I'd mentioned in my first story that one way I had masturbated as a teenager was by sticking my penis into a suitably sized bottle neck and pumping into the bottle, sliding back and forth through the smooth, slick, tight ring.
I dropped this method in college and hadn't done it for many years. Then when I was 25, I was enjoying a 'friends with benefits' relationship with a younger (college age) woman. To be honest, she was a little too wild for me; I didn't really want to be one of a number of her admirers, and the sexual part of our friendship cooled off after three or four months, though we still spent a good deal of time together for a couple of years afterwards. Came the time, though when her then boyfriend and my soon to be fiance didn't take too well to our relationship, and we amicably drifted apart.
When we'd been hot'n heavy, as we used to say, I'd confessed to her, among other indiscretions, my masturbatory exploits, including my enthusiasm, when younger, for copulating with bottles. One evening some time after we'd stopped sleeping with each other, we'd cooked and eaten a nice quiet dinner at her apartment, and shared a small carafe of wine. As I was doing dishes at the sink, she came into the kitchen and leaned against me and gave me a hug, which we often did. I hugged her back and snuggled against her, not havng any intentions of doing anything more. She pulled away slightly, gave me a mischievious look, and dropped to her knees and unzipped my jeans. She, somewhat roughly, pulled me out of my pants and boxers and I, expecting what I hadn't had for some time, slipped my rapidly inflating penis into the wine carafe.
The fit was a little loose, at first. I wasn't fully erect and as she moved the carafe back and forth on me, I quickly hardened up and was suddenly surprised at how good it felt. Unlike the bottles I'd once used, the carafe's neck was gently curved, widening at the mouth and at the bottom of the neck, but fitting softly against me in the narrower, middle of the neck. It felt so good I gave a couple of little thrusts. We both laughed. She asked me how it felt, and I described it. I wasn't too sure about it, doing this carafe thing, but as you can guess, I didn't protest too much. She'd move the carafe a little, then I'd hump a little. It wasn't a tight fit like the bottles had been, more of a gentle caress, but it was slick and smooth and felt good. I fucked the carafe for a little bit, us looking at each other, then at my erection sliding inside the glass. I pushed in all the way, the mouth pressed against my jeans, my length inside the carafe. She sort of swirled it around on me. She was watching me as I tried to pull back out but there wasn't enough lube and I stuck in the neck about halfway out. The carafe was pretty heavy, but I didn't want to take a chance on it breaking and sending me to the ER, and I told her to hold still.
She gave me another mischievious look. She must have felt me sticking in the carafe and so she began walking backwards, gently tugging me after her by my erection. She was teasing me about fucking the carafe. We finally ended up in the living room by the couch where we determined how we were going to do this. She knelt on the couch and hiked up her skirt, with the carafe clamped between the tops of her thighs. I was still wedged in the mouth, afraid to pull out, but stimulated by the movement. I stood for several moments, her hands on my hips, mine holding her arms, willing my erection to go down. When it did start to soften, I gently withdrew and spitting in my hand, slathered myself in my own saliva and re-entered the mouth of the carafe. I rested my hands on her hips. She slid her hands into my back pockets, and I started fucking the carafe.
I was a bit self conscious at first. Sure it felt good, but the whole thing was pretty strange. But I quickly stopped caring and just enjoyed it. Slow and gentle proved to be the best and so I stood there holding her and pumping in and out for many minutes. I had to stop and re-lube a couple of times. The fit was not tight, just enough to provide a gentle caress, and I soon realized I could go for a long time this way. We didn't say much as I was fucking the carafe. I let her guide my hips with her hands and control my movement. It took me a few mintues to notice that as I was pumping into the carafe, or more accurately, she was now pumping me into the carafe, she was pressing herself against it, or I was pushing it against her and she was being stimulated through her panties. Her hips began to make little jerks against my thrusting and I had to push in all way in to get the sensitive end of my shaft out of the tight neck and keep myself from cumming from excitement as I watched and felt her getting more aroused. She pulled me back out and then started moving us faster and faster. She was starting to breathe a little harder. She rocked the carafe back and forth with her hips, and worked me in and out of it with her hands on my ass, stuffed in my back pockets.
I was then quickly getting to the point of cumming but then I could see her thighs clenching, and all of a sudden I had visions of the carafe collapsing, shattering, and horribly injuring us. Then my zipper suddenly started pinching at the base of my penis. Frustration! Fear! Hell, with that zipper, hey that HURT! I thought I was going to lose my erection, just as it was getting really good. But I was still fucking, and it felt good and I really wanted to cum. We were both fucking in rythym then, and she told me she was going to cum. I held her hips and tried keep her still as I jabbed into the carafe, trying to bring myself off and hoping she'd cum before the carafe shattered or my zipper severed an artery. But there was little resistance from the carafe's neck and I slid back and forth faster and faster. She came then and sighed, a sound I'd heard before, and pressed against me. I held her steady and determinedly fucked the neck of the carafe, keeping my penis in position for the most stimulation and then felt my orgasm nearing. It was maddeningly slow to arive but when it did I actually felt my balls tighten up and my cum moving through and out of me with some serious force in these odd lingering spurts as I, came. I kept fucking the carafe and it sort of teased the orgasm out of me, since it never gripped me very tightly. I'd just about finished cumming and leaned forward and kissed her. She leaned against me and kissed me back, and the carafe slipped from between her thighs. It was hanging on my erection, and slowly slipped off, in a very pleasurable way surprising us with this 'thhluuuooop' sound when my penis popped out then loudly shattering as it hit the tiled floor at my feet.