The Widowers Solace Pt. 02

I was never really an overly sexual person.

Don't get me wrong, I do like to have sex, it's just that I didn't spend every waking hour thinking about it.

Before I had met Glen, I had sexual experiences with four people.

I lost my virginity at Prom to Marie Rose she was my high school sweetheart and it was only memorable as she was my first and I blew my load almost as soon as I felt her moistness around my stiff cock.

My second experience was almost as forgettable, Martha was my collage roommate's sister. She and I got drunk, and we work up naked in bed together.

My third was a stripper in Vegas. Peaches was her name, she lay me on my back and straddled me until I came deep inside of her.

Then my wife, Margret. We had a pretty normal sex life; well, I think we did. We had sex once a week for close to thirty years. We both preferred missionary position, I loved to look into her eyes as I climaxed, I would nuzzle her boobs as I made love to her.

We tried other positions; cowgirl was nice watching her boobs dance as she bounced on my cock. Doggystyle was fun while her knees held up especially in later life. But we almost always ended up in the missionary position.

I didn't really have any kinks or fetishes to speak of, so I was well satisfied with our weekly roll.

I was and am a transvestite, but this had almost always been about stress release rather than sex.

Then I met Glen. In the first instalment of this story, I described how Glen and I met, how our relationship went from mutual admiration of fine wines and petticoats, to hand jobs and recently blow jobs.

We hadn't seen each other in quite some time, and I spent this week looking forward to seeing him. I could not wait to hang out with him, to show him my new dress and heels. But I was also looking forward to being in his arms, to feeling his arousal, to tasting his breath and to looking into his eyes as I sucked on his cock.

I had done all this and as I stood in the mirror cleaning my face of his spent seed, re-applying my make up something was not quite fulfilled yet.

He came up behind me, and nuzzled into my neck. "Everything okay?" he asked between kisses.

"I'm not sure?" I answered looking at our reflections.

I consider myself a transvestite, I have no interest in transitioning to become a woman. But when I shed the mask of masculinity I do so with all my heart. My aim is to become the woman in her late sixties, not a parody of femineity, not some fetishized old man in a school uniform etc. I become my female self.

I wear suitable clothing not too drab, but not overtly sexualised. Outfits that any well to do pensioner would wear during her day-to-day activities. I shave my body; I wear an expensive silicone chest plate giving me a suitable bust for a woman of my build. I wear a long wig, and full make up, false nails and stylish jewellery.

Glen considers himself a crossdresser. He doesn't put as much effort into feminising himself, so take him out of his expensive lingerie and sky-high heels and he is his normal self.

I looked at the man in the mirror gently placing kisses on my neck, and I feel a yearning that I can't quite figure out. In the small of my back, I feel his lovely member stiffen, I reach behind and rub my manicured finger over his shaft and gasp, "Again?"

"What can I say, I get turned on by a woman in stockings and heels." He said placing his hand on my panty covered penis which has not recovered from the lovely attention he paid me at the start of out evening together.

"Come back to bed, and I will give you a back rub and see if that doesn't get you going again."

"I Guess." not quite sure where the reluctance in my voice came from.

I took off my lacy corset and folded it over the chair next to the bed. He laid me down on my belly and started to apply baby oil liberally over my flesh. With his hands he began to work it in.

"Oh my Gosh!" I subconsciously exclaimed, surprising myself.

He started at my shoulders, which I knew were tense. Once he had worked the knots there loose he massaged my neck, and firmly worked his way down my spine.

Soon he straddled me sitting on my upper thighs, I worked my lacy pink panties down a bit so he had unhindered access to my lower back. He sat up allowing me to move them all the way under my fleshy buns.

He kept working on me for a while, he brought me to a state of equilibrium, somewhere between arousal and a peace. I was brought back to the real world when I felt his stiff shaft nestle between my butt cheeks.

"Hey." I faux protested. He apologised and began to put his member back in his skimpy black satin thong which would never be able to control his length and girth especially now his was engorged and throbbing.

"Its okay. I don't mind." I said hoping that he would go back to the massage.

Thankfully he did. But he subtility began to gyrate his hips. My cheeks had been slicked up by the baby oil, and his cock slid easily between them.

Again, I let out a moan, for some reason it felt wonderful to have this man use my bum cheeks for his pleasure.

"You, don't mind?"

"No, it's lovely."

Once or twice his thrusts met my little opening, the first couple of times the stinging pain was excruciating, but it was less and less each time.

With all the oil he had used, he was struggling to get any purchase on my ass cheeks, and I could feel his frustration build in him as he just could get enough to bring him to orgasm. In that moment I wanted to please him.

I had never wanted to please him before, well not in this way. We mutually got each other off, either using our hands or mouths. I sucked his cock hoping that he would return the favour, or because he had just sucked mine. Like I mentioned earlier, I was never overly sexual. At least until I felt his rock-hard cock between my ass cheeks.

"You can put it in if you want." I said trying not to sound like it was for my benefit.

He froze, had I crossed the line? I panicked that I had.

After what seemed like an eternity he asked, "What?"

"I mean, if you want, you can try putting it in me."

"I thought..." He stumbled over his words, before asking, "Are you Sure?"

"No, but I think I would like to try."

He didn't say anything but lying on my belly I could hear his smile. I felt him lining up to take my virginity.

"Please, be gentle."

His tip of his hardness, touched my little opening, he rested there before gently pushing forward a little, and withdrawing, every time he pushed it in just a little deeper. In and out, deeper in and almost all of the way out, deeper still then almost out.

I was expecting it to be worse, I was expecting agony. It stung a little; sure, but it was pleasant. I was able to enjoy it.

"Are you okay?"

"Huh?"

"I am inside you; I just want to make sure your okay." I reached behind me and fondled his manly balls and felt for his shaft and sure enough he was all the way inside me.

"Yeah, I just feel full. Its kinda nice." I wasn't lying, it wasn't unpleasant but neither was it world altering. It was just as I said, kinda nice.

He pulled out and asked, "Do you want me to stop?"

"Glen, I think you should stop worrying about it and fuck me." The words sounded strange coming from my mouth, not nearly as strange as when I added, "Please Glen I want you fuck me."

He began to up his game, he pushed his cock back inside of me. It slid all the way in, I let out a groan as his pelvis made contact with my rump. I let out another groan as he withdrew. Soon he began to build up a little bit of a rhythm, I quite liked it. he roughly took my hips and plunged forward again, something was happening inside me. He pulled me up onto all fours, my panties stretched between my legs. He tried to pull them down, but the stocking straps meant that he couldn't pull them any further down.

He pinched the flesh of my hips as he gripped hold of me, almost slamming forward deep inside of me.

I was leaking gallons of precum all over the bed, I could feel it oozing out of my limp cock.

I would love to say I came as a result of his expert lovemaking. But he was way too excited to last long enough for me to experience my first anal orgasm, that would come another time.

I would love to say I felt his seed gushing inside of me, but the only gush happened when his cock went limp and plopped out of my hole several exhausted minutes after his climax.

He forced me forward with such force I ended up back on my belly with him lying panting on top of me.

I was worried, Glen never lost his cool.

"Are you okay?"

He answered in between panting breaths, "Sorry, I needed that."

"Did you just come in me?"

"Oh, shit sorry."

"Arnt your worried that i might get pregnant?" I joked. He stifled a laugh.