A Date with Destiny

Hi! I am Scott, 24 years of age and like most of my generation, constantly horny.

I am 5'11" tall with jet black hair and blue eyes. I am a decent build, go to the gym twice a week but not a freak.

My favourite haunt is a little, trendy bar down town, that brings in a lot of the office workers from the centre. I've scored a few times in there and with different kinds of girls.

Some, like me, are just young and horny, looking for a one-night stand, if even that long.

Some are nervous young things and I have popped the occasional cherry in there.

And then there are the older women, looking for some extra-marital fun that only a young cock can provide.

Anyway, on this particular night, a damp Wednesday, I was on the lookout. It tended to be older women and was often like shooting fish in a barrel.

I had been delayed by a couple of events. I'd had to work a little later to complete a report, which resulted in me missing my normal connection into town.

By the time I had arrived, it looked like most of the available talent had been taken. I groaned but thought I'd have a quick drink then head off elsewhere.

I'd drained my glass and was about to leave, when my eyes caught a solitary figure in the corner. From my position I could see she had a lovely bouffant hairstyle. Nothing ventured, nothing gained, I reckoned and so made my way over to her.

She sat with her knees together huddled over what looked like a pink gin and tonic.

She was wearing a black faux leather jacket, and a leopard print dress that stopped a fair bit above her knees. Her legs were encased in sheer black lingerie.

She had smallish tits but was only about 5'8" tall.

She looked up and smiled, a soft genuine smile that invited me to make a move.

"Hi, I'm Scott. I couldn't help but notice you. Can I get you a drink?"

Her hazel eyes looked me up and down as if deciding whether I could join her or not.

"Sure, why not, I'm Destiny." She smiled again as she offered a hand to shake. She had a strong, confident handshake and her eyes drew me in.

She had gone a little heavy on the make-up and I reckoned she'd be up for some fun. I was already thinking of her glossy red lips around my cock!

I couldn't be certain but I thought that she was around the 40 mark. That was fine by me, as experienced women are definitely more fun and tend to be really dirty in bed.

I brought drinks over and made a point of sitting beside her, with an arm immediately snaking round her waist. Destiny didn't resist, instead she leaned into me.

We spoke for a while. Destiny told me she was a divorcee and let it out that she hadn't had sex for eight months.

I thought I'd hit the jackpot! Especially when Destiny started to rub the inside of my leg. My seven inch cock had by now expanded to its full length and Destiny brushed over it.

"Do you like that, Scott?" She purred, as she traced a nail over it.

"What do you think?" I gasped.

"I'm thinking you'd love me to suck you off." Destiny giggled.

"You're a mindreader honey." I replied.

Destiny moved her lips to mine and before I knew it, she was aggressively pushing her tongue deep. It surprised me but it made me so horny. Destiny moved in for the kill.

"You'd love to come to my place, wouldn't you?"

I nodded furiously.

"You'll have your wish but you need to be aware of one thing.....our bodies are the same."

Destiny looked prepared for the worst.

My mind was doing cartwheels, along with my stomach.

What was going on here? Destiny was a guy? Surely not. She...or he... was beautiful and had certainly aroused me.

I wasn't gay, it had been a female I had been attracted to, not a guy but I found I wasn't revulsed, more curious to have a man's lips around my bulging manhood.

I was still in a bit of a daze when Destiny got up, stating he was going to powder his nose. I watched as he walked to the ladies room. What a beautiful ass! It wiggled so tantalisingly and I now knew I wanted to fuck that too.

We left the bar arm in arm. Destiny said it was only a ten minute walk to her flat. In the end it took forty minutes as we stopped in every available doorway for some more snogging. Every time we stopped, my mind kept reminding me that Destiny was really a guy. By that point I cared not a jot what Destiny was. All I was interested in was the sex.

We arrived at Destiny's door and I was given an ultimatum.

"Scott. This is it. You go through that door and gender becomes irrelevant."

I laughed at that comment.

"No Scott, I'm being serious. Go through that door and cast your inhibitions aside."

"Destiny, just suck my cock and I'll be happy."

We went to the soft couch, Destiny's jacket being discarded. I sat back and let Destiny drop to his knees.

"Prepare for the blow-job of your life, honey."

"That's a big promise to make, babes. I hope you deliver."

At that, Destiny undid my belt, then slowly unbuttoned my pants.

"God, I love cock." Destiny said to no-one in particular.

My cock was straining at the leash. It's full seven inches pulsing and throbbing.

Destiny kissed the tip and licked the pre-cum that was gathering. His tongue ran slowly under my helmet then tickled the rim.

That made me thrust up but also allowed Destiny to find my ass. HIs finger started to toy with my hole as he took my cock in, inch by inch. Those brown eyes looked up at me as he sucked and I'll admit I was in heaven.

My cock was now fully immersed in Destiny's mouth and his finger drew a gasp from me, as it entered my ass. I had never thought about anyone fingering my ass and now I was being driven into a horny fervour.

I could feel that I was ready to erupt and warned Destiny. He paid no heed and continued to suck on me. I felt my legs stiffen and I fired out a huge load of cum in a series of five spurts. Destiny didn't waste a drop!

His finger remained in my hole.

"You like that, don't you?" Destiny said smugly.

I smiled and nodded.

"How do you fancy my cock in there?" He asked whilst strumming my prostate.

I no longer cared if this made me gay or not, I was just following the flow of the situation.

Destiny lifted her dress, exposing the top of her tights. I pulled them down and his gorgeous cock sprung out. At least eight inches long, it was mercifully thin.

"I'm going to fuck you Scott. By the time I'm finished you'll be begging for more."

I was too excited to argue and in fact, was now anticipating his cock with glee.

I held my legs up by the ankles and Destiny started to rim me.

"Take me Destiny! I need you." I couldn't believe my own words. Here I was, a straight guy, wanting my ass to be fucked by a cross dresser.

After preparing me, Destiny lined his cock at my hole and teased me with it.

Without warning, he pushed in roughly, causing me to whelp in pain.

"Don't worry honey, it gets so much better." He assured me.

I gritted my teeth for the next stroke and gradually the pain subsided.

I could hear myself moaning as his cock rhythmically pumped in and out. My cock was hard again as Destiny fucked me as hard as I had planned to fuck him.

"Here I cum sweetheart!" The warning was as much an announcement as anything else. Now I felt my insides being coated with his cum. I then ejaculated again. As my cock was angled towards me, I took it in the face, lapping at my own cum.

Destiny had now withdrawn from my ass and offered me his cock with a simple command. "Clean it."

I had never had a cock in my mouth but then I'd never been fucked by one until a few minutes previously. I did not even think twice, my tongue ran over his hot meat.

At that point it hit me that I loved his feminine beauty but topped off with a hard cock. Life would never be the same again.