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

Just discovered this subreddit recently and I’m a total nube to writing about my experiences–so hopefully these won’t be a waste of your time. Please be gentle!

Should probably start with a little explanation. As I was growing up I was tall, gawky, had glasses and an overbite. Then I was a wrestler 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.

I remember hearing my dad and his buddies laugh about how ridiculous and unrealistic “I can’t believe it happened to me” letters that were in Penthouse (or Playboy? Both?) and that’s kind of how I feel about the experiences I’ve been fortunate enough to have–I don’t consider myself overly sexual or deviant, but I’ve somehow managed to have a lot of encounters that, upon reflection, are large in volume (everything from college girls to probably an unusually high amount of milfs/cougars) and kind of unusual (in semi-public rooms, fingering under the covers in front of the girl’s family, threesomes, with food, tying up, and so on) and seem like bs.

So this isn’t the first experience I had or necessarily the hottest (though I think it’s pretty hot), but the easiest to write–my first experience with an older woman, which really got me into enjoying older women. I really am into the build-up and noticing details and emotions and hope you are too.

I was a junior in college, fall semester, still living on campus. On Tuesdays my best friend and I had a large open swath of time just after 11am, so we’d usually do something together–go shoot ball, grab lunch, go to a bookstore, lift, etc. For some reason on this half-cloudy, half-sunny early October blah Tuesday we decided to go off campus and treat ourselves to that fine restaurant chain known as Chilis. We’re seated round table next to three women in their late 40’s, early 50’s. My friend and I order our drinks (water for him, coke for me) and start looking through the menu. The women’s food arrives and it smells amazing–sizzling fajitas, some sort of roasted chicken, fish tacos… My friend, being more outgoing than I am, turns to the table and asks about their orders. Well, this begins a whole conversation between him and the table. He’s asking about where they work (two at a bank, one is an accountant), they’re asking what he studies, they’re talking about the weather, about our college’s football team (SEC)–the chit-chat goes on after we order our food, after we get our food, while we’re eating our food. He’s basically been co-opted by their table…but I really don’t say a whole lot. Not annoyed, just kind of eating my food and listening, chuckling at the jokes, just letting them all engage.

Toward the end of the meal the one closest to me starts asking me questions directly in her southern accent and I talk with her a little bit. We’re talking about the town (it’s pretty much a small college town) and she tells me what neighborhood she lives in (one of the nicest) and the church she goes to. We get to chatting about school and, in classic mom fashion, she asks if I knew her daughter, who was a sophomore at the school and in a dorm near mine. Of course I don’t know her daughter, but she says she thinks we’d get along well and she needs to meet a sweet, cute guy like me–flattering but also silly (yeah, her daughter’s going to want to hang out with a guy her mom met at lunch). I really didn’t think much of it–she was just being a mom, we weren’t flirting or anything. At that point I’d never been with anyone over 3 years older than I, so it didn’t even cross my mind to flirt with her. She was your average conservative mom. As they’re getting up to leave she asks me for my number so she could give it to my daughter. I gave it to her just to be nice (but also kind of amused that she asked for my #, at that time if you really wanted to hit someone up you’d Facebook–this was right before insta and twitter took off).

A few days later (in retrospect exactly one week later–a Tuesday) I get a text from a random number saying, “Hi JT, this is Kim from lunch the other day. Remember me?” Texted that I did and asked how her day was going, expecting her to pivot and then either tell me her daughter’s info or that her daughter said thanks but no thanks or whatever, but instead she actually tells me about her day (crazy client, she was sitting at her desk now, just finished lunch) and then texts “you’re so sweet for asking!” I wrote back “yep, I’m everybody’s college sweetheart” pretty much as a throwaway line. I get back from her “awww so cute” and then “I just want to eat you up” with a smiley face. That was my first twinge of, is this just a mom thing or is she laying it on? I started trying to remember what she looked like. Curvy, not fat (20-30 pounds heavier than her prime?). Short, maybe 5″4″? Cute, youthful face (smooth skin, no wrinkles) with gray and white hair, kind of a fashionable bob haircut. Medium skin color, kind of reddish like she had a tan that was fading but still had the freckles. She’d been wearing a blue silk top that swooped from her neck but was relatively fitted elsewhere and black dress pants that did accentuate her ass (ok, I might’ve noticed her ass a little as she was walking away that day–but that’s just normal guy instinct).

At this point I’m actually considering my next text instead of just sending the first whatever that comes to mind…trying to think of something possibly suggestive but also totally innocent but also in a lexicon that would relate to her, so I write, “well, I am very yummy”. I’m walking along campus and at this point am actually looking at the phone to see what she’ll send back. She told me later her fingers were shaking as she typed her next message, which comes through as “well a girl would be lucky to get a taste” and a wink. Still I’m not totally sure, because she says “a girl” . . . so is she saying any girl, her daughter (a little strange), or her? Also, is she looking at this as the general, taste of hanging out with you message or as the specific, taste with her tongue message? I also probably think way to into things so I noted that me using “well” and then her using “well” was a good sign too.

I had no idea what to write next…again, a part of me is thinking this is a conservative Baptist mom (presumably single? really had no idea) so I’m not going to push the innuendo button too heavily. So to kind of force her to be the one to do so I wrote “haha” and then yes, something really corny, “i’ll take that into ‘account’-ing” (she is an accountant). I know, total cheese but people I’m not great with the game, so forgive me. She texted back a haha and then we just had some general text about the day–almost like we were friends. Never got back to any flirting really UNTIL . . . she texts me later than night.

Now this might be an unfair generality, but in my personal experience (and I have some other great examples of online-initiated romances/hook-ups to back this up) if you have a flirty moment that you walk away from and then THEY hit you up that night (in my case only with women, but I’m assuming it would be true reversing genders), then they’re interested in you on a different level.

So it’s a weeknight, close to 10pm, I’m in my room studying/procrastinating, when I get another text from her…the I-have-nothing-to-say-but-am-thinking-about-you kind of text. She says “hope you had a great rest of the day!” with a wink face. I go from full slob laying in bed mode to sitting up, engaged and alert. I don’t remember exactly what we said the next few texts, but I know where I led the conversation, because it was my first time ever knowingly doing this and it’s a pretty good method (granted, maybe this is Game 101 and I’m naive enough to think it’s cool). I asked what she was up to, and after she responded (“reading and watching tv”) I said “I’m laying in bed studying”. Then before she could text back I wrote “learning as much about history as one can while in sleep pants and a white t-shirt”. I figured, she can either read this as me simply describing that I’m doing homework, or she can picture me in bed in a t-shirt. If she’s being innocent, I haven’t said anything offensive and we’ll move off of it. If she’s picking it up then she can take the next step.

Thankfully, Kim dutifully texts back “I’m on my couch” and then “in a pink tank and blue sweats” with 3 smiley faces. At this point I’m totally engaged and we’ve both totally blown off any thought or pretense about her daughter.

Me: Hm.

Me: That sounds comfy

Her: it is :)

Me: is that enough to keep you warm? I mean, couldn’t you still get a little chilly?

Her: well if I had a man with me he’d keep me warm

Me: all night?

Her: yep! :) :)

(jackpot, btw)

Me: Well I don’t know any men to keep you warm unfortunately haha

Her: Aw

(she later told me she thought I was blowing her off there…which in retrospect was kind of what I wanted her to think)

Me: I only know a college boy in a tee

Her: (she sent a kissy emoji)

Her: haha

(at this point I did want to make sure I wasn’t messing with someones wife)

Me: what about hubby? shouldn’t he keep you warm?

Her: divorced :(

Then she explained her divorce a little, how she’d been single for years…didn’t get into a sob story fortunately. I wrapped it up with the cliche, “he’s missing out!”, to which she agreed and then I texted “it’d be ashamed for a college boy to miss out”. For some reason I still didn’t want to go entirely first person. She did a you’re-so-much-younger-than-me and I’m-not-cute-like-girls-your-age thing, which is really just a need for reassurance, I did the don’t-sell-yourself-short-you’re-cute message and I’m-more-into-intent-and-desire (which is true). We ended up doing a little more light flirting and called it a night with some innuendo about tucking to sleep.

The next day I figured it was my turn to reach out to her, and I thought I’d take a risk. “Are you free Friday night?” I asked. She texted back “yep! :)” and we started talking about making plans. It was cute in that she said she didn’t want to interfere with my plans, not knowing/realizing that Thursday nights and Saturday’s after a game are the primary party nights. The tricky thing was figuring if I should pick her up or if we should meet somewhere (we decided to meet), and then figuring where. There weren’t an unlimited number of options in town and I think we both knew to avoid anything too romantic/intimate, anything where we might run into people she knew, and anything that would be too young/rowdy. Ultimately, we decided to meet up at a little bar near campus.

Now, I was pretty sure I knew what this was, but I’m never ever positive–it could just be she wants to grab drinks with a young guy, it could even still be she wants me to meet her daughter (who hadn’t come up in conversation and ultimately never did). Also, I had no idea how to get her from that bar to where we could be alone…in college you’re either within walking distance or in the same car or just need to duck into another room. I figured she would lead the way, but it had been a while for her (and her game seemed even clumsier than mine), so I really just focused on having a good time without thinking about if we hooked up or not.

But then on the Thursday morning she erased any and all doubt. After her usual pleasantries, about my day, her day, and so forth she asked “Would you want to just come to my house instead?” I understood that it meant no public risk, but obviously it also meant she was inviting a college kid she’d only met once to come directly to her house. I texted back “sounds good” and then “you want a college boy to just warm you up and tuck you to sleep?” She wrote, “exactly! :)” We figured out the time (randomly, 8:30) and she texted me her address. Needless to say I was pretty stoked.

In college sometimes you want to look older and more mature–that was not at all my concern as I got ready that Friday. I showered at 7:30, shaved, trimmed and groomed everywhere, wore a plain gray t-shirt, dark jeans and flipflops. I could still taste the toothpaste as I pulled into her neighborhood. It was a really nice neighborhood, too. The kind that is new enough to not have any tall trees, but not just cookie-cutter houses. Her house was one floor (and a basement) but was pretty spread out and luxurious. I had the impression she kept it in the divorce but didn’t ask. The inside, in retrospect, reminded me a lot of the movie It’s Complicated. Lots of space, nice stuff, tasteful but again not like a throw-em-up McMansion.

Anyway, I got out of my car and rang the doorbell. I stared at the pumpkin and hay themed wreath as my heart was pounding in excitement. I heard the door unlock and saw some movement through the glass. The door did that solid, heavy sort of swing open. There she stood with a very happy (but a little bashful/shy) smile. She had on a black sweater that did the same swoopy neck thing as her silk blue shirt, showing just a bit of her upper chest, but tight at her breasts (this one was more of a soft cotton cashmere material). She had on black pants that were pretty fitted around her hips and ass, but flared from the knee. No shoes or socks. A little bit of make-up and lighter lipstick and a lot of perfume…that mom perfume. But something about it–knowing she’d thought about what should she wear for me (of all people), and that she chose this outfit and this makeup and this perfume…I dug it.

As I said hey and stepped in the door she grabbed me by both cheeks (face cheeks), threw her body into me (temporarily knocking me off balance), and kissed me deep on the lips. It was kind of a let’s get the jitters out of the way kiss, very forceful…and really pretty cute. I could tell she was more nervous than I was. Her hands slid down to the back of my head and pulled me close. My hands went around her hips and we kissed, kind of mashing honestly. I pulled back, we looked at each other, and then readjusted for a real kiss, heads turned slightly, my hands running up her back, her hands pulling at my hair, down to my neck, I leaned back onto the closed door and let her just put all of her weight onto me. We kissed like that for quite a bit (tongues teasing each other, switching my concentration from her tongue to her bottom lip) maybe 5 minutes or so, then took a breath and looked at each other–almost giggly. She took a big breath and said, “let’s get a drink.” As she turned I reached out to grab her hand so she would lead me into the kitchen–I like little intimate moments like that, where you’ve got skin to skin contact. As we walked in her kitchen I reached out for her other hand too, so she was holding both my hands as she walked forward. It was awkward but kind of fun, we stumbled for a second and I bumped into her.

In the kitchen I helped her make the drinks. I can’t remember exactly what she had but it was a Skinny Girl type mixed drink. I had a small amount of whiskey, neat. Drink in hand, I leaned back against her counter and she leaned her body into me. Our faces were inches away from each other (her face a little lower) kind of editorializing what had just happened. “Did you find the house okay?” “Yeah, I almost turned a full right instead of just curving right on such and such street.” . We’d take a drink. “You have a great house here.” “Thanks.” . We’d kiss quickly. “I was afraid you wouldn’t show.” “I didn’t know for sure if you were into me.” Drink. “How could you not tell? I asked you to come straight to my house.” “Yeah, I know.” Drink. Kiss. “You’re a very good kisser.” “Thanks, you too.” Kiss.

I don’t know if other people feel this way, but always before my first time with someone I get so excited I’m kind of shaking. I’m usually able to keep it cool so she won’t notice, but I’ve had some girls notice and comment on how nervous I am. I’m not actually nervous (that I’m aware of) but just overly stoked. With Kim it was an excitement for the ages. Thinking later, I realized it was the first time I was ever with someone I wasn’t supposed to be with–wrong age, seemingly not super-sexual–and have come to realize that’s probably the thing that turns me on the most: being with a “good girl” (as I am a “good guy”) who is really just as lustful and longing as anyone else. Basically, doing the thing I’m not supposed to do.

I was nearing the end of my drink and I said, “I can’t wait for what comes next.” She got a huge smile on her face and said, “I can’t either . . . but I probably won’t be as good as the girls you’re with.” I kind of chuckled and said “let’s not worry about anyone else. Let’s just concentrate on you and me and have fun.” That seemed to really relax her and she snuggled her face against my chest. I laid my drink on the counter and she did likewise. With less panic and more lust we locked eyes and went in, slowly, for a kiss. It was a kiss in stages, first our lips meeting, parting, playing for a bit, then tongues coming into play. Her arms were kind of scrunched up to her, cuddling up to me, as my hands went down her upper arms, sides, over her hips, and blatantly palming her ass. I have to confess, her hips and ass were much larger than I was use to, but the novelty of the whole situation (and the size of her hips and ass) were such a turn on. She was moaning into me as I kneaded her butt. I’m sure she could feel my hardness through my jeans. I ran my hands back up to her neck and gripped her hair lightly, just pulling her back to kiss deeper. I wasn’t totally sure if she liked having her hair pulled or not so I let go and put my hands back to her hips. Her hands were actually at my hips and eventually our hands found there way to each other. At this point I was leaning against the counter, her basically on her tip-toes leaning into me, our hands intertwined at our sides. We broke for a break. She let out a big breath again (I came to find out she did that a lot). “That’s what I was hoping for”, she said. “Oh yeah?” I asked with a little smirk. “Yeah,” she said as we went in for another kiss.

Finally we broke again and did the awkward holding hands / walking thing out of the kitchen. She lead me into a dimly lit living room and onto the couch. She sat down with her left leg under her and her right leg free. I sat beside her and she swung her free leg over mine, looking at me in a totally ego-boosting way (taking me in like I was her trophy–which made me feel great) while she played with my hairline. I didn’t exactly know what to do at this point so I did nothing. I figured that was better than pushing the situation too quickly. I wanted to enjoy it and remember it, to take it in. I actually leaned by head back on her leather couch and closed my eyes for a second as she started to play with the top of my hair. “Does that feel good?” She asked. I just murmered a “mm-hmm.” and let her keep on. My hands were brushing over her right leg, getting increasingly more active, going up to her ass. (This particular moment actually has some parallels to another experience I had a few years later with a cheating milf). Eventually she just moved to where she was mounting me and we kissed again deeply. I put my hands inside her sweater and ran them up the sides, feeling her goosebumps go up everywhere I touched. The way her body felt was totally different than any girl I’d been with before. First, it had a heavier center of gravity, less of the lightness that I was used to. Also, her skin wasn’t as tight (two years later I had a FWB my age that was a little more overweight but even she felt tighter than Kim). It didn’t matter though–I was totally aroused, as aroused as I’d ever been.

She was kissing me with a wanton desire, her body grinding against me with barely any rhythm, just all passion. I went to pull her shirt off but she tugged it down. She made up for it by reaching down and gripping my hard-on over my jeans. I took that to mean, correctly, that she wasn’t saying no to what was going to happen, she was just a little shy about her body. Totally got it. I ran my hands back up the inside of her sweater and put my hands over her bra, the kind that has lace on the outside to be feminine, but plenty of support against their skin–so not see-through lace. I ran my hands to her back and quickly undid her strap, which seemed to impress her. My hands came back to her chest and reached under the now loosened bra. Her breasts were very large–at least a double-D I would guess. I let my hands softly touch around the outside curves, taking a finger from each hand and brushing it against her nipples. She audibly gasped when I did and humped her back pushing her kiss into me more (which actually made it harder to touch her breasts). Her hands went around the front of my cheeks, kind of at my neck at a little. Then her hands trailed down the outside my shirt, going to my hem and lifting. A little double-standard, but I didn’t mind. I was feeling super-full of myself, thinking it’s been a very long time since she’s felt a physique like mine (I’m not super-muscled, but I’m pretty sure I was better than what her husband had been). She lifted the hem, her hands trailing up my chest (hairless at the time), taking the shirt off over my head.

Like a magnet as soon as my shirt was off she went straight to kissing my left nipple. I don’t particularly find that a super turn-on, except that she was so, frankly, thirsty, for it I was blown away. She was wanting me, like really really wanting me (I feel that surprise every time I have sex, as odd as that sounds). She was now on her knees in front of me, her hands supporting herself on the couch and sometimes on my stomach, kissing and manipulating and licking and tweaking my nipples. It was a little unusual but I didn’t care. Eventually she moved lower and started kissing my stomach with loud smacks of her lips. I was looking down at her, just running my hand through her hair. What she was doing wasn’t anything someone of my age has really done to me–she was like 10% too desperate, 10% a little awkward–but that was exactly what made it so hot. She wasn’t a pro raised on modern Cosmo and porn, she was the mom of a college girl having a fantasy-like situation play out.

After a bit I started to pull her back up to me to kiss but instead she got up (total lust in her eyes, her hair a little askew . . . lust in my eyes too) and grabbed my hands to make me get up. I did and we kissed as I stood up. Then, with the same awkward two hands-holding walk, she led me through the house–and finally into her bedroom. It was darker in her bedroom, with only the moonlight through the windows. The room was immaculate by the way, with like 7 pillows on a huge bed. Once in the room she shut the door and instantly took off her sweater. Her bra hung loose on her shoulders so she reached up with one hand and threw it off. Her body actually was pretty decent after all, not that I had a ton of time to look. She went in for a kiss again, our chests pressing against each other (well, my chest was a bit higher). That’s a feeling I dig, that body to body intamicy. I wrapped my arms totally around her back and pulled her tight to me. We broke our kiss and I reached down to pull down her pants. She stepped back and did it herself. I followed her lead and started to unbutton and unbuckle, but really I was mainly just watching her bending over taking off her pants. Once off, she stepped toward me to help take off my jeans. She pulled them down and got down on the floor, pulling each pant leg off each foot. She stood back up and we pressed into each other, my leaking hard-on soaking my boxer briefs as we kissed. I cupped my hand on her lacy black panty-covered ass, pulling the bottom parts up to make it more of a bikini cut so I could feel the skin of her cheeks. I gripped them, spreading and kneading them. I was taking baby-steps backward as we kissed and until the back of my legs felt the bed and I sat down. Again she got on her knees and played with my nipples, this time her hand resting on my hard-on, starting to subconsciously knead it.

I figured it was her turn so I stood up and had her stand up, I turned to put her on the bed, meaning to lay her on her back but instead she laid down on her stomach (again with a big breath). I followed her lead and ran my hands up the back of her legs, over her waistband, up to her back. As soon as my hands hit her back she let out a biiiig moan. I can take a hint. I probably spent 10 minutes giving her a deep back-rub. I don’t know that I’m really that good at it, but she was moaning like I was a pro. After a while I started mixing the rubbing with kisses, soft ones down her sides, skirting across her back, kissing her shoulders. As I kissed her shoulders more and more my hands went lower and lower on her back, until my right hand was rubbing just her butt cheeks.

By now I was basically laying next to her, with her face looking at me as we were kissing. I ran the hand from her butt to in between her legs. She squirmed a little thinking I was going toward her crack, so I adjusted to let her know my hand was going lower. Maybe I imagine this but I believe you can sometimes literally feel heat coming from an aroused pussy–and I felt it in this case. My hand pushed her panties to the side, brushing the outside of her, which was absolutely soaked. I started gently stroking up the outside of her lips with my index finger. She was moaning pretty deeply now, not even girly just kind of rougher and primal. Sometimes I try to tease until my partner can’t stand it–but this wasn’t the time to do that. She was more than ready, had probably been ready for quite a while.

I shifted tact and started to brush my thumb against her clit, going just a bit more inside her with every flick. Finally I just worked my thumb into her wetness, angled down (think of thumb war). I was sitting up more now, pressing my covered hard-on into her hip, my left hand up by her face (she was kissing it, kissing the fingers, thumb, sucking some), while my right thumb was curling around her g-spot. After a while she was basically humping my thumb and I could hear her breath get heavier. She stopped kissing my fingers and concentrated on her coming orgasm. With an open throated moan she came loudly, totally soaking herself and her bed. After she calmed a little I took my thumb out (little bit of a plop actually). And moved toward her legs, pulling her panties off her. Again, there were little differences between her and younger girls–girls my age let you pull of their panties, she actually turned on her side and helped me pull them off, bringing her knees up and reaching down with her hand to help them around her feet.

She was totally nude, her weight supported by one arm, totally flushed looking at me. I was above her, boxer-briefs on. We locked eyes for a second and then I just pounced on top of her so she was on her back and we were making out again. She broke the kiss and said, “let me repay you,” while she reached in my waistband and grabbed my cock (actually it was already peaking out the top of the waistband). Something in the way she said it I just didn’t really feel like that’s what she really wanted to do in that moment so I said, “there’ll be plenty of time for that later. Why don’t we have sex?” Her eyes lit up as she said, “Oh god, yes.” I pulled my underwear down and stood up beside the bed, letting her eyes drink in my body (and drink in she did). I’m just as amused that I’m somewhat attractive as she was, so it felt great to have her look at me like that. I found my jeans and pulled out a condom. I prefer for my partner to put it on me (just sexier) so I handed her the wrapper to open. She was so cute trying to get it opened but couldn’t so I took it back from her and opened it, then handed it back to her. She was really concentrating as she took it out and put it on me, almost squinting at my cock to make sure the condom was unrolling properly. It was so cute to see someone really take their time (versus the usual blind, reaching between the legs roll-down while we kiss). It was also the first time she really felt my cock with her hands. She was rubbing up and down the shaft, looking down at it. kind of alternating which hand was holding it, like she was weighing it. “you’re big!” she said, looking in my eyes.

About my cock: I feel like I’m decent size. Not huge, but fine. Maybe I’ve seen too much porn and think I’m smaller than I am. Almost every girl has told me I’m big, but with varying degrees of sincerity (in my mind, at least). I try not to be the humblebrag (though maybe this whole thing is a humblebrag?) but I’m doing pretty well, good length, good girth, head in proportion, thicker than the shaft. I haven’t measured but I did do the toilet paper roll test once and I’m thicker than that (obviously longer).

I moved down between her legs and thumped my cock some against her clit before I started to slide it in. She reached down and helped, one hand kind of spreading her outside lip while the other guided me in. I was watching it slowly get deeper and stole a look up at her–total look of concentration. Eventually we got the head in and she was doing a breathing thing like it was a breathing exercise almost and I could feel her walls gripping my cock, contracting and releasing. I really couldn’t believe how tight or wet wet she was. For some reason I wasn’t even sure (before then) if women her age still got wet or if the had to use lube and just assumed she’d be looser–no idea why I thought that. With one hand on the front of my hip, one on my ass she guided me in slowly, not inch by inch but like quarter inch by quarter inch. It took a good 30 seconds at least until I was mostly in her. She let out another big breath and moved both hands to my ass. I started off slow, kind of grinding my hips against her, then changed to a pretty consistent thrusting. I know this will sound dumb, but her next two moves kind of surprised me–first, she started rubbing her clit. Not that I haven’t been with other girls who’ve done that, but (at the time) she still seemed like that type that wouldn’t even know to do that. But she did. Within probably a minute she was cumming again, but she didn’t stop and kept playing with it, first with two fingers, then kind of just brushing her whole hand over it, probably cumming 2 or 3 more times (each time with a high-pitched squeak followed by a “aghhhh” primal sigh). The other thing she did was keep a hand on my ass, first trying to knead my cheek (my cheeks are a little too hard to knead) and then–this is what surprised me–she moved her hand to my crack. It was a little strange (at the time . . . she ended up being much more open minded than I perceived), and she’d been nervous about my hands doing that to her but she was doing it to me. In full disclosure, it wasn’t the first time a girl had done that to me–but that it was her, this conservative older woman . . . it felt amazing. We were looking right into each other’s eyes and I’m sure she was reading my mind because just as I barely felt myself starting to cum, she surprised me again–she could tell I was about to cum (maybe she felt a pulse? Maybe she could see it in my face?). “Yes,” she said. “Do it. Do it now.”

“Yes. Do it. Do it. Do it, do it, do it. Doit, doit, doit doitdoitdoitdoit” she kept saying over and over as I was pumping in and out of her, her breasts bouncing with every sway, big areolas hypnotizing me. Between staring at her breasts, feeling her finger on my ass, the grip and release of her pussy, smelling her perfume, and hearing her encouragement in that accent, I was beyond ready to explode–and I did. I actually let out kind of a roar, surprising myself, feeling pulse after pulse shoot through my shaft and out my cock. It was one of those full-body, from the toes on up orgasms. Just total release. I kept pumping and pumping even after my cum was out, feeling the aftershocks course through me. Eventually I slowed down and pulled out, sitting on my haunches breathing deep.

I feel like I actually look my best right after sex (maybe all guys think that?), my abs are really defined, I’m breathing heavy but controlled, and my cock is still pretty big but not hard. So I pulled the condom off and sat there like that for a minute, watching her watching me. Again, maybe I’m just all ego but it really felt great to have her eyes on me. After a while she started to wriggle and took the condom from me. She was much less concerned about her body now and got off the bed to throw the condom away. I sat up by her pillows as she came back. She was glowing and looked so fulfilled, so flush, so confident…so damn hot–maybe not like the girls my age, but like a woman who knew herself. My perception of sex and age and what makes a woman “hot” pretty much flipped in that moment.

Okay…plenty more happened in that relationship (including later that night), but I feel like I’ve practically written a novel already. If you dig this experience, I have quite a bit more I could share, from the cheating woman to the one semi-cuckold situation to the variety of girls my age (the examples I gave above but also road head, sex on a dock, bj in a canoe, once wearing panties at my ex’s request during a work day, etc.) . Let me know!

Source: reddit.com/r/gonewildstories/comments/598ol8/late_40s_f_and_the_college_boy_m_a_first_for_both