Disclaimer. The following story is complete fiction detailing cross dressing and consensual sex between two mature men so if thats not your thing I suggest you stop reading now, unprotected sex is not encouraged and any similarity to anyone living or dead is purely coincidental.
Henry and I have been friends for over five years, finding myself unexpectedly alone and in my late fifties I decided to get out into the world again instead of moping around the house aimlessly looking for mundane things to do.
I had tried the gym which turned out to be a boring solitary experience, then the local cricket club which was in fact an excuse for a collection of annoying rich idiots to drink in the afternoon and bitch about the lack of sex at home. A local choir came next but it turned out that I was tone deaf and asked to sing very quietly somewhere near the back!
Then a neighbour suggested a small tennis club not far away, being half handy with a raquet in my youth I went along for a taster session.
And it was fun.
After a brief introduction and the inevitable health and safety monologue I was paired with a slender guy, probably early sixties with grey hair and a warm smile.
He stuck out his hand "Hi its Henry, and you?"
"David" I replied noticing his handshake was a little limp and lingering for an unnecessary length of time.
We hit it off immediately on the court narrowly losing our first game together but the tone was relaxed as if the score didn't matter, it was the social interaction that was the theme which suited me.
I began attending at least three times each week sometimes paired with Henry, sometimes not, but I always sought him out after the showers for a chat and a catch up.
Regarding the post match showers I had noticed Henry was a little nervous about using them, he would rush in drop his towel and stand with his back to everyone finishing in lightening speed and hurry out. Perhaps he was embarrassed about his size I thought, he had no need to be ashamed of his body though, I had noticed his lean back and taught buttocks before but not, or as I thought, in a sexual way.
His body when viewed from behind was almost feminine with long slender legs, if he were a woman I thought I wouldn't hesitate, feeling embarrassed and oddly aroused I hurried out to dry and dress.
My first season at the club came to an end and was marked by a great evening of drinks and laughter and as the group began to disperse I found myself with Henry drinking and chatting about nothing in particular. With a few G&T's in him Henry was frankly hilarious, both of us constantly ending up in stitches at some sly innuendo or comic remark.
When it was time to get going I suddenly felt a bit maudlin as I was going to miss my new group of friends, especially Henry. It was going to be a long lonely winter, again.
Henry sensed my low mood and asked what was wrong, I felt a bit embarrassed to say, not wanting to sound needy and pathetic, he took his phone from his pocket and asked for my number, my phone buzzed and he smiled.
That winter was so rewarding for both of us, we walked, talked and discovered that we had much in common. We both could often be found in each others company and I began to get him round to mine for a meal and good conversation. Henry, I had discovered, was incredibly intelligent with a razor sharp mind and wit, we could talk for hours on numerous topics from politics to art, science or nature, basically he had become my best friend and confidante.
One evening after a little too much good wine we sat outside chatting idly away until the subject of relationships came up. He asked why I hadn't reciprocated the advances of several women at the club, I was dumbfounded and honestly replied that I had been oblivious to all. I knew he was a young widow and asked him about his late wife. He described her as beautiful but very conservative, not very "adventurous" in the bedroom, I laughed but I sensed Henry welling up, I reached around him and gave him my best man hug, his body stiffened and he suddenly stood ready to leave.
I was confused to his reaction to my affection but shrugged it off.
Until one fateful day.
It was Henry's birthday on Saturday and his sister had concocted a plan. She was taking him out for the afternoon to return around 6pm where a surprise party awaited him, not a huge crowd, maybe ten or fifteen of us. I was tasked with sprucing the place up so at 4pm I let myself in using the hidden key safe and armed with balloons and banners began to decorate the lounge.
An hour later I sat back and surveyed my work, the champagne was on ice and the canapes laid out in the kitchen, smiling to myself I wandered around putting the finishing touches to the scene.
The polished coffee table was cluttered with my stuff and as I began to clear it away my gaze fell on a dog eared journal that I hadn't noticed before and the title "Diary/David."
Picking up the book I turned the cover, the first entry was dated over five years ago and detailed our first meeting at the club, Henry had written how handsome I was and how he was looking forward to me joining and becoming a member. All innocent stuff I thought until I flicked through and stopped randomly at the next entry. It detailed showering at the club and how my body looked even describing my flaccid cock and how he had become aroused sexually at the sight of me naked, he went on to wonder how big I was when erect. Oh shit I thought I should stop but I didn't.
Sitting down I began to read more. The language became more erotic as I progressed until he began to list his sexual fantasies between the two of us. One included acts of oral sex described in great detail, others involved kissing and caressing each other naked. Then things took an another unsuspecting turn as I read an entry for a Sunday entitled "Dressing Day."
A photo slipped from the pages and I froze, a figure stood in front of a bedroom mirror dressed in a red bra, matching garter belt, lace top stockings and sheer knickers which left little to the imagination. The head was obscured, could this be Henry dressed like this?
My hands were trembling now and my heart rate was increasing as I began to read the Sunday entry which listed, again in great detail, a scenario in which I came round unexpectedly catching him dressed in lingerie ultimately ending up in bed together and making love. The writing was so vivid that it felt as though it had actually happened, he on all fours as I slowly entered him from behind fucking him with slow sensual strokes then faster as my cock bred his man cunt until I came inside him.
Slamming the book shut I stood and paced around the room muttering to myself but realizing my cock was now painfully hard. Surely this couldn't have come from my mild mannered friend? I shook my head in disbelief.
What happened next I am frankly ashamed to recount, I climbed the stairs and entered his bedroom, I paused as I noticed an open washing basket and lying there was the aforementioned red lace knickers, and I picked them up.
No I couldn't possibly, no please dont a voice in my head implored me to stop, picking up the journal and the knickers I hurried to the downstairs toilet locked the door and freed my hard cock. I found a page where Henry was giving me a slow sensual blow job and began to stroke my shaft, the language was so erotic I felt my orgasm begin to build, then I raised the knickers to my face and sniffed the gusset, it was a sweet musty aroma of cock and cum, flicking through the pages frantically looking for the photo and gazing on his panty clad cock I spewed my load into the hand basin.
Consumed with embarrassment and guilt I tidied up and began to leave.
Then the dilemma hit me, I couldn't leave the diary on the table but if I hid it he would know that I knew.
"Shit, shit, shit" I muttered what a bloody mess, why did I have to stick my nose in and compromise our relationship
