Let’s Talk About Sex, Baby! Your First Time Experiences, in All of Their Awkward Glory

These bloggers/Betty readers took a trip down memory lane (with a condom, a partner, and a pickup truck).

The To Do List sex

My first time should have been perfect. My grandmother was gone for the day (or so I had thought), my room looked halfway decent, and I was wearing a cute printed camisole and mini skirt. My date and I were listening to music and making out when one thing led to another. And when I like something, I really like it. I was so loud that I was worried that the neighbors were going to call the cops. Oops! When we were finished, I heard the television set blaring from the living room. As it turns out, my grandmother had gotten home early. We both got dressed as quickly as possible, but it was incredibly awkward. To make matters worse, she was watching the Discovery Channel (animal sex, anyone?) and had heard everything.

Whether your first time was exceptionally awkward (but still okay), kind of hot, or downright terrible, you’ll never forget it –though some of us may have tried. I’ll always remember my very first sexual tryst for the insanely uncomfortable hot mess that it was. As you relive your own steamy (or not!) encounters, let these five bloggers help!

Who’s Your Daddy?

-Liz Marie, WeLoveDates.com

I once attempted to have sex with a single dad. He assured me his seven year old son wasn’t home when he invited me over for a glass of wine after our third date. I knew exactly what going over to his house for “wine” meant and while I wasn’t sure we were compatible as far as long term relationships go, I did know that he was super attractive, charming and did crossfit five times a week, so I was very much looking forward to seeing him sans clothing.

We skipped over the whole wine part, things really began to heat up and then it happened. A small voice called out “Dad?” His son and a woman who appeared to be his ex-wife were standing in the doorway. The woman told the kid to leave, while she crossed her arms and stared at the man who was inside me 20 seconds earlier. I gathered my things, throwing my shirt over my head and stuffing my bra in my clutch, walked past his ex and left. I still have no idea what happened that night, but I also knew I didn’t want to try again to find out.

He’s Seeing Red

-Erica R.

I haven’t had many crazy experiences, but my first time, the guy flipped out because I started bleeding and he panicked. He was a senior in high school and I was 13. We dated for two months and then went for it. But when he realized I was bleeding, he jumped up and got off the bed thinking he had hurt me. He ran and grabbed a towel for me, having had no idea that this typically happens the first time a girl has sex.

Read Spice Up Your Sex Life Tonight! 3 Hot Ways to Get Down and Dirty


Ack! She’s Gushing Over…Everything

-Betty W.

Okay, so not officially my “first”, but my first in 3-1/2 years and my first with “him”. Needless to say I was nervous, felt like it was my “first” time. And my God he was endowed. While making love, I felt a little “pop”, but it didn’t hurt, and he didn’t seem to notice anything. So, I just carried on. We finished and as he “withdrew” and started to roll over, he screams “My God, there’s blood all over the place!”  I look down and he was so right. The thought occurred to me that “hey it is my first time in three plus years, maybe this is normal.” I tried to act casual as I draped myself with the sheet trying not to leak blood all over his carpet. I was so embarrassed, what a romantic finish, I bleed all over the place, ruin the mattress and the sheets! After having my feet in the air for five or so minutes, I knew my hopeful remedy wasn’t going to work as the blood continued to gush. I ended up in the Emergency Room and had emergency surgery! He had popped my thinning vaginal wall.

So the best sex turned into my worst nightmare, but in spite of it all, we got married one year later! And today we laugh about it…but we are a little more cautious, trust me.

(Not So) Single And Ready to…

-Samantha N.

The first time I had sex after losing 300 lbs. wasn’t as bad as I thought it was going to be. I don’t know if I was just comfy with the gentleman in question or the fact that it was also the first time I had drank in 3 years – but it was like shooting fish in a barrel. Except he was the one shooting….never mind.

I won’t lie, I was petrified that first time – for as ‘skinny’ as I am now, I’m still in Fat Girl Headspace and when you lose that much weight, your body doesn’t just go to the shape you want to be. If only we were like shrinky dinks! So sex means being naked and yeah, I’ve lost weight – but Kate Upton I’m not…but then again, who is? Damn genetic freaks. So with some well timed swigs of vodka & a pitch black room, I was able to get down to business.

It took me a few minutes to get out of my head (that is a scary place) and just enjoy myself. But once I did that, it was great. I had fun, he had fun, we had a fun a few more times and called it a night. The fun ended after I found out he was married. Could be worse I suppose? I knew someone who had sex with some old dude and he dropped dead after he finished on her face. So I got that going for me…

The Girl Woman Next Door

-Darren Michaels, author of Flipside Erotica Presents: Both Sides of the Story Vol. 1

My neighbor –let’s call her “K”– kept telling me someday she was going to do me a huge favor. At the time, I just giggled nervously and probably blushed when she said something like that, not really knowing what she had in mind. One fateful summer day, when my parents and sister were out of town and I was alone for a long weekend for the first time, she made good on her promise. I remember it like it was yesterday.

She was 35 when she knocked on the door, and I answered to find her standing there in a long T-shirt. She sat down on the couch, looked me up and down in a way that made me shudder.  Part of me wanted to turn and run, but part of me wanted to know what she had in mind. I was 17 and I was about to learn what being a man is really all about.

She leaned over and kissed me, soft at first and then with growing force. She took the lead, encouraging my touch and gently giving hints of instruction. It was my first time, and I was an eager student. We spent the afternoon in my living room, touching and tasting, teasing and exploring one another. I was nervous at first, but she put my mind at ease. I am sure I have her to thank for my career as an erotic novelist.

Diana Denza is BettyConfidential’s contributing editor. 

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