This happened when I was 17, and unlocked me sexually as a person – I discovered how much betrayal turned me on and that I was partially bisexual/very submissive.
I was on holiday/vacation – just a week in a Spain, my grandparents had bought a Villa as a project to improve and sell on (something they did a lot) and we’d usually get a free holiday out of it. I’d gone with my best friend “D” and both our mums, we were close as families and had been friends for over 12 years at this point.
A quick overview of everyone involved –
Me and mum look pretty similar, both short and blonde, I’m naturally pretty skinny but toned and athletic, mum on the other hand is just plain skinny, no curves and a little underweight. She was 41 (I think?) at the time. We’re both cute, not ugly by any stretch.
D was tall, I think 6’3 and whilst he wasn’t toned like me he was built like a man at 18 – a slab of a chest forming already and quite a hairy guy. Him and his mum are both dark haired. They’re both pretty average looking, but Ds mum is quite overweight.
Right.
The first day we walked to the nearest shop for some food, checked out the villa and sorted out sleeping arrangements. We had three bedrooms (we knew this ahead of time, wasn’t a shock) the mums got a room each and me and D would take turns in room #3 and the couch. The shop was a good 20/25 minutes walk away so we tried to buy enough to last half the week and avoid too many trips. The day remained pretty frantic as we cleaned the pool of debris/leaves(?) and unpacked – the pool guy also left awful instructions for how to set up the crappy hot tub which came with the villa but me and D had it ready before night.
Our holiday was honestly pretty regular, it was isolated and boring but we knew that before hand, and it was relaxing to spend time in the pool and tub – we’d play cards and watch what films the housekeeper/pool guy had left for us in the evening and got comfortable getting a little drunk together.
On day three me and D had both experienced the awful sofa and decided we should just sleep at opposite ends of the bed (we weren’t afraid of contact it just meant more space). Me and D were racing lengths in the pool when my mum came to sunbathe – and oddly – stripped down to do it, I know it’s pretty normal to do that but she had never on holidays with me so I was taken back a bit by her confidence to do it with D and his mum around. Looking back I was right to find it odd.
Day four – I woke up pretty early and got up carefully to let D sleep in, I found my mum and Ds mum were already up and
chatting having coffee. Ds mum asked if I’d walk to the shop with her so I said sure – I did ask if we should all go so we’d have enough for the rest of our stay but she said we should just go now so we had food ready for the rest of the day. I got a big bottle of water for the walk and headed out with her, it gets way too hot around midday and I wasn’t gonna wait for D just to walk in the heat so it seemed smart. Me and Ds mum chatted on our walk and she flirted with me a little complimenting my body, I was flattered but honestly not too attracted to her – about 10 minutes into the walk one of my flip flops broke (I’d bought a cheap pair at the airport and was now seriously regretting it) I told Ds mum she should keep walking and I’d go back for my running shoes and catch her up but she insisted I just walk the rest which was blatantly a stupid idea – she got really upset trying to convince me but after some arguing I promised her I’d catch her up and would be back soon, and hobbled back to the villa as fast as I could.
I got back pretty quick and once inside pulled the door shut behind me. I’ll remember forever how the sound of the door shutting and the outside noises being cut off was instantly replaced by noises straight out of a porno, skin slapping on skin and undoubtably the sound of my mum letting out a cry every hit. My stomach dropped realising what was happening, I stood and listened and it was clear the noise was coming down the hallway – mums room was at the very end and parallel with the hall entrance. I grabbed my trainers by the back door and on my way back the slapping suddenly stopped. I freaked out and thought they’d heard me and ducked behind the sofa, peering out at the hallway. I sat there for a good 30 seconds and nobody came so I stood to leave. I’d be lying if I didn’t say I was turned on, and curiosity got the better of me – I wanted to know if it was really my mum and D, I wanted to know why the slapping had stopped – I edged around the corner of the hall and saw instantly. Hearing them fuck had been hot, her ass slapping against him and her cries – its fucked up but it was hot, but seeing them was too real, it was more than some weird fantasy when I saw them, it wasn’t just sex noises anymore it was my best friend fucking my mum – at the end of the hallway was my answer to the slapping stopping, it was a pretty long way but I could easily make out my mums ass facing me, a pair of hairy legs either side, definitely Ds, and my mums head bobbing up and down between them. I took it in for a few seconds and left feeling angry and confused.
I ran all the way to Ds mum as fast as I could. I was clearly upset and she asked what was wrong but I kept quiet and just got the shopping and left. About half way back I asked for a break to sit on a wall, I confessed about what I saw (sparing most details) and said I was sorry but I can’t process it alone. Ds mum apologised too and said she already knew – this caught me off guard. She explained how her and my mum decided to get me out of the house this morning so they could have fun, and that’s why she’d insisted I walk without a flip flop (she apologised for that too and we had a good laugh and tensions left a little) I was less emotional but still confused and asked a few more questions, I wanted to know why she was cool with what they were doing and she admitted it felt wrong to her and unnerved her but what was she supposed to say? She explained how D and my mum had been flirting and shared a few kisses and that my mum was the happiest she’d seen in a long time – she felt bad for intruding on that. She also said she’d feel bad if she stopped her teenage son from getting laid – I agreed and told her I was upset at first but they’re adults and I guess it’s okay. She hugged me and admitted she thought they were being selfish but her situation was tough. We chatted about the scenery and Spain for the rest of the walk, about 5 minutes out I stopped us again and confessed I felt jealous – I asked if she felt jealous too and if it was wrong, she said she did and she didn’t know if it was wrong, she got teary eyed and I hugged her hard and held her for a few minutes – during the hug she started to push her hips into me and I admit I did the same and it became sexual quick – she was rubbing me through my shorts and I lifted her chin to kiss her. We made out (messily) for about 30 seconds whilst she rubbed at me and then *snap* like magic we both pulled back, I wasn’t hard and the kiss had felt wrong. We agreed maybe there was just no chemistry and just because they were fooling around didn’t mean we had to, we hugged one last time and took the bags back to the villa.
That night things carried on as normal, they had no idea I’d found out and Ds mum said nothing – I picked up on some flirting but they did a really good job of hiding any feelings. I’d calmed down a lot and knowing they were doing it behind my back was turning me on again – though confused I was getting my first bi impulses and viewed D as an alpha male I guess. I felt pretty tired after my run and headed to bed early (12am was pretty early for this holiday) I slept for a few hours but woke up thirsty and went to grab a drink, D wasn’t in bed so I figured everyone was still up. Whilst I was pouring a drink I saw Ds mum smoking by the door and went to stand with her, as I approached she shouted my mums name out the door, turned to me and apologised – she’d clearly just warned her I was coming.
My mum was walking towards us in a towel, she smiled and scurried past us and said she was going to dry off and play cards if anyone wanted. I said sure and then walked down to the hot tub where she’d came from. Once I rounded the corner I found D in the hot tub relaxing, I wondered if they’d been kissing or anything else and got turned on again. I asked D if he was gonna come play cards and he said sure, I waited for him to come but he didn’t move and I asked how long he’d be – he told me I should go inside and he’d be in soon. Now I was super suspicious and excited to figure out why – and thats when I saw his shorts on the floor next to the tub. He had been naked and didn’t want to stand. I thought about confronting him right then but I couldn’t deny how much their sneaking around turned me on, so I let it slide. I asked D if he minded if I joined him and this caught him out, before the awkward pause took too long I stripped to my underwear and hopped in.
What I saw was the biggest lesson in my sexuality I’ll ever have. I get in with a splash and make a point to not look under the water, I just look around and at Ds face and feign total ignorance. When I look him in the face it’s so obvious he’s nude in my peripheral vision but I didn’t want to let him know. I loved that I was in on their secret and I loved the feeling of betrayal that came with it. He slowly relaxes as he realises I haven’t noticed he’s nude and we have a genuine laugh and chat, we’re good mates after all. I’m aware I’m basically holding him hostage as he wouldn’t be able to stand until I left so I know I should get up soon – I wanted a peek at his dick before I went though. I tried giving it a discreet glance but my god, I could not look away. I thought maybe the bubbles were distorting it or he had the biggest, thickest cock I’d seen. He saw me looking and panicked, started spurting out an explanation – probably for being naked with my mum, but I cut him off. I believe I said “holy shit” and as his confused protest/explanation died down I asked boldly if I could see it. I’ll be honest I would’ve cut him off just to keep his lies going – I didn’t want him to explain or suspect I knew anything – but I genuinely was interested. I wanted to see it.
He asked if I was sure and I nodded and said it looked huge. He stood slowly and revealed the cock that would rock my entire world – this thick, heavy cock confused me, turned me on…it’s the cock that would open my bisexuality, drive my cuckold fantasies later in life and all around change who I am. It didn’t stop there, behind this fat cock was the heaviest, fullest set of balls Id laid eyes on. I’d seen Ds package plenty of times and always assumed it was all balls, this wasn’t a shock – he had a deep voice and was hairier than most men at 18, but the dick was a surprise. We stood in silence for nearly a minute, every second that passed his cock grew – I wasn’t confused at this point, I knew I was at least orally bi – I wanted to suck it. But D looked like he was confused, something about the situation was exciting him too. He asked what did I think and I told him honestly – it’s amazing. He grinned and played with it a little. We both came to our senses when my mum called us and got out the tub, I watched him put his shorts on and we locked eyes for a few seconds before heading up to play cards.
When we eventually went to bed I couldn’t breathe I was so nervous/excited. I wanted to confess my fetish to D, how I’d heard him fucking my mum and enjoyed it. We got in bed and kept the light on for a little while whilst we chatted. We avoided the hot tub subject until we turned the lights out, we were both a little embarrassed.
He asked if I was gay and I told him I thought I was bi, I -awkwardly- explained how I didn’t feel romantically attracted to any man, I hadn’t felt physically attracted to a man before today. He said he thought he understood and we lay in silence for a few minutes. He suddenly said if I wanted I could touch it. I didn’t say anything back, but moved my foot under the covers between his legs. I felt gently with my foot – I couldn’t feel much definition through his underwear but it felt huge, I immediately got hard and ashamedly thought back to the noise of my mum bouncing on this thing. I needed it – I told him to take his underwear off and he did straight away without a word. I moved to his end of the bed and sat next to him, I couldn’t see much in the dark but his thick pale dick really stood out, I grabbed it in both hands and started to wank it, making it hard. I cupped his huge balls with my other hand just to feel the weight briefly but quickly went back to wanking this huge cock. Within minutes he shot a decent sized load over his chest and I got back into bed whilst he cleaned. When he was back I asked if he was bi since he let me, and he said no because he imagined I was a girl, he just liked handjobs. We both knew that probably wasn’t true but I left it. We lay in silence again for a while before I blurted that I wanted to suck it tomorrow. He said I should and we went to sleep.
The next morning we stayed in bed a little longer and chatted. We tried finding a football channel on tv to keep up with results back home but had no luck, it did give me an excuse to sit at his end of the bed whilst we looked though. We spoke about the usual things – mainly sport but I had my hand under the cover feeling him through his underwear again. He finally got impatient and pulled them down but before I continued I asked if he liked me doing this stuff to him – he again said he was just pretending I was a girl, I gave him a look that said we both knew better but he still argued. He said because he has no girls to fuck on holiday he was frustrated and didn’t mind using me – that was bullshit and I knew it *insert flashback of my own mother blowing him*. I liked that he lied again. I took my own underwear off and got under the cover with him, and started sliding my hand up and down his cock getting him hard, and once it was I pulled it out from beneath the covers. I loved how huge it felt in my hands – my finger and thumb didn’t touch when grabbing it.
I started to suck it and quickly realised I had a hard job on my hands, I could only really focus on the head with my mouth and jerked his dick in time with my mouth. Soon enough he was moaning and holding my head/running his hands through my hair. I stopped and told him to be quiet, then asked again – are you sure you’re straight – as I readjusted our position. He assured me again he was as I lay on my side and he followed, getting into a spooning position. I raised one leg up and pulled his cock between my legs, then put my leg back and squeezed slightly. It felt huge between my thighs and I thought back to the noises my mum made getting fucked by this thing. I pushed my hips back and started massaging and stroking the tip of his cock. I repeated what D had said earlier – how he was just using me because he hadn’t been laid for a week and he happily agreed, starting to pump his cock between my thighs. My dick got hard as his (easily twice the volume) pushed through my thighs and moved my balls on every pump. I quietly said “but you fucked my mum” and he froze. I felt his cock get harder and his breathing stopped, waiting to see if I was upset.
As I got out of our spooning position I said it was okay, I think it’s hot – he didn’t look like he quite believed me so I sat between his legs and got ready to suck him. He asked if I was really fine with it and I nodded. I told him I would suck him off if he admitted he wanted it and he hastily said he did, I opened my lips and kissed the tip before saying one last thing, I asked him to not tell my mum that I knew, just carry on. He nodded and I carried on blowing him. I used both hands in time with my mouth again and milked him quickly, I felt his huge balls tighten as he came and tried to swallow as much as I could. He came a lot more this time and after three swallows I felt like it was burning my throat, I let the rest slip back out onto him.
This was a really big write up and not everyone’s cup of tea hahaha but I wanted to be accurate and get the whole situation explained – looking back this really targeted/kickstarted some of my biggest kinks and it’s no wonder I went from straight to slut in one week. If it isn’t obvious I learned I was orally bi – and specifically for big dicks. I tapped into cuckolding a little bit with the fucked up mum situation – weird I know but the whole holiday turned him from my best friend to an alpha male and it’s a huge turn on for me. Back home me and D fooled around a lot more and he remained active with my mum for about a year.
Source: reddit.com/r/gonewildstories/comments/6jx4p5/mm_mf_sharing_my_best_friend_with_my_mum_first
great honest story…more please?
Tbh I thought you were going to fuck your mum.