Josephine Ch. 02

After coming out as a cross dresser to my sister, I spent almost all of my time at home dressed as a woman. I reasoned with myself that it was a phase triggered by my newfound freedom.

My sister continued to be very supportive and treated me perfectly. She delighted in showing me how to do my hair and makeup. We went shopping together and helped me buy clothing, makeup, shoes, and accessories when I had some spare money.

My hair grew longer and when I was being a man I would wear it in a ponytail like some guys seemed to do. Except for the ponytail, my male personality became slightly exaggerated. People at work began to joke about how I couldn't keep my eyes off of a beautiful woman. Little did they realize that I was not just lusting after them, but also studying them. I watched how women walked and moved. How they did their makeup and hair. I paid attention to how attractive women, particularly attractive larger women, dressed.

My girlfriend, Anna, loved it. The more feminine I became, the wilder and more ecstatic our sex became. Anna began to dominate me more and more. It began slowly, and I would submit knowing that the pleasure would make it worthwhile. But Anna had a way about her. Soon I was spending entire weekends at her apartment being "trained".

I lost weight and some upper body muscle mass while she convinced me to do exercises designed to make women's bottoms stronger and more curvy. To further enhance this I spent a great deal of time wearing waist cinchers and tight thongs that compressed my waist and boy parts to enhance my feminine appearance. Over time I noticed that my boy parts actually seemed to shrink a little

I became the perfect curvy, girly cross-dressing submissive and Anna became a dominating man. And with her collection of strap-ons, she played the part perfectly.

I'll save those stories for another day. Today I wanted to tell you about Darren.

Darren was a bisexual friend of my sister's, and he had hit on me several times when I was being Joseph. He obviously liked me as a person, and we hung out quite a bit even after he gave up on hoping that I'd "turn".

At some point I started thinking about him while I was dressed as Josephine. I dismissed it at first, but when I was alone I started thinking about how nice he smelled. And how strong he was. And soon I was rubbing myself while thinking about his lips and imagining what his cock looked like.

Eventually Anna and I slowed our pace and she acquired other interests to play out her fantasies with. No longer having a sexual partner, I began masturbating more. And when I was dressed as Josephine I began to obsess on Darren. I would kneel in my room, slobbering over my favorite mouth dildo and dreaming that it was Darren's cock. And whenever I slid a plug into my ass, I almost couldn't resist whimpering his name.

Eventually, confused, I had to confess to my sister that when I was dressed as Josephine I couldn't keep my mind off of Darren.

"Darren is fucking hot," she said. "I've hit on him a bunch of times, but he keeps telling me that he didn't think you'd like it."

She looked at me, and a smile crossed her lips.

"Which totally means he's holding out for you!" she exclaimed. "Oh. My. God."

I blushed.

"So you don't mind," I said quietly," that I might be gay or bi or something?"

My sister rolled her head back and laughed quietly.

"Mother Mary," she said rolling her head against the back of the sofa. "No. Sweetie, you're my family and all that matters to me is that we can all be happy."

I was quiet.

"You're thinking about Mother, aren't you," she sighed.

I nodded and started to weep. I hadn't wept in a long time. She put her arm around me and pulled my head to her shoulder.

"Sweetie," she started, "I know this sounds like junior high school, but would you like me to ask Darren out for you? For Josephine?"

I knew that some of our friends had probably guessed my secret. Others probably knew from Anna. Maybe that's why Darren had asked me out a few times.

We had gone to "drag" parties, which I absolutely loved because I could be Josephine in public. Realistically, I probably looked way too natural walking around in heels for people not to figure it out.

"Let's invite him over to meet my sister," she said, "and see what happens."

I chewed my lip a little.

"Does that sound good? Would you like that?" she questioned.

I nodded, still chewing my lip.

She put her hand under my chin and lifted my eyes to meet hers.

"Jo, this is a big step. I need more than a nod. I need to know that this is what you want," she said. "I can talk to him so he understands ahead of time, but I need you to tell me very clearly that this is what you want or I'm not doing it."

I chewed my lip and thought about it.

"But one of us is going to get this guy into bed. Because my GOD is he beautiful," she grinned.

"He is," I whispered with a smile.

"He isn't easy, either, you know," she said. "A bunch of people have tried and he's kind of ... well, he isn't easy to seduce."

I could feel a shift in my breathing and my face felt warm.

"You're blushing again," my sister intoned.

"When do you think," I started and stammered. "When would you ..."

"Do you want me to invite him over to meet you?" she asked again. "I think he's really going to like you if that's what you're worried about."

I was so nervous that I almost giggled my answer, "Yes."

My heart was racing in my throat. I was excited and hopeful, but terrified all at the same time.

"I want him to like me so badly," I whined.

My sister laughed, "You are such a girl. He obviously likes you. In that way. It's Thursday. I'll invite him over tomorrow for drinks."

I must have looked at least a little scared.

"Jo, I'll make sure it's cool before he gets any information," she said. "If I don't know for sure that he's gonna be cool with this we'll avoid it altogether."

We decided to make it a double date. Her primary lover, John, would come over with Darren. Somehow letting John in on my secret didn't seem so difficult. He had already figured it out anyway.

I wore my best simple black dress with a padded bra and slip underneath it. I had my best shaper undergarments to cinch my waist down and enhance the curve of my well-toned bottom. For my legs, I had a new set of thigh highs and low pumps.

My sister helped me with my makeup and hair.

I looked as beautiful and as feminine as I ever could. Actually feminine. Not like a man with clownish amounts of make-up on or a stripper looking to conceal her features. I wanted so badly for Darren to like me, and my sister was so excited to be helping her sister get ready for her first real date.

John and Darren showed up at eight. Darren looked stunning. He was perfectly groomed and he wore a dark jacket and shirt that made the green in his eyes even more vibrant than I had remembered.

My sister introduced us.

"Darren, this is my sister Josephine," she said.

Darren took my hand gently and smiled as he bowed a little.

"I'm very pleased to meet you, Josephine," he said. "You are even more beautiful than I imagined you would be."

I was completely lost to the moment. All of my nerves and fears disappeared when I felt his lips on the back of my hand. The scent of him almost made me faint.

The evening went beautifully. We sipped gin and tonics and talked. When my sister saw how well things seemed to be going, she found an excuse for her and John to go to the convenience store around the corner. They said that they would be back in five or ten minutes.

"I must confess," I said looking at the top button of his shirt, "that I've been thinking about you."

"I'm glad to hear you say that," he answered with a smile.

I slid a little closer on the couch so that I was under the arm he had propped up on the back.

"I know it must seem odd," I said.

"Your sister explained some things to me," he said, "and I'm comfortable. And I'm honored that you would see me."

He seemed sincere. My heart started skipping beats. This man was too good to be true.

I shifted closer and we turned toward each other. My hand touched his cheek and his lips followed it back to meet my own.

I had never kissed a man before, but it was more magical than any kiss I had ever experienced. Our mouths melted into each other. He was gentle and followed my lead. His left hand slowly drifted down my side to rest high on my hip.

I pushed my tongue into his mouth and found myself pushing his hand down further to rest on my bottom. His hand explored the curves of my hips and bottom and I had slowly begun to slide my hand down the front of his shirt when the door opened.

Darren and I straightened ourselves up hurriedly as my sister and John entered the living room.

"You two are hitting it off, I see?" my sister smirked.

I was feeling confident. I was feeling bold.

"We are," I said standing up and adjusting my dress. "I don't believe Darren has actually seen the rest of the apartment yet."

My sister would sometimes joke about giving men and women a tour of the apartment, which really meant that she as taking them to her room.

I could see her and John's eyebrows raise a little.

"Would you like the full tour?" I asked looking down at Darren.

He answered by standing, the bulge in his trousers obvious, and following me down the hall. As soon as we entered my room I shut the door and gently pushed Darren up against the wall. Our lips met and we immediately returned to exploring each other's mouths.

Most men don't realize that an erection isn't necessary to feel pleasure or even to cum. The form fitting undergarments I wore pressed my boy parts deliciously snugly against my body, preventing them from becoming hard, but my crotch was still alive with nerves firing in pleasure.

Darren's hands explored the curves of my ass until finally he grabbed my ass with both hands and pulled my body even tighter to his. I could feel his rigid cock pressing against me through his trousers.

I pushed him back just enough to slide my hands down to his belt buckle.

Our kiss broke and we looked into each other's eyes as I pulled his buckle loose. I rubbed the palms of my hands down across his cock. He tilted his head back and moaned in pleasure.

He lowered his head and our lips met again as I slowly dragged his zipper down. My hands were in his pants. I found his beautiful, magnificent cock. He moaned and I felt it pulse in my hands as I pulled it from his trousers.

"I've never done this," I panted, "but I want to so badly."

I slid down his body until I was on my knees. I had never seen a cock this close. Anna had trained me as a submissive to "pleasure" her strap-ons, but this was a real man's throbbing cock.

It was almost a dream and I couldn't have resisted if I had wanted to. I certainly knew how I liked women to treat a cock. I held it firmly with one hand and stroked it lightly with the other.

This gorgeous man was already leaking precum!

His desire for me spurred me on and I ran my tongue up the bottom of his shaft and right across the head. He moaned. My god, his precum was absolutely delicious.

I wrapped my lips around the head of his cock and began using my lips and tongue to slowly swirl and slurp. I was in paradise! I had never imagined that I would enjoy this so much.

I felt his hands on my head. They were just resting lightly. He had been gentle and passive so far, but I was rapidly becoming crazed with lust and I would not have minded at all to feel his hands gripping my head to take control.

But he remained passive and gentle while I began to bob my mouth up and down his cock. Anna had trained my mouth and throat vigorously, and after making sure my mouth and Darren's cock were both lubricated enough I pushed all the way down until my nose was buried in his pubic hair.

He gasped, perhaps shocked. I loved the feel of his thick member pulsing in my throat. Strap-ons don't pulse. Or taste very good. I could feel his cock throb and it drove me wild with lust. And the way it tasted ... you could not have convinced me at that moment that my mouth had ever had held anything finer.

All I wanted was this god's throbbing cock in my mouth and throat and hands. I could feel my own drool dripping down my chin.

Finally I felt his hands grip my head and I thought, "Yes! Do it! Fuck my mouth and throat!"

But he pulled me back instead and I looked up at him with nothing but raw lust.

"I'm about to cum," he gasped.

"Yes," I hissed. "I want it. Please! Fill my mouth with cum."

His hands were firm on my head. I reached up and held them there with my own hands. I felt him pull my head forward almost undetectably.

"Yes," I begged. "Yes. I want that."

I was breathing heavy. I was panting. I was possessed. I relaxed my mouth open into an "O" and slid my tongue out. His eyes gleamed and his hands wrapped around the back of my head and into my hair.

I lowered my arms and stuck my ass out behind me to give him a good look.

He pulled my head forward and I didn't resist. When his cock passed my lips I wrapped them tightly about his shaft and began sucking while he made love to my mouth.

He wasn't rough, like Anna had been. Darren held my head like a man might hold a woman's hips and made slow, passionate love to my mouth, sliding his cock into my willing throat every fifth or sixth stroke.

Every nerve in my body and mind was on fire with joy and pleasure.

It was not long before I heard him start to moan and his thrusts became more frantic and forceful. Every thrust drove his cock forcefully into my throat and I was in heaven. But I was starting to choke and gag.

Darren stopped immediately and looked down at me pleadingly.

Without a thought, my hands flew back to his cock. His cock was absolutely dripping with drool. It was so big and hard. I knew he was right on the edge.

I held the head of his cock between my lips. I looked up into his eyes and began stroking is shaft. I wanted him to fill my mouth with cum so badly, and I wanted him to see how badly I wanted it.

His eyes stayed locked on mine until I felt his cock begin to surge and his eyes crossed a little and closed.

His cock exploded cum into my eager mouth. I could feel it hit the roof of my mouth and it filled my senses. I began moaning with joy and pleasure as I swallowed again and again. It seemed like he would never stop cumming and I didn't want him to.

Finally his orgasm passed and he leaned limply against the wall. I held his flagging cock in one hand, while the other reached up under my dress and rubbed my squashed boy parts. God, it felt so good.

I rubbed the head of his cock against my lips and cheeks. I could feel semen smearing.

After a moment, he caught his breath and asked, "What would you like?"

I stood and bit my bottom lip. Pressing my body against his, I leaned in close and pressed my lips to his. The flavor of his own cum didn't even slow him down, and we kissed deeply until I whispered, "I want your cock to get hard again."

He looked at me and smiled.

"I know it's a lot to ask, but I will do almost anything," I whispered as seductively as I could, "for you to be the one to take my cherry."

"You've never done this before?" he asked.

"Only for a woman with a strap-on," I answered in quiet, quivering tones between kisses. "But your cock ... I love your cock. It felt so natural in my mouth."

I felt his cock staring to grow hard in my hand again. Between deep kisses I spurred him on.

"In my throat. Your hands in my hair," my voice was shaking with desire. "Your cum. Oh god. I can still taste it. I've never tasted anything so good."

His cock was firm in my hands again and his hands were up under my dress. His hands found my pretty, silky ruffled boyshorts.

"I never knew it would be so good," I moaned.

My garters were unsnapped.

"You are so beautiful," he whispered with his eyes caressing mine. "So passionate."

My boyshorts were at my knees and his hands were gripping my cheeks.

"I want you so badly," he whispered while nibbling my earlobe.

My dress was over my head and flung to the floor.

"Please," I moaned. "Please. Make love to me."

I was on my back and his weight was over me and his elbows on either side of my chest. My knees and feet rose into the air.

"In the top drawer ..." I motioned.

He slid it open and immediately saw the bottle of silicone lubricant.

It was all a blur. I felt his fingers pull the back of my thong aside. I watched him slather his cock with lubricant. His fingers, his beautiful sensual fingers, massaging lubricant against my waiting entrance.

I felt the head of Darren's magnificent cock press against me and pause. He looked longingly into my eyes. Never had I felt so desired.

"Yes," I begged. "Please."

Slowly he pushed the head of his cock against my ass while we gazed into each other's eyes until the resistance was overcome and I felt the head of his gorgeous cock begin to spread my ass and slide in.

"oh god, yes," was all I could say over and over.

I looked deep into his eyes and begged, "Yes. Oh Darren. Oh god. Yes."

He was slow. It took a small eternity for him to slide his cock into my ass. Small motions. First the head slipped in and he held it there for just a breath while I begged him to continue.

He rocked back and forth so little you might not even see it, but with each rock I could feel his glorious cock massage my ass and stretch it back and forth over the same millimeters of his divine member.

Having a woman fuck your ass with a strap-on is nothing like having a real man make gentle love to you.

Slowly he rocked his cock into me. Never once did he take his eyes from mine. I could see the raw desire burning in his eyes, and I'm sure he could see it in mine.

Finally I felt his hips press firmly against me and I knew there was no more depth for him to take. He withdrew so slowly it was torture. I felt the ridge behind the head of his cock against the inside of my ass and I pleaded, "No. Please. Don't take it out."

I knew he had no intention of pulling out, but there was an overwhelming fear that he would. I wanted this beautiful being to stay inside me so badly that even the idea of him pulling out was the most horrible thing imaginable.

His cock rocked its way back in and out. He never took his eyes away from mine. Then the rocking shifted to slowly sliding. All the while I was begging and pleading for him to continue as if he would do anything else.

Sliding tuned to slow thrusts and every fiber of my being screamed with pleasure and joy. I never could have imagined how good it would feel.

Our lips locked in a deep kiss. I held my legs as high in the air as I could as he made love to me. Every thrust and slide of his cock stroking something inside me that felt so amazingly good.

Even though my boy parts were still contained and held limp, I could feel an orgasm rising.

My nails raked his strong back and I could feel him picking up the pace. I was so close. I had no control. I tilted my head back and began to moan, "Oh god. Oh yes."

I could feel his cock get even harder than it already was and I could feel his cock pulsing as he drove it without mercy or thought deep into my ass. We had stopped making love. We were fucking like mindless beasts.

And I went over the edge. I could feel every nerve and cell in my body vibrating with pleasure, and even though my cock was limped and trapped firmly against my crotch my entire being exploded into orgasm and I could feel my cum pumping and spilling into my undergarments.

My vision was full of stars and all that I could hear was his hot breath. I could feel my orgasm push him over the edge into his. I could feel his cock throbbing and his hot cum spilling into me. I felt like a sacred vessel being filled with holy fluid.