Meeting a Friend-With-Benefits via Internet Dating:

[TigerJim]

True story.....
(you won’t believe me - believe me, it’s true – fortune smiles upon me!):

A few years ago, I put up a perfectly normal internet dating profile with all the usual: about me, pictures, likes and dislikes etc….
But, my profile clearly stated in there, that ‘I like to striptease for my date, masturbate, and ejaculate for her’.

Well, let’s just see how that goes! – (It could be a ‘disaster’! – (Spoiler: It wasn’t!)).

I’ve always been a firm believer that; ‘if you don’t ask, you don’t get’.

Well, I very quickly got a date! – with a very attractive lady in her 50s.
(She was single, I was single – Absolutely no reason to do this - So let’s DO this!).

We met at a bar and had drinks etc. She asked me, ‘So what’s with all this stripping, masturbating, and ejaculating nonsense on your profile?’
– (it was good that she was clearly already aware of that!).
I said ‘Well, it’s a simple as that; I very much enjoy entertaining a lady by strip-teasing and being watched whilst masturbating and ejaculating'.
She laughed and told me that I was ‘completely nuts! ’. Of course, I was!

Perhaps she didn’t believe me, perhaps she was intrigued, perhaps she wanted to test me, perhaps she was just a very naughty lady who wanted to see a very naughty private sex show!....... But either way, she did invite me for a second date with her – This time, at her house!
(and I’m sure that you can begin to see exactly where this is all going!).

She did dinner for us both – Very nice! After dinner, she mentioned my profile description again, and asked ‘So, are you going to entertain me in your ‘completely nuts' way?’ – (which was nice because it confirmed that she still aware of my ‘entertainment’ speciality, and was perhaps suggesting that she was willing to engage in such a process! – YES!).

I said ‘Well, let me just show you!’.

– (Care and Caution was required here! – this could go horribly wrong!)
– (I would, of course, have stopped at any point and respected her wishes if she would have raised even the slightest kind of any sort of objection – but she never did! She seemed perfectly willing to be ‘entertained’ in this way!
- (YES! – She is ‘up for it!’)………….

She poured herself a large glass of wine, sat down, got comfortable, and let just me press on with it, and ‘entertain’ her!
- and so, I just pressed on with it!)……

I put on some stripping music, strip-teased, danced naked, oiled myself up, masturbated, and ejaculated for her as she watched!.……

(….. That description made it sound as if it was all over in a few seconds. It wasn’t. It was a carefully choreographed 3-track 10-minute show: Dancing, Teasing, Stripping, Dancing, Teasing, Naked Dancing, Erecting, Teasing, Dancing, Oiling, Masturbating, Dancing, Teasing, Masturbating, Ejaculating!). – (Yes, now that sounds more like a decent show!).

She absolutely loved it! and was very complimentary,
she said ‘That’s the best thing that I’ve ever seen!’.

I thoroughly enjoyed it too!

(You see, it’s true; if you ask, you can get! – I asked, and I got!).

So………. It turns out…….. She WAS just a very naughty lady who wanted to see a very naughty private sex show!

Furthermore, she wanted another date!

I regularly saw her and ‘performed’ for her about every two months or so.
She did the dinner , and I did the sex show .
It was as simple as that!

On the second date show, she took hold of my cock just before I came, saying ‘let me do it’, and she ‘finished me off’ – that was nice!

As time went on, she took over most, if not all, of the ‘wanking duties’; I would striptease and dance for her, and then she would take over; oil me up, get me fully hard, and masturbate me all the way to ejaculation – that was very nice!

(Plus, she had this ‘thing’ whereby she liked me to actually come on her, on her clothes – (Certainly quirky and unusual! – but delicious!) – She had me stand in front of her and she would make me splash my come all over her - I don’t know why, but that was somehow always extra naughty and nice!).

She was a very nice regular sensible 50 something lady who went about her life: work, shopping, gardening, etc, when we first met , and then when I first showed her some of my ‘evil pervertedness’ , it clearly stirred her own hidden inner ‘evil pervertedness’ , and she went way beyond anything that I could muster, and she became quite the ‘Queen Evil Pervert ’…….. But, she was always still that very nice regular sensible 50 something lady! – (at least just on the outside!) – It shows that there is a devil in each of us! - What is not to like!

She certainly was a very nice and very naughty lady indeed.

So, It wasn’t a normal boy-girl love type of relationship. We were companions, we enjoyed each other’s company, and we brought, and met, our own needs. We were truly; ‘friends with benefits’.

So, there’s my internet dating tale, with a friends-with-benefits tale included.

Anybody else got an internet dating tale or a friends-with-benefits tale they wish to share please?

We would love to hear!

[Bitsnbobs]

Wonderful story.

I shared lots of nude photos with an online friend, on another forum. Maybe if I had pushed, it could have progressed to video dating, which would certainly include me stripping for her, but possibly nothing more. Although she asked for close ups of my "manhood", she never asked to see me aroused. She loved the shots I sent from nudist holidays, with varied locations - she got off on me being naked outdoors, and with other people in the background. She sent some pictures of her wearing provocative clothes, but only one nude. It was full frontal in a mirror, so somehow I knew it had been taken specially for me.

Were your encounters always one sided?

I was not looking for a deep and meaningful relationship, but your experience sound exciting.

Edited too add, I have shared nude photos with several women on forum pms, but the one above was the only long term arrangement.

One of my partners loved watching me shower. At first she would pretend to come in to pick something up, but later she started watching me undress first, then I would lead her to the bathroom. I always made a show for her. Washing, towelling down, wiping down the shower and bath, all completely naked of course.

[gunairre]

Woah, fantastic story and opportunity you got there!

I want to share a similar story:
I had a few encounters like this, my first one was on reddit / snapchat when it was still relatively new, when I was i think 15 or 16... (i know, i was an idiot, i shouldnt have done what i did, they couldve been a creep, but anyways, im glad i did because it was a good few weeks).

Basically this guy messaged me a few times, we found out that we were in the same country. We exchanged photos, all was well, until, we got on the topic of relationships. At that point, i didnt have any girlfriends, so i said i didnt have one. he said he had one but they broke up. we then switched off of reddit, i dont know why. In the new app we started sharing photos of ourselves, at one point, she showed a photo of himself shirtless. so i returned that with my own shirtless photo. then after some more, she then showed one in just his underwear... So i also returned one of my own. then a while later, he sent a photo where hes completely naked, then i returned it with my own (i was very shy so i dont know how i even managed to work up the courage to do that, but then again, i didnt know this guy so maybe its like that thought experiment of would you rather get seen naked by a stranger or someone you already know). He then started sharing photos of naked girls, his past girlfriends, and some sextapes of himself and a few of them (which i sadly didnt save because my parents would have sold me to some tribe deep in the indian forests if they found out).

Basically it escalated from there, etc etc, then one day in my head i was like, this feels very wrong, all of his girlfriends didnt consent to this, and im not gay so what am i doing? I then didnt respond to him and eventually blocked him. I somewhat regretted it at that time but not that much.

Looking back at it, he was probably gay or partly gay and wanted to do something that didnt tarnish his reputation at the time (cuz of the stigma of being gay at that time, it was relatively recent but still, the stigma was very bad)

---

My second time was about a year after that, on instagram, it was my birthday and i was sharing some birthday wishes people have sent me onto my page, and then a random girl who i didnt know wished me a happy birthday. I didnt think much of it, because i got some other strangers wishing me a happy birthday. Then she started messaging me some more and we talked for a while, i got to know that she was 17 and then she told me that she had a gift for my birthday and sent me some nudes, i still somehow have them ingrained in my head until now, she sent me two, one was a full frontal, (She was cute, had a nice body, boobs were on the smaller side but it suited her well, and she was very pretty, so i immediately got a crush on her) and another one was a butt/pussy pic. We talked more and more, it felt like we were gonna make a connection, and after a few months we planned to meet up because we lived in the same state, and then she randomly ghosted... very sad about that, wish i couldve met up with her or do something more at the time.