Bobby 01

Hi, my name is Bobby.

It's amazing what you can do helping people out in your neighborhood. Cleaning gutters, working in the lawns or gardens, moving some furniture, cleaning cars, all that stuff. It's not just the money. That's rarely the only compensation.

If you do a good job and if the neighborhood likes you they give you tips on interviews, leads on jobs, recommendations, advice, which shops do the best this or that, vegetables from their gardens, some even make you food.

Not just cookies and things, and those are great. I mean stew, chili, soups, meatloaf, lasagna, and whatever. If you play your cards right and you make a good impression they have friends and family with nice girls to date. They put a good word in for you too. One family let me use their car to take out their niece.

If you treat people well they might just treat you well.

One neighbor treated me very well. Very very well.

I had a large territory, so I helped people out a couple miles away from my parent's house in any direction. It wasn't that everyone on every street knew me, but every street had someone that knew me.

Mrs. Carter was a sweetheart. Divorced with kids in college. She looked really good. I didn't really know how women in their 40s were supposed to look. All I knew was Mrs. Danielle Carter was a knockout. Classy too.

She liked to look nice whatever she was doing. It was easy for her to look nice whether she was in the garden, going to the store, running or exercising, it didn't matter.

Great curves doesn't begin to describe her, and she had more than just a beautiful figure. She had this gorgeous smile and stunning eyes. When she talked to you you felt like someone really paid attention.

Needless to say I would have bent over backwards to help Mrs. C, and not just because of her looks.

Whenever I took a break she played old songs from the 50s and 60s, she'd serve some iced tea or cold sodas and we'd talk for a little while.

Through the summer after my first year in college Mrs. Carter asked how things were for me since high school. She didn't realize I rarely dated back then. She boosted my confidence saying I was too good looking to not have girlfriends.

Over the course of several conversations I opened up little by little. It was kind of an embarrassing subject for me, but it was so easy to talk with her. I explained that I had one long term girlfriend. We were together for about two years, but she graduated a year before me and moved out of state.

She wondered how I could get through my senior year without any dates. "I hope you're not telling me you were the love-them-and-leave-them type, Bobby," she teased.

Actually, I was teased for being so shy and withdrawn. Gossip ran through certain circles, which made it worse. She took a genuine interest and asked how bad the gossip got.

Depending on who you talked to some girls claimed I was gay, or had thick body hair, or didn't know how to kiss a girl.

"They knew you dated Jessica for a long time, didn't they?"

I felt so comfortable and safe talking to Mrs. Carter by this time that it just slipped out that Jess and I never slept together.

She was shocked that two high school teenagers together for two years never had sex. She admired that kind of commitment from two young kids.

"Well," I told her, "It's not like we both didn't want to... you know, do it." I couldn't believe I was telling her this stuff. "It's not like we didn't almost do it. Something always got in the way."

She said she was sure we got up to enough mischief without actually, "doing the deed," as she called it.

I got very embarrassed and turned red. It was obvious from my expression and body language that while Jessica and I never had sex we certainly had explored each others' bodies.

In one of the conversations we had I told her how my first year in college wasn't great in terms of dating.

She assured me that a guy like me should try to ask girls out a little more. "I can't imagine why they wouldn't say Yes to going out with you. They should be falling over each other to be the first."

"Well, I went out on a quite a few dates last year, but none of them went out a second time," I explained.

"Did you ever kiss any of them, Bobby?"

"Um, well," I started out rather embarrassed.

"Oh, young man," Mrs. Carter said with conviction, "this year I want you to promise to yourself you will kiss your first college girl."

"I kissed them all, Mrs. Carter," I replied. "That's not it. It's really very embarrassing, I'm not sure how to say it."

I explained that some girls went out with me on a dare. They tried to find out what my story was. In fact, they were usually just interested in sex. However, I wasn't like any of the boys in school they were used to.

"Oh, Bobby, I'm so sorry for bringing it up," Mrs. Carter apologized again. Clearly she felt awful for mentioning a sore subject, "Girls can be so cruel to guys if they don't... measure up in certain ways."

"No, that's not it." I was unsure how to handle the subject. I didn't want her to assume I had a tiny penis, but blurting out a denial sounds like desperation.

"Mrs. Carter, can you keep a secret?" I asked quietly.

She assured me, "Bobby, you know I won't say a word."

"Those girls didn't go out with me a second time, because of something else," I tried to find the right words. "It wasn't because my... um, penis was smaller than they expected. It's actually... the opposite. My, ah, you know... penis was much bigger than they thought it would be."

Her eyes widened and her jaw dropped.

The next words came out of her mouth involuntarily.

"How much bigger, Bobby?" she whispered. Suddenly she covered her mouth with both hands, shocked that she wondered about the size of my cock and even more shocked that she asked me directly.

"Oh my God, I'm so sorry!"

The next words came out of my mouth involuntarily.

"I'll show you, if you want to see it," I whispered.

Before I could apologize or take the words back Mrs. Carter's head nodded slightly and her lips silently formed the words, "Yes, please."

She took my hand and led me into her house. We walked through the living room and past the kitchen.

Mrs. Carter placed both hands over her chest, either to feel how fast her heart was beating or to keep her breasts from heaving up and down as she breathed in excitement.

I nervously unbuttoned my shorts, slightly pulled them down, and slowly drew out the subject of our most recent conversation.

Her eyes didn't move from my penis as she asked, "Is, uh, this the reason you and Jessica didn't..."

She must have been imagining my petite girlfriend struggling to work with my large dick. Her eyes were fluttering.

Just then the phone rang and shook Mrs. Carter back to reality.

"Um... it's my office calling. I need to take this. Uh, let's see. Why don't you come back tomorrow to work in the back yard, Bobby."

I quickly tucked my oversized manhood back into my shorts. She walked to her kitchen talking on the phone while I opened the door to exit through the open garage.

The image of Mrs. Carter's shocked face as she stared at my penis turned me on. It obviously caught her off guard and fascinated her. It distracted me so much I forgot all about my keys. I had taken them out of my pocket because they kept slipping out.

I went to grab them and overheard Mrs. Carter talking on the phone. She wrapped up her work call and immediately dialed another number. She thought I was gone and started talking about me, although she changed some of the details.

"Sarah, hi, it's Dani. I just got back from jogging around the lake. You'll never believe what I saw."

She said she saw another jogger, a younger man, have a wardrobe malfunction and described seeing what she called a massive dick. Her voice sounded gleeful. She added that the younger man caught her inadvertently starring, and then admitted that she got wet.

By this time I had retrieved my keys as quietly as possible. I was less concerned about my keys because I was practically rock hard. Hearing Mrs. Danielle Carter talk so positively about my big cock was gratifying.

Girls in school heard rumors about my penis. Some said it was tiny, which is why I was so shy. Others said it was huge. Whenever they saw it the typical response was for the girl to either be disgusted or freak out.

Mrs. Carter sounded like she wanted to see my cock again. While she talked she caressed and cupped one of her big breasts. She didn't see me, but I sure saw her.

She said she just got a call from work and had to go. When she hung up her phone she used both hands to hold and squeeze her well-shaped tits. Soon she had one hand working down between her legs tucked into her leggings. This gorgeous woman was going to touch herself until she came.

Unfortunately it was not to be. She stopped after a couple of minutes, but she went off to take a shower. On the positive side this allowed me to get out unseen and unheard.

I almost snuck over to her bathroom door while she showered. No doubt I would have opened the door a crack to see and hear her better. The idea of seeing her curvy body sent me home to take a shower of my own.

I imagined Mrs. Carter's wide-eyed amazement and stunned expression as I masturbated in the shower. I imagined what she would look like and what she would say if she watched me pump my powerful prick for her.

Maybe she would say encouraging things and talk dirty while looking at my cock.

Maybe she would speak softly. Maybe she would look into my eyes. Maybe she would ask to touch it. Girls in school always wanted to touch it, but almost always lost their nerve when they actually made contact.

When I came I released a massive load of cum. I turned off the water just before I reached my climax so I could see how much I actually shot. I like to think that if Mrs. Carter would have seen it she would have been twice as surprised.

I was so turned on I jerked off later that day.

*

To be continued in Chapter 02