My [F]irst time cheating on [M]y boyfriend (long story)

This is the story on how I cheated for the very first time. Back at that time I was 17 years old.

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A summer vacation was the only thing ahead of me that summer, my family and I were staying in Italy for two weeks and were looking to take in the food, culture and everything in between.

My boyfriend stayed back in Germany, he had to see through his summer job and also my parents weren’t totally comfortable with him tagging along. I knew I was going to miss him, I cried the night before I left.

Once we were on the plane and Italy bound, excitement bubbled up inside of me. I had only ever met a handful of Italians and we had so many plans, my boyfriend, although on my mind for a while, did fizzle out of my mind a few hours into our journey and all that was on my mind was this vacation.

We arrived at our first destination and the hotel was outstanding, high ceilings, huge chandeliers and friendly staff who ushered us into our rooms. I had my own room away from my parents, it would have cost way less money to just share with them but spending that much time together with zero alone time would have ended in disaster.
The first few days were splendid, we made our way around the small streets, took every tour and activity that was offered our way and ate so much food each night that we felt like kings at a banquet.

It wasn’t until a few days in when I decided to stay by the hotel pool whilst my parents headed on yet another tour that I spotted the most gorgeous tanned gentleman I had ever seen in my life. He worked at the hotel pool bar and looked as though he was a son of Zeus himself. He was tanned, he had dark hair, dark eyes and the most incredible body.

I felt my entire body shift, I was like a whore. I pulled my bikini bottoms higher up on my hips to give my legs the appearance of being longer, I sat up straighter and I made sure my bikini top was ultra tight to give my full breasts the appearance of being even slightly larger.

There were so many people around the pool but I needed to talk to this man, I wasn’t going to do anything, I just wanted attention from him. I had a boyfriend after all.
I made my way to the hotel bar and sat on one of the bar stools that lined the wooden shack. He turned from the coffee machine and smiled at me, at the moment I forgot that I was supposed to be a mature whore and instead lowered my head and giggled. I thought I had blown it with him but he continued smiling at me, asking what drink I would like. I told him to ‘Surprise me!’.

A few cocktails later and I was telling him all about my life in Germany, he was genuinely intrigued and actually listened to me. He seemed to be hanging onto my every word, everything I said was met with smiles and nods and he even told me bits about himself and his life. It was so refreshing to talk to someone that actually got me and who wanted to hear about me instead of just themselves all of the time.

I was aware the whole time that I was sitting on this bar stool in my very tight and small bikini and although not creepy in any way I did notice him stealing glances at my breasts every now and again and although I said nothing because I had a boyfriend, it drove me wild. It drove me especially wild as a cool breeze made my nipples erect and clearly visible through the thin material, it should have bothered me that he could see but it just didn’t.

We sat and we talked for hours, I eventually glanced at the time and knew my parents would be heading back any time soon. I stood up from the bar stool, making sure to bend over slightly as I tucked it back into its place so this man could see the curve of my ass.

He came around from behind the bar and took my arm, asking if he could take me to dinner that night. I was taken aback and I should probably have said no but he was so damn gorgeous and I was on holiday. It also was innocent, we had been talking all day it would have been a shame to have just left there and then and never seen him again. So I said yes.

I told my parents I had met some other girls from German around the pool and that we were heading to a local restaurant, somehow they just believed me and didn’t even question it. I remember getting ready in my hotel room and feeling butterflies in my stomach, I kept reminding myself I had a boyfriend and to not get carried away, this was innocent. Regardless I put on my favorite white silk panties and lacy white bra, I wanted to feel good at least. I chose a tight red dress to slip on over my lingerie, it was about the only dressed up thing I had brought on vacation with me, so I would just have to wear it.

I met him at the hotel reception and he looked, even more, dashing in a white shirt, black linen shorts and flip-flops. He smiled at me and told me I looked beautiful, taking his hand and running it down the back of my hair and all the way to the tip of my ass, pulling me in closer and kissing my cheek.

We strolled to a nearby restaurant and he got us a table with the most beautiful sea view. As the sun was going down the waiters lit small candles on each of the tables, it was so romantic but I just had to keep reminding myself that I had a boyfriend and this was just a friendly encounter. The whole time the candlelight flickered and made him look even more beautiful, I would sit with my elbows on the table, pushing my breasts together just daring him to look down at them.

After a bottle of wine and some of the most delicious steak I had ever eaten, we decided to take a walk on the beach. I felt so wonderful by his side, he was so tall and strong and whenever I spoke he hung on to my every word. As we walked onto the moonlit beach, slightly tipsy, he took my hand. I felt my stomach turn with lust and eagerness, that one small touch sent shivers around my body and I didn’t stop him, yes I had a boyfriend but this wasn’t cheating, it was friendly.

We walked and talked for ages until I realized that I probably should have been heading back, we looked at each other, our eyes lingered for far too long and a wave of excitement flushed over me as I pulled at my red dress and over my head, exposing my lace lingerie and silk panties. His mouth hung open as I began running into the sea, he realized what I was doing and started to unbutton his white shirt. I watched him as I stood giggling watching the sweat balls run down his neck as he continued undressing, such a simple thing but so erotic to me at the time.

We began running together towards the sea, pulling at our clothes as we ran. I kept my bra and panties on and he kept on his Calvin Klein boxers as we dashed into the cold sea, we laughed and we hugged and I could feel his hard cock rubbing up against my leg as we twirled and splashed one another in the sea.

Unfortunately, it was still late and just getting later and I knew I had to get back to the hotel. I had no phone and I knew my parents would have been getting worried.
We got out of the sea and we were both trying so hard not to look each other’s bodies as we dressed, I turned from him as I put my dress back on and I could feel his eyes staring into the back of me. I must confess I slowed down and pulled the dress as sensually as possible down my body. Luckily it was such a warm evening that we dried off pretty quickly.

We walked quickly back to the hotel and I did something that I still don’t regret. As he went to let go of my hand, I squeezed it and kept on holding it until we got to my room. I pushed him inside and went to knock on my parent’s door to tell them I was back.

I got back to my hotel room and he was still stood up, I told him that I wasn’t ready to say goodbye yet that I wanted to talk some more and I genuinely did.
We sat side by side on the bed and switched on the TV. He told me all about his family and I told him all about some of my deepest secrets, keeping out the part that I actually had a boyfriend.

We were both still a little tipsy but we took some wine from the mini bar and sat sipping it whilst the TV played some garbage. I felt so at home with him that when his hand rested on my leg, it gave me a shock. His hand was cold from the AC but extremely welcomed on my leg.

He turned to look at me on the bed and told me for the millionth time how beautiful I was, but this didn’t make it any less meaningful. He took his hand and ran it down my cheek, I could have cried at that moment. It was one of the most sensual moments of my entire life. As his hand reached my neck, he moved it to my shoulder and began to move the strap of my dress down my shoulder, he then did the same to the other side.
I knew I shouldn’t have allowed it, I knew I had a boyfriend at home but I just didn’t want to say no. This man was amazing, he really wanted me and I really wanted him. Would my boyfriend ever find out?

I allowed him to keep peeling off my dress until I was left in just my white underwear. I then undressed him, undoing each of his shirt buttons and finally undoing his shorts and exposing once again his Calvin Klein boxers. He was extremely hard but he made no move to try and hide it, he just lay looking at me. We hadn’t even kissed yet and I was so turned on.

With that, he pulled himself up and pushed me on to my back, smiling as he did so. He straddled me and lowered his head to kiss my neck, it felt surreal. He then moved and planted the most beautiful kiss I had ever had on my lips. This inflamed a desire and passion inside of me that made me grab at his head and kiss him, I slipped my tongue between his lips and began to moan at this alone. I felt a shift, there was no holding back now.

He moved down to my breasts, leaned his hand around my back and unclasped my bra. He then pulled the straps down my arms and threw my bra down by the side of the bed. Leaving my breasts exposed. He smiled and told me he had never seen breasts quite so perfect. The accent is what did it for me, it was like I was dreaming. He kissed my nipples and took his perfect tanned hands to grab at them, the whole time I could feel his cock pushing up against me and I wanted nothing more than to grab it and fuck him.

Thoughts of my boyfriend melted out of my head, I knew I was never ever going to have an experience like this again. When he was done with my breasts, he slowly started to move down to my pussy. I was nervous. He pulled at the silk, which showed the outline of my pussy lips, there was also a small wet patch where I was so horny and had obviously soaked through.

He kissed my pussy from outside of my silk panties and pulled on the material tighter and tighter, exposing more and more of my pussy. He kissed everywhere apart from my clit and it drove me insane. Before long he finally pulled my panties down and over my knees and over my feet and he placed my panties down next to my bra. I was now fully naked in front of one of the most gorgeous men I had ever seen. I didn’t feel self-conscious I just felt like I wanted to show him how he was making me feel and how much he was driving me wild.

He took my body in and sighed, shaking his head and smiling. He told me he just couldn’t believe that I was real and that this was really happening, I tried to tell him that I felt the same but I could barely speak in anticipation for what I wanted so desperately to happen. My clit was tingling with desire.

I gently parted my legs and moved one hand to my lip and the other to my pussy. I moved my hand and dipped one of my fingers inside. The look on his face is one that will be forever etched into my memory, his cock twinged and I knew it was driving him insane seeing me like this. I had gone from a slightly shy and reserved girl to a temptress in a matter of minutes. He moved down on top of me and kissed me, I grabbed at his body and finally at his cock. It was large, very hard and trying to burst its way out of his Calvin Klein boxers.

I slipped his cock out and he moaned during our kiss, it was bigger than my boyfriend’s and felt so soft and amazing to anything I had felt before. My pussy was dripping wet and his cock gently slipped inside of me, both of us were moaning with the thrill and sensation of it all. He thrust inside of me and just stayed there, he told me he was going to cum if I moved, he told me that this never happens.
We stayed in this position for a while, kissing and only moving in short bursts to prevent him from climaxing. The problem was that I was also on edge and with each thrust, my pussy felt like fireworks were exploding inside of me. I had never felt anything so truly amazing.

He picked up the pace, closed his eyes and flipped onto his back, gently bringing me up so I was straddling him. I bounced up and down on his cock and tried to remain mindful that my parents were just a few rooms away, but at that moment I just didn’t care. I was completely naked and had one of the most beautiful men I had ever seen inside of me, He kept his eyes shut as he grabbed at my boobs and I moaned louder and louder.

He then took his hands around my waist and on to my butt, he lifted his knees slightly and moved his fingers to my pussy, I was soaking wet and with that, he moved his slender fingers to my butt. Nobody had ever touched my butt before but I just let it happen. With my pussy juices soaking his hand he slowly pushed his index finger into my butt, groaning in the process, he kept telling me that he couldn’t open his eyes and look at me because he would cum everywhere.

His index finger made it into my butt and I was uncontrollable, I still don’t know how there wasn’t a noise complaint. We stayed in this position and I fucked him as hard as I could whilst he tried to suppress my moans with his hands. Before long he told me in his beautiful accent that he was about to cum, so I stayed straddling him whilst he thrust hard and deep into me and came incredibly hard.

I sat panting as I kept on riding him slowly, moving my hips up and down. I didn’t want it to end, I was having so much fun so after a few minutes I kissed his neck and he turned to smile at me, that beautiful gleaming white smile. He walked to the bathroom and came back soaking wet from his quick dip in the shower and made his way onto the bed.

Without even looking at me he spread my legs open and thrust his fingers deep into me and played with my clit with his tongue, I was screaming out in pleasure, I tried to catch glimpses at him but every time I lifted my head a new wave of pleasure overcame me. I was in heaven.

His fingers became faster and his tongue keeping the same rhythm brought me to a beautiful orgasm, my whole body felt like it had died and gone to heaven. I lay there panting whilst he sat and smiled at me before taking my hand and leading me into the bathroom. I could barely walk, my legs felt like they were made of jello. He made sure the water was warm enough and we both hoped in, completely naked and we kissed, a deep passionate kiss that once again sent shivers around my body. He gently stroked my nipples and pushed a finger in my pussy whilst I grabbed his once again erect cock.

We stayed there for some time just enjoying the moment before heading to the bed and falling asleep in each other’s arms. The next morning we woke up and it wasn’t awkward, there was no regret and we both dressed and headed to the pool. He was working again, my parents went out without me again and I stayed by the pool just watching him, we stole glances at one another all day long.

Leaving the hotel was heartbreaking but I never felt any regret for cheating on my boyfriend and I never contacted that beautiful man again, I sometimes wonder what he is doing now but I hope he is happy.

Source: reddit.com/r/gonewildstories/comments/xkh0e7/my_first_time_cheating_on_my_boyfriend_long_story