Welcome to Ask Harper!
Relationships can be confusing and terrifying, and sometimes you need an outside perspective. When you need kinky relationship advice, who do you turn to? Asking for help in your relationships can be the most terrifying thing you’ve ever done, because it goes directly against every expectation and assumption we have in our culture and society about how a relationship is meant to look. So kudos to those brave folks who do seek out relationship advice and counseling! Go you, you pillar of strength and paragon of kinky, dirty, awesome virtue!
Our first correspondent asked:
“Harper, how do I convince my wife that I really do want to wear her panties while she goes out to fuck other men? She thinks I’m kidding.” –Pantie Wearing Cuckold.
Well, Pantie Wearing Cuckold, sometimes the direct approach works. If your wife or partner is a pretty laid back person, and it looks like they are from your question, try grabbing a pair of panties and letting them see the effect the underthings have on you. Laying on the bed, turned on and horny, trapped in panties while describing how hot it’d be for you if she was getting ready to go out to see a lover… Well, it’s hard to think it’s a joke when you’re busy making a wet spot in your panties right in front of her! If your wife is the more serious sort, take her out for a cup of coffee, and tell her straight up that you mean it when you say you’d love for her to cuckold you like that. Honesty is often the best possible tactic to use.
Up next, we have Nervous Butt Slut, who asked:
“I really want to be able to take a huge dildo in my ass, but I’m kinda afraid it’ll leave me stretched out forever! Help!”
Don’t worry! As long as you don’t go from zero to humongous and rip your sphincter, you’ll be fine. Start small, and work your way up to something really big. Use plenty of lube appropriate for your dildos and anal toys, and size up carefully, slowly, and don’t rush into the deep end (or big end) of the pool too fast. Your ass will shrink back down, provided you don’t leap to the biggest thing ever too fast, and that you allow time between big dick fucking for your ass to relax and recover from what you just did to it. It takes a surprising amount of ass play to permanently stretch an anus.
Got a question for Harper?
The Kinky Relationship Advice column is open! Feel free to email me with your questions, and let me know I can use your questions on the blog! No question too silly, no question too weird, I’ll answer ~anything~!
Dear Miss Harper
i was out the other night and drank too much. Ended up at some guys place (i’m straight) and he virtually seduced me – stripped me and got me to put panties on. It was quite exciting. He then treated me like a chick and took control. i told him i’d never done it before and wasn’t like that but he just did it. He made me do oral then had me. He was quite big and it felt funny so deep inside me – and he had a nice body. And i must admit i did cum from it all. He did it again the next morning.
My question sorry – does this make me gay ? He wants to see me again. i have a girlfriend.
robb
Hey Ms Harper!
What a helpful post! You’re right, many come to us for advice because , hey asking your BF about ass pleasure advice is just not something people often do. I’d much rather they ask us vs “learning from porn” Ug……… ??
I know your advice is going to help many!
See you around the Empire!
Hi Ms Harper-I’ve spoke with Ms Erika about my feminization. I’m not gay nor into guys just like wearing bras,panties,breast forms,yoga pants,leggings,blouses,makeup,lipstick,dresses. It fits and feels so much better then my guy clothes. I have friend that has taken pictures of me with her phone as I wanted her to do this and she did. She told me not to worry about her husband and not care or worry what others this as this is who I am and become and to accept this. She’s right. I have girls who I play tennis with and I’ve thought about coming out to them. I’m thinking wearing my women’s yoga pants/panties/bra underneath along with perfumes mixed with lotions and unisex top with ankle boots once summer is over. Hopefully they will notice and say something to me as I would be honest and upfront telling them this is more comfortable then my guy clothes. If they are great friends they should be ok and accept this. I do have hots for both but are 25 & 31. 17 & 23 years younger then me 🙁 what are your thoughts about this?
Also with friend who took pictures of me with her phone. I want her to give me feminine arched eyebrows but she’s looking out for me as she doesn’t want my family to know. I respect her opinion but Feminine arched eyebrows are so hot!! I could tell her if anyone noticed she wanted to do experiment on me.
Ms. Harper- LOVE the advice given here. I agree, some things people just can’t talk about to their more vanilla friends, but coming to you or another LDW Mistress is a great place to get open-minded, honest advice and opinions. I’m so glad you have started this column up, you always have such great wisdom!