[M]y best friend begged me to sleep with his girl[F]riend [MF] [Very long, part 1]

Hi. Long time reader, first time poster here. I have long wanted to post my confession here to make myself feel better, but never had the guts to do so. Finally I decided that I needed some closure so that I can stop thinking about my past flings. English is not my first language, so please bear with me if my story below is poorly described. With the exception of names being changed and the conversations translated from my native language, the entire story and context below is true. If it is too long, just skip to the part with [TLDNR].

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To begin with, I was very close friends with Zack. Although I am 6 years older, he was very mature for his age when I first knew him back then. He was 14 and I was 20. All these while, I have not met him for a long time when I got a job in a different suburb of the city we live in, while he continued schooling.

Fast forward a few years until this story happened (somewhere 2013). Zack has recently started working while I met an intern at work called Sue. She mentioned that we have met before during a career fair we both attended several months before she started interning at my workplace. Although I had no recollection of ever meeting her before, she definitely caught my attention now. Sue has a petite frame of almost 5 feet, with straight, long hair. She has a shy but very sweet smile, which somehow makes a great match with her beautiful, oval face. She clearly has good fashion sense and was good at her make-up which accentuated her beauty. She always wore clothes which hugged her very slim figure, and it was obvious her C-cup breasts was very noticeable to men nearby, always causing heads to turn. She was shadowing my work as part of her internship, and 6 months later from the day she showed up at my workplace, she was gone.

I did not give Sue much thought until several weeks later, I bumped into Zack at a newly opened mall in the city. After exchanging pleasantries and having a quick update on each other’s lives, he told me that he was waiting for his girlfriend who was at the fitting room trying on outfits. Turns out his girlfriend is none other than Sue. None of us knew about us knowing each other, and we had a good laugh about it. As we went our own ways I recall turning back and noticed how radiant and sexy she looked.

A week or two later, Zack texted asking me to come over to his place for a party. Although most of his friends are too young for me, I didn’t want to disappoint him and agreed. I reached the party and true enough, most of the party-goers are either in their late teens or early 20s at best. When I was there, I saw Zack flirting with a very attractive girl (Quinn) while Sue was in another corner, clearly green with envy. I said a quick hello to Zack. He managed to tell me that he needed to ask for a favour in private later, and he immediately turned his attention back to Quinn. I later talked to Sue, and I remembered clearly how her face lit up when she saw me. She later returned back to her sad frown. I asked her what is wrong, which she pointed out at Quinn. I gave a lame response about how he is just entertaining the guests but I know that was futile considering he was only entertaining one girl that evening. I later found out that Zack met Quinn at a bar several weeks ago and they have been in touch everyday since. As most of the guests have left, I stayed back to help Zack and Sue with the cleanup. When Sue was out of earshot, Zack whispered to me with a wicked grin “About that favour… can you fuck Sue for one night?”. I was caught off guard that I nearly dropped the glasses I was washing. I managed “Excuse me? Are you crazy?”. Zack explained that he had a thing for Quinn for a while and that he knows Sue has been fantasizing about a man during her internship which he later found out was me. He needed that favour from me to bargain with Sue in exchange for a fling with Quinn. I was silent the whole time trying to process these thoughts in my head. I am not the attractive sort of guy that I would expect a beautiful girl like Sue to fantasize about me. Zack was persistent in asking for my agreement. As much as my manhood was dying for a taste of Sue, I did not feel comfortable as he was one of my best friends for a long time while Sue became from a mere workplace acquaintance to a friend. I left abruptly blaming that I had too much to drink.

Over the next week, Zack was texting me almost on a daily basis to ask me if I was OK with his proposal. I did not want to spoil our friendship as it really meant a lot to me, and I certainly did not want Sue to blame me for the failure of their relationship. One day Zack texted me when I had a bad day at the office, and I responded with “Let it go. Sue will not be OK with this if she found out about it”. To my amazement, Sue texted me a few hours later with the subtle “We need to talk”. I met with Sue for drinks after work, and she did not beat around the bush “I know about it. I am the one who told Zack about this idea”. I was dumbfounded. I then half-heartedly tried to talk Sue out of that idea, until she shot me down with something I did not know. “We are on the rocks for some time now. Sex is boring and if this is what we both need maybe we should live with it and try to fix our relationship to move on.” After a long silence with me trying to process all these drama the both of them laid on me, I told her “Alright, I am in”. I could tell there was a twinkle in her sweet smile which she tried to hide. I added “Let me be the one to tell Zack”. Sue nodded in agreement.

********* TLDNR *********

On the Friday of that week, Sue called me as I was about to leave the office and asked “Are you free tonight? Can I come over?”. I did not expect that phone call as both Zack and Sue were silent ever since the last time I told them I agreed to their plans. I managed “What about Zack?”. There was a short pause until Sue said “He is out of town for the weekend with Quinn”. I agreed to her coming over to my place, and I got a pack of condoms on my way back.

I tidied up my apartment and took a quick shower when I heard a ring on my doorbell. I grabbed a towel and quickly put on a pair of shorts. I looked through the peephole and saw Sue. I ushered her in and ask her to take a seat while I continue to dry myself. She was carrying her handbag with a matching red tone with her dress. Her dress in turn hugged her figure tightly and accentuated her breasts even more. She looked shy and uncomfortable, but I thought that I would leave her alone for now. I put on a shirt and went back to check on her. She did not move from her seat. I said “If you don’t want this, then don’t. Tell Zack how you feel.” Her reply was forever etched in my mind to this day: “I fantasized about this for a long time. I just want to know if you do as well.” I only managed a nod and I leaned in for a kiss. Till this day, I can still remember the soft, sweet kiss and the intoxicating smell of her perfume mixed with her body’s aroma. The kiss was slow at first with us exploring each other’s lips. Then, she jumped into my arms when I hugged her waist. We wrapped our arms around each other as we continued to move around and explore each other’s body. I could feel her breasts pressing through the fabric that I was rock-hard instantaneously. She pushed me away gently and started walking towards my room and told me to walk in after 5 minutes and seduce her. I barely waited for the 5 minutes she asked for before I felt silly, and I walked in as I could not wait for what was about to happen next.

Sue was lying under my blanket, and her dress was already dropped on the floor. I undressed myself with the exception of my boxers and joined her under the blankets. As I touched her I can hear her sigh. I discovered that she is wearing only her lingerie, but also she put on a blindfold on herself as well. I moved my hands all over her body until it rested on her stomach and pulled her to me. I kissed her passionately and as her tongue touched mine I could swear that it tasted like sweet berries. I moved my hand to grope her breasts before deciding that I could wait no longer and moved to her back and unhooked her lacy bra. I threw it on the floor and mouthed a very loud “Oh my god” as I fondled her very generous breasts. They felt even bigger than the C-cup I thought they were, and they are definitely perky yet firm. Sue moved her hands inside my boxers to stroke my erect cock. I moved my hand to massage her clit over her panties as she moaned continuously. Her panties was getting soaked so I pulled them down and continued to massage her clit. I moved my hand lower to massage her soaking pussy and continued to tease her until she begged me to put my fingers in. As I did, I can hear her squeal in delight as I stroked my fingers inside her. It was such a turn on and she was so good at stroking my cock as well. The sloshing sound that was produced by her tight, wet pussy did not help matters at all as I was afraid I might orgasm soon. She groped around as her blindfold was still on until she pulled down my boxers and held my cock in her grasp. She smiled and said “I don’t even do this for Zack” when she wrapped her lips around my cock and sucked on it. I could tell she was not exaggerating when she sloppily sucked my cock, but it got better as it went on. To be honest, I did felt a pang of guilt when she muttered my best friend’s name, but that quickly evaporated when I looked down on her naked body.

I continued to stroke my fingers up and down inside her pussy while she sucked my cock. I was afraid I might not last long as she was picking up the pace, until I told her to slow down and she said she wanted me to fuck her. I slipped on a condom and I changed my position so I could enter her in a missionary position. As I entered her, she asked me “Are you wearing a condom?” I said yes, when she reached around for my cock and pulled out the condom and threw it away. She said “I’ll get the pill tomorrow morning”. I did not bother to utter a protest as I entered her bare. The feeling of the bare skin on my cock when it entered her very wet and tight pussy was so overwhelming I had to go really slow. I pulled her hips down on me so I could penetrate deeper. She was moaning louder and louder while shouting my name at some point which I find it impossible to bear. To delay myself from having an orgasm too early, I slipped my cock out and went down on her. She was so wet she made a huge spot on my bed already. She tugged at my hair and pressed my head down on her as she wrapped her legs around my neck. I continued to lick her wet pussy and fingered her clit at the same time. At some point when I went down on her, she took off her blindfold. She was nearly close until she pushed my head away and said she wanted to ride me. As we swapped positions, she tried to position herself on top of me. As she was extremely tight and I am below average in length (about 4 inches I guess), we didn’t make much progress and I fucked her doggy-style instead. I thought going slow will slow things down, but the sight of her cute ass throttling on my cock was just too much for me to handle. I reached forward and cupped both her breasts, and she arched her back upwards so she can reach behind and pull my heard closer as I licked her neck. I released her breasts and she went back down on all fours. We later switched back to the missionary style she seemed to like a lot. I had to constantly distract myself as her tight pussy squeezing on my bare cock drove me insane. She started squealing again and when she wrapped her legs around my back, I picked up the pace. I could feel her fingernails digging into my back but all I could feel was ecstasy at this point. She started contracting her muscles and I had an orgasm almost immediately, unleashing a huge load inside her. I continued to pound her while she fingered her clit. Her legs started shaking and had a full blown orgasm not long after. Her contraction was so intense I thought her pussy was going to push my cock out. As it subsided, we both rolled over, panting while she rested her head on my chest. I could not wipe that grin off my face, and I can still remember her sweet, blissful smile as she rested on my chest. We both fell into a deep sleep not long later.

I woke up in the middle of the night with a numb arm that Sue was sleeping on. She was a light sleeper and I woke her up as I tried to push her away gently. She mumbled an apology and went back to sleep. As my arm was recovering, the memory of fucking Sue last night was still vivid in my mind. I realized that I am fully erect again. I woke her up for some slow, vanilla, missionary sex. About half an hour later, we both rolled over to sleep.

Despite her initial intentions to stay at my place for 2 nights, the awkwardness in the following Saturday morning prompted her to go back home. Despite the insane sex from last night, I did not bother to persuade her to stay as I was a bit uncomfortable with it myself since we both partially came to our senses. She texted me that she got the morning pill later. Zack came back on Sunday night feeling extremely pleased with himself. The smug on his face somehow triggered the second time I hooked up with Sue again, but more on that in part 2 if you guys liked my confession here.

Source: reddit.com/r/gonewildstories/comments/9y67ek/my_best_friend_begged_me_to_sleep_with_his