WARNING: This post goes into quite a bit of detail regarding my sexual history. If you’re a family/friend/person who would rather not know these things about me, turn back now! 

Ok good.

I also want to preface this by saying that I’m extremely freaked out about posting this. In this, I will be sharing some things that very few people know, that will most likely change the way you view me. I like to say I’m an open book, so transparent. But there’s a couple of things that have been my secret for years. And today, I’m going to lay them bare. Part of me wonders if it’s a dangerous, bad idea. But the other part of me thinks it’s extremely important to acknowledge and share my extremely unconventional journey. So…here I go. 
I was born in a conservative Christian family in a conservative predominantly Christian part of the country, and, to top it off, was homeschooled from 2nd grade all the way through high school. (You can read all about it in my previous post here)

My sister and I were taught the Ten Commandments in our Christian-based curriculum, and the seventh commandment, “Thou shalt not commit adultery” had an addendum in our “easier to understand” version:

SEX IS A GIFT FOR MARRIED COUPLES.

I wasn’t really sure what sex was at that point, but okay. Sounds good.  

My mom was a registered nurse, and we were taught that we had “vaginas” but weren’t supposed to touch them.  

While my mom owned several books about sex ed from a Christian perspective, she never really brought them out and made us read them. They sat on the shelf, seemingly forbidden but utterly tantalizing. Every once in a while, nervous and sweating, I would carefully lift a book out of its place on the shelf, terrified I would leave a noticeable track of the lack of dust in that area. I wasn’t supposed to be curious about this. That was surely a sin too. 

Through my sleuthing, I was able to learn that sex was “when a man puts his penis inside a woman’s vagina and that’s how babies are made.”  

What?! Weird.  

At one point, when I was probably in early high school I remember that my mom had gotten a book about “intimacy in a Christian marriage” from our church library, and there were a bunch of statistics from polls that had been conducted with Christian couples. It had some statistics regarding “oral sex.”

What the hell was oral sex?  

As far as I could tell, it was probably some sort of kissing. Probably, you moved your tongue around in your partner’s mouth like I heard you did in French kissing, but then maybe you put your tongue in a really specific spot and that was oral sex. But what if I got a boyfriend and started French kissing and we accidentally started having oral sex because I didn’t know where the spot was?! I looked for a diagram to figure out where this spot was. There were none on the subject. This was a problem. Would I still be a virgin if I had oral sex? It had “sex” in its name, but if it was just kissing…could you get pregnant from oral sex?!  Oh no!  Could you?!

I worried about it so much, but I had no romantic prospects, so I decided to push those worries aside until it became more relevant.  

I still have no idea when I learned what its true definition was, but I do know it was at least late high school, perhaps early college.

Abstinence only sex education, folks.


In high school, I was known as the “Purity Police” amongst my friends, who were the most worldly homeschoolers I knew (which, face it, was still pretty not-worldly.) I remember when my best friend told me that she had made out with a guy and they French kissed, I was concerned about her. It was a slippery slope.   

I was so very single through most of high school, wondering why no boys showed any interest in me. And then, the day after I got my wisdom teeth removed, when I was starting my senior year of high school, I met the guy who would become my first boyfriend.

He was a self-proclaimed bad boy, though he was actually more of a nerd who loved video games and The Matrix and wore terrycloth wristbands with Green Day pins and Flogging Molly patches on his backpack. He was brought up Catholic and viewed himself as agnostic, or perhaps borderline atheist.  

He was dangerous for Little Good Girl Amanda.

I was only mildly physically attracted to him though, so that bode well for my purity.  

To be honest, I was terrified. It took three months into our relationship to allow him to kiss me. And then I discovered how awesome it was. Of course, he wanted to allow his hands to wander, but he knew that was strictly off limits.  No boobs for him.  Not even an ass-grab.

There were a few times in which I let him push me up against a wall and kiss me passionately, and, though I felt so very dirty in doing so, I felt some tingles of excitement heightening the experience even more.  

He would have debates with me about how “2nd base is really nothing. (Insert homeschooled friend) and (friend) have done it. It’s no big deal.” This argument wouldn’t change my mind about anything, and only prove to be the catalyst for judging my friends even more for their evil, sinful ways.  

This relationship was over by the time I graduated high school, and I never let him past “first base.”  

From xkcd.com

I was never explicitly told about masturbation. I never officially got “the talk.” I learned through various means that touching yourself “down there” wasn’t something you should do. Sexual feelings were a sin. I had “accidentally” experienced a couple of times in which I got stimulated, and I was both captivated and disgusted with myself. I wanted to experience more of that, but it was so bad. I just couldn’t try it anymore.

Fast forward to the fall of my freshman year of college. I had recently started dating The Guy Who Is Legally Banned From My College Dorm.

My roommate and I were talking one night, and she asked me if I had ever had an orgasm. I told her I hadn’t, that I wouldn’t do such a thing, and she laughed at me good naturedly. 

I don’t know at what point it was, but I finally gave in and let this boyfriend touch my boobs over my shirt. There wasn’t much there anyways.

And then I discovered grinding, the juvenile “dry humping.” And I experienced my first orgasm. I don’t remember it much, but I’m pretty sure I cried. I had no idea it could feel this amazing. But immediately, I was plagued with guilt. I shouldn’t be experiencing this. It wasn’t for me.  

Slowly, I became more adventurous. He was the first boy who saw me topless. Who used his hands on me, first over my underwear. And then I would once again experience the guilt and self-loathing. I would cry to him and tell him we shouldn’t be doing things like that anymore. But soon, I would miss it, crave it, and we would inch a little bit forward each time. 

I touched him for the first time, and I was surprised with how hard it could get. It felt like a warm garden hose or something. It was so strange and alien and enthralling.  

It became routine to get each other off…but only with our hands. Never our mouths. That was where I drew the line. We both teased each other. We both wanted it so bad, but I knew how incredibly guilty I would feel if we did. 

At some point, I wanted to feel these sensations more often, and I would touch myself. But he would ask about it and I, incapable of lying, would admit that I had. He would get insanely jealous, and beg me only to get off with him. He didn’t want me to orgasm without him. Looking back on this, I acknowledge how incredibly problematic this was, how downright abusive. Which only added to my weird sexual hang ups.

I was with him for nearly two years, and this was all we ever did sexually, bringing me up to the summer I turned 20.

I had my first summer fling. He was an actor at my first summer stock theatre job, and the night we met, we had attended a party. He was a real bad boy, super sexy with a white spot in his otherwise black hair. He had an exotic name, he rode a motorcycle, and he tasted of whiskey and cigarettes. It was intoxicating, and, to this day, the smell and taste of cigarettes is still a turn-on for me, even though I hate the concept of smoking itself. 

We would sneak away to hidden rooms in the dorm in which I was housed, which led to an accidental hand-job in the chapel. I didn’t realize there were crucifixes on the wall until after we were done. Oops. God is watching, indeed.  

For the first time in my life, I too felt dangerous and sexy. Not quite enough to give a blow job, but sexy enough to proudly go to work with hickies on my décolletage. I was finally beginning to embrace my sexuality. 

Rebelling against my smothering, abusive relationship from the previous two years, I swung my arms open wide and pledged myself to enjoying the independence of singlehood.

It was New Years Eve and I was attending my friend’s Punk Rock Formal party. I got cigarette burns on my arm and Doc Martin footprints on my sandaled toes, and I had a blast.  

It was there I met my friend’s next door neighbor. He was six years older than me, a professional in a creative field, and had a sexy maturity about him. Far different from the boys I had been with in the past.  

We started to spend time together, and I still remember that our first kiss was during the credits of Garden State, which we had watched in his living room. I still smile when I hear Frou Frou’s “Let Go.”  

With him, I experienced my first long-term “friends with benefits” situation.

With him I experienced my first oral sex…I knew now what it was, and it was given and received.  

And with him, I experienced my first introduction to kink.  

It was he who first tore my fishnets off me. Gave me bruises that I looked at fondly for a week after I last saw him. Spoke to me in a low growl, calling me names.   Smacked me hard in my face because I asked him to, choked me with just the right amount of pressure.  Allowed me to blindfold him with a necktie and tie him to the bed.  Begged me to do all sorts of things to him.

We had a lot of fun together, but we were never actually a couple.  At times, I kind of wished we were, but we had a great thing going.  I still look back upon this time as “The Great Unfurling” of my sexuality.

Throughout the next few years, I “messed around” with lots of guys, but never went any further physically.  

I’m sure a lot of them lost interest in me because I wasn’t willing to actually have sex with them. 

At this point, my mindset was shifting. Now, I wasn’t so sure I wanted to wait until marriage. I wasn’t so sure about where I stood religion-wise.  And I knew most Christians my age hadn’t even waited. At this point, I just wanted to wait for a guy I really loved.  

I had begun to develop a reputation at my college for being a bit of a slut, which was hilarious to me because: 

1) I had never gotten with anyone from school until the very last week of my senior year, which was basically a glorified makeout session.

2) I had never had sex. 

And by this point, at age 21, I was getting to the age that it was kinda weird I hadn’t, even at a Christian college.  

But hey, I was fine with the reputation. I was having tons of fun.  

My gay BFF would tell anyone who would listen about my “insatiable sexual appetite.” 

I went straight from undergrad to grad school, and during the extreme stress of my first semester, I discovered I had HPV. 

What a cruel joke. The virgin with HPV. Turns out that any form of genital to genital contact can spread it, and it happened to me. 

It was my punishment.  

I have always kept a Word file on my computer with a list of everyone I’ve ever done anything with, from kissing onward. I even have a complex series of symbols to denote what was done to whom. Yeah, seriously. 

And so I took it upon myself to contact every guy with whom I’d been intimate in the last two and a half years, disclosing what had happened, just in case.  

There has been a lot of research that has been done regarding HPV in the last ten years. At this point, Gardasil had been recently introduced. Apparently most guys never present any symptoms, and are often just carriers. Some doctors say you don’t even need to disclose. And the most recent statistics say: “Throughout the course of their lives, about 75 to 89 percent of all males and females in the United States will contract one or more types of HPV.”

It’s so common, but that didn’t change things. I was damaged goods already.  I felt so dirty, so disgusting, so utterly broken.  My body that I had grown to love for giving me such pleasure had turned into an inhospitable place.

I was told that it would most likely clear itself out of my system on its own within a few years, and that was comforting.

But what about now?

I was tormented by the fact that, with each new partner, I would have to disclose this information, and let them decide what they wanted to do about it.  

Reactions were always understanding, and often, they conducted their own research. Most guys decided they didn’t feel comfortable going down on me, which I understood.  

So now I was girl who wouldn’t fuck you who also had an STI. What a catch.  

Then I met The Guy I Thought I Was Going To Marry

We were so perfectly sexually compatible. We both enjoyed kink, and were both switches–neither of us wanted to settle into a solely dominant or submissive role. He was fucking gorgeous, so sexy, and always knew exactly what to do to, as cliche as the phrase is, “drive me wild.”   

We experienced some of the most amazing, hot, beautiful moments of my life together.  

He was in bible college for homeless ministry, but he was one of those cool Christians who sought to live like Jesus in a radical way. We both really wanted to have sex together, but I wanted to be really sure.  

I was still in grad school, and one of the things that scared me the most was getting pregnant. I didn’t have time to worry about shit like that.  I had never been on birth control and the idea of that still freaked me out. But for him, I thought it might be worth it.  


But around the time I began seriously considering losing my virginity to him, he went completely off the deep end with religious fervor and deemed anything physical we had done before completely immoral. And then he broke up with me, completely unexpectedly. 

I was almost 25.

There was a smattering of casual hookups after that, but nothing of consequence. 

Next was my ex-boyfriend who was transgender. That was my first experience with a strap-on.

And then there was my wife. The first and only woman I’ve ever been with. And about a year into our relationship, my antidepressants rendered me completely asexual. Because of these reasons, I never had much sexual confidence with womens’ bodies. And we had sex once during our year of marriage, against all of her wishes and pleading. 

Part of me wondered if I would regret never having had sex with a dude.

Then the divorce happened.

This brings us up to this spring.  

And I found myself, months before turning 30, still by the world’s standards, a virgin. No “P in V” has ever been had.  

And there I was, contemplating the subject. 

Few of my closest friends even knew. If being a 22 year old virgin was awkward, imagine introducing myself as a 30 year old virgin. Who the hell would want to take that upon themselves?  Talk abouy baggage.

It was shameful.   

But also, what was I waiting for anymore?

I had been married. I had been divorced. I had become a verifiable Blow Job Queen in my younger days, because what the hell else could I do?  

Was I waiting for marriage?

Nope. Been there, done that. 

Was I waiting for True Love?

What the fuck did that even mean anymore?

What about…a decent guy who understands? 

Yeah. I could do that.  

I made an appointment with Planned Parenthood to get an IUD installed.  

I chose to go with Paragard, a copper IUD that is hormone-free and lasts for ten years with at least a 99.4% success rate. 

I still really don’t want babies. I’m almost 100% positive that I will never want babies, and if I do, I would adopt. (That’s another post…) So the idea of not having to worry about birth control until I’m 40 sounded perfect. 

I made the mistake of googling animations of the installation process and almost puked the night before, but it went in with less pain than I was expecting. Ya know, for plumming the depths of my uterus for placement, dilating my cervix, and shoving a copper T up into my baby-palace.  

The cramps were pretty gnarly for the next couple days, and I cramp more during my period than I used to, but it’s been an overall great experience for me. 

I had a one-night hookup with a guy just before I got the IUD put in. The first cisgender guy I had been with since fall 2010. And my first hookup with a sex drive in years. Yup, I still liked guys. Yup, I still felt super sexually confident with them. Yup, I still had kinky inclinations. Yup, I was still the Blow Job Queen. 

“I don’t have any condoms,” he confessed. 

I knew he was a total douchebag, but I was just using him for his body. I was good at that. I’ve always been excellent at the emotional detachment if I chose to be. “That’s fine,” I replied, glad I didn’t have to turn him down. It sure wasn’t gonna be him who deflowered me.

“If a guy has a problem with the fact you’re a virgin when you bring it up, he shouldn’t be ‘allowed in’ anyway,” a guy friend told me.  

Right. 

So I got my IUD and went to my summer job, not quite sure what was going to happen. If I was going to put it to use, or if it was just gonna chill up there in my uterus for a year or so (dear lord, I hoped not.) 

The prospects were pretty bleak at work, which was probably for the best because that gets messy.  

I had begun to amuse myself by setting my Tinder age range from 19-40 (and both men and women because I’m me) and seeing how many of my coworkers’ profiles I could find. The answer was: tons. I never told anyone I saw them on Tinder but every time I was around them I considered it. I never got drunk enough. But let it be known: if you worked with me this summer and were a dude who likes girls or a girl who likes girls in my age range, I saw you.  

But there was this one local guy I actually swiped right on. I didn’t really mean to because I’m only in Central NY for two months out of the year, and I only had three more weeks in my contract, but he intrigued me.  

He messaged me, opening with “So, who’s your favorite serial killer?” We bantered back and forth about H.H. Holmes for a while, discovered we both have art degrees though he has a real adult job now, he knew what Victorian mourning hair jewelry was, and also collected weird antique things. He used to be in a pop punk band. He had tons of tattoos.  He was pretty damn cute.  He’s an unconventional Christian. We clicked.

We texted until 4 am the next few nights, and agreed to meet that weekend. 

The sexual tension was there, so I put it all out there that I was still a virgin but just got my IUD in preparation for such an occasion.

“Okay, that’s fine,” he said.

“But if things end up being cool with us and you don’t murder me first, and if you’re okay with it, I’m ready.”  

Yup. I lost that pesky virginity this June, a month after I turned 30.

I told you this was going blow your mind just a little. Bet you never would’ve guessed that about me, the Theatre Department Slut.

It wasn’t a big deal, seriously. Sure, I feel like there’s a lot that I have yet to figure out (well, it’s not really that difficult, but still…techniques and whatnot) but I’m so glad that it’s finally out of the way. 

And, even though after I left town, we’ve done the slow fade, I’m glad it was with him. He was pretty cool.  

And now I can finally move on, with no awkward secrets to disclose. I feel free. 

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