Have you ever had sex with someone, and thought “I am never doing this again?” I know I have sis, a couple of times. But this time, I felt like I had let my inner goddess down.
I had a crush on this guy, let's call him Tom, forever. Like 11 YEARS forever and It wasn’t like it was one-sided crush. He was the first to speak up, but at the time I had a boyfriend so he didn’t truly act on it. We would talk on and off for 11 years, but we never saw each other because of distance. Plus, we were teenagers in high school. We had talked about sex a couple of times but it never led anywhere. Not going to lie, I wanted him to be my first. I thank God every day that he wasn’t.
I had spent endless nights dreaming about having sex with Tom. I dreamed about how we would do it. If he would be rough and fast or nice and slow, and of course, how big his dick was! Imagine my surprise, when he popped up in my Instagram DMs after I posted a risqué story. The post said something like “I want somebody to eat me like a strawberry starburst.” It was originally my sisters post, I just screenshotted it to say she was out of control. Tom hit my DMs asking if he could have a taste. Bitch, when I say I was geeked, I was GEEKED. I’m sending my sisters and my best friend screenshots and everything.
I quickly began to scheme, I’ve been wanting him for 11 years and for once I was single. I hit him back saying yes, (I mean duh), and we made our date, a Friday night. The day comes and I’m anxious. I’m shaving every hair on my body, making sure my room is clean from top to bottom, etc. I’ve never been so excited, yet so scared to have sex with someone. I go to work and it felt like the hours flew by. I get home, I take another shower and let him know he could be on his way. I kept getting this bad feeling, like something was going to go wrong but I pushed it to the back of my mind. Nothing was going to ruin this night! That is when I should have listened to my intuition.
Tom tells me he’s on his way and says he got me some food. I was surprised, like you bringing food to the party? I just knew the night was going to be lit! He comes over with some Captain Jays rip-off, but it was good. He rubbed my feet as I ate and asked me about my day. I just knew I found my husband! There was no doubt about it. We turn on Netflix and this is when the fuckery started.
He didn’t waste any time to start touching and feeling on me, which was no problem. But boy was rough as hell and he could not kiss for shit. But I let that go and told him I didn’t care for kissing. Not even 20 minutes into the movie and I’m getting some of the best head I’ve had in 2 years. Tom has braces but I couldn’t tell in that moment. I was running, well attempting to run from it. It was just that good. I just knew his dick was going to be awesome. He finishes me off and I couldn’t stop smiling. I knew dick was next on the list.
Now, I’m quite shy when it comes to sex with someone for the first time. So, I was hesitant to grab his dick, but this night, I simply didn’t give a fuck. I reached into his pants and that is when I felt it. I could literally fit my entire hand around it, over it and nothing would show through the top of my hand. AND IT WAS HARD.
It was like he brought the food, the massages, the good head but no dick whatsoever. Internally, I was screaming, crying and punching the air. How dare Tom be this fucking fine, tall, athletic and have a shrimp dick. The nerve. The audacity. But I was in too deep.
Before I knew it, he’s pulling me on top of him and I didn’t even feel it go in! Then he starts to moan and was moaning more than I am (I mean I didn’t even have a reasonto moan), it was such a turn off. I like it when guys moan but when I’m enjoying it as well. I hadn’t even started to bounce good before he had came. Like I was up there for all of 2 minutes. I tried getting up to go pee (good after sex etiquette), but he would not let me up. Instead, he held on to me with a death grip and kept asking me why my pussy was so good. In my head, I wanted to ask how did he even feel it.
I was so over the night. I was praying my sister would come knock on my bedroom door or something. I just wanted him to leave. As I was about to hit him with the “I’m tired, I gotta work in the morning” (I didn’t), he pulls me onto his face. Have you ever tried climbing up a wall? It doesn’t work. After I got myself down, he climbed on top of me and I couldn’t look him in his face. I kept turning my head and closing my eyes as I faked moan. He turned me over and if I thought I didn’t feel him while he was on top, I was sorely mistaken. He came again in 2.2 seconds and I was finally able to escape to the bathroom to give myself the cuss out of a lifetime.
When I came back, I hit him with the “I’m tired” spiel, we hugged and he left. I called my best friend and cried laughing at myself. She was cracking up, but she was also sympathetic to my problem. I’ve talked to Tom a couple of time after that and seen him once. I successfully ghosted him after changing my number in February.
I know we all have terrible experiences, but this was definitely the worst I’ve had in all my years of having sex and would probably always be.