[M] Story of my first time. Have told only a few people, I think it will feel good to tell this story. After typing all this out, I realize I still love this girl.

I am 32 years old now but was 18 when I had sex for the first time. This story means a lot to me and I don't make a habit of telling everyone all about my sex life. I think it will feel good to tell this story 14 or 15 years later.

I was raised in a conservative home and started to have doubts about a lot of things in high school. So the summer after I graduated I rented a cabin in the Adirondacks to be alone, to hike and to see if I could figure some things out. I had met a girl in the previous year while on a retreat and had exchanged info so I figured I would take a weekend trip to see her now that I was on my own. Now, being a good Christian boy for so long, I didn't know what to expect. I hoped that maybe we would make out or, if I was really honest with myself, that sex would finally happen. I show up for a party at her house – her parents were out of town – and she turns out to be a total B. She ended up with another guy and only said a few words to me the entire night.

But, it turns out her best friend was there. We'll call her Jess. She had a beautiful, confident face and amazing curves. She had just had a fight with her step dad and was ready to let go, get drunk and forget about the horrible situation her parents’ divorce had put her in. And me? I was totally ready to let myself suffer for the mistake I had made driving 4 hours to Rochester to fuck a girl. Did I really think she would just jump into bed with some desperate dude who was spending the summer alone in a cabin? I didn't drink, I didn't smoke weed with the long haired guys in the backyard. I sat alone paying the price for me ignorance.

Meanwhile, Jess was getting herself into trouble. She had drunk a lot and was getting out of control. So I figured I'd help out. I took her out to the screened-in back porch, got her some water and talked her out of doing whatever crazy thing she thought would help her feel better.

We woke up the next morning next each other in uncomfortable lawn chairs on the dusty back porch. She looked at me, realizing I didn't take advantage of her, she had let me take care of her the night before, fully expecting that I would. We chatted while we cleaned up beer bottles and exchanged email addresses before I went back to my cabin.

I believe this would have been 2000, before we had constant access to everything via smartphones. I checked my email at the library in the nearby town on Tuesday's and Saturday's. So the Tuesday following the party I get an email from Jess, sent the evening after the party. It was a pretty flattering email, about how she attracted the worst kinds of guys and had forgotten that most men were well meaning and kind like I was to her. And at the end she said she wanted to come see me. Of course I didn't want to get mixed up with a girl with as much baggage as she had so I politely declined but she pressed in a subsequent email that I didn't get until the following Saturday. I caved and gave her directions. Now all the stuff you've been waiting for.

She shows up and I have no idea what to do. Should I take her out to dinner, should we go for a hike? I have no clue. Up to this point I had dated one girl and even that was behind my parent's back. We end up walking around the town where the library was and did some window shopping before going back to my cabin to play cards. Now remember, I didn't really want this girl here with me. She seemed like trouble and, being a nice buy in high school, girls like this had been attracted to me before. I wasn't interested in the drama. Anyway, my cabin had one bed and I start to make a place for me to sleep on the floor and she says, no, there's plenty of room in this bed for both of us. I climb in and lay awkwardly on the edge and she laughs and dares me to get closer. I roll on my side and look into her eyes and really see her for the first time. She is beautiful and fierce and kind all at the same time. And I'm all of the sudden comfortable being there with her. We end up chatting and laughing and snuggling the rest of the night.

We wake up together for the second time, much more comfortable than the first time. I have a huge boner and she knows it. I'm so embarrassed and she knows that too. She tells me to hang out in bed while she showers. I doze off a little. When she's done, she steps out of the shower into plain view in nothing but a towel and tells me to sit down on the chair by the table. She starts to move her hips and dance a little in front of me. She undoes her towel a little and lets me see her naked back, then she turns and there are her boobs. The first time I had ever seen boobs fully exposed like that right in front of me. Then she drops the towel all the way to the floor. She does her dance for a little while and I'm going crazy, I knew right then that I'd be addicted to sex for the rest of my life. If this is what sex and foreplay were like I'd never get enough. I felt things in that moments that I will never be able to put into words. I was so enraptured, she had to tell me to take my pants off. To this day I have a thing for curvy chicks thanks to her. She was the perfect kind of curvy; great hips, tight waist and flat stomach, a big round ass and the most amazing tits you can imagine.

She then proceeds to give me my first blowjob. As you can imagine it takes me no time to cum. I forget where I came, not on her, probably in a paper towel or in the shower. I wish I could remember. When it's over I'm breathing heavy and my world is spinning. This is the most earth shattering moment of my life and we haven't even had actual sex. She tells me that I should go down on her to return the favor. I had only had a fleeting experience with porn by this time because of my conservative upbringing and I'd never been with a girl like this and had no clue what to do. I was super nervous. She showed me around, and ultimately it wasn't great for her, I don't think. Now I'm thinking sex might be a possibility but I have no condoms. I'm not going to do anything without a condom but I want to put my penis in her vagina so bad right now. I stall and up to this point she has taken the lead on all of this, which is totally a turn-on for me now by the way, I hope maybe she has a solution. But we just snuggle a little more and talk about how sheltered I was as a kid and how inexperienced I am, which she loves. I don't remember how long we stayed in bed and I don't think anything else happened.

We end up going back into town after I mention the condom thing. I grab some beer from the guy who works at the general store who didn't ask for ID the last time I tried to buy beer. With condoms in hand we head back to the cabin, drink some beer in the clearing overlooking a river and some hills before the bugs start to bother us. We go inside and fall asleep together in each other's arms.

I wake up and I haven't had sex yet. I had fully expected that it would happen last night. I'm a little mad at her, a lot mad at myself. I decide I'm going to play the tough guy so I start kissing her and grabbing her boobs. I think I got out of bed and made her get up too because I remember telling her to put the condom on me while we were standing. I jump on top of her back in bed and decide not to try anything fancy, I go missionary and struggle to get it in, she grabs me and pushes and squirms but I eventually figure it out and she's a little wet by now so things are moving as they should. I lasted a little longer than I expected, I think because of the condom. I remember burying my face in her neck and watching her boobs bounce underneath me and that's it, I'm not a virgin anymore. We used the rest of the condoms that day and the next morning, experimenting, making mistakes and just having fun.

It was the best way for it to happen. I had an extended period of time to try things out, instead of sneaking around while my parents were out of the house or something. She was not a virgin and loved being the experienced one, showing me things and making me feel like a champ.

We said goodbye and she drove off. I had this stabbing fear that I would never see her again. Now it’s my turn to write her a gushing email. I’m sure that if I went back and read that email I’d be embarrassed for myself but it was totally sincere. I had this amazing weekend with this girl and had an emotional connection with her unlike I’d ever had and it made me really sad that it was a fleeting moment in my life, a duty that had to be performed in order to find myself and become an adult. It was so much more than that.

There is more to this story. If anyone has read this far and is interested in hearing it I can share more of our story. I have a feeling I went really long and no one will read this far but will see. If you did make it this far, thanks for reading. It felt good to share this with the world and now that it’s all typed out I realize there is more to this story that needs to be told. Please let me know if you’re interested.

Source: reddit.com/r/gonewildstories/comments/3idkek/m_story_of_my_first_time_have_told_only_a_few

10 comments

  1. Would like to hear more. I’m kind of in the same boat as you in terms of upbringing and how I lost my virginity etc so I kinda know what it’s like. I encourage you to keep writing if you like :) I thought this one was well written but perhaps could use a little more detail

  2. Thank you for the feedback. It’s nice to know there are others in the same boat as me. It felt really long as I was writing it. I was afraid to add too much detail otherwise it would have been too long. maybe for the next one I’ll share some more juicy details.

  3. I really enjoyed this story. I wouldn’t be surprised if it gets a modest reception here, being more context than sex, but I appreciated the context. I also appreciated the small side notes about how little aspects of the experience evolved into turn-ons today. I too grew up in a conservative Christian environment and find it fascinating to uncover the ways that has shaped my present day sexual proclivities. In case you’re interested in that aspect, I’ve written one story [here](https://www.reddit.com/r/gonewildstories/comments/38uwcj/from_religion_to_hedonism_the_erotic_pinnacle_of/) that touches on it. Anyway, thanks for sharing.

  4. I know I would normally look for more sexy details than context, but in this case the context is important to me. Thanks for reading!

  5. I’m not as turned on by this post as some of the others, but I’m certainly more engaged. Would love to hear more!

  6. Sweet, it looks like a few of you want more. I’ll should be able to have something a little later.

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