Personal FAQs

Here are answers to commonly asked questions I receive, in no particular order:

Biggest and smallest penises I have encountered

The biggest I’ve ever had was 9.5 inches and the smallest was probably 3-4 inches; both were difficult in different ways. The big one became very painful very quickly, especially with the extra friction from a condom, and I couldn’t manage many traditional positions. The smallest belonged to a guy who was a terrible lover; he didn’t care about my pleasure at all, and thought he was bigger than he actually was. I never corrected him but I was mentally laughing at his ego. Suffice to say that Small Boy only had one chance and never heard from me again.

My preferred penis size

I generally prefer anywhere from 6.5 inches to 8.5 inches at the absolute most. But I won’t turn down a potential lover if they fall outside that range because vaginal sex is only one part of sexual activities. It doesn’t take a well-endowed man to bring most women, myself included, immense pleasure.

Best and worst lovers I’ve had

My worst lover was Small Boy, as mentioned above, but once again not because he was small. His selfishness and ego, and total disinterest in making me feel good, are why he was awful. Had he actually cared about my pleasure even a little and he might have redeemed himself.

My best lover was a brief but intense affair. He was very passionate about pleasing me, not only for my sake, but because he genuinely got off on making me orgasm. It was almost like he could orgasm just from making me climax. He would beg to be allowed to please me – although not in a submissive way – because he loved doing it so much. He loved the scent, taste, and sight of women and femininity. His enthusiasm and passion were extremely arousing to me and made me feel relaxed and comfortable around him. He legitimately worshiped my body; he helped me feel sexy and cherished.

Best and worst sexual experiences

My best sex was the first time with my best lover, as described above. I was surprised because usually the first time with someone new involves a lot more fumbling and sloppiness than actual pleasure. But that first time we were together, when I experienced that level of passion, was something I’ll never forget.

I’ve had plenty of awful sex before, but there’s one specific instance that comes to mind as being among the worst. I was with my high school boyfriend and we were going at it. Right when I was about to orgasm, I heard one of my cats barfing up a hairball in the room. It completely ruined the moment and we couldn’t recover from the interruption that night. We laughed about it but I remember feeling extremely frustrated.

Turn ons, turn offs, and dealbreakers

My particular turn ons include blue eyes, being taller than me, and intelligence. If someone can talk philosophy or politics with me, I’ll be way more interested than some chiseled idiot. Also compassion, kindness, and an open mind are really big. Sure there are plenty of physical traits I love (like a cute butt!), but a personality can make or break attraction for me. As an example, I once worked with a guy who I thought was very, very sexy. I loved staring at him. Then one day he spewed vitriolic, misogynist nonsense from his mouth-hole and the attraction was instantly gone. It never came back.

I have several major turn offs: selfishness, egotism, willful ignorance, rudeness, and right-wing blabbermouths (see: Donald Trump). Again the basic physical appearance is much less important than personality, integrity, and strength of character. Also I really hate when men wear socks during sex.

I have only a few select dealbreakers: when someone doesn’t speak English fluently (that becomes a communication issue); guys who don’t trim their toenails; not liking animals (in a platonic way – I just don’t trust someone who can’t connect with animals on some level); people who judge others for stupid reasons; and people who are pushy. Anyone trying to impose their values on me will get an earful and/or blocked; I don’t judge you, so you don’t get to judge me. End of story.

I also feel inclined to post this disclaimer: EVERY WOMAN IS DIFFERENT. What I find attractive or repulsive is totally irrelevant. You need to find someone who YOU find attractive, and who reciprocates that sentiment.

Best and worst ways to meet someone

I am in no way an expert on this subject. I have met people in many different ways: online, through mutual friends or friends of family members, at common activities (school, work, etc), and randomly. What I can do is give a breakdown of how many people I’ve met through different activities as follows:

meetinglovers

In a future post, I will review various dating apps and websites based on my personal experiences. Online dating seems to be the way to go these days for many reasons; it’s certainly an arena that’s expanding rapidly.

Happy playing!

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Personal Sexperience & Life Lessons

My first time wasn’t very glamorous. I was 15 years old and had been dating my boyfriend (we’ll call him Justin) for about a month. He was the first one to ever get past first base – in fact we rocketed from first base to third without much preamble. I liked him, I trusted him, but I didn’t love him. We had fun and we cared about each other, but I didn’t love him.

One day we were getting hot and heavy and our clothes ended up strewn all over the floor. He was hard, I was wet, and we were grinding against each other. Then somehow it just ended up inside me (I should mention here that I accidentally broke my hymen when I was 8 due to a gymnastics mishap). We both looked at each other, wide-eyed and unsure, before lust overcame us both and we just went with it.

I didn’t particularly enjoy it – I was caught up in how weird the sensation felt. Once Justin was spent inside me (we didn’t use a condom), we kind of lay there together not speaking. It wasn’t awkward or uncomfortable, we just had no idea what to say. We hadn’t discussed sex, nor had we planned for anything to happen. It was accidental sex.

I’d had opportunities before but they never seemed like ideal situations. I wasn’t someone who expected roses and candles for my first time, but I trusted my instincts. I wasn’t mad, sad, or upset in any way that my first time wasn’t special. I felt different afterward. It took me a good two days to really process what had happened, and get used to the idea of no longer being a virgin.

Now, with 20 years of hindsight, I have much more perspective on things.

I don’t regret dating Justin, nor do I regret that we were intimate. I do wish I had waited to have actual sex, because 6 months later I could have shared that gift with my first real love. Justin and I will always have that connection of being each other’s first. Although we remained friends on and off for another ten years, we are no longer in contact; I can’t help but wish I’d given that gift to someone special. It is an incredibly personal thing to give someone your virginity.

I’m also incredibly grateful that the lack of condom didn’t lead to pregnancy. I was VERY lucky in that regard.

Some people say giving yourself at any time is special, whether it’s the first or not. Some hold sex as a sacred thing to be shared only when truly in love. I’ve even met someone who couldn’t physically be with someone unless there were strong feelings between them. I personally don’t subscribe to that philosophy.

The best sex you can have is with someone you love, that much I won’t debate. Being able to fully trust someone and let go in a supportive environment makes everything that much more potent. Sex is at its finest when you know your partner is genuinely interested in pleasing you.

But you can still have a lot of fun without an emotional connection. It won’t be the same level of deep satisfaction – it may get you off, but it won’t fulfill you to the core. And sometimes that’s okay! I think having mediocre or less satisfying sex is good, in a way, because it helps us to appreciate the good stuff even more by comparison. And being able to fulfill your particularly lewd/kinky fantasies is immensely pleasurable. Most of us have a sexual bucketlist, and not all items can be fulfilled while in a relationship. Experimenting is great, expanding your horizons can be fun, and experience helps us fine tune our technique as we learn from others. Sex is awesome.

In the 20 years since Justin, I have had a full spectrum of amazing and horrifying experiences. I have learned a lot and tried many things, pushed my limits and pursued challenges. And I have gained a lot of perspective about sex, relationships, and everything in between.

Here is a list of conclusions I’ve drawn from my experiences:

  • Unless you know with absolute certainty that your relationship is monogamous without cheating, always use a condom. ALWAYS. STIs are common and very annoying. Most of them are easily treated but they’re a huge hassle. It’s a good idea to keep condoms with you at all times in case you need one.
  • NO MEANS NO. Never let someone talk you into something that makes you uncomfortable. If they try, get up and walk away. There are plenty of other people who will be respectful of your limits.
  • The best lovers are those who want to please you more than they want to be pleased. Someone who genuinely enjoys giving pleasure, and even gets off on doing it, is usually great at what they do. ALWAYS reciprocate the attention they give you.
  • Sex is only good when there’s communication. Don’t be afraid to say if something hurts, or if they’re doing it wrong. Talk about your needs, desires, and hot spots. Everyone is different and most people want to learn how to please you. If they’re unreceptive, walk away.
  • Similarly, let your partner know when they’re doing well. Moans and groans go a long way.
  • TRUST YOUR INSTINCTS. If a situation/person/activity makes you hesitate, then get out of it. Your subconscious brain can pick up on subtle cues that the conscious brain often ignores or minimizes. Your gut always knows best.
  • NEVER openly criticize someone’s body. You’re lucky you get to see it at all. If you think there’s something to be concerned about for health reasons, be tactful and respectful in mentioning it.
  • Try not to compare different partners. Everyone is unique and no two experiences, even with the same person, will be exactly alike. Comparisons don’t serve any purpose except to make us critical and judgemental.
  • Penis size matters a lot less than most people think. I’d rather be with a man who’s smaller but talented than with some hung idiot.
  • As long as they’re legal, safe, and consensual, explore your fetishes! Don’t feel guilty for having them – no one has to know but you and the person you play with.
  • The number of partners someone has had does not reflect who they are or their level of skill. Someone can have 100 partners under their belt and still be a terrible lover. Also, just because someone has had lots of partners, it doesn’t mean they don’t have standards. Numbers don’t really mean a whole lot in the bigger picture.
  • The brain is the largest erogenous zone. Example: I find a hearty philosophical debate more of a turn-on than dick pics. Stimulate the mind, then stimulate the body.
  • There are many different types of sex. Each has an appropriate time and place.
  • NEVER CHEAT ON YOUR PARTNER. They will always find out one way or another. The satisfaction you get from a night of passion isn’t worth the heartache you cause someone you care about. If you’re tempted to stray, sit down and figure out why that is. Cheating is often reflective of a deeper issue in the relationship, which isn’t necessarily about sex.
  • It’s a fact that you will be rejected far more than you will succeed; learn to shake it off.

Bros Give Advice for First Timers

I asked a bunch of men, friends and otherwise, to share with me the most important piece of information they wish they had known before having sex for the first time. Here’s what they said:

-The vaginal opening is a lot closer to the anus than you think. Most guys think it’s right up front, like their dicks, but that isn’t the case

-Your expectations probably won’t be met the first time – it’s rarely “magical”

-Try to be in a relationship because it’s easier to say if you’re uncomfortable with something

-If you don’t stimulate her before deep penetration, you’re going to have a bad time

-Foreplay and making out makes sex feel better and last longer – don’t just “stick it in”

-Even if your first time is with someone you’re close to (mine was with a gf at the time) the fact that no one knows what they’re doing just makes it an awkward experience. You can visualize and plan it all you want but there’s no way to imagine that

-Foreplay can matter for the guys too, and girls CAN climax so much that it becomes painful

-It’s never perfect – don’t put pressure on yourself, just have fun and enjoy the ride

-The definition of sex is broader than just penetration, so don’t put so much pressure on that one act

-Try to communicate more with your partners from the start, take everything slow, ask them what they like and be open to criticism

-Take the time to make it meaningful and don’t rush

-Don’t rush it. Make sure you’re ready. It’s OK not to be “in love” but just make sure it’s really what you want

-It really does matter who it’s with and not just something to get over and done with

-Girls are sometimes more worried about themselves than what they think of the guy

-I wish I’d known how to get a girl to have sex with me

-Wear a condom