Nice Guys Finish Last Ch. 06

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Phillip's bully helps him get ready for his first date.
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Part 4 of the 7 part series

Updated 12/24/2023
Created 09/24/2022
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Warning: This is a non-consensual fem-dom story. There are scenes that might make readers uncomfortable. All characters are above the age of eighteen. Please enjoy!

Chapter 6

Oddly enough, things started to change drastically after that fateful day. At first, I thought it was a bad thing, but as the days went by, I couldn't deny that some of the changes were positive.

After months of feeling invisible to the world, I suddenly had friends. I was skeptical about them at first, of course, but having people to talk to and study with was pretty nice.

The best part of all was that my study dates with Tina had actually been quite successful! I wasn't the best at reading people, but she always looked grateful to have me there, the way she smiled and laughed at almost everything I said.

Having Romeo present really helped as well. There were times the conversations would lull, and he'd be there to pick things up with funny stories. Best of all, he'd hype me up around Tina, making me feel as smart and confident as ever.

Spending so much time with a smooth guy like Romeo not only boosted my ego, but gave me someone to look up to as well. Seeing as he was the jock type, I decided I wanted to start working out. However, I was much too insecure to go somewhere public, like the gym.

Instead, I would just do push-ups and sit-ups in my room from time to time. And sometimes, early in the morning or late at night, when I was sure there was hardly anyone out, I'd go running... or try to, at least. At first, I could only do about five minutes, but I got to the point where I could do about twenty... if I mixed in some walking.

The main reason I started working out was to boost my confidence, but there was also another reason for getting in better shape. It was to impress Tina... or at least appear suitable. I just didn't want her to think of me as this pathetic little weakling. There wasn't much that was manly about me, especially compared to a guy like Romeo, but I figured if I started working out, maybe she would see me as a bit more masculine than I really was.

I was actually clueless when it came to the way she felt about me. Of course, she had been nice, and even agreed to go on steady dates with me, but could someone as pretty as her think I was manly enough to find attractive?

One thing that gave me hope, however, was that Tina was quite short and petite. Being taller than her actually made me feel good about myself. Perhaps from her shorter perspective alone she already saw me more manly than... well... Julia...

Not that it mattered or anything, but Tina and Julia were so different, not only in the way they treated me, but in their physical appearances as well. Obviously, my bully was tall, and with all the swimming and working out she did, she was so fit... Everything about her was more intimidating than the much smaller Tina.

Julia just looked so athletic in general. And sure, she had muscles in all the right places, but it never took away from her sexuality. She was just strong... and dominant... and looked great in athletic clothing...

Also, not that I had any right to be picky or anything... but my evil bully had pretty big boobs and a nice ass... I'm guessing Tina wore A-cups; not that I understood how bra sizes worked. I just knew she wasn't as... blessed... as Julia was, unfortunately...

Speaking of Julia, however... yeah... she was officially back in my life... And as much as I hated that, she constantly reminded me that I was the one who opened that can of worms back up.

I truly believed that if I had just walked past her that day, instead of stopping and congratulating her for winning that swim meet she said she didn't care for, she would have never forced herself back into my life. Julia said so herself, which she liked to remind me of every time she ended up in my room...

Although I was confused about her last message to me, and her communication skills in general, I started to think she was truly upset that I let her back into my life. For whatever reason, she was angry that I didn't ignore her like she previously demanded. Perhaps that's the reason she started spanking me from time to time... which I definitely didn't masturbate to, by the way...

Often, I wondered what the meaning was behind her words, and why she could be so upset at me for congratulating her on a swim meet. But whenever I attempted to dig deeper, my mind would eventually wander back to that kiss we shared, and whether or not that was real passion I felt in that moment.

Whatever the case was, Julia was now back in my life, and she'd come over every now and then to torment me just like she had in the past. It was always in my room, which was easy for her since I didn't have a roommate. To make matters worse, she ended up stealing my spare key card, so all she had to do was manipulate me to open the deadbolt once she got into my building.

Julia's visits were pretty erratic. Nothing was ever planned; I would just get a message on my phone that she was coming over, or sometimes I'd find out when I heard a knock at my door. But no matter what the circumstances were, her appearances always ended up the same; constant tormenting.

It was similar to the way things went towards the end of high school. We didn't share another passionate kiss like the one before, nor did we ever even mention it. Instead, my bully would just force me into embarrassing sexual acts while berating me like the little pervert that I was.

The main difference from high school was that instead of blackmailing me into doing her homework, she was now mostly just making fun of how pathetic I was. I definitely didn't need a reminder that most women found me unmanly, but there she was to tear me down every time I saw a glimmer of hope.

I ended up admitting that my dates with Tina were only study dates, just like she already assumed. She made fun of me for it, of course, but I didn't have the courage to admit that I needed another man there with me. I could only imagine how badly Julia would torment me if she knew that part of the story.

Regardless of what Julia knew, she forced me into embarrassing acts and then made fun of me for the way my body responded to them. Wanting her to leave me as quickly as possible, I'd just go along with it, allowing her to lick my nipples, spank me, and tickle my balls. Probably the most humiliating of all, she would force me to masturbate in front of her, which was even more embarrassing when she was fully clothed, pretending to have a conversation with me.

No matter how emasculating the acts were, I'd still end up cumming very quickly... and very hard.... She'd always laugh at the big mess I'd make, and warn me how embarrassing it would be if I did that with Tina or any other woman.

Eventually, I got to the point where I not only needed to prove her wrong, but I needed to prove to myself I could be more than what she made me out to be. After weeks of push-ups, sit-ups, running, and three square meals a day, I finally decided that I needed to ask Tina on a date... a real date. I didn't want there to be any studying for once, and I definitely couldn't have Romeo there if I ever wanted to see myself as a man.

One day, after chemistry, I stopped Tina before she left for her next class. "Hey, Tina..." I started, mustering up all my confidence as I stood there shaking. "Would you like to get together sometime?"

Immediately, a smile came over her face, and she looked nowhere near as panicked as I did. "That sounds great," she said nonchalantly. "With finals coming up, I could use some extra help."

"Oh, not a study date..." I explained as my heart almost burst out of my chest. "I mean... we can study later, but... I kind of just wanted to hang out... without studying for once..."

An uncomfortable look came over her face as she put her head down, most likely searching for the right words to reject me. However, much to my surprise, a smile eventually returned as she answered, "All right... sure."

"Really?! I mean... yeah, let's do it!"

"Yeah, I'm free this evening," she explained as she pulled out her phone to check her schedule. "How about that coffee shop on campus?"

Without even thinking it through, I immediately blurted out, "That sounds great!"

***

The rest of the day was a bit of a blur as I suddenly found myself on cloud-nine. My heart was still racing from the adrenaline of actually asking Tina out. A combination of excitement and anxiety rushed through my body as I waited for my chance to see her later on.

Feeling that I had finally done something manly in my life for once, I decided to text Julia in an almost "I told you so" fashion, even though I knew she'd never back down from her stance about me. In typical Julia fashion... she hit me back with a, "Lol, don't fuck it up," text that brought me back down to earth.

I didn't know why she had to say that, or why she felt the need to bring someone like me down after finally achieving a milestone. However, I wouldn't receive any further information through text that day, as she stopped responding to my messages.

When I got back to my dorm room, I was suddenly a mess, as my date with Tina was quickly approaching. I hadn't decided on what to wear or what to talk about. A nervous wreck like me needed to be prepared for a date with a cute girl like her.

After finally picking out an outfit, I got changed and practiced some common conversational lines in the mirror. I was then interrupted by a knock at the door... who I could only assume was my worst nightmare...

Of course, I was correct. It was my long time bully, Julia, presumably there to ruin the first positive moment in my potential future love life. Just the sight of her left me trembling at my knees, frantically asking, "Julia... uh... what are you doing here?!"

"I'm just here to make sure you don't fuck this opportunity up," the evil but beautiful woman explained as she made herself comfortable in my bedroom. "Since this is my only opportunity to get rid of my stalker, I want to make sure this date goes well."

Before I could even muster up a response, she cut me off by asking in an accusatory way, "What were you up to? Practicing what you're going to say to her in the mirror?"

"What?! How did you know that?!"

"Because you're a loser with no social skills," she explained, laughing at my expense. Then, furthering the humiliation, she walked over to my closet and further tormented, "I bet you were also stressing about what to wear."

"Huh?" I reacted, while pointing at the collared shirt and jeans I was already wearing. "I figured I'd just wear this..."

"That?!" she asked, looking as if she were trying to hold in her laugh.

"Yeah... What's wrong with this? It's a nice shirt."

"Pretty casual for a date, don't you think?"

"Uh... I guess I hadn't thought of it..."

"You want to impress her, don't you?" she asked as she sifted through my clothes once again. Then, pulling out my one dress shirt and some slacks, she suggested, "Wear this. It's much better for a date."

"Don't you think that might be a little too fancy? We're just going to a coffee shop."

"Eh, going out for coffee isn't much of a date, but I think this outfit still works. Plenty of people wear nice clothes to coffee shops."

For some reason, I decided to take heed of Julia's advice. This didn't seem like a trick for once, and I actually valued her opinion, seeing as she had much better insight into what women liked than I did.

Seeking more help from her, I decided to swallow my pride and ask, "Do you have any more advice for my first date?"

After scratching her chin for a second, thinking with deep intent, she finally came back with a question I thought was rather pointless at first. "Well, since you're going to a coffee shop, what do you plan on ordering?"

"I was thinking maybe a latte," I answered once I determined her question wasn't a joke. "I've only recently started drinking coffee at all, so I like my drinks to be very sweet. I was even thinking of just getting a smoothie, since it's already going to be pretty late."

"A smoothie?" Julia asked, almost fighting off another smile.

"Yeah, what's wrong with that?"

"It's just... pretty unmanly to order a smoothie at a coffee shop... You might be better off with the latte, though that isn't very masculine either."

"Does any of this really matter?" I asked, growing frustrated by her constant tormenting. "Will she really develop an opinion of me over a simple order at a coffee shop?"

"Well, a black coffee would have definitely made you seem more manly, but go ahead and get your little latte. Just please... for the love of God... do not order anything juice related in front of your date."

Rolling my eyes, I just groaned, "Whatever," as I grabbed the clothes and began walking off so I could change in the restroom. However, Julia then asked a question that stopped me in my tracks.

In a nonchalant manner, I heard her voice from behind me, asking, "Which underwear do you plan on wearing?" Then, as I turned my head in fear, I witnessed her going through my underwear drawer, while playfully expressing, "These are all so cute!"

"What are you doing?!" I whined as I quickly ran over to shut the drawer.

"Quit your pouting," she replied as she pulled out a couple of pairs of my boxers and briefs. Then, holding one of the small pairs up, she suggested, "You should probably wear something tight like these."

"Why is that?" I asked, raising my eyebrow. In reality, I knew there was no chance I would get far with Tina that night, so I didn't understand why it mattered what I wore underneath my outer clothing.

Instead of giving me a straightforward answer, Julia just stared at me, smiling with that devilish look she always had. Then, as I looked on confused, she finally peaked down and pointed out the tent I was pitching in my pants.

"That's the reason you need tight underwear," she said, laughing at my expense once again. "We all know what a pervert you are. You'll need to hide Little Phil in your waistband or something."

Embarrassed yet again, I tried to cover up even though she'd already seen my erect penis so many times in the past. By now, being seen with a hard-on should have only mildly affected me, considering what she had done to me before.

"You might want to take care of that little situation," she suggested, gently poking my penis through my pants. Then, completely throwing me off, she asked, "Do you still think about me when you jack off?"

"Huh?!" I reacted, looking on with big eyes and an open mouth.

"I'll take that as a yes," Julia confirmed as she took my wrist and led me towards the restroom. "Now, let's kill two birds with one stone and get you into the shower."

"Get me into the shower?!"

"Uh, yes... Did you really think you were going to go on a date without cleaning yourself up first? That's rather inconsiderate."

"I don't have a problem with that!" I quickly argued, unsuccessfully pulling away in fear. "But why are you taking me?!"

"I thought we already covered this," she responded as she turned the water on and began stripping me of my clothes. Once I was naked, she looked me in my eyes as she placed her hands on her hips. Pointing at my erect penis again, she explained, "Since you're such a little pervert, we need to take care of your boner before your date notices it and gets creeped out."

Though I had orgasmed several times before at the hands... literally... of Julia, it was still just as scary and nerve-wracking as it was the first time she so embarrassingly forced me to cum all over the place. I was suddenly in another situation where I knew she would be forcing sexual acts upon me against my will, yet somehow, it felt even more messed up knowing I was about to go on a date.

Surprisingly, after my bully pushed me into the standing shower, she did something that left me completely breathless. Slowly, Julia started to take off her clothes, every last article, including her sexy little underwear. Before I knew it, the beautiful woman was standing right next to me in the shower, completely naked with her hair tied up.

Of all the times Julia had ever forced me into sexual acts, this was the first time I had seen her full body exposed. There were times I had seen her in something as small as her swimsuit, or even just a thong, but now her voluptuous body was covered by nothing but the droplets of water coming from the shower head.

Of course, I appreciated her beautifully sculpted breasts as much as I did every time I was lucky enough to see them, but in this instance, it was her uncovered crotch that I got to lay my eyes on for the first time that had most of my attention. I immediately noticed that she was either shaved or waxed. There was only a smooth, unblemished surface, complimenting that cute looking slit of hers.

It wasn't like me to stare at a vagina or a crack whenever I watched porn, but there was something about every inch of Julia's body that made her look masterfully crafted. It was almost infuriating that the evil woman I grew up hating could be so perfect. However, before I could curse the world for making her so physically flawless, my mind went into a haze as I felt her soapy hands rubbing up and down against my vulnerable body.

"What are you doing?!" I reacted in a high-pitched voice.

"What does it look like I'm doing? I'm washing you." Not stopping for a single moment, she continued, "I don't trust you to wash yourself thoroughly before such an important event."

Having her soft hands roam up and down my body was almost more erotic than any of the extremely kinky things she had done to me in the past. To make matters worse, the hot bully was completely naked, and I couldn't take my eyes off every inch of her silky smooth skin.

Suddenly, when my eyes moved up Julia's body, taking a second to appreciate her breasts again before meeting her eyes, I realized she was staring at me like the creeper I truly was. "Do you mind focusing for a second?" she asked, causing me to blush before darting my eyes away from her. "Quit staring at me like some kind of pervert."

"Oh, I'm sorry... It's just... I've never seen you completely nude before..."

"Well, you're not supposed to be getting off to me," Julia explained as she let her hand roam closer to my private areas, teasing me just the right amount to make me desperate. "You're supposed to be thinking about this mystery girl you're about to go on a date with. I don't know why you'd be staring at me, unless, of course, she has a body like mine."

In that moment, as my uncontained lust was at an all-time high, I was forced to admit to myself that though Tina seemed like a good fit for me, she didn't come close to having a body like Julia's. Of course, I had never seen her naked, but there was no way she had the perky tits and the voluptuous ass that my lifelong bully did. That, I could give Julia credit for, no matter how mean she was to me.

As my mind continued to ponder the differences in the two women's bodies, Julia grabbed my hand and forced me to take a hold of my own cock. "You're supposed to be taking care of yourself so you won't have an embarrassing hard-on during your date," she whispered into my ear, sending chills down my spine.

I did as I was told and began stroking my ever so erect penis as I felt Julia's soft hands thoroughly cleaning my body. With my heart racing, and adrenaline rushing through my veins, I just knew I would reach an embarrassing climax like I did every time she was there to force me to cum against my will.

Much to my surprise, however, as I tried to fixate my mind on the much sweeter... but flatter... Tina, I noticed that I wasn't achieving an orgasm as quickly as I expected. I ended up lathering my hands with soap several times, attempting to get myself off while fantasizing about the girl I was about to see instead of the girl I was actually with, but I just didn't have any luck.

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