So I’ve always wanted to write about the time when my line manager at work and I slept together. It was a few years ago and I’d spent about a year in my graduate role at the time.
I’ve always been attracted to women with ambitions, independent and driven; so I guess naturally this has led to a bit of a fetish for older women. I’ve moved on since and now work for a completely different
company so I’m a bit more comfortable writing about this now.
I was about a year in, as mentioned, and my team had a great year; we were up for a couple of awards at an industry awards event. I worked in the marketing team and my line manager was the Director of
UK Marketing, she reported straight into our international HQ in Paris. We lived in the same town, just one over from where we worked. We had a good working relationship, she wasn’t the most professional boss but
she was super friendly; incredibly helpful on a personal level and was well-liked by everyone. After being invited to the industry awards with the rest of the team, she suggested we meet at the station in our
shared town and travel to/from the event together. Of course, I figured it would be a good idea, I didn’t fancy the idea of travelling alone with no one to talk to; and I was nervous for my first industry event.
We got to the venue at about 7pm, a bit later than the rest of the team so we went in and met them at the table, it was pretty cramped so we had to sit closer than I thought comfortable at the table on the two chairs they’d left for us. Our arms/legs kept brushing and I leaned slightly away, assuming she’d do the same but she didn’t. I figured, oh well she’s comfortable with it, I’ll just sit as normal and after the official stuff things will loosen up a bit.
We got through the 3 course meal, there was free wine and beer included; and everyone took advantage of that. It wasn’t carnage like you see at weddings but it was definitely an eye-opener for me to see that people aren’t always straight laced, they are humans at the end of the day and like to have a good time. Anyway, we won 2 of the awards we were nominated for – great! It was about 9:30 when we got through the official stuff and people started to mingle and congratulate each other. We’d gotten through about 5 bottles of wine as a table of 6, so we were in a merry state but not drunk yet. One of
the account managers from our top retailer came over to congratulate us; he had wine teeth and eyes were a bit glassy “Congrats guys! Oh, and you’ve brought your cub along with you, nice!” he jokingly said to my manager/director. Immediately I tensed up, that’s a bit inappropriate right? She giggled and linked her arm with mine, “oh well, if you want to live the glam life you need a handsome man on your arm” she laughed, I forced a laugh, still wasn’t comfortable but at least she thought it was funny. She
put her arm on my opposite bicep and squeezed “oh and a strong one too, just the kinda hunky young guy I need” she cackled. Again, I was taken aback but laughed for real that time, kinda cringe but ok.
“Careful mate, she can get a bit feisty after a couple of wines” the guy said laughing again; she let go of my arm and placed her hand on my lower back tapping a few times just above my butt, immediately I felt the tingling in my stomach shooting south, she must have touched me there for 2 seconds but it felt like 10 minutes. I made a quick excuse to use the bathroom, did my business and then bumped into a
colleague on the way out; he said “oh mate wait for me, lets hit the bar and celebrate.” I did just that and forgot about the interaction before.
I was shooting the shit with someone from another company, joking about who’s awards were better; bit of banter about who’s company was better – all in good taste. Anyway I realised it was pretty late
and I wanted to grab some fresh air so I nipped outside to cool down. Bad idea. The alcohol all hit me at that point and my head suddenly starting spinning, I figured a quick vomit would sort me out so I ducked into the alley and stuck two fingers down my throat. I checked my phone and saw some missed whatsapp messages from my line manager, “You ok honey? X still ok to share a train home? Last one is 1am x”
I saw it was 12, we were 10 minutes from the station
“Yeah no problem, I’m actually kinda hungry, I might head to Waterloo now and grab a Mcdonalds – meet me on the platform?”
“Hmm, I’m hungry too – I’ll get us an Uber we can share, as long as it’s not too close for comfort for you? ?x”
“Lol, yeah ok – meet me at the cloakroom”
I rushed over there to get my jacket, I felt a slap on my butt and jumped. Turned round and she was there beaming at me.
“Oop did I make you jump?” She looked at me in the eye and pulled a puppy eyed look, pursed her lips out “ooh is baby scared, has baby been sick?”
“Ha, yeah a bit – just tactical chunder though; I feel fine now, but I could smash some food.”
We jumped in the Uber when it arrived, it was pretty small so again we were cramped, both of us were pretty boozy though so didn’t bother, she tucker her arm under mine again and rested her head on my shoulder until we got to the station, I didn’t think anything of it, just put it down to her being tired.
Anyway we grab food and get on the train, there wasn’t much space – last train back so a lot of people were on it. We had to take the only seats right next to the toilet, again she leans her head on me, I thought the alcohol might be getting to her now whereas I was sobering up. She put her hand on my leg,
I thought for stability at first, but she left it there. I could feel myself getting hard, I think she could tell, I had slim fit suit trousers on with tight boxer briefs underneath. I’m quite proud that I have a well-sized cock, it measures 7.5 inches when erect and quite thick, even though I’m only just under 6 foot I’d say that’s a good achievement. Anyway I quickly nip into the toilet to rearrange as it was getting painful in the tight clothes; I’ve locked the door and I can hear her laughing and going “I can see you in therrree!
Oooh I’m gonna open the door!” I start laughing and come back out to sit down again, I’ve rearranged myself now so my cock is in a much better position to get hard in these trousers. I come back out with a
smile on my face and say “not in front of all these people, I don’t want them to think we’re joining some kind of train-themed mile-high club”. Some other people in the carriage I could see where smirking, she
laughed at me and said “don’t worry honey I’m just joking.” But as she smiles up and me her gaze wonders down right at my crotch and I can see her sizing it up, I was bulging through the material and she could see it. I saw a small lick of her lips while her eyes lingered there and I quickly sat down again.
“I’m so glad you joined the team this year” She said
“Yeah, me too. I think I’ve done quite well and the performance has obviously been great”.
“Absolutely, but for me I really like my team to have good chemistry, I like to think we’re like a little family in our part of the office; we do our thing together and get great results that are for us only.”
“Yeah I like flying under the radar so to speak.”
“You mean, under the sheets?”
I went red and she cracked up; “don’t be so up tight you need to let loose!”
I was at that point where I was thinking that it had been a good night, I figured it was ok to relax a bit but things had got a little too relaxed and I was terrified of being THAT guy who read things the wrong way and made an advance and ends up getting fired. I thought the best thing at that point was to get off
the train at our stop and get separate taxis home, and I was fully prepared to do that. But I was also at that point where I had sobered up a bit and felt like I could’ve had one or two more if were going on a
proper late night out. The train pulled in and we got off, there is a pub right next to the station and we saw it was open. She linked my arm and said “one more in the pub and then home?” I obliged and we went in. I asked for a vodka mixer and she a red wine, we sat next to the window and she seemed to be taking quite large gulps of her wine. I though maybe she was just antsy to get home and was regretting the night cap, so I also started drinking mine quite quickly. I realised I’d got to the bottom a bit faster
than planned, it was also quite strong – I figured she’d got me a single but it was definitely a double. She started talking about my performance, and how she wanted me to gel a lot better with her as she didn’t
think we were quite close enough yet. I could feel the alcohol hit me right away again and already felt sinking into my chair; she leant forward and touched my leg “I really need us to be closer if you’re going to keep on at the company and move out from your temporary contract into a permanent role here. Tell
me about yourself, your love life? I love gossip.” I chuckled and said something about just out of a long distance thing because we realised we were in different places. She laughed and said “Oh don’t you get enough?” I said “Probably shouldn’t be talking about this but I’d say not for what I think I need. Anyway I’m pretty tired, I’m going to walk home from here.” She looked at me and said “I don’t think you should
walk home actually, looks like that vodka hit you pretty hard; why don’t we share a taxi and you can stay in my spare room?”. I nodded, thinking about what she had said about us being closer, figured it would
be fine, I’d just grab a quick shower and walk home early the next morning. Next thing I know we’re in a taxi outside the pub, we’re mid conversation about what I want to do at the company and how she can help me with that – my memory here gets pretty hazy – I think the alcohol had got to me. I can
remember her running my leg again, but this time I could tell she was definitely feeling the alcohol; her face was close up to mine and I could feel her warm breath on my cheek while we’re talking. At one point her hand moved right up and squeezed my cock, and she was saying “…closer, if you’re going to
make it here in my team we have to have chemistry.”
The taxi pulls up and she thrust the driver £10 and told him to keep the change; she pulled me by the hand out of the car and I clumsily slammed the passenger door shut. I could hear him saying “go easy on
that, lad” while it was closing. We went into her kitchen and I quickly grabbed myself a glass of water, while I was downing it in front of the sink I suddenly felt her grab and squeeze my waist – I’m super ticklish and this made me jump and I spilled water down my front. Immediately she went “oops, lovely
wet t-shirt contest! Let’s get that jacket off you, it’s like you’re giving me a striptease!”. I laughed and went to the sofa, I’d kicked my shoes off at some point and dropped myself down on it, unbuttoned the top of my shirt and undid my belt to relax a bit. I could feel her standing behind me, she put her hands
on my shoulders and start rubbing and squeezing them, then she moved up to the back of my hair, running her fingers through it. “You know you’ve got lovely soft hair, I always think you should smile more.” Then she pulled my head back vigorously and kissed me upside down. I was a bit taken aback but then thought about the taxi ride, and suddenly I got rock hard again. Her mouth was cold on account of the drink. She reached down and grabbed my junk again, immediately I thought “this is the do or die
moment” I froze for a second, and looked at her, all the things she’d been saying, does this mean if I don’t do as she says she won’t extend my contract next month? I don’t want to lose this job, it was hard enough getting through the interview process. I turned to look at her, I hadn’t realised she’d unzipped
her dress while I was distracted and she was standing there in this lacy underwear. I was nervous, this was what I’d always dreamed about, but not with her – I’d always dreamed about I being a neighbour or someone outside of my personal circle. This felt too close for comfort, but I was already in too deep, I shouldn’t have taken the taxi ride home to hers or just gone straight home from the station. If I back out now, it’ll be embarrassment for both of us and she’ll find a way to make it affect my review, we don’t
want to always be looking at each other knowing that I turned her down one night and so she’ll get rid of me.
I knelt up putting my hands on the back of the sofa and leaned into her, she grabbed my face and pulled me in; an awkward kiss but I guess she was going for passion. I clumsily clambered over the sofa so we were both standing, she started to unbutton my shirt and I put my hands on her butt. It was soft, squidgy, and not very toned, I’d only been with women under 25 by this point, all of whom worked out. It was surprising but not unwelcome. She crouched down and dropped my trousers down, my cock was
poking out the top of my boxers now and she very gently pulled it out and took it in her mouth. This was it; my fantasy, an older woman who knows how to suck cock, I was hard as a rock while she ran her tongue up and down my shaft and over my foreskin. She licked the head and then took the whole head in her mouth, she swirled her tongue around my head, and bobbed her head up and down. She couldn’t deepthroat me, but I didn’t mind, I always find it kind of hurts anyway. She squeezes my balls while she
slobbers all over my dick, and then the bit that I will always remember in my minds eye as clear as day, she looked up at me with her blue eyes, and smiled, biting her bottom lip with her perfect teeth while she stroked her saliva up and down my shaft, squeezing it hard. I still think of that moment, it pushes me over the edge when I’m having sex with my now-girlfriend or when I’m touching myself. It was so hot. “Use me” she said, and I put one leg up, feeling her hair underneath my thigh, planted my foot on the stair just behind her and thrusted in and out of her mouth while I held her head in place with
my hands. It felt good, but clumsy, her teeth kept brushing the top of my cock as her mouth wasn’t quite wide enough for me to comfortably do it. This happens a lot, I always need lube for full sex. After a short
while of doing this I was getting uncomfortable, I said “let’s take this upstairs” and followed her to her room.
She sat down on the bed to face me and took her bra off, I knelt down between her thighs and started to kiss them; moving further and further down. I ran my tongue down the inside of her thigh right into
the crease between her lips. I pulled her panties down and saw the smooth skin, she’d recently been waxed, which definitely helped as there was a very slight lingering smell to her vagina. I can only imagine
how bad it would have been if she hadn’t waxed. I began to lick her, up and down, I can feel how wet she’s getting. So I moisten my first two fingers with my spit and put them inside to rub her, I plant my
mouth right over her clit and begin to circle my tongue round and round it, all while stroking her g-spot with my fingers. I could hear her breathing heavily “oh fuck, wow, shit, fuck, wow”. It just made me keep
going, going, going, what felt like forever, my jaw was just starting to get sore when I can feel her trembling, her vagina tightens and relaxes, tightens and relaxes again, then suddenly she gasped and felt her orgasm. “I want you now, properly” she said. I stand up and get her to drool over my cock again,
then slide it inside her. Slowly at first, but she’s already pushing into me, she wasn’t scared to get straight into it.
The next hour is a blur, we move from the end of the bed, over to the top, from behind I’m pushing into her while standing on the floor with her on the bed. Her butt is getting redder and redder, I’ve been spanking it and grabbing it; just using it as a handle to push deeper and deeper into her. I flip her over
and lift her legs up over my shoulders, I pushed my cock down as far as it would go, my god she was so wet and dripping; I sloshed in and out until I could feel my load making its way up my shaft. She’s saying
“cum for me baby, I want it, yes, fill me up you naughty little boy” and it just sent me. My brain pulsated as my cock just exploded with cum, I kept pushing into her, I must have spurted 3 or 4 times and then a huge load followed, it just flowed out of me like a river. I collapsed on top of her for a moment or two;
came to my senses almost immediately. The post-nut clarity is so real. I thought “oh shit no condom, why am I here? I need to get home, so sleepy…” I pulled myself out of her and walked to the bathroom; grabbed some tissue and wet wipes she used to take her makeup off – I assumed – came back in and
gave them to her. “Wow, stud!” she said “I got the feeling you were good but…wow!” I smiled and mumbled about grabbing my clothes from downstairs. I went back down and grabbed my clothes; pulling my boxers and trousers back on; I grabbed a drink of water and went back upstairs. She must
have cleaned up pretty quick because the covers were pulled over her and she was facing away on the bed. “OK, I’m going to head home” I said, I thought loud enough but definitely awkward! She mumbled something incoherent and pulled the covers tighter over her. I took that as an “OK” and just left. I walked home with thoughts racing through my head all the way back to my shared house. I kept an eye on my phone through the weekend just to see if she’d say anything, nothing. I didn’t know whether to message her about it or just to leave it. I left it. Monday would come and I’d just deal with
whatever the vibe would be. I went back in the office on Monday morning, she looked up and beamed at me “Happy Monday! Bright-eyed, bushy tailed right?” I guessed that was that, we’d just forget about
it and move on. I don’t think anyone knew what happened, or at least they never let on that they did. We never had any sexual contact again after that night, so I put it out of my mind.
Source: reddit.com/r/gonewildstories/comments/hnlpra/i_25m_slept_with_my_line_manager_42f_so_shed_keep