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Me: tall, gawky kid growing up, with glasses and an overbite. Then wrestled throughout high school, got contacts, and dental work fixed my alignment to where I’m actually a pretty good looking guy (I’m told I look like the senior in Sixteen Candles–I’m 6′, brown hair, blue eyes, fit), but I still have the perception of myself as a gawky kid with glasses and can still be somewhat shy until engaged, and alternate between overconfidence and no confidence.
I’ve been going through a stretch lately where I’m happy with my friends, I’m very busy professionally, and I’m not looking for a relationship…but I am human.
However, I guess I’m a little unusual in that I do primarily prefer, if I’m going to strictly hook up, to hook up with women older than me (I’m in my late 20’s)–it’s intrinsically established that this will not evolve into a relationship, they seem to enjoy having a young energetic guy to play with, and I enjoy the maturity and lack of pretense (and definitely having absolutely no pressure to turn it into a real thing).
Also, it’s just a little kinky–being with someone I theoretically shouldn’t–and I like that, especially because I’m pretty straight in real life.
To make it easier to find older women I joined a dating (but not hook-up) site. I also usually reach out only to women who are actually looking for a relationship (seems counter intuitive, doesn’t it?), not just specifically looking for friends with benefits–makes the sex a little more pure and less pre-determined.
Often we just start out chatting and then I might drop a hint or very light double-entendre or two but let them take the lead if they’d like to turn the conversation sexual–usually the fact that they even decided to chat with a younger guy means they’re only seeing me as a casual opportunity.
It’s surprising how easy it is to set yourself apart in online dating–apparently most guys just send, as a message, “hey”. So there’s like 100 “hey” messages in a girl’s in-box. I always read the profile and acknowledge a thing or two written, as well as a lightly flirty comment about the pictures (she is proud of the pictures, after all).
The first woman I met up with this way was a 42-year old mother of two, Michelle, divorced about a year and a half, who’d recently taken to exercise. About 5’6″-ish, she was a brunette with shoulder-length hair, and a touch of a stocky build–not a BBW, but just a little bit wider frame nice round, wide ass, probably B-C breasts? Imagine the actress Catherine Keener–Michelle had that type of vibe and look but more the build of a short former soccer player.
We’d started chatting over the course of two evenings, complementing each other’s profiles, then looks, then light flirting about those looks, then turning sexual. She sent me a few photos (nothing X-rated, but her in workout tights and a sports bra, one without the bra but from the side and her hand covering her nipple), I sent her some (again, nothing crazy) and then suddenly we were planning to meet strictly to hook-up. She had her kids over the weekend, so we decided to meet at a hotel on a Thursday at 4pm–she’d be wrapped up teaching kindergarten for the day and her ex had her kids that evening (yes, the naughtiness of the illicitness was not lost on either of us…and turned us both on).
I can’t remember how we agreed on this but I was to book the hotel, bring protection (naturally) and bring some drinks for us to relax–she specifically requested Skinnygirl vodka–strawberry or cherry. The whole conversation was so fun and casual it almost didn’t seem real.
It was a rainy, dreary Thursday when I left the office. The hotel was a Hilton Garden Inn just off the expressway, and I got there early to get the room. Honestly, I was nervous. I went up to the room (third floor), texted her the room number, put our drinks in the mini-fridge, and waited. I was too anxious to turn on the TV, but as I was sitting down to take off my shoes she texted that she was on her way. The nervousness was still there, but it was mainly replaced by a coursing energy.
I sat on the bed and intermittently glanced through the sheer fabric window shades at the parking lot. At 4 o’clock sharp a silver Honda pulled in but I couldn’t see inside of it. A few seconds later the door opened and she stepped out, reaching back in to grab her purse.
For some reason seeing her step out, knowing that she was into this as much as I was, knowing that this kindergarten teaching mother who was theoretically looking for a relationship but was turned on enough by our interactions to have this mid-day, mid-week hotel hook-up (throwing caution to the wind) gave me a huge rush of adrenaline.
I didn’t want to creep in case she looked up so I went back and sat on the bed, wearing my jeans, boxer briefs, and a light blue oxford button up. A minute later I came four clear, sharp raps on the door. It was on.
I opened the door and we gave each other nervous smiles and a friendly hug (real smooth, I know). She came in, laid her bag on a chair, and sat down on the edge of the bed, legs crossed, one arm slightly back supporting her and we talked about how nervous we were as I got our drinks (I had a bourbon and coke, neat). We sat next to each other and drank, our shoulders and arms touching, but chatting like we were still teenagers on a date. She looked very much like a sweet kindergarten teacher, in a loose green linen top and skinny light jeans.
We were about halfway finished with our drinks when we had that moment-of-silence locked eyes and went in for the kiss. We kissed once, slow and with lots of tongue and lips, then I sat up, took our drinks and put them on the table, came back and laid behind her. She leaned her body back into my chest and turned her head to the side to resume the kiss.
Soon she rolled over to straddle me and started kissing my face and neck, giving me the chills, unbuttoning my shirt one button at a time as she went lower, lightly kissing my chest and down to my stomach.
Once all the buttons were undone and my chest and stomach exposed she kissed just to the top of my jeans’ waistband and then I sat up to take the shirt off completely. She sat up too, still straddling me, so my head was even with her chest as she pulled her top off (revealing a purple and black lace bra). I started to kiss the skin between her breasts, my hand reaching around her body to pull her tight to me. She moaned and tossed her head to the side as her legs collapsed a little, bringing me even with her neck and clavicle. I started to kiss those, not softly but actually pretty wet and aggressive, at the same time unbuttoning her jeans.
I was unbuttoning the jeans just to be ready for them eventually coming off, but I guess she interpreted it as meaning I wanted them off now, so she got up, stood in front of me and started to pull them down. I scooted to the edge of the bed, my eyes totally enthralled as she twisted so I could watch the jeans slowly come down over her ass, exposing her matching lace panties (kind of a pro move, but done with a dose of innocence). As she pulled them off her ankles she bent over as sexy as she could to remove them, her ass now inches from my face.
She stood back up, almost looking over her shoulder and hooked her fingers in her panties, then pulled them down and off in the same fashion.
That ass though. Round, decently tight but with quite a bit little jiggle (and some cellulite–nothing wrong with that), I couldn’t help but bury my lips into her left cheek. She reached back with her hand and half-played / half-grabbed my hair. It was insanely hot to pull back for a breath and look up at her as she looked down at me, still with a bra on but nude otherwise. I kissed all over her left cheek and then the right–staying away from the crack only because I thought that might be a little much for my first move.
After a while I pulled back and she turned to fully face me, revealing that she was fully shaven. Other than noticing that detail I didn’t really have time to do anything else as she right away dropped to her knees in between my legs. She had the slightest little smile on her face, not breaking eye contact at all as she unbuttoned my jeans and pulled them and my underwear down. She didn’t even look down as she took me in her hand and lowered her mouth for an initial lick.
It was as if someone had told her that you have to look into a guys’ eyes as you blow him–or she just really dug seeing my reaction. Either way she did eventually look down and took my head into her mouth. She mainly stayed around the head, slurping on it while her hand gripped the bottom of my shaft and she looked up at me for approval. It was different, but did feel great–it wasn’t really a move to make me cum though, which was fine because we both couldn’t wait any longer for me to be in her.
I scooted up to the pillows as she stood up to take off her bra, revealing her motherly (slightly stretched, full, large areola), but still fairly perky, breasts. While I reached over to grab a condom she crawled up the bed and blew me a bit more, this time taking me deeper in her mouth–I’m assuming to get me wet enough to enter her, although it didn’t really matter since we were using condoms (she later told me she’d only been with one guy one time since her divorce, so maybe she wasn’t fully used to condoms yet?) I still definitely appreciated it.
I gave her the condom to put on me, which she did, then squatted over my cock and guided me in with her hand, sliding me in. It’s always so hot to watch your head, then your shaft, slowly disappear, feeling the warmth and firm, tight squeeze as you get deeper. Once she had in as much as she could take she started to bounce up and down, still not taking the entire thing but enough that it felt amazing. I was so turned on I was worried about cumming right then so I concentrated on the faded shamrock tattoo on her left ankle.
We really hadn’t spoken much since we started making out, but something got into me and I decided to start talking dirty to her, asking if she liked riding my cock, to which she replied she fucking loved it, she fucking loved how my cock filled her pussy, feeling it slide in and out…well, dirty talk is definitely my weakness and her indulging just sent me over the top. I could feel my load start to build up and though I think I’ve only cum from bottom about half-a-dozen times in my life I knew this would be one.
Telling her I was about to cum only made her talk dirtier, saying she wanted me to cum in her pussy so she could feel it pulse, to feel me cum in her (again, I wore a condom so she wouldn’t actually feel my load–but wasn’t one to argue)–and that absolutely drove me over into a huge full body, ball-draining orgasm.
I pulled out and threw my condom away as she laid across the bed. I grabbed our drinks, gave hers back to her, and then stood in front of her, nude, as she leaned back on her elbows, also nude, and we drank and chatted in the most casual of manner.
It was almost strange how quickly we went from sex to chatting and I felt a little bad I hadn’t got her off yet. She was playing it cool but I could see her eyes glance over my body, trying not to be obvious–giving me a big ego stroke.
After a few minutes (maybe we were now 3/4 finished with our drinks?), I took her vodka out of her hand and laid our drinks on the night stand. I remember her saying, “that was a quick recovery” as I started to kiss in between her breasts, then going from one nipple to the other, sucking gently while looking into her eyes.
I went up and gave her a kiss, about a minute long, lots of tongue and lips and eye contact and her hands holding my head, then moved back down her body, kissing her stomach, moving to the sides of her thighs, then moving between her legs, breathing heavily on her hairless pubic bone. It was really cute when, at that moment, she excitedly told me that she’d gotten it waxed two days before just for this. I good-naturedly laughed with her, kissed the bare skin, then lowered my face to lick her clit–looking into her eyes as I did so.
Almost instantly she threw her head back onto the bed and within 30 seconds I heard the first major moan come from her. We were going a bit slower now, almost romantic, the nervous tension gone, her hands playing with my hair and my hands running up her sides. I licked and sucked her clitoris at the same time, avoiding any sloppiness, letting all the wetness be her own. I would lick, then suck gently, lick, then suck, the suck always commanding a big response.
I kept at a steady pace, showing my excitement only by moaning, allowing the vibrations of my moan to escape. Before long her moans were louder, not changing in pitch, just volume. I could see her stomach start to flutter, could feel her leg start to shake, and as she started to orgasm her leg started to kick–the bed, the air, my back. I was loving it (it’s always so hot/rewarding to give a partner an orgasm, isn’t it?).
I eased up as her orgasm did, giving her clit and pussy light kisses, hinting that I was finished going down on her. I actually rose my head up to go towards her face and she brought her hands up to greet me, but I went back down quickly, this time bringing a finger with me, easily sliding in and curling up to stroke inside her while I lightly kissed her clit. I heard her say “oh my god!” and felt her stomach tense up. I purposefully didn’t want to kiss too fervently on her clitoris, as I thought it might be sensitive, so I only put enough pressure to support my finger stroking her g-spot.
After a few minutes I could feel her pussy start to push on my finger, her orgasm starting to build. I thought it would come quickly but she just kept pushing and pushing and building until she let out a huge breath, a very loud and sharp “aaaaaoow” with a trailing w, almost like a howl. Since her pussy pushed with such force, I thought for sure she was going to squirt or gush but she didn’t (totally fine), just had a very loud and intense orgasm. I say intense because as I let her come down by softly kissing her stomach and as she was breathing heavy and wiping her eyes she said, “that was intense.”
I was very, very horny again and crawled up to mount her, grabbing a condom on my way up. This time I put it on as she moved some hair out of her face and watched (she reached out to stroke my stomach before guiding me in her). I rode on top of her for a few minutes, good strong thrusts. I wasn’t really close to cumming or anything but we were having fun kissing each other and running our hands over each others’ bodies.
At one point she asked, “want to see how flexible I am?” I’ve never heard that asked during sex so I said sure, and she had me dismount her. She stood and bent over to grab her ankles, totally presenting herself to me. It was a little strange but also very very hot. Again, this is a woman who uses baby talk in her daily life, stereotypically the profession of innocence, showing me her flexibility by offering my cock an easier angle to fuck her. So I did. Hard. I hadn’t really exerted a ton of energy and this was quite a site, so I had a crazy energy spike, my hands wrapping just under her stomach to hold her up.She asked me, “do you like when I hold my ankles while you fuck me?” I could just manage a grunting affirmation. With that, I really didn’t expect it, but suddenly I felt her pussy pushing again, tightening quickly as she had an orgasm.
I could feel my own orgasm building, yet didn’t want to cum in a condom again so I withdrew. She turned around, sensing I was going to cum. I motioned for her on her knees, which she did, her back against the side of the bed, her head cocked back on the comforter. I pulled the condom off and she stroked me, looking into my eyes, said “cum for me” twice through gritted, determined teeth and I did, squirting on her chest as she switched rhythms, going from that quick firm grip to longer, slower strokes, almost milking the semen out of me and onto her breasts (the excess cum that got on her hand she wiped on her chest too). Coming down from my orgasm I went to get her a tissue, came back and she wiped herself clean.
This was my first random meet up with a stranger and for some reason even after the sex I was still a little shy/nervous–as was she… It was like when we were having the sex we switched personalities, but afterward we were ourselves. Because of that, I was kind of ready to go. So we chatted as we dressed, she kissed me goodbye (somewhat chaste) and left. I cleaned up the room and left shortly thereafter.
Unfortunately, I kind of ghosted on her because of travel and being busy and didn’t contact her for about two weeks–which is terrible. By the time I contacted her, just to say hey I had a great time and see how she was doing, she told me she was dating a guy from her gym (and sure enough he was prominently in her Facebook profile picture) so we never got together again.
Ok, hope you enjoyed this a tenth as much as I enjoyed participating and will post my second success from online dating soon.