Fearless - A Big Girls & Bad Boys Romance

by Cameron, D. H.

  “I don’t know. That’s quite a tale. You’re kind of scaring me and I’m just not sure you’re my type,” he said with a perfectly straight face. He was in range, however, so I reached over and punched him.

  “Ha ha ha. Very funny!” I said and Jack laughed at his little joke. I couldn’t help but join him though. I took another sip of beer and found it was my last. I shook the bottle, Jack took it from me and got up to go fetch two more. He was gone a moment and I knew when he came back I had to ask about Sarah. I needed to know how he felt for some reason. I don’t know why but I felt like if he couldn’t accept her, then we weren’t meant to be.

  It shouldn’t have mattered. It wasn’t as if dating Jack and being friends with Sarah had anything meaningful in common. I could have relationships with both no matter how each felt about the other but I didn’t want that. I needed Jack to accept her. I needed to know he was what I hoped. His lifestyle and his home made me think that he was but I needed to know for sure. Jack sat back down and handed me one of the beers but before I could ask Jack, he answered without me having to.

  “Your friends sound cool. I’d like to meet them,” he said.

  “Really?” I asked a bit surprised and Jack picked up on that.

  “Yeah, why?” he wondered.

  “I thought...well, I...,” I began to say but without much success before Jack smiled and jumped in.

  “Look, I can’t live the way I do and not accept others for who they are. I’m used to being judged, even by you,” he said and I nodded accepting the truth. “I’m a scruffy, outlaw, dumpster-diving biker. Who am I to judge? I live the way that makes me happy. Sounds like your friend Sarah’s found what makes her happy. Good for her,” Jack said and I suddenly had a big smile I couldn’t shake.

  “Thank you,” I said.

  “No need. So, I have a question. Did I pass the test?” he asked. I was surprised at that.

  “What test?” I asked innocently. I guess I was testing him but I was testing myself too.

  “Don’t bullshit a bullshitter,” Jack replied. I laughed at that.

  “Yeah, you passed. I passed the test too,” I said and then Jack really surprised me.

  “I like you a lot, Brandy. You’re...fearless,” he said. Oh my Lord. That’s what Sarah told me too. Be fearless. What the hell was with everyone quoting each other?

  “Do you know Sarah or something, she used that word too. Fearless,” I asked rhetorically but Jack answered anyway.

  “Yeah, she’s my brother,” Jack said straight as can be leaving no doubt he was serious. I choked on the beer I was trying to swallow but as soon as I saw the grin on Jack’s face, I knew he was screwing with me.

  “You’re an idiot. She’d be your sister anyway...I think,” I said and we both laughed at my confusion.

  “So, I assume your cool being my old lady?” he asked but it was a statement of sorts. Old lady? I knew that meant I’d be his girlfriend. Yeah, I was more than cool with that.

  “If you don’t mind being my old man, I could be your old lady,” I replied. Jack put his hand out, palm up and held it there. I looked at it, then at him and took his hand in mine.

  “Good! I need a decent lawyer,” he said and squeezed my hand. I smiled and took a sip of beer as Jack puffed on his cigar. I guess we were dating and I couldn’t have been happier. No reservations and no worries. If people didn’t like it, fuck ‘em. I was Jack’s old lady and I was proud that he was my old man.

  >>O<<

  Jack took us to get some burgers and fries after a bit. We took his truck so I didn’t have to get dressed for real. After we ate them back at his trailer sitting at the bar on those old stools, we cuddled up on his big leather sofa daybed thing and watched a movie. I slept over and we made love again that morning. OK, we fucked like bikers. Making love is for normal people. In any case, when I finally made it home the next afternoon, I was on cloud nine. I had to tell someone and there was really only one someone I wanted to tell.

  “I’m so happy for you, Brandy,” Sarah exclaimed when I told her all about my night with Jack.

  “Thanks. It’s partially you’re doing,” I told her.

  “Meh, you would have figured it out on your own,” she replied.

  “Um... can I ask you something, Sarah?” I replied.

  “Yeah, sure,” she replied. I know what I wanted to ask but I wasn’t sure how to ask it. I wasn’t sure it wouldn’t sound stupid. But I had to be fearless.

  “I like you a lot, Sarah. I know you’re a crossdresser and all but we can be like girlfriends, right?” I asked and it did sound kind of stupid. Sarah didn’t say a word for a moment and I wondered if I might have said something wrong.

  “Really? You mean that?” she asked and her voice was a bit shaky.

  “Yeah, I do,” I told her.

  “I’d love to be your BFF, Brandy,” she replied. Now I was getting emotional too.

  “Cool!” I replied but I had another question. “What’s your name? You know your dude name?” I asked. Again Sarah hesitated.

  “Why?” she asked in return and I could hear that she was hesitant.

  “If we’re going to be friends I just thought...,” I began to say but she interrupted.

  You’d better just call me Sarah,” she said and I thought I’d offended her or something for a moment until she added, “It’s Jack. I mean it’s really John after my dad but everyone calls me Jack so there’s less confusion.”

  “No shit?” I asked her.

  “No shit. Besides, I want to be Sarah with you, you know. I don’t mind you meeting the male me but I don’t want to be him with you. I want to be your girlfriend, OK,” she explained.

  “OK, but if I want to hang out on a Wednesday night, you might have to get all made up and put on something pretty,” I teased.

  “Promise?” she replied and we both laughed. We talked for a while about Jack and stuff and agreed to get together soon and go shopping or something. I felt like everything was clear suddenly. I had Jack and now I had a best friend. This was so cool. Better yet, I didn’t feel like I was struggling to fit in or make everyone else happy. I was just being me, doing what felt good and right, what I wanted and I loved it.

  The next morning, I went into work and Vic was already in his office back from his vacation. I’d had quite a week while he was gone and I looked it. The pink streak was still in my hair and instead of my usual skirt suit, white blouse and conservative heels, I wore something that I liked instead of what I thought I should wear. I wore a short leather skirt, a red blouse and matching heels. Underneath, it was all black lace including the garter belt that held my sheer black stockings with the seam up the back tight against my shapely legs.

  “Morning, Vic,” I said as I stood in his door.

  “Place looks nice. Thanks for cleaning...,” he began to say until he looked up and saw me. “You look...different, Brandy,” he told me as he looked me up and down with obviously inappropriate thoughts running through his head.

  “Do I?” I replied being coy appreciating his wandering eyes.

  “Yeah. So how’d everything go with Jack Anker?” he asked after shaking his head and forcing himself to look me in the eye.

  “I got him off. I got him off good,” I replied and giggled to myself. Vic couldn’t figure out what that was all about but I enjoyed my little turn of phrase immensely.

  “Uh...good. Anything else happen?” he wondered.

  “Nope. Pretty uneventful week,” I told him but it was anything but. I was Jack’s old lady and my new best friend was a crossdresser. I’d danced on the bar half-naked at Hogs and Heifers, won a wet t-shirt contest and smoked pot. I’d found my inner bad girl and let a dumpster-diving biker have his way with her. Best of all, that fearless, curvy vixen was here to stay.

  “Right,” was all Vic said. He knew something was up but for the life of him he couldn’t figure out what.

  “How was Hawaii? You and Lacey have a good time?” I asked changing the subjec
t. Vic’s expression changed.

  “Yeah, it was a good vacation,” he replied.

  “Well, how about I make us some coffee and you can tell me all about all the juicy details before we get to work,” I offered.

  “Yeah, OK. You know, whatever happened to you, Brandy, I like it,” Vic told me. I smiled as he handed me his empty coffee cup.

  “So do I,” I replied and went to go get us some coffee.

  >>O<<

  Fearless - Act II

  “Morning, Vic!” I greeted my boss after another fantastic weekend spent with Jack. We’d been going out for almost a month, well, it had been a month since Jack took me to Hogs and Heifers where I danced on the bar, took him back to my condominium and then kicked him to the curb the next morning. Since then, I’d learned a lot about myself. I’d learned to live fearlessly, to live and love like every day might be my last.

  “Morning, Bran...,” Vic began to say but he stopped as he caught a glimpse of me. I was in a black leather skirt that hugged my broad hips, a red satin blouse unbuttoned enough to reveal my black lacy bra and deep cleavage along with my usual matching garter belt and panties, black stockings and red pumps with little bows on top. A big, somewhat puzzled smile crossed his face. “I like how your hair matches the outfit,” he finally told me at a loss for anything else.

  “Oh yeah, I did this on Saturday,” I replied lifting the lock of my almost black hair that was dyed red. Vic could barely contain his appreciation. He tried hard to look me in the eye but his eyes wandered south over and over. I wasn’t interested in Vic and I don’t think he was interested in me but he was a man and I enjoyed the effect I had on him. I’d always felt a bit self-conscious since Vic’s wife was an ex-stripper and amazingly beautiful but now Vic couldn’t stop staring at me.

  “Uh...you look...,” Vice began to say.

  “Careful, boss man,” I warned playfully.

  “...nice,” he finished and smiled at me. I winked at him and then asked if he wanted some coffee. “Yeah, I was going to make some but I got busy. I’m wiped today. Lacey was rather...demanding last night,” Vic told me.

  “You poor, old man,” I teased and scurried away as Vic threw his pen at me.

  “I wasn’t complaining,” he shouted after me. I giggled. I still wasn’t sure this job working for Vic, an ex-con defense attorney representing the dregs of society, was what I wanted to do forever but it was growing on me. Besides, I met Jack Anker, Rogue as he liked me to call him in bed, here and that turned out pretty well. I still had dreams, however, of finding a job at a big prestigious law firm but for now this paid the bills.

  I got the coffee pot going and then went back to my office. The hallway was still lined with boxes and files but it wasn’t quite as bad as it used to be. The unit next door had been vacated and after much pleading and finally a few threats, I convinced Vic to rent it out so we could clean up a bit. He finally relented and did but we hadn’t had a chance to get the office cleaned up. He promised we’d come in on a Saturday and do it but Lacey always had plans for Vic that superseded work on the weekend. Baby steps, right?

  “Hey, kid,” Vic called to me as I passed his office. I stopped and leaned back to regard him.

  “Yeah?” I asked.

  “I just wanted to say that I really like the new you. And you don’t look nice...you look naughty as hell,” he told me. I bit my lip and smiled despite myself.

  “Thanks, you dirty old man,” I replied. Vic chuckled and I joined him, laughing as I went to my office to dig into the pile of files and dockets. I liked the new me too. I hadn’t been this happy in...well, ever. I was living life on my terms now, I had a new best friend and I had Jack. I should have felt like I had it all but I was eager to push the limits of my newfound courage and see what kind of trouble I could get into.

  >>O<<

  My face was pressed into the mattress, my arms stretched uncomfortably behind my back. Jack held my wrists firmly with one of his powerful hands, the other hand tugging at my dark hair as he hammered into me. I absolutely loved it when Jack got rough and took control. I squealed and screamed as he thrust into me, another fabulous orgasm ripping through me. Jack let go of my arms and I immediately brought them down to the bed, grabbed handfuls of the comforter, and squeezed for all I was worth. Jack wasn’t being nice, however.

  Jack was everything a girl wanted in a man and everything that girl’s mother told her to avoid. Tall, muscular and fit was an understatement. Rogue, his road name and the name I called him when we had sex because it was so damned hot, wore his sandy hair just past his shoulders and his scruffy beard and gray eyes made him look a bit dangerous. But beneath his rough, biker exterior, however, Jack was a caring, tender man with a hard, no-nonsense attitude. Especially now, as I submitted to his sexual desires, naked and losing my mind.

  “Fuck!” I cried out as his hand smacked my generous backside. I knew he’d left a red handprint on my ass as I savored the sting. But Jack had plans for me. He bent and held his thumb just in front of my mouth. I greedily took it between my lips and began sucking it as Jack continued to thrust into me. A moment later, he pulled his thumb from my mouth and began massaging my backdoor with it. “Oh God! Do it, Rogue!” I demanded. I never thought I’d like it this dirty and rough, but with Jack, it was all I wanted.

  Jack ignored my plea, instead continuing to massage my pink flower. I was going to complain but the stimulation sent me over the edge and I climaxed again before I could say anything. As the orgasm had its way with me, Jack pushed his thumb into me. Holy shit! Between his thick, rigid manhood filling my wet tunnel and his thumb tormenting my anus, I lost control. Thank God we were at my condo because my screams and shrieks would have had Jack’s neighbors at the trailer park calling the authorities.

  “Yeah, you like that, you sexy slut?” Jack demanded of me. I couldn’t answer. I managed to look back at Jack, tears filling my eyes and he saw that I did. Suddenly, Jack pulled from me and roughly rolled me onto my back. He took my stocking clad ankles in his hands and plunged back into me. I climaxed yet again but Jack was almost finished. I shook and shuddered as he desperately fucked me and then once the orgasm had passed, Jack pulled from me and covered my belly in his own orgasm.

  “Yes, baby! Come for me!” I urged him as I propped myself on my elbows and watched the amazing show. Jack’s thick cock twitched as he coaxed more and more of his thick orgasm forth. I loved it when he did that. A moment later, Jack was spent and I grabbed his big shaft and pulled him down on top of me.

  “Kiss me, Rogue,” I ordered him. Jack did as I wanted, his warm tongue forcing its way into my mouth. I greedily sucked on it before Jack rolled off of me and lay next to me, his arms and legs spread wide to catch his breath and cool off.

  “I love morning sex,” he told me as he found enough strength to turn and drape his arm over me.

  “Oh, so last night wasn’t any good?” I teased.

  “It was OK,” he replied and cringed, waiting for me to slug him. I didn’t.

  “Yeah, you were kind of a dead lay,” I chided Jack. He smirked and raised an eyebrow.

  “I did all the work, as usual,” he countered.

  “Piss poor work if you ask me,” I told him flatly. Jack glared at me for a second and then laughed out loud. I joined him. I loved the free and easy way we had together.

  “You nervous?” Jack asked changing the subject.

  “No, not really. Why would I be?” I wondered. Today his motorcycle club had a ride planned and it was the first time I’d meet most of them. I wasn’t really nervous. I mean I was a bit worried that I might not fit in or that they wouldn’t accept me. Maybe I was a little nervous.

  “They’re an easy going bunch. They don’t like cops and prosecutors but they love defense attorneys,” Jack said and winked.

  “Hey, don’t start talking shop or I’ll have to bill you, one hour minimum,” I warned. Jack smiled.

  “I like it when you demand payment, doll,” he said.
I rolled my eyes.

  “Shut up and make me breakfast while I take a shower,” I told him, grabbing Jack’s face and kissing him. As I broke the kiss, I slapped his face lightly. “Don’t forget the coffee either,” I reminded him. Jack liked cooking and never forgot the coffee but I had to keep him on his toes. I climbed off the bed and went to shower, feeling Jack’s eyes following me. I put a little wiggle into my step for his benefit. “Scrambled with hash browns, I said as I entered the bathroom.

  “Yes, dear,” he replied just before I shut the bathroom door smiling to myself. Thirty minutes later, I found Jack sitting at my table in the same apron I found him wearing when he made me breakfast after our first night together. A plate of steaming scrambled eggs and hash browns with plenty of pepper and a cup of coffee made just like I preferred sat waiting for me.

  “I’m beginning to think you like that apron a bit too much. I’m not going to find you in my lingerie one day, am I?” I asked.

  “No. I borrow Sarah’s clothes when I’m feeling girlie. You’re too short,” Jack replied. Sarah was my new best friend. She was a man and a crossdresser. Sarah was the funny and sexy alter ego of the high school vice-principle my longtime friend and former college roommate, Trudy, had introduced me to. She was the friend that helped teach me how to stop being afraid of what everyone thought and just do what made me happy. Considering she was a proud crossdresser, Sarah knew what she was talking about.

  “Short?” I replied. I was kind of short but he didn’t have to point it out.

  “Sorry, doll,” Jack said as I took a seat.

  “Just because you’re a giant and Sarah insists on wearing high heels everywhere, doesn’t make me short,” I complained.

  “It doesn’t make you tall either,” Jack said. I stuck my tongue out at him and then winked at him. Jack chuckled. We ate in silence, Jack’s eggs and hash browns too good to let get cold. I did the dishes as he showered and when Jack was done, I kicked him out of my bedroom to get dressed. I wasn’t going on a ride with his motorcycle club dressed in the tank and boy shorts I’d thrown on after my shower. I’d been thinking about what to wear all week. It was too hot for much leather but I’d found a killer black leather vest when I’d met Sarah for lunch earlier that week. That took care of my top and for the bottom half, I made a pair of Daisy-Dukes from an old pair of blue jeans. Besides a black thong, a studded leather belt and some black platform boots I’d picked up a few weeks back, that’s all I wore.