by John Dylena
“Brian, how do you feel about being a woman? Talking like one, dressing like one, acting like one… getting fucked like one?”
Brian jerked back at the bluntness of her question.
“I, uh, well…” He scratched his head. “I mean, at first I was apprehensive about it. Like when I had to put on a maid’s outfit and clean the apartment. But as the day went by, I grew to like it. I don’t know, I think it brought out something in me, something new, and I found that I enjoyed it.”
“What about afterward? What about when we went back to my condo and I dressed you up in those different outfits, got you a new wig and breast forms, and made you come back here all dressed up?”
“Oh, well, I enjoyed that because…”
“Because?” Leah leaned forward.
“I was with you,” he said quietly, his face turning red. Leah blushed as well.
Brian continued. “It’s not something I want to do twenty-four-seven. I have no desire to transition or anything. I enjoy being a regular guy, but I do have a lot of fun when you turn me into Brianna.”
“I was afraid…” She trailed off.
“Of what?”
“That I made you gay.”
Brian fell back onto the couch, laughing. Leah looked at him, unsure of whether to be confused or upset.
“Leah, I am not gay. I mean, sure, I sucked Lee’s cock once, and he fucked me, but that was done in the heat of the moment. I had gotten so aroused—not to mention he threatened to send the pictures of me to everyone we knew if I didn’t do it. I had no other choice.”
He leaned forward and kissed Leah. “That doesn’t mean I’m now attracted to men and men only. Women are still my preferred choice ninety-nine times out of a hundred. But I’d be lying if I said I didn’t enjoy sucking his cock.”
Leah grinned and cocked an eyebrow. “Really, now?”
Brian’s face turned a deeper shade of red. “I mean, I’ve always been a little curious about it. I believe a lot of guys have at least thought about it once in their lives.” He shrugged. “So, no damage done. But it’s something I don’t want to do again for a little while.”
“Thank you, Brian,” Leah said, her voice soft.
He looked at her and saw tears in her eyes. He watched them fall slowly down her cheeks to her chin and onto her skirt. She took his hand and he looked back into her eyes.
“I’m so glad we have had this opportunity to connect—to really get to know each other as we should have months ago. All this time, you and I could’ve been together and happy.”
Her sadness quickly gave way to anger and frustration. She gritted her teeth and snarled.
“Fucking Lee. He had to do this to us—to tear us apart like that—and all for his own selfish needs.”
Brian put his hand on Leah’s cheek and turned her face toward his. “Leah, I am here now. His deeds are but a flesh wound that’ll heal in time.”
“I know,” she said, her anger subsiding. “But I won’t be able to put it behind me until he gets what he deserves.”
“Does this mean you’ll finally tell me what your plan is?”
Leah smiled and laughed a little. “Yeah, sorry about that. Here’s my plan…”
“Guess who’s back?!” Lee called, then frowned at the silence. His apartment was empty and dark as if no one had been home for days. That’s odd, he thought. Leah said she’d be here waiting for me…
He walked further into the apartment, his suitcase trailing behind him, and stopped when he saw his door closed and the light coming out from underneath. Lee grinned and left his suitcase in the living room.
“Hey, Leah. You in here?” he said, slowly opening his bedroom door. He stopped and stared when he laid eyes on his bed and the woman sprawled out on top of it.
His room was barely lit. A couple of small candles strewn about the bedroom created just enough light that she could be seen in all her beauty. Leah sat up onto her elbows and winked, and Lee’s eyes moved slowly down her body, taking in every inch of her perfect flesh wrapped in beautiful lingerie.
She wore black lace lingerie with dark stockings connecting to her matching garter belt, as well as a pair of shiny black pumps. Leah rubbed her legs together and bit her lip as he took her in.
“Like what you see?” she asked playfully.
Lee stumbled and grabbed onto the doorframe as Leah rolled over onto her belly and bent her legs back, showing off her perfect ass. He swallowed hard as he stared at the lace thong that slipped in between her cheeks and the garters that followed the curves of her body.
“I’ve been waiting for you to get home,” she said as she rolled on to her back and tugged at the bridge between the cups of her bra. “I have a surprise for you.”
“Oh? What is it?” he said as he lurched toward her like a zombie, his eyes glued to her breasts. He got onto the bed and climbed on top of her.
“Well, you know how you’ve always wanted a threesome?”
Lee’s eyes widened with excitement. “Really? You mean it? We’re finally going to have one?”
“Yeah, that’s your present.” She looked past him at the door and shouted. “Come on in!”
Lee’s smile stretched from ear to ear as he climbed off of Leah and looked to the door anxiously.
“I had her hide in Brian’s room,” Leah whispered into his ear.
Lee heard the door open and shut, then the sound of high heels slowly traipsing across the wooden floor. They echoed in his head, and with each step, his excitement and anticipation grew.
Leah knew how much he wanted a threesome. He had brought it up after their third date. It was only in passing, but after their first month together, he had plainly asked for it to happen.
She did find the thought of playing with another woman hot, as it brought back her memories of her time in college where she’d had a girlfriend for a couple months. But as usual, Lee didn’t consider her interests or desires, and she highly doubted she could convince him that the third be a man instead.
Boy, is he in for a treat tonight, Leah thought, grinning wickedly as she watched Lee.
Brian came into view wearing his pink dress and heels, and Lee’s jaw dropped.
“Lee, this is Rebecca. She is a friend of mine from college. We dated back then.” Leah winked at Brian and he giggled. “Say hello, Rebecca.”
“Hello,” Brian said in his best female voice. He bit his lip as he waved, and he had a hard time hiding his laughter. His roommate was a hundred percent sold on the scenario. He had no idea.
“Well, hello, Rebecca,” Lee said, moving his hand though his hair and putting on a cocky grin. “Why don’t you join us in bed?”
Brian’s face was bright red as he climbed onto the bed next to Leah. She wrapped her arm around him and brought him close. She looked back at Lee, saw the excitement on his face, and reading his mind, she brought her lips to Brian’s and kissed him.
“Oh, fuck, that’s hot,” he said as he watched the two “women” make out. His mouth became dry and his cock grew hard as their hands fondled each other’s breasts and their tongues danced.
“It’s only a threesome if the man is included, ladies,” Lee said as he squeezed Brian’s ass.
“I-It’s okay, Leah,” Brian said as he climbed off of her onto Lee. Leah watched him carefully and put her arm around Lee.
Brian reached down and unbuttoned Lee’s shirt, pulling it off of him and tossing it aside. He bent down and kissed his chest as he slid further down. Leah threw her leg over Lee and straddled his chest as Brian undid his roommate’s pants and pulled them down off of his legs, tossing them aside.
Lee smiled as he was stripped down to his underwear and socks. He loved being serviced by two gorgeous women. Leah rubbed his chest and bent down to kiss him, her hands grabbing his arms and lifting them up toward the headboard.
Brian rubbed Lee’s cock through his boxers and kept his roommate oblivious to Leah’s movements. She reached under the pillows and pulled out a pair of
cuffs and handcuffed Lee to the metal headboard.
“Uh, what’s going on?” he said, tugging at his bindings.
“I’m sorry, babe,” Leah said as she caressed his cheek. “Rebecca is into that kinky stuff, and she said it would be hotter for the three of us if it were involved.”
“It’s all right,” he said, looking past Leah to Brian. Brian smiled as he played with the waistband of Lee’s boxers, slowly pulling them down. “We can do it this one time. Just no whips or any of that freaky stuff.”
Leah rolled her eyes and looked back at Brian. He climbed up off of the bed and returned moments later with a blindfold. Lee pulled back as she brought it toward his head, but he eventually let it put it on him.
“Yeah, okay…” he said. “This is kinda hot. Though if you two are going to make out again, then I’m going to be upset.”
Leah nodded, and Brian pulled Lee’s boxers and socks off of him. She turned around and wrapped her lips around Lee’s cock as Brian climbed off of the bed.
“What are you two girls giggling about over there? Better not be about the size of my cock.”
“No, we’re just laughing about how much fun we’re going to have.” She signaled to Brian and he returned holding a pair of panties. He smiled as he slipped them onto Lee’s feet and pulled them up to his knees.
“Hey, what are those?”
“Oh nothing,” Leah said, going back down on Lee’s cock. She licked and stroked it as Brian bunched up a pair of stockings and slid them on to Lee’s feet.
“Okay, what the fuck are you doing?!” he said, raising his voice and tugging at his handcuffs. “I said no kinky shit!”
“Aw, but babe…” Leah grimaced as she talked to him. She always hated calling him pet names, but it was something he wanted her to do. “I promised Rebecca.”
Lee grunted, but Brian and Leah didn’t even wait for his answer before they slid the panties up to his crotch and pulled the stockings up to his thighs.
“This had better be fucking worth it!” he said, his body shifting uncomfortably.
“Oh, it will be,” Leah said with a sweet, devilish smile.
Brian climbed back onto the bed and switched places with Leah. He bent down and kissed Lee as she climbed off and grabbed her phone.
“I’m all wet,” Brian whispered into Lee’s ear.
“Oh?”
“Would you be a gentleman and tongue me? I promise I’ll give you the best blow job ever.”
“Deal,” Lee said, grinning wide.
Brian looked over to Leah, who was giddy with excitement. She held her phone up and gave him a thumbs up. He scooted forward and lifted up his dress and pulled down his panties, letting his rock hard cock fall out and into Lee’s face.
“Let me see that tongue,” Brian purred.
Lee chuckled as he stuck his tongue out. All at once Brian removed Lee’s blindfold and stuck his dick in Lee’s mouth. Leah quickly pressed the button on her phone, taking as many pictures of Lee sucking Brian’s cock while wearing lingerie.
Lee spat and cursed, yelling and screaming and kicking his legs as Brian quickly got up off of the bed and stood next to Leah. They laughed at the pictures of Lee and he stared at them, both furious and confused.
“What the—”
“Oh, shut the fuck up, Lee,” Brian said in his native male voice.
Lee’s face twisted into confusion and his jaw dropped when he finally recognized who “Rebecca” really was.
“Holy fuck. Brian? That’s you?!”
“What? The cock didn’t give it away?”
Leah burst into laughter as she snapped a couple more pics of Lee in her lingerie. “And… done!”
“ ‘Done’ what?! What did you do?” Lee shouted as he tugged on his handcuffs.
“I uploaded the pictures to my cloud drive. Now if you want them deleted, there’ll be some things you have to do for us.”
“Brian, let me just say that you look like a real chick. Did you go and get implants or something? I mean, if you really wanted to fuck my girlfriend, you could’ve just asked. I wouldn’t mind having a submissive fag—”
“Enough!” Leah said, slamming her heeled foot onto the ground. “You insult him one more time and I’m sending these pics to your frat buddies. Understand?”
Lee grumbled and she walked up to the bed and showed him the screen. Her thumb hovered over the “send” button.
“Yeah, yeah. Okay.”
Leah canceled the text and took a calming breath. “Your answer to this next question will decide your fate.”
“What does that—”
Leah interrupted him. “Did you or did you not sabotage me and Brian’s first date?”
Lee said nothing.
Leah took another breath. “I said, did you or didn’t you—”
“Yes, I did,” Lee muttered. “You want the truth? Yeah, I wanted to date you. Brian had been turning down the women I hooked him up with, and I realized that after I set him up with you that he would probably just say no again, and then I would have a shot. But he didn’t say no, and I wanted to go out with you instead, so I ruined it for you.”
“And to think I called you my friend,” Brian spat.
“Heh, look at you, all slutty and shit. I figured you weren’t man enough for Leah. Guess I was right. You know, I don’t mind if you want to suck my cock again.”
“That’s where you’re wrong, Lee,” Leah said, surprisingly calm. “The only one sucking a cock here is you.”
Leah gestured to Brian and he climbed up onto the bed and placed his cock in Lee’s face.
“Get that thing away from me!” Lee shouted.
“I’m not going anywhere,” Brian said, slowly stroking his cock. “I think it’s time you paid us back for not only ruining our date, but also blackmailing me into sucking your cock.”
Lee looked away from Brian to Leah. She shrugged and waved her phone.
“I don’t have any choice, do I?” Lee said, his rage dissipating.
“Nope. But don’t worry, I’ll be gentle,” Brian said, sliding closer.
Lee stared at his roommate’s cock, frowning and looking away from it to Brian, then to Leah. They just stared back, patiently waiting for him. Leah smiled as she climbed onto the bed behind Brian and gently rubbed Lee’s cock through his panties.
“No, stop that,” he said, squirming.
“What’s the matter, Lee? Is this turning you on?” He bit his lip and continued to writhe on the bed. Leah rubbed his cock harder, smiling as it grew hard in the panties. “I think you like it.”
Lee closed his eyes and moaned, his cheeks turning bright red as the lust flowed through him. When he opened them up, Brian’s cock was right in front of him. His mouth watered as he stared at it hungrily. Leah continued to rub him, and he finally caved.
He opened his mouth and Brian placed his cock on Lee’s tongue. He pushed it forward and Lee wrapped his lips around it. Brian smirked at the way Lee’s face twisted in disgust, but as he slid his cock in further, his contempt faded away into pleasure.
Brian pushed his hips forward, sliding his cock even further. Lee’s tongue rubbed the underside of his shaft and he pulled back. Then he pushed his head forward as Brian withdrew.
“I think he likes it,” Leah teased as she pulled down the waistband of Lee’s panties and letting his cock freely harden. She gripped his rod and slowly stroked, rewarding him with faster, firmer pumps as he took in Brian’s cock.
Lee moaned through the thick, meaty dick inching toward his throat, and Brian moved in closer and pushed his cock all the way into Lee’s mouth. His roommate looked up at him, his face flushed and his body aglow.
Brian bit his lip as he picked up the pace of his thrusts, fucking Lee’s mouth as Leah jerked him off harder and faster. Lee’s moans grew louder and louder, and Brian was getting closer and closer to cumming.
“Wait,” Brian said, pulling out of Lee’s mouth. He looked back at Leah and she stopped stroking, forcing
Lee to whimper.
“What is it?” Leah asked.
“Flip him over onto his knees so I can fuck him properly,” he said, quoting what Lee had said when he’d fucked him back when Brian was dressed up as a maid.
Leah nodded and Brian climbed off of Lee. He reached into the dresser by his bed and pulled out one of Lee’s many condoms. He slipped it on as Lee obeyed Leah’s command to roll over.
Lee looked back at the two of them and whimpered as Brian lined up behind him.
“All of this could’ve been avoided, Lee,” Leah said. “Not only did you cheat on me, but you sabotaged our date for your own selfish desires and blackmailed Brian into having sex with you. What do you have to say?”
“I’m sorry,” Lee groaned.
“I believe you. But that’s not going to get you out of this.”
Lee yelped as Brian thrust his cock into Lee’s ass. He would’ve fallen forward onto his face, but his hands kept him up. He gripped the bed frame as Brian buried his cock in his ass.
Unimaginable pleasure washed over Lee as Brian fucked him. His body rocked back and forth and his jaw hung slack as moan after moan escaped his lips. Leah couldn’t control herself. Her own body flushed, and she was filled with so much arousal that her fingers moved of their own accord down to her soaking wet cunt.
She pulled down her panties and climbed up onto the bed, shoving her cunt in Lee’s face and holding it there until he started lapping at it with his tongue.
Brian’s thrusts grew wilder as he drew nearer to his orgasm. He reached around and grabbed Lee’s rock hard cock and stroked him, shivering at the sensation of milking his roommate for his load.
All three of them climaxed within seconds of each other. Lee’s quick tongue made Leah squeal with delight, and her lust-filled moan pushed Brian over the edge.
His hips jerked as he pushed his cock in as deep as it would go into Lee’s ass, filling his condom with his seed. Lee pulled his head out of Leah’s pussy and cried out in ecstasy, shooting strings of cum onto his bed. Brian milked him until the very last drop, then pulled out.
Brian and Leah climbed down off of the bed, both breathless and exhausted. Lee fell over onto his side, his chest rising and falling quickly as he gasped for breath.