The Good Guy Always Loses Ch. 01

It was getting late and I had quite a bit to drink, far more than she did at least. My mouth started running, and I started spilling my insecurities out. I told her about how I can never measure up to the douchebags in our school in both body size and the ehhmm... "other" size. She just giggled and told me not to worry about it.

I would win her and other girls over with my friendliness and personality, my diligence and patience. When I finally brought up the taboo subject of Todd and his douche persona, I saw her smile a little. I asked her what was so funny and she replied "huh... oh nothing. I just uhh- I think it's funny how he gets under your skin. You're a much better person than him, don't let him affect you." I smiled and thanked her.

The rest of the night after I had brought up Todd, she seemed very distracted and aloof. I spilled my insecurities further and told her how much I hated him, and him constantly calling me "small boy" and "tiny dick" to which she giggled and repeated "tiny dick..." under her breath. I loved making her laugh. I told her I felt so insecure around him and he emasculated me a lot. She seemed to find all of this quite funny, and I mentally congratulated myself for being so hilarious.

She went on to say how she definitely thought Todd was attractive, but that was it, she knew he was a major douche. Again, I never ever thought anything of her giggling and distraction, just assumed she found my story-telling and talking style very entertaining. I said, "All I ever want is for you to be happy." She smiled at me.

Jenny and I went on more and more dates until finally one day when we were back home at my place, I managed to get my hand up her shirt while kissing her and things got hot from there. We moved it into the bedroom all the while with me whispering how "I've wanted this for so long," and "I thought this day would never come." After a handful of more self-depreciating comments, until she finally put her hand on my mouth and said, "shhh... stop, I'm here now, so let's just do it."

I managed to get her shirt and pants off so that she was only in her underwear. After that she took off my shirt. I felt a little self-conscious about my lack of muscle, but she told me she thought it was cute. She finally managed to get my pants and briefs off, after which my erection stood free in the air. She paused for a moment to look at it, then looked back at me and bit her lip, trying to stifle a smile. When she saw I was a little hurt she put her hand on it.

She lied me down on the bed and sucked it into her mouth. It fit inside her mouth without a problem until my pubic hair tickled her lips. She finally got up and straddled me, rubbing her thighs against my cock. I told her I had a condom in my drawer, after which she took of the rest of her clothes and went over to get it. She tore the condom wrapper and tried to slowly put the condom on me.

I don't know why but the condom seemed suddenly bigger. It wasn't like this was the first time I had had sex, and weren't all condoms the same size, except magnums (Which I would never dream of buying)? My dick could barely fill it up. She looked a little puzzled as to how and why I didn't have a dick big enough to fill even a regular condom. She tried to squeeze the sides down along the length of my penis, but to no avail. She looked a little disappointed, but she tried to hide it.

She said, "Oh it's ok, we don't really need to have sex do we? We can still enjoy ourselves right?" This time I was the one who was disappointed, but of course I didn't show it. 'Having her here is more than enough,' I thought. We just cuddled and kissed.

I admired her flawless angelic body all night long. She was completely hairless from the eyelashes down. It really made me wonder if she was an angel in terrestrial form. I admired her milky white complexion and gorgeous fluffy pink pussy and pink nipples. Over the course of the night I sucked her nipples constantly and came at least four times as she stroked me with her extremely soft hands. There was barely any motion as she stroked, as moving her hand up and down just an inch or so already made it slip of my cock. She seemed amused at the idea and there was something else too... But I was too inebriated and in too much ecstasy to notice anything strange. In the morning she was gone when I woke up, and I went about my day as usual.

When heading to class, I noticed her outside talking to a large guy, who I couldn't make out from the back. She was giggling and blushing slightly and when I came up to them I saw it was Todd... fucking Todd. "Hey little Dick? How's it going?" he asked, and chuckled. A couple that walked past us chuckled at the comment as well and the guy high fived Todd on the way past.

"Fuck you Todd!" I retorted. "Ohhh... Careful now, little dick here has a temper," he said, directing his talk to Jenny. "Better be careful baby, he'll snap in a second. Come sit with me and the guys, we'll take care of you..." he continued, winking at her. She giggled and playfully hit him, "Stoooppp... be nice!" to which he put his hands up playfully, slowly pivoted around and headed to class. I was angry, so I said nothing of the issue.

Over the next two weeks, Jenny would text me saying she was heading to class a little earlier than normal, it was curious, but nothing strange. I would catch him at least three times a week chatting with her outside class, till the point where she would actually be laughing while blushing, and smacking him playfully. When I asked her about it, she replied, "Oh nothing, he's just a big douche... uhh- and he was... just... saying some stupid things, so it was funny. That's all."

One day I came around through the exit of the class from the other side, so I was approaching my seat from the top of the hall, down the stairs. There were no pillars past my desk further up, so coming down from the top, my view of the front of the class was unobstructed, all the way till the exit. I walked down especially slowly and saw Todd making faces at my desk, with Jenny already there. Obviously I couldn't see her face since I was behind her, but I was able to see the motion of her giggling and quickly looking down.

As I finally approached the table, she gave a surprised "Oh!" and said, "I was looking for you in the front of the class." I asked her about the faces Todd was making and again she said something along the lines of, "Baby don't worry, he's just a big idiot, and sometimes he does and says funny stuff, that's all." I just accepted it and moved on, and since the midterm session was coming close, I couldn't have any distractions.

Through our many sessions of studying and many more dates, I progressively fell more and more in love with Jenny. She was so beautiful and funny, and charming too. She kept telling me how smart I was and how much of a good person I was. It continuously convinced me that she was the kind of person who would make the perfect wife.

She obviously didn't care about the physical aspect too much, since she didn't pressure me into sex at all, and while I did want to keep seeing her milky white body and angelic pussy lips, I didn't want to have another embarrassing session like the first one. We went to dinners, and movies and yes occasionally fooled around, but I made sure never to mention condoms ever, so we just touched and I gently played with her body. She never got to orgasm, but I came regularly four or five times. Her hands were just so unbelievably soft. But it was limited almost exclusively to that, because she would want to finish quickly so we could just watch another movie at home or play a game.

Again, as I always would, I told her "All I want is for you to be happy."

Then one day I was walking to class when I walked past one of Jenny's friends who smiled pleasantly and waved. "Hi Tiny di—" she stopped mid-sentence and spun around to look at me, and I looked at her.

"Uhh... uhhh Hi uhh—Jeff. How's it uhh... How's it going?" she managed to stammer out.

"Umm... okay I guess?" I replied, quizzically. "Okay, Bye!" she said quickly and hurried off. It was odd, because that girl wasn't in my class, and definitely wasn't friends with Todd and the other douches, so how...?

When I made it to lunch I told Jenny about the run in with her friend and what she said. Jenny quickly turned red, looked around and nervously giggled "Well... Oh I'm sure Todd being the douche he is must be telling some other people and... well who knows? Who cares really? Right baby?" she spluttered, with little confidence in her voice. "Yea... I guess so..." I replied, concerned.

We continued working on the Psychology lab, but the entire time Jenny was furiously texting on her phone, and seemed a little annoyed at someone on the other end. I managed to read the first line she typed into the iPhone, which was tilted down towards me. It said, "Amy, why the hell did you say..." and then she pulled the phone towards her and continued typing.

"Everything okay?" I asked.

"Oh. Perfect, my friends are just being unreasonable about something," she replied.

The night after, Jenny and I went to catch a movie at the cinema. As we were walking out of the theatre, we ran into Todd and his buddies. "Ohoohh... look who it is. Small Dick! What's up man?" he said as he slapped me on the shoulder. "Oh and what do we have here? Bonjour Mademoiselle..." He gestured towards Jenny, immediately after which she smiled and blushed.

Then Todd moved his elbow back and touched one of his friends on the arm. It seemed odd, but the other two guys came up to me, 6'1" and 6'3" respectively and started asking me polite, yet unnecessary questions. "Yo dawg, what movie were you watching man?" they asked, after which I told him, and the other replied, "Oh man we saw that, it fucking sucked!" and they both laughed.

As they were barraging me with questions, I saw Todd approach Jenny and start talking to her. He sort of moved into her and she was very close to him. He was saying something undecipherable, but I could tell he was trying to make her laugh.

Over the blur of chatter, movement and laughter of his two douche friends I could barely see Todd hold his hand out in front of Jenny and indicated between his index finger and thumb a small distance, then pointed his thumb behind him directly at me. Jenny giggled and looked away a little, while playfully slapping his chest and mouthing what looked like "stop..." Then she caught my eye, and stopped giggling. Todd turned his head to see me looking at them, and looked back at her, and put a hand on her bare shoulder and nodded to her while saying something. She nodded back and offered a cute smile.

He then backed off just a little. "Alright guys, that's great but we really got to get going," I said, and pushed through the two friends to go rejoin Jenny on the other side of Todd. I grabbed her hand and we headed back home.

I confronted Jenny about what happened and she promised me he was just being "extra-douchey" and nothing was the matter. It seemed that he was acting that way around her a lot lately. I expressed my concern and told her she should stay away from him, to which she agreed and told me not to worry. We got drunk again that night, and since I was upset I spilled more insecurities to her about how I think Todd is up to something with her and how I am such a small guy. I brought up the small penis again and I could swear I saw her cringe a little, before taking another sip of her drink.

She seemed extremely quiet the entire time, and didn't want to speak much. I kept confessing how much I loved her and cared for her and that I would do anything for her, because it was true. The more I spoke, the quieter she got. She said very little, but one line I could remember vividly was, "You're such a sweet, emotional guy Jeff. Don't ever change that." She may have even said it multiple times, but it made me feel good so I had no problem with it.

The next week, everything went on as usual, Jenny was quiet, and Todd was an extra douche, constantly finding ways to spend time with Jenny alone, but I was always there to stop it. Jenny didn't show up Monday night. When I asked her the next day, she seemed completely non-receptive. When I asked her what was wrong, she said, "Oh nothing sweetie, I'm just really tired. I didn't get too much sleep last night." I found that quite odd, since the mid-term period had passed, but what could I possibly know about her other classes?

Then I spotted a bruise on her right arm, since I sat on her left side, I couldn't see it very well. "Oh crap, what happened there?" I asked. "Oh uhh... nothing baby, just fell down and uhh... hit my door... Yea that's it," she said as she put her head back down to rest on the desk. I gave her the benefit of the doubt, because I myself have gotten bruises from falling and hitting myself. Todd walked towards the exit and gave a smirk when he saw Jenny's head on the table. Again I gestured, "What?" with my hands. He just disregarded me and left.

Wednesday night was date night, but I got a text from Jenny saying she couldn't make it and that she had to meet a friend from another school. I told her I was disappointed, but that I understood. I ended up getting drunk alone that night, when my sister messaged me, and then my brother consecutively. They both went to school in Salem and told me to come up since the family was gathering for the weekend.

My sister continued to tell me that she would be coming down for the rest of the week, and then on Friday night we would go up together. I wasn't too thrilled, since I knew I would be hosting her in my house. I filled them in a little on life, and what was going on, telling them about all the people over here. After I finished texting them both, I decided to call Jenny, in my drunken state to tell her the news.

I called her and after about three rings, I hear the phone being answered. There were muffled sounds and what sounded like a guy's voice asking, "Who the hell is that?" and then I recognized Jenny's voice soon after. There was a bit more struggling and what sounded like the phone dropping.

"Oh fuck it's... stop give m—" she said, and the line was cut.

I sat up, a little weirded out by that, but remembered that she said she was going to another school to meet a friend, so there may have been some people I wouldn't have recognized. I tried calling her again but it went straight to voice mail. So I left her a voice mail asking what was going on and informing her about my sister. I quickly fell asleep after that, only thinking fleetingly about the phone call I made to Jenny and how strange it seemed.

In the morning I woke up to knocking on the door. I went to open it and standing in the doorway was my sister. "Hi loser!" she said excitedly.

"Oh great... Nice to see you too Stacey." I managed to say.

"God you look like shit, what happened to you?" she said pushing past me into the house. I told her about the alcohol. "What? You were drinking alone? What happened to Jenny?" she asked, in quick succession.

I told her how she went to go see friends from another school. As I was talking to her, I suddenly flashed back to the weird phone call from the night before, but decided not to say anything, because obviously why would she care?

Stacey went on to tell me her plans and that we would only stay here for tonight, then head out the night after. She told me to introduce her to Jenny and then we could go to the movies at night. I proceeded to tell her that I had work and school today, and would only be back by 7pm. She said she would just roam around, "it's not like I'm new to Massachusetts."

That night I went the entire day without seeing either Jenny or Stacey, because Jenny was not in class that morning. As class went on I started watching people going to the bathroom out of boredom. I noticed Todd wasn't there either. 'What a fucking moron,' I thought to myself. Right after class I got a text from Jenny telling me she got my message from the night before and that she'd love to meet my sister today. After telling my sister, I swung by work for a short day and headed back home in the evening.

At home I heard the shower running and assumed Stacey was washing up and getting ready to meet Jenny. So I too went to the other bathroom and took a quick shower to get ready. When I got out, Stacey was ready and was sitting on the couch on her phone. I got changed and came out. I saw she was wearing a low cut tank top and tight jeans, revealing her well rounded tits and great shape. I knew Stacey was relatively promiscuous, well, pretty much every girl with her shape would be, but damn!

She gave me a look and went back to typing on her phone. "I want to make a good first impression on your girlfriend don't I?" she asked rhetorically. "Uhh... yea, but just remember, I'm the one dating her... got it?" I replied in a joking manner.

Stacey shot me a lame look, and then went back to typing.

I heard a knock on the door. I went to open it and kissed Jenny when she came in. Jenny walked into the living room with a bottle of wine and set it down on the table. Stacey got up and said, "Wow... so you're the famous Jenny. I've heard a lot about you. God you're gorgeous!"

"Oh my god, stop it!" Jenny said in response, then asked, "That coming from you, seriously?" Both girls laughed and hugged, then sat next to each other on the couch.

"So I hope Jeff has only told you good things about me!" Jenny exclaimed.

"Oh my god..." Stacey replied, "This fool cannot stop talking about you. He tells me you're the greatest, such an amazing girl, so shy and honest and beautiful, and this and that and blah blah blah. Get him to shut up about you, that's the trick!" Stacey laughed.

Jenny gave a weak laugh and looked down at the table. I could tell that Stacey noticed the peculiarity in that too.

It was a little quiet for a moment before Stacey hesitantly asked, "So... let's open this wine bottle shall we?" She looked at Jenny who nodded with rejuvenated enthusiasm. "Yes, Please!" Jenny exclaimed in reponse. They both giggled a little. I went into the kitchen and got three glasses, and we each poured one.

After the third glass each, Stacey told Jenny about the movie plan. I was still a little apprehensive, because of the incident from last time but decided, 'What the hell... it won't happen again.' We got into a cab and headed to the theater.

Just as we finished the movie, we were heading out of the cinema and walked down the hallway of the complex towards the cabstand. As if right on cue, Todd and his friends show up out of nowhere. "Oh shit..." I muttered to myself. I noticed that Jenny's eyes widened with apprehension too.

"Heeeyyyy... Tiny Dick! What's happening my man?" Todd shouted across the hallway.

'Motherfucker!' I thought. "Wow wow wow!" Todd said and stopped. He put his hands out stopping his two buddies as well. "What the fu—Damn it Pencil Dick! How is it that you're always hanging around gorgeous girls?" He asked motioning towards Jenny and my sister.

"Todd please just go away," Jenny said. It seemed odd, since Jenny had never confronted him openly before.

Todd replied, "Oh damn. What's the matter baby, didn't you li—"

"TODD!" Jenny interrupted, "Stop it." She seemed uncomfortable.

"Ok, relax baby, I just want to say hi to this gorgeous girl over here," He said, motioning to Stacey.

Before he could say another word my sister was in front of him with her hand out, "Hi. I'm Stacey. Jeff's sister."

"Holy crap!" he said, while the other guys laughed. He asked, "You're Limp dick's sister? How the hell did that happen?"

Stacey bit her bottom lip and looked up at him. "Beats me, Jeff's told me a lot about you" she said.