Man to Woman

by Jane Futa

  She played the coy woman well. She sat there batting her eyelashes at me and tucking her hair behind her ear. I leaned down slowly, watching every shift of her eyes as I did so. They swept left to right a few times before locking on me. I saw her pupils dilate as I closed in and the pace of her flaring nostrils told me she was nervous. I reached my hands for her wrist and grabbed it tenderly.

  Then I planted my lips on hers, kissing her for the very first time. She pushed her lips back into me and exhaled through her nose.

  I released my soft grip on her wrist and let my hand slide slowly up her arm. I’d never been this tender before, and I wasn’t sure what had come over me. All I knew was that I wanted to remember every second of being with Sheila, especially since I was worried it’d be my only time with her.

  As my fingers neared her shoulder, I felt goose bumps forming on her skin. I smiled mid-kiss and she pulled away with a look of confusion.

  I could tell she was worried that I was taking advantage of her. It surprised me that she would care since she’d been such a tease all week.

  “I really like you,” I whispered in an attempt to reassure her.

  She cocked her brow at me and her diamond eyes scanned my face for answers. “You don’t even know me,” she fought back.

  I brought my hand back to my side, sensing frustration from her. “I’d like to know you,” I admitted.

  “I’m not like everyone else,” she said.

  “I know.”

  “What do you know?”

  “That you’re trans…”

  Her eyes widened and then she looked toward the floor. “Is this some kind of joke to you?”

  “Not at all,” I shot back. Pain swelled in my chest. Perhaps I’d been too forward with her. She obviously had a host of her own conflicts. This must be why Brandon warned me about trying to get with her. “I can leave if you want.”

  She bit her lip and kept her gaze on the floor. I stood up slowly and started to turn toward the door when I felt her delicate hand grab mine. I turned my head back to her and she was looking up at me with wide, sparkling eyes. “Don’t go,” she said.

  I sat back down and ran my fingers from her temple to her chin. Then I leaned in again for another kiss.

  She pushed into me with more passion than before. Sheila sat up mid-kiss and wrapped her arms around my neck. She slid her fingers through my short, dark hair and played with the strands. Her warm, soft tongue slid into my mouth and I devoured every inch of it.

  There was another loud interruption from her brother from the other side of the wall. We both chuckled through our kiss. Then I cupped her cheek and brushed my thumb against her skin.

  Sheila grabbed my hand and lowered it to her chest. She wore what must’ve been an A cup padded bra. There wasn’t much flesh there, but it turned me on all the same. I massaged her breast and she slid a hand over my chest.

  She lowered her hand slowly down to my waist and unfastened my jeans. My cock was rock hard. I wanted to slide a hand between her legs, but I wasn’t sure how she’d feel about that. I decided to let her run the show.

  She pulled away from our kiss and pushed on my shoulders to guide me down on the bed. I lay back and let her climb on top of me. She straddled me and I watched her long hair slide down her gorgeous body.

  She lifted her top up over her head, revealing a matching pink stain bra. I reached for her waist and held her hips to me. Then I sat up to kiss her stomach and chest. She held my head to her and moaned against my ear. I wanted to roll her over and bang her right there, but I also wanted the moment to last so I held back as difficult as it was.

  I looked up into her curtain of hair and she leaned in for a kiss. I ran my hands up her back and started to unhook her bra. She smiled and helped me slide the straps off her shoulder. Her chest was flat, but no different than any other flat-chested woman. I ran my hands over her nipples and pinched them in my fingers. She moaned and bit her lower lip. She grabbed my hands as I massaged her chest, and she started rocking her hips over me.

  I didn’t want to move too fast for her so I stayed like that a moment. Then she slid one of my hands down her torso toward her skirt. She moved it over the bulge I knew had been there all along. For the first time, I felt her small cock pressed tightly up against her stomach.

  Unsure of how to touch her, I let her guide me. She formed a cup with my hand and slid my fingers toward the base of her cock. I held her pelvis as if a wet pussy was there. She rocked against me and moaned.

  Then she climbed off of me and stood at the foot of the bed. She finished removing my pants and briefs. She came face to face with my hard cock again and licked her lips. She climbed in between my legs and wrapped her tiny fingers around the base of my shaft. She opened her mouth and wrapped her lips around the head of my cock.

  I closed my eyes and fell into ecstasy. Her soft, delicate mouth felt as euphoric as before but with the twist of knowing now that she was trans. I wanted to give her all of the respect she deserved, but I couldn’t help enjoying the taboo feeling that swept over me. This was completely new to me and if it hadn’t have been Sheila, I know I wouldn’t have gone through with it. There was just something special about her. It stretched beyond her just being a trans woman, but I knew that experience must’ve added to her unique beauty.

  She slid her mouth further down my cock until it hit the back of her throat. I looked down at her and watched her diamond eyes gleam back at me. I reached my hand to her head and stroked her golden locks. She moved her head up and down faster.

  “Fuck,” I moaned as she devoured my hard cock. I wanted to fuck her so badly. I wanted to cum down the back of her throat. I wanted to ravish her and make her mine. Take your time, I reminded.

  When I felt like I might explode I lifted her off of me. “Is everything okay?” she asked with a worried expression.

  “Yeah. I just don’t want to cum yet,” I admitted. She smiled brightly and then we both heard Brandon shout again. We laughed and then she crawled up next to me on the bed. I stretched out my arm and let her lay against it, my cock still throbbing.

  I rested my hand on the outside of her thigh and slid it slowly under her skirt. I dipped my index finger into the fabric of her panties, keeping to the outside of her thigh. She closed her eyes and moaned softly. I kissed her and slid my tongue between her lips. Then I moved my hand back around to her bulge and rubbed gently.

  She writhed in my arms like a virgin who was sensitive to every touch. I wrapped my other hand around to her side and dragged my fingers along her ribcage. She swirled her tongue around mine and moaned. She pressed herself up against me and reached her hand for my cock. Her hand started stroking it slowly as I massaged her.

  I groaned with pleasure and then pulled gently on the elastic of her panties. I moved slowly to allow her time to stop me, but she didn’t. I tugged further, releasing her small cock and balls from their bondage. I slid the satin fabric down her knees and she shuffled them off her ankles.

  I glided my knuckles across the underside of her cock and she moaned. I wrapped my hand around her shaft, surprised that she never stopped me. This was my first time with a trans woman, and I wasn’t sure what to do. I stroked her slowly as she stroked me, both of us moaning into each other’s mouths.

  She pulled away from our kiss and looked deeply into my eyes. “I want you to fuck me,” she whispered in the most seductive tone.

  “I want to fuck you,” I whispered back. Then I kissed her quickly and bit her lip with my teeth.

  She moaned and then added, “I have lube.”

  We both released our grips on each other and she rolled over to her nightstand. She pulled the drawer out halfway and grabbed a small bottle. She squirted some in her hand and then slid it along her ass. Then she reached for my cock and rubbed the slick wetness over my shaft.

  It was cool and warm at the same time and my head started spinning. “Fuck,” I groaned as she stroked. Then she removed her hand and rolled onto her s
tomach, tossing the lube to the side of the bed.

  I kissed her quickly and then climbed on top of her. I lifted her skirt above her ass, showcasing her perfect cheeks. She had her cock and balls tucked under her stomach. From this angle, she was 100% woman, and I was about to fuck her cute little feminine ass.

  I stroked my cock a few more times and then rested the head against her hole. I watched as her hands gripped the bed sheets in preparation. I hesitated, wondering if this was her first time. I rubbed her back gently, just in case it was, and then I pushed my cock head in.

  I groaned as I felt her ass stretch wide around my shaft. She released a strangely quiet scream. I held my cock at the entrance until her ass relaxed around me. Then I pushed in further. I groaned as she moaned. I slid in slowly until my balls were pressed against her.

  I leaned over her and stroked her hair. She smiled and said, “It feels so good to have your cock in me.” I nearly came right there. I clenched my jaw and pulled out slowly, careful to leave the tip inside her at all times.

  I pushed back in more smoothly this time and pulled back out. Each time I pulled out, I never pulled out completely. The longer my cock was inside her the more comfortable she became. I saw her grip on the sheets start to release as she relaxed. When she seemed to be feeling more pleasure than pain, I picked up my pace.

  I started pumping my cock in and out of her quickly. I huffed and puffed as I pushed myself on top of her. I saw her reach a hand under her stomach and start stroking her cock.

  “Oh my, I’m going to cum,” she whispered.

  “Me too,” I grunted. I slammed into her over and over until we both let out stifled screams. Her eyes were gracefully clenched as she came and mine nearly rolled into the back of my head. It was the greatest orgasm I’d ever experienced.

  “Fuck!” I cried out as my last drops of cum spilled into her.

  “Shhh!” she said with a finger to her lips. I realized I might’ve shouted too loudly. I hoped I didn’t blow our cover.

  “Sorry,” I whispered. She giggled and my spirit lifted. I almost didn’t care if I was caught. Sheila was the most exciting thing to happen to me in a long time. I pulled my cock out of her and lay down beside her.

  We stared at each other and then she kissed me. “That was my first time,” she admitted. I looked at her with round eyes and I felt my lip tremble with worry. I hoped I hadn’t been too rough with her. “I hope it won’t be our last time together,” she added.

  “Definitely not,” I replied, stroking her face. “I don’t know how, but I have to see you after this week ends.”

  She smiled brightly and kissed me. “I’m sure I can figure out something,” she said with a wink.

  “Well you did figure out how to get me into bed with you,” I joked. “Even though Brandon specifically asked me not to.”

  “Oh, he’s just overprotective,” she said. I could tell she cared a lot about Brandon. “It’s nice to have a brother like that.”

  “I imagine it is,” I said. I wrapped my arm around her and pulled her close to me. I couldn’t believe I just fucked a trans woman for the first time. Not that it mattered much to me. Sheila was beyond gender to me. All I knew was that I wanted to have her again and again. She was the most exciting woman I’d ever met.

  “Maybe we’ll find a way to tell Brandon about us,” she said with a hopeful look.

  “I’d like that,” I told her. “As long as you don’t think he’d kick my ass.”

  “Not if I hold him back,” she joked. Then I heard Brandon call for me from the other side of the wall. I sat up quickly as my heart raced.

  “Guess I better get back for now,” I told Sheila.

  “Guess so,” she said.

  “Do you want to come with me? We could tell him together…”

  Her face lit up like a kid on Christmas. “I’d love to,” she said, quickly grabbing her clothes and throwing them on. When we were both dressed, I grabbed her hand and walked her to Brandon’s doorway.

  I turned to Sheila who was already looking at me. She flashed me a big smile. Then we pushed open the door.

  There’s no turning back now, I thought as I smiled from ear to ear.

  Dressed for the Tips

  Chapter 1

  “Hey, Rob. Time to cash out,” said Cindy after tapping me on the shoulder. I was in the middle of wiping tables clean, but as a waiter you drop everything to cash out. It was always the best time of the night, finding out how much you made in tips. I always tried to keep track in my head, but I’d always be a little off.

  I followed Cindy’s perfect round ass to the counter where everyone laid out their receipts and bills. I stood next to Cindy and occasionally peeked over at her slightly open blouse. It was difficult to ignore her large, round breasts, especially since clothes never seemed to quite cover her. My cock stiffened as my eyes traveled along the smooth curves.

  I caught myself before I stared too long and pulled out my black bill holder. I looked up from under my brow ridge and saw Chris eyeing me from across the counter. He had a half smirk and one eyebrow lifted at me as if he caught me checking out Cindy’s body. I’d be more worried if I hadn’t caught him staring at her numerous times throughout the day. I brushed it off and started counting.

  It was typical of us to share what we made, either for bragging rights or to vent about the slow day, but Cindy rarely told anyone what she made out with. We were all curious…her hot body had to have scored her a few more bills than the rest of us. Not to mention her sparkling smile. Even other women would throw their wallets at such a charming and sexy woman.

  I knew this was my only chance. When everyone was distracted with one another, I peeked over at the tally she had on a sheet of paper. I did a double take. There was no way I was reading that correctly. $500? In tips on a Wednesday?

  My heart nearly stopped from shock. I swallowed hard and moved my eyes away quickly before she could catch me. I tried to reconcile what I saw. I knew she’d make more than us, but hundreds more? She was good, sure, but her body had to be the only reason for the large discrepancy.

  The rest of us finished cashing out and cleaning. We all said our goodbyes and then headed to our cars. Chris followed me to mine.

  “Dude. Dude!” he said desperately as he shuffled toward me. “I saw you looking at Cindy’s tally. Did you see anything?”

  “Yeah mean. You wouldn’t believe what she makes.”

  His eyes were wide and his body was bouncing up and down. “Tell me, dude.”

  “$500.”

  “No. Fucking. Way.”

  “I don’t really believe it myself.”

  “I wish I was a hot chick,” he said, thrusting his hands into his front pockets and looking off into the distance. I could almost see his mind traveling to the image of him as a hot chick. I laughed to myself and then stopped abruptly.

  Why not? I started to wonder. I looked down at my thin, lanky body. I could pull it off.

  Chapter 2

  When I first came up with the idea, I wasn’t completely serious. But I couldn’t keep my mind from considering it all the way home. I was met with quite a few rebuttals, as well.

  How would you get hired?

  What if everyone noticed you?

  What if you slipped up?

  Somehow, none of them were good enough to chase the idea from my mind. No matter how many reasons I came up with not to go through with it, my mind still circled back to that number: $500.

  I got back to my apartment and threw myself on the sofa. I stared at the ceiling, trying to comprehend how I was considering what I was considering. How would I get my hands on women’s clothes, anyway?

  Then I remembered. A suitcase my ex-girlfriend left behind. I hadn’t gone through it. The memories would be too painful. But it had been over a year. And it wouldn’t hurt to try on a few things. Just to see…

  Confused by my enthusiasm to try on some of my ex’s clothes, I downed a quick shot of whiskey to take off the edg
e. Then I darted into the bedroom and opened the closet doors.

  I dug through piles of accumulated junk until I found it; her pink suitcase. I pulled it out and set it on the bed. I unlocked each clasp, one at a time, and pried it open.

  Inside laid a mountain of clothes. There were panties, stockings, lingerie, swimsuits, and dresses. There was even a pair of heels and women’s sneakers. Everything I could ever need to pull this off was right in this little case. My eyes were wide with disbelief. Could I really do this?

  I reached in for a black, lacy thong. I held it up to my chest and stared down at it. I gulped and looked around as if someone would see. Chill, Rob. You live alone, remember? Oh yeah. That’s right. Still, I couldn’t help feeling like someone was going to catch me if I slid on my ex-girlfriend’s underwear.

  I double-checked the blinds and the locks. There was no way anyone would be able to find out. It’s just a pair of panties, I told myself. I exhaled and then dropped my pants and boxers to the floor. I stepped out of them and kicked them to the side.

  I looked down at my small cock, barely noticeable as it dangled from my hips. I pressed the lacy fabric against my cock to get used to the sensation. Immediately, something foreign and pleasurable came over me. I leaned my head back and moaned as I rubbed the fabric around my cock and balls. It wasn’t soft material, but it was delicate and taboo against my manly genitalia.

  It didn’t belong, and that’s what made my cock stiffen.

  I tossed the panties to the bed suddenly. What the hell is wrong with me? It was one thing to tease the idea for a moment. It was another to officiate it by pulling a pair of panties up to my hips.

  No one would know, I reminded myself. But I knew that I would know, and that was almost enough to throw the panties back into the suitcase and close it for another year. But something adventurous tugged at my chest. I was curious, and the curiosity had a hold over me.

  I reached over and picked up the panties again. I exhaled and lowered the elastic to my feet. I stepped through each small leg hole and slid it upwards. The lace brushed against the back of my calves, stretched over my knees, and then tightened around my thighs. When it finally reached my cock and balls, I was already halfway to orgasm.