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A New Sort of Study Session (Closed for justmethatswho + sissykaitlin)

Olivia smiled as Alex emerged from the closet. "Oooh, that's a great choice! Just look how skinny your waist is and your thighs fill those pants perfectly, Alex. Good job picking out an appropriate outfit for today. Here, this is the last item you need." Olivia held out a small black collar.

"You made a good choice, Alex. My little something extra compliments it all so nicely. Hehe, we're going to have so much fun today!" Dawn had left the room and Olivia and Alex were alone. Now that it was light out the room was more visible with a large poster bedwith scarves that Olivia liked to use to tie up her guests, at times. The large picture windows looked out on the street and anyone walking by could see right into the room if the shades were pulled.

Olivia smiled as Alex reached up to brush some hair from his eyes. "Okay, babe. Let's get going we've got a couple of errands to do. We're going to start at one of my favorite shops! I haven't ever brought anyone with me, so you're going to be my first. But the girls go on dates there all of the time. I'm sure we'll run into a couple of them!"
 
sissykaitlin said:
Olivia smiled as Alex emerged from the closet. "Oooh, that's a great choice! Just look how skinny your waist is and your thighs fill those pants perfectly, Alex. Good job picking out an appropriate outfit for today. Here, this is the last item you need." Olivia held out a small black collar.

"You made a good choice, Alex. My little something extra compliments it all so nicely. Hehe, we're going to have so much fun today!" Dawn had left the room and Olivia and Alex were alone. Now that it was light out the room was more visible with a large poster bedwith scarves that Olivia liked to use to tie up her guests, at times. The large picture windows looked out on the street and anyone walking by could see right into the room if the shades were pulled.

Olivia smiled as Alex reached up to brush some hair from his eyes. "Okay, babe. Let's get going we've got a couple of errands to do. We're going to start at one of my favorite shops! I haven't ever brought anyone with me, so you're going to be my first. But the girls go on dates there all of the time. I'm sure we'll run into a couple of them!"
Click to expand...

Alex takes the collar, not having any idea what or if there is any significance to it. Part is thankful as i will hide his small adams apple.

"thanx Olivia ... btw you look ... quite hot like that .. well you always do, but I love that outfit on you."

"Okay, babe. Let's get going we've got a couple of errands to do. We're going to start at one of my favorite shops! I haven't ever brought anyone with me, so you're going to be my first. But the girls go on dates there all of the time. I'm sure we'll run into a couple of them!"

He pauses and then asks. "So this is really happening isn't it ... or is this some prank on me ... please be honest with me Olivia .. I have always had a crush on you ... but please don't humiliate me or something like that."
 
He pauses and then asks. "So this is really happening isn't it ... or is this some prank on me ... please be honest with me Olivia .. I have always had a crush on you ... but please don't humiliate me or something like that."

Olivia smirked and her fingers ran through Alex's hair tugging on it sharply. "I won't humiliate you, honey. You know all of the girls are going to love you! Just you wait and see how popular you'll be with them."

Olivia leaned in and her hand went to the back of Alex's neck pulling him in for a kiss. Her tongue darting out and wrapping with Alex's. "You have no idea how long I've wanted this, Alex. This is what I always dreamed about when we were younger."

Olivia led Alex outside to her car and slid into the driver's seat.
--

Olivia drove to a popular spot where her teammates often hung out and had fun together--knowing that they would run into at least a couple of the fellow cheer squad. "You're always going to be a man, Alex. But, in order to fit in with the house and with the team you're going to have to work hard to understand what makes us happy and what makes us such close friends. We're going to start here, today, and see how you do."

The door opened with a jingle of bells announcing their entrance. Olivia waved to the woman at the front counter. "Hi Joy, is it okay if we go back?" Olivia nodded towards Alex and winked. "I've got a new recruit for the girls to get to know."
 
This last day had Alex's head spinning ... finding it difficult to believe what was happening ... still feelinga t any moment it was going to end.

"You're always going to be a man, Alex. But, in order to fit in with the house and with the team you're going to have to work hard to understand what makes us happy and what makes us such close friends. We're going to start here, today, and see how you do."


He pondered Olivia's words ... knowing there was a spot in his soul he did not want to be a man .. not in any way. Yet there was some relief in that he would still be Alex. He wondered what she meant by being close friends with the girls and making them happy.

"Hi Joy, is it okay if we go back?" Olivia nodded towards Alex and winked. "I've got a new recruit for the girls to get to know."

Alex smiled at Joy admiring her and her outfit, before fianlly catching himself.

"Joy it is nice to meet you ... I am Alex ... well Alexa .... I love your outfit ... I wish I looked that good."
 
"Joy it is nice to meet you ... I am Alex ... well Alexa .... I love your outfit ... I wish I looked that good."

Olivia smiled and took Alex's hand. "Very good, Alexa. Thank you, Joy. I'm sure that we'll see you later this afternoon when you get a break."

Olivia pushed open the door and they stepped into a long corridor with at least five doors on each side of the hallway. Olivia led Alex back. "Now Alex..." Olivia stopped walking and turned to face Alex. Her eyes meeting his and her thigh pressing against his groin. "You're not to be overly forward. When the girls are ready to introduce themselves they will but for now we are just shopping for your wardrobe. Do you understand what I'm saying?"

Olivia opened the door and they stepped into a room that looked like it came out of the local mall. Only there were women, there looking at the items. Olivia, still holding Alex's hand, led him deeper into the strange room to where she intended to begin their day. "Hi girls! We've got a new recruit." Olivia pulled Alex forward and spun him around. "Alex, these are some of the girls that you're going to be performing with..."
 
As quick as we see joy, Olivia is leading me down another Hall, we stop I think she is about to kiss me, her though pushing into my crotch my cock perfectly tucked awake, I look to her eyes hoping for a kiss. Then her words telling me to behave.

" Yes Olivia I understand, we are just shopping.... For my wardrobe?". I say this whole thing puzzling my mind.


...


We continue to another door and enter, my eyes stunned by what I see, the women so sexy, most in panties and bra. Olivia speaks,.I am in a trance I cannot help but stare. Finally I think enough to stutter the words. ,
" Hi I I am Alex .... "
 
Olivia smiles as she knows that she has surprised Alex by what they have found. "You didn't know what you had gotten yourself into, did you, Alex?" Olivia leans over and whispers--her lips brushing against his ear. "Did you ever think that you would find yourself here?" Olivia leads Alex into the room. They can see the other team members looking at heels and panties and other items that they can wear during the week.

Olivia squats down and pulls some items off of the shelf and hands them to Alex. "Here, Alex" Olivia pulls a few more items. "Why don't you go try these on--we're all waiting here to see what our newest team member looks like."

Olivia waves to the other girls. "Are we all ready for practice this afternoon? Alexandra here is going to require a lot of work, girls. But, he'll turn out to be a great addition once we have him properly trained!"
 
sissykaitlin said:
Olivia smiles as she knows that she has surprised Alex by what they have found. "You didn't know what you had gotten yourself into, did you, Alex?" Olivia leans over and whispers--her lips brushing against his ear. "Did you ever think that you would find yourself here?" Olivia leads Alex into the room. They can see the other team members looking at heels and panties and other items that they can wear during the week.

Olivia squats down and pulls some items off of the shelf and hands them to Alex. "Here, Alex" Olivia pulls a few more items. "Why don't you go try these on--we're all waiting here to see what our newest team member looks like."

Olivia waves to the other girls. "Are we all ready for practice this afternoon? Alexandra here is going to require a lot of work, girls. But, he'll turn out to be a great addition once we have him properly trained!"
Click to expand...


"You didn't know what you had gotten yourself into, did you, Alex?" Olivia leans over and whispers--her lips brushing against his ear. "Did you ever think that you would find yourself here?"

"umm no ... I still don't ... only in my dreams have I been in a place like this ... I am not dreaming am I" Alex asks in all seriousness.

"Here, Alex" Olivia pulls a few more items. "Why don't you go try these on--we're all waiting here to see what our newest team member looks like."

Alex looks around and sees the other girls looking at him. He takes the first couple outfits and looks for the changing room, finding it . "This may take a bit .. I am so new to all of this."

Finally he returns in outfit number 1

First

Then the
Second

Third

Alexandra was getting into this ... shopping had never been so much fun ... he was learning how much the outfit changed his appearance

Fourth


Fifth

And Last

Lastly he was handed his workout outfit for practice
 
Olivia smiled and turned to her friends--noticing their nods of approval. "Fuck, Alex. You're perfect. The girls just love what they see of you!" Olivia twirled her hair with her finger as Alex spun showing off the outfit that she had picked out for him. "You're going to look so good on the practice field. Am I right girls??"

Olivia smiled and turned behind her to find one last outfit. "Here Alex. Here's the last outfit that you're going to model for us. It's for the team party tonight--we want you to look extra good. And just remember--there's no getting too wild because we've got to practice early tomorrow morning and as your captain I don't want anyone to be late."

As Alex returned to the dressing room Olivia waved to the girls in the room--inviting them to sit with her and wait for his return. Olivia turned to Dawn and leaned in kissing her softly. "What do you think? Will Alex work out?"
 
The attention felt good to Alex .. he never was one to be noticed in a room, in particular by the attractive girls.

"Sure as you wish Olivia." Alex took the outfit back to the dressing room.

It was not until he began to dress that he relized there were no panties. He hated what he saw between his legs, in spite, his cock grew rigid.

Alex returned, his hands covering his semi erection.

"Oh my olivia .. yes I think she will work ... with a bit of work ..
her body is great, fit, trim, but we will need to adress the are of her breasts and what is between her legs.
 
Olivia smiled widely and invited the other girls over to check out their new teammate. "Come on girls. We've got to make a decision about our new recruit! What do you think? Will she do a good job for us?" Olivia stood up and walked towards Alex--taking her cock in her hand she paraded around the room.

"Well, we'll have to do something about this but I'm sure you girls know what will be required." Olivia paused in front of Dawn. "Why don't you show everyone what fun you had last night, Dawn? Then once he's spent we can take some time to dress him and get ready for practice this afternoon."
 
sissykaitlin said:
Olivia smiled widely and invited the other girls over to check out their new teammate. "Come on girls. We've got to make a decision about our new recruit! What do you think? Will she do a good job for us?" Olivia stood up and walked towards Alex--taking her cock in her hand she paraded around the room.

"Well, we'll have to do something about this but I'm sure you girls know what will be required." Olivia paused in front of Dawn. "Why don't you show everyone what fun you had last night, Dawn? Then once he's spent we can take some time to dress him and get ready for practice this afternoon."
Click to expand...

Alex was tunned and embarrassed, as his cock wanted to be touched. Was this the moment he finally found his satisfaction.

"This" The words echoed only making him more embarrassed from his ugly manhood. "Of course" Alex whispered.

Then Olivia asked keli about last night. Alexandra's face was clearly red now. "Uh" Alex had no idea what to say.
 
Olivia winked at Alexandra wickedly and turned towards Dawn nodding as she watched her drop to her knees. Dawn crawled towards Alex and from where she knelt she reached up fondling his balls and gently stroking his shaft. "Mmm, Alexandra. You were so good last night. Everyone needs to know what a good team member you are going to be!" Laughing Dawn pulled herself up to a standing position and pushed Alex down to his knees. Stepping forward she straddled him. "That's a good girl, now..."

Olivia smiled and watched as the rest of the room focused on Dawn and Alex--knowing that it wasn't going to take much to convince everyone else that Alex was going to be a good team member. "That's it Alex. I just want you to show everyone that you're willing to do whatever it takes to join this team because this is how you're going to earn your spot."
 
Alexandra was nervous, his cock seemed to grow harder and harder as Dawn crawled to him, His everymove reminding him how he was dressed in the lingiere, the stockings the heels.

He hoped as Dawn crawled to him he would finally get what he desired, yet as she stood, he knew he would soon again be at her service.

She heard the encouragedment, and soon was leaning forward, his hands sliding to Dawns hips and pulling down her leggings. Alexandra kissed her thighs and moved to her pussy, lapping, soon hearing Dawn's encouraging moans.
 
Olivia giggled as she watched Dawn ride Alex's face. She looked towards her teammates and nodded her encouragement. As she did so her teammates moved forward and knelt besides Alex. They reached out squeezing his cock and teasing his balls. Dawn rode out her first orgasm and stood up as Olivia knelt in front of Alex. Her hand reached out and she wrapped around Alex's neck as she kissed him. "Mmm, you taste so good honey. These other girls are going to get jealous if you don't give them as much attention as Dawn commands." Olivia giggled and pulled back from Alex and stood up.

Gathering her things Olivia picked up the bags with Alex's outfits. "Here you go girls. I'm going to pay. Make sure you get what you want from our new teammate before practice starts this afternoon! She needs to be broken in before she meets the team!"
 
Feeling the girls around him only made Alex more excited, one was touching his cock, he was so close to erupting.

Then Olivia left him after the sensual kiss. "Ovliva ... don't leave me." He begged, as she walked away with his new things. Leaving him alone with the other girls on the team.
 
Olivia smiled as she walked away. She knew how close Alex was to exploding. "Have fun, girls."

Olivia sat out in the lobby as she waited for her teammates to finish up with Alex. She knew that they were going to get all of the pleasure that they could from him but wanted to keep herself. Olivia knew that when the time was right she would take Alex for herself but for now she was more than happy to share.

Looking through the outfits Olivia smiled and sorted through them. She had purchased everything that Alex was going to need for the first day of tryouts and had purposefully selected a sexy pair of pink boots that matched her own. Whistling to herself she smiled at the cashier. "I'm going to have the girlfriend that I always wanted to have soon, Ms. We're going to have so much fun together!"
 
Alex looked around hoping Olivia would return, though by now it was clear what was expected of him, he looked up and smiled shyly as she waited for one of her future teammates to present herself.

"Hi girls ... I ... I am Alexandra." she whispered embarrassed.

(Love the pink boots)
 
Olivia sat in the lobby with her legs crossed--listening to the moans that came from the room that she had just left. Knowing that Alex was likely going to be a while she started to plan for their evening together.

**

Dawn smiled at her teammates. "Well, if you didn't hear me last night, girls, then you'd better take a turn with our new teammate. She's going to need to be broken into the team." Dawn lowered herself from Alex's face and motioned for her other teammates to take a turn. While they did this Dawn slid between Alex's legs--her lips wrapped around his shaft and she looked up--meeting his gaze.
 
Alex's tongue and lips we beginning to ache, as Dawn called upon another girl to take her place. yet Dawn did not leave, she slid to his lap, his cock feeling her thighs rap his cock tight. The touch reinvigerated Alex, as for a moment he hoped Dawn would satisfy him sexually.

From the corner of his eyes, he saw a petite bloned grip his head and pull his head into her crotch, lifting her skirt as she did.
 
Dawn smiled and took Alex's cock into her mouth. Her tongue danced over the tip of his cock teasing him and making him moan loudly as the other team members took their turns sitting on his face.

Olivia came back to the room and smiled. "Ooh, my, Dawn. That cock does look yummy in your mouth." She giggled and sat down--crossing her legs. She enjoyed watching her teammates take advantage of her new recruit. She had some special plans for Alex this evening but first she knew that her recruit would have to prove himself to the rest of the team. "That's it Alex. You need to show them just how enthusiastic you are!"
 
Alex about erupted as he felt Dawn take his cock in her mouth. He had hoped it was Olivia, yet at this point he was not going to argue. She was magic upon his cock, He did not even see when Olivia came back in unitl she spoke.

"Ooh, my, Dawn. That cock does look yummy in your mouth."

Alex looked up to her, his face red with embarrassment, his lips glistening with a strange girls juices. He wanted to tell her he was sorry, yet could not find the words.

"That's it Alex. You need to show them just how enthusiastic you are!"

"Ohh" Alex moned and his arm reached out finding a petite brunette, in one motion he lifted her small skirt and buried his head in her pussy, soon he heard her moans. Soon she was moaning as she was certainly climaxxing.

Alex had not recovered, when he looked up, seeing the cute girl in the pink dress. Soon his head was under her skirt.
 
Olivia smiled as she watched her teammates sharing Alex. "Mmm, that's it girls. Show me what a good teammate Alex will make! Before he leaves today you're all to orgasm at least once." She smiled, pleased with how enthusiastic her teammates were about the newest recruit. Olivia nodded to Dawn and winked. "Mmm, which of you is enjoying this more, Dawn?" Olivia squatted next to Dawn and ran her hand up the woman's back--gently tapping her ass as she did so.

Dawn pulled back from Alex's cock and giggled. "You know that I'm having fun!" Dawn leaned forward and pulled Olivia towards her--kissing her passionately. Olivia moaned as she tasted Alex on Dawn's lips. "Mmm, Alex, you're such a naughty gurl! What are we going to do with you??"

Olivia sat back on her heels and winked at Dawn. "Why don't you finish him off for now? It looks like the girls are just about done with him. And, then, girls it's almost time for practice." Olivia stood up and went back out to the waiting room. She knew that she was going to have some plans for Alex that evening and didn't want to spoil anything.

As the girls wrapped up Olivia slipped into her cheer outfit and went out to the car to wait for Alex and her other teammates.
 
Alex heard Olivia's words telling Dawn to finish him off. He had lost track of the girls he had pleasured, his tongue was getting stiff, all he could smell was the juices of the women, his face covered.

"Oh ... fuck." He moaned as Dawn retured to finish him off. He looked to Olivia as if needing her approval ... yet it was too much ... he could no longer hold back ... for the firt time in his life ... his cock erupted ... with a touch other than his own .. but that of a woman .... "Oh Dawn ...." But it was too late to warn her as his cock erupted .... Alexa was aware of her surroundings, the lingerie she wore ... everything in this moment ... she moaned .. "I want this to last forever.
 
Olivia smirked as she heard Alex's last remark about wanting it to last forever. She laughed and looked over her shoulder. "Oh, it will, Alexa, it will."

"Now girls. You all need to clean up and get ready for practice! We've got a busy day today at the field house and I'm not going to wait on any of you if you're not ready to go this afternoon." Olivia opened the door to go back out to the lobby and turned to Alex. "Hurry up Alex, you're going to be coming with me. I've got some prepping to do with you."

Olivia swung her bag over her shoulder and nodded to the receptionist. "Thanks Bri! We had a great time today. You know... sometime you'll have to come back and have some fun. I'm sure your boyfriend won't mind you having some fun with us girls."

Olivia slid into her car and her skirt rode up her thighs--she rolled down the window and waited for Alex to join her.
 
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