Today, my boyfriend and I were trying to have sex for the first time. Not only did he struggle for five minutes to put on a condom (repeatedly snapping himself in the balls), but he then had to ask me "which hole" to put it in. I'm dating a thirty-four year old virgin. FML
Collection
Halloween
A failed costume, stolen candy and a very real scare: Halloween, the one night when fear is allowed.
Today, I was ready to have sex with my new boyfriend. Turns out he's a 30 year-old virgin who doesn't know shit. He couldn't find my vagina and was just humping my crotch, then when he finally got it in it was 5 pumps, a squirt and done. He thinks he did a good job. Now I have to teach him how to do it properly. FML
Today, my boyfriend and I decided it was time to lose our virginity. After our clothes were removed, we spent 30 minutes trying to figure out how to actually have sex, and eventually gave up. FML
Today, my boyfriend and I tried to have sex. Foreplay was amazing, but as soon as he started to get it in, he lost his erection because he was too nervous. He's a 30-year-old virgin and this has happened at least 10 times. FML
Today, I was messing with my boyfriend in my basement. We are both virgins and he wanted to perform oral sex on me for the first time. Naked, we finally decided to try to have sex. We discovered the act is much harder than it may seem. We're both still virgins. FML
Today, I finally lost my virginity to my boyfriend. It hurt like hell, was over in less than a minute, and he tried to reuse the condom for a second round. FML
Today, after a year of coaxing, I got my boyfriend of 18 months to agree to have sex with me. He decided his first course of action was to try to shove his flaccid penis into my unlubricated vagina. FML
Today, after making out with my boyfriend for the first time, it took me an hour to convince him he was still a virgin. FML
Today, I finally felt ready to make love to my boyfriend for the first time. It all went great, until I tried putting the condom on him. In the process, I managed to nick his penis not once, but three times with my nails. His eyes brimmed with tears and he completely lost his erection. FML
Today, my boyfriend and I tried to have sex for the first time. Everything was going well, until he tried to put it in. A few minutes later, he said, "It's not hard enough." We tried for another half hour to fix that. We ended up eating ice cream. FML
Today, while finally about to make love with my long-term boyfriend, he came from putting a condom on. FML
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Top comments
epoh_fml 0
aw it sucks but you're doing him a great deed. My brother is a 31 year old virgin (I am 85% sure of this). SOMEONE has to help those poor guys out!
jf7609 0
which hole? this guy hasn't seen any ****?
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Comments (147)
AxCxDxDx 0
Yeah, how do you snap yourself in the balls? Were they out of extra small condoms, so the ones he got were waaay too big?
Jaded4good 0
Be glad he's not second hand. At least you can train him to do the things you like.
saaaammmmm 0
What does it say about you if you are upset over dating a 34 year old virgin? There are women who would have been honored to take his virginity.
what_the_fail 0
At least **** the guy. Look, if you do you'll make him happy and he won't be a virgin anymore. If you don't, he will eventually become depressed or suicidal. Or he will become a serial rapist as chronic masturbation just doesn't do the trick for him anymore. I wonder how you'll feel seeing those poor little rape victims of your boyfriend on the news then. So make the right choice OP. =)
logieebearr 0
has he never fingered you?I mean fingers and a penis most likely go in the same hole(not talking about anal..)and ya he's never seen movies or ****? wow
Sekococo 0
perdix you made my day :D i wish i had some gentle asking me which whole he wants to go in :) ...execpt the commentors
Sekococo 0
give him a preview and take out a strapon and give it to him ;) that will pop his cherry
von_brown 0
is it any wonder he's still a virgin?
itsgen 16
hahahah this one made my day!!! wow which hole, priceless xD
annalovescheese 0
he sounds really dumb. its not that hard to put on condom and figure out which hole to put it in