The Scarlet Letters: The Accidental Virgin and the Sexting Newbie
Tuesday, June 30, 2015
The Sexting Newbie
Dear Scarlets,
I’ve been with my boyfriend for three years and he’s just started traveling a lot more for his new job. Most months he’s gone for about a week now. So far, I kind of like it. The sex we have when he comes home is better than we’ve had in a while, for sure.
I don’t know if he has an Osmond fetish, but the last time he was in Utah, we were chatting via text and he started to get a little frisky. He asked me what I was wearing and whether I was touching myself.
I was wearing a stained sweatshirt and I definitely wasn’t.
He obviously wants to start sexting, and it makes me really nervous. I’m as dirty as the next girl, but I’ve never had much of an imagination when it comes to writing. How do you keep things interesting each time? Do you have to come up with different scenarios? He seems to fantasize about me with other men so I could use that, but it seems like there’s only so many times that’ll work. Are there sexting guidelines written somewhere? I need help.
Signed,
ISO a Sexting Cyrano
Dear ISOSC,
First off, you're in a good position to start sexting. You never want to sext with someone you've just met or are in a new relationship with. You don’t know how those are going to end and therefore whether you're going to see your boobs (or stained sweatshirt) on a revenge porn site. Three years is a safe bet, so we say, sext on!
Here are a few do's and don'ts:
DO your research. If you feel like your imagination won't cut the mustard, try looking up erotic stories that fall into his fantasy realm. Google "cuckold erotica." There's even a Tumblr!
DON'T do anything that makes you uncomfortable. Saying or doing something in the bedroom that you later regret is bad, but at least there's not a permanent digital record of it. When you're not in the throes of passion, looking back on sexts will probably always be a little embarrassing, but it should never, EVER make you feel used or humiliated. Unless you're into that.
DO indulge your own fantasies. This shouldn't just be about what he wants. One great thing about this medium is that often it's a lot easier to say what you want when you're not face-to-face. Tell him what you want him to do to you, and hopefully that'll transfer to the real world when you're together.
DON’T leave evidence of your playtime on an unlocked phone. If you must keep the conversation for later use, that’s fine, just make sure your phone is locked up TIGHT. (Ever have a friend who looks at the picture you show him on your phone, then starts SWIPING? You don’t want that slo-mo “Noooooooooo!” moment.) There are apps you can use to lock up pictures and conversations—we highly recommend using them. But the only thing that will truly protect you is deleting everything like “The Wolf” in Pulp Fiction. BE THE CLEANER.
DO find your boobs' best light. Any pictures you send will likely be... "used" by him for a while, and you don't want to send anything you don't want him looking at repeatedly.
DON'T send pictures of your face if you can avoid it. We know from “Fappergate” (the cloud hacking scandal that revealed way too much of stars like Jennifer Lawrence) that nothing is safe and sometimes things go to the cloud even when we don't specifically send them there. A picture of your ass on the internet is only recognizable to those who you've already shown it to by choice, and even then you can totally deny it unless you have a Michigan-shaped birthmark or a buttplug with a picture of Channing Tatum on the nubbin. (New product idea? DIBS!)
DO be yourself. If you normally say “Make love to me, you stud!” and you suddenly start sexting “Shove your giant _____ pump into my wet, hot _____ hole like I’m your ______ slut, my hot Weapon of Ass Destruction!,” your partner will have to check his contacts to make sure he’s talking to you. You can get dirtier than usual, just don’t go nuts.
DON'T sext drunk. If your boyfriend's name is David and your drunk fingers accidentally stop at "Dad," you could find yourself across the Thanksgiving table from a father who can't look at you due to DBPTSD (Daughter's Bush Post-Traumatic Stress Disorder).
DO wait for the right moment. A man loves to receive a photo of your lady junk, just not, hypothetically, in the middle of a city planning meeting about clogged waste disposal issues. A quick text like, “You alone, sweetie? I’ve got something special to send you,” to check in works wonders for avoiding IWCs (Inappropriate Work Chubbies.)
As long as you follow those guidelines, you should be fine! No need for a sexting Cyrano—your boyfriend clearly finds YOU sexy. So give it to him. Digitally speaking.
Love,
The Scarlets
The Accidental Virgin
Dear Scarlets,
I’m a 42-year-old woman who also happens to be a virgin. It’s not by choice. I don’t talk about it and I assume most people don’t know -- although I’m sure many suspect, and that makes me uncomfortable.
I feel like a freak. Our culture jokes about people like me, who have reached their forties and not had sex. Maybe I just haven’t found the right guy, ok?
Or maybe there’s something wrong with me. I’m starting to feel that this may be the case. I’m not Cindy Crawford but I used to think I look okay. I’m a good dancer. I’m nice. My veal scallopini is to die for. But I don’t meet men I’m attracted to who are also attracted to me.
It’s not like I hold my virginity sacred. I’m not waiting for Mr. Right. I’m just trying to meet Mr. Good Enough. So there’s that.
Also, what do I do when I do meet him? Do I tell him I’m a virgin? Will he be put off? Isn’t that a lot of pressure for him to deal with? Will he be able to tell even if I don’t?
I don’t want to die with my hymen intact but I’m not yet ready to settle for some horny douchebag who will never call me again and laugh with his friends about me. Is a nice, patient, understanding fella too much to ask for? That is not a hypothetical question. I really need to know.
It’s obvious neither of you are virgins and I’m trusting you not to judge me.
Thanks for that and for any advice you can give me.
Signed,
Enough Virginity Already
Dear EVA,
We would never judge you for doing what’s right for you, and apparently so far circumstances have conspired to make virginity right for you. Brava for not settling for a douchebag -- it’s a common rookie mistake.
Since your immediate circle isn’t providing you with options we suggest online dating. You will get to meet men who would otherwise not cross your path. While you may not immediately meet Mr. Right, you will most likely meet Mr. Good Enough.
During tryouts for the position, keep in mind that this is a practice run and don’t be too critical of the applicants. We are not advocating settling for a douchebag! We’re just reminding you that you’re looking for Mr. GE, and he might be awkward, or need a haircut, or work for Microsoft.
It’s ok not to spill all your secrets on the first date, but we recommend telling him you’re a virgin before things get too heated. For some your virginity will be a turn-on. Others will want no part of it. Mentioning your virginity when the pants are already off could be a big disappointment for everyone.
When you do tell him, give him an out. Let him know that you know he may not want to participate, and that’s ok. If he takes the exit you’ve provided, be gracious, don’t take it personally, and go on to the next contestant.
When you have found a willing Mr. GE, we recommend buying some smaller toys and experimenting with them prior to the act itself—we’ve found that getting used to penetration prior to being penetrated by an actual penis makes the experience significantly easier. This “Lime Teaser Mini Smoothie” will do the trick—then try a couple progressive bigger ones until you’re at his Actual Size.
Once you’re ready to do the deed, set the stage. Make it comfortable for yourself in a way that says sexy to you. Ideas: good lighting, clean sheets, music if it won’t distract you. USE CONDOMS. Have some lube handy. It will make penetration easier for you the first time. And USE CONDOMS. (Did we mention CONDOMS? Getting an STD your first time is ridiculously UNsexy.)
Set ground rules, e.g., he stops when you say stop. Go slow.
Explore what feels good to you. Don’t hold yourself accountable to any porn you’ve seen. Every body is different -- find what works for yours.
Don’t expect to be “good” at it, just have fun with it. Practice makes perfect. That said, research never hurt anyone. We’re big fans of The Guide to Getting it On as a great resource for sex-havers at every level.
We know you don’t feel like it right now, but you’re lucky. You are in a unique position to start your sex-with-another-person life in a conscious way. You’re older and know how everything works: the biology, contraception, STD prevention. You’ll be in a comfortable, safe spot and you’ll USE CONDOMS. You get to be in control of whatever happens, and that is unfortunately not true for a lot of women who lose their virginity at a young age.
We’re excited for your adventures in sex! Keep reading The Scarlet Letters for more hints and tips, and write us again. We purely adore getting TMI details.
Much love,
The Scarlets
You’ve just read The Scarlet Letters, a sex and relationship column written by two redheads on a mission to eradicate slut shaming, uninspired oral sex, and the myth of “normal.” Send your sex and relationship questions to [email protected]. (Want your email address anonymized? Try Anonymouse here, or any number of other email anonymizers on the webernets!)
The Scarlets:
Allison Picard had a long career in publishing before she got antsy and divorced, and then one in event planning before she got tired of working. Now that she's retired she can turn all her attention to sorting out your sex life. Other issues, proposals, invitations? Write to [email protected].
Courtenay Hameister is the Head Writer and Co-Producer of Live Wire Radio, a syndicated radio variety show distributed by Public Radio International. She is currently working on a book that will be released through Audible.com in 2015. Follow Courtenay on Twitter at @wisenheimer.
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