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
I decided I had to hide it and take the consequences later, tucking it under paperwork in a desk drawer I left.
Back at home I couldn't concentrate, my mind was racing trying to process the recent events and my reaction to Henry's hidden desires, and the photo, my god that image was firmly lodged in my memory.
I could vividly picture his slim frame dressed in the lacy red lingerie, his semi erect cock curling to one side in the sheer panties. My cock began to stiffen again, I needed to get a grip, what the fuck was I doing getting aroused at the thought of my best friend, a man for pities sake.
I decided to shower before the party and quickly undressed discarding my clothes through the house toward the bathroom. I stood before the mirror analysing my older physique, not too bad for a fifty something I thought, perhaps a little soft around the middle. Absentmindedly I began to stroke my semi erect cock thinking of Henry knelt before me naked sucking in my swollen head. Fuck, the thought of it had me fully erect in seconds, I was seriously losing the plot here and needed to stop fantasising.
Turning on the water I stepped in and let the cool spray calm me down.
How could I go to the party now? He would surely find out it was me who was there earlier and had seen his personal diary, I shouldn't have read it, I had violated the trust of my friend and felt terrible. But on the other hand he had written these fantasies down and should have kept the writings secret, I felt completely torn at at an utter loss.
Also I had to admit that I felt sexually excited for the first time in ages it had been probably six or seven years since my last sex and I was flattered that he liked me in that way. The detailed description of our lovemaking was incredibly stimulating and it had been a long time since I had anyone kiss me below the neck. I lay back and wondered what it would be like if he were here now naked on my bed perhaps in a 69 position both of us greedily sucking each other to completion, or me behind him slowly easing my steel hard cock into his tight hole, fuck I was at it again masturbating like a teenager and in seconds shot my seed over my body.
**********************
With a heavy heart I waited with the other guests, all of us hidden from view, I was behind some heavy curtains waiting for the birthday boy to appear. The lookout near the windowsill hushed us into silence as a few seconds later Henry appeared through the door.
"SURPRISE" everyone shouted and tumbled from their various hiding places, the look on Henry's face was not of amusement but sheer terror as he scanned the coffee table, a glass of champagne was thrust into his hand as his sister wished him a happy birthday and then thanked us all for coming, I was thinking I'd got away with this until my blood ran cold as she turned to face me and thanked me personally for coming over earlier to decorate the house.
Another cheer rang out as Henry and I locked eyes from across the room, our friendship was either over or the dynamics had shifted and at this point I really didn't know which scenario I preferred.
I hung around for a while then made some feeble excuse of feeling unwell I said my goodbyes and left.
Angry with myself I strode home and once in the safety of my kitchen grabbed a bottle of Scotch and decided to drown some sorrows, it was going to take a lot of whiskey.
I sat and nursed my drink musing over the current situation, my mind kept going back to Henry's journal and his sad face from earlier this evening. After an hour or so and a third of the bottle gone I grabbed a coat and headed out telling myself I was just going for a walk to clear my head, yeah right.
My cock was controlling my legs as I approached his house which was dark and it seemed as all the guests had departed, glancing at my watch I noticed it was nearly midnight. Peering through a gap in the curtains I saw Henry slumped in a chair his head in his hands.
I knocked gently on the window and he sat bolt upright in shock, he saw me and assumed the same position waving with his hand for me to go away.
