I discovered my favorite sex act – deepthroat – when I found videos of the G.O.A.T. Heather from iDeepthroat, back in my college days. There’s something about watching someone looking up at you, with your cock vanished into their mouth. In general, I prefer oral sex over all other sexual acts, and could basically 69 all day with the right partner. It’s been difficult to find a partner who can satisfy my desire, but with … her … I had a chance. This is how it happened.
Quick aside – this is a true story to the best of my memory, though I’m changing the names of the people involved just so I feel more comfortable. This story also happened a number of years ago but I will *never* forget it. Going to give some backstory and build-up here, but if you really can’t wait, scroll down to the next line break after this one to more or less get into the action.
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I first met Cara online, through a mutual friend of ours named Vicky. Vicky and I had dated briefly but decided to just be friends after some time, and we grew closer as friends over the course of a few years. I’m a big nerd, and I wanted to get Vicky into Dungeons and Dragons, so I decided to throw together an online game. When we were looking for players, Vicky reached out to Cara. They hadn’t spoken much since they graduated from high school together, but they were Facebook friends, and Vicky thought Cara might be interested in playing.
It wasn’t long after the group got together that I ended up chatting with Cara regularly. I don’t remember how exactly the topic moved to sex, but I suppose it’s pretty likely to happen when two single people start talking. She told me she loved giving blowjobs, and that she was really good at deepthroating. My heart skipped a beat while all the blood rushed downward. Immediately, my jaw dropped and I had to pry. We talked a bit more, and I let her know that I’m fairly well endowed – which has been a stumbling block for my favorite sex act in the past. She looked me dead in the eyes (as much as you could over a video chat) and said “no problem.”
At first, I wasn’t sure how serious she was about her skill, or her desire to get with me. We started talking about meeting up somewhere for a fling – while I had some small feelings for her, I knew in the back of my head that nothing but a fling would ever happen between us. We lived at completely different ends of the country. She’d send me pictures in lingerie – never showing her bare chest or anything else. She took a picture while licking a popsicle, and then another with the entirety of it in her mouth. The build up was intense.
Eventually, fate smiled upon us, and we had an opportunity. Vicky was staying in their hometown for a week to house-sit for a relative, and Cara was flying out there for the weekend to visit her family. I got a really cheap bus ticket, and the plans were set. I’d go visit with Vicky for the week, and on the weekend we’d meet up with Cara and hang out – and hopefully, more.
When it became clear that Cara was completely serious, I grew nervous. I’m a fairly anxious person in general, but the idea of meeting up with someone who was effectively a stranger, and having them fulfill a life long fantasy of mine in a wild fling is exciting on paper, but very far out of my comfort zone. We discussed how we thought things would happen, and she made one thing crystal clear. When the time came, and we were alone together, I was not to ask her. I was to just wordlessly initiate contact with her, and take. I have a feeling I was fulfilling a fantasy of hers too. So, we agreed.
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The week with Vicky was fun – video games and laughs all around. When Cara arrived, we had a pleasant and platonic moment of greeting, and spent some time hanging out with Vicky, shooting the breeze. Cara seemed cold – not rude necessarily, but not flirty. I’d seen pictures, I’d seen her on a webcam, but seeing her in real life almost made my heart beat out of my chest. I like busty girls, and while she wasn’t massive in that department, she definitely had a chest I couldn’t wait to play with. She’s curvy in all the other places, and I was ready for a taste.
When it got somewhat late, Vicky said she was getting tired and so stood up to leave and bid us both a good night. (She knew, more or less, what we were going to be up to and was cool with it. “Just don’t stain anything.”) I was laying down on a futon bed in the room we were all hanging out in, and stood along with Cara to walk to the door. Cara moved to close the door, and time slowed to a crawl. She’s been acting somewhat coldly, did she change her mind? This is the moment, if I try to back down and make some conversation or something, she might think I chickened out. If she’s for real, she told me not to ask, but to just go for it. This is the moment.
I went for it.
Right as she was turning towards me, I gently grabbed her shoulders and pushed her back against the wall, leaning down slightly to kiss her. She returned the kiss with passion – and my heart fluttered. I got the hardest, largest boner of my life instantly, and the next few seconds were a blur of kisses, awkward backpedaling, and a whirlwind of clothes being thrown about the room. When we got back to the bed, she playfully pushed me down and worked herself between my legs.
The first touch of her hand as she grabbed my cock sent a shiver up my spine – but I couldn’t afford to get distracted. I locked eyes with her. She settled herself in, and looking right up at me, effortlessly took the full length of my cock into her mouth and down her throat. No hesitation, no trouble, she laid out all the cards right there. She really could take all of it. My heart began to pound in my chest as she started sucking, varying the pace and depth to tease me at just the right times. I knew I couldn’t last all night, but the stars were aligned and I got to enjoy the best blowjob of my life for a few minutes.
I’m fairly loud, and thankfully Vicky was far upstairs and there was no way she could ever hear us, so as I got closer to orgasm, I gave her the feedback to let her know. She had previously told me she loved to swallow, and the more cum the better, so I had resisted any form of masturbation for two weeks despite all of her teasing. (No idea if it helps that much, don’t care.) Through the intensity of her lips, tongue, and throat massaging my cock in every which way, I stole another glance at her, and her eyes said she was ready.
I grabbed a fistful of hair, shoved my cock as deep into her throat as it would go, and gave her the biggest load – and the loudest moan – of my life. As it flowed, it became a bit too much for her to handle and she ended up coughing and snorting a bunch of it out. She had told me there was no way she couldn’t handle it. I was worried for a moment I had hurt her. I let go of her hair after I was done and she gently slid me out of her throat and through her lips, giving a kiss to the tip as the contact ended. I’m not normally a fan of extremely rough deepthroat or blowjobs – I want the giver to be controlling the pace, not choking herself or gagging but just showing her skills and passion. She smiled as she sat up, and laughed about how it came out her nose, and she asked me for a tissue.
Relief washed over me, and I helped her get cleaned up while we laughed about the events. We both went to the washroom so she could look in the mirror to clean herself up, and I played with her tits. She rolled her eyes and playfully told me to stop, but I knew she didn’t really want me to. After she had cleaned her throat and nose out and was feeling better, i led her back to the bed, and decided to take my turn between the legs.
I think that’s going to have to be a tale for another day, as this is getting really long already. This is my first time ever writing something like this, and I hope someone enjoys it and gets something out of it. I honestly felt like this was just a big humblebrag or something, so hopefully it doesn’t come across that way. If there’s interest, I will write what happened the rest of the night and the day after. And yeah, I haven’t seen her or even really talked to her since. I’d love some feedback!
Source: reddit.com/r/gonewildstories/comments/ikb2la/i_34mustered_up_the_courage_to_do_exactly_what