I wrote this post originally in my 20s. Sometimes I’ll update the posts with commentary from a 30 something year old … and sometimes I’m a purist and want to leave posts as they are. Either way, yes, I did lose my virginity in a cheap motel to a boy I met in a pool hall.
I finished high school early, and was planning on moving out to NYC. I was going to be studying at the Lee Strasberg Theater Institute in Manhattan, and the parentals were gracious enough to help out with an apartment one minute from the school. Yep, I had my own apartment at 17 in Manhattan. Kinda rad … but either way, I had this odd irrational fear that by being a virgin and officially “living on my own” – I would do something stupid … or boys would be able to smell that I was a virgin and it would be weird.
I’m not kidding. I thought people could “smell” that you were a virgin.
I’m sure I even justified said irrational fear by saying that well technically speaking, the sweat your body secretes when you have anxiety over a situation you’ve never been in before …. blah blah blah. I assure you, I probably at the time had a very valid reason for thinking this – hahahaaha I was killer in debate, and loved researching weird shit online.
I never dated in high school. Like at all. Like anyone. Like ever.
Well, Joshie and I kinda dated twice – but he didn’t want anything serious until he had his license and frankly at that point, I was already done with school. But yeah – either way, I had no one on my radar screen.
My best friend and I followed a bit of the alternative crowd, so we used to go to some pretty dodgey places – one of them being this pool hall on the Berlin Turnpike. We were always on the look out for boys, and thought the boys in Berlin were uber hotties.
Anyway, April 2001, we get to the pool hall, scope around – TOTALLY on the prowl … not necessarily thinking about looking for a guy to take my virginity, but just our normal Friday night hunt. I walk over to this one table, and see these two boys; one of them in particular is just wow, unbelievable, jaw droppingly beautiful. Super dark hair, light eyes, pale skin – I mean wow. Could to this day TOTALLY pass as Pete Cashmore’s brother or cousin.
They seemed a bit lost in their own world so after 5 minutes of batting my big blue eyes I thought, well, I’m not getting any younger here … and stroll up to their pool table.
At the time, I was a newbie to playing pool – and very literally didn’t even know how to hold the pool stick. With my best practice audition for a porno, I sashay on over and say excuse me – my names Jen, I’m new at this whole thing … I place the pool cue on the ground mimicking rather sexual movements and say, can you show me how to hold this thing?
The guy I was eyeing was just in fucking stitches. He turns BRRIIIGGHHHTTTT red, laughing, and his friend pipes up and goes – oh SURE, as he grabs his own pool cue and says, place your left hand up here and the back one supporting this …. his flushed friend cuts him off saying, YO, she’s hitting on me.
Yay! He got it!
I grabbed my friend and introduced her to his friend, and we had such a fun night. Totally hit it off. Super super super cute and super super super smart dudes. They went to Xavier which is a prep school in Middletown, and ooohhhhhh myyyyyyy I liked this boy.
At the end of the night we swapped digits and AOL SNs, and went on our merry ways.
I remember dashing home, popping on my computer and immediately adding him to my buddy list. OMG OMG OMG he’s so cute! Does he have an AOL profile? or is he just on AIM? OMG please don’t have a sub profile to see that I’m stalking you. (oh bless the days of pre-social media-ness. Even just the screen name popping up with the sound of a door was enough to give a young girl chills.)
A few days go by, and I couldn’t stop thinking about this boy. I was crushing so hard. I would intermittently restart AIM a few times as to not appear that I had really been online for 48 hours straight.
Either way, a couple days go by, then his screen name pops up on my buddy list. OMG OMG OMG OMG OMG … he’s online. Is he going to message me? Am I going to message him? My screen name was Perfect80sgirl, but sometimes people misspelled it, or put an O for the zero, he seemed smart – I don’t think he’d do that, but what if my handwriting wasn’t clear, I do have very messy handwriting, hence why I type … I click his screen name … ::sound of keyboard keys:: h-i-y-a
Hiya works. Sexy, and inviting without being come over here baby. K … ::click enter::
The blue font shows up with the word, yo.
We start chatting. We both had pretty intense ADD, so I’d like to say that there were fireworks and long loving poetic gestures …. but there weren’t. I think he said school was lame, and he was getting ready for work … bbl.
Alrite, alrite – I can do this.
A few more days go by, I hit him up again asking what he was doing for the weekend. He said he wasn’t sure, but what did I have in mind? What did I have in mind? A candlelight dinner, roses, strawberries with champagne, garnished with Godiva chocolate. Oh wait, snap out of it Jen … ::sound of keyboard keys:: I dunno. Wanna kick it?
Blue Font: Sure.
Red Font: Cool. Call u l8tr.
We hang out, and by hang out – I mean literally. He picked me up and we drove around for a while settling on some lovers lane in East Hartford, or some place I had never been.
We start making out.
OMGGGGGGGGGGGGG he is a good kisser. Like wow. wow. wow. Nice lips, good tongue pressure, sweet spit.
Then, before things got too hot and heavy, he takes out a joint and asks if I wanna smoke. I pretended to take a hit, but didn’t even inhale. (Dude, I was suchhhhhh a goody two shoes. Drugs in high school just weren’t my thing.) We then talked about goals, and what he wants to do with his life. I think at the time he actually wanted to be a pharmacist. I told him I was going to move to NYC when I finished school. He thought that was cool, and then continued to make out with me knowing it was that much hotter that I was leaving in a few months.
He drops me off back at the house, I don’t even think I let him get to second base. There was some major heavy petting, and some motion over the crotch area – but other than that, nada.
I get back to school, and everyone starts buzzing about prom. It was a few short weeks away, and I still didn’t have a date. FUUUCCKKKKK MEEEEEEEE!!! Like literally can there be anything worse in life than high school when you’re such an outsider? I was there to study, do my thing, and leave. I didn’t date anyone, at all, ever. Thought no one is going to ask me, I can’t not go to my prom. FUUUCCKKKKKKK!!!!
I get home, pop online, and message the pool hall boy. Now, I had to be careful with exactly how I worded this … prom is a big big big deal. This boy and I had gone out, but we weren’t even remotely considering dating each other. I was leaving for NY, and he was going to go to college. I think about how I wanted to word this; I can’t just point blank ask him to my prom, why don’t I tell him about my plan of not wanting to be a virgin while I’m living in NYC, and ask him if he wants to take my virginity!
Yep. This happened over AOL instant messenger. hahahahaa
Blue Font: Are you sure?
I explained to him that I hadn’t really dated anyone, and I really enjoyed spending time with him. I failed to mention my irrational fear of being released into the real world while still holding onto my cherry – but eh.
Dude, a chick you just got hot and heavy with asks you over AIM to take her virginity? Like really? HAHA what do you all think he was going to say …
Blue Font: I’d love to.
BOOM! Jen’s got a prom date. ::happy dance::
Then came the logistics of planning this thing. I didn’t want to lose my virginity in a car as yes, vehicular sex can be quite nice … but this is my virginity, and my life evolved around John Hughes. Losing it in the back of his car just wasn’t going to happen.
We went back and forth on messenger, he suggests a hotel on the Berlin Turnpike. For the life of me I can’t remember what it was called – can see the sign, had a moon on it – other than that, I got nothing! Mind you too, he was 18 – so he could get a motel room.
Sounds perfect, I thought.
Berlin Turnpike … prom night … me …. and the hottie from the pool hall.
Prom to me was unbelievably anticlimactic. I didn’t do the whole group picture things with your friends; I was a loaner. I bought my dress on a half whim with my mom, and did my make up myself. I had however, gotten my hair done – so that part was pretty kosher. Oh, and I think my grandparents were over for dinner that night, and my mom might have made a casserole. Like literally … hahaha. John Hughes this was not.
After arriving about a half hour late, pool hall hottie finally shows up. The parentals snap a few pics, and on our way we go. I didn’t do the whole limo thing – again loner … party of one … loner …
We get there, and the place was still filling up. We were pretty early. I remember sitting at a table with a few of my friends, but I wasn’t really interested in talking to anyone. Only my best friend knew what I was planning on doing that night, and I forget why she wasn’t there … but whatevs.
I was so nervous, I had such a shit eating grin on my face. I just couldn’t believe I was about to have S-E-X.
We stayed for a bit … and I remember one song we danced to, Bryan Adams Everything I do – I do it for you. In my head, that became our official prom song. Not like the actual prom, but the little fantasy version of awesomeness that I was living in my head.
It was weird, I wasn’t in love with him, but I trusted him. He was really wise for all of 18, really really absurdly hot, I just very much wanted to do this. Whatever it meant. The time was now. Like right now.
We leave the prom early. I had asked my parents if I could spend the night out after prom and they said oh hell to the fuck no. My parentals were actually pretty lenient considering all of the bullshit I could have gotten involved with – but thankfully, they raised me to keep my noggin on relatively tight. In high school, I assure you, they had nothing to worry about.
We get to the hotel, and hahahaha omg it was hilarious. You can totally rent the rooms by the hour. I forget how long he booked for though. I literally just remember being half out of body wondering if this was going to happen, and what it was going to feel like – while at the same time trying to not be mortified that it was SOOOOOOO obvious what we were doing as we were both still in our prom outfits.
I would PAY to see that security tape – hahahaa goodness gracious.
We get in the room, and pretty much just get down to business. There were no candles, but no vibrating bed either. It was a queen sized bed in a very dark room, with a bathroom and a TV.
No foreplay, no nothing – he coached me into it. He kept saying, are you sure you want to do this? Are you sure?
I took a deep breath, yes I’m sure.
This was just such a surreal experience for me from head to toe. I had never even been fully naked in front of a boy, or anyone outside of the family doctor – now this is totally happening? FTR, I wasn’t a complete prude. I had done my fair share, but not much … and certainly not anything like this.
Totally naked. Boy totally on top of me. This is happening.
He goes to try and put it in, and I literally almost die. I had seen one or two penises before, but this one was … omg … fucking huge. Yeah, imagine Ron Jeremy taking your virginity. I hadn’t even let a boy finger me – now you’re going to stick WHAT inside of me? Ohhhhhhhhhhhh mmmmyyyyyyyyyyy gooooooodddddddddddddddd.
hahahaha worst. experience. ever.
Well, not the worst, it had to happen – but no one explains to you just how painful it is for a female to have sex for the first time. There’s no lubrication, or barely any – and it’s not like an 18 year old boy knows what the fuck he is doing either. He kept trying, and eventually succeeded. I don’t even remember him coming or anything – I think the pain literally shot me into another world.
When it’s over there was no cuddling, no nothing – he kissed me and asked if I felt okay … I lied and said yes even though when I stood up I could barely walk it felt so uncomfortable. He kissed me again, and let it linger. I didn’t know what love was then, but I know in that moment, he cared. That was a first for me.
I got dressed, and he drove me back home. I remember stumbling for my keys, as my dad opened the front door.
SOOOOOOOO not the person that I want to see. He asked how it was, etc … I said I was tired and was going to go to bed. Had fun, but really exhausted. OMG, I do not want to see my dad’s face right now!!! Why are you still awake?!?! Stop it!! Stop it!!!!
I turn on my TV and fall asleep. Wow, I just had sex.
I felt like a different person the next day. It wasn’t this moment of, man, I feel like a woman – it was just more of …. that’s what all the fuss is about? I don’t get it!
Sex, like prom, was very anticlimactic. They prepare you for it so so so much in school, you learn about every body part, and about 15 different types of birth control – but I just have one question for the school system, why does not one prepare you for the emotional toll that having sex at a young age can do to you? Literally. I do not remember a single class where anyone, anywhere talked about emotions regarding sex, only the physical mechanics of it. Was I supposed to talk to my parents about that? My parents who have been married since they were in their late teens, and were each others firsts onlys and everythings? With the next person I have sex with, I have doubled my parents record.
I was feeling very confused.
I putzed around my day in a bit of a fog. It’s not like I loved him, but I certainly didn’t think of him just as a friend – but what was he? The guy that took my virginity? Really? And that’s it?
I waited by the phone for him to call … it never rang.
I didn’t dare get on AIM, I know I may have asked him to take my virginity over AIM – but I felt he should have still been man enough to just pick up the phone and fucking call. Nada.
I remember writing in my journal what had happened, and I literally wrote – “I’m curious to try the sex thing one more time, but I don’t know if he’s going to call.”
And very honestly – he didn’t.
After a week, I took him off my buddy list.
A few months go by, and I move to NY as he heads to college. I wasn’t heartbroken, more just incredibly confused and a bit hurt by everything. I know he didn’t owe me anything, but I felt so blah. Plus too, he was so incredibly big it wasn’t like I enjoyed any bit of it.
I proceed to do the only thing I knew how to do – get to work. I threw myself in my studies at Strasberg. My class load was incredibly intense – I had writing classes, acting for film and TV, dude, I even got into the super secret wednesday advanced acting class. I loved what I did – but I put boys out of my mind for a while. I was here to study.
Then shortly after the new year I got an IM – it was from the boy. A bit shocked, I didn’t really know how to respond to him.
Blue Font: Hey.
Red Font: Hi.
Blue Font: How r u?
Red Font: okay.
Red Font: What happened with you?
Blue Font: What do you mean?
Red Font: I never heard from you again.
Blue Font: Yeah, sorry about that.
I don’t honestly remember the excuses he gave me for not calling – I just remember knowing that it was complete bullshit. He asked if he could make it up to me, he wanted to come to NYC. HAHA yeah right. You’re going to come down here to see me after you couldn’t pick up the phone to call after you took my virginity? Yeah! My sister is there too.
Ah fuck. This is happening.
He knocks on my apartment door. I open the door, ddaaaayuuuummmmm he looked good. Like looked good good.
He kissed me on my cheek.
I invite him in, and we start talking. He immediately apologizes again for what he did. I said I was kind of over it …. which was a total and complete lie. I’m two for two with this dude.
What was I supposed to say? Yes, you hurt me. Now you’re here, in my life again – what is supposed to be accomplished here? I’m not really understanding any of this.
He asked me if sex got any easier (or something more likely a little more classy, but you get the idea), I said no, I hadn’t even had sex again. Really? he replied. Yes really. I told him I’ve been focusing on my studies – which was half true, but half a defense mechanism from not wanting to get hurt again.
He kissed me, and laid down in the bed next to me. We fell asleep. No sex.
In the morning he went on his way to see his sister, and I went to class. I wasn’t really sure what any of this meant, but I just didn’t care at that point. I didn’t regret letting him take my virginity – in fact, I was still glad that he did. I probably would have just done something stupid and gone home with a stupid boy at some stupid party. At least I cared for him, and I knew in that very moment when I was getting dressed in the motel room – he cared for me too. That’s all that mattered to me in that very moment.
A couple of years go by, actually more than a couple almost 8 until I hear from him again. I had left my AIM open on an old computer and when I went to boot it, BAM! There he was!!! I was surprised. Again, I don’t really know what to say … but I don’t want you out of my life. I just … don’t know what to think of you.
He then tells me that he was engaged, but he also has a baby girl!!! He sends me the picture over AIM, and ommmmmgggggggg this little peanut is BEAUTIFULLLL!!! Like crazy beautiful!!! Looks just like her daddy, only in female form and not the creepy wow, you take a little after your father too much kind of way.
He still lives in CT, and is a chef now. I guess you could call him a happy little clam. hardy har har har.
I actually just became Facebook buddies with him about a month ago, and sent him this message …
Since this post originally went live, we have caught up many times. There was a brief second in 2015 where I thought we might actually date, but thankfully what was in the past remained in the past. I’m now happily married to a man who has heterochromia (meaning one eye color is different than the other), and I don’t need a chef because during the pandemic I learned how to cook for myself.