Where it happened: A friends house
Langauge: English
Sex: Male
Rating: 5
Category: Straight
My first time wasn’t planned and happened so fast that I didn’t even realize that I wasn’t a virgin anymore until someone asked me days later.
I had to stay with some friends of my parents because they had to go out of town for my uncle’s funeral. I knew their daughter from school, she was three years ahead of me, but we lived in a tiny town where the middle school and high school were one building so I knew just about everyone that went to our school. Her name was Missy, and I’d had a crush on her for a long time, so when my parents told me I was going to stay at her house I was elated.
Anyway, the first day sucked because Missy stayed at a friend’s house and her parents were both alcoholics that yelled more than they talked. I went to bed early, I had to sleep on an old broken down couch, and went to school the next day before they even got out of bed so I wouldn’t have to talk to them.
That day I saw Missy in the hallway between classes and she asked if I was staying at her house. She had never really talked to me before so I was stoked that she even knew my name.
I was happy to inform her that I was indeed staying the night at her house and she asked if I drank alcohol. I had drank a beer once before that, but I didn’t want to seem uncool so I lied and told her I drank “all the time”. That seemed to make her happy and she informed me that she and a friend were going to get some liquor for that evening and that I could ‘hang’ with them if I wanted, but I would have to chip in if I wanted to drink. My parents had left me some money before leaving so I gave her twenty dollars.
I hurried to Missy’s house after school full of the anticipation of spending time with her. I was disappointed when she didn’t come home after school and figured she had decided to stay at her friends house again and that they were going to use my money to get drunk.
But she finally showed up around 8pm and true to her words she had gotten some booze, a lot of booze. She had bought a bottle of Malibu Rum, a bottle of Black Velvet, a couple six packs of wine coolers, and a twelve pack of Bud Ice.
And she had brought a friend with her. Her name was Dana who was a high school drop out that had a reputation for getting in trouble and being a slut. She was a couple years older than Missy and though she wasn’t ugly, she wasn’t pretty either, just kind of plain and chubby.
After Missy’s parents left to go out to the bar, we hung out on the couch watching MTV and drinking. The first beer I had went straight to my head and I had to slow down so I wouldn’t pass out, but Missy and Dana drank like sailors- putting away two or three wine coolers to my one beer. I remember feeling cool because I was partying with older chicks and I couldn’t wait to tell my friends about the experience.
Around 10:30 or so her parents came home and we migrated upstairs to Missy’s room to listen to music and continue our drunk-fest. We all sat on her bed in a little triangle, trying to ignore the fight that her parents were having downstairs,and talked between swallows. I mostly just sat there and listened to them talk about guys, drinking, celebrities, and other random girl talk. They acted like I was just one of thier girlfriends and weren’t shy about divulging embarrassing stories or secrets. The way Dana talked I knew that the rumors of her promiscuity were true as she recounted fucking several guys and who had a big penis, who was a lousy lay, and which guys in town would buy her stuff so that she would sleep with them.
That went on for quite a while, but I was intrigued because all my friends ever talked about were sports, comic books, and the girls they wanted to kiss. There I was getting the inside scoop on what girls talk about and I was learning what things like ‘clit’, ‘going down’, ‘rubbing on out’, and many other sexual terms meant. My friends wouldn’t (and didn’t) believe me when I told them about the raunchy tales.
My interest was piqued when Missy, who by that point was slurring, said she liked to masturbate with cucumbers. Dana burst out laughing, but I started thinking about her laying right there on the bed I was sitting on and having sex with a cumcumber. I seemed a little strange that she would use a vegetable, but after I visualized her doing herself with one, I found the idea intriguing and arousing.
So far I had been mostly a spectator, but as I was lost in daydreams of Missy and the cucumber, I realized that Dana was talking to me. After I returned to reality, I asked what she had said and she asked if I was a virgin. I lied and said no, I didn’t want them to realize that I wasn’t cool and that they had just shared their sexual secrets with a young boy who knew next to nothing about sex.
I must’ve took too long to respond or something because Dana challenged me by asking who I had had sex with. I racked my brain to come up with a girls name, but I was too nervous and after a long silence I said I had screwed a girl that lived in Seattle. Dana demanded a name and I blurted out the first name that came to me, I don’t remember the name I said, but it was obvious that she didn’t believe me. She looked at me with a knowing smile and changed the subject. I felt like a fool and pretended not to be embarrassed, but I remember feeling like the biggest loser, and I was sure that Missy would see right through me and see that I was just a boy, not a man, and I was pretty sure that she had no interest in a mere boy. I was so ashamed that I couldn’t even look at her, and I had to pee for the millionth time, so I excused myself and got up to go to the bathroom.
When I stood up I realized, to my horror, that I still had an erection and the cotton basketball shorts that I was wearing did nothing to conceal that fact and Dana started cracking up laughing and pointing at my ‘tent’. I looked at Missy and saw that she too was giggling.
I practically ran to the bathroom and locked the door. I wanted to go home and die, but I couldn’t. I contemplated staying in the bathroom all night, but I knew that wouldn’t work either, so I decided to sneak downstairs and go to bed.
I used the toilet, then I tried to sneak past Missy’s room and down the stairs, but I was drunk and managed to trip and fall just outside Missy’s room. Dana came out and asked if I was okay. I didn’t look at her, I hated her for making fun of me, and I told her I was fine and that I was going to go to bed. To my amazement, she apologized for teasing me and said she was just messing with me and that it was cool that I was a virgin. I felt a little better, but I wasn’t sure if she was messing with me again, or if she really did think my being a virgin was cool.
I tried to play it off like I wasn’t offended and told her everything was fine, and once on my feet I turned away to head down the stairs to be alone. Dana asked me to come back to Missy’s bedroom and hang out with her because Missy had passed out but she wasn’t ready to go to bed. I thought about it and decided that I would rather stay up and chat with Dana than lay on the couch in the dark and berate myself, so I agreed and followed her back into Missy’s room. Missy was sleeping in a little ball on the left hand side of the bed and we had plenty of room to sit opposite each other on the other side of the bed.
At first we didn’t talk, the music from Missy’s boombox was quiet, but it helped fill the void. I started feeling uncomfortable and looked at Dana, who was looking back at me like I was some sort of wounded animal. My intoxication had obliterated my inhibitions and I was still a little pissed off, so I asked her if she really thought that it was cool that I was a virgin. She told me that it wasn’t as big of a deal as people made it out to be, and that she had been a virgin until she was fourteen. That made me feel better and I let my guard down.
Dana asked if I wanted to do a shot and I agreed. I think we both had two shots, but it might have been three. Either way, I was happy to seek the escape from my thoughts and worries that the Black Velvet offered. The first shot went down like fire and I almost puked, but the second (and possibly third) seemed smoother. Dana and I sat there talking for a long time about all kinds of stuff from bands we liked to why girls are called sluts for sleeping around, but guys become studs when they do it.
Sometime late that night Dana asked me if I wanted to be a virgin, or if I just hadn’t met the right girl. I remember being honest and telling her that I hated being a virgin and that most girls would fall into the ‘right girl’ category. She laughed at that and scooted closer to me, we were both sitting ‘indian style’ and she got close enough that our knees touched. She leaned in and asked me with a whisper if she fell into the ‘right girl’ category. I suddenly felt really nervous, I don’t know if it was her proximity, her tone, or her reputation for being a slut, but I knew at that moment that if I said yes, I could have sex with her and get it over with.
I told her that she was in that category, and that I thought she was pretty (the alcohol had somehow made her look quite attractive). She looked over at Missy who was out cold and when she looked back at me she was grinning. She got up from the bed and told me to lay down, and I laid on my back next to Missy. I was so turned on that I didn’t care that Missy was asleep next to me, in fact I remember feeling even more aroused by the thought of having sex for the first time while the gorgeous Missy slept right next to me.
My attention turned back to Dana who crawled on top of me and straddled my hips. My penis pushed against her crotch through my shorts and her jeans, and I could feel heat radiating from her pussy. She pulled off her teeshirt and sat there looking down at me in her bra. Her breasts were large and were spilling out of their restraints. She asked if I had ever felt a girls boobs and I didn’t even try to lie, telling her no. She took my right hand and pulled it up to her left breast. I had no idea what to do so I squeezed it. She smiled and unhooked her bra then I moved my hand as she let go of her bra and let it fall onto my stomache. Her breasts were heavy and saggy, with fat pink nipples that were as big as my pinky toe. I had seen boobs in movies and magazines and they were always firm and perky, but Dana’s soft saggy breasts were even more arousing because they were real and they were right in front of my face. I reached up and cupped one, then the other, and squeezed them, pinching the nipples softly. Dana seemed to enjoy it and I noticed she started breathing heavily.
I was close to having an orgasm from merely playing with her boobs when she got off of me and stood back up. She asked me to get up and I did. She stood in front of me then knelt down. She pulled my shorts down, then my boxers. My penis, still small with adolescence, sprang out at her. She smiled and I remember thinking that she was going to make fun of me for having a small dick and call it off, but to my surprise she leaned in and kissed the tip.
I wanted her to put it into her mouth but she quickly stood up and laid down on the bed. I took my shirt off and crawled on top of her, basically kneeling between her legs. I thought it natural to kiss her, but when I was all puckered up and going in for the kill she pushed me back. She told me there would be no kissing, that she only kissed guys she loved. It didn’t make any sense to me, she would fuck anybody, but she wouldn’t kiss them? I didn’t care however, I just wanted to have sex, so I sat back and reached for her fly. She didn’t resist as I unbuttoned then unzipped her pants. She was wearing green cotton panties with a little red heart on the front. Dana arched her back and I realized it was so that I could pull them off of her. I pulled her jeans off her hips then her legs and tossed them on the floor. I moved up and slipped my fingers into the waistband of her panties, she lifted her hips again,and I pulled them off too.
Right there in front of me was a naked woman. She had saggy boobs, thick thighs, wide hips, and some tummy chub, but she might as well have been Aphrodite herself because I was enthralled by the smooth curves and soft white skin of Dana’s body. Then I noticed the smell eminating from her crotch, it was that sweaty fishy smell of a woman who had a lot of sex and probably needed to douche. But at that time I didn’t know what constituted a smelly vagina and what didn’t, so I figured they all smelled like that and proceeded to move up so I could finally put my penis in a woman.
Dana had other plans and just before I was about to consumate my manhood, she informed me that it was customary for the guy to get the girl off first. I was under the impression that girls orgasmed when the guy put it in, so I tried again to move in, but she grabbed my hips with her legs and stopped me. I looked at her and she must’ve seen my confusion because she told me that she had some rules; number one was that a guy had to lick her and make her cum before sex, number two was that I couldn’t cum inside her, and I don’t remember three, but it had something to do with putting it in her butt. By that point I would’ve jumped in front of a bus if she wanted me to, just so I could have sex with her, so I decided to get licking.
I moved back down the bed and looked at her crotched which was covered in a thick bush of black pubic hair. I had no idea where her clit was, so I just dived in. I put my head between her legs and began licking the outsides of her labia. She giggled and reached down with both hands and spread her lips open to reveal her pussy. Her hole was gooey with juices and she was loose enough that I could’ve put my index finger in her pussy and not touched the sides, but to me it looked sexier and hotter than anything I had ever seen. I moved my mouth down to it and stuck my tongue out, licking her opening with enthusiasm,and I wanted to make her feel good for being willing to be my first. Again she laughed. I pulled my head out of her bush and looked up at her, I was clueless, was I supposed to lick fast or slow? Around her hole or inside it?
She smiled at me and told me to look for the “little pink nub” at the top. I looked and saw what she was referring to, so I asked her what I was supposed to do. She told me to lick the nub, so I did just that. Within minutes my tongue was sore and it was starting to cramp up, but she was really getting into it so I just kept licking, I switched up my rythm and moved my tongue around in circles to help alleviate the cramping and Dana inhaled sharply, grabbed my head and pushed my face hard into her pussy. She started rocking her hips and moaning as she squeezed my head with her legs and rubbed her pussy on my face. I first thought I was hurting her and stopped licking, but then it dawned on me that her moans were full of pleasure and not pain, so I resumed licking and I went along for the ride as she ground her pussy against my face and bucked back and forth. Then she relaxed and pulled my head up. I looked at her and she was laying there with a huge grin on her face staring at the ceiling.
She looked down at me and told me that I had done good for my first time and I could have sex with her now. My penis had somehow gone soft while I was concentrating on licking and I was at a loss as to what to do. I tried rubbing it with no effect, and Dana noticed that I wasn’t screwing her and looked down at my flacid penis. She must’ve seen the look of shock and terror on my face because she smiled and told me to calm down and relax. I told I was sorry and, instead of laughing at my inadequacy, she asked me what turns me on. My head was spinning from the booze and the wild ride of Dana’s orgasm so I blurted out that I wanted to get a girl pregnant.
As soon as I said it, I regretted it. The thought of squirting sperm in a girl and getting her pregnant was my deepest secret fantasy. I cursed myself in my mind for saying it and searched Dana’s face for her reaction. Her brow furled like she was angry, but then her brow, then her whole body relaxed and she looked at me seriously. She told me that she wasn’t on birth control and that’s why she doesn’t let guys cum in her. Then she went on to inform me that, since it was my first time and I would probably do it accidentally anyway, I could cum inside her and if she got pregnant she would deal with it. I asked if she was sure, my penis growing hard at the thought.
She told me to hurry up and do it before she changed her mind. I needed no further suggestion and crawled on top of her and pushed my penis against her wet pussy. Dana reached down, informing me that I had found the wrong hole, and guided my penis to her hole. I slid my penis inward, but she was so loose that I wasn’t sure if I was even in, so I pulled back out and looked down as I put it in again. I was so turned on that the mere heat and wetness were enough to send me into a mind spinning state of arousal and I began moving in and out of her sloppy wet pussy.
Then it happened, way too soon, and five or six thrusts into it I reached the point of no return and ejaculated in her. She giggled as I finished cumming so hard my toes involuntarily curled and my whole body shuttered in ecstasy. She told me that I would have to last longer than that if I ever wanted do it with a girlfriend, but she was okay with it because she got off too. I remember collapsing on the bed next to her, but after that I never saw her again. I heard she moved to the city shortly after and nobody knows if she ever got pregnant from my first time, but I am so glad she was my first because she taught me how to be a man and didn’t judge me….
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