The Single Girl Diaries is a series where we explore the many interesting, unfiltered stories and experiences of single girls everywhere. From the good times to the challenges, we’re here for all of it. The stories cover a wide range of topics, from dating and self-growth to matters of the heart and mind and everything else in between.
In our latest story, *Victoria recounts her first sexual encounter, which led to a friends-with-benefit relationship that eventually drove her to celibacy for 3 years. She details how they met, their first sexual experience, how she got stuck in a love triangle and her decision to be celibate.
“My name is Victoria, and I was 20 when it all began. I was studying at Jomo Kenyatta University of Agriculture and Technology in Kenya and was part of a Christian community in school. That’s where I met him—Dylan. He was on the media team, and I was drawn to photography. We didn’t plan for things to get serious; it was just a few hangouts that somehow grew into something more.”
Meeting Dylan
It all started a couple of years back. Once, we went on a group hike, and by the end, my shoes were completely ruined. It began to rain, and I had no choice but to walk back down the mountain barefoot.
*Dylan offered me his shoes, which was really sweet because we weren’t close or anything. He walked all the way down without shoes, but his gesture stayed with me, and this led to a friendship that had us hanging out more. Soon after, we crossed the line from friendship to something more—that’s how I ended up losing my virginity at 20.
My Sex Life with Dylan
We were at his house drinking and trying to paint each other’s faces, and that’s how we ended up kissing. I told him I wanted to go all the way. He asked me a couple of times if I was sure about it, and I told him I was. I guess he couldn’t believe I wanted to do that with him. And then, I guess we did it, but it wasn’t what I expected.
The sex was painful for me when it came to the penetration part. But I figured that after hearing about how many other people’s first times were painful, it wasn’t a red flag. But yeah, it was painful, and I didn’t really enjoy it. Then we fell asleep cuddling, and the next morning, we tried again. I was hopeful it wouldn’t be painful, but it still was.
We had a conversation after this happened, but it wasn’t along the lines of dating or exclusivity. It was more of the opposite. We both wanted to be basically friends with benefits -so all the intimacy and no strings attached. I think, at the time, that was what I wanted. It seemed like it would be the ideal situation.
Typically, when you start that kind of relationship, it’s because the sex was great. But this time, it was painful. However, I enjoyed other aspects of sex that led to the penetrations. If we could have done all those things without penetration, that would be the ideal setup for me.
I never spoke to him about the sex being painful and that I would have liked to instead focus on the other things. We didn’t really have that conversation because I could tell that he was very excited about the penetration bit of it. So, at times when I didn’t want to, or I just wanted us to go some distance but not the whole way, he would be disappointed.
The First Breakup
I thought keeping it casual would simplify things, but it became more of a mess. The first time I admitted, even to myself, that I had feelings for him was at a party thrown by one of his friends. It was a typical college scene—loud music, people making out in corners. Around 2 am, I was sitting on one end of a three-seater couch, nursing a drink and watching music videos on TV. Suddenly, I noticed some movement from the corner of my eye.
Dylan was on the other end of the couch, making out with another girl sitting on his lap. Seeing him like that hurt. I felt like a secret he kept in the background. I knew he wasn’t mine, so I just looked away, staring blankly at the screen. After a while, I left, but since it was late, about 2 am, and the campus wasn’t safe, I had to go back to his place, and I found a quiet corner to crash.
The next morning, I got up and left without his hoodie, which I had been wearing from the previous day. He called me later to ask if everything was okay, and I told him everything was fine.
We had a mutual friend, Paul, who wasn’t at the hike. However, we all hung, but we never let Paul in on the fact that we had a separate relationship. After that, when the three of us hung out, I wasn’t really talking to Dylan—just Paul. I gave him one-word replies or changed the topic if he asked me anything.
When we were going to a sleepover/party at one of our friends’ places, he asked me what was wrong, and I told him that during this party if he found time to talk to me, I’d tell him what was going on. I didn’t really think he’d find the time because he’s usually the life of the party who tries to engage the crowd, but he did. So I told him that watching him make out with someone else made me feel bad, which made me realise that I had caught feelings for him. But I told him my feelings weren’t his responsibility and that I’d find a way to sort them out.
He responded that he wasn’t looking for a relationship either, and I told him that’s why I said that my feelings were my responsibility. I wasn’t telling him so he could do anything about it. I just wanted him to know why I was acting like I was. We left it at that.
A Near-Rape Scare
Though we agreed to take a break, I still had feelings for him. A couple of days later, we went to another party, and one of his friends showed interest in me. I wasn’t against it, and I figured it might make Dylan feel the way I had. At some point, this guy and I were smoking shisha, and he passed the smoke into my mouth, making it look like we were kissing. I could feel Dylan glaring, and oddly, it felt satisfying.
Later, the guy invited me to his room, and I thought, Why not? We went to his room, we started talking and listening to music, and next thing, he started trying to kiss me. I didn’t want to go there with anyone else, and I tried to push him away, but he was being a bit forceful.
I started fearing I was going to get raped because I was trying to make a guy jealous. Eventually, he got off me after I started having a mild panic attack because he felt so strong, and there really wasn’t anything I’d be able to do to stop him, even though I had told him that I didn’t want to do it. Once he got off me, I managed to run into the bathroom, where I hyperventilated before I got calm again. After that, I went back to where Dylan was sleeping on the couch and asked him to make room for me, and I slept there.
The next morning, we went to his house and had the same conversation we had at the sleepover. But the roles were reversed this time. He said that seeing me make out with someone else made him feel bad, and it made him feel even worse for what he did with that girl. And I had to clarify that what was happening wasn’t what he thought, and I told him about that guy basically trying to force himself on me.
The conversation ended with us deciding that we needed to get some space from each other because we were at a place where it was getting complicated, and none of us wanted to have that talk about “exclusivity.” So we decided to take a break.
The Cycles of Getting Back Together
After the conversation about getting some space, I don’t think we made it past a week. A week later, we had another conversation in which we resolved to sweep our past issues under the rug and start over. Again, while we had several conversations, we never exactly defined what we were doing.
What complicated it was the fact that we were actually friends and really close. So much so that when something really nice happened to me, the first person I thought to tell was him. It was also the same for him, and that’s how we kept falling back into the cycle. He would call me to tell me something about him, and we’d end up talking and then fall back into the friends-with-benefits relationship.
He was still hanging out with the girl from the party, but he didn’t attempt to hide it.
He was trying to see where things would go with both of us. What made it exhausting was that because of that, he started doubting me, saying I was seeing other people, just like he was with her.
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We had countless conversations where he’d tell me he didn’t trust me and thought I was playing him. No matter how much I’d reassure him that he was the only one I was seeing, he’d never believe me. It became a pattern; he’d get upset over something I said or did, and I’d have to coax him. I’d call him before bed, asking what was wrong. He’d deny anything at first, then finally open up. We’d talk, and he’d say everything was fine, but the next day, it would be the same script with a different line.
The final breakup
The moment I realised how bad things were getting was when he moved in with Paul, and they became roommates. One month, they needed rent, so they each put up their share. Instead of paying it, Paul gambled it away and lost everything.
That month, they couldn’t pay rent, and when he told me, my first thought was to bail him out with my savings. I was actually about to offer when something clicked in me, and I thought, Why am I even considering paying rent for a guy who can’t choose me?
It was a wake-up call. I was willing to do all these crazy things for him, and he couldn’t even choose between me and this other girl. After that, I just told him that I hoped he figured things out and that he’d probably be fine.
Later, I went home and called him over. When he came, I told him we couldn’t keep doing this. I said he had to choose between me and her because I was done. I don’t think he believed me. He probably thought it was just like the other times we’d agreed to take a break, but this time, I was serious.
After he left, I decided to join a gym to focus on myself. I figured that if I could get physically stronger, I’d eventually gain the emotional strength to resist taking him back. He did come back, eventually. Something happened, and he needed someone to talk to, so he reached out to me. But this time, I told him I couldn’t do this for him anymore.
The whole experience had been exhausting, and I was scared of getting trapped in another cycle with someone else. That’s when I decided to go celibate. It was supposed to be for a year, but one year turned into two and then three.
I was 20 then, and from ages 20 to 23 or 24, I didn’t have any relationships, situationships, or anything else. I was completely celibate. Now, at 26, I’ve finally met someone, and for the first time in years, I feel like I’m ready to try again.
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