Man to Woman

by Jane Futa

  I returned to the sports bar to meet back up with my buddies. I felt defeated and weak. Why couldn’t I talk to her? I’d never been so nervous around any other girls.

  “Is everything okay?” asked Bryce with a half drunken smile on his face.

  “Yeah,” I said. I was grateful they were all a little buzzed so they couldn’t read me as easily. I downed another shot with them and then we headed to our gate. The three of them made asses of themselves as we waited to be seated. They were drunk and young, and I would’ve joined in if I my mind wasn’t so stuck on the mysterious flight attendant. I tried mentally slapping myself. You’re on a perfectly fun, wild vacation. Stop being so depressed.

  I tried to brush my thoughts of her away and join in on the jokes. One of the desk agents came over to ask us to keep it down.

  “You guys are disturbing everyone,” said a tall blond woman with her hair pulled neatly back into a bun.

  Bryce and Sam laughed quietly. “Sorry, ma’am,” they said. She raised an eyebrow at us disapprovingly and walked back to the desk.

  “If only I had time to take her behind that desk and, mmm…” said Bryce, eyeing her tight ass as it walked away.

  “Yeah and you’d get us all kicked out of the airport,” said Rob.

  “It’d be worth it,” he said.

  “For you,” said Sam.

  “I get it,” I said, thinking again about the sexy flight attendant.

  “Thank you!” cried out Bryce loudly. The blond desk agent shot us an angry look and Bryce immediately quieted himself. “I guess I had a little too much to drink,” he said.

  It was finally time for us to board so we grabbed our things and stood in line. The guys were still obnoxious but quieter than they had been. The blond desk agent stood by the doorway to check everyone’s boarding passes. When we approached, she rolled her eyes. “Try to behave in there, okay?”

  Bryce snickered as he eyed her body up and down. I could tell she was glad to be getting rid of us for the time being. We walked down the long walkway toward the plane and boarded. As I stepped my first foot into the plane I looked up. The flight attendant that was greeting us was the same one I was temporarily infatuated with. My chest seized up as my eyes met hers again and she smiled.

  This is a sign, I thought. I can’t let her get away this time without talking to her. But the timing was all wrong. We were being quickly ushered to our seats so the passengers behind us could board. I walked quickly past her, keeping my head turned over my shoulder to watch her as long as possible. She glanced back at me a few times between greetings to other passengers. My eyes traveled down to her large breasts and my cock stiffened slightly.

  I exhaled and broke my gaze before I developed a full erection. We loaded our baggage into the overhead bins and then took our seats. We had two rows split between us. Bryce and I sat in the back row and Sam and Rob were in front of us. We joked around until the rest of the passengers boarded. The flight attendants walked around to check everyone’s seatbelts. Bryce intentionally left his unfastened.

  “Fasten your seatbelt, please,” said the flight attendant.

  “I think I need a little assistance,” Bryce joked. He looked down at his crotch as if willing her hands to graze it.

  “You seem perfectly capable of doing it yourself,” she said. Then she looked at me and winked. I couldn’t help but smile and stare at her huge breasts. Suddenly she leaned across me and reached for Bryce’s seat belt straps. She fastened it and he chuckled. Then she stood up slowly, brushing her chest just past my face. I wanted to reach out and grab her hips and pound her right there.

  “What about you?” she asked. “Do you need any help?”

  I looked down, disappointed to see that I’d already strapped myself in. “No,” I said. “But I’d love to know your name.”

  She pointed to her chest where a little plastic nametag rested. “Brianna,” she said. I gulped and looked back into her eyes. They seemed to be communicating something to me. I couldn’t help but feel as if she wanted me as badly as I wanted her. But how would we..?

  She moved on to the other passengers and I caught my breath again. My head was spinning as the guys continued to joke around.

  “Did you see that?” teased Bryce. He pointed his thumbs to his chest. “She totally wants this stud!” I couldn’t help but smile at the thought that she probably wanted me more than anyone. But this time I had a starting point. I had her name.

  Brianna moved to the front of the plane to give the Emergency Evacuation talk. I watched her soft curves shift as she pointed to the exits and demonstrated how to put on a life vest. Her skin was smooth and her hips were to die for. Her legs stretched out under her skirt and I couldn’t help but imagine myself between them, pumping in and out of her. I leaned my head back against the headrest and took in every drop of her beauty, as if I was falling into a daze.

  The talk was over and she disappeared to the front with the other flight attendants. Bryce was still talking but the plan was starting to take off so I could barely make him out. I started to enjoy the silence that the plane’s vacuum was providing. Before long, we were in the air flying along the clouds. I looked past Bryce and out the window for a moment. It really was a miracle that man was capable of flying.

  I felt a tap on my shoulder and saw that Bryce was pointing past me. I turned my gaze to meet Brianna’s as she pushed a cart full of beverages and snacks. I asked her for a soda and she blushed while smiling. I was positive after that. She liked me. If I could only get her alone somehow…

  She handed me a bag of pretzels and my drink and I lowered my tray. I watched as she made her way down the aisle, serving every passenger. When she reached the end, I saw her take a seat toward the back near the bathrooms. She was surprisingly alone.

  I turned in my seat to face her and was met with her gaze again. She shifted her legs and crossed one delicately over the other. My eyes traveled up her calves and to her thighs, eager to know what was under her skirt. I watched her breasts rise and lower as she breathed heavily. Then I saw her lips which were slightly parted and she looked as if she were already being pleasured just by the sight of me.

  Without even thinking, I unfastened my seatbelt and started to walk toward the back. I’ll just go to the bathroom… I was standing right next to her, towering over her, and her beautiful, round face looked back up at me. This time she wasn’t smiling but, instead, practically begging me with her eyes to please her.

  I opened the bathroom door and stepped inside, holding it open for a second. She looked at me questioningly and I curled my index finger, signaling for her to join me. She stood up and looked down the aisle nervously. Then she followed me into the airplane bathroom.

  The space was small and we were instantly pressed up against each other. Her breasts were squeezed against my chest. Her lips were inches from mine. I stared into her eyes and placed my hands on her hips. I slid them slowly up to her chest and squeezed her breasts. She moaned but it was inaudible due to the sound of the plane engines. I leaned down and pressed my lips to hers, sliding my tongue into her mouth.

  Her back was up against the door and her hands lay on my chest. She slid them down my torso until they reached my shorts. She unfastened them and felt my growing cock through my briefs. I moved my lips to her ear and to her neck. I could just barely make out the sound of her heavy panting.

  I quickly unbuttoned her blouse and ran my hands over her bra. She arched her back, pressing her torso up against me. I cupped a hand over her ass. She pulled my cock out of my briefs and began stroking it.

  I can’t believe I’m doing this. I can’t believe I’m getting a hand job in an airplane. I moved my mouth to her chest and kissed her full cleavage. I reached my hands for the clasp of her bra and unhooked it. Then I took each hard nipple into my mouth and flicked my tongue against them.

  I could hear her moaning now. I put a hand over her mouth to keep her quiet. That seemed to turn her on even more and she stroked me
faster. Suddenly, she pushed me back in the last few inches of space that we had, and she dropped to her knees.

  I stared down at her beautiful face, her slick brown hair, and her bare breasts dangling just under my cock. She parted her full lips and brought the tip of my cock toward her. Then she wrapped her entire mouth around it, sending a jolt of ecstasy through me.

  “Fuck,” I moaned inaudibly. She moved her mouth back and forth expertly. She was no stranger to a hard dick. Her tongue flicked along the underside and swirled in various patterns. She grabbed my balls and massaged them while she sucked.

  I leaned my hands against the door and stared down at her gorgeous brown eyes. The sight of her beautiful face swallowing my dick was almost excruciatingly pleasurable. I didn’t know how much longer I could last, but I knew we were pressed for time anyway.

  Suddenly, I let go and exploded my load into her mouth. She tried her best to swallow everything, but a few drops trickled down the sides of her chin. I reached down and wiped the streams with my thumb and watched as she licked my thumb clean.

  She stood up and dressed herself. I kissed her one more time and then she turned around to leave. Shit, I thought. I need proof for the guys. I almost forgot about our bet in the midst of my lust for Brianna. I leaned my lips to her ear and whispered, “Could I have your wet panties?”

  She hesitated and I wondered if I had crossed a line. With her ass pressed to me, she lifted her skirt and slid her panties down. They were more soaked than I’d ever seen and that only turned me on more. I bunched them up and put them in the pocket of my cargo shorts. I kissed her cheek and watched her leave the bathroom.

  When I came out, she was no longer sitting in the back. Instead, she had returned to the front of the plane and was starting to collect trash from everyone. I made it back to my seat and exhaled. Bryce had finally tired himself out and fell asleep.

  I can’t wait to tell them I already won the contest. I leaned back and smiled. When Brianna came to collect my cup, she blushed and diverted her gaze. But she smiled, and that made me very happy.

  Chapter 3

  I hardly saw Brianna much the rest of the flight or when we landed. I brushed past her on my way off the plane, but that was it. I felt like I was leaving a small piece of myself with her on the plane and I wondered if there was any way I’d ever see her again.

  We got to the hotel and threw our things on the bed. “This is fucking amazing!” cried Bryce. “I’m totally going to get laid first.”

  Rob and Sam laughed at him and I only smiled. “Sorry to break it to you, Bryce. But I already beat you guys.”

  “No. Fucking. Way.” Sam said. I reached into my pocket and pulled out Brianna’s pink panties. I presented it to them as if it were some holy grail. Their mouths opened and their eyes widened. They couldn’t believe it.

  “How did you get laid already? And when?” asked Rob.

  “On the plane. With a flight attendant,” I said.

  Bryce pulled the panties from me and carefully inspected them. “The one with the big tits?” I nodded. He smiled like he was impressed. Then he looked at the crotch and sniffed the wet stain left by Brianna. “The fuck is this?” he asked suddenly with a scowl.

  “What’s wrong?”

  “You trying to cheat? This is cum on these panties!”

  “What?” I pulled the panties from him and smelled. It didn’t smell like a pussy would smell. It smelled like cum, just as Bryce had said. “No. But I did it with her in the bathroom.”

  “If you honestly didn’t cheat then…she must’ve been a dude!”

  “No. No way. There’s no way that gorgeous babe had a dick between her legs.”

  The guys started laughing. I felt my cheeks grow red hot. I could at least lie and convince them that I had tried to cheat, but that wouldn’t change the fact that I knew I hadn’t. That wouldn’t change the fact that Brianna somehow ejaculated onto her panties.

  My stomach was doing flips. I was horrified and completely bewildered. Yet, my cock didn’t seem to get the memo. My cock stiffened a little at the thought of her hiding a cock. I didn’t understand it. I didn’t understand how she could not be a full woman and I didn’t understand why I was still attracted to her.

  I’d never see her again, either. I’d never be able to find out if I really let a trans woman suck my cock. Her breasts were so full and developed. She was a perfect, curvy, sexual woman.

  “You’re right,” I said, shrugging my shoulders. “I tried to pull one over on you.”

  “Aw,” said Bryce. “You sure you’re not embarrassed that you fucked a tranny?”

  My stomach felt queasy. As if Brianna was suddenly less than because she was different. I couldn’t speak up, though. I was too ashamed and confused. All I knew was that I’d gladly let Brianna suck my cock again. I remembered her gorgeous face as her mouth moved back and forth along my shaft. I remembered my cum dripping along her chin. Dick or no dick, she was the sexiest thing I’d ever seen.

  “I got her panties, but we didn’t fuck,” I lied. Their expressions turned to frowns.

  “Well, anyway,” said Bryce. “Let’s check out the bar!”

  I was glad he changed the subject so quickly. We set our things on the beds and then headed downstairs to get drinks. We chose a booth, this time, in the back corner. Shortly after the waiter delivered our shots, I noticed a flight crew walk into the restaurant.

  Then I recognized one of them. It’s Brianna!

  Chapter 4

  I excused myself and walked over to their table. “What are you doing here?” I asked.

  She blushed and looked up at me. I had embarrassed her around her coworkers. She stood up slowly and pressed her lips to my ear. “Sometimes we stop for the night and stay in a hotel. It’s just part of the job,” she whispered.

  I couldn’t believe it. I never thought I would see Brianna again and here she was in my hotel. No fucking way, I thought. I looked back at my booth quickly and saw that none of the guys had noticed she was here. I was hoping to keep it that way.

  “Can we meet later?” I asked her quietly. She nodded and then sat back down. I quickly returned to my booth and tried to be the life of the party. I wanted to distract the guys from noticing Brianna.

  The guys and I went to town to bar hop and meet ladies. I flirted superficially so I didn’t look suspicious. One girl threw herself on me and pressed her tits to my chest. I leaned down to kiss her but it just wasn’t the same. All I wanted was Brianna and to unravel the mystery around her.

  All the guys had found a girl to bring back to the hotel with them. None of them seemed to mind fucking in the same room as the rest of us. To keep up appearances, I invited the girl who threw herself on me. I think she said her name was Maria.

  Once we were back in the room the girls quickly stripped. I looked to my friends and they all had their hard cocks out while their girls played with them. Maria had small breasts that poked out toward me. I reached for them with my hands and she smiled while moaning.

  I lifted Maria’s skirt above her hips and picked her tiny body up in my arms and pushed her up against a wall. I moved her panties to the side and slid my cock into her wet slit. I was only half-hard and that half was only because I was thinking about Brianna. I pumped my cock in and out of Maria reluctantly, and then I turned to my friends.

  “Sorry, bro,” said Bryce who was pounding his girl on the bed. “I beat you. I win the bet.” I looked at Sam and Rob who both were getting their cocks sucked side by side, their girls occasionally breaking off in order to kiss each other.

  I pounded Maria harder against the wall. She had her hands above her head and she moaned wildly. She was attractive enough, but I closed my eyes and thought of Brianna’s mouth wrapped around my cock. Soon, I was filling Maria up with my cum and she was cumming with me. I felt my cum slide back down my cock and then I lowered Maria back to the floor. After the other guys finished cumming we sent the girls home and collapsed on the beds.

&
nbsp; I waited for everyone to pass out from drinking before I slipped out of the room. I went down to the bar and waited anxiously for Brianna to meet me. An hour passed and I thought about giving up, when I saw her turn the corner.

  She looked beautiful. She wore a short, tight, low cut black dress and sparkling earrings which dangled along her neck. She saw me, lowered her gaze nervously, and then approached my table.

  “Do you want a drink?” I asked her.

  “No,” she said, her eyes burning into mine.

  “Do you want to sit down?”

  “No.”

  I suddenly understood. I stood up and she turned around, walking back out of the bar. I followed her out into the lobby. I followed her onto the elevator. I stood beside her as we rode the elevator up to the third floor. My fingers reached down and grazed her fingers, but we didn’t look at each other. When the doors opened, she stepped out into the hallway and I followed her to her room.

  Chapter 5

  The hotel room was dark save for the alarm clock on the nightstand. I felt a pair of lips push against me and then Brianna’s familiar breasts. I cupped them with my hands and felt my cock harden. I rubbed my thumbs where I knew her nipples to be and I heard her moan, clearly this time. It was sexy and invigorating. I wanted more of her, all of her. I wanted as much as she would give me.

  I slid my tongue into her mouth and she swirled hers around mine. Her hand moved down to my groin and rubbed over my pants along my shaft. I felt it throb in her grip and I moved my hands to her hips, pulling her into me. I reached down for her ass and grabbed it, slowly lifting the skirt of her dress up until I felt her bare cheeks in my hands.