By Tiffany McHugh | Your Tango
Do ever end well?
To sleep with or not to sleep with, that is the question — at least the one that runs through the mind of any single gal with a great guy-bestie. An admittedly far stretch from its Shakespearian derivative, you've got to admit, this question requires some serious thought. He already puts up with your obnoxious Nashville obsession, listens to you bitch about co-workers, and makes a mean bacon egg and cheese … why wouldn't you have sex with him?
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It worked out well (in the end) for Justin Timberlake and Mila Kunis in Friends With Benefits — but we all know that's not always the case.
Here, six unattached 20-somethings dish on time (or times) that they decided to blur the lines between friends by knocking boots.
1. It can be a vaulable lesson in sex ed.
I'm sure there are tons of searchable quotes out there insinuating that the best friendships are the ones that you learn from, but I bet that none of them are referring to circumcision. When Jamie realized that she and her guy friend Ben shared similar sexual appetites, she decided that it was worth a shot to invite him to visit her at school to see where the night took them. “I instantly regretted it,” she said. “He danced to house music in the bars like he was at a ska concert, and was clearly more interested in getting a taste of ‘the college experience' that his small university was lacking than hooking up with me.”
Rather than chalk the whole visit up as a loss, Jamie went for it anyway and ended up getting a lesson in sex-ed rather than getting off. “It was the first time I'd seen an uncircumcised penis,” she said. “After he left, I was suddenly repulsed — not by his penis, but by his personality and the night as a whole — and actively avoid his texts and calls to this day.”
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2. “Every f*ck-buddy has an expiration date.”
So you better take that into consideration before getting it on with someone you can't imagine your life without. Karen began hooking up with her friend Chris last April, who introduced her to a new sexual experience, and eventually, feelings of attachment. “The first time we hooked up, I told him that I had never had an orgasm from having sex, while we were having sex,” she said. “He quickly let me know that I was about to learn.” Turns out, he was right, and she continued learning all summer long. “I lied and told him and his friends that I didn't have feelings for him and that it was strictly business, so to speak,” she said.
Despite her growing attachment to him, the two continued to hook up … until she found out that he was dishing about their sexcapades all over the place. “He told all of our friends that I squirted, and now they refer to my vagina as ‘The Holy Grail' and have nicknamed me ‘Squirtle,' after the Pokemon character.” Yeah, consider that friendship (benefits or no benefits) officially over.
3. It's possible to maintain the friendship after sex.
The first time that Steph and her best guy friend moved past their usual PG-13 make out sesh, she learned that mid-blowjob giggles aren't exactly a turn on. “I couldn't help it! I was going down on him and I laughed because I just thought it was so funny, which apparently made him nervous,” she said. “I told him I wasn't laughing at him, I was laughing at the scenario, but it didn’t change anything.”
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Needless to say, she never ended up finishing the job, but the two still maintain a great friendship … outside of the bedroom.
