Picking Strawberries

"Nice color." I heard the voice behind me and froze. "You remember Rachael, don't you?"

"Rick, what the fuck? You're supposed to be in Colorado. Rachael? What the hell...? What are you doing here?" I froze.

Let me back up a bit. I'm Robert, well, to my mom and dad, anyway. Rob to everybody else and Bobbi on those occasions when I get some uninterrupted time to myself. This was supposed to be one of those 'Bobbi' times.

Your average American guy, fresh out of high school, I'm going off to the state university in the fall, enjoying my summer, or I was. I'm 5-10 and weigh about 140 pounds, shaggy auburn hair. According to my mom, I have the prettiest green eyes anyone has ever seen, but she's my mom, so...

I'm in good shape and like all the things other guys like, sports, video games, hanging out with my friends. I was even the kicker on the football team. Where I diverge is, well, I like to dress up like a girl, a lot. That's where my 'Bobbi' time comes in.

What can I say? I've been doing it for as long as I can remember. Stealing things from the laundry hamper, usually my sister's stuff, wearing it and then putting it back before anyone could notice. With her moving out, I had full access to everything she had left behind, including the little pink bikini I was wearing while I painted my nails out by the pool.

My parents are on their way to California, helping Grace, that's my older sister, move and set up for her new job. My best friend Rick was supposed to be visiting his aunt in Colorado, except I just found out, he's not. I was supposed to have an entire week to myself, or Bobbi was.

Rick had just walked up behind me mid stroke with his girlfriend Rachael. The bright red polish looked amazing on the two and a half toes I had painted. He had caught me red-handed, or red-toed, and, like I said, acted like it was the most normal thing he had ever seen. Petrified and completely exposed, I was clueless about what to do.

"Relax, Rob. I've known about your hobby for a while, and just so you know, your parents, your sister and my parents know, too. As of a few weeks ago, so does Rachael. It's all cool."

"What?" The idea of them all knowing mortified me. I had always been so careful. How did everybody know? "How?"

"Let's just say you weren't as careful as you thought. Grace noticed some things out of place in her room and set up her GoPro. She caught you putting on a few of her dresses. She freaked and showed the video to me, hoping I knew about it and could tell her what was going on. I freaked and talked to my mom, which meant my dad. They explained it wasn't a big deal. Hell, my dad even admitted he experimented a little when he was younger. That made me feel better. I told Grace what they said. We went to your mom, and she laughed, telling us you had been doing it since you were little, and it was just part of who you are. 'It's just too bad he has to hide it.' The way she said it was a little sad."

"We talked some more, and I went back to talk to my parents. Didn't it seem odd that your parents didn't ask you to go help Grace move?"

"Huh?" I slowly turned to look at him. Rick looked like he always did, calm, cool, collected, like everything was in complete control. It was an annoying trait he had that also made him an excellent quarterback. Nothing phased him. Rachael was standing next to him. She was smiling and grinning like it was Christmas and she knew where all the really good stuff was under the tree. I would soon find out. She did.

"Buddy, I guess this is an intervention, except we're not here to get you to stop. We're here to help you. Why don't you let Rachael help you finish your nails while I put our bags in the guest room and change into my suit?"

Stunned, I sat with my mouth wide open as Rachael gently took the polish from my hands and finished painting my toes before moving to my hands. "Red is such an amazing color, don't you think?"

Dumbfounded, I just nodded.

"Now mine." She smiled and handed me the polish when mine had dried.

They really were ok with me being in my tiny little bikini.

I relaxed and took the polish. Taking my time, I meticulously painted Rachael's toes and fingers.

"You girls getting along alright?" Rick returned with three glasses of tea.

I wanted to protest Rick calling me a girl, but decided it wasn't such a bad thing under the circumstances.

"Exceptional. Just like besties." Rachael had one of those bubbly personalities that was infectious. It was honest and heartfelt. She was just a good person. "Now you two chat while I go put on my suit."

"Rick, what the hell is this?" I looked up at him, completely lost.

"You remember about six weeks ago when you and I went camping?" He started explaining that while we were gone, our parents, Rachael, and my sister had a massive meeting discussing my hobby. They had all devised a plan to help me come out of the closet safely without getting embarrassed too much.

I would stay home instead of going to help Grace move in. Grace would leave behind some things from her wardrobe that she could live without and that she knew I would love; like the pink bikini I was wearing. Rick's parents would go to see his aunt in Colorado, leaving him behind to be my support while Rachael helped me with the finer points of being a girl.

With me believing everyone I thought had any chance of coming to the house gone, it was the perfect opportunity. One they all knew I couldn't resist. I had to admire their thoroughness.

"So, you and Rachael?"

"I'm support, heavy lifting. She's implementation." He smiled. "You are going to have a few interesting days. I can't wait to meet this girl you've been hiding from me for all this time when Rachael's done."

"You're..., I mean everybody is really ok with this?"

"Everybody that loves you is ok with you being happy. If that means you dress like a girl, if that means you become a girl, we all love you, so yeah, it's ok."

I cried. Right there in front of Rick and Rachael, I cried like a little girl. I guess it was appropriate.

When I finally stopped sobbing, I realized that both Rick and Rachael had me wrapped in their arms.

"Thanks guys. I guess I got a little overwhelmed." I gave a weak smile.

Rachael smiled back at me, wiping the tears from my eyes just before Rick picked me up and tossed me into the pool. He did jump in after me and I tried to dunk him, but he was six inches taller and easily outweighed me by eighty pounds. I got tossed into the deep end for my trouble.

We spent the afternoon by the pool, lounging and talking.

"Rachael, can you do my back?" I handed her the suntan lotion as I flipped over.

"I have a better idea." She grinned and handed it to Rick.

"OK, hottie, lay down." I did, and he unfastened my top and moved my hair out of the way, squirting lotion down my spine and giving me the most sensuous massage I had ever had. My best friend was rubbing my back, my legs, my arms, and my butt, getting the lotion up under my bikini bottoms. Pressing his fingers into my flesh, squeezing my butt cheeks. Rachael giggled when I moaned.

I moaned even louder when my little cock escaped my suit and exploded all over the concrete below my chaise.

Rick swatted my butt and gently refastened my top. I looked over at Rachael as she lay in the chaise next to mine. "My turn." She smiled at me and then at Rick. "I think maybe Bobbi needs a boyfriend." She giggled. I wanted to object, but I couldn't move.

The sun finally won, and we headed inside. I smiled at myself, admiring the tan lines from the bikini as I rinsed off in the shower before letting Rick and Rachael take their turn. From the sounds emanating from the bathroom, they were doing more than just showering. I imagined the two of them together and what they were doing to each other. For the second time, my little cock spurted. This time, all over my hand.

Mindlessly lost in the images of Rick and Rachael coursing through my imagination, wondering what it would feel like to be buried inside a woman. I tried to imagine her ecstasy, her pleasure from having Rick's massive beast driving into her, his balls emptying into her. Remembering how it had felt to have Rick's powerful hands on my body, I brought my hand to my lips and licked it clean. Going back and squeezing the last drops of cum from my softening cock, I did it again.

Rick had been busy when he unpacked. All the clothes Grace had left behind were in my dresser drawers. Well, her panties and bras were in my underwear drawer and my boy's briefs were gone. I could only guess what my closet and the rest of my drawers looked like.

I don't know why I was nervous; they had told me it was ok. They explained what they were doing, that they were here to help me. My hands trembled as I reached into the drawer and pulled out the matching panties and bra. Slipping the panties up my legs and nestling them in place, tucking my little soldier in place, and running my hand over my now smooth crotch. It always felt so nice.             

"Let me help." Rachael came up behind me as I adjusted the socks I had stuffed in the bra. She was in her underwear, carrying a small box in her hands.

"These will help." She set the box on top of my dresser and slipped the socks from my bra. Opening the box, she inserted modest fake boobs into the empty cups. "They glue on, but for now, your bra will hold them in place, and they look a lot better than socks." Her smile put me at ease. When I looked at myself in the mirror, I smiled. They even had small pert nipples that poked through the bra.

"Now finish getting dressed. Rick is taking us out for pizza."

"What?" My smile disappeared, replaced by a look of sheer terror.

"Come on. That's what this weekend is for. Rick and I will be right there with you, and trust me, after I help you with your makeup, it will be fine."

"Makeup?" I whimpered like a little girl, then grinned at the irony.

"Yes, makeup, and tomorrow, a full makeover at my spa." She pulled my hair back behind my ear and kissed me on my cheek.

Shorts and a loose-fitting tank top with flat sandals. I decided I looked cute, and I really liked the way the forms moved with me and loved the way they looked. My stomach was still full of butterflies at the prospect of going somewhere dressed like a girl.

Rachael sat me down and slowly explained everything she did to my face, foundation, blush, eyeliner, and eye shadow. The icing on the cake was the bright red lipstick that matched the polish on my nails.

My butterflies changed ever so slightly, the trepidation slowly becoming anticipation. I was pretty.

"Holy shit. Rob, is that you?" We had walked into the pizza place right into the middle of a bunch of our old teammates. I froze, frantically looking at the guys staring at me, glancing at Rick and Rachael, trying to decide if I should run, cry, throw up, or all three.

"Hey guys. Listen, she likes to be called Bobbi. If any of you have issues, you can take them up with me." Rick moved in front of me while Rachael grabbed my hand, leading me to a table in the corner, away from prying eyes.

"I'm sorry Bobbi. We should have thought about something like this happening." Rachael sat next to me in the booth and wrapped her arm around me while I trembled. I could hear them talking about me, a few cracking jokes and a few telling them to shut up. Most didn't say a word. Almost all of them watched Rachael lead me across the small restaurant.

"Yo, Bobbi. It's cool, man." It was Tiny, one of our defensive tackles. He had joined Rick as he came to our table. "Any of those guys bother you, you tell me, or Rick, and we'll take care of it, understand?" At 6-8 and 370 pounds, Tiny was a good person to have on my side. "You look nice, real nice." He gave me a gentle smile.

"Thanks." I felt a little better.

A few more guys came over and apologized for the rest, and one or two got up and left. Those that stayed got quiet. Part of me felt bad, but a larger part wanted to stand up and yell, "Fuck you!" As loud as I could. I guess it was a lesson I was going to learn - eventually.

The last thing I expected was the text I got on the way home. It was from Steve, one of our receivers; "Hey, Bobbi. Sorry for those jerks. You looked nice. Was wondering if maybe you'd like to do something sometime. Let me know."

I sat and stared at my phone the rest of the way home. Why would Steve want to go out with me? He'd barely even talked to me, and we'd been on the team together for three years. Now, suddenly, he's asking me out. Maybe he was gay, and he thought with me showing up as Bobbi, I was, too, or maybe he had a thing for tall red-haired girls. Maybe he had a thing for girls like me, because that's what I was today, a girl.

Rachael helped me take my makeup off and glue my new breast forms to my chest. I slipped my bikini back on, noticing how much better it fit with the fake boobs and just swam laps, letting the day wash over me like the cool water of the pool. Each little detail had been a tiny step to here, to now. I had gone out as a girl. I had been pretty. Rick, Rachael, Tiny, and Steve had told me so.

Even the way the other guys on the team reacted confirmed it. If I had looked like a guy in drag, they would have laughed at me mercilessly, but they hadn't. They found me attractive, and that was what bothered them. I was cute, and it threatened their masculinity. I was cute. Screw their masculinity.

I slept like a baby, no, like a princess in one of those fairy tales, waiting for some prince to come kiss me and wake me up.

Rachael's spa was both terrifying and wonderful, terrifying because it was full of people, specifically women. I was the only 'boy' in the place. Not that they noticed. I had my forms in and a cute skirt and top with light makeup that Rachael had shown me how to do, but still.

The wonderful came later.

"Bobbi, this is Terry. She's a friend of mine and she is going to take good care of you, ok?" I nodded nervously. I felt like I was five again on the first day of kindergarten, my mom dropping me off with Miss Weatherstone.

"Where are you going?" I gave Rachael a panicked look.

"Most of what they are going to do to you, they are going to do to me, and we can't be in the same room at the same time for parts of it. It will be ok, trust me. Remember, I'm on your side. So is Terry. She knows everything."

What little hair I had was quickly gone. Terry was brutally efficient. I winced a lot and cried a little, letting out a massive sigh as she slathered me with lotion. I had to put the lotion where they did the Brazilian part, but I understood.

Rachael was waiting in the main salon when Terry and I came out of the waxing room. She had an apologetic grin on her face. I read between the lines. She was right. If she had told me, I would have bolted.

Hair and nails were next. What had been a shaggy mop turned into flowing locks almost to the middle of my back. Terry had trimmed and shaped my natural hair and meticulously added extensions. While Terry worked on my hair, another girl worked on my hands and feet. I was in sensory overload.

When Terry and the other girl were done, my nails were once again bright red, with my fingernails being a half inch longer. That was going to take some getting used to, but looked amazing and made my hands so feminine. Looking in the mirror, I couldn't tell where my hair ended and the extensions started.

"This is just like your real hair. You can do anything with it you would normally do. I just hope you take a little better care of it," Terry laughed. "I'll send you home with some products that you should start using."

"One last thing and we can go meet Rick for lunch." Rachael smiled at me.

"Little stick." Terry pulled my hair back, and something stung my left earlobe. I looked in the mirror to see a single stud with a red crystal. "Now the other." Pop. A matching stud appeared in my right ear.

Overwhelmed was the only word I could think of that fit how I felt. The girl looking back at me was beautiful. Tears found my cheeks, and I chewed my lips. This was what I had always imagined. This felt so right. I needed to say thank you. I needed to validate what they had done. "Can you do my belly button?" were the only words I could find.

Terry and Rachael both laughed, understanding fully what that request represented. I was never going back. We picked a red heart with a butterfly bangle. It was perfect.

"Wow." Rick just stared at me when Rachael and I got to the restaurant.

We ordered, and I filled him in on The Great Spa Scam, as I called it. "I mean, I have to go back every three or four weeks to get my nails redone, and every six for the waxing stuff, and every three months to have my extensions redone. It's like indentured servitude. I'm going to end up working for the spa just to pay my bill."

Rachael laughed. "You're the one that wanted to be a girl. We're just here to help. We can always go back and have it all undone."

If my eyes could have shot lasers, Rachael would have been toast. Rick hadn't said it, but his reaction confirmed what everyone at the spa had said. I was beyond pretty. There was no way I was going back to being just Rob.

"I'll suffer." I grinned.

After lunch, we went to Disney Land. Well, really, it was Sephora in the mall, but it might as well have been Disney. Rachael had signed me up for a one-on-one class, intensive training on makeup. I did mine, then Rachael's. When I was done with hers, I did the instructors, a guy named Bryan. He jokingly offered to hire me to do it again for his drag show. It was wonderful.

Rick hadn't been idle while Rachael and I played. He had completely redone my room, replacing my brown and gray bedclothes with pinks and yellows and purples, all pastels. There were pillows with flowers, and in the corner next to the window, a brand-new vanity. Rachael helped me set up my makeup and showed me how to adjust the mirrors and lights for the best effect. It was more girly than Grace's room had ever been.

We ordered Chinese and ate by the pool, talking about stuff. Mostly I talked about how I felt about everything that had happened since they found me by the pool doing my nails in my bikini. Even running into the guys from the football team at the pizza place had been a good thing. Sure, a few were probably going to give me a hard time, and I was certain that word was spreading quickly among our common friends, but I was loving it. Was this even who I wanted to be? Not Robert, or even Rob, this, Bobbi, the pretty girl with the long red hair I saw in the reflection of the sliding glass door on the back of the house.

Probably. I had fantasized about it enough, and now it was a real possibility. I thought about Rachael's joke about needing a boyfriend and what had brought it about. Maybe. I smiled.

"Rick, how well do you know Steve?" I was looking at his text on my phone again.

"Nice guy. Kind of quiet. Good receiver, I think he got a scholarship to State. Why?"

"He texted me. After pizza yesterday. He wants to go out or something. He never even talks to me. Part of me is afraid it's a joke, but part of me wants to say yes. I don't even know how he got my number."

"Invite him to come hang out by the pool with us tomorrow." Rachael piped in. "That would be safe." She got 'that,' look on her face. "So... You think he's cute?"

It was a good thing it was dark, because I could feel myself blush. I didn't know anything about how I felt about boys other than the images of Rick that ran through my head when I heard him and Rachael together in the shower. I knew it excited me and that the idea of being the girl in the equation wasn't unappealing, but did I think Steve was cute? Did I want to do anything with him? I just didn't know.