I Had A 6-Month Plan To Lose My Virginity, Here’s How It Went


Before I tell you the 6 month plan I had to lose my virginity, you need to understand a little bit more about me. I’m 22 years old and just graduated college. I was the stereotypical “good girl.” I got good grades, had a lot of friends, a close knit family, and went to church on Sundays. I gave food to the homeless, volunteered my time at hospitals and food banks, and gave money to charities. I always believed in doing good in exchange for good in return. But when I graduated college this past May with no job, no boyfriend, no place of my own, and nothing ahead of me that I could see, I wanted the “good girl” reputation gone and I was determined to make a plan to make that happen.

June 2014.

I was miserable. I had just turned 22 years old and graduated from college with a degree that I wanted nothing to do with. It was too late to start grad school in the fall, but even if I did, I didn’t know where I wanted to go or what kind of degree I wanted to pursue. I had just moved back home in a house filled with my parents and siblings after I had been away for over 4 years. All through my life, I had always been one to keep busy, have a lot of things on my plate, spread myself too thin, however you want to put it, I was always booked solid. All of a sudden, I graduated, it was summer, and I had nothing to do. I desperately needed something to do while I applied for jobs at companies that I had absolutely no interest in working for. Now would have been the perfect time for a summer romance to come into play, but of course life never sends what you want, when you want it. I needed something I could make happen. I’m a little bit on the shy side, so whenever guys come my way, I sheepishly shew them away. It was time to work on that.

July 2014.

Miserable — go figure. I had finally gotten a part-time job which got me out of my house for about 20 hours per week. But my job was in sales, so I heard the work no all day, every day. I heard it from people of all ages, all ethnicities, men, women, and I heard it in every nasty way possible. I just wanted to scream back every time I was bitched at — “Do you think I want to work in sales?! Do you really think this is something I enjoy?! I’m a 22 year old recent college graduate who can’t find any other job!!!!” So I had a job, but not one I enjoyed. I joined a gym to fill another couple of hours every day, but mostly I joined to work on my confidence. I gained the freshman 15 and managed to lose it by the middle of my senior year, but if I wanted to lose my virginity to a guy without him knowing what he was taking from me, I needed to feel good. To feel good, I needed to look good. To look good, I needed to bust my ass. I had already lost some weight, now it was time to get toned and fit.

August 2014.

Miserable again. Same job, same home life, same boring life. It was time to pick it up a notch. The summer was almost over and I couldn’t find a single guy to have any relations with. So I did it, I joined Tinder. What many call “the most shallow dating site” or “the hook-up site,” I was now part of it. The first week I had it, I spent hours on it. I’d wake-up, Tinder. Get home from the gym, Tinder. Get home from work, Tinder. After dinner until I fell asleep, Tinder. It had completely consumed my life. I was hardly interested in entertaining any conversations, I just wanted an ego boost by guys showing any interest in my looks. I didn’t do what I assumed most girls did on Tinder. I had taken pictures that showed my silly side. I was never really one for taking “sexy” pictures, so I posed as a girl out exploring the world with a sense of humor — essentially, I posed as myself. If I wanted to lose my virginity I wanted guys who thought I was sexy for me (or at least what they could see of me).

September 2014.

Miserable, still, but at least I was miserable with a little something to show off. My body wasn’t anywhere near perfect, but it was pretty toned. I at least had a job, so when people asked me what I was doing, I had something to say. Tinder matches continued to flood my inbox and I decided that maybe it was time to take the next step. I started answering. I got plenty of crude pickup lines, but I just ignored them and answered the standard “heyy” or “wow you are beautiful!” or “I see you went to Ireland, I love it there!” Some conversations flowed and others dwindled out. I got plenty of offers to meet up, but I continued to turn them down. I was just too nervous, and to be honest, my tinder conversations at this point were the most experience I had with guys at all (pathetic, I know). Someone great would come eventually, at least that’s what I kept telling myself.

October 2014.

Misery — it hit an all time low. My 16 year old sister got a boyfriend before 22 year old me. And the questions came pouring in. “How does it feel that your little sister has a boyfriend before you?!” “Doesn’t it make you feel lonely?!” That was the last straw, I couldn’t take it anymore. *Cue Tinder login. This process needed to speed up. I answered the crude messages and all I did was talk dirty. Once I started, I just couldn’t stop. The words came pouring out of my mind onto my phone screen and before I knew it I was telling guys that I wanted to sit on their faces and how I wanted to tie them up and let me use a whip on them. I spent the entire month of October sexting close to 20 or 30 different guys.

November 2014.

Mis–NO. Not. This. Time. I wouldn’t let my misery get in the way. Now it was time to do something about it. I stayed on tinder and cut down the guys from 20 or 30 to 5. That way I could keep them thinking about me and I could learn exactly what I needed to about sex. I tried to tell my mom that my doctor told me I should be seeing a gynecologist since I had never seen one before (really, I just wanted birth control), but she just said “we’ll work on finding one, but you probably won’t get an appointment until the new year, but that should be okay because you’re not complaining about any problems and you’re not sexually active.” She was right, for now, but not for long. I needed a new plan. I researched birth controls and cheap ways to get it.

I landed on Planned Parenthood and made myself an appointment and got it for a good price. This wasn’t the only thing I was researching. I watched porn every night. Every kind. Kinky, romantic, and just plain fucking. I watched the girls and wanted to mirror exactly what they did, not matter how good or bad it felt for them. I read books and articles on losing your virginity, psyched myself out every time, but I wanted to know what it was going to be like, I needed to know. I learned sex positions, imagining a guy telling me how he wanted to fuck me and I would have no idea what to do.

I made my way into Spencer’s and bought myself a vibrator. I needed to pop my own cherry. There was no way I was going to let any guy know that he was taking my virginity. I couldn’t get it in the first few times, it hurt too bad. But I was persistent. Every time I tried to put it in, I pictured the porn I saw, the porn that really made me wet. Still didn’t work. Finally, I pictured my 16 year old sister, my cousins ages 20, 14, and 13, all with boyfriends or girlfriends. And then there was me. My blood boiled and my adrenaline started pumping and I shoved it in and I had to muffle my scream because it hurt so badly. I moved it around a little and continued to do this every night for a few days until it didn’t hurt anymore. I went to the store and bought a box of condoms. I was ready. I had learned the sex moves, kicked my ass into shape, popped my cherry, and learned to talk dirty.

December 2014.

I was ready. I had 4 of my original 5 guys left practically begging to fuck me. I started sending them Snapchats and they progressively got pretty dirty. And by pretty dirty, I mean raunchy and vulgar. I had to pick one to fuck first. #1 seemed to have a pretty good sense of humor, we really seemed to click. #2 sent me a text every morning that said “sit on my face” or “suck my cock.” #3 sent the occasional Snapchat and asked me if I was nearby (we both live in Philadelphia, but he goes to school in Connecticut). #4 also goes to school far away, but lives in Philadelphia. His girlfriend had recently broken up with him and he constantly sent me Snapchats or texts saying that I was hot and asking how I was doing. Usually I turned the conversations dirty. I decided that #4 was the one that I wanted to lose my virginity to. One day I went to work with a packed bag…mostly full of condoms, kinky sex toys (he had told me about a fantasy he had where the girl was controlling him), and lingerie. I texted him saying he should meet me at a motel at midnight.

He said he had plans to go to New York for the night with his friends. In that moment, I felt rejected, humiliated, and ashamed. I had just practically thrown myself at a guy and he was making up some excuse to get out of it (I later saw pictures he posted online and figured it must be true, but I didn’t know that at the time). My blood was boiling. I went to #3 figuring he must be home for winter break (hadn’t talked to him in a couple days) but I just sent him a message saying “When are you going to fuck me?” He responded saying a couple of hours sounded good. Before I knew it, I was home from work loading on tanning lotion, makeup, nail polish, and sending Snapchats to #3 so he could have a little preview.

I threw on a coat and walked out my door at midnight. He lived a half hour away. I swung by the liquor stores (there was no way I’d get through this soberly) and before I knew it I had parked my car on his street, threw back two shots, and stepped my 5 inch black heels out of my car. I stood in the cold for about 10 minutes before he finally let me in. He told me to come in quietly because his family was upstairs sleeping. I started walking down the stairs and I only got half way before he had his hands around my waist and pinned me against the wall. “I’m gonna fuck you so hard,” he said between kisses.

We went the rest of the way down, as he plopped on the couch and I threw my jacket on the floor revealing my red lace and silk slip. I climbed on top of him and we started feverishly making out. His hands were all over my body and it only took about 30 seconds before he was slapping my ass and stuck his fingers in my vagina. I let out a quiet moan and he said “I’ve gotta tease you a little first right?” He flipped me off of him so he could lie on top of me. He pulled my underwear off and put on a condom and before I knew it I was wearing nothing but my black heels and my legs were around his shoulders and he stuck it in.

It was smaller than my vibrator, so it didn’t hurt, except for when he started pounding me like a jack hammer. He liked doggy style, so we did it for a while, but then he wanted head. Man, did he love that. He came in my mouth and I asked if he was going to get hard again. He said I’d have to suck his dick to get him off-so I did. He put on another condom and went at me again doggy style, except the first time he missed and it went in my ass. That hurt like hell, to say the least. Eventually I just started giving him head again and I told him I wanted to 69, but he said he doesn’t do that. So I gave him head while he fingered me. I couldn’t really complain, it felt amazing. Then he finished and said “alright, I think I’m gonna pass out.” I took the hint. Found my underwear, threw on my clothes and coat and he walked me to the door. Said he’d talk to me soon and he’d be home all of break and I left.

Just like that, my virginity was gone. 6 months of planning and it was over. The sex was a little awkward (for me) but I would imagine that’s because I had only met the guy 5 minutes before he was inside of me. It was good though, and I didn’t feel any remorse or guilt over letting a stranger take my virginity. Probably because, I had handed him my virginity on a silver platter (but he’ll never know that). I had been waiting for this moment and thinking about it over and over again every single day. I psyched myself out every day, but in the end, I’m glad I did because I was ready. 100% ready. My only complaints were that he wouldn’t go down on me, wouldn’t make-out with me after I gave him head, and he didn’t kiss me goodbye…I’m not looking for any type of relationship with this guy, but I mean c’mon you were just inside of me and I was all over your naked body and you can’t even give me a peck goodbye?! I don’t regret it a single bit — I was safe (birth control and condom), well educated, and mentally prepared. And now I’m hungry for sex. Got plans to see #1 on Friday and to fuck #2 on Saturday. If #4 ever texts me, I’d probably fuck him too.

But one thing that having sex taught me was that it didn’t change me. That “good girl” everyone used to know — she’s still here. She still values her family, friends, her religion, and her education. She still feeds homeless men on the streets, and donates her extra money to charity. Sex didn’t change me, it may have added to my confidence a little bit, but it didn’t change me. But maybe, you shouldn’t call her the “good girl” anymore. And maybe you shouldn’t call the girl you think is bad, “the bad girl.” Maybe you should just call them by name and understand that we are all pretty similar when it comes down to it.

Sex doesn’t define us and losing your virginity really isn’t that big of a deal. It’s something that you should do when you’re ready. I was ready. Even if it was with a complete stranger (and probably a little risky), I was ready. And now it doesn’t consume my thoughts, I think about it pretty frequently though and I’m hungry for more, but it doesn’t stress me out anymore and I can focus on other things that make me happy too…but I have to say, I’m glad I finally know that sex is one of those things. To the next guy though; go down on me please.

Epilogue: I decided to go back to school part-time and now I have a job that I kind of like…and I still love sex. Thought Catalog Logo Mark

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