Welcome to Rough Love, the column where we share your craziest, funniest, most embarrassing dating related stories. If you think you can top this batch of rough loving, submit your story at the bottom of this page.

I Fingered Her Belly Button


So It was first week dating my now-ex girlfriend. And we haven't brought up the topic of sex yet. And this one time I brought up the topic of longboarding over text. I told her I should teach her how to ride my longboard sometime. To which she replied "which one?". This ensured sex in the next few days.- asuley

It was mid morning and I really wanted to smoke so i hit up my friend with benefits and we started to hot box his car. We got super high and things started to get heated. He really wanted me to suck his dick. i was high and didn't mind. While i was doing my thing he said keep your head down someone is walking by. I thought he was joking and just wanted me to keep his dick in my mouth. So i lifted my head and saw some guy walking his dog by. After he walked by i paused and looked to make sure the coast was clear. All of a sudden a Jewish family walked by. I thought this was really weird and thought about it for a while. Finally figured it out and said "Its the Sabbath Day, Isn't it?"… He then said "yeah this side of town has a huge orthodox population." I was so ashamed but all i could do was laugh and went back to giving head. Forgive me Lord!- just-callmev

So I'm very ticklish in various different places. Unfortunately, my crotch is one of the most sensitive areas, and my girlfriend takes full advantage of this during sex. Even though I'm significantly larger than her (I'm 6'1", she's 5'0") and can easily pin her down on the bed, she merely has to lightly tickle my crotch and I instantly freak out. Needless to say, she does this often and with much amusement.- Anonymous

So one night I was on skyping with my girlfriend on my laptop and being that we hadn't been "intimate" in a while, we started to mess around. It got to the point when I finally started jerking off on my bed while she watched. Then out of nowhere, my roommate, who also shares the same room with me, opens the door. In the blink of an eye, I pulled my pants over my parts, pulledts, pulled up the screen from them, and pulled the laptop up to my stomach. He just wanted to know if I wanted to play king's cup with the others. My girlfriend and I laughed for five minutes straight.- Anonymous

My junior year of college I started hanging out with this girl whom I'd met at one of my frat's parties at our live-out house (party house for you GDI's) and things were rather frustrating. I wanted to be exclusive but she was apprehensive since I lived in the live-out she thought I would cheat. This back and forth went on for about a week until I completely fucked everything up. At our Friday party she texts me saying that she was coming over but asked me if I would let a guy from another fraternity into our party. Being very drunk when I received the text I thought she was playing games. I then thought that two could play and decided to take a random girl up to my room. I thought I had gotten away free and clear but when I checked my phone I had another text from her reading: "I was going to say hi to you but you left with that girl." To make matters worse the guy from the other fraternity that I mentioned earlier was her brother and a TA for one of classes. I saw him on campus the next Monday and he yelled at me for being a douche to his little sister. In retrospect, I was pretty douchey…- Anonymous

My girlfriend works in a nursing home where she helps some of the residents perform the more unpleasent aspects of daily living. She once told me a story about how an elderly woman was constipated and she had to reach up with a gloved hand and scoop out the poor woman's bowels. She describes this like its no big deal to her, but if my hand casually brushes against her feet she jumps up and screams. Why? "Because feet are gross", she says.- Anonymous

I had given to the girl I like a napkin engagement ring so we could marry in the Mexican night the next day at school. Everything went according to plan, I got on my knees and asked for her to marry me, she was really, REALLY excited. So anyway we got to the "Church" and got married, almost kissed. I thought it was the perfect time for her to take me serious. However another girlother girl I was hooking up one month ago got jealous (she's prettier) and asked me to get married with her. I told her that I would If I had any money on me and she paid…So the first girl went ahead and thought I was joking… And to make it worse, the sister of the first girl also asked me and made me marry her. Now the first girl think's I'm joking, the second likes me and I don't know what to do and lastly, one of my best friends is the brother of the first and third girls.- Anonymous

Okay, so I hooked up with this chick once. We went to her room, and things got hot and heavy. About halfway through, her friends bursts in, and we have got just enough time to pull out and cover ourselves with a blanket. Her friends was under the assumptation that we had "finished", and so didn't leave us alone. We never finished.- Anonymous

While fooling around in her basement, my girlfriend asked me to "touch her belly button" and was astounded that I didn't know that "if you touch a girl's belly button, she can feel it 'down there.'" Needless to say, I fingered her bely button — hard. After faking it for a solid minute, she fell off the couch nearly in tears, and laughing. Sadly, I didn't realize it was a joke,alize it was a joke, yet, and proceeded to apologize if I had hurt her while frantically asking what I did wrong so I didn't make the same mistake next time. It was a decent story until she told her room mates.- NVM