How my ex girlfriend bragging about my dick size led to me fucking her best friend
So a little backstory, me and my girlfriend of almost 2 years who I’ll call Sarah broke up over the summer. It was mutual but not exactly on good terms. Honestly it was pretty nice to be single again so I didn’t really mind. I’m not the vengeful type so I wasn’t at all looking for a rebound until a few weeks after we broke up her best friend who I’ll call Emma messaged me on Snapchat.
Me and Emma went to middle school together and being that she was my girlfriend’s best friend we knew each other pretty well. At first Emma was just checking in on me to make sure I was handling things well which I thought was nice, but also surprising since I assumed she’d hate me now that I broke up with Sarah. After a few minutes of messaging back and forth, Emma cut to the chase. It turns out that over the time that I had dated Sarah, she would often brag about me being hung, telling stories to not only Emma, but also her other friends. Emma was flying back to college in a few days and wanted to know if I would be willing to let her try my dick. I was going to say no at first feeling bad doing this behind Sarah’s back, but changed my mind remembering that it was mostly her fault we broke up. I agreed and me and Emma made plans for me to come over to her house the next day.
The following day I drove down to Emma’s house where she eagerly let me in, and you could really see the excitement in her eyes. She had made sure her parents were out for the afternoon so we had the house to ourselves. Emma’s a pretty tall girl, probably 5’10 with brown hair and a nice ass. She led me up to her room feeling at my crotch the whole way up the stairs. After entering her room she quickly got undressed as I pulled my shirt off. I let her do the honors and pull down my shorts, revealing my heavy semi hard cock. Emma was squirming with excitement and motioned me to lay in her bed, telling me she wanted to ride it. I went to put on a condom but she quickly told me not to as she was on birth control and really wanted to feel it. No problem with me, I let her crawl over me and try to ride it. Turns out I was even bigger than she thought and she quickly realized that it was too hard to ride on my cock. I reassured her it was normal, and had her lay down so I could eat her now dripping pussy to try and have her relax and be able to take my dick. It took just a few minutes for me to make her cum for the first time, and Emma told me she thought she was ready to take it. I told her to stay there, as I got up and started tapping my cock on her pussy. Emma reached down with her own hand to line the tip of my dick up with her pussy, not being able to take the teasing anymore. I slowly started going back and forth, making Emma moan louder and louder as I started to go deeper and deeper. As she got more used to my size, she started begging me to go faster. I loved seeing Emma this turned on, and had to control my breathing to make sure not to cum before her. Right before I was about to cum myself, Emma starting shaking and covered her own mouth to avoid screaming her moans. It only took a few more strokes while she was mid orgasm for me to cum myself, shooting my load deep inside of her. After a few seconds I realized I had made Emma cum so hard that a few tears were streaming down her face, a rather proud accomplishment of mine. After a few minutes, me and Emma went for another round, once again both cumming. It was a huge turn on for me making my ex's best friend cum this hard.
Unfortunately, I haven't seen Emma since this, however a little over a month ago she asked me to tell her the dimensions of my cock so she could order a similarly sized dildo which felt nice. Maybe in the future we will hook up again, as I have a feeling she wouldn't mind it.
Posted Jan 14, 2026, 3:06 AM UTC