I guess I will tell the story of one of my regrets. I’m not one of those people who says, “I don’t have any regrets. I’m happy where I am today etc.” I’m not ashamed to admit I have a ton of regrets. While I’m happy with where I am in life right now, there are some things I would totally go back and change.
I’ll share the story of when I lost my virginity. I was never the kind of girl who was saving myself for a special guy or marriage or anything like that. I kind of just wanted to get rid of it. A lot of my friends were sexually active and it felt like I was the last one with my v-card. I wasn’t about to give it up to just anyone though.
When I was a senior in high school I started talking to this guy who we will call Jacob. Jacob was a junior or senior at UH and he played on the football team. We met on Facebook. We had been friends for a while (I can’t remember who added who), and one night he messaged me asking if I was going to this party. I had no idea about the party, but I pretended I was undecided so I could get some details about it. I was like, “Oh, I’m not sure yet. Where is it at again?” Once I got all the information about the party, I contacted my friends and let them know we were crashing a party. Brittany was like, “Ugh, I already planned on going to that party anyway.” Of course.
It was on a Friday night. Brittany drove us to the apartment not far from campus. I remember first spotting Jacob in the kitchen, tossing the ball in beer pong. Even though he was leaning over the table I could tell he was really tall. He had brown hair, bushy dark eyebrows and blue eyes that I could see all the way from across the room. One really distinct feature about Jacob is the small mole on the side of his face a la Enrique Iglesias. I thought it was really cute for some reason. When we walked in the kitchen, he looked up at me with his pretty eyes and smiled.
Jacob and I made out before we ever had an actual conversation. A few of us were standing out on the balcony hanging out when I suddenly felt someone’s arm around me. Jacob!
He leaned down close to me and asked, “What was your name again?”
“Reese,” I answered.
And then Jacob leaned down and kissed me. We stood there making out for like a minute then he pulled away and said, “Are you having fun yet?”
“Yeah, kinda,” I replied.
“Come meet my friends,” Jacob said then pulled me inside. We went down the hall to a back bedroom where a bunch of guys were sitting and drinking. He actually didn’t introduce me to anyone and instead sat down on a bean bag chair and pulled me on his lap.
All the guys were talking and pretty much ignoring my entire existence. Jacob kept an arm around me, but didn’t say anything to me for a while as he talked to his friends. Then he leaned back so he was close to my ear and said, “You’re so cute, you know that right?”
He just had a way of sucking me in. I don’t know if it was because he was hot or because he was a college football player or because I loved the way he talked to me, but I was instantly infatuated with him and almost like, attached to him. I didn’t want to leave his side.
One of the friends wanted to go on a food run and Jacob turned to me and said, “You coming?” And he was looking at me expectantly, like if I said no he would be heartbroken. I nodded.
We ran into Brittany and my friends on our way out.
“We’re going to get food,” I informed her.
She turned to Jacob and narrowed her eyes at him. His arm was still around me because at this point we were practically attached at the hip.
“You better take care of my friend,” Brittany said, pointing an accusatory finger in his face.
Jacob flashed her an award winning smile. “Relax. I got her.” And then he brought my hand up to his face and kissed it.
So we all piled into an SUV and due to lack of space, I ended up on Jacob’s lap again. He held onto my hips, taking care of me just like he promised Brittany. We took a sharp turn and I slid further into his lap and I could feel his boner on my lower back. I turned around and smiled coyly at him.
Jacob smiled back and whispered, “It’s cuz I like you.”
We went to Whataburger and ate then headed back to the party. On our way inside, Jacob stopped me and said, “Give me your number.” I recited it to him and he put it in his phone. I didn’t realize it at the time, but that was his way of saying goodbye. We got back into the party and he kissed me quickly before disappearing.
After that we texted all day, everyday and would spend hours on the phone at night. Usually he would call me around 10:00-10:30 and we would stay on the phone until 5:00 in the morning. I was freaking obsessed with him. It was ridiculous how much time I spent on my phone either texting him or talking to him. Kendra seemed really concerned and kept asking, “How old is he again?” and “What does he want with you?” I insisted that he was just a nice guy and we were vibing which was true. Back then I didn’t even know I could talk to a guy that much and not get sick of him.
The first time we hung out after the party, he invited me to his off campus apartment. We hung out with his friends in the common area for a little while then Jacob motioned for me to follow him down the hallway to his room.
When we were alone, he said, “I’m so glad you’re here, babe.” Aww. I was “babe.” He pushed me on the bed and we spent the next few hours making out, dry humping and with his hands down my pants. When he tried to take my jeans completely off, I stopped him because I wasn’t sure if I was ready to actually have sex with him.
The next time we hung out, I decided I was. We had spent the evening at a house party playing beer pong with vodka so we were trashed by the time we got back to Jacob’s apartment. We ended up in his bed and I was on top of him. He was trying to put his penis in me, but he seemed to have a mild case of whiskey dick and couldn’t get hard enough. Eventfully, I took charge and grabbed his penis and stroked it a bit before forcing myself on it. I don’t know who I thought I was because I had never done this and had no idea what I was doing.
I can’t remember it lasting very long, but Jacob was just kind of laying there. He let out a moan here and there, but let me do most of the work. It wasn’t great and kind of hurt, but I was excited to be losing my virginity – especially to Jacob. I noticed his face all squished up so I looked down and saw that he came without even telling me (obviously we were too stupid to use a condom).
The next morning, I woke up in Jacob’s bed and he was laying next to me snoring. I felt a weird, wet sensation between my legs so I got up to use the bathroom and investigate. I was shocked and horrified when I saw that my underwear was filled with blood! I literally screamed. Luckily though, after further investigation, I realized that the blood was contained to just my panties and wasn’t all over Jacob’s bed.
I was obsessed with him before so imagine how in love with him I was after we had sex. I wanted to spend every waking hour with him. It was sick. We had sex every weekend for a few weeks, almost always after a night of drinking. It was never particularly great, but I thought that was just how sex was. I was thinking, “Oh, I’ve been waiting to do this? Meh.” But it was with Jacob so I continued.
One Friday night, there was a bonfire and of course, I asked Jacob if he would be there. He informed me that he would and that he’d see me there. I really wanted him to pick me up so we could arrive together (desp, I know), but I figured we’d meet up eventually and spend the entire evening together.
So I got ready – putting on cut off denim shorts and two tank tops to show off the girls (remember when wearing two layered tank tops was in fashion?) and Brittany came to pick me up. When I got there I texted Jacob, “Are you here yet?” He didn’t reply quick enough so I called him. No answer. I put my ringer on loud and hung out with my girls while waiting for him to call back.
He didn’t call back. But I ran into him a little bit later. I saw the back of him first, but it appeared that he had his arm around a girl so I wasn’t sure if it was him. I mean, it couldn’t be. We were a thing, right? Then they turned around and it was indeed Jacob. He was with a girl. Tall. Blonde. Legs that went on forever. His arm was around her and her hand met his near her shoulder, their fingers laced together.
“Hey you,” Jacob smirked at me.
Before even responding, I stepped forward and pulled their hands apart because I couldn’t just stand there watching some girl canoodle with my man. The girl said, “What the hell?” before Jacob even registered what was happening.
“Dude,” was all he said and put his hands up like he was surrendering.
“What the fuck are you doing, Jacob?” I demanded. Can I just reiterate how infatuated I was with this boy?
“What are you talking about?” Jacob asked, looking completely and utterly confused.
Brittany was still standing near me and grabbed my arm to pull me away from the drama. I was seriously embarrassing myself and she was nice enough to try to save me.
“Do you like me or not?” I asked, sounding like the desperate high school girl that I was.
“I barely even know you, dude.”
The blonde girl grabbed Jacob’s bicep and they both scowled at me before walking away.
“Ass,” Brittany muttered and then continued on with the bonfire like my heart hadn’t just been ripped out.
I pretended I didn’t care and stayed at the bonfire until my friends were ready to leave. Kendra sensed something was up, but I told her I was just tired. I even kept yawning to make it more believable.
I texted Jacob before we left, “What’s your problem?” and he responded, “Don’t talk to me. You’re crazy.”
I was depressed for two solid months. Like really depressed (enough to need therapy). I couldn’t do anything without thinking about Jacob and how disgusted I was with myself for allowing it happen. He texted me a few weeks later to see if I wanted to come over. Can you believe the fucking nerve of that asshole? Needless to say I didn’t respond and I never saw him again after the bonfire. He ended up moving to Colorado.
None of my friends knew that I had sex with him or worse, that I’d lost my virginity to him. To this day, even Kendra doesn’t know. They would kill me (and back then, I thought I deserved it). I don’t know if what happened with Jacob made me the way I am now, but I totally regret ever having sex with him. I definitely learned from it, but yikes. I should have known better.
10 thoughts on “stories i’m not proud of – part seven.”
Ugh! I’m so upset on your behalf! Such an asshole! Reminds me of half the guys in my high school and most of the guys in college. So glad those days are behind me. I totally get the not being able to tell your friends about what really happened with you two. There are some hook ups I could never tell my friends about. No judgement here. Lol!
The good old you’re crazy card that guys pull. What a loser. I’ve been there. Was regularly seeing this guy and then one night I ask if he’s gonna be at our usual weekend bar. He takes longer than usual to reply and is just like “yeah maybe”. Walks in with some girl. I get shit faced and end up screaming obscenities at him across the bar. He ends up texting me later that my behavior was so atrocious he will never see me the same again. I win in the end because he and that girl dated 5 years and she left because he wouldn’t give her a ring. I got a ring. He sucks.
Jesus, Jacob is an asshole!! Ew, God. This is why I HATED dating and 99% of guys ingeneral back in high school and beginning of college. UGHHH! Sorry you went through that, but you’re right: at least it is considered a lesson learned! I hope Jacob got uglier and grosser (if possible). hahaha
I wish I had some flowery, romantic story about losing my virginity but alas, that’s not the case. It was unimpressive, seemed “meh” (like you said), and I was totally underwhelmed. Plus, it had been something special to me until it wasn’t and I kind of wanted to just do it. Looking back, not the smartest choice. I broke up with the guy a month later (he was sweet, but I was bored, and still underwhelmed). Moved on a couple of months later to the biggest douche ever who I still regret ever dating, let alone have sex with. My dating choices at 17 were awful. We all have our regrets. Thanks for sharing yours. It makes you so much more of a real person to me.
I’m glad I’m not the only one with regrets 🙂 I lost my virginity to a guy who ghosted on me a week later. We had been seeing each other multiple times a week for almost 2 months before we had sex, so I thought I deserved at least a simple “it’s over” text or SOMETHING! Guys are jerks sometimes. You definitely deserved better than Jacob! The way I look at it is we can’t change the past, only accept it and learn from it. What matters is that you have great sex now with someone you care about and who cares about you 🙂
Yeah, Jacob sounds like a jerk! Just had to say that I love these TBT posts – very fun to read!
so disappointing – what a d-bag. Love these flashback posts; super impressed with your memory lol
totally unrelated but I am visiting Chicago next month; can you recommend any cool bars/lounges/restaurants etc. that my hubs & I should hit?
my memory is so selective… I can remember what I wore seven years ago but I can’t remember what I had for dinner last night. ridiculous. and recommendations? omg so many! I recommend Three Dots and a Dash, such cute drinks – really good and fairly strong. el hefe is good for food only. some of the rooftops are fun and cute for tourists (the Godfrey, the wit, etc). Summer House is also a place you might check out, it’s pretty good. and au cheval is kind of a Chicago must! piece pizza is good for pizza and beer! wildberry is a must for brunch!
sweet … thanks for all the suggestions girl!! 🙂
Omg. I always remember clothes I wore etc. I’m clearly jaded by dating because NOOOOONE of this surprises me (boyz suck); however, you deserve better.