Aunt Becky helped me finish getting ready. According to my Aunt Becky, I was perfect. Aunt Becky packed my purse and added a couple Tampax pearl tampons, lubricant, and some condoms
I was going to question the extra supplies, but I kept my mouth shut. I touched up my makeup and lipstick. I started to walk downstairs with my Aunt Becky. No, no, you stay up here and wait for me to call you down!
Why Auntie Rebecca?
A young man is picking you up. It's customary for the woman to make an entrance.
Yes ma'am.
It was 6:58 pm when Kevin rolled into the driveway. He drove a 2002 Camaro SS. It was all Black, even the wheels and windows. I was peeping through the window. He and Emma got out. Emma looked stunning in a white mini-dress. I was excited to see them. The doorbell rang at 6:59 pm.
Aunt Becky answered the door.
Come in, welcome. Kevin, Emma, nice to see you again. Said Becky.
Brianna!!! Becky called out.
Here goes nothing, I thought to myself. I made my way downstairs. Emma was chatting with Aunt Becky. Kevin waited at the bottom of the steps.
He looked at me and smiled. So far, so good, I thought to myself.
Kevin was handsome, he was over 6 feet tall, very muscular, and fit. He had light brown hair and brown eyes. He had a smoothly shaved face and an earring in each ear.
You must be Brianna, said Kevin, smiling with approval.
Hello! You must be Kevin! I said.
He held out his hand and I took it.
Thank you, I said demurely.
Brianna, you're beautiful, said Kevin. He softly kissed my cheek.
When I was at the bottom of the stairs, he offered his arm, and I took it. We walked into the Kitchen together.
Well! Exclaimed Aunt Becky. Aren't you two a lovely-looking couple!
Emma greeted me with a hug. She had the same dress I did, but it was white leather, and she had similar shoes too
Are you girls ready? asked Kevin
I'm starving, Brianna said.
It was nice to see you again, Kevin!
You too, ma'am!
Have her home by 1 am!
Yes ma'am.
Emma sat in the back, behind me
I love your car! I said acting girly but impressed.
Thanks, said Kevin.
Where are we eating? Brianna asked.
I was thinking Macaroni Grill, said Kevin.
Ohh! Love Italian! I said, smiling with approval.
Emma said quietly all the way to the restaurant!
Kevin asked me if I was going to high school here this year and what my interests were. It was typical first-date questions. He seemed genuinely interested in me. I wasn't sure if it was to put me at ease or if he really was interested.
I answered honestly and put a girly spin on things. As we drove, he slowly worked his hand onto my crossed legs. His hand was a little rough, but not bad. His touch was soft and inviting. He started working his way up my inner thigh, which I loved.
I stopped him at the hem of my dress. I wanted him to go further, but I figured I should exercise the control now, or I'd never have any. I didn't want this to go the way it did with Autumn. I like Kevin so far.
Because I liked him, I stopped him. I held his hand on my leg. I didn't push it off. I just didn't let him move it up any higher.
I squeezed his hand slightly, and he smiled. When Emma told me about you, I couldn't believe it. You're much prettier than your pictures.
Thanks, you're more handsome than your pictures as well. I heard you play football.
Starting Quarterback!
Wow! Emma didn't mention that.
Are you going to try out for cheerleading? Kevin asked.
I haven't really thought about it!
You should, Brianna. Cheerleaders get a lot of perks! Emma said.
Like what? I asked.
Being invited to all the parties, events, and extra pictures in the yearbook. Cheerleaders always go to every dance and social event. Tiffani and I were cheerleaders last year.
I've never cheered before!
Oh, it's easy, Brianna, Tiffani, and I can coach you before tryouts. Said Emma.
Don't take this the wrong way, Brianna, but I would love to see cheering on the sidelines.
Brianna blushed.
Kevin parked the car, like a gentleman. Emma and I each hooked an arm, and he walked us in.
Kevin asked for a booth, and Emma sat across from us. He had his hand on my leg almost the whole time. His hand went up and down my thigh. I never had to tell him to stop at the dress hem; he just did.
Kevin is charming and funny. He talked to me about school and how great it would be if I attended.
Emma was the same about it, too. We talked about the party coming up in a couple days.
Kevin said he was dying to see our uniforms.
Emma looked at me a little closer and said, You did something? What's different about you, Brianna?
You have tragus piercings! How did you manage that? My Mom told me no said Emma.
Brianna smiled. I got this, too! Brianna tilted up her nose and showed her the small septum piercing.
OMFG!!!! You lucky girl! I'm so jealous! Said Emma. How?
Aunt Becky got them for me as a surprise after my physical today!
Physical, you mean The Physical? The one where you get...
Yes, that one! My therapist approved me!
OMG, girl, that's fantastic! Emma exclaimed.
Kevin was confused. Physical, a therapist, are you alright, Brianna?
She's fine, Kevin, better than fine. Emma said, giggling.
Kevin, your mother told you all about me, right? I asked.
Yes. Kevin answered.
Everything? Including why I am here for the summer? I doubled down on my question.
Yes! She told me you're a girl trapped in a boy's body and wanted to live as a girl for the summer, said Kevin.
Yes, Kevin, that is all true. But what you don't know is that starting this afternoon, I am on hormone replacement therapy. Brianna said, smiling. Yes, I am looking forward to going to school here.
I just hope I won't have bullying issues at school this year. Said Brianna.
Brianna, if you have any problems with anyone, let me know, and I will take care of it! Kevin said Flatty.
Tiffani and I have your back, too, Brianna, said Emma.
Our school has a very strict policy on bullying. There's no bullying in our school. If you have any problems, just tell me! I'll handle it. I hate bullies and their bullshit! As the starting quarterback, I get to have a little more say in the matter. I know what to do and who to talk to. Kevin said. Besides, the football and wrestling teams will back me up!
Kevin smiled at me and squeezed my thigh with affection and assurance. I looked at him and felt very warm and safe.
We had dinner and continued to chat about the summer and everything. Kevin was really looking forward to seeing me at the party.
Kevin paid for dinner, and we left. We went to a teen night to dance. I was nervous because I had never danced before.
We got out of the car, and I walked in front of both of them, and they saw my tattoos.
OMFG!!!! Bree, what's on your back? Asked Emma.
Kevin looked at it. That's super sexy!
Ohh! Forgot to show you. When did you get those, asked Emma.
Today I said. They're temporary tattoos. I saw them, and my Aunt Becky insisted I get them. To try out.
Do you like them, Emma? Brianna asked.
I love them; I want them, too! I know Tiffani will flip!
I love them, said Kevin. They suit you very well!
Thank you! I looked at Kevin with a smile and tilted my head.
Kevin ate up the look I gave him.
Emma smiled, and she noticed the flirting that was happening between Kevin and Brianna. Emma has seen her brother with many girls. Kevin was acting a little differently around Brianna. He was a bit more sweet and affectionate towards Brianna.
Kevin was in pure gentleman mode. He brought drinks to the table. Kevin introduced Brianna to a few friends. Emma showed Brianna how to dance with her hips. When the slow music played, Kevin asked Brianna to dance.
We had fun for a couple hours. Emma wanted to make sure Brianna and Kevin had some alone time together. Emma asked if Kevin would take her home. Emma whispered to Brianna. Show him your room when he drops you off. Emma winked at Brianna
Kevin dropped her off at home and took Brianna back to Aunt Becky's.
Would you like to come in? Have a drink? Asked Brianna, she touched his hand softly.
Sure! Said Kevin.
They walked inside, and Aunt Becky wasn't home.
Brianna grabbed two bottles of water from the fridge, took Kevin's hand, and led him to her room.
Wow, this is so pink!
Aunt Becky decorated it for me.
It's you, Brianna!
Thank you! Brianna said demurely. I'm going to take this off and put something on and get comfortable. Go ahead and get comfortable, I'll be right back!
Kevin turned on the stereo and put on some Kenny G.
I touched up my makeup and made my lips look bigger. I wore my pink bra with my inserts and a pink chemise's half slip that exposed my naval and matching panties. I put on my pink mules and walked out to him.
Kevin was standing with his shirt off! He was ripped with muscles and washboard abs. He was completely hairless on his upper body. Becky was right! He's all man!
His eyes went wide, looking at me! I loved it. I sat on the bed and crossed my legs.
Sit with me, I patted the spot beside me.
Brianna could see she had control now. The confident Kevin was not nearly as aggressive as he was in the beginning.
Kevin put his hand on Brianna's thigh. Brianna moans softly; mmm, that feels very nice.
Kevin took a sip of water and started moving his hand up and down Brianna's leg. Kevin watched Brianna smile with approval.
Kevin started sliding his hand under her shorts. Brianna stopped him.
Kevin, you do know I'm not like other girls, right? I asked.
I know Bree, your secret is safe with me. I can't help myself, you're so sexy and feminine. You're more of a than any girl I know. I want you, but I swear I won't hurt you or do anything you don't want me to do.
Are you sure about this, Kevin?
Kevin French kisses Brianna. Ohh! I'm very sure, Brianna. Are you?
I smiled and French-kissed Kevin.
Kevin returned Brianna's affection. I guess that's a Yes, said Kevin.
I noted my first kiss from a real man!
We laid on the bed, kissing and feeling each other through our clothes. I noticed his huge erection. I wanted that inside me. But not tonight, I told myself.
Kevin felt up her tucked clitty and Brianna moaned. Thank gosh for the tight gaff.
Brianna didn't want to be a tease. She undid his jeans and pulled down his boxers.
His manhood sprang out it was enormous. It must have been 11"-12" long and thick. Kevin was a very big boy. Brianna noticed he had no pubic hair.
I massaged his manhood with my fingertips and nails. I licked my lips and started, very slowly Began taking care of him. Kevin was in ecstasy, moaning with pleasure.
I slowly began servicing him. I tried to take all of him, but it was too big. I started massaging him
I could feel his warmth. I was lost with my desire for him.
.
Ugh!!! Ohh! Gawd!
I enjoyed my accomplishment.
I savored his essence for a few seconds. Kevin saw it, and kissed me. As we kissed, I felt very warm between my legs.
I started to clean myself up. Kevin walked behind her and held her tightly. Brianna loved the secure feeling he gave her.
That was incredible! Your incredible. I hope we'll be seeing more of each other!
You never know big boy! Said Brianna smiling taking control of him. Brianna spun in his arms. She kissed him deeply and responded with his tongue.
Kevin was admiring my tattoos. These are so sexy Brianna.
Just wait! I'll have breasts growing soon. Said Brianna.
I can't wait. Said Kevin.
Kevin got dressed and he walked Brianna downstairs.
Brianna turned on the TV.
I have until 2 am I could wait until Becky gets home if you like? Kevin asked.
I'd really love that, I said, acting in a demure manner. I was using the tricks that Autumn used on me. It was working very well for me so far.
Kevin laid out on the couch sitting up. He patted his lap. I laid on top of him, resting my head on his chest. Gosh he's gorgeous! I thought to herself. I was petting his body.
Kevin stroked my hair softly. He lifted my Chemise and was checking out my ink. I love this ink on you. It's so sexy.
Will you go out with me next week Saturday night I could pick you up at 6 pm we could have the whole night together.
I would love that Kevin! I have to check with Aunt Becky first.
I'll make all the arrangements.
What should I wear?
Casual jeans or something similar, if the plan changes I'll let Becky know. Just be your sexy self! He leaned down and kissed me
Becky arrived home and saw Kevin's Camaro outside. She smiled at herself. Her idea worked. Now she was wondering how well and if Brianna let that young stud hit a home run.
As long as she didn't catch either one with their pants down. Becky walked in as quiet as she could. She heard the TV on.
Becky walked into the living room and Brianna was cuddling on top of Kevin. They were petting and Kissing. Becky thought it was cute. Brianna was ready for bed, but she had her panties on. Kevin had his pants on.
Good evening love birds! Becky exclaimed!
Auntie Rebecca! I'm so glad you are home! Kevin was keeping me company!
I can see that! I take it you two are getting along?
Yes ma'am! Brianna has been a gracious hostess. Said Kevin.
Kevin it's almost 2 am, you should probably get home! Said Becky.
Yes ma'am, thank you, said Kevin!
You're welcome, Kevin.
Ms Becky?
Yes Kevin!
Can I take Brianna out a week from Saturday?
Yes if you promise to have her home by 1 am young man!
Yes ma'am, of course!
Brianna, I had a wonderful evening!
Me too, Kevin, thank you for the dinner and dancing. I had a great time! Brianna tilted her head demurely at the front door. Kevin leaned down and kissed Brianna good night.
Becky watched from around the corner as they kissed. Bree's left leg went straight up. Brianna watched Kevin get in his car and drove away.
Brianna was wearing a look of satisfaction until she saw Aunt Becky standing there.
Brianna's face turned to shock!
So tell me, how was your date?
He was wonderful!
And? Asked Becky
And what, Auntie?
Brianna! There are no secrets about you between you and me!
So tell me, girl! I want details.
He was a perfect gentleman, Auntie.
He opened doors, paid for dinner, and took us dancing.
Emma was tired so he dropped her off and he brought me home.
And?
Did you? Asked Becky
Brianna blushed, she was embarrassed but also very proud.
You Did it! Didn't you? You gave him your first oral service!
Yes, Auntie Rebecca, I did it. It was really big and beautiful and I did. He was so sweet to me. I never knew boys could be so nice.
Did you do anything else?
No ma'am! I wanted too! But I didn't think it would be a good idea.
Good girl! If you give a boy what he wants on the first date he'll never call you again. You should wait at least 3 dates before you offer yourself to a boy. Said Becky.
Auntie, can we make love? Brianna asked with a demure look and smile.
Of course sweetheart. You poor thing, you! You've been pent up all day haven't you?
Yes, Auntie Rebecca, I really need to climax..
Give me 15 minutes, then knock on my bedroom door, and don't forget to kneel!
Yes Mistress!
Very good Brianna.
Brianna touched up her makeup and when she got to Aunt Becky's bedroom there was box and note. Brianna opened the note.
The note said put this on before knocking. In the box was a very small pink latex bikini with a g-string bottom and matching 7-inch stiletto heel shoes, a collar.
Brianna, was full of questions, but decided to submit to Becky's wishes. Brianna really loves the outfit and was thinking maybe Kevin would like it!
Brianna put on the contents of the box and kneeled then knocked. Brianna was half excited and half scared. This was not what she had in mind at all. Brianna couldn't stop herself. She knew Aunt Becky only wanted the best for her.
Becky opened the door and smiled at her femboy niece kneeling. Brianna has been obedient from the moment she arrived. Becky was proud of her.
Becky closed the door, walked to the bed and pointed at her feet. Brianna crawled over to her. Brianna never said a word. Becky was extremely proud of her obedience.
Brianna began worshipping Becky. Brianna appreciates everything Becky has done for her. Brianna thinks this is the least I can do.
Brianna worked gently, while listening to the occasional instruction and Aunt Becky's moaning. Brianna loves the sound Aunt Becky makes as she services her.
Brianna loves making Aunt Becky happy. Brianna takes pride in her every orgasm. After 3 orgasms Becky decides it's time to make love her young adopted femboy niece.
Brianna sees the toys and immediately assumes the position on the wedge pillow. Brianna awaits anxiously. Brianna never dreamed sex could be so much fun and adventurous.
Brianna moans are soft and feminine. Becky has always loved Brian. He was always a sweet boy. Now Brianna is in transition and Becky has made herself Brianna's Mistress.
Becky begins to relax Brianna.. Becky thought it was so adorable how feminine in nature her adopted niece was acting. Becky realized, to Brianna this wasn't role-play, this was making love to her and she is the girl. Becky continued to play with Brianna, making her climax twice. Becky watched her niece as facial expressions and moaning began. Becky was pleased with Brianna and her willingness to offer herself and her freewill to Becky.
There was some discomfort, but she relaxed and took deep breaths allowing her body to accept the toy. Brianna was really loving the feeling of receiving. Brianna closed her eyes and imagined it was Kevin. Brianna rocked her hips as Becky moved in and out. Brianna felt a new internal sensation. Brianna was lost in pure pleasure.
Becky counted at least three orgasms for herself and another two for her sweet adopted niece. Becky always wanted a live-in lover. Becky wasn't sure it would be right to make Brianna that kind of lover.
Becky also knew sissies attract other sissies and Brianna might be the key to her having the partner she desires. Recruiting a sissy, especially the right kind of sissy is a near impossible task.
Becky decided it was time to put Precious to work.
It was after 3 am when Brianna fell asleep with Becky.
In the morning Brianna woke up first. Becky was lying on her back. Brianna began worshipping Becky. Brianna felt obligated to thank Becky for everything.
Becky purring, ohhh!!! Brianna darling that was magnificent.
I love pleasing you Auntie Rebecca. I love being here. I am so happy to be here.
I don't think I've ever seen you smile so much Brianna.
Is this what it is like to be a girl Auntie?
Becky pats the bed beside her. Come here honey.
Brianna cuddled beside Becky. Becky embraced her adopted femboy niece.
For the most part, yes Brianna. Some girls your age and in college experiment with both boys and girls. I experimented a lot in college and after.
When you arrived I could tell immediately you had zero sexual experiences. I decided you should experience all of them. I could tell from the start you had the heart of a girl.
Never having sex I thought it would be best if I was your first. Your first time with a woman should be very special. I was very honored to be your first. It was a test of sorts. You passed with flying colors too!
A test? I, I don't understand Auntie!
It's very simple really, Brianna. Most boys become more macho and confident after having sex with a woman. You became a more considerate and affectionate person. You are more confident but more feminine as well.
I must say you are a wonderful lover. You're submissive, obedient, loving, and very attentive to your lovers needs and wants. You are going to be a great lover sweetheart. I am so proud of you.
Becky kissed Brianna deeply.
Come on! It's almost noon and we have your therapy appointment at 2:30 pm. You need a bath and we need to disinfect your piercings darling.
Becky ran a warm water only bath for Brianna as Brianna prepared her enemas. They used Becky's Jacuzzi tub because it was bigger so they could bathe together.
Brianna finished her enemas and joined Becky in the Jacuzzi. They bathed each other with affection and showered together.
Becky disinfected her new piercings. While treating her piercings Becky started planning more body jewelry for her young charge. Brianna didn't know it yet but Becky has big plans for her body!
Becky picked out a pink skaters dress and white sleeveless blouse, Becky laid out her pink thong gaff and her pink bra. Brianna smiled at the outfit. Brianna realized the blouse was semi sheer in front with two breasts pockets covering her breast area. The back of the blouse was almost see through. Brianna realized her tattoos were on full display.
Becky handed her 4-inch wedge sandals. Becky could see the concern in Brianna's face.
Auntie, isn't this too much for a doctor visit?
Nonsense my beautiful niece! You're a girl now! You want the therapist to look at you and see the girl you want to be, right?
Yes I do! I just figured I'd be dressed a bit more conservative, that's all.
Have I ever steered you wrong?
No ma'am!
This is what you want, yes? Asked Becky
Yes with every fiber of my being yes! Said Brianna.
Brianna, this summer is supposed to be an adventure, your adventure to find your true self. I know you said you would do anything I asked you to. But it also has to be what you want to do!
We are team Brianna! If you want to become a girl Brianna, I will do everything in my power to make it happen. If you decide along the way to be a boy, I will love you just the same. Everything I do for you, to you, and with you is to give you a 360 degree vision of experience so you can make an informed decision.
Does that include our role-play? Asked Brianna
Of course it does sweetheart. I very well can't have you out there having sex by yourself without knowing what to expect. Sex with men is a 50/50 toss of a coin when it comes to partners. Women are more stable but there's always the coin flip with good and bad too.
I guess I've got a lot to learn, said Brianna.
Yes you do, but you're catching up very fast young lady. Just make sure to go slow especially with new people. Not everyone is as enlightened as my friends and I are. Our way isn't conventional by normal society standards, but it's better and makes for a trusted, happier and better relationship.
Aunt Becky wore a tan tank dress that hugged every voluptuous curve and tan 6-inch hidden platform heels. She looked beautiful and powerful. Brianna admired how she walked, it was like gliding across a room. Aunt Becky was pure grace in her movements.
We got to the therapist's office almost an hour early. It's a good thing we were early, Brianna thought.
The receptionist gave Brianna a 12-page questionnaire about gender transition. Brianna filled it out as honestly as she could. Brianna felt drained after filling out all those deeply probing questions. Many of the questions Brianna never thought of.
.
Brianna had just finished when the Therapist called her in. Becky stood up and the Doctor said just Brianna please. Both Brianna and Aunt Becky looked disappointed. The therapist looked at Brianna and said it's all right Brianna, you're going to be alright! With that Brianna stepped through the door.
Brianna's first appointment was almost 2 hours long.
Brianna was asked about everything, childhood, how old was she when she felt different from other boys her age. She asked about getting along with both boys and girls.
She asked about her long hair and her piercings and tattoos. She wanted to know how she felt dressed as a girl. She asked if she was sexually aroused dressing as a girl.
Brianna was scared at first but once she started talking the weight of everything on her narrow shoulders fell off and she felt relaxed.
Brianna didn't realize it at the time but her feminine characteristics started flowing from her. Brianna was talking with her hands. Brianna had a squeak and musical tone in her voice.
Brianna went in the session scared and nervous. Brianna at one point broke down and cried for at least 15 minutes. By the end Brianna was in full girly mode
The therapist Dr Maria Hayes called in Aunt Becky.
Ms Strong, May I have a few minutes. Asked Maria
Of course, please call me Becky.
Brianna waited outside in reception, the ten minutes Brianna waited was difficult for her to say the least. Only on her second day on HRT and Brianna could swear she was already feeling it.
The two tiny pills and almost horse sized anti-androgen pills twice a day. She's only had two shots and three pills and she swears it is already working.
Waiting was killing Brianna. It was almost 20 minutes when Aunt Becky walked out with a folder and several brochures. Aunt Becky was smiling as she walked towards Brianna.
Well, Aunt Becky?
Let's talk in the car Brianna.
Brianna began to worry again, she could feel her anxiety and emotions shifting.
Becky waited until they were in the car.
Well! Brianna asked a bit worried.
Brianna, sweetheart! Calm down, everything is fine. Said Becky.
Maria and I were discussing your visit.
But isn't that private? Asked Brianna.
Not from me sweetie, not until you are finished with therapy.
Maria thinks you're a good candidate for transition therapy. She signed off on the visit to the endocrinologist for next week. You my darling niece are on your way to becoming a girl.
Brianna smiled, thank you Auntie!
Just then Becky's phone rang.
Hi Alison!
Yes we can stop by. See you very soon thanks.
Brianna recognized the adult store as Becky drove in the parking lot.
Annah Rourke
2025-05-28 22:41:00 +0000 UTCAmanda
2025-05-28 12:57:43 +0000 UTC