Sexy Time: My Most Embarrassing Sex Tales

Last week, I wrote about my poor relationship with masturbating. Someone called my story disturbing. I was far more taken aback than offended because I feel like it was a pretty tame, innocuous tale especially compared to other dalliances on my sex résumé. Since I am pretty open (read: shameless) in this column, I’ve decided to highlight four of my experiences that I was actually disturbed (or just plain embarrassed) by.

By Jasmine R.

My first kiss
I was 19. I was at a party with a whole bunch of lesbians and one straight guy. After a few drinks, he found me appealing enough to kiss, and well, it was late enough in the evening that he had started looking like Justin Timberlake to me, so we started kissing. By this point, the party had wound down and we were the only ones still in the living room. In the process of making out, my dress and bra came off, and my first kiss went from G to PG-13/R with a quickness. After it was over, I was emotionally perturbed and anxious about the not-so-romantic way in which everything had occurred, and things were compounded the next morning, when I found out that we were in fact not alone in the living room…and that the witness to my shenanigans? Was a 15 year old boy (someone’s little brother had tagged along…so appropriate). While I’m certainly somewhat of an exhibitionist now, I certainly wasn’t back then, and I still get queasy about the fact that a strange child was 10 feet away at the very beginning of my deflowering process.

My first FWB.
He was a decade older than me. He was an ex-coworker’s ex boyfriend, which was kind of sticky in and of itself. And, I found out later, he was dating other people the entire time we were hooking up. Um, I’d like to at least actively consent to being the side ho, thank you very much.

That time I sobbed during sex.
This was less than a year ago. I was visiting my family for a week for Thanksgiving, which was stressful in and of itself. And I was majorly bummed about being separated from my boo (trust me, I felt sufficiently embarrassed/ashamed/pathetic). So we were having goodbye nookie, and I couldn’t hold it together and started bawling. One of those extremely ugly, but super cathartic cries. While he was still inside me. I feel like I’m often teetering on the brink of sanity, but that moment…I was feeling very girl, interrupted.

That summer I had an online fling with a dude from Craigslist.
I had moved to Washington, D.C. for a summer internship. It was towards the end of the summer and all of my friends were gone, and I was extremely lonely. Naturally, I turned to Craigslist, and really did had every intention of keeping things platonic with anyone I chatted with (my naivete is absolutely stunning at times, I swear). This guy emailed me, and he seemed totally normal at first…until he started talking about erotic asphyxiation. Yes, he got aroused by the thought of being choked and choking women. I was morbidly intrigued, and for several weeks, we sexted. Luckily, I always rebuffed his invitations to meet in real life, and I’m comforted by the fact that I never told him my last name, but I admit, I was a hot, vulnerable mess for awhile and that really could have gotten me into trouble.

Am I going to regret not writing this anonymously? It’s very possible. But I’m a huge proponent of talking about sex comprehensively – the good stuff, the bad, the scary, the erotic, the complicated…and the humiliating.