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

Alex was still in disbelief, a he had erupted for the first time in his life at the feel of a real woman. He averted his eyes from Olivia embarrassed, though she did not appear to mind. Olivia was in a hurry.

Alex looked around for something to wear, thinking it not appropriate to walk out in only the lingerie, with his cock hanging out, though Olivia had taken all the newly purchased items.

The cure blonde found him a black skirt. "Here ya go cutie, you are quite a lover, though I don't think you will be wearing white for long.". She smiled to him.

....

Alex pulled the skirt on, reaching behind to shipping. She then made here way to find Alex sitting and waiting in the car. Alex moved briskly, yet was allowed by the heels.

Reaching the car he opened the door, as he say his shirt raises exposing the tip of his soft cock.

"I am sorry Olivia, I hope you are not upset with me. It all just kind of happened.

Olivia pretended to busy as Alex rode out his orgasm and she smiled as she saw what a large load he produced. She gathered their items and walked out into the lobby--waiting patiently.

As Alex came out of the backroom Olivia giggled as she noticed his shirt catch and lift to expose his cock. Olivia stepped forward as he started to apologize and reached down her hand moving underneath his shirt and touching the tip of his cock. "Oh, my, Alex. You're still leaking." Olivia lifted her hands and held them to his lips. "Now, be a good gurl and taste yourself for me."

Olivia giggled and winked at the woman at the counter before turning and leading Alex to the car. "Come on, honey. We've got to make sure that you're ready for practice today. I'm going to show you where the lockerroom is and we'll have to get you fitted for a uniform. Our coach is a lovely woman and the football team is going to enjoy meeting you!"

Alex did not want to taste himself, yet as her finger approached his lips, he closed his eyes and puckered ... readying himself for the bitter awful taste. Though it was not as he thought it would be, the warm, mild salt, thick, but not awful. His lips relaxed as he sucked Olivia's finger.

...

Alex could not believe what was really happening, this last day was a whir in his mind. As he walked his heels .. yes his heels echoed. For a moment he wondered what Olivia meant when she said the football team would enjoy meeting him. These same players who in his former world would never know he existed. "Yes that will be fun." He responded naively .. "It will be nice to meet them ... I suppose."

"Did you say uniform ... I suppose ... there are guys on the cheer squad too." Alex asked not trying to be too optimistic that he was going to be one of the girls.

Olivia smiled. Pleased that Alex had turned out to be so obedient. She giggled quietly as she realized that this was precisely what she had been missing in her life.
**

Olivia drove fast. The wind blowing in their hair--the windows down. She smiled as they arrived at the football field and waved to some of the men that stood around waiting to get ready for their practice. Olivia winked at Alex and told him to wait a minute before she walked around the front of the car and opened the door for him. Knowing that she hadn't taught Alex anything she giggled as he moved to get out of the car--flashing the panties that he wore to the football players. "Mmm, the boys are certainly going to enjoy you, you tease. Just you wait and see!"

Olivia thread her arm though Alex's arm and led him towards the locker room. "We have our own fitting room but the men just love to drop in on us something so you have to be careful if you don't want to get caught, honey. Or, if you don't mind I'm sure they'll be okay nonetheless. You'll see how they are." She completely ignored Alex's comment about other guys and let her hips swap as they approached the gym. The boy's eyes followed them and Olivia winked at them before leaning over and kissing Alex on the cheek. "I'll keep you safe, if that's what you want, honey." Olivia giggled.

The locker room was well lit and clean when they entered. Olivia led Alex to the locker that had been assigned to him. "Here you go, gurl friend. Our uniforms are going to vary game to game but your practice gear should be in there with some spanx. "Those spanx will help keep your secret as long as you want it to be kept--or at least until we start getting you properly feminized..."

As Olivia led Alex he was oblivious to the male eyes of the athletes following him

"Here you go, gurl friend. Our uniforms are going to vary game to game but your practice gear should be in there with some spanx. "

To Alex's surprise his name had already been mounted on the locker.

"So this is really for me ... Olivia ... I am going to be one of the girls ... not a male cheerleader ... for like real." Alex asked trying to hide his nerves.

The locker room was so different than a typical mens locker room. Instead of bad odors, there was a feminine fragrence abounding.

spanx

Soon ALex was modeling the spanx for Olivia. "Oh my gawd .. you cannot even tell and now I have an ass." Alex smiled.

will help keep your secret as long as you want it to be kept--or at least until we start getting you properly feminized..."

The words echoed in his head and finally he asked. "Olivia ... I understand most men would not to know what I really am ... but what do you mean .. properly feminized."

The words echoed in his head and finally he asked. "Olivia ... I understand most men would not to know what I really am ... but what do you mean .. properly feminized."

Olivia giggled. "Oh, honey. Just you wait and see what I mean!" She winked and smiled broadly knowing that she had started slipping a supplement into his drink the first night they had partied together with her family. She reached out and placed her hand on Alex's ass. "Everyone's going to love this, baby. Just feel how tight your ass feels!"

Olivia took off her own clothes before stepping into her uniform. She smiled as she caught Alex staring. "Come on, Alex. You'd better hurry so that we're ready to go once practice starts!"

Olivia's hand lingers upon Alex's ass, she is right his ass is tight and curvy and well sexy. Everything a guys ass should not be. "Wait and see ... huh." Alex quizzes Olivia hoping for more info. "I hope they love me ... I am not used to people seeing me .. let alone as a cheerleader."

With veteran expertise Olivia was quickly dressed in her uniform. "Oh my Olivia .. that is even hotter than it looks. Thankfully I will be wearing the guys version ...." As Alex stares at Olivia he knows the answer to the question he just asked. "I mean it looks really nice ... but I mean look at me Olivia ... I do not think I have the boobs to pull it off.

Olivia smiled. "Honey, everyone's going to love you! We lost one of the most important members of our team last year--and she was always holding others up in the air. You've got some important shoes to fill but I am so sure that you'll be up to it!" Olivia squeezed Alex's arm. "You're going to be my superstar."

Olivia watched as Alex dressed and smiled. "You look great, Alex." She stepped forward and ran a hand over Alex's chest. "We're going to fix that chest issue, but don't worry about it for now." Olivia's fingers lingered on his chest--kneading it before she pulled her hand away. "Now, come over here and help me get some things together so that I can run you through some routines before the other girls get here."

Olivia purposefully bent over in front of Alex exposing her covered rear end. She backed up and said "Ooops" as her ass pressed against Alex's midriff. Standing up she smiled to herself and turned taking Alex's hand and leading him into the practice space.

"I hope nothing bad happened to her.". Alex told Olivia about the girl he was replacing.

Soon he was dressed similar to Olivia, his hair pulled into a point tail, lip gloss upon his lips, his manhood tucked tightly away, his best mid riff on display. Thankfully Alex was quite slim and had good giving him the appearance of a young yet flat cheated woman. Olivia bent to tease him pushing her as to his bear tummy, them teased Alex for her flat chest. As she did Alex felt a single in his nipples. Olivia mentioned doing something about it. "I hope so, I always wished that."

Soon she lead him to the practice space, Alex following her lead.

Olivia smiled as they stepped out onto the field. "You're so cute, Alex!" She waved to the other girls on the practice field and introduced Alex to the last members that he had not met. "Come on, Alex, it's time to get stretching and ready for practice." Olivia giggled as she watched Alex's reaction as he watched the women stretch around him. "I hope you're ready to show off, honey. Because these girls are so ready to put on a show!"

The practice started as it normally did with stretching and warm-ups but as they got further into practice Olivia realized that Alex was going to have to learn how to properly move his hips. She smirked as she turned to her teammates. "Come on girls, Alex needs to learn how to properly move his hips for us." Olivia leaned in close to Alex and whispered in his ear, "Watch and learn, honey. You're going to be a big tease soon."

The girls formed a triangle and as the music started to beat across the practice space they began by shaking their asses. Olivia's hand smacked her own ass as she bounced across the field and she winked at Alex before playfully smacking the woman next to her on the ass.

"Come on Alex, you're going to have to learn sooner or later what it means to bounce your ass so you'd better get over here and join us."

Alex joined in on the stretching, though his lean body was quite flexible, there was work to be done to be as flexible as the girls are.

"Watch and learn, honey. You're going to be a big tease soon."

"Only a tease?" Alex smiled back at Olivia trying to be one of the girls. Alex was so enthralled in trying to look natural he had not even noticed the boys ogling upon the cheerleaders.

"Come on girls, Alex needs to learn how to properly move his hips for us." Olivia leaned in close to Alex and whispered in his ear, "Watch and learn, honey. You're going to be a big tease soon."

"Really ... I have no choice do I." On his first attemp, he bent forward and wiggled, soon all of the girls were laughing, Alex turned red, and tried and tried and tried again until he was getting closer and closer to what the girls were looking for. Soon Alex was in line with the girls wiggling his ass to the delight of the onlookers and the other cheerleaders.

Olivia watched proudly as Alex worked his way through the movements until he had the motion down just right. She giggled with the other girls before stepping forward. She placed her hands on Alex's hips and smiled. Leaning forward she spoke just loud enough for Alex to hear. "That's a good girl. Now shimmy like you were--I want you to give a little show." Olivia's hands roamed over Alex's ass and she playfully spanked him as he bounced his ass on her waist.

Olivia playfully pulled on Alex's hair and reached around his waist so that her hand was pressed against him. She teasingly started to grind her hips against his movements as her hand played with his cock. "Mmm, don't you just love all that attention Alex?"

Olivia stood then and her hands pulled Alex back to a standing position before she leaned in kissing him passionately--her tongue snaking with his. She pulled back momentarily. "I've always wanted a gurlfriend. I'm so happy that we're exploring this together." She smiled and kissed him lightly again.

"Okay girls! What's next??"

sissykaitlin said:

Olivia watched proudly as Alex worked his way through the movements until he had the motion down just right. She giggled with the other girls before stepping forward. She placed her hands on Alex's hips and smiled. Leaning forward she spoke just loud enough for Alex to hear. "That's a good girl. Now shimmy like you were--I want you to give a little show." Olivia's hands roamed over Alex's ass and she playfully spanked him as he bounced his ass on her waist.

Olivia playfully pulled on Alex's hair and reached around his waist so that her hand was pressed against him. She teasingly started to grind her hips against his movements as her hand played with his cock. "Mmm, don't you just love all that attention Alex?"

Olivia stood then and her hands pulled Alex back to a standing position before she leaned in kissing him passionately--her tongue snaking with his. She pulled back momentarily. "I've always wanted a gurlfriend. I'm so happy that we're exploring this together." She smiled and kissed him lightly again.

"Okay girls! What's next??"

Click to expand...

Alex was getting into the movements, concetrating to much on her own moves to realize the other girls were watching and judging her. Then she felt Olivia's hands on her skinny hips

"That's a good girl. Now shimmy like you were--I want you to give a little show."

Olivia's slap upon his ass nearly woke him from his state, startling the newest girl on the squad.

"huh" Alex asked surprised unsure of Olivia's intentions.

Alex's hair was in a pony tail, making it easy when Oliva pulled his hair back, causing his back to arch and flat chest to jut forward. to the football team across the way, it was a sexy silohette, none was wise to Alex's true identity. Feeling her hips against him, her hand reaching around to play with him, the tight shorts made his cock near invisible, though the sensation was devine. Alex wanted to turn and kiss her, as his head turned he met Olivia's lips. Their tongues swirled teasing each other. Oh how long he had dreamed of kissing Olivia.

She then pulled Alex upright, he still was lost in the kiss and passion.

"I've always wanted a gurlfriend. I'm so happy that we're exploring this together."

Alex heard the words but had never had a girlfriend ... let alone the girl of his dreams. "So am I" he whispered, meeting her lips again for a kiss.


"Okay girls! What's next??"

Alex did not even hear her words, lost in his lust, his desire, feeling so feminine, a moment he did not want to end.

Olivia smirked as she watched Alex gathering himself. And twirled to face the rest of the team. She knew that the football players were still watching them and she turned on the next song. "Okay, ladies, here we go!" Olivia moved behind Alex and put her hands on his hips again but instead of having him do anything she instructed him and guided him as he started to match the movements of the rest of the team.

Olivia watched the sidelines as the football team got ready to start their own practice and smiled knowing that they were all staring at her and the others ladies. The school was fairly strict about the fraternization between the cheerleaders and the football players--especially during the season but there were still moments when they could have fun together.

Olivia called the end of practice and the girls gathered by the stands and watched as the football players warmed up. Olivia leaned forward and whispered in Alex's ear--her tongue gently licking his skin. "Won't you just look at those big boys." Standing up Olivia winked at her teammates and lifted Alex's skirt flashing the men on the field.

Alex was doing his best to keep up, though quickly realized that cheerleading was more that pretty hair and uniforms. The dancing was more of a workout than he had ever had. Though, he had danced throughout his life and that was definitely help him keep up and not look totally lost as he followed along.

Finally, Olivia called for a break and she was quickly near him. Though Alex was thankful, she was close, allowing him to not feel out of place. Alex was out of breath and did not even realize when the girls lifted his shirt giving a show to the football team.

"Huh what.". He said to Olivia. Finally he turned his head as he heard the tells from the team. Still he did not realize the noise was for him, and the boys lusting at what they saw.

Olivia giggled and patted Alex's bottom. "You did great, honey. I knew you would be up for this. The rest of the girls just love you and the boys seem to, too! Okay girls, time to hit the showers!"

Olivia led Alex towards the lockerroom and as they passed the football team she winked at them and introduced Alex. "Morning boys, this is our newest teammate Alex. I'm sure you all will get to know her soon!" The star of the team smiled broadly as Olivia introduced Alex. He held out his hand. "Good Morning Alex. We look forward getting to know you. I hope that the girls are treating you well!"

Olivia smiled and smacked the man playfully on his chest. "You know that we're teaching her the ropes. You're just going to have to wait your turn..." Taking Alex's hand Olivia led him back to the lockerroom where the ladies were waiting. As Alex entered they cat called him and told him that they were ready to be cleaned-up after such a hard workout!

Alex for the first time in his life felt accpepted. "Thank you Olivia. thanks I really like the girls too ... but the boy's ... you know all they want?" Alex asked naively.

Alex held Olivia's hand as she led him off the field and then past the football team. Alex was blushing seeing them up close and how they looked at both himself and Olivia.

"Morning boys, this is our newest teammate Alex. I'm sure you all will get to know her soon!"

"umm .. hello." Alex spoke softly.

"Good Morning Alex. We look forward getting to know you. I hope that the girls are treating you well!"

Alex took the hand he offered, making certain to grip softly. "um lie yes ... I look forward to that. The girls are very accepting of me ... it is nice."

"You know that we're teaching her the ropes. You're just going to have to wait your turn..."

Alex smiled shyly. "Yes they are .. and doing a great job ... I just hope I meet there expectations." Alex smiled, tilting her head.

...


Soon Olivia led him off and took him to the cheerleaders room. He was surprised at what he saw before him, looking to Olivia as if asking if this was serious.

Olivia giggled and nodded. "Well, it looks like you've got some plans for the start of your afternoon. When you're all done I'll have to give you a treat." Olivia watched as Alex dropped to his knees and assumed his position behind her teammates. She was so proud of how quickly he had caught on and how willing he was to please everyone. She had been slipping him extra hormones during meals and knew that soon he would be facing changes that were going to be changing his life.

Olivia lowered herself next to Alex's ear where he knelt and whispered, just so he could hear. "If you do a good job with these girls I'll give you a special treat before dinner tonight. We're going to be having some professor's over tonight for some extra tutoring..."

Olivia went back to the showers and turned the water on warm and decided to take a long shower to help herself relax. She knew what she had planned for the afternoon with Alex and she wanted to ensure that she was ready for him. She wanted to let him have one meaningful sexual encounter where he could maintain his manhood before his life changed for the better.

"Well, it looks like you've got some plans for the start of your afternoon. When you're all done I'll have to give you a treat."

Without a word Alex dropped to his knees to diligently service each waiting girl until she was satisfied. Thinking how days ago girls would not look at him and how they smiled at him now. How lucky was he he thought. It did not occur to him the changes taking his own body, his own cock stirred but not a a viral young moan, and the last day his nipples ached, though he thought little of each.

"If you do a good job with these girls I'll give you a special treat before dinner tonight. We're going to be having some professor's over tonight for some extra tutoring..."

Alex looked to Olivia smiled and leaned in stealing a kiss from her. Then Olivia was gone, leaving Alex to take care of things. He did so satisfying each of his teammates, Alex was exhausted when he found the shower, taking time to relax, and as he was alone he stroked himself but stopped as he recalled the words of Olivia and hoped he would have that encounter he had wished for so long.e

Olivia lounged around the house for a while. Getting the tub ready she took an hour to soak and relax her muscles. She knew what she had planned for Alex and was ready for him to have his first and last experience as a full man--she had teased him for long enough and watched him grow into his new identity and role.

After finishing her bath Olivia toweled down and got ready for the evening. There were going to be some professors over this evening as occurred every week. They dedicated themselves to helping the team pass their classes and Olivia always ensured that everyone was treated well. Plus, the girls loved the extra attention and the professors always seemed happy to give their time outside of the classroom.

Olivia took some time to bake some mostaccioli as she waited for Alex to get home and for their professors to arrive.

It had taken Alex sometime to get home, with satisfying his teammates and all. Than and the guy who had stopped her and asked her out. "So sorry I have a girlfriend" Alex told him which only exited him more.

When he arrived Alex was in the kitchen Alex hugged her and kissed her, before heading to his room, taking a quick shower. As he did he noticed the small bump on his arm and that his chest and balls ached some. The shower helped ease her.

By the time he was ready talking longer than expected, the other girls were already down the stairs and most of the professors had arrived.

Alexhttp://i.dailymail.co.uk/i/pix/2015/03/13/26955B0600000578-2992577-image-a-50_1426207413511.jpg

Olivia has freshened up while Alex has been making his way home. When he came into the kitchen she smiled and twirled for him. "You'd better hurry, honey. Our guests are going to be here soon and you're going to be on my arm all night."

She winked and giggled. "I've laid out a sexy little outfit for you to wear tonight. You and me are going to have some fun." Olivia smiled wickedly and went back to finishing the preparations for the party. Tonight she was going to make Alex very happy but she also knew that they were going to have a bit of an audience if everything went appropriately.

As guests started to arrive Olivia made her way quickly upstairs to make sure that Alex was ready for a fun evening. When she entered the room she smiled as she looked Alex up and down. "Dam, Alex. You look hot." Olivia stepped forward and her hand went to the back of Alex's head pulling him in for a deep, passionate, kiss.

Seeing Olivia, Alex stared at how sexy she was. "Oh my Olivia you look so sexi in that."

Suddenly Alex felt he was not dressed for the night, though he looked cute, apparently sexi was on the menu for the evening study session.

As if on cue, Olivia told him. ve laid out a sexy little outfit for you to wear tonight. You and me are going to have some fun."

"I guess maybe like .. I am dressed a bit ... ummmm .. like too casual for the guests." Alex responded, though thinking he may be put up to service the girls and/or guests tonight. Though she did say Alex would be on her arm all night, so hopefully tonight was the night he finally ... well got to have Olivia, with more than his mouth. "Really something little and sexy for me ... I can hardly wait.

...

Alex followed Olivia to her room, his eyes wandering across her body.

"Dam, Alex. You look hot." Olivia stepped forward and her hand went to the back of Alex's head pulling him in for a deep, passionate, kiss.[/QUOTE]

Alex was stunned by the amazing kiss, something about the kiss and the night gave him hope. Catching his breath he finally whispered. "thank you Oliva ... for giving me a life."

(So how are you dressing Alex?)

Olivia smiled and watched as Alex lifted up the dress from the bed. She smiled playfully as she stepped forward and lifted Alex's top up and over his head. "Mm, you're going to get all of the attention in this, tonight."

Olivia giggled and smiled knowing that the outfit would be see thru in all of the right places. Olivia stood behind Alex as he looked at himself in the mirror. She wrapped her hands around to his front side and allowed her fingernails to trace over his cock. "If you're a good gurl tonight I'll have to reward you, finally."

Olivia giggled and bit her lower lip. She could hear everyone starting to gather downstairs.

sissykaitlin said:

Olivia smiled and watched as Alex lifted up the dress from the bed. She smiled playfully as she stepped forward and lifted Alex's top up and over his head. "Mm, you're going to get all of the attention in this, tonight."

Olivia giggled and smiled knowing that the outfit would be see thru in all of the right places. Olivia stood behind Alex as he looked at himself in the mirror. She wrapped her hands around to his front side and allowed her fingernails to trace over his cock. "If you're a good gurl tonight I'll have to reward you, finally."

Olivia giggled and bit her lower lip. She could hear everyone starting to gather downstairs.

Click to expand...

"Mm, you're going to get all of the attention in this, tonight."

Alex took the dress looking at it, realizing it was for him. But not for him as a guy, yet him as a girl. "Thank you Olivia ... I hope it fits." In front of her he began to undress, thinking nothing of disrobing in front of the girl ... girlfriend of his dreams.

over his cock. "If you're a good gurl tonight I'll have to reward you, finally."

Alex bit his lip upon feeling her touch and his raw, now growing cock. His smile quivered thinking this may be the night, he looked and saw the green dress picked by his lover for him.

Softly he whispered to Olivia. "What do I need to do to make certain I am a good gurl." He said wanting to please his girlfriend.

He stepped back and pulled the dress over his head, past his aching chest, to his hips and finally over his full cock. "Should I wear panties?" He looked at her seeing his reflection in the mirror, for the first time in his life liking what he / she saw as her refection.

Alexa