My (only ever) threesome with my Head and TA in my second year of teaching [MFF]

Had a threesome with my teaching assistant and headteacher after Saturday class in my second year of teaching. TA suggested it after we had started drinking and playing ‘never have I ever’. I said I’d never had a threesome, and none of us drank! We joked about all being boring and then in a bit of a lull of conversation she said something like, ‘Well, there’s three of us here, just saying’. They were both over 40 and I was 24 (maybe just turned 25?).

Still the number one hottest moment of my life!

Just to set the scene a bit, we were at school running extra classes on a Saturday and we’d just sent the kids home. It was the last session before their exams and my Headteacher got a few bottles of wine from her office as a ‘thank you’ to us for giving up our time. We started drinking and were all sat around one of the tables.

So after my TA (refer to as A), pointed out there were three of us there, I joked that she must be really desperate to get out of going home to do all the washing (she’d mentioned that earlier in the day about how she didn’t mind giving up her Saturdays atm). A laughed and my head (we’ll call her K), said ‘So desperate you’d even sleep with Havinitlarge? Wow’. (Obviously, I can’t remember exactly what they said but I’ll keep it as true in essence as possible). I pretended to be offended but A said that she definitely was – anything not to iron!

I told them I would sacrifice myself to save them both from housework, and K said I was so chivalrous. At this point, it was still very jokey and playful. We actually kept going with the game, but the questions were much more sexual now. At some point, A got up and went to the toilet, and when she came back, she didn’t sit back in her chair but stood, leaning against the table, next to me.

She was flirting heavily at this point, slapping me on the shoulder and stuff. I remember the never have I ever question was ‘Never have I ever been with an older woman’, which I drank to. I can’t remember which of them asked it, but I reckon it was A because she used it as an excuse to move to sitting on my lap to poke fun at me for being a ‘lothario’. We were talking more than playing the game by this point, but every now and then someone would put out a question. During the conversation, A began slightly gyrating against my crotch while on my lap, and I distinctly remember my hand moving over her waist and the outer part of her bum over her jeans quite a bit. I also remember K giving A a look like, ‘What are you doing?!’ and I think A shrugged or laughed.

When she first sat down, A was facing K and away from me, but while we were talking, she’d subtly shift around every time she spoke to me until she was eventually sat sideways on my lap and her arm was around my shoulder. There was a point when we were talking, or Karen might have been, and we caught eye contact in that way you do when you’ve been flirting with another person and it reaches that ‘point’. We both moved forwards quite slowly and all of a sudden A and I were kissing. K said something like, ‘You two are ridiculous!’ and when we broke apart, we began laughing. K wasn’t actually annoyed; she was smiling but in an exasperated way. I pulled A back in and we went for it a bit more this time; I groped her more heavily and there was a lot more tongue. This might have happened on and off three more times while we still sat talking with K. Eventually, A broke off during a kiss and said, ‘K, it’s getting a bit weird you just sitting there watching us. Like, can you not see where this is going?’

K said sorry, did we want her to leave? Looking back, it was strange seeing her so out of her depth – she was a really efficient headteacher and was always professional. She’d also admitted to me in the past that she’d had multiple affairs with married men when she was in her twenties, so you’d think she’d have been more open about joining in. Anyway, A said, ‘Well, unless you want to ‘get involved’ ‘. K pointed out it was pretty hard when we were all over each other. I can’t remember what I said, but it was something to do with swapping places. A got up and K sat on my lap instead. Even though A is much better looking – blonde, very tanned, brilliant blue yes, white teeth – she’s a lot heavier than K who’s not the best-looking woman, but slim. K sat on my lap and I recall us both laughing a lot as we tried to kiss. Eventually, we got down to it and started kissing. My hand went up her dress and stroked up her bare legs. Then I felt hands on my shoulders as A began to massage me. I broke from K to look around (mostly in surprise), and A kissed me. When we stopped, I was about to go back to K but A grabbed the back of her head and kissed her first. I kissed K’s chest and took one of her breasts out of her dress and bra (the left one, if that’s of interest to anyone) to lick her nipple. She has those areolas that cover the whole of the tip of the breast and they were quite saggy with a lot of give to them (she’s a mother of two so I presume breast-feeding did this).

We were at this for a bit before I had to shift K around because my leg was falling asleep – I was so scared that if I broke the magic it’d all stop so I’d tried to just grit my way through! I really thought I’d ruined it because A said that the classroom probably wasn’t an ideal place for threesomes (she definitely joked with something like, ‘I presume – it’s not like any of us know!’). We were all stood up and there was another lull, and I desperately thought of a way to get back on track, before K shrugged with a bit of a grin and said, ‘Library?’

The library is not far away from my classroom, literally a 2-minute walk down one hall, but it took us a while because A and I were all over each other. Somewhere down the hall we ended up against a wall and me fingering her (have no memory of how we got to that point), and K came back and said exasperatedly, ‘You only have to wait 30 seconds to get to the library!’

When we finally got there, K had thrown the cushions together. Yep, if you’re queasy about something to do with school library cushions being used for a threesome, time to stop reading. A was out of her jeans so quickly I didn’t even register that she was taking them off until she was kissing K again. I went over to them, pulled down A’s underwear and began kissing her fat bum cheeks (seemed like a hot idea at the time). When I stood up, we all started kissing each other in a kind of free for all, both of them at different points feeling me through my trousers and I presume each other. A just had her top on (she didn’t take it off during at all – I think because of body issues) and K was still in her dress but without her heels. One of them undid my belt and I think it was A that took me out of my boxers and began stroking me.

At some point in this encounter, A disappeared from the kissing and travelled downwards. K and I were locked together but my mind was all downstairs, waiting for the moment when I’d feel A do it. And then the unmistakable feeling of your cock being in someone’s mouth came over me. K stopped kissing me and stripped. I wish I’d watched her more but as soon as she stopped kissing me my eyes were glued on A giving me head. K stepped out of her underwear and then went to her knees in front of me too. She touched A on the back and A opened her eyes, saw her and came off me so K could take over. This is my first and only threesome and I’m not some master in the bedroom (I was pretty good in my day, I will say though), but maybe because of the wine or the shock of what was happening, I never had a worry about cumming early – actually I had more times of my cock going down during the whole thing, but I won’t put every one of those bits in this for my ego, unless people want me to be more honest lol. Anyway, that was the only time I really had to look away from what was happening and replay boxing matches in my head to not cum. I’ve never had two women do that before or since and fuck me it’s so fucking hot. While K sucked my cock A kissed my legs and felt my balls, and when I asked them to both suck each side they did (though one closer to the tip, the other closer to the base as my cock isn’t quite thick enough to have two girls be straight across from each other – and K has a big nose too!).

I stripped off and when I stepped out of my jeans and boxers (which were around my ankles), we moved so that I was lying down and they were on either side of me. A was kissing my body and K was giving me head still. A asked if anyone had condoms. I had one but that was it. There was some joke about making it last, which in hindsight wasn’t helpful! I raced back to class to get it from my wallet, and when I came back K was on top of A, kissing and fingering her. A’s pussy was one of those fat ones bigger ladies have with fine blonde hair that was trimmed. I started masturbating to try and get my erection back while watching them. It took ages and I wish I’d spent more time getting myself going, because as soon as I had a half-hard cock I rushed getting the condom out and rolling it on. I said I had the condom on and A said she’d ‘take the bullet and go first’. K moved out of the way and I went to my knees between A’s legs. She held her legs apart and I put my cock inside her and started moving in and out.

It was not a great experience – K rubbed my body as I pumped away and A made little noises and looked into my eyes as she did so, but eventually she said (looking apologetic), ‘It’s…not very hard is it?’

I mean, the worst thing to hear is that. I gave up and took it out. It really had shrunk a lot and the condom was all crinkled up. I took it off and god the shame was terrible lol (I can laugh about it now but…oof). I reckon I’d have been ready to call it a day there, but K just kissed me, pulling me down on top of her. I think I tried to apologise but she told me to shut up and kiss her. We rolled and ended up with A going down on me while K kissed me. I tried to relax and focused on kissing K and looking at her naked body. Then, bam! Up it went and oh my god I was so relieved! I shot up onto my knees with my cock out in front of me. I asked did they mind not using a condom. A said she was on birth control and joked, ‘Doesn’t bother me as long as you’re not all diseased!’. I think K made an allusion to menopause? But she was only like 45 or something so I’m not sure if that would have actually been a true comment or a joke too. She definitely said, ‘Might as well carry on at this point’, though.

I decided to go for A again, probably to repair my ego. We kissed for a bit before this time and when I pushed it in, she gasped and said, ‘It’s definitely hard now!’ (might have just been being nice me though upon reflection).

I started fucking A on the cushions, her legs up on my arms and me going at her hard. K and I kissed during this and there is a bit of a memory blank for me here but she was kneeling over A’s face at one point to kiss me while A fingered her.

I remember that because while I don’t recall getting to that position, K stood up from there and put her pussy on my face, so I was fucking A while trying to lick K out. Finally, I got tired and K told me to lie back. I did and she got on top of me. She squatted on my cock, angling it into her with her hand, and I could see everything. K was really hairy. She was pale with dark thick, wiry pubic hair that went on her innermost thigh and all around her pussy. Now I’m older it wouldn’t bother me, but 25-year-old me was a bit shocked by an unshaven woman!

I watched her bounce on me, leaning back, before A climbed onto my face. I ate her out, trying to find her clit. If I just think of that moment now, I can cum, but sex always seems crazier when you remember it. At that point, I wasn’t really thinking ‘Oh shit, my boss is pounding herself up and down on my cock while my TA is grinding on my tongue’, I was just desperately trying to lick her properly and angle my body so K didn’t end up coming off my cock because she was treating it like it was longer than it really was!

They handled the transitions by saying it was ‘their turn’ now – again, so hot when I think of that now! But positions were kind of sorted out between us on instinct. There are snatches of conversation in my memory, like A saying that this still counts as overtime and me that hopefully it wouldn’t be awkward on Monday, but we definitely talked all the way through, joking and giving instructions.

I came the first time when I was doing A from behind and K was kissing her. I said I was getting close and A said I could do it in her if K didn’t want to. K said she didn’t really mind and so I pounded A until finally emptying myself inside her. I kind of fell back out of A onto some cushions and she cupped herself to stop all the cum from going everywhere. Then A took herself off to the bathroom to get cleaned up.

While she was gone, K and I started kissing and I went down on her, her lying back, legs apart. When A came back, she said something about carrying on and then I saw from my periphery her sit over K’s face. I stopped licking K to watch because up until then, they’d kissed, fondled and fingered each other but nothing quite so full on as K eating out A’s pussy (especially after I’d just came inside her). That got me hard again so I got up from lying down and went back inside K. We were like that for a while until A said we should swap – we kept the same position but they swapped places.

We moved around a bit (my dick went down again tbh), and the next position I remember clearly rather than quick snap-shots was lying down on my side, spooning and fucking K from behind while A lay in front of K, sometimes kissing her, sometimes leaning over her shoulder to kiss me. I asked if I could cum on their faces and they both gave a pretty firm no lol. A said she’d already had to clean up once so didn’t mind me cumming in her again, and so I rolled out of K, and A got on top of me and rode me until I came. I think K might have been lying there or possibly masturbating while we did that.

This time, when A went to get cleaned up, she took her clothes and got changed too. When she came back, she said she really had to go and there was this kind of awkward ‘Bye, see you Monday!’ thing between the three of us, and K and I said we’d tidy the library as she was late getting back.

A went and K and I slept with each other one more time, and then put the cushions and everything back in its correct position (at some point I fucked K on the little sofa, and it had been moved around). I tried to cum in K’s mouth, but there wasn’t really much cum left in me. K took her stuff to her office, and I went to sort out my classroom. I went to call in and say goodbye to her before leaving the school but she’d already gone.

Aftermath was fine, though I think it did erode the relationship with myself and K over time, as any time I voiced a disagreement with her, I think it she felt that she couldn’t jut dismiss me because I could end her marriage if she didn’t let me have my way (I never would have, but I think it explains some of her actions before she left to be a head somewhere else). A and I did have a few other drunken times, like after a staff party once where I walked her home, but then she went to a new class and we’ve grown apart since (still work in the same school though).

Hopefully I’ve made this whole thing somewhat clear because memory is not always very clear and coherent!

Source: reddit.com/r/gonewildstories/comments/dp8f23/my_only_ever_threesome_with_my_head_and_ta_in_my