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The Chance Meeting

The Chance Meeting

by The_swallower
10 min read
4.48 (3300 views)
eroticorgasmgay maleanal
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Let's get the introduction over with. My name is Derek and I'm a 40 year old divorced guy, with strong bi tendencies.

I'm 5'10" in height and have a decently maintained body, now hairless like my head.

It was my 'bi tendencies' that led to my divorce. I had been meeting a suck buddy for a couple of months and my wife unexpectedly walked in to the room with my lips fast around his lovely curvy 7" cock.

Maybe the fact I didn't immediately stop didn't help matters but he was so close to cumming and I wanted my fill.

We didn't have kids, so breaking up was easy. I had been on my own for 3 months now, trying to figure out the direction I wanted to take but cock was ruling my thoughts. Every time I wanked, I was thinking about hard cock, filling both ends.

So it came to pass, I was sitting in the bus station in Edinburgh one evening.. Thoughts of my last suck flying through my mind.

Around ten yards away sat a couple. I recognised him straight away. He was a smaller, slightly chubby guy I had seen before on the bus. What drew me to him was his wonderful smile. Without being stereotypical, you could tell he was gay.

Strangely though, he had a friend with him, sat towards him so I got a sideways look.

I noticed the long brown hair and the short skirt. what really drew my attention were the legs, encased in a flower patterned purple pair of tights. The legs were gorgeous, then they turned and I saw the face. Definitely a guy but maybe with some make-up he would pass muster.

The small guy kept catching my eye and my mind thought about them as lovers and I had to cross my legs to hide my stiffy. He smiled at me, knowingly and blew me a kiss. I blew one back and I knew that the night would prove interesting.

Shortly after, a third person arrived, in a long dress & overcoat and blonde wig. The three hugged. The latest addition to the group was taller than me and seemed a little awkward in female clothes. She sat beside the other two but shied away into the background.

How would I get to know them, I wondered, leaving me to watch them. My eyes enjoying the legs on display.

The bus pulled into the stance and the small amount waiting queued to board. I motioned for the three of them to go ahead and was rewarded by smiles from each of them.

The brunette went to get on but suddenly howled that she had lost her return ticket and didn't have any money to pay for a ticket. The others didn't take her seriously, thinking it was a joke.

"You'll have to go on the game to pay for a ticket. We'll not expect you home anytime soon, Jillian." The other two laughed.

"I'm not joking. I really have lost my ticket and don't have any money left." She sounded genuine to me.

The other two realised the gravity of the situation, checking their pockets for cash but coming up way short.

This was my chance to introduce myself.

"Don't fret love, I can pay for your ticket."

Jillian looked at me, eyes agog.

"You'd pay for my ticket?" she asked, surprised.

"Of course, I couldn't see you stranded. Someone could take advantage of you."

"Ah, you're so sweet." she said softly.

If only she knew what I wanted to do to her.

The smaller guy introduced himself as Ashley, or Ash to his friends and iintroduced the blonde as Alexis. She was still withdrawn but gave me a fleeting smile.

I paid for myself and Jillian and followed them to the back of the bus. The back seats had two blocks of two facing each other and Jillian took the back window seat facing Ash and beside Alexis. I sat next to Ash and we started to chat.

I couldn't take my eyes from Jillian's legs. I was in heat and my cock stiffened, noticeably enough for Ash to comment.

"Someone's got you excited, I wonder who?"

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I decided to speak my mind. "Jillian, of course, she has the most beautiful legs."

Jillian blushed and Ash added "What about the rest of her?"

"To be crude, I wouldn't kick her out of bed."

"Woo! Jillian's clicked tonight!"

She blushed again and I apologised for embarrassing her.

"Don't be silly, I'm just not used to getting compliments, when I'm dressed up." she paused a moment, then continued "You do know I'm dressed up, don't you?

"Honey, I know exactly what you are and my earlier comments stand."

It wasn't long before our journey was complete but before getting off, Ash suggested I join them at his place for a drink and maybe some fun. I eagerly accepted and walked hand in hand with Jillian. Ash went ahead, his arm around the waist of Alexis, keeping her dress up I think.

Jillian stopped and pushed me into a shop doorway and started to kiss me as her hand roamed to my crotch. I slid my hand under her short skirt and soon found my desired destination. Her tights were tented and I longed to taste her. I traced along the outline of her hot cock, it was thick and quite long and I wanted it.

Jillian's tongue pushed into my mouth and I surrendered myself, quickly dropping to my knees in the sheltered doorway.

I quickly pulled down her tights, discovering there were no panties beneath, just her gorgeous meat. I wasted no time getting my lips around her helmet, her soft moans encouraging me. My tongue slid along the surface, slipping into her pee-hole, drawing a gasp.

Her cock pushed against my throat and my ability to deepthroat surprised her, making her push all the way in.

I sucked like my life depended on it and eventually I slipped a finger into her ass. That was the trigger and her legs started to shake before spilling her sweet load into me. She kept pumping and I swallowed four shots of her love juice.

I was loathe to remove my lips as her meat gradually shrank.

"Next time it's your ass." Jillian promised.

"I look forward to it." I answered as I stood up, kissing her again. I felt such a gay slut but I liked this side of me.

Ash and Alexis were a short distance ahead, arms around each other, kissing.

"Alexis doesn't normally dress up, in case you couldn't guess but Ash likes her." Jillian commented, a little sarcastically. I just squeezed her hand.

Ash's flat was on a side street, on the second floor. It was quite small, just one bedroom and a combined kitchen/lounge.

There were two battered leather two-seaters and we sat as couples, the lighting quite low.

Ash got us beers and we sat snuggled close. Me in the knowledge that Jillian wanted to fuck me.

Ash started a conversation by asking me a question.

"So Derek, what did you think of us at first sight?"

"Truthfully? When I saw Jillian's legs I immediately got hard. They're better than my ex-wife's."

"Did you know she had a little extra to give?"

"It didn't take me long to work it out."

"That didn't bother you?" Ash pressed.

"Not a bit. I love cock. Just ask my ex."

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I then related the story of my wife catching me with another guy.

"Wish it had been me." Ash said, winking.

"So do I." I blew him a kiss.

"Hey guys!" Jillian interrupted our flirt. "Look at Alexis. She's fast asleep."

It was true. Dead to the world, head tipped back, her wig about to fall off.

"Fuck! Looks like I'll be having a quiet night then." Ash groaned disappointedly.

"Why? You've still got us." I said, looking at Jillian for approval.

"He's right, Ash. You know I'm up for anything" Jillian said softly, rubbing my knee.

Ash's eyes lit up and he crossed the short space to sit sideways on my lap, facing Jillian. The two kissed tenderly and my hand stroked his chubby butt as I delved inside his trousers. There was a soft down there and he shifted to give me access to his hole. I licked my finger and entered him, without any opposition. He was beginning to tent and so I pulled down his zip and felt him harden through a silky thong.

I soon had his cock out. it was quite small, maybe just over 5" but it was thick and covered in precum.

Jillian now made her move and stood up. I thought at first she was wanting Ash to suck her but she lifted him up and span him round.

"Fuck him Derek, look at his lovely ass." Jillian ordered.

Ash bent over the arm of the chair, his bubble butt inviting me. My trousers were soon at my ankles and I leaned forward to lick his ass, spreading his chunky cheeks.

Ash moaned as my tongue worked inside him and he begged me to fuck him.

I had almost forgot Jillian was there but was soon reminded as her cock prodded my cheeks.

She was going to fuck me as I fucked Ash!

I slid into his sumptuous hole and Jillian soon followed into mine.

Ash was an energetic lover, those bum cheeks wiggled constantly as I speared him. He gave out little girly moans, which turned me on even more.

I put my arms around him and squeezed hiis titties. He probably needed a bra more than Jillian. I knew at that moment that cock and ass was my future a d regretted it not a bit.

His ass was clamped on my cock as we rhythmically fucked.

Meanwhile, at the back, Jillian was now plowing into me. She had teased me at first, just rubbing her pole against my puckered hole, then delved into me. I was glad I'd been using toys on my ass or it might have hurt.

Jillian was an animal and started shouting "Take it, you cockloving whore. You love it, don't you?" At that, she slapped my cheek hard, making it sting. I yelped but carried on fucking Ash.

As Jillian rubbed my prostate, I knew I was going to cum. Seconds later, I flooded Ash's insides with my cum. I gave him more than I had ever given my wife. He groaned in pleasure as he tried to wring every last drop out of me.

Jillian took command again, telling Ash to stand up and feed me his cock. I had always fantasised about being spit roasted, now it was happening. I opened my mouth for him, letting him go where Jillian had been an hour previously.

Smaller cocks are great to suck as you get more down without gagging. I savoured Ash's thick cock as Jilliam pumped me relentlessly, slobbering on his meaty helmet.⁶

Ash was gracious enough to warn me that he was about to cum but I wanted to swallow it. Jillian started breathing heavily too and the two of them reached a crescendo together.

What an amazing feeling! Cum shooting into me from both ends. Waves of cum meeting in my stomach, leaving me used but sated.

At that moment, Alexis decided to wake up, drowsily asking "What's been going on?"

"It's a long story." I answered, as the others laughed.

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