Annie's Big Fling

Story Info
Special goodbye to a special man.
9.3k words
2.94
29.6k
6

Part 1 of the 2 part series

Updated 10/29/2022
Created 07/17/2013
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
mjar65
mjar65
1,235 Followers

John has never written about my relationship with Damien or even really mentioned Damien in his stories. He always felt Damien was something very special just for me. Lately, however, John's wanted to record some of my memories of my time with Damien. So this is my story told by John trying to use my words. This happened a few years ago now so some of the details have been lost. Enjoy - A

Damien was my 'other man'. He was my 'lover on the side'. This is a story about one amazing, sex-filled, debauched week I had with him.

I met Damien some years ago at one of my first sex parties. He was serious looking and polite which I found very attractive. I didn't mind that he was younger than me. John, my escort at the party and my life partner, encouraged me to take an interest Damien. When I discovered how much I enjoyed sex with Damien, John practically insisted that we become lovers. I was keen on Damien and so I was happy to comply. It turned into a wonderful and fulfilling experience for us all.

John and I have that kind of relationship. We have never been exclusive to one another. Neither of us believes a person can obtain all the pleasure and satisfaction they need from just one sex partner. Its a mutual arrangement and John usually has an 'other lover' of his own. That's on top of the sexual adventures that we have as a couple. Its healthy and natural for people in a relationship to have passions they don't share with their partner. Some women have coffee with girlfriends away from their menfolk to engage in gossip. I have my 'men on the side'.

You should understand that John is number one for me in life, love and sex. But Damien was special too and, in a way, what I felt for him I would also call love.

We quickly established a wonderful relationship. What is more, I found that the longer it lasted the better the sex became. I enjoyed Damien's young, slender body and loved his big, vibrant cock. He was so different to my John and that was part of the thrill. Very quickly Damien was permitted to fuck me bareback. He was a major reason why John and I agreed I would go onto birth control.

It is so wonderfully decadent to have a lover to call at short notice whenever I feel the urge or the need for a few hours of wonderful, no-strings fucking. I guess that's what guys refer to as a booty call. With Damien the feeling would usually hit me every couple of weeks. Sometimes he would call me and I would rush to meet him, peeling my clothes off for him and surrendering to his needs.

John didn't always know when and where I was fucking Damien. That was important to the whole thing. But the two men knew all about each other. Damien was so special to us that from time-to-time we included him in our sexual adventures. Sometimes John and Damien would get together to give me an adventure all my own – a mind-blowing threesome.

I cannot describe how it feels as a woman to be the focus of the affection and lust of two men at the same time.

Damien and I maintained our relationship for years. It went on far longer than I could have really hoped for. Deep down I always knew it had a limited lifespan. One day Damien would find himself a 'real' girlfriend and then I would have to give him up.

Still, when the day came and Damien told me about Claudia a little bit of my heart did break. I cared for him very much and so I was also very happy that Damien had found someone he could love with all his heart. I was glad he had found someone who was right for him and a person with whom he could make a life with the way I've done with John.

I tried not to think about it, just enjoying my time with Damien and all the things we did together. John and I even suggested that we would like to meet Claudia and introduce her to our fun ways. I've never met Claudia but I've seen her picture and if Damien liked her then she must be a good person. But Damien didn't want that. He said that he wanted a more 'mainstream', monogamous relationship with Claudia and that she'd never agree anyway. John and I understood his position and I could see the inevitable was approaching.

Then, one day, Damien had a serious chat with me and told me that he was going to ask Claudia to move in with him. He had decided she was 'the one' and he wanted to take the relationship to the next level. I hugged him and told him how excited I was for him. But inside another crack was appearing in my heart.

I talked with John about how to end things with Damien. Once he was living with Claudia they planned to become exclusive to one another. So I started to plan for how to end my sexual relationship and allow Damien to move into his new life.

Then John had one of his bright ideas. Damien had told me that Claudia was going to be away for a week – travelling for a work conference overseas. She would fly out on a Sunday evening and return on the following Saturday morning. Damien intended to ask her to move in when he picked her up from the airport.

John decided I should use that week for a big finale with Damien. It would be a last giant fling to celebrate the relationship and mark the end of our time as lovers. His idea was that I would spend the week living with Damien. We would fuck whenever and wherever we could for that week and Damien would get his first taste of what its like to have a live-in lover.

I was surprised when Damien agreed but very excited. No matter how we did it, ending the relationship with Damien was going to hurt. I was going to give him up for another woman. So a full-on week of sex in advance seemed a great idea to me.

This is the story of how that wonderful week unfolded.

Sunday night

When Damien returned from the airport I was waiting with my bags. I was ready for a whole week with him and had brought work clothes and all kinds of stuff to last till Saturday. I was wearing my skimpiest outfit. Damien was looking a little guilty but he smiled his usual sexy smile at me and we went straight inside.

We ended up in bed very quickly and this night we both seemed happy to take our time. After all we had the whole week to fit in as much fucking as possible. That first night there was a lot of oral given and received. I thought a little about Claudia and how many times she'd pleasured Damien in the same bed. Mostly, though, I thought about how his hard cock felt in my mouth and the way he tasted. I delighted in licking his pre-cum from the head of his cock as I stroked him with my hand.

He gave me plenty of attention as well. I just lay back for him and slowly thrashed around the bed as he expertly licked and sucked at my cunt. I gushed my juices into his mouth over and over as I came for him just as I had so many times before.

Finally, when our mouths were tired and I'd had more orgasms than I could count, I pushed Damien back and climbed on top of him. I wanted to fuck him, to pleasure him. I was his live-in lover for the week and I wanted to show him a little of what he should learn to expect.

Without a word I slid down onto his beautiful cock and slowly impaled myself. Then I fucked him slowly while I played with his nipples. Damien loves having his nipples sucked and pinched. I didn't cum that time but I made sure I rode Damien just the way he likes it. I loved hearing his moans and groans as he got closer and closer to his orgasm.

I took my time, stretching it out to make it last for both of us. Finally he couldn't take any more. My reward was to feel Damien exploding his cum into me. I stayed on top as he shot high up into me over and over. I squeezed my cunt muscles to milk his hard cock as best I could.

Afterwards, once we'd finished and I climbed down, I lay next to Damien and softly licked his cock clean, removing both sets of juices from his softening member. For a little while I forgot about everything except Damien and how good it felt to fuck him. It was a wonderful way to start our week together.

Monday morning

As soon as we were both awake I insisted on Damien fucking me. There was no need for foreplay. Seeing his cock already growing nice and hard, I pulled him on top and soon he was thrusting into me. I was so horny that morning as the sun began to warm the day. He was enthusiastic as well and gave me a good humping and a very nice orgasm before he shot his load deep into me.

We both needed to hurry off to work. I left the house without knickers and decided to stand for the length of the bus trip. I didn't mind at all since I could feel the last of Damien's seed dripping down the inside of my left thigh for the entire journey.

Monday night

I got home first and stripped down to a T-shirt and my tiniest g-string for Damien. As soon as he walked in the door Damien got an eyeful and it had the result I'd expected. Barely stopping to remove his jacket, Damien pulled me into the loungeroom and quickly was taking me on the furniture. I didn't mind, I like fucking that way. He left my g-string on and it was so tiny anyway he had no trouble sucking and fucking me either side of the tiny material. I came over and over as he expertly pleasured my body and took his fill from me. It was a great way to start the week.

After a while he had me bent over his sofa and was sliding his cock into me doggy-style. I could not have been happier. Then Damien asked me if he could use my bottom. He asked me very politely of course, as always. My reply to him was very simple - 'My sweet man, you can go there any time you want.'

Just as I instructed him the first time, he started to prepare me by gently licking my little hole. I love the sensation and its even better when I know the tongue will be followed by a cock. But I was already so very turned on that I didn't need long before I was moaning and urging him to fill my bottom with his cock.

I stayed in position, bent over the sofa, as Damien slowly pierced me from behind. His cock is a perfect size for fucking my bum and he didn't need any lube as he worked his length into me. I actually saw stars as he began to fuck my tight little bottom but they were stars of delight. Soon he was moving faster and deeper and I could even feel his balls slapping against my cunt as he fucked me towards his own release.

I didn't cum from the fucking and I rarely do from anal alone. But I was loving the heat and the pressure of a hard cock in my backside. When Damien got to the edge of his orgasm we were both moaning and wanting more. I felt him when he erupted in my bottom, shooting into me from behind, each time a deep, firm thrust into me as he deposited his seed inside my bowels. I could have taken still more from him but we did have the rest of the week to enjoy ourselves.

We had a quick dinner, his semen dripping from my arse, and then we showered together. I loved the chance to wash my darling Damien and, naturally, gave special attention to his cock and his large hairy balls.

Back in bed Damien wanted to start with a 69 and I didn't argue. I asked Damien to use his fingers as well as his mouth. There is nothing better when it comes to sex than the feeling of flesh on flesh. After all his training and practice of course he did a wonderful job. He knows just where to touch me and how much pressure I need. I was cumming regularly and hard.

I was also trying to concentrate on Damien's pleasure but it was hard with everything he was doing to me. Instead I just had to be content with stroking his cock and his balls as they lay close to my face. He looked so beautiful and hard and I was enthralled by the sight of his pre-cum oozing from the head of his cock. From time-to-time I reached out with my tongue to clean away the silvery, shiny liquid.

Only after the longest time, at least half an hour of almost continuous orgasms, did Damien finally relent and leave my cunt alone. I felt pretty-well sated by that time. There was one more thing to take care of, however.

I shuffled around to get better access to my young lover and proceeded to suck and stroke his cock. I worked slowly and deliberately just as he had done to my cunt. I kept him on the edge for as long as I could. Eventually even Damien couldn't hold-off any longer. I released him from my mouth and stroked my hand along his entire length as he moaned and bucked his hips. I was thrilled when he finally came, shooting big wads of soft, warm cream across my chest and my belly.

With Damien and with John I am rather somewhat sexually submissive. I love it when they make me explode with orgasms but I always want to make sure I am the one giving pleasure to them. That night with Damien, feeling his hot cum shoot onto my skin and feeling it cool and harden, I could drift off to sleep content that I'd done my duty.

Tuesday morning

We didn't have much time that morning. I still managed to get in a lovely blowjob, however. Damien stayed on his back and I wanked him with one hand while sucking him as deep as I could. Of course Damien had woken up horny again so I didn't have to make a lot of effort to get what I wanted.

A morning blowjob is not a treat I get very often. His sounds were wonderful, a real turn-on for me. I wanted to take my time but really we did both have to go to work. I bobbed up and down quickly, using my tongue to maximum effect. Its a thrill to make a man lose control by using my mouth. I let Damien erupt into my mouth and naturally I swallowed it all. Not straight away. I let his semen roll around inside my mouth, savouring his taste as well as the moans and groans he was giving up. Finally we both left and I was sure I could taste his cum in my mouth for the rest of the morning.

Tuesday night

Damien beat me home and had dinner almost ready by the time I arrived. After the success of the previous night I'd decided I would stay naked for him for the rest of the week. So I ate dinner that evening without a stitch of clothing, trying not to splash any on my bare skin and watching Damien try to move around the kitchen with a big hard-on stretching his pants.

After that we were both naked under a doona on the sofa, watching TV. I played with Damien's cock and we both did some licking and sucking of nipples. That didn't last long before we were in his bed again.

I sucked Damien some more before I rolled over and indicated that I wanted him inside me. I pulled him on top of me and quickly he was in the right position and giving me a proper fucking. The morning headjob must have done the trick because Damien seemed to have even more stamina than usual. He stayed up there for ages, slowly pumping his hard cock into me. He knows what to do for me and he made me cum again and again.

There's not much more to tell except that my dear Damien was seemingly happy to focus on fucking me and make me orgasm as many times as he could. There was no complaint from me. I lay back and let my sweet lover fuck me to his heart's content, letting him plunder my depths and thrilling at the way his beautiful cock stayed so hard for so long. Damien was in exactly the right spot and had his cock pressing against my G-spot in just the way I need. I lost the ability to speak and all I could do was moan my pleasure and my thanks to him. I truly did lose count of my orgasms. I was in heaven.

After one of the longest fucks I can recall I needed a break. But Damien was feeling extra horny so he didn't let me rest for long. Soon he was on top of me again, thrusting his wonderfully hard cock back inside my cunt. I could only groan at the pleasure he was giving me.

I was building up nicely to my first orgasm of the renewed session when I sensed that Damien was about to unload. I forgot all about my orgasm, I'd had plenty, and gently played with his nipples. I wanted him to cum really hard inside my cunt.

He did, his face contorted and his limbs rigid. Damien groaned loudly as his cock spasmed and he pumped his juices deep into me. I moaned my pleasure up at him and waited as he thrust again and again, emptying his balls and glowing through his own, well-deserved climax. I could not have been happier as he rested on top of me. He softly kissed me and whispered his thanks as I felt his cock soften inside me and imagined his cum sloshing about inside my cunt.

Wednesday morning

That morning we both had to leave early for meetings at our respective offices. So there was no time even for a quickie. That left us both feeling horny all day.

Wednesday night

As soon as I walked in the door from work Damien dragged me off to the bedroom. I was pleased to see him too!

He stripped me naked and within minutes we were fucking, his cock like steel and his face afire with his lust and his need. I just let Damien have his way with me, my own body heating up in response to him and my cunt quickly flooding as he got into his rhythm.

We fucked in so many positions I lost track. All I know for sure is that his cock was like a piston as he thrust in and out of me, fucking me over and over, going deep and stretching my little cunt. I know I had a couple of small orgasms as we swapped around but I was more taken by how much of an animal Damien was that night and how much energy he had for me.

After a time he let me settle back into the missionary position. I knew I was going to be properly fucked now. Damien wanted me to cum and to cum good. He quickly got into the right position, his cock rubbing against that special spot up high inside my cunt, right under my pubic bone. I came alright, my entire body shuddering and shaking as orgasm after orgasm swept through me. I love that man and his cock and he's learnt well over the years exactly how to fuck me to best effect.

Then, after about 10 minutes of constant climaxes he suddenly stopped.

'I want to fuck you hard,' he said softly. I wasn't sure exactly what he meant.

'Fuck me sweet man. Fuck me as hard as you want.'

'No Annie, I want to fuck you really hard. Just go hard into you.'

We had hardly ever really done anything like that. I was a little surprised. But it was my sweet lover, my Damien, so I just let him have what he wanted. I nodded and lay there limply as he lifted my legs to place my ankles on his shoulders. We'd fucked in this position before but now I saw what he wanted. I understood he was going to fuck me with all his strength. I was sure he was going to hurt me, even just a little.

Still I didn't question or argue. It was my Damien and this time, more than any other time since I'd met him, I wanted him to use me just as he wanted.

Damien didn't wait to ask me again. He shifted his weight and began to pump his hard cock into me. I actually groaned with pleasure at the first few strokes because it felt so good to have his cock fucking me again. Then Damien started to get faster and harder and slam deeper with each thrust.

In a few moments I was bent almost in half as the weight of his body and the force of his fucking began to have their effect. He slammed into me harder and faster, seemingly oblivious to me and my needs. Damien had not fucked me like this for a long time. It did hurt but I was rapt in his animal passion for me - it was like he knew he was fucking me for the last time. I was happy to take anything he wanted to give me, even his lovely cock banging against my insides while Damien lost himself inside his own wild desires.

The frantic, brutal fucking lasted for several long minutes. I just hung on, folded and squashed under his attack, until at last I heard, more than felt, his erupting climax and Damien flooded me once more with his seed. I still don't know if it was passion or anger but he finished off that night with a few short, powerful jabs of his cock deep into my cunt, milking the last of his orgasm and forcing his last drops deep inside my upturned cunt. I just grunted with surprise as each thrust banged against my cervix. Damien had certainly fucked me hard. I'd been little more than a body to receive his fury. It had left us both a little breathless.

mjar65
mjar65
1,235 Followers