So a few years back, I decided to dive into the world of online dating. I wasn’t necessarily looking just for sex (although Tinder is the best platform for that, on nights that I was swiping I was usually pretty successful), but I was open to a relationship, too. Anyway, I met this girl Hannah on eHarmony and we ended up going on a few dates. I was a definite gentleman at first, just giving her a hug and a quick kiss on the first few dates, but after five or six we had moved on to more intense making out, and I had grabbed her ass a few times. The story I’m about to tell happened on our seventh (I think?) date, the first time we had sex.
Now, I’ll go ahead and let you know now that I’m built pretty average. 6 feet, dad bod, nothing to write home about. But Hannah…damn. I’m pretty biased because I still love this girl, but I’m not joking around when I say her body was kickin’. 5’5, Malibu-tanned, tight little body. Her tits were a full C cup, always perky and ready for me, and that ass is something men might dream about. The amount of times I rubbed massage oil on her bubble butt and hit it from the back…still one of my favorite things to think about when I beat it. But anyway, back to the story.
This particular night I was coming back from a trip, in a location where I had shitty service, so we hadn’t texted in a few days. Thankfully we had made plans for our date beforehand. She had asked me to pick her up before we headed out to get sushi, so I washed my truck, shaved and showered, and was on my way to her, flowers in hand, about a half hour before the reservations I had scheduled. She normally dressed pretty conservatively (although always fashionable), but on that night she had on thigh-high leather boots, a tight black skirt that showed off her ass, and a scoop-neck lavender blouse. I figured maybe she was trying to give me the green light in a subtle way. She loved the flowers, and invited me in while she went to find a vase and cut them. Seeing her bend over to look for the vase, watching her juicy ass in that tight skirt, I thought I was going to break through my zipper. At this point, she had never resisted my attempts to further things, and I knew I was going to push it to see how far she would let me go.
I pressed my luck, grabbing her hips as she was leaning over looking in the cabinets. “Mmmmm, babe, I missed you this week,” I said. She giggled, found the vase, and promptly stood up. I still had my hands on her hips, and I pulled her ass closer to me and heard her gasp when she felt my chub. At first I think she was in shock, so I rubbed my hands down the sides of her thighs and took the vase and flowers from her to put them on the counter untouched. I turned her around as she got her wits, and pressed her against the counter, kissing her long and slow, still pressing into her so she could feel how hard I was getting. She tried to make a joke, giggling and saying “What kind of girl do you think I am?” but I could hear her breath quicken and see her face flush red when, instead of responding, I hooked my thumbs into her skirt and tugged.
I could tell she was still surprised, but she obliged, stepping out of her tight skirt to reveal her beautiful thighs and plump ass in a skimpy little thong, complicated with straps in the back. She did full body turn for me, showing her sweet, full ass off and giving me a sort of smirk when she saw my dick raise even higher through my jeans. She looked nervous, and maybe I should’ve been too, but I could no longer control the animal inside me when I saw this beautiful brunette standing in her kitchen in thigh high boots, panties, and a flimsy purple top. I quickly peeled her shirt off to reveal a matching black lace bra, and used one hand to squeeze her ass while the other was tearing into her bra, pinching at her perfect tiny pink nipples that were all of a sudden standing to attention.
She loosened my tie and, to my surprise, put it on herself. That sent me over the top. I’ve always had a thing for tight little bodies in costume. She unbuttoned my buttons and pulled off my undershirt, til I was down to just my jeans. She squealed and wrapped her legs around my waist as I placed her on the counter. I unhooked her bra, revealing her perky nipples and started to tug at her panties when she gave me a wicked smile and told me they were crotchless. I swear to god I rested my head on her stomach, hot breath on her pussy, and whimpered. Not my proudest moment, but this girl was killing me. I got back to work.
Over the next ten to fifteen minutes, I slid my tongue across her clit as she laid back on the counter, moaning and raking her nails into my hair. Her legs were shaking with the need to cum, but I told her she couldn’t until I asked her to. At some point, I guess it became pretty unbearable for her, because her wails got louder and she could only say one thing over and over: “Fuck me.”
I stopped sucking on her clit for a minute, resting my head on top of her, both of us breathing heavy. Then, without a word, she sat up and hopped off the counter, grabbing my hand and pulling me into the bedroom. She had a king-size canopy bed, with a bunch of throw pillows. She swiftly cleared the bed so there was only one fluffy pillow right in the middle. “Sit here,” she said. “If you want a show.” I sat.
She dimmed the lights, and I watched in amazement as she lit a few candles, still only wearing those thigh-high boots, crotchless lace panties, and my tie around her neck. She plugged in her iPhone to the stereo and sensual music began to play. As she swayed and danced to the music, swinging around the bedpost, I started to touch myself, but the look she gave me made me stop in my tracks. She tossed my tie aside and bent over to take the panties off too. At this point she was wearing nothing but those thigh-high leather boots. Goddamn. I still get hard just thinking about that body. She got up on the bed, climbing towards me on all fours, and straddled me, positioning her smooth pussy right over the head of my throbbing cock.
“You’ve been a bad boy,” she said. I nodded furiously as she started kissing my neck and sucking my earlobe. I was acutely aware of how close she was to sitting on my dick, and I tentatively put my hand on her ass to try and guide her down. She let me put the tip in, and then just as quickly took it back out. I couldn’t help but let out a small noise. “You like that?” She asked. Again, I nodded furiously. She giggled, and slid down once more, this time taking my whole seven-inch shaft. Her cunt was so slick with wetness we both moaned as she started to bounce up and down on my cock. She was so tight it almost hurt, and I remembered how she had told me she hadn’t had regular sex with anyone in almost a year and a half.
I could tell how much she was enjoying it, closing her eyes while her tits bounced up and down beautifully. I was still gripping her ass, and each time I gave it a nice hard smack, she would let out a cry of pleasure and tighten up around me. She pressed her tight body against mine and kissed me long and hard, letting me thrust into her over and over again as she rode my cock. As we let the anticipation build I had one objective: I wanted to let her cum before I filled her up with my own. At one point I was so close I thought I wasn’t going to make it, but a few more hard thrusts into her and she begged me. “Oh, God, please let me cum for you. Oh, God, I need to cum for you.” All I could do was nod.
The climax was exhilarating. She trembled and moaned for probably a full thirty seconds or more, closing her eyes and riding my shaft like an expert, like her life depended on it. Halfway through, she noticed my breathing get heavy and I let out a few groans myself. Encouraged by her (“Oh, God, fill me with your cum. Oh my God. Yes. Yes!”) I squirted my hot load into her tiny pink pussy and we finished at the same time, with the bedsheets soaked and us panting loudly. She curled up next to me in bed, with my boner wilting from exhaustion, giggled, and said “I think we missed our reservations.” Read more »