Stupid BoyChapter 2: Many Firsts free porn video

Labor Day was the busiest day of the season for Dad and his Parks and Recreation staff. The parks would be full and it was the last day they had the public pools open. Greg and I always had to help in some way. For some reason Greg had gotten out of helping this time. He got up early and left for the day. Dad made me help the lifeguards at the main pool. You had to be 16 to do it for money so I was an unpaid volunteer, or that was what Dad told me.

By 11:00 am the pool was packed. It was a perfect end of summer day with the temperature going to be in the low 80's and not a cloud in the sky. For many of the teenage girls it was a chance to even out their tan. For the guys it was a chance to flirt with the many pretty girls.

I was put in charge of gofer duty. Anything the lifeguards or staff needed I was sent to fetch. I was getting everyone's lunch orders when I saw Bill Rogers and company show up. They were all scruffy looking guys and you could see the crowd keeping a watchful eye on them. They were making no secret they were looking for female company. When they found some prime lounge chairs, they chased off the hapless guys sitting in them.

It wasn't going to be long before they pissed someone off and there was either going to be a fight or the staff was going to be forced to get involved. I had not seen Bill since the night of the party. I could feel the hair go up on the back of my neck. This guy scared me. He was a complete wild card and I know he could become violent at the drop of a hat.

Knowing all this, I had no idea why I went up to him. "Hey Bill, how's it going?"

It took him a minute to realize who I was. "Dawson, it's good to see you man. I didn't know you worked here. How was your summer?"

"I was sent away for the summer."

"Oh yeah, I heard that somewhere. Hey, thanks for keeping us out of it."

"No problem. I wanted to ask you a favor."

Bill tipped his head forward so he could look over his sunglasses. "What kind of favor?"

"You are making our guests nervous. I was wondering if you would do me a favor and leave."

Bill and my eyes locked. Out of my periphery, I saw two of his goons stand up on either side of me. I knew if I showed any fear they were going to jump me. Bill was looking pissed.

"Listen pussy, do you see all this prime trim that needs my attention?" He pulled his sunglasses off and made a circular motion to indicate all the women close to them.

"Bill I understand, but to be honest I'm not seeing anyone who is interested. They seem nervous. Today is supposed to be a fun day for everyone. We both know at some point you or one of your guys is going to cause a confrontation."

He chuckled, and not in a nice way. "David you have balls. I think our confrontation is about to begin with you getting your ass kicked."

"Hang on Bill. You do owe me a favor and I'm calling it in now."

He got up and got in my face. Next thing I knew he slugged me in the gut. I went down to one knee and doubled over. Bill grabbed me by the hair and pulled my head up. His face was a mask of pure evil.

"No one tells me what to do! Do you hear me?"

I choked out, "Yes."

He seemed to make a decision. He jerked my hair back causing me to sprawl on the pool deck. He got down close to my ear and spoke so only I could hear him. "You're lucky. I normally wouldn't let something like this go, but I do owe you a favor. We are even now, but keep an eye out. I may need to kick your ass just to make an example of you."

He stormed out with his goons in in his wake. I got to my feet and several people gave me appreciative looks. None of them seemed to want to check on me. I think they were embarrassed because they were going to let me take a beating. I went to the office and collected myself. It was never good to get on any bully's radar when you are a nerd, especially a bully like Bill. I would have to be careful at school for the next couple of weeks.

Tuesday September 3, 2013 – Freshman Year

I came to school with my new haircut and in the first outfit Cindy told me to wear. I was wearing a fitted black t-shirt and tight black jeans. The shirt was almost worse than going without one. It showed every bump, curve and ripple. The jeans were very tight and Cindy said they made my butt look cute. After the summer of farm work, I was no longer embarrassed about my body, so I was not too worried. Jeff and Alan were out front. They started giving me a hard time. Jeff fired the first shot and nodded to Alan to turn around as I came up. "Alan, do you know who the new guy is?"

Alan spun around and faced me. "Hey GQ, where is the photo shoot? Is it true all models are gay?"

"Yes we are and I have to say I'm into nerdy little guys. What are you doing after school today?"

Alan started to back up and Jeff burst out laughing. Jeff asked, "So what is with the makeover? Did Tami get her wish and turn you into her little Ken doll?"

I gave them a scowl. "No actually Cindy got her claws into me. Seriously guys, this isn't too gay is it?"

Talk about walking into it. I thought they were going to stroke out they were laughing so hard. I was ready to head home and change when Peggy came up. My back was to her and she saw my best friends cracking up.

"Hey guys what is so funny?" I heard her gasp and I turned to her and she was slowly checking me out. I was starting to worry something was wrong because I couldn't read her expression. Her hand came to her mouth and I heard her whisper, "Oh my."

"Are you okay?"

She seemed to come back to herself and she looked me in the eye and blushed. Peggy Pratt, my wet dream was checking me out and blushing. To hell with what Jeff and Alan thought. If Peggy liked it, I would be dressing up like a GQ model every day of the week! Thank you Cindy!

"No, I just never realized, uh, dang ... Dawson you are a hottie."

To their credit, Jeff and Alan shut up when they saw Peggy's reaction. I think Tami had smacked Alan enough in the past few days to slow him down. They were looking at me in that weird way they do when an older good-looking girl talks to me and I act like it happens all the time. I leaned in close so only Peggy could hear. "Not too gay?"

She actually snorted. She seemed fascinated with my new haircut. She reached up and ran her fingers through my curls. Any time Peggy was touching me like this was a very good thing. She leaned in a little closer and said, "No. Seriously, I like the new look."

Then she shocked me when in a breathy whisper she said, "A hard man is good to find."

My eyebrows went up. I'm sure the guys had not heard her because they didn't react. Peggy was eyeing me as not just a friend! Then she jerked as if she realized she had said it aloud. I just winked at her. I put my arm out and said, "Madam, may I escort you to your locker?"

"Why sir, it would be my pleasure." She noticeably relaxed. I am sure she was glad I had not pressed the issue, but I was filing this away for future study. I made a significant step in getting out of the 'friends' penalty box where so many nice guys find themselves. At least she was looking at me with a little heat.

We giggled as we entered the building. Then things got a little weird. As we walked down the hall, the crowd seemed to part as we walked to Peggy's locker. She stood a little taller, pushed her tits out, and put a little wiggle into her walk. I could tell she was enjoying the attention. When we got to her locker, she gave me a peck on the cheek.

"Thank you kind sir ... You can walk me to my locker anytime." I had a stupid grin on my face all the way to my first class.

At lunch, I caught a nice looking brunette, who I remembered from World History class, checking me out. She must be from one of the other junior highs who came to this high school because I couldn't remember her name. She was petite with cute little breasts and the killer little butt of a teen who was just starting to become a woman. She seemed like someone I would like to go out with so I walked up to her and said, "Hi, my name is David."

"Hi I'm Tina." The good news was she hadn't run off screaming. She seemed nervous. Without my brother's coaching, I would have just frozen up. Seeing her fidget was liberating. I felt enough in control to ask, "I would like you to go with me to have ice cream at Jerry's on Friday after school." Did I just say that? I held my breath waiting to hear her response.

She smiled and said, "You mean ... with other people?"

Did she not want to go with me? Not wanting anyone to overhear I leaned forward and whispered in her ear. "No, it will be just the two of us on a date."

My hot breath on her neck caused her to shiver. Her eyelashes did this cute little flutter thing as she stammered, "I ... I ... I would love to."

She obviously was not expecting me to ask her out. Her eyes were darting around looking for her friends. I let out more of my hot breath on her neck. Her head went back just a little, and she closed her eyes for a moment. I glanced down and noticed her nipples getting erect. Heck yes! It felt really good to be in control. I stepped out of her personal space. "I will meet you out front after school on Friday and we can walk over."

The bell rang and I headed to class. I noticed she and her friends were all huddled together sharing all the details. I was about to find out girls are bigger gossips than guys.

Tami corralled me and headed me towards class. "What was that about?"

For once, it felt nice she didn't know everything that was going on with me. She obviously noticed the new look and my confidence. I know this was just the opening question in my interrogation. I had three choices. Clam up and let her puzzle it out herself, let the interrogation continue, or just tell her. I decided on the latter.

"I got myself a date for Friday night." She actually stopped in her tracks and snagged my arm spinning me around to face her. Okay, I didn't actually choose to tell her everything. She did rather scare the crap out of me.

"I asked Greg to help me, ummm ... socially. He enlisted the help of Cindy to do me over." She just nodded. "They have been coaching me and my first assignment was to get a date for Friday night, so when I saw Tina checking me out I decided to give it a try. Normally I get all tongue-tied with a pretty girl, but with Greg and Cindy's coaching, I had a plan. Greg helped by telling me the girl I asked out would probably be more nervous than I was. So when I saw she was nervous I felt at ease." I tilted my head indicating we needed to head to class and I started walking. She fell in, remaining silent.

"I asked her out for a date on Friday night. I'm taking her to Jerry's for ice cream and then a walk in the park. It is low pressure and gives us a chance to get to know each other."

We reached her class and I was happy to see she just shrugged and went in. It was her subtle way of letting me know she approved. She could tell I was not being a horn dog. I was elated the rest of the day.

After school, I tried to call Tami again, but no answer. It was as if she was trying to avoid me. I was starting to get pissed. It wasn't as if she was mad at me, but something had changed. The only thing I could think of was it must be her dating Bert. I debated sending her a text but decided to take my Dad's advice and wait it out before I let my emotions get ahead of themselves.

After I hung up on Tami's voice mail, my phone rang. I looked at the caller ID and it was Cindy. "Hey boy toy, how did it go today? Did the new look have the girls drooling?"

"Yep, I had to beat them off with a stick. Actually it went pretty well."

"Spill it."

"Well to start with I got a kiss on the cheek from Peggy. That made it worthwhile. At lunch I asked a girl out and she said yes."

I had to pull the phone away from my ear as I heard her squeals of joy. Girls crack me up when they get this excited. I can imagine her doing a little Snoopy dance of joy. I interrupted her little celebration and asked, "Is Greg there, I want to share this with him."

She calmed down and said, "No, I haven't seen him since lunch today."

"Oh, he's not home, I just assumed he was with you."

"Nope, I'm flying solo tonight." She then spent the next ten minutes telling what to wear tomorrow. Today went so well I was not going to argue with her.

Greg didn't get home until about six and I was dying to tell him. "I have a date for Friday night!"

"Great job man, I knew you could do it. I guess I'm going to have to jam about twelve lessons into one tonight."

We headed up to his room. He smelled of sex and went to take a shower before Mom found out. While he was taking his shower, I was trying to put two and two together to figure out where he had been. I sure hoped he wasn't cheating on Cindy, but it just didn't make sense. Greg had a strict code of conduct that I had NEVER seen him violate. Part of his code was not to cheat when dating someone. Either he hooked up with Cindy in the last hour or he wasn't dating Cindy. The last one was impossible so he must have shown up right after she and I got off the phone.

Before I could get too far into trying to solve the mystery, Tami called. "Hey David, I see you called."

"Hey, long time no talk. What have you been up to?" I was trying to sound upbeat even though I was worried inside. I needed my best friend back.

Taking a deep breath, she exhaled slowly she said, "I have had a lot on my mind. I need to work through some things."

I grimaced, knowing how much we each cared about the other and yet unwilling to risk losing her friendship I wasn't certain how to respond. In these kinds of situations, I would ask Tami, but I couldn't with this. I felt my soul was bared and very helpless.

"Anything you would like to share?" I think I let some of my concern bleed through, but I had to know.

"Yeah I would like to share. You are my best friend after all. But I can't do it over the phone." THANK YOU! She was still my best friend. I had been holding my breath. I let it out in a whoosh. "I have an idea. Beth Anderson invited us over to her place on Sunday to go swimming. I haven't had a chance to ask, but would you be willing to go?"

"Perfect. I will meet you there. I'll get the details from Beth."

She actually sounded like her old self. I felt a huge weight lift from my shoulders. I had not appreciated how much this was affecting me. I suddenly needed to say something. "Tami, you do know that I love you?"

"Yes David I know. You have never told me before and it is sweet, but I have always known you love me. And best friend of mine, I love you too."

I heard the phone disconnect and I knew all was right with the world. Tami Glade loved me. We never looked at each other in a sexual manner. We never played doctor or you show me yours and I will show you mine. Tami was my twin sister. Maybe not biologically, but we are as close as twins are. We just made each other better people. I think the most confusing thing was seeing her with Bert and thinking it could be me. I know our friendship meant more to me than to risk it. She was too important to me. I know I would just be happy for her. I know she would feel the same way about anyone I dated.

I was riding high when Greg was done with his shower and he came to my room. I hadn't forgotten he came in reeking of sex. For some reason I suspected it was not with Cindy, but was it really my business? I loved my brother and I really liked Cindy. They made a great couple.

Greg jumped back into the conversation. "Okay, who are you going out with?"

"Tina ... and I just realized I don't know her last name."

"It is probably best you don't know a lot about her. It will give you something to talk about."

He thought for a moment and then he told me. "On your walk to Jerry's I want you to do a couple of things. The first is to tell her she looks nice. When you tell her that, look at her mouth. If you are looking at her tits, she will think you are a horn dog and just want in her pants. If you stare her in the eye, she will get nervous. Just glance at her mouth and say it. Then glance away, reach down and take her hand. Once you have her hand, start walking."

"Really... ?"

"Yep, it is an early indicator if you are doing well or not. You have basically taken possession of her. You will see many girls will take notice of this as you walk off the school grounds. This will pay off in spades later on."

"What do you mean by pay off?"

"Okay, I'm about to sound like a complete ass but if you want to date someone like Peggy you have to become someone she can date. She can't have an awkward freshman chasing her. She will cut you off at the knees. A girl that is a junior will only go out with a freshman if it is socially acceptable."

I smirked, "You're right, you do sound like a jerk, but I think I understand. I have to become cool enough so I can get out of the friends zone."

"Don't get me wrong. Peggy is not like that. If she wanted you, she would move heaven and earth to be with you. She is one of the best human beings I know. You will be the luckiest guy in the world if you date her. But the cold facts are she will never see you for the great guy I know you are until other girls start to notice."

"Yeah, Cindy was telling me a little about that. She said girls are attracted to men other women want."

"Cindy is a smart girl. You would do well to listen to her. The goal out front of the school is to get the girls to start buzzing about you as a potential date. Up to this point has been about you coming out. You started out by showing up at school all grown up. Then you did a brilliant thing in just being you. You gave Peggy a shirt when she really needed it. You have no idea how that affected the girls at this school. It created a buzz about you being a nice guy. Cindy took all that and put it into a package which had all the girls checking you out. Friday when they see you with a date, they will be jealous as heck. Next week you will start having girls approach you."

"Okay, I get what you guys are doing. What do I need to do to make this date a success?"

"It is just human nature that boys try to chase and capture girls. It is a girl's job to run and ward off guys. We need to change that mind set or you will never get past the first date with this girl. On the walk over take your time and ask her about herself. Let her feel you care about her. You will never get into trouble if they are talking about themselves unless you become judgmental or get too personal too soon."

"Got it..."

"When you get to Jerry's, find out what she wants to order and then order for her. This shows you are a gentleman and you are taking care of her. You are no longer chasing her; you are taking the initial step in changing the dynamics so she can get to know you. She probably has very little experience and this may put her off a little bit, but it just shows you're confident. This is the type of thing that will set you apart from all the other guys she has ever gone out with or will ever go out with."

I nodded. He was the master so I was not about to question him. "If she asks you about yourself give her a complete answer and then turn the conversation back to her."

I was a little confused, "What do you mean by giving a complete answer?"

"If you give her a half-assed answer she will think you're a fake. Take your time and tell her what she wants to know and then turn it back to her. You want the conversation ratio to be about 85% about her."

"But what if she asks me about something that is personal?"

"Good, you are thinking. You can tell her it is personal."

"But won't she think I'm being evasive?"

"Maybe, but you will get more respect having some boundaries than telling her things you probably shouldn't. Here is a great example. Cindy asked me yesterday if I had ever dated Peggy. I told her yes I did, my junior year for about six weeks. I felt comfortable telling her because I'm sure she already knew. If not, it was something she could ask Peggy about. Then she asked me if she was a natural red head. Once again, she already knows she is, but it is not my place to tell Peggy's business. The real question was did we sleep together. That is nobody's business but Peggy's and mine." I nodded in understanding.

"While talking to her, make sure you are sitting on the edge of your seat facing her. By doing this, your body language is telling her you are interested in what she is saying. Don't stare at her, but be sure you make eye contact. Don't make her think you have anything but her on your mind."

Good to know, I knew I hated it when I was with someone and it seemed as if they would rather be somewhere else.

"Okay, controversial subjects to stay away from ... do not ask her about her ex-boyfriends or her sexual experience. Do not gossip. If you are a big gossip, she will assume you will gossip about her. Do not put anyone down. I think you get the idea, keep it positive."

Greg gathered his thoughts and said, "After you are done eating tell her she is going for a walk in the park with you. If she does then things are still going well. If not this is her chance to bail, and this is important. I don't care if you are having the worst time in the world, you ask her to go for the walk. The reason is your date will set your reputation. She will be telling her friends all about it. If you are an ass you will never get another date."

That made sense. Greg had a great reputation and had dated all types before he and Cindy hooked up.

"The reason I told you to tell her you were going for a walk is because most guys are whiney little beggars. Girls hate that. You hear them say stuff like 'please baby let's do this' or 'can we do that'. As soon as you go there, the girl will have you wrapped around their little finger and they know it. By you taking control it breaks the whole run, entice and evade cycle. They turn themselves over to a more mature and confident man."

I was wrapping my brain around what he said as he continued, "Head over to the lake area and go to the bridge. When you get there tell her you are going to kiss her. Most guys make the mistake of asking if they can. If you ask and she is nervous, she will tell you no nine times out of ten. I take that back, she will probably kiss YOU because you are a Dawson." He smirked breaking the tension. "What it will do is take your nervousness away. You will feel more confident knowing she is more nervous than you are. If you tell her and she doesn't want to be kissed she will tell you. You telling her you are going to kiss her will give her permission to do it."

"Now this is the tricky part. YOU WILL NOT FORCE HER! If you are going to be in control you have to take the responsibility of making sure she is a willing participant. If you have any doubt, ask her."

"How do I pull that off?"

"Tell her what you are going to do and then pause. If she looks hesitant then ask her if it is okay. Let me give you an example. You are going to kiss Tina. Say I am going to kiss you. Don't just grab her and kiss her. Take your time. Look her deep in her eyes and then kiss her. If you see her hesitate, ask her. Tina is it okay if I kiss you? If she does not answer right away, tell her it is all right to say no. If she says stop you will stop right now. I mean it David, NO means NO."

"I know."

"David, the one thing that will disappoint me is hearing you are the kind of guy that forces himself on a girl. I can't stress this enough. Don't be that loser."

I had never seen Greg so intense. At that moment, I never intended to let something like that happen. We had been raised to respect women. I was a little choked up so I just nodded.

"I don't think you need any advice on kissing. You seem to have it down according to Cindy. Do not become an octopus. If you go straight for her ass or tits, you will be shut down before you get going. No one wants to be fighting off his or her date all night. She will revert to the run and hide and you will get a rep as a guy that can't be trusted. Keep your hands on her waist until she gets into it. Once she is going good take her by the hand and take her to the picnic area just off to the side of the bridge. It is secluded and you will have plenty of privacy. That will give her confidence and you will get much farther. And finally, be prepared."

I looked at him and said, "What do you mean?"

"Okay, not that this date is going to go anywhere, but if it does you need to have condoms. Part of being in charge is the responsibility side. It is NOT the women's responsibility for birth control. If you are not protecting her, you are not man enough to be having sex, and going on a date unprepared is setting you up to fail. When the time comes, it is very hard to stop in the heat of the moment. Don't put yourself or her in that position."

"Oh." I looked at him confused as he got up and left the room. Where the heck was I going to get condoms? A minute later, my big brother came to my rescue. He tossed two foil packs to me.

"Thanks man."

"No problem. If you are going to be man enough to have sex then you are man enough to buy your own condoms. I expect you to get your own supply. I honestly don't think things will get so far you will need them. I will leave the sex talk for later. No need for information overload."

After my brother left, I thought I would never get to sleep. I was trying to remember everything he had told me. How could one date be so complicated?

Friday September 6, 2013 – Freshman Year

The rest of the week was a blur. I went to class and then football practice until I was exhausted. When I went home, I studied and crashed. Then I got up and did it all again. I was nervous about Friday, but Greg and Cindy kept coaching me throughout the week. By Friday, I was ready to go.

I awoke Friday morning to the sunlight peeking around my bedroom curtains. My stomach started to knot up when I thought about today and the anticipated 'first date' with Tina. The night before Cindy jumped onto video chat and I took my iPad to my closet so she could pick out my clothes.

She then took the time to walk me through how to do my hair. I was not used to using hair products and she was not happy with how I was slipping on doing my hair each day. I tried to explain that at least three showers a day meant having to fix my hair each time. She gave me a look and I meekly decided to do as I was told. This morning I was up twenty minutes early to shower and do my hair. If the guys only knew, I would be catching it all day long.

Greg gave me a ride to school and Cindy did a visual inspection when we arrived. We arranged to meet right before my date since she knew I had PE and would need to do my hair again. I was trying to decide if this was irritating or helpful. The sad truth was Cindy was so hot I enjoyed her fussing over me. It gave me an excuse to be around her.

Alan was a big pest all day wanting to know details about my upcoming date with Tina. I actually threatened to punch him if he didn't stop. I guess he had sex on his mind 24/7 like almost every other 15-year-old boy. Alan was impressed I had one of our fellow freshmen going out on a date the second week of school. I guess I can see his point. I never dated much in junior high. I was confused as to how Alan knew so much about the date. I didn't give out any details and I knew Tami, Greg or Cindy wouldn't tell either.

Apparently, Tina was talking. I found it hard not to share with Jeff and Alan what Greg had told me. I probably would share with Tami, but we hadn't had our talk yet. The one thing I always admired about Greg was he never shared personal things about someone else. With Tina blabbing to all her friends, I could see where Greg's approach was better and I wanted to follow his example. I noticed several girls were taking an interest in me once word got out. I liked the attention, but Greg cautioned me it was not a good idea to do anything about those girls until I was done dating Tina, but I was making mental notes in case this date didn't work out.

Finally, the end of school came and I dropped my books off at my locker and went to the front entrance. Cindy found me before I went out. "David, come here." She was like a mother hen fixing my hair, making sure I was presentable and told me, "Word is there are 30 freshman girls hanging out front to see you guys off on your date."

Was she kidding me? "Are you joking?"

"Nope, and that is a good thing."

"How can that be good?"

"It means they have taken notice." By 'they', I assumed she meant the freshmen girls. Ah, Greg had warned me but I really hadn't believed him. If there is a crowd, I had to remember not to make a fool out of myself.

"Thanks for warning me."

"Okay, you look ready, go have fun and don't do anything I wouldn't do," she said as she gave me a smug smile that begged for a comeback.

"Someday you will have to tell me what you wouldn't do." I arched my eyebrows and her grin got bigger. I decided to beat a hasty retreat. She stuck her tongue out at me and just smiled. Did I say Greg was a lucky guy?