my first time riding bareback (mf, long, detailed backstory)

There's a bit of background to get through here… Quick description of me- 5'2, 125 pounds, slim but with disproportionate chest (30F), light brown long hair, green eyes. I get a lot of attention from men, but because of my breasts it's often from the wrong sort of men unfortunately.

Ever since I lost my virginity at age 17, sex has been a very casual thing for me. If I feel like having sex, I have sex, and I have moved so far from fear of being perceived as a slut. While this has been liberating, it has also been damaging, as with each new partner the association between sex and love/romance becomes weaker and weaker. I suppose you could say I've become disillusioned.

Then, in July, I met James. And no- this story isn't cliche romantic. But the sex was instantaneously fantastic. It was effortless and fun- and perhaps most surprising of all- it was consistent. I've found that casual sex relationships usually expire after about a month, as you just grow tired of each other. But this kept going. Despite being over ten years my senior (36 to my 25) his libido was impressive, with our best record being seven times in one night. We also had sex in the hospital where we both work- a story for another time.

Obviously we are attracted to each other, but sexual chemistry is where it ends. Physically he is ok, although I hate his hair, which is shoulder length and curly. He has a degree, but has been working part time as a hospital porter for the last ten years because he doesn't want to be 'tied down', we don't like any of the same things, and he doesn't get my sense of humour at all. He often suggests we get food or watch a movie after sex- but I don't know why because we ultimately end up bickering and I am genuinely a very passive person! We had a conversation early on that we both just wanted something casual and it clearly wasn't an exclusive thing. At one point we were both also sleeping with another person, and we're open about it and everything was fine.

Well I suppose it can't stay simple forever. My other sex buddy became a lot less reliable, while James was still seeing his other girl quite a lot. Jealousy ensued. I told him I was starting to feel jealous and I didn't want him to mention her to me anymore. Around this time, I also started taking birth control, as James and I had both been recently tested and were looking forward to doing away with condoms. I texted James, saying I might call over after a night out (this would be our first night not using condoms, but he didn't realise at this point I had started birth control). He replied yeh cool but Lisa might text me too. I obviously got really annoyed, we had a big fight, and I didn't end up going to his house. I broke it off with him the next day, told him I was deleting his number and I didn't want to hear from him anymore, but it was all very civil. He thought I was being dramatic and was angry at first but was ok about it in the end.

Fast forward two weeks, the anger has dissolved and I am missing him terribly. I relive every encounter we ever had over and over in my mind. I can vividly reimagine how his cock felt against my lips, his fingers in my hair. My whole body craves him and every other man had become invisible to me. One Friday night, while out with my friends, I decided drunkenly to go to the bar where we first met in the hopes of running in to him there. I saw him almost straight away, and he came over and hugged me tight and told me he had come hoping to run into me.

My heart was racing, I just felt this crazy joy to be near him again. I kept up the pretence that we were just friends for the rest of the night, but we didn't leave each other's side and held hands a few times. At the end of the night he asked me to stay at his house, and that he misses sleeping next to me. I agreed, and we got a taxi back. He gave me a tshirt to sleep in and we cuddled close, my head on his chest. He eventually sighed into my ear, 'I've missed you. I'll never see her again if you don't want me to' Which of course, was all I needed to hear. I told him I didn't need him to myself, I'd be a fool to even try, but I need to know he wants me the most.

At this point we are hugging each other tight and I can feel his cock poking into my stomach. It had only been two weeks but I craved him so much I almost forgot to kiss his lips before taking him in my mouth. He groaned my name as I licked him from base to tip, before impatiently sliding him deep into my throat. He rests a hand on the back of my head, encouraging me, and I look up at his face as I bob up and down. His heavy breathing is making me so turned on, I am so eager to climb on top of him at this point. But I am very submissive and obediently suck him until instructed otherwise.

He asks if I am wet, and I take my cue to kick off my underwear and crawl on top of him and kiss him, sliding my wetness against him, and I whisper in his ear 'please fuck me, I've missed your cock so much, I've thought about you every day', and he positions himself as I lower myself down on him, feeling him bare inside me for the first time. We are looking each other in the eyes as he slowly pushed in to me, I can't actually believe how much better it feels even for me without the condom. I realise I'm still wearing the tshirt and discard it, and James wasted no time in pulling me down and biting and sucking me as I slowly grind against him.

I pull myself up straight, so I can ride him hard, he is grabbing my hips with his strong hands and I am literally bouncing up and down on his cock, hard and fast, screaming out his name. The whole time we are saying all these things we would never normally say- like how good it feels, and that I was all his, he was the only man that can make me feel this way etc- which made it so much more intense.

I could feel my orgasm building, it had been a long time coming and I knew it was going to be intense. It kept building up, and James would change rhythm at the last minute and I'd lose it, I was getting exhausted and frustrated. I was still on top, so uncharacteristically took control and pinned James's hands down over his head so that I could move at my own speed. I loved the look of surprise on his face as I rode him, using him to get off my way. My orgasm was building up again, I was grinding my clit against his pubic bone and it was too much- it kept building up and up, I could feel myself at the edge for what felt like forever, almost holding my breath, my face so hot, so so close…

From somewhere far away I hear James say 'wait stop I'm going to cum' and he tried to unpin his hands (coming inside me was something we had discussed before and concluded it was too intimate for us). But I barely heard him, as I released his hands and collapsed onto him, literally screaming as an earthquake of pleasure coursed through my entire body, over and over, and his arms wrapped around me, pulling me closer as he unloaded deep inside me, shaking underneath me. We looked at each other and kissed slowly, smiling at each other before I slid off him and we fell asleep in each other's arms.

That was all about 3 weeks ago, we have seen each other a few times since, but never for real dates, just hook ups. I guess I just got carried away with the romantic reunion, and all the stuff we said that night was just over enthusiasm. He went away on a month long trip to Singapore with some friends a week ago, he texted me before he left and said that he would miss me, and not just the sex, and he cares about me. I told him I'd miss him too but I haven't heard from him at all while he has been gone… The whole thing has been a mind fuck. Is sexual chemistry really enough to create genuine affection? Should I see where this goes, or get away while I still can? Sorry I know this isn't the right place to ask for advice- but would appreciate any advice people have about it!

Hope you enjoyed the story and it wasn't too drawn out with boring details!!

Source: reddit.com/r/gonewildstories/comments/3zy8eh/my_first_time_riding_bareback_mf_long_detailed

12 comments

  1. Great story :) my advice is to go out and play the field for numbers (not sex, necessarily). Go on dates. Basically keep your perceived value up by showing that you have plenty of options. You sound like any guy would be lucky to have your attention. In my opinion, if he knows he’s your only option, he may exploit that and lose interest altogether. Good luck!

  2. I really, really enjoyed this story. You guys clearly have great chemistry. What’s different about this guy – is it his cock? I have only limited info, but my feeling is you should keep seeing each other. Maybe he will start to understand your sense of humour, and you can negotiate a bit of a haircut!

  3. His cock is very nice but that’s not all there is. He is very communicative during sex and totally honest with me always. And he doesn’t get freaked out by anything I say, so I can be totally honest with him too- like anything goes. So I guess I trust him a lot, but then I remember there’s this other girl, and she might feel all these things about him too (she doesn’t know I exist) and then I think I need to back away again. Thanks for your reply

  4. Sometimes it’s said that dancing is a precursor to sex. I don’t think it’s said that sex is a precursor to dancing. I hope it’s not true either way, because I’m a terrible dancer. But I think sex can be a precursor to character: i.e., if someone is patient, open, and communicative between the bedsheets (or over the desk, as it may be), then it’s a really good sign. It means the raw materials might well be there for something meaningful. Throw in the intimacy of sex, and it’s clear that at least some of this is impacting how you think about him. So I think it’s not worth brushing aside simply because, till now at least, you’ve both had an open arrangement. One thought: you guys arranged to have sex without condoms. He’d be a real shit, I expect, if he made that arrangement with the other girl too. So (unless I’m wrong) it sounds like he was happy to take that step with you, not her. That’s positive. In any case, she doesn’t have to be in the frame for discerning how you yourself feel about taking things further. Difficult as it may be, you can ascertain that without thinking of her. If you would like to be with him in perhaps more than a casual sex way, then I think it’s worth broaching with him when he returns. My two penneth :)

  5. Hmm let me spell this out for you. No dates, just random hookups, he has another girl that doesn’t know you exist. Oh dear, you’re the side piece and that’s where you’re staying. Sweet talking bs means crap. If anything was really there you wouldn’t be his dirty little secret. Make sense?

  6. I think the raw materials are there, but having reflected on the whole thing, it’s clear to me now that he just doesn’t care about it as much as I do. That’s not a position I want to be in. If I don’t hear from him at all this month I will know for sure that I am right and I need to walk away. But if I do hear from him… I have a weakness for him, I doubt I’ll be able to stay away

  7. Yes this makes perfect sense. I think I was a bit naive and too easily swayed by anything remotely romantic he said. I’ll need to be wiser in the future

  8. You may be right. Then again, guys are notoriously bad at letting their feelings be known. Either way, it’s probably a good idea, as you say, to see if he contacts you. I wish you the best of luck :)

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