What’s With Picky Orgasms?

By Kendra Holliday | August 27, 2014 at 5:00 am

Dear Kendra,

I’m 18, in college, and Female-to-Male transgendered. I have had three male sexual partners in the last eight months or so. Of the three, TWO have claimed that a handjob or blowjob WILL NOT DO, and absolutely NOTHING but penetration will get them off, and in the case of one of the guys, even that wasn’t enough, and he had to turn to his own hand.

However, on your site and elsewhere, I see tales of guys that can get off with ease using various methods beyond penetration.

So what gives? These guys are 20 and 21, respectively, shouldn’t they be rarin’ to go? What on earth is going on that penetration is the only thing that seems to get them off?

My reply:

It’s unusual that you ran into two men in a row who require penetration to get off. I think it’s a fluke. They probably both used penetration in their early masturbation routine and have become dependent on that way.

I’ve been with a couple guys recently who needed to take over and finish with their own hand. It didn’t bother me, as one was new and the other often finishes that way, but can just as easily get off other ways.

I think everyone should experiment solo and with partners to expand their menu if possible, but hey, at least they know what works! I have a few girlfriends who can ONLY get off via clit stimulation with a vibrator. Some of their partners are bothered by that, but they aren’t, and that’s what matters. They know their body and what they like.

What about you all – can you only get off one way? Can you only get off solo but not with a partner? Does it bother you if your partner can only get off one way? Do you think it’s important to train yourself to get off in many different ways? Have you ever been surprised at an atypical orgasm? Do you find a difference in how you respond when engaging in casual sex vs long-term partner sex?

What’s your favorite way to get off? Mine is lying back, relaxing, and having my pussy worshiped with an experienced tongue.

PS: Have you seen those videos where a woman gets off using a door? Never would’ve thought of that!

The #1 Way to Please Your Man: How to Give an Extraordinary Blowjob

By Kendra Holliday | August 26, 2014 at 5:15 am

I blow, therefore I am Goddess.

Oral sex is the #1 way to send your man into ecstasy. It feels incredible and few men can resist the opportunity for their cock to be worshipped and loved. Best of all, his deep gratitude is bound to pay off considerably later on when he eagerly returns the favor. Here is a breakdown on how to give a great blowjob, TBK style.

Great conversation topic

Before you put your mouth to good use, ask him what he likes so you know what to lay on thick and what to avoid. Does he like his balls licked? Teeth? Lots of suction? Strong head stimulation? Slow or fast? You can have this conversation over dinner or while sitting on the couch watching TV, but be prepared to stop what you are doing so you can practice. OR employ tech foreplay and do it over IM or text during the day so you can prime his pump for when you see each other that evening.

Tease him

Take the tease trail. For example, start by kissing your most fortunate test subject, then slowly head south, kissing and licking his nipples, chest, belly, thighs, balls, shaft, then finally make your way to his cock head.

Once you’re there, open your damn mouth. I keep hearing from both men and women about these women with small mouths who can’t get the job done. Despite what you might think, my mouth isn’t that big, and I can stuff something substantial in it. Though I can’t fit a soda can in it like I saw one woman do. That’s impressive. If you have TMJ/jaw issues, do the best you can and supplement with edible lube/hands.


Vanilla Night

By Kendra Holliday | August 17, 2014 at 9:51 am

Pretty please?

Pretty please?

You know how some people have a kinky night, where they bring out the fuzzy handcuffs and the whip cream in order to spice things up?

Well, every once in awhile – like, every three or four months – Matthew and I have a Vanilla Night.

We’re so used to fucking around with our kinky friends and enjoying extraordinary encounters, that we enjoy the challenge of switching gears and trying our damndest to be normal.

We even give ourselves normal names on these nights. Instead of Matthew and Kendra, we’re “Randall and Michelle.”

We’re monogamous, married eleven years, and he is pussy whipped and I’m a bitch.

Instead of me washing the dishes while he steps outside for a drink and a smoke, he cooks dinner AND does the dishes. I don’t say please or thank you.

Instead of talking about a porn clip or the upcoming pirate orgy, we discuss what we should get our friends Roger and Stacie for their big Chicago wedding, and if we should attend the baseball game while we’re in town. I tell him I’d rather go shopping and that he better not have more than two beers because he has to watch his carbs.


Local Couple Tries Grapefruit Trick!

By Kendra Holliday | August 12, 2014 at 11:57 am

Have you heard of the grapefruit trick?

I read this review from a woman who tried it and was intrigued. I love grapefruit, and my man loves blowjobs!

I asked him if he wanted to try it and he flat out said NO.

“Why not??” I exclaimed.

“I have a Tenga and a Fleshlight. Plus, I don’t like mixing food and sex.”

Fair enough. So much for getting my daily dose of Vitamin C (as in Cum!)

My friends tried it, though! Here is their experience:

Grapefruit trick!

Grapefruit trick!

“I watched with anticipation as she cut the grapefruit. I’ve had no experience with Fleshlights or any other sort of masturbatory vaginas, so I thought,  ‘This could be interesting!’

I lay back on the floor of my kitchen, towel beneath me as she stripped down to arouse me (and keep the citrus off her dress). She began by teasing me with her mouth, my penis coming to attention the flood the pleasure rushing to my head. My eyes were closed because the instructions called for the recipient to be blindfolded because the procedure was supposed to be a surprise.

Suddenly in the midst of the warmup came the main attraction. She slipped the fleshy citrus donut over my cock and squeezed it while continuing her ministrations. There were moments where I felt as though I were inside a Vagina Dentata, a soft, pocket purse of flesh with a hungry mouth at the other end.

And then there were other moments I was a dude with a piece of fruit on his dick.

I was thinking about Led Zeppelin’s “Lemon Song“: “Squeeze my lemon ’til the juice runs down my leg’, as it was a messy affair.

She sucked and licked while squeezing the grapefruit around me. “Slurp! Slush! Squish!”  My eyes rolled back in my head. Back and forth my mind went, between Toothed Pussy and Fruit Cock, the pleasure rising from the base of my balls, rising then holding, not going anywhere.

I had peaked and the  awareness of the cool sticky juice running my leg took over, and I asked her to stop. I didn’t want her to waste her time. I wasn’t going to cum this way. My lust had only taken me so far, what I really wanted was to be buried inside her listening to her moans of pleasure, something I couldn’t do covered in citric acid.

For hygienic purposes , I jumped in the shower and rinsed off, then met her in the bedroom where the games began in earnest! Orgasms for everyone!

Overall, I would have say I had more fun being smeared with Nutella. It’s messy, but the attention I get is greater than grapefruit. There’s nothing a grapefruit can compare to when someone is excellently working the shaft during a first rate blow job.

I would give it a 4 out of 10 as orgasmic tool. Worth trying, but sort of ‘Meh’ in the end.”

Tools and Tips for Women Seeking Orgasms

By Kendra Holliday | August 11, 2014 at 5:34 pm

Are you a woman who hasn’t had an orgasm in a few years? How about ever?

Want to expand your orgasmic repertoire?

Here you go. Read this post by Joan Price. Then, watch this.

Betty Dodson has been a pioneer of female orgasm for over 40 years. She’s 85 now, and while she tends to rub some people the wrong way, I have to admit she is on to something!

She’s known for her book Sex for One, as well as being a champion for the vulva and clitoris.

A few years ago, she had an advice column in Bust magazine, and I was dismayed at some of her replies. She seemed very dismissive of women masturbating outside the box and seemed to be on her way out, introducing her sidekick, Carlin Ross.

But then earlier this year, she caught my attention by pissing off a bunch of politically correct people at CatalystCon East. She joked about grabbing someone’s ass and fucking a dog or something, and people were outraged.

So that got me interested in her again, and then I heard her piece on the RISK! podcast and that was great. And then I read Jenny Block’s account of a group masturbation workshop hosted by Betty. Mark my words – we’re totally going to do something like that in St. Louis in the near future!

So I’m back to being a Betty fan (just like how Dan Savage won me over again by being bold and owning up to past foibles, while still sticking to his guns.)

My friend who is in her 40’s and newly dating just discovered the Hitachi Magic Wand. She CROWED about how she doesn’t NEED a man now! The wand helps her take the physical edge off when her hormones are raging, and allows her to take her time finding her next partner, one who is well-suited for her.

So, yeah. Click around this blog post and discover some new tools and tips. I love learning something sexy and new everyday!

And spreading the good word!

Getting to Know Each Other

By Kendra Holliday | August 10, 2014 at 8:16 pm



Matthew sends me a challenge via email:

“You are to seduce me soon… Entice me like you would someone you are fucking for the first time…Again. Take Control. Show me you want it and you won’t stop until you get it.”

It’s a challenge all right! It’s difficult to make the first move on someone who is so dominant in your life. Someone you know so well in one way, but not others. Someone you’ve known for years and take the comfort and familiarity for granted.

I’m up for it.

“I’m ‘that guy’ from okcupid,” he tells me. OH I get it. We’re pretending like it’s our first date.

The day of our date, I get a message on okcupid from him telling me that he’s looking forward to our date, and that he’ll pick me up at 6:30. I message him back in kind.

We have dinner at a sushi restaurant and have a fucking blast. The waitress Ling loves us. Sake and beer flows, we eat Hot Mama rolls, and get to know each other.

Throughout the evening, we ask each other questions as if we don’t already know the answers, and we actually learn new things. For all of you in long term relationships, you should totally try this!


Male Sex Workers for Women

By Kendra Holliday | August 10, 2014 at 8:02 pm

A perverted gentleman.

A perfect gentleman.

The other day I received this message:


I was wondering if you could offer advise on how to get started or if its even plausible to do what you do but as a male instead of a female?”

First of all, I offer consultations for this type of thing. You can check out my website for more info.

Second, the answer is yes, it’s possible to be a male sex worker for women. You can apply to be a Cowboy 4 Angels, a service that offers straight male escorts for women.

From the website: “Cowboys need to be very attractive, dedicated to a top level of fitness, presentable, well-groomed, stylish, charming and desirable. Cowboys need to be confident but not arrogant, yet savvy. All need to be emotionally mature, stable and possess a genuine respect for women.”

Read this interesting article inspired by the television show “Hung” on male sex workers representing all kinds of niche markets – black men serving as “bulls” for parties, men hired for cuckolding fantasies, strippers and more. If you’re going to be a sex worker, figure out what your specialty is – working with people with disabilities? G-spot orgasms? Tantra? Massage?

Here’s an article featuring a man in Australia, where prostitution is legal. He seems to have a handle on what women want – to be pampered, worshiped, made to feel special, and oral. Lots of oral sex.

If you want to be a successful male sex worker, in addition to looks, brains, and personality, you need to be compassionate, confident, sexy, mature, intuitive, a great listener, and able to read body language. The focus should be on the woman – not your penis. You also need to be able to see the beauty in your clients, no matter how old, fat, or annoying she is. You need to be good with condoms.

What other qualities would be important for a male sex worker who is seeking female clientele?


Mating in Captivity

By Kendra Holliday | August 9, 2014 at 8:30 am

Mating in Captivity, by Esther Perel

Mating in Captivity, by Esther Perel

Mating in Captivity is a great resource for anyone who is unhappy in their traditional, monogamous marriage.

The author and therapist Esther Perel notes that her husband is also a therapist, but he works with people who are refugees and have been tortured and have PTSD. She says her husband deals with pain, and she deals with pleasure. I say she’s also dealing with pain, just on a different level. And yes, pain and pleasure are intimately connected. Both make us feel ALIVE.

How do we get more pleasure in our lives, and less pain? Ultimately, we are in control of our lives, and can make choices that will lead us to a happier, healthier place. These choices can be difficult, and take a lot of work. They take courage and strength.

I was counseling a couple recently who have been married for over 40 years. Their relationship is spectacularly dysfunctional. I gave them real advice on how to change things (as opposed to a pep talk), and it fell on deaf, stubborn ears. Neither of them want to make the first move. They don’t want to leave their comfort zone, even though it has pot holes and bear traps. So frustrating.

Esther very patiently takes an entire book to break down what we all want – we want EVERYTHING. We want adventure, security, passion, love, independence, to be appreciated and desired, comfort, happiness… and guess what?

It’s really difficult balancing all of those things, especially if you are counting on one person to fulfill all of your physical and emotional needs. Most people cannot have everything. And if it is your goal to have everything, it’s really challenging finding the right balance.

For instance, Esther gave some couples some pretty hardcore advice. Going beyond the usual tips of scheduling dates on a regular basis and cute relationship exercises, she suggested one couple get divorced, but still live together. She advised another couple to live in separate homes.

You can wallow in the known and complain about it and let resentment build, or you can take a risk and make real changes. Sometimes happiness is handed to us, but more often than not, it takes hard work and courage to obtain.


Henna on Heavenly Bodies

By Kendra Holliday | August 5, 2014 at 6:01 am

I’m FINALLY posting a follow up to this henna post a while back. My sister inspired me! (Scroll down to see what I mean!)

Here is some amazing henna artwork by Jeanjoel from a couple years ago. I love having milky pale skin and a blank canvas for artists to work on…

Henna drying

Henna drying

It’s so relaxing to lie there and be still, feeling the paintbrush tickle.



Don’t you love my little willow tree pubic hair in this shot?


Cuffed and Stuffed

By Kendra Holliday | August 3, 2014 at 8:34 pm

I had another wild-n-crazy roleplay date with my friends Capn Marrrk and Bianca. They always do such a good job of creating an elaborate scenario and are so clever with costumes and props! For example, there was the time we pretended to be two sisters disciplined by a military instructor…

This time, I was playing the prisoner, Bianca was playing “Mama” the police officer, and Capn was the mean Prison Warden.

They kicked it off with a letter that announced I was up for a parole hearing:

Parole hearing notice

Parole hearing notice

I showed up with my orange prison costume on hand so I could change when I got there. Truth be told, I had a terrible day and was stressed and overwhelmed. I didn’t feel like an elaborate roleplay scene. I felt like vegging on the couch and whining and being coddled.

But when I got there, I discovered they were already dressed up and in character! She was wearing a tight, sexy blue police uniform, and he was wearing a brown suit and police sunglasses. Both had their arms crossed and looked STERN. They meant business!

Right away they addressed me as Prisoner #23049 and escorted me upstairs to change. OK, here we go!

As soon as I was in my jumpsuit, they cuffed me and led me to the chair for interrogation.



The Warden asked me all kinds of probing questions and grilled me. He made me state why I should be allowed early release, my plans on the outside, etc.

He informed me that if I wanted to get out of prison, I had to do whatever they say, including being their sex slave! They both were very serious and weren’t going to let me off easy.


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