Ted to Teddy

"This weekend. She thought it would help our, um, intimacy." I could feel myself blush. I had known Ben since I started. He was older than me by about ten years but the two of us had become friends, building the IT infrastructure pretty much from scratch, at least twice.

Tall and muscular, he was one of those football player type guys I had always been so jealous of. He turned out to be more of a big brother than anything else.

"But at work?" He gave me that look he used when he thought I was about to do something stupid.

"I sort of liked it." I smiled. Why I was being so open was beyond me. He was my friend, but did he need to know this much detail, and why was my little cockette straining against my cage?

"Well, if you're going to make a habit of it, just keep your shirt tucked in, ok?" He smiled.

"You're really not freaked out by this?"

"I have to admit, I'm not all that surprised. You have a certain almost feminine vibe, and I've always thought you had a nice ass." He laughed out loud, which got the attention of some nearby tables. We finished our lunch and headed back to finish with the servers. We would have a week of configuration and software installation before they could go live.

"Ben knows." I kissed Sarah when we met in the lobby to head home. "My shirt came untucked. He saw my camisole and my thong."

"How did he react? Is it going to be a problem?"

"No, he was cool, maybe too cool. Sarah, I think he kind of hit on me. He said he thought it was hot. I don't think he was joking."

"Don't worry about it. You guys have been friends for years and what's the worst that could happen? I mean, you like cock and from the size of his hands, he's got a nice one." She kissed me again and gave me a devious smile.

"I like your cock." I glared at her, emphasizing the word 'your'.

"Po tay toe, po tah toe." She giggled.

Sarah and I talked, discussing how far and how fast I wanted to go. I told her how much I loved everything about what we had discovered, and over the next few months, we found our new normal.

The sex continued to be mind-blowing. I was becoming a total cock bottom, and I was loving it. My cockette wasn't even an afterthought, only coming out when I needed to clean it.

My wardrobe morphed and changed, with my jeans getting a little tighter and my ability to hide what I was wearing under my work clothes improving. Of course, Ben still teased me a little about my new 'hobby', but I was comfortable enough that I would flash him a little lace and we would both laugh. Sarah got promoted again and started traveling once or twice a month, going out to vendor sites to close deals when there was an issue. Even staying over the weekend a time or two.

At home, I wore dresses, skirts, blouses, and assorted outfits, some you would expect to see on a street corner out near the airport. The girlier, and sometimes the sluttier, the better. Sarah was right there encouraging me at every step.

I got home one Friday to find the little red cocktail dress with all the sequins laid out on the bed, with a garter belt, stockings, skimpy thong, and matching bra.

"Girls' night out 😊," the note said.

My heart started racing. I wore lingerie under my clothes every day, but this would be the first time that I had gone anywhere in all-out Teddy mode. The thought of going out as Teddy, in that dress with those heels, both excited me and scared me to death.

I took my time getting ready, using the depilatory cream, and luxuriating in the lotion I put on after. I made sure my makeup was spot on, sexy but not quite slutty, and slipped into the sexy lingerie Sarah had left out for me.

Sarah got home just in time to zip me up and double check my wig was secure. I waited while she got ready, admiring myself in the mirror.

"Are you ready?" I just nodded. Sarah was stunning in her little black dress, which, if possible, was shorter than mine. She handed me my purse, smiled, winked, and took my hand, leading me out to the car.

The nightclub was standing room only. Sarah and I made our way to the bar. I swear I felt someone grab my butt. As soon as we got to the bar, the bartender set two margaritas in front of us, pointing down the bar to two men. Sarah picked up a margarita and took a sip, smiling at the men. I followed her lead and watched as they made their way down the bar to us.

"I'm Rick, this is Steve. We have a table if you'd like to join us?" Rick was tall with brown hair, dark brown eyes, broad shoulders, and the most disarming smile I had ever seen. Steve was just as hot, but with blonde hair and crystal blue eyes.

"I'm Sarah. This is Teddy. We'd love to." Steve took my arm and Rick Sarah's. We worked our way through the crowd to a table toward the back of the club.

I reached out and squeezed Sarah's hand.

"Just relax and be yourself." Sarah whispered. "You'll be fine."

Steve was a software developer and Rick an account executive for a company that sounded familiar. They were college buddies and next-door neighbors.

Steve was as charming as he was good looking. He had us laughing and giggling with his stories and me as nervous as a cat with the way he reached out and touched my arm. I watched Sarah and tried to mimic her behavior as she responded to similar attention from Rick.

We danced and talked and drank. I lost track of how many margaritas I had. When Steve ground his rock-hard cock into my ass on the dance floor, running his hands up my sides and touching my fake boobs, I leaned back into him, and let out an audible moan as I watched Rick lean in and bury his tongue in Sarah's mouth. She didn't pull away, instead wrapping her arms around his neck and pulling him close, grinding her crotch into his.

Back at the table, I grabbed my purse and stormed off to the bathroom, locking myself in a stall, trying not to cry.

"Teddy. Talk to me." Sarah knocked on the door. "I'll bet Steve is a good kisser, too, and you looked like you were really enjoying the way he was pawing all over you."

I had to admit it felt good to have his firm hands on me, and the thought of how he would feel inside me was still running through my head.

"Sarah, I'm just scared. Rick is so good looking and the way you two are behaving. I'm afraid I'm going to lose you." She pulled me close and hugged me.

"Oh, baby no."

It was Sarah's turn to look scared. "I owe you an apology and an explanation." She took a deep breath. "We both know there are things I can't do for you and things you can't do for me, right?" I nodded.

"And some of those things you fantasize about, I know you do because you have asked me about it. Things like being with a real man. I fantasize about the same things."

Sarah took my hands in her and looked at me like her heart was about to break. "I love you and I love what we do, but just like you, I want to feel a real man inside me. I want to feel his cock pulse deep in my pussy as he fills me with cum."

This was killing her. "Teddy All those servers you and Ben just installed. Rick's company sold them to us. I set this whole thing up. Steve knows your trans and he doesn't care. In fact, he's kind of into it. If we go back out there, they are going to take us home and fuck us until we can't walk straight. I'm sorry I didn't tell you, but I was afraid you wouldn't come if I did. Can you forgive me?"

"And what about after?"

"We can talk about that when we get home when you tell me what it was like to get fucked by a real cock."

"And if I say no?"

"Then we go say goodnight and go home and I fuck you silly anyway. They know that's a possibility." The look on her face had turned to pleading.

"You really want this, don't you?"

She nodded. "I think you do, too."

I turned to the mirror and dumped my purse, fixing my makeup, I thought about everything Sarah had done for me over the past five years, all the way back to that night she saw my cockette for the first time and let me fuck her anyway.

Pressing my lips together to smooth my lipstick, I started tossing thing back in my purse. There, with my license and keys, was a bottle of lube. I picked it up and gave Sarah a glare. "You really want this." I smiled and laughed.

She nodded. "Yes baby, I really do."

"Well, I guess it would be a waste to look this good and not get to take advantage of it."

Sarah tried to kiss me, and I stopped her. "Sorry, love, I belong to Steve tonight."

"What was that about? You girls were gone for a long time. I was starting to think Steve and I got stood up." Rick smiled as Sarah slipped under his arm and kissed his cheek.

"Girl stuff." I smiled and took a big sip of my drink, grabbing Steve's hand and dragging him back onto the dance floor.

The DJ played a slow song. I melted into Steve's arms, letting him guide me around in slow circles. "Sarah told me knew about me. That I'm a... or used to be a man. She also told me you were into that. I didn't know men liked girls like me."

"A lot of men are very into sissies." He spun me out and pulled me back in.

"I don't think I really qualify as a sissy." I gave him a coy grin.

"Well, you're small and have a naturally feminine body. You pass better than any sissy I've seen, and from what I've heard, you like to get fucked a lot. That pretty much screams sissy."

"Well, I do like sex but I'm not a sex toy and I am not calling you daddy. I don't like to be talked down to or humiliated, and nobody punishes me except Sarah." I stopped dancing and stood there, looking up into his blue eyes. "Are you ok with that?"

"If it means I get to spend more time with you and get to fuck that amazing ass I've been dreaming about since you walked in the door, I think I'm good."

I looked for Sarah and Rick, but they had already left. "It looks like it's just you and me, anyway. So, why don't we take this conversation somewhere a little more private?" I raised up on my toes and pulled his lips to mine.

"Have fun. 😊," Sarah had left me a note on our table by my purse.

Sarah's Tahoe wasn't in the parking lot, which I surmised meant that she and Rick were at our house. I thought about someone else having sex with my wife in my bed and it bothered me for a minute or two until I remembered why I was doing this in the first place. Sarah needed this. Hell, I needed this.

Locking my fingers in Steve's, I let him walk me to his car.

"Nervous?" He ran his hand across my thigh.

"Yes. I, um, I've never been with a man. In fact, I've never actually seen a real penis."

"But you're... I mean, you've got one, right?"

"Sort of. It's about the same size as my little finger. That's how Sarah and I got to this point. I've never really been able to please her like a real man."

"Wow, I didn't know that." He gave my thigh a squeeze.

"It's ok. We've worked around it for a long time. We love each other and I'll do just about anything to see her happy, so..."

"So... You're doing this for her?"

"Not entirely. I do really like to get fucked. I've just never done it with a man, Just Sarah's strap on." I blushed, and he laughed.

"You know this is weird, right? You hooking up with me so your wife can fuck another man?"

"Any weirder than you being Rick's wingman and having sex with me so he can fuck my wife? In the end, we all get what we want, so nobody gets hurt, right?"

"It could change things, you understand that?"

"I guess it could, but, like I said, I'd do just about anything for Sarah to be happy, so I'm just going to see where it goes. It's been working out ok so far, ever since Sarah first saw me naked."

"You guys are amazing. However, this plays out. Whoever ends up with you and Sarah is one lucky guy."

"I guess you'd better impress me then." I reached over and squeezed his cock, letting out a small gasp. He was as big as Sarah's dildo.

We pulled up to a split-level duplex in a very nice neighborhood. Steve parked next to Sarah's Tahoe, and I let out a sigh. She wasn't using our bed.

"Rick has one side and I have the other. It's like being roommates, but with more privacy." Steve took a bag from the backseat and came around and opened my door. The butterflies in my stomach took flight. Was I ready to do this?

"Would you like a drink?" Steve asked as we entered his duplex.

"I think I've had enough." I laughed.

Simple and clean, it was obviously a man's space with hardwood floors, leather furniture, and lots of glass. I liked his artwork, risque, but not quite erotic. A huge T.V. with a gaming console attached, small bar, and a basketball hoop in the corner.

"This is nice." I stepped out of my heels and went to look out the window. The duplex was on a hill and had an amazing view of the city below.

"You're not what I expected." Steve slipped his arms around me and gently kissed my shoulder.

"How so?" I leaned back against him, closing my eyes and letting his powerful embrace engulf me.

"I guess I was expecting someone more submissive, a little sluttier."

"This dress is pretty slutty." I laughed, pulling his arms more tightly around me.

"It's pretty hot. I guess I was thinking about the sissies I've been with. I half expected you to pull me into the restroom and give me a blow job or something. I like this better."

"I'm glad to hear it, and I thought about it a time or two." I turned in his embrace, looking up into those gorgeous blue eyes and bit my lip.

Steve lowered his lips to mine. I closed my eyes and lost myself in his kiss. This was so different than with Sarah. My knees got weak, and Steve just held me, pressing his lips to mine, exploring my mouth with his tongue as mine joined his in a delicate ballet.

My hands roamed over him, relishing the muscular body beneath his clothes. I felt so small, so petite, so feminine. I wanted this. I needed this.

Pulling away, my lips aching for the feel of his once again, I smiled at Steve and slowly dropped to my knees, sliding my hands down his chest and stomach to his waist. His belt first and then the button on his fly and the zipper. With a gentle tug, his pants slid down his athletic legs.

He watched intently as I ran my hands over his beautiful thighs, grabbing the hem of his boxers and dragged them to his knees. His cock feigned protest, doing its best to snag the soft cotton, but I prevailed, smiling to myself as it sprung free, bouncing up and down.

Sarah's cock was cold and lifeless. Steve's was warm and twitched and flexed at my touch, sending shivers through his body, eliciting soft moans. When I reached out with the tip of my tongue and licked the tip if his glans, he shuddered. When I twirled my tongue around the head and slipped it into my warm mouth, his knees almost gave out.

"Lean back." I smiled up at him. "I don't want you falling on me when you cum."

Steve leaned back against the window as I gently squeezed his balls and licked him from the base of his cock to the tip before taking him all the way down my throat.

"Holy Fucking Shit!" Steve cried, grabbing my head, and holding me there. "I thought you had never..."

I pulled him from my mouth, kissing his spongy head sweetly. "Not with a man, but I've had lots of practice with Sarah's dildos. You like?"

"Fuck yes!" He grinned down at me.

I took my time. I had done this before so many times with cold silicone lovers, but the feeling of the soft flesh in my mouth combined with the hardness of his arousal, the musky scent, and that delicious flavor I couldn't quite describe, it was true ambrosia.

I worshipped his balls, sucking them one at a time into my mouth, sucking and lapping at them with my tongue while my hands slid up and down his shaft.

I could feel him getting closer and closer, but this wasn't what I wanted.

"Unzip me." I kissed his cock one more time and stood up, turning my back to him.

His hands were shaking as the zipper slid down my back to the top of my butt. The sequin covered satin glided down my body, exposing my red and black lingerie.

"You like?" I smiled at him in our reflection in the window as I slipped my soaking wet panties down my legs, bending from my waist, letting him admire the ass he had been fantasizing about all evening.

Swishing my ass back and forth, I went to my purse to retrieve the bottle of lube Sarah had packed for me, stepping back into my heels as I sashayed back to the window, and handing Steve the lube, I leaned against the glass, arching my back, sticking my ass out and spreading my legs.

"Come on, big boy, show me how you fuck those sissies of yours."

I recognized the feel of the cool liquid on his fingers as he prepared me for his cock, moaning as he slid one, two, three fingers into my ass, spreading my sphincter open and teasing my prostate.

"Your ass is so perfect." He kissed my neck, placing one hand on the small of my back as the other guided his manhood into my eager hole. So familiar, but so different. His cock felt alive inside me. I could feel it twitch and throb as he slowly pushed it into me. And the feeling of his large powerful hands was magic, so strong yet so gentle as they teased my body, tracing the lines of my garter across my butt and thighs.

I understood what Sarah meant. I loved her and what we shared was wonderful, but I wasn't sure it would ever be enough again.

"My god, you feel so good." Steve kissed my shoulder as he bottomed out inside me. "So tight." He let out a soft moan.

"Please fuck me." My moan matched his as I clenched my butt and felt his cock twitch in response.

"My pleasure." He pulled almost all the way out, leaving just the head of his cock inside me, and started thrusting, his massive snake rubbing across my prostate with every push.

I bit my lip and lay my head on my arms, my moans getting louder and louder, one following the other faster and faster, my head bouncing off the cool glass of the window.

"Oh yeah. Oh, fuck yeah." Steve cried as he started thrusting harder and harder.

I couldn't stop it and wouldn't have if I could. The wave of pleasure that tore through me was stronger than anything I had felt with Sara and our toys. "My god, Steve, fuck me harder." I cried. "Make me yours, please, make me yours."

I was screaming as another orgasm ripped through me. I had had Steve in my mouth, teasing him with my lips and tongue for fifteen minutes before we started fucking and he had been inside me for over twenty minutes when he finally thrust into me as hard as he could, spewing hot thick liquid into my bowels. 'Oh, fuck. Oh, fuck. Oh, fuck." He was panting as he slipped his softening manhood from my throbbing ass.

"Don't move." He rubbed my back and kissed me on the ass.

"I don't think I can. That was amazing." I tried to laugh, but couldn't catch my breath.

Cold and hard, it was the perfect contrast to Steve's hot shaft. He pressed it into my hole, filling the feeling of emptiness growing in me.

"You put a butt plug in me?" I giggled.

"You said to make you mine." He helped me to stand, wrapping me in his arms and kissing me hard.

Pulling my lips from his, I started unbuttoning his shirt. "Someone is over dressed. I smiled as his glorious chest slowly revealed itself to me. Pushing his shirt off his shoulders, I ran my hands across his perfect pecs, letting my fingers explore the soft hair that covered them.

"This is a real man." I thought to myself as Steve slipped his shoes off, leaving his pants and boxers in a pile on the floor.

"Why don't we take this to my bedroom." He smiled at me. "Unless you want to give them another show." He pointed out the window. The duplex was in the shape of an 'L'. Sarah stood, wrapped in Rick's arms, on the balcony outside his bedroom, grinning. They were both naked, the afterglow of their sex as evident as my own. They had seen everything.

I smiled and waved, taking Steve's hand and letting him lead me up the stairs to his bed.