The Encounter with Robin

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A Shy Man. A Sexy Crossdresser. A memorable first encounter.
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I had always been a curious guy. Despite this however I never had the courage to actually experiment. That was until that Friday night.

It started off like a usual Friday night here in London, everyone from the office left a bit early to go to the local pub around the corner. I joined in with them despite feeling that I don't actually fit in but it usually meant a free drink and hey, that was good enough for me. They were all fast talking businessmen who threw around words like 'banter' or 'classic' so often that it just became white noise to me. One of them was just in the middle of describing one of their conquests with a busty nurse from the other night when someone in the pub caught my eye. I saw the sexiest person I'd ever seen. There amongst the white noise was Robin.

Long messy red hair sat upon her head. She had a gorgeous freckled face with big, bright red lips, a sharp nose with a piercing on the left side and dazzling green eyes framed in black, misty eyeshadow. My eyes went down further to notice her tall and slender figure wrapped in a red rubber dress that only just covered her ass. My eyes reached her legs, which were covered in fishnet stockings and black thigh high boots. I couldn't take my eyes off of her.

Robin was dancing around to the pop song playing on the pub radio, swaying her hips side to side, back and forth. She turned around and noticed me staring at her and smiled. She looked me in the eye and gave me a wink. I must have been hypnotised as without thinking about it I was making my way over, excusing myself from my work colleagues. It was only when I was halfway there, my mind decided to question the situation.

'She is probably already with someone,' my mind argued.

It didn't matter, I was still going over.

'What makes you think she will be interested in you?' my mind whispered.

For the first time, I ignored all my minds warnings and made it to the person who had caught my eye and to my surprise , she was the first to speak as she moved in close and whispered in my ear.

"I saw you over there, staring at me," she said with a Scottish accent. This just added to the sexiness.

'Oh shit,' I thought, 'she suspects you are a weirdo.'

"My apologies, I didn't mean to stare and make you uncomfortable," I replied, hoping she wasn't too offended.

"Oh I'm not, in fact I kind of liked it. I'm guessing you like what you see then," she said cheekily.

"Oh, definitely!" I said excitedly before adding, "Would you like something to drink?"

"A true gentleman!" she remarked "I would love one. Get me a porn star martini."

"Coming right up."

I relayed the information to the bartender and ordered a pint of beer for myself.

"I'm Robin," she chirped.

"Jack," I replied.

It wasn't long after that the Bartender handed us our drinks. Robin held out her martini.

"Cheers."

"Cheers." I clinked my pint glass against Robin's martini.

We spent the next several minutes drinking and talking about all sorts. Movies. Games. Robin attending the local university where she was a first year majoring in Graphic Design. Somewhere in the middle of our small talk, Robin suddenly exclaimed "Whoops, I dropped something.", and proceeded to turn around and bend over as if she was going to pick whatever it was up. I tried to help by looking out for this mysterious lost object but all I ended up seeing as I looked down was Robin's thong, Black, lacy, and riding up between her perfectly formed asscheeks, perfect for squeezing. Robin backed up, so her ass was against my crotch and moved it from side to side so it rubbed against me and made me moan. She was teasing me, in public no less, and I wanted more. Robin stood back up and turned back around to face me again.

"Did you find whatever it was you were looking for?" I asked, knowing there was nothing down there and it was just an excuse to tease me.

"Oh I found something alright," she replied in a seductive tone.

"Maybe we should go back to mine and see what else we can find?"

I still can't believe I had said that, I was never the kind of guy to go over and invite a girl back to mine after only just meeting them. I was convinced Robin had bewitched me and I was under some sort of spell. I decided though that it didn't matter if it meant spending the night with her.

"Then you better call us a cab," she said with a cheeky grin.

I quickly arranged for a cab to pick us up from the pub to take us to my place and after a couple of minutes, one arrived promptly.

As we sat in the backseat, I looked at Robin and moved my eyes from her green eyes down her body and noticed something I didn't before in the pub. A bulge between her legs. Robin was a crossdresser. Part of me was nervous and unsure but this didn't change the fact Robin was still the sexiest person I've ever seen. Robin bit her lip and blushed, looking all embarrassed. She tried to hide her bulge in her hands.

"You've discovered my little secret then," Robin said bashfully. "I'll understand if you want me to get out now."

There was a tone of sadness in that second sentence. I responded by moving her hands away and rubbing the bulge over her dress. Robin gasped and bit her lip, trying to prevent any moaning sounds from coming out. She wasn't quite successful. I smiled knowing I got Robin back for that stunt earlier in the pub. Meanwhile the cabdriver was switching his gaze between looking at the road and us in the backseat. I guess he was enjoying the view.

It wasn't long after that when we got to my apartment. Taking a ride in the elevator to the ninth floor, Robin took this opportunity to hitch up her dress, revealing more of her bulge contained in her thong. I was glad I was almost at my apartment as I could feel my cock getting hard and pushing up against my jeans. Robin noticed this too and went to go to touch it, but at the last second she changed direction and her hand went around my waist to pull me closer. Our cocks were rubbing against each other. Divided only by the fabric of the clothes we were wearing.

Ninth floor. We got out and located my door number. I inserted the key and twisted it, the door was now unlocked. Robin pounced on me and we flew backwards through the door. Our mouths were pressed against each other, kissing ferociously. My jumper was the first thing to go, followed by my shirt, which Robin ripped off with alarming ease. I led Robin to the bedroom and pulled her onto the bed where Robin straddled on top of me, swaying her hips back and forth, rubbing against my cock. No longer in public, I was free to moan as much as I liked, as was Robin, who had took this time to slip off her rubber dress, showing off her full lingerie set, belly button piercing and smooth body to me. The bra was just as black and lacy as the thong.

"Maybe you should remove my jeans," I suggested.

Robin bit her lip and nodded, getting off of me in the process. Her hands made quick work unbuttoning and pulling off my jeans. My erection was finally allowed to breath. Robin took a long look at the tent I was pitching in my boxers and removed her bra, revealing her flat chest and petite nipples. This was the moment I took charge. I got up and pushed Robin so she was lying on her back and I got on top of her. The sudden rush brought a smile to her face and I, once again, found myself surprised at my actions. Who was this new confident Jack that Robin was unleashing in me?

"I wasn't expecting you to do this!" she said with a coy smile.

I leant over and whispered in her ear, "You haven't seen nothing yet."

From there I kissed Robin's neck. She was squirming and moaning. My lips moved to her nipples and bit them gently. Robin's moans only grew and I could feel her cock twitching against me. Lower and lower I kissed until I reached the top of Robin's thong. I stopped and looked her in her green eyes. She gave the go ahead and I slid off her thong, revealing her cock. It was bigger than I thought and the area surrounding it was smooth like the rest of her. I was memorised by it. I bent down and took some of it in my mouth.

"Oh Jack!" Robin exclaimed in ecstasy.

I kept going. I could feel her cock getting harder in my mouth as I continued to suck it more and more. Robin held my head there for a while until she told me to stop.

"I don't want to cum," she told me. "Not yet."

I stood up and slid off my boxers, my cock was now free and fully erect. Robin got on her knees and returned the favour by sucking it. She was an expert at this, I could tell by the way she was using just enough mouth and just enough tongue and it felt amazing. She licked all the way up my shaft to the head, before deep throating all 7 inches of me.

"Robin. Robin. Robin!" I was unable to think straight, just barely getting out her name.

She sucked harder and faster, looking me in the eye as she did. This was it. I was going to cum. I was about to tell her but Robin already knew and prepared for it. She held my cock an inch from her face and rubbed my cock as fast as she could. Then it happened Cum shot out of my cock and landed all over Robin's face. She used a finger to get some of it that was dropping off her chin and sucked it clean. She grinned in satisfaction and delight.

I went to the bed, exhausted yet relaxed at the same time, and lied down. Robin got off from her knees and stood back up, cum was still all over her face.

"I hope you aren't too exhausted because I want a round 2," she said putting her hands on her hips, her cock still erect.

"Round 2?" I asked.

Robin responded by turning around and bending over, then with her hands, spreads her asscheeks apart revealing her tight butthole.

"I don't have any condoms though," I foolishly said.

Robin turned back around and crossed her arms. "I don't know if you haven't noticed but I can't get pregnant." She seductively added, "Plus I want to feel your cum inside my ass, dripping out of my hole."

The way she said it made me excited and without a second thought I agreed to fuck her ass bareback. Robin knew exactly what she was doing to me and took the news with the great joy, jumping up and down, before diving on the bed with me. Together we just laid there. Naked. Waiting until I was ready to fuck her tight ass. With how horny I was feeling that night, Robin wouldn't had to wait long.

When I told Robin I was ready, she responded by immediately getting on all fours on the bed with her ass out in the air, wiggling side to side. I got behind her with my throbbing, erect cock. I started by teasing her, rubbing and pushing my cock's head against the entrance of her ass. I could hear Robin's moans and could only imagine the big smile she had right now.

"Are you ready?" I asked, knowing the answer.

Robin bit her lip, looked back at me and enthusiastically nodded.

My cock slid into her asshole, which made Robin moan the loudest this night. 'The neighbours must be awake and listening in on us by now,' I thought.

My cock was slowly pumping in and out of her asshole.

"Harder!" Robin demanded loudly and I happily obliged.

My cock was now deep in her asshole as I fucked her harder and harder. My hands grabbed hold of Robin's asscheeks, squeezing them hard as my pace quickened.

"YES!, YES!, YES!" Robin cried. "Breed me! Make me your Cum Dumpster Jack!"

I spanked her ass just as my cock was now balls deep inside of her.

At this point we were both just moaning and grunting, unable to make out even the basic of words anymore, as if we had become two savages with no concept of words. Just how to fuck wildly.

I was so close to cumming for the second time that night and it was going to go all inside Robin's ass. In 3, 2, 1.

"Uggghh!" I cried as I ejaculated in Robin's asshole.

"Oh yes!" Robin exclaimed as she felt the cum inside her, just as cum also shot straight out of her throbbing cock. "Oh fuck! That was good."

I pulled out my cock slowly and collapsed on the bed. Robin cuddled up to me. We were both covered in sweat and out of breath. Robin's eyeshadow was running down her face, mixing with my cum from earlier.

"I've never felt like that before," she said as she was panting.

"Me neither," I replied, trying to catch my breath.

I don't remember much after that, only that I fell asleep sometime afterwards. When I woke up in the morning, I was disappointed there was no sign of Robin. I was almost convinced I made the whole thing up. Then I saw my phone laying next to what I recognised as Robin's black thong. I had a new message from Robin or, as she put in my phone, Cum Dumpster Robin. It read:

"Sorry, I won't be there when you awake. I took the liberty of adding of my number on your phone. Let's meet up again sometime? PS enjoy my panties as a souvenir of a great fuck ;)"

After the message there was two photos, one of Robin on the street with my cum still on her face and another of Robin posing naked in her bedroom, with her big erect cock in her hand.

Seeing the message and the two pictures brought a smile to my face and I wrote back with the following:

"I enjoyed last night, I hope you got back okay with my cum all over my face. I'm free this weekend if you want to meet."

It didn't take Robin long to get back to me. I received this message only a couple of minutes later:

"I did get some funny looks mister ;) but I got back okay thank you. Yay! What about next Saturday? Meet me outside my university at 2pm? xxx."

I couldn't believe I will get to see Robin again. I quickly wrote back:

"That works for me. See you then Cum Dumpster ;)"

"I'm seeing Robin again next Saturday." That's what I told myself that morning as I pictured in my head what I had in store in our next encounter. However they all paled in comparison to what actually happened that day but that is a story for another time.

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5 Comments
hotwillyhotwillyabout 4 years ago
Surprising meet

Good story, led the reading from expecting boy meets girl to male / male meet very well.

Enjoyed the story and would enjoy swopping places with him

woodseaveswoodseavesover 4 years ago
love dirty encounter

Wow, that is so hot, I could almost be jealous that you had met the ravishingly sexy Robin. I love her wanting to wear your cum on her face and feel your cum dripping out of her hole

AnonymousAnonymousover 4 years ago
Hot stuff

Just read all of your stories !!! Love them all !!!

DianeRedfernDianeRedfernover 4 years ago
Very sexy brief encounter

A great start but hopefully only the beginning.

xoxo,

Di

AnonymousAnonymousover 4 years ago
Good stuff

Hope we see more of them or other TS/CD stories from you

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