Halftime was my home away from home, an All-American sports bar with cold beer, tons of T.V.’s and waitresses in short shorts and halter tops, I had found it my freshman year of college when me and the five guys I shared a house with wanted to watch the game, but it wasn’t on our cable package. The food had been better than I expected, and the beer was just as cold as advertised and we had won the game, so a new tradition began.

Saturday, game day, you would find me, I’m Rick, Steve, Roger, Dave, Eldridge, and Benny in our jerseys, at our lucky table watching the game, flirting with our waitress, eating wings, and drinking beer. Sometimes we won and sometimes we lost but it was tradition, so we didn’t mess with it.

That had been five years ago, we had all graduated and most of my old roommates had moved off, on to better things. I had stayed here, gotten a job as a web content developer, I wrote and edited stuff for corporate websites that my company hosted, and hung out at Halftime.

I knew most of the waitresses by name and had become kind of an unofficial mascot of sorts, they all hung out at my table when it was slow or if they just wanted to chat for a minute. My table was a safe space, I had officially been deemed harmless and was in the biggest friend zone on the planet, surrounded by gorgeous scantily clad women that found nothing wrong with talking about the intimate details of the scumbag they had hooked up with last night in front of Rick.

A lot of it was my fault because I watched people, especially my old roommates, and noticed how they treated the girls, I refused to be one of those guys, openly ogling the waitresses and making lewd comments, ‘accidentally’ putting a hand where it didn’t belong and then laughing it off, I was courteous and friendly. My roommates gave me a hard time, but I knew the girls appreciated someone treating them like a person instead of a piece of meat, it just didn’t get me any dates.

Of course, It didn’t help that on the machismo scale, I had a negative score. Don’t get me wrong, I got compliments on my looks from the girls all the time, mostly how they were jealous of my eye lashes or my big blue eyes, my long shapely legs, my cute butt, or my shoulder length blonde hair. The running joke was that I could easily get a job working here as a ‘Halftime Girl’.

My waitress was Jenn, she knew how I liked my wings, what I wanted on my burger, how many Sweet-and-low packets to bring for my tea, and what beer I drank, never forgetting to bring the bottle cap so we could do the puzzle underneath, she had waited on me and the guys the first time we had come in and sitting in her section was a tradition too. She had also become a good friend, possibly my best friend.

“You got big plans for Thanksgiving?” Jenn brought me another beer.

“Nope, just gonna hang out, probably come in here and watch the games, you know me,” I laughed.

“What about your family, aren’t they getting together?”

“Mom and dad are going on a cruise, nobody else wants to host, so we’re all on our own.”

“Then come with me to my family, it will be great, it’s huge, one more won’t matter, I promise.”

“What about Mike?”

“Yeah, he’ll be there too, you know he likes you and besides, he knows your safe,” ouch, she could have used any other word.

“Sure, why not, beats being alone, especially if the best waitress in the place isn’t going to be here to make sure I get my bottle caps,” we laughed.

Jenn wasn’t kidding, there had to be a hundred people at her grandparent’s house for Thanksgiving, her aunts all brought something, and her grandmother cooked enough for everyone, I had never seen so much food. We ate until we were stuffed, went back for seconds, and then had dessert, everyone pitching in to help clean up before the games started. The guys went into the den to watch football and the girls went to the living room to gossip and talk.

“Rick, right?” Papa Joe, Jenn’s grandfather, called my name.

“Yes, sir?”

“Can you get me another winter wheat, the kegs are labeled,” he handed me his cup.

“Happy to,” I got up and headed out to the breezeway where the beer kegs were. Papa Joe was a home brewer and I had to admit his beer was pretty good, unfortunately, the winter wheat was too good, the keg was empty.

I let him know and he directed me to the basement to grab another one, he had planned for exactly this event. His brewing setup was impressive, it looked to me like he had two or three batches working all in different phases of the process. I found the five-gallon keg he wanted and threw it over my shoulder, losing my balance just enough to bump one of the tables and knock something loose, creating some type of comic chain reaction that ended up with me covered from head to foot in the grossest mess I could imagine.

To my credit, I made it back upstairs with the keg Papa Joe wanted only to hand it off to one of Jenn’s uncles as Grandma Emma led me to the bathroom to get cleaned up. I must have looked like a drowned rat, nobody laughed, but there were plenty of snickers.

Jenn stuck her head in the bathroom while I showered letting me know she had found some things I could wear home and informing me my beer drenched clothes had already been put in Mike’s car. We could leave as soon as I was cleaned up. I recognized the bag as soon as I saw it, it was Jenn’s work bag, I had seen it time and time again when I had been at Halftime when she either got to work or changed after the end of her shift.

I grabbed my phone from the countertop, “Really???” I hit enter.

“Sorry, no one else here is even close to your size, that’s why I said we could leave as soon as you’re ready. Mike understands.”

“K,” I couldn’t believe this, I laughed at myself in the mirror.

Unzipping the bag, I perused my choices, a pair of very pink, almost fuchsia tights or a pair of her work shorts and either her work halter or a large t-shirt that matched the tights with the word PINK across the front. At the bottom of the bag were an extra pair of purple panties and a lace demi bra that matched along with a pair of sandals, my boots were full of beer.

“Suggestions?” I hit enter.

“Shorts please, if you can get in them, those tights are new and I’m afraid you might stretch them out, sorry.”

There was no way the shorts were going to hold everything in place, they just weren’t going to do it, so I slipped the panties on. I had to adjust things a bit, so I didn’t hang out of the panties, ultimately shoving my penis back between my legs and snugging the panties up tight to keep him in place.

The shorts were next. I had to give myself a bit of a wedgie to get them fastened and zipped, half of my butt cheeks were exposed, these were probably my favorite shorts that Jenn wore at work, I had to admit, her butt looked better in them than mine, but not by much.

I started to pull on the t-shirt when I saw the bra laying there by itself, I couldn’t explain why, but I picked it up instead, slipped it up my arms and fastened it behind my back, adjusting it so that I had a small amount of cleavage. If it hadn’t been for the shorts, I would have gotten hard immediately. The t-shirt fit fine and while the sandals were maybe a half-size too small, they would work.

I put my hair in a ponytail with one of the scrunchies in the bottom of the bag, zipped it closed, took a deep breath, and opened the door.

This time, they all laughed, and I had to admit, they had every reason to

“Papa Joe, you still need that beer?” I decided to just go with it, it was very funny after all, I laughed right along with them.

I gave Jenn her bag and headed out to the breezeway to get Papa Joe his beer, grabbing one for myself at the same time, we stayed until the second game was over. I caught some of Jenn’s cousins and one or two of her uncles looking at my ass hanging out of Jenn’s shorts, there was some light-hearted teasing, but it was all in good fun, I even played waitress a little garnering a whole quarter tip from Papa Joe, I was sternly instructed to ‘not spend it all in one place.’

The ride home was uneventful, I had gotten used to the shorts and had almost forgotten I had the bra on, it just struck me as odd that Mike kept taking overt glances at me in the rearview mirror, looking away quickly when I caught him.

We were all tired when they dropped me off, so it was no surprise that I forgot the bag of beer-soaked clothes in the trunk, I had my keys wallet and phone in a small purse Grandma Emma had given me as a joke, I really liked Jenn’s family. An air hug from Jenn and a knuckle bump from Mike and I climbed out of the car and headed up the stairs to my apartment.

It would be three weeks before our schedules meshed and we returned the clothes we had, I couldn’t bring myself to tell Jenn I had worn hers more than just home from her grandparents’ house, of course we met at Halftime. Jenn and Mike were arguing about something when I walked in the door, “just ask, ok?” Mike said just as I got to the table.

“Ask who what?” I sat down and slid the bag with Jenn’s clothes across the table to her, she motioned to a larger bag on the floor, I could see my boots on top of the pile.

“Mike is freaking out and wants me to ask if you will do him a favor,” Jenn looked out of the corner of her eye at Mike.

“Sure, for you guys, anything, well almost,” I laughed.

Jenn elbowed Mike in his side.

“Look, this is really awkward, but I don’t know who else I can trust, Jenn can’t go to my company Christmas party with me and I have to go,” he took a deep breath,” anyway, there’s a girl from work that is going to be there and she keeps hitting on me, I’m about to get promoted and the last thing I need is some office drama, I need a blocker, someone to run interference.”

“And exactly how can I help you with that? I’m guessing them thinking you’re gay would count as drama, right? What about one of the girls from here?”

“I was thinking about you, as, as a girl,” his voice got slower and slower as he finished his sentence.

I spit my tea all over the table, “What???”

“Just think about it, ok? We know you wore the panties and the bra home from Thanksgiving, so you kind of like to dress, and the way you behaved, well, you were getting a lot of looks that didn’t go with you being a guy. I just thought that well, maybe it was something you liked to do, and it would be fun for you, and you know me and Jenn well enough to pretend, that’s all.”

“So, you want me to pretend to be Jenn?”

“No, just be my date, I don’t talk about my personal life at work, they just know I have a girlfriend.”

“Jenn, you’d be ok with this?” I couldn’t believe I was even considering what he was asking.

“Rick, I have been looking for a way to dress you up since I met you,” she laughed at me,” I think you’d be gorgeous with a little makeup and the right outfit; you’ve already got everything else.”

“And just when is this party, Christmas is next week?”

“Saturday.” It was Thursday.

The look on my face said everything, I clearly thought they were out of their flipping minds.

“Rick, you’re my size,” Jenn jumped in, “I have everything, I can do your makeup and you can wear one of my dresses, probably even my shoes, You can take a sick day tomorrow and we can go to the spa to get you ready, I already have some dresses picked out, we can practice all afternoon and you can practice again Saturday before you have to go, Don’t tell me you’re not interested, I mean come on, you took my bra,” she smiled at me.

“Spa, what happens there?”

“Manicure, pedicure, style your hair a bit, and maybe a little waxing depending on where there’s hair we don’t want anyone to see, nothing major,” Jenn was leaning forward practically crawling across the table toward me. Mike was just staring at me, his eyes begging, as if this were the biggest favor he could possibly ask and he knew it.

“it’s that important to you guys?”

“Rick, everything depends on this promotion, and I mean everything,” he shot a furtive glance at Jenn, and I knew exactly what he meant.

“Ok, what time do I need to be where?”

If it hadn’t been for the three glasses of complimentary wine, I would have bolted. Jenn flat out lied to me, there was no ‘maybe a little waxing’, they did my face, my chest, my arms, and legs, under my arms and even gave me a fricking Brazilian and that shit hurts. The lotion they used to sooth the burn helped a lot and smelled nice too. I liked the way they styled my hair, and I couldn’t stop looking at the red polish on my nails. Jen crossed the line when they snuck up on me and pierced my ears, or so I thought until I saw myself in the mirror, even without makeup, I was more than cute. Jenn’s smile was the loudest ‘told you so’ I had ever heard.

We met Mike for lunch and the way he looked at me made me nervous, Jenn just giggled. After lunch, Jenn called an audible and booked an appointment for me with a makeup consultant who spent two hours working with me on how to apply and remove my own makeup. I started to complain but was beginning to realize that there just might be more to this than I would ever have thought.

With a whole new look and fresh makeup, we headed to Jenn’s apartment to go shopping in her closet; her closet was bigger than my bedroom by the way. In all the years I had known Jenn, I had never been to her apartment, we had met for drinks, and I had hung out with her and Mike on many occasions in public, but this trip to her inner sanctum was a first.

The apartment was very nice, large, and spacious, well decorated with nice if slightly erotic art on the walls. Her bedroom was dominated by a king sized four poster bed and, as I mentioned, her closet was bigger than my bedroom, it was packed with clothes, how she found anything was beyond me.

On the bed were four matching bra and panty sets, one of them the purple I had worn before, the others were red, pink, and black, and just as lacy. She let me know we would be choosing my underwear after we found the right dress for tomorrows party.

“First, strip,” Jenn smiled at me, “down to your boxers,” she added a wink. I did as I was told. She eyed me up and down, I guess trying to get an idea of what might or might not look good on my slender body. “They did a nice job with the waxing, don’t you think? It feels sexy, doesn’t it?”

I nodded, agreeing that it did.

Jenn shook her head and walked to her dresser, rummaging through one of the drawers pulling out some simple white cotton panties, “those boxers just ruin the mood, don’t you think?” she tossed me the panties, I slipped them on as she disappeared into the closet to start her treasure hunt, the feeling of the soft cotton snug against my crotch, holding my manhood in place sent a shiver up my spine.

Looking in the mirror, something was off, I slid my hand down inside my panties and tucked myself back between my legs like I had done the first time to get the super tight shorts on, this time it wasn’t out of necessity, it was because the girl looking back at me just looked wrong with a penis.

Jenn came out of the closet with an armful of what she called cocktail dresses, there were black ones, red ones, a green one, a couple of blue ones and a deep purple that immediately caught my eye. I knew which one I wanted immediately but decided to try them all and thoroughly enjoy the process. I started with the classics.

The little black dress I tried first was amazing, it was snug against my body and fell about halfway up my thighs, the stretchy fabric moved with me, and I felt sexier than I ever thought possible. Jen looked me over and smiled, cocked her head to the side and went back to her dresser, pulling a small box out of a drawer.

“Here, put these on, they have a sticky back, so they’ll stay in place without too much help,” the box said ‘Venus, Secret Breast Enhancers,’ they were small boobs, “I wore those when I started at Halftime, before I got my own,” Jenn blushed a little and helped me put them in place. They gave me just enough bust that the black dress filled out, the dress went into the maybe pile.

The enhancers stayed in place as I changed dresses, the next addition to the maybe pile was a red one, like the black one, it fit like a glove, I was discovering I liked showing off my lithe little body and with what looked like modest breasts, it was even more fun.

The green didn’t catch my fancy and Jenn and I both agreed that even with my eyes, the blue ones just weren’t the right color for the event. The purple one, though, rich velvet, longer than the others, it had a slit up to my hip to compensate, I couldn’t stop touching myself, running my hands up and down the luxurious fabric, I was glad I had tucked, otherwise there would have been a problem. From Jenn’s expression, I knew she agreed, we had a winner.

I slipped it off and put on the purple bra and panties while Jenn put most of the dresses back in the closet, adjusting the bra as I had done before, and put the dress back on. It looked even better, the enhancers making my small boy boobs look like modest girl ones.

I must have stared at the girl in the mirror for ten minutes before Jenn got my attention by dropping three pair of heels next to me, one red, one black and the third a rich purple velvet matching the dress I had chosen. I slipped them on and while just a bit tight, they fit.

“Why the red and black?” I motioned to the other shoes she had brought me.

“To go with the dresses,” she smiled, “every girl just has to have at least one little black dress and one little red dress in her wardrobe, it’s just the way it is.” The red and black dresses I had liked so much were still laying on the bed where I had put them.

“Jenn, seriously?”

“Ricki, look at yourself again and tell me you don’t want this,” I looked at the girl in the mirror one more time and just smiled, “Besides, you’ve seen my closet, I’ll never miss them, and you’re worth it,” she smiled at me, I didn’t even realize she had feminized my name.

We spent the next few hours working on teaching me how to walk and act like a girl. Each time I looked in the mirror, it got easier and easier until she started laughing, telling me to tone it down a little so I didn’t get Mike too excited.

She found a bag for my underwear and my shoes and a garment bag for the dresses, I swear her closet was like a department store. I had put the simple white panties back on without even thinking about it, when Jenn saw me, she grinned and went back into her closet coming back with some opaque leggings, a sweater dress and a pair of riding boots with four-inch heels, my jeans, t-shirt, and sneakers went into the bag with my shoes.

When she saw I still had the enhancers stuck to my chest, she found me a simple t-shirt bra, it occurred to me that everything she was giving me was from Jenn PBJ, or pre boob job. I stifled a giggle.

“Now get out of here, I have to pack,” Jenn hugged me and patted me on the butt.

“Purse?” I realized I was going to need someplace for my wallet, keys, and phone.

Once again Jenn vanished into her expansive closet. She brought me four, one for each of the dresses, red, black, and purple clutches, and one with a shoulder strap for everyday use. We spent a few minutes discussing what a lady should keep in her purse, I followed her instructions, reminding myself to add my lipstick and compact from the makeup session when I got to my car. Hugging her again, I headed for the door; I’d have to think about her recommendation to include a few condoms, just in case.