[M]y [F]irst time being fucked with a wine bottle in my tight pussy

This is a story of an experience I had in college that I often go back to when I’m wanting to get off, mainly because it was a first and I love firsts when I comes to sex. So I thought I’d finally share with you all. ***names have been changed to protect the guys identity***

I met Derek during college, he was in my group for a project my senior year. We had known each other since sophomore year but only cordially. When I saw he was in my class at the beginning of the year, we sat by each other and within that first week of school we had fucked twice. Both times were apparent that he was just as much a freak as I was, and I liked that. (Side note: I consider myself a closet freak, you would never know by meeting me that I enjoy (now in my late 20s) getting fucked in the ass, being dominated, spanked until I cum, wearing my ben wa balls in public, or having my nipples pulled so hard that they could one day come off (hopefully not cuse I like my nipples).)

It was mid-November by the time Derek and I were fucking on a regular basis. He and I were starting to explore BDSM, a first for both of us. I learned quickly how much I liked being dominated and having a man inflict sexual pain on me. He is also a very smart guy and clever, so it was him that would come up with new shit to try. That day he sent me a text asking if I was at my apartment alone and I knew what that meant, and god it was perfect timing because my pussy had been aching for a few days at this point.

I’ve basically been doing the same masturbation since I was 20, using my vibrator on my clit while I fucked my suction cupped dildo. As I got older, I still appreciated that “routine” but I slowly added in fucking myself in the ass using a smaller dildo while I put my Ben Wa balls in my just-dildo-fucked pussy. After only riding my dildo that week as my young and naive self would, I was beginning to realize I needed more stimulation and exploration. (The stars were fucking aligned with Derek coming in hot, ok?)

By the time Derek had gotten to my apartment, I had already soaked through my panties. He told me to drop my shorts (I fucking loved it when he commanded me.) I obeyed and could feel my wetness dripping. He noticed how wet I was, I could tell because he smiled at me and demanded I take my shirt off and go sit on the bed, he’d “be there in a minute.” I squirmed on the bed hearing him open kitchen drawers and cabinets. He walked into the bedroom with a bottle of wine and coconut oil.

He told me to put a pillow under my butt and lay back and spread my legs as far as I could. I happily obliged. He put his fingers inside me, just two at first and then he was trying four. My tits were swelling up and my face started to feel hot. He hand-fucked me for a minute and then put his fingers in my mouth, I licked off my juices and sucked a little… I taste myself often when I’m playing with myself so I was glad he let me.

He opened the coconut oil and started lathering up the top part of the full wine bottle. Now I’ll tell you at this point I started to panic a little because he’s fisted me before and although he got his fist in, it hurt too much and I had to use my safe word. I’m a petite girl, standing 5 feet tall, and my pussy follows suit on those proportions. So when I saw him with that fucking wine bottle I said, “maybe not yet” but he told me to shut up and spread my legs farther. (I was curious anyway… I was wanting to learn.)

He put the neck of the bottle inside me… it was cold and hard, foreign, but I liked the thought of it down there. I spread my legs as much as I could, the pillow under my ass helped level the playing field. He gently started twisting the bottle to get the oil all around my pussy. The neck was fully inside me and I could feel the thick part of the bottle rubbing against my clit. Hello eyes rolling in my head.

I can’t explain it other than this: the anticipation that he was going to try and fit the thick part of the wine bottle in my pussy was a lot to process but I was down to try. The bottle got thick about two inches from the cap and stayed that thickness. So once he started pushing it in, forcefully, it hurt. I felt my bones ache, I felt my skin being pulled, thought it was tearing, and I didn’t think I could do it. I heavily considered my safe word but right then he stopped pushing and said, “Feel it. Now.” I opened my eyes (shut them while I was panicking haha!) and the expanded part of the bottle had completely stretched my pussy…I had never seen it that stretched before or any pussy for that matter (my porn searches weren’t fully hardcore yet.)

The bottle took up all of the space where my pussy was… my folds were pushed to each of my thighs so all I saw was bottle and bulging. I reached to touch the tightened skin and he jerked the bottle out, and suddenly my pussy looked like nothing had happened. That’s when I understood… I was fucking CRAVING for it to be back inside me. It’s like it stretched me so far at just the right pace that I needed it. No turning back, no chance in hell I’d be using my safe word.

I asked, “Sir, will you please put it back in and push it more?” He smiled and put it back in, this time the thick part went in slightly easier… although it felt like I was being ripped apart. I fucking. loved. it. I remember later that I whimpered loudly and I didn’t realize it in the moment. He twisted the bottle round and round and tried to pump it, swiveling it… the pain was unreal and it hurt so good. He pulled my hips forward until my pussy was almost vertical on the pillow, he had to reposition himself and lift up the wine bottle.

When he did, the wine in the bottle fell toward the neck and it was all the sudden very heavy inside me… the bottle fell so far in from the weight of the wine and my reposition that I felt it in my stomach. It felt incredibly hard, warm now from my throbbing pussy, thick and full. I could feel the top of the neck at my cervix every time he twisted and pumped the bottle, letting go every now and then allowing it to just sit in my pussy… the wine doing the work inside the bottle creating a heavy movement inside me. He would pull the bottle down toward my ass and we could see the neck bulging through my skin. He was now fucking me HARD with this bottle. I couldn’t move any part of my body it hurt so bad… but like I said… it hurt fucking perfectly.

Every time he pushed the bottle from the top side downward, it would stroke my g spot. He did this in a pattern, watching me while I was sweating and trying not to cry but I didn’t want to cry because it was a wonderful sensation of pain. I like pain, remember? My legs were shaking, my clit was stretched so far at this point that it stuck straight out, there was no skin left to hide it per the usual. He tortured me by slapping it hard with his free hand. I remember out of reflex I squeezed my puss and it had no muscle left to squeeze… it was maxed out and I had no control.

He took the bottle out and fucked me in the same position until he shoved his cock in my mouth for me to swallow. He grabbed my hair so forcefully that I gagged on him but he didn’t let me go, I could taste myself on him until his cum spewed down the back of my throat. He let go of my hair, assuming that I’d take my mouth off but I sucked the tip until he cried out… you know, my way of sweet revenge for the times he slapped my overly exposed clit. He slapped my face for this. Fucking yes.

I want to say my favorite part of this “first” was during the wine bottle fucking but honestly, my favorite part was how sore my pussy was the next two days. The skin around my pussy was bruised and it hurt when I sat down, stood up, walked… it was sore doing anything. Where he had pushed the bottle so far that he could see it move through my skin? Bruised.

I wore the bruises like battle scars because that’s how much I enjoyed it. Years later this story still gets me going, and I’ve incorporated wine bottles every now and then into my personal play time. It’s also propelled me into my sexual awakening and exploration with men. Stay tuned ;)

Source: reddit.com/r/gonewildstories/comments/8lv1lg/my_first_time_being_fucked_with_a_wine_bottle_in