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1. He’d Learned About Sex From Porn…
My first time was with a fellow virgin. This was a guy who’s sexual knowledge began and ended with pornography. There was some foreplay, but when it came time to actually begin, the guy tried to insert his entire member, all at once…like they do in porn. Instant anguish. I pushed him off me and curled up in a ball. The poor guy had no idea what went wrong.
2. This Is SOOOOO Common, Guys. Stop It!
I wish I hadn’t been guilt tripped into doing it.
3. Allergies Plus Giant Dong
If I had known I was allergic to condom lube (and most lube in general, actually) and if my boyfriend had realized his penis was giant.
4. Romance
If he wasn’t watching football throughout. Sadly, I’m not joking.
5. “Friends” Judging You Afterward
I lost my virginity in college with a guy I trusted and who was very nice. The whole experience itself was good, but after when I told my best friend she was really judgmental.
No matter how much I told myself losing my virginity isn’t that big of a deal and this is the 21st century I’ll be fine it was still an emotional thing that dredged up a lot of cultural baggage and I could use if not the support of my best friend then at least not her outright condemnation. She made me feel like crap and our friendship wasn’t really the same after that.
6. A Family Setting
If it wasn’t in a minivan, that would have been a step up.
7. Just Trying To Get It Over With
If I actually loved him and wasn’t just suddenly impatient to lose my virginity at 21. It was ultimately “meh.”
8. Trophy Collectors Should Be Banned By Law
It probably shouldn’t have been with a pathetic asshole. It should have been with someone who cared about me as much as I cared about them, and not just some guy who wanted another “cherry trophy.”
9. In A PT Cruiser
If it wasn’t in the front seat of a PT Cruiser…and if the car hadn’t died promptly after, forcing us to go look for help in the rain.
10. Would Have Like To Know It Might Hurt
I wish I had been better prepared. I knew about my hymen but I never had someone to tell me how it was going to be. It hurt and there was blood. I felt really awkward and hurt for a few days. I was looking at the movies where it was so blissful and got a horrible experience. They should tell you these things in sex education.
11. The Man In The Sky
Coulda done without the crushing mormon guilt. At first, my bf at the time couldn’t get hard, lots of nerves, and I actually thought ‘God’ was giving me one last chance to save my virginity.
12. Would Have Waited Until It Felt Important
Not drunk for the first time. Not with a boy I had gone to high school with, but had just met at the party. Not on my friend’s family’s basement chaise lounge. Not with other people sleeping in the room. Not without protection
In short, I should have waited until it was someone important to me. Nothing about the sex was terrible, but the situation was embarrassing, and although he asked me several times (knowing that I was young and drunk) if I was SURE I wanted to do this, I should have said no. I was naive enough to think that if I did it, he would be enamored with my sexual maturity and we could go out. Nope, his friends all silently judged me when I ran his shoes upstairs to him as they were trying to sneak out the next morning.
13. Classic Disappearing Asshole
He told me he loved me, but that was a lie. Then he left almost immediately afterwards so he could go set off fireworks from China in the woods with his cousin. He even borrowed $20 bucks from me for gas money and told me he would call me later. Never even saw him again after that.
14. Definitely Not Brittany
Not being called Brittany…. my name is definitely not Brittany. Also, not him getting me pregnant after he SWORE that gel was spermicide and then dipping off to Florida to never be seen again. Yeah, being loved and not feeling like a used up whore in his eyes would have made the experience better. Oh, and warn her if you’re not circumcised…. Okay, I don’t want to talk about this anymore…
15. The Dane Cook Of Sex
I wish that I had told him that it was my first time. Maybe he would have made it a bit more special. Like we wouldn’t have been watching Dane Cook the entire time.
16. Using Sex To Try To Keep A Man
It wasn’t terrible, and I loved the guy (ended up being with him for close to 7 years), but I should have waited a little longer. I did it to keep him around because I thought he was losing interest and we ended up splitting two weeks later and beginning a destructive cycle of being together / breaking up / friends with benefits / jealous rage / back together + random amounts of cheating and lies on both parts. The entire relationship gave me a fucked up sense of how a healthy relationship goes and it took me a long time to straighten myself out.
17. The Chafing
If he didn’t “go in dry.” Ahhh, 17-year-old me was heaps smart.
18. Checking Every Terrible Box
*if he had loved me.
*if he had turned off the TV
*if he had taken off his socks
*if he had gone down on me first
*if he had done ANYTHING to make me feel sexy, loved and wanted
*if he didn’t cheat on me a month later by asking his ex for nsa sex.
*if I hadn’t stormed out immediately after
*if he didn’t run and tell my friend as soon as possible
Christ, regrets.
19. *Cringe*
…I thought it would be a good idea to have John Mayer playing in the background. Then when it started to hurt like a bitch, it felt John was just mocking me with “Your Body Is A Wonderland,” and all of a sudden I felt like a cliche.
20. The Orgasm Riddle
I just remember being super pissed that it was never really explained to me that penis in vagina doesn’t automatically mean fireworks and orgasms.
21. Always Pee Afterward
If I hadn’t immediately contracted a urinary tract infection and assumed I had a deadly STD.
22. Identity Issues
It would have been less traumatic if either of us had known he was gay.
