Indecent Proposal

Author's Note: This idea came from someone who commented on one of my other stories as a possible continuation. I thought it would be more fun as a standalone. Reminder that this takes place in Fantasyland and was written for your reading pleasure and any other pleasure you may get from it ;)

Indecent Proposal

Jessica and I got married right out of college. We loved each other very much, but like a lot of marriages the romance fizzled over the years. While we were dating and newlyweds, we would have sex almost every day. Now I'm lucky if we do it once a month. In addition to the sexual frustration some real world problems hit.

I had a great job and Jess didn't need to work. We were both happy with the arrangement until I got laid off. We had a little bit of savings and Jess took a job in customer service working out of the house while I looked for work. In the current economy it was hard to find anything especially at my previous pay level. Things were starting to get tight.

Our 10th Anniversary was coming up and I wanted to do something special for Jessica. I had a little bit left in the stock market and I cashed it out so I could surprise her with a nice romantic weekend. We also hadn't had sex in a while and I was looking forward to that. My first stop was to Victoria's Secret to buy her some sexy lingerie and that's when things got interesting.

I walked into the store and began to look around. A nice saleslady asked me if I needed help and I told her I was just looking. I already knew what I wanted to get her. There was a mannequin decked out in the sexiest pink lingerie I had ever seen. Jessica mainly wore black and white bras and panties, so the idea of seeing her in pink got me excited. I found the set and rubbed my fingers over the fabric. I had made sure to confirm her size before I left the house and I began to pick the pieces off the rack.

From over my shoulder I heard a man's voice.

"I think that would look great on you!" He said.

Confused by what I thought I heard, I spun around quickly and said, "WHAT?!"

"I said that would look great on you," he said.

A little embarrassed I said, "Um, this is for my wife."

"Sure Honey, that's what they all say," he replied.

Was this guy seriously hitting on me? I am a married man with a beautiful wife.

I raised my voice a bit and said, "Not that I have to justify anything to you, but this is a present for MY WIFE for our 10th anniversary!"

"I'm not sure if I believe you, but that's okay," he said, "It's really a shame, now that I see your face and your eyes, pink really is your color."

"Please just leave me alone," I said and began to walk to the register.

I checked over my shoulder a couple times and was relieved that he wasn't following me.

"Find everything?" The nice saleslady asked.

"Yes," I said.

"Would you like to sign up for our mailing list? It will give you 10% off today," she asked.

"Sure," I said, figuring every dollar I could save would help in the long run.

She spun a tablet over and I proceeded to enter my info. I paid and walked to my car.

On the drive home my mind started to spin. I can't believe a guy hit on me. What the fuck? Pink is my color? Where did that come from? I've never had a guy approach me and I've never had a single thought of being with one. As I continued to drive I decided I needed to prove my manhood to myself. I started to get hard and decided I wasn't going to wait for the weekend to have sex with Jessica.

I pulled into the driveway and quickly stashed the bag in the trunk of the car. I walked in the house to find Jessica sitting on the couch in a t-shirt and shorts watching television. This was typical for her as we usually hung out in casual clothes on the couch.

"Hi My Love," she said.

We were always affectionate like that because we truly loved each other. I didn't respond verbally this time though. I walked over to her and leaned down. I put my hand on her chin and pulled her into a kiss. This was typical in our younger years, but not much at all recently. She kissed me back and I picked her up off the couch with our lips still locked. She had always been petite and I was able to get her up easily. She wrapped her legs around my waist and we continued to make our as I carried her to our bedroom.

I slowly lowered her onto her back on our bed. She was panting and trying to catch her breath. I felt great that I had surprised her so far, but she had no idea what she was in store for. I stripped my clothes as fast as I could and yanked down her shorts to reveal her black bikini cut panties. I would call her underwear cute, but it was nothing like it used to be when we were younger and she would wear all kinds of colors and skimpy things.

I crawled onto the bed and looked into her eyes. She gave me a big smile and I was ready to make her happy. I yanked down her panties and threw them across the room. Jessica was obsessed with hygiene and she always kept herself clean and smooth. I reached my hands under her beautiful ass and lifted her up a bit. I moved my head in between her legs and kissed the center of her pussy.

"Mmmmm," she gasped.

Just like the rest of our sex life oral had decreased too, but I hadn't forgotten how much she enjoyed it. She was already wet in excitement and when I gave her clit a nice long lick she really let me know how excited she really was.

"OH MY GOD! YES!" She screamed.

Encouraged by her sounds I continued to go down on her as best as I knew how. I alternated between licking and kissing while introducing some fingers.

"Yes, Yes, Yes, Right There!" She moaned. "I'm gonna cum!"

There was no stopping me and I watched her body tense up. Then she started to buck her hips towards my mouth and screamed!

"Niiiiiiick!"

I continued my oral assault as she came down from a wild orgasm. My erection that started in the car had only gotten harder and was about to explode. I crawled up her body, kissing her as I moved. I stopped briefly to play with her B-cup boobs. They were perfect for her body and her nipples were almost as hard as my dick.

When I reached her head she didn't hesitate to pull me into a kiss, not caring I was covered in her juices. I reached down and lined myself up. She broke the kiss for a second to smile at me. I entered her slowly, but then thrusted in all the way.

"Holy Shit!" She screamed.

I covered her mouth with mine and we kissed as we made love. I felt harder than I had ever been and I wondered if she noticed. I was so worked up that I fucked her as hard as I could. After having sex hundreds of times over the years I could tell she was really enjoying it this time. Her legs were wrapped around my waist and she was doing her best to keep up with me. I'd like to say that we had sex for an hour, but it was probably closer to ten minutes when I exploded inside of her.

I rolled off her and we both lied on our backs gasping for air.

She was the first to speak, "Wow, that was great. What got into you?"

"What? Can't I make sweet love to my beautiful wife of almost ten years?" I asked.

"Of course you can. Maybe we should do it like that more often," she said.

"You don't have to ask me twice!" I said.

We kissed again before taking turns in the bathroom. Tired from our activities we both fell asleep quickly.

I woke up alone which wasn't unusual. Jessica's job required her to sign on by 8am. What was unusual was the smell bacon cooking. I got up to investigate. Jessica was in the kitchen in another t-shirt and shorts making breakfast.

"Everything okay Sweetie? Why aren't you logged into work?" I asked.

"I have something to tell you. I got laid off. I was gonna tell you last night, but well you know," she said.

"Oh, I'm so sorry," I said.

"That's okay. I hated it anyway. Besides I can always find something similar and I have a feeling this is gonna be your week!" She said.

"Have I told you how much I love you?" I asked.

"Yes, My Love, but I never get tired of hearing it. I love you too!" She said.

"I love you more," I said and we kissed.

"Doubtful!" She said.

"I was going to tell you something too," I said.

"What's that?" She asked curiously.

I planned a trip to go away for our anniversary, but maybe we shouldn't go now," I said.

"Yeah, you're probably right, but we can have a repeat of last night right here in the house if you're interested," she said.

"Um, yeah!" I said.

We sat down to eat breakfast and when we were just about done my phone buzzed.

-Text from an unknown number: "It was nice meeting you yesterday, I bought the pink set in your size just in case."

What the fuck? I thought to myself. I ignored it.

-Text: "I'll make it worth your while if you're interested." Attached to that text was a picture of the same set of lingerie I had bought for Jessica.

-I replied: "Who is this?"

-Text: "You know exactly who this is."

I was startled as my phone rang. I wanted to get rid of this guy so I decided to answer.

"Who's that?" Jessica asked.

"Probably just spam," I said as I got up and started to walk to the other room. "Let me check just in case."

"Hello?" I answered.

"Hi Nikki," he said, making my name sound feminine.

"How'd you know my name?" I asked.

"The girls behind the counter don't make a lot of money. A $50 bill goes a long way with them," he said. "But that's not important right now. I did some research and I see that you're having money trouble. I have more money than I know what to do with and I like to help people, but they have to help me too."

"And how would I help you?" I asked.

"Spend the night with me and I'll give you one hundred thousand dollars," he said.

"WHAT?!? No way!" I said in shock.

"Can you use the money?" He asked.

"Yeah, but not like that," I said. "If you have so much money you must have businesses. Give me a job and let me earn it!"

"You're saying you'd rather have a $100,000 a year job and work your ass off to earn it instead of making it in one night? He asked.

"Um," I hesitated.

"Exactly," he said.

I was stunned in silence.

"Come on Honey, it will be fun and it will solve some problems for you and your lovely wife," he said.

"Don't call me Honey!" I said loudly. "And how do you know about my wife?"

Jessica heard me and walked into the room. "Who is that?" She asked me.

"Nobody," I said to her.

The voice on the phone said, "Put her on."

"I'm hanging up now," I said.

Jessica grabbed the phone from me and asked, "Who is this?"

There was silence for about 30 seconds and then I could only hear her side of the conversation.

"Uh huh, yeah, okay, one sec," she said into the phone.

She walked into our bedroom and closed the door. I knocked but it was no use. A minute later Jess came out and handed me my phone. He had hung up.

"So you what did you get me?" She asked.

"Huh?" I asked, confused.

"At VS" She said.

"It was supposed to be a surprise for our anniversary," I said.

It sounds like you made a friend too," she said, giggling.

"What? No!" I said, offended.

Jess laughed. "I know, but he did make some interesting points."

"What did he say to you?" I asked nervously.

"He mentioned that he is a very wealthy man and is willing to help us," she said.

"But did he tell you what he wanted me to do?" I asked.

"Yes," she said.

"So why are we even talking about this?" I asked.

"Because it's One Hundred Thousand Dollars for one night! You worked really hard to make that in one year," she said.

"That's what he said," I replied.

"We can at least talk about it," she said.

"I don't know what there is to talk about. We're married, I don't think I could do things with a guy, and I'm not a prostitute!" I said.

"I know. I love you and would never want you to do something you were uncomfortable with. I just thought it was worth a conversation. It is a lot of money," she said.

"Would you do it?" I asked her.

"Not without your permission, but it doesn't matter. I offered myself as a replacement and he said the deal was only for you," she said.

"So you would do it?" I asked, surprised.

"Like I said, it's worth a conversation. A hundred grand would put out a lot of fires. I mean it's just sex for one night," she said.

"Yeah, a man having sex with me," I said, "I don't know if I could go through with it.

"Then forget it. I'll try to find another job to hold us over and you keep your search going for the big bucks," she said.

I kissed her and said, "I love you."

The week went by quickly and we found ourselves having breakfast on Friday morning, both still unemployed. Our anniversary was on Saturday and instead of getting ready to celebrate we were both depressed.

"Any leads?" She asked.

"Not really," I said. "There's always next week."

"There is that other offer," she said.

"You don't mean?" I asked, knowing exactly what she was hinting at.

"Think about it. Maybe he's available tonight, and then we can have a very happy anniversary tomorrow. We can use some of the money to go away for a couple days," she said.

"Yeah, but you're not the one who has to take a man's dick up your ass," I said.

"How about this, if you do it I'll take a man's dick up my ass, yours! I know you always wanted to try anal," she said.

"So you're telling me if I spend the night giving up my ass I can have yours?" I said.

"Yeah, plus the money of course. Seriously My Love, think about how much that will help us. It's only one night. How many times can he really go?" She said.

"You really want me to do this?" I asked.

"I want you to make the decision. You would be doing it for us," she said.

"And I get to try anal with you?" I asked.

"You know what, three times," she said.

"I really do love you. Promise this one night won't change anything between us," I said.

"Never!" She said.

We kissed.

"Give me your phone," she said.

She scrolled through and found his text. She saw the one was the picture of the pink lingerie he had sent on Monday.

"Oooh that's pretty. You'll look great in that," she said."

"Jess!" I said, a little insulted.

"To be fair I would look even better in that!" She said.

"You're in luck, because it's in the trunk of my car. That's what I was buying for you when he approached me," I said.

"Way to ruin my surprise!" She said, giggling.

-She texted him from my phone: "Hi, wondering if your offer is still available."

-He replied almost instantly: "Absolutely!"

-She texted: "Are you available tonight?"

-He replied: "Actually yes."

-She texted: "Wonderful. Give Jessica all the details. Here's her number. Can't wait to see you!"

"Was that last part necessary," I asked.

"Sorry I got caught up in the moment," she said.

Her phone rang and she answered it while walking into our bedroom.

Five minutes later she came back into the kitchen.

"Okay here's the story. His assistant will be here in an hour with a box of goodies. I'm gonna help you get ready. He will pick you up at 6pm tonight and bring you back at 9am tomorrow morning. He said he's just going to take you to his penthouse. He will have his chef make dinner and then whatever happens after that," she said.

"You forgot about the most important thing," I said.

"What's that?" She asked.

"The money," I said.

"Taken care of. I gave him our wiring instructions. He will send us $50,000 when he picks you up and the other $50,000 when he drops you off," she said.

"So I'm really doing this," I said.

"It might be fun. There are plenty of men who enjoy having sex with other men for free. You'll be doing it for us and our future. I'll be here waiting for you when you get home," she said.

I took a deep breath and said, "Okay, for us."

"While we wait for his assistant, my first instructions are to get your body nice and smooth from your eyebrows down. So follow me into the shower and I'll take care of all that hair," she said.

She warmed up the shower and we got in together. It had been years since we showered together and I didn't expect our next time to be her shaving my body so I could meet up with a man. She lathered me up and shaved me. It was pretty uneventful. I was getting excited from staring at her naked body, but any time I tried to touch her she reminded me she had a razor and needed to concentrate.

We were just about done when we heard the doorbell ring. Jessica was never shy and she just threw on a bathrobe to answer the door. I would've needed to be fully dressed. She told me to dry off and wait for her in the bedroom. When she came into the bedroom she was carrying a garment bag, and two boxes.

She started to unpack everything as I watched. The smaller box contained a pair of heels. If I had to guess they were only 2" but either way I would be wearing high heels tonight. The next box had a smaller box inside of makeup, and another smaller box with a Prada purse.

"Wow, this is some fancy stuff, I hope I can share it!" Jessica said, teasing me. "And I'm definitely borrowing that handbag!"

"Jess!" I said, not happy with her teasing.

"Let's see what other goodies are in here," she said.

She pulled out the familiar pink lingerie set. It was definitely bigger than the one I bought for her. While it made sense, because I my body was larger than hers, I wondered how he knew my size. Next she pulled out a Blonde wig. Lastly there was a tube of something and an object I couldn't identify that had a red sparkle to it.

"What's that?" I asked her, pointing at the object.

"It's a butt plug," she said.

"What?!" I exclaimed.

"Actually it's not the worst idea. You've never had anything up there before and a little stretching might make things easier," she said.

"You can't be serious," I said.

"You do whatever you want, but since he sent the plug over he's definitely planning on tapping your ass. Why not be prepared?" She said.

"You really think it will help?" I asked.

"Well I don't have any experience in that area either, but like I said, it can't hurt to be ready," she said.

"Fine," I said, "What's in the garment bag?"

"Saved the best for last," she said, knowing what was in the bag.

As she unzipped the bag my eyes were blinded by the bright red coming from inside. It was a mini dress that was shorter than anything I'd ever seen Jessica wear.

"I hope I guessed your size right," she said.

"Oh, so that's how he knew what sizes to get," I said.

"Yeah, when we spoke I told him what sizes I thought were best," she said.

"Where do we start?" I asked.

"Come over here and bend over," she said.

"The plug? First?" I asked.

"The longer you have it in the better," she said.

I walked over to the bed and dropped my robe. I heard the top of the lube snap open and Jessica pressed a finger against my hole.

"Ouch," I yelped.

"Oh yeah, this is definitely necessary. Even if he's a little smaller than you it will be a tight fit. You definitely need to be prepared," she said.

She pressed her finger inside of me and I yelped again. The finger fucked me slowly to let me get used to it. When she put her second finger inside me I got hard immediately. I felt embarrassed that my dick was betraying my manhood by getting excited with fingers in my ass. At least they were my wife's fingers.

She fingered me for a bit longer until she felt I was ready for the plug. She pulled her fingers out and I involuntarily groaned in disappointment from the sudden emptiness. Over my shoulder I could hear Jess giggle.

"Ready?" She asked, pressing the plug against my hole.

"Ready as I'll ever be," I said.

She pressed and didn't stop until the plug was all the way inside me.

"Holy Shit!" I screamed.

"How does it feel?" She asked.

"Really full!" I said.

"Just relax, you'll get used to it," she said.