Trophy Wife

Author's Note: Thanks to everyone who read the two versions of My Best Friend and Husband series. I'm taking a break from them for now, because I can't think of any other situations to put them in. If anyone is invested in them continuing, I'd love to hear suggestions on what to do with the characters. Anyway, I'm trying something a little different. Hope you enjoy!

TROPHY WIFE

MASTER BEDROOM -- EVENING - PRESENT

What am I doing? How did I let myself get talked into this? I'm getting nervous because I know he'll be coming in any minute. I've gotten myself into this situation, and I have no choice but to go through with it. Maybe it will be ok? Maybe I'll hate it. I've just had a full makeover from a friend of ours from high school. She waxed my whole body, shaped my eyebrows and gave me a blonde wig. Before I could stop her, she pierced my ears. I had nothing to compare it too, but it seemed like she put a lot of makeup on my face. By the time she was done I didn't recognize myself. The whole time she was working on me she was talking me up. She would say how pretty I was going to be, how my body was always so feminine, and how I was going to love tonight. When she played with my nipples and told me how cute my little titties were, I got a huge erection. When she looked down to see it, she told me to stand up while she got something. She came back with an ice pack and proceeded to rub it on my dick to shrink my erection. I had my eyes closed, trying to deal with the cold when I felt her put on a plastic device on my shrinking penis. I started to object, but she reached behind me and inserted a lubed butt plug into my ass. I was caged and plugged. When I asked her what she was doing she told me she was just following orders.

Next was my lingerie. I looked over to see a pile of pink lace. First she attached the bra around my back. She was right about my little man breasts, because they fit snugly in the cups. She told me to stand up and she attached a garter belt around my waist. The feeling of her running the pink nylon stockings over my newly hairless legs was amazing. Last were the panties. They were so small I couldn't believe they were classified as underwear. As she pulled them up my newly caged dick fit perfect in the front and thin strip of fabric in the back of the thong fit tight against my plug. After a quick check in the mirror, she told me I was ready. She gave me a kiss goodbye on the cheek and said see you soon. I thought that was strange, but I shrugged it off as I had bigger things, literally, to worry about. I got in bed and waited because he would be in any minute.

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PROLOGUE

My name is Eric and this whole thing started when I met a girl named Lisa in college. She was awesome and we had tons of fun together. The only hang up was that she insisted on saving herself for marriage. We made out and I got to play with her boobs, but that's as far as I got. One time I talked her into giving me a handjob, but halfway through she decided it wasn't right and I was left to take care of myself. Here I was a guy in college with a steady girlfriend and I was still a virgin.

Wanting to speed things up, I asked her father for his permission to ask her to marry me. Her parents loved me, and it was an easy yes. The problem was my parents hated her and her family for some reason. They told me if I married her they would disown me. I was conflicted. I had this beautiful woman that I loved and was dying to have sex with. I believed she loved me too and I wanted to spend the rest of my life with her. I chose her over my family, which ended up being a horrible decision.

I found myself living the good life. We had a nice apartment that her parents paid for. Her dad set me up with an excellent job at his company. Things were going great, but when we started to make the wedding plans, it started to change. All of a sudden I saw less and less of Lisa. She kept going out without me and coming home tired. I figured she was having an affair so one day I followed her. She met up with a redhead at a bar and they walked inside holding hands. I followed them in and watched from the other side of the bar. Lisa and the redhead began making out right at their table. When I confronted her that night, she confessed she was a lesbian and she didn't really love me. She had been using me this whole time to hide from her parents. She decided it was time to come clean with her parents and she broke up with me. Since I was no longer her boyfriend, her dad fired me. Everything in the apartment was hers, so I all I had to pack were some clothes..

I suddenly went from being engaged, living in a beautiful apartment, and having a great job to sitting in my car with a suitcase. I reluctantly drove to my best friend Jim's house. I've known Jim all of my life. We were neighbors and best friends since we were 4. Even though I was embarrassed to be in my situation, he was the only one I could turn to. Whereas I was down on my luck, Jim had made it for himself. He was a successful lawyer and had a huge score with a winning lotto ticket. Add a few good investments and Jim was rolling in cash. Normally I would see Jim a few times a month for lunch, a baseball game, or something. Now I was visiting him to see if I could crash at his place until I got back on my feet. I knew Jim would let me stay there, but I really hated to ask him for anything.

After settling into his guestroom we found ourselves watching TV and drinking way too much. I was moping about Lisa and how if I was only a woman she would love me back. I'm sure it was the booze talking, but he played along.

"If you were a woman I would marry you," he said, giggling. I started to laugh too. Then he kept going, "I'm closer to you than I have been with any woman I've ever dated."

Not wanting it to be awkward, I joked back, "Well, if you pay for my breast implants!" I laughed while holding my hands a foot out from my chest, "and buy me new clothes, I'll think about it."

He paused and stared at me for a second.

"What?" I asked.

"Oh nothing, I was just trying to picture you with long hair and cock sucker lips," he said in kind of a serious tone.

"Alright, enough," I said.

He got up handed me another beer and said, "So what are you going to do with your life now that Lisa has dumped you for a woman?"

I realized that I had been drinking this whole time and he had stopped a while ago. "I don't know. I have no money and no job. Too bad I'm not girl, life would be so much easier," I laughed again.

"Interesting that you say that," he said, totally sober.

"What?" I asked, "About being a girl?"

"Yeah, think about how much fun that would be," he said.

"Are you saying you think I should actually become a girl?" I asked, confused.

"Why not?" He asked.

"Because..." I started to say, trying to find the words.

He interrupted, "Think about it, if you did it, you could move in here. I've never met anyone who I'm more compatible with than you. You wouldn't have to work anymore. You would have no responsibilities, except for being there for me. We spend a lot of time together anyway, why not make it permanent? We like all the same things. We are perfect for each other. It will be just like things are now, except for a few differences."

"Dude, you're kinda blowing my mind right now," I said.

"I'm serious. This would be the best thing that ever happened to the both of us. I'm sick of those gold digging whores who are just after my money. I don't ever think I would find a girl I would want to settle down with. You on the other hand are my best friend. I know you would never hurt me and I'll love you Eric. I'll wine and dine you and buy you expensive clothes and gifts. You'll drive a nice car and we'll take beautiful vacations all over the country. Your life will be a piece of cake, no more job, no more debts and no more pain of not being loved, all in exchange for a simple change of wardrobe," he said.

"You're really asking me to suddenly become a woman now? Put on a short dress, some high heels, and dab some lipstick on? Perhaps you want to see me in some sexy lingerie and proceed to give you head before you fuck me?" I said sarcastically.

"That didn't sound like a no," he said winking.

"I don't know what to say," I said.

"Come on Erica, I know you want to be my girl," he said, making my name female.

"Is this really what you want?" I asked.

"I want what's best for me and my best friend. This solves both of our problems. Plus I can see from that tent forming in your shorts that you like the idea too," he said.

My cheeks started to turn red and all I could get out was "I..."

"Let's make a deal," he began, Remember Shannon from high school? She has her own salon. I've had her do hair and makeup for some of the girls I've been with. I'll have her come over tomorrow and give you a makeover. Spend the night with me and then you can decide what you want to do, no pressure."

"Ok," I said, "But don't get your hopes up."

"I'm not worried," he said.

"I'm kinda tired, do you mind if I go to sleep?" I said.

"Of course not," he said, "I'll call Shannon in the morning. Good Night."

I walked into the guestroom and got ready for bed. As I lied down my mind started to spin. Did I really want to be a girl? More specifically, did I want to be Jim's girl for the rest of my life? Did I really want to have huge breasts and have my body altered to be a gorgeous girl for him? Did I want to be on my knees sucking his big dick, or on my back with my legs on his shoulders as he pounded into my ass? Was all this worth everything he offered? Maybe it is. Real girls do it all the time and most would never be as happy as I would. Could I spend the rest of my life with my best friend and have full financial security in exchange for giving blowjobs and getting fucked? I already agreed to spend the night with him, so let's see what happens.

I slept pretty well and once I got myself settled, I went into the kitchen. Jim was already inside. We ate breakfast and talked. Neither of us mentioned what we spoke about last night other than him saying Shannon was coming by around 7 after dinner. The rest of the day was more of the same. We went in the pool and played some basketball outside. When we were tired we came in to play some of his arcade games and watch some TV. He had an amazing house. I always loved coming over and couldn't help thinking what it would be like to live here permanently.

Jim and I had a nice dinner. He had thrown some burgers and hot dogs on the grill which was perfect. Before I knew it the doorbell was ringing. He opened it for Shannon and we all said hi. She had two big bags with her and was ready to get to work. Jim wouldn't tell me what he told her, so I was acting shy. I didn't want to admit to anyone, especially someone I knew from high school, what Jim and I had discussed. She acted cool though and tried to make me feel comfortable.

MASTER BEDROOM -- EVENING -- PRESENT- CONTINUED

I am laying on Jim's king size bed waiting for him to come in. I am dressed like a hot blonde wearing pink lingerie and stockings. My dick is locked in a cage and there's a plug in my ass. All we discussed is that we would 'spend the night together,' but I can guess what Jim is expecting. Honestly, it's not the worst thing. If I'm going to seriously consider being a girl for him, I should experience everything I'll be expected to do. I am brought out of my thoughts when I heard the door open and Jim walked in naked with his boner sticking straight out.

"Wow, Shannon did a great job! You look amazing Erica!" He said.

I blushed, hearing my girl name for the second time. "Thanks," I said, sitting up.

"Are you ready?" He asked.

"I think so," I said, "I'm not sure what you're planning.

He walked over to the bed and hopped on. He moved his mouth close to mine and said, "Why don't we start here?"

He kissed me! It felt weird. This was my first time kissing a guy and the first time I was the one being kissed. The pressure of his lips was a new feeling and then I felt his tongue licking my lips. I don't know if it was a reflex or if I wanted to, but I opened my mouth and he stuck his tongue inside. We started making out like we were teenagers. He started rubbing my little boobs and I reached towards his crotch. For the first time in my life I was touching a cock that wasn't my own. The weird feelings started to fade and in my mind I was thinking I could get used to this. Kissing Jim was better than it had ever been with Lisa. It was so nice to feel desired. Maybe this arrangement wouldn't be that bad. He reached inside my bra and rubbed my nipples. This gave me a tingle and I felt a stirring in my panties from my caged cock. I started to stroke his dick which gave him the idea I was ready for more.

He stopped kissing me which made me whimper for more. Wow, I really was into this. He scooted up on the bed and sat on my chest. I was face to face with his rock hard erection. I didn't hesitate to give the tip a kiss and lick off the drop of precum that had formed. He looked down at me and smiled. No time like the present, so I opened my mouth and took in as much as I could. He touched my throat and I gagged a bit. I'd have to worry about that later. I started to suck the tip while I stroked him. Then it hit me. This was my first blowjob ever because, Lisa never gave me one. I decided I would make it memorable. I took him as deep as I could again. I must have been doing a good job because he let out a big moan.

"Oh baby," he said, "This is amazing. I knew you'd be good at this!"

I was happy he was enjoying it while also wondering why he knew I'd be good. Anyway I focused on the task at hand and started sucking as fast and as hard as I could.

"Erica, I know you've never done this before, so you should know I'm about to cum. If you don't want a mouthful..." he said.

I appreciated what he was saying, but in the heat of the moment I considered two things. First, this might me the only time I do this and second, if I agree to do this all the time, he would expect me to swallow his load. Either way I had to swallow this time. I felt his dick expand in my mouth and he yelled "I'm cumming!" I lost track of how many times he shot, but I was swallowing as fast as I could while trying to taste him. By the time he finished, I had swallowed it all, making me feel proud that I did a good job. His dick started to shrink as it left my mouth. He scooted up beside me and we were lying in bed facing each other.

"Whoa Erica," he said, "That might have been the best blowjob I've ever had."

"Glad you liked it," I said, "That was my first one ever, giving or receiving."

"You mean Lisa never?" He asked.

"No," I said, "I never said anything because I was embarrassed. Her ruse to cover for her being a lesbian was to say she was waiting for marriage to have sex."

"So you're a...?" He asked.

"Yes, I'm a virgin," I said as my face got bright red.

He rubbed my face gently and said," Oh Baby, I didn't know. You need this more than ever."

The fact that he was being so sweet made me feel good. We haven't had sex yet, and I think I'm ready to say yes. The chances of me finding a girl I would be as compatible with as Jim is next to impossible. If I need to be a girl to be happy, I think I'm going to do it!

He leaned in to kiss me again, not caring that he just had his dick in my mouth and I swallowed his cum. We made out again for a while until he stopped kissing my lips and started kissing down my body until he reached my panties. He took them off and looked surprised I had the cage on and the plug in.

"I wasn't sure if you would let her do that," he said.

"She kinda did it without asking," I said, "And then she said she was following your orders, so I didn't want to argue."

"How do they feel?" He asked.

"A little weird, my dick keeps trying to get hard and my asshole feels really full." I said.

"If you're going to be Erica, you're going to have orgasms with her clit and her pussy, not Eric's dick. I've heard if your prostate is being massaged correctly, an orgasm with a cage on is mind blowing," he said.

"I'll take your word for it, because the only time I've ever cum is from jerking off and it was never anything special," I said.

"I'm going to do my best to make it pleasurable for you," he said, "Are you ready to try?"

"Ok," I said.

He put my feet on the bed so my knees were bent. He lifted my ass off the bed and pulled out my plug slowly. I gasped at the feeling of emptiness. I didn't feel empty for long because he started to lick my hole and made me squirm. I never had anyone touch my hole before and now he's licking it like it's my pussy.

"Ahhhhh," I screamed as he stuck a finger in.

"It's ok Erica," he said, "Just relax."

"Sorry," I said, "You caught me by surprise."

"I'm going to put another one it now, ok? It's important that I get you ready so you enjoy the next part," he said.

"Ok," I said still wincing.

He worked a second and then a third finger inside me and was finger fucking me gently. When he felt he was ready I watched him lube himself up. He put my feet on his shoulders and moved up until his face was in front of mine.

He kissed me on the lips and asked, "Ready?"

"Slowly," I moaned. He pushed his tip into me and I felt a searing pain. "Hurts, hurts, hurts!"

"It's ok Baby, you're so brave right now. Just breathe and it will get better in a second," he said.

I was panting now, taking deep breaths. I felt myself start to open up. He must have sensed this too. He brought me into a deep tongue kiss and pushed in a little more. It still hurt a lot, but I tried to focus on the kiss, hoping it would relax me. The pain started to fade and it actually started to feel good.

"Oh My God, you're so Big!" I screamed. "You...feel...so...Gooooood!"

"Get used to it Baby," he said, "I'm gonna make you feel like this every day!"

"Ohhhhhh," I screamed as he bottomed out inside me.

"You like that Erica?" He asked.

"This is awesome! I've never felt anything like this!" I said.

"Told ya Baby, and I haven't even started fucking you yet," he said.

Then he pulled back to the tip and thrusted back into me all the way. I screamed louder than I ever have before. He repeated this motion over and over. I started pushing my ass back against him. Then he slowed down and kissed me again.

I pulled off his kiss and asked, "Why did you slow down?"

"I thought I might be going too hard for your first time," he replied.

"No, come on and Fuck Me!" I yelled.

He continued with his slow thrusts and said, "Hang on, I want to ask you a few questions and I want you to focus, ok?"

"Ok," I said, "But hurry up because my whole body is tingling and I'm about to explode!"

He pulled back and thrust into me hard and asked, "Erica, are you going to be my girl?"

"Yes!" I screamed.

He thrust into me hard again, "Are you going to get huge boobs for me to play with?"

"Yes!" I moaned.

Thrusting hard into me again, this time nailing my prostate, he asked, "Are you gonna dress sexy for me all the time?"

"Yesssss!" I screamed trying to concentrate.

Keeping his attention on my prostate he asked, "Are you going to give me blowjobs and let me fuck you anytime I want?"

"If you make me feel like this, you can do whatever you want to me!" I yelled out in between deep breaths.

"Last question, Erica will you marry me? Will you be my bombshell blonde trophy wife?" He asked as he went full speed on my prostate.

"YES! YES! YES!" I screamed as I came and passed out.

I woke up to the feeling of him pecking my lips. "Welcome back," he said.