Straight Male / 30
How I Lost My Virginity.
I have been wanting to share a story on here. I have had some exciting sexual adventures, but I'll start with some background and how I lost my virginity. If anyone reads this, I hope you enjoy!
When I was in 6th grade I became friends with Nick who was a classmate of mine. We spent a lot of time at each others and it was fun to go to his house because his parents were not strict at all. Neither of them worked because they had inherited more money than someone needs, but they didn't live a super fancy and lavish lifestyle either. Nick had an older sister named Bridgette and I had a massive crush on her the first time I saw her. Seeing her was the first time I realized I loved boobs because she had nice tits and always showed a ton of clevage.
One day Nick and I were playing some video games and I started to hear moaning and a bedframe banging on a wall. At first I figured it was some kind of prank so I asked Nick and he said that Bridgette and her new boyfriend are having sex. I was in complete shock and disbelief. Their parents were home, it was the early evening and they were not hiding it at all. My parents would have probably come into the room and shot the guy. Nick told me his parents always said they were allowed to have sex once they got to high school, the only rule is we always need to use a condom. I was stunned with surprise, not only the fact that I was so close to someone having sex, but that it was allowed and encouraged by the parents. I later found out that they also allowed the kids to drink when they got in high school and wisely said the only rule for drinking was to never drive after. I wanted to try and sneak and see Bridgette having sex and was so turned on by this idea that I couldn't focus. I said I had to go to the bathroom and walked past her room, but the door was closed, and I was too scared of getting caught opening the door.
Shortly after this event I started jerking off and I would always think about banging Bridgette or their mom because of how open they were about sex.
In my sophomore year of high school, I was over at their house on a summer night and we had been playing beer pong with Nick, some of Bridgett's College friends, and their parents. Their parents were going to bed and they put a box of condoms on the kitchen counter telling us to make sure we stayed safe tonight. Every one was feeling pretty loose from the drinking and I said "Maybe someday I'll get to use one." I was a virgin at the time and Nick's parents were polite about it saying that everyone goes at their own pace. Bridgette on the other hand was surprised and said "Thomas! You are a virgin?!" and then to one of her friends she said "ooOOOO Meghan." I was shy and embarrassed, but the topic faded.
Meghan was a pretty brunette. Her breasts were smaller than Bridgette's, but Meghan had a very enticing dark eye makeup on that was getting me hott and bothered. With some liquid courage, I worked up the nerve to talk to Meghan and asked why she particular was called out when the news about me came up. "I've never taken anyone's V-Card. All my exes had lost their's before me." I had never heard the term 'v-card' but due to my Sherlockian use of context clues, I was able to figure out it meant virginity. We started talking and played some Beer pong together and getting a little flirty but I was so scared to make a move. Bridgette came up to us with a condom, gave it to me and said "Go up in my room and fuck her already." I was shocked and excited, I asked Meghan if she wanted to and she said "I mean, I've been trying to give you some hints for awhile now, so yes."
I was so excited I started to shake a little and got a hefty case of the butterflies. I was drunk so I think that helped dull the symptoms of overwhelming excitement. I was already rock hard on the walk up to her room. We laid on the bed and started making out and dry humping. She pulled her shirt off while we were making out and then asked if I had ever taken a girls Bra off. I had not and so she asked me to try. I fumbled with it for a moment but I did end up getting it un hooked while reaching around her. Her bra slid off and I could feel the pre-cum on the tip of my dick as I saw real tits right in front of me. She had amazing bikini tan lines. I grabbed them and remember thinking her areola felt so much bigger than mine. They were not larger than a normal girls, I just had never felt a real boob and that was the feeling of it that stuck with me. I started to suck on her breasts and I felt her hand start unzipping and unbuttoning my jeans. Her hand slid into my boxers and wrapped around my dick. A paralyzing and amazing sensation flowed from my crotch to my whole body as she started to slowly stroke it.
After a couple minutes of getting to suck her tits, she rolled to be on top of me and started to kiss her way down my chest. Her hands grabbed my jeans and boxers and lifted them up so she could slide them down past my cock. I saw a string of Pre-cum from the tip of my dick to my boxers and had a weird fear that if she saw that it would be a deal breaker. The cool air of the room cradled my now fully exposed cock for a moment. My pre-cum fear was quickly eased when I felt the warmth and wetness of her mouth wrap around and slide down my dick. Seeing her tits hang and swing as she knelt over me, bobbing her head up and down on my dick, was the most beautiful thing I had ever seen in my life. I kept having the though that there are people in the world watching porn right now, and I am actually getting my dick sucked by a topless chick. I had to look up at the ceiling fan and try not to think of what was happening so I wouldn't cum too early. My mindset flipped and I just became focused on making sure that she would also enjoy this. That mindset, paired with the drinking helped me lose the feeling like I was about to cum.
She sucked my dick for a few minutes and then reached into the pocket of my jeans that were now on the end of the bed and pulled out the condom. She gave it to me to put on while she slid down her jeans, revealing a lacy black thong, that quickly followed her jeans down, exposing more bikini tan lines. I got the condom on and was filled with disbelief that there was now a fully naked chick, headed into position to straddle me on a bed and put my dick inside her. I knew people actually had sex, but part of me just didn't believe it would ever actually happen to me. She got in position above me, bent over to give me a kiss and said "just relax" Her hand grabbed my dick and pressed it against her pussy as she slowly slid down onto it. The first few strokes were very slow, but each one got a bit deeper until she was sitting all the way down on it. She started to speed up as bounced up and down The condom was super tight on the head of my dick and was actually hurting me a little bit, but I was happy about that because I didn't have to worry about cumming. I kept switching between playing with her bouncing tits and getting a handful of ass cheek. She bent over and started to make out with me while still rolling and bouncing her hips.
After going at it with her on top, I wanted to try and impress her. I took control, rolled her over, and slid my dick right back into her. She bit her lip and said "Ooo." I was thrusting my hips into her like a jackhammer but the condom started to hurt too much so I pulled it out to try and adjust. "Looks like you need to leave more space in the tip" she said. I made the adjustment and now it felt soooo much better. I started to get back to my jackhammer speed but this time it was felling too good so I slowed it down and bent down to make out. She started nibbling my ear lobe and that surprised me, but felt amazing. I started to try and do what I had seen in porn and pulled her to the end of the bed and stood between her legs and I pounded her again. The bed was a bit low so I put her legs up over my shoulders and after just a few thrusts my dick was feeling amazing. Up til now she had been moaning, in this position she let out a loud "Ohh fuck." I knew I was not going to last long like this so I started to brace for the eruption. I wanted to give her one last jackhammering before I blew my load. She was loving it and said the magic words "Don't stop." my nuts tensed up, my body froze, but I tried my best to power through and keep thrusting. My head got light and the floodgates opened. My thrusting slowed down as I slid my pulsing cock in and out of her until I was completely drained. I pulled out and a pond worth of white cloudy goo had filled the area around the head of my dick in the condom.
"Was that really your first time?" She asked. I affirmed that it was and she told me "You are pretty good at it for a first time." We returned to the party and those who were still awake cheered us on. We slept on a couch together that night and it felt so amazing to sleep with a little spoon. We exchanged phone numbers and texted each other a bit but she told me she didn't want any kind of relationship. I didn't either, I was just ignorant to the fact that some girls are cool with one night stands.
When I was in 6th grade I became friends with Nick who was a classmate of mine. We spent a lot of time at each others and it was fun to go to his house because his parents were not strict at all. Neither of them worked because they had inherited more money than someone needs, but they didn't live a super fancy and lavish lifestyle either. Nick had an older sister named Bridgette and I had a massive crush on her the first time I saw her. Seeing her was the first time I realized I loved boobs because she had nice tits and always showed a ton of clevage.
One day Nick and I were playing some video games and I started to hear moaning and a bedframe banging on a wall. At first I figured it was some kind of prank so I asked Nick and he said that Bridgette and her new boyfriend are having sex. I was in complete shock and disbelief. Their parents were home, it was the early evening and they were not hiding it at all. My parents would have probably come into the room and shot the guy. Nick told me his parents always said they were allowed to have sex once they got to high school, the only rule is we always need to use a condom. I was stunned with surprise, not only the fact that I was so close to someone having sex, but that it was allowed and encouraged by the parents. I later found out that they also allowed the kids to drink when they got in high school and wisely said the only rule for drinking was to never drive after. I wanted to try and sneak and see Bridgette having sex and was so turned on by this idea that I couldn't focus. I said I had to go to the bathroom and walked past her room, but the door was closed, and I was too scared of getting caught opening the door.
Shortly after this event I started jerking off and I would always think about banging Bridgette or their mom because of how open they were about sex.
In my sophomore year of high school, I was over at their house on a summer night and we had been playing beer pong with Nick, some of Bridgett's College friends, and their parents. Their parents were going to bed and they put a box of condoms on the kitchen counter telling us to make sure we stayed safe tonight. Every one was feeling pretty loose from the drinking and I said "Maybe someday I'll get to use one." I was a virgin at the time and Nick's parents were polite about it saying that everyone goes at their own pace. Bridgette on the other hand was surprised and said "Thomas! You are a virgin?!" and then to one of her friends she said "ooOOOO Meghan." I was shy and embarrassed, but the topic faded.
Meghan was a pretty brunette. Her breasts were smaller than Bridgette's, but Meghan had a very enticing dark eye makeup on that was getting me hott and bothered. With some liquid courage, I worked up the nerve to talk to Meghan and asked why she particular was called out when the news about me came up. "I've never taken anyone's V-Card. All my exes had lost their's before me." I had never heard the term 'v-card' but due to my Sherlockian use of context clues, I was able to figure out it meant virginity. We started talking and played some Beer pong together and getting a little flirty but I was so scared to make a move. Bridgette came up to us with a condom, gave it to me and said "Go up in my room and fuck her already." I was shocked and excited, I asked Meghan if she wanted to and she said "I mean, I've been trying to give you some hints for awhile now, so yes."
I was so excited I started to shake a little and got a hefty case of the butterflies. I was drunk so I think that helped dull the symptoms of overwhelming excitement. I was already rock hard on the walk up to her room. We laid on the bed and started making out and dry humping. She pulled her shirt off while we were making out and then asked if I had ever taken a girls Bra off. I had not and so she asked me to try. I fumbled with it for a moment but I did end up getting it un hooked while reaching around her. Her bra slid off and I could feel the pre-cum on the tip of my dick as I saw real tits right in front of me. She had amazing bikini tan lines. I grabbed them and remember thinking her areola felt so much bigger than mine. They were not larger than a normal girls, I just had never felt a real boob and that was the feeling of it that stuck with me. I started to suck on her breasts and I felt her hand start unzipping and unbuttoning my jeans. Her hand slid into my boxers and wrapped around my dick. A paralyzing and amazing sensation flowed from my crotch to my whole body as she started to slowly stroke it.
After a couple minutes of getting to suck her tits, she rolled to be on top of me and started to kiss her way down my chest. Her hands grabbed my jeans and boxers and lifted them up so she could slide them down past my cock. I saw a string of Pre-cum from the tip of my dick to my boxers and had a weird fear that if she saw that it would be a deal breaker. The cool air of the room cradled my now fully exposed cock for a moment. My pre-cum fear was quickly eased when I felt the warmth and wetness of her mouth wrap around and slide down my dick. Seeing her tits hang and swing as she knelt over me, bobbing her head up and down on my dick, was the most beautiful thing I had ever seen in my life. I kept having the though that there are people in the world watching porn right now, and I am actually getting my dick sucked by a topless chick. I had to look up at the ceiling fan and try not to think of what was happening so I wouldn't cum too early. My mindset flipped and I just became focused on making sure that she would also enjoy this. That mindset, paired with the drinking helped me lose the feeling like I was about to cum.
She sucked my dick for a few minutes and then reached into the pocket of my jeans that were now on the end of the bed and pulled out the condom. She gave it to me to put on while she slid down her jeans, revealing a lacy black thong, that quickly followed her jeans down, exposing more bikini tan lines. I got the condom on and was filled with disbelief that there was now a fully naked chick, headed into position to straddle me on a bed and put my dick inside her. I knew people actually had sex, but part of me just didn't believe it would ever actually happen to me. She got in position above me, bent over to give me a kiss and said "just relax" Her hand grabbed my dick and pressed it against her pussy as she slowly slid down onto it. The first few strokes were very slow, but each one got a bit deeper until she was sitting all the way down on it. She started to speed up as bounced up and down The condom was super tight on the head of my dick and was actually hurting me a little bit, but I was happy about that because I didn't have to worry about cumming. I kept switching between playing with her bouncing tits and getting a handful of ass cheek. She bent over and started to make out with me while still rolling and bouncing her hips.
After going at it with her on top, I wanted to try and impress her. I took control, rolled her over, and slid my dick right back into her. She bit her lip and said "Ooo." I was thrusting my hips into her like a jackhammer but the condom started to hurt too much so I pulled it out to try and adjust. "Looks like you need to leave more space in the tip" she said. I made the adjustment and now it felt soooo much better. I started to get back to my jackhammer speed but this time it was felling too good so I slowed it down and bent down to make out. She started nibbling my ear lobe and that surprised me, but felt amazing. I started to try and do what I had seen in porn and pulled her to the end of the bed and stood between her legs and I pounded her again. The bed was a bit low so I put her legs up over my shoulders and after just a few thrusts my dick was feeling amazing. Up til now she had been moaning, in this position she let out a loud "Ohh fuck." I knew I was not going to last long like this so I started to brace for the eruption. I wanted to give her one last jackhammering before I blew my load. She was loving it and said the magic words "Don't stop." my nuts tensed up, my body froze, but I tried my best to power through and keep thrusting. My head got light and the floodgates opened. My thrusting slowed down as I slid my pulsing cock in and out of her until I was completely drained. I pulled out and a pond worth of white cloudy goo had filled the area around the head of my dick in the condom.
"Was that really your first time?" She asked. I affirmed that it was and she told me "You are pretty good at it for a first time." We returned to the party and those who were still awake cheered us on. We slept on a couch together that night and it felt so amazing to sleep with a little spoon. We exchanged phone numbers and texted each other a bit but she told me she didn't want any kind of relationship. I didn't either, I was just ignorant to the fact that some girls are cool with one night stands.
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