The Literotica Challenges

The Literotica Challenges Pt. 01

Emily is the love of my life. She is beautiful, wonderful, amazing, super hot and super sexy. Our life together is an absolute wonder and I still have to pinch myself to make sure I'm not in a dream, that Emily isn't a figment of my imagination, and I still find it amazing that Emily thinks the same about me too.

To me, she is gorgeous, the most beautiful woman that has ever existed. She has medium length golden blonde hair, bright, sparkling blue eyes and a lovely curvy size 14 (US 12) figure with the most perfect D cup breasts ever!

I think I'm just an average guy, standing about six feet tall with dark hair and as Emily tells me constantly, a warm, loving and caring smile.

We have been together just over three years now. We aren't married yet, but we have set a date, and in fourteen months time, we will be married in a small, private ceremony. It will be the second time for both of us. Our respective first marriages both ended due to infidelity and we have spoken at length about why the marriages ended. Yes, finding out hurt, but for us both, the hurt wasn't so much that our exes were having sex outside of the marriages.

We had both, separately, explored the possibility of swinging or being in the lifestyle when we were married to our now exes. But what hurt us both was the lies and deceit. Our trust in members of the opposite sex had been severely damaged but at the time, we were then both twenty-six when our divorces had been finalised, we knew we had time to heal and to learn to trust again.

Then Emily and I found each other and we have never been so happy. Emily and I had been introduced to each other through Chloe, a friend of both Emily and my now ex, Alison.

There was an instant attraction, though with us both being hurt before, we took it slow and steady in the beginning.

We both agreed that honesty was the best way forward. Whatever we wanted, liked, hoped for and even fantasized about and of course, what we found upsetting, was discussed there and then. We had no secrets and in truth, that is the only way to be. So together, we began the healing process and now, three years later, we had set our date and Emily now wore her engagement ring with pride. We were both looking forward to spending the rest of our lives together.

I know it sounds like a cliché, but Emily and I were meant to be, we are so perfect together. Our one regret is that we hadn't found each other sooner. There are subtle differences obviously, but we liked the same foods, restaurants, films, shows and we also share, amongst other things, a love of history. We go away a lot, weekends away and on holidays, to find out how a place, from the capital to a small rural village came to be and how it had changed, if at all, over its history. We also loved old buildings like castles, manor houses, churches, monuments and things like that.

And of course, we share a love of sex. Sex for us both is amazing, varied, wonderful and passionate. As a couple, we have done everything a loving couple could do. But we are always respectful to each other, never demanding. For both of us, sex should be fifty-fifty and be enjoyed by both to the same level.

Alongside our love of sex, we also share a love of erotica. We both love to read novels and stories online, particularly the stories on Literotica and especially those in the Loving Wives, Erotic Couplings, Group Sex, First Time and Exhibitionist and Voyeur categories. Neither of us like porn however. We found it too staged and fake and we also steered clear of the more extreme categories on Literotica like Fetish and BDSM.

The novels and online stories allowed us to use our imaginations and picture for ourselves, the places and situations that the characters found themselves in. We both find it highly erotic and Emily and I sometimes used the stories to roleplay when we were having sex. We would imagine another couple making love next to us and later switching partners.

Emily also had a thing she loved to do that was a huge turn-on for her and she would enjoy a huge, explosive orgasm every time. It was a fantasy that she hoped and dreamed would one day become reality. She would lie naked on her side, either in bed or on the sofa, with my cock in her mouth and her hand and fingers exploring her sex. As I would start to fuck her mouth, she would work her fingers deep inside her tight pussy and I would gently say to her, "Imagine a nice thick cock where your fingers are now darling! Fucking you deep as I fuck your mouth!" This would send Emily's imagination into overdrive and like I said, this would give Emily huge orgasms and her body would shake and quiver and she absolutely loves it when my own orgasm fills her mouth moments later.

One mid-week night in mid May, we were both in bed reading Literotica. I was reading a dogging story by drscar called 'Dare to Dog - Ben'. I had read the first story in the mini-series, 'Dare to Dog' the night before after Emily had mentioned it to me. This was a new direction for us both as we'd previously stuck to group or lifestyle stories like 'Golf Club Swingers' by Mag58 and 'Tom and Lori Learn to Swing' by Arpea to name but two.

As I read, I noticed Emily's hand slide gently down between her legs and she slowly started to pleasure herself as she read whatever story she had selected on her phone. I watched silently as she finished the story. She then let her phone fall onto the bed and her hand became a blur as she vigorously but sensually rubbed on her clit. Moments later, Emily heaved and she sighed and groaned loudly as her orgasm washed over her.

When her breathing had slowed and her body had calmed, Emily faced me and said, "Sorry, got a bit carried away. You didn't mind, did you? It's just, it's just that story got me so turned on. My imagination kind of... ran wild with me."

"Mind? No. God no. It was fun to watch you lose control like that. You haven't done that in a while." I said in reply. I then gestured to her phone. "So what got you so turned on then my love?"

Emily looked a little sheepish and guilty, like a little kid that had been caught with their hand in the cookie jar. But finally she showed me the story that was still on the screen. I took her phone from her and began to read. It was a short story, shorter than most that we have read and it was entitled 'My First Trick' by Owned_Wife.

I looked at Emily and handed back her phone when I had finished reading, and if I'm being honest, I had a very hard cock between my legs demanding attention. This hadn't gone unnoticed by Emily and she was soon straddling me and guiding my cock into her hot, tight hole.

Our fucking was both heated and passionate and Emily bounced up and down on my shaft as she built herself up to another orgasm. We were both so turned on and I could now feel my own cum fast approaching so I tensed and gritted my teeth in an effort to hold off until Emily came. Seconds later she screamed and her tight pussy clenched my pulsing cock and I finally let loose and spewed my seed deep into her.

Emily collapsed against my chest and we lay in each other's arms for several long minutes until I lowered my head, kissed her lovingly on her lips and said, "So, the thought of selling yourself turns you on, darling?"

Emily stayed silent as she composed her response in her mind. Like the 'dogging' stories we had both read recently, we had discussed it at length with the possibility of actually doing it and were now actively looking on the internet for suitable and safe places to try. We were, without much success so far, also looking for suitable swinging or lifestyle partners.

"Sorry," Emily said quietly, her voice barely a whisper. "But it does. I don't know why, but it does." I held her tighter against me and kissed her again.

"No need to say sorry darling. We both agreed in the beginning to be open and honest with each other so thank you for your honesty." I had been giving it some thought as to the reasons why we had both become so turned on with the 'dogging' stories and now with the 'prostitution' story that we had both just read and it came to me quite clearly in my mind.

"I know why my love. At least I think I do, so please tell me if you think I'm right or wrong on this."

Emily sat up. She was still straddling my legs and she locked her arms around my neck and stared into my eyes.

"You do? What? Tell me what you're thinking darling."

I took a deep breath. "My love, my gorgeous Emily." I began, "I think we both like them because of the randomness that those stories convey. The fact that they are strangers, faceless and nameless strangers. It's a one time thing and they would never be seen again. There is also a taboo factor to them. It's also something that many feel is wrong." I paused and ran my hands slowly up and down Emily's thighs. "Anyway," I added, "that's what I think. Do you have any thoughts on it? About it at all?"

Again, Emily stayed silent and she chewed her bottom lip as though she was afraid to truly say how she was feeling.

"Shall we," I said before Emily could reply, "shall we, before we get married... maybe, I dunno, use the stories on Literotica as inspiration to, to maybe draw up a list of things we both would like to do, to say, maybe, we've done that, experienced it, to..."

"Be adventurous?" Emily blurted, interrupting me. "Be a bit wild? A bit free? But do it with each other of course. Well, as much as we can anyway."

"Yes." I said. "'Adventurous'. Nice way of putting it darling. But would you? Could we? I mean, shall we?"

Emily kissed me. "I think we can. What happened to us before, yes it hurt. But it was because they kept it hidden, a secret. They lied to us and were deceitful. Darling, we won't be. We never have and never will! We will do this together. So, my darling loving Steve, my handsome husband-to-be, do you want to? Do you want this as well?"

I smiled, kissed Emily again and reached for a pad and pen from my nightstand drawer and passed them to her. "Ok darling, what shall we put on the... the 'Literotica Challenges' list?"

Emily smiled sexily then thought as she chewed the end of the pen. Then she started to write as I silently watched her. When she had finished, she turned the pad to face me. On it, there were three lines of writing.

1. Dogging.

2. Anonymous sex. (One night stand. Totally random. No names!)

3. Be a whore for a night.

I arched my eyebrows at the last one. "Really? You really want to sell yourself for a night, love?" But then I remembered the 'First Trick' story from earlier and how much it had turned her on and how much I had been turned on too! But, I was worried at the same time. Emily nodded. "I know it could be dangerous. But I wasn't thinking of walking the streets in a short skirt, tight top and ridiculously high heels. I dunno. I think, no, I know, that one might need a bit of planning. Quite a bit actually as I don't want that, or any of them, to be near. But that, I think, might be asking too much. Not keeping it near I mean."

"I agree." I said and took the pad and pen from her so I could add a couple of lines of my own before turning it back to face Emily and her eyes widened as she read the two extra lines that I had written.

4. Emily to have girl on girl. (Me to watch and maybe join in after.)

5. Make a porno.

I shrugged apologetically. "Sorry darling. Cross either out if you don't want to do them."

"Girl on girl?" Emily said thoughtfully. "Never done that before, but I admit, I've been curious." She then turned the pad and tapped her finger against number 5 before I could comment further. "A porno? We hate porn darling."

"We hate the porn on the internet, gorgeous." I said, lovingly correcting her. "I was thinking more of us being filmed professionally. I know it can be done."

"How?" Emily asked with mild surprise.

"John, at work. His wife and he had one made a couple of years back. I paid no real attention to it at the time though. He said he went to a studio somewhere in North London, but what I did take note of however, was how professional he said the whole experience was and how good it looked when they watched it later."

"Get details Steve. I like the sound of that!" Emily enthused and she kissed me again.

We had time, I knew that, but at work the following day I soon went to look for John, eager to get the details of the studio he had used, only to be told he was on holiday and not due back till Monday.

That night, Emily told me not to worry but understood my eagerness as she was feeling it too. After dinner, we fucked each other on the sofa and it was the same on the Friday and most of Saturday. We were loving all the sex we were having. We were both so turned on. It was like we had a new lease of life where sex was concerned and our love for each other, if it was even possible, seemed to grow and grow.

Emily's period started on Sunday just as she knew it would, and this gave us pause to sit down and talk through it more. We both wanted it to happen and we agreed to take our time and if and when we found something, we would check it out properly before going ahead. Emily also used the time wisely and the following Thursday, told me she had hopefully found a dogging site that fit our requirements. It was called Beacon Park and we agreed to go and look the following weekend when there was a bank holiday giving us both a long weekend. Nearby was a manor house and gardens that we were keen to visit so I set about booking a hotel in readiness for our weekend of fact finding and being tourists.

Before that though, on Monday morning, I finally found John and he was only too glad to give me the contact details of the studio. I didn't tell him our real reasons, as it was for Emily and I alone. But John knew of our wedding plans so assumed I wanted the details for that.

Emily was excited when I gave her the contact details and she immediately sent an email to the owner, a lady called Carol, briefly explaining what we wanted and saying we had been given her details from a previous and very happy customer. Carol replied two days later saying she was quite busy but could see us in four weeks time, just for a chat and to show us what and how she liked to do things. A date and time was set and our plans seemed to be progressing nicely.

On the Friday before our weekend, two things happened. The first happened midmorning as I was getting a cup of tea.

"Hi Steve." A pleasant female voice said from behind me and I turned to see Michelle walk into the small kitchenette where I was making myself the tea. Michelle is gorgeous. She is beautiful with long flowing chestnut coloured hair and a very attractive, curvy body. All the guys, married or not, would drool whenever Michelle walked past and I admit, I wasn't immune to her beauty either. But at least I was always civil and pleasant towards her, unlike most of the others in our office.

"Ah, don't mind them." Michelle said with a dismissive wave of her hand as she read the look on my face which showed disgust at the blatant sexist looks and occasional comments that Michelle had to endure. "I don't and that's all that matters. I know they want to get inside my knickers and I, well, take it as a compliment. But yes, it can grate sometimes. You're not like that Steve. Never have been and for that, I thank you." I smiled my acknowledgement and Michelle gave me a light hug and a kiss on my cheek. I liked Michelle for the person she was. She was a good hard worker and a valuable member of our team. Michelle though, was also gay. That was something very few knew and I think I was the only one in our office she had confided that in. I don't know why I was the only one. Michelle must have had her reasons. But like I said, I was always civil, pleasant and courteous with her so maybe that was why.

"How's that gorgeous wife-to-be of yours?" Michelle asked as I made her a coffee just how I knew she liked it.

"Fine." I answered with a beaming smile. "Better than fine. She is amazing, Michelle. I'm not ashamed to admit that. I love her to the moon and back and will do forever!" Michelle smiled warmly as I handed her the coffee.

"Good. I'm so happy for you both. Thanks for this." Michelle said, taking her coffee then she turned to leave and headed back to her desk.

"Michelle." I called after her and she turned and again entered the kitchen area where I was still standing.

"Yes?" She asked. "You ok Steve? You look, I dunno, different, like you need to get something off your chest. Are you sure you and Emily are ok?"

"Yes. Yes. We're fine. It's just...it's, Michelle, are you free at lunchtime for a drink?" I then held my hands up defensively. "Nothing untoward, I promise. I... um... want to ask you something. Something I can't talk about here."

Michelle studied me curiously. Then in a very quiet voice said, "Steve, I have told you I'm gay, right? I like you, but not in that way."

"I know and yes, you've told me. It's... it's.., please Michelle, can we talk later over a drink?" Michelle thought further then said, "Ok. Kings Arms at 1." She gave me another peck on my cheek then left.

Just before leaving to meet Michelle, Emily texted me to say we had received a reply from a couple we had seen on the internet and had sent a tentative message to some weeks previously. She also said she loved me and would tell me more when I got home. I thought about calling her, but I knew she had meetings most of the day and I was sure our timings wouldn't coincide, so I texted her back saying I loved her too and was looking forward to hearing all about it later and hopefully, I might have some news as well.

I met Michelle outside the pub and we walked in and she found a table at the far end as I got the drinks. "So," she asked and she smiled as I sat down opposite her, "what's so important and secretive that you couldn't say earlier?"

"I'm sorry," I began after taking a sip of my drink and several deep, calming breaths, "that things didn't work out for you and Zoe. Are you ok?"

Michelle shrugged. "Yeh, I'm fine. Knew it wouldn't have lasted. But it was fun while it did. But Steve, what's bothering you? You didn't ask me here to ask after me did you?" As she spoke, Michelle reached over and took my hand in hers and before I could reply added, "You've always been supportive of me, of my life choice, of who I am. You have never judged me and you have always asked me how things are and how I am, even when you were... er... going through your divorce." Her face then saddened a little bit. "I'm sorry too Steve. I should have been there for you more."

"It's ok Michelle, it really is." I paused again to collect my thoughts. "The... the reason I want to talk to you is, well, it's a bit difficult to explain."

Michelle gripped my hand tighter. "Just say how you're feeling Steve. We can iron it out later."

"Ok. Here goes. Emily and I have, kind of, drawn up a little list of things we want to do before we get married. It's a..."

"List? What sort of list?" Michelle asked then looked deeply into my eyes as if to literally pull the answer from my mind.

"A... um... kind of... sex list." I said, stammering my answer.

"Oh! Ok!" A clearly surprised Michelle replied. "And you've asked me here why? I'm gay remember."

"I know. I don't want anything for me. It's for Emily." Michelle still looked clearly confused and a little shocked. "I'm sorry. You've been through enough recently. I should go. I'm sorry I asked..." I added and made to stand up

"What Steve? Stay. Please. What do you want to ask me?"

I made myself comfortable again. "As I was saying, we have this list," I began. "I won't tell you all that's on it but one of the things is, well, Emily is bi-curious. She's never been with another woman and I was wondering if, maybe, with you I mean, if you want to of course, and you can say no." I paused, knowing I probably wasn't making a lot of sense and took a larger sip of my drink. "But I like you because of who you are, Michelle. You like to keep things private." I paused again and breathed deeply. I'd said it now. I couldn't un-say it and I looked up at Michelle with a very guilty and apologetic look on my face.