What should I do?

[Doughboy48]

Curious what you would wear do in this situation. There is a 22 year old young woman that is the daughter of some of my friends. Over the last 6 months or so I have noticed whenever I wear pants that show my bulge it is hard for her to take her eyes off it. She has not made a move but last time this happened she stared and then made some decent eye contact. I’m going to an event tonight at our church and wondering if I should push the envelope a little bit and wear something that makes it stand out even more. I can always wear a longer shirt to keep it covered when she isn’t around. I have these one shorts that are tight in the crotch area and depending on underwear you can even see the outline of my cock. Just looking for opinions.

 

[Britva415]

The short answer is just "go ahead and push the envelope," but what kind of an outcome are you looking for, here? What's your goal?

Do you just want to enjoy getting your crotch looked at?

Do you want her to know you see her looking?

Or do you want something to happen between you two?

You talked about her "making a move." She almost certainly is not going to. So if you want something to happen, you need to be prepared to be the one to make a move. Catching her looking is a good pretext for that. Wear something super revealing, then show her that you know she's looking.

Depending on how she reacts to getting caught, either move things forward or drop it.

 

[Doughboy48]

I decided to wear a pair of shorts that were somewhat revealing but could have been better. She will be at church tomorrow so I’ll wear something just as revealing.

The problem is most of the time she is staring we are not alone. If we were I would just ask her if she likes what she is looking at or something like that.

I doubt she wants an old mans cock maybe it is just material for her to have in mind when she is in bed using her vibrator.

 

[Papi34]

I doubt she wants an old mans cock maybe it is just material for her to have in mind when she is in bed using her vibrator.

Don't doubt what she might want. Don't let your mind convince you that there's no chance that is what she wants. If you're just getting a thrill from her looking and that's as far as you will let it go for whatever reason, then fine, don't take a chance......but if that is what you want, you gotta roll the dice and take the chance

 

[LegendInMyOwnMind]

So you are twice her age. If you are sure that you want this, get to know her better. Let her realize you enjoy her company, particularly if she sees you choosing her over others. Then wait on the right moment to make a move--though with young women today, she may have made one by then.

 

[Doughboy48]

Thank you for the advice.

What is everyone’s thoughts on her possibly wanting me?

A little more context to help you answer this: whenever we are at church or another gathering she always seems to find where I am and then she is in the same spot usually standing next to me or directly across from me even when she has friends that she could be hanging with. She always wants me to give her a hug or rub her back. Her background is very strict Christian values. No bad movies, books or music. Wait till you’re married for sex or any sexual things like self pleasure. She has failed here and I know for sure she has slept with at least one guy. She was also asking my friends wife about self pleasure so I am sure she does that. She is very emotional or I would even say needy and lacks any boundaries in relationships. This is the only reason I would not pursue something with her. Last thing I need is a crazy girl chasing after me.

 

[PapelDoll]

When I was that age I was in. A similar situation. There was the father of my best friend who I did a lot sleep overs. He was a single father and he clearly wanted me in his bed but he never made a move. girls don’t jump to you they like to be chased and act innocent. The guy never made a move and I would have love that he did a move. I fantasize with him all day everyday but I was to afraid that if I did a move he would think I was a slut. In my mind we could have a real romantic relationship, dates, go to movies, Like a real relationship. Looking back I should have had that moment and enjoy him and let him know that I wanted him as much as he wanted me if only for sex. But I get too involve emotionally, for me sex is never just sex I feet too deep.

 

[TinaG_2023]

Curious what you would wear do in this situation. There is a 22 year old young woman that is the daughter of some of my friends. Over the last 6 months or so I have noticed whenever I wear pants that show my bulge it is hard for her to take her eyes off it. She has not made a move but last time this happened she stared and then made some decent eye contact. I’m going to an event tonight at our church and wondering if I should push the envelope a little bit and wear something that makes it stand out even more. I can always wear a longer shirt to keep it covered when she isn’t around. I have these one shorts that are tight in the crotch area and depending on underwear you can even see the outline of my cock. Just looking for opinions.

I would guess she probably wants it!

 

[live4thebj]

Tread carefully. Are you prepared to possibly lose friends?

 

[Doughboy48]

Yesterday at church I decided to wear a pair of golf shorts that are very stretchy and thin and clearly show the outline of my cock. Unfortunately I choose a shirt that was a bit to long and covered my bulge but if you looked hard enough you could still see the head of my cock hanging below the bottom of my shirt stretching my shorts out. She definitely was trying to see it because I caught her several times looking. At one point we were standing in the kitchen I was on one side of the island and she was on the other. She was checking it out and then leaned down on the counter while wearing a low cut shirt. Unfortunately I was a little to far away to see anything but it stood out because I have been around her long enough to know that when she normally wears shirts like that she always puts her hand up to push the shirt tight so there is no chance of seeing down her shirt. Later in the day we were playing a card game and she came and sat very close to me to join in. Close enough that she sat Indian style in her chair and her leg on my side was bumping up against my leg. In all these situations my friends wife was standing there along with a few other people so I couldn’t really do anything other than look. In my opinion she clearly at the very least enjoys the attention just not sure if she would take it anymore than whatever you call what we are doing.

 

[Doughboy48]

Any other thoughts or advise on what I should or shouldn’t do.

I don’t want to come across as a creepy old man and I also do not want to read to much in to her actions that I make a fool of myself.

 

[Ballsy8]

Curious what you would wear do in this situation. There is a 22 year old young woman that is the daughter of some of my friends. Over the last 6 months or so I have noticed whenever I wear pants that show my bulge it is hard for her to take her eyes off it. She has not made a move but last time this happened she stared and then made some decent eye contact. I’m going to an event tonight at our church and wondering if I should push the envelope a little bit and wear something that makes it stand out even more. I can always wear a longer shirt to keep it covered when she isn’t around. I have these one shorts that are tight in the crotch area and depending on underwear you can even see the outline of my cock. Just looking for opinions.

First of all, I always go commando unless it's really cold outside. I'd recommend that, along with the tight shorts. Let her get a good look.

Is this simply you expressing your inner exhibitionist? Or would you really like to bed this younger woman? Maybe you really have fantasies about the woman who is your friend and her mother? Perhaps you'd like to fuck them both?

What's your best case scenario?

 

[Ballsy8]

Yesterday at church I decided to wear a pair of golf shorts that are very stretchy and thin and clearly show the outline of my cock. Unfortunately I choose a shirt that was a bit to long and covered my bulge but if you looked hard enough you could still see the head of my cock hanging below the bottom of my shirt stretching my shorts out. She definitely was trying to see it because I caught her several times looking. At one point we were standing in the kitchen I was on one side of the island and she was on the other. She was checking it out and then leaned down on the counter while wearing a low cut shirt. Unfortunately I was a little to far away to see anything but it stood out because I have been around her long enough to know that when she normally wears shirts like that she always puts her hand up to push the shirt tight so there is no chance of seeing down her shirt. Later in the day we were playing a card game and she came and sat very close to me to join in. Close enough that she sat Indian style in her chair and her leg on my side was bumping up against my leg. In all these situations my friends wife was standing there along with a few other people so I couldn’t really do anything other than look. In my opinion she clearly at the very least enjoys the attention just not sure if she would take it anymore than whatever you call what we are doing.

This seems easy. If you're both in the kitchen. How difficult would it be (notice, I didn't say hard) to rub against her ass and check her reaction?

 

[Doughboy48]

First of all, I always go commando unless it's really cold outside. I'd recommend that, along with the tight shorts. Let her get a good look.

Is this simply you expressing your inner exhibitionist? Or would you really like to bed this younger woman? Maybe you really have fantasies about the woman who is your friend and her mother? Perhaps you'd like to fuck them both?

What's your best case scenario

With her and I sharing the same friend group the best case scenario is we decide to have a sexual relationship that know one knows about that way if we decide to end it it doesn’t damage that group.

Definitely don’t have a thing for her mom just the daughter!

 

[Doughboy48]

This seems easy. If you're both in the kitchen. How difficult would it be (notice, I didn't say hard) to rub against her ass and check her reaction?

If the kitchen wasn’t so big that would be easier to do.

She was over for dinner last night and I slipped in to a pair of basketball shorts without anything underneath. She couldn’t keep her eyes off it. When she was leaving she gave me a hug and I anticipated her grinding her pussy up against it but she didn’t. If my daughter wasn’t standing there maybe it would have been different.

 

[Doughboy48]

I would guess she probably wants it!

What makes you think that?

 

[Britva415]

What is everyone’s thoughts on her possibly wanting me?

If you really want this to go somewhere, then, you have to stop worrying about whether she already wants you, and you have to either make her want you or else give her the opportunity to act on it if she already wants you.

She is almost certainly not going to make a move without you creating an opportunity. An invitation. You, making the move so she can react. I mean, it could happen, but when guys wait for the girl to move things forward, it doesn't work, she loses interest, and nothing ever happens. So don't count on that.

As far as "the possibility of her wanting you" goes, if you aren't the one who is forward and you don't reveal your desire for her, then, she probably isn't going to want you enough. As it is right now, she probably doesn't want you - she's simply enjoying taking looks and doesn't have any expectation that anything would ever happen between you.

That probably won't ever change unless you do something to show her that it's a possibility, that "more" is on the table. At that time she could decide, yeah, I could be into that, or, not. But she almost certainly won't if you don't do something to give her the occasion to think about it.

Next time you see her looking, use your face and your eyes to make sure she knows you know she's looking and you like it. Once you see on her face that she knows you have caught her, do something encouraging and/or suggestive, depending on how daring you feel: Smile knowingly. Let your hand brush the area, drawing attention to it again. Step closer to her and create the opportunity for one of those hugs or back-touches or the other kinds of touchy acts you say she likes so much. Then if this is all going well and she seems receptive and not like she wishes she were somewhere else, then, just tell her you want to call her later and get her number.

If she gives it to you, you're golden. Just pursue it. If she doesn't, just drop the whole thing.

Don't overthink it all. Either you want something to happen or you don't. If you do, then act. If you don't, then make up your mind and decide to stop considering it.

I mean, it's fine if you decide that all you ever want to do is to keep revealing yourself to her and enjoying the wordless attention. It's fine if you decide that you want to put a stop to all of it and wear something modest in the future. It's fine if you decide you want to find out if she likes you and wants you, and do something about it.

Just figure out what it is you want, and if you want to take a chance, then take a chance.

I would not just grab her ass like someone else said. That's too forward. But if you can get her to give you her number, then that's a green light to go ahead and pursue her.

 

[Doughboy48]

If you really want this to go somewhere, then, you have to stop worrying about whether she already wants you, and you have to either make her want you or else give her the opportunity to act on it if she already wants you.

She is almost certainly not going to make a move without you creating an opportunity. An invitation. You, making the move so she can react. I mean, it could happen, but when guys wait for the girl to move things forward, it doesn't work, she loses interest, and nothing ever happens. So don't count on that.

As far as "the possibility of her wanting you" goes, if you aren't the one who is forward and you don't reveal your desire for her, then, she probably isn't going to want you enough. As it is right now, she probably doesn't want you - she's simply enjoying taking looks and doesn't have any expectation that anything would ever happen between you.

That probably won't ever change unless you do something to show her that it's a possibility, that "more" is on the table. At that time she could decide, yeah, I could be into that, or, not. But she almost certainly won't if you don't do something to give her the occasion to think about it.

Next time you see her looking, use your face and your eyes to make sure she knows you know she's looking and you like it. Once you see on her face that she knows you have caught her, do something encouraging and/or suggestive, depending on how daring you feel: Smile knowingly. Let your hand brush the area, drawing attention to it again. Step closer to her and create the opportunity for one of those hugs or back-touches or the other kinds of touchy acts you say she likes so much. Then if this is all going well and she seems receptive and not like she wishes she were somewhere else, then, just tell her you want to call her later and get her number.

If she gives it to you, you're golden. Just pursue it. If she doesn't, just drop the whole thing.

Don't overthink it all. Either you want something to happen or you don't. If you do, then act. If you don't, then make up your mind and decide to stop considering it.

I mean, it's fine if you decide that all you ever want to do is to keep revealing yourself to her and enjoying the wordless attention. It's fine if you decide that you want to put a stop to all of it and wear something modest in the future. It's fine if you decide you want to find out if she likes you and wants you, and do something about it.

Just figure out what it is you want, and if you want to take a chance, then take a chance.

I would not just grab her ass like someone else said. That's too forward. But if you can get her to give you her number, then that's a green light to go ahead and pursue her.

I totally agree with your assessment! Thank you also for the suggestion on what to do. I’m am reserved and not very good at things like this so I either overthink it or just enjoy the status quo. Not what I want to do but just how I am.

Tonight when I see her at church and she checks out the bulge I’ll do just like you said and let her know she is caught but that is ok and she can have more if she wants it.

I also don’t want to come across as that creepy old man that she gets grossed out by. It doesn’t appear that is the case so far since she has let me touch and rub a lot of her body already. This is taking it to another level though and she is very emotional at times so it is a little risky.

What is your thought if I came up behind her and gave her a hug that way? Would that seem to sensual or do you think considering the situation she would be ok with it. I know when my daughter is around and I hug her that way this girl always stares and I wonder if she is hoping I’ll hug her the same way. That would also allow my cock to rub up on her ass which she may like to cop a feel subtly.

 

[Britva415]

What is your thought if I came up behind her and gave her a hug that way? Would that seem to sensual

No. And it's not about "too sensual."

That would just be creepy.

I mean, you're on the right track: You're already hugging and touching (according to your first post.) Just do a hug or touch the next time the same way you have been all along, only once it starts, then you can allow it to linger and feel more sensual.

It has been perfectly chaste up until now, right? Gently raise the stakes a little bit so that she senses that there could be more to it than that.

Be subtle but not undetectable with this. Let her feel/know that she probably isn't imagining it but allow her to wonder about it. What does it mean? What's behind it? What are you thinking, what are you feeling? Send a signal but NOT one that's so blatant that it forces her to immediately decide what to do with you.

Sneaking up behind and grabbing her into a hug would force her to immediately decide: Am I OK with this? Or do I need to shut him down right now? It wouldn't be sensual, it would be too much too fast. Unless you build up to that first. Before you can do this, you have to first get to where she's okay with it, and that takes several smaller steps and a pattern of green lights from her.

Be safe enough that she can decide to be OK with you as things escalate over time. Be subtle enough that she can spend at least a little bit of time wondering how you feel about her and thinking about how she feels about you.

What do I mean by "time"? Not too fast and not too slow, but especially not too slow. If you're timid or seem unsure or seem indecisive or seem unconfident, and you keep slowing things down in hopes that she will be the one to actively move things along, then, she won't and she will lose interest.

But at the same time if you don't actively escalate things yourself with a series of flirts and provocations, and you don't pick up her green-light signals and use them to keep escalating, then she won't be ready when you do make the move and make it sensual and you'll give her the ick.

 

[Pornfan77]

Any other thoughts or advise on what I should or shouldn’t do.

I don’t want to come across as a creepy old man and I also do not want to read to much in to her actions that I make a fool of myself.

Sounds like what you really need is the chance for the two of you to be a little more alone. A time where you can make sure she sees everything she wants, and she knows you want her attention. And vice versa, you need a way to be able to admire her assets and make sure she knows you like what you see. If the two of you are never lonely, I doubt there will be much more than you’ve already experienced. A little time alone to flirt would go a long way?

 

[Doughboy48]

No. And it's not about "too sensual."

That would just be creepy.

I mean, you're on the right track: You're already hugging and touching (according to your first post.) Just do a hug or touch the next time the same way you have been all along, only once it starts, then you can allow it to linger and feel more sensual.

It has been perfectly chaste up until now, right? Gently raise the stakes a little bit so that she senses that there could be more to it than that.

Be subtle but not undetectable with this. Let her feel/know that she probably isn't imagining it but allow her to wonder about it. What does it mean? What's behind it? What are you thinking, what are you feeling? Send a signal but NOT one that's so blatant that it forces her to immediately decide what to do with you.

Sneaking up behind and grabbing her into a hug would force her to immediately decide: Am I OK with this? Or do I need to shut him down right now? It wouldn't be sensual, it would be too much too fast. Unless you build up to that first. Before you can do this, you have to first get to where she's okay with it, and that takes several smaller steps and a pattern of green lights from her.

Be safe enough that she can decide to be OK with you as things escalate over time. Be subtle enough that she can spend at least a little bit of time wondering how you feel about her and thinking about how she feels about you.

What do I mean by "time"? Not too fast and not too slow, but especially not too slow. If you're timid or seem unsure or seem indecisive or seem unconfident, and you keep slowing things down in hopes that she will be the one to actively move things along, then, she won't and she will lose interest.

But at the same time if you don't actively escalate things yourself with a series of flirts and provocations, and you don't pick up her green-light signals and use them to keep escalating, then she won't be ready when you do make the move and make it sensual and you'll give her the ick.

I agree that it may be to strong to soon which is why I was hesitant doing it.

Tonight at church after everything was over a buddy and I turned on a game and were watching. She was talking to some ladies but per usual she soon found me and came and stood directly in front of me talking about her bracket. She checked out my bulge a few times and I made sure to keep eye contact. I got talking to a buddy and she left while I was in mid conversation so I didn’t get to hug her or really do anything to tell her a quick goodbye between sentences.

Here is a little more context: her and I have known each other for years. She actually worked for my parents when she was 13-14 years old and then when she was a little older would house sit for me when I would go on vacation or travel for work she was probably 16-17 at the time. Since then her parents and I have just been good friends and gone to church together so we have gotten close over the years. Her and I text on occasion but it got a little strained because I mentioned we should keep how often we text between ourselves and she didn’t like that so she just said she would text me less when we were texting about everyday or every other day. We still text but it is very rare and usually small talk. She has told me on several occasions I’m like her bonus dad. My usual attitude around her is joking around and teasing her plus talking to her about work and her classes she is taking. We almost always hug and tell each other we love each other. She is open to me rubbing and scratching her back, arms and sometimes legs and feet.

I think that about sums up our relationship and adding context so you can understand the bigger picture.

 

[Doughboy48]

Yes that would for sure be a good thing! We unfortunately just do not get time alone for extended periods. We may get a minute or two here and there but that is about it. I’m going to the town she works either tomorrow or one day next week and plan on texting her and asking if she wants a coffee or something to try to get some alone time. We will see how it goes! I do try to plan times to get us alone it just never seems to work out.

 

[Pornfan77]

I know I don’t need to tell you, but be careful with any texts. Casual meet ups for coffee etc are fine, but limit it to that. I do hope that you can find a way to get time with her and no one else who knows the two of you. I’m an older guy(61) and thought I had learned my lesson about saying what I feel and not caring what people think. Last night, I was with my wife(not in a happy marriage, sex is few and far between). We went to an ice cream place and a woman came and stood in line behind us. I turned, and she was one of the most stunning women I’ve ever seen. She smiled at me. A big smile that made me think she wanted to talk. I turned back to my wife as she moved to sit at a table. I turned back to the lady and she smiled even bigger and almost looked like she wanted to say something. I wanted to tell her I thought she was beautiful, but with my wife there, i chickened out. We glanced at each other numerous time and I would catch her looking at me out of the corner of my eye. I didn’t have the balls to introduce myself, or ask for her number because of my wife. The chances of me ever seeing this woman again are incredibly low, and I’ve been kicking myself all day for not letting her know how I felt. We exchanged a few words, and I know I’m not always able to tell when a woman is into me, but she made sure I knew she was into me. If I ever see her again, I will not make that mistake again, whether my wife is there or not.
The point of all that is, if you get the chance, let this girl know you are interested and want to know if she is into you too.

 

[Doughboy48]

Yesterday after church some people stayed to watch the games. I was sitting on a couch talking to buddies and watching the later game. The young woman was sitting behind me with my buddies wife working on a computer. During the game I caught her several times looking over my shoulder down at the bulge in my pants. I made sure to let her know I had caught her and adjusted myself a few times and made good eye contact. Later when they were done working on the computer she was still sitting behind the couch. I had moved to put my arm along the back of the couch like you would if you were putting your arm around someone but my hand was down below the back of the couch. I did this with the hope she would slide over and brush her pussy or tits up against my hand when she got up and moved since that area is just wide enough to walk behind. At one point she did lean over the couch where her chest was perfect level with me being able to rub them she was just a little to far from reach. Not sure if I was reading to much in to it but she seemed to be subtly teasing me with her actions because she would look at me when she would make certain moves. I never flinched and just kept my hand in place letting her know it was there to please her. She could have easily sat that way and let me feel her breasts without anyone knowing and I have a feeling she was seriously considering it.

 

[Britva415]

I still can't figure out what you want, here.

Like, you could have encouraged her to go through with that. But you didn't.

What stops you from putting your arm behind (around) her, instead of putting it behind the couch?

You keep asking for opinions and thoughts, but it's hard to know how to answer without knowing what you want.