Save the Cheerleader's Boyfriend Ch. 02

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The unhealthy self-deprecation continues.
5.7k words
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Part 2 of the 2 part series

Updated 03/05/2024
Created 05/14/2023
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Decided to take my worst-rated story and make a sequel where things would get even more controversial. I hope at least some of you will find it entertaining.

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"Oh, you're going to do it. You will do it as long as I like and you're going to thank me after you have done it," said Shania staring at me with her beautiful brown eyes.

"But honey I don't want to do it. You are taking this too far. I'm not comfortable with all these things you insist on me," I resisted but with a faltering voice.

An increasing pain inflicted upon my balls made me stutter. My girlfriend of two months had encircled them with her hand firmly and as she started to squeeze I saw sparkles in the corner of my eyes and couldn't say another word.

Menacingly she took over,

"Fine. The date is off then. Furthermore, I will have to consider this whole arrangement. I'm starting to feel it doesn't work for me as well as I thought it would. I'm having doubts if you love me at all. Yes, I think that is it. If you would truly cherish me you would give it a try at least."

Then she stared me down as I started to whimper. Pleading her to re-consider and telling her that we should just go back to how things were in the beginning. It was completely useless. She kept squeezing and staring me down and in the end I meekly told her what she wanted to hear,

"Ok, I'll try it. But if I don't like it then that's the only time."

Her mood changed on the spot. She released my balls from her iron grip and was now hugging and kissing me.

"Thanks, babe, you're the best. It'll be so much fun - can't wait!"

My cock had been hard ever since she took my balls in her hand. Now that I could feel her huge boobs against my skin and her kisses on my face I felt ecstatic. Some doubts remained regarding what I had promised to do but I did not let it spoil the moment.

Hugging and kissing her back I placed my hands on her pantie-covered well formed ass and pushed my erect cock against her thighs. Sort of poking in between them. She laughed and told me that she could feel my little soldier all up and ready. Then she announced that we should save it for the evening. I started to protest but one mean glance from her told me that she was ready to go back into her angry mode in a blink of an eye if needed. So I dropped it and she had another idea for us,

"But hey you know what. You can rub my feet while I watch this new show on Hulu. Wouldn't that be fun?"

This was only a small request on a long line of demands which had started almost immediately when she had first time reached out for me. My buddies had been flabbergasted when they saw her with me. Just when I had broken up with my ex, the head cheerleader Jessica, Shania had shown up and kissed me right in front of my friends.

I as well had been more than positively surprised by this unexpected turn of events. Very soon I learned that there were going to be some minor not-so-common details related to my relationship with her that I better not explain to my friends at all. But in retrospect, I was extremely excited about this opportunity to date her. Even if she wasn't a classic beauty such as Jessica had been she was still an absolute knockout. And she had these huge double D or even E cup-sized breasts that could wondrously resist gravity even when she had nothing on her. Combine that with a large but sporty ass and a black girl's assertive attitude and you have the picture of her.

At first, it was nothing big. I was driving her to school and taking her out whenever she wanted. To the mall or movies and that sort of a thing. And in return, she was willing to have some intimate moments with me when she was in the mood. But it is safe to say that right from the beginning, both on the dates and in her bed, she required the highest level of devotion from me.

The first couple of times we slept together it was more or less traditional. Well, she did comment on my dick when she first time saw it,

"Oh, what a cutie. Jess told me you were neither shower nor grower but that has to be the smallest cock I have ever seen."

I considered myself to be more or less average but what could I say? Strangely enough, her belittling my dick did not stop me. To be honest I think it made me even harder. Moving myself on top of her I pushed myself in while simultaneously playing with her spectacular boobs. She sort of stroked my hair and let me suckle on her nipples.

Her pillow talk was like "Oh big stud please fuck me," and things like that but her playful tone carried enough sarcasm to let me know it was just a game to her. And since it was a game she soon started to push my boundaries to the greatest extent.

One night I arrived at her place all ready to go. She had hinted to me during the day that she would like to get laid that night. Letting myself into her bedroom I could see she was sitting on her bed playing with her phone. When she saw me entering she smiled and tapped her hand next to her on the bed wanting me to join her.

"Come here, baby. I need your help with something," she said and then I could see various men on her iPhone screen. She didn't need to explain it to me at all since I was familiar with the Tinder app.

"Wouldn't it be hot if you helped me to select my date tonight?"

With a horrified expression, I looked at her phone and soon realized she was looking at my face. Amused by my discomfort. But dead serious about me helping her with the the selection.

"But...but...I thought that you were dating me," was all I could stutter.

"I am baby. These are not boys I would go steady with. But I bet if we choose carefully we may find someone who can give me a decent fucking tonight."

The buts were almost coming out of my mouth again but she stopped me,

"No buts now. I told you in the beginning that I'm going to meet other guys also. So don't act all surprised. Besides you did let Jessica do it. Did you like her more than you like me?"

Since I had already had my chance with her I should have said no then. Just walk out and forget about her. But I was falling in love with her and something in the insecure back of my head was telling me that I would never score a girl like her again. So I stayed. And I did not just stay but I even assured her with many words that I liked her far more than Jessica. She acted out a little hurt and to my dismay, I promised to help her with the app and her upcoming date.

Leaving me with her phone she started to put on some makeup and to test various lingerie and clothes on her. Ogling at her preparations as often as I could I sat on her bed and went through the Tinder matches. Shania made me describe the men to her in detail. She wanted to know about the height and age and ethnicity and that sort of thing. Soon enough I learned that I was supposed to describe if the guys seemed to have a stout jaw or wide shoulders or sixpack and so on.

All the too-young and too-old ones were skipped and it became evident she was looking for someone approximately 10 years senior to us. Also, she informed me that she would like me to find her a white boy for the night but not a sissy like myself. Someone more manly. Then at the end, she wanted me to present her my top choices. One of them got her interest. It was a good-looking bad boy type of character. Could have been in a rock band. Like a Tommy Lee or something of that sort.

If I thought that would be it I was sadly wrong. She continued her preparations and made me chat with the guy. Pretending to be her. First I was supposed to ask him if he was free tonight and so on. But in the end, she ordered me to punch in the question if he had a good-sized cock.

My life had been crazy with everything that had happened with Jessica but it seemed now that it was nothing compared to what was coming. There I was watching as she was dolling herself up and chatting with some unknown guy about his dick size.

The guy answered confidently enough and she told me that it was settled then. I should write him that her friend would drive her to his place if it was ok for him. Naturally, it was. When I left her at his apartment door the last thing she said was "See you tomorrow" and then she was gone.

Driving back at my home in silence I already had an idea how my evening would turn out. I would resist it for a while but in the end, I would be jacking myself off thinking about my girlfriend having sex with another guy. Shania had looked so goddamn good. With her pushup bra and tight one-piece dress. There was something twisted with my thoughts but I had gone through all of it when I was dating Jessica. The cruciating fact that right at the moment my girlfriend was in someone else's bed excited me in some unexplainable crazy fetish-like manner.

Maybe she would be dropping her panties to the floor and straddling him on his sofa at this very moment. He would be hastily fumbling with his jeans and pushing them down and then she would sit on his cock. Maybe it would not be humongous but I was pretty sure it would be bigger than mine. She would be pushing her titties to his face and gyrating her hips on his lap.

I practically ran from my car to my apartment so that I could get rid of my raging hard-on. The drill was more or less familiar to me now and immediately after cumming into my hand the guilt kicked in. Just like I had known it would. My girlfriend had just gone on a sex date and I was tossing myself thinking about her. What the fuck is wrong with me?

Then I could hear my phone buzzing. When I had the message open I stared at it with glassed eyes. Shania was smiling in it with the widest of smiles. Looking gorgeous. In the background, I could see she was on her knees and that she had pushed her tits up with her hands. Next to her face was a big, hard, and veiny white cock. A BWC if you will. Her face and tits glistened with sperm. There was a small message from her telling me that I had found a great cock for her. And just like that, my cock was hard again.

The next day when I saw her she was all touchy and feely. Holding my hands and kissing me multiple times was the first thing she did when we met. She was acting out like a proper girlfriend. When we got indoors that changed a bit. She told me she was horny and she wanted me to go down on her. When I hesitated she looked down at me and pushed her pussy closer and closer to my face saying,

"Don't worry. I have showered after yesterday. But please be gentle - he used it quite relentlessly."

She made me lick at her pussy for at least 20 minutes. After she came she turned around and relaxed on her tummy and had yet another new way for me to serve her.

"Honey, why don't you lick my ass? I've read about it but no one has done it to me before." was her instructions. Looking at her well-formed black behind I decided that this wasn't a completely awful task. It was all new to me as well and I approached her from behind.

She asked me to hurry up and not to be shy about it. And then wiggled her ass in front of my eyes. Offering it to me as some sort of birthday cake. Feeling her firm ass cheeks on both sides of my face I dug in. Using my hands to make some room for me to operate.

First I gave it a little lick and was happy to find out that at least she was clean. Then with increasing intensity, I gave some sort of tentative kiss directly on her backdoor. She let out some sort of giggly moan and arched her back more.

At that phase, I was more or less used to giving her pleasure and went on for more. In the end, I was French kissing and feasting on her butthole and she squirmed happily under my tongue.

When she finally was satisfied with my efforts she sort of relaxed down and told me I should stop. I had been slowly stroking my cock while licking her bum and was now horny as hell. So immediately when I stopped licking her I tried to mount her from behind but she asked me what was I doing. Then she told me that she needed her sleep and I should let myself out and go home.

From then on forward her routine was to meet other guys now and then. Sometimes she made me operate her Tinder and arrange the when where and who of her dates but sometimes she didn't let me in on any of the details. Surprisingly the latter bothered me even more. If she only told me that she was busy and could not see me that night it left more room for my imagination. Almost as if she was cheating on me somehow more if she did it without telling me about it.

It would be difficult to explain all this to a normal person. Why would a young guy go along with such a one-sided relationship? There were many nights when I tried to figure it out even to myself. It had to be something to do with the fact that whenever I thought about being without her I felt miserable. And whenever I thought about her dominance over me I felt anxiously excited and sexually aroused.

Day after day she masterfully manipulated my feelings for her and we did have tender moments and even intercourse every once in a while. She let me enjoy her young sexy body if she was in a really good mood but according to my calculations, the other guys got to have her at least as often as I did. My tongue however saw a lot of action and I was rapidly becoming a pro-level cunnilinguist and an expert on how to make her cum.

And this is where my promise to her actualized. We could hear the doorbell and knew that it would be her date. She looked at me smirking. Making a nod and a significant look towards her walk-in wardrobe. Telling inaudibly me to hide myself there. Just like she had told me before. Head hanging low I went in.

Her closed door had these fixed wooden shades and if I pushed my head close enough I was able to get a decent view of her bed. Shania and her date soon arrived and without further ado started to make out on the edge of her bed. It should not have come as a surprise but the guy was someone I knew. Thus far she had stuck with people outside our college but now she had one of the football team's linebackers with her. I was pretty sure she had mentioned earlier that they had fooled around in the past.

"Shania, babe. I'm so glad that you called." he told her and continued between their kisses, "I thought you were dating that guy, Jess's ex, what was his name?"

"Shh baby. Are you here to talk or what?" she silenced him but then added, "What he doesn't know won't hurt him!"

So she wanted him to know she was still with me. That he would be doing her behind my back. And from the look of it, he did not mind at all but advanced on my girlfriend. Slowly pulling off the rest of her clothes he pinned her under him to the bed.

There was slow music which Shania had made me fix for them earlier and slowly they made out in the rhythm of it. Through the shades of the wardrobe door, I could see how she pushed her hand between them to adjust his cock to a better angle and then they were doing it.

"Oh baby you feel so good! Fuck you have such a great cock!" she panted and he started to give it to her. He lifted her legs a little and placed them firmly on both sides of his torso. And pumped his ass between her legs with long strokes. The romantic music in the air was mixed with the passionate pants and moans of my girlfriend having sex with her lover.

They had a good fucking session going on and when his movements were getting rougher and more urgent I could hear Shania telling him to shift the position. They maneuvered themselves in such a manner that he was still fucking her in some sort of missionary but her ass was on the edge of the bed and he had planted his other feet firmly on the floor. The other feed was on the bed and her calves were on his shoulders.

The angle of their position was optimal for me to see it happen. My own cock was iron hard and I had opened my trousers and pulled it out. Slowly masturbating while staring at them in shame. Focusing my eyes on his muscular ass. Further down between his thighs, I could see his cock penetrating her pussy. His large ballsac was swinging and slapping against her ass with every inward push.

Then I could see her hands. With a dexterous move, she reached between them past his cock to fondle his balls. Squeezing them magnifically every time he went in and easing her hold when he withdrew. This milking gesture seemed to be utterly enjoyable for him and he was bellowing how he was going to cum.

There was lots of vocal encouragement from her. She pleaded for him to fuck her deep and cum inside. The whole bed shrieked under them as the athletic man pounded away both her and her bed. In the end, he collapsed on top of her and there they rested. I was able to see how his balls rested against her ass twitching some final times while filling her up.

I was just about to wonder if they had fallen into sleep when she playfully slapped his ass and told him to get up. Hinting him that even though it had been really good, he would have to leave since she was expecting to see me later on.

The guy thanked her elaborately and with some last kisses told her to call him anytime she wanted and he would make time for her. I guessed he would not mind at all having some sort of friends-with-benefits relationship with the big-titted cheerleader even when she was dating someone else.

After he left she called for me. As I emerged from my hideout she laughed. Asking if it had been as good for me as it had been for her. Had I seen how well he fucked her? She could see my erect cock out in the open and it amused her greatly.

"Oh, my little closet cuckie-boy has definitely enjoyed himself. Did seeing his bigger cock make your little boy's pee-wee all hard?" she asked rhetorically and laughed even more.

Standing next to her bed I stared at her. Mesmerized by the sight. She was still lying on her bed naked. I was looking at her freshly fucked pussy and she was looking at me. Her laughter died away and a silence fell between us. The romantic playlist was still playing a slow piece about love. If I'm not mistaken it was Beoncé's Halo.

In the pressuring atmosphere, I hesitated. So she decided to give me some words of encouragement,

"Go on now. You promised to do it. Become my willing cuckold. Kiss me like you have never kissed me before."

Felling down on my knees I stared at her pussy knowing very well what was expected from me. I could see her staring down at me behind her gorgeous boobs. Her feet were wide apart and I was there on the floor in front of her and her bed. Her neatly trimmed bush was small enough to show her bare pussylips and her somewhat erect clit. Those were more than familiar to me as I had spent hours after hours caressing them with my lips and tongue but now there was something white oozing out from her.

I was delaying the inevitable long enough for her to lose her temper. She whispered irritatedly,

"Get on with it, bitch! You promised to do it. I know you want to submit yourself to me."

Inch by inch I proceeded closer and as I breathed the scent in there was no doubt that her pussy was full of semen. Just when I was about to make contact with my mouth she made a small contraction with her pussy and I could hear a quiet but obscene pussy fart and I froze. Looking at it there was more semen running out of it now and with some air coming out of her pussy there even was a small bubble of cum on the entrance.

She had had enough of my hesitation. With an angry grunt, she grabbed the front of my hair and pulled my reluctant face to her naked crotch. My tongue had been out to some extent and I could feel the warmness of it all as she smeared my face with the creampie in her pussy.

"That's more like it," she purred. Satisfied now that I was doing it. I felt like I was going to puke. But she had me so well trained on licking her pussy that little by little I was doing it like so many times before. Holding my hair she guided me through the experience. Soon I was lapping on it like a madman. Wondering how much of it would be in there. I tried not to swallow and kind of let it flow out of my mouth as soon as it went in. But it was not possible to do it so that I would not have ended up with a decent amount of another man's cum in my mouth.

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