Late 40’s [F] and the college boy [M]: A first for both of us Pt. 2

Thanks for all the positive notes on my first post–really glad everyone liked it. I’ll definitely get to the PMs soon. That post is [here](gonewildstories/comments/598ol8/late_40s_f_and_the_college_boy_m_a_first_for_both).

I actually was about halfway through writing about getting my a previous gf off under the covers with her dad in the room (and how she paid me back w/ a quickie just as he walked out), but really do appreciate the asks for me to finish telling about my first night with Kim–so I’m sharing that instead.

As a refresher, I was a tall, gawky kid growing up, with glasses and an overbite. Then I 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), 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.

Again, Kim was in her late 40’s, curvy but not fat, maybe 5″4″ with a cute, youthful face (smooth skin, no wrinkles) and gray and white hair, cut kind of in a fashionable bob haircut. I should define fashionable bob, because it’s basically the hair style that it seems women over 35 have–where it’s kind of longer in the front framing her face and then gets shorter toward the back (I find it the perfect mix of cute/professional/sexy). Medium skin color, kind of reddish like she had a tan that was fading but still had the freckles. She had wide hips and a large, very nice ass that still had some perk to it (though larger than what I was used to), and–by my estimate–double d breasts with fairly large areolas and eraser-like nipples.

We met pretty much by accident when she was eating lunch at a table next to me and asked for my number to introduce me to her daughter. Through texts we got to where she, as she once told me, “kept you all to myself” (I never did meet her daughter–although I saw her photo in the house and on facebook…cute, I’m sure a great girl, thin with long brown hair but kind of plain and not really my type to date). She invited me to her house in a really nice neighborhood (that I assumed was part of the divorce–but I could absolutely be wrong about that) and after some making out in the kitchen and dry humping in the living room we went to her bedroom where we had sex. That’s all described in my first post.

I didn’t mention this before: physically I did find her attractive, but I really found the way she carried herself so insanely hot–a comfortable sweetness in her decisions while sometimes shy about her age, but always open and wanting, with her southern accent. She was also genuinely just a sweetheart. It was the good, decent quality about her that made her sexuality even more attractive to me. Those opposing qualities are absolutely my biggest turn-on and probably where most of my sexual experiences stem from.

After our first session I sat, sweaty and naked, by the pillows on her bed while she stood to throw the condom away (I know I mentioned the difference between her and girls my age a lot previously, but this was another example–I’m almost always the one who disposes the used condom, but in this case she did it for me. As minor as that sounds, it’s another example of how giving she was; she really was sweet and giving to me in every way–whether out of a desire to please me or just because she was a nice person). She walked back to the bed nude and free (at that moment) of her previous concern of how her body would compare to that of a 20-something. She crawled onto the bed and, with a big sigh, laid her head on my stomach, then instantly popped up, crawled up to me quickly, gave a quick peck on the lips, and crawled back to lay her head again on my stomach, her cheek against my abs, wrapping her left arm under my upper thigh to where actually her fingernails were touching the skin of my boys, so lightly I wasn’t sure she realized it. She straddled the rest of my leg and her right arm went up across my chest. We lay like that for a good while–maybe 5 minutes–with my cock softening a little bit but remaining fairly hard and firm against my left thigh. It felt great to feel her against me, to feel her softness against my body, and I reached to gently scratch the back of her hair. She sighed again and nuzzled her cheek back and forth, ending with a kiss on my stomach. That seemed to excite her because she kissed it again. Then again a little louder. Then again with a slight nibble on my abs. Then again, but longer–almost like she was trying to give me a hickey (which I don’t even know if that’s possible?). It was unconventional but really really hot because it was like she was lost in her own kissing game, just playing with my body–stopping to see how wet / red she’d made the spot she’d just kissed/sucked on, not asking me if it felt good…just, playing. And it wasn’t like she’d seen this in a movie or read it in a magazine (at least I’ve never heard of what she was doing before), it was just that she really enjoyed it. After a while she gradually calmed down and brought her left hand to my stomach to wipe away any saliva. Then she lay again, cheek on my stomach, her hand back up across my chest.

A part of me was absolutely ready to roll her over and go for another round, fast and primal, our thighs slapping together, really showing her what I, as the young cock in her bed, could do…but I also didn’t feel the nervous energy from before, so I was able to lay and just take in the moment. I looked down at her hair, I looked at the freckles on her shoulders, I ran my hand across her back. I looked at the ceiling. I looked out the window at the darkened golf course past her yard. I really felt content.

Eventually I started to kiss the hand on my chest, just the tips of her fingers at first, softly. To make it easier she moved her hand closer to my face, not looking at me but brushing it across my cheek. She’d brush my cheek and I’d turn to kiss her hand, then she’d brush my other cheek and I’d turn the other way to kiss. It was a very cute, flirty, sexy thing to do–which my cock definitely interpreted by getting harder, turning up toward my stomach, until it was at my belly-button–basically right in her face. The fingers of her hand wrapped around my leg started to move, gently pressing the skin at the base of my shaft. She brought her other hand down from my face and cupped it underneath the top of my cock–picking it up and then letting it flop down. This seemed to amuse her so she did it again. Then she gently pushed it away from her face and watched it swing back. It amused her even more. She stood my penis straight up and watched it do that boing thing back to my stomach. I stiffened it so she could see how it I could make it stand up or lay down without touching it. She looked up at me like it was a magic trick, her lips just parted, eyes a little wider (I really don’t think she was doing it to be sarcastic–not that she was blown away by it, but like, oh-I-didn’t-know-it-could-do-that… Which, every guy can do that). It was such a hot moment because it wasn’t really about getting me more aroused or closer to an orgasm, just about playing with the hard-on in front of her. She’d seen a cock that close before (though it had been a while–she later told me her last blowjob was 8 years prior), but she played with it like it was a new discovery–but again, not sexual.

Once she was done playing she removed her left hand from under me, and shifted to laying fully on her stomach, still straddling my leg. She gripped the base of my shaft with her right hand and looked up at me. It had probably been at least 10 minutes since we last had actually said a real word, so it gave me chills when her first words were, “can I repay you now?” I moaned in approval and she lowered her head, lifting my penis so it was pointing straight up. She tried to lick from the shaft to the head, holding her hair back with one hand–but she was delightfully awkward, which just made it even sexier. Her kiss only got about halfway up my shaft before she had to readjust to keep from falling, so she sat up on her haunches and brought her face over the top of my cock–kissing around the head in big, loud, wet kisses–her saliva mixing with the combination of fluids from our first session (the residue never bothered her in any of our sessions–very sexy to be that open). After she’d kissed all around for a while she tried to lick from the shaft to the head again, but again halfway up she stumbled, this time her tongue breaking contact with my skin. Not stopping, she licked from where she’d left off back down to the base, then gave the base of my penis another big kiss. She sat back up and jacked me off for a while, brushing something from the side of her lips with her free hand. I wasn’t even really watching her hand, I was just looking at her reactions–this was clearly an experience that she wasn’t experienced at, but she was really kind of thrilled to be in that moment (she later texted me that “two weeks ago I never thought I’d be holding a a 21 year olds erection in my hand”).

Eventually she sat a little taller on her back legs and reached her other hand down to use both in stroking me. Every so often she’d lean over and, with both hands wrapped just under the head of my cock, kiss the tip. A few times after kissing the tip she’d kiss my abs, too. She really had no idea what she was doing as I wasn’t getting anywhere closer to an orgasm, but it didn’t matter in the least…her enthusiasm was incredible and I was almost painfully hard. Actually, some of the pain was because my shaft was fairly dry by this point, so I sat up and kissed her on the lips. She kept stroking me for a little bit while we kissed, but eventually she brought one hand up to my jaw (I could feel a drop of my leakage on her finger), still stroking me for a bit with one hand, now putting her whole arm into it, until she brought both hands up to my jaw and we kissed for a while.

I reached between her legs and felt her wetness in the curly triangle of her dark pubic hair. She kept her pussy clean and neat, but didn’t really shorten the patch that remained–which was fine by me. I ran my index finger over her clit and down to her lips, slipping it in a little to test if she’d be okay for another round. It went in fairly easy and she let out a big breath. “Sex?” I asked (really romantic, I know). She was in the middle of taking a deep breath when she nodded her head yes. We had to break while I scrambled over to the other side of the bed to reach into my jeans and grab a condom. I came back to her and opened the condom wrapper, handing it to her. I was sitting up while she hovered above me on her knees, unrolling the condom on my cock, her face full of concentration. She slowly started to sit down, just letting the head in (with a tiny little gasp) and then kind of sitting lower and lower until I was mostly in but she had to reach back with one hand to support herself so she wouldn’t lower too much. I figured this position wouldn’t last long (her arm would tire) but let her grind on me in this way for a while. The inside of her pussy was again squeezing and releasing around my shaft–as she had during our first session–only this time I could feel it a lot more because we were fairly still.

She soon moved to lay down on her back toward the pillows and I followed her, never letting our bodies disconnect. She laid kind of 3/4 of the way down, where her upper back and head were supported by a pillow and I noticed her looking down to see my cock still inside her. I figured I’d put on a show and slowly pulled out until only about half of my head was still in her wetness, then I slowly went in again, making a satisfyingly gushy sound from inside her pussy. I repeated the action, slowly in and out again, probably another ten times or so until I started to pick up the pace. She brought her hands up to my shoulders and pulled me in for a kiss–a good long one with lots of soft lips and tongue. I was starting to go in and out at a faster pace now and her hand once again went down to her clit, playing with herself slow for the first 10 seconds or so and then suddenly going really fast, bringing her to a pretty quick (and to me unexpected) orgasm. I started pumping faster and faster, but not slapping down with my thighs onto her, just a smooth in and out motion. She brought her hand down again to play with herself and I reached up with my right hand to hold her breast–it wasn’t the softest, most graceful hold but I just really really needed to feel all of it in my hand, to just blatantly lust after a part of her body. She kind of looked down at my hand for a second, almost surprise, then made eye contact with a little smile. Shortly after I did that she did the slow rubbing followed by quick rubbing thing again and had an insanely sexy orgasm wherein she had this sudden exhale/gasp and then mouth made a noise almost like she was about to cry. I couldn’t stop watching her face because her expressions were so, so sexy, but eventually I did look down between us to watch my cock disappear into her. I was starting to get closer to my own orgasm and I felt her free hand go around to my butt again to brush against the sensitive nerves on the outside of my asshole–but the angle was difficult this time for her to put her finger in my sensitive spot. It felt great when she did that the first time but I really didn’t need it to cum and kind of huffed “felt good, but don’t need it” (couldn’t really string together a full, formal sentence in the particular moment) as I continued to slide in and out of her. That seemed to reassure her and she went back to fingering herself, cumming again after maybe 30 seconds but not as powerful as before. It kind of hit me that she was almost climaxing on command which I’d never seen before and haven’t since in that capacity. I didn’t want to let my orgasm get in the way of however many orgasms she might be able to have, so I changed my rhythm slightly to where I was almost kind of hooking up and down rather than in and out. Her fingers were all over her clit now, almost kind of palming it, and she reached her other hand up and put it on my shoulder. I was still watching her fingers go, not even really looking at her expression, when I heard that same exhale/gasp and crying noise. I looked up and it almost looked like a pained expression in her eyes…but in that hot, I’m-having-an-orgasm-right-now way. It was so sexy I really couldn’t hold out much longer and went back to a pretty good pace. After maybe 10 seconds she hooked both arms under mine and grabbed my back, trying to but her hands kept slipping so she’d readjust, grabbing at my back again and holding me closer, to where her face was about at my upper chest. As I started to cum I could just feel her giving my chest light pecks of kisses…but honestly I was a lttle distracted by my second orgasm-just as full as the first, releasing and flowing and clenching and releashing up my shaft and out the tip, that tingly/painful/nirvana feeling, pulse after pulse until I ultimately just arched by back and let the last pulses flow out.

Her cheek was against my chest but she turned to give my pec a light kiss, then moved down to give my nipple a kiss and I think she would have kept kissing it but I pulled out of her and kind of sat on my haunches again. “You are sexy,” was just about all I could say, I didn’t know how else to describe her in that moment (kind of hard to think straight after an orgasm). It brought a big smile to her face, which really thrilled me.

I stood up and walked over to throw the condom away, feeling her eyes watch my naked ass as I did so. I came back to the side of the bed and sat down. She reached over with her right hand and held my neck and we had another big, long kiss. After that broke I said, “when can we do this again?” and she smiled and said basically the most southern thing possible, “anytime you need loving.” She ran an index finger up my torso and then started running it around my chest and nipples. She did that for a while and we both watched her finger, not really knowing what to say next. There was actually a pretty long silence. I didn’t know what she wanted me to do next but it felt like she was either going to ask me to stay the night (and I think she would’ve been nervous that felt too clingy) or basically lead me out the front door (and I think she would’ve been nervous that was rude).

From my point of view, I try not to stay the night, for a variety of reasons too innumerable to get into here (also I’ll probably sound like a real jerk), and prefer for my partner not to stay over with me–unless that partner is officially a girlfriend. Having said that, I’d rather stay the night if she asks or wants me to vs leaving with hurt feelings.

After the extended silence I put on my best I’m-content-but-this-is-the-way-it-will-happen expression, caught her eye and, holding her gaze, said “I’m heading out, okay?”, throwing in the “okay?” just to check and make sure it was okay with her (I’ve since found I actually do leave an older partner’s place one way vs a girl my age’s place…with girls my age, I never throw in a thoughtful “okay?”, and half the time they beat me to my announcing I’m going to leave by saying “I’ll see you tomorrow” or “See you around” or something like that–one time after a quickie one-nighter during a trip, literally as I was throwing away the condom. pants still at my knees, the girl said, “make sure you kill the lights when you leave”). I can’t remember exactly what Kim said to me, but basically it made me feel okay to go. I started to get up to put on my clothes and she didn’t really move, just sat there, one arm supporting her weight, watching me get dressed, a little giddy smile on her face. I felt good.

I was almost totally dressed before she moved, getting off the bed and going over to her closet to grab a modest black robe. We walked toward the front door, her in front of me, holding both of my hands with hers (the same way we’d walked into the bedroom). An awkward way to walk, but cute and intimate.

In her foyer we kissed for a little while and I told her I’d text her tomorrow. The whole mom side of her accidentally spilled out in the cutest way possible when she responded, “Text me when you get home so I know you made it okay.” I laughed and said okay. Full disclosure, it was only about 11 by then so I actually ended up meeting some friends at a diner and texted her from there that I was home (I thought it would diminish how awesome our experience was if she knew I was now out with other people). I did text her the next day though–imo it’s really rude when people ghost.

So that was my first night with Kim–I tried to describe the sex itself and her body a little bit more in-depth this time. We kept hooking up for the rest of the semester and a few times early the next, with some really hot and cute moments throughout that I’ll write about at some point–but I do want to share some of my other experiences, too (if that’s cool?).

Source: reddit.com/r/gonewildstories/comments/59xwkg/late_40s_f_and_the_college_boy_m_a_first_for_both