Ted to Teddy

I wanted to believe her, and I absolutely believe that she believed what she had said, but sometimes the most impassioned words are the most prophetic.

I took a shower, and we ordered Chinese for dinner, cuddling on the couch, watching some old romantic comedy like we had when we were dating. I was so lost in all the confusing thoughts running through my head, I couldn't even tell you what we watched.

After a fitful sleep, I awoke to the wonderful feeling my Sarah's lips around my tiny cock and her slick fingers sliding in and out of my ass. I let out a loud moan, subconsciously moving my legs apart to give her better access.

"Oh, Sarah, that feels so good." I moaned as I squirted into her mouth.

"I'm glad I could make my little man feel good." She slipped her fingers from my ass and positioned herself between my legs.

"Oh, fuck." I sighed loudly as she pushed her fake cock inside me. Pulling my legs up to my chest, I rocked into her advances, opening my eyes to see the hunger in hers. It felt so good.

I reached up to massage her perfect breasts while she fucked me, pulling my feet behind her to keep her as deep inside me as I could. This was so much better than any meager attempt I had ever made to fuck her. Maybe I was never meant to be a real man. Maybe this is what I was made for. Maybe... I arched my back and let out a soft scream as an orgasm ripped through me, my little cock still flopping softly between my legs.

Sarah shuddered above me, chasing her first climax of what would be three. I laid there beneath her, riding the waves of pleasure coursing through my body, rationalizing and justifying how much I loved her fucking me like a bitch in heat.

Sarah collapsed on top of me, her cock sliding from my ass as we moaned together in the afterglow of our sex. I pulled her close and kissed the top of her head. She was my love, my life, and I could still take care of her, even if it meant I wasn't the man I always thought I wanted to be.

"Ted?" Her voice was soft. "Can I watch you clean it? Like you did yesterday."

"What's that babe?"

"My dildo. Can I watch you clean it like you did yesterday? With your mouth. It was really sexy the way you played with it."

"You want me to suck your cock?" I let out a small laugh.

"If you want to look at it that way, I guess so. You seemed to enjoy it yesterday, and I thought maybe you'd want to." Where had I heard that line of logic before? I watched as she slid the harness down her legs, letting out a soft moan as the slick phallus slipped from her dripping wetness.

"I think I'd rather clean you." I gave her a devilish smile.

"Do the dildo first and give me time to recover." She handed it to me, biting her lip seductively.

I did my best impression of what I thought a blow job should look like, knowing that this was all for Sarah's benefit. I could hear her moaning and knew she was fingering herself as I worked the fake dick in and out of my mouth, and that seemed to inspire me.

I went well past the point of the shaft I was worshiping being clean, letting Sarah's moans fill my ears, imagining that it was me bringing her that pleasure by what I was doing. Laying on my side bobbing my head up and down the slick shaft, rubbing my little cock between my thighs, I felt myself cum when Sarah let out a long sigh, telling me she had, too.

"Did you enjoy yourself? I know I did." Sarah ran her fingers through my hair. "That was so hot. Watching you do that."

I let out an exasperated sigh as I rolled onto my back, my legs spreading open, sticky strings of cum stretching between my thighs.

"Teddy, you came sucking a cock." Sarah's voice sounded more excited than anything else.

It didn't bother me at all. I didn't even notice she had called me 'Teddy.'

It was Sarah's turn to be quiet. It differed from my melancholy funk from Saturday. I could see the wheels turning in her head. She was working on something. I knew from experience; she would tell me all about it when she knew what she wanted to do.

She disappeared into our office, and I went out to the garage to reorganize some shelves that I had been avoiding for a while. When I came back inside, Sarah had gone somewhere.

"Be back soon. Love, 'S'" was all the note she stuck to the refrigerator door said.

She found me on the sofa wrapped in a book I had been wanting to read but never made the time for, some Jack Reacher type thing with a strong manly hero that always gets the girl.

"I've been thinking." She smiled and sat down next to me.

I knew more changes were coming.

"Sometimes the best way to get past something that is bothering you is to embrace it, right?"

"Sarah, what are we talking about?"

She looked away and took a deep breath. "I'm talking about you being afraid that you're not a man anymore, and how much you like getting fucked like a girl, and then you came sucking that dildo. I was just thinking instead of trying to prove you're still a man. Maybe we should go the other way just a little."

"And...?"

"And." She smiled. "I went shopping for a few things I think might help." She pointed to the shopping bags on the floor next to her. One of them was from Victoria's Secret.

"Just hear me out, ok, Teddy?" She cut me off before I could protest.

"It's bothered you since before we started dating that you don't have a real cock. I Accepted it because I love you, and we have worked with it. But the past few days, it has really hit home with you. I can tell. It hurts me that I reopened that wound, so I want to try and fix it. We can't do anything about the size of your penis, but maybe we can find a way for you to be more comfortable with who you really are."

The brutal truth of what she said hit me like a hammer. She bit her lip. The expression on her face was begging me to understand.

I thought about what she said. "What do you mean 'who I really am?'"

"Teddy, I'm just going to be honest, so please don't get upset. I've thought about some of this for a long time and, well, you were right that day we first had sex. You aren't a 'real' man." She did the air quotes thing. "You are soft and sensitive and caring, so supportive and easy to talk to and willing to explore new things. You are everything I want in a partner, but masculine, you just aren't. I want to help you figure it out. I don't know how far we'll need to go, but I need you to be happy with yourself again. The way you were yesterday ripped my heart out."

"So, what do you want to do?" I knew she was right. I had been fighting a losing battle my entire life. In the past two days, what masculinity I had had been destroyed. Maybe it was time to just go with it and see where it went.

"First, you and I are going to take a shower together and get rid of all your body hair. Then, we are going to play dress up and see how comfortable you are with your feminine side. That may take a while." She smiled at me coyly. "Once we figure out where you're comfortable, I'm going to fuck you until you scream like a little girl."

I liked that last part.

I helped her carry all the shopping bags to the bedroom. She grabbed the one from the pharmacy and took my hand, leading me to the bathroom, organizing the bottles while I stripped.

Sarah covered me from face to my toes with a thick cream. "Wait five minutes before you get in the shower. I'll be right back." She smiled and left to get things ready in the bathroom for when we had finished with the shower.

She was excited. I was more nervous than a cat at a rocking chair convention.

I had just stepped into the shower and just begun rinsing the depilatory from my body when Sarah came back into the bathroom, setting some things on the vanity before stepping into the warm spray to help me. My whole body tingled. The feeling of the water sheeting across my now hairless body was electric.

"You like?" Sarah smiled at me. I moaned, running my hands across my skin, and nodded.

As I washed my hair with the new shampoo and conditioner, a soft floral scent filled my head. I always loved the aroma of Sarah's hair, and this was even softer, more delicate. I decided I liked it.

"All over." She handed me the lotion as she laid the other items she had brought with her out on the counter.

The lotion felt amazing as I spread it across my now hairless body, the fragrance complimenting the smell of my shampoo perfectly.

Looking at what Sarah was doing, I recognized the panties, the garter, and the stockings. "What's that?" I pointed to the small pink object that looked a little like a bottle cap.

"That is for your little 'cockette', if you want to wear it." She said it so matter of fact. "It will keep it from getting hard and make it easier to conceal in your panties." She brought it over for me to examine.

"Ok." I handed it back to her.

"That's a big step. Are you sure?"

"I thought about it in the shower. I think I want to go all the way. You're right, I need to figure this out and that's the best way. Like taking off a bandage."

I watched as she slipped the ring around my 'cockette', as she had called it, pulling my small testicles through before inserting the hollow sleeve in my urethra and locking the cap in place. My cockette disappeared, only the pink cap remained almost unnoticeable against my crotch.

"You'll need to sit to go potty," she smiled up at me.

The panties were pink, satin and lace and felt magical against my crotch, the lace trim gently caressing my butt. I couldn't help running my hands over them and admiring myself in the mirror. Sarah helped me fasten the garter around my waist, slipping the straps under my panties, and showing me how to slip the stockings up my legs. I could feel my cockette try to stir only to be denied by the cage. This was too erotic.

I didn't even notice Sarah leave the room as I preened in front of the mirror, my hands sliding over my stockings and my panties. Everything felt so delicious.

"Turn around, silly girl." She was laughing at me. "It feels nice, doesn't it?

I almost said, "You have no idea" but realized that she knew exactly how wonderful it felt.

"I hadn't expected you to be so eager, but since you want to go all the way, we'll need these." She opened a box and showed me two modest breast forms.

We followed the instructions and applied the adhesive to the forms, pressing them to my chest. Sarah smoothed the edges. They looked like they were real. I liked the weight and the way they moved with me.

Once more, my cockette tried and failed. I smiled and, using my finger to catch the clear liquid it was leaking, brought it to my mouth, tasting it with the tip of my tongue.

The bra matched the panties and garter. I had to admit, I had a hot little body. Sarah didn't say a word, she just watched my reactions as she added one piece and then another to the puzzle.

I was both excited and confused and a little worried about the wet spot growing in my panties. I liked the way I looked, the way the panties accented my ass, the way the satin and lace felt on my body as I moved. And my perky little boobs, all wrapped in lace, it was all too perfect. But was it really me?

"Are you OK?" Sarah had picked up on my nervousness.

"I think so. If all feels so good, but part of me feels wrong."

"We can stop if you want." I shook my head no.

Sarah sat me at the vanity, pulling out her makeup and doing my face in a very subdued style. When she set the deep auburn wig on my head, and I looked in the mirror, I was speechless. I was almost as pretty as she was.

"Is that really me?" I couldn't take my eyes off the girl in the mirror. My cockette strained against the cage and more pre-cum leaked. "I may need to change my panties." I heard myself giggle. The wet spot was getting obvious.

"Take them off." Sarah gave me a devious smile and went back to the bedroom. I slipped the now soaked panties down my legs and stepped out of them, once again admiring the beautiful girl in the mirror, the one with the small pink cap where her clit should have been.

"Bend over Teddy." Sarah pulled my wig to the side and kissed my neck and shoulder, applying gentle pressure to my back.

Placing my hands on the vanity, I arched my back, getting ready for what I knew was coming. I spread my legs just enough and watched as Sarah fucked the girl in the mirror. The look of pleasure on the girl's face, the way her tits bounced with each thrust, the sound of her moans, the little squeals she made when the cock in her ass hit her prostate, the way she bit her lip, she was in ecstasy, and she was me.

I watched as Sarah dominated her, a look of lust and determination on her face, thrusting hard again and again into the girl's eager ass.

It was beautiful. When the girl screamed, my cockette erupted covering my fingers with sticky goo. When I was sure I had it all, I brought my fingers to my mouth and licked and sucked them clean.

Using a warm washcloth, I cleaned up the rest of the mess between my legs. Turning to Sarah, I Dropped to my knees and used the same cloth to clean the silicone cock she had just fucked me with before taking it in my mouth and burying it in my throat. Sucking and licking, using my hand to tug and pull, I maneuvered Sarah, so she was resting against the vanity and continue my onslaught.

Her hands found the side of my head and she began thrusting, matching my motion as her moans grew louder and louder until, shuddering, she shoved the dildo down my throat and screamed as she slowly collapsed to the floor.

We nestled in each other's arms on the cool tile floor, Sarah running her fingers through the auburn strands of my wig while I continued to lick and tease her cock.

"You would make some man so happy." She laughed and hugged me.

"Is it better with a man?" a hint of doubt drifted through the air with my words.

"It's different, but not really better or worse. A man's orgasm is so intense and when they cum deep inside you, well, it's pretty awesome." She said it so matter of fact, like I didn't know what she was talking about, and, I guess, to a certain extent, she was right, as I had definitely never cum deep inside her.

She gave me a clean pair of panties and we spent the next few hours doing our own little fashion show. Dresses and skirts with cute tops, all of them on the slutty side. I took to wearing heels like I had been doing it my entire life.

Prancing around in a tight red sequined cocktail dress that pretended to cover my garters, and six-inch heels, I looked like I belonged either in a high-end nightclub dancing or on a street corner selling myself. I had never felt so alive.

Spinning in a circle, arms wide, I fell back onto the bed and giggled. "Sarah, what is happening to me? I love this. I want it all. What are we going to do?"

"For now, we are going to get you cleaned up and ready for bed. It's eleven o'clock and we both have work in the morning."

Giving her a pouty look, I got up, turning around so she could unzip my dress. Once we had everything put away and she had shown me how to remove my makeup, we slipped into bed together in matching pink chiffon baby doll nighties. I drifted off to sleep with her spooning behind me, holding me tight in her arms.

Wonderful feelings ran through me as I slowly woke up. Realizing that it wasn't a dream, I pulled my right leg up to my chest to give Sarah better access as she slowly moved her cock in and out of me.

"Reach under your pillow, baby. I have a surprise for you."

Still half asleep, I slipped my hand under the pillow to find a third dildo. Smaller than the other two, I immediately knew what it was for. I brought it to my lips and started licking and sucking, moaning loudly as Sarah brought me closer and closer to my peak.

What a wonderful way to wake up.

We exploded together, my orgasm coming from deep inside me, tremors of delight surging through my body.

"Stop. Stay." I moaned as Sarah pulled herself from me. I knew that as soon as we got up, it would be over. I would have to get dressed for work and all the joy I had felt when I saw myself dressed in lace and satin and heels and, oh my god, that red sequined cocktail dress would vanish. I knew things would go back to 'normal' and I wasn't sure I wanted that.

Sarah nestled behind, gently caressing my body with her hand as she slowly thrust into me. We cuddled together, somehow her understanding the gravity of the moment, at least for me.

Just 48 hours ago, Sarah had taken me for the first time, changing me forever as she opened a door to things I would never have considered. Taking me to a place that if you had asked me before, I would have vehemently denied existed. And now I lay next to my wife, not wanting her to stop fucking me like a girl, trying to figure out how all the new feelings and sensations I had discovered would fit into our world.

"Baby, we're going to be late for work." She pulled up and kissed my cheek. "As much as I'm enjoying it, and I think you are too, we can't stay here like this all morning."

"I know." I moaned softly as she pulled from me. "I just wanted it to last a little longer. This weekend was, I don't know how to describe it, but I kind of don't want it to end. I liked everything we did. Everything."

"Even last night, when I dressed you up?"

I rolled over and blushed. "Especially last night. When you fucked me in the bathroom and I watched in the mirror, it was like watching someone else, two beautiful women having hot steamy sex, and the orgasm. Only one of them was me. Holy fuck, it was hot." I smiled.

"Well, come on girlfriend. Let's get cleaned up. I followed her to the bathroom, and we took a shower together. Afterward, she helped me slather my body with lotion and I almost begged her to be late and fuck me again. I was so far gone; it wasn't even funny.

"Ted, are you sure?" Sarah was giving me a curious look as I slipped the lacey bra on over my arms and fastened it around my forms.

"It goes with the panties, and I'll be in the server room all day installing new server blades. It's cold in there so I'll have a jacket on. Nobody will notice."

"I have created a monster. You are such a girl." She laughed. "A least put a camisole on over it to help hide the lace and straps." The look on her face was a mix of amusement and satisfaction. I caught myself wondering how far she wanted this to go.

Sarah had meetings all day while Ben and I got lost in the server room, swapping out and configuring new blades.

My idea of wearing a jacket sounded good in theory. Server blades aren't heavy, but they come individually boxed. With unboxing, installation, and wiring, that's a lot of moving around. My jacket lasted all of thirty minutes before I started sweating. Even at the balmy 68 degrees, we kept the server room.

All that bending and stooping and moving around, I was so busy I didn't notice what had happened. "Hey man, you might want to tuck your shirt back in. I can see your panties." Ben ran his hand across my back, running a finger along my bra as we headed out the door for lunch.

I ducked into the nearest men's room and sure enough, my shirt was completely untucked in the back, the lacey fringe of my camisole exposed and if I bent over, the top of my thong was obvious. "Fuck."

Trying to stay composed, I joined Ben in the cafeteria. "About that..." I started.

"Hey man, whatever you and Sarah are into, that's between you and her. It's cool with me." He paused, looking down at his food. "Just so you know, I think it's hot."

Double Fuck, I worked with Ben every day and he was hitting on me.

"Is it that obvious?" I could feel the panicked look on my face.

"No, unless you bend over, and your shirt comes untucked." He smiled at me.

"How long?"

"Pretty much since you took your jacket off. What can I say? I was enjoying the show. I could ask you the same thing."