A Bend in the Road Pt. 03

I soon moved in with Paul. I was spending all my free time there anyway and I was bringing two sets of clothes, the male clothes I wore in pubic and lingerie I wore underneath, to every visit. We decided it was easier and more convenient to just live together. Once I moved in, my lingerie collection grew rapidly. I gained a wide array of bra and thong sets, teddies, bustiers, garter belts and stockings in a rainbow of colors and fabrics. I could dress in everything from frilly and lacy pink to black fishnets and leather. I also had heels for every occasion -- strappy, pumps, pumps with ankle straps (Paul's favorite style), and high-heeled knee-high boots. If I was dressed in lingerie, then I also had some kind of heels on. Over time, I learned to walk in them gracefully.

Paul and I had sex a lot after I moved in. And why not? We made good use of the bed, sofa and shower, of course, but we also found ways to use nearly every other piece of furniture in the apartment. Not long after I moved in, I was making dinner in the kitchen. I was feeling girly wearing a pink satin cami, pink garter belt, white stockings, and pink pumps. Paul walked up behind me and began stroking my ass.

"I just love the way a garter belt frames your ass," he said.

He knelt and kissed all over my ass. Then he spread my cheeks and began licking my anus. My eyes closed and I gasped. I felt his hand behind my right knee lifting my leg off the floor and up toward the counter. Realizing what he wanted, I propped my right leg on the countertop. Paul kept licking my anus as he reached between my legs and stroked my hardening cock. All too soon, he stood, reached past me, and picked up a bottle of olive oil I was going to use for dinner.

"Do you think this would make good lube," Paul asked.

"Only one way to find out," I breathed.

Paul poured the oil into his hand and stroked it onto his cock. I bent forward and gripped the countertop as he lined up his cock with my anus. My ass was now accustomed to fucking, and he was inside me in a smooth stroke. The olive oil did, indeed, make a good lube as Paul fucked me in a steady rhythm, his hands gripping my hips to steady me since I was standing on only one high heel. After fucking me steadily, Paul thrust hard into me and pumped his cum deep in my ass. Without taking his cock out, Paul reached around with his oil-coated hand and began stroking my cock. With his other hand he played with my nipples through the satin cami. It didn't take long for me to begin throbbing in his hand. He kept stroking and cupped his other hand over my cockhead. A moment later I spewed my cum into his hand. As I came down from the climax, Paul held his cum-covered hand up.

"I guess I should wash my hand before eating," he said with a devilish grin, "or..."

I took his cue and his hand. I lovingly licked my cum from his palm before sucking each finger into my mouth.

"That's a girl," he murmured before kissing me passionately and holding me against him in a firm embrace.

Sometimes when I was alone I took stock of my life. I had become a femme crossdressing gay bottom. Paul was my top. I was regularly taking loads of Paul's cum in my mouth and ass. Sometimes I jacked him off or he jacked himself off on me, but usually he came inside one of my holes or the other. I now enjoyed the taste of his cum. I was always dressed in lingerie at home and I only wore male clothes in public and then only on the outside with lingerie underneath. Unless I went to the doctor, of course. Then I wore my only remaining pair of boxers. It was such a dramatic change from the straight married male life I had known. But I had discovered something about myself. I was enjoying the hell out of this new person I was becoming.

The problem, as I saw it, was that my transformation was only halfway. I was hairless below my eyebrows like a woman. I dressed like a woman, though not in anything I could wear in public. I liked to think I sucked and fucked like a woman. But above the neck, I didn't look like a woman because I had the same male haircut and male features. I knew what the next step was, and I wanted to take it, but I didn't know how.

One night I surprised Paul with a sexy schoolgirl costume complete with white knee-high stockings and high-heeled Mary Jane's. We carried on an impromptu roleplay of a lecherous teacher seducing an innocent student. I sucked his stiff cock before riding him as I jacked off on his chest. After licking him clean, Paul pounded me doggystyle until he exploded in my ass. We didn't exactly follow the original roleplay idea, but the sex was good. After we caught our breath, Paul asked what I thought about trying wigs and makeup. I laughed and admitted that I'd been thinking the same thing but didn't know the first thing about either. Paul said he had a solution, but wouldn't tell me what it was.

Not long after, I was surprised one Saturday morning by a knock at the door. Paul answered it and welcomed someone he was clearly expecting. I didn't recognize the husky female voice. I was shocked when Paul called to me from the living room. He knew I was only wearing a white babydoll nighty and matching thong. I quickly threw on a robe -- black satin, which wasn't exactly manly but the only one I had -- before walking out to meet out guest.

Paul introduced me to Ash. She was an attractive soft butch with visible tattoos and several piercings. Ash, Paul explained, had been a costuming coordinator for movies and theater. She was there to help me with wigs and falsies, show me how to paint my nails, and teach me how to apply makeup.

"When I'm done with you," Ash stated matter-of-factly, "not even your mother will know you're a man."

Paul announced that he was heading out and leaving me in Ash's capable hands. Even though this was exactly what I wanted, I didn't know what to do. Until that moment, nobody knew we were gay lovers or that I crossdressed. But Paul had clearly revealed everything to Ash. But she put me at ease as soon as Paul left.

"You look nervous as hell, like your mom just caught you with porn," Ash said. "Look, I know this is probably weird for you, but it's not my first rodeo. I've turned men into women and women into men. I've even turned both into androgynous neithers. Relax. Take a breath. Take off your robe so I can see what we're working with."

I slowly untied the rob and slipped it off my shoulders. Without thinking, my arms moved to try and cover the white lingerie. Ash stopped me, however, and looked me up and down. Then she walked around me.

"Well, the good news is you're doing a great job shaving so we're already ahead of the game. Looking at your height and weight, you won't ever want to use more than a C cup in public. If you want D's to play with at home, that's fine, but they're going to look too big on you to seem natural. And remember, in public you're not going for porn star. You're going for real woman. There are two kinds of second looks. One is you see an attractive woman and you take a second admiring look. The other is you see a woman and you're not sure it's a woman. People need to have no reason to question whether you're a woman. Boobs that don't fit your overall physique are one way to attract unwanted attention."

Ash measured me and gave me suggestions on styles and sizes of dresses.

"What were you thinking for wigs," Ash asked.

"I think I'd like something long and blond, and also a bob that's brunette?"

"That's fine. You can probably get away with either. Just remember that you can't switch back and forth quickly at the same places or around the same people. Nobody grows their hair from short to long overnight, so people will question if you show up within days and your hair is a foot longer." She gave me a website to order high quality wigs and warned me against costume stores.

Then we spent several hours on makeup. What to use. How to use it. When to use what. How to take it off. Ash kept stressing a natural look so that I would be seen without getting noticed too closely. She told me to think about matching my look to where I was going; that I could turn up the wattage for a nightclub but not for a stroll in the park. Eventually she made me apply and remove several looks until she was satisfied that I could do it correctly. Ash told me to practice and shop for the next month. When she returned, I was to appear my most convincing.

Ash was so relaxed and casual about the whole thing that I entirely forgot I'd spent the entire time with her while wearing a white satin cami and matching thong. It was one more step in my transformation.

I dutifully followed Ash's instructions and spent the next month practicing and shopping. I bought two high-quality wigs, a long dirty blond and a medium brown bob. I bought C-cup falsies with realistic areola and nipples. I also bought a pair of D's because, well, I couldn't help myself. And I bought a range of dresses -- sundresses, cocktail dresses, and even a tailored work-appropriate dress -- plus some skirts and tops. In the spirit of Ash's advice to go for natural looks, I also bought jeans and pants plus the obligatory yoga pants. I added low-heeled riding boots, sandals, and flats to my shoe collection. I wasn't completely staid, however. I did pick up a slinky LBD, too.

On the day that Ash was to return, I kicked Paul out and spent the day getting ready. I showered and carefully shaved everything below my eyebrows. Then I painted my fingernails and toenails with a clear glossy polish. When they dried, I put on beige lace boyshort panties and a matching bra. I slipped the falsies into the bra, noting that the dark nipples showed subtly through the lace. I pulled on nude thigh-high stockings with lace tops. Then I carefully applied makeup including burgundy lipstick. I put on the dirty blond wig, adjusted it, and brushed the hair. I went to the closet and picked out a burgundy belted shirt dress that stopped tastefully above knee. The belt helped give me a womanly shape. Then I stepped into nude three-inch pumps. I picked out some bangle bracelets and a necklace with a charm of my adopted name, ____________. Last, I spritzed on a little perfume.

I took a deep breath and stepped in front of my full-length mirror. I could hardly believe what I saw. The person in the mirror showed no trace of being a man. She could've been working in any office or walking down any street without raising a single doubt or questions. The dress fit well and the outfit worked together. The woman in the mirror was quite attractive. I was wearing sexy lingerie, but I was feeling something more than sexiness. I felt... feminine and beautiful.

Just then, there was a knock at the door. Ash. The surge of confidence I felt a moment before suddenly evaporated. I felt a flutter in my stomach and a wave of nervousness washed over me. But there was nothing for it. I couldn't leave Ash standing outside. I brushed my hair again, stood up straight, took one more look in the mirror, and then turned and walked to the door. I opened it and invited Ash in.

Ash looked hot. Her butch haircut was spiky and aggressive. She work black leather pants tucked in black patent leather high heeled boots. Her red blouse was sheer and revealed a black bra underneath.

Ash sat on the couch. I went to join her, but she told me to wait. She looked me over carefully. She had me turn and, even when I faced away, I could feel her appraising eyes on me. When I turned back, she gave me a soft golf clap and told me I'd done very well. I sat next to her and told her about my purchases and progress with cosmetics. She gave me a few suggestions about my makeup -- just fine-tuning really. Ash surprised me by saying we were going out. I objected that I wasn't ready, but she assured me that I was far more convincing than she'd expected me to be.

I couldn't drive on my man's license (I hadn't even thought to buy a purse to put a license in), so we went to Ash's car. She drove us to a bar and, after more reassuring from her, we went in. We got a table and Ash ordered for us. It was only while waiting for our drinks that I realized there were no men to be seen. I asked Ash, who replied that I was likely to be the only man there that night or any night. It was a lesbian bar. I wasn't sure whether to be relieved or not. On the one hand, I was petrified about being hit on. On the other hand, there really wasn't any difference for me between being hit on by a man or woman.

I told Ash I thought we should leave. She slid next to me and put her arm around my shoulders. She took my hand with her other hand. She looked me in the eye and told me to relax. She explained that everyone would think we were a couple and nobody was going to talk to me. "To make sure," Ash said, "I'm going to send a message to everyone here." Then she leaned in and kissed me. The kiss was soft at first, as if just for show, but became more insistent. I felt Ash's tongue and opened my mouth to let her in. Our tongues danced as I felt the hand on my shoulder move to my neck. Her other hand released mine and moved to my knee. She broke the kiss and gazed deeply into my eyes. I felt her pull gently on my hair, realizing, of course, that it was a wig. I let my head move with the wig, which exposed my neck to her. She leaned in and kissed up my neck, across my jaw, and back to my mouth. As she kissed me again, I felt her hand moving slowly up my thigh. Under the table the dress bunched up. Her fingers reached the lace stocking top and then my bare thigh. My gasp broke the kiss. Ash smiled in response.

"Ash, you can't," I breathed. "You're making me hard." Ash shut me up by kissing me again.

When the kiss finally ended, Ash invited me to dance. I tried to plead no with my eyes, but Ash stood and held her hand out for mine. I owed her much and I didn't think it was right to say no, so I accepted her hand and stood. Ash led me to the dance floor where she put her arms around my waste. For the first time ever, I danced with my arms around my partner's neck rather than their waist. Ash pulled me in closing, hiding the bulge in my dress, and she began kissing me again. Soon her hands had drifted down to my ass. When the kiss broke again, I rested my head on her shoulder. I couldn't see Ash's face, but somehow I knew she was smiling.

After we danced awhile, Ash invited me back to her place. We left the bar and she drove to an upscale apartment building. She parked in the underground garage and we took the elevator to her floor. Ash took my hand and led me to her apartment. Once inside, she pressed me up against the door and kissed me hard, forcing her tongue into my mouth. Her hands pulled up my dress and cupped my ass over my panties. Too soon she stepped away and led me to the living room. She sat on the sofa, but told me to remain standing.

"You've done well," she said. "You're really quite beautiful. So beautiful, in fact, that I'm going to make love to you. Take off your dress." I unbuckled the belt and undid each button from neckline to hem. When they were all loosed, I spread the front of the dress and let it fall off my shoulders. As Ash's eyes wandered from my pumps to my eyes, I was rapidly getting hard again and I knew my cock was tenting my panties.

Ash crooked her finger at me and I stepped closer. She reached for my panties and pulled them down my legs. My stiff cock sprang forward. She looked up at me and said, "this is the one and only blowjob you're getting tonight and you're only getting it because you were such a good girl." As her hands stroked my legs and caressed my ass, her tongue danced on the head of my cock. Just when I thought I couldn't take any more, she took my cock in her warm mouth and began sucking me. I wanted it to last forever, but I was so turned on that the telltale throbbing began quickly. Ash stopped sucking me and stood. She looked me in the eyes as she began stroking me. In no time I exploded. My cum shot all over the crotch of her leather pants. After looking down at the white cum on her black leather she told me to get down there and clean her up. As propped one foot on the sofa as I knelt in front of her. I licked my cum off the smooth leather until it was clean.

Ash helped me stand and led me to her bedroom. On the bed was a black dildo in a leather harness and a bottle of lube. The dildo was 8 inches long and realistic. Ash had me sit on the edge of the bed while she stepped through the straps and slid the harness up her legs. She tightened the straps, causing the dildo to point straight out in front of her. Then she took of the sheer red top revealing a black leather demi bra. She was a goddess.

Ash stepped closer to me and said, "you know what to do." I did know what to do. It had become as natural to me as breathing. I leaned forward and opened my lips. Ash put a hand on the back of my head and began fucking my mouth. Eventually, she pulled the dildo out, put a hand under my chin, and tilted my face up toward her. "Now your ass," she said huskily.

Ash picked up the lube and handed it to me. I squeezed a generous dollop on the head and smeared it around the shaft. Ash told me to lie down and I crawled up the bed and laid on my back. Ash knelt between my legs and I lifted my knees to my chest. Ash positioned the dildo at my anus and gently pushed into me. The dildo was bigger than Paul, but my ass, which had become accustomed to fucking, relaxed quickly. The dildo slid in inch by inch until I felt the harness against my checks. Ash put her hands on the backs of my thighs, pinning them against my chest. Then she began fucking me with steady strokes. Her techniques was to thrust in hard and withdraw slowly. It felt exquisite and soon I was pushing my ass up to meet the trusts. After a while, Ash put my legs over her shoulders and laid on top of me. She kept fucking me while she kissed me. I reached down and cupped her leather-covered ass, pulling her into me deeper. When moans broke the kiss, Ash lifted up and pulled the dildo from my ass. "On your hands and knees," she said. I turned over quickly and assumed the position. Ash pressed the dildo past my sphincter and deep into my ass. She grabbed my hips and began fucking me fast and hard. I gripped the sheets to hold my position against her thrusts. Ash began hissing "yes yes yes" through her teeth as she pounded my ass. All too soon she gripped my hips, thrust into me, and stopped. I heard and grunt and gasp and realized she had an orgasm from fucking me.

Later as we cuddled on the bed I asked Ash what we were going to tell Paul. "Who do you think set this up," Ash asked incredulously. "It's part of my fee that I get you for a night." She gestured at a mini cam positioned on her dresser. "And he knows exactly what we're doing. He saw the whole thing." I stared at the camera for a moment before giving it a wicked grin and bending down to give the strapon another blowjob.