How to Lose Your Virginity ...And How Not To (5 page)

UNCLE KNOWS BEST
Corey, 34
I was cruising down the back roads of Michigan on my Honda Spree. I’m minding my own business then I see this girl in a Bon Jovi, stone-washed jean jacket with the fringe, walking along the side of the road. I was 15, this probably would have been in 1988.
I whip up next to her like I’m on a Harley or something instead of my little scooter, and I say, "Hey. What’s going on?" She’s like, "Going to the store to get some smokes." So I’m like, "Sweet. Want a ride?" like hop on my fucking tiny Honda Spree. It was the first time I rode with someone else on that scooter and it could barely take off. It was bogged down so I had to run along side it to get it moving.
Finally I get the thing going fast enough so we won’t tip over. We’re going down maybe a mile and she starts feeling my stomach. Then she reaches around and grabs my package, I’m like, "Whoa." "Pull over," she says. In Michigan there’s a lot of like two-tracks where you can just peel off into the woods. We find someplace secluded and start kissing.
We lay down in the dirty, sticky pine needles. I get on top of her and she takes just one of her legs out of her Palmettos, not even Guess jeans, but like the cheap Palmettos. At this point in my life I had not even jacked off. This was it, this was the very first. We’re doing it and it was the weirdest thing, my leg cramped up and my body seized and all this stuff came out of my penis and got all over the place. It felt really good but I was alarmed by it.
We got dressed and I drove her to the gas station and I didn’t even get her name. She got cigarettes and I filled my tank and I peeled off. I was still freaking out about the orgasm. AIDS was still mysterious and scary to me and I didn’t know if stuff coming out meant something was wrong. I didn’t know. So I went home and I couldn’t tell my dad so I called the only person I knew I could talk to about this: my mom’s brother, Uncle Lenny.
Uncle Lenny is totally super cool. I’m 34 and he’s 75 now and he still gets all the chicks. Really laid back and he’s kind of connected to the Detroit underground. I knew he was the guy who could give me some insight into what went down. I told him the situation and said, "I don’t know what happened. This like pus stuff came out of my penis." He was like, "You never jacked off before?" I said, "No." He was like, "Get into the tub. Draw a hot bath. Burp the worm for a few minutes and tell me if that stuff comes out again."
I followed his instructions, got in the tub, jacked off; it felt good and I was like, "Oh, awesome." For some reason it all made sense to me.
REACHING FOR NIRVANA
Emil, 36
Back in high school, in North Austin, sex wasn’t the first thing on my mind but I always wondered when it would happen. At the time I was more concerned with making a lot of money and a friend of mine and I created a business… well… manufacturing ecstasy. He actually got in trouble for it. I, by chance, missed out on any repercussions.
This was back right when ecstasy first started to get big. That was my thing in high school. I would go to a party, hang out. I always had girlfriends but I never slept with anybody, and the first girl I ever wanted to really sleep with, we talked about it, she was uncomfortable with it and I was like, "OK. Not a problem." As I started straightening out, stopped selling and trying to turn a new leaf, I became a Buddhist and my best friend at that time, Owen, his mother was Buddhist. That's how I was exposed to it, through her. We had talked about how the biggest things you could do that are wrong were stealing and lying. I never stole anything, I never lied about anything. I sold drugs, I did a lot of things that were really fucked up according to societal views but according to her she's like, "There's nothing wrong with that." We would chant together, we'd smoke pot, get high, hang out. She told me, "Anything that you chant for, you'll be able to get." And this woman was the most incredibly beautiful woman I had ever met before. She was married, she was my best friend's mother, not to mention my family's next door neighbor. My parents didn't really talk to their family because my parents were hardcore fucking Episcopalians - different worlds. But I would go over to that house all the time and I'd chant and... and all I ever wanted... I wanted to be with her. Was her husband going to have a problem with it? I didn’t know. That wasn't an issue as far as stealing or lying. He was a vice president for a pretty major international financial conglomerate, so he was never home.
Months had gone by since I started chanting and there were other girls that I had been with, made out with. I went down on girls, girls went down on me and you know, according to whatever you think sex is. Had I had sex? Not really. Every single time the possibility of sex came up, you know, they were hesitant. It's like OK, not a problem. I wasn't out to hurt somebody. If they didn't feel comfortable with sex then that's cool. We'll drink and hang out, we'll have fun, we'll take some X. We don't have to have sex, we can do other things. Kissing and touching was great but at the same time, these were young girls. Loretta on the other hand was a woman and incredibly beautiful. And every day she’s all I'd ever fucking chant for.
Then one day, I'm at the house and her son Owen and our other friend Jay were like, "We're gonna go out and do some military maneuvers and sleep out in the woods." They were hardcore into playing D&D but they also liked to go out and do weird covert operations and fuckin’ sneak around people's backyards. I was like, "All right dude. I'm just going to spend the night at your house. You know, if that's cool with you." They left and Loretta said I could watch a movie with her in her bedroom. So we're sitting there watching a movie, the movie that actually later on got me thinking of joining the Navy... An Officer and a Gentleman. And there's some steamy parts in it.
She's in her bed and I'm lying on the floor and she says, "You can lie on my bed if you want to." So now I'm lying in her bed and she had always told me how attractive she thought I was. She never looked at me as though I was the type of person her son was, running around in the woods playing war games. She thought I was very mature. Nobody else was there. Her son was gone, her husband was gone. It started with her putting her hand on my arm and we made love for hours. I had thought, from the time I was 12 years old until the time I was 15 years old, about sex with girls but I knew it wouldn’t be a pleasurable experience for them so I never wanted to go through with it. Not to say that it was a religious experience but the fact remains that it did enlighten me spiritually... it was incredible. And she was my spiritual teacher, as well as my sexual one.
Nobody knew what I was chanting for. Her son didn't know what I was chanting for. I wasn’t gonna tell Owen that I wanted to do it with his mom. Chanting and praying for what you want, it's inside of yourself. As far as the prayer goes, you're not verbally asking out loud, it's just the heart's desire that is inside of you, what you want. To actually be with her after wanting that for so long it was very spiritual. And every time that I've been with anyone else after that you know, I always looked at sex as a spiritual event as opposed to just having sex... just doing whatever with anybody.
All my buddies growing up, they'd screw whoever. They didn't care about people's feelings or emotions. But for me, if I'm to learn how to make love to a woman, I need to learn from a woman.
Owen found out about it though. Our buddy Jay told him. Because... once again... high school, these guys were trying to have sex with whoever and whatever and Jay was sleeping with this girl Donna and he'd never been with anybody before so he was always pre-ejaculating all over her. But Donna also had a crush on me and so she and I later on slept together but because I'd already slept with Loretta it was like I knew what I needed to do to make this something enjoyable for her as opposed to just concentrating on how I was going to get off. Donna had told me what happened with Jay and wondered why I didn’t have the same problem. I was like, "Well I need to tell you something. I slept with Owen’s mom." And so high school still being high school, she told Jay and Jay told Owen and Owen confronted me during our high school graduation.
He was all right with it. His mother was married to his stepfather so she had obviously had several different men in her life before. He wasn't upset with me but he was weird about it. But what can you do? It wasn't like she was drunk, I didn't take advantage of her. If anything she took advantage of me. She stayed married to her husband and I don't think he ever found out. But it was great. And it wasn't like something she did all the time, sleeping with a bunch of young guys. I waited for the longest time and then when it happened for me it was... it was religious.
BIG BROTHER KNOWS ALL THE TRICKS
DJ Ronrific, 33
I'm originally from St. Joseph, Missouri. Been out in Denver for about the past 20 years. I left the "Show-Me State" when I was like eight years old, moved up here to Colorado and lived in a suburb of Denver called Arvada. It’s predominantly, I’d say, 95% white.
The first time I kissed a girl I was about 13 years old. Kissing pretty much just lead to other things, you know touchy-touchy, feel-feel… experimenting. She was my neighbor and her name was Charity. We always played downstairs at my house. Pretty much how it started out was like with most kids, "Let's play doctor." It stopped there for a couple weeks and we went back to just being friends. Then one day it came down to it. We’re back in my basement, that’s where Mom always sent us kids, you know, "Go down there and play." So we're down there playing around and it was me, Charity, and two of our other neighborhood friends. We had a pool table and we were playing pool or whatever. Anyway me and her got to wrestling and it led me to getting an erection. She could feel it which got her kind of curious, but also kind of scared. We were both scared, shocked. We’re still wrestling around and things and we started kissing. Then I started feeling on her and she was happy with that and now we’re both really horny.
The other couple was still in the basement and they were laughing and kissing and doing their thing. They were pretty much boyfriend and girlfriend so they were in their own corner.
Charity and I got to rubbing on each other more and then pants came off so I started rubbing it on her vagina. That got her hot and I was hot too. I'm trying to get in there she's helping me at the same time. I'm so erect and she pretty much gets the head in for me. We're both virgins, you know, so of course she’s tight. So anyway I get the head in a little bit and to make a long story short... after I got the head in after a good minute, I was done. That's it, all of it down. My virginity was broke, hers was partially broke because she experienced something, but she didn't get to climax like I did.
So we’re sitting there underneath the pool table and she's like, "Oh, wow." And we got semen everywhere and we were freaked out about that. And we're looking at each other all crazy ‘cause for one thing it's a black guy with a white female, plus she was new to the neighborhood. She had never had a black friend or even talked to a black guy before.
We were kind of distant toward each other and a couple of weeks down the road, eventually we were in the basement shooting pool again and the pants came down.
I had had a talk with my older brother and he told me to slow it down a bit to make it feel better for her. He was 18 so of course he knew. He was like, "Aw man, it happens to every male." So he gave me a little knowledge, you know slow it down, kiss on and rub on her clitoris and rub on her boobs and things. And I'm like, "Clitoris!? Wow! I'm 13." You know they gave us a little bit of sex education, but they just said how to make babies, they didn't say how to make it feel good.
So I get to rubbing on things and I'm taking his advice and I’m concentrating so much on what he told me to do, so my erection went away. I get to rubbing on her vagina and everything and I didn't know it but I found the clitoris and I felt her jump and she's like, "Huhhhh!" You know like, "Ooh, what was that?" It kind of shocked her a little bit. Body kind of clenched and shivered. Bam! New discovery... for me and her. Of course she knew what it was, it's on her body. But this was the first time she felt someone else touch it.
So now I'm rubbing on that and everything and kissing on her titties and things. It pretty much got me erect again, so I'm like, "Wow, I got to try to not bust a nut so quick like I did last time." So I get down there and I'm rubbing and I'm so erect I can't really get in cause she's so tight. I had to have her take her two fingers and try to hold her snapper open, her vagina. So she kind of opened it a little bit and I'm rubbing on there and I get the head in, and it got in a little easier this time. And she's draining on me, you know, and I'm like, "Whoa!" Once again I almost nutted. I pulled back and kind of walked away for a second from it, you know, tried to calm myself down, like I was told to.
Pretty much what my brother told me was "Shit, man, take a sandwich or a Twinkie down there. If you're gonna bust, roll over and take a bite of Twinkie or something. Give your guy a chance to calm down." Anyway so I back up off it and walk away for a second. I settle myself and I come back. I get to rubbing on her again and I was like, "Wow, hold that open." I'm so erect and I get the head in and she starts draining on me again.
We get back on the grind and I'm moving back and forth, you know, and in the meanwhile she's pretty much got her nails all in my shoulders and I'm like, "Arghhh," about to go down cause my back's hurting. She’s getting a little loud and I’m trying to jam it in there and she's pretty much like, "Stop, stop, stop." I get scared, I stop like, "Why? It's supposed to be feeling good, right?" She’s kind of holding herself like, "I don't know... I want to quit." So you know, wow. Did I hurt her or something? But of course I’m a male so I’m also thinking, "Give me more." She’s kind of crying a little bit and I'm like, "Whoa, should I cry too?" I'm kind of freaked out. We get to talking and I'm like, "Wow. I'm sorry if it hurt," things like that. Anyway she's, "Oh, it's OK. It's just me." We ease back into it and we’re kissing and rubbing and I'm on top of her, she's on the bottom. I got her legs open and had her hold it open once again and I got the tip in and we're trying. She's just like, "Just be careful and be slow." So I'm being careful and slow and it's wet and it’s starting to get in there a little bit. In the meanwhile I'm like getting ready to nut so I'm trying to stop and just hold it there and she's squirming and I'm like, "Whoa, easy." I'm trying to hold her from moving to calm down a little bit, all of it wasn't in yet. I'm like, "Wow, before I nut I need to at least try to get it all the way in there." Like my brother said, take your time getting in there and then when you do, take your time when you’re in there.