Author: SituationMain791

Ex-gf tries anal for the first time with hung coworker [MF]

**Read First:** If you haven’t already read my other post, I’d suggest glancing at it as the story includes some background on me and Nicole, as well as the first “cuckolding” experience that she did to me. This story will be so much better with the context of the other story. [Other post link.](https://www.reddit.com/r/gonewildstories/comments/oiazfl/how_i_developed_a_cuckold_fetish_with_my_ex_mf/)

Nicole’s birthday was coming up and I wanted to get her something sexual. I thought about lingerie but ended up making the decision to ship her a butt plug from Amazon. You’ve probably seen those gem butt plugs before, that’s what I bought for her in a medium size. When we were together, she never liked having her ass played with and we certainly never got to try anal.

She texted me when she opened the package laughing about the “gag” gift I had sent her. I tried to play it off like it was a joke and she should like it since it was her favorite color (pink). She laughed and said she’d have to pick out matching panties when she wears it. Read more »

How I developed a cuckold fetish with my ex [MF]

**Background:** This will be the first of **many** stories (if people enjoy them) involving me and my ex-girlfriend. She is *the* reason I developed a cuckold fetish and it only dawned on me recently as I’ve started to think about these stories.

I’ve always been on the shy side when it comes to dating. I met Nicole in 2nd grade and we were always close friends growing up. Of course I had a crush on her during this time and only got the nerve to ask her out during my senior year of highschool (over 10 years later). She said yes, which still shocks me to this day, and we dated for a little over a year.

Nicole is a total bombshell, petite blonde with boobs on the smaller side (~34B) but with a gorgeous butt. I’m about average height, but very skinny and have always struggled to put on muscle. She took my virginity and basically taught me everything I know about sex, which I admit is still not a lot. She wasn’t a virgin when we started dating and was very open sexually, willing to try almost anything. Our sex life was pretty vanilla for the entirety of our relationship. Although she was very sexual, she always had trouble cumming with me. I could get her to orgasm with a lot of effort by eating her out and using my fingers but always failed to get her to orgasm during sex. My penis is ~7 inches long but I always struggled to last a long time, even with a condom, which we used almost every time. Read more »