Ted to Teddy

A couple of things before we get started.

First, you know the rules. Everybody's at least 18 and I only do happy endings.

Second, while I reference it and use it as a trope, this is not a sissy story. If that's what you're looking for, well, you may enjoy this, or you may not. Just be warned.

And finally, there are somethings like STDs, wearing breast forms with adhesive, and preparation for anal sex, that are very real and require our attention. We all know that, so I'm not wasting your time with a detailed description of an enema every time someone gets fucked, ok?

Good, glad we're on the same page. 😊

Enjoy and please leave me a comment.

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Compromise is the foundation of a successful relationship; any guy that has ever gone to the mall to look for a special pair of shoes with their girlfriend instead of going to Hooters to watch the game with their friends knows this, and usually, the tradeoff is worth it.

Sarah and I knew that from day one and had been doing our best to make it work for the last five years.

We had met at the NCAA Division II diving championships. I caught her attention with the same dive Greg Louganis made famous at the Olympics, the reverse 3 1/2 tuck, and I nailed it. My 88.2 points gave our small college its first ever DII championship.

Of course, Coach Rivers should get most of the credit for teaching a bunch of wannabes how to be champions, but that's not pertinent to my story. What is, is that it put me on Sarah's radar.

I discovered diving in high school to hide from the bullies after school. With my coaches' help, we had discovered my thin, agile body was perfect for some of the more difficult dives. I took to it like the proverbial fish to water. At 5'8" and as flexible as I was, I could get into nice tight tucks that made diving almost too easy. I worked tirelessly on my legs to give me maximum launch off the board, and as a side effect, a killer ass. That was the reason I needed to hide from the bullies.

Sarah and I ran into each other at a party a few weeks after the championship. She recognized me immediately. I knew her too. I had been secretly stalking her since my freshman year. Tall, athletic, long blonde hair, longer legs, and the biggest smile I had ever seen. She was a literal goddess. I was one of a dozen secret admirers she had accumulated since she walked on campus, but the first she deigned to talk to.

"That was some dive, and your entry. There was barely a ripple. I gave it a nine easy."

"Thanks. Maybe you should be a judge." She laughed, and I smiled. I fell in love with her on the spot. She could have asked me to walk into traffic and I would have done it.

We chatted for a while and eventually some football player looking guy came up and kissed her, pulling her out of my life and crushing my soul.

Life went on and I graduated with honors and took a job with a financial services company as an IT specialist. As fate would have it, Sarah was the junior business analyst for my team. With Mr. Jock out of the picture, we clicked immediately. We went to lunch and hung out with the same coworkers, becoming a little more than friends.

One day, it was just Sarah and me in the small café on the ground floor of the building our offices were in.

"I don't understand how we never met before that party. We took a lot of the same classes. We should have been running into each other everywhere." She laughed that magical laugh.

"I have a confession." I could feel myself blush. "I saw you on the first day of class freshman year. I just never thought I was in your league. You were always hanging out with the football team and, well, I can't really compete with them."

"Yeah, Mr. perfect dive, and how many national championships did those guys ever win? Besides, you're cute and easy to talk to. I'd go out with you in a heartbeat."

"How about Friday?" The words just came out of my mouth. I think she heard them before I did.

"I'd like that. You can pick me up at seven." She smiled again and gave me her address. "Now we better get back to work or we're both going to be looking for a new job on Friday and I'd hate to miss our date."

Friday couldn't get here fast enough. I nervously knocked on her door and audibly gasped when she opened the door wearing a short, red cocktail dress and four-inch heels. She towered over me.

"Oh, Ted, I'm sorry. I can put on some flats if it would make you more comfortable."

"Don't you dare." I smiled.

Dinner at a quaint little Italian place I had found online and a pleasant walk in the park down by the river. It was as perfect as a first date could be. When we got back to her apartment and she stepped out of her heels and let me kiss her, I was right back at the party where we had first met, completely in love and lost in everything that was her.

Lunch together every day, dinners and walks by the river, movies and even dancing, where I surprised her with my moves. Sometimes we just hung out and watched old movies on the couch at her apartment. They always seemed to be those sappy romantic comedies, but she liked them, and I got to be with her, so I didn't complain.

'When Harry met Sally' ended, and I yawned, getting up to leave.

"Ted, why don't you ever try anything when we're together? Kissing you is nice, but don't you want more? Don't you want me?" Tears welled behind her perfect blue eyes.

"Sarah, yes, I don't just want you. I love you. I just never want to disappoint you."

"You love me?" she smiled, and I nodded.

"I have for a long time." I leaned over and kissed her like it was going to be the last time.

"Then why don't you want to be with me? I've tried to give you every hint I could. If you love me, why?"

"I want that so bad, but I didn't think you would want to be with me. Not like that anyway."

She attacked me. Not in a bad way. She pinned me to the couch and drove her tongue into my mouth, eagerly pulling my shirt up over my head, kissing my neck and licking and biting my nipples as she moved lower and lower.

Grabbing frantically at my belt and undoing my fly, she was a beast on the hunt. If I wouldn't give her what she wanted, she was going to take it. She was going to show me how much she wanted me.

I just lay there, terror filling my heart, knowing that once she found out, it was all going to be over.

Sarah rose above me, pulling her dress over her head, exposing her exquisite body. Clad only in matching pink panties and lacey bra, she took my hands and slid them under her bra, urging me to massage her perfect breasts.

I could see the frustration on her face as she got up and grabbed the legs of my jeans, ripping them from my body.

"Dammit Ted, can't you tell how much I want you, how badly I want to be with you?"

Another jerk and my boxers joined my jeans on the floor.

There it was in all its glory, my pathetic three-inch penis standing proud and leaking pre-cum like a faucet.

Her face went from frustration to confusion to compassion in a matter of seconds.

Humiliated, I cried.

Through my tears, I watched as she stood up, removed her bra, slipped her panties down her perfect legs, climbed on top of me, and took me inside her, taking my virginity. I came almost immediately.

"I love you, too. We can make this work, I promise." Sarah laid down next to me and held me like a small child. We married three months later.

I'd like to say we found the perfect solution. She let me fuck her, or pretend to, as often as I wanted. I knew she got little to no satisfaction, so I tried to make it up to her by burying my face in her crotch and licking and sucking her lips and clit until she came all over my face. Her orgasms were impressive. With what she allowed me to do to her and the occasional blow job, we had what passed for a sex life, but I could tell she wanted more.

Things changed just a few days ago. Sarah had received a promotion, and I had gotten a nice raise, so that Friday night, we were celebrating. With the help of a little too much whiskey, I was on my best game. I fucked Sarah and then slipped down to her crotch and eagerly started licking and sucking her clit, totally oblivious to the slightly salty flavor that blended with her juices. She came hard, and I kept going, driving her to a second orgasm.

When I pulled my lips from her aching core, she collapsed next to me and started licking and sucking my little cock, massaging my tiny balls, and rubbing my perineum with her hand. I moaned. She pressed harder. Shit, it felt good. The more I moaned, the more aggressive she became, finally sliding a finger down between my cheeks and slipping it in my ass, curling it forward and pressing on my prostate. My entire body shook, tremors ran down my legs and up through my torso.

I let out a cry and erupted into her mouth. "Holy Fuck, Sarah. What did you do to me? That was amazing."

Sarah brought her lips to mine, kissing me hard, driving her tongue into my mouth and sharing the salty, bitter juice with me.

Her finger still in my ass, she looked down at me. "My honey likes it when I do this?" She pressed on my prostate again. I held my breath, nodding and letting out a long sigh.

"How about this?" She slipped a second finger into me and started moving them in and out. I couldn't believe it. She was fucking me with her fingers.

I don't know who was more amazed, her or me, but I got hard again and after about ten minutes of thrusting her now three fingers into me and massaging my prostate, I came for the third time. I had never had that kind of stamina. I was usually lucky to get hard the second time.

Sarah slipped her fingers from my ass. Using them to wipe the meager mess from my stomach, she let me lick them clean.

Exhausted, we fell asleep in each other's arms.

I woke up alone the next morning. In the bathroom, I found a bag from the pharmacy down the street and a note from Sarah.

"Ted,

I had so much fun last night. It was so hot watching how much you enjoyed our new discovery. Use this to clean up a little and DO NOT get dressed. I'll be home shortly.

Love Sarah."

When I saw the enema bottle, it wasn't difficult to figure out what was coming next. She had made me cum harder than I ever had before by shoving her fingers in my ass. I was about to get fucked and probably fucked hard.

I followed the instructions on the box and cleaned myself out before jumping in the shower. I was shaving. when Sarah came up behind me, running one hand up my back and the other between my legs, probing my ass.

"Is my baby all nice and clean?" She pressed her finger against my hole.

I smiled and nodded at her in the mirror. Trying not to cut myself as I finished shaving, I leaned over just a little, and she slipped her finger inside me. Damn, that felt good.

"Have you figured out my surprise?" she kissed my cheek as I wiped the residue of my shave from my face.

"I'm pretty sure I have an idea." I turned and pulled her into a full-on kiss.

"And you're ok with it?"

"Last night felt pretty amazing, so, yeah, I think I'd like to try it." I smiled.

"Goodie." She jumped up and down like a little girl.

"Now scoot. I need to clean these before we use them." She pulled two dildos and a leather harness out of the bag, handing me a large bottle of lubricant. The dildos had to be eight inches long if they were an inch. One of them a lot thicker than the other.

"Go get on the bed and I'll be there in a minute." She looked more excited than I had seen her in a long time. I absent-mindedly clinched my anal sphincter a few times as I walked across the bedroom.

"Teddy, honey, can you help me with this?" I watched in awe as Sarah came out of the bathroom naked. Shit, she had shaved her crotch. I could see her lips glistening from across the room. I was so hard I thought I might explode before we even started.

I guess it shouldn't have been a surprise that Sarah was getting the thicker dildo. I mean, this was my first time at this, and my ass wasn't technically designed for what we were about to do.

I knelt in front of her and watched as the huge phallus slipped inside her. It was both the most beautiful and most emasculating thing I had ever seen. It was easily four or five times the size of my little cock.

"Oh, my god, Ted." She fell into my arms. "It feels so good." I knew what she meant, but it still hurt.

If my letting her peg me with a strap on would get her what I hadn't been able to give her, then I would let her fuck me silly whenever she wanted, and I would love it.

Buckling the harness, I helped her to the bed and laid down next to her. "You know, I think I'm the one that's supposed to have trouble walking." I smiled and kissed her gently.

"You're really ok with this, Ted?"

"Baby, I love you and I want you to be happy. If this is what I need to do to give you what I haven't been able to, then I'll gladly do it. And from last night, I think I'm going to enjoy it too. Now, how do you want me?"

She rolled me onto my back and picked up the bottle of lube.

I watched as she slathered the dildo with the clear liquid and moaned as she slid her slick fingers into my ass. I pulled my knees up toward my shoulders and closed my eyes, waiting for what was next, moaning loudly as she pressed the tip of the dildo against my rose.

Slowly, it slipped inside me. It felt even better than her fingers. Deeper and deeper she went. I had expected it to hurt. Perhaps it was what we did last night, maybe it was the anticipation, but all I felt was oh so deliciously full.

Sarah was moaning as loudly as me as she thrust in and out of my ass. The silicone phallus rubbed against my prostate. With each thrust, the same wonderful feeling I had found last night grew inside me. It was so different from what I was used to.

First, I was lasting a lot longer than the one or two minutes I usually lasted when I fucked Sarah. Second, it was rising from deep inside me, not from my cock. Sure, I was dribbling pre-cum like a champ and I felt the pressure growing in my balls, but this was different, so wonderfully different.

"I'm cumming!" Sarah screamed loud enough that I'm sure the neighbors heard her. "Oh, fuck, I'm cumming so hard." I could feel her trembling above me.

The way she shuddered, and shook, made her drive the dildo into me with quick short bursts, perhaps like a vibrator. The sensation threw me over the edge, and I joined her. My cock exploded over my stomach, that wonderful feeling I had felt before radiating out through my body. My body spasms matched hers. It was as if the same wave was rushing through her body into mine and then back again. It was nothing but pure ecstasy.

Sarah lay on top of me, forcing my legs apart, the dildo still buried inside me, moaning loudly as her orgasm crested. "Oh, fuck Ted. This is amazing." She started thrusting into me again.

I came once more, followed by Sarah's second earth-shattering climax. She collapsed next to me; the dildo sliding from my now gaping ass.

Sarah started laughing. "Holy fucking shit, I never knew it could feel like that. Thank you, Ted."

I reached down to fondle my tiny little cock as she laid her head on my shoulder and cuddled next to me.

The dynamic of our entire relationship changed in that single act. I no longer had any claim to being the alpha. She had claimed that title, making me the beta. I was the fuckee, no longer the fucker; I was a bottom to her top. I was her bitch.

"Mmmmm, Ted. How do you feel?" Sarah lifted on her shoulder and smiled at me.

"A little sore, but you're right, that is amazing." I reached behind her neck and pulled her into a kiss.

"Maybe good enough for round three?" She drove her tongue into my mouth.

Sarah rolled me onto my stomach, and I raised my ass in the air, letting her take me again. My balls and prostate empty. There was no cum or even pre-cum, but that strange, wonderful feeling filled me again and again as Sarah drove herself from one crest to another. She fucked me until neither one of us could move.

We cuddled together, neither of us saying a word, until nature demanded my presence in the bathroom. I unbuckled Sarah's strap on and eased it from her throbbing pussy, taking it with me as I went to take care of my business. Without thinking, I brought the dildo that had been in her dripping cunt to my mouth and started licking it clean, even taking it in my mouth as If I were sucking a cock.

I let my mind wander, lost somewhere between feelings of emasculation and gratitude. On the one hand, this fake dick had given my wife more pleasure in a few scant hours than I had managed in five years. For the first time since we had been together, Sarah lay in our bed, completely sated. On the other, what I had experienced with her fucking me like a cheap whore was beyond anything I could have imagined. The orgasms ripped me apart and somehow mended me at the same time.

We had both risen to new and amazing heights of pleasure and deep inside; I didn't know if we would survive. We had opened a door to a world where sexual completion was no longer a compromise. It was real, tangible, attainable. It was something I couldn't give her but that she could take, something that I would receive only as a side effect of her pleasure.

"Do I need to get another one?" I could tell from the tone of her voice she was kidding.

"Another what?"

"Another boyfriend for you to play with. I saw you kissing and licking it. I just thought maybe you'd like to have one for your mouth, too." She slid her hand around my waist and squeezed my cock.

It was a joke; I knew that. She was teasing me, something we had been doing to each other since we started dating, but there was too much truth in it.

"I just like the way you taste; you know that." I tried to brush it off. But my masculinity took yet another hit.

I left the dildos on a towel on the counter to dry and went to change the sheets on the bed, leaving Sarah by herself in the bathroom.

Saturdays were housework days. Sarah and I fell into our routine, but the lighthearted banter we normally shared was stilted. It was my fault. Wrapped up in the thoughts going through my head, I went from task to task on auto pilot.

"Ted, baby, what's wrong? You haven't said a dozen words all day. I thought you liked what we did. Did I do something?" Sarah came out into the garage as I put the mower away.

"Nothing and everything." I could feel myself breaking.

"Talk to me Ted. Just tell me..."

"I never made you feel like that. I'm scared you'll leave me for someone who can."

"Oh, Ted. No. I love you. I'm not going anywhere. It felt that good because it was with you."

"But I'm not... I don't feel like..." I fell into her arms and cried.

We ended up on the couch in the living room. Sarah held me until I stopped trembling. "Talk to me, Ted. I can't help you if I don't know what's hurting you."

"Do you remember the first time we were together? When you saw me naked, saw how small I am, and you made love to me, anyway. It was the first time I ever felt like a real man, wanted, desired, like a woman could actually love me. This morning was amazing, but something changed. I liked it too much. I came so hard and my pathetic excuse for a cock didn't even matter. I lost that feeling. I'm not sure I feel like a man anymore, and that scares me. You deserve a real man, a man that can give you the things I can't."

"Yes, I remember." She was pissed. "And do you think for one minute that I fell in love with you because of the size of your cock? Do you think for one second that I practically raped you because the size of your cock mattered? I did all of that because I wanted to share the most intimate parts of myself with the most amazing man on the planet. Last night and this morning, we found a whole new world to explore together. I can get myself off with a dildo anywhere. And you're right, I could find a man with a big fat juicy cock to fuck, and it would feel good, but I can only make love with you."