Fantasy Weekend

Took me longer than expected since I wasn't happy with the original ending and had to rewrite the entire ending...hope you enjoy.

*

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.

I followed Ally to the front door my cock aching under my pants. Ally knocked on the door and we waited. Melissa opened the door...her beauty struck me right away. She was really a stunning girl...long brown hair to her shoulders...perfect breasts...round and firm just as my sister's. She was wearing her short pleated cheerleading skirt showing off her legs, and a tight halter top...apparently with out a bra, her nipples pressing against the sheer material.

"Hey...Ally...the girls are in the backyard...come on in."

Ally stepped aside to reveal my presence.

"Mel...you know James...he's decided to join us for the weekend."

"Ohh...hey James...that's great...come in come in," she shrieked.

Ally and I followed Melissa inside...Ally dumping her bag at the base of the staircase.

"Well James...I'm sure the girls will be delighted you're joining us...I know I am," Melissa said while leading us into the backyard.

Feeling shy...and blushing quite a lot I murmured back, "Umm...thanks Melissa."

We finally made it to the back yard to greet the other two girls.

I stood in awe at the two beauties I discovered in the back yard. Ashley the blonde haired vixen wasn't wearing much...a sports bra to support her pert breasts and one of those skin tight shorts that ended on the curve of her ass. When I first saw her she was stretching...in preparation for practice. She was bending over her arms outstretched in front her...the tights she had on caused a perfect camel to be displayed. My loins immediately began to stir...then I turned my attention to Roxy...she was sitting on the grass...her legs spread wide apart...if there wasn't the presence of her short pink skirt I probably would have exploded right there in my pants. When the girls saw us they came over and hugged Ally, then turned their attention to me.

"Hey James...what are you still doing here? Trying to catch an eyeful I bet," teased Roxy, causing me to blush more than I already was.

"Oooo...he's going to be spending the weekend here with us," announced Melissa.

"Awesome...glad you could stay Jimmy," Ashley said shyly. She was the youngest of all the girls...yet still a year older than me.

"Well...I guess we better get started girls," Melissa said...taking my hand and leading me over to the patio table and chairs.

"You sit here James....you could help judge our moves."

"Umm...sure thing Melissa," I casually replied.

I sat down while the girls lined up on the grass and started their routine. Needless to say, the sight of these four girls frolicking around in their skimpy attire...their toned bodies filling out the right places was a major turn on. I kept shifting in my chair trying to adjust the position of my hardened cock which was now permanently stiff...thanks to Ally's cock ring.

"Damn...we need Steven to do the lift...how else will we know if the routine meets the time requirement," I heard Roxy angrily grunt.

"Maybe James could help...you wouldn't mind that would you James?" chimed in Melissa

"Umm...I guess not...just tell me what I have to do," I reluctantly said.

"All you have to do is grab Melly by the waist and lift her above you head when I give you the word...in the meanwhile...just stand behind the line and wait for your cue...you think you can mange?" Roxy informed me.

"Sure...no problem." I replied.

"Great...lets go!" and excited Melissa shrieked.

I stood behind the four girls. Ally to my far right...then Ashley...then Melissa in front of me...and Roxy to my left. I stared at all of them from behind; Ashley's ass in those tights was amazing...perfectly round. Melissa's and Roxy's skirts were so low...the lower half of their firm butt cheeks were visible from under them.

"OK....lets go!!" screamed my sister.

The girls started their routine...jumping, kicking, and screaming when Roxy gave me my cue.

"Now James!" she screamed.

I immediately put my hands of the small of Melissa's back...lifting her above my shoulders...allowing me the perfect view up her skirt to see her white cotton panties...the lips of her pussy pressed tightly against them. I sat her down on me...her firm ass pressed on my shoulder. When we were done I brought her back down to her feet. Thankfully we had to practice this over and over again. About a half hour later we were still practicing when rain slowly but surely started to fall. I looked around to see the girls slowly becoming exposed by the wetness hitting their bodies. Everyone was now soaked and it was apparent that the between Roxy, Ally, and Melissa...only Roxy was wearing a bra. Ally and Melissa were so soaked that their pert breasts were clearly on display. Their bra-less tits showed how cold they were with their nipples fully erect...poking through their shirts. I looked at Ashley, her blonde hair plastered to her face...water running down her stomach...drenching her shorts. As I turned to Roxy...I looked down to her wet skirt clinging to her ass. Her top stuck to her skin... her lace bra showing clearly through the almost transparent tee shirt, her rounded breasts and her nipples, hardened by the cold.

We continued practicing...as Melissa mounted my shoulder for like the 12th time...I began to lose my grip...due to her now slick body. Melissa came crashing down on me...I leaned back and fell to the floor so I could break her fall. Melissa landed straight on top of me...her legs wrapping around mine. I looked up at her...she was staring into my eyes with a smile. The rest of the girls started to laugh at what had happened. In the meantime...a soaked blonde haired girl lay on top of me. My permanently stiff cock began to twitch beneath my pants. My dick was lodged into Melissa's inner thigh...and no doubt...she felt it. Melissa looked down at me...a wide grin across her face as she shifted her legs a bit...sliding it along the length of my hard cock...subtly enough not to lead on the other girls but to make sure I knew what she was doing.

After a few seconds of Melissa grinding into me she got off...offering me her hand to pull me up. As she brought me to her feet she said to the other girls.

"I think James' hands are tiring...and with the rain and all...we better call it a day...what do you say we hit the mall?"

"Sure thing," replied Ally.

"Ok...Ally...you're bunking with Ashley and Roxy...so you can carry your bag in the downstairs guestroom with theirs and you all can get changed," announced Melissa, the three girls following her instructions and heading inside.

"James...you're all alone in the upstairs guest room next to my bedroom so you can get changed there."

I nodded my head and Melissa and I headed upstairs to the guest room. Melissa went into her room and closed the door and I went into the guest room...where it then dawned on me that I had no clothes. I had totally forgotten. I headed downstairs to the girls' room to speak with Ally but she was in the shower. I headed back upstairs to wait for her....right before I entered my room I heard Melissa's voice.

"James...is that you...are you ready?"

"Umm...yea...about that...I kinda forgot...I have no clothes...I guess I'm going to head home to get some...I'm just waiting for Ally to get out the shower to tell her."

"Ohh...nonsense James...you cant drive home soaked like that...come in here....I'm sure we can find something for you to wear."

I opened the door to Melissa's room and entered. I found her standing by the bed. She was wearing a pink bra that squeezed her B cup breasts together and a black skirt. Upon seeing her I quickly closed the door.

"I'm sorry...I thought you said to come in...I didn't know you weren't dressed," I tried to explain.

"James...its ok...I did say you could come in...its not like I'm naked," she replied, laughing as she did so... "Now get back in here!"

I re-entered the room and now found Melissa rummaging through her draws...then her closet.

"Here we go," I heard her say as she emerged from her closet.

"I knew my ex forgot these," she continued...tossing me a pair of jeans.

"Now for a shirt," she said as she perused her own clothes to find something suitable.

"Ahh...this'll work," she said handing me on of her shirts...it looked as if it would fit.

"Now...lets get these off," said Melissa...as she held on to my wet t-shirt, pulling it over my head.

"Umm...I can handle it...I'll just do it in my room," I tried to protest.

"Well...James...I need to see how it looks...I can't have you out there looking foolish in a girl's shirt...I wouldn't want to embarrass you like that," Melissa explained as she completely removed my damp tee revealing my chest. I shivered a little...feeling the cold air of the AC hit my naked wet skin. I quickly put on the shirt...it was a bit tight but was usable. Melissa took a step back to get a good look and nodded in a sign of satisfaction.

"Now...lets get these icky wet pants off," she continued as she started unbuckling my belt....followed by the button of my pants.

"Melissa...I don't think we should be doing this," I said in an attempt to stop her.

"James...don't be silly...we're all adults...its not like you have anything I haven't seen," she said as she hunched over and unzipped me. In the position she was in...leaned over...I was able to get a great view of her cleavage...her pink bra pushing her firm breasts up. The sight caused my penis to twitch ever so slightly. As Melissa finished unzipping me...she pulled my pants down to my ankles...coming face to face with my wet boxers snaked around the length of my hardon.

"These wet boxers will have to go too," and without hesitation or before I could stop her, Melissa pulled the wet material clinging to my crotch right down...my dick bouncing up as she passed my underwear over it. Melissa's eyes locked onto the sight of my cock...and then she realized the ring.

"What's this James?" she questioned...trying to hold back laughter.

"Umm...well you see...hmm...it's a...umm...it was Ally's idea...she said if I wanted to spend the weekend I'd have to wear it the whole weekend," I tried to explain...feeling completely embarrassed.

"Oh...that Ally...such a devil...anyway...its nice," she replied with a smile.

"Now...unfortunately my ex didn't leave behind any underwear...and considering the state you are in...it's not a good idea to go commando...in someone else's jeans no less...you wouldn't want to catch something."

"Well...what would you suggest?" I asked.

"Hmm...let me see," Melissa replied as she got up and again started rummaging through her draw. "You could wear this," she excitedly said pulling out a pair of navy blue bikini cut panties"

I was shocked, "What...no way...are you crazy?" I protested.

"James...don't be a baby...its only a piece of clothing...no different from briefs...we will however need to give you a little trim...I wouldn't want your pubes getting all over my knickers."

Without even getting my consent she grabbed me by my hand and pulled me into her bathroom.

"Sit here!" she said pointing to the edge of her tub...I complied...

"Spread you legs...I promise to be careful."

"Ally said I was not to remove the ring though," I protested.

"No problem," replied Melissa...taking the ring in her fingers rolling it up my shaft...right up below the head of my penis. "There...it's not off...and it's out of my way...now...spread em!"

I opened my legs as Melissa went to work on me with a pair of scissors. With every snip I saw my pubes drop to the white tile floor of the bathroom. When my hair was relatively short...she grabbed a can of shaving cream. "As long as we're doing this we might as well do a good job," she coyly said as I nodded, giving her permission. Melissa sprayed the cream into her palms and started rubbing it over my crotch building up lather. She took hold of my cock...sliding her warm hands over the slick shaft. Then she turned on the faucet of the tub...and wiped her hands clean. Melissa then took a disposable razor in her hand and began to slowly stroke away my pubes. After each stroke she would let the water of the faucet run over the blade...washing it clean. As I sat there in utter bliss, I took a moment to admire the sheer beauty of the girl before me. Melissa was in fine shape...every inch of her body toned...her flat stomach...up to her delectable breasts. Melissa took the tip of my penis and held it between her index finger and thumb while she used the other hand to shave around the curves where my shaft met my body. When it was all over...I was completely shaved...Melissa running her hands over the now smooth surface of my crotch...and enjoying it quite a bit. She finally rolled the cock ring back down from the tip to the base continuing my agony. Melissa saw the pain/pleasure the device was causing me.

"Don't worry James...I'm sure you will get some before the weekend is over," she said with a smirk... as she laid a quick but wet kiss on my lips...her tongue briefly exploring my mouth. "Now lets get you dressed...you're now able to wear these," she said...holding up the panties. She slipped the garment under my ankles an up my legs...stretching them a bit to fit around my waist. She took hold of my stiff cock one last time to stuff it into her panties and adjust it into a comfortable position. "You can finish getting dressed now...meet us in the car." I watched as Melissa left...grabbing a shirt on her way out. I quickly put on the jeans and made my way down to the car.

"Hey James...have a seat," said Ashley from the backseat of Melissa's yellow Volkswagen Beatle. Ashley slid over...her pink short dress riding up her legs to giving me an enjoyable eyeful. I sat down beside her; Melissa was in the driver's seat and Ally shotgun.

"We're just waiting for Roxy," Ashley informed me.

As Roxy came out wearing a short white skirt and tank top we realized that there was not enough room. No matter how we positioned ourselves...the three of us could not fit.

"Well...Roxy...just sit on James' lap...it's not a long trip," suggested Ally

Roxy quickly took that as a personal invitation from me and plopped herself down on my lap...adjusting her skirt so she wasn't revealing too much. Her hair was right in front my face...and the smell was amazing...the great scent that only a female has. As we made our way down Melissa's street we passed over some speed bumps in the road. The frequent movements up and down caused Roxy to be frequently pressing down weight on me...almost jiggling up and down on me. Soon...my hardon began to grow...poking Roxy from below. She let out a soft gasp as she felt me. The others were not aware...but Roxy looked down at me...holding my face in her hand smiling at me. Roxy began shifting her weight around...sliding her ass over my dick....all the while looking at my eyes and smiling as she gyrated over me. Thankfully we had arrived at the mall...I didn't know how much more teasing I could have taken before cumming in my pants. We all filed out of the car and into the mall. After about an hour of walking around we found ourselves in front of a Victoria's Secret.