I have a very small penis. It is only about an inch long when it is not erect, and when I have a hard-on, it's only about two and a half inches. It's not very big around, either. My penis is so small that I need to sit down to piss. Otherwise, all I do is water my shoes.
Please don't tell me that size doesn't matter, the vagina is flexible, women care more about intimacy than they do about size, blah blah blah. I've heard all of that before, and it doesn't help. I got bullied about this in school so much that I had to get a doctor's note to use a private shower. I've been rejected by a long line of women. The kindest one said she had a headache; the meanest one just pointed and laughed, picked up her purse, and let herself out the door.
What can I do about this? I have investigated every quack method that seems to promise to make my penis longer. I have tried stretching it and had to stop before I did permanent nerve damage. Is there anything that isn't a rip-off scheme for making money off of desperate men? For example, can plastic surgery do anything?
I feel like I will never have the things that other guys my age take for granted. I will never find a woman who loves me. I will never be able to have children. This has affected every area of my life. I am sure I would be more ambitious and have a better-paying job if I wasn't so insecure about my body. There are days when I wonder if I would have been better off if I'd been born a woman, but the idea of having sex with a guy makes me nauseous, so I guess that's not an option.
You are kind of my last resort. Anything at all in your bag of tricks? Anything?
Biology has not been kind to you. I am not going to lie to you. You've got a major challenge to overcome. But you can do it. I've had sex with hundreds of women and men, and a series of committed, open relationships, and my penis is a hell of a lot smaller than yours. Of course, because I am a female-to-male transsexual, people expect slightly different things of me than they do of you. But I too have been rejected by women who won't consider sex with a man unless he's got a flesh-and-blood cock that is average size or better. Gay men are not the only ones who are size queens! It's ridiculous to say size doesn't matter. A big penis or toy will feel different than a smaller one. But sometimes bigger is not better—sometimes it's just painful and unwelcome.
I suggest a three-pronged strategy. The first step is to find a decent counselor and get evaluated for depression. See if it helps to have somebody to talk to about your lack of empowerment. If therapy doesn't work, a coach might be more useful. It's important to learn to be more assertive and to have a more optimistic view of the future. None of us really knows what will happen tomorrow; anticipating the worst only makes us miserable. You might as well expect that things will improve—and if you do the work to make your life better, your prophecy may turn out to be correct!
The second step is to stop trying to have sex with bitches. I hate to use sexist language, but just between us guys and a few politically incorrect dykes, I think it is safe to say that some women are rotten people. They are status-drive, they use sex as a weapon to humiliate men (or butches), and if they have a choice between doing something shitty or being kind, they will decide to do evil. In short, they are bitches. Although that is rather a slam on female doggies, who tend to be sweet and loving creatures.
You need to learn how to tell the difference between pretty girls who are jerks and attractive girls who have a heart. We all have insecurities about sex. We all have deficits to overcome. Someone who has a cooperative attitude about sex, who wants to find solutions to any problems that come up, and values vulnerability would be a much better fit for you. So if you've been looking for a date in stylish nightclubs or business conferences, switch venues. Go someplace where you can talk to a woman and get to know her before you decide whether to ask her out or not. Do some volunteer work. Get a hobby. Take some classes. Try a bunch of different things. Something will eventually click.
Your third step is to learn how to be a good lover. Okay, so you are not going to be a porn star style fuck. But that's only one sexual technique about of the hundreds of positions in the Kama Sutra. You can be good with your mouth, your hands, the rest of your body, and your imagination. Read up on sex techniques. Don't waste time with porn unless you want something for J/O enhancement. The oral sex in porn is crappy. Women want you to get your whole face in there. They don't want to be licked with your tongue stuck out like it was frozen to the water pump in January. Much as I am glad that porn now shows women getting cunnilingus, you need to know that each woman likes to be licked in a different way, and you just have to get her to talk to you and experiment until you find out what she likes. Commitment to her pleasure is what makes you a good lover.
If you have a partner who likes deep penetration, you can use your fingers or a toy. There are so many different types of dildos out there that there must be one who will make your sweetheart happy. I prefer the soft/firm feel of cyberskin and similar prostheses. The fact that you are a bio guy doesn't mean you can't use a dildo harness. I've made harnesses for a couple of men friends of mine who want to be able to fuck with a toy that was bigger than their natural-born equipment. Think of yourself as challenging the boundaries of gender. Or you can simply sit between her legs and hold it in your hand. A little fantasy, some lube, and stroking of her clit will combine to send her into sexual release. Maybe even more than one orgasm could be achieved. Unlike a cock, a dildo will stay hard as long as you need or want it to.
You don't need to find a dozen women to fill out your dance card. You only need to find one. And I believe there is somebody out there who will see your loving heart and your authentic sexuality, and believe that you were put on earth for her. So don't give up. For example, I have one woman friend who prefers small penises because she likes sucking cock, but she has a very sensitive gag reflex. She found a partner whose erect cock fits in her mouth perfectly, and both of them couldn't be more happy in bed. She prefers oral sex and mutual masturbation to intercourse, and so they have found a space of compatibility that may not be the stereotype of true love, but certainly looks and feels real and true for them.
Self-love is a good place to start. That's where you dig the well that fills up with water that you can offer to someone else who is thirsty for love. (I know I"m being corny, but love IS corny. So there, hipsters.)