Took me longer than expected since I wasn't happy with the original ending and had to rewrite the entire ending...hope you enjoy.
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I got home late Thursday night...exhausted from a long day at school. Luckily tomorrow was a holiday and I had just completed my midterm and turned in all my papers. I had absolutely nothing to do...and was very much looking forward to the three day weekend. It had been a couple weeks since that magical spring break week at the beach house with Ally. I had high expectations for this weekend...perhaps a tryst with Ally. But all that was shot to hell when I learned that Ally would be spending the entire three day weekend over at Melissa's house. Melissa and Ally were both on the cheerleading team at their college and a group of girls were spending the weekend over at Melissa's house to practice over the long weekend since Melissa's parents were not going to be at home the entire weekend...something about an out of town wedding they had to attend. I was crushed upon hearing the news...Ally and I hadn't really gotten the opportunity to fool around much since the beach house and I was sure that this would be the weekend for an opportune encounter....but alas...I guess it was not to be.
After learning the devastating news I made my way to my room collapsing on my bed...falling fast asleep. I tossed and turned all night due to my sexual frustration. I was awoken early Friday morning by Ally who was standing in my room with her bags.
"Hey James...sorry to wake you...but mom's a bit busy...could you give me a lift over to Melly's place?" she questioned.
Not wanting to disappoint her I agreed, "Just give me a few minutes...I'll meet you in the car."
"Thanks lil bro," she bubbly responded planting a kiss on my cheek, and making her way out my room.
I got off my bed...and made my way into my bathroom...after a quick shower and brushing my teeth I went down to the car to meet Ally. She was patiently waiting sitting on the trunk of the car...her legs crossed beneath her cheerleading skirt and a bag pack on her lap.
"Took you long enough," she jokingly said.
I stuck out my tongue teasingly at her in reply.
"Don't show it if you don't intend to use it!" she retorted...with a sly grin.
I hopped in the car and started the engine...Ally soon followed and we were off.
"So James...what are you going to be doing this weekend?" Ally questioned.
"Well I don't know...you're gone so there'll be less excitement than expected," I replied.
"Awww...I really wished I could be with you this weekend but we have a big game coming up this weekend and the girls and I really need to practice."
"Yea...I know...don't even worry about it...I understand."
The rest of the trip was pretty much Ally and I making small talk. As we neared the corner of Melissa' house Ally turned to me.
"Jimmy...when was the last time you masturbated?"
Catching me a bit off guard with her question I was a bit confused. "Umm...well I haven't really masturbated since we umm...you know..." was my reply.
"So that'll be like two or three weeks right?"
"Umm yea...I guess so."
"So I guess you're probably going to beat off this weekend being so long since you hadn't and since you're all alone?"
"Well...I hadn't really thought about it...but I guess I would," I told her as I pulled up in front Melissa's house.
"What if I made you an offer that would be much more enjoyable than jerking off by yourself?" she continued.
"What kind of offer?" I inquisitively asked as I began to become intrigued.
"What do you say you come spend the weekend with me and the girls?"
Befuddled and excited at the proposal "Well I don't know Ally...that'll be kind of awkward...they're all your friends."
"Ohh come on James...you know they all love you, and you could help us...you know tell us if any of our moves need improving...and I promise you...it'll be the best weekend of your life...I'll make sure of it," she replied smiling at me.
"Well ok...but we'll have to head back home for me to get some clothes." I finally agreed.
"Ohh...no don't worry...we'll figure something out when that time comes," she replied, with that coy look on her face as though a million ideas were running through her head.
"Well ok...I guess we better go inside now," I said opening my door to step out.
"Not so fast mister...there's just one little catch to this fantasy weekend," Ally said grabbing my hand preventing me from leaving.
I closed the door to hear what she had to say.
"You have to wear this the entire weekend...and only remove it when I give you permission," Ally instructed rummaging through her purse and raising her hand which was gripping some sort of rubber ring.
"It's a cock ring James...it's designed to keep you in a certain state and help prevent you from cumming."
Shocked at Ally's intentions I didn't know what to say. And without waiting for an answer Ally unzipped my fly. She dipped her hands through the fly of my boxers and retrieved my cock, her warm hand wrapped right around me. My shaft was semi erect only till the point that Ally started stroking me. After I became fully erect Ally placed the ring on the tip of my penis. She then started to roll the device down the length of my shaft. The rubber ring was sturdy...and tight around my cock. Ally rolled it right down to the base of my shaft. When she was done she gave me two more quick strokes smirking at the predicament she had put me in. She stuffed my cock back into my pants against its will and zipped me up.
