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Shy virgin surprises me

DarkJedi

Tool-Bearing Hominid
Tool-Bearing Hominid
Joined
Aug 3, 2020
Messages
167
My first LR!

This was an interesting one. With girls like her (shy, not giving me much physical attraction signs), I would get confused about what to do and botch it up before. But I kept to my process this time, chill and not attached to the outcome, and it worked out!

TLDR
Met a girl in the street, instant date with a kiss. Very shy girl but friendly over text. Ask her to come home and cook for me as a next date, gives me a handjob coz she was on her period. The next time she's over, we have sex and I realize she was a virgin (never mentioned it to me before that!).

Approach
I had been working from the cafe that day and was taking a walk in the city center after work.

Saw her while coming out of a store. She was walking by in the street, dark-haired, petite, just my type. Didn't seem to be too much in a hurry, just looking at shop windows, which was a good sign.

I hesitated a second, then walked up to her. I walked slightly in front and opened across the shoulder:
DarkJedi: "Hey, excuse me!" (In a calm, slightly quizzical way)
She smiles, and I smile back
DarkJedi: I just came out of that store and you were walking past. (pause) You look very interesting, and I'm wondering where you're from
She was all smiley, tells me where she's from. She's been working and living just a few months in the city.
The talk was some fluff about the city and where she's from, some light teases, and I complimented her glasses, saying that they look cute on her.
She seemed very receptive, giggly and qualifying herself.
DarkKnight: So what are you upto this evening?
HB: I'm just looking at shops and seeing if I can find something interesting
DarkKnight: In that case, how about I hijack you for a bit to have a drink with me?
HB: Sure, why not?
So we start walking towards some cafes.

Instant Date
We walk into a big cafe with an indoor area and an outdoor garden patio. Since I had never sat in the garden part, I decided to take us there.
I wanted to get us seated somewhere we could sit side by side, but I see that the only tables that were left were all opposite-seating ones. Reluctantly I took one of those (didn't want to seem indecisive and go back inside).

We sat and ordered some beer. She asked me what would be good to order and asked her to order the same as mine.
HB: I trust that you have a good recommendation for me
I noticed these small signs. This girl was pretty compliant.

But on the flip side, I was realizing more and more that she's pretty shy. She would give answers to my questions, but not contribute much from her side. It was me carrying the whole brunt of the conversation.
In earlier times, I would take this as a sign of her not being into me. But this time I'm like "she's here with you, and all other signs point to her being very compliant. Let's see where this goes"

At some point, while we were talking about home or family (don't remember exactly), I was looking into her eyes and just took her hand in mine. She seemed pretty fine with it. I held it for a while as I kept talking and then let it go. Touch barrier broken.

I repeated this a few times throughout the conversation, holding her hand longer.

It started raining, and I suggested that we go and sit inside.

Inside, there are tables with chairs side by side and leather couches on the other side. I sit by in one of those, and then she again sits opposite on a chair!
We talk for a minute, then I take her hand and say, "come, sit beside me"
Normally I would add a small excuse, like "its more comfortable here", but I figured she's pretty compliant and its more dominant if I can get her to comply without an excuse.
She comes and sits next to me, our legs touching, and I continue the conversation. She says now that its a bit unusual for her since she's not dated someone for a while, but she likes it.

As we continue the conversation, all the while I keep on upping the kino, touching her neck, her hair, resting my hand on her thigh the rest of the time. Once she said something funny, we laughed, there was a lull in the conversation, and I turned her head by her chin and kissed her. Very slight resistance, and it was just a peck. Now she said that this seems too fast for her and she isn't very comfortable with it. I smiled and said:
DarkJedi: I understand. But hey, maybe this makes you more comfortable for the next time ;)
HB: Yes, I guess :)
She said that it has been years since she dated someone. Here I had a sneaking suspicion that she could be virgin, but then she talked about some guys she dated before, and I figured I might be wrong.

I didn't kiss her anymore, kept up the rest of the kino, and since it was getting late on a weekday, I suggested we leave (always better to end the date yourself).

Seeding the date
As we were walking out to go to the bus stop, we were talking about food. She mentioned that she's been cooking more lately and considers herself to be a good cook. I said:
DarkJedi: Is that so? I dunno. You should cook something for us, and then I can judge ;)
HB: (laughs) ok sure :)
I had also asked her what she plans to do for the weekend at some point, just to figure out logistics. She was pretty much free.
I hugged her goodbye after that after a bit more talk.

Inviting her over
I texted her the next day with some callback humor. She took her time to reply but was pretty warm over text and less shy, making jokes and trying to gain rapport. After a few back and forth texts I asked what she was upto that Sunday. She said she was free and if I'd like to have drink outside. I asked her to come cook for us instead, so that I could check her cooking skills. She agreed after showing some mock frustration (I think seeding the date helped here).

At my place
She came over and we bought stuff to cook from the supermarket before going back to my place.

At my place, we started with some beer and I put on some chill music.
After talking and bantering for a bit, I kissed her again.
She then says that she's still not comfortable and she usually takes a while to kiss someone.
DarkJedi: What do you mean? We already kissed twice! :p
She then said that she'll not like it if it happens again.
I just smiled and let it go
Would have got frustrated if would happen before, but I've taught to control myself and not react

We were talking about random stuff, and she mentioned a few times that she was surprised she decided to come directly to my place. That she is new to the city and has a tendency to be anxious. She joked that I could be a serial killer and no one would ever know. I agreed and amplified the joke. I sensed that she's trying to be funny but actually had genuine concerns and I'll have to be dialing up the comfort a lot.

I propose that we start cooking after sometime. While she cooks we talk about food and what we like etc. Some light teases here and there about how she does things in the kitchen. Some light kino. We eat. She asks how it was, I pretend to thing long and hard and then compliment her cooking.

We finish up and are chilling again. I am escalating my kino again. At some point, I just pull her into my lap. Keep on with the kino. I'm caressing and lightly pulling her hair, she mentions she really likes that. The music changes and she mentions she really likes the song. I suddenly notice a change in vibe from her. Can't really explain, but it felt like she was more receptive (maybe more dreamy/bedroom eyes). I kissed her and she kissed me back hungrily. We made out in our couch. After a while I feel she's pretty aroused. I said:
DarkJedi: Let's go to the bed. It's more comfortable
HB: I don't want this to go too far
DarkJedi: (smiles) We won't do anything we're not comfortable with
We go back to my bed. Continue making out. Top comes off pretty soon. We keep at it, but I can't get her to lose the pants. I try being chill, fractionating, but she firmly said no twice. I take it that its not happening. Also I didn't wanna push it too much since I felt she needs comfort. Ask her to give me a handjob and she does. After that she mentions she is on her period. I smiled and said that that's not a problem for me. She said she's not comfortable. So I left it at that.

We talked for a bit after that and she left. Texted her to text me when she gets home (more comfort), and she does.

Next Date
We were keeping on lightly texting and a week later I proposed for her to come by and I'll cook.

This time it was all smooth sailing. After dinner, I escalated, took her to bed. While having sex, I see that I need to explain her what to do (like how to get into a position etc.), which felt weird at first. Then I notice the blood. She then admits that this was her first time! I mention that she should have told this to me earlier, and I would have made it more comfortable for her. Anyway, I take things more slowly from then on and things turn out fine.

Takeaways
I was surprised that she is so shy and still was fine coming down to my place so soon and also having sex for the first time. This was a new reference experience for me.
My biggest takeaway here: being calm and unreactive and sticking to the process, while calibrating to her state.
 

Kaida

Cro-Magnon Man
Cro-Magnon Man
Joined
Jul 6, 2020
Messages
633
Great lay brother! Props on getting the virgin to relax man, its harder than it sounds.

How did you get her comfortable to push through the pain with you? Or did this girl just not hurt at all her first time
 

DarkJedi

Tool-Bearing Hominid
Tool-Bearing Hominid
Joined
Aug 3, 2020
Messages
167
Great lay brother! Props on getting the virgin to relax man, its harder than it sounds.

How did you get her comfortable to push through the pain with you? Or did this girl just not hurt at all her first time
Thanks man!

No, she did feel pain. After I realized what was happening I just took it super slow. Stopped everything and talked. Made some jokes to lighten the mood. She was feeling anxious, so I calmed her down, saying that its perfectly natural to have these thoughts since it was her first time. Also that if she had told me before, I could have made it smoother for her. I also said that in the end I want her to have a good first experience. We'll go slow and stop anytime she does not feel good.

All of that calmed her. We started back slowly, and I made sure that she was super wet before I entered.

EDIT: I entered super slow too and thrusted very little till she got more used to it and I could feel her relaxing.
 
Last edited:
the right date makes getting her back home a piece of cake

Jan

Tool-Bearing Hominid
Tool-Bearing Hominid
Joined
Jun 28, 2021
Messages
412
We were talking about random stuff, and she mentioned a few times that she was surprised she decided to come directly to my place. That she is new to the city and has a tendency to be anxious. She joked that I could be a serial killer and no one would ever know. I agreed and amplified the joke. I sensed that she's trying to be funny but actually had genuine concerns and I'll have to be dialing up the comfort a lot.
I think you've done very well, especially when it comes to comforting her, being patient and not getting angry when things didn't sail smooth.

I have just one comment. When a girl mentions the risk of serial killer, she doesn't do this as a joke. Even if they sometimes may sound like that. It's a nervous type of laughter, and it has more to do with the fact that she is attracted to you, she doesn't want to accuse you of something negative, but she has to raise this issue for obvious safety reasons.

In my experience, the best way to handle this objection is to be understanding, consider it as real concern of her (be serious about it) and speak briefly but firmly. I usually say: "I understand you have this concern, but I'm not a serial killer. I'm safe." The most important part is that you are speaking the truth. It's easy to speak the truth in situation. Just do it.

If she mentions this again later, just say: "Relax I'm safe. You can leave any time."
 
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