13 Women Tell the Sweet, Funny & Terrible Stories of Their 'First Time'

Wendy Robinson | Jun 7, 2016 Love & Sex
13 Women Tell the Sweet, Funny & Terrible Stories of Their 'First Time'

kissing couple Whether waiting until marriage or having barely waited until puberty, there are few moments in life as unforgettable as when the first time sex is experienced. The nerves, the excitement, the anticipation -- the feelings before the first time are almost indescribable. Of course, unforgettable doesn't always mean the experience was an amazing, or even enjoyable one.

All of those feelings can naturally lead to some fumbling, and some awkward moments. And there is no shortage of insane bedroom possibilities when it comes to two newbies trying for the first time. 

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I spoke with a group of women about what they remember about their first time and the answers were incredibly diverse. There were moments of real love as well as awkward encounters in the backseats of cars and even the presence of the band Def Leppard, just to keep it classy.

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From honeymoon sex to hammock encounters, we've got some hilarious true stories of first times that will have people giggling as they click on! And heck, maybe it'll help some folks feel better about their first times too. 


Image via iStock.com/Courtney Keating

  • Madly in Love

    1

    Image via iStock.com/ abezikus

    "I picked out some super love-making music and embarrassingly bought some condoms because the boyfriend was too nervous and that is what I was waiting on. Let's just say the song barely started and it was over. It was very sweet and a good experience. He was a good guy. I was madly in love, of course. We were 15." -- J.P.

  • Safety & Snacks

    2

    Image via iStock.com/ KatarzynaBialasiewicz

    "High school boyfriend -- it just happened and I remember being like, 'Wait, this is what sex is?'

    My dad then found a Walgreens receipt in the basement a couple weeks later with Sour Patch Kids and condoms on it. That was a fun conversation." -- L.C.

  • Dorm Room Love

    3

    Image via iStock.com/ paul kline

    "Freshman year in a lofted dorm bed in Eau Claire, Wisconsin, with a boy I loved. It felt like a razor blade going into me and lasted a few pumps and I definitely bled. I walked to class the next day assuming every single person knew I had sex the night before and I felt like a rock star. I was a late bloomer and was so super stoked I had finally done it." -- V.R.

  • Hammock Time

    4

    Image via iStock.com/ anyaberkut

    "I lost my virginity in a hammock! Who does that? It was a very short, very swingy experience. I was 17, and he was a random guy I met on vacation. I came home with more experience and, sadly, an STI. I want my daughter to have a totally different experience than I did." -- L.N.

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  • Pour Some Sugar on Me

    5

    Image via iStock.com/ svetikd

    "Sex on the hill at an outdoor concert while Def Leppard was playing 'Pour Some Sugar on Me.' Yep, classy 16-year-old. Needless to say every time I hear that song I can't help but laugh. No wonder my parents didn't want me to go!" -- M.C.

  • Jealous?

    6

    Image via iStock.com/ MrKornFlakes

    "I was 14. I used my babysitting money to buy matching bra and panties because I knew my boyfriend's parents were out of town and it was going to be 'the day.' I walked a long way to get to his house. His friend was there but left (so we thought).

    Nope.

    Mid (awkward, silent) coitus, [my boyfriend] cleared his throat and asked if I could 'grab his ass or something.' I was just about to when the door swung open and a cat went flying through the door and landed on his back. Apparently his friend came back.

    Coitus interuptus.

    Oh. And that guy is gay now." -- L.D.

  • Not Impressed

    7

    Image via iStock.com/ skynesher

    "I was 16 and it was a guy I dated from sophomore year until freshman year in college. It was fast and I really wasn't impressed. I kept wondering what all the hype was about. It got better as I got older and was with someone who was better at it." -- E.S.

  • Good First Time

    8

    Image via iStock.com/ wundervisuals

    "I had just turned 17. It was the summer after junior year of high school. I had been with my puppy love boyfriend for almost a year. He was not a virgin, I was.

    My parents were out of town. He came over to my house and we both knew what was going to happen. I remember Marvin Gaye's 'Sexual Healing' was playing on my CD player. Ha! It hurt like hell! But he was gentle. Overall, it was a good first experience." -- K.C.

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  • First Time With a Girl

    9

    Image via iStock.com/ BraunS

    "First time with a girl, I was living with a married couple and their three kids and the wife and I got super close. There was a lot of pot smoking in those days and we had sex all the time. The husband never knew. Until one day the daughter caught us kissing and me sitting on top of her mom. I was not a good person back then! I would never ever do something like that again!" -- K.M.

  • In Wilder Days

    10

    Image via iStock.com/ AntonioGuillem

    "I wanted to wait until I was married to have intercourse. It didn't stop me from doing other fun things though, but the older I got, the more I felt stupid for waiting. I finally caved in at 27 and did the deed with my boyfriend, now husband.

    I totally expected it to hurt, but it didn't, and I was a nympho for a while after that. Eleven years later I might as well be a born-again virgin cause I'm too tired and totally not interested, and would rather just sleep!" -- E.K.

  • Total Cliché

    11

    Image via iStock.com/ Wavebreakmedia

    "I had sex for the first time in the backseat of a Volvo. Total teenage cliché of an experience -- it was over fast, it wasn't great, and I was so worried about getting caught. Sex wasn't really fun until years later." -- S.T.

  • One Time at Band Camp

    12

    Image via iStock.com/ FangXiaNuo

    "I was on a trip with my high school band in another state. The air conditioner broke on the 10th floor, so we got moved to the 6th floor. My boyfriend kept the room key, and unbeknownst to me bought condoms that day.

    So after lights out we snuck up to the 10th floor and did it. It was over so fast. We washed up and got caught on the stairs of the 7th floor by his mom, a chaperone. She didn't *know* what we did, but she probably *knew.* It was a week before my 16th birthday. He was 17.

    Good experience? Meh. Wish I had known what a female orgasm was much much sooner than that boyfriend." -- J.R.

  • So Ready

    13

    Image via iStock.com/ TriggerPhoto

    "It was on our wedding night, both of us virgins. We'd only ever made out before and were nervous as hell, so there was lots of exploration and gentleness. It was amazing. We didn't sleep much -- did it SEVEN TIMES that night. Making up for lost time, I guess! Not that we've ever done it that many times again! Poor guy, I think I set him up with much higher expectations than I should have! Had no problem O'ing my first many times, maybe because I waited so long? I was 25 and READY." -- M.O.

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