The Widowers Solace Pt. 01

I looked into the mirror, I still had his cum caked on my cheeks and some on my neck. I smiled a smile of near contentment. Something was missing, I wasn't completely there, yet.

"You coming back to bed babes?" Came the invitation from Glen, whose cum I was washing off my face.

"I just want to freshen up a little. You really did a number on my make up." I heard him chuckle.

The reflection was not kind to me. My face was old, I shaved a few hours ago and already the stubble was visible.

I fixed my bra and tucked my cock back between my legs. I remembered the face that looked out from this mirror the first time I wore a bra and panties. It was over forty years ago.

I reminisced as I washed my face and reapplied my lipstick.

I had just got married and Margret and I had bought this house, I had a good job and a loving wife. Life was good. But, I always liked the feel of ladies under things. My dad had given me a few thrashings in my childhood, after I got caught wearing mums satin underwear.

A few weeks after we moved into this house Margret came home early, she was supposed to be looking after her sick mother, and I wasn't expecting her home. I was wearing one of her satin slips, a pair of her tan coloured nylons and a lovely lace bra.

I was standing in this very spot, looking into this very mirror when I saw Margret's reflection. There was no madness or anger in her face, just disappointment. That was a long night, but I told her the truth.

I was a transvestite. Sometimes I like to dress in her things, it wasn't a sexual thing for me. For some reason I just felt relief when I dressed.

I assured her that I wasn't a homosexual.

I honestly wasn't. I know I am cleaning another man's cum from my face as I recount this, but back then I wasn't a homosexual.

Things got back to normal. Margret was a class act! Once every month she would go to the store and pick up some new lingerie. She would leave it in my closet and would make plans to go out with her girlfriends, allowing me time for my little hobby, as she like to call it.

The years went by, and we got old, our kids got old.

Then Margret got sick.

I was lucky to be with my best friend in the whole world as she passed away. Before she died, she joked that I would have lots of time for my little hobby now.

A few weeks after we buried her, I was clearing out one of Margret's closets when I found a suitcase. In it, Margret had left me a treasure trove of femininity. Lingerie, hosiery, shoes and make up.

I was an old man now, and I looked like an old man. But I was able to dress as I pleased. My house was remote enough that I rarely got bothered.

I was searching the internet, that's right I maybe old but I am not decrepit, and I know about the internet. Anyway, I found a site, like a facebook for transvestites. In no time at all I had made a few friends.

Most people on there want sex. I didn't want that, I wanted to make friends.

The guy currently lying on my bed, whose spunk I am washing off my face, was one of my first friends on that site.

Glen and I started talking. He was a divorcee whose wife caught him dressed and kicked him out. We exchanged emails, and eventually we started to call each other. Other than high heels and lingerie we shared several other passions. We both liked the same football team, "Go Chargers!"

We liked to paint, and we both liked fine wines.

Eventually I grew the courage to actually meet Glen, and we met as guys and did a tour of vineyards only a couple of hours from where he lives.

It was really nice. When we got back to our hotel, the two of us would carry on as if we were still closest trannys and act as normal guy friends would. We would get back to our own rooms, and I would dress. Little did I know he was doing the same. We would call each other and talk the way we had done before we met.

Nothing sexual, just girlfriends talking on the phone.

On our last night I got a call at the door, it was Glen. He looked fabulous, black lace Basque, black stockings, black lace panties, patent leather stilettoes and a wicked grin.

Of course, I let him in. I hadn't had sex in over a year, and Margret god rest her soul, only wore this sort of outfit once before.

"Glen." Was about all I could manage.

"Leo, I know your straight. But I need to say this, or I will hate myself forever."

"Ok." I closed the door behind him.

"I am not a fag. When I dress, something comes over me, and I feel like a slut. I need to be treated like a slut. Ok maybe that does make me a bit of a fag." I am not sure he had ever uttered this confession out loud before.

"Honey, this has never been sexual for me. I don't dress to please myself; I dress to relax. I am sorry."

"So, there is no chance?"

"I'm sorry." I couldn't look at him, I felt like I was breaking his heart.

He gently lifted my chin, and softly asked, "None?"

I shook my head, and he softly kissed me on the lips. I pulled away, not immediately but I pulled away.

He forced a smile before saying, "I had to know. Sorry." He walked toward the door, and I knew that if I let him walk out then everything would change, I didn't want a sexual relationship with Glen, I really didn't want to lose his friendship which I had begun to treasure.

"Glen, you don't have to go." I almost begged.

"It's probably for the best."

"Please stay?" I probably sounded as desperate as I felt.

He stayed, and I opened a bottle of wine that I had bought earlier that day. We drank and talked for hours. We were girlfriends, it was a night I would never forget, it was a night that changed my life.

Glen and I became friends, glen and I also became girlfriends.

While I hadn't regretted rebuffing Glens advances, I had thought about them a lot. I even found myself getting aroused once or twice thinking about it. Which was very new for me.

A few weeks later I went to his house to stay for a while. We visited a couple more vineyards as guy friends and hung out and gossiped at night as girlfriends.

On the last night, we were having dinner. I was wearing a long flowery dress, a pair of cork wedge sandal shoes, a pearl necklace and my blonde wig. Glen as ever had really put the effort in. He wore a leather pencil skirt, a white satin blouse, and the white stilettoes with the longest heels imaginable. He still had the body for it, while I was a lot chubbier.

Our feet brushed against each other under the table as we ate. Nothing was said out loud, but for the next ten minutes we effectively had foot sex under the table.

Later I was doing the washing up, when glen needed to get passed me, and I felt him brush past me. His crotch lingered just a little longer than it needed too at on my rump. It was quite obvious that he was aroused. I was tingling with excitement, as much as I didn't want anything to happen, I was longing for it to occur.

We ended up in the lounge drinking more wine, somehow the conversation got onto sex. We began to share stories of our sexploits.

Glen had led a much more exciting life than I had. I had been with four women in my life. Mary Rose was a cheerleader I got with just before I left for collage. My roommate's sister, then there was Margret and a Vegas stripper called Peaches that I got with after my Batchelors party.

Hearing about glens frolicking adventures, got me quite uncomfortable in my black satin panties. I sat up to adjust myself without thinking and Glen must have saw me. "Here let me help with that." He offered and was on my in the blink of an eye.

He had his had up my dress, and was rubbing my throbbing cock through my satin panties. I gasped, but I didn't stop him. This was amazing.

He softly retrieved my cock from my panties and gently began to jerk me. I looked down and shook my head. He looked into my eyes and kept jerking my cock. His other hand made its way up my inner thighs and cupped my balls, while he jerked me off.

"Is it ok?" He sought reassurance.

"Please don't stop." I urged. Closing my eyes in bliss, I soon felt a new sensation a warmness, and moistness around the tip my penis. I opened my eyes to see my friends' lips wrapped around my hardness.

Margret didn't like to give blow jobs, so this was a very unusual sensation for me. But I knew that I would not be able to last very long, his hands were still fondling my balls. One of his fingers brushed my rose bud, and I yelled as I came hard into glens mouth.

"I'm sorry." I offered, as the world came back into focus.

"You enjoyed that?" He asked.

"It's been a while."

"I could tell."

He stood to his feet and said, "Thank you." He leaned down to kiss me but had second thoughts.

"Excuse me, I will go to the washroom and a.." he hesitated.

"And what?" I asked dumbly.

"I'm going to jack off."

"You could do it here, if you want."

"You're sure?"

"Yea, I think I would like to watch." He hitched up his skirt, and I saw the lace tops of his stockings, he pulled the black lace panties aside and pulled out his thick uncut cock, and slowly began to jerk it.

He was standing just in front of me, the motion of him wanking off was hypnotic, I was in a trance. Without thinking I reached out and touched another man's cock for the first time in my life. I held the underside of it, I fondled his balls, they were colder than I was expecting.

A droplet formed on the tip of his cock, and for some reason I had to taste it. I leaned forward and licked his penis.

What the hell was happening to me? I am straight, but he I was dressed in a dress and heels and the only thing that could satisfy me right at that moment was to suck on this guys cock.

That's what I did.

"Are you sure?" He asked. I didn't wait for an answer, I lunged forward, and took his manhood in my mouth.

As I mentioned before, I have not had too many blow jobs in my life, so I was quite inexperienced. My only point of reference was porn. In porn it's all about deep and hard. What I was about to learn a few seconds later was that giving blow jobs was quite sore. My Jaw ached. Porn stars must have snake like jaw muscles.

But I soldiered on and tried to jam as much of Glens seven inches into my mouth.

Eventually Glen came to the rescue. "Babes, just suck the tip, and jerk the shaft."

With that pointer, I stopped retching on his cock and moved to the pleasure phase. I sucked on his tip, using my tongue to tickle the underside of his helmet. While I gently jerked his shaft with one hand and rolled his balls in my other hand.

Who says Tranny's cant multitask?

After a few short pleasurable minutes, (yes, I was really enjoying this) Glen warned me of his impending climax. "Watch out babes, I am going to cum."

I think he expected me to dive for cover, but I had earned this reward. I know when I was about to spurt, I like to force myself deeper in my lover. So, with this in mind I relaxed my jaw a little and sucked him as deep into me as I could.

I felt him swell up, then I felt the warm spunk run down the back of my throat. It was too much and I pulled him out of my mouth, and I was rewarded with another load on my cheek.

There was a weird awkward silence for a few months while we both composed ourselves. He offered me a towel to wipe my face with and as I was cleaning, he said. "Wow!"

Before offering, "You can fuck me if you would like."

I desperately wanted to fuck him, but my "sensible" hemisphere was in control again, and I declined his offer.

We met up a few more times and fooled around in the same way. We would jerk off and suck each other. But as I stood in the mirror a few months after I first sucked Glens cock, I felt like I need a little more.