Advice: FWB Turned Sour

Dear J,
How do you be friends with someone whom is gay, that you had a sexual experience with, but found there was no sexual gratification in it for you, but you still love them like a brother? How do you stop them from being vindictive and mean? I'm a sensitive male, but I am straight. I was abused as a young kid and I have bad flashbacks. I have a lot of gay friends I'm comfortable with around me. But things are weird now with my best friend because of what happened. I do love him. I'm just not gay.
-Anonymous


Dear Sensitive Straighty,
As you can see sex and friendship doesn't always mix. It's never ever a good idea to go down that road with your friend unless you both have mutual feelings for one another or have some kind of NSA/FWB arrangement. Someone always ends up getting hurt and in this case it's the both of you.

The first thing you really need to do is talk to your best friend. I would avoid the phrasing "I didnt have any sexual gratification from our hook up." that is just gonna make your best friend feel like shit. Like a used up cum rag! Nothing can wreck someone's self esteem quicker. Also avoid the word "mistake" because in his eyes it probably didn't feel that way. You need to tell him you value your friendship with him and that you do love him. But you just want to stay friends and the sex shouldn't happen again. Even saying that will feel like daggers stabbing his heart. If he is being vindictive and mean that is because he is hurt. You hurt him by rejecting him. Gay guys can be mean if they are hurt and trust me we aren't afraid to hit below the belt! He may need time to get over it. So talk to him, apologize the best you can and give him some space. True friends can always work stuff out. Remember actions speak louder than words, so showing some type of remorseful gesture will help.

The second thing I want you to do is to think about why this happened in the first place? Were you confused about your own sexuality and needed to test it? Were you thinking that maybe a relationship with your best friend would work and then when it actually happened you realized for sure you're straight? You need to figure this out, so something like this doesn't happen again. My best friend Kevin would say, "most straight guys would fuck anything, a warm hole, is a warm hole!" But if you are truly sensitive like you stated then this probably isn't the case. So why did you hook up with your best friend? If you feel it may be because of the abuse you received as a child then perhaps you should seek professional help from a therapist. They can uncover those underlying issues and hopefully help you out. And if you still really aren't sure about your sexuality just remember the anus has 8 more working muscles and is 4 degrees warmer than the vagina... Just saying.

Make good decisions,
J


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Advice: Sexually Incompatible

Hello J,

I am 20 years old and My boyfriend is 24. I have been with my boyfriend now for over 3 years in a monogamous relationship. He is the first person that I have been with, but I am NOT his first. Lately (last year or more) I have been getting the urges to explore new avenues. The thing is, I love him very much, and I want to be with him. We are just not sexually compatible. I have tried to talk about it with him, but he doesn't want to lose me or share me. He tells me he doesn't want me to be shared with anyone. Sometimes I feel like I can't do anything without him along. I just need that space. I feel like I want to try new things with other people, and I don't want to cheat on him. I am not really sure what I should do. If I break it off with him, I feel like I will regret it later down the road. I also feel if I stay with him, I may cheat on him. What are your thoughts...

Thank you 


Dear Sexually Incompatible,

Congratulations on the 3 years together you guys made it passed the terrible two's. Relationships are hard! There's a lot of give and take. Both of you are so young. I think maybe the reason why you feel the need to spread your legs grrr I mean wings is because he is being too clingy. Your early 20's are suppose to be a time for you to explore and figure out what/who you are. This is the time where most guys "sow their oats." You need space to grow. Perhaps the reason he is clingy is from issues from a previous relationship. In that case there's really nothing you can do. It's his own inner demons. You should be able to have your own friends and own activities outside of the relationship though. (Well as long as it doesn't involve cheating of course.) It's healthy. You can't spend every minute with each other that would drive anyone nuts, no wonder yours aren't getting licked. Just remember no matter which friend or what activity you do, don't be shady about it. Always tell your boyfriend what you're doing or going. It will make him feel more secure. Remember to put yourself in his shoes. How would you feel if it was you?

Very few guys your age are in a committed relationships. Most go for the "Open Relationship." An open relationship is when you see other people purely for sex, but stay with your boyfriend for the emotional connection. I know a lot couples that engage in this and each have their own set of rules. Some only "play" together, others hook up with guys and never discuss it among each other and then some only hook up with people they both approve of. Ultimately most open relationships never last. I've seen couples get jealous because the trick was into one more so than the other. Plus, people change! Sex seems important now, (and it is important to a degree) but down the road when you're older you're going to crave that emotional connection more so than that penis in your ass. I don't think an open relationship would work in your case. You stated he doesn't want to share you with anyone and since being in this type relationship involves sharing bodily fluids with strangers it's not going to work.

Since you guys have been together for over 3 years, you should be able to talk openly about what you want sexually. Communication is the key. Since you feel you are sexually incompatible you need to tell him exactly what you want. Guys are clueless sometimes you need to spell everything out for them. If you have a fantasy, see if he would fulfill it for you and vice- versa. Maybe there's something he wants you to do for him. Most likely you aren't really sexually incompatible, It could be you're just stuck in a sex rut. When you're together for awhile, after awhile sex starts to feel like a chore. I suggest you try spicing it up alittle. “Whips and chains excite me!” Role playing could be a good idea in this case and it's the only way it will feel like having sex with someone else without actually cheating on your boyfriend. I personally like men in uniform. So talk about your fantasies with each other and try to rekindle that fire.

Cheating is never a good idea ever. If he ever finds out he will never be able to trust you again and what's a relationship without trust? Remember talking to each other is always the best thing. If you're truly unhappy though perhaps the best thing you can do is break up. I sincerely hope it doesn't come to that. I hope you're the donut hole to his banana. Good luck.

Make good decisions,
J

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Advice: Reformed Whore

Dear J,

I would call myself a "Reformed Whore." When I was younger I used to sleep with everyone. My numbers are probably up in the 100's and I had a new so called "boyfriend" every couple of weeks. I'm now alittle older and have met the man I want forever! We are in a committed monogamous relationship. We saw previews for that movie "What's Your Number?" and he asked me what mine was. I was reluctant to tell him and I changed the subject. I am ashamed of my promiscuous past! My boyfriend has asked me a couple times now "what my number is" and each time I come up with excuses not to say. Because he doesn't have a "colorful" past, I fear I will lose him if he finds out mine! What should I do?

Dear Reformed Whore,

You can't run from this topic or the past, but the past is the past! What you did when you where younger actually shaped who you are now. You learned and grew from your past relationships or tricks. Sowing your wild oats prepared you for this relationship now.

My advice is to be completely honest with your boyfriend. Chances are is if you keep averting the subject he will become suspicious. Being shady about certain things could make him question, “What else is he hiding from me." and you don't want that. I know it's hard to tell the one you love that you once let every Oompa Loompa in your chocolate factory. BUT trust me it's best he hear it from you that you rode every Sit~N~Spin. You don't want some jealous angry mo you once slept with telling him all your dirty secrets.

Kevin and I actually had this "What's your number" discussion a couple weeks ago. When I asked him (I was just being curious.) he said, “Well what do you count?” I first said only anal and he easy remembered how many and it was a small number.  Then I said, “What if we counted oral?” His response was he would have to "try" to figure it out by year! And asked me if straight guys counted! Kevin says he can turn people on to anything! Sarah Michelle Gellar, Ashley Tisdale, his dick! So when you talk to your boyfriend you have to make sure you know clearly what he would count as sex. Who knows maybe you weren't as big of a whore as you thought you were! Maybe you just left your mouth open and their penises just fell in. Who's to say?

Remember honestly is the best policy. He loves you for you as you are now! Plus all that sex helped hone your toe curling technique and who doesn't love that? Oh and remember a nice dinner and flowers helps to smooth things over.

Good luck! And always make good decisions,
J

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Advice: Bottomed Out

Dear J,
I don't have a lot of gay sex experience and neither does my boyfriend. He has been with one other person and I haven't been with anyone else. We mostly have oral sex but would like to try anal. He wants to top and I don't have an issue with that, but every time I try to bottom it really hurts. I can only handle it for a couple minutes and then I just give up. Can you give me any tips?


Dear Bottomed Out,
First let me start off by saying that I am not doctor so the advice I'm going to give you is only from my own experience. Second, please, please, please practice safe sex. Make sure your boyfriend always wears a condom and you always use safe sex practices.

Anal sex can be very satisfying for both parties. Pleasure can be derived from the nerve endings around the anus and the anus itself. It is an extremely intimate act that should bring you and your boyfriend closer together on so many levels. There are a few things you can try to help ease yourself into it so to speak.
The first thing I want you to do is some "self exploration" on your own aka I want you to explore your own butt before your boyfriend does.

-Find a nice place you can relax. A warm bath is nice or shower.
-Rub your fingers on the outside of your anus. If you're in a bath or shower make the area wet. If you are on "dry land" try some lube.
-Slowly insert a finger. Take a couple breaks, relax, and probe the area again. Each time you go back in things will be more relaxed and it should be easier.
-Next grip and release your sphincter muscles. (it's like clenching your buttocks) This is actually a form of male Kegel exercises. This will help you have control and will also feel good for your partner. The sphincter muscles can also expand and contract on their own when something is in there so it's good to know how this happens.
-Move your finger back and forth. Once you are comfortable with one, try two fingers, then try three. Try masturbating while you're doing this if you like. Remember to stay relaxed.
-Next move one finger around inside until you find your prostate. The prostate gland is a muscular gland encircling the urethra in the male that produces much of the seminal fluid. It is located just under the shaft of your penis. You will know when you find it because the sensation is very unique. This is also a very healthy practice to do. It stimulates blood flow and helps prevent cancer. I suggest you explore your butt every time you get a bath or shower until you are used to it. It's also a good activity to do daily. It will help you stay more relaxed during sex and it's healthy for you.

When you feel ready to try "the real thing" in your butt, have your partner do the above activities to "loosen you up." To avoid pain the key is patience. A lot of guys rush into it and start pounding away that's why it's painful! Before you actually have the penis inserted there should be a lot of fingering, tongue play, and perhaps toys. (Dildo, butt plug etc.) Be sure to use lots of lube. (There's special lube for anal sex that will help numb the area as well.) Anal fingering is an effective way of stimulating the prostate gland and can bring the receiver to orgasm without the penis being inserted. Make this a fun activity before you try his penis.

When it's time to insert the penis make sure he is a wearing a condom and use lots of water-based/condom friendly lube. Your partner should rub his penis all around the outside of your anus. Occasionally adding some pressure but not completely entering. It's like "cock teasing!" This actually drives me wild because of the anticipation. Next, slip the tip of the penis in. This is where the term "Just the tip!" came from. Have him hold there for a bit till you're relaxed, then have him go in further. It is ok to stop a few times, relax and try again. You may need to add more lube. Communication is the key. He should know by your facial expressions if he is hurting you, but speak up anyways.

Your booty can accommodate just about any size penis unless he is hung like an elephant. It is just a matter of relaxing the muscles. Have him go inside you for a bit and then pull out for a break. Each time you do this the sphincter will be more relaxed. You may feel some pain but it should start to subside to pleasure and then he'll be able to stay in longer and start to move back and forth and in and out.

Once you are completely relaxed and get the hang of it, you'll start to experience a lot of pleasure. The constant probing and massaging of the prostate and nerve endings of your anus could make you produce an anal orgasm with or without ejaculating. You could experience multiple anal orgasms and even ejaculate from your penis without your partner even touching it. Your partner may actually feel your orgasm. He should be able to feel the rapid, rhythmic contractions of the anal sphincter, and the prostate while he is inside you. All of these things have happened to me and they are amazing. Don't be discouraged if they don't happen for you right away. It takes patience and relaxation. Good things are cumming! See gay sex is sooooo much better!

Good luck with your probing activities, be safe and remember...

Make good decisions,
J

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Advice: Crushed!

Dear J,
I recently discovered that I'm falling in love with my best friend. I don't know if I should tell him or not. I have the worlds biggest crush on him. We have been friends for about two years now. Part of me wants to tell him and part of me is scared it will ruin our friendship. What should I do?
~ Anonymously



Dear Crushed,
Crushes can be hard! I'm sure if they were easy they would be called something else. I've struggled with this issue a few times, most recently with my friend Andy. If you look at my earlier posts you'll see my struggles. It all started with my post: It's Just A Little Crush, Right???

You have two options; First, tell your crush how you feel, how the sun sets in his eyes and how badly you wanna ride his fun stick. Second, keep it all to yourself and hope the feelings go away, before you are reduced to making small cuts on your leg to feel better. Personally I've learned that telling someone you have feelings for is better than keeping it to yourself.

Three things could happen when you tell the truth; First, he could feel the same way actually. It's hard to tell people how you and he could be waiting for you to say it. You'll live happily ever after, buy a couple cats and call it a day. Second, he let's you down the easiest way he knows how. He may say something like "I love you, but only in a friend way." or "Our friendship is so important to me I don't want to ruin it." I know it's still like daggers to the heart, but he does care obviously. Third, He gets so freaked out he cuts all ties with you and you never talk again. Honestly the latter one rarely happens! And if it does he never was really your friend anyways and obviously has issues deeper than yours.

In my experience, my declaration of love came out in a heated argument. (Again something I don't recommend. Tell him before that happens. See the post: Resolutions.) Everything in the end though did work out. It turns out although he didn't love me the same way, he still very much loved me as a friend and I am important. He also then understood why I was so moody and acted the way I did to certain things. I actually felt like our relationship as friends grew a bit closer. Everything worked out for the best.

So what has been the outcome? We are still friends. Still talk every week, but unfortunately I don't get to hang out with him as often as I like. He currently is dating a wonderful guy. (I do approve!) I'll admit it gets me down a little, but in the end I do care about him and his happiness. And of course you know it would damage my car to much if I ran over his boyfriend.

My advice to you: Tell him how you feel. You may not get the answer you want, but sometimes just saying it and getting it out there helps. This could help you move on from your crush. If he is truly a friend, he won't go anywhere and will be flattered. It may take sometime to get over the whole thing and you may even need to take a little time and distance yourself. This is normal and your crush will understand. Hopefully in the end it will bring your friendship closer together.
Make good decisions,
J


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