Fearless - A Big Girls & Bad Boys Romance

by Cameron, D. H.

  “But...well...I’m a man, Jack. You’re not...,” Sarah tried to say delicately and failed.

  “So what? Life’s short and I’ve never been with a girl like you. Brandy and I would love to have you join us,” Jack said. I was so proud of him. I think Sarah was feeling a little down about being different and Jack was trying to make her feel better.

  “Really?” she asked still not quite sure about the idea. I was and I think Jack was too. Did it matter if Sarah was really a man? She was a good friend. Besides, the idea was deliciously kinky.

  “Yeah, really. Go get the key to that stupid cage and come to our room. But don’t take it off just yet, OK?” I told her. Sarah thought it over for a second and then smiled. She stood up and hugged Jack, almost as tall as he was. I got up too and she pulled me in for a hug as well.

  “You guys are awesome,” she told us.

  “Yeah, yeah. Go get the key you sexy bitch,” I told her. She let us go and dashed off in her tiny dress and high heels. I wasn’t sure how far this would go, how far Jack was willing to go, but in any case, this would be fun. Sarah disappeared and Jack pulled me into his arms.

  “You’re a naughty girl,” he told me.

  “I just want to see how far you’ll go,” I teased.

  “Do you?” he asked.

  “You don’t mind, do you?” I asked. I didn’t think Jack did. He typically didn’t do anything he didn’t want too.

  “No, I’m actually kind of excited. Nervous but excited,” he admitted.

  “Maybe if you do well, we can find a big, strong man and I can watch you two get all gay,” I told him. One of Jack’s eyebrows went up and he frowned.

  “Somehow, I think you’ll manage to talk me into that,” he said. I giggled.

  “I wore stockings under my skirt,” I told him. Jack’s hand slid over my ass and he found the clasp under my skirt. I was in a black pencil skirt, a red satin blouse, black stockings and red heels.

  “Yeah, I figured you did. We should go,” he said, took my hand and led me off towards the elevators. I had a tummy full of butterflies myself. This was a bit deviant but that didn’t bother me. Jack said it. Life was short. Sarah was pretty and a sweetheart. So what if she was a man in a dress? Who cared what people might say? It was none of their business what we did. I’m sure they’d call us names like those two bikers at the pool had but those were just labels meant to demean and divide.

  If Jack and Sarah actually did it, did that make Jack gay? No. Was Ruth a lesbian because she found Kat attractive and wanted to have sex with her? No. Hell, I’d have sex with Kat. Was Sarah gay because she dressed up like a girl, went to bars and sucked off strange men in the parking lot? Well, maybe. It didn’t matter. We were who we were and who we chose to sleep with didn’t define us anymore than what we looked like, what we did for a living or where we came from.

  Jack and I found Sarah at our door waiting impatiently. I really looked at her as we approached. She was really sexy. She wore a white clingy dress that failed to completely hide the device she wore to keep her chaste. It was subtle but if you knew it was there, it was unmistakable. I’d played with it when she told me Kat had put her in chastity device, teasing Sarah, but that was just for fun. OK, I was being kind of mean. Suddenly, I wanted to really tease Sarah, however. She had revealed that she liked being teased and I meant to give her what she wanted. She liked being denied and she relished the humiliation.

  “Been waiting long? I asked as we approached.

  “No, I was about to knock when I heard the elevator bell,” she said. Tonight she was in a flame red wig, long and straight. It looked good on her, almost natural against her light complexion. She held up the chain that held the key to the lock on her chastity device. I took it from her.

  “Don’t get too excited, girl. You’re going to have to earn your release,” I informed her as I fastened the chain around my neck. Sarah appeared shocked but pleasantly so.

  “I should have never told you all of that,” she replied.

  “Too late. Now, get on your knees and suck Jack’s cock, you sexy slut,” I demanded. Sarah and Jack were surprised by my order and my tone, almost as much as I was shocked at my own words.

  “Right here, doll?” Jack asked.

  “Yeah, right here in the hall,” I said. Jack and Sarah looked around but the hallway was empty. Sarah hesitated a moment but then did as I wanted. She fell to her knees and began working at Jack’s belt and blue jeans.

  “I can’t believe we’re doing this,” Jack said but then sighed as Sarah pried his semi-hard manhood free and wrapped her lips around the crown. “Oh fuck!” he said as Sarah began to suck my old man’s cock. God, that was hot! Jack was suddenly the shy one, unsure of my demands. I had become a bit aggressive. Maybe I had a mistress lurking inside.

  “You’re officially bisexual,” I teased Jack. Sarah giggled despite her obvious discomfort at doing this in a public place.

  “You’re crazy, doll!” he told me as he watched Sarah work. The elevator dinged and Sarah pulled back but I quickly pulled out my key card and unlocked our door before taking up position between Jack and Sarah and the elevators to block anyone from seeing exactly what was going on.

  “Keep going!” I told Sarah.

  “Brandy!” she complained. I looked over my shoulder.

  “Do it!” I urged her. She rolled her eyes and took Jack into her mouth again. I looked back down the hallway and an older couple emerged. I was ready to tell the pair behind me to rush inside the room but the couple went the other direction, not even noticing us. “They’re heading the other way,” I said and moved aside. Sarah glanced down the hall. Jack just smiled at me.

  “Keep going, Sarah,” I told my best friend and ducked into the room. I began undressing. Jack watched me as Sarah sucked him.

  “Damn, I love those lawyer suits,” he told me as I revealed my underthings. I wiggled out of my skirt and then undid my blouse and shed it. Next was my bra and panties leaving me in just my red and black lace garter belt, stockings and heels.

  “Get your asses in here, you exhibitionists,” I joked. Jack and Sarah scrambled into the room and Jack slammed the door closed.

  “You’re going to get us arrested, Brandy,” Sarah said. I laughed.

  “I already got Jack arrested,” I replied. Sarah giggled but Jack just shook his head at my brazen behavior. “Get undressed, old man. You...,” I said to Sarah, “...know how to eat pussy, I assume.” I climbed onto the bed, flopped onto my back and spread my legs. Sarah looked at me with lust.

  “That’s about all I’ve done since I met, Kat,” Sarah told me.

  “Good, but take that dress off first,” I ordered her. Jack was busy trying to get naked, having trouble with his boots as usual. He had a goofy look on his face, almost as if he didn’t quite believe what was happening. Sarah peeled her dress over her head. She was in shimmering tan pantyhose and a bustier. I could clearly she the cage made of clear plastic she wore. “Leave the pantyhose and heels on but loose that bustier,” I demanded.

  “But my tits,” she complained.

  “Loose those things too,” I said. Sarah shrugged and did as she was told. It didn’t take long but the adhesive holding her breast forms in place left her chest red after she peeled them off. Honestly, it looked painful as she did it but it was obvious that Sarah was as excited as I was and didn’t mind. A moment later, Sarah lay between my legs and without hesitation, she began lapping at my pussy. The scene was a bit surreal but it felt damn good.

  Jack got his underwear off and came to the bed, his cock rigid and standing at attention. “About time,” I told him. And pushed my plush breasts together. Jack knew what to do. He straddled me and flopped his thick shaft between my boobs. I massaged him with my soft, womanly flesh. I felt so darned naughty. “Are you going to fuck my best friend with this thing?” I asked. Sarah’s rhythm was interrupted when she heard that but she didn’t stop. Jack didn’t hesitate in answering.

  “Dam
n right, doll,” he said. Sarah stopped eating me when she heard that and gasped. I peered around Jack at her.

  “You want it don’t you, Sarah?” I asked her. The look on Sarah’s face was priceless.

  “Yes!” she admitted, her voice shaky.

  “My old man’s going to fuck you hard and long, Sarah, and if you make him happy, I’ll make you happy,” I told her.

  “OK,” she replied quietly. She was obviously overwhelmed.

  “Are you hard in that cage, Sarah?” I pressed.

  “Very,” she told me.

  “You are a slut, aren’t you?” I asked but Sarah didn’t answer. Her mouth was busy again between my thighs. Jack had a wild look in his eyes.

  “You’re a bitch,” he mouthed at me. I giggled and ran my long nails down his hairy chest and over his tattoos.

  “I love you too,” I mouthed back at him. He pulled his cock free of my breasts and shoved it in my mouth roughly. I gladly sucked him like my life depended on it. Maybe it was the drinks or the fact Jack’s freedom was in jeopardy. Maybe it was the fact I was sharing Jack with a crossdresser but I was aroused beyond belief. I was a bit out of control and the night took on a life of its own. This was just flat taboo. Jack wasn’t gay but Sarah was, sort of. I’d never been with a woman but being with Sarah kind of felt like that. In any case, this was dirty, naughty and deviant and I loved it.

  How far I had come since I met Jack and Sarah. Back then, I was so worried about what other people thought. I lived to please others, to live up to their expectations or too often what I perceived they expected from me. I lived on the straight and narrow, never deviating too far from what most people considered normal. I wasn’t bothered too much by my weight but I wasn’t proud of it. I saw it as a liability that I had to deal with.

  Now, I just didn’t give a fuck. The more I experienced the wild side, the more I wanted. After I had the threesome with Jack and Butch, I wondered if maybe I was overcompensating, getting carried away with my new freedom. Since, I had decided otherwise. This was me. There was no going too far if it’s what I wanted. It was part of the adventure and regret was foolish.

  I no longer worried about my weight either. I was big. Hell, I was fat. I had curves and Jack loved me for them. I figured out somewhere along the way, probably when Jack and Butch were sharing me, that sexy wasn’t about how I looked. It was about how I acted. Sexy was an attitude. Sarah didn’t pass all that well. I mean she looked feminine and pretty but it was obvious she was a crossdresser. But she pulled it off not just because she looked and acted female but because she had a confidence. Now I was proud of my body and I liked showing it off. My body didn’t make me sexy, it was my attitude.

  In fact, she was the one that taught me to live like this even more than Jack. She taught me that living fearlessly was the only way to live. Life was too short and precious to let other people place limitations on you. That didn’t mean there were no limits at all, but they were self-imposed limits and I didn’t have many left. I loved my new life, the freedom to explore my desires, sexual and otherwise. Sarah had helped teach me that and tonight I was going to thank her properly.

  “Get off me you big oaf,” I said after I managed to get Jack out of my mouth. I shoved him aside and watched Sarah as she lovingly lapped at my soft, swollen sex. “Make me come and I’ll make it worth your while,” I told her. Sarah smiled and sucked on my swollen nub as she slipped a finger into me. I sighed as she found that magic place inside. The climax that hit me came fast and sudden. I squealed as the pleasure overcame me.

  “Fuck that’s hot,” Jack growled as he watched the oddly arousing scene. Sarah kept up the pressure, indulging me fully and completely, a dutiful sissy serving her mistress for the evening. I needed to the pay her back for being such a good friend but she could keep that up all night for all I cared. I let her give me another powerful orgasm before I decided to let her join in on the fun.

  “Get up here,” I said and stirred my finger in the air. Sarah understood and turned around to straddle me as her head dipped between my thighs again. I dug my nails into her nylons and ripped them open aggressively. I had a great view of her equipment now. A clear, curved sheath held her penis and didn’t give it much room to roam at all. A ring locked behind her balls but left them free. Sarah was completely smooth, girly almost. Her pretty ass was spread wide and her pink orifice beckoned.

  I ran my tongue over my best friend’s anus and she gasped. I dove in, eating her like she was eating me, soft and slow. Was this what it might be like with a girl? I imagined it probably was. Jack sat next to us, watching Sarah and I sixty-nine. He couldn’t help but stroke his big shaft as Sarah and I began to writhe next to him. Soon I was on the edge of climax but I knew Sarah couldn’t attain any satisfaction. The idea she had to endure this without relief pushed me over the edge.

  I moaned and sighed as a wave of deep pleasure consumed me. My hands roamed Sarah’s surprisingly smooth body and her nylon clad legs as I orgasmed. For a moment, Jack was forgotten. It was just Sarah and I, pleasuring one another. I abandoned her ass and sucked her balls into my mouth. Sarah whined as she enjoyed the stimulation. I sucked on her jewels as Sarah’s hips began to undulate in desperation. I enjoyed another delicious orgasm as Sarah struggled to get more than the chastity device would allow.

  As the orgasm waned, I let her soft balls free. “Do you want me to suck your penis,” I asked. Calling it a cock just didn’t seem right.

  “Oh my God! Yes, Brandy, yes!” she exclaimed excitedly. Sarah was worked up and it was sexy. She was desperate, in fact. As far as I know, she had been wearing that device since she told me about it several weeks back. She had probably been denied pleasure the entire time. But Kat had given her permission to seek relief. I don’t think Sarah’s lesbian mistress foresaw my best friend being relieved quite like this, however.

  Sarah climbed from me and she was shaking. Her penis was swollen in the sheath that contained it. I got up and invited her to lie down. Sarah did and I knelt between her long legs. It was hard to forget she wasn’t a woman, despite her nudity and her penis. She was soft and pretty. Her chest was flat but still she looked feminine without any body hair. I ran my hands over her pantyhose encased legs and then up over her smooth torso. Sarah sighed deeply.

  Then I fished the key from between my cleavage and held it for her to see. “So, Jack, should I release her?” I asked. Jack had figured out the game.

  “No way, doll,” he replied. I shrugged and Sarah looked like she might start crying. For some reason, that was sexy as hell. But just because Sarah was still trapped in that device didn’t mean I couldn’t make good on my promise. I bent and took the sheath into my mouth and lovingly sucked it as Sarah looked on with desperation in her eyes. “Damn, Brandy. That’s brutal,” Jack remarked.

  “You have no idea, Jack. It’s been almost four weeks. I’m dying,” Sarah told him. Jack wasn’t all that kind either.

  “Maybe this will take your mind off your problems,” he said as he moved next to Sarah and offered her his cock. Sarah greedily rose up and wrapped her lips around Jack, sucking him as she stroked him. Sarah’s hips churned under me, the device fucking my lips but with little effect. Still, Sarah couldn’t take her eyes off of me as I pleasured the plastic sheath even as she did the same to Jack’s impressive manhood.

  I spent the next few minutes tormenting Sarah. By the end, she was pouting and writhing in frustration. I pulled my lips off of the sheath and licked it seductively. “You want some satisfaction, you sexy sissy? If you were a real man like Jack, you could just fuck me silly but you’re not. You’re a crossdresser. You don’t fuck girls, you get fucked like a girl, isn’t that right?” I asked. Sarah pulled Jack from her mouth and nodded vigorously.

  “Oh God, yes!” she replied.

  “You want Jack in your ass, don’t you?” I pressed her.

  “Please, Brandy. I need it so bad,” she pleaded.

  “Jack, you’re up,” I told my old ma
n. He nodded and took my place between Sarah’s legs. He was sopping wet and oozing his slippery juices. Jack was as excited as Sarah. He seized her legs and pushed them over her head as his thick cock hovered near her back door. Jack was fuming like a mad bull. Sarah was in for it. “You ever fuck a man like my old man?” I asked Sarah.

  “No, not like Jack. Fuck me, please?” she begged. Jack obliged my crossdressing friend, pushing himself into Sarah. She began to hyperventilate as Jack entered her. I knew Kat had prepared Sarah well for this moment and it wasn’t long before my old man was balls deep in my best friend. But even Kat’s strap on hadn’t prepared Sarah for the real thing. Jack pulled himself back and then after a pause he began to thrust into Sarah.

  She screamed as Jack built up speed. I looked around hoping the walls weren’t as thin as they looked. Soon Jack was hammering into Sarah, unconcerned with her comfort but then again Sarah wasn’t complaining. I sat back and touched myself as I watched Jack and Sarah. It was so sexy. Jack’s lust and Sarah’s desperation were palpable. Sarah moaned and sobbed, almost as if she might cry. I knew the feeling. Jack had taken me to that place but I was climaxing endlessly instead of being denied.

  But this couldn’t go on for long. This was about Sarah now. I’d received enough physical satisfaction. I needed to satisfy my darker desires. I unfastened the chain about my neck and then unlocked Sarah’s device. It took me a moment to figure out exactly how to remove it but when I did, Sarah’s penis swelled to its limit. She wasn’t big but she wasn’t small either. Sarah’s penis drooled in need, purple and quivering.

  “I hope you’re ready, girl,” I warned her. Sarah regarded me. Her eyes were a mix of anticipation and fear. I settled next to my best friend and as softly as I could, ran my fingers over her length. Sarah cried out as her body tensed. “You’re so sexy, Sarah. You’re so hard. I bet you want to come, don’t you?” I asked.