We drove the back way into the conservation park using our parking lights to find an area to ourselves. That meant we were twenty-five feet from the next car. There was even a small tree with low branches between us and the next car that helped.

I’m not experienced, but between what Haley told me and Sarai helping me, Caryn, I was going to learn. We got into the back seat and helped each other lose our dresses. Sarai even took off her bra.

She asked, “Do you mind if it is Caryn and me at first?” I was fairly sure that meant for tonight. This being further than I would have hoped, it was fine by me. We kissed and hugged. “Caryn, if you don’t mind, I’m going to guide your hand. I hope you are open to touching my breasts and then some.”

With the first touch of her pillow-soft tissue, I responded, “You feel even more wonderful than before. Doing as my mother insisted I’m wearing a gaff and it is not simple to get off and on,”

We both giggled, and she asked how I used the women’s room. I didn’t explain much more than that I managed. She asked, “Is it alright then if we just act like two girls in love?”

“I don’t know how much more of a girl I can be, but I’m open to trying,” I said to her.

She guided my fingers around her nipple and said it was her ‘areola’. I remembered learning it in biology and health, but this time it registered. Nor did it seem funny like before, now it was beautiful. When I felt little bumps rise, I sensed she was more excited. Without thinking or asking I kissed her nipple. It wasn’t quite as soft as before, but I was pleasing her.

We did more, but all I’m comfortable saying was I blossomed and learned.

Once we were put back together, I wanted to fully redo my makeup. Sarai helped me to do what she said was more than enough. “Our mothers will know we were making out some; just assure her you were safe and didn’t go too far. I don’t think she’ll ask more.”

We threw our panties in the trash. Scott two cars over said loud enough for me to hear him. “Way to go, Caryn, some first date.”

It was 12:30 when we met up with Katie and Josh. We talked outside the cars for a while. It became a small crowd with Ashley, Jon, and their dates. I didn’t act embarrassed nor shy.

It was just after one when Katie suggested I take Sarai home, and her date would take her home.

Two cars drove by as I walked Sarai to her door and we kissed. Sarai asked, “Are you happy with having lost our bet and having this time as Caryn?”

“It’s the best thing to happen to me, I’ve loved being Caryn, and once I’m cleared to run I’ll continue wearing my running skirt for the season. I hope you won’t mind if inside I’m still Caryn some of the time?” I said. Sarai gave me one more hug and kiss before she slipped through the door.

I took a slightly longer way home. I looked at myself in the mirror and then took a selfie before going into the house.

Once through the door and to the stairs, my mom spoke up. “Why don’t you take a quick shower after Katie gets out. Then if you are up to a short visit come down in your sleepwear. I set something nice out on your bed.”

Katie was out of the shower, by the time I was undressed and had my dress hung up properly. I knew it wasn’t as special as a prom dress but it would be the best I’d get to wear. I was very pleased.

I sang as Caryn as I was showering. I had seen that mom bought me a nice lavender satin negligee to wear. It was modest and permitted me to wear Katie’s light nylon robe.

Dad had gone to bed, which enabled Mom, Katie, and I to visit as three women. Thankfully, no details were mentioned, but Mom was happy for Katie in her senior year. Mom alluded to me becoming a young woman and hoped as Gary I was alright with that. “I think it was a special night for Caryn and Gary, one you’ll never forget.”

Katie gave me a hug, whispering, “But you should be discrete and not just share with anyone. Did you have a good time?”

It was Caryn’s voice but both Gary and Caryn answering. “You both helped it to be a night to remember. I’ll return to being Gary, but it won’t be an easy thing. The nice thing is being Caryn broke all the emotions and fears that were holding me back.”

My phone buzzed and there was a message from Sarai, “Please know, I look forward to being with you Gary.”

My smile was all the explanation I needed for Mom and Katie.

It was seven-thirty in the morning when my phone buzzed again. I answered and it was Sarai. “Are you going to church with us; I’m going with Katie to your church I’ll be wearing Friday’s dress. You can come as Caryn or Gary, but I hope you’ll come.”

I started to moan as Gary and Katie knocked on my door, “Get up and get dressed. I hope you'll dress as Caryn; it was her weekend.”

I put on a robe and made my way downstairs. I was hungry and wanted to make sure things were okay with my parents. Breakfast was simple, danish, rolls, coffee, and juice. Dad spoke first and Mom confirmed whatever I did this morning was okay. I was told that we were meeting the Duvalls for Sunday dinner out.

We went to the ten o’clock service which gave us plenty of time. I dressed as Caryn in my lace dress but kept my makeup simple. I found a pair of two and a half-inch heels of Katie's that I fitted into. With the extra time, Katie helped me to change my nails over to a soft rose red.

Mom knowing I had a doctor’s appointment with Michele Watts, said I could keep them through the doctor’s appointment and during school on Monday. But there was a ‘but.’ You do need to return home and go to school as Gary.

Going to church with Sarai was fun. Not everyone was pleased to see Caryn but I did not overreact and let things quietly be. Being in a town and church where I grew up, most of the comments I received were supportive.

Dinner out was kind of anti-climactic as the three of us, Katie, Sarai, and I had trouble staying awake and eating properly. The Duvalls and our parents were the ones who reminisced three weeks and my blossoming.

Once we got home modesty became hard, as I barely hung up my dress. Mom helped me to take off my little makeup and cleanse my face. I dropped into bed at three and didn’t wake up until seven that evening.

Sometimes while I was sleeping much of Gary’s clothes were returned. Only half of Caryn’s clothes disappeared to the guest room. The coral pink dress had to go to the cleaners. A few panties, bras, and camisoles stayed in the bottom of my dresser, along with stockings, and girls’ socks. Several skirts and blouses remained in my closet along with the return of Gary’s slacks, shirts, and denim jeans.

I did go to the school track and jogged five laps. Each lap I picked up a little more speed as I stretched my stride. It was no way near what I needed to run cross-country, but it was a good start. I felt soreness where I had been bruised, but nothing hurt.

I thought I was alone until I came off the track. Sarai and Katie were there. “Look who has grown up,” said Katie. “I was sure we were going to have to stop you from running too fast and too long.”

Sarai hugged me, “Gary, you have most of the week to see if Saturday’s meet is possible. I know you will be a force to be reckoned with next year.”

I said, “I might be fooling myself but I hope to be full-stride come districts and state.”

Katie asked, “Doesn’t conference come first?”

I replied, “If possible, I’ll run fast enough to move on to districts.”

It was nine-thirty when we shut-off the track lights and went home.

Monday morning, I put on my gray mock suede skirt and pink blouse. Mom took her last picture of me as Caryn. It was time to leave for the doctor’s but Katie didn’t pick up her purse to go with me. There was a beep or a horn and I looked out to see Sarai ready to give me a ride. Mom rode along but let me sit in the front seat. When we got there, Mom let me know she had shorts or a swimsuit if I was to use the whirlpool.

When I went to be examined, I needed to take off my stockings. But Michele gave me the choice of putting on their paper exam outfit or just sit in my skirt and blouse. “You have healed faster than one might expect. Part of that is due to you being in shape. What I didn’t take into account was you taking it easy as I told you.”

While she examined me, she asked about homecoming and if I had pictures. I only had two, one from the Duvalls and another from the dance. Dr. Michele was pleased with both.

She said, “I can release you to begin running again, but I’d strongly suggest you don’t run tomorrow or run full speed before the weekend if then. If you begin to hurt, pull back some you’re just to be stretching those muscles.”

“If it is okay with you, I’d like to have your mother in here to talk about your blood work and testicles.”

I agreed but requested knowing some information before we called my mom back.

“Gary, you need to know I am not an expert in this, but your testosterone is just under fifty percent of normal for a boy your age.”

I took a deep breath and said, “You might as well call my Mom in; you can tell us both what this means. And if I’m in trouble.”

Michele said a muffled, “No, not trouble.” She went to get my mother.

Michele came back smiling, “I met your girlfriend Sarai. She is a very attractive girl.”

“Mrs. Miller, as I had begun telling Car… Gary; I’ve received his blood work back. I did that in part because his testes had not fully dropped and his skin tone is more delicate than most boys his age.” She paused for that to register for us both. Gary’s testosterone level is just about half that of the average boy his age. Boys also have estrogen in their blood and while he is slightly high in its range that is not alarming… I don’t think any of this is due to tight underwear he may have been wearing the past few weeks. Gary, I encourage you to be checked by a specialist and consider what if anything you might want to do. It could yet correct itself on its own.”

I waited until Dr. Watts finished speaking before I asked my question, “I was just thinking and my Mom will be as surprised as any. I’m not planning on it.” I stammered as I wasn’t sure if I wanted to say anything. “What if, what if I’d rather be Caryn?” I was trembling a little as I finished asking. I reached out my hand to my mom hoping she’d grasp it. I was afraid she wouldn’t. I hadn’t had time to think. I probably shouldn’t have said anything.

“I can’t even remember if that would make me a transgender boy or girl. I’m sorry I shouldn’t have said anything.”

My Mom was also speaking, “It’s my fault, I should have known it would be dangerous for you to pretend like that. What did I do? I’m sorry Gary.” We shot out more thoughts and questions. Dr. Michele calmly said as she allowed us to ramble on, “It's neither of your faults, don’t worry all those thoughts are normal from what I understand.”

Mom had grasped my hand and we were hugging as we turned to Dr. Michele. Ms. Lea came to see if there was a problem. Dr. Michele told her, “Just some growing pains that need time.” Ms. Lea waited to see if she should leave or not.

“It will be okay Ms. Lea, thanks for checking. If you can, stay a moment in case one needs your support while I help the other.”

“Mrs. Miller and Gary, I’m glad you felt safe to share your concerns, but there is no blame needed. Gary, if I’m correct this didn’t start just three weeks ago. You’ve wondered about things and have been proving your masculinity for some time, am I right? And I don’t think you are quite ready to give up being Gary.”

“Mrs. Miller, I think everyone thought Gary was shy and withdrawn, but he was wrestling with this deep down inside. I think part of you knew that and gave Gary the room to discover himself with his committing to his bet Sarai. What the two of you did was quite healthy. I think Dr. Gamble knew Gary’s testicles had a problem, but no one saw all of this emerging at this time.”

She saw us looking at the clock, “I gave myself extra time to be with you once I saw the blood test results. It is a concern, but nothing to be alarmed about. Everyone needs to take this step by step and not rush to conclusions. Even if Gary would be transgender, the past three weeks seems to prove he/she can handle it.”

“My immediate advice is to take the time to continue to experience life as Gary in his regular routines. You might want to seek out a counselor who is experienced in these matters. Do you know if there might be opportunities for Gary to be Caryn again?”

Mom and I begin to speak at the same time. I stop and indicate for her to go first. Mom said, “His Cousin Megan is stopping by overnight on Thursday. She is getting married next summer and she’s actually entertaining the notion of asking Caryn to be a bridesmaid. Gary’s sister Katie is, and after another one of Megan’s bridesmaids became pregnant Megan thought it would be cute to have Caryn.”

I asked, “Is it possible for you to be my regular doctor?”

Michele’s eyes became brighter, “Yes, it is if you’re serious. Only two-thirds of my time is in sports medicine. You could even come to the clinic as Gary if you so wish.” She continued, “Would it be okay to see you a week after your first meet, or sooner if you have a problem?”

I didn’t tell anyone, but I felt good that Caryn would continue to be.

I went home and changed for school. I changed my hair to Gary’s ponytail but had to live with my painted nails until after school. My blend of being Gary and Caryn did raise a few eyebrows. The Principal spoke once to me between classes and she was fine with how I came to school today. “You know that you’re causing us to think outside of any preset molds. It should be good for us in the long run. Keep me informed if you or others run into problems.”

Mom went to work after we got home and Sarai gave me a ride to school.

“Gary, you are looking good,” I was surprised to hear Sarai calling me Gary. “I do miss seeing your good looking legs.” Several around us laughed.

Jon complained, “You’re still too much girl for me. I’ve had it for now.” Jon slapped hands with Marc Davies a long-time nemesis of mine and they walked off. Jon was a geek and loner; I didn’t give any friendship with Marc long. It was more about his anger with me.

Ashley asked, “Whenever did they become friends?”

During study time, I received permission to visit with Coach Higgins. He was happy to hear that I was approved to begin running again. He agreed that I shouldn’t be running in tomorrow’s meet, and wonder out-loud if Saturday might be too soon.

He did approve that I could begin light running after school. “Why don’t you jog around the track and see how far you can run; I’ll probably have you stop early.”

Once I got to the track I found out I only had my shorts with the running skirt. Matt said, “What did you expect? You’ve been running great, we want you to keep the spirit of what you’re doing. You have two weeks before districts and state. I want you pushing me by then.” Matt spoke to the other guys on the team. It was the first time I knew of him verbally acting like the captain of the team.

I felt good in the shorts with the skirt flapping against my legs. With my fingernails still painted, I felt more like one of the girls as I ran around the track. It was only a glorified trot but Matt said, “That’s at least six laps. I want you to walk around and cool down. That was impressive for the first day back.”

I did at the Coach’s request go in early and ride a stationary bike and then used the whirlpool. Once back out, and changed and I waited for the others. Sarai was possibly even more joyful than I was that I was not feeling sore. “I can’t believe you did that much running and aren’t sore. Please wait and I’ll give you a ride home.”

Once again, I was reminded that girls take longer to change than guys. The only exception being many girls won’t change at the field house. Sarai came out in flip-flops and used the remote on the car to have it started and warming up. I asked, “Since when did your car become able to do that?”

She confided in me, “This is not for others to know, but Rachel had a scary encounter at college. And only because another person came by she wasn’t badly hurt. My folks updated both of our cars with these features. With you acting as Caryn, it might not be a bad idea for you.”

I said, “Maybe for Katie. If I suggest it to me, it would likely be the last time I crossdress.”

“Then maybe your parents would be right if they stopped you from crossdressing.”

We changed that discussion and she was soon letting me off at my house. Soon as I was in the door, Katie grabbed me and took me up to her room. I knew she had gone out to get a few winter outfits. “Relax Katie, I will enjoy your seeing your clothes, just let me catch my breath.”

She said, “No, I want you to help me so I can see what goes with them.” She was undoing my belt when I understood what she was asking. “I even brought a pair of your panties and a bra that will do. Please, help me, Ashley’s coming over and I want a few outfits figured out before she gets here.”

My pants fell to the floor, “Good,” she says, “Your legs are shaved. I have a new tweed skirt and I have two tops that I want you to wear with them.” Katie is hurriedly brushing out my hair more to her style.

I turned from her to take off my underwear and put on the panties and bra. She put in a pair of cutlets, but they were larger than mine. I said, “I didn’t know you had these?” She told me they were for her bulkier sweaters. “That silver blouse and the other top aren’t bulky,”

She retorts, “And you not as big as I am; I want to see how I’d look?” I pulled off my top and happily put on the bra. I too wanted to see what I’d look like noticeably chestier.

Thankfully, I snuggly fit into the tweed skirt. It was shorter than I’d be comfortable in. I put on a faux turtleneck to go under the silky silver blouse.

Mom knocked on the door and was coming in, “Katie did I hear Gary come home. He didn’t stop to let me know he’s here and now I can’t… Oh there you are, I see you already volunteered to be Caryn.”

“No, Mom, I got shanghaied. I’m not protesting too much, as I like the new skirt. How does this outfit look on me?”

Katie quickly says, “It’s not your outfit, and you don’t have permission to wear it… Don’t move too much; I want to take a picture and then have you try this red holiday top.” Katie had a dress and a pair of dress slacks with two new tops as well.

The dress was a red knit dress. I was surprised by how the dress snugged my body. Katie had me temporarily take it off to put on a black camisole underneath it. “Mom, do you think that will keep me reasonably warm if I wore it for caroling outside?”

I joked, “Isn’t the point to get a boyfriend to keep you warm.”

She said with a cold stare, “If that is an attempt to say it looks nice, you need to get back to being Caryn.” I think it hit the three of us, that it was part of the old Gary creeping in.

The dress is nice and I had to keep it on to try jewelry, scarves, and purses with it. Mom volunteered the idea, “You’re going to need a new coat before Christmas if you’re going caroling in that.”

“I was not trying to hint for that Mom.”

Mom said, “It's your senior year and you also have one college visit before the holidays. It was something I already knew was needed. If we find a good sale and half off on a second, we might get one for Caryn.”

I jumped in, “I don’t need one as Caryn, I could use one of Katie’s.

Mom and Katie remark, “That won’t do, you don’t usually look good in the same clothes. When you’ve chosen clothes for Caryn, you have shown good taste in clothes. There are times you will have to make due, but a new coat is needed in this case. Your grandparents Keith and Marie Miller want you to look good if they’re to see you as Caryn for Thanksgiving.” That stopped that discussion.

I was shimming up the dress slacks when Ashley came into the room. “I thought the new clothes were for Katie?”

“Can’t I get any privacy?”

Katie responded to Ashley, “You’re a half-hour early, and Caryn’s modeling them so I can see how I will look in them.”

“With Caryn having extra help on top; I’m not sure you’ll look that good,” Ashley says.

Katie says, “Brat! That’s enough, I don’t need the help on top.” Ashley knows Katie and says, “Unless you wear the bulky sweaters you like.”

I stayed and talked with Ashley and Katie and it was after 8:00 in the evening before I realized I hadn’t eaten. My parents and Katie had eaten before I go home. Dad had a meeting, Mom had a project and Katie had her new clothes. Mom had made homemade soup and that and the bread was enough for me. It wouldn’t have been before.

To be continued…