did, her tits started to go in circles. I mean actual 360 degree circles and it was so… Appetizing.

I have grabbed them both, squeezing very hard. She let out another moan, this time it included pain but I was not going to stop unless she openly tells me to.

Tell you this; if tit guys and ass guys go into a war, I would be a fucking Field Marshall in tit guys army and hers were really really huge.

On the other hand, her pussy was also so soft because of her body. I couldn’t feel the hip bones as I thrust myself in. It gives me a feeling of completion. You know, I am hitting her and crashing her hip bone, so I have achieved this single thrust let me go for the next one kind of thing. This was not happening with Jess and this got me really ambitious. I stretched my legs and rose on my toes, hitting her even harder. Still no hip bone, but the sound got me crazy. I started slapping her tits, but wasn’t enough, I went down and started sucking and biting them. She was basically screaming at that point.

“Please fuck them too” she said eventually. “Take it out on them, please!”

I complied. I positioned myself on top of her belly and she held her tits tight. I stuck my dick in between them and OH MY GOD.

Fellow men, imagine a calm masturbation session which I know we all have sometimes. Not one of those that we do out of boredom or those that we do to get rid of some uninvited boner. No, the ones that we do on a comfortable place, just for the pleasure of it. Her tits felt exactly like that. They were so big, normally when I titfuck a woman the tips goes out of the top, but hers surrounded every single bit of my dick. So soft, so warm, they calmed me down. Even she was surprised that I was taking my sweet time. I could really stay there and cum, but this could potentially be my only time with her so I could not risk it. I moved up and put it in her mouth again. This time, due to the position, I was fucking her mouth but cautiously. But I became really eager in no time and wanted to ravage her throat. Of course I didn’t, but I did push myself a little deeper to make her gag. This was part of a plan: I did make her gag a couple of times and every time I did, I stopped and pulled back to look at her as if I was thinking she could throw up, not that I knew she would.

That was enough for now, I got up and said “All fours now.” She obeyed me like the good slut she was. I got behind and started fucking her in doggy. I was thinking about a way to fuck her ass without making it obvious that I know she was an anal slut. However, I realized her asshole looked nothing like an anal virgin’s ass. So I put my left thumb in it.

She gasped “Oh you could have asked!”

“Your asshole makes it obvious that it has been fucked before” I answered, followed by a slap on her right butt cheek.

“Oh it does?”

“Yes, you are an anal slut aren’t you?”

“I guess I am!”

I gave her cheek another slap, it was well deserved.

“Did my friend fuck it?”

“Yes he did, he loved it.”

I pulled my thumb out of her asshole and filled my palms with her meat. I literally did what I just said, I squeezed my fingers into her sides and grabbed a handful of skin. I started fucking her so fast and thanks to the alcohol, I wasn’t even feeling close.

“He fucked you a lot didn’t he?”

“Yes he did, he did fuck me a lot!” Her answers were now mixed with moans.

“A slut like you deserves to be fucked! In every fucking hole!”

“Yes, yes she doe-e-e-s.”

She got another slap, her moans were becoming louder. She was close.

“Were you a good slut to him?”

“I wa-a-a-as! But I… I wish… I wish I was your slut… All these times…”

She was fucking GOOD at this game.

“Why would you say that bitch?”

“I am being fu-u-u-ucked… Like a whore like… Like me… Deserves… I wish for two-o years… You were my ma-a-a-a-an!”

She got really really loud and I got really really fast, slapping her ass cheeks really hard at the same time.

“Would you let me fuck all of your holes as well.”

“Ye-e-e-es! I would beg for it! Beg for it! Beg for it!”

“I’m going to fuck your asshole just as I’m fucking your pussy right now.”

“Oh yes you will! Yes you will! Yes you will!”

“Are you my fucking whore now?”

“I… I a-a-a-am! I… am… your… fucking… whore!”

“Beg me to fuck your ass!”

“Ple-e-ase fuck my a-a-ass!”

I pulled her hair roughly.

“Not enough!”

“Please fuck your whore’s a-a-a-ass!”

“More bitch!”

“Fuck your friend’s ex girlfriend’s ass please! She belongs to you now! Use her!”

“Yes I will!”

I got to my maximum possible speed as she started another one of her uninterrupted long moans.

“Can I… Can I come?” she asked. She was getting tighter and tighter.

“No.”

“Plea-a-a-asee…. Please-e-e-e…”

“No!”

“Have mercy pleaseee… Pleasee!”

“Now.”

She immediately started shaking and fell forward. She was clearly enjoying it but I didn’t lose even a second. I held my dick which was very much lubed with her pussy juice, and stabbed her asshole with it.

She screamed and moaned. The sexiest sound from a woman imo. She was shaking and having anal spasms that squeeze my dick inside. It made it hard to pull my dick back so I waited, laying down on her, until she got relax.

Couple of minutes later, I felt her grip loosened around my dick. So I started fucking her ass. Her moans were different this time, pain was involved. I then realized I haven’t checked on her for a while so I said “Are you okay?”

She looked like she was about to pass out and moaned “Mmm-hmm”

“Do you have a safeword?”

“No…”

“Say red flag if you want me to stop. Do you understand that?”

“Yes.”

So I thought, all set, let’s go.

I got out, told her to position herself face down ass up then to spread her ass cheeks with her hands. She obeyed, what a good whore. I stood up on the bed and got low, without putting my knees on the bed, restarted fucking her ass – balls deep. Her ass ring was indeed loosened by previous anal whorings, but it was still holding my dick tight. It felt amazing when it was around the base of my dick, basically urging me to impregnate her asshole. I really was going to but the final act was more appealing. I thought of the better asses I fucked and creampied before and got myself away from the idea. Enjoyed it little bit more and got out and stood up next to the bed.

“What happened?” she asked.

“You gagged when I fucked your mouth, didn’t you?”

“Yes I did.”

I grabbed her hair and pulled her off the bed. She was on the ground on all fours now. I kept pulling her, made her crawl to my bathroom. When we were in, I pulled her up, detaching her hands from the ground and made her sit in cock sucking position.

It was go time.

I grabbed her head with both of my hands and pushed my dick in her mouth. Ass to mouth is a very rare thing and I wanted to make the best of it. Pushed my dick as deep as I can. She gagged and tapped my legs. She coughed, tears running down her face.

“How does your asshole taste slut?” I asked.

She got herself together, looked up to me and said “Disgusting!”

“Good.” I stuck it back in but this time I was fucking it as hard and deep as I can. She gagged, gagged and gagged until eventually making a choking sound. I pulled myself out and right as I did she fucking threw up all over my dick and legs.

I’m going to describe the feeling for curious readers, if you feel like you are going to be disgusted, I suggest you move on to the next paragraph. You have been warned. So for me, only downside was the smell. If you do pukeplay by making your partner drink milk or something I don’t think it would smell that bad. But that was not my case. All that snacks and drinks… Other than that, it was warm and slimy, but it was a thick puke so I guess this is the reason of the latter. If you are into humiliation and degrading (with consent ofc), you will love the view. Her face and your dick covered in puke that you forced out. Her eyes are wet and red, she is trying to catch her breath. Just so fulfilling…

I couldn’t wait, and stuck my puke washed dick back in her mouth. I didn’t fuck it this time, I pushed it as deep as I can and waited because this time I knew what I was waiting for: the choking sound. When it came, I pulled myself out and there, second one came out.

No time outs! I did it again, and again, and again.

It took us five times until her stomach was fully empty. Then it was time to refill.

I started fucking her skull. I pushed myself with all the power I had, my balls were now at her chin. She was ready.

I fucked her face mercilessly and I felt that I was coming. Before it hit the point of no return, I pulled myself out once more so she could have enough breath. I wanted it to be perfect for me.

She must have understood, because she took breaths through her nose, and opened her mouth for me. So I fucked, and fucked, and fucked her mouth and when it was my time, I buried my whole shaft down her throat, cumming directly to her stomach. I was fucking yelling with pleasure with every spasm.

“Gulp it bitch!” I said. “Gulp it gulp it gulp it!”

She obeyed, and tried to gulp. Her throat muscles squeezed my dick and she finally did gulp it. I slowly pulled my dick out and said “Good girl.”

We got into shower and washed ourselves quickly, clearly we were tired. We half dried ourselves and went to bed.

Well, this turned out to be an amazing experience and since it was not on my agenda for the day, it was even better.

Next morning, we woke up simultaneously and started chatting. I can’t say she regretted it but she was a bit scared. I thought this could be because she thought I could tell my friend about it and this would be bad for her image, but I wouldn’t. So I assured her, “Hey, I do not regret what happened last night, and I won’t tell anybody.” She visibly relieved. We kept chatting on the bed about last night and I got a little bit horny again. But it was the action that got me going, not the girl. I wasn’t going to repeat it sober. However, I remembered what I wanted to do last night and asked for a titjob. She agreed, so I slowly fucked her tits as she held them together. It was a lovely feeling, lovely… But I wanted to cum in her mouth so I told her to open it. I kept fucking her tits until I was just about to cum, and when it happened I put only the tip in her mouth. I came and it felt like the whole titfucking session, slow and relaxing. When I’m done I pulled my dick out and told her “Open and show me.” She did, I saw my cum filling up her mouth.

“Swallow” I said, she closed her mouth and let me enjoy a loud gulp. Then opened her mouth again, showing me she ate every single drop. I said, as last night, “Good girl” then laid down again.

We spent a few hours enjoying the bed doing nothing, then she left.