I [F] 22 an getting married in two weeks and I have been cheating on my fianceé for years.

I all started back when in 2018 when I was 18 and was preparing to graduate from high school and move on to college. Me and my best friend (M same age as me) from high school would hang out all the time and we would talk about which colleges we wanted to go too and how we both wanted to go to the same one so that would both have someone we knew there. We spent almost all of our time together; playing video games, Pokémon go since that was still popular and just discussing the future.

once college came around it didn’t go exactly as we planned, we both became so busy with things that we really never spent time with one another and for about two years basically never saw or spoke to one another during that time. Over that time, I met my then boyfriend, now fiancée and soon to be husband. when in March of 2020, right before my birthday he messaged me wishing me a happy birthday and from there we began to reminisce about old times. We spent hours talking and eventually decided to hang out that weekend and play some games and talk like just like we used to do. A few days after this my birthday happened and my boyfriend proposed to me. I had expected him to do so sometime in the near future because we had spent a lot of time recently speaking about it but nonetheless, I was taken by surprise.

This weekend together did not progress as either of us had planned. As soon as I arrived at his apartment the first thing that happened was, we hugged, and I was surprised about how I was almost moved to tears since it had been so long since I had spent time with someone who was so important to me. We continued on from a few days before and continued to carry on and catch up and after laughing a story he told me I looked up and he was staring at me, with an almost sad look in his eye. I asked what was wrong and he said nothing and that he had saw my boyfriend proposed and said he was happy for me. and then he asked me if I had ever loved him. And my answer was of course, he was my best friend and even though so much time had passed he was still special to me. Then, we locked eyes again and this time all that emotion I had felt when we first saw each other again came flooding back to me and before I knew what was going on I was leaning forwards and kissing him. This was a total shock to the both of us considering we had only ever been platonic friends but in the moment, it just seemed right, like something both of us had always wanted. We kissed for a few seconds and then he pulled back and apologized and I told him not to apologize because I was the one who kissed him.

From that moment our relationship changed, it was only around noon, and we had planned to hang out all day and over the course of the day that kiss welled up inside both of us. It wasn’t exactly awkward but rather like both of us had something to say but were waiting on the other to say it. Eventually though, he decided to go first. He told me how he had loved me since we first became friends almost 6 years before then, how he wishes that he told me then and that he had not become so reclusive in the previous years and had all but pushed me out of his life. I wasn’t naive, I knew that he had a crush on me, and he was someone who I cared deeply for, but the right time or situation never presented itself and thus we never dated. But here it was, finally in some sense, the moment he had waited years for, the same moment that until it came, I did not know I wanted just as badly. We began to kiss again, far more passionately this time as all these repressed feelings between the two of us came spilling out.

We kissed and I enjoyed the feeling of his lips on mine, his tongue as he licked my upper lip, the smell of his hair, his hands as he caressed my face. Then the strong sexual urges between us became evident. Both of us are religious and both of us had been saving ourselves for marriage. I told him that I was still a virgin and he told me he was too. He asked me if I wanted to go any further and that it was ok if not. I told him that I was nervous, no one had ever seen me fully naked before, not to mention the prospect of having sex. He told me that we would figure it out together and that he was just as nervous as I was. I said ok.

We began to kiss again, this time his hands his hands worked their way down from my face down to my waist, he pulled me forward into his lap and then used his hands to move me slowly back and forth as we made out, I couldn’t help but feel his semi erect penis rubbing against me through his basketball shorts. I had never experienced the rush that this experience was bringing, my heart was pounding I felt myself actually desire to have sex with him, a feeling I had only felt with my fiancée before. he moved his hands down to my ass and squeezed it, he told me that I had a great ass and I told him I’m glad because I spent a lot of time in the gym to get it. He then took his hands off my ass, leaned backwards and took his shirt off, asking afterwards if he could take mine off. I hesitated for a moment, but that moment passed quickly, and he took off my shirt too. while he was removing my shirt, I couldn’t help but think about how a man was about to be a bra away from being the first man to see my breasts, but then my shirt was off, his hands on my waist pulling me into him again and I forgot all about that as I felt his penis rubbing against me once again.

he ran his hands up my waist to my back when they stopped on the bottom of my favorite orange sports bra I had chosen to wear for today. we stopped kissing for a moment and looked one another in the eyes, without either of us speaking he knew that I was ok with him taking it off and he did. I raised my arms over my head, and he lifted it off of me. when my bra was lifted over my head no longer blocking my vision, I saw him simply staring at my breasts. I became self-conscious and covered myself with my arms. He moved his arms from my waist and grabbed my wrists, looked me in the eyes and said, “you’re perfect. I looked at him for a moment, I couldn’t help but smile and then I put my hands on his face and began to kiss him again. after a few seconds he asked me to lean back and then he grabbed my breasts. my nipples were sensitive and felt almost ticklish against the palms of his hands. he continued to feel my breasts and eventually rolled my right nipple between his thumb and index finger. it was such an incredible feeling, sending shivers down my spine causing me to realize that I was feeling something I had never really felt before, I know now that I was incredibly aroused, but this was the first time that I had ever felt that way and I was surprised at just how exhilarating it felt.

He then put his hands in my armpits and stood me up, then lifted me into the air and laid me on my back on his couch. He got on top of me, and the cycle began again we made out, he felt my breasts and then he reached down and squeezed my upper thigh, only a few inches away from my pussy. I stopped him and said that we would be more comfortable on his bed, he agreed, and he carried me to his bedroom where he again laid me on my back, my legs dangling off the edge of his bed. He was standing in front of me looking down when he asked me if he could remove my skinny jeans to which I said yes. He then unbuttoned my jeans and pulled them down to my knees. pulling on the pants leg for each leg to get them the rest of the way off. At this point, I no longer had feelings of doubt or fear, it didn’t even cross my mind that he was also about to be the first man to see my pussy. the panties I was wearing weren’t exactly sexy, considering I had never imagined this day going like this. He grabbed my waist and got ahold of my panties and then slid them off much easier than my jeans had come off beforehand.

I again caught him just staring at my now exposed pussy. This time however, it wasn’t nervous about my looks as I recalled him looking at my breasts that same exact wat. He then looked up at me and then laid on top of me kissing me deeply, slowly running his right hand down my body, finally reaching its destination. I was surprised by how sensitive I was, my whole-body quivering as he ran his finger between the lips of my pussy. He rubbed me that way for a while before inserting one of his fingers into me. It was an unusual yet erotic sensation at first but very soon it began to hurt a bit as he continued to finger my pussy.

then, as expected I began to bleed a bit and he stopped. He got up and grabbed a towel and placed it under me, then began to remove his shorts. suddenly the nervous feelings had returned to me, and I had certainly seen a penis before but not one that was right in front of me. Then he was standing before me in his boxers, his penis fully erect and poking out. I had no experience with sex or really anything sexual. But I knew his penis was big, I thought it had to be at least eight inches, he pulled his boxers off. He grabbed my arms and pulled me up, his cock running against my thigh. he asked me if I was ok with grabbing, so I did.

As soon as I grabbed it, I felt his cock pulsate, him moaning along with it. He then laid down next to me and asked me to jerk him off. I had no idea what I was doing, I wasn’t squeezing hard enough, I was squeezing too hard, I wasn’t going fast enough, I was going too fast. but eventually I found a rhythm and a grip that he was happy with, and he laid there as I ran my hand up and down his hard cock. Eventually though, he complained that it was too dry and that it wasn’t very comfortable for him. So, he asked me to put it in my mouth. That, I was not interested in doing. Frankly the idea of putting it in my mouth repulsed me and we talked about it for a while, but he settled for me spitting onto it or onto my hand until it was to his liking and then I began to jerk his cock off again. (I have since had a change of heart on this particular subject) It didn’t take long for his cock to begin to pulsate just like it had when I first grabbed it, and he made me stop.

He told me that he was about to cum and did not want too yet. So, he then presented another idea, he requested to eat me out, which he had to explain to me because I did not know what that meant. I was similarly repulsed by this idea for the same reasons, though I figured since I wasn’t putting anything in my mouth it was ok, so I let him. for the 3 seconds it lasted it felt wonderful, but he quickly stopped due to the blood. It was shortly after this that we both realized that neither of us had a condom. we talked about it, and he assured me he would not cum inside of me and because I was not interested in taking a thirty-minute break to get a condom I agreed. He spat on his hand and lubed up his cock in preparation for penetrating me, he grabbed my feet and put them on his shoulders and brought his groin to me and placed his cock on my stomach. the base of it resting just above the entrance to my pussy and the tip reaching past my belly button.

I couldn’t help but wonder out loud how that was possibly supposed to fit inside of me, to which he muttered he didn’t know. I could tell at this point he was extremely nervous, but I didn’t want to embarrass him, so I said nothing. he then pulled his cock back and began rubbing it between my pussy lips, with each stroke he grew softer. His nerves had got to him, just like me this was his first time, and he was so worried about messing up it, that he began to mess it up. eventually his once giant cock was a shell of its former self as he desperately tried to get himself hard again. after around 30 seconds I told him to look at me and I said, “you’re perfect, and I want this.” After that, his confidence returned, and he got himself hard and lubed up again. He began to rub his cock between my pussy lips again, this time each stroke making my pussy hotter and hotter until it was almost unbearable, I wanted nothing less than to feel him inside of me. Then he finally pulled back and began to insert his cock into my virgin pussy.

He barely made it inside of me before it began to hurt, and I was only able to take barely past the head of his cock into me. But for the both of us, that was enough. He slid in and out of me, slowly pushing deeper inside my now deflowered pussy. we didn’t have sex, we made love. We looked deeply into each other’s eyes as we shared ourselves with one another. He would occasionally use the towel to wipe the blood away as he stretched my hymen. This absolute euphoria and pleasure came to an abrupt end however, as after about two minutes he suddenly pulled his cock out of me moments away from cumming, he didn’t know what to do but he certainly did not want to cum on me considering he had not asked but it was too late, my legs on his shoulders prevented him from turning away from in time resulting in a long gooey rope of cum landing initially between my breasts and coming to a stop just below my nose, the second covering my thigh as he pulled away and the rest finding its way onto the floor in his bedroom.

This was not the last time we have had sex. I have had sex with him more than a dozen times and all the while remaining abstinent with my soon to be husband. My story is something I have been thinking a lot about lately and I have been wanting to share it with someone and I found these nsfw confessional subreddits. While I personally am not a slut, I believe that my story has a place here. I hope you all enjoyed and feel free to leave any questions in the comments below or dm me!

Source: reddit.com/r/gonewildstories/comments/vorsxx/i_f_22_an_getting_married_in_two_weeks_and_i_have

3 comments

  1. Very well written, it’s wrong but it’s still hot. Have you had any urges to have sex with any other guy apart from your bestie?

  2. Will you continue to fuck your bestie on the side after you are married?

    How will you feel when husband’s dick is smaller and you’re used to getting off with a big one?

    Do you worry that your husband will know that you’re not a virgin from the fucking skills you’ve learned, confidence in the sack?

    Is your bestie invited to the wedding? If so, is he going to come?

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