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My First Anal Experience
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So this is an older story about when I took someone's cock the first time in the swinging scene, when I was a lot younger and still exploring my sexuality. It wasn't my first time with a man, as I played casually or met guys for them to give me head but nothing more.

I met this guy on a swingers site, where he posted that he was hosting a gloryhole/darkroom session. Wanting to be more relaxed, I opted for the darkroom session and organised a meet. He'd leave his door unlatched, and instructed me to take my clothes off fully and lie on the bed and then he'd join me.

I parked up the road from his apartment and he buzzed me in, and went to his door which was indeed partially open. The corridor is lit, so I start stripping as I walk up it to the bedroom as he instructed and entered a blacked our room where the only light was from the hall. I placed my clothes on a chair, closed the door and stumbled from memory to where the bed was and lay spread eagles. I heard the door to his ensuite open, and him also stumble to the bed feeling for my legs and when he found it got straight to work spreading my legs and sucking my cock and balls with intensity and pleasure few women have ever achieved. I don't cum easily from oral so he worked his magic for nearly 10 minutes, getting me close but not quite there. He asked if I wanted to fuck him,which I definitely did at that point and admitted I've never fucked a guy before. He said that's fine, and climbed into bed with me to kiss me. I realised then that he was also naked, slim and muscular and a massive cock which rested against me. I had no idea what this guy looked like but he was physically amazing, better that some of a fattening husbands I've share before. We made out as we stroked each other, and then he reached over to his dresser pulling out condoms and lube. In the pitch black I put the condom on as I felt him lube himself up and we got into doggy style, where he guided my tip into his entrance and pulled me into him as I slipped out a few times. I finally slid in, and after the first 3 inches he pushed back into me to take me the rest of the way. He asked me to fuck him slow and hard, which I did as instructed following his lead and reaching around to stroke his now semi hard cock to get him hard again. He was super tight compared to pussy and had me at the edge within minutes until I finally came and collapsed on top of him.

After lying together and recovering, he asked if I wanted to get fucked and in a moment of horny haze I said I'll definitely try it but I haven't prepped in any way aside from a shower. He was too horny to care, he rolled me off his back and told me to take off the condom which he put to the side. He cleaned up my cum glazed cock, then grabbed my legs, lifting them up and spreading them as he started rimming my ass.

He came up for air, and asked if he could finger me first and reached over for another condom to put on his finger, with some lube and started working my ring in the dark. As he pushed in further he continued to suck my soft cock to distract me from the feeling. Once he got his middle finger in, he started to finger fuck me as I felt like I imagine every other girl I did the same thing to felt when I ate them and fingered their ass. After my 5minutes of fingering and me acting like I'm having a seizure moaning he tells me to get into doggy. Now this guy is bigger than me in every way, 8 inches and thick so I hold my breath as he lubes me again and I feel his tip push into me. I'm basically in the downward dog position as he slides in and spreads me wide, a pressure where it feels like my small intestines are. I ask him to take a break as I adjust to his size, I reach under and there's still enough cock for my hands to wrap around which he let's out a laugh, saying "not all the way yet". He then begins to pull out ans push in, slowly fucking me and pushing deeper with each thrust slowly until he's fully inserted into me. Getting into a more comfortable position, he slowly starts pumping my asshole with full strokes which has me absolutely melting down from the feeling of him in me with twitches and grunts as his thighs smack my ass and his balls hit mine. I tell him I feel like I'm going to cum, even though I'm semi hard and he tells me to switch positions to my back, he pulls out and he changes condoms to a cleaner one and then gets me into missionary.

I'm relubed, spread wide and he enters my ass again facing each other as we kiss (its still pitch black). He sits up, my legs on his shoulder as he starts jerking me off and I get rock hard within moments, as he also plays with nipples. He tells me to cum if I feel like it and with each stroke from him in me and on me, I get closer and closer until I finally climax with spurts of cum over his and mainly my chest. I feel absolutely drained by the seizure inducing orgasm and he starts to fuck me even hard like a sex doll until he also cums in me, me feeling every throb of his cock. And collapsed on me also.

We cuddled for a bit longer and then told me to use his bathroom as I saw fit and can leave while he uses the guest bathroom. I cleaned up, got changed and left quickly while he was in the bathroom knowing I'd be in pain the way home. We became semi-regular meets for a bit after, sharing girls and TV/TS girls between us until moving away a few months later.

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1 year ago