Man to Woman

by Jane Futa

  “Um, anyway,” he started, rubbing the back of his neck.

  “Want to show me around?” Chelsea asked.

  “Uh, sure,” he said, before waiting for the girl to step out of the room.

  “Um, I’m kind of naked here, so you might want to…” Edward said, nodding toward the door.

  “Wow, um, Melissa didn’t say you were so… naughty,” Chelsea said. The girl smiled and neared Edward before the blonde called toward her.

  “Hey; I wasn’t asking you into bed. Can you give me a minute to get dressed?” He asked in frustration. The girl turned slowly and on her way out of the room, turned back over her shoulder. Her raven hair tossed as she shifted her eyes.

  Edward could tell that she was going to be a handful at the very least, and perhaps trouble by the end of the week.

  Edward gave Chelsea a small tour of his house and showed her to her temporary bedroom. As the afternoon progressed, the two seemed more comfortable around one another, with Chelsea seeming to find herself right at home. As the next few days passed, Edward tried to contact his sister, hoping for more details on his new transient roommate, though Melissa was unavailable.

  Unexpectedly, Edward had no real trouble with the girl for the first half of the week. She kept to her end of the house, and seemed to spend the good part of the day either in her room, or bustling about in town. The blonde couldn’t have been more relieved.

  “Hey,” he said, knocking on Chelsea’s door one evening. Though the dark-haired girl had remained mostly to herself, she hadn’t missed an opportunity to tease the older blonde. She’d found him most of the day in his home office, running his investment business. In the midst of an important conference call, she decided that it would be fun to pretend to drop something in the foyer and bend over, giving the stud a full view of her perky ass as it sat snugly in her little cotton thong.

  The girl knew what she was doing, clearly. And given that his latest sexual distraction had continued to ignore his texts, Edward paid attention. He also resolved to keep his distance, however. Chelsea was his sister’s best friend, and he certainly didn’t want to cross any boundaries.

  But once the dark-haired girl crossed a rather big one herself, he knew that something had to be done.

  Edward returned to his bedroom on the third night, after having been out most of the day. Too tired to go chasing any girl at the club, he reached under his bed for the sex toy a previous girlfriend had given him as a gag gift. His fingers grabbed for the little red box, but he felt nothing but space and carpet beneath the bed.

  Pulling up the sheets, he saw nothing but the same. “What the…” Edward started, before scanning his room and noticing the opened box sitting on his night stand.

  He became more confused than ever. Shaking his head, he sifted through the evidence of a sex-toy thief. There was only one likely suspect, but he couldn’t figure out what motivation Chelsea would have had. The sex toy had been a fake rubber vagina, and aside from pure female fascination, he didn’t know why she would have swiped the toy.

  Edward dropped the box and headed down the hallway before stopping outside of Chelsea’s room. He noticed the door was cracked as light spilled out from her bedroom, and into the dark hallway. Peering inside, his jaw dropped as he swore he could see the girl stroking the sex sleeve back and forth over her groin.

  “Hey,” Edward said, pushing the door open.

  The girl turned her face to see him, and gasped in horror as she flung the sex sleeve to the side and pulled her skirt down, out of view from the blonde alpha.

  “What the hell is this?” Edward growled as he stepped into the room and neared the bed where the beautiful girl was sitting in fear.

  Edward grabbed the warm sex sleeve in his hand and held it out. “What are you doing with this?”

  Chelsea only grinned and laughed nervously. Clearly, she would have had more leverage against embarrassment if Edward hadn’t walked in on her using the toy. Now, she knew she must explain herself.

  “Um,” she started, struggling to speak.

  Edward’s eyes flared. “You think that it’s okay to take things that don’t belong to you? I can’t believe this.” Edward started to pace around before her and shook his head. “I can’t believe I let Melissa talk me into this dumb idea. I mean, sure, you’re a total babe, but that’s beside the point.”

  Chelsea grinned devilishly. She suddenly realized that she’d had an out. She’d been attracted to the blonde alpha from the moment Melissa had shown her a picture of him back in Boston, but she never could have expected the blonde stud to feel the same way.

  “Edward, I’m so sorry,” Chelsea sighed. “I…”

  “What were you even doing with this? It’s not like you could use it. I saw you trying to, though. Were you just mocking me? You know, I’ve only used this a few times, I’ll have you know. This is just for when I’m feeling lazy and… wait a second; I don’t have to explain any of this to you.”

  Chelsea giggled in that moment. She enjoyed seeing the alpha so frustrated and felt the swelling beneath her skirt start to grow stronger and stronger. She’d been thinking of Edward as she fingered herself and stroked the toy, and now here he was, ready for her deepest apology.

  “I… I don’t know how to explain this but…” Chelsea started. “Well, maybe you should just see for yourself.”

  “See for myself?” Edward asked. He couldn’t help but salivate at the idea of seeing the teen’s precious little pussy. He’d wondered just how smooth and tight it was from the moment he saw her eyeing his cock beneath his bed sheets. And now she was somehow giving it up – and so easily? He shook his head.

  “I don’t understand,” he said.

  “I haven’t been entirely honest with you. I mean… it’s not like I’ve been lying to you or anything but I um… well, there’s a good reason why I took the sex sleeve.”

  The girl brushed her dark hair to the side and shifted her eyes mischievously. She grabbed Edward’s hand and brought him toward her, until the hulking alpha towered over her lithe body.

  The girl dragged Edward’s hand toward the inside of her smooth thigh. The alpha’s breath grew short and the hunger in his body spilled out. Edward’s cock swelled as he felt the heat from Chelsea’s pussy radiating against his fingers as he neared her sweetest, most private place.

  “Go ahead,” Chelsea begged in a whisper, all while eyeing up at the delicious hunk. She watched as the lust in Edwards’s eyes built. She was about to be taken by a real man. Her entire life had prepared her for this moment. All the make-up, the dress-up and the pretending; it had been for the alpha sliding his curious fingers toward her warmth.

  Edward lowered his hands to her little skirt, and gave a quick yank, revealing the pole that had set a tent in the plaid fabric around her waist. There, just beneath his hand, was a nice, plump, six inch penis that jutted straight from Chelsea’s pelvis. The girl sighed as Edward’s smooth hands came dangerously close to her hard, sensitive cock.

  She pulled her eyes from her waist and back up toward Edward, waiting in suspense for the man she’d found so attractive, to make his next move.

  “There’s no fucking way,” He said, pulling from her and running a hand through his golden blonde hair.

  “What’s so unbelievable about it?” Chelsea said with a little giggle. Her lithe little finger cornered her lips as they curled into a satisfied grin. The red lipstick beaming from them, only proved another level of deception.

  “Because you…you were hot,” Edward explained, pacing back and forth before her.

  Chelsea laughed even harder at this. “Am I not hot anymore?”

  “What? Of course you are. I mean… I don’t know,” Edward said.

  His mind raced with conflicting thoughts. Try as he might, he couldn’t deny that his cock was throbbing painfully hard in his jeans, desperate for sweet freedom from his boxers. He looked down and eyed Chelsea once more, taking in her beautiful, wide blue eyes that sat behind con
stantly batting eyelashes. She pulled her skirt down and adjusted the white blouse around her giant breasts, brushing down the silky fabric and sitting back on the corner of Edward’s bed.

  “Calm down,” she said, grabbing at Edward’s jeans as he passed by. She pulled him closer to her and looked up into his dark eyes.

  Edward’s lips hung open as he eyed down, only to see his bulge a scant few inches from her smooth, inviting little lips.

  “What’s wrong?” She asked. “Do you want me to go?”

  “No way,” Edward said. “I’m just… still sort of shocked.”

  “So I have a dick,” Chelsea said with a little laugh. “I’m still plenty girl. In fact, I would argue that I’m all girl. I just have a little extra. Is that so wrong?”

  Edward wasn’t sure what to believe. The only thought passing through his mind right then, was that a beautiful, gorgeous girl was only moments from his cock, as it sat behind his tight jeans. Chelsea ran her hands up and down the sides of Edward’s legs, and watching in delight as he sighed with relief.

  “I feel like I’ve betrayed you somehow,” she confessed. “I’ve really screwed up. And I know Melissa is never going to let me live this down.”

  “There’s no need to tell her,” Edward said. “I’m really not that pissed off. I’m just… confused, is all.”

  “Well, would it help if I showed you a way to relax?” Chelsea asked, with a tone of mischief singed on the tip of her tongue.

  “How so?” Edward asked.

  Chelsea slid her tongue to the corner of her mouth and concentrated. Her smooth pale fingers moved atop Edward’s cock and ran up and down, ever slowly. The touch left Edward’s cock pained and ravenous for release. His hips buckled forward slightly and he bit his lip, watching as the raven-haired slut sitting on the edge of his bed guided him into seduction.

  “That’s it,” Chelsea whispered, before undoing the brass button at the top of his jeans, and slowly unzipping them. As the denim loosened around his waist, he felt the cool air slip inside. Chelsea’s hungry fingers grabbed the jeans and pulled them down, along with Edward’s boxers. As his chest heaved with tense breath, he watched his cock spring out into the air and nearly slap Chelsea’s smooth face.

  “Whoa,” Chelsea said, moving her face back and giggling.

  “Oh my god,” she added with wide eyes and parted lips. She immediately broke into a smile as she wrapped her fingers around Edward’s long shaft. “I can’t believe this… it’s so massive.” Edward of course, wasn’t about to argue with her. He only sighed in delight as the girl’s smooth fingers slid over his dick and gifted small little teases to the sensitive skin.

  Chelsea stared down the wide, flared cockhead, and felt as her own shaft continued to swell beneath her skirt. She couldn’t help but feel like the perfect little submissive right then. She wanted to please this cute alpha in any way possible, and she knew that offering her sissy little mouth was a nice place to start.

  She parted her dark bangs and tucked them behind her ears before stroking Edward’s smooth, warm cock properly. She felt each vein as it throbbed in her palm. She felt as though she held his entire strength in her grip, and watched with delight as she looked up and saw his delicate sighs of pleasure.

  “This isn’t so bad, is it?” She said, stroking Edward’s cock and watching, mesmerized, as his heavy ball sack swung back and forth. She bit her lip, imagining all of the virile seed held inside of them, and how soon enough, it would be inside her.

  “Hell no,” he said, shaking his head back and forth and smiling in satisfaction. Edward ran his hand through Chelsea’s dark hair, guiding her firmly toward his cock. “You know what would be better, though?”

  Chelsea didn’t need to hear any more. She looked up and watched, her eyes wide, as she parted her lips and swallowed Edward’s cockhead.

  “Oh fuck,” the blonde said, sighing hard as the warm, wet mouth surrounded his hard tool. He thrust instinctively and winced as his long shaft sank deeper inside the sissy slut’s tight little mouth. A sense of satisfaction swept over him. This is only right, he thought. It’s the fitting punishment that I stuff that dirty lying mouth of hers.

  Chelsea sucked hard over Edward’s cock as it stuffed her mouth and moved down her tongue, toward her throat. She stroked his base, trying to accommodate his unusual length. She wondered just how she would fit all of him in her naughty ass, but she knew she would find a way.

  She reached down and snuck a hand beneath her skirt, stroking her own hard cock and mimicking the rhythm of her mouth as it slid back and forth over the blonde alpha’s gorgeous, pink cock.

  Chelsea closed her eyes and tasted every inch of sweet skin. She felt that whatever he wanted, she would give to him. He was hers to use, and as he grabbed the back of her head and pulled her mouth deeper over his cock, she obeyed with a sense of loyalty.

  “Mm,” Edward moaned. His lips hung open and he looked down toward the dark-haired slut on her knees before him. He reached down and massaged her large breasts, feeling each full orb in his palms as he ran over her stiff nipples. He was growing hungrier for her body than he could stand.

  “I can’t believe I’m letting such a dirty little whore suck my cock,” he growled. “I usually waste my time going after the obvious girls – the partiers. I had no idea that it was you quiet bookworm types that were the dirtiest ones.”

  Chelsea moaned on agreement, stroking her cock and pulling her mouth back off of Edward’s cock. She wiped her mouth and sighed. Smiling, she looked up to see Edward, who was reached down to pull her up. In doing so, he suddenly tossed her onto his bed. Chelsea landed on her back, giving a little squeal in response.

  With her little skirt flinging back over her belly, she revealed her juicy cock and balls. She splayed her smooth, silky thighs, spreading eagle and biting her finger nervously. She had no idea what Edward would do, and certainly hadn’t expected him to do anything beyond receive an easy blowjob.

  But the blonde stud neared her and flashed a look of pure lust in his eyes. He reached down, after hesitating a moment, grabbed Chelsea’s cock. His mind rattled with conflicting thoughts as he gripped the girl’s warm shaft and jerked it.

  “Fuck,” Chelsea moaned, rubbing her perky breasts as the alpha jerked her cock fast and intent.

  “You like that, you little sissy?” He growled. Chelsea nodded in pure pleasure as the blonde made his way out of his t-shirt, revealing his ripped chest and abs. She noted the various tattoos across his shoulders and smiled; he was just as bad as she’d thought. She suddenly feared that she could take his dominance, but she knew that she had to – it was the only way to make it up to Edward, who had been so generous.

  “Mm,” she smiled, as Edward pulled his jeans and boxers off his legs before returning to her cock.

  The stud didn’t know how he would later come to terms with this dirty little afternoon, but he didn’t care. Chelsea was right – she was a girl, who just happened to have more to play with. Edward found himself hungrier than ever, as he stroked her cock and watched as her face gasped in response.

  “I’m going to make you cum harder than you’ve ever done,” Edward said with a low, deep whisper. “What does my little fuck toy think about that?”

  “Please,” Chelsea moaned. “If you insist.”

  Chelsea’s legs writhed as Edward parted his lips and decided to return the favor. Chelsea at once felt the alpha’s mouth over her cock, sucking hard and fast. He pulled back for a moment and growled, “This isn’t going to last long. A little slut like you isn’t worthy of a blowjob. After all, I know you really want it in that dirty pussy of yours.”

  The fire gleamed over Edward’s eyes as he grinned and returned his mouth, sliding the warm, wet spit over Chelsea’s stiff shaft. She reached down and just barely touched her asshole with the tip of her finger. As she did, Edward slapped it down and pulled off her cock.

  “That’s not for you,” he said. “That’s for me.”

  T
he stud immediately lowered his mouth, sliding his tongue along the rim of Chelsea’s ass. The dark-haired girl writhed and heaved with breath as Edward’s mouth slid over her opening and left it quivering uncontrollably. The sensation was unbearable; she wanted one thing more than anything else, and hoped that Edward would want it just as much as her.

  He spit against her ass and ran his finger along the edge, before sinking it just inside her. Watching her body break open around him, he watched as this dirty little sissy moaned and contracted at his touch. He realized then that he was happy Chelsea had fooled him. He found himself hornier than ever as he watched the girl’s cock twitch and throb with every inch his finger dove into her. The unexpected enjoyment overtook him, and he stroked his own cock, preparing for the fucking of his life.

  He’d pounded so many girls on that very same bed, but certainly none like Chelsea. She was far different, and he was going to treat her as such. She demanded a big cock and a relentless, merciless fucking – it was only proper for a whore like her. And Edward sought to give her just that.

  “You thought you could crash on my couch and use my things without asking,” Edward growled. “You thought you could bat those pretty eyelashes of yours, toss that long dark hair of yours, and I would follow you around like some horny loser, hoping to bang the hottest girl he’d ever seen. Little did you know that you were messing with the wrong guy.”

  “Fuck,” Chelsea breathed heavily, rubbing her breasts as Edward fingered her ass deeper and deeper; first one finger, then two. She didn’t know how she was going to take his cock, which seemed at least five fingers worth. But she didn’t care. As his fingers stroked her prostate, she felt the blissful sting and tickle of a climax edging near. She didn’t want him to stop, but he pulled back, as if he could see it in her eyes.

  Edward grabbed Chelsea’s ass cheek before slapping it harshly. The crackle echoed through the room and left a small pink welt as the dirty transgender teen moaned in response.