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Let's Talk About Sex

Let's Talk About Sex

Written by The Walkers

You asked, they answered.


Dear Mr. & Mrs.Walker,

I’m a smaller girl (down there) and the guy I’m seeing is very big. I want to be intimate with him, but honestly, I’m a bit scared and have no clue how sex with him would work. I feel silly having this problem. Do you have any suggestions?

Question #1:  Size really does matter.

TS Walkers Image2

Mrs. W: I know this is going is going to sound cliche but PREHEAT THAT OVEN baby!!! Before jumping into sex, get him to focus on you, wherever you may like. Relax and stop thinking about the logistics. It will fit, but the oven needs to be heated and ready to go before you stick the baguette in. My two other suggestions for you include lube, and taking it slow. Even once the oven is preheated don’t just ram that baguette in. Take it nice and slow, and before you know it you’ll be begging for more!

– P.S. Play with yourself while he’s entering you. That always loosens things up a bit 😉


TS Walkers Image3Mr. W: Size differences, in either direction, can be a big adjustment for a couple. You might be in the lucky position where your guy is just a bit overqualified for the job. You really need to have a man who is sensitive to your needs in this situation, for you to be able to open up to him. If he is too long for you, then try asking him to keep to smaller and
more gentle thrusts. You two can work your way up to deeper penetration as you become more aroused, but it is important that you start small here. If he is too thick, then you may be finding it difficult to relax enough to really let him in. Don’t forget to be playful at this stage. There is no rush to get it in there, and taking your time will make things much more comfortable. Unless your guy doesn’t have the patience and respect to help work through this, or his size is just too much to handle, you should be able to find ways to adapt to your differences here and still have a lot of fun together.


Dear Mr. & Mrs.Walker,

I’m 28 and interested in a coworker, but have always struggled with how to approach men. I simply don’t feel comfortable being the aggressor. Can you give me some tips on how to let him know I’m interested?As we work together, I’m afraid to make things awkward.

Question #2: Caution is advised when mixing business & pleasure.

TS Walkers Image2

Mrs. W: Due to the nature and environment of this crush, I would suggest you take the more subtle road. This will also give you a chance to see if he feels the same way towards you, or a chance to back out if you change your mind.

1. Smile a lot – but in a natural way (don’t get crazy now)
2. Gentle touches whenever it is appropriate (again, don’t get crazy)
3. Ask him out for after work drinks

Okay, maybe number 3 isn’t so subtle, but it works because its not a date. It’s after work drinks, and you’re just asking as a co-worker. There are high risks involved in a work crush, which is why I suggest taking it slow and giving gentle hints. Trust me, if he’s interested in you he will take the bait.


TS Walkers Image3Mr. W: I would be very careful before jumping into anything with a coworker! It can really complicate things in your career, and often lead to more stress than pleasure! Having said that, I can still give you some tips on how to test the waters without making a big splash. Guys are pretty thick when it comes to catching signals from girls, and they won’t pick up on the little things. Next time you two are alone in the copying room, see how he responds to your eye contact. You can say a lot with your eyes without using any words, and men are visual creatures. Keep this going, and notice if things become more playful between you two.

The key is to make a deeper connection, and then see if there is something worth pursuing further.


Dear Mr. & Mrs.Walker,

My boyfriend of a year spends more time masturbating than having sex with me. Our sex is pretty vanilla, but I’m not sure how to begin adding more spice.

Question #3: Take the gentler, less ego-bruising approach.

TS Walkers Image2

Mrs. W: Nothing is tastier than adding more spice to your sex life!!

I have two suggestions for you:

1. Start small and within your comfort zone. Maybe test the waters with a pair of hand cuffs, a blindfold, or some rope… and get creative.
2. Go to an adult toy store with your partner. Take a look around and see what speaks to the two of you as a couple. Just remember to go in and   home with an open mind!

You also mentioned above that your boyfriend spends more time masturbating than having sex with you. I want you to think about that for a sec. There is nothing wrong with masturbating, even when you’re in a relationship; however, if the masturbation is coming before having sex with you (the real McCoy), then I think there may be an issue there.


TS Walkers Image3Mr. W: You are hopefully in a very manageable situation here! It is fairly common for guys to start to masturbate a little too much, especially if they lack confidence in the bedroom. Unfortunately, too much masturbating (especially with porn) can also lead to erectile dysfunction, which is a real confidence killer. A man’s sexual prowess must be approached with sensitivity, or else you may trigger a negative reaction. So, using a soft and sensual approach, try to ask him what he thinks about while he is masturbating. If he is watching porn, ask if you two can find one together. Hopefully he trusts you enough to be honest and open, and remember that any step here is one in the right direction. You might find that just talking about this stuff gets him hard. If so, try to lead things to the bedroom, and keep that dirty talk going. Talking during sex can activate your mind, and bring in new flavours that you didn’t expect. Talking about your fantasies with him, and watching videos together (if that is your thing) may help you two find the right doorway to a sexier lifestyle.


Dear Mr. & Mrs.Walker,

I love watching porn and I’ve always wanted to watch it with a partner. I think it’s hot! I’ve been seeing a guy for a few months now, and I want to suggest watching it together, but I’m afraid to scare him off. This question is more for Mr.Walker: Would a guy think it’s too aggressive or forward if I bring this up?

Question #4: Girls can enjoy porn too.

TS Walkers Image2Mrs. W: I know this question is intended more for my husband, but I thought I would add a little of my own advice. First of all, I think that it is great you love watching porn and I feel like most guys would feel the same way. Just don’t come off too strongly about it. You don’t want to intimidate the guy. Which brings me to my second point, breaking the ice in a gentle manner. You can take the easy way and just wait for the conversation of porn to naturally come up, then just squeeze in the question, “Would you ever be interested in watching a porno with me?”. Or you can take the lead. Next time you guys are hooking up at your place have the porno ready to go, once things get a little heated ask if he minds if you turn on a video.


TS Walkers Image3Mr. W: Unless you have found yourself with a conservative fellow, you are probably safe to bring up the idea of watching porn together. If you know that your guy is already into watching porn on his own, you could start the sharing by telling him about some video or pictures that you found hot. Maybe tell him that you left a couple of videos open on his computer of some things that you’d like to try together. If you can tell that he is feeling it, then odds are he will be pretty excited about watching it together.

This is a great way for the two of you to explore things that you want to try, or even just fantasize about.


Dear Mr. & Mrs.Walker,

I’ve always considered myself to be a straight woman, but recently, I’ve been having feelings for another woman. I’m not sure if it’s just curiosity, or if it’s something more, but I want to pursue these feeling. I’ve never pursued a woman before and am not sure on the correct approach. How should I go about this?

Question #5: Explore away.

TS Walkers Image2Mrs. W: You go girl! Pursue away, I say! The only way to know if the feelings are there to last is if you give if a fair try. Get out there, whether its via online dating, or going to a gay bar. Put yourself in the environment. Go on a date, see how it feels. If it feels good then you can step it up to the next level. Always stay in your comfort zone and be honest with the other person. Let them know its your first date with a girl, or the first time getting intimate with another female. I assume most people would be understanding.

Worse comes to worst, you find out that it’s not for you and you move on.


TS Walkers Image3Mr. W: It is great that you are exploring your sexuality to see if you have something more than curiosity. Is there anyone that you have in mind already? If you are getting the feeling from someone that she might be wanting more as well, then this might be the best place to start. So you don’t risk jeopardizing a friendship, you might want to ask more general questions about the topic, to see if she has ever considered it herself. Maybe you are looking to find someone totally new. If you are feeling adventurous, then you could try looking for some activities where you can meet like-minded women in your area, or even out of town if that is more comfortable.


If you’ve got your own questions for The Walkers, send them to: askthewalkers@thestrategy.ca

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