My name is Ann and I am eighteen years old and in twelfth grade. I can remember the first time I met Will. He was the “new kid” in school, having just transferred to Elmore High School. He came to live with his grandmother while his parents were overseas for his father’s work. Will came at the beginning of the summer and it did not take long for him to get the reputation of being a “bad boy.” Not that he caused trouble or anything but because he wore a leather jacket and like to drag race. He was soon a member of The Dragsters race club. He was also in the twelfth grade and by the time school started in August, he had most of the females under the age of nineteen all atwitter over his good looks and sex appeal. Hell, even my best friend was hot for him and she preferred girls.
Will was about five foot seven inches, muscular although a bit on the heavy side, with soul-searching brown eyes and brown hair that just touched his shoulders. On the first day of school, Will and I literally ran into each other. My locker stuck, causing me to rush to my last class of the day. As I came around the corner of the hallway to my English class, Will ran into me, knocking me on my butt. My books and papers flew all over the hallway. My little brother, who was with Will, started to laugh but did not even offer to help me out.
“You cock sucker!” I screamed at my brother. “You could at least help me up?”
“I am going to tell Dad what you called me,” Randy said. “You know that is not right.”
“Sorry I forgot,” I said as I struggled to my feet. “You are a cunt licker want-to-be virgin boy.”
In the meantime, Will was picking up my books and papers, listening intently to the conversation between my brother and me, although at first he did not know realize we were related because we looked nothing alike. I was five foot three inches, long blond hair midway down my back and green eyes with a sprinkling of freckles across my nose. Randy was six foot even, had brown hair and green eyes.
“So Randy,” Will began, “according to your sister here you are a virgin, right?”
Randy turned three shades of red, glared at his sister, and then said, “She does not know what she is talking about. However, I do know she sucks cock and a whole lot more so if you want Will, I will hook you two up.”
If it were not for us being in school I would have knocked my brother on his ass for spreading tales about me, even if they were true. Grabbing my things from Will I muttered thanks and headed back to my locker. English was half over so I saw no sense in walking into class now. I took the books I had homework in and stuffed them in my backpack. I was determined that my brother was going to pay for his big mouth, especially to Will.
I was no virgin and had not been since I had my cherry popped by a camp counselor ten years older than I was. I always looked older so he had no idea I was only sixteen. He made the summer fun but it was just that – a summer fling. How Randy knew I was not a virgin any longer was a mystery to me because I was very careful and discreet. However, on the other hand, he might have just said it because of what I said about him. Halfway home I heard the roar of a motorcycle coming down the road. As I glanced to my left, I saw it slow down, and then pull to a stop in front of me.
“Want a ride, Ann?” Will asked as he took off his helmet
Looking down at the short skirt I was wearing I knew if I climbed on the back I would probably give him a good view of my hot red thong, but then all things considering it might not be a bad idea.
“Thanks, but only have a couple of blocks to go,” I said.
“If you do not have to be home for a while we could take a ride,” Will suggested. “I promise to be the perfect gentleman.”
I started to laugh and said, “Then why would I want to take a ride on your Harley if you are going to be a gentleman. Riding on a Harley, that vibration on my pussy, makes me horny and I don’t need a gentleman for that. I need a bad boy.”
Will started to laugh and then said, “I like your sense of humor, Ann, but you need to watch the talk of not being a virgin because some boy is going to believe you and then you are going to pay.”
“It is not just talk Will,” I began, “because I am not a virgin.”
Will was not a virgin either but he had never met such an outspoken girl that had no qualms about admitting she was not a virgin. I didn't know it at the time, but he thought I was just pulling his leg, and he decided to call me on it by stopping at his favorite spot by the lake out of town.
Before he could ask me again if I wanted a ride, I thrust my book bag at his chest. “Do you have somewhere to put these while we go for a ride?”
“Sure,” he told me as he put them in the compartment under the rider’s seat.
I hiked my skirt a little more to make it easier to get on the Harley, making sure that he caught a glimpse of my red thong. By the look in his eyes, I had succeeded in getting his attention. He got on and I wrapped my arms around his waist, letting my hand momentarily slide down to the front of his jeans and giving him a squeeze. Before he could say anything, I moved my hands back up to his waist.
I put on the helmet he had taken out of the storage area before he put my book bag there. Soon we were flying down the back roads, over the different hills, and around curves. The vibration from the motorcycle was doing a number on my pussy and I knew it would not be long before I cum. I did not want to cum from the vibrations from the motorcycle but by Will’s tongue on my clit.
It seemed like I might be getting my wish when he pulled down a dirt road that led to a summer hangout for the kids of town. At the end of the lane, there was a huge grassy lot and a big lake we all used as a swimming hole. Stopping under a tree, Will got off and offered me his hand. He put our helmets on the handlebars and pulled out a blanket from another saddlebag. We walked over to the tree holding hands, and while he spread it on the ground, I pulled off my t-shirt and shimmied out of my skirt. When Will turned around, I was standing there in my skimpy lacy red bra and matching thong.
Seeing him watching me, I slowly slipped the straps of my bra down each arm, one at a time, then reached behind me, unfastening it. I took it in my hands and threw it at Will, but he did not even attempt to catch it, leaving it to fall to the blanket.
“What the hell do you think you are doing?” he asked as he stared at me.
“Well, I thought we would fuck,” I said, “unless you are like my brother and a virgin boy. If that is the case I will be glad to take your cherry,” as I walked over to him, playing with my nipples. “I have plenty of experience taking boy’s cherries.”
Wrapping my arms around his neck, I pulled his head down and kissed him hard. Will figured I was playing at being grown up and acting like I was a sex symbol so he decided to give me a little scare. He scooped me up in his arms and lay down on the blanket with me in his arms, his mouth seeking my nipple. As he latched on to my nipple and began to suck and pull on it, I felt my thong getting wetter. I grabbed his hand and pushed it toward my pussy since he apparently did not know what to do. However, I was wrong; Will pushed my thong to the side and inserted a finger into my pussy, seeking my clit.
Finding his target, he began to rub my clit hard while sucking and pulling on my nipples, alternating from one to the other. I was horny from the vibration of the Harley and soon I was wiggling all over the blanket, my pussy clenching his finger so tight he had trouble moving it. Within minutes, my juices began to flow as my orgasm ripped through my body.
Will quickly pulled his finger out and stood up. I looked up at him, wondering if he was going to remove his jeans so I could give him pleasure. To my surprise, he gathered up my clothes and tossed them to me.
“Get dressed, Ann, before I do something I will regret later,” as he went over to stand by the motorcycle with his back to me.
I gave an un-ladylike snort as redressed, trying to figure out what was going through his mind. I wadded up the blanket and threw it at him asking. “Are you bi or gay?”
“Hell no!” Will yelled. “Whatever gave you that idea Ann?”
“You had a chance to fuck me and you didn’t.”
“Just because I did not fuck you does not make me bi or gay, little lady.” Will told me. “Now get your ass on my motorcycle so I can take you home before your dad comes looking for me with a shotgun.”
I laughed and climbed into the passenger seat, putting on my helmet. When I put my arms around his waist this time, I kept them away from his crotch. When we got back to my place, he gave me my book bag, put the helmet away, and roared off, leaving me standing at the end of the sidewalk. As I walked up to the front door, lost in thoughts, I did not notice my brother sitting on the steps.
“Well, sis, did you fuck him?” he asked. “You were gone long enough to.”
I had enough of my brother’s mouth so I swung my book bag at him, catching him on the side of the head. “I am a fucking virgin,”
“Not according to Fred Wilson.”
I knew exactly whom he was talking about and he was the one fuck I regretted but I pretended I did not know whom my brother was talking about. “I do not even know who you are talking about,” I said as I went in the house after kicking Randy in the hip.
For the next month, I did not see Will except in passing at school but he said nothing to me except "hi", but only if I spoke first. I was not used to a boy ignoring me so I decided I would have to seduce him if I wanted him to fuck me. In October, the school has a dance and this year the tenth graders were in charge of picking the theme. The theme they picked was a Sadie Hawkins dance based on the Little Abner comic and movie where the girls chased the boys. For this dance, the girls asked the boys and the boys could not refuse.
As soon as I heard this, I cornered Will before he even got off his motorcycle the next morning.
“Morning Will,” I said. “You are going to be my date to the Sadie Hawkins dance. It is Halloween night. Casual dress and I already have tickets. You can pick me up at six o’clock,” and with that I walked away, leaving him staring open-mouthed at me.
For the next two weeks, Will once again avoided me so I was unsure if he would take me to the dance or not. On that Saturday evening, I was dressed in a pair of tight blue jeans, a button-down red-checkered shirt, tied at the bottom, tennis shoes, and I had my hair divided into two pigtails. My brother was out with some of his friends for the weekend. Mom and dad were also gone for the weekend so I had the house to myself. I had plans to have Will in my bed that night, come hell or high water – unless he did not take me to the dance. A few minutes after six I heard the sound of a vehicle pulling in the drive. Looking out the window, I saw Will climbing out of a dark grey pickup truck.