I Cheated On My Boyfriend With His Best Friend
Let me start from the beginning. My boyfriend and I had been together over 3 years. We met in high school, we got pretty perfect together. There wasn’t any abrasion with us; fights never happened, there was a lot of trust. We moved in together by year two, and we were in track to buying our own house by year 3.
He was easy, I was easy, and he treated me great.
But maybe you get too used to something sometimes. Our sex life was never great. I was his first, and despite trying to teach things to him to make sex better for me, he simply [is not a sexual person]. I had a few nights I’d break down and cry about how unhappy I was about it, and often small changes were made but nothing changed long term. I was bored with our relationship, and my life in general. I was quite young so I began thinking of settling down was really all I wanted.
Let’s introduce who We’ll call T. T was our best friend, both of us. He was apart of my boyfriends friend group (of which I was apart of). He was a couple years older than us, and originally we were just close friends. Eventually him and I became weekly texters, and he really was my best friend besides my boyfriend. Nothing came from hangouts, texting. It wasn’t until the last few months when I began questioning my life, and T exited a relationship did anything spur.
We had a drinking night when my boyfriend went to bed and T and I were up talking. There was small touches made, the type that make you wonder you know? We had some deep conversation about things, and eventually went to bed. My brain was buzzing. We all three would sleep in the same bed, as none of us were large people and it felt unfair making T sleep on the floor all the time. I spot was in the middle, as I’m only 100lbs and the smallest. Sleeping next to him mixed with the alcohol caused some intensified feelings towards him.
Over the next few weeks, things picked up. We started texting daily. We played video games together. I felt happy again, and it scared me a bit. I wondered why I enjoyed texting and talking to him more than my boyfriend, but at the end I assured myself that T was my best friend and that was it.
One night, my boyfriend had dropped me off at Ts house to hang out with him and our two other friends, while he went home as he had to work really early. We smoked a lot of weed, and I ended up falling asleep in Ts bed watching TV. Several hours later, I wake to find just T getting in the bed. He tells me that our friends were going to sleep on the couch downstairs. I crawled back under the blankets next to him. We talked a little before I was in the half asleep half awake stage. I felt him poke my hand playfully, and I sleepily did the same, and I felt my hand fall right into his. And they stayed there. Neither of us moved, we just kinda glanced at one another. I felt his stroke my hand softly, and we entwined fingers for several minutes.
I didn’t really think at this point, I just knew it felt good to hold his hand. He was my best friend, there was a part of me that really loved him and it’s been cleared to me he felt the same.
When his other arm placed right on the curve of my waist. I felt myself light up like a Christmas tree inside. I let out a light sigh, pulling myself a little closer to him. I felt his thumb rub across my ribs as he caressed my back lightly. My hands also couldn’t seem to control themselves, as they began running across his arms and side and stomach. I felt his hand drift lower and he now held my hip.
My brain hesitated as I felt him run lower on my ass. I was ungodly wet already by this point, but I was scared. I would be a cheater. I would be breaking every bit of my boyfriends trust. And he would be too. I’d like to give you, as a reader, a reason why I chose to do this that makes sense, but I can’t. It felt so natural with him, and I knew at this point I was in love with him (though I didn’t want to admit it) My boyfriend and I had been stagnant for a long time, and maybe it was that I got caught up in the excitement of it. Or, it might of been the fact that I wanted to fuck him, and I wanted to get that. Whatever reason suits you.
He was slow as he went further down, never directly touching my pussy and it drove me insane. He ran his hands through my hair as he did this.
The second I felt him gently run his fingers across my lips through my sleeping PJs, I shivered. He smirked a little, and sat up a bit, and I could Now see his hard cock through his basketball shorts. I stared at it letting out a small Moan. He was focused on me though. He couldn’t stop his hands running all over my torso and legs. When his hands reached my chest, I shyly let him grab them. Like I said earlier, I am only 100lbs, so my breasts are only about a 36B. His eyes softened and I watched a drive build in his face as he gently caressed them, softly pinching them. The entire time, his other hand was sliding under my undies.
I had gotten my hands to the front of his pants and I gently tugged them down playfully. He pulled out his cock without hesitation, and I was surprised to see him smaller than my current boyfriend. The fact that he was smaller isnt what surprised me, what did was the fact that I wanted his cock more than I had ever wanted my boyfriends. This was the point in my life I found out I love smaller cocks.
I ran my hands first across his balls, (some of the nicest I’d seen) gently tugging. I let my fingers dance across his tip and down his shaft, gripping a little tighter.
He shifted so I couldn’t touch anymore. He pushed me back against the bed and looked at me as his fingers slipped across the water park my pussy was. He was breathing heavily as he looked at my body and tiny lips, his fingers lightly circling my clit. I gasped in pleasure and laid my head back. This is when I figured out he was REALLY good at this. Nothing like my boyfriend.
I felt his other hand sliding up my leg and his fingers gently push into me. My legs shook. He held my chest lightly as he slowly pushed in deeper. He slide them back out and continued to finger my clit, going back and forth between penetrating and fingerings my clit. I could barely control myself at this point. He then slide his two fingers back inside of me, and used the other hand to massage my clit. His cock was sticking up against the blanket, and I reached back over to begin lightly jerking him.
I finally couldn’t go any longer. I finished hard right on his fingers. I’d never cum from another person at this point, not from my boyfriend or any other. It was my first real orgasm and it was unbelievable. He seemed pleased with my state at this point and allowed me to draw closer to his cock. I could tell he didn’t have long, precut was dripping off onto his bed. I slowly jerked his cock, playing with his balls in my hand. My face was only inches from his cock now, and he held my head, gently massaging it. I finally let my lips wrap around the tip of his cock, and I ran my tongue in circles around it, flicking gently. He squirmed, and let out a moan. After a few more minutes of sucking his tip, he pulled my head back, and laid my down, and I jerked his cock until his hot cum covered my breast and chest.
After this, neither of us said anything to anyone. We continued a tight relationship for a while after this while I still lived with my boyfriend.
Maybe I’ll write more sometime and finish out how other times together ..(continue confession)
