Introduction

Recently moved to Lisbon due to a job offer. The search for a place to live was not easy, and the best place I managed to found was a student residence. As of now, I've been living there for 4 months. Most students in the residence are way younger than me, somewhere from 18 to 23, therefore I'm one of the oldest residents. There are tons of cute girls, but I don't feel that comfortable making moves, as not to be labeled the creepy guy. However, I still get some attention from some girls, and with this particular one, things progressed.

Me: 30M, Portuguese, fit, fair skin and blonde short hair. I'd say I'm reasonably attractive and look a bit younger than I am.

G: 26F, Spanish, fair skin, quite skinny but fit, and short. She's really shy, but cute and good-looking.

Random encounters in the residence

On several occasions, I've came across G in the residence, either on the elevator, the hallway or the gym. We rarely spoke, but I always gave her a smile whenever we made eye contact. I noticed every time we came across each other, she'd look at me, and smile back. In my mind, I was thinking that I have to talk to this girl someday. She seemed quite young, around 21 or 22, like most people in the residence. I don't want to be perceived as a creep, especially due to the big age difference, and so I might've been a bit too passive.

Her initiative <2024-05-25 Sat 15:00>

This past Saturday, I met G in the hallway once again. Gave her a big smile, she did the same, and went to my room. Later I get a text by an unknown number, and it's her. Apparently she stalked me in our residence chat, and decided to text me. I was pleasantly surprised, especially since she was being flirty in the text exchange.

*Remark 1:*

On all these interactions, I had a feeling she was curious about me. I was reading all these signs, but what held me back was the fear of being perceived as a bit creepy. Maybe I should've stopped her and talked to her for a while.

Brief chat by the door <2024-05-25 Sat 21:00>

We keep chatting via text through the afternoon, while I was working in my room. By the end of the day, I went to the kitchen to cook. As I was coming back to my room, she stepped in the hallway right in front of me. She was wearing a tight dress, and so I notice she had quite a nice body. She didn't noticed me at first but when she got to the door, she turned and I engaged in conversation. We chatted briefly, just getting to know each other a bit more. I had my dinner getting cold in my room, so after a short while, we both went back to our rooms. I received a text from her shortly after, where she expressed she felt lucky she got to see me twice in the same day, alluding to the fact that we always met briefly on random days.

Having a beer together <2024-05-25 Sat 22:40>

We start making plans by text, to check when we can see each other again, possibly during the week. But I'm thinking that maybe we don't have to wait that long. Once I'm finished with some urgent tasks, I invite her for a beer in the residence's lobby, and we talk for an hour or so.

I notice this girl is pretty shy: she has a hard time maintaining eye contact with me, and smiles quite nervously whenever I look into her green eyes. However, she's being flirty, in a most direct way. She explains that she noticed me many times, that she finds me gorgeous and wanted to say something but never found the courage. She mentions she finds me beautiful several times while we talk.

So I'm thinking, this girl is super shy and she still gathered the strength to initiate with me. I'm quite flattered obviously, as she's really into me. However, I'm also a bit concerned, because I should've picked up all these signs and talk to her ages ago. I mention something interesting I have in my room, and I invite her to check it out, to which she agrees.

*Remark 2:*

Considering we don't know each other that well, she's pretty nervous around me, and considerably more physically vulnerable compared to me, I'm being cautious and making an effort to make her feel comfortable while we're alone in my room. I also make no overt moves, just being charming and funny.

We leave the room, and then she shows me her room. When I'm leaving, she hangs by the door, and mentions it seems to her I don't want to stay in her room. The way she expressed it, I instantly noticed she wanted things to happen. I followed up by asking if she wanted me to stay in her room. Consider that there isn't any apparent reason for me to hang in her room, especially because the rooms are a bit cramped, so it must mean something else. She replied that we wouldn't be comfortable in her room, since she had a friend that was crashing there and would arrive any time. So I invite her to mine, to which she responded positively. She asked for 5 minutes, and then she knocked on my door.

Spending the night together <2024-05-26 Sun 01:00>

I'm a bit nervous by the suddenness of the situation and she is too, I can tell. We're both shaking, which is a first for me. I ask her what she'd do if I were to give her a kiss.

We take it a bit slower, intermingling kissing with chatting, so we can ease into it. We stayed up until 03:00 and then went at it again in the morning. She's pretty nervous and shy, even when we're in our most intimate moments. After a while we both had calmed down a bit, and we're just enjoying it. She mentioned we can make this a regular thing

Conclusion

Overall, I'm pretty happy with myself, obviously. I'm desired by a cute girl, who overcame her own shyness just to be with me. This is not something I'm used to, I'm used to pursuing and being the one initiating. What's more interesting is that this girl is super shy and timid, and even then, she managed to make all the situation happen. To be fair, I think all this happened mostly due to her actions, I just spotted the cues and responded to them. Literally, this girl fell on my lap. I guess it's the benefits from working out and taking care of myself, and my appearance and friendly demeanor.

So, I'm also considering that I could've approached this situation much better, I could've been more forward. However, I'm worried I start creeping some girls out, or start getting a reputation. As I mentioned, girls in the residence as super young, and comparing to me, there's a huge age gap. I find many of them quite attractive, however I restrain myself from being more forward due to this. In G's case, she's closer to my age, so it's more acceptable. Maybe I'm overthinking.

My results for the night:

  • Solo approaches: 0

  • Group approaches: 0

  • Number close: 1

  • Kiss close: 1

  • Fuck close: 1

Points to improve:

  • I either need to overcome my worry of being perceived as a creepy older guy, or I need to realize things with G went well due to our closeness in age, and with younger girls it wouldn't necessarily be that straightforward. I'm not sure.

  • What I'm also noticing is that sometimes things happen more easily because the girls also wants it. In this case, I had only to ask for it to happen, as she was already down for it, but was unsure if I was interested. So I need to be more confident and start taking more risk, especially when it comes to asking or leading towards something more sexual. I've missed many opportunities for more intimate times simply because I thought the girl wasn't interested in sex right away, and she needed to get to know me better.