Married co-worker [F] and the young man [M]: an affair (LONG)

Everything I’ve written previously has been about my collegiate experiences–my first time with an older woman ([1](https://www.reddit.com/r/gonewildstories/comments/598ol8/late_40s_f_and_the_college_boy_m_a_first_for_both/), [2](https://www.reddit.com/r/gonewildstories/comments/59xwkg/late_40s_f_and_the_college_boy_m_a_first_for_both/)) and about [an experience with an ex girlfriend, where I gave her an orgasm in front of her dad without him realizing](https://www.reddit.com/r/gonewildstories/comments/5aykbh/orgasm_in_front_of_girlfriends_unknowing_dadmf/) (most of the commenters believe he knew–but I still naively don’t think so!). I have to confess the following experience does come with a little bit of guilt because she was married (it’s so weird how the married also makes it exponentially sexier, which she did specifically mentioned quite a few times). Our first interaction was last March and we decided to chill out recently.

As a reminder, 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.

I don’t know if these tellings are great masturbation material or not, totally realizing they’re long and I go into a lot of detail about the set-up (which is what I find most interesting) but these are very cathartic for me to recount and document–and I do hope you like. Sorry to paraphrase a Drake song but, *hope you enjoy reading half as much as I enjoyed participating. Because I had a ball.*

So last January I accepted a pretty good position at a company you’ve definitely heard of that has around 6,000 employees–although in the headquarters there are less of us, maybe 300-400. We also have traveling representatives for the company who don’t work primarily at the headquarters but do have a role that requires them to spend about a week each month in our office.

I’d been with my new company for a month and a half when we had a four-day out-of-town conference/presentation in Chicago that about 15 of us from the office attended and about 5 of the traveling reps, none of which I’d ever met before. On the first day my buddy and I decide to duck out early and run across the street for a few drinks at a bar. A few minutes later two of the reps come in and joined us–a guy and a woman named Erin. Mainly they just sat next us and talked to each other while my buddy and I talked amongst ourselves and with the bartender, but a little while in the four of us chatted some. About what I can’t remember, but it was my first time meeting Erin. I didn’t really think anything of the meeting or of her at the time–just that I’d met two perfectly nice reps from our company.

The next night, after a long day at the conference, a handful of us decided to walk together to dinner. It turns out Erin is good friends with a headquarters guy, Mark, who I also get along with really well and he invited her to join us. I also have some friends who live in Chicago, and are in the same industry, so I invited them to meet us there. Because I knew more people at the dinner than anyone else the conversation just happened to flow through me (which is pretty unusual, I’m really not very talkative)–in retrospect, Erin probably thought I was a bigger deal than I really am because of my popularity at that dinner.

The third day was our company’s high-stress presentation. I can’t remember why but for some reason Erin and I exchanged numbers that morning and had to text each other once or twice during the day–strictly about presentation things. The presentation was in the evening, and was followed by a cocktail reception. After the reception wrapped most of the same group decided to go out to dinner again, and by then we were all feeling elated (the presentation had gone well) and a little tipsy (the reception had, too). As we’re walking down the street, being silly, Erin put her arm around my shoulders and I returned the favor. We walk down the street like that for a few seconds, making jokes, being loud, but I didn’t think anything of it–except I did notice her look over at Mark and heard him say, “Just don’t take it too far.” Again, at the time I didn’t even really consider any of this beyond the ordinary. Primarily because, while I am attracted to older women, I still didn’t expect a woman I’d really barely met, and totally in a professional way (and at my work I’m 100% professional–never flirt or even really talk about my personal life at all) to have any potential. At the time I didn’t realize she was married, but I guess I also just kind of assumed it–she seemed married, if that makes sense.

We went to dinner, then went out for drinks, then met up with most of our company’s attendees in the hotel lobby. By now everyone was entirely casual–some standing, some on one couch, some on the other couch, and I’m in an armchair chatting with whoever comes by. Erin moved a big pillow so she could sit beneath me, just to the right of my chair. By this time I’m starting to notice her more because I’m noticing no matter who I’m talking to she’s watching me the whole time, and if I turn to look at her she looks away, unless I talk to her, wherein she’s being kind of nervous/flirty. Knowing now she’s digging me, I really started noticing her around this time. She was short, with olive skin (Italian heritage), a cute face with a girly little upturned nose. A brunette, she had shoulder length curly hair and green eyes. Actually, she looks like a little bit like the Apollonia Corleone character from The Godfather–but when I met her she was a little chubby (not commenting negatively, this will come back later). That night she was wearing blue jeans and some sort of short sleeved floral auburn blouse.

Soon I was getting pretty tired and told everyone I was heading up to sleep. As I’m standing at the elevator, she comes to join me and gives me that certain sort of look again. We stand there, not talking, just waiting for the elevator. I’m absolutely planning on taking a chance and inviting her to my room but when the elevator arrives three other people run up to get on with us. The elevator gets to my floor and I say, rather lamely, “this is my floor”, hoping that’ she’ll pick up on my drift and say it’s hers too and get off with me (at this point I definitely don’t feel it’s appropriate to invite her in front of this group). Well, either she doesn’t get it or she doesn’t have the nerve to get off or she’s really tired because she doesn’t get off. I head to my room, heart pounding and half-hard. I decide to stroke off to relieve the tension, so get a tissue, climb onto bed, pull my pants down just a little (fully clothed except my shoes and socks) and start stroking away. Suddenly it hits me that I should text her…so I do, just to say hey (my jeans and boxer-briefs at my thighs). By this time it’s 1am–and we end up texting for the next two hours–just light flirting, nothing really too serious, the whole time I’m sitting there edging myself (well, sometimes I am; sometimes I’m not really stroking too much). I was thinking about inviting her down to my room but I was also exhausted from the conference. As we’re saying goodnight she invites me to breakfast the next morning. I take off my shirt, jack off, squirt all two hours of built up pressure (missing my tissue, some getting up to my chest), clean up and crash.

The next morning I meet her downstairs and we go to breakfast. At breakfast I notice she has a huge rock on her finger. She notices me noticing it and asks, “did you know I was married?” I told her I thought she might have been but I didn’t know. She said, “yeah, I didn’t think you’d be flirting with me last night if you knew I was.” During breakfast we just chat about me being new at the company and what I thought about it, her take, etc. We get back to the hotel and I have to go check out to catch my flight so I run up to grab my luggage. When I come back down, she’s in the lobby chatting with some of our coworkers but crosses we chat some more. Soon I have to go and she gives me a big hug. I hop into a cab and am heading to the airport when she starts texting me. It’s a fairly brief text conversation but she does say, “I was bad to flirt like that last night but you were hard to resist”. The irony being I hadn’t been overly flirtatious or really done anything to deserve the attention.

I hop on the plane, fly home, and am out at dinner with friends that night when I get a text from her. A picture. It’s a picture of her hand. All I really notice is the big wedding ring on her finger. I’m confused.

Me: ?

Her: I’m still wearing the wristband from the conference haha

Me: Oh yeah

Me: That’s funny

Me: What are you up to?

Her: We’re having family over tonight to watch the game.

We text infrequently for another 15 minutes or so when I ask:

Me: Do they know who you are texting?

Her: No

A pause.

Her: I’m dumb, just forget I’m texting you please

Me: Sorry, didn’t mean to upset you

Her: No, I shouldn’t be doing this

Me: Understood–well have a good one!

Her: Ok

Me: See you around–bye

Her: bye

And I figured that was that. A little light flirting, which we shouldn’t have done, but nothing too egregious.

Until she texts me the next week, at night. Nothing too heavy, mainly work stuff. We text again the following night. And the following night. In her position she travels two weeks and stays home a week, so we fall into a rhythm of texting late at night some of the weeks she’s traveling. At one point for whatever reason she compliments me on a shirt I wore at the conference, which was gingham (I didn’t know that was the name of the pattern, but she told me):

Me: Yeah, I like gingham lot. Have a ton of them.

Her: Oh really

Me: Yep, gingham shirts, gingham sheets, gingham ties

Me: gingahm underwear

So I did take it a little far there…but then at some point we start talking about her underwear situation. Turns out she favors lace underwear.

Eventually we planned on meeting up the next time she came to headquarters for a week–in mid-March. Unfortunately, as the week got closer our nights kept filling up. Originally we were both free Monday to Thursday nights, but then it turned out she was leaving Thursday. Then she had to stay late on Wednesday, then I had a function scheduled for Tuesday…so that only left Monday.

We met for drinks at 8 in a fairly high-end lounge, after work and after she went to inevitable after-work dinner with the other reps. When I got to the lounge she was seated at a table (not the bar, not a booth) and everything was just off. With the table between us we couldn’t accidentally touch, the lights weren’t dimmed enough, and the place just wasn’t sensual/romantic enough at 8pm on a Monday night. Also we were both awkward and nervous…I’ve had online situations before were I ended up hooking up asap, but those were where we literally met with the stated intent to hook up–this was just awkward, as we’d really only met once before in person, a month before. To make the whole situation more touch-and-go (although this also made it hotter later) a decent amount of our co-workers either lived near the office or were staying in hotels near the office (her rooms literally faced our office building, and I only lived 3 blocks away), so we were pretty nervous about someone seeing us. I walked her back to the door of her hotel, we hugged, and that was it.

As I was walking in my door she was already texting me, like that didn’t go well and was awkward. We ended up texting the rest of the night, just to get over the awkwardness of what had just happened. Also, apparently Mark had asked her about going out that night (btw, he’s gay, so not interested in her like *that*–though she did once say she thought he liked me like *that*, which is flattering) and she said something about getting drinks with me–so he started asking her about our relationship, with her insisting we were just friends.

We kept texting one or two nights a week, whenever one of us wasn’t busy or I didn’t have a date. Usually our texts are from about midnight to one, with the texting getting pretty heavy, but we never exchanged photos and never really got to the “when we’re together this is what I’ll do to you” level. Also, she told me that she and Mark were challenging each other to lose weight–and also told me he was asking her more about our relationship. Apparently she’d mentioned something we’d discussed (regarding business) from one of our texts.

Finally she had to come into town again–in May. We had Monday-Thursday evenings free except for Tuesday because I had prior plans (a date, which I didn’t tell her of course). We planned on meeting up at 9pm that Monday at a park between her hotel and my condo, unspoken that it’d be dark outside and we’d be alone.

On my way walking to meet her I thought, as soon as I see her I’ll kiss her. As I walked closer I saw her from about a block away–and she looked amazing. She’d lost a good amount of weight and was wearing tight white jeans and a white shirt that was unbuttoned to show a healthy amount of cleavage. When I got to her though she didn’t really give me the “in” to give her that kiss, so I didn’t. “Oh crap,” I thought. “Here comes the awkwardness again.” We started to walk around the park, and the tension broke. We were laughing and chatting, but as much as I wanted to, she never really gave me an indication that I could even flirtingly touch her.

We headed out of the park and I told her about my apartment building and I’d show her the pool (lame, I know). As we walked to my building this car full of teenage dudes catcalled from across the way–that’s how good she was looking (she said they were catcalling me but of course they weren’t). We got to my building, looked around the public amenities, and I told her about the view from my apartment (it actually is a pretty awesome view). However, she misheard me or was still too nervous and declined (we’ve talked about it since and I still can’t tell). Well by now I’m thinking this woman is a tease / disinterested so there’s really no point in making any move…also, she’s married. I really don’t want to make *the* move on a married woman unless she makes the move on me, you know?

We decide to head back to the park, by now it’s 11:30 and we sit down on a bench and chat. We’re talking for a while until she stops the conversation and says, “what are we doing?” I’m thinking maybe she’s feeling guilty? I awkwardly say something about following her lead when finally she gives me that look and I know what to do. I lean in to kiss her and when our lips meet it’s like she’s had years of pent-up tension. She wrapped her arm around me, totally around my head to where her hand was on my opposite shoulder, her chest pressed into me and our tongues are just going crazy. We break for a second and she adjusts, sitting on the bench but with her legs across my lap. We ended up making out for a good hour before deciding to call it a night. We’re holding hands walking toward the exit of the park, still in the dark but toward all the streetlights and people, knowing we can’t hold hands once we’re out there, so about 30 feet before we do I pull her against me and lean against a tree, where we start making out again. She felt my hard-on against her stomach and moaned and we made out even more fervently. She’s kissing me and pulling at my hair, pushing my head to the side so she can kiss my neck, getting a little rough for a make-out session (which I dig). Eventually when we break there is total lust in our eyes and her hair is a mess. She watches as I readjust myself for the walk back. We get back to her hotel, I hug her goodbye and we make plans to meet in her lobby on Wednesday night at 9.

I got back to my place and she texts me “that was so hot.” I said I knew and couldn’t wait until Wednesday–she texts that she agrees and then we go to sleep. On Tuesday we really didn’t text much, and on Wednesday only to confirm the time and to meet in her hotel lobby.

Wednesday comes and I head to the lobby–it’s a big lobby and a nice hotel, lots of people checking in and lounging around (which made our tryst that much more illicit). She comes up to me with a big smile but says, “we should hurry to the elevator, Chad (another rep) is in the bar and could come out soon.”

We headed to the elevator, joined by two business men probably around her age (she never actually has revealed her age–once asked me if I wanted to know but I said I didn’t care. Pretty sure she’s 41). Being in the elevator with these two unsuspecting dudes, her ring blinging in the lights and the mirror, knowing I’m about to walk off with her and into her room, was quite the thrill. At her door she pulled her key card out from the back pocket of her blue jeans and I noticed how tan her skin was under her thin white tank top (the kind with a little lace detail around her cleavage).

Entering the room, the bedside light was on and the TV was on to some contest show (America’s Got Talent maybe?). I sat down on the edge of the bed and she slid on the bed beside me, turning with one leg up facing me. We chatted for just a minute about the day, before sliding into our first kiss, now a little bit more warm and welcoming since our passion of two nights before. She then straddled me and we made out some more. I reached down to the hem of her shirt and pulled it off, revealing her bra–a very “mom” bra, white lace but covered. Making out again I did the one move I’m good at and reached behind her back to quickly unsnap her bra. She let it fall off and I broke the kiss to have a look. She had a big smile on her face, as she later told me she was so happy to have a guy wanting to look at her sexually, to see her body and to lust after it. While I looked at her body, with the distinct tan lines from a bathing suit (probably c-cups?) she started to unbutton my shirt. Recently I’ve taken in the habit of wearing a buttoned shirt the first time I hook up with a girl–having her unbutton me is a great building of anticipation and she seems to always like it to…there’s a formality to it. Plus I’m not just another guy in an old t-shirt at that point. This shirt was, naturally, gingham.

She got the shirt fully unbuttoned and pushed it off over my shoulders, while also pushing me backward so I was laying on the bed. Then, both of us topless with jeans on, she mounted on top of me, her back arching down so we could kiss, her hair covering both of our faces. We kissed for a while longer, her lips very soft and active, her tongue playing with mine. Erin was/is a very giving lover, which I dig because I like to put in effort too. My hands ran up and down her tanned back, firmly pressing against her, causing a quick sigh/moan to escape. She almost kind of hopped down next to me, laying on her side with a big smile, and we kept kissing. It felt great to press our upper bodies together, arms and legs entwined, hands running up and down one another.

Our pace and urgency began to pick up as my left hand came around to the front brushing against her stomach. In full disclosure, she’d lost weight quickly and had a daughter, so her stomach wasn’t tight, but that almost made it better–like she wasn’t supposed to be doing this. Then I unbuttoned her jeans and unzipped them, my hands returning back to the back–her fly just open now, revealing her lace white panties. I chuckled and said “lace white panties, huh?” as we kissed and she giggled and with a smile and cock of her head said, “just for you”. I reached around into her jeans and grabbed her ass, which felt really really good. She started to unbuckle my belt so I laid on my back and watched as she unbuckled, unbuttoned, and unzipped. I lifted my ass as she pulled them down off of me, and then crawled back up towards me. My hard-on was on my thigh inside my boxer-briefs and she cupped it with her left hand while she came up to kiss me. I couldn’t help but notice her huge wedding ring was sitting right on top of my cock. We kissed more while she began to squeeze and press.

I felt a surge of energy and rolled her quickly on her back. Went down to her waistband and now it was her turn to lift her hips (maybe the best moment–that first lift of the hips). I pulled her jeans off of her so we were both just in our underwear. If I’d been thinking I probably would have prolonged the moment, but I was crazy with lust and build-up and reached up right away to her panties. Again she lifted her hips and I pulled down the panties, too. I started to kiss up her leg, planning to really kiss all over her body when she said, “just put it in.” I was torn because I wanted to kind of tease her and be a “good” lover so I paused but kept kissing up her tan leg, getting closer to her neatly trimmed landing strip. “Put it in,” she repeated. “Just be in me.”

With that I awkwardly crawled up toward her and she sat up, reached in my waistband, and pulled my boxer-briefs (white against my own tanned skin, thank you) down. I raised each knee up to pull them the rest of the way down and then noticed she was inches away from my cock and was running her fingers up my thigh. We made eye contact. “Kiss it,” I teased her. She gave the head a quick kiss (but did press her lips into the sponginess) then looked back up at me and laughed. I stood up and walked down to my jeans to grab a condom while she laid on her back and adjusted some pillows for her head.

When I looked back up her knees were spread open, and she absent-mindedly had her left hand brushing around her pussy as she gave my body a look up and down (ego-boost). Again, seeing that huge sparkly rock as she played with herself and stared me down just made me hornier. “Come here” she said and crooked her index finger from her right hand and then giggled. I have to say, she knew sexy things to say but would always giggle in a really cute way afterwards as if she couldn’t believe she’d just said it.

As I’ve mentioned previously, for some reason I really dig having my partner put on my condom, so I walked up to where she was laying and handed her the condom. She smiled, opened the pack, took out the condom, and rolled it down over my shaft. Sometimes, and I find often with women who are older than me, this is a moment when they really give my cock a look-over, and Erin was no exception. She was totally focused on it, stroking me as she rolled the rubber down. Once she fully on she gave the head another quick kiss.

Then she laid back again and I crawled above her while grabbing a pillow to put under her hip (I didn’t want to just lay on her, I wanted to be vertical, but sometimes it’s hard to do that unless the hips are a little elevated). I was feeling pretty full of myself when as I started to ease my way in she ran her fingers up and down my chest. As I eased my way in I could hear her start to breath heavy through her nose. I’d been watching my cock slide in her, but I looked up and was so pleased to see the pleasure on her face as her eyes were closed. Once I was in I really thought I’d show off and started rocking my hips, kind of in a figure-8, and did this for about 30 seconds until she showed my she had other plans. She grabbed my hands and pulled them up toward her face, kissing the fingers but also causing me to lay down on top of her. Once my face was right above her she wrapped her arms around my head and kissed me, our kisses getting more and more fervent as she started to hump up into me–for a minute I wasn’t doing anything with my hips at all. She held me tight against her, basically so I couldn’t move, and she started humping faster and faster like I was just a stationary toy (which btw was awesome). I could tell her orgasm was coming fast because her mouth was now near my ear and I could hear her breathing getting more and more ragged. As she started to cum she started to dig her fingernails into my back–hard. Like, it hurt. But I just stayed still and let her reach and recede from her orgasm, her humping getting a little slower and her breath catching and then relaxing.

After a while her orgasm passed and I raised my head to kiss again. This got a little more passionate, then a little more, until she was just as hot and heavy as before, and this time I was the agent in motion, pumping into her. The harder I pumped the more she dug her nails into my back. I’d never had a girl do that before but it was pretty hot. Soon we were just straight out fucking, me pumping into her as hard as I could, one of her hands digging into my back while the other hand gripped the sheets and her mouth was wordlessly wide open, eyes closed. She was cumming again and started humping up into me again. I just looked down at her hips and fucked her as hard as I could. I wasn’t really close but it felt amazing. She let out a little throaty “ugggh” as she came and then I started to slow down still thrusting in and out but not as hard or fast. Almost as soon as her second orgasm went away she turned her head to the side, eyes still closed, and said “harder”, so I picked up the speed I was at again, soon fucking her just as hard as before. Within 90 seconds she was cumming again, humping her hips up into mine, her right hand digging into my back with her left hand on my face (I could feel that ring against me). As her orgasm subsided our eyes locked and she said “one more”. I chuckled and she kind of giggled but she was much more serious than before the sex had started. This time I went back to be vertical (rather than laying on her) and started right into pumping–not even building up. Her legs wrapped around my lower back and I tried to pump as hard as I could, but it wasn’t quite as full as when I’d been laying more on her, so I went back to that position and heard her sigh–clearly she’d prefer me fully on her. For her fourth time I fucked her has hard as I could again, and this time she started scratching up and down my back, though one time she turned her fist around to run it up my back and I felt the diamond of her ring. Within two minutes she was humping me again, climaxing with the same open mouth, throated “ugggh”. I totally could have done this for the next hour except by now the condom was kind of dry, so once she relaxed again I pulled out. She looked at me with a bit of disappointment so I said, “changing condoms” as if that’s a thing you do a lot, and she relaxed her expression to kind of a stretch.

I pulled the condom off, threw it away, and went down to my jeans to put on another. (I’d brought two packs of 3). Once I had it on I noticed she’d flipped over and was now on her stomach, eyes closed and arms tight. I crawled on top of her and heard a giggle and moan of pleasure as I laid my weight against her, my cock resting between her cheeks onto her lower back. We stayed like this for a minute until I lifted myself up a little, allowing her ass to raise for easier access. I slid in and she continued to press back into me until she was up on her knees, with her head on the pillow. Her right hand gripped her breast and her left hand just kind of went out to the side, the wedding ring just begging to be seen. I started a bit slower this time but soon had picked up the pace and was back to fucking her–pretty hard. Her hips and ass were meeting me thrust for thrust, to where there was a slight ripple on her ass cheeks every time our bodies met. Her hand that was on her breast moved down to her clit and she started fingering herself, which caused me to slow down so I wouldn’t break her rhythm. We continued like this for a few minutes until she started lifting her ass higher, another orgasm sweeping through her. Her mouth went open and that sexy “ugggh” happened again, not loud like she was trying to put on a show with her orgasm, but just kind of raising out of her body. Feeling and seeing her cum, and seeing her in that position, ass against me, cheek against pillow, eyes closed, just in ecstasy, I could feel my orgasm coming fast, too. Almost before I knew it my cock was twitching inside of her. This wasn’t a full body orgasm but I could feel pulse after pulse shoot up the shaft of my cock. I leaned back a little, just in heaven as she continued to fuck against me, not stopping until I sat back up and grabbed her hips.

After disposing of my condom we collapsed into the bed, me on my back and her with her head on m chest, her leg thrown across me, the top of it brushing my wet cock. We laid like that, totally content, for a good 20 minutes. I drifted in and out of consciousness, snapping too whenever I got too deep because I didn’t want to fall asleep and sleep there.

Soon we were kissing again, lots of lips and tongue, pretty wet actually…which I dig, personally. We were totally naked, lights off, with the lights of the city coming through the window. She crawled down the bed and took my now dry cock in her hand then, surprising me, put it into her mouth (surprising because it had the smell and taste of sex on it). From her previous quick kisses of it I had suspected she didn’t like to give oral, but I was wrong. She wasn’t super-skilled at it, but was into it, making eye contact with me as she did. Her left hand ran up the side of my stomach, resting on my pec and she kind of squeezed it–that ring right in my face again, causing me to twitch. What we were doing was so so wrong, she has a husband and daugther, but damn that has always made it hot (she once even said almost exactly that, as we were resting after sex). She sucked for quite a while, about 10 minutes, then came up to kiss me.

We kissed for a minute and then she sat up–but this time I had plans. I grabbed her ass and kind of held it and pulled it up the bed, up my torso. She started walking up the bed on her knees, giggling, not knowing what was happening. Finally once her pussy was about at my chest she realized what I was doing and let out almost an, “oh!”. A few more small movements, a pillow under my neck, and she was mounted on top of my face. I held her body and controlled her, first sticking my tongue inside, then coming back to hungrily lick her clit (which was pretty engorged). She alternated between her hands on the headboard and her hands on my head, finally keeping them on my scalp and pushing my mouth onto her as she began to climax. I had my eyes open so I could watch her arch. Right before she climaxed I dug my nails, best I could, into her ass cheeks, which seemed to put her over the top.

After her orgasm wave she lifted both legs, one at a time, and kind of shook out any cramp or tightness–it wasn’t sexual at all but the need to do so made it kind of hot. Then she walked, on her knees, back down so her pussy was hovering right over my cock, almost taunting it. She kept it there for quite a bit, finally saying “you have amazing self-control” . . . but really I didn’t and don’t. I’d already cum so I just didn’t have that I’m-going-to-die-if-I’m-not-in-her feel and was willing to wait for a condom.

This time *she* crawled off the bed while I laid on my back, *she* grabbed a condom, opened it, and crawled back up. Her eyes focused on my penis, she unrolled the condom on me, then grabbed my hard-on, swung her leg over me, and lowered herself. The head entered slowly and she actually gasped a little this time, taking care to lower herself more and more. I was loving it, loving her expressions, loving her gasping, loving the care she was taking, loving her left hand balancing against my stomach, just watching enthralled. She really wasn’t having sex with me at this point, she was having sex with just my cock. Finally, after she was in for a while and had been looking down at my body, she looked up into my eyes and noticed my rapt expression. She giggled then got serious again and kept the eye contact for quite a while. She bounced up and down, changed her leg position to were she was grinding, then bounced from the grinding position. She leaned forward and put her hands on my shoulders and I raised my knees a little and she rode me that way, her ass bouncing into my thighs. After a while she shifted her legs again to where her feet were firmly on the bed. As she did so she said, “I could watch you watch me like that all night,” then started bouncing up and down pretty hard and had an almost wicked smile. As hard as I was before, this just drove me harder. I started thrusting my hips up the meet her and almost instantly her hands went down to my chest for support, her eyes went closed, her mouth open, and she was clearly close again. This time, as she climaxed, while her throat did the “ugggh” again, she looked right in my eyes. I could actually feel a pulsing wetness in her pussy during this orgasm, seeping out onto the top of my balls. We were fucking pretty hard when I felt myself have a rare on-bottom orgasm, this one with a slow build. As I began to orgasm I grabbed the fleshy part of her hips and slammed myself up into her, grunting loudly (which I usually don’t do). Erin rode me for a while afterward, not stopping until my cock was basically back to it’s softness–which is actually not the safest thing for a condom but as she pulled off me I held the condom tight and nothing seeped out.

She laid on top of me again, condom still on, both of us naked and sweaty. We laid for a while, maybe 5 minutes, not saying a word. Finally I said, “what time is it?” and she looked at the clock. “It’s almost midnight,” she replied. I said I’d better head out and we got up so I could put my clothes back on. She sat on the edge of the bed and I noticed she wasn’t making any effort to get dressed (which I find hot–that confidence/unabasahdness of a nude woman). She was just sitting on the side of the bed, weight resting on her arms, watching me get dressed. With my pants pulled up I went over to her and she zipped up my fly, buttoned my button, looped the belt, and gave my stomach a kiss. I put my shoes on and then my shirt, went over to her again and she stood up and buttoned up the shirt. That buttoning turned into our goodbye kiss, which became more and more passionate until my back was against the wall, me fully dressed and her totally naked. Our hands ran up and down each other’s bodies, me gripping her ass, her pressing her body into my once-again hard cock. She reached into my pocket and tried to pull out the second strip of condoms, put they caught on my pocket. However, I got the clue and was in full agreement. I pulled out one pack and she unzipped my fly, unbuckled my belt, and undid my button. While kissing, she grabbed the open button of my jeans and pulled my toward her until she backed into the bed. I pulled my pants and boxer-briefs down to my knees and she spread her legs wide, actually totally in the air. I handed her the condom and she reached down to put it on, which meant her legs had to come down. Once on she started to guide me towards her wetness, and I hooked under her legs and spread them open again, holding her ankles.

This was a primal, in-case-this-is-it fucking, hard again. Her hand reached up to my shoulders and those fingernails dug in. I thrust in and out, but with her legs up she couldn’t buck her hips like before…which I didn’t really care about because she looked so hot, totally open to me. After a bit I released her legs and she wrapped them around me, thrusting again in rhythm with me. I had never just straight fucked this much in one night, just this much primal pumping. It actually crossed my mind that I was surprised I wasn’t tired but one look at the lust she had gave me an adrenaline shot and I kept fucking her as hard as I could. She reached up and grabbed under my shoulders, pulling me toward her, and once again she dug her fingernails in. This time I grabbed her left arm and pinned it across her chest, basically forcing her to play with her nipple–and she did, pulling it and tweaking it. She was cumming again, this time her “ugggh” catching more with each thrust. Between that and staring at her ringed hand tweaking her nipple, I could feel my own climax approaching again. My cock starting to swell my balls starting to tighten. Again I was cumming, fucking her as hard as I could. I buried myself as deep as I could, feeling her clamp around as much of me as possible–and just held it there until the last pulse.

Then I actually was ready to leave. I pulled myself out of her, took off the condom, through it away and zipped up. She was somewhat in afterglow mode, but did stand up after a a few seconds and joined me. We kissed again and she walked me to the door, still totally naked. We kissed at the door and I wrapped my arms around her–this time more romantic. We said goodbye, kissed again on the lips, and I headed out.

A few things went down this summer. For one, whenever she would visit for a week she would leave her hotel key in a certain drawer (that we’d determined) and she’d text me her room number. I always came over at 9pm, open the door and she’d be ready for me to undress her. One time I told her to be naked when I came in and she was–right behind the door, totally naked. Another time we had sex next to the window so we could both look out at our office (her hotel was right across the street). I asked her about lingerie once but she was nervous to pack it, so we never did that.

Sometimes in the weeks we weren’t together we’d be texting and I’d mention a date or that I’d been with someone the night before. She’d get kind of possessive and jealous, which I found hot–although she admitted she knew she had no right to be. Also she always wanted me to be more open with her and talk about my feelings, but I didn’t feel comfortable doing so. I didn’t want to get into feelings with a married woman and, to be honest, I think the mystery she felt toward me made her more attracted to me.

We never ever talked about her marriage situation until August when she asked why I never asked about her marriage and I told her it wasn’t my business and I wasn’t trying to break them up (I know, strange logic–but in my mind I’m not asking her to run off with me). She didn’t really say much except something about “if that was going well we wouldn’t be here right now.” That kind of bothered me, for her. Between the creeping guilt, Mark asking her over and over what was going on between us, and, frankly, the novelty wearing off we decided in September to stop the affair and just be friends.

Of course it wasn’t that easy and we started texting a few weeks later. There has been something about her, this pull–the lust I get from her is so unabashed it’s difficult to not want her badly. We had a long texting conversation and I told her she was my kryptonite and I felt it was best to just not talk altogether because if I talked to her I couldn’t avoid lusting after her. Well what she texted after that was unknowlingly about the hottest thing ever. She texted, “omg I’ll touch myself thinking of that for about forever.” And of course that led into us having a sext session that night. The next day we did text though and say that’s it–and we haven’t texted since.

However, I did see her in a meeting three weeks ago when came to town–a meeting I co-ran. When I was standing up talking and looked out and saw her, those eyes had the same look of lust and I was totally thrown off. Despite that, we’ve stayed true to our word and haven’t texted since.

Thanks again for all the kind words so far! Hope you enjoyed my reminiscence!

Source: reddit.com/r/gonewildstories/comments/5eyzuu/married_coworker_f_and_the_young_man_m_an_affair