I first came to know Lily through Twitter. (It’s one of my weird abilities in life to convert “online interaction” into “woke up next to her.”) In her case, she was friends with another play partner of mine that I had spent a marvelous weekend in the Reeperbahn district. Although my history with her friend was never REALLY made explicit, we kind of knew what was up. Lily, however, was married, and in a very conservative religious community. While I was trying to be circumspect about who I chose as partners at the time, and avoid the drama of an angry spouse hunting me down, there was a chemistry there I couldn’t ignore. Especially after seeing her get involved with a second-rate character in an online-only thing, I kind of felt that stupid male competitiveness thing kick in.
So I finally decided to parlay the online chemistry into a date, which turned out to be a very easy proposition, as she was even more interested than me. We picked a weekend her husband would be away, which he was on a regular basis, and I booked a hotel room in her city but a different neighborhood. Although traffic wasn’t my friend, I made it there within a reasonable time of my target, and she was waiting in the lobby, her hair neatly tucked under her hat, dressed conservatively. She was short, about 5’2, with dark hair and pale skin. I’m about 6’4”, so the difference in height was really noticeable.
On first “real” meetings for online dates, I have a rule that I make sure we go out for dinner before anything happens. It just allows some time to get past the awkwardness of it all, and allows you to really connect the feelings you have online to the person you are with. So we went to a nearby Italian restaurant that, although the food was good, was just a disaster for being too loud. After making it through dinner we walked on the riverside, and as we passed through a construction area, with canvases draped over the sidewalk, I stopped. While not exactly private, we were hard to see here. I turned and pulled her close, kissing her on the lips, which soon parted and turned into a deeper kiss, our tongues caressing each other. As I broke the kiss, her hand shot to the back of my head, pulling me back in to kiss some more, one of my favorite moves any woman can do.
After kissing for a few minutes there on the street, I broke the kiss long enough to ask if she wanted to go to my hotel. She nodded hard against my chest, and I all but carried her there in a dead sprint. Once we got in the room, I didn’t even let her get past the doorway, but instead pinned her to the wall, kissing her there, using my size to trap her. Her hands pushed my coat off my shoulders, and I pulled her hat off and then yanked her back by her hair, turning her chin up so I could kiss down her neck. She moaned appreciatively, and I let go of her hair so she could push my coat off. I started unbuttoning her blouse, revealing the dark tank top underneath, and nearly kneeling to kiss her chest along line of her top.
After he blouse fell away I went to work on her jeans while she stepped out of her shoes, kneeling down as I pulled them to her ankles and she stepped out of them, bracing on my shoulders so as not to fall. As I knelt, I could smell her wetness, rich and sweet, soaking her underwear. In just her tank and underwear I pulled her from the wall and led her to the foot of the bed, facing away, and then stepped behind her. I told her to open her eyes and she saw herself in the mirror, with me behind her, kissing her necking. I watched her face as I slid my hand into her underwear, finding her wetness and slipping inside her. Her eyes fluttered closed for a moment as she felt in, and my other hand rose under her tank to hold her breast. That got very little reaction (I later realized she doesn’t enjoy attention there as much) so I slipped my hand out and wrapped it around her throat instead. With our size difference, i could almost get all the way around her neck with one hand. Her eyes snapped back open, and her arm reached behind, grasping the bulge in my slacks behind her. I continued to work my fingers in and out of her while holding her throat as smile grew on her face, then I turned her around, pushing her to her knees.
She was eager to follow the wordless order, and began unbuckling my belt, then pulling the zip down and taking my underwear with my jeans. Her cool fingers wrapped around my erection and her mouth sunk onto me. I looked in the mirror as I watched her head move on my body while I unbuttoned my shirt. A flash of pain shot through my body as her teeth grazed my hardness. She kept going as if nothing happened, and soon I realized each time she took a really deep motion, I would feel all of her molars grazing the sensitive head of my erection; her mouth was just too small for me. The flash of pain with each bob of her head was just not going to work, so I pulled her back, bending over to kiss her, since I love tasting myself on a woman, and then pulling her top off.
I sat back in bed, pulling her to her feet, and then hooking my fingers in the waistband of her black cotton underwear. I looked at her a moment, to make sure she was happy, and she smiled back and kissed me, so I pulled them down and she crawled into bed on top of me. As we kissed, she ground her hips on me, spreading her ample wetness all over me, grinding on me without taking me inside. Over and over, with a puddle starting to collect on my hips.
I finally reached over to the nightstand, where I had left the condoms, pulling one out as she kept grinding. I groaned a bit and pushed her back as she playfully tried to resist. In record time I had the condom on and pulled Lily back. Without using her hand she slid onto me, taking me inside. I saw her eyes close and a contented smile break out on her face as she finally felt me inside her. She began to work her hips up and down. I reached between our bodies, where her wetness was everywhere. I snuck my thumb between us, turning the pad of my thumb up so her clitoris could rub on it, and she was quick to take advantage. Lily was not to type to orgasm quickly, and she liked it that way. (Later on, when I was giving her oral trying to get her off, she pushed my head off, teasing me “what’s your hurry?”) it must have been ten or twenty minutes like that, and only my focus on wringing an orgasm out of her body was keeping me from exploding inside her – and I think she was trying to do the same. Eventually, I pulled my hand back, and she smiled again, grinding her hips DEEP against me, clenching her muscles. That was just too much, and I felt the wave of electricity erupting inside me, and my body clenching as I emptied myself into her, in what felt like my entire body pouring fourth. She smiled contentedly and curled up on me, cuddling close while holding me still inside.
After holding each other like that a while, and feeling myself starting to slip out, I pulled her off and went to the bathroom to dispose of the very full condom, and wash the latex smell off of me.
When I got back, she was lying on the bed, legs apart, inviting me between them again. This was going to be a long night…
Source: reddit.com/r/gonewildstories/comments/7vg3tr/playing_with_things_that_are_not_mine_mf