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If it's a missionary style interaction then it's too much either grinding a cushion or banging into a head board.
Hell, that's half the fun of you, I can pick you up with little effort. That said, just holding you up for 10 minutes can become awkward. On the other hand, backing you into a wall or you wrapping your legs around me well can make it far less awkward. I wouldn't call it challenging, you get used to it. The nice parts of the height difference balance out with the less nice parts really the only thing I've ever found annoying is that my walking pace is your running pace.
For example, hugging you is great, I can wrap my arms around you and pull you into my chest, since you're a full head shorter. I have to bend my knees to hug her properly, and the wedding plhotographer made her stand on two phonebooks: D, but apart from that it's no big deal. While joking around, wrestling, whatever, with my ex I always told her that if she was going to continue being a jerk I'd hide her foot stool that she got from my mom who bought it so my little cousins could reach the sink in the bathroom at my mom's place.
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Bending down isn't uncomfortable, it can be nice to pick up a short girl, you can stand on a step or something to boost yourself up or just crawl in his lap if you're sitting down. My wife is 5'11" and I'm 6'4", and we do the same thing I did when I dated girls who were 4'11": She jumps into my arms, wraps her legs around my waist, and we're face to face. With my wife it's just fun; with past girls it was a necessity. But it was always pretty easy.
No, it isn't painful. I actually like it, it makes me want to protect my little lady and she loves the feeling being protected.
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To this point I haven't had the situation where a girl wanted that from me but I guess I would just do it. My impression is that especially smaller girls like to be lifted by a strong man: You can either grab his t shirt where his throat is, I don't know the word for that and pull him down OR which I like more bring your knee up to his hip and guide his hand to your butt. I don't know a single male friend who would understand this as something different than "lift me up! I love smaller girls. I like picking them up or sitting them on my lap to make out. It's no trouble at all.
I'm 6'2'' if that's relevant. I don't mind picking up the girl, but you don't need to "ask" for it. Just stand on the tip of your toes, wrap your arms around the guy's neck, and lean against him. He'll get the message if he isn't completely stupid. It does put a strain on my back, as I have to bend so far for a full contact hug or kiss. But on the other side, their necks do hurt from having to look so far up.
But we also have fun with it, finding different height stairs to change the geometry, and generally trying anything to make it enjoyable. I'm fine with picking up girls to make out with them, but i would rather it happen organically rather than be asked to do it. The biggest problem I have is when my SO does something to break the mood, such as making a comment "out of character" or basically that is not directly relevant to the current activity.
Realize while we are tall, it isn't always fun and games for us. I have plenty of scars and dents in my head from cabinet doors and other objects most people can avoid easily. We don't all play or enjoy basketball. We want to be loved and to love regardless of any physical attributes. As a side note, Heels!
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I'm 6'6" and have had three girlfriends; 5'3", 5'4", and 5'6". No its not painful at all or uncomfortable. I have to bend down for plenty of other stuff that isn't made to my height so its not some weird foreign action or anyhting. I would love it. I love holding girls while I make out with them. It's easier because I don't have to bend down, we're now at eye level, and because they generally seem to find it really hot which heats up the mood.
Short girl dating really tall guy ~ Restricted Growth Association UK
Honestly it's not challenging or a burden at all. It's just standing that has to be adjusted. When I sit or lay down with a shorter girl we're eye level. I just prefer shorter girls. I have no idea why, I just always have, I guess I like the pettitness. So me adjusting to it is normal, honestly I think it would feel more weird for me to date a tall girl and not have to bend down.
The only thing I've gotten consistently from gf's is I walk to fast because my stride is so much bigger than theirs, so overtime I've had to learn to walk slower but thats about it. I'm 6'2, and the majority of the girls I've slept with or dated were about a foot shorter than me. Kissing was no issue, and in my experience, both they and I loved picking them up. My current girlfriend is petite enough that i can almost effortlessly lift and toss her around, which is awesome. So for me, if a girl wants to be picked up, all she has to do is either her best impression of a face hugger or just ask.
I find it really hot.
18 Men Admit Why They Love Dating Short Girls
I'm 4'11" and my husband is 6'3". It works because we make it work. I've never seen our height as a challenge or an issue, except shower sex, because dammit I'm just too short and he's too tall to make it work. To answer your questions, yes my husband has to bend down to kiss me. He's never said anything about it. Or sometimes we'll kiss while he's sitting No, he's never picked me up to kiss. Though I did stand on a chair when we got married so I could smash cake in his face. He does pick me up for hugs though, or to pop my back.
I love doing this. I used to carry her to bed all the time. Asking does not kill the mood, if I didn't get the hint.
The first time we kissed, I was sitting on a stool and she was standing. Make out sessions were usually sitting or laying down, so height really didn't matter. Sometimes I would pick her up and set her on the counter-top Depends on where we are. Outside a bar is sort of strange, try to find a bench or something to sit on in public. At home, especially in the bedroom, by all means climb into my arms.
I know it sounds silly, but if you are walking down a set of stairs or something, linger back a step or two, make him stop below you and then plant one on him. If a guy has this problem he's a weak sap. I'm a tall guy and have dated plenty of shorter girls. If I'm going in for a quick kiss, it's no big deal.