Our Journey Ch. 01

Story Info
Maddie's first adventure.
4.5k words
4.14
27.8k
34
Story does not have any tags

Part 1 of the 5 part series

Updated 06/10/2023
Created 08/26/2020
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Throughout the 20 odd years of my marriage I have had many fantasies of involving others in our sex life. These fantasies come in many forms including; threesomes, wife swapping, wife sharing and even her playing without me. My wife Maddie is fairly conservative when it comes to sex and she believes strongly in our vows of, forsaking all others. She rarely lets herself 'go' in the bedroom and I believe this is why she doesn't get as much enjoyment from sex as she could do. Maddie doesn't come easily but when she does it is very powerful! Having said all of this, we are not total prudes and have enjoyed a bit of experimentation over the years. Occasionally we have anal, light bondage, rimming and even some water sports. While she might not always be dynamite in bed, Maddie's greatest skill is giving head. I've experienced numerous blow jobs from different women in the past and none of them compare to Maddie when she's in the mood!

Before I go on I guess I should tell everyone a little bit about us. My name is Pete, I'm 48, average height and build. Even my cock is average. Maddie is a size 12 with B cups that aren't as pert as they once were, three kids will do that. She will also say her thighs could use some toning, but I'm not perfect and I still find her very sexy. At 45 she still attracts attention from men of all ages, we men love a MILF!

Like I said earlier I have many fantasies of including others in our sex life. While the thought of being with two women is very appealing, Maddie would never be down for this and my main goal was her pleasure. To have her totally let go and discover herself as a sexual being. I figured if she could experience sex for sex sake, not some notion of sex being the embodiment of two people in love, she might be able to let herself go and just enjoy the raw physical enjoyment that can come from fucking. Besides this, the thought of seeing (or hearing about) her getting fucked by another man was a huge turn on. It was almost an obsession that was never far from my mind.

I often brought this up with Maddie, we even roll played it a bit during sex, but while she seemed to enjoy it at the time she later always dismissed it as her acting for my pleasure. This was typical of her, never letting herself go with the pleasure. Always maintaining the proper wife and mum persona that she believed was her role in life. I grew frustrated, to the point where I gave up. I stopped instigating sex, I stopped suggesting ideas to spice things up. When she wanted sex I would go along with whatever she wanted. Usually it meant missionary until she was ready for orgasm, then she would use her toy, buzz, on her clit until she came. Most times I felt like a real live dildo, only there to help her get off. Sometimes if she was having trouble I was relegated to spectator status. Once she was done I would resume and finish as quick as I could before she got sick of it.

Now you might wonder why I hung around, after all sex was important to me and I wasn't having my needs met? But at the end of the day I loved her, I loved my family and I loved the life we had built together. In short, I decided to sacrifice one aspect of my life and focus on the positives.

Things suddenly changed when Maddie had to go away for a few days for work. She is a teacher at a local school and was selected to attend a three day conference in Brisbane. Prior to leaving, I reminded her that she had a hall pass and that she should feel free to enjoy herself. She immediately dismissed this telling me this would never happen. Ah well, I could always dream!

Throughout the first day we exchanged numerous messages, just everyday stuff. How was the conference? Did they provide good food? How was my day and did I miss her? Once her day was finished she called me and told me she was going to have a drink with a few other attendees. I resisted the urge to ask who with and just told her to have fun and treat it like a short holiday. I did find it interesting that she was doing this as she didn't tend to drink often and she certainly wasn't a particularly social person.

I didn't hear from her for a couple of hours, which didn't bother me as I occupied myself reading Literotica.com stories and, well you get the picture. At about 8pm I got a text from Maddie, it went something like this. Well actually exactly like this cause I still have the whole conversation saved and look back at it regularly!

Maddie: "Hey babe how are you?"

Me: "Good, just had dinner and watching some TV."

Me: "What about yourself?"

There was no reply for about 10 minutes.

Maddie: "Yeah good. I've discovered a new wine that I really like. Not too sweet but its pretty strong and I can feel it affecting me!"

Me: "Cool. Make sure you don't get too drunk and can't find your way back to the motel."

Maddie: "You told me to have fun. Besides there are a few of us here who are staying at the same place, I'm sure they'll make sure I get home safe."

Me: "Absolutely. Let your hair down, have some fun, just be safe."

Maddie: "Don't worry, my new friend has promised to take good care of me."

New friend? Now this sounds interesting.

Me: "Well if he said he'll take good care of you that's good."

Maddie: "Why do you assume its a he?"

Me: "Well is it?"

Maddie: "Maybe, you did say this wouldn't worry you. You even told me that you would like this."

Me: "Absolutely! Have fun, but I will want ALL the details!"

Me: "Maybe even a picture or two?????"

Maddie: "You wish! Anyway they are all telling me to stop being anti-social and get off my phone, I'll call you later."

Me: "No worries, talk later."

I was intrigued but trying not to read too much into the conversation. I had fallen asleep by the time she messaged me a few hours later at 10pm to see if I was awake. I told her I was and the phone rang almost immediately. She didn't sound drunk or even chirpy as I would have expected after a few drinks. In fact she was very quiet and kinda sad. I asked what was up and she told me nothing, just tired. I suggested she get some sleep which she agreed with, however she continued with a painful conversation, you know the type that you have when you don't want to talk about anything in particular but don't want to finish. I sensed there was something she wanted to talk about but couldn't bring herself to. Despite my earlier curiosity I was now feeling very tired and ready for sleep. I said goodnight and ended the call. With in a minute my phone buzzed with a message.

Maddie: "I love you xxxxxx"

Me: "I love you too xxx"

Maddie: "Are you sure?"

Me: "Absolutely! xxxxx"

Maddie: "I kissed him!"

Well I was awake now! I sat up in bed and called her. She answered on the first ring. I could tell she was nervous, almost in tears. She said she was so sorry and it was a huge mistake and could I forgive her. I rather sternly told her to stop, that I loved her and that there was no way I could be mad at her cause I had been pushing her into this for a long time. After a while and some solid reassurance I convinced her that I was totally fine with whatever happened and that I could even show her my hard on to prove it. She called me perverted but I could tell by her voice that she was relieved and I sensed a smile in her voice. I said, "but now I want to hear all the details."

This was a verbal conversation so I don't have a saved transcript, but it is burnt into my brain.

"His name is Jake and he is a bit younger than me, 38. He is married with 2 teenage girls. This makes me feel bad cause I am cheating with someone else's husband."

I said, "you are not responsible for his actions, apart from being so hot that he couldn't resist you!"

She laughed, "not sure about that, I'm sure he was just looking for some fun and thought I was his best chance!"

"Baby, don't underestimate your hotness." I assured her. "Please go on."

"Well we were in the same group for some activities and I noticed how well dressed he was, you know how I like men who take pride in their appearance. He was also quite attractive and in good shape, not muscle bound but a bit sporty looking. Throughout the day he was always making jokes, a bit like you do. During afternoon tea he said a group of them were going to have a drink afterwards and I should come along. I thought 'what the hell' and said yes. At the pub we talked a lot because I didn't know anyone and you know I'm not particularly outgoing. I guess we flirted a bit too. By the time we decided to head home there was only 5 of us left. The other 3 were staying at a different motel so it was just Jake and I heading back to our motel. He was staying on the floor below me but insisted on walking me to my door. When we got to my room and I opened my door we both just stood there, it was sort of awkward. I guess we were both wondering what the other was expecting. After what seemed like minutes he said goodnight and leaned in for a hug. I hugged him back, he smelt so nice! He pulled his head back and we stared at each other. He then leaned in kissed me on the lips. I hesitated for a second then opened my mouth turning what was probably only meant to be a quick peck on the lips into a full on pash. We made out like a pair of teenagers! My heart was racing and in that moment he could have done anything to me! I'm sorry to say but I have never been so turned on by kissing! His hands moved down and cupped my arse, pulling him into me. I could feel his hard on pushed up against me so I knew he was excited too! We made out for a while and it felt so good. His hands roamed up and down my back and arse. I could feel my pussy getting wet as I tried to rub it up against the bulge in his pants. Suddenly the elevator doors opened just down the hall from us and I jumped back. Then reality set in. I'm married. He's married. We shouldn't be doing this! I told him I better get to bed and I'll see him tomorrow. I went into my room and closed the door. I looked out the peep hole and saw him stand there for a moment before heading off down the hallway. I sunk to the floor and cried. After a while I went and had a shower to wash away my guilt then called you."

"Wow!" Was all I could say. "Baby that has got me so hot!"

Maddie replied, "I'm glad you enjoyed it cause I feel like crap."

I spent the next hour reassuring Maddie that I wasn't upset and that I loved her. I also thanked her repeatedly for taking the first step in making my fantasy come true. I don't know that I was very successful but in the end the need for sleep won out and we said our goodnights before hanging up. I had a very restless night dreaming of the events Maddie had told me about. I also had multiple wanks!

The next morning was a mad rush to get ready for work, meaning I only had a brief chat with Maddie. Neither of us made any mention of the events of the previous evening. Like the previous day, we exchanged messages of a fairly general nature. It wasn't until just before lunch that I decided to address the elephant in the room.

Me: "How is Jake today?"

Maddie: "He is totally ignoring me. I think he is pissed that I shut the door on him. Or he's decided that I'm not going to put out so he'll target someone else. It's a bit awkward, I feel like a piece of shit."

Me: "Well it is possible that he has decided to move on to someone else who will be willing to go all the way but I doubt that. The more likely scenario is that he is feeling pretty awkward himself. He is probably worried that you're pissed at him and you'll let his secret out. I'll bet, just like you he is unsure how to act and has just decided to avoid the situation altogether."

Me: "Do you see him chatting up another chick?"

Maddie: "No, not really. He has been hanging with a bunch of guys from the coast."

Me: "Yep. Thinks he has fucked up and trying avoid any trouble."

Me: "Here's what you need to do. At lunch talk to him. Walk straight up to him, tell him you enjoyed the drinks last night and thank him for making sure you got home safe. Tell him how nervous you get finding your way around in the big city cause you're such a country girl. I'll bet he will soften his attitude, probably ask you to drinks again this evening."

Maddie: "Do I want to go to drinks again?"

Me: "Yep. You had a good time and you know what to expect so you are totally in control. I love you xxxxxx."

Maddie: " I love you too. I don't understand you, but I know I love you!"

Me: "If you understood me it would be boring!"

After lunch I got a message telling me I was right. I was busy so just replied with a thumbs up and said I would talk later. Once I finished work I called Maddie and she told me nobody was really interested in going for drinks so she was meeting Jake in the bar of the motel they were staying in. I refrained from saying I told you so and said have a great night. I had a soccer meeting and wouldn't be home until late so I would message her once I was done. Surprisingly I didn't really give the situation much thought over the next few hours as I was pretty wrapped up in what I was doing.

When I got home around 9pm I called her but she didn't answer. Typically this wouldn't be unusual as she doesn't have her phone in her hand 24/7, but since she had been away she had been responding promptly to all my messages and calls. I was curious but went about getting myself showered and ready for bed. About 20 minutes later she called. Straight away I could tell she was excited, maybe a little drunk also. I asked her how her evening was.

There was no nervousness or concern in her voice tonight. She told me she had a great evening. Her and Jake had had a few drinks and a bit discussion about the previous night. She said I had been right about everything and that he was very grateful that she had spoken to him as he was feeling very nervous about talking to her. Then she told me that since I was so clever I obviously knew what I wanted and that she was ready to go along for the ride. When Jake suggested they take the party up to his room she didn't hesitate. Of course I did insist in hearing every detail of their conversation at the bar but I won't bore the readers with that. Rather I'll pick up with when they got to his room.

"When we got to his room Jake told me to make myself at home while he grabbed a drink. I blocked his path to the fridge and embraced him. I wasn't sure how far this was going and still didn't think I was willing to fuck him, but I knew I was up for some serious making out. You always tell me how good I am at giving head so I was confident I could enjoy myself, leave him satisfied and still not totally breach our marriage vows. The passion in our kissing grew. Our tongues wrestled. And his smell! Did I tell how good he smelt? His hands were all over me as we made our way over to the couch. He fell back on it and I straddled him. Dry humping him. i could feel his hardness pressing on my pussy. I almost felt like I could come just from this!"

I said earlier how hard it is for Maddie to achieve orgasm. Usually she needs the help of her vibrator on her clit. But here she was feeling like she could come without even undressing! Now you might think that this would make me jealous or inadequate but I honestly felt joy for my wife. She was enjoying the moment. It wasn't that he was somehow better than me, or that she had found her perfect lover. She was just letting herself go, raw passion, and I couldn't be happier for her.

"After a while I knew I wouldn't quite make it to completion and I was keen to see what he had in his pants so I moved off of him and knelt on my knees beside him on the couch. The whole time our lips were joined in the longest kiss I had ever had. His hands were exploring every inch of my body over my clothes. He untucked my shirt and slid his hands up to my tits pulling the cups of my bra down so he could play with my nipples. One of his hands made its way down to my crutch, rubbing my pussy over my pants. It was then that I wished I had taken your advice to tidy up down in there 'just in case'. Never mind, I still had this thought in the back of my head that I wouldn't be fucking him. I moved my own hands down to his belt and pants button to undo them. I broke the kiss to look down as I undid his zip. I reach in and retrieved his cock from his pants. The first cock, other than yours that I had held in over 2 decades. Unfortunately this was my first disappointment of the night. He wasn't small, probably very similar to you, but I had anticipated so much more. It had felt bigger when I was dry humping it, and I guess when fantasising about a strange cock you imagine it to be huge like in porn. It was beautiful though, his pubic hair was well groomed and while I'm no expert and its hard to explain, it just look like a very nice cock. I went back to kissing him while I stroked it. Meanwhile the work he was doing on my boobs and pussy was getting me extremely worked up. I was starting to think that his beautiful cock would be a perfect fit in my pussy. Who cares if I was a little bushy down there. I certainly didn't think his cock would mind! Then came the second disappointment of my night. He broke away from my kiss and groaned. I looked down and sure enough he was coming. Shooting several spurts onto his belly."

"He pulled his hands away from me and looked at me slightly embarrassed. He then apologised saying I had got him so worked up, he lost control. I was initially annoyed, but quickly thought about all the times you had told me how hot I was. Annoyance was quickly replaced with pride as I realised that this middle aged mother of three had made a man come from foreplay. Perhaps I still had some sex appeal. After this we made some small talk and he made some comments about returning the favour or getting his second wind but I knew the moment had past. I left soon after feeling quite good. I had had fun, he had fun and I knew you would be pleased. Best of all I hadn't had actual sex which I knew I wasn't ready for."

After Maddie finished telling me all of this I was in quite a state. Two strokes and I shot my load into the jocks I had wrapped around my dick. I told Maddie this proved how hot she was, she had made 2 men come without fucking either of us. She said that as she had been left high and dry I had better be ready to fuck her tomorrow when she got home!

When I got home from work the next day, Maddie was already home. The moment I walked through the door she embraced me and started kissing me with passion. She dragged me down to the bedroom and dropped tp her knees. In seconds she had my pants down and my cock in her hands. Looking straight at my dick she said, "I've missed you, you're my favourite, I know you won't let me down!"

With that she licked the length of it before taking the whole length in her mouth. She bobbed on it for several strokes before taking it out and saying, "I need you to fuck me!"

She laid back on the bed and started removing her her pants, she had no knickers on. The first thing I noticed was that her pussy was clean shaven. She must have done that as soon as she got home. I couldn't resist and drove straight in to her cunt, licking and sucking it from top to bottom. I especially love sucking on her bald lips. She only let me do this for a few minutes before pushing me away, standing up and forcing me to lay on the bed. Without any ceremony she mounted me, taking me all the way in one motion. She was so wet! She mixed it up with some long strokes and grinding against me. After several minutes I was struggling to control myself so I tried think about mowing the lawn, football, anything to try and hold off from coming. It was made even more difficult by her moaning. She sounded just like she does when she is about to come. She was getting very vocal. "Oh fuck! Oh my god! Fuck this feels good!"

12