Going to write this while it’s still etched in my mind, just gonna be straight up honest here. I’m writing this for my own masturbation material so it’s gonna be pretty explicit, it is true though. Fair warning, this is long.
Small bit of context. Boyfriend of 11 years dumped me with no explanation, we were each other’s first everything’s so this was all a new experience. After he left me I went to a hotel, went on tinder and found the first guy that caught my eye and invited him over, he quickly accepted. Also, this happened about two weeks back.
Once he arrived we said our hellos and all that, after a while of small talk I told him my situation so he’s aware, he told he knows I’ve only had sex with one man and I’m in a the middle of a breakup etc and if I want to back out or just watch a movie we can do that. I said no, I was determined to follow through. I was actually a little offended that he was talking to me like I was innocent so I began to feel up his crotch and I straddled him.
We went at it for a few minutes before he put his hands on my ass and picked me up, taking me in his arms and walking me to the bedroom. I loved it, I felt like a princess as he held me, it was borderline romantic. He put me down on the bed and began to stroke my thighs as we made out further, it wasn’t long until we were both wearing nothing but our underwear. He ran his fingers gently over my boobs and grinned, I pushed his hands off playfully and told him to take his pants off. He was quick to comply.
Now I’d seen photos of his dick before when we verified we were both real on Snapchat but seeing it in person was something else, it was very, VERY intimidating to say the least. He said he’s a bit under 10 inches and that’s certainly believable, his thickness was what scared me the most, he was almost as thick as my wrist. He looked at me quizzically so I quickly took my bra off and crawled over the mattress towards him. Hopefully I didn’t appear to be too awkward as I started to jack him off, my ex boyfriend is a bit smaller so that’s what I’m primarily used to and working with a penis this size was a real process. This guy was also uncut so that was another new toolset I had to work with.
I put my mouth over his dick and slowly began to blow him. I don’t think I did a great job as I was very nervous and I wasn’t used to dealing with one that thick but he seemed to enjoy himself regardless. I couldn’t get it very far down but I kept flicking my tongue on the tip while slowly moving up and down until I had about half of it in my mouth and judging by his moans, it was much appreciated.
After about 5 minutes of that he put his hands on my face, kissed me and moved my body so I was on my back looking up at him. He looked at me questioningly and I nodded as he began to pull my panties down my legs and removed them from my body. He smiled at me reassuringly before gently slipping a finger inside me, by this point I was very wet and knew I could take more so I told him as much. He put two fingers in then three, he started to move his fingers around and I just weakly smiled and closed my eyes as I took in the feeling. He continued with that for a few minutes, stretching me out with his finger to prepare me. After a while I heard him open a plastic container, he began to coat his hands in lube. The aching feeling I had when I felt the coldness of the lube on his fingers enter me was indescribable, my mouth was actually watering as he worked away to coat my insides with it. Once he pulled his hands from me and began to apply lube to himself, that’s when I really started to get nervous, the reality of the situation finally hitting me. I was about to let a man I’d known for about an hour fuck me. I was honestly pretty tempted to back down but I couldn’t find the words, I stayed quiet and he got back on the bed and positioned himself over me. I brushed my thoughts aside and began to make out with him again.
As we were kissing I began to feel tugging feeling on my clit, his hands were still all over my hips feeling me up so I realised that had to be his dick pressed against my crotch. It felt so wrong but so good too, I felt like I was doing something wrong and it was a huge turn on.
After a few minutes of kissing and groping he pulled away, I smiled and shakily said I was ready. He kissed me softly once more before putting a hand on his penis and pushing it inside me. I don’t know why but I shivered slightly when he entered me, I wasn’t cold at all but it just happened. He started slow, barely putting the tip in to gauge how I’d react, I smiled and he pushed a bit more before stopping, after that I lost patience, wrapped my hands round his neck and pulled his face to mine, driving his dick into me in the process. He pushed a little more and I felt my vagina stretch to accommodate him, he was fully in, as far as he could go. I had a mini panic attack and took several deep breaths as I adjusted. Having him in me was quite the experience. It was… tight, not painful thankfully but very tight. I panicked a little but he pressed a hand gently over my mouth before I could say anything and told me just to be still for a couple of minutes. We did that and it was surprisingly intimate. We didn’t kiss, we just looked each other in the eye as his dick sat motionless inside me.
After what felt like forever but was probably only a few minutes he looked at me with a cute little smile and asked me if I was okay, I sorta nodded and he asked me again more assertively and I told him I was. He called me a “good girl” which drove me nuts for some reason, he began to slowly move out, the head of his penis stopped right at the entrance to my vagina, we smirked at each other for a moment before he pushed himself back inside me with a sigh.
As he thrusted into me gently I stretched my arm down the length of our bodies and began to softly stroke his balls as he began to pick up the pace, it felt incredible. Before long I lost my focus and just gave into the moment, wrapping my legs around him as I did my best to just hold on. I’m pretty awkward with noises so I usually try and stay quiet beyond some soft moaning but with this I was pretty much panting as he worked on me. It felt incredible. I enjoy sex but I’m usually more of an oral kinda girl but this was just so much better. I don’t know if it was due to his size or the length of time since I’d last gotten laid but I felt everything so much more here. It was quite literally orgasmic.
He also kept deliberately making his dick twitch while it was in me and oh my god it feels so good, it’s only a minor physical sensation but there was something so nice about it that just sets me off and really gets me going.
Now as I said, I’m not much of a moaner but the warmth, sensation and the moment got to me. I wasn’t conscious, not really, I was just there as he was laying into me. I made noises I never knew I could make without trying to make them. I think I even giggled at one point, there wasn’t anything funny going on I was just so high on emotions and lost control of my inhibitions and let loose.
Soon enough I felt a warmth began to fester in my feet before working its way up my legs, I giggled slightly and shivered again as I had my first orgasm of the night. It was lovely, in that moment I felt so close to him and honestly it’s the happiest I’ve felt in a good while, it was very liberating to just be there with another person so close to me and feel that good.
The emotions definitely were there as I actually started to cry after cumming. I think it was a mixture of pleasure and feeling overwhelmed. I’d never kissed another man let alone this and I felt guilty that had just orgasmed to another man thrusting inside me. I kept thinking about my ex boyfriend and how he would feel if he knew about this, I knew we were over but still it was a lot to process. I’d always assumed we’d be happily married by now, not him being at home and me being in a hotel bed with a strange man. Life’s weird. The worst part was as guilty as I felt my priority was still what I had in front of me and the event at hand, I’d come here for sex and that’s what I needed.
He told me we could stop if I wanted to but I just shook my head and asked him if we could please continue. He wiped some tears from my cheek and started to kiss me passionately, cuddling me as he pressed his weight onto me, pushing me down into the mattress. I just pressed my face to his neck and closed my eyes as I felt his dick begin to move about inside of me once more. What followed next was the longest orgasm I’ve ever experienced. I don’t know how long it was exactly but it was damn close to 10 minutes of fairly consistent pleasure. It was honestly so good I thought I might faint. It was blissful.
Before long my sighs were met with his, his pace intensified and lost its tempo as he got more wild and he began to pretty much thrash about inside me, he was literally pounding me me so hard he had to hold my shoulders to stop me from hitting my head against the backboard. He growled slightly in my ear as he came inside me, it felt great. His cock kept twitching uncontrollably and I fucking loved it. To me having a guy cum inside you is one of the highest praises you can get.
Afterwards he went out to pick us up some food, when he got back we ate and chatted before deciding to go for another round. This time I rode him on the couch until we both came. I’m no longer intimidated by his size, I definitely couldn’t take it without being warmed up but I now know I can take it and at quite a pace. I’m actually quite proud of myself for taking such a big dick without much struggle, definitely underestimated myself on that front. That being said, it’s also a process to take it and I felt sore every time after.
After about a week of us hooking up I blocked him, I don’t want to go into the details of why but trust me, it was justified. Since then I’ve had sex with one other guy, a friend of mine, I don’t know where things will go but it’s fun! Better too, with this guy from a pure sexual point of view he’s the best I’ve had by far but my friend is more of a manageable size, he’s nicer and I feel comfortable with him.
Anyway, that’s my confession I guess feel free to PM me if you want to chat! Just don’t be too weird please.
Source: reddit.com/r/gonewildstories/comments/mx9unl/f_the_first_time_i_had_sex_with_someone_other