A Scout leader's Reunion, Kinda

This story is a complete work of fiction. Any similarity to people living or dead is purely coincidence. All characters are 18 years old or older at the time of any sexual activity.

I first met Kevin when he was seven years old and he joined the Cub Scout pack I oversaw. He was a cute kid. Red hair with pale skin covered in freckles and green eyes that were both inquisitive and troubled. You might say he had a bit of a feminine appearance, but at seven is any boy masculine? Before you go down that path, no, this is not that kind of story. I was a scout leader for ten years and not once, even for a split second, did I ever have inappropriate thoughts about any of my boys. In fact, I was very strict about myself as well as the other leaders in our pack adhering to the youth safety policies put in place by the Boy Scouts. The last thing I ever wanted was for the boys' experience in scouting to be ruined by even the impression that something wrong was occurring. I was also very protective of "my boys". I loved them all in the same way a father loves his children.

No parent (or scout leader) will admit it, but we have favorites. Ok, maybe not favorites. But there are certain boys that you feel you are bonded with more closely than others. Kevin was one of those boys. When Kevin first joined us, he was so quiet and reserved that you could easily miss him if you were not looking for him. He was shy and had virtually no self-confidence. That had a great deal to do with, in my opinion, his parents. To say they were overbearing was an understatement. They demanded perfection in everything he did. Even at such a young age they expected him to be flawless in anything he did. It's not that they didn't love him. They did. They just were so committed to his success as an adult that they wouldn't let him be a kid.

That's where the scouts and I came in. We gave Kevin a safe place to just be, well, Kevin. A place where it was ok to struggle and not get it right every time. A place where you could make mistakes and learn from them instead of being chastised for them. A place where it was ok to have fun. I spent many hours reminding Kevin that it was ok not to be perfect. When he struggled with something, I helped him improve in a constructive way (just as I did other boys in the pack). I was proud to see the changes in him by the time he left us. He was still not what you would call an extrovert, but he was far more confident in himself than he was when he joined us.

We lived in a small town, so it was not unusual to see some of my previous scouts in the store or at a restaurant or school event. I always enjoyed catching up with them and hearing where their lives were taking them. This included Kevin. It always made me happy to hear that they were doing well. One by one the boys grew up and moved away to college or pursued whatever the next stage of their lives was. After that I had to settle for getting updates second hand from their parents when I saw them.

It was one of these run ins that would leave me quite shocked. I Happened to run into Kevin's father, Rick. Rick was the more tolerable of the two parents. While he was often just as pushy about perfection, there was a certain part of him that was willing to let Kevin have a little slack. After exchanging the normal courtesies, I asked how Kevin was. That's when I got the shock of my life.

"She's doing pretty good, I guess. She's doing college online. It's been easier while she has gone through her transition." Rick said.

I wasn't sure I had heard him correctly. The look on my face must have conveyed my confusion.

"I thought you knew?"

"Um, no. To be honest I haven't seen him, er her in a while."

"Yea," Rick started. "She started hormone replacement after he graduated high school. Last year she got, um, the top done. Now I guess she's waiting to, well, um, finish."

I was stunned. Nothing in Kevin's behavior had ever indicated any kind of confusion about who he was. Or had I missed it?

"How is Karen taking it?" I asked, fearing I knew the answer.

"She freaked. Started drinking. Pretty much stayed that way until Kelly had enough and moved out."

"Kelly?" I asked not following.

"Kevin's new name." Rick replied.

"Oh, yea. Of course. So where is she staying? Is she ok?" I was genuinely concerned.

"Last I heard she was living with some friends nearby. She doesn't really reach out to us much anymore."

I could tell that it hurt Rick. He really did love his son. But it was a tough spot to be in between his son and his wife. We spoke for a few more minutes before we went our separate ways. I hated to think of Kevin out there on his own with no support.

It had been nearly five months since I had seen Rick. I must admit that the news of Kevin's change hadn't exactly changed the way I lived my day-to-day life. Nevertheless, he (or rather she I guess) crossed my mind.

I was walking out of Dollar General one day when I noticed a car in the parking spot next to mine. It was an older four door that had obviously seen better days. The hood was up and standing leaned over into the engine compartment was a pair of long, toned legs that ended in the most amazing little ass I had ever seen. The ass in question was covered by a pair of short cutoff jean shorts. Every time the owner of the ass leaned further into the hood, the shorts rode further up revealing more of the firm, milky, ass cheeks.

"DAMM IT!" I heard a voice say from under the hood.

"Do you need some help?" I asked

"I doubt it. I think this piece of shit is done for." The voice said as it removed itself from under the hood and stood to make eye contact.

What was standing before me was gorgeous. The firm legs and cute ass were attached to a perfect little body. Thin, but not overly skinny with a pair of firm B cup breasts that, while not large, fit the frame they were on perfectly. The only way to describe the face that looked back at me was adorable. Soft, pale skin. A cute button nose. Perfect soft lips. Beautiful green eyes and a dusting of freckles. All framed by long, fire red hair. As beautiful as she was, she was also very familiar.

"Mr. Mike!" she squealed jumping into my arms. "Oh my God I can't believe it's you!"

I stood, thoroughly confused for a moment before realization kicked in.

"Kevin?" I said shocked.

"Um, well, its, uh Kelly now." She said embarrassment and a bit of shame on her face.

"Oh my God, of course. I'm sorry. I was just a little caught off guard." I said, fumbling with my words a bit.

"I get it. I'm pretty used to it." She said sadly.

"I'm sorry. I really am. I'm really happy to see you. Ive been thinking about you."

Shit, that came out weird.

"You, you have?" she asked confused. I explained how I had talked to her dad and how I had been concerned about her wellbeing. This caused her to smile a beautiful smile.

"So, what's up with your ride?"

"I dunno. It started running like complete shh.... crap. I barely made it in here before it died completely."

I spent the next thirty minutes trying to diagnose the issues with the car and came to one definite conclusion. It was done for.

"Damm. Just what I needed." Kelly said, obviously very upset.

"No worries. I can give you a ride home. Tomorrow we can arrange to get your car taken care of." I offered.

"Um, yea. No I'm ok. I'll just call a friend and have them pick me up." Kelly said.

"Nonsense. I'm already here. There's no reason to make your friend drive over here."

I had seen inside Kelly's car while trying to get it running. It looked like everything she owned was in it. I had a feeling that there was no "friend" to call.

"No really Mr. Mike., I'll be fine." Kelly said with no real confidence in her voice.

"Kelly," I said, my voice firm "What's the deal? Where are you really staying?"

Kelly hung her head. She said nothing, simply pointed at her car.

"You're staying in your car?"

"Yes sir." She said. The shame was evident in her voice.

"Well, not tonight. Gather what you need. You can crash at my place."

Kelly looked at me shocked. "Youd let me stay with you?" she said surprised.

"Of course. You're one of my boys um well, so to speak. I always told y'all if you ever needed anything I'd be here for you. Now get your stuff."

A few minutes later Kelly had gathered a meager selection of belongings, and we were heading for my house.

"Are you sure Mrs. Kinley will be ok with this?" Kelly asked.

"Um, well, her and I aren't really a thing anymore. It's a long story." I replied.

It wasn't really all that long of a story. I had come home early to find my wife in bed with another man about a year ago. I had suspected it but could never prove it until that day.

When we arrived home, I helped Kelly carry her stuff in. Once inside I told her to make herself at home. I showed her to a spare bedroom where she could put her things. I got some extra bedding and gave it to her. After she had made her bed and got her stuff settled she came out of her room.

"Um, Mr. Mike, would you mind if I grabbed a shower? I haven't had one in a couple days." she asked shyly.

"Sure." I grabbed her a towel and showed her to the bathroom.

"I'll be quick." She said.

"Take your time. I have my own bathroom in my room so consider that one yours."

While Kelly showered, I made some hamburgers and fries. I was fairly certain it had probably been a while since she had a decent meal. I was just finishing up the food when Kelly came into the room. She was wearing a pair of white sweatpants and a camisole that ended just above her midriff. She was running a brush through her damp red hair. I was kind of taken aback. If it hadn't been for the fact that I knew Kelly's backstory, I would have never in a million years guessed she was trans. The thin shirt clung to her firm young breasts. Her exposed belly showed a silver navel piercing, and her sweats hung loosely from hips with the slightest curves. I had to admit, she was beautiful.

"It smells good." Kelly said with a smile.

"I figured you might be hungry. It's nothing fancy. How was your shower?" I asked.

"Mmmm, It was amazing. It's been a while since Ive had a nice hot shower."

I sat a plate of food down in front of my guest then joined her at the table. I was amazed at how fast she blew through the first plate of food. She asked for seconds. I told her to eat as much as she liked. She grabbed a second plate and rejoined me. I asked her what she had been up to since I had seen her last. She filled me in on how she had started online schooling. She had wanted to be a dental assistant. Unfortunately, she had run out of money and her situation at home (or rather no longer at home) had made it nearly impossible to continue. She had worked a couple menial jobs. Her most recent job had been as an office assistant. She had made enough at that job to get a small apartment. Things were going pretty well when her boss had started making moves on her. When he had found out that she was trans, he had fired her. I was pissed. I asked why she hadn't gone after him for sexual harassment. Her response we simple. In her mind, lawyers cost money and she didn't have that. The job market had been tough. She had tried but couldn't find another job. Eventually she had been evicted. Since then, she had either been couch surfing or living in her car.

"Well, I'm not going to have you out on the streets. You can stay here as long as you need to get back on your feet."

"I couldn't do that. I wouldn't want to be in the way." She said.

"You're not in the way. Besides, I'd be worried about you nonstop. Obviously, it's your choice, but you're more than welcome." I said.

"Youd really be worried about me?" she asked, unsure if I was serious.

"Of course I would. I'm not going to have you out there with nowhere to stay."

She thought for a minute. "Ok." she said smiling. "But I want to earn my keep. I don't want to be a freeloader."

"Fair enough. I'm sure we can come up with something that works."

When we were done eating, I got up to start cleaning. Kelly insisted I relax however. She wanted to show her appreciation by cleaning up. I tried briefly to argue, but finally gave in. We chatted as she cleaned up. Not really about anything specific, just talked. At one point I mentioned something about scouts.

"Those were my best times." She confided. "I never felt more comfortable or more accepted than when I was in scouts."

"Well, that's what the program is all about." I said.

"Yea. But it was more than that." She said, sitting at the table again.

"It was you." She said, putting her hand on mine.

"Me?" I stammered, not sure how to react to her touch.

"Yes. You." She said, her green eyes burning into mine.

"You never judged me. You allowed me to just be me. You were always so encouraging and supportive. Even when I failed, you just encouraged me to try harder. I didn't have that at home. You will never know how much that meant to me. I never had that before. Or since, to be honest."

"Well, um, I'm glad I could be there for you. I don't really feel like what I did was all that special." I said, not sure how to react to such a heartfelt revelation.

"Believe me, you're more special than you know. Not many people would have put that much love and effort into us kids."

"I don't know about that." I said.

"Really? How many other leaders would have allowed their trans former scout to crash in their home no questions asked?"

I had to admit; she had me there.

"See. Special." She said laughing.

"On that topic," I started without thinking.

"What?" she asked.

"Nothing, sorry, it's none of my business." I said, now suddenly ashamed that I brought it up.

"Why did I become a girl" she asked smiling.

"Well, yea. Sorry I wasn't thinking. It really is none of my business."

"It's ok. I don't mind talking about it with you. I guess I've always known I was different. I never fit in with the other boys. At first I thought that maybe I was just gay. I discovered I was attracted to guys about eighth grade. But I started feeling like it was more than just that. I don't know how to explain it, but I just didn't feel right in my body. I found myself being more obsessed with women's clothes. Started thinking about how a woman would feel doing different things. To be honest, I became obsessive about everything female. Then one day I was reading an article about trans women and gender dysmorphia and it all clicked. By ninth grade I had pretty much figured out that I was trapped in the wrong body. So, one night I sat down with my parents and told them and told them I wanted to start hormone therapy."

I knew her family too well. "I bet that didn't go over well." I said.

"Yea, no shh,, no kidding. Mom completely freaked. Dad kinda went into denial. They flat out refused to allow it so I had to wait until I was eighteen and could make my own medical decisions to start. Of course, Mom couldn't handle it and started drinking. Dad tried but he was catching hell from Mom. So, a year later I did two things. Number one, I left home. Number two, I took every penny I had ever saved and got breast augmentation."

"I'm sorry you went through that." I said, genuinely sad to hear what she had suffered with her family.

"Yea. It wasn't easy. But the truth is, once I was out and had the surgery, things started to feel right. I finally felt like I was becoming who I was supposed to be. I even went on a few dates with some guys as a girl. It was exhilarating."

"Did they know?" I asked.

"No, uhuh. I wasn't that brave yet." She said laughing.

"So, you never um, well, you know?"

"Had sex with them?" she said

"Um, yea, sorry. You don't have to answer that." I said blushing.

"You know you're cute when you're embarrassed?" she laughed. "No. At least, not all the way. Ive let a couple feel me up. Upstairs of course. And Ive given a few head. But no, I haven't gone all the way with a man. I guess I'm just afraid of what would happen when they found out."

"I see." I said, unsure of what else to say.

"Actually, I kinda owe all of this to you." Kelly said, her tone turning slightly more serious.

"You mean, I'm the reason you became a girl?" I asked confused.

"No, silly. Ive always been a girl. You didn't do that. But you gave me the confidence to face it and face my parents about it. If you hadn't taught me to have faith in myself and be more self-confident, I might still be trapped in my old self. And that would have been truly miserable. You're part of the reason I was able to take the steps to make myself happy."

"Well, uh, I'm glad I could help. And I'm really glad you're totally happy." I said.

"Well, I'm not TOTALLY happy yet. That would require finding a man who will love me for who I am." She said with a bit of a frown.

"Well, you're a beautiful girl. Any man would be lucky to have you." Where the fuck did that come from, I thought to myself as the words left my mouth. I had never, not even once, thought about sex with a man, or trans girl, or whatever. But I couldn't deny how beautiful the young woman sitting across from me was.

"Really, you mean that?" Kelly said, her eyes getting a bit misty.

"I do." I replied.

"Awwww, thank you Mr. Mike." She said. Kelly jumped up from her seat and bound over to mine. She plopped herself in my lap and gave me a huge hug. Her firm breasts pressed into my chest as she wiggled slightly on my lap. Despite my best efforts, I felt my cock begin to rise under her weight. Apparently, Kelly felt it to. She leaned back and looked me in the eyes. She smiled. It was an impish kind of smile. The kind of smile that told me something was going on in her head.

"And any woman would be just as lucky to have you." She said before kissing me on the cheek. As Kelly stood, I noticed a slight bulge in her sweats. She caught me looking and smiled again. I blushed furiously.

"You really are cut when you're embarrassed." She said. "I'm tired. I'm going to head to bed." She said as she walked away. Her hips were swaying gently as she walked. When she reached the door, she turned and caught me staring again. "Goodnight." She said. Her voice had a seductive tone to it.

I made sure Kelly was long gone before I stood up. My engorged cock strained at the confines of my pants.

"What the fuck is wrong with you." I thought to myself. I went to my room, stripped, and climbed in the shower. I was hoping it would help. I didn't. As the warm water flowed over me, I leaned my head against the wall and closed my eyes. Visions of Kelly's firm breasts and plump ass entered my mind. I reached down and started stroking myself. I couldn't help but imagine how she had looked sucking her other boyfriends. I wondered how it would feel having those lips around me. And I imagined how it would feel to be the first to fuck her tight hole. My stroking got faster and before I knew it, I was spraying my load on the shower wall. When I recovered, I finished showering. I dried off and went into my bedroom. I usually slept in the nude, so I thought nothing of climbing into bed naked.

I had just started to drift off when I heard my bedroom door open. My bedside lamp was on and shone a soft light on Kelly as she made her way to my bed. She was wearing the same thin shirt, but in place of her sweats she now wore a pair of black lace thong panties. She said nothing, simply lifted the covers and slid into bed next to me. She looked into my stunned eyes only briefly before kissing me. I didn't fight it. I didn't want to. I wanted this. I wanted her firm young body. I wanted to make love to her. My had slipped behind her neck and pulled her mouth tighter against mine. Our lips parted and our tongues began to explore each other's mouths. She moved closer to me. Her leg draped over mine. She let out a slight moan when she realized I was nude. Her hand worked it's way down my body eventually finding my rigid manhood.

"Mmmm, Mr. Mike." She sighed with approval. She started slowly stroking me as she kissed my neck and chest. I hadn't been touched by another person in so long and Kelly's hands were working magically on me. I could feel her lace sheathed bulge grinding against my leg. I wasn't sure, but I thought I felt a damp spot. She continued kissing her way down my body until, at last, I could feel her warm breath on the head of my cock. Then I felt her tongue. First licking the sensitive under side, then cleaning the leaking precum from my slit.

"Mmmmm, yesss baby." I moaned. I looked down and saw Kelly grin. Then, her lips parted, and she took me into her mouth. "Oh fuuckk" I groaned as she took my full length into her mouth and down her throat. She began to massage my balls as her mouth worked it's way up and down my shaft. She was definitely skilled. Every stroke of her mouth was heaven. My hands entangled in her hair guiding her. Her mouth moved up and down my full seven inches with ease. After several minutes of this oral assault, I felt myself getting close.

"Oh Baby, you're gonna make me cum."

Kelly removed her mouth from my throbbing meat.

"Not yet Mr. Mike" she said as she slinked her way back up my body. She returned her lips to mine. Kissing me passionately. I didn't care that those lips had just held my leaking cock. I wanted to kiss her. After a couple of minutes she broke our kiss and stood up beside the bed. She stripped her panties freeing a thin, four-inch girl cock. She looked at me for a minute, judging my reaction. I smiled.

"Come here Baby." I said. She smiled and slipped back into bed. I grasped her hips and pulled her towards my face,

"Mr. Mike you don't have to.."

"Shhh" I said, before lifting my head and taking her in my mouth. She sighed as she slid past my lips. I wasn't sure what to expect, but I liked what I received. I could taste the slightly salty and bitter taste of her precum. I ran my tongue over her tip gathering more to try.

"Mmm, oh yesss" she sighed. Her hips started to pump, slowly fucking my mouth. I grabbed her firm ass cheeks and encouraged her. She reached for the bottom of her shirt and lifted it over her head. As she did, two beautiful breasts came into view. They were perfect. Firm and round, topped by two small, light pink nipples. They seemed to defy gravity. She began to massage her pale orbs as she worked her cock in and out of my mouth. I could taste even more of her warm jizz leaking from her.

Finally, Kelly pulled back, freeing herself from my warm oral confines.

"I want you to fuck me Mr. Mike. I want you to be my first."

"Anything you want Baby." I said.

Kelly stepped away and grabbed a bottle of lube she had brought in with her. She lay down on her back, and after applying some to her fingers, began to work the viscous liquid into her hole. I took the bottle and applied a liberal amount to my own shaft. Setting the bottle aside, I positioned myself between her legs. She pulled them back lifting her ass off the bed. I grabbed a pillow and placed it under her before lining myself up with her puckered hole.

"Ready?" I asked. She bit her lip and nodded.

I pressed against her, and, to my surprise, found little resistance as I slid nearly all the way into her in one stroke.

"Mmmmmmm, oh my God yessss!! Fuck that feels so good."

"It doesn't hurt?" I asked amazed.

"Hell no, its amazing. Fuck me, please"

I pushed a bit further, burying the rest of myself inside Kelly's tight love canal. This elicited more moans. I began to pump in and out of her slowly. God, she felt amazing.

"Faster Mr. Mike, please, I need more."

I started working my cock in and out of her at a steady rate. I would pull all the way to the head before plunging back in.

"Ohh fuck yes, more. Give me more!" One of her hands grabbed my ass encouraging me to increase my tempo. The other began to stroke her small erection. I started fucking her in earnest. Pounding in and out of her.

"Oooohh yessss fuck! That's it, fuck that boi pussy Mr. Mike. Own it. Make it yours."

I was fucking her ass with a reckless abandon. My hips slammed into her every time I bottomed out. The look in her eyes was pure lust.

"Fuck yea. That's it. Pound me. Destroy my hole. I want your cum Mr. Mike. Make me pregnant. Give me your fucking babies pleeeaasseee!"

I could feel that I was getting close. The combination of her tight hole and the dirty talk was driving me to the edge.

"Mmmm fuck that pussy feels so good. I'm going to blow my load so deep inside you!" I grunted

Her hand was pumping away furiously at her cock. After two more thrusts I felt my balls tighten as I unloaded deep in Kelly's bowels. As I did, her own cock erupted shooting her load all over her belly and breasts.

"Ohhhh fuucckkkk! I can feel it! Fuuck that's so good! Breed me!" she screamed.

As I finished, I collapsed on her chest. Kelly's hot, sticky load was trapped between us. I felt her hand begin to rub my back as we both lay there panting.

"Oh my God. That is soooo much better than anything I've ever had." Kelly finally said.

"I thought you said you've never been fucked?" I asked sitting up and looking at her.

"No, I said I've never been fucked by another guy. That doesn't mean I haven't used my fair share of toys on myself. I had to get off somehow." She laughed. "But trust me, nothing Ive done to myself comes even close to what you just did to me."

We lay there for several more minutes before we decided we should get cleaned up. We showered together where we spent a slower, more relaxed time exploring each other's bodies.

When we got done, we dried off and returned to my room. I crawled back into bed. When Kelly came in, she gathered her clothes and started for the door.

"Where are you going?" I asked.

"I don't know. I just figured you'd want me to go." She said a little sadly.

"Now why would I want that?" I said lifting the covers.

"Really? I can stay?"

"I wouldn't want it any other way." I said smiling

"Yayyy" she squealed before bounding across the room and diving into bed next to me. She snuggled up against be and gave me a quick peck on the cheek before resting her head on my chest. Within minutes, she was sound asleep.

I lay there awake for quite a while pondering everything that had happened. Before today I would have never imagined myself sleeping with anything but a natural born woman. And now, here I was, a beautiful young trans girl sleeping happily on my chest. I wasn't sure where this was going, but it was safe to say I was open to a whole new world of possibilities.