This wasn’t meant to become a series of stories but it looks like it’s gone that way. There are actually plenty of tales to tell about this particular person, and I’ve had more than a few comments and messages about it, so let’s dive in.
A few things out of the way first… The title makes this out to be a cheating story but it isn’t. It just sounds better than the alternative title of “Wanking with Amy”. So if you’ve come here expecting some form of infidelity, now you can masturbate guilt free.
Some of you who are more familiar with the stories I’ve posted here may remember Amy, a former ‘Emo/Scene girl’ who had grown out of that phase of her life but retained all of the dirtier and sluttier aspects of her personality she’d developed during it. At one point in my life, Amy actually was “my girlfriend’s best friend”. The background to this and how the story here really started was [when Amy sneakily watched me fucking my then-girlfriend Jane](https://www.reddit.com/r/gonewildstories/comments/tcn2jo/the_time_my_girlfriends_best_friend_watched_me/).
And it escalated when [I bumped into Amy years later](https://www.reddit.com/r/gonewildstories/comments/uqg4iv/fucking_my_girlfriends_insanely_competitive_best/). That story was so long I made [a second part](https://www.reddit.com/r/gonewildstories/comments/uw8v2c/fucking_my_girlfriends_insanely_competitive_best/).
None of that is really required reading but it helps set the scene a little. So for those with little time on their hands and want to catch up quickly, the TLDR:
**I fucked my first real girlfriend from behind whilst her best friend watched me doing so from the sofa next to us. Never confirmed it but pretty sure she was playing with herself whilst taking in this visual and she definitely enjoyed the show we put on. After splitting up with Jane, years later I ran into Amy on a night out and it turned out there was something between us. Things escalated from making out in the bar to Amy gagging on my cock in her room. She was a very competitive person and this translated to her outdoing Jane in the bedroom in every way she could and “fucking me properly”.**
When I saw her last, I promised her that I would contact her should I ever be in her area again. In truth, I got in touch before that because I just couldn’t help myself. It wasn’t long after our first encounter I sent her a message telling her how much fun I’d had and that we should definitely meet up again. To help fuel her ego, I also mentioned mentioned just how good *she* was (“You were right, you *were* better…”)
After a bit of back and forth, it was clear we were both up for getting together again. Not necessarily in a dating or romantic way but in a “I think we need to fuck each other’s brains out again” way. Our schedules each turned out to be pretty hectic so it was a little while before we could make it happen unfortunately. The plus side of this however was that we were given plenty of time to discuss, in detail, plenty of our wants and desires, and new things to try. I’ll be honest, my list was bigger than hers – Amy was (and most likely still is) much more experienced than I.
One of those things was the title of this story, mutual masturbation. I’d never done it before but the idea turned me on and I thought it looked like a lot of fun. Turned out I was right.
When the stars finally aligned (no family visits, no friends staying, no conflicting work schedules and the wonderful words, “my flatmate is gone for the weekend”), it was time to meet up. I hopped on a train to Manchester one Friday evening and we grabbed a drink and a bite. We both knew what we were wanting though and we rushed through this part of the evening. Before I knew it, we were back at her flat and in her bedroom, making out like giddy teenagers.
Now is probably a good time to describe Amy and I once again. As I said, Amy was once what you would call “alternative”, very much an emo/scene kinda girl – think ‘Suicide Girls’ but not on the extreme side. She had multiple tattoos all over and plenty of piercings too though had dialled the latter down by this point. She was also a very small and dainty girl in just about every aspect. She barely weighed much and was skinny (but not *too* skinny), barely over 5ft tall and had B-cup breasts. I previously compared her to [this Suicide Girl](https://ilarge.lisimg.com/image/5881335/800full-mendacia-suicide.jpg) though her hair was now her natural colour rather than another shade of neon.
As for me… Not quite 6′, reasonable shape as I was frequenting the gym often, a short back and sides haircut and a pretty standard dress sense. Honestly I’d say I was your average white guy with a couple of standout features, those probably being my jawline and, to be frank, my cock.
Amy removed my shirt for me and she took her dress off quickly after. I unbuckled my belt and got rid of my jeans as she stood there in her underwear, watching. It was a black lacey combo with a floral design, somewhat see-through giving me a view of her pierced nipples I had so much fun sucking on last time. She looked delicious. I walked towards her, effectively being pulled in by how amazing she looked but she stopped me.
“Hey! What are you doing? You know what this is. Now sit down.”
She gestured towards a chair next to her bed that had a cover thrown over it. Not like a wooden chair or anything like that, I think it’s called a “snuggle chair”. Felt pretty cosy as I sat down, now just in my underwear.
Now I’d never been into the whole Jerk Off Instruction videos (or JOI as they tend to be known) but after this I definitely had more of an appreciation for them at least. I didn’t realise this was quite how we were going to do things until it had already started happening but I was most definitely onboard.
Amy opened the top draw of her beside table and grabbed something out of it. She turned around and took a few steps towards me and handed me a small unopened bottle of lube.
“That’s for you.. Well, for *this*.” she said, squeezing my bulge through my boxers. “Open it.”
I took the plastic wrapped off and set it down beside me.
“So, are you gonna start stroking that for me? Don’t take him out just yet.” she continued.
I started rubbing my cock over my boxers as she climbed onto her bed and sat back on some cushions, spreading her legs and giving me an incredible view.
“You getting harder for me, Benjamin?”
Her eyes were fixed on me so I simply nodded in response.
“Good, keep rubbing that dick.”
As I relaxed further back into my chair, I started gripping it through my boxers a little more, stroking up and down. Amy started joining in and was rubbing herself over her panties. She let out the softest moan.
“I’m already wet for you, Benjamin. I can feel it through my knickers.”
There is something altogether different about hearing a woman talk dirty to you in real life. Online or via text is one thing but in-person is another level. Within just a minute or so I was feel incredibly aroused. I plucked up the courage to dirty-chat back.
“Good. Just like I said you would be.” (I had promised a pair or her underwear would be soaked one way or another)
“Mmm, yeah!” she said, “Are you gonna take that out for me now?”
I did as she asked and removed my boxers in a swift motion, and now feeling more relaxed than ever, I sat back with my cock in hand.
“There’s that big cock I remember. God I can’t wait to suck it… *fuck* it..”
I was feeling so turned on, I let out a moan of my own and started jerking my cock. Up and down slowly as Amy’s eyes followed my movements.
“Let go for a moment.” she told me.
I was hooked on her every word now and released my grip as she asked. I was pointing directly at the ceiling I was so stiff.
“Move it for me. Five times. I’ll count for you.”
*Fuck*. Ok, as she wants. I flexed my cock for her.
“One…”
“Two… Three… Four…”
I saw her licking her lips in between counting.
“Five.”
It was as if I was somehow harder. I told her how it wasn’t fair that I was naked and she wasn’t. She responded by removing her bra and playing with her breasts, rubbing them and pinching her nipples. Then she stood up and walked towards me, spun around 180, bent over and took her panties off, dropping them by my feet. I started leaking precum in response.
“Better?” she asked me, following it with, “Looks like you could use a hand.”
She bent over towards me and grabbed my cock and then, leaning over a little further, gave the head one single passionate suck, lapping up the fresh pre-cum. After the teasing this felt absolutely heavenly but it was short-lived as it was just part of a bigger overall tease. She resumed her position on the bed and told me to “just watch now.”
She spread her legs wide for me and started playing with her pussy. At first she was slow, methodical, massaging her clit and her lips, occasionally pulling her hand away to give me a view. She was dripping wet. With her free hand, she was rubbing her tits, just as delicately. Her moans were growing in frequency and intensity. At first it was just heavy breathing but then soft moans, then harder moans, then *louder* moans. I was just sat back, enjoying the show, stroking my cock slowly.
After a few minutes, she looked over at me and told me to “lube that thing up”. Without hesitation I squirted some on my dick and rubbed it all over, making sure it was coated. She didn’t break her own rhythm and continued to rub herself but her eyes were fixed on me whenever she could keep them open. I could tell her pleasure was building. Then she asked, “You gonna stroke that huge dick for me now Ben?”
I most definitely was. I started jerking my dick up and down with a bit more pace.
“Grip it hard for me!”
I firmed my grip a little more – I would literally do anything she said at this point.
“Use both hands.”
So there I was, both hands wrapped around my cock, stroking it whilst enjoying Amy get more and more pent up on the bed in front of me.
“I want you to bring yourself close for me, Benjamin. Mmmmmphhh” her moans were threatening to stop her ability to talk now, “Ughh… but don’t cum just yet.”
I did as she said for a minute or so, definitely bringing myself close. When she asked me if I was ready to cum, I told her yes, just to be met with a “don’t!” and an order let go and then slowly resume. We repeated this cycle a few times, bringing both of us ever so closer to a big orgasm.
Amy reached for her side table again and took out one of her toys, the trusty rampant rabbit and slide it inside herself. It looked like it glided in with ease and I heard the buzz of the toy turn up as she went to town on herself. With this, her moans just went that bit harder. They were near enough constant now. She started writhing around on the bed.
“Start pumping that cock for me…. I want you to… I want.. you to cum for me soon. Mmmphhh..”
She was looking over my way but barely, she could hardly open her eyes. I started stroking myself faster but I was holding back because I knew I was ready to burst any moment. I was moaning with her now.
“Fuck… I’m gonna cum Amy.”
“Don’t stop it, cum for me.” She could probably sense I was keeping a part back
“Oh fuck!” I could not help but get vocal.
“Oh god, I’m close… Are you… oh fuckkkk… Are you gonna make that cock explode?”
“Mmmmmm FUCK.” There was no way to hold back anymore. I was trying to enjoy the amazing view of her fucking herself with her toy and squirming all over the bed but my eyes were rolling in the back of my head at this point.
She clearly could tell from my moan that I was about to let loose, and she let out a high pitched scream, an “OH FUCK YES!” and started soaking the bed. It wasn’t a fountain or an insane gush but like a heavy steady flow of liquid. The sight of her squirting was the final nail in the coffin and I started cumming with her. I must have shot so many ropes over my chest and stomach, and several that went beyond, dowsing the throw on her snuggle chair.
We both sat there across from each other breathing heavily, trying to catch out breath. We had barely touched one another the whole time, yet were both extremely satisfied and covered in sweat and cum. After a necessary few minutes of readjusting, she asked me, “Was that as much fun as you thought it would be?”
“Yeah it definitely was.”
“Ok, good! Now get over here and fuck me!”
Source: reddit.com/r/gonewildstories/comments/vzth6q/mutual_masturbation_with_my_girlfriends