Tuffy Luv Has Conniptions

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Dear Tuffy Luv,

The last two years have been a whirlwind for me. I was really overweight pretty much all throughout high school and was really shy/awkward towards anyone who I didn’t know very well. A year after I graduated high school, I decided to start losing weight and since then have lost nearly sixty pounds. I still have a little weight to lose, but this new body of mine has definitely caused me to feel more comfortable with myself, and the male attention has increased drastically. I didn’t date in high school because I felt so bad about how I looked, and only until this year did I start going on dates. Since then, I have dabbled in oral sex with a few different men I knew casually but I never get off from receiving it. Actually, it has never felt good receiving, but I still continue to do it in hopes of that changing. I never went all the way with any of these guys, partly because I am not still not 100% okay with how I look yet and I would silently freak out and back off. I am turning 20 in August and did not want to be a virgin when my teen years came to an end.

So, after not being able to go through it with any of the men I had gone down on, I decided to take action and find a random guy I would never have to see again on Craigslist. Well, I found the right man, we talked for about a week, and we met up, hung out and had sex. That’s where the next part, and my problem, comes in. It didn’t hurt at all, but it didn’t feel good either. I could feel him but there was no pleasure. I saw him again a few days later and nothing, even though I’m highly attracted to him not just physically but I felt mentally as well from what I did know about him. I even suggested he take off the condom the second time we were together thinking maybe that was the problem, but nothing! That was nearly six weeks ago, and I have since slept with two other guys who have approached me and it is the same thing. I am attracted to them and I like going down on them, but I have yet to receive any pleasure when it comes to receiving oral and intercourse. I feel hopeless. I was not expecting fireworks or anything, but no pleasure from any of these encounters is leaving me frustrated and insecure. Is there something wrong with me? I finally have had sex and it is such a major let down.

Can’t Enjoy Sex

P.S. I forgot to mention that I have had orgasms before, plenty actually, with the help of a vibrator. I started using one more than a year ago and was (obviously) still a virgin at the time. I know that I may have to take a break from it since I am probably used to the strong vibrations to get me off, and that could be a part of the problem, but I still don’t know why I can’t at least feel some sort of pleasure from oral and/or intercourse.

Dear Can’t Enjoy Sex,


Seriously, I just about had a heart attack reading your stupid, foolish letter. Gurgling sounds rose in my throat. Or perhaps that was the vomit.

Look. You can’t just go around meeting strangers on the internet to have sex with. And you CERTAINLY can’t be having sex with random strangers and taking off the condom. You also should not be having unprotected oral sex. Okay? I’m serious here. You march your tushy to your OB/GYN (or to Planned Parenthood) RIGHT NOW and get tested. You can get all kinds of nasties this way.

DO NOT HAVE UNPROTECTED SEX!!!!!!!! You are opening yourself up to disease, and you are opening future partners up to disease too. I swear to Gaga. CONDOMS ALWAYS!!!

And, for real, picking up random strangers to have sex with is really, really foolish. You don’t know these guys. You could be raped, or killed. It is really, really dangerous. Please don’t do it. Herpes is almost the BEST case scenerio.

Okay, but let’s deal with your actual question now, which is neither stupid nor foolish. You are worried about not being able feel pleasure during sex. And, girl, you deserve to be feeling pleasure during sex. Pre-babies, that’s the whole point.

There’s probably nothing wrong with you. It usually takes several gos for sex to start feeling good. And in terms of oral–well, a lot of guys suck at oral (no pun intended). You just haven’t found someone who knows how to make you, the sexual person YOU, feel good.

And that’s really probably at the root of all this. Girl, one-night stands are fine (IF YOU USE PROTECTION). But for someone to know you and what feels good to you, and even what turns you on, you’d be much better off finding someone you connect with on a more personal and intimate level. It doesn’t have to be the guy you’re gonna marry. But a guy that you’d like to keep seeing–well, that might really help. That’s the guy who will be willing to find out what sex stuff works for YOU. Those are the kind of guys you should be sleeping with.

Of course, that said, if you continue to find that sex is uncomfortable or just never ever good at all, it couldn’t hurt to get checked out by a gynecologist, just to make sure everything is running smoothly. Especially since you WILL be going there anyway to get checked for STDs.

More importantly, you gotta ask yourself–why are you being so reckless with your body? You are literally putting yourself in harm’s way by being with random guys and having unprotected oral and intercourse. I suspect it’s because, as you yourself said, you’re still feeling bad about your body. But you worked so hard to lose all that weight! Don’t squander it on some random guys who may leave you hurt or diseased. Save that good body for the guys who are worth it. And, more importantly, respect yourself and not just your body but your heart and mind.

Seriously, please be more careful with yourself. Aunt Tuffy’s over here having conniptions.

Hearts & Skulls,
Tuffy Luv

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