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

Olivia sighed. It had been a long day of classes at the University today. But she was happy with her progress and knew that her hard work was paying off.

The best part of growing up in a University town was that the opportunities for scholarships and opportunity were forever present. She had recently accepted a scholarship and had joined the cheerleading team which she was quite proud to be a part of. But, she was different than the other women on the cheer squad. Whereas they were often bubbly and outgoing Olivia was more reserved and self aware. That partially came from knowing that she was always on display but also from the fact that having grown up in this town she knew that everyone knew who she was.

Stepping into the shower Olivia decided that she was going to relax and allow herself to soak before toweling off and heading back towards the flat that she was sharing with some classmates. She had decided not to live at home because she knew that it was going to be weird once she started wanting to go out with her friends during the week. So, instead, she was sharing a small home with a couple of her girlfriends. But, she still stopped at the house a couple of nights a week to catch-up with her Mom and sisters.

Tonight was going to be one of those nights when she stopped at home and she was planning on spending the night in the small three bedroom house. It was her birthday after all, and her Mom had insisted that she be home to celebrate, with the neighbors' and her cousins, just as she always was. Olivia dried off and threw on the clean set of clothes she had packed before heading home.

Alex was just finishing his present and cupcakes when he saw Olivia arrive at her parents. Whether she knew it or not she was his best friend growing up, even though she was a couple years older than him. The two had grown up playing with one another, well until Olivia reached high school, she was still nice to him it was more of a time issue.

See Alex never really fit in, he was different, and never fit in with the boys in the neighborhood. He tried playing sports, he was not just bad at it, he hated sports. Anymore the only sporting events he goes to is to see Olivia cheer, deep in his soul he wished he could be there with her.

As he wrapped her gift, he recalled several times in his youth, the two had played dress up. He loved those times. Alex was always tiny, thin boy, never rough and tough. Even though now he was 19, he was still quite boyish, he never shaved, his voice could easily be mistaken as a girl.

Alex made his way, carrying the tray of cupcakes and the gift for Olivia's birthday. Pushing the doorbell with his elbow he waited patiently for someone to answer the door.

Olivia was happy--her parents' were not home yet which allowed her a little time to get settled in and prepare for all of the guests to arrive. She dropped her things up in her old room and went about her business of getting ready for the party. She had decided to change her outfit so that she was at least a little dressed up for the party.

Smiling she heard the doorbell ring downstairs--before she had a chance to get her bra on. She decided to answer it and let in the first couple of guests before everyone else arrived. Olivia smiled widely as she opened the door and laid eyes on Alex standing there with some cupcakes and a wrapped gift. "Oh, Alex! You know you didn't have to get me anything." Olivia leaned forward and placed her lips to Alex's cheek and pulled him in for a hug. "It's soo good to see you! You know I didn't move to the other side of the world--you should come hang out with me at my new place sometime!"

Olivia stepped back and invited Alex into her parents' home. "Everyone else should be arriving a little later, I guess. But it's so good to see you! We'll have to catch-up before they get here." Olivia closed the door behind Alex and smiled. "I've just got to finish getting dressed... Why don't you come up and we can chat--you remember where my room is right?" Olivia ran up the stairs as Alex put his stuff down and took his coat off. Olivia quickly picked out the panties and bra that she planned to wear under her dress and disrobed so that she could put them on.

Seeing the dress Olivia was wearing caused his heart to skip a beat. The way the dress accented her body, the color bringing out her eyes, the twist in the skirt drawing teasing attention. For a moment he stood admiring, before handing her the gifts.

"Oh, Alex! You know you didn't have to get me anything." Olivia leaned forward and placed her lips to Alex's cheek and pulled him in for a hug. "It's soo good to see you! You know I didn't move to the other side of the world--you should come hang out with me at my new place sometime!"

Alex smiled enjoying her pulling him close. "I knew it was your birthday and you would be home ... I just thought I should do a little something for you Olivia. That dress looks wonderfull on you .. I must admit. I should come hang with you ... really ... I would love that ... get taste of a real college compared to the community college I am at .. I would really enjoy that ... if you do not mind."

"Everyone else should be arriving a little later, I guess. But it's so good to see you! We'll have to catch-up before they get here." Olivia closed the door behind Alex and smiled. "I've just got to finish getting dressed... Why don't you come up and we can chat--you remember where my room is right?"

Alex follows Olivia, knowing the way. Of course he recalls a few days the two had spent there in their younger years ... something he hoped he could relive sometime ... but doubted he ever would. As usual Alex and Olivia where talking as if they spent everyday with each other, their friendship was that way, they could just pick up. "Sure ... if it is ok to come up ... I would love to chat ... but I really did not know there was a party ... I am not really dressed for it. Maybe I should go home and change my clothes."

"Oh, don't be silly Alex! You know everyone that's going to be here." Olivia stuck her tongue out and giggled. Olivia smiled at Alex as he opened her door.

She had just finished putting her panties and bra on. She turned to greet him and caught him staring at her--and giggled. "Haven't gotten out much, lately, Alex?" Olivia turned on some music from the radio that was in the corner and turned. "Come on, Alex, let's dance!"

"My roommates are so boring. Maybe we can find a way for them to welcome you into the house..." Olivia smiled to herself knowing that her roommates did not want a male living with them but what they didn't know couldn't hurt, right? Olivia spun around and shook her ass at Alex teasingly then smiled. "You know Alex..." she trailed off and walked towards him running her hand up his bicep. "We could figure something out. Do you really want to change your clothes? I've got some right here that might interest you. We could be best friends, like we used to." Keli smiled and opened her closet.

sissykaitlin said:

"Oh, don't be silly Alex! You know everyone that's going to be here." Olivia stuck her tongue out and giggled. Olivia smiled at Alex as he opened her door.

She had just finished putting her panties and bra on. She turned to greet him and caught him staring at her--and giggled. "Haven't gotten out much, lately, Alex?" Olivia turned on some music from the radio that was in the corner and turned. "Come on, Alex, let's dance!"

"My roommates are so boring. Maybe we can find a way for them to welcome you into the house..." Olivia smiled to herself knowing that her roommates did not want a male living with them but what they didn't know couldn't hurt, right? Olivia spun around and shook her ass at Alex teasingly then smiled. "You know Alex..." she trailed off and walked towards him running her hand up his bicep. "We could figure something out. Do you really want to change your clothes? I've got some right here that might interest you. We could be best friends, like we used to." Keli smiled and opened her closet.

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"Haven't gotten out much, lately, Alex?" Olivia turned on some music from the radio that was in the corner and turned. "Come on, Alex, let's dance!"

"My roommates are so boring. Maybe we can find a way for them to welcome you into the house..."

"Really keli ... you live in all girls housing ... I know I am not much of a man ... but I still don't think I qualify to be living with you ... though it would be much better than living at home and going to community college." Alex smiled as they danced. "I should go home and change."

"You know Alex..." she trailed off and walked towards him running her hand up his bicep. "We could figure something out. Do you really want to change your clothes? I've got some right here that might interest you. We could be best friends, like we used to."

Her words caught his attention, recalling the sound of her voice when she had a devious idea which could not be denied.

"Figure something out like what .. I mean my khakis and t-shirt do not exactly say party. I have to change into something a bit more well party like. " She then went to her closet, a closet she knew Alex loved to see and touch the clothing ... to the left were outfits he had worn for her ... or she had dressed him in. He recalled how they had bet ... if she could make dress him in the cheer uniform, and take a picture ... he could pick her outfit to wear to school the next day. Then he saw the picture, she had taken in the back yard of him. (Alex in uniform)

Keli I know you could figure something out ... You have before .. but do you think there is really time .. I cannot believe you still have theat picture ... remember that day ... you parents came home early and found us in the back yard, I was still in your uniform, your parents thought I was a girl on your squad. I was soooo embarrassed." Alex blushed though the thought could not escape his mind.

"You know I have always loved your closet ... I mean if we have time .. you know I could not resist. Best friends you say." Alex smiled an image of the friends forming in his mind.

Keli I know you could figure something out ... You have before .. but do you think there is really time .. I cannot believe you still have theat picture ... remember that day ... you parents came home early and found us in the back yard, I was still in your uniform, your parents thought I was a girl on your squad. I was soooo embarrassed." Alex blushed though the thought could not escape his mind.

Olivia smirked. "Believe me, Alex. We'll get you to fit right in." Olivia moved to her closet and started to look through for a couple of items. She smirked seeing Alex looking at the photo on the inside of the closet door. "Oh, don't you ever think that I forgot what fun you can be!" Olivia giggled and laid out a couple of items. "Why don't you try on these for me while I find a good top for you. Maybe we can get you into the cheer squad with enough work!"

Olivia smirked to herself and pulled out a pair of panties and a belly top. "Here, you've got to play the part! I've got sweatshirt that you can wear over this top but I think it'll work well. Or would you like to pick something out for yourself?"

Olivia giggled as she watched Alex's reaction. "We'll get you to fit right in with my roommates, I promise." Knowing that her parent's and the other guests would be home Olivia moved to her door and closed it so that there wouldn't be any unexpected visitors. "Let's go, Alex, we're going to have to mingle in a little bit."

sissykaitlin said:

Keli I know you could figure something out ... You have before .. but do you think there is really time .. I cannot believe you still have theat picture ... remember that day ... you parents came home early and found us in the back yard, I was still in your uniform, your parents thought I was a girl on your squad. I was soooo embarrassed." Alex blushed though the thought could not escape his mind.

Olivia smirked. "Believe me, Alex. We'll get you to fit right in." Olivia moved to her closet and started to look through for a couple of items. She smirked seeing Alex looking at the photo on the inside of the closet door. "Oh, don't you ever think that I forgot what fun you can be!" Olivia giggled and laid out a couple of items. "Why don't you try on these for me while I find a good top for you. Maybe we can get you into the cheer squad with enough work!"

Olivia smirked to herself and pulled out a pair of panties and a belly top. "Here, you've got to play the part! I've got sweatshirt that you can wear over this top but I think it'll work well. Or would you like to pick something out for yourself?"

Olivia giggled as she watched Alex's reaction. "We'll get you to fit right in with my roommates, I promise." Knowing that her parent's and the other guests would be home Olivia moved to her door and closed it so that there wouldn't be any unexpected visitors. "Let's go, Alex, we're going to have to mingle in a little bit."

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Alex loved the way the leggings hogged his legs. "Why is it girls clothing feels so much better and sexier." He asked Oliva as she slid the sports bra on. "I guess I am a bit flat chested." He giggled. "I think we should add the sweatshirt ....or maybe those shiny leggings.

Soon Alex was again dressed. "Not only am I flat on top .. but on the bottom as well ... though that is a good thing right."

Alex in leggings, sweatshirt and heels

"These shoes take some getting used to. ... don't they."

HE then heard someone or several people downstairs. "You were serious aren't you ... you are going to make me mingle ... dressed like this."

Olivia smiled wickedly. "Come on, Alex. We've really got to get going downstairs. They're all expecting me!" Olivia spun and stuck her ass out towards Alex. "What do you think--we look good don't we??" Olivia's hand moved over Alex's ass and smiled.

Olivia moved quickly downstairs greeting all of her aunts and uncles and introducing Alex as "Alexandra" so that there wasn't any specific confusion as he had met everyone at one point or another. It was going to be a fun evening with lots of alcohol but luckily her family was open and encouraging of Olivia drinking in safe spaces and knowing that she could walk home from here only encouraged her.

Moving across the house Olivia said hello to her cousins but didn't really stop until she approached her mother. Holding out her hand to Alex Olivia winked and smiled wickedly. "Mom, this is Alexandra. I'm hoping that I can convince my roommate to let her live with us." Olivia stepped back and let Alex speak with her mom want to see just how far this could go without anyone finding out.

He felt Olivia's hand on his ass, little did he know it would not be the only hand to grope him today.

"Olivia I can't, everyone will know.", Alex tried to convince her. "I thought this was our secret". Though soon Alex football himself being pulled and introduced.

Alex had met most of them before, though thanks, none picked up he was the neighbor boy. Most have hugs welcoming Alexandra to the party..

Then Olivia was pulling Alex to her mother, surely she would pick up on who her friend really was. Her mother seemed to start, as if she knew who Alex was. Olivia ntroduced her mother to alexands. Alex smiled.

Her mother, Aled smiled and said hi, but looked to Olivia and at the ground.

"I know you, it's been a few years but you and Olivia were working on cheers and taking pics in the backyard, she still has that picture of you on her closet door."

Olivia smiled as she introduced Alex to everyone. The nice thing about such an androgynous name was that there was little reason to change it just to hide an identity. Olivia stuck close to Alex in case he became uncomfortable but as the evening progressed she allowed herself to relax and could feel the effects of the alcohol that they shared.

"I know you, it's been a few years but you and Olivia were working on cheers and taking pics in the backyard, she still has that picture of you on her closet door."

Olivia smiled. "I'm so glad you remember, Mom! What do you think--did I do a good job?" Olivia twirled Alex so that her mom could see the work that they had done earlier. "We've got a lot of work if Alexandra is going to join the cheer squad but I think I've got something to work with, don't you?"

Olivia giggled and subtly tapped Alex's ass.

Alex was nervous as Olivia introduced him/her around the room. Worrying that her just so t calling him Alex would be a clear sign and expose his true identity.

One thing he discovered quickly was that some of those and not just men while given a welcoming hug allowed there hands to touch Alex's ass.

Now the biggest test was olivias mother, who knew sex well. Olivia spin Alex to display her work to her mother. Alex was unaware how good his own ass looked, though his chest was a bit flat and her mother had no issue saying. "Yes Olivia, her backside and figure are quite nice, but ... Well her chest is a bit small."

Olivia smiled as she watched the surprise on Alex's face as she was discreetly groped by her relatives. She leaned into Alex and whispered in his ear. "I hope you don't mind... They're all a little over welcoming, sometimes." Olivia giggled and kept Alex close.

"Yes Olivia, her backside and figure are quite nice, but ... Well her chest is a bit small." Olivia smiled and spread her arms with a shrug. "Well, I'm working on it... Not everyone can look like you... Actually, I'm thinking that Alexandra could be great for the cheer squad! Don't you think? We've got an open bedroom too--it could be a great fit for everyone!"

Olivia blushed but she knew that everyone had had a crush on her mother when she was younger. But she couldn't change that fact. "Would you like a drink, Alexandra? I'm going to get something for myself so if you want something you better speak up now." Olivia's eyes roamed across the room and she relaxed everyone appeared to be accepting of Alex and no one but her mom knew the secret. But, that was to be expected as Olivia and Alex had never been super shy about what they had done back before they left for university.

Alexandra was quickly beginning to think this was all a bad idea, this outfit, why had she let Olivia do this to him ... her.

"Would you like a drink, Alexandra? I'm going to get something for myself so if you want something you better speak up now."

"Yes please ... surprise me." Alex responded softly, not wantint to sound too manly. He knew the family and chances are the drink he was brought would have alcohal.

Turning to Olivia. "She knows ... you told her ... she has known since that day ... I am so embarrassed. Does anyone else know ... be honest Olivia. You are going to so owe me for this." I threaten as if it meant something. "You know your uncles seem to like looking at me and touching my ass and you think this is funny."

Olivia left Alex with her mother--knowing that she was in good hands while she mixed two vodka and tonics. Olivia chatted with her relatives and made polite conversation before bringing the drinks back to Alexandra. She had made certain that his had much more vodka than tonic.

Turning to Olivia. "She knows ... you told her ... she has known since that day ... I am so embarrassed. Does anyone else know ... be honest Olivia. You are going to so owe me for this." I threaten as if it meant something. "You know your uncles seem to like looking at me and touching my ass and you think this is funny."

Olivia giggled. "I haven't told anyone--not even my mother--though, she just seems to have a natural way of sniffing things out that she shouldn't know...! Have you told anyone?" Olivia stepped forward just slightly and squeezed Alex's ass. "You should really tell people to stop doing that, Alexandra. It's not appropriate."

Olivia smiled and winked before taking another drink from her glass. Olivia led Alex across the room to the couch where they sat down next to one of her Aunts. "So, Alex, do you want to try living with me?"

Alex jumped when Elizabeth groped him. "Hey stop that." He said a bit too loud. "Please Olivia you are embarrassing me. Though he felt his little cock jump from it's tuck. "Please excuse me for a moment, and can you watch my drink."

Alex excited herself to the rest room, repositioned herself and returned to Olivia before she could do a thing Olivia pulled her close and sat her next to her hot aunt.

"Would I like to live with you, well sure it would be fun. You could teach me slot.". Alex said playing along with Olivia's lead.

Olivia giggled. "Sure, you're going to tell me to stop!" Olivia looked around the room and smiled. "Okay, I'll stop embarrassing you." Olivia twirled Alex's drink as she waited and took a pull of her own drink. The alcohol was flowing freely and everyone seemed to be having a good time. Olivia waved to her Aunt and crossed the room striking up a conversation just as Alex returned from the restroom.

"Have I introduced you to my friend Alexandra, Auntie?" Olivia giggled and gently nudged Alex forward before sitting down on the couch next to her Aunt. Olivia patted the spot between her and her Aunt expectantly. "Come on, Alex, why don't you join us?"

Olivia smiled. "You're right, Alex. I could teach you a lot. So, it's decided then. We'll just have to get you ready to impress my roommates."

"Have I introduced you to my friend Alexandra, Auntie?" Olivia giggled and gently nudged Alex forward before sitting down on the couch next to her Aunt. Olivia patted the spot between her and her Aunt expectantly. "Come on, Alex, why don't you join us?"

If Olivia's objective was to humiliate Alex tonight she was doing a fantastic job. Though he smiled to the two attractive Aunts and then Olivia tugged him so that he was sitting between the two Aunts. "Well I guess I will." Alex smiled a bit embarrassed. "She likes to do things to me." Alex tried to explain.

Olivia smiled. "You're right, Alex. I could teach you a lot. So, it's decided then. We'll just have to get you ready to impress my roommates."

Alex could tell from her smile, that she was again going to push his buttons, then he heard the question. This time Alex decided to play along. "Yes Alex, though you have already taught me so much ... I am certain you could teach me so much more. I guess it is decided then ... we are moving in together ... sharing a room ... and a bed." Alex smiled. "I do hope I impress your roommates ... I just hope they accept me ... for who I am." Alex then turned to the aunts' Your niece Olivia has always been so sweet to me ... she is such a sweet girl."

Olivia smiled. She was so proud that Alex was able to slip back into the role that they have created for him years ago. She watched as he interacted with her Aunts and sat back on the couch--her hand moving to Alex's back, she started to gently rub up and down his shoulders and spine.

"Yes Alex, though you have already taught me so much ... I am certain you could teach me so much more. I guess it is decided then ... we are moving in together ... sharing a room ... and a bed." Olivia giggled and shot Alex a wicked look. "Oh, my roommates are going to love having you around!" She smiled at her Aunts who were looking between the two of them with raised eyebrows.

"Well, I'll be right back. Need another drink if we're going to be so open with everyone, Alex.." Olivia smiled and winked at her Aunts. Leaving Alex, Olivia poured herself a drink and then added extra shots into a drink for Alex. Taking her time she snacked a little bit and socially polite--knowing that her Aunts would keep Alex from getting bored--before heading back with both drinks in hand. "Here, Alexandra. Have another drink. We'll probably head home within the next hour and a half, or so."

sissykaitlin said:

Olivia smiled. She was so proud that Alex was able to slip back into the role that they have created for him years ago. She watched as he interacted with her Aunts and sat back on the couch--her hand moving to Alex's back, she started to gently rub up and down his shoulders and spine.

"Yes Alex, though you have already taught me so much ... I am certain you could teach me so much more. I guess it is decided then ... we are moving in together ... sharing a room ... and a bed." Olivia giggled and shot Alex a wicked look. "Oh, my roommates are going to love having you around!" She smiled at her Aunts who were looking between the two of them with raised eyebrows.

"Well, I'll be right back. Need another drink if we're going to be so open with everyone, Alex.." Olivia smiled and winked at her Aunts. Leaving Alex, Olivia poured herself a drink and then added extra shots into a drink for Alex. Taking her time she snacked a little bit and socially polite--knowing that her Aunts would keep Alex from getting bored--before heading back with both drinks in hand. "Here, Alexandra. Have another drink. We'll probably head home within the next hour and a half, or so."

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Alex was left sitting with the Aunts, who were full of questions and comments.

"Alex you are so cute .... So you and Olivia ... are you two close .... " Soon they were touching Alex's leg "You know Alex I bet you would be cute as a blonde ... you know Alex you are too thin ... you should present yourself better ... with a bit more up top.... so are you two more than friends." Thankfully Olivia finally returned before Alex had to answer the last question.

"Here, Alexandra. Have another drink. We'll probably head home within the next hour and a half, or so."

"Um yes ... I will have another." Alex took the cocktail, tasting immediately that Olivia had not skimped on the booze.

"Olivia did you say home ... like at your college ... I have not even packed yet ... or told my parents.... I don't have anything to wear." Alex words now slurred a bit, she tried to stand and slipped back into the lap of one of the Aunts.

"I ... i mmm sorry ... I usualllly dnt drnk." Alex stumbled through the words, the drinks Olivia had made, clearly doing what Olivia had intended.

Olivia smiled at Alex. "Well, we're going to have to go shopping, aren't we? If you want to fit in with the other girls in the sorority we'll have to get you some new outfits and proper underclothing..." Olivia giggled and flashed a smile conspiratorially looking to her Aunts.

"I ... i mmm sorry ... I usualllly dnt drnk." Alex stumbled through the words, the drinks Olivia had made, clearly doing what Olivia had intended.

Olivia stood up and walked over to Alex. She put her arm through his arm and helped him out of the chair. "Come on, Alexandra, let's get you something to help you feel a little better. It looks like everything is wrapping up here, anyways."

Olivia led Alex to the bathroom and helped him to sit on the toilet so that he could catch his breath and so that the room would stop spinning. "You've got to get used to this, Alexandra. Especially if we're going to be living together. You know these girls that you're moving in with expect a lot from me and you! And you'd better live up to the expectations because it's going to be my reputation on the line."

"Come on, Alexandra, let's get you something to help you feel a little better. It looks like everything is wrapping up here, anyways."

"I feel great Alex responded to Olivia. "Is the party over?" She asked clinging to Olivia's arm to try to keep her balance. "I am sooo sorry Oliva ... I'm usually not like this."

"You've got to get used to this, Alexandra. Especially if we're going to be living together. You know these girls that you're moving in with expect a lot from me and you! And you'd better live up to the expectations because it's going to be my reputation on the line."

"Used to what Olivia ...." As Alex walked he felt the cool air upon his bare belly, the tight leggings felt devine, though each step he wobbled a bit in the tall heels. "Did I tell you how much I love dressing like this. We are moving in together .. oh thats right ... will I be one of the girls ... I better be good .... I want to impress them and you ... ecspecially you Olivia ... I like you. I will work extra hard for you ... make you proud .... do as you please .. whatever you want .... so no one knows our little secret." Alex pulled Olivia's hand to his crotch. "Out little tiny secret."

Olivia giggled. "You're such a lush, Alexandra! We're going to have so much fun." Olivia leaned forward and gently pinched Alex's butt. "Aren't we?? And the party isn't over, yet. But my Aunts wanted to have a word with us..."

Olivia had led Alex away from the main party and back towards her room. She wasn't entirely certain what her Aunts had wanted to speak to them about but figured it would be harmless enough.

"You're going to go home with me, tonight. We'll get everything else figured out tomorrow afternoon. Okay?" Olivia squeezed Alex's tiny cock and smiled to herself. "You're going to make such a good gurl, Alexandra. And the rest of the cheer house is going to love molding and shaping you into a proper team memeber..." Olivia's hands traced a little lower as they walked and she gently cupped Alex's small balls before entering the room where her aunts were waiting.

Alex was lead easily away by Olivia. Thankful to be saved from the aunt's. That was until the door closed on the room and she felt Olivia's hand side to his ass feeling his tiny balls and cock.

"You are serious aren't you, about me living work you, I thought this was just today, but you are taking me to the cheer house. Do they know,. Will they know my secret? Is there another gurl like me there."

Olivia leaned into Alex and giggled. "Ooh, honey we're going to have so much fun."

"You are serious aren't you, about me living work you, I thought this was just today, but you are taking me to the cheer house. Do they know,. Will they know my secret? Is there another gurl like me there."

"Ooh, no, Alex. You'll be the first gurl of the house and I'm going to have so much time teaching and molding you to be a proper team member. Just until you find out what they like to have young recruits do to earn their spot on the team!"

Olivia smiled and slipped her hand into Alex's. "We're going to do some shopping tomorrow so for now we're just going to head back to the house. You can share my bedroom for the time being."