Written by Paul

16 Feb 2015

I'd been idle for a while last year with little happening on the dating front and had slipped into a comfortable rut.

Being a man just the wrong side of 50 I'd started spending more time at work or the pub and was fairly happy with my dull routine. One day at work I was e.mailed by an ex colleague asking all the usual bland stuff. She's not long turned 40 and recently separated from her husband of 20 years. She eventually suggested we go for a drink as "friends" and I agreed readily.

I was obviously hoping for more but after the 3rd meeting I'd cooled on the idea. The nights were basically her saying how her man had let her down and us getting drunk and going our separate ways at the end of the night. Just at the point of pulling the plug she text "do you want a proper date next time".

Thinking the situation had improved I agreed to meet and raised my hopes. The date did end up back at her house but the usual frosty atmosphere was still there and you didn't need told it was a hands off stand off. After a few more failures I thought the best way forward was meeting with a couple I knew in their late 40's called Tim and Jesse. It did improved the atmosphere but she was still lamenting the past at every turn.

Tim is approaching 50 and a bit bigger than average build just like myself but still attracts the ladies.

Jesse is superb for a woman of any age but exceptional for a lady about to exit her 40's. She is very pretty and her shoulder length dark brown compliments her hazel eyes with that appealing come to bed look about them. Her body is well defined with a cleavage of about dd which she usually keeps well hidden. Her bum is eye catching and you find it hard not to look at it.

The dates were now well into in double figures and leading up to Christmas there was little sign of improvement. One night after being out with Tim and Jesse she asked me if I wanted an early present. "Bingo" I thought. Once back in her house she started back tracking and my bubble burst.

Just before I was ready to leave she seemed to panic and asked me to wait a minute. She charged upstairs and came back down with a dressing gown on. Again she dropped a bombshell by saying "we can't go all the way but you can wank yourself looking at me". She lay on the couch and opened the gown but still half covered her pussy. The rest is still a bit of an awkward haze but I did stand over her and wank on her tits. Her body was as awesome as I'd imagined but I felt weird and awkward throughout.

Next day I got a text saying "this is not working out we need to finish". I happily agreed to that.

Tim text me the same day asking did I fancy a pint to watch the football down the pub. We met that night and I filled him in about the whole mad episode. He commented that he and Jesse always thought I looked under pressure and they had noticed me always try to re-route the conversation away from her ex man. He said he admired my patience and a selfy wank was not much to show for double figure dating. We got drunk that night and I did feel a weight off of my shoulders telling him.

Tim phoned me the next day and said he'd told Jesse but she wouldn't breathe a word but was feeling sorry for me. I said not to bother as I felt happy again and lucky to escape the madness. A week or so passed then Tim and me met again for a pint between Christmas and new year as we'd all had previous arrangements. Once the drink kicked in he told me Jesse had admired my self restraint and fortitude as the woman was playing with fire. She also said a man should cum at least every second day or they become really frustrated and not very pleasant to be near.

I told Tim I'd actually have been happy with an ocasional bit of self relief at that point as my ex wife who is still fiends with Jesse still gives me a flash now and again as I wank off to her. I've grown to appreciate our secret meetings despite the restrictions as she loves the thrill of her flashing and of me wanking but is limited as to how far she'll go as she's since remarried. She's always prepared for my arrival and wears a little red kimono for easy access for our secret sessions.

I told him I'd loved to have seen that stunning body of my recent date a few more times as my memory of that night was a blur and there was never any chance sexy photo's would have been exchanged to keep you ticking over between dates.

Just into the new year Tim asked me over to theirs for a drink as Jesse was going out to her pals house. When I arrived he seemed ill at ease and I thought they'd maybe had words before she left. Tim got drunk very quickly before asking if I wanted to see the holiday photo's. This is usually a guys worst nightmare but before I could say no he followed it up with the warning that there might be a few of Jesse topless amongst them. I said he'd better not then as she would blow a fuse. He quickly followed on with "we've spoke about it and she wants you to see them". Gulp! "Er, aye okay then" was all I could mutter.

Quick as a flash the i.pad was connected to the big tv and Tim sat next to me on the couch. He gave me a nod and started it on a slideshow format. Nothing was said and it did feel strained as the photo's flashed past about every 5 seconds. It was all tame to start with and the usual airport and hotel pics leading up to the nights out etc before the first ones by the pool appeared.

Initially Jesse had a costume on, then a bikini, then suddenly bingo, "topless" holding a drink up!

He looked at my face and I gave a nervous cough before saying "you lucky man".

"You like mate, there's more" he said.

One by one the topless by the pool pics flicked passed as I praised them all in turn. There had probably been about a dozen topless before the slideshow went back to the start and he paused it.

"They are beautiful mate" I said.

"More?" Tim said.

"Only if you are sure Jesse is okay with it" I said.

Tim opened the next folder and as the pics flicked passed they began with the standard nights out ones. He paused the slideshow and said to me "I'll slow them down now the good ones are coming". He restarted the slideshow and there was Jesse back in the hotel room laughing getting undressed after their night out. Bit by bit the top, then the skirt, then at last the bra were removed. She faced the camera in just her panties with a confident pose before holding and squeezing her tits in the next.

They were clearly more than just your run of the mill holiday pics now. The next had me on the edge of the couch as Jesse had her back to the camera and was taking her panties off. The next was her naked with her back to the camera walking into the bathroom with her awesome shapely bum taking centre stage in a full length photo. Next was a series of Jesse in the shower with her back to the camera and the water and suds flowing down her body.

Tim paused the next photo and it was one of Jesse from waist up on the bed propped up by pillows. He pointed out how Jesse's nipples were erect in this pic and and told me that's because he was fingering her at the time, and judging by her expression you couldn't argue the point. Tim left that one paused as he poured us another drink and looked at me as though gauging my reaction.

He looked at me and said "Jesse wants to show you a couple of full frontals if you want to see them".

"Are you two sure, obviously I do" was the predictable reply.

The first few were as gorgeous as you can imagine with Jesse walking about the room and in the shower with her shaved slit in full view. I praised every picture but felt a bit anxious too as Tim still seemed a bit nervous but excited. I knew things were going to get even better when he paused it again and looked at me. I looked back and just nodded as he started the next series of pictures.

The first was obviously a follow on from the stiff nipples picture as it was of Jesse propped up on the bed with her legs wide open and her pussy slightly open and soaking wet. She had her head slightly back and was squeezing her tits again. There was about another 10 full frontal and althogh not as graphic were pure pre cum quality. When the slideshow finished Tim suggested we have another drink as the pace had slowed due to the wonderful entertainment.

After an awkward silence Tim took a deep breath and told me my stories of wanking to my ex wife and ex date had put Jesse in pure lust overdrive and they had played out some bedroom scenarios recounting them. He told me Jesse always had fantasies of being wanked to after catching her first boyfriend wanking on her drunk pals face when they thought Jesse was asleep.

Tim then said "do I need to spell it out to you mate"

"Probably" was my coy response.

Tim sighed then said "Jesse wants us both to wank on her tits, but you need to take a day to chill out and make your decision so she 's not through drink"

"My answer tomorrow will still be yes but only if you two are sure you can cope with it" I reassured.

Things kind of went on to usual football stuff after that but we did the man hug thing when I left and felt fairly confident it would happen.

The next day all three of us text each other without a mentiion of the events of last night or the conversation we'd had though I think we were all hoping the other would say something.

About 7 o'clock that evening Tim text me and said "Jesse's bought a lovely little kimono".

I took the hint and text back "she'd better not show me it then or it will probably end up in the washing to get the stains out". Just as I popped a viagra I sent the text. My nerves had been frayed all day and now more so waiting for a response.

As hoped Tim text back saying it hopefully be going in the wash that night if I could get there in about an hour. For all my thrills and spills over the years the anxiety and stress were kicking in big style. This could be incredibly good or bad depending how up for it they "both" were.

An hour later I was knocking on their door and a smiling Tim let me in wearing just shorts and a tee shirt and pointed to the living room. His expression settled my nerves a good bit but I'd still not seen Jesse. I sat on the same couch that I'd sat on as this plan had been hatched and looked nervously at the door as Tim poured me a drink. I noticed the lghts had been dimmed and the oil burners were filling the room with a lovely aroma.

Just as Tim turned to bring my drink the door opened and Jesse walked in with her little red kimono tied round her waist. It took my breath away to see her standing there with a gleaming big smile and her cheeks slightly flushed. Nothing had been said as she walked over to me and gave me a kiss on the forehead. Her kimono was only loosely tied and I could see her breasts inside as she leaned forwards. My heart was thumping hoping this was just a little preview.

Jesse took the initiative by telling me I looked great but was overdressed for the occasion and guestured for me to undress. As I stood to undress I turned to see Tim already bollock naked with his cock standing to full attention and them exchanging a smile.

"So the naughty boys have been looking at pictures of me have they, and leaving me out of the all the fun" said Jesse.

She seductvely sat on the couch I was undressing at and undid the belt on her kimono as she slumped back and opened it wide. She was in charge for sure.

Jesse kept eye contact as she informed me "You know why you are here, and you know that I want you two naughty boys to wank your cocks and cum on my tits. I'll do my best to make you nice and hard and if we all like what we see, well who knows".

She sat back and opened her legs as Tim crouched on the floor in front of her and gently parted her pussy lips and started licking her gorgeous shaved fanny.

It was Jesse who was leading and said to Tim "see, I told you I would do it, I told you I wanted it, I told you I wanted to show Paul my pussy, I told you I would open my legs and show him my sex, I told you I wanted his spunk, I told you I would do this because we both want it".

She was pulling Tims head tight to her cunt and had a very noisy orgasm as he licked frantically at her wonderful fanny slit. It was obviously planned that as soon as she came they made their way to the reclining chair and she slumped back and raised the foot rest. Jesse opened the kimono and dropped it from her shoulders as she sat down and opened her legs wide. She licked her fingers and began carressing her clit as her head rolled from side to side.

She was in full flow and by now we were stood either side of the recliner with Jesse fingering furiously at her pussy and us stroking our cocks slowly so as not to cum yet.

Jesse's next comment was "so I hear you like wanking to girls in kimono's bad boy, but my pussy is younger and wetter than hers so if you want to wank to a girl in a kimono it had better be me from now on"

She was gasping as she said it and had another orgasm as she said to Tim "see, I told you I would do it, I told you he would love my pussy, I told you I really did want two cocks and I told you I wanted two lots of spunk on me"

Jesse then got off the recliner wobbling at the knees and sat upright on the couch laying back to push her fanny out. She was still fingering and rubbing her clit and demanded "one at a time between my legs and wank your cum onto my cunt"

I was closest to cumming and kneeled on the floor with my cock pointing directly at her pussy from all of an inch away as Jesse told me "from now on this is where you shoot your spunk when you are horny".

I couldn't take my eyes off it as stream after stream of spunk covered her pussy as she fingered some inside. I could feel Tim at my shoulder urging me to the side and watched as he took his place between her legs and shot his cum on Jesse's pussy and tummy.

Jesse was in a frenzy now rubbing the spunk up and down her body as she squeezed her tits saying "I told you I would, I told you I wanted two men to cum on me, look at all the spunk on me baby".

There was no awkwardness afterwards as we sat naked and had a drink and talked honestly about what had happened. We have had a fair few meetings since with me even staying the night and being allowed round for a wee treat even when Tim's at work. It took another three meetings before we all got intoxicated with lust took it further than had been intended.

Cheers, Paul