Awkward Virginity Sex Stories You Have To Read

Losing your virginity is exciting, but sometimes things don’t go as planned. Whether it’s something you didn’t plan for or your partner blurts something out that you don’t expect, having sex for the first time can provide you with a story to tell your friends for ages! Check out some of the most awkward virginity sex stories that are sure to make you laugh — or cringe!

10. He Was Really Well-Endowed

The Underwear Expert

Size matters, but how about when it’s too big?

“I was so excited for my first time… Until I saw the size of his package. It was as long and as thick as my forearm (I’m really petite). I just gulped and asked him to go slow… He didn’t…”

9. She Only Wanted Anal


“My girlfriend told me she wanted to lose her virginity with me. But when I got into her bedroom, she said that she only wanted to give me anal. Apparently she wanted to stay a virgin till marriage, but anal was her way of ‘cheating.'”

And the guy in #8 was also in for a surprise.

8. She Was So (Unexpectedly) Dirty


“I was totally surprised at my girlfriend when she finally gave me her virginity. She had the dirtiest mouth I’ve ever heard. She wanted me to call her a slut and a whore, and was begging for me to go harder the whole time. I don’t even want to know where she learned to talk like that…”

Most guys would rather have a girl with a dirty mouth over #7!

7. She Wouldn’t Stop Crying

The Tab

“I thought losing my virginity would be fun. But as soon as I started taking off her clothes she started sobbing. I asked her and she was crying and she said she didn’t know. I wanted to do it some other time. But she said she wanted to do it anyway. She never stopped crying the whole time.”

Some people are really emotional when it comes to stuff like this — and sometimes people can’t control how they feel or what they say, like the guy in #6.

6. I Said The Most Awkward Thing Ever

The Healthy Bits

“I had been dating a girl from school for two years, and finally she agreed to have sex with me. Everything was going fine, but as soon as I put it in, it felt so weird. I just blurted out, ‘It feels like a warm melon!’ She looked over at me with the most disgusted look on her face. She broke up with me soon afterward.”

5. She Wanted It All


“She was waaay too eager when she lost her virginity. I thought she would want to go slow. Nope. She wanted me to pound her as hard as possible. Then she wanted to deepthroat. Then anal. I felt like I had just awoken a demon.”

Some guys would consider this a virgin jackpot. But what about #4?

4. We Got Caught

Daily Shares

“I somehow managed to convince a girl to give up her virginity to me during class at our high school. We sneaked off to the janitor’s closet. I was in mid orgasm when the janitor opened the door. He just stood there and said ‘Can you kids hurry it up? I need to grab a mop from in there.'”

That could have been so much worse! Just like #3!

3. She Wanted To Get Married After

Daily Shares

“The most awkward thing happened when I lost my virginity. The sex was amazing, we finished and then we collapsed next to each other on the bed. Then she turns to me and says, ‘So, when are we getting married?’ I asked her if she was joking. She shook her head and then started to look really mean. I pretty much ran out of there.”

2. Her Little Brother Watched

Daily Shares

“I was only 14 and we were having a sleepover at my friend’s house. Her older sister was super hot and we always flirted. We were all sleeping in sleeping bags in the living room when his sister sneaked in and told me she wanted to ride me. We did the deed, (she lost her virginity) and halfway through I looked over to see her brother looking at us with a horrified look on his face.”

Speaking of family members overstepping, the #1 story will absolutely surprise you — and it’s not what you think.

1. Her Mom Walked In And Handed Her The Morning After Pill The Next Day

Daily Shares

Having mom walk in is one thing. This? Is Another.

“I was texting a girl from high school, and she said to sneak in through her window one night. We both lost our virginity that night. The next morning, her mom walked in and handed her a morning after pill. She didn’t even say a word to me.”


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