Straight Male / 34
My First Real Girlfriend Was Wild
When I was 16 I had my first proper relationship, long-distance, with a girl for almost 1.5 years. We were teenagers madly in love. We'd speak for ages on the phone every night, and once every 3-4 weeks I'd travel by train for a couple of hours to visit her. Being long distance was difficult and we were ultimately too young for it to work. Eventually I became so insecure, naive and worried she'd cheat on me, the relationship ended.
Shortly after, I met my now wife and moved on. I love my wife but she is quite conservative sexually, and doesn't have a high sex drive. Myself, I am extremely adventurous and sexually liberal. This previous girl was incredibly sexually adventurous and kinky too. We were on the same level and I regret that I was so insecure at the time that I never really took advantage of fully exploring my sex life then to the maximum. I wish I had done all the crazy things we could've done, and then moved on knowing I'd had all those experiences that I will now never have.
Here's some stories from that time, that I remember fondly...
The first time I ever went to visit her (we met online) was after about 3 months of speaking every day online or on the phone. We just spent time around her city. We couldn't go to her house because her dad would've killed me probably (random teenage kid she met online and brought back to hers). We spent a lot of time just talking and making out. Before I had to leave we waited at the train station for an hour or so. Sitting on my lap, she asked me quietly how big my cock was, obviously able to feel my hardening shaft straining to get out of my jeans. I told her 7" (the truth) and she passionately grabbed my face and forced her tongue wildly into my mouth again. She went to use the toilet at some point. Later, on another occasion, she told me that she had been so wet that she'd gone to clean up. Her underwear was soaked through. She also said she'd considered dragging me into the toilets for a blow job so she could get my cock out. I went home on the train with severe blue balls though, still never having had a girl touch me.
We would have phone sex, text each other dirty talk, or have online sex over AOL Messenger almost every day, and we had the discussion of having actual sex the next time we met came up. We agreed we should if we got the opportunity. We were both virgins.
The next time she came to my house. My siblings were at school (I had finished school at this time), and although my mum was downstairs, we spent the whole time in my room, where for the first time as she sat on my desk, I pulled her jeans and thong off and buried my face in her soaking wet c**t. I lapped at pussy for probably an hour. At some point my mum went to pick up my siblings from school, and we had literally 15 minutes max before they all came home. The minute she closed the front door, she asked me if we should have sex and we agreed to. I quickly put on a condom and climbed into my bed naked with her. I slipped my throbbing cock with ease into her sticky, wet pussy, all the way to my balls. There was just no way I would be able to last and I shot my load within about 30 seconds I think! She still loved it. In about 5 minutes I was ready to go again, and we went for round 2. I really wanted to last longer this time. Unfortunately, as we were about to get into it, everyone came home and I had - no exaggeration - about 20 seconds to leap out of my bed, throw all my clothes back on, get rid of the condom, tuck my erection into my belt, and make a mad dash for my bedroom door as I could hear my brother running up the stairs. He just about burst into my room as she'd gotten dressed and jumped out of bed. It was a miracle we didn't get caught!
The next time I went to visit her we decided to stay in a hotel (I don't know how I convinced my parents to let me go to another city and stay overnight with some random person they didn't really know that I'd met online). That night we were able to have proper, uninterrupted sex. We got to our room at about 3pm and immediately she was on the bed and wanted me. She was on the pill by this time and I simply fucked her missionary, with her legs wrapped around my waist. I came inside her and it was amazing. We went out for dinner at some point, but basically spent all night fucking. We had sex 10 times and I myself came 6 times, which I have never gotten close to before or since in one 24 hour period, let alone a single night. We tried all the basic positions and exploring oral sex and other things. It was a great night and she was very adventurous and insatiable.
We continued to have phone sex regularly. I'd go downstairs and watch TV late at night in the dark, lying on the sofa naked with a blanket over me while everyone else was in bed. I'd call her and we'd have a whispered conversation about all the filthy things we wanted to do to each other. One time I remember she was masturbating down the phone to me while I was talking to her, making her more and more turned on. She went quiet for ages and was simply moaning heavily. I asked her what she was doing and she told me she had just slipped a finger into her ass. I almost exploded in my hand then and there, thinking of her pleasuring herself in both of her holes.
At this time, porn magazines were still a common thing, and I had loads that I'd found in the woods, stashed under my bed. I told my girlfriend this and she was quite excited by it. She asked me to bring her some to see next time I went. I got my porn mags out of my bag and she was so visibly turned on by them. She flicked through the pages of proper, adult women with mature, trimmed pussies, full breasts, spreading their lips and showing their holes. She told me the thought that I wanked to these magazines turned her on. She told me I was a dirty boy, which was kind of hot. I wish now that I'd explored this further with her - watched porn together, masturbated to these things together. I would've found that so hot, wanking myself off to pictures or videos of other naked women for her, and vice versa. As I said, I was naive at the time and missed a lot of the potential that now I would've gone crazy for.
One time she wanted to try anal, so she got on all fours and I lubed up my cock. I went slow and fucked her ass gently but we didn't really get into it. After 15 mins it was a bit boring and didn't actually feel that great to me compared to her pussy, and I think she had also expected to feel more. In retrospect, I should've put something in her pussy at the same time and rubbed her clit for her to make it more of an experience.
We began a regular thing when I went to visit, where if we wanted to fuck during the day (which we always did), the only place we could go was public toilets. So we'd go to the cinema, both walk round the corner to the disabled toilet which was large and isolated, and fuck on the floor. Gross, in retrospect, but it was hot at the time knowing we might get caught.
Once we were in the cinema seeing a comedy of some kind, it was three quarters full. We were on the back row towards one corner but people were sitting a few seats down from me. She encouraged me to put my hand down her pants and I rubbed her clit and tried to get my finger into her wet pussy for probably an hour. She kept reaching over to rub my hard cock in my jeans but I didn't want the people next to me to notice, so I'd stop her. I wish I'd been more adventurous about that now. She came twice on my fingers.
After a while, our ..(continue confession)
Shortly after, I met my now wife and moved on. I love my wife but she is quite conservative sexually, and doesn't have a high sex drive. Myself, I am extremely adventurous and sexually liberal. This previous girl was incredibly sexually adventurous and kinky too. We were on the same level and I regret that I was so insecure at the time that I never really took advantage of fully exploring my sex life then to the maximum. I wish I had done all the crazy things we could've done, and then moved on knowing I'd had all those experiences that I will now never have.
Here's some stories from that time, that I remember fondly...
The first time I ever went to visit her (we met online) was after about 3 months of speaking every day online or on the phone. We just spent time around her city. We couldn't go to her house because her dad would've killed me probably (random teenage kid she met online and brought back to hers). We spent a lot of time just talking and making out. Before I had to leave we waited at the train station for an hour or so. Sitting on my lap, she asked me quietly how big my cock was, obviously able to feel my hardening shaft straining to get out of my jeans. I told her 7" (the truth) and she passionately grabbed my face and forced her tongue wildly into my mouth again. She went to use the toilet at some point. Later, on another occasion, she told me that she had been so wet that she'd gone to clean up. Her underwear was soaked through. She also said she'd considered dragging me into the toilets for a blow job so she could get my cock out. I went home on the train with severe blue balls though, still never having had a girl touch me.
We would have phone sex, text each other dirty talk, or have online sex over AOL Messenger almost every day, and we had the discussion of having actual sex the next time we met came up. We agreed we should if we got the opportunity. We were both virgins.
The next time she came to my house. My siblings were at school (I had finished school at this time), and although my mum was downstairs, we spent the whole time in my room, where for the first time as she sat on my desk, I pulled her jeans and thong off and buried my face in her soaking wet c**t. I lapped at pussy for probably an hour. At some point my mum went to pick up my siblings from school, and we had literally 15 minutes max before they all came home. The minute she closed the front door, she asked me if we should have sex and we agreed to. I quickly put on a condom and climbed into my bed naked with her. I slipped my throbbing cock with ease into her sticky, wet pussy, all the way to my balls. There was just no way I would be able to last and I shot my load within about 30 seconds I think! She still loved it. In about 5 minutes I was ready to go again, and we went for round 2. I really wanted to last longer this time. Unfortunately, as we were about to get into it, everyone came home and I had - no exaggeration - about 20 seconds to leap out of my bed, throw all my clothes back on, get rid of the condom, tuck my erection into my belt, and make a mad dash for my bedroom door as I could hear my brother running up the stairs. He just about burst into my room as she'd gotten dressed and jumped out of bed. It was a miracle we didn't get caught!
The next time I went to visit her we decided to stay in a hotel (I don't know how I convinced my parents to let me go to another city and stay overnight with some random person they didn't really know that I'd met online). That night we were able to have proper, uninterrupted sex. We got to our room at about 3pm and immediately she was on the bed and wanted me. She was on the pill by this time and I simply fucked her missionary, with her legs wrapped around my waist. I came inside her and it was amazing. We went out for dinner at some point, but basically spent all night fucking. We had sex 10 times and I myself came 6 times, which I have never gotten close to before or since in one 24 hour period, let alone a single night. We tried all the basic positions and exploring oral sex and other things. It was a great night and she was very adventurous and insatiable.
We continued to have phone sex regularly. I'd go downstairs and watch TV late at night in the dark, lying on the sofa naked with a blanket over me while everyone else was in bed. I'd call her and we'd have a whispered conversation about all the filthy things we wanted to do to each other. One time I remember she was masturbating down the phone to me while I was talking to her, making her more and more turned on. She went quiet for ages and was simply moaning heavily. I asked her what she was doing and she told me she had just slipped a finger into her ass. I almost exploded in my hand then and there, thinking of her pleasuring herself in both of her holes.
At this time, porn magazines were still a common thing, and I had loads that I'd found in the woods, stashed under my bed. I told my girlfriend this and she was quite excited by it. She asked me to bring her some to see next time I went. I got my porn mags out of my bag and she was so visibly turned on by them. She flicked through the pages of proper, adult women with mature, trimmed pussies, full breasts, spreading their lips and showing their holes. She told me the thought that I wanked to these magazines turned her on. She told me I was a dirty boy, which was kind of hot. I wish now that I'd explored this further with her - watched porn together, masturbated to these things together. I would've found that so hot, wanking myself off to pictures or videos of other naked women for her, and vice versa. As I said, I was naive at the time and missed a lot of the potential that now I would've gone crazy for.
One time she wanted to try anal, so she got on all fours and I lubed up my cock. I went slow and fucked her ass gently but we didn't really get into it. After 15 mins it was a bit boring and didn't actually feel that great to me compared to her pussy, and I think she had also expected to feel more. In retrospect, I should've put something in her pussy at the same time and rubbed her clit for her to make it more of an experience.
We began a regular thing when I went to visit, where if we wanted to fuck during the day (which we always did), the only place we could go was public toilets. So we'd go to the cinema, both walk round the corner to the disabled toilet which was large and isolated, and fuck on the floor. Gross, in retrospect, but it was hot at the time knowing we might get caught.
Once we were in the cinema seeing a comedy of some kind, it was three quarters full. We were on the back row towards one corner but people were sitting a few seats down from me. She encouraged me to put my hand down her pants and I rubbed her clit and tried to get my finger into her wet pussy for probably an hour. She kept reaching over to rub my hard cock in my jeans but I didn't want the people next to me to notice, so I'd stop her. I wish I'd been more adventurous about that now. She came twice on my fingers.
After a while, our ..(continue confession)
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