The Naked Advice

Dating, Sex, And Relationship Advice with Liz LaPoint

I’m Confused wrote: “Hi Liz, I am a crossdresser and have a fantasy about giving a guy a blow job while in a dress. I consider myself straight but this fantasy is overtaking my mind. What should I do?”

Liz says: This is a pretty common fantasy for straight men who enjoy being sexually submissive, although I’m not sure how often it’s actually played out. There are a lot of things that can be hot in fantasy but in real life would make us cringe. So what you “should do” depends a ton on your level of experience and comfort.

For some hetero men with this fantasy (whether or not they crossdress) they’re aroused by being in the submissive (female) role, to the point that even servicing another man is part of the fantasy. Many will allow that fantasy to remain a fantasy, and others will experiment (with varying results).

But there’s also the possibility you’re not totally straight or cisgendered. So what?😉

male model wearing dress

Pantyboy wrote: “Hi Liz, I’ve watched some of your videos on Youtube and I think you’re great. I hope you can help me with my issue and questions. I’ll start off with a little story. 2 years ago I got a gift card to Macy’s and decided to explore a little bit with women’s panties. I bought myself some Maidenform boy shorts (yeah I know I got out of my comfort zone haha) and I really liked them once I tried them. They made me feel sexy and even though they were for women, they fit my physique really well. As you can imagine I became increasingly curious as to what the other styles felt like. One by one I tried them and I liked them with exception of Victoria’s Secret cheekies (they didn’t accommodate my package).

Now I have an entire drawer full of women’s undies that I enjoy. I do have some questions though. Is it okay for men to wear women’s underwear? What do women think about it? How should I handle changing in the gym locker room? How do I approach a female romantic partner about this?

Liz please help me and shed some light on this topic. I really do enjoy wearing panties!!”

Liz says: This is fascinating to me because I’m curious what exactly it is about wearing our underwear that you enjoy. Is it the texture/sensation of the material they’re made out of? Is it that it feels sexy to wear something under your typical male attire that goes against gender norms? Is it about submission and humiliation?

I will answer your questions in the order you asked them.

  1. Yes, it’s okay. You’re not breaking any laws, hurting anyone, and what you choose to wear is your own damn business.
  2. What “women” think about it will depend on the woman. Chicks who lean more submissive and expect men to conform to the macho image of manliness will probably be turned off, and women who lean dominant and are more sexually free-spirited will probably find it hot.
  3. My first suggestion is to simply avoid wearing panties on the days you know you’ll be hitting the gym. But if that kills the panty party for you, change in a stall?
  4. If I were dating a dude secretly into this, I would want him to just tell me about it when he feels ready to. It’s probably wise to wait until you know there’s something strong between you, when you’ve been dating a few months or something. This isn’t something that you incorporate into the bedroom (yet?) so since it doesn’t really involve her participation, it’s not something I would encourage coming out with right away (but also isn’t something I encourage hiding forever, either). It’s really about when you want to share it with her.

Happy panty-wearing!😉

“Ben” wrote: “Hi Liz, I’ve got a few questions and hopefully you can help me out with them:)

1. Ballbusting: I’m into ballbusting but only videos of people doing it. I’ve always wanted to do it with my girlfriend but I’m scared it will hurt too much and also scared that when I ask her she will be freaked out by it, so any input on that would help a lot.

2. Panty Sniffing: When my girlfriend stays over she normally leaves her dirty clothes here when she goes out, so I always masturbate to her underwear. Is this normal??”

Liz says:

1. You should be scared it will hurt too much! That’s a natural concern, as it’s healthy to want to protect your family jewels. So why can’t you continue enjoying the videos while not participating? Not every sexual fantasy needs to be experienced (nor should every sexual fantasy be experienced!) and it seems to me your hesitancy is a good reason not to have your nuts kicked. But if your fear ever subsides and you happen to be with a woman in touch with her dominant side, then perhaps it would be something to try.

2. Yes, it’s normal to be aroused by your girlfriend’s natural aromas.

Keep on keepin’ on😉

Stomach Cramps

 

A.B. wrote: “I am at a loss when it comes to my boyfriend and I. I don’t even know where to begin. For being a relationship that has only been together for a little over a year we have had our fair share of struggles and disagreements. The one thing I can say is there has been nothing normal about our relationship. We have been through a lot since day one. Since day one my boyfriend has had to be my rock cuz I lost my aunt, plus we both had school, and then he went out of state for 4 months for his police academy. From my point of view the problem is that I am just not feeling like he is not as serious in our relationship as I am, and that he just doesn’t seem to understand that the little things matter.

We have been talking about this for a few days now and then I get this today: “I’m honestly not as happy as when we first dated. It seems like everyday brings a new challenge and then we fight. We fight a lot. So much that even your family jokes saying ‘they fight like a married couple.’ That’s not good. As far as a future goes, if I were to go from right now where we are currently at, I don’t see a future. I feel like I’m just not fully committed like you said. Idk what is wrong with me. I’ve just been in a funk and I feel terrible because you deserve so much better than me. I literally feel like such a piece of shit. You deserve to be treated like the queen you are. I feel like I can’t meet the expectations you want. I do love you.” –that’s his view point.

I don’t know where to even go with all this…I don’t know how to fix it. I try to take little steps forward in our relationship and he seems to just push us back. I really hope you can help and can give me some good advice. I am truly caught between a rock and a hard place cuz I know I’m gonna break my heart in losing him and I know he truly cares for me and loves me and is just stubborn.

Liz says: All you need to know is in these words your boyfriend wrote: “I don’t see a future”.

When you’re with the wrong person for you, or one of you is not ready to be in a committed relationship, it’s a constant struggle. You’re two puzzle pieces that don’t fit, but you want to “make it work” so you try and try but really, it gets to a point when you both realize you’re just not meant to fit together. You realize that instead of forcing these two pieces together, you could be spending that time finding the piece that fits you.

Sometimes, one of you figures it out before the other one does. I hate to say it, but it appears that your boyfriend is the one to figure this out already. He’s telling you he can’t (or won’t) meet your expectations, that he’s not fully committed, and he’s not going to be the one who “treats you like the queen you are”.

It’s not that two compatible people never fight, but the fighting isn’t usually over fundamental differences in personality, life goals, or values. I was in a relationship with a man for 3 years once, and we fought constantly. At the time, in my naivete, I thought, ‘Well, all couples fight.’ I finally figured out that we were simply incompatible and that it wasn’t healthy to fight that often.

When you meet a puzzle piece who fits you, someone with whom you share values, interests, goals, energy levels, sexuality, backgrounds, and personality traits, you’ll feel more relaxed and free to be yourself. You’ll look back on all the time with exes that you spent trying to “make it work” and realize what was missing. When I met my husband, it was like ‘Finally!’ We felt right together almost instantly, and it’s 6 years later and we still feel right.

The little things do matter, but he will naturally be inspired to do the little things when he’s mature enough to be in a relationship and he’s with the right woman for him. You don’t want to be with someone who needs to be nudged into showing his feelings with romantic gestures, you want someone who’s so blown away by how wonderful you are that he’s inspired by love to show them!

Trust me, don’t ever settle for someone you have to talk into:

  1. showing you affection
  2. claiming you as a girlfriend or boyfriend
  3. living together
  4. marrying you
  5. staying faithful to you
  6. treating you respectfully and lovingly

When the right guy comes along, he’ll be jumping out of his boots to do the things on that list!

puzzle pieces

“Matt” wrote: “I just found your channel. After looking over a few of your video titles it sounds like a pretty interesting channel. I’m looking forward to watching your videos.

So I have a question for you: every female now owns a pair of yoga pants, right? Sure, when they first came out they were a turn on for me. I mean what guy wouldn’t get some sort of turn on by them?

I don’t know if I’ve become immune to them after seeing them on everyone everywhere or if it’s just me being less of a perv but they are actually becoming annoying to see in public now.

I’ve been wanting to ask a female this for a little while now and figured after seeing your channel I thought you would be the perfect person to ask…

I don’t know if you own a pair or several pairs of yoga pants but from your point of view, if you’re wearing a pair of these “pants” in public and you catch a guy staring at your ass or legs do you A. feel flattered to have a guy stare or sneak a peak at you or B. do you think he’s an absolute perv?”

Liz says: It’s perfectly natural to look at attractive people and admire their style and physical features, but some guys get the message that glancing at someone’s assets makes them a “perv”. There’s nothing perverted about admiring from afar someone’s sexy arm tats, or chiseled biceps, or perfect bum in yoga pants.

But like with anything else, context matters. Were you:

  1. Admiring women in yoga pants through binoculars across the street from a yoga studio?
  2. Not looking away when she caught you staring at her ass?
  3. Following the ladies around, to continue ogling them while they shop/walk?
  4. Snapping pics of their bums without their consent for your private jerk-off collection?
  5. Hitting on them by saying “Hey girl, you look mighty sexy in those yoga pants” and then calling them bitches when they rejected your advances?
  6. “Bumping” into them to cop a feel?
  7. Calling them sluts and telling them they’re “sinners” for wearing yoga pants?

Simply noticing an attractive person and being turned on by their appearance doesn’t make you a pervert, it makes you horny (and horny isn’t synonymous with perversion), but anything from the above list would certainly make you a creep.

I think most women (myself included) would find it flattering to see someone admiring them from afar, as long as none of the above was accompanying it!

VS yoga pants

C.R. wrote: “I just discovered your blog/YouTube today and really love your work. I have a bit of a pressing issue and could use your advice.

I am a sissy. I love the idea of wearing adorable outfits – French maid, Alice in Wonderland – and also have an affinity for diapers and abdl accessories. I am completely straight and love being a man. I just wish (and fantasize about) from time to time, I could be a cute little princess.

My partner knows. We have experimented but it’s not something she enjoys so I have kept my activities to myself out of respect. We do enjoy some D/s play for what it’s worth.

Before meeting her (and for a while after we started dating) I would binge and purge my closet … Acquire 2 or 3 outfits (usually second hand) wear them a few times, then throw them away in shame. For the last five years I have not owned any sissy items.

Recently, my partner suggested I buy a dress of my own to wear in private. I have found a perfect dress from a sissy clothes maker on etsy … It is within my price range and a sissy dream (satin with lace and a petticoat) … But I can’t bring myself to buy it. I just keep re checking my measurements and debating whether to get the purple, pink or blue dress.

I really don’t know why I am so nervous to order it.

Any ideas on where this hesitancy might be coming from? Do you think it’s a mistake to buy the dress? Is this my subconscious trying to tell me something or am I just overwhelmed that my fantasy is within my grasp?

Any thoughts are appreciated!

P.s. If you do think I should get it … Any votes on whether I should go pink, purple or blue?”

Liz says: I suspect your hesitancy is from a combination of shame and guilt. Shame because you’ve internalized our culture’s message of what masculinity is supposed to be and guilt because you enjoy something your partner doesn’t and you’re concerned she’ll want a “real man” instead of you one day.

We are constantly re-defining what femininity and masculinity means, and when you look at other cultures or our own throughout history you’ll note that society often changes its tune with what it deems appropriate clothing for men and women. I don’t know too many people who would say a man in a kilt isn’t masculine. There was a time men wore tights and wigs, too. But you do this in private anyway, so why feel shame over something that hurts no one and doesn’t affect other facets of your life negatively?

It sounds to me that your partner knows what makes you happy, is accepting of it even though she doesn’t care to participate anymore, and doesn’t want you to resent her and feel deprived just because she doesn’t join you in your sissy activities. Plus, she still enjoys D/s with you! In other words, it’s hardly the behavior of someone who’s hoping you’ll change or wants to leave you. This might not even be something you worry about but I thought I’d point this out just in case.

As to what color dress you should get, it depends on your hair color and skin tone! Go with pink if you’re tan and have dark hair, purple or blue if you’re paler.😉

MenInKilts7

B.F. wrote:Ran across your videos and figured I should write you for advice. My wife and I tried cuckolding starting back in 2006. She had started working and mentioned to me that she had been hit on and to my surprise, I liked it. She mentioned she liked the attention. Long story short, she has been with three lovers since 2006. The play wasn’t very often. We even did chastity play. I was really into this lifestyle, but it turns out that she isn’t into it any longer. I’m not exactly certain why, or if she ever liked it….she says she did it for fun at first and then to entertain me/keep me near the end. She feared I wouldn’t want to stay in the relationship if she didn’t do it. So, here we are, years later and I am so fascinated by cuckolding, chastity, strapon, etc….and she now has no interest with any of it. It even brought up the topic of us potentially going different ways. Sigh. While I love her, here I am wondering about life being short, and what should I pursue???? Am I settling if I stay in this current relationship. Would there be a better fit for me who embraced these things?

Liz says: This is tough because on one hand, she will resent you (if she doesn’t already) for wanting her to participate in sexual activities she has no interest in continuing, and on the other hand you will resent her (if you don’t already) for preventing a lifestyle you enjoy that requires her participation. She probably feels like you should just appreciate that she gave it the old college try (hell, 3 lovers over 10 years is more than many other wives would’ve done!), and you probably feel like you’re being deprived of the kind of fun you really want to have (like you said, life is short!).

Incompatibility in bedroom desires is different from incompatible hobbies. If your wife loves mountain climbing and you don’t, she can simply climb with her friends. If you love mountain biking and she doesn’t, you can go biking with your friends while she climbs.

But when Person A in a relationship enjoys sexual activities that Person B doesn’t, we still expect Person A to stay loyal and not enjoy said activities with anyone else, for understandable reasons. No one will get pregnant or catch an STI going mountain biking with someone other than their spouse (although the risk of falling in love with someone else is present). This makes differing sexual desires a special issue in committed relationships.

If you two truly love each other and can still see a future together, then discuss things further with this understanding: you two get to decide what kind of marriage you want, not friends, not parents, not society. If you both decide to compromise by having an open marriage, for example, it’s no one else’s business. You probably already know this, but it’s possible that shame or concern about what others might think if they found out could be playing a role in your wife’s desire to stop.

But if she makes it clear she never wants to participate in cuckolding you again in any way, her wishes deserve to be respected. Try to put yourself in her shoes: how would you feel if you tried something that doesn’t turn you on (or even repulses you) just to make your wife happy but she felt like your quitting was depriving her?

I hope you two can work this out. Good luck, cuck😉

 

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