It Started with a Hand Job

All characters in this story are eighteen-years-old or older.

I was never the prettiest or most popular girl in school but I had a small circle of friends including my best friend, Diane. Diane was far more popular in school than me, especially with the boys. She was pretty, outgoing, and always seemed to have a boyfriend. Me, on the other hand, had only been on a couple of dates but nothing extraordinary ever happened. Maybe that’s why Diane and I got along so well, we were almost complete opposites.

Diane tried helping me with the boys but things never seemed to work out. The boys that were interested in me weren’t my type, whatever that was and the boys I was attracted to didn’t want anything to do with me. I was fine with that. I would spend my free time with the few friends I had and was happy. Even though I say I was happy, I think I just accepted the fact that boys didn’t find me attractive. I didn’t have a lot of confidence and had body image issues like most young women.

I’ve known Diane since grade school; she was older than me by a couple of months. Her birthday was early in the school year and mine was in January so we were usually the oldest kids in our class. She was way more adventurous than me while I was mostly a scaredy cat and afraid to take chances. Any time I got into trouble, you could bet that I was with Diane. I admired her risk-taking and she did help to teach me to be less cautious and to try new things.

Shortly after I turned eighteen, Diane told me that for my birthday she was going to find me a boyfriend. She told me I was single for too long and now that we were in our senior year, it was time for me to come out of my shell. I laughed at her but didn’t discourage her either. The first thing she did was take me shopping for some new clothing.

She would always tell me, “You have a cute little body. You have to start accentuating your assets.”

Diane had my mom get me several gift cards to some clothing stores for my birthday and we spent the entire day at various stores trying on clothes and buying a new wardrobe. My best friend convinced me to get out of my comfort zone of wearing only jeans and sweatshirts. By the end of the day, I had several new tops that consisted of tank tops, crop tops, and some camis. She also convinced me to buy a couple of pairs of leggings and shorter skirts than I was comfortable with. I also bought a couple of bra and thong sets.

We even had a sleepover at Diane’s house that night where we put on makeup and she gave my dark brown hair blonde highlights. She snuck a few of her dad’s beers up to her room where we talked about going away to college and boys. Diane was currently dating Mike and I knew she was no longer a virgin. She was telling me how great sex was and how she lost her virginity on her eighteenth birthday. I had nothing to compare it to other than using my hand and fingers and watching an occasional porn flick.

As we were having our girl’s night, Diane mentioned to me, “We have to get you laid, Carly. You’re eighteen now.”

“There’s one problem with that, Diane. I have to have a boyfriend first.”

“If you follow my lead, we’ll fix that problem. Your new hair color and a touch of makeup will help. When you start wearing your new clothes, the boys will notice so that won’t be a problem.”

“That’s easy for you to say, you have a great body. Boys barely know I’m alive.”

“Trust me, we’ll fix that. Besides, I’ll talk to Mike. His friend, Dan, just broke up with his girlfriend and is available.”

“Dan is cute but he would never go out with me.”

Diane shook her head in pretend shame, “Didn’t I just get done telling you to trust me?”

“Okay, okay.”

We talked well into the early morning hours with Diane telling me about giving hand jobs and blow jobs. Mike was pretty good at licking her pussy too. She said sex was even better but to make sure we used protection. I told her I didn’t think a guy would want to go out with me because my breasts were too small and my butt was too big. We were feeling buzzed from the beer we drank and Diane told me to take off my nightie and panties. We stood naked side-by-side before her full-length mirror.

She got behind me and cupped my breasts and said, “See you have nice tits. They aren’t much smaller than mine.”

Diane then had me turn around and we compared our butts.

“See, they’re about the same size. You just need to start showing off your booty more. Be proud of it.”

“You might be right, Diane, but I’ve only been on a few dates and haven’t made out with a guy. I’m not even sure I’d know what to do.”

“You worry too much. Just do what comes naturally and you’ll be fine.”

That Sunday, Diane came over to my house and picked out the clothes I’d wear to school the next day. We started with a simple pink tank top and my new black leggings. A push-up bra made my breasts look bigger and enhanced my cleavage. The thong made sure there were no panty lines in my leggings and helped define my ass cheeks. Monday morning at school, I thought I noticed some boys looking at me differently. Maybe they didn’t like my new clothes but Diane assured me otherwise. That’s when Mike and Dan came up to us and I saw them looking at me like they were undressing me with their eyes.

Mike was the first to comment, “Wow, Carly, I like the new look.”

“Yeah, you look great,” Dan added.

Diane smiled at me with a grin that said, “I told you so.”

The guys followed us to class and as we were walking, Diane whispered to me, “Bend over at the waist to pick up your books.”

I was confused because I was holding my books when Diane reached over and knocked them out of my hand. Now I knew why she did that. I bent over at the waist and stuck my butt up in the air. As I was picking them up, I saw Dan and Mike checking out my ass. That made me feel great. I noticed some of my teachers checking me out too which gave me a rush of excitement. Maybe Diane was right after all.

My best friend was trying to fix me up with her boyfriend’s best friend whose girlfriend had just dumped him. I had a crush on Dan for a long time but he always had girlfriends that were much prettier than me so I figured I would never have a chance to date him. He was so cute, my heart would beat faster whenever I saw him. Both he and Mike were on the baseball team which made them very popular

It would get excited when Dan would smile and say, “Hello Carly,” when he saw me in the hallway in school. I was happy that he knew I existed.

When Dan asked me to go to a movie with him, part of me thought it was a practical joke. I couldn’t believe he would ask me out even though Diane said she would arrange it. I was naturally excited and went searching for Diane to tell her the good news. I had never been so happy in my entire life. One of the cutest guys in school just asked me out.

When I told Diane, she gave me a knowing look and said, “I told you to trust me, didn’t I?”

“Yeah, but I never thought it would happen.”

“You need to have some faith in me. Now, we have to get you ready for your date.”

Diane came over to my house late Saturday afternoon to help me get dressed. She picked out a low-cut yellow tank top that showed off a lot of cleavage and a very short blue mini-skirt.

I told her, “If I wear this won’t it send him the wrong message? You know, that I want to turn him on.”

“Oh my god, Carly. You’re my best friend but sometimes you’re so naive. That’s exactly the message you want to send him and you want to turn him on. If you want my help, you need to follow my advice.”

“Okay, okay.”

I was scared to death by the time Dan picked me up. I found it hard to believe a guy so cute wanted to go out with me and I didn’t want to ruin this chance. When he picked me up, he gazed over my body. I was terrified he wouldn’t like what I was wearing but my fears were unfounded.

“You look great, Carly. I wish I would have asked you out sooner.”

I was so relieved to hear that and secretly wished he would have asked me out before too. I thanked him and he escorted me to his car and opened the door for me like a true gentleman. I made sure to keep my legs tight together so I didn’t flash my panties at him. My skirt did ride up further on my thighs when I sat down and exposed more of my thighs than I wanted even after I tried to tug it down.

Dan took me to a sit-down pizza place for dinner before we went to a movie. I didn’t care where we went or what movie we saw as long as I was with Dan. I can barely tell you the plot of the movie we saw. He put his arm around me several minutes after it started and I just about melted in my seat. All I could think about was how good it felt to be held by him. It was impossible for me to concentrate on anything else. When the movie was over, all I could think was that I didn’t want the night to end.

Dan asked me, “What do you want to do now?”

“I don’t know.”

I started to panic when he suggested, “We could go up to the lake and uh, talk.”

The lake was a local lover’s lane at night and I knew that he didn’t expect much conversation but I didn’t want the date to end and I didn’t want it to be our one and only date so I replied, “Uh, yeah sure. We can go to the lake?”

I had heard of what some of the other girls did up there and I wasn’t prepared to go that far. We were both eighteen but I was still a virgin and was caught off guard by his suggestion but I desperately wanted to make out with Dan. It would be a dream come true. I was super nervous as we drove to the lake. I worried that he wouldn’t like the way I kissed. I wondered if my breath was okay. What if he wanted to have sex but I didn’t, would he ever ask me out again?

Once we arrived at the lake, there were a few cars already there so he parked far away from them. Dan shut off the engine and I was now facing the moment of truth. The suspense of what this evening would bring was killing me. It was like a life and death situation for me and my dating future. I desperately wanted to continue to date Dan but I wasn’t ready to lose my virginity the first time we went out.