Q I was with my wife for nearly 20 years before she passed away. A while has passed, and now I have this new girlfriend. She is great and all and does more stuff for me than what my wife would do in the bedroom. However my wife and I had a great sexual relationship. She would do all the stuff I asked but only on special occasions – not like this new girlfriend who will do them on command. But my wife came all the time. She was even a squirter. She would always orgasm in any position – from clitoral stimulation, vaginal sex and sometimes from anal sex as well.
My new girlfriend, who is 11 years younger, doesn’t do that and I’m beginning to feel inadequate. I’m an average-sized guy and was able to satisfy my wife all the time, but with this girl, the only way she gets stimulation is if I hold her legs together in missionary or doggy – oh, and also if I pound the hell out of her. I can see she’s liking it, but she never seems to orgasm. I’ve given her plenty of clitoral orgasms with my fingers, and she enjoys when I use my mouth, but my tongue can’t create the same pressure as my fingers.
She’s also different from my wife in that after she has an orgasm, her clit gets extremely ticklish instead of sensitive and she starts laughing, which sort of kills the mood. It is frustrating when you go from a woman who is getting pleasure from your penis in every position to a woman who just says it’s ‘okay’ if she doesn’t have her legs together. For me, seeing and hearing her enjoy the sex is what turns me on.
This girl is addicted to me because she says she’s never had someone make her feel the way I do. I love the fact that she does all this stuff on command, but I feel like I’m doing something wrong. And all of the sudden, me being average, which satisfied my wife perfectly, has me wondering if the only way she’ll orgasm is with a dude who is really big. She did mention to me that she’s had a guy larger than me and it felt the same way. So I’m wondering whether Kegel exercises could get her to feel me better. She has had a child but had never heard of Kegels when I mentioned them to her.
I’ve read one of your posts that suggested the lube-on-the-belly thing with her on top. Out of the question for me. Got a bit of a beer belly. Can’t rub her clit in doggy: she’s got a bit of a booty on her, and if I lean over to reach for it, I lose the ability to thrust her well, being that I’m not 10 inches.
With all the girls I’ve been with when I was a teenager up until I met my wife (seven in total), this is the first time I’ve come across this problem and felt very inadequate about my size. And it’s hell going from 20 years of having a woman who I made squirt with my penis inside her, to a woman who can barely feel it unless I squeeze her legs together. I know every woman is different, but she is unique. She’s the first woman to be this uninhibited but also the first to make me feel like I’m not up to par. - Beer Belly Bart
A It is impossible for a normal woman to compete with a squirter who comes in every position. That voodoo pussy your wife took with her to the grave is a rare thing. If you keep comparing every woman to her, you will remain frustrated. I still think you should lie on your back, on the floor (naturally on a blanket) and let her ride you, so she can come like that, belly or not. The belly may even help make her come as her clit rubs against it. Try it. What’s the worst that can happen? Most women NEED clit stimulation to come, so please do not be surprised that she can’t come in the positions you mentioned that avoid clit contact. It’s SEX for fuck’s sake, not boot camp. Every partner is different. This woman is “addicted” to you, loves you and does what you want on command. You’re the envy of most men at this point, yet you’re still whining. Asking her to Kegel is like her asking you to take Viagra. If she is open-minded and has a good sense of humor, buy her the Kegelmaster (Google it). Either work with what she has or find another partner. Not sure why you are already settling down with another woman when you have only had seven in bed so far. Perhaps it is time to enjoy playing the field a bit, as this one you have now literally doesn’t seem to fit.
Q My boyfriend and I just started going out and we both love to do it doggy style, but whenever we try, he can’t enter me, almost like he doesn’t reach. He’s not small – he’s an average size, like six inches – but I have a crazy hourglass figure (aka: a big butt). Is this what’s causing the problem? And how can we fix it? - Berth Butt
A You are telling me your ass is literally too big to mount, which I find very difficult to visualize (although I’m sitting here trying). How about you sit him on a stool and squat on him instead? That way you will get all of his whopping “six inches”. If you really insist on doggy style, try it standing up (put one foot on a step). Where there’s a will, there’s a way.