Awkward Firsts: Losing Your Virginity Isn’t Always Fun
October 26, 2008 12:00 pm Posted in Relationships, Sex Sarabeth - University of Texas g+ page

Some women get to have the dreamy, stereotypical first time. The love of your life surprises you with a romantic evening alone and it ends up in the bedroom. He tells you he loves you and all that jazz.
Well, you know what? Some of us would like to forget our first time, and “some of us” includes me. I’m not saying I regret it, but I sure as heck wish I’d put more thought into it and had better judgement.
I was young and stupid, and depressed. I was 16, a junior in high school, and had never been in love. My friends were hooking up and wondering why I’d never been able to have a boyfriend for longer than a week. I was never the “It” girl, I was more of the “one of the guys” girl. I’d never been told I was beautiful by any guy, I’d never been told I love you by anyone besides my parents.
So, my self-esteem really wasn’t all that great when my ex-boyfriend put the moves on me. During a play rehearsal. In a storage closet. And the cherry on top was the fact that after 2 minutes he just got dressed and left. TOTAL D-BAG!!!!!
No romance. No foreplay. No cuddling afterwards. Sooo not the ideal conditions to lose your virginity.
At times I regret the choice, but overall it’s not so bad. It’s a funny story to tell at parties, and it pretty much prepared me for any awkward sex situation that would ever happen again. Basically, it prepared me for the real world. Plus, now that I’m having great sex with a man I love, it makes me appreciate it more. My bad first time ended up helping me in the long run.
I know I’m not alone out here. Any other awkward/bad first time stories?
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Meg says:
Sun, 26th Oct 20087:49 am
My first time was supposed to be romantic, but right in the middle of it our friend who had moved away and was coming into town that day, and my boyfriends other best friend bust through the door.
We were happy to see our friend, but mad at the same time. Now we just laugh about it.
Carla says:
Sun, 26th Oct 20088:07 am
i dont know whats worse, whether remembering an awful first time or you cant remember at all! Honestly, mines a little hazy how it happened. I know I had it with my very first boyfriend who I've been dating for almost 4 years (now he's my ex- don't ask). but i think we did it in his bedroom while his parents were just across the street at a neighbours bbq party. We did it once and it lasted for probably 5 mins or less. I asked him if we could do it again (coz obviously i didnt reach peak) but he got worried that his parents might come back home… i think tht was it… We were 16 when we met and we did it at 18, unlike any other couple in high school, we kinda waited till it was the right time. I thought that was sweet, and yeah, i dont regret that at all.
oopsie says:
Sun, 26th Oct 20088:59 am
my freshman year in college. i was pretty much a fat loser in high school and guys didnt acknowledge me and if they did they just wanted my homework. but i lost 50 lbs before going away and guys actually found me hot and cool and such so i was just happy to have someone want me. i was drunk though. with a guy who i was drunkenly hooking up with for a semester-which hey i held off for a whole semester. as you can tell my self esteem was in the crapper. but i've learned and grown from the experience and i know i'm better than that now. i just wish i could have my first time back…. well at least the guy was smokin
Lyra says:
Sun, 26th Oct 20089:02 am
mine is pretty boring compared to those stories..
i was 15. it was in the summer holidays, while i was visiting my native country (i'm an international school kid). i kinda had only known him for.. two weeks? yeah, two weeks. his first time was at 13, so he knew what he was doing. also, he loved me. me? nah. didn't really care. i was just curious and he was a sweetheart, so, whatever. i don't regret it, even though i had zero feelings for him.
Audrey says:
Sun, 26th Oct 20089:08 am
I wish I could erase the sterotypical senario from my head… My moment of truth happened in the backseat of a jeep.. at the city park. Pretty sleazy. I still shudder with horror sometime when I see a certain make/model of Jeep. My only saving grace is that we weren't interrupted by the cops or something. Although that could only make the story better now….
Sam says:
Sun, 26th Oct 200810:23 am
Uh, my first time involved being handcuffed to the bed in my dorm, and then my suitmate busting in through the bathroom door.
Awesome story though, right?
Laura says:
Sun, 26th Oct 200811:24 am
I lost my virginity when I was 21 to a guy friend who I was friends with for 6 years. He was visiting me at the time and we fornicated in a hotel bed. Haha. Now that I'm thinking about it, this is some funny stuff.
Overall, the whole experience really wasn't great. It was awkward, we were fumbling everywhere and he didn't know how to unhook my bra. Yeah I know, right? Anyways, it didn't last long. No foreplay whatsoever and it was so horrible that I told him to get off of me. Talk about a bruise to his ego but i lost my horniness and I knew I wasn't going to get it back with this guy.
He avoided my phone calls and messages for 2 weeks and I found out that he had a serious girlfriend the whole time. Talk about a major dickhead. I don't regret that I lost my virginity to him cuz I had to start somewhere but I wish he wasn't such a coward about the whole situtation.
Sam says:
Sun, 26th Oct 200811:57 am
My first time was with my then boyfriend, I felt ready; I was a late bloomer of 18. We start hardcore making out and all that jazz when he whips it out and puts on a condom after making sure it's what I wanted to do.. I lay there thinking 'wow this is it..' and then bam it was all over. One minute man? Probably like 5 seconds. It was bad and every time I was with him after it seemed to somehow be shorter.
Casey says:
Sun, 26th Oct 200812:44 pm
well I'd like to forget my first time, my virginity was stolen from me. But my first time willing was awkward It was with a guy I had a crush on and we had joked about doing it for awhile and then his 16th birthday I bought him a pack of condoms and he came over to my house after school and literally he put it in and went. It was less than 3 seconds. He just sat back and looked at me in horror. After about a minute of silence he asked me if I wanted to try it again, I said "no let's just go for a walk". Then we realized we had completely forgotten to use a condom.
Meg says:
Sun, 26th Oct 20081:15 pm
within the first two weeks i'd been at college, some smooth talking dickhead managed to get me into his loft bed. he had sex, i watched Laguna Beach trying to concentrate on steven & kristen and not the horrible pain i was in. He pulled a "bugs bunny on the moon" in about 5 minutes (i was thankful). after, we got into a shouting match after because there was blood on his sheets. pretty much as unromantic as it gets.
Dina says:
Sun, 26th Oct 20081:23 pm
what does bugs bunny on the moon mean?
Casey says:
Sun, 26th Oct 20082:04 pm
Dina, I'm only assuming she means he was bouncing (or thrusting) really really fast and a lot. But that's just a guess.
Cali says:
Sun, 26th Oct 20088:59 pm
it is a dane cook reference
Krista says:
Sun, 26th Oct 20089:38 pm
I was 18, I met him at a party, we started making out (it was a sleepover party cuz everyone was too drunk) and I knew he wanted to have sex so I asked if he had condoms. He ran around the place looking for condoms, finally found one, we wen't down to the basement and did it. Regular pain from losing it plus doing it on wooden floors. We actually had to stop because I was in so much pain and he couldn't really….stay in me…haha…I think he was a little too drunk.
Cookie says:
Mon, 27th Oct 200812:46 am
I can't believe you guys were all done in less than 10 minutes; mine lasted hours! Movie first (Happy Feet is kinda ruined for me), then drove out to a park with a lookout where you could see the whole city lit up at night. He was really fun and sweet and naughty…though we weren't planning on going the whole nine yards we got a bit carried away
marie says:
Mon, 27th Oct 20087:17 am
i was 19, and not in love, wasn't with the guy actually i had only hung out with him 4 times or so. i remember being ready to lose it, i hated being a virgin, not that i was embarrassed by it but i hated the way guys reacted to it when ever they found out,they made a HUGE deal about it.it just felt like a load on my shoulders. anyways back to the story i invited him over to my house while my parents were out of town to watch movies and whatever, and one thing led to another until he asked me if i wanted to have sex, i believe i replied with a "hmm…" and we laid in bed for about a min while i thought about it and finally said 'do you have a condom?'.it really wasn't a huge thing to me, i just figured 'hey he's nice, he's not crazy and he's hot..why not?'.haha. my first time lasted HOURS though, he was really slow and kept asking if i was ok or if i needed to stop, so that was nice, but it still really fucking hurt :/. we actually ended up together a few months after and we're still together a year larer. i guess it some how worked out.
Lucy says:
Mon, 27th Oct 20087:53 am
I was 21, lost it to my "friend" of 2 years at a party at his house. I was just talking to him drunkenly and he kept pushing a drink at me. Eventually we somehow ended up having sex. I remember it hurt a lot, and then he was a jackass to me from them on. Oh yeah and he booty-called me once a month later, and for some reason I went back. Damn, I was stupid.
Melody says:
Mon, 27th Oct 20087:56 am
I lost mine when i was 16 years old. he was my first boyfriend and we had been dating for about a month. i know i wanted it to be with him. so one day he invited me over when his parents werent home. i figured something might happen but i still wasnt sure. we started watching the producers in his room and one thing led to another and we started having sex. it hurt like a bitch and he felt so bad he was kinda losing it. but eventually got better and it started to feel good. it lasted about a hour which was pretty good for my first time. i could hardly walk after but i looked at him and i knew i loved him and he loved me.
Abernathey says:
Mon, 27th Oct 20089:36 am
Get In. Get out. Put on your jacket and get the hell out of there. I like that guys style.
Cuddling is for wussies.
Sarah says:
Mon, 27th Oct 20084:26 pm
Oh wow is my story interesting.
First of all, the dirty deed took place at church camp (I worked there; I wasn't a camper).
Second, it was definitely not all romance and rose petals. He was horny and I took the opportunity to finally prove to my then-boyfriend that I wasn't the innocent, virginal little girl he thought I was by giving him head (for the first time, I might add). Needless to say that I hated it because he wouldn't stop trying to force my head down (consequently gagging me–not cool).
For some unknown reason I felt bad when I stopped, so I told him I was ready to have sex. His eyes lit up and he fucked me for the first time on my bunk. I literally saw stars because as he thrust at me emphatically, my head was beating up against the head-board in time. All this made me wish that it was over in 1 minute. However, it took about 15 minutes of pain (both in the crown of my head and in my nether-regions) for him to get off and finally get off of me.
O, it is a night I will never forget (and never not regret).
Gina says:
Mon, 27th Oct 20086:44 pm
Ah, The Story. It was this guy I'd sort of been talking to this past spring. The whole thing is complicated, so I'll just give the highlights.
1) Before the sex, but when I was very naked, his best friend walked in.
2) He used this "tingly" lube that made my vajayjay sore for a literal week afterwards.
3) It lasted for-fucking-ever. No pun intended. We got started super late at night, and the sun was literally up before it was over. I'm estimating 40+ minutes.
4)Zero orgasms were had. I was too nervous, and he "held himself back". For 40 minutes.
Oy…definitely one for the books.
Lindsay says:
Tue, 28th Oct 20082:40 pm
Both of us were 15. I had known him for a year and we were dating for 4 months. We had just finished eating dinner, and the party was still going on downstairs. But we were getting antsy so we went upstairs. We began making out and doing the usual, when it got to the point when it was obvious when we were going to have to either stop or he was going to have to put on a condom.
I guess I was pretty lucky, my experience was really good. He was really sensitive and let me take the lead alot of the time. Honestly it didn't hurt at all. I think the actual sex lasted like 20 minutes. And afterwards we just lay there, smiling and holding each other.
nicki says:
Tue, 28th Oct 200810:00 pm
Oh wow, my first time was ughh interesting.
I was about to be 15, and out with some friends. They got boring really quick, and I didnt have to be home untill 12. I had met this guy who was older than me and thought he was just great. I was wrong. ANYWAYS, I called him up and he came and picked me up. i thought we were just going to hang out and stuff but no. He asked me if I ever has sex before I said no. He asked if I wanted to try, I felt so awkward so I said yeah.
[ keep in mind I was the girl who kisses one guy haha ] we pulled over at a park, and I cried through the whole thing it was so bad!!! the worst part was, I didnt know that your "cherry pops" your first time. so yeah his back seats were stained, and everyone found out about it.
Not a good time =[ but hey what the hell I was young.
Joe the Plumber says:
Mon, 3rd Nov 200810:30 pm
I couldn't wait to have sex so I actually had sex with my dog. I was only 13 and hadn't been through puberty, and it was a big dog, so I think the dog was ok.
jenn says:
Tue, 11th Nov 20089:24 am
My first time was when I was 19. My friend introduced me to her old neighbour when we went camping for may run, so we hung out for awhile. I was a a little drunk when we did it, so some details are fuzzy, but my friend and her boyfriend interrupted half way through.
Lully says:
Fri, 14th Nov 20086:48 pm
I was seventeen. He was seventeen. I'd vaguely known him for about five years (same school, some same classes) he refused to use my real name and instead called me by a similar name of another girl in our class. I called him by his full name he got offended so I started calling him Shnookum's as a joke. After that I saw him pretty much everywhere, it seemed like every time I looked up he was looking at me.
Sound like some romance story? Pfft. Hardly.
He invited me over to his house one afternoon to work on an assignment, since I was topping the class and he was trawling the bottom.
Things were said, various kissing took place, and somehow we wound up on his bed, topless, pantless, underwearless.
He whips out a condom says: Only if you want to.
Oh I wanted to. I was so naive, I didn't think it would hurt, at all.
He was a lot bigger than i'd anticipated, so, when the cherry popped and it hurt a lot I screamed, I just don't have a high threshold for pain.
So his parents come bursting into his room, freaked out. And well. That sort of ended the proceedings for the evening. I think after his father (who probably thought he was raping me) took him away for a bit of a talk, and his mum (who was totally sweet about everything) gave me a coffee. I went home.
He called me later, said he was sorry, asked me out. I said yes, he had a car, he had money, he had an incredibly good body. And when it came back to it the sex was great, just not the first time.
We're actually still together, and the awkwardness with his parents has disappeared, although it's still weird that they know what we do.
Lully says:
Fri, 14th Nov 20086:49 pm
my story was long. Sorry.
Cassie says:
Sat, 29th Nov 20087:53 pm
Well my first time was without consent…He got me totally plastered and then led me to the beach. Where we then went for a nude wade through the water and then proceded to have sex on a towel of his. I only remember little flashes of that night, but it lasted a measly 10 min. And he was just overall bad too…
But my first time willingly, that was amazing. We had just finished watching 2 movies together (Saw 3 and Stay Alive) and were just relaxing together on the futon in his room. Both his roomies were gone for the weekend and we just started really making out. At first I was reluctant to give in when he started grabbing for my zipper (due to the above occurence with that other guy) but once I did it was the most amazing sex ever. 3.5 hours straight with plenty of stimulation and such. He truly did care that I got all the possible pleasure I could. Thank God.
T says:
Tue, 23rd Dec 20084:21 pm
It happened on one of those swively computer chairs… can't help but laugh.
Shayla. says:
Thu, 7th May 200911:57 am
my first time was "okay".
boyfriend of four months, fifteen years old (he was seventeen), in his bed, quite drunk, but not too drunk that i don't remember it.
my main problem was the fact that i was so tight (true story. eurgh.) that it took a while to uh.. get in there.. and once he did it was just paaaaaain. then the cherry popped. even more pain. he seemed to be quite enjoying himself. hah.
it felt okay, but definitely no first-time orgasm.
it was good to lose it to someone i loved though, and them to still be there in the morning.
Brittany says:
Sun, 31st May 20094:29 pm
Oh God. First time, I was seventeen. We were at a party, I had had (quite) a few too many and decided to take a nap on my friends bed. A guy I had been talking to all night came in, we started talking, one thing led to another and we ended up having sex. It actually didn't hurt, but it definitely wasn't great. My friends boyfriend walked in about halfway through, and I ended up getting said friend very very angry. Oops
Willy says:
Sun, 31st May 20097:25 pm
shit man, I pops all kinds of Cherries in my bed
Emi says:
Tue, 11th Aug 20093:25 am
I made my guy wait, it was a few months before my 18th and he was 19 and we had been dating for years. We had been fooling around for months, doing just about everything but. He had already accidentally ripped my hymen, but it still hurt like hell the first time. Basically we were fooling around on the living room floor and I remember him being on top of me and I just told him to just do it, but he chickened out and I got ontop and did it myself. It hurt so bad I kinda fell off and we stopped for the night but we tried again in the morning and it was fun.
Sara M says:
Sun, 26th Sep 20109:07 pm
My first time happened when I was 19. I was a freshman in college and all my friends had lost it in college, so when a weekend football game trip came up I decided I was ready. It was a sorority/fraternity trip where all the guys ask a girl to go to the game with them, stay in the same hotel room, get wasted and have sex…pretty lame. I don't regret it but definitely wish it had been a more special experience
Ella says:
Tue, 5th Oct 20103:25 pm
my first time was definetly not romantic. just like you i was 16 and a junior and feeling left out that all my friends had had sex and i was still a virgin. so one night at a party i was at my ex boyfriend also started making moves on me. to make matters i was drunk and my judgement was definetly impaired. and he didn't use a condom. the one good thing about it was that it didn't hurt as bad as all my friends said it would and said it hurt them. i don't regret losing it then, i just wish that the circumstances had been different and i was in love… but it opened up the door to have great sex after that. i honestly don't believe your first time is the most important or most memorable, its just the beggining of better sex to come!
kerry-anne says:
Fri, 12th Nov 201012:01 am
Hmm im kindar confused and need help ? i had sex with a guy and it was my first time im only 14 and i think it was because i was too tight his penis kept slipping in and out and i had no pleasure what so ever i dont think my cherry poped but straight after i felt sumet wet and i like checkd and a little bit of blood come on my finger then after that none blood came at all jus like a drop on my finger does that mean my cherrry poped or not i couldnt carry on with the sex after 5mintues becus it hurt to much i mean the pain was horrible :/
lostitinthelovesack says:
Mon, 27th Dec 201012:04 pm
I just lost mine last week….
I'm 19 and I had been waiting for that special someone and that perfect moment.
Of course it was nothing like that
I met him when I was drunk and after I sobered up (I think) we had sex in his room on a beanbag chair with his roommate sleeping not 10 ft away
needless to say it wasn't what I imagined but it was good and he was sweet and gentle
now the question is……Do I try and contact him? or wast a one night stand?
shauna says:
Mon, 6th Jun 20114:22 pm
well, i was 12, he was 17, i was in love, he fingered me for the first time ever, it hurt really bad but i loved it, he carryed me to his car and strapped me down with the seatbelt, i trusted him untill i realised i was to embrace a penis, i wasnt positive about my actions and it hurt like hell, im not sure why he did this but i didn't see him ever again, i couldnt even walk. i swear i was drugged.
Olivia says:
Mon, 2nd Jan 20121:33 pm
I'm 15. I dated a boy my age for about 5 months twice. He was always really kind to me, and he an interesting person, and we never did anything sexual aside from cuddling. We had just broken up the second time when I told him I wanted to have sex with him. We were both virgins. He invited me to his house a few months ago while he was babysitting, and we did it. It was awkward to say the least. It hurt like a bitch, and I bled a little on his sheets. When we were done, he walked around singing "I JUST HAD SEEEXXX!" And just left me in the room so he could go play video games.
Well, a month later, he hooked up with my BEST friend. Behind my back, of course. So they both lied to me. He was trying to hook up with me AT THE SAME TIME. Knowing that hurt me so much. I obviously still liked him, and we cuddled every day after school. But now I know a lot more about him. Now he calls me a stupid whore… Girls, wait until you love him and he loves you. Be in a relationship, it'll be that much better(:
Kerryn says:
Tue, 3rd Jul 20125:16 am
Mine was like that too. Except is was with my family friend who was 5 years older than me (he was 21 and I was 16). Mine lasted about a half hour though. I was nervous as hell and he was gentle but still. Once we were done, I told him to leave even though I didn't want him to and once he left I couldn't stop crying. Before he left, he told me to make next time not so awkward for me and when we see each other again, to not feel weird around each other and to be relaxed the next time we did it. There was no next time, and now when I look into his eyes, I know he doesn't remember because he's that typical hot bad boy who says he loves you one minute and ignores you the rest of your life. He didn't even use a condom either and I had a pregnancy scare. My family (mom and sisters) know I'm not a virgin but my dad doesn't. They think I did it with my ex boyfriend who I was supposed to have sex with when I was 15. They think that because I told them that. They don't even know it's our family friend. Now that I'm 18, I'll tell them it was him, but I'm still iffy about it. March 7, 2011 is definitely a day I will never forget.
Ann Onymous says:
Thu, 27th Sep 20126:01 pm
YOur cherry did pop honey.
Ann Onymous says:
Thu, 27th Sep 20126:03 pm
Lol, learn english sweetie/
andrea babson says:
Sat, 16th Feb 20131:36 am
the same as yours,,i lose also my virginity when i was 12 years old and he is 12 also,,.but the diffference is i was not inlove with the guy..well..this is my story,,me and my friend xander,,played bahay bahayan..at the back of our house,,and he told me that,,.if it is ok with me..to have sex.., with him.. in my curiosity,,.i answered him yes,,for me to experienced sex,,it hurts me so much..after our sex..now that i was 18..i regret it so much,,with my whole life..that i did the bad things in my younger age,,
andrea bason says:
Sat, 16th Feb 20131:38 am
lol
andrea says:
Sat, 16th Feb 20131:41 am
is your cherry pop darling?