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Ally was my first ‘love.’ I was 14 and so was she. We met online and underwent an ‘internet relationship’ for about a year. We were both inexperienced but eager to please one another. I wasn’t sure if I was a lesbian or bisexual at this point but being with Alexa felt right so her gender was unimportant for me. We eventually ‘broke up’ cause we were both just too immature.
Kim was another girl I met via the music bulletin board I frequented. I chatted with her nonstop before we finally decided that I would spend a weekend at her parents with her. Kelly was incredibly athletic and gave amazing head. We eventually broke up because the distance was too much for either of us.
I met Cyndi in Las Vegas when I was 16 (and there without my parents’ knowledge). She was 21, a bit butch but incredibly charming. After a hot and heavy game of spin the bottle which ended up with us basically fucking in the hotel bathroom. She was vastly more experienced than me and very tender while being passionate. That night in Vegas still stays with me to this day.
We attended the same high school, she was Mexican and beautiful with green eyes and light brown hair. After making eyes at each other for a couple of weeks, we went out for coffee and ended up making out in the back of her car. She had amazing huge tits and despite her beauty was pretty butch, but her father was a police chief and didn’t know his daughter was gay. We ended it after only three months.
I lost my ‘male virginity’ to Homer when I was 16 a few months before my 17th birthday. I don’t even remember how I met him. He was 19, El Salvadorian, pretty nerdy, totally obsessed with Metallica and short. For some reason, I liked him all the same. The night when we finally decided to do the deed was in the trailer where he lived with his parents who were right next-door watching Matlock. After about 10 minutes of missionary thrusting, he dismounted and looked down to explain, “It looks like I shot you!” apparently I’d started bleeding. This was humiliating and resulted in my racing to the bathroom where I stayed for about 30 min before sneaking out the front door.
We had lots of mutual friends and despite his being quite a bit older than me (he was 25 and I was 17) we had a lot in common. He was a bit on the chubby side, but he was a big guy in general. He was the jokester of the group and made me laugh. After a long night of drinking with all of our friends, in a drunken haze I dragged him out of the bar and back to his truck where we had drunken forgettable sex. We ended up dating for about two years despite that unfavorable encounter. Two years into my relationship with Isaac, things had gone stale. We had been living together and having taken on the mother role as he’d just moved out of his parent’s house, all passion was gone. We eventually made up and remained good friends after that.
I heard John’s band play as an opener for another band and sent him a message via Myspace that I really loved the music. He was quite a bit older than me, I was 19 and he was 37 we stayed in contact and eventually ended up going on a few dates (nothing happened because I was still with Isaac). Isaac broke up with me and accused me of being a whore. I decided that since I’d been accused of the deed I might as well.
When we finally hooked up it was a bit of a sexual awakening for me, his vast amounts of experience opened me up to trying things like dirty talk, phone sex, and even anal. He always made sure to get me off and had a fantastic curved penis and was also the first circumcised man I’d been with. After a few months of non-stop fucking like rabbits I discovered that he’d been lying about his age – he was actually 42. We broke up shortly after. Almost six years later I would still get the occasional message from him asking me back.
I knew James via some mutual friends, he lived about two hours driving away from me. He was a year older than me, had long hair, and was a drummer so I was keen to meet him. I drove up on a whim to hang out and watch a movie and have some drinks. We ended up fucking in his room in his parent’s house, which was absolutely disgusting. There was tons of trash on the floor and the walls had been written all over with sharpie. He seemed to take the jack rabbit approach to fucking and I had to remind him several times to slow down, it was one of the most uneventful and forgettable sexual experiences of my life to that date. I left that night directly after he finished. I never called him back after that.
He was a good friend of my ex-girlfriend Kim, whom I had stayed in contact with and had a good relationship with. He was pretty short in stature, with lots of dark curly hair everywhere and was a total pothead. He had recently broken up with his long-term girlfriend and was lonely and horny as was I. He came over to my place and after talking and a few glasses of wine we ended up ripping each other’s clothes off. He was by all means not bad in bed but sweat so much it was actually dripping off of him, until at one point a single bead of sweat dripped into my eye. I limited our contact after that and we remained as friends.
I don’t actually remember this attractive stranger’s name whom I met while at a music festival during my first time in Germany. I only knew that he was Spanish, had gorgeous long flowing hair, and was a great kisser. I took him back to my tent and as we prepared to have awkward tent sex, he revealed one of the biggest dicks I’ve ever seen. He left the next morning and I never saw or heard from him again.
While still on holiday in Germany I attended another music festival. I’d already been in contact with Simon via Myspace as he was interested in my ex John’s band. I’d sent him a message that I’d be travelling alone in Europe and would be cool to have someone to hang out with. After meeting up at the festival, the skies opened up and a torrential rain poured down. Simon’s tent had been blown over by the winds and was completely flooded inside. I offered for him to stay in mine and we ended up drunkenly making out. He was very thin and his bones jabbed into me with every movement. He was also one of those intense people that liked to look into your eyes while you had sex which I found incredibly awkward – especially after a lot of Jack and Coke, in a tent. We stayed in touch and I eventually ended up coming to live with him in Europe. We got married so I could stay in the country and stayed together for three years. Things got really bad at the end and after he cheated on me with a colleague we split up.
Chris was the first person I had sex with after my separation from Simon. Chris was tall, blonde, very clean cut and very handsome. He was also extremely drunk. I was attending a music festival with some friends in Germany when he started talking to me in incoherent half English/half German. I dismissed him but he kept following me around like a puppy dog. As the night progressed and I became more and more intoxicated I relented and let him lead me by the hand back to his tent where we fucked for what felt like hours. He didn’t have the biggest or most impressive dick in the world, but he had stamina.
I waited until he fell asleep and snuck back to my own tent. We found each other again months later via Facebook and ended up meeting up again afterwards around Christmas time. In a drug and alcohol induced haze, we ended up fucking on his friend’s sofa in every position imaginable. After that we stayed in touch, when I attended a concert and he appeared with his girlfriend, I was very confused. He explained they had an open relationship but I decided that from that point on, we were better as just friends. To this day we have an incredibly close friendship and he is one of my best friends.
I had met Sam one drunken night in a shithole town in Belgium after a gig. He was half Costa Rican and half Belgian and very attractive, despite being very short (what is it with me and short guys?). We stayed in touch via Facebook and eventually met up again after that. I’m not even sure how, but I’m pretty sure it was an alcohol-induced evening that led me to sleep with him. We had very forgettable sex mostly due to his very small penis and his overenthusiasm. We stayed friends but never slept together again.
I’d known Mike since I was 16 via Myspace but we only actually met when I was 24 in person. I attended his band’s gig in that same shitty town in Belgium and afterwards we started talking regularly. I’d always been extremely attracted to Mike. He was tall, long brown hair with the totally heavy metal look I was so very into. I had planned to attend a concert in the city where he lived and needed a place to stay so I asked if I could crash on his sofa. We stayed up all night just talking and hanging out after the gig but when it came time to go to sleep he took the sofa and offered his bed, so nothing happened.
A few months later, I needed to take a flight back to the states and the airport was two hours away from me and only 5 minutes from his place so I asked if it would be alright if I stayed over again. We started making out and he was a very sexy and tender kisser and also intent that I get off, he had a big dick, endurance, and was very aware of what he was doing. We both agreed neither of us wanted anything serious and have continuously been ‘friends with benefits’ and very good friends. Mike remains the best sex of my life and I doubt I will ever have as much sexual chemistry with anyone the way I have with him.
I knew who Joe was via some mutual friends when I met him at a music festival in Holland. We stayed in touch and after a few weeks of furious texting, I drove up to see him in the Netherlands. We went to go see Megadeth play and then drank some strong Belgian beers before going back to his place. The sex was good but he seemed to believe that some weird swivel movement with his hips was a key to getting a woman off. He came to see me again once after that, we had a nice long hot steamy bath and then passionate sex. After discussing that he didn’t want a relationship, we cut it off.
A friend introduced me to Philip at a music festival and I was instantly attracted to him but far too drunk to do anything about it. He was Chilean, really tall, with long dark hair. We exchanged information and met up again a few months later with much anticipation at a concert in Germany but his flight back home was early the morning after the gig so we ended up just chatting and enjoying each other’s company. He was a total gentleman the entire night and we parted ways but decided we had to see each other again. The opportunity arose to go to Sweden where he lived as my favorite band was playing. I booked a hotel room and after the gig we came back and practically ripped one another’s clothes off before engaging in what can only be described as a sex marathon. He had a huge dick and was a big fan of giving oral, which I am always a big fan of. We went back to his place an hour away and I stayed there for a week just sitting around watching movies and listening to music and fucking. I was quite into him but he wasn’t ready for a relationship so we both agreed it would be better to just be friends.
After Philip, I was feeling a bit dejected and like I really need to be desired so I tried the dating app ‘Tinder’ – basically ‘Grinder’ for heteros. I was initially attracted to Jim’s profile picture and we exchanged a lot of messages. However, when I finally met him, the reality wasn’t quite like the picture. He was much shorter than I’d expected, a bit doughy and had bad teeth. We got on really well though and the conversation was never lacking so as the drinks flowed I cared less and ended up back at his place. The sex was pretty vanilla and his dick fairly unimpressive.
The weirdness started when he had me sleep on the sofa-bed afterwards and he slept on his single bed. I met up with him a few times after that but we didn’t fuck, the second time because he didn’t have a condom and nor did I. The third time couldn’t bring myself to sleep with him again after he incessantly talked about his irritable bowel syndrome and felt comfortable enough to fart constantly throughout the evening. I broke things off with him and ‘lost’ his number.
Brian and I met originally after a crazy night of partying, I knew his housemate and myself and my friend Chris had arranged to stay at their place. We didn’t really talk and I didn’t think he even remembered me. But I was overwhelmingly attracted to him. He was tall with long hair, a full beard, piercing eyes and a strong physique to match. The following week we met again, this time we started talking and hitting it off immediately which ultimately led to the very high school act of making out in the concert venue for about an hour. I offered for him to come back and stay in my hotel room with myself and my friends, we laid down together, and after kissing and heavy petting he told me he didn’t want just a one-night stand so he’d rather just hold me.
I was smitten for sure. He came to visit me a month later for a long weekend and I was incredibly nervous around him, when we finally fucked we were both quite drunk and there was a few issues with him getting hard so we gave up and went to sleep. He more than redeemed himself the following morning however. A few months later I went to see him again and we had an amazing four days together. The last day felt bittersweet and I could tell something was up. He admitted that he really liked me but the distance was too much. I’m still not over this one and don’t think I will be for awhile.