There’s the voice at the other end of the phone, “Sam, will it be okay? I would like to know one way or the other.”

“Mr. Kincaid, it sounds silly, but I’ll do it if you’re sure it will be okay.”

Mr. Kincaid laughs at the other end of the phone; “We’re not worried; I just hope Jennifer doesn’t get carried away with makeup when you’re here. She hopes you can be here and have the pool ready for the day by 9:00 a.m.” Then Mac ended the call quickly after that.

“Mom, are you serious that it’s okay about me doing this?” Sam asked.

She said, “Are you ready to tell me about getting into your sister’s clothes again? That includes her delicates.”

“Mom, I didn’t do that.”

She said, “Then enjoy helping Jennifer this weekend. She said something about showing you how wear makeup. Why would you need to wear makeup over at their place?”

Sam, “I hope she doesn’t plan on our going out.”

Sam was ready to go to the Kincaid’s, and he wasn’t taking any of his sister’s clothes. His mother said, “I changed the clothes you had in your small suitcase. What you have should last you the weekend. Now get going.”

Mac was there as I entered the house at 8:10. “Thanks for coming early; it will give you time to change and start on the pool. Please let Jennifer help you with a little makeup. That way, if someone stops by, they won’t recognize you.” Mac showed Sam to a spare bedroom, “It’s a little girly because her nieces sometimes stay here.”

Saying goodbye to me, he patted me on the shoulder. “Take care and have a good time, Samantha.”

I was left to change as he went to say goodbye to Jennifer and Sheri. He told Jennifer, “I called him ‘Samantha’ as you suggested. You take care and be nice to the sweet boy.” He kissed Jennifer and held Sheri and gave her a big hug. “You be good, Sheri, and Daddy will have something for you when I get home.”

Sam had found that his mom had put a pink wrap-around denim skirt along with two tops that kind of complemented the skirt as an outfit. There was a pale yellow bra and panties set, and two others that he saw. There was a red mini-skirt with a floral print. Its tops were an off-white cashmere sweater and a white blouse with wavy lines like a rainbow of sorts. Sami chose the pink wrap-around denim skirt paired with yellow panties and a bra. When he put on the first top, he found out it was a see-through blouse. He was ready to take it off when Jennifer and Sheri appeared. Jenn quickly said, “Don’t”. And with that, the bra hugged my skin.

Jennifer said, “Doesn’t that look pretty on you?” She asked, “Do you need help with the gaff that you wear under your panties?”

I hadn’t felt anything, so I said, “No.” Jennifer walked over to me and handed Sheri to me. She whispered in my ear, “Are you excited to see me? That is one reason for the gaff.”

“Relax,” she told me, “The gaff comes with a pad, you will be safe.”

Jennifer asked if I had breakfast, which I had. “Then would you go out to the pool and make sure the skimmer’s working and that the water tests are good.”

I had checked the pool and tested the water. I was using the net to pick out a few leaves and a pool toy that had blown into the water.

When I was done, I saw Jennifer and little Sheri coming to the pool wearing two-piece swimsuits. Jenn said, “I bought a powder blue suit for you. It is in the bathhouse, please go and change into it.”

I stuttered trying to say, “No.”

She asked, “Do you want to do it on your own or with my help?” She twirled her finger. and I knew to turn around, go inside the bathhouse, and put on the swimsuit myself.

I was surprised when I took off my top and bra that there were breast forms that stayed on me. There were two pieces of clothing with tags that indicated they were swimsuits. It was a girl’s two-piece suit. The gaff once on properly stayed in place and was not visible, nor were any of my boy parts.

Jennifer called for me as I came out, “There are three terrycloth wraps, one for each of us. Please bring them with you.”

Jennifer said, “Samantha, please walk with Sheri and me in the shallow end,” which I did. She asked, “How does it feel to be in the water?” I was up to my waist as she handed me Sheri. “Sheri likes it when you dip into the water and come up with her.”

Samantha said, “The swimsuit is skimpy, and I’m not used to the water running down my body through a swimsuit.” Sheri is kicking and splashing; “I’m not sure she likes this.”

Jennifer giggles, “I thought you’d like the feeling of being like a girl? …The swimsuit material is light, but it will stay on you. And as I said, Sheri seems to enjoy you holding her. It is your chance to learn what she likes.”

Jennifer’s tone changes, “Your mother said you could go home at noon, and be all done with dressing as Samantha.”

“Though your Mother gave me a hundred dollars for you to spend on two outfits, plus the use of her credit card for whatever else we decide you need. That doesn’t sound like she wants you to go home.”

I said, “No, it doesn’t.” I realized my voice was changing to sound more girl-like and that I’m liking being Samantha.

I stepped out to where the water was about four feet deep. I spun around and watched Sheri giggle and enjoy herself. Sheri splashed in our faces and slapped her wet hands all over my face. She giggled when I made faces. Finally, she splashed too much water in her face and coughed up some water. She was ready to cry. I used my hand to wipe Sheri’s face and gently tell her, “You are okay, Sheri.”

I walked out of the pool to a fluffy dry towel, saying, “There, there, you are alright.”

Jenn spoke up, “You did right well; she’s bonding with you. You are a natural babysitter.” Jenn put sunblock on her daughter and placed her in a playpen in the shade. She took some sunblock for herself and gave some to me. Jennifer had spread it on her front, arms, and legs. She then helped me do the same. Finally, she said, “Now lie down and I’ll do your back.” When I was on my stomach, Jennifer undid the strap of my top and then put on the unblock. Jennifer was on her back as we lay in the sun.

Ten minutes later, Jenn sat up. “Sami, I fixed your straps.” She checked on Sheri, who was asleep in the shade. Jennifer unhooked her straps, and after she lay down, she asked me, as Samantha, to spread the sunblock on her back. When I thought I was finished, Jennifer said, “You have to go a little under my suit bottom, so I don’t burn if the panty shifts.”

Sami moaned, Jenn said, “I don’t want to hear it. I was nice to you.” Sami did as instruct and her hands shook as they were under the material and between Jenn’s legs. Jenn said, “Thank you, it is better if you just do it and don’t make a fuss.”

When we had done that twice, Sami and Jenn finally got up, dove into the pool, and swam until Sheri stirred. “Pat yourself dry and let’s take Sheri inside for lunch.”

Jennifer made two salads with tofu, romaine lettuce, cherry tomatoes, fresh spinach, grated cheese curds, and a vinegar and oil dressing. Sami didn’t know about the tofu, but she ate and enjoyed their lunch together. Jennifer nursed Sheri, and when Sami turned away, Jenn chided her to turn back. “You think you’d like to be a girl; this is one of the most beautiful parts. Please don’t turn from us, even if it embarrasses you a little.”

Sami, with a soft voice, said, “Thank you.” A short time later, he said, “It’s beautiful to see.”

Sami was to check and change Sheri’s diaper, which was more than just wet. Jenn asked Sami, “Do you know how to properly change a baby when messed like that?” When Sami indicated she wasn’t sure, Jenn instructed her, “Wipe her bottom clean and wipe away from her front. You don’t want her to get a urinary infection.” She watched closely, and I was proud when she told me I had done well.

Jennifer told, “Samantha, if you ever have sex with a girl, make sure you are clean and use a lubricant for your fingers and your penis.”

Sami started to say, “I’ll never.”

“Don’t say never; I hope one day you will.”

Jennifer said, “I have a cute outfit out for Sheri; after you change into something nice, I want you to dress Sheri. We are taking you shopping.”

“I can’t go out in public?” said Sami.

“You can’t get two outfits and your first bra fitting by staying here. Now get going,” Jennifer went to her room, expecting Samantha to change without arguing.

Sami chose the miniskirt and put on the cream-white cashmere sweater. With two small breasts poking out under the sweater. She put on the nude-colored pantyhose and then the skirt. There was nothing boyish about Sami. She checked Sheri’s diaper. Sami dressed Sheri in a pretty sundress with bunnies and kittens. Waiting for Jenn, she brushed Sheri’s hair and used a white daisy hair clip to brush back Sheri’s hair.

Jenn had entered the room, “That is quite nice, Sami. I told you, you have a natural way with Sheri.”

Jennifer said, “Here is your purse with your money, credit card, and identity in it.”
Sami said, “I’m too nervous to do this.”

Jenn asked, “Do you trust me when I say, I won’t let anything bad to happen to you?”

Sami paused, “You are really asking me to trust you, aren’t you?”

Jennifer said, “You would like to buy two outfits, maybe a nice dress, don’t you?”

Without thinking, Sami said, “Yes,”

“I don’t want you to grow up scared, do you?” Sami once again agreed, “No!”

“And you’ve dreamed about a day like today, haven’t you?”

Without thinking, Sami answered, “Oh, yes!” I meant to say, no.”

We walked out to the car, and Sami put Sheri properly into her car seat. Jennifer asked for Sami’s hands, palms up. Jennifer used a wand to touch Samantha’s wrists with a light scented perfume. Sami rubbed her wrists together and touched her wrists to her neck, “Well done, young lady. You know what you’re doing. Where did you learn that?” Sami felt embarrassed and sat quietly; we were on our way.

We went to Oakridge Mall, which was a distance away. We had Sheri’s stroller out when we walked into the mall. Jenn saw that Sami was getting nervous and asked. “You’re happy and excited, right?”

Sami looked up and smiled, “I’ve waited five years for this. Thank you.”

We walked into Victoria's Secret, and Jenn suggested Sami take her time and look around. We had been there a few minutes, which would have been an eternity for Sam. Sami finally spoke to a saleswoman close by, “Can you help me?”

Amy was more than happy and asked, “What do you want?”

“I’m looking for a bra and panty set or two. It will be my first bra.”

Amy smiled, “So let’s make this special.”

Sami and Amy looked at different bras and took one from each. Amy took Sami back to a private changing area. And Sami asked, “Can I have my friend come in with me?” Jennifer and Sheri were invited in.

Sami was asked to take off her sweater, and Amy took several measurements. Amy said, “You have a thirty-two-inch chest and should be wearing a B-size cup.”

Amy suggested out of the bras, that Sami choose something for everyday and a nicer bra for special occasions.

Amy asked her, “Please try this pretty bra for everyday wear? And if you would allow me, I would like to suggest what I think would be a lovely bra for you on special occasions?” As Sami was changing into the first bra, Amy had gone back out to the sales floor. She came back with a pastel pink satin bra. “This one is a few dollars more, but it looks lovely and wears better than the others.”

We had been in there for forty minutes. Trying on the bras with my sweater. I tried on each of the bras, but I always came back to the pink bra as my favorite. “I can’t believe I’m buying my first bra.”

Sami thanked Amy, “Amy, it might only be two sales to you, but I am appreciative of your help.”

Amy said, “Your appreciation means more than you think.” She gives Sami a card that says, “Please take an extra 15% off Sami’s next purchase.” It was signed “Amy Carson, Assoc. Mgr.”

Jennifer whispered, “Your mother will need to buy a better breast form for you to wear these bras properly.” Sami was wearing the better of the two bras.

Jennifer, Sheri, and Sami shopped for another half-hour without buying anything before lunch. Jennifer took Sheri into a personal care restroom for Moms and Babies. She nursed and changed Sheri. Sami wanted to help, but Jennifer said she loved some personal time alone with Sheri.

We ate at Bennigan’s inside the mall. A waitress asked if Sami was a niece or a cousin. Jennifer said, “A neighbor girl who helps me.”

Jennifer ordered two crab cakes, one for each of them, but Sami spoke up, “Don’t waste your money, I won’t eat a crab cake.”

Jennifer asked if Sami had tried crab cakes before, and then asked, “Sami, I ask you to give them a try. Another lunch will be ordered if you don’t like it.

Sami did not need to order a second lunch. Sami was learning to trust Jennifer, who was becoming her heroine. “My Mom won’t believe what I am eating or wearing!”

It was later in the afternoon, with packages in tow, when Sami bumped into another girl. When the high school girl turned around, Sami recognized Barb Sterling and said, “Sorry, Barb.” Barb started to ask who she was, before she recognized “Sam!”

Sami shyly said, “It’s Samantha when I’m dressed like this.”

Sami wanted to run and hide, but knew that would make it worse. She didn’t make excuses: “This is Jennifer Kincaid; she’s helping me to embrace myself.”

Barb asked, “We’re far from home; don’t worry, this is our secret?”

Jennifer spoke, “I brought her out this far, hoping we wouldn’t be seen; I’d appreciate if you helped keep our secret until she’s ready to come out?”

Barb complimented, “Samantha, is it? I’ll be honored to be quiet, but I’d hope you will stop by so we can talk and be friends. I think you are a beautiful person. I have a stash of makeup I’d like to give you, if you want some of it.”

Samantha was taken aback, having met Barb there. She got angry at Jennifer, “Just because you look hot and people like you, this ain’t me.”

Jennifer snapped back, “You’re the one who called me ‘a hot mama’ behind my back. I am a mom, and I work to be a good friend. Yes, I’m pushing you a little because you needed to come out of your shell. You can’t live in fear.” Jennifer hugged Samantha as she apologized for what she said. “I take pride in being Sheri’s mom and the son or daughter in me now. I’ve taken pride in you helping to take care of her. I’d love you to help me more this summer, but not if you’re unsure of my intentions.”

Tears come to Samantha’s eyes, “You’re going to have another baby, yet care enough to help me. I’m a selfish boy, but you’re taking the time to warm my heart.” Sami goes to a knee, hugging Jennifer around her waist, “Please help my heart to become my eyes.”

Jennifer’s hands settle on Sami’s head as though she’s blessing her. “I hope this is a sincere step you are taking?”

Barb’s still there, wondering a little about what she stepped into.

To be continued…