Man to Woman

by Jane Futa

  My cock throbbed with full intensity. I hoped they’d let me come by the end of it all, but I knew the wait would be worth it. I couldn’t believe how lost I became in the sensation. The touching became a blur but every inch of skin tingled with delight.

  A pair of hands ripped my panties down to my knees. A tongue slid along my cock, but the mouth didn’t suck it in. I hunched over, my ankles getting weak, and a few shoulders slid under my arms to keep me supported. My head hung low as it became harder and harder to remain standing.

  A wet finger slid into my ass and I bucked my hips forward. My cock swung against a girl’s hand and she stroked it for a moment. A pair of lips found mine and a tongue swirled inside of my mouth. I kissed back through moans. I wasn’t sure how much longer I could last. These girls were torturing more than I’d ever thought possible.

  Several hands reached for my waist and the girls gently pushed me toward one of the Mid-Century sofas. They positioned me as if I were their sex doll. They placed my knees into the seat of the couch and rested my arms against the back of it. I was completely bent over at the hips, and my panties were still wrapped around my knees. My cock and balls hung forward and my skirt had been lifted up around my waist.

  Four hands petted my ass and there was endless cooing and moaning from the girls. I looked forward toward the dining room across the house as I waited. One of the girls walked to the back of the couch and stepped into my gaze. Her tight stomach was at my eye level and she leaned down while smiling. She kissed me and grabbed my hands. She pulled my hands behind me and reached over my head to place the handcuffs on. I could smell the scent of her wet pussy inches away from me.

  A different slick finger entered my asshole, followed by a second. They were preparing and stretching me. I heard a bottle of lube pop open and a squirting sound. One hand lathered it along my crack, lubing up my hole by sliding a finger deep inside and wiggling it around.

  A hand stroked my cock and another hand caressed my balls. I felt the tip of something silicone push against my tight entrance. It’s too big, I thought. It’ll never fit!

  These girls were determined, however. They lubed and lubed, occasionally spitting. They pushed gently at first and then more forcefully when they saw how tight I was. I heard them giggling as they played with my body. One hand still stroked me and I became dizzy from pleasure. The lack of release was draining the blood from my head and I was thankful I no longer had to stand on my feet. I was worried I might faint.

  With one hard shove, I felt my ass split open wide for the toy. I let out a yelp as they worked it in deeper, giggling through my pain. Once it was completely in and I relaxed around it, I started to see the merit. It felt good. I couldn’t believe how much pleasure I was getting from being fucked in the ass. The pleasure combined with my arousal while sucking Tom’s dick made me wonder my sexuality even further. Maybe it wasn’t so black and white to me after all.

  They slid the dildo out and pushed it back in, picking up their pace as the minutes passed. The redhead walked around the sofa, still holding the purple dildo. I knew then that I had the blue one probing my ass. She slid a thumb inside my mouth and pulled my jaw open, shoving the purple dildo inside. I was double penetrated and it only turned me on more and more.

  Between the handcuffs, the two dildos, and the constant stroking, I knew I was going to come whether they wanted me to or not. I let out a choked groan with the dildo halfway down my throat. My cock swelled and squirted come all over their antique sofa. I blushed, feeling as embarrassed as if I’d just urinated my pants in public. There was a come stain on their nice couch, and it was because I couldn’t hold back any longer.

  “Ohhh,” cried a few of the girls when they realized.

  “Looks like our little slut couldn’t hold back any longer,” said Devina, inspecting her sofa. “She’ll have to be punished though for that stain.”

  One by one, the dildo slid away from my body and the handcuffs were removed. My panties were pulled up and the hands flipped me over onto my back beside the stain. Devina pointed toward it and shook her head as if I were a pet that had misbehaved.

  “You’re going to have to clean that up,” she said with a slight smirk. “I can’t have my parents finding out what you did to the couch they bought for this house. We entertain here. I can’t have people asking questions about our little sissy experiment.”

  “Yes ma’am,” I told her which made her smile even wider.

  “Good sissy,” she said, patting my head. She turned to face the group of roommates. “Alright girls! Let’s get ready for the party!”

  “What party?” I asked, wondering if it had anything to do with dildos and handcuffs.

  “It’s at the frat house, West Alpha,” said one blonde. “Do you want to go?”

  I thought about it for a moment before nodding. “Of course,” Devina jumped in, “you’ll have to go as a girl.”

  My adrenaline raced at the thought of returning to West Alpha as a girl. Will they recognize me? Will they whistle at me like they did earlier? The curiosity was enough for me to agree. I had to know what would happen if I approached them again with my newfound confidence.

  “Of course,” I said finally to Devina’s delight.

  “Excellent. Let’s find you a different outfit, then. Something a little more convincing.” Devina grabbed my hand and took me to her room. She found me a tight red dress and added heavier makeup to my eyes. When she finished dressing me, I sat on the edge of her bed while she dressed herself. I saw her fully nude as if we were two girlfriends hanging out, but I couldn’t help thinking about how she sat on the end of this same bed earlier while I had licked her pussy.

  My chest swelled with pride and I couldn’t help but smile. I felt more included and popular than ever, and I didn’t mind being their sissy one bit. In fact, dressing up was more fun than I thought it would be and I was excited to try out my new outfit on the guys at West Alpha.

  “Ready?” said Devina when she had finished.

  “As I’ll ever be,” I said with a smile. I took her hand and we followed the girls outside to walk toward the frat house.

  Chapter 6

  The house looked different at night. It was eerie despite being full of life. Several of the fraternities and sororities had shown up and were already inside playing drinking games and failing at keeping their hands off each other. Netflix was streaming in one room and music blared in another. I walked in the center of the group of girls that brought me. No one had noticed me yet and I hoped I wouldn’t stand out too much.

  As the girls dispersed, attempting to find their place in the crowded house, Devina and Beth stuck by my side. I was grateful to both of them. Devina held my hand and gave it a squeeze as she looked around the foyer.

  She leaned down and pressed her lips to my ear, “How’s your ass doing?”

  “It’s okay,” I said. “A little sore, but nothing I can’t handle.”

  “That’s my girl,” she teased. She kissed my cheek which immediately caught the attention of some of the West Alpha guys.

  “Well, well,” said Tom, stepping forward from the crowd. “Who’s this new whore of yours, Devina?”

  Devina wasn’t fazed by the insult. “I heard you let a pledge suck your cock the other day, faggot.”

  I glared at her, worried he would recognize me and rightfully pummel me for talking about his little secret. Instead, he scoffed as if he didn’t believe she really knew anything. He wrapped an arm around her shoulder and whispered, “How’d you like to suck it?”

  She pretended to vomit and pushed him off. “You’re scum, you know that?” Knowing that his chances were blown with Devina, he quickly moved toward Beth.

  “What about you, baby? Want a piece of this dick?”

  “That depends,” she said. “Can I cut you into pieces after?”

  “Baby, you can do whatever you want after,” he said with a deep laugh.

  “Ugh,” said Beth after leaning in to smell his br
eath. “He’s not even wasted and he’s this obnoxious.”

  “I know someone who might be interested,” said Devina suddenly. I turned to her and saw her looking at me. My body shook in the new red heels she leant me. I can’t possibly do something with him again. He’d remember me for sure.

  I let my eyebrows open to display concern. I shook my head. “Devina,” I said in a higher pitched girly voice, “I can’t.”

  Tom leaned in, his curiosity peaking. “Come on, baby. You’re hot as fuck. I’d treat you real good.”

  “Oh right,” said Devina. “She’s a virgin. She probably doesn’t want you to be her first time.” I elbowed Devina gently. She was only making me seem more appealing to him. She leaned down to my ear and whispered, “Come on. Think of this as just another one of your chores.”

  “What did you say?” asked Tom who hadn’t heard Devina. “You talkin’ shit about me?”

  “Yeah right,” she said. “Like I would waste my breath.” When Tom seemed convinced that she hadn’t spoken any ill of him, he wrapped an arm around me and pulled me in close.

  “Let’s go up to my room. I’ll show you a good time, I promise.” I followed him up the stairs but looked over my shoulder. Devina and Beth were both giving me a thumbs up with smiles on their faces.

  I hope I make it out of this alive, I thought as we entered the bedroom.

  Chapter 7

  The room was dark with only a hint of moonlight illuminating the bed I’d seen in the days before. It looked different in the shadow of the night, like it was meant for sex. During the day it had seemed like an innocent man’s bedroom. Now it seemed like the perfect place for a sleeze like Tom to take unsuspecting women. If I was helping the girls avoid him for a little while then that was enough to satisfy me.

  Tom leaned in and kissed me, forcing his tongue into my mouth. I swirled my tongue against his, tasting the faintest drop of whiskey. He definitely wasn’t drunk, but he’d had something before he brought me up to the room.

  Tom grabbed my hand and rubbed it along his groin. I could feel his erection building in his pants and hoped he wouldn’t grab mine and find out that I was really a guy. I knew if I could distract him enough with my hands and mouth, he wouldn’t ever have to find out.

  I unzipped his pants and slid my hands inside of them. I kneeled on the floor, pulling his pants and briefs with me. His familiarly long cock sprung forward and the memories of sucking it came back to me. I was hungrier for it this time and more excited since I was dressed as a girl. I wrapped my hand around the base of it and then sucked it into my mouth.

  “Oh fuck,” he moaned. “You don’t waste any time.”

  I pulled in my cheeks, drawing him back along my tongue. I swirled the tip of my tongue in a zigzag pattern along the underside of his shaft. I tried to suck him a little differently as a girl than I had as a guy so he wouldn’t notice it was the same mouth. Something told me, though, that he’d had plenty of mouths to shove his cock into. So many, I hoped, that he wouldn’t remember the specifics of mine.

  I felt his head bang against the back of my throat and I thought about the dildo in my ass earlier. My cock hardened, but I knew it was a good time to practice not coming. I couldn’t come in Tom’s room or he’d know for sure I wasn’t a chick.

  I swallowed his cock over and over until I was choking on it. I reached up and fondled his balls as I sucked. He kept a hand on my head and rocked his hips against my face. He moaned with each thrust and I waited until he was about to come to pull off of him. I felt his cock swell in my mouth and his balls draw up toward his body. His legs quivered and his abs tightened. I pulled off quickly and he hunched over in response.

  “Oh fuck,” he said. “I almost came, baby. Why did you stop?”

  “Because,” I said coyly. “I like it in the ass.” I knew I had him hooked when his eyes widened to the size of golf balls.

  “Ohhh,” he said with a smile. “You’re one of those virgins! I can respect that, baby.”

  “Yeah,” I said, shifting my eyes to the side and chuckling to myself. “I’m one of those. Just leave my pussy alone and you can have all the fun you want.”

  “Right on,” he said. He reached down for my shoulders and pulled me up to standing. He shoved his tongue down my throat and squeezed my nearly flat chest. He spun me around and then walked me toward the bed, bending me over the edge of it. He spanked my ass and lifted the bottom of my red dress over my hips. I reached quickly underneath me for my cock and balls to make sure they were hidden from sight.

  He rubbed my ass with his hands, giving each cheek a little squeeze. He disappeared for a moment and when he came back, I heard him squirt lube into his palm. He rubbed it on his cock and then fingered the lining of Devina’s black panties. She had let me borrow a whole new outfit and I was grateful for all the clothes she was willing to share with me.

  Tom pulled my panties down slowly to my knees and over my ankles. He tossed them to the side and lowered his face to my ass. He flicked his tongue across my sore entrance and teased it. I clenched the sheets in my hands and moaned as he slid his tongue deep inside me. I wondered if he could taste the lube or silicone from earlier.

  He picked his head back up and rubbed lube along my hole. He slid a finger inside and pulled it out. “You’re pretty tight,” he said. I imagined he was smirking as he said it.

  “Thanks,” I mumbled, remembering the sensation of the blue dildo splitting me open. I was grateful the girls had primed me for this experience. I knew this time would be all pleasure.

  Tom pressed the head of his cock to my entrance and pushed in. I felt the familiar splitting but it was less severe, less painful. Pleasure quickly overwhelmed me and the pain subsided. I moaned as he pushed all the way inside of me. He growled with every new inch that slid in.

  I felt his balls almost touch my balls, so I pulled mine up as far as I could. Tom slid out of me and pushed back in. He quickly picked up speed and pounded me harder and harder.

  “Fuckin’ slut!” he cried as he rocked his hips against my ass. “You little virgin slut. I’m going to give it to you good.”

  “Yes,” I groaned. “Fuck me good. Teach me a lesson.”

  “Yeah. I’m going to punish you for being such a slut,” he said. He kept pounding his long, thick cock into me until I felt his entire body tense above me. “Ohhh,” he groaned. “I’m going to come!”

  His cock grew and hardened until it spilled its hot come deep inside of me. I felt his warm pool fill me up in a way the dildos couldn’t. It felt like it was meant to be there. I moaned and couldn’t hold my orgasm back. I spilled my come all over the inside of Devina’s red dress.

  Fuck. I hope the stain isn’t noticeable at the party. When Tom had finished, he pulled out of me and collapsed on the bed. He closed his eyes while he tried to catch his breath. I sat up and inspected Devina’s dress in the moonlight. From inside the dark room, I couldn’t find a stain and breathed a sigh of relief.

  “Thanks for the fun,” I told Tom, searching the floor for my panties. When I found them, I slid them up my long, slender legs. “But I better get back downstairs to the party.”

  Tom mumbled and shrugged. I took that as permission and entered the long hallway outside his door. In the hallway, under better lighting, I could see that the stain was hardly visible. I huffed out an exhale and walked downstairs, my ass still throbbing from the pounding I’d received. Each step I walked down released more of Tom’s come from deep inside my ass. It wasn’t long before I felt a stream of wet heat collect on my inner thigh. I reached behind me and wiped it with my fingers and then I licked them clean.

  I quickly found Devina and Beth in the kitchen with their drinks. They smiled at me and waved me over. “Oh my god,” said Beth. “So what happened?”

  “He fucked my ass,” I said with a proud smile.

  “Oh my god, girl!” cried Devina, giving me a high five. “Way to go! Was he wise to any of it?” I shook my head, feeling the pride sw
ell up in my chest. “Good job!”

  “We’ll have to take her to every party,” said Beth to Devina.

  “For sure,” she replied. The rest of the night they kept me by their side to fend off any unwanted guys. I enjoyed my new role and looked forward to fulfilling it in many different ways in the future. The rest of the night was filled with laughter and drinks. The girls and I eventually went back to the house together and had a giant slumber party.

  The girls passed around stories of their night. An hour into it, Devina looked in my direction and said, “I think we should accept our new sissy as a regular sissy sorority sister.” The other girls nodded in agreement and held up their cups of hot tea in a toast fashion.

  “Our sissy will need a girly name, of course.” The group discussed and debated until everyone finally decided on Brittany.

  “Do you like Brittany?” Beth asked me.

  “I think it’s perfect,” I said, beaming the biggest smile.

  “To Brittany!” cried the redhead.

  “To Brittany!” cried the rest. Everyone drank from their tea and continued their storytelling. I watched and listened in amazement. All I had wanted when starting college was to be accepted and to be popular. I was apparently looking in all the wrong places. I watched Devina and moved my gaze to Beth.

  Brittany, I thought. I had finally found the place where I belonged and I couldn’t have been happier.

  Summer Camp

  Chapter 1

  “You ready, Frank?” asked Peter with a cocked eyebrow and a fiendish smile.

  “For what?” I asked as if I didn’t know what he was about to say.

  “For the week of shenanigans and tom foolery, of course!” He swung his arm around me and hugged me close to him. My heart raced just thinking about the crazy fun we would inevitably have over the next week.