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.

Yay, Boobs - Image 3


Me and my boyfriend were hanging out when things started getting hot and heavy. When I took my top off, he looked at me and exclaimed "Yay! Boobs!"… He's 25…. I'm pretty sure his mind stopped at 14…. It's justified with his love of comic books!- Anonymous

You see, I'm quite the nerd. When I first started dating my girlfriend, we went at it in my storage room. I then proceeded to have sex with her on top of my vintage Star Wars action figure collection. At that moment I felt like I shattered nerd stereotypes. But I also found out the packaging on the top layer of figures are now in less than mint condition :(- Anonymous

A few years ago, in a galaxy far, far away, the stars aligned for me, and I somehow managed to gain the affections of this girl who was physically waaaaaaay the hell out of my league. Seriously, this girl was drop-dead gorgeous. Sexy as hell, five feet tall, jet black hair, perfect figure, a few sexy tattoos…the whole nine yards. She looked like the women on SuicideGirls.com, if that gives any indication. Weird thing about her was…she was hardly ever in the mood to fool around. Aside from some very light making out and cuddling, she really didn't even liked to be touched. But almost like clockwork, she would suddenly be in the mood to get it on like a porn star after 3 or 4 weeks of absolutely nothing. I could almost swear her sex drive would go into hibernation for a month or so, and then would re-emerge with a vengeance. And when she was ready, she was READY. She would go from having absolutely zero sex drive to suddenly being one of the horniest women I've ever encountered, even if only for a day at a time. Don't get me wrong…I very much enjoyed this beautiful young lady begging me to fuck her brains out and cum all over her, but let me tell you, the times in-between all the hanky-panky were trying, to say the least. Every day she would come over, smelling good and looking good…and to make her even more difficult to resist, she wasn't shy about taking off her clothes at the sight of a camera. If it had been up to me, I would've laid the pipe to her every single day. I showed restraint, however, because…for one, I'm not a rapist, and two, I kinda considered myself lucky that this damn near perfect looking female specimen would even allow me to touch her in the first place. Ah, memories. And yes, I still have naked pictures of her, and no, I'm not sharing.- Anonymous

This one is for the books. Me and my "friend" who assists me from time to time with certain carnal womanly needs picked me up in his car and we decided to travel to an empty warehouse parking lot to do the deed. After all this was said and done he goes to turn on the car and it would not start. Considering that we were nowhere near civilization we had to call our good friend to friend to come and give us a jump start. When she came, she could not stop laughing at us for a good 10 mins. Needless to say, I have awesome friends.- Anonymous

Ironic how my ex girlfriend was the one who taught me how to sell things on eBay considering everything she bought me is now up for auction.- Anonymous

Hopeless romantic…almost told a girl that I loved her on the first date—she didn't take it that well…- Anonymous

When my girlfriend goes out of town, she asks to spray my perfume on all her bedding so she won't get as lonely, and she can pretend that she is hugging me at night to help her fall asleep.- Anonymous

My boyfriend told me that he was an Eagle Scout. I found that kind of funny until he demonstrated his knot-tying skills one night…Let's just say I'm a little more appreciative of what the Boy Scouts of America have taught him.- Anonymous

My, now ex, girlfriend and I were driving back to my house after dinner. I was driving, and she decided she wanted to get "frisky" on the way back. Obviously, I was 100% O.K. with this, so needless to say my pants were off and I was getting some oral. On the way home there is this really, really big "dip" in the road. The signs say you have to slow down to 15 MPH to go over it. I was busy, so I kept going 50 MPH. Lets just say the timing was perfect. As soon as I hit the "dip", she "dipped", and I ended up with a very angry, choking, and gagging girlfriend.- Anonymous

Usually guys don't know where the clitoris is. I introduced my girlfriend to hers.- Anonymous

My ex-girlfriend was…how do you say….really stupid. Every morning when we'd wake up I'd have our daily quiz, because I liked feeling good about myself first thing in the morning. Some of the quiz highlights of our relationship were her not knowing the capital of the state she lived in, her thinking there were 47 oceans, 58 states, and that the moon was a planet.- Anonymous