The Loser 3

I'm sitting at a bar with my newfound reporter friend Tom who I have opened up to about more then any of my other friends since he seems so trustworthy and willing to me listen all the time. What I don't know is that he is in fact only interested in my girlfriend Natalie, who he is trying to get closer to through me while he is hoping to find a way to sabotage our relationship so that he can get her instead.

That evening, I notice a older woman sitting a few tables away, she has a very pale, rough and bloated skin and a look of someone who is thoroughly displeased with life.

Tom notices me looking at her and says: "Ah, that's Olga, we work at the same place, she's in charge of the cleaning and I've heard she's super mean and bossy to her coworkers. I mainly feels sorry for her, she hasn't had a man in her life for ages and I believe she must be very lonely and takes it out on her staff... But I mean look at her, are you surprised that she's alone?"

I look at Tom and say: "I see what you mean, however, if what you say is true then she fits perfectly for the sexual fantasy that I was telling you about before. If... if you be my wingman this once, I'd really appreciate it man!"

Tom smiles slightly and then looks at Natalie and says: "Say, if you are sure that this monogamous thing you guys are doing is going to work then sure I can do that."

I tell him to wait while I talk to Natalie and explain the situation, while she is not to keen on the matter she agrees. In the meantime, Tom talks to Olga who by the looks of it thinks he is joking, but after a moment Tom signals me to sit with her. Right before I sit next to her, Tom claps my shoulder and says with a smile: "Don't you worry about Natalie, I'll take good care of her."

Not really understanding what he meant by that at the time and because I was to nervous about fulfilling my fantasy, I didn't give it much thought. A rather awkward encounter issues as I am incredibly stressed about the whole matter, but after we'd exchanged a few flirtatious words, Olga seemed too impatient to stay any longer, so we leave and she invites me to her flat nearby.

While I went home with Olga, Tom was going to try to swoon Natalie the best he could, especially by undermining me since I had just left her for someone else. The efforts bore little fruit, yet.

As I went to up to the flat with her, I could better notice her cheap clothes and furniture, as if she had no taste for the finer things, saving on everything. She offered me cheap wine and we sat together in a rusty sofa and chatted. As I was very shy and afraid to fulfill this shameful fantasy of giving into sleeping with someone I thought was ugly, I couldn't make a move. She instead started stroking my leg which encouraged me to give in. We thrust ourselves at each other in a nasty way. Her tongue was all over as if she didn't know how to kiss and her breath smelled.

But it didn't matter, it made me all the more eager to get inside her. With some effort we took of her tight clothes, which was apparently holding her fat wrinkly body back. She was around 50 years old but did not look good for age. We resumed kissing and stroking each other vigorously. I laid her down in her bed and could see her bloated pussy with long hard white hairs. It was as if she was made for my fantasy. I imagined the shame if someone where to find out I'd fuck that. It was time, she was wet and ready. So I laid on top of her fat stomach and thrust myself inside of her. I was to nervous and heated so I couldn't control myself and was coming to quickly.

I thrust her so hard while she said demandingly: "Cum inside!", so I did with all my force, nothing held back.

After a while I was ready to go again and this time she was on top, I tried to navigate through all the fat as she was leaning over me but since I was failing miserably she simply pushed my hand aside and said "Useless", grabbed my cock and pushed it inside of her, I could feel her saggy boobs and bloated stomach all over me and looked at her bloated red face as she moaned on me licking her lips in a nasty way, she was in complete control and rode me like a play thing. She then rose to a squatting position and I could see her flapping body bounce as she dominated over me, it was too much and I burst again inside of her. We then resumed to pleasure her, at first she kept calling me "useless" and "worthless" but then I found out how to stroke her in a manner she liked, and very quickly she wanted it hard. As her fat hairy pussy wriggled, she came with and explosion and we fell asleep.

As I woke up I realized that Natalies deal was that I wouldn't stay the night but come home after, in all the excitement I had completely forgotten. I texted her saying I'd be home shortly, then I thought "One last time". I woke Olga up by stroking up against her and fucking her sideways, then doggystyle where we came at the same time, it was amazing. I could feel all her bloated body flap against my body as I pounded her. However as I proceeded to leave, Olga said demandingly, "Where do you think you're going?"

I stammered, clearly not expecting that question, "Sorry, I'm... I'm just going to head home now, this has been truly wonderful."

"No, no, you don't go anywhere, you stay now here, and I cook food." She said this in a manner like there was simply no question and that I didn't have a choice, reluctantly I obeyed, it was as if she had some invisible power over me.

While this was going on Tom tried to charm Natalie the whole night up to a point where she was getting annoyed by him at which point he stopped but assured her that she could confide in him if things went sideways with me. When I didn't text her until next morning and then seemed to disappear after that, the first person she went to was indeed Tom. Playing along, he assured her and asked if there was anything he could do. Since she was so angry at me, she invited him over since he was there for her and was the only one who knew what the situation was about. As the day went by with only a few excuses in text messages from me Natalie started to get really frustrated and angry with me.

Olga was controlling me completely at her home, almost like she had some invisible leash she held me with, we ate, fucked on the sofa where I spread her fat legs and pounded as hard as I could and we were getting better at cumin at the same time. I was getting increasingly stressed about the situation with Natalie and felt incredibly guilty, but I was like a string puppet Olga was controlling, using me as she saw fit, breaking me down with humiliating words, using my codependence against me. I was quickly becoming her slave, and a part of me liked it in a strange way. She owned me now.

That night Natalie had had enough and since I had betrayed her trust so completely, she was going to have her revenge. Tom had been very kind and supportive the whole time and it was finally going to pay off for him. Natalie thrusts herself at him and in a frenzy they both go wild. They stroke and groped each other uncontrollably as their lives depended on it. She jumped on him and he was all too eager to indulge her. As she was already all wet from the excitement, she grabbed his hard cock and shoved it inside of her. Tom tried to hide the nasty smirk on his face, but he had won, his plan had worked! She rode him like there was no tomorrow, letting out all her frustration and was going to make sure to fuck Toms brains out to get back at me. Tom was thrusting as hard as he could with nothing held back and as they climbed together they both came in an explosive ecstasy. There was allot of fucking that night, Tom sealed his victory from the back, sideways and on top. He was going to make sure to satisfy every inch of Natalies body and she thoroughly enjoyed it, it seemed that the frustration was a good driving force for the both of them.

This continued for a long time, as Olga was breaking me more and more in, controlling my every move and using me to satisfy her needs, Tom and Natalie's bond was getting stronger and they eventually started living together.

One day as we were fucking in reverse cow girl, a delivery man knocked the apartment doors but noone answered as we didn't hear it. He enters the apartment with a package looking lost, he turns around and she's Olga in all her glory wide open and me under her. He quickly runs out and throws up in disgust. As Tom was a good reporter he found a way to write a piece about this incident and how this all came about and truly making sure my name would forever be marked with this shameful act of betrayal. Now everyone thinks less of me because I sacrificed a truly wonderful person for an old grumpy hag.

Even Olga thought less of me after reading it, and somehow she says that she could do much better and that I am lucky she keeps me at all. She threatens to leave me if I don't marry her now. She has convinced me that because of the article no one else would want to be with a lying scumbag such a me. At this point I've lost all resemblance of what it means to be free, I'm hers completely. As we marry, Natalie and Tom crash the wedding party. They don't stay for long because Olga doesn't want either of them there but while Natalie won't look at me Tom comes up to me, grabs my shoulder and says: "Truly, thank you man! I would never have a chance with Natalie if it wasn't for you, and now we are expecting! Congratulations on your wedding, and hey," he says blinking "I told you I'd take care of her."