How I Lost My Virginity
July 23, 2008 
30 Comments
How I Lost My Virginity by David Wygant
Over the weekend at the bootcamp i was asked by one of my clients how I lost my virginity and if it was a special night.
Lets just say it was and still is a very funny story that i love to tell.
Todays video is all about how to expand your social network.
I have been asked this question so many times that today i decided to share with you one of my most comical days ever!
I was in college, and I remember my roommate was named Jim – he was a big football player for Northeastern, and we were freshman. We’d drink on the weekends – he’d get a case of beer and sit in front of my black-and-white television. Black-and-white: it was 1980!
He’d sit in front of my little 13” TV – he watched that TV so much, he burnt the bulb out! So he sat in front of my TV, and we’d drink a case of beer. One night, Cindy Cassman and I got high, and we were stoned out of our minds. I’d did not have much to eat, and I was stoned.
We’re walking around the dorms, and we went back up to the room, and we get naked. We’re fooling around, and she asked, “so, do you have any condoms?” Of course I did – I had 36 of them! When I went to college, I bought three dozen condoms because I was thinking, college girls? I’m going to get laid! I was the low man on the totem pole.
So I had 36, but they were the red box – the unlubricated ones. The cheaper ones. So I said, “sure I’ve got some rubbers,” and I grabbed one and put it on my dick, and I start to feel it getting softer, and I’m thinking, oh shit, I’m nervous…
So I quickly get on top of her and as I’m getting on top of her, it was like my dick saw the vagina and just freaked out – it just fucking lost it. I came before I even got inside her. And I started mumbling something because I was so embarrassed, and I was just mumbling.
I took the condom and I threw it across the room. And you know – at 18 years old, you’ve got big loads! You could hear the thing thudding against the wall. At 45, your loads are pretty light – they could fly for a while. So I threw it across the room, and it might have hit Jim – but he had a case of beer, so what the hell did he know?
So Cindy looked at me, and asked, “well, what happened?” “Oh, um..” I grumbled and pretended to pass out. And I lay there, and I remember the whole night thinking, holy shit man – 18 ½ and I almost got laid, and I blew it – literally. This is ridiculous!
The next night, we decided to go out again, and we went to this place that served pu-pu-platters and scorpion bowls. In Boston, it was a bitch to drink – in New York, the drinking age was 18, but in Massachusetts the drinking age was 20. So I had my paper license from New York – every other state had picture licenses, and so I couldn’t get into any bars.
I was the low man on the totem pole – except for this one Chinese restaurant, which served everybody. And it was a stereotypical Chinese restaurant: you walk in there, broken English, “oh we help you very much tonight.” Everything was very stereotypical. The umbrellas in the drinks – it was hysterical. So we went and got a scorpion bowl, and we got loaded.
At this point, you’ve got to think about my stomach – now my first 21 or 22 years of my life, I was known as “diarrhea Dave.” You have to realize a night of drinking the night before with some beers and a scorpion bowl coupled with bad Chinese food – you have to figure what was going to happen.
So here we are, we sucked down the scorpion bowl, we sucked down the Chinese food, and we go to her dorm room. We get there and we’re naked again, fooling around, and all of a sudden I saw a diaphragm. I knew she had a boyfriend back home, but I guess the diaphragm was reserved for him – that’s what you do at 18, you reserve your diaphragm for your boyfriend, but you can still have sex someone else!
She looked at me and asked, “do you have any condoms?” And I said, “no. Do you want me to get one?” She answered, “absolutely.” I’m thinking, great!
It’s 1981. I put on my tight jeans, my white and brown-tipped cowboy boots, and my leather jacket. I’m in Boston, and it’s February. I walk out of her dorm, which was right around the corner from my dorm room. I walk out and around the corner, and I start running. I’m thinking, I’m getting laid finally! I’m so happy.
And as I turn the corner, I wipe out on a patch of ice, I go flying up in the air and land right square on my hip – BOOM. I’m lying there, with the wind knocked out of me in the middle of Huntington Avenue in 5° Boston ball-breaking weather, trying to get a deep breath.
Finally I get a deep breath, and I get up and realize I’m hurting – it’s throbbing a lot. I landed right on my hip! I’m like limping my way back to the dorm, it’s cramping up, and I’m thinking, goddamnit this hurts! This is going to bruise; it’s going to be ugly.
So I get back into the dorm and all of a sudden I feel the scorpion bowl start to move around a little bit. I hear this sudden noise and I realize, oh, man – I have diarrhea! I don’t even make it to my floor – I make it to the third floor men’s room, and I go in the toilet and I’m basically hanging out for quite some time.
I’m there for like 20, 25 minutes –i was so nervous and my nervous stomach was acting up to say the least. I came the night before and I couldn’t even get inside her – now we’re going to try to have sex again and this is 18 ½ years of pure pressure building up!
So finally I emerge from the stall, and I was white as ghost. I go up to my room and I get a couple of condoms. At this point, it’s about 45 minutes later.
As I walk back to her dorm room, I see the patch of ice and walk AROUND it. My hip is still killing me, my stomach is burning, and I’m dehydrated from having the runs for 45 minutes!
I get there, and she asks, “what took so long?” Now I can’t tell the girl that I’m about to have sex with for the very first time in my life that I slipped on a patch of ice and had diarrhea – these are the reasons it took me 45 minutes!
So I said to her, “I couldn’t find the condoms.” So I get undressed, and I’m looking at my dick, and it’s starting to get a little bit bigger. I’m thinking, thank god that’s still working! Sometimes when you get painful diarrhea anyway you lose all sense of sensation in the rest of your body!
So all of a sudden, I look at her, and she says, “well aren’t you going to warm me up again?” I said, “fuck no! Let’s just do it, I’m ready,” I’m still turned on. Meanwhile my stomach still hurts, my mouth is completely dry and I have an awful taste in my mouth from getting sick.
And you only do this in college – I put the condom on, I’m still somewhat hard, so I do the Popsicle stick method: where you take your dick between your fingers and you start jamming it in there? You figure that the warmth will get you nice and turned on.
So I jam my dick in there, I move once, and I cum! I’m thinking, man, this is crazy. I was in there for three seconds! She looks at me and says, “I thought you’d said you did this before?” I then learned the greatest excuse ever, which we use throughout our entire lives (some of us): I said, “well I’ve never been so turned on. Don’t worry about it. It will bounce back up in 15 minutes.”
Fifteen minutes later, it bounced back up – I’m rock hard now. This time it’s going to be good. So I put the condom on, and I get inside of her, and after five seconds, I fucking come again! I’m thinking, This is ridiculous! I couldn’t wait to get back in, and this is how it ends? I was so embarrassed; I couldn’t ever see her again.
That was the end of Cindy and I but she had a cute friend that I also like.
I should ask out this girl Maryanne, who was really cute. She was Cindy’s friend, and I asked her out. We had a date, and she cancelled at the last minute. Do you know why? Because my nickname was “one pump!”
So I transferred to American University because I could not stay there with the nickname “one pump.” That and I hated Northeastern.
But that’s how I lost my virginity. It sucked. The worst.
And my high school girlfriend, who didn’t want to sleep with me? When I came home after quitting Northeastern in March, I had like seven jobs that summer. One of them was a delivery guy for a pharmacy. My high school girlfriend decided it was time for us to sleep together, so we had sex like six or seven times a day.
So I made up for it! Every morning I would pick her up before high school. I had to drive my dad to the train station every morning by 7:35, and hustle from Mamaroneck all the way to the other side of the town to Scarsdale.
My girlfriend had first period free, and her dad would be pulling out of the driveway as I’d be pulling in – he wouldn’t see me. We would have sex, I’d drive her to school, and then I was the delivery guy. So whenever she had a free period, I’d pick her up and fuck her. So we’d have sex like three or four times already by 3:00. It was great.
She used to say to me, “god, do we have to do it this much?” And I’d say, “that’s what you do when you’re in love: you have sex all day.” The typical depth of a 18-year-old!
So by the time 3:00 rolled around, I’d smell of sex the whole day, sweaty – I was always sweating. I was stealing a box of condoms a day! This guy Dwayne and I would take everything we wanted – condoms, mints, other things. We would just take it out, throw it in the garbage, and pick it up on our delivery run.
I was the condom broker with all of my friends too. They all needed them, and nobody wanted to buy them, so I was always driving around in my Toyota – actually, I had my car by then so I didn’t have to drive my dad to the train anymore. I was driving around with boxes of fucking condoms – cases of them in the back of my Celica.
And that’s how I spent my summer..
So I made up for it. But virginity, man, that was the worst. God, I hated being a virgin. It was the absolute worst.
Todays question is how did you lose your virginity?
On a more serious note todays video talks all about expanding your social network and why it is the only way to meet more members of the opposite sex.
lol David that reminds me of my first bj. After she put my penis in her mouth, i can not control it at all and just let it out after like 5 seconds or less.
She wasn’t too amused :/ we still haven’t talk until t his day.
Great Story…
I was seduced! At the very tender age of 16 – I had no idea what I was doing, except that it felt so very very good.
It was New Years Eve, my g/f at the time was alone – she invited me over -got me drunk and then took me upstairs and took advantage of me!
Ah that girl…. will always have a special place in my heart!
damn you guys. I am still a virgin!
Not giving me the greatest of confidence here, David
David!
This was a great story, lol. Man, you need to share more like this! Im 19 now, and my first was about 2 years ago, and it was really akward to say the least…but ya it felt great to get the whole “V” thing off of my chest. Lol, me and my friends also never want to buy condoms, so one of my friends stole some and he gives them to us. One time however, I went into my university’s health center were they give you free ones and it was pretty akward. A 19 yr old guy asking a 45+ yr old feminist for condoms lol. never the less, a great blog as always!
Dan
Also, too anyone who is a VIRGIN:
Once you do it the first time and look back on it you realize a lot about how to properly do it and everything it involves. When I first did it I had no real clue except for what I have seen in porn, which isn’t the best way to do it lol.
Dan
Thanks!
One day I will share the day my brother lost his that is a classic as well!!
Tariq
Your day will come!
Plus the first time really is not that great!
If mine did not have the crazy happenings it would have been a 3 second night!
Kevin
You were seduced!
That was always a fantasy of mine when I was 16!
I was so nervous at 16 it would have taken a whole bottle of vodka to calm my nerves!
LOL
this was a great story! So many things happen in college dorm rooms…
Mine was five years ago.
I used to play soccer for a local team, where my parents live. I seduced (somehow it just happened) my team-mate girlfriend and took her on the date the following week.
We proceed it to her room on second date and Slava lost his virginity at the age of 20!!
How funny is that!? I lasted exactly 3 seconds and of course I told her that she made me sooooo hot that I just could not resist her awesome body…
She took it but from then on I got better
David,
thank you so much for your advice, I feel more and more confident. I basically listen to your 9th episode of the Mastery series over and over again
It gives me so much energy man!
Great job!
Glad that was a long time ago …
That was sooooo very funny, thanks!
Mine was in a car in a cemetery my senior year in high school. Ever since then I have a phobia about being in a cemetery, I thought that Freddie or Jason was going to pop out of a grave and whack us any minute:-)
Dan
That was funny!
I once saw Jason running in my living room when I had too much tequila!
Glad he did not show up on de virgin night!
mine, was in a threesome at my friends house.. it was quite amazing.. and a hopefully not a once in a lifetime experience.
cheers,
Joe
Joe
A threesome i am really impressed. That was a dream for me.
I agree with Dan– blogs like these shed light on real nuances of what it’s like to be young.
David, get a load of this one:
My first time was nearly three years ago (I’m currently 19). It all happened after a day of playing intense doubles tennis with a few friends. At the time, I was a bit out of shape and quite fatigued for the rest of the day in question.
Then, I get a call from the girl I was dating. We decided to meet up at my place– luckily my parents were not home–and I showered up before I heard the doorbell ring.
To be honest, I was surprised by how smoothly everything was going– no condom complications, no initial “one-pump” …but then… both of my calves cramp up!
So now I’m in between thrusting for dear life and a muscle contusion that could bring down the Berlin wall! I can look back on it all now and laugh, but damn was that first time painful.
Looking into the eyes of my girlfriend after our first time– I saw she was crying. I was too, but only out of pain…I never did tell her that that was the real reason for my tears!
I guess that experience taught me the real value of staying hydrated and being limber!
>>>>>>>>A threesome i am really impressed. That was a dream for me.
It still is for me!
Dan
A threesome is great as long as it is all about her:)
Slava
GReat story and i think most men lose there virginity in the dorms!!! and most are one pump at best!!
Was that during the summer break?
Cody
Nothing is more painful that that cramp in the calves.
I have had that happen during sex once before and you feel like you are getting shot.
Almost impossible to maintain the erection!!
Joe
A 3 some.
That is a great way to lose your virginity!!
Mine was with a mixed doubles partner during a tennis tournament. I had lost in the first round of singles and was later paired up to play in the mixed doubles draw with this really cute girl. She came up with me to my hotel room where I was supposed to just grab my rackets. Well, let’s just say that I ended up scoring some aces with her in bed. We missed our doubles match, but it was sure worth more than whatever prize money was available in that tournament. I was 22 at the time.
I was in love and lost my virginity on my 17th birthday, my girlfriend age 16 was also a virgin. It was a planned event. We had months of being naked fun leeding up to the big day. Its a great memory, but in the end my heart was broken, and I was changed forever! SIGH! Love sucks!
..Lost mine at a whorehouse, at 20, I remember being nervous…I did go back for more…
Sometimes… being prepared with the right knowledge makes your first time just that much better ;p
….I remember asking questions, few, not very many, (few couselors/psychologist) risk talking about sex, and what leads up to it.
Hunter,
I remember doing a lot of my own research. I never really asked anybody… except look for great books and videos on the topic… b/c I knew I was a “late bloomer” so I had to “compensate” for lack of experience to make my first time a good experience.
Personally, videos along with a couple sexual psychology books were the best instructionals… and no, I’m not talking about porn when I’m referring to videos.
Oh lord, it’s been a while since I’ve been here. I hope you all are well.
I’m with Tariq. Still a virgin. I can’t speak for him, but I intend to stay one until I’m married.
lmao, this reminded me of some pathetic things that happened to me. Like instead of press on hang up on the phone, I pressed on speaker while having sex. Luckily, my parents weren’t the callers. Then I was having sex with my first boyfriend(well, real boyfriend, not foolish middle school crap at spin the bottle) and we had one condom left and it was on the counter near the bed and the guy hits it by mistake and it goes under the bed. He had to move the bed and get it and I couldn’t stop laughing. My first blowjob was probably the lamest thing ever. I was afraid to do anything because maybe I’ll hurt the guy.
I’m thinking now… If I’d have a lover who is virgin and he’d tell me, I’d make it a game and dress as a teacher for him and make teaching him how to have sex fun.
I don’t know, if I really care for the guy, it could be fun and I wouldn’t care. But if it would be a one nighter and he’d be a two pump chump… 
I am not the Cindy Cassman you’ve posted about…
I google myself frequently as I’m an author. I’ve always done so under my current name. Tonight I decided to google me under my maiden name and your blog post came up.
So I just want to let your readers know, I was Cindy Cassman before I got married, however, I am not THIS Cindy Cassman this man is refering to.
Everyone has the right to blog what they want, so being the “good sport” and “Christian” that I am, I’m not going to ask you to pull this post. However, I hope you will maybe “update” this info on this particular posting at some point (preferably like within the next few minutes – hint – hint) with a NEW post, not an edited version, to let your readers (and google bots!) know that you were not refering to your “loss of virginity” with me, but with another person (sorry, can’t think of her as a lady) with the same name.
… and if you’re unsure, you can always pop in to visit my website at CindyBauerBooks.com and click on my biography page. Though a wee bit older, I still look pretty close to what I did in my “younger” days……..
Thanks and God bless you anyway, son.
Cindy (Cassman) Bauer
ps… my maiden name is very uncommon. I’ve run across a few on the web, but NEVER another Cindy! Wow! My mouth dropped to the floor on the name and about dislocated my jaw on the blog posting! If I’d had a few more “years” under my belt, I probably would’ve had a stroke or heart attack! Egads!!!