So where do I start this story, I guess at the beginning which was last summer where, whilst browsing through members on here I happened to come across her, Jeanette.

Her portrait photo was of a slim,mature elegant lady in a black dress and a light blonde wig, that look in her eyes and that enigmatic smile pulled me in as I devoured every detail she dared give to what at the time was a total stranger.

Sadly just the one photo but that's all it took, something inside me acknowledge the fact that this could be the one I'd desperately been looking for since my mistress of similar years moved away.

Apart from looking so innocent that butter wouldn't melt, I read what I wanted to read the most. Jeanette, an experienced crossdresser was 82, just over 20 years my senior.

The age gap was never the problem as I actively seeked out the older partner having had a couple in the past, both sensual and very active partners with a large variety of, well let's say interests, but the main thing was they looked after me which suited my submissive demeanor perfectly, I was never just a mere fuck and go person, I had a real strong sense of connection with her and that was only just by checking her profile out, those butterflies in my stomach were playing havoc with me, a very strong indication that I really fancied her but too scared to make that initial move!

I'd look at her profile most nights just to see how active she was online, regularly which was a positive sign.

Then one night when I had the chance, whilst having a wank I unconsciously clicked that friend button and liked her photo, nothing will come of it I thought as I reached my orgasm, for a sixty something I could still produce a lot of

spunk if my minds focused on something or in this case, someone.

For several weeks I'd more or less do the same thing, work myself into a frenzy then look at her picture then shoot my spunk into a kitchen towel.

By now this was really the only sex I was having as the wife, sexually, had lost interest in it.

I thought that was just us at our time of life but if you've read some of our exploits from our earlier days, a leopard never changes it's spots and i’d eventually find out why she wasn't interested in sex with me, a frustrating situation but we both played by the same rules so fully aware of each others ‘ extra marital interests’ but that's a story for another time.

That first inquisitive message was so welcome, it was like being a love struck teenager again being asked out for a first date.

Well our friendship started with just suggestive messages which got saucier every time we hooked up, this eventually turned into him sending a few photos of him dressed in his favourite lingerie and wanking for the camera.

I'll admit, I really enjoyed looking at them to the extent my hand found its way into my boxers and gently caressed my hardening cock until BAM, I'd ejaculated inside them with very little warning!

Yes Jeanette really had reawakened my fetish for ‘self love’ and the fact, despite his age I was strangely attracted to him dressed the way he was, that didn't go unnoticed and soon was asking if I had any pictures to share.

That request caught me off guard as we'd not known each other long and I was playing it safe but after he sent a photo of him fucking his love toy then I knew something special was starting to happen.

Apart from some dated photos taken by my then mistress some 15 years ago ( see profile pic) , I had nothing, this would soon be rectified as I looked through my wife's ‘special draw’.

To a sexually starved cross dresser, this was an absolute gold mine!

Searching through I found a few items which I knew would interest him, it was what I did to myself in them that caught his eye.

The first, a red satin like camisole, not quite long enough to hide my cock , coupled with my black hold ups

I had to wait until the wife went out so I could actually take some photos, I will admit the excitement of it all was just like my first time. It would be a few days before suddenly that time came and as soon as she was out the door I rushed upstairs to become Christine.

I had to be careful putting on the camisole but it was slightly tight but accentuated all my curves, especially my artificially enlarged and now hard nipples, my excitedly hard cock hung down, nothing special in the bedroom department but as they say, it's not the size, it's how you use it

Camera setup the impromptu photo shoot began, I did the usual format front side and back and a few suggestive poses hopefully Jeanette would like.

Once finished, and I don't know why I did it but the sudden urge to wank myself off took over and I started to rub away at my very excited and unusually hard cock.

The pleasure I was giving myself was off the scale, I looked at the camera and thought why not.

Was it just the pure excitement or was it the pervert in me that made me do this?

I decided to video the occasion, I couldn't believe what I was doing but now I was in total abandonment, I just needed to cum and cum fast.

Slowly I massaged my cock and nipples to the point I'd totally forgotten myself and just went for it as I gripped my cock hard and pulled my foreskin back which pulled my glans downwards with the strain, the urge to wank myself off was too strong to resist as I pulled away at some speed, my climax was extraordinary to say the least this wasn't just a normal wank, in my head this was Christine being wanked off by another, Jeanette perhaps as I rapidly brought myself to orgasm.

That moment came too soon as I felt myself getting close, my hips bucking away as I was basically fucking my hand now firmly clasped around my cock, a few more violent thrusting from my hips were rewarded with a rope of semem under extreme pressure shooting out towards the camera, the sound of relief from myself very evident, I'd not had sex like this for so long and suddenly it was like the Floodgates opening and torrents of pent up sperm finally released.

That feeling of elation soon turned to panic as I heard my spunk hit the carpet rather than the strategically placed towel.

Looking down the unmistakable streaks of spunk settled onto the carpet and began to be consumed by it as it soaked in.

Turning the camera off I quickly cleaned up that sticky mess to conceal any evidence of my newly reawakened passion. Once all evidence of my ‘ indiscretion’ was removed, Christine was carefully packed away in the ‘special’ drawer. I just sat back and reviewed my morning's unexpected photo shoot.

Some of the photos weren't that bad considering I'd put on a few kilos in the past 15 odd years, weirdly I was getting another erection looking at them until I watched the video, that look on my face as my hand pulled away at my cock, then by using my hips,forcing it through a tightly clasped hand, I don't know if this is normal but i had to rush to the bathroom and urgently relieve myself as I watched myself on the video.

Two wanks in under an hour! Suddenly my life was getting back to some normality!

I picked the best two photos and without hesitation sent them to Jeanette.

I heard nothing from him for 3 days which put me into a panic, had I been played by a picture hunter? Just that very thought made me feel vulnerable and ashamed.

The elation when that email finally arrived, it felt like a millstone had been removed from around my neck.

The mail was short and to the point, ‘ Absolutely fabulous’

Jeanette xx.

Then another email, ‘would love to see more of you but first, more of me’.

With that a couple of him wearing a short black hemmed dress and stockings, he looked so……memories of my previous mistress flashed through my head as I visually devoured the images before my eyes. Yes, Jeanette had my full attention from above and below.

Then the clincher as another email came with a video attachment.

Although I was beginning to trust him I still scanned the file which turned out fine.

I clicked on the icon. A picture appeared of him in that dress, then it started as he caressed himself before pulling up the hem of the dress, revealing quite a sizable erection, thin but long, almost 6 inches I'd guess as his hand started to play with it, nothing special here I thought, then he reached for a tube and momentarily showed it to the camera, well actually me, one end resembled a vagina, the other end look like an anus.

Although his cock wasn't massively wide it still looked like it wouldn't fit in that tube, that critical observation was answered immediately as he reached for a bottle of lube and teasingly applied it to his hard cock, by now mine was in a similar state as with careful positioning with the camera he introduced his cock to the tube.

In my time I've seen many things but nothing as erotic as this as he put the tip of his cock against the entrance of the tube and gently pushed against the entrance, the simulated vagina opened up to accept it.

Jeanette moaned as his cock slipped all the way in, by now my focus was firmly locked on his cock and toy as he started to, at first, wank himself.

The sounds similar to love making, the sound of his shaft slipping in and out with ease due to the lubrication, squelching away as his hand now rapidly shuffled up and down his shaft, I really thought this was it until that magical moment when he'd fill it full of spunk, myself thinking that it was in my mouth and I was just about to be rewarded but then he stopped and pulled it off his still hard shaft, it made a sucking sound as it was unceremoniously pulled off his cock.

No, he hadn't cum, he just walked to the dressing table where there was some clamp contraction attached, he reattached the tube to the clamps the other way around so now the tighter hole was available for him to penetrate.

He gave a cheeky look at the camera, ‘ Christine, this is for you’ as he re-oiled his cock and placed it at the tighter entrance, the hole looked impossible for him to push his cock in what looked like a virgin arse.

Carefully he placed his cock at the tiny entrance and managed to push the top of his cock in, so tight his foreskin was mercilessly pulled as far back to the base of his cock as physically possible, a very defined curve in his cock as he pushed hard into his toy, now he looked like he was struggling, I just watched the video as he tried in earnest to force his cock into what I thought was an impossible hole, he kept up the onslaught of his prize to the point his cock bent to such a degree it plopped out leaving his cock frustratingly hard , twitching away with what I believed was some pre cum oozing from the slit of his cock.

Getting his breath back he started again, this time with the extra lube his cock slipped effortlessly in a few inches, the tight latex expanding to engulf his rampant cock, again his cock bent under the force of trying to penetrate this thing but he continued unabated, his goal was to fill that hole like he'd probably done to countless ‘ friends'.

Jeanette readjusted her hips to an angle that now made his toy more vulnerable as he forced his cock deeper into it, I watched in amazement as slowly his cock slowly slipped in all the way up to his balls, I wasn't sure if the sounds he made were of pain or intense pleasure as he waited, I guess maybe for his cock to get used to its new tight confines.

Then he made an announcement which really caught me off guard but at the same time actually excited me bringing back memories as he proudly announced ‘ Christine this is for you’ with that he started to fuck that toy,

What I was watching looked physically impossible as his cock now forced its way into that tiny hole in the toy turning it into a more accommodating fuck hole.

The first several thrusts looked gentle, my own excitement now getting the better of me as I started to wank myself.

Jeanette’s thrusts about to accumulate into a crescendo of rapid thrusting as he fucked that toy with No mercy.

He must have been close to cumming from the onset as he was really fucking that toy hard, so much the dressing table started to lift off the ground, he placed both hands on it to steady it as if flat on someone's back, mine perhaps?

He now really started to fuck that thing in earnest and moaning as he built up to filling that hole with his hot sperm.

I'll admit this was too much for me given my sexual drought and I unashamedly ejaculated as the video played on, I stopped the video whilst I cleaned up my indiscretion then rewinded the video to just before I lost control of myself.

There he was, fucking that toy for all it was worth, he really was pounding away at it, a very naughty thought crossed my mind that he was behind me , fucking me, every thrust lifted the dressing table off the carpet, then it happened, several independent hard thrusts as he cried out my femme name, ‘ oooooo Christine ‘ it was then I noticed a small photo of me in my dress on the dressing table , ahhhh, that explained his enthusiasm in his fucking, i guess I should be honoured as his hips now really forced his cock into that tight hole, there was no mistaking his orgasm as he cried out my name again, that orgasm must have been intense as for a moment it looked like he was having spasms, his whole body jerking away as he flooded that tight little hole with sperm, now spent he stood there for a moment, still fully inside his toy then looking at the camera with a big grin, he pulled out as evidence of his lustful endeavors oozed from the end of his cock and toy, his cock now wilting, fully used, his face said it all as if he'd just fucked my tight barely used arse.

The last few seconds of the video was of him reaching for the camera that look on his face of total satisfaction as it switched off.

Well I must admit, I wasn't expecting this, the fact that I totally enjoyed it, was beyond belief

I'll be honest I really didn't know what to do with myself, Then a message which totally threw me and totally unexpected just two words

‘Your turn’ Jeanette xxx

A wave of fear then excitement as I read the message again, could I actually do this? it wasn't like we didn't know each other but this relationship was fairly new so unsure at that moment but……..

Perhaps?

So, did I do it? ……………