This is the first of many Nude Awakening Advice Columns where I will tackle your questions of sex, love, dating, and all that in between from the perspective of a Naked Therapist. The inaugural inquiry involves questions of inadequacy, insecurity, and the always troublesome threesome!
Dear Sarah,
I am an adult male and currently I am having some insecurities concerning sex and intimacy. I am an adult male and I have a small cock. I am currently in a sexual relationship with someone and I don’t think I am pleasing her the way she wants to be pleased! She loves to suck on my dick and says that my cum is really ”sweet and delicious” and she loves it when I give it to her anally, but when we have intercourse frontwise she barely even makes a sound and it really bothers me. Lately she’s been wanting us to have a threesome with another guy. I know him and I know he has a big cock, and I think she wants him in the mix because I’m sure he can satisfy her the way I can’t. I honestly don’t know what to do. Should I take her up on her threesome request or just walk away? Please let me know. Thank you so much!
First off, it’s so great that you can identify the times and ways you’ve pleased your partner! When struggling with insecurities—especially sexual ones—it’s difficult to recognize how sexy you actually are! It speaks a lot about your character and your relationship that you’re able to recognize the many ways you HAVE PLEASED your woman.
Believe me, not every gal is willing to have anal sex, let alone enjoy it! And it sounds like your partner wishes there was an ice cream flavor inspired by your cum’s taste profile! I know a lot of men who would be jealous of your sex life 
But it’s hard to focus on these great qualities when you’re preoccupied with your perceived shortcomings. It’s even harder when you start to compare yourself to other men. Which brings us to your question…to threeway, or not to threeway?
Normally, I’m an advocate of a little adventure (and company!) in the bedroom, but only if it’s something you’re curious about. It sounds like in this case, however, you would only agree to the ménage a trois to please your partner. Which is honorable, of course, but in the long run could be destructive to your relationship.
Whether penis-size has anything to do with her motivation, your inherent insecurities (which are normal, and TOTALLY common, by the way) will make you interpret each action from the lens of inadequacy. While she very well might just want to add a bit of spice to your sex life, it’ll come across as her dissatisfaction or wandering eye. And how could that possibly help your relationship? This may be a pandora’s box best left unclosed.
That being said, I don’t think you should walk from the relationship. It sounds like your partner is supportive, and sexually attracted to you…don’t let yourself convince yourself otherwise! My biggest piece of advice to you is to open the communication pathways so you can stop guessing. Ask her why she doesn’t make noise when you do it from the front. Ask what appealed to her about a threesome. And work together to find adventurous alternatives that you would both enjoy. Consider toys and dildos for extra stimulation, or if it’s a stranger she was craving…try role-playing. Use your imagination for good instead of evil! Don’t conceive of all of the ways you may not please a woman…instead, conceive of all the ways you can!
Hope that helps
OMG THAT IS SO FREAKIN AWESOME THAT I’M THE INAUGURAL INQUIRY FOR YOUR NEW COLUMN!! Aww I really appreciate that you would do something so sweet for me (many many hugs!). If my dick was any smaller I’d be crying right now lol jk (smiles!). You truely are a sweet and caring person and from the bottom of my heart you mean so much to me right now. Thank you so much Sarah. Because I’m a man, I would expect people to think that I’m being such a sissy with my issues right now. And because of that its so hard to open up about the threesome and especially the small cock issue. So many people in this world are so judgemental, but they need to realize that a man is a human being before he’s even a man. I know that alot of times on my e-mails I’m very positive and fun hearted, but it also really hurts knowing (or thinking) that someone you care about so much and share your body with so much might (and the keyword is Might) is not satisfied sexually as they used to be. Reading and after reading your column lead me to really think about how I HAVE PLEASED her and all the moaning she makes as she sucks on my cock and as she tastes and swallows my cum (whew is it getting hot in here? lol). Lol I thought your ice cream flavor comment was so cute! I’m thinking vanilla with a touch of hazelnut and don’t hold the nuts (wink wink lol). She has told me before that she was happy about my small dick because it doesn’t hurt her when I’m giving it to her anally. Lol she said it ”fits in perfectly”. Reading your column makes me think about all the times we just hold each other after we have sex. Before reading your column I was so cinical about myself that I didn’t even realize the ways that I do please her, and even the ways she pleases me! Me and her 69 so good and my God can she make me scream when she fingers me! Wow you’ve opened my eyes to things that were staring at me in my face all along! While the whole frontal thing is still an issue for me, I think she hasn’t ”dumped” me sexually because of the OTHER ways I please her. The menage a trois issue is definately a serious one for me. You’re right Sarah, doing it out of honor only will definately destroy our relationship in the long run. Honestly, I’ve been scared to bring it up to her and tell her that I am very uncomfortable with it because I don’t want to look like a jerk. She’s already told me that they have talked about it. She wants him to suck my cock and eat my cum while she watches and masturbates. She also wants him to give it to her frontal as I give it to her anally at the same time. It is arousing to me I’ll admit but thats like a whole new thing for me. You’re right Sarah, I definately do need to communicate my feelings to her. Keeping all these feelings bottled up inside of me is not healthy for our relationship. She deserves better than that, we deserve better than that. I’m just so afraid I’m gonna make her mad. I guess I just need to be man enough to reap the rewards as well as accept the consequences. The role playing idea sounds really fun and kinky! I’m gonna ask her if she’d be into that. Maybe we’ll do a whole hot for teacher thang lol jk. She does have a vibrating dildo already that she has used on herself and on myself already, but I’m gonna see what other toys we can bring into the bedroom. I know Adam and Eve.com has some good stuff! Thank you so much Sarah. Your column has definately given me my self esteem back and the courage to confront my issue. I will communicate with her, and lol who knows, maybe she’ll be able to convince me to do the threesome. It does turn me on sometimes when I think about it. But I will definately do it only if it pleases us both equally. Again thank you so much for caring Sarah. You have such a warm heart and your column and advice has helped me so much. I consider you my friend already (hugs). I will definately let you know what happens. I’m so glad I had the courage to reach out to you. Thank you so much!