How I [21M] cheated with my high school best friend (21F)

Hi everyone, it’s my first post on Reddit and english isn’t my native language so please tell me if something sounds weird !

The story I’m about to tell you happened a few years ago. I was hosting an Halloween party at my parent’s house (we have a nice place with a pool and not a lot of neighbors, so ideal to party !) and my girlfriend back then couldn’t come because she was studying really far away.

It was basically me, my sisters and 30+ friends of us, including some of my girlfriend’s friend and my best friend Anna.

Anna and I knew each other since the first year of high school, we used to take the same bus every day for at least 45 min. We always sat next to each other to talk, so we deeply knew each other personality, private and sex life.

She’s a petite blonde with a great body (I’d say a good B/ small C cups) and she exercise regularly. I’ve always thought that she was hot but never really wanted to date her because I knew she was not really the "faithful" type (sweet irony). But sometimes, listening again and again to her story describing precisely what she was doing with her body was a big turn on, I can’t deny.

Back to the party. It’s about 3a.m and at this point we’re all more or less drunk and starting to think about going to sleep. Since my gf wasn’t here, I asked Anna if she wants to come with me. It was not a big deal, we had already slept in the same bed several times before and nothing really happened.

Of course she said yes (As I said I didn’t plan anything anyway).

Here we are laying in the bed next to each others, cuddling a little.. Maybe a bit too much and she said something like "oooh we shouldn’t do that..". I stopped and apologized quickly and put more distance between us because I really didn’t want her to feel awkward.

At this point I need to add that I really didn’t plan to cheat on my gf on this particular night, even less with Anna.

Apparently she didn’t mind that much because she quickly came back over me, her head over my chest. We didn’t really say anything to each other but I could definitely feel my pulse raising up and I was afraid that she could notice it. With that started to come the typical half boner and I knew that I had to do something or I would get busted.

Here’s the crazy part.

Without warning she jumped over me and we started french kissing a lot. My brain couldn’t really process what was happening : it was so forbidden and so good at the same time that it’s hard to describe. I now have a full boner that she must be aware of. My hands slowly reached her boobs under her shirt and god, that’s always amazing.

Sadly, the thought of my gf started to make me feel uncomfortable and I asked if we could slow down a little bit. She was really comprehensive and lied down next to me. We were quiet for a bit and then she said "Great… now I want you…". I knew I didn’t want to sleep with her because of the guilt, but at the same time I knew that I wouldn’t be able to go to sleep with my dick that hard…So I asked if she would agree that we just continue the foreplay without going too far.. you know.. to release the tension (yeah, best plan ever).

Didn’t need to say it twice. She undressed me and start sucking me like a pro. I already had several girls going down on me, and I don’t know if it was the fact that we knew each other so well for so long or if it was her training but it was the most amazing blowjob I ever had. Of course I didn’t want to let her do all the work and I started rubbing her clit through her panties. It was so soaked that my hand almost sank in it. I swear I’ve never met a girl so wet before. She moaned and the deeper I went the louder she was. I was a little bit worried that the others at the party may heard us but it was so intense that I almost didn’t care anymore.

She jumped again on me but this time for a 69. I licked her for a good 20" and hopefully my dick in her mouse was preventing her moans to alert the whole house. She seemed to really enjoy it and she even deepthroat for a while, best feeling ever. I wanted to finish but deep inside of me I was still feeling guilty for doing all this.. After a while I asked her if she mind that I jerk off myself and she answered by "Ok but can I watch ? I like to watch..".. O-M-G ..hum..Why not ? It wasn’t really difficult and I was soon relieved like never and we both quickly fall asleep naked.

But there is more.

Around 7A.M I woke up with the morning boner + the sight of her naked just next to me… I was still really tired and I thought I should discretely jerk off as it’s usually really helpful. I was quietly doing my business but it must have been too much cause she woke up and asked what I was doing..

I was really embarrassed and didn’t really know what to say so I just stared at her with probably the dumbest look on my face. She laughed and without saying anything else, she went down on me again. I was so surprised and it felt so good that I probably almost fainted. We basically went for another round and I fingered her super wet shaved pussy until she orgasmed with my dick still in her mouth. The guilt was now gone for the most part as you can imagine and she was almost begging me to finish in her mouth. I execute myself with pleasure, unleashed the bigger load I could and she swallowed it. We went back to sleep shortly after.

We didn’t even fuck, but it’s still one of the hottest memory I have to these days.

Shortly after I broke up with my gf, didn’t tell her about that of course. I didn’t date Anna and we’re still best friends even if it sometimes with benefits.

Source: reddit.com/r/gonewildstories/comments/3x5yrt/how_i_21m_cheated_with_my_high_school_best_friend