First Taste of Cheating

Story Info
Fiance gets her first taste of cheating.
4k words
3.74
97.4k
42
9
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

***Author's Note: Hi everyone. This story is 100% true and as accurate as I could make it given my memory! Feel free to leave comments and I love feedback...enjoy!***

********************

My fiance and I had been discussing the possibility of me fucking another man for years. His cuckolding fantasy was something we had discussed and he had fantasised about openly for the duration of our relationship. Coming up to our six year anniversary, we decided to give it a shot.

I wasn't particularly sure how to go about finding someone to have sex with. Until now, I had always been in a relationship when I had sex and had never set out to find a man for the explicit purpose of fucking. It soon came to me though - the wonderful world of the internet.

So, there I was with pages of google results for "no strings sex" in front of me. In my research I then discovered that the easiest way to meet men for no strings fucking was on swingers sites, where single men are ripe for the picking.

Finding a free site, I clicked the link, had a little browse around and decided to sign up for an account. I was faced with a few options though, should I sign up as a single female or a couple? Couple, I decided. Although my fiance had expressed his fantasy as being for me to go out and get fucked then come home and tell him, I hoped to talk him round to being involved.

Within a few hours I had my first few messages. The profiles of these men were certainly interesting; most boasting some impressive photos of their cocks and - for the most part - very fit bodies.

Chatting back and forth with a few men, I started to feel very turned on. The chat was almost purely sexual as I talked to men about how they would like to fuck me. After a few days I added some private photographs to allow me to send them to men I felt I would possibly like to meet. I was nervous about doing this, as I didn't have the best body in the world. After growing a massive bump during pregnancy and then 14 months of breastfeeding, my tummy and breasts weren't as flat or pert as they used to be. However, I figured if I was going to finally meet these men, they should at least know what I looked like.

At 5 foot 3 I'm fairly short. My curvy, size 16 figure didn't help me to feel any better about my body. However I was confident in my breasts, still a 36FF and although not pert, they felt and looked good. My brown hair and blue eyes gave me an innocent look and I only just looked my 23 years.

The men I seemed most drawn to while chatting were all older, around 35. Old enough to just want to fuck was my thinking. And they were mostly married with children. Another factor that would ensure the no strings nature of any possible meetings. I initially felt some guilt, as though I should have some inbuilt feeling of female solidarity. But that was soon pushed aside by realisations that these women were obviously not giving their husbands what they wanted.

After some chatting and exchanging of photos with a few men, I talked to my fiance again, telling him what I had been up to and it led to me getting fucked like never before. He was so hard at the thought of what I could be saying to these men, so I told him. All the ways the men told me they would lick me, bite me, spank me, stroke me and fuck me. How they told me they'd like to be licked, sucked, stroked and fucked by me. He came hard hearing how I would love to swallow another man's cum.

Talking after this passionate fuck on the living room floor, he told me to go for it. To meet another man and fuck him. Then come home and tell him about it.

I felt my pussy respond in a way I didn't know possible. Over the past week or so the chats with the men had made me feel similar to this, just not as intense. The longing feeling in the pit of my stomach, the deep pulling in my pussy, the instant wetness that flooded my knickers whenever I received a thoroughly filthy message. That was how I felt at that moment, but even more so. Being given permission to fuck someone else was a very strange, yet incredibly hot feeling.

With permission granted I set about arranging a meet. I chose one of the first men I had spoken to and had a meet arranged that then fell through at the last minute - the complications of wanting to fuck married men really. So I went onto the next man I had been chatting to.

I had been speaking to him for a couple of weeks on and off. If I'm being completely honest with myself, he scared me a bit. His messages quite often came across aggressive and arrogant. He was very turned on by the cheating aspect to his behaviour and also if the woman he was meeting was cheating then even better. He was what would be called a bull. Yet there was something incredibly sexy about him. He had been somewhat wary with me, not fully trusting me at first (because of lots of fake profiles on the site) but eventually he sent me a message and gave me his phone number, telling me to phone him.

I felt very nervous, but managed to dial the number, wetting my lips as he answered.

His voice was exactly as I had thought it would be - dominant, deep and with a hint of aggression. We spoke for a while, just some relatively normal chat, every now and then descending into something incredibly dirty. My knickers were soaking within a few minutes, just hearing his voice and thinking of all the things he had said he would do to me. He asked about why I was on the site and if I loved my fiance. I explained the situation to him. He said he loved his wife very much, but she didn't like to fuck the way he did. She liked to make love. He liked to fuck. Hard. And rough.

Hearing those words made me slip my hand into my trousers, rubbing my clit through my knickers. He heard me gasp as I came in contact with it. He asked if I was rubbing my cunt, which I confirmed with a yes and a moan. He called me a dirty slut, which only elicited another moan.

This had been the general content of our messages - I had told him how I longed to be fucked so hard I screamed, verbally abused for being such a slut and enjoying it. I wanted to be spanked, hard. Harder than my fiance ever could because he always held back for fear of hurting me.

We chatted some more on the phone, alternating between dirty and normal chat. After hanging up, he messaged me on the site, telling me he was pleasantly surprised by how I sounded and that he definitely wanted to fuck me now. That message made me breathless.

A couple of days later we were messaging and he suggested meeting that morning. At first I was reluctant. Scared even. I was scared of him turning up and finding me unattractive. Scared of his arrogance and aggressive attitude. But I decided, why not? I managed to convince my friend to take my toddler to soft play for a few hours, pretending I had housework to do. That left me half an hour to ready myself. I showered, shaved my legs and trimmed my pubic hair. I washed my hair carefully. Stepping out of the shower, I dried myself and dressed in my most sexy outfit. He had said he wanted me in a skirt. I quickly decided he wasn't the type of man to defy and found a black dress I'd worn for some interviews. I rolled on a pair of black hold ups, followed by a small pair of black, lace edged knickers and a black, balconette bra which pushed my breasts up and made them look very enticing. Pulling the dress over my head, I quickly dried my hair, moisturised my face and smoothed on a light layer of foundation. I've never been one for making a lot of effort, preferring the natural look and I wasn't going to change that.

I sat nervously waiting with a glass of water, trying to keep calm. I read back his last message in which he explained just how he would make my nerves and his nerves disappear. I couldn't quite believe anyone could be so forward as he was suggesting. I was soon to be proven wrong.

The doorbell rang, sounding so loud to my nervous ears. I answered the door and stood in front of me was a very nice looking man. Older, but he didn't look 35. Inviting him in, I stood back to let him pass me, my pussy tingling at the thought of what were about to do. I closed the door as he asked how I was. I replied in a very shaky voice that I was nervous, as I turned to face him. He motioned for me to come closer, so I did. He put his hand on the back of my head, weaving his fingers into my hair and pulled me even closer to him and kissed me. My bottom lip was quivering with nerves, but soon stopped as he thrust his tongue into my mouth, pulling me harder into him, his other hand on my thigh, under my dress, stroking the top of my hold ups. I moaned into his mouth, he commented that I didn't seem nervous to him then asked where I wanted to go.

I tried to speak, but couldn't at first. After a deep breath, I said upstairs, to our bedroom. He told me to lead the way. Walking back around him and starting up the stairs he slipped his hand up my dress again, stroking the lace edge of my knickers. I stopped walking, finding it difficult to concentrate on putting one foot in front of the other and he lightly slapped my ass. I continued walking, into our bedroom, stopping at the foot of the bed and turning to face him.

He unzipped his jacket and shrugged it off, took a couple of steps, closing the gap between us and kissed me again. His hand in my hair again, pulling me into the kiss. His other hand guiding my hand down to his crotch, placing it against his cock. I felt it twitch under my hand, under the denim of his jeans and moaned again. I could feel how big he was, even soft. My hand started to move gently against him as he kissed my neck and stroked my pussy through my knickers.

Placing both hands on my shoulders he pushed me down, telling me to sit. He unbuckled his belt, pulling down his zip to reveal his cock. I reached into his jeans, helping him to release his cock.

"What do you think?" he asked.

I was shocked at the size of him. He was the biggest I had ever seen in person, let alone touched.

"It looks very big," I said, "and very, very nice."

With that, I leaned down and tentatively licked the tip, my bottom lip quivering again at the thought of having another man's cock in my mouth for the first time in over 7 years. I licked his cock more and more with encouragement from him, his hand in my hair. I used my hand to stroke him in time with my licks and sucks, cupping his balls and gently tugging on them, before wrapping my lips tightly around him and going down as far as I could. I have always been pretty much able to deepthroat my fiance, but there was one last inch or two I just couldn't manage with this man and he wasn't even fully hard yet. His hand kept a firm hold of my head, pushing me down onto him and pulling me up, setting the pace. I gagged several times, which only made him groan. Pulling my mouth from his cock and taking it in my hand, I slid off the edge of the bed and on to my knees in front of him and started to lick his balls, making him groan louder.

After a few minutes, he tugged on my hair, pulling me up to standing. He slid his hands up my thighs and got his thumbs in the sides of my knickers, pulling them down my legs and telling me to step out of them. He then slid hid finger into me, I could feel how wet I was already, his finger slid in so easily.

"You really are wet aren't you? You're such a fucking slut, enjoying cheating like this," he said.

My pussy tightened around his finger, just confirming what he said. I moaned into his mouth as he kissed me again. He took his finger out of my pussy then and pushed me down on to the bed as he stripped. I watched as more of his body came into view. Slim, but very muscular and defined. He sat down next to me, his cock hard and prominent.

"Do you like what you see?" he asked.

"Yes, very much so," I replied.

"What do you want to do?" he questioned.

"I want to suck your cock again," I practically whispered, nervous of speaking such words aloud.

"Well. What are you waiting for?"

My pussy tingled at the tone of voice he used; dominant and no nonsense. I leaned over his leg, licking my lips before taking the head of his cock in between them. I flicked my tongue over the tip, tasting him, swirling my tongue around the head, before starting to move down further into his lap. One of my hands was supporting me beside his leg, while the other cupped his balls, massaging them. His hand came up to rest on top of my head, pushing me gently down at first as his other hand lifted my skirt to expose my ass. The first hard spank caused me to jump and moan around him, but I couldn't lift my head, his hand stayed firm, keeping my mouth on him. He spanked my ass again, harder this time. I could feel the sting then the warmth radiating across my ass afterwards.

His hand on my head reached down over my cheek, pulling away my hair to hold it at the back of my head, as he told me to watch myself in the mirrored wardrobe that faced the bottom of the bed. To watch myself sucking a stranger's cock.

"Good girl," he praised.

I moaned again, as I watched my mouth take his long cock impossibly deep into my mouth, my eyes slightly watering. I still couldn't get it all in.

"Get me a condom. I want to fuck you," he said, startling me out of the rhythm I had started to build up.

I sat upright, pointed to my bedside table, where there were two (a girl can wish) sitting waiting. He stood up and went to the side of the bed, watching me the entire time. I unbuckled the thin belt around my waist and pulled the dress off over my head. I decided there wasn't much point in coming over all shy now. He told me to lie down on the bed, he wanted to be on top the first time, watch my face as I felt my cunt being stretched by his cock. I quickly did as he told me, lying down with my head on the pillows, my legs apart, but not very much so. He climbed on to the bed and placed his hand on my thigh, pulling it away from my other leg roughly, before kneeling in between my legs. He stroked my pussy a few times with his fingers and asked me what I wanted.

"I want you to fuck me hard with your big cock," I said quietly. That was all the invitation he needed as he positioned his cock at my pussy, lay down on top of me, grabbed my hair with one hand and thrust deep into my pussy in one movement. I felt his cock deeper inside me than any cock as ever been before. I screamed out, mostly from shock but also from pain. He didn't let up, continued thrusting into me, pounding my pussy hard. He was leaning on my thigh, his hip digging into me with every forward movement.

At first I was straightening my legs, attempting to reduce the ferocity with which he was banging at my pussy, but as I got accustomed to the depth it was reaching, I began to relax. I let my legs fall apart and then I really felt him fill my pussy, hitting off my cervix with every thrust. His hand stayed firm in my hair, causing just the right amount of pain to be pleasurable and also to keep me from squirming out of his grasp.

He pulled out of me and I was surprised to feel my pussy attempting to contract around something that was no longer there. I wanted more. He ordered me to get on my hands a knees. I quickly complied. Again, I kept my legs mostly together. He knelt behind me and using his hands and his knees he spread my legs wide apart, forcing me to lean over further with my top half. My breasts were almost touching the bed like this.

He stroked my pussy a few times more, before pushing into me with no warning.

"I want to make you scream," he told me, as he picked up the pace. I couldn't believe how hard he was fucking me, his fingers were digging into my hips to hold me in place. Every now and then he would pull on my hair as he pushed in to make it deeper. He started to spank my ass again like this. Hard precise slaps that caused me to try and jump forward and to moan with desire. After several slaps I started to bite the pillow to muffle some of my moans and groans, his hand pushing into my head every few thrusts.

Again, he pulled out, leaving me feeling empty.

"I want you on top. I want you to ride my cock," he told me, giving my ass a light tap, right on top of the other spanks.

He lay down on his back, and told me to climb on reverse cowgirl. He wanted to watch me watching myself in the mirror.

"It's been a while since I've been on top. I hope you enjoy it," I told him as I swung my leg over his body, facing his feet and the mirror as requested.

Propping myself up on one knee and one foot, I grabbed his cock from underneath me and guided it inside. Settling down so I was on both knees, I sat straight down on top of his cock, gasping at how full I felt.

"Fuck, that feels good. You have such a tight cunt," he growled as I moved myself up and down on his cock.

I reached both hands back, pulling my ass cheeks apart to allow him to see his cock disappearing into me.

"You really do have a beautiful cunt. So lovely and tight. And so wet. Can you hear and feel how wet you are?" he commentated as I fucked his cock, making me blush furiously.

He spanked my ass, "I told you to fucking ride me.". I started to move faster, leaning down with my hands at his knees and moving my hips and pelvis back and forth and up and down, eliciting moans of pleasure from him. He continued to spank me hard. He asked what my fiance would think if he found another man's handpint on my ass, making me gasp, realising I hadn't thought about that possibility.

"Right now, I don't care," I replied eventually, which was quickly rewarded with another spank.

He pushed me forward then, telling me he wanted to fuck me from behind again but this time, facing the mirror. Once again, he pushed my legs wide apart and thrust into my pussy, making me scream out. I had my ass in the air for this stranger, my chest, shoulders and face pressed against the bed, my hands grasping the duvet so as to stop myself from moving as he fucked me hard. After a few thrusts, he pulled on my hair, forcing my head up, ordering me to watch. I was looking at myself in the mirror, with his muscular body behind me, moving hard against me. I barely recognised myself - my cheeks were flushed, my eyes were bright with lust. He looked similar, his eyes dark with desire as he pounded into me.

"Tell me what I want to hear. Tell me why you want me to fuck you." he said as he slapped my ass again.

I knew what he was asking, but I couldn't bring myself to say it. He wanted me to tell him I wanted him because my fiance couldn't satisfy me because he had a small cock. But I felt guilty thinking it, let alone saying it.

He spanked me again and tugged on my hair, "tell me."

"I need you to fuck my cunt hard because it's what I need," I answered him with. Trying to skirt around actually saying what he wanted me to.

"And why do you need that?" with another spank and even harder pounding.

"Because I need a bigger cock. I need to feel your big cock filling my cunt, fucking me harder than he can," I relented, giving in to his will.

"Good girl," he said as he dug his fingers into my hips and really pounded into me. My face fell forwards into the bed again, my teeth finding the duvet and biting it as I tried to muffle my screams.

He pulled out of me, leaving me feeling empty and wanting and took off the condom. Kneeling over me on the bed,he pulled my head towards him and pushed me to his balls, telling me to lick them again. I eagerly licked him as he wanked his cock over my face, his hand still in my hair pushing me into him. I could feel my jaw starting to ache as I licked and sucked his balls, but his hand kept me in place. He told me he was going to cum in my mouth, I tried to pull away, but his hand kept me there.

"Not yet, stay there."

I continued to lick his balls, getting firmer with my tongue, feeling my saliva over my face and his balls. I was beginning to get desperate for his cum. If I'd been able to speak I would have been begging him for it, begging him to shoot his load into my mouth, begging him to let me taste it.

12