What a Surprise!!

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A night out ends up with a most amazing surprise.
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litty700
litty700
145 Followers

I had the experience of my life a couple of weeks back which I like to share with you. I work in the centre of London and as was the norm for a Friday night I was out with my colleagues for a drink after work. We normally went to a bar just round the corner from our office, but this time decided to venture further afield. I'd never been to this place before but it looked a lively old venue, with some good loud music going on and a good mix of people in there. As usual we took in a few double G&T's between our group and the conversation turned ever more ridiculous. I had been to the Men's Room a couple of times and on each occasion had spotted a very attractive young lady...well young to me, I'd have put her mid thirties, looking at me. I didn't give it too much thought and carried on my evening. Gradually my work colleagues began to drift away for the weekend, leaving just a few of us left.

"Anyone fancy heading off elsewhere?" One of them suggested.

Those that were left were in agreement, but I decided I was done for the evening and decided to call it a day. These guys had twenty years or so on me and I knew they would still be going for another few hours at least and I knew I wouldn't be able to handle it. After jokey accusations of being a lightweight, I grabbed my jacket and we all made to leave, with me intending to head straight to the nearest tube and go home. However, as I looked back into the bar, I once again noticed the lady, who was with a group of friends, looking at me with an inquisitive smile on her face. I wasn't quite sure what to make of this, but left the bar with my group. We said our farewells and they made off down the street. Not really sure why, but something about that lady smiling at me had peaked my interest so I decided to head back into the bar and have one for the road. As I walked back in I noticed she was no longer at the table. Oh well I thought, maybe she'd left by the other exit whilst I was outside. I thought I may as well get another drink as I'd come back in and it was then I saw she was actually at the bar waiting to be served. I was a bit out of practice on this front, being married, and knew I really shouldn't be doing this, but totally blaming it on the drink I took the plunge and approached her.

"Hi," I said, appearing to make her jump as she hadn't see me.

"Oh, hi", she replied, that warm smile once again appearing on her face.

It was now I really just how attractive she was. She as slightly shorter than me and had long wavy dark copper hair, presumably not her natural colour, and big blue eyes. She was wearing red high heels and a knee length black skirt and a red patterned blouse. I assumed she was dressed up for the night and hadn't come straight from work.

"I'm Dale," I offered.

"Nice to meet you Dale, I'm Stacey," she answered, shaking my hand. We both laughed and I felt myself visibly relax.

"Can I get you a drink?" I asked.

"Ah, I was just about to get a round in for my friends, but tell you what, I'll grab those and you can shout me one. I'll have a Vodka and Soda please."

"No problem, a double good for you?"

She laughed, "Hell, why not, it's Friday after all."

We both eventually got served, always a challenge on a busy night in these places.

"I'd ask you to come and join our table, but some of those guys are mad and will probably send you running. How about we see if we can grab a table elsewhere?" she suggested.

"Good with me," I replied.

Stacey took her tray of drinks over to her friends whilst I made my way to the back of the bar and managed to find a couple of seats at the end of a long table. Stacey joined me shortly afterwards. Maybe it was the drink, but I felt very relaxed chatting to this lovely young woman and we ended up having a few more drinks and staying even after her friends had come over and tried to persuade us to go with them to a nightclub. We both politely declined and were met with comments of "Don't do anything I wouldn't do" and "Make sure you use a condom" etc. etc. Stacey jokingly told them to "Piss off" and go and have a good time. They left the bar, by which time it was around ten thirty.

"So have you got a home to go to?" Stacey asked me, "and a wife?" she added, clearly having noticed the gold ring on my finger.

"Oh, well yes I suppose, but..."

"Hey, who am I to judge," she said, "Your secret is safe with me. My place is a few minutes around the corner if you wanted a night cap?"

I quite often stayed overnight in London, either booking into a hotel or crashing down at one of my workmates, so my wife would be none the wiser. I could probably still catch the last train home. Then again what was I even thinking? This wasn't like me at all.+

"Actually I probably should get going," I told her.

She put her hand on my leg and slowly moved it upwards.

"Okay, if that's what you want, I understand, but I've really enjoyed your company, would be a shame to call it a night wouldn't it?"

Christ, I could feel my cock starting to harden, and I was sure this wasn't going to end well.

"Oh why not, the night is but young," I replied.

"Drink up then," Stacey told me.

We both downed our drinks and then left the bar. The cold night air quickly seemed to sober me up and I had all sorts of thoughts battling in my head, but it was the lower end of my body that was winning that particular battle. I had a look around to make sure I didn't recognise anyone. I was sure my work colleagues would have long since gone. Stacey noticed me looking a bit nervous.

"I can walk in front of you if that would help," she suggested with a wink.

"Ha ha, no it's fine, it's not like we are doing anything wrong," I replied.

"Are you sure about that?" she said suggestively.

About five minutes later we had arrived at a modern looking block of flats and made our way to the fifth floor. She had a very nice apartment, very modern and clean looking, with a view out of one large window in the lounge area looking out across the river. Must have set her back quite a bit.

"You like?" she asked taking her coat off and hanging it up, motioning for me to do the same.

"Yes very nice," I answered.

"I work in the Banking Sector," she offered.

I nodded. That would explain it, I knew there was a lot of money to be made there and if her working abilities were on par with her looks, then little wonder she was doing so well for herself. She went to the drinks cabinet and grabbed a couple of glasses.

"More Gin?" she asked.

"Yes please, probably best not to mix it up," I'd already had more than enough, but the walk had helped.

We sat, quite close together, on the sofa and chatted for a while. It wasn't long before Stacey reached over to kiss me and I responded. She tasted very sweet and I couldn't get enough of her. We eventually broke apart.

"Wow, that was nice," she giggled. I just smiled in response.

She slipped off the sofa and knelt down in front of me.

"May I?" she asked. Not sure anyone had been that polite before.

"Go ahead," I smiled in response.

Stacey slowly undid the belt on my trousers and then in one move pulled my trousers and pants off, letting my now raging hard-on spring free.

"Impressive," she said approvingly, "and you keep yourself nice and trimmed down there, I like that."

"Makes it look bigger," I joked.

"It's big enough for me," she replied with a glint in her eye.

She began to trace her tongue up the inside of both my legs. I was so turned on it was beyond belief. I could already see the pre-cum at the tip of my cock and she hadn't even touched me yet. It was long before her mouth was within touching distance of my balls. Stacey gave them a little flick with her tongue and a I let out a little cry of approval. She looked up at me with a big smile on her face. I sat up a bit straighter and she positioned herself so my cock was nicely in line with her mouth. Stacey slowly ran her tongue up the length of my shaft before wrapping her hand around it and starting to wank me. I let out another groan and put my hand on hers to stop her.

"Is everything okay?" she asked, looking a little disappointed, "I understand if you're having second thoughts."

"It's not that," I groaned, "but if you stroke my cock anymore I'm going to cum everywhere."

Stacey laughed. "Well that's okay, isn't that what you are here for?"

"I suppose, but there's no rush is there? How about you lie back and take your turn?"

"Okay," she replied, but something in her response seemed a little odd, "I'm quite happy to sort you out."

"I couldn't let you invite me into your home and then let you do all the work," I teased.

I stood up, my erection still proudly on show, and guided Stacey onto the sofa. I undid her blouse, revealing a very sexy black silk bra and then I headed downwards parting her legs so in return I could trace a path to her waiting pussy. Stacey seemed to have visibly become a bit nervous as I stroked my hand up the inside of her thigh and even more so when I reach the top of her stockings. It was now her turn to grab my hand.

"Stop," she begged me and I did as she asked. "There's something I should have told you."

I didn't quite understand, but I'm sure whatever it was it couldn't be that bad. Time of the month perhaps?

"What is it?" I asked genuinely concerned, "is everything okay?"

Stacey was looking very sheepish. "I'm so sorry, I should have told you, but you seem so nice and I didn't want to scare you away."

"I'm not quite sure what you mean," I replied.

"Okay, look feel free to carry on, but honestly I will understand if you grab your coat and run out of the door."

I honestly had no idea what she was so concerned about, if it was her time of the month I'm sure she could tell me. A weird birth mark perhaps? I was still very turned on, so whatever it was I wasn't going to let it spoil this moment with the lovely Stacey. She let go of my hand and lay back down, whilst I got back on with venturing north of her stocking tops. Moments later I felt the silkiness of her underwear and as I touched it, I then, with some kind of shock and also curiosity that had my cock get even stiffer, if that was possible, felt a bulge that I knew could only be a pair of balls in the bottom of her knickers. It seemed that both of us froze for a brief moment, but what the fuck I thought to myself, in for a penny and all that. I slowly massaged her balls through her pants and felt her relax back down as she let out a groan. I stopped and then pulled her skirt down to reveal a fully fledged rock hard cock poking out of her skimpy underwear.

"Well I wasn't expecting that," I laughed, in a nice way of course.

"I really am sorry, I should have told you, I never really know how to quite broach the subject."

I guess like most men I'd had the odd fantasy about being with another man, so I suppose this was the best of both worlds.

"Shush," I whispered and peeled her knickers down over her stockings and let her kick them away.

Stacey's balls and the surrounding area were completely shaved, as was the rest of her body from what I could tell. The scent from balls was intoxicating and I suddenly found that without hesitation I wanted to suck her.

"Stand up," I said to her and she duly obliged, leaving her cock nicely in line with my mouth.

I had never done this before so I hoped I wasn't about to mess up. Taking her cock in my right hand I leaned forward and wrapped my mouth around her glistening helmet. I'm not sure what I expected it to taste like but it was actually rather pleasant As I sucked on Stacey's helmet I found myself getting more and more turned on and began to stroke my own shaft at the same time. Stacey unclipped her bra and threw it onto the sofa. She was now down to just her stockings and shoes. Not that I could see much, but I could tell she was now playing with breasts whilst I was going down on her.

"You are doing that so well," she moaned, "are you sure this is your first time sucking a dick?"

I chose not to answer that and carried on sucking her beautiful cock whilst wanking mine, which was now close to exploding. Too late to think about that any longer. I suddenly let go of Stacey's cock and cried out in ecstacy as cum exploded from my cock all over her stockings and shoes and, embarrassingly, her very fancy looking carpet. I was past caring.

"Oh, that is so hot, go on shoot it all over me," she urged, starting to stroke her own cock at the same time.

I furiously pulled at my cock draining every last bit of cum that I could from it and wiping it down her stockings. I could hear Stacey groaning as she too pulled at her cock which was still very close to my face.

"Open wide, I'm going to cum," she called out.

I didn't have any time to think and just opened up my mouth, whilst still stroking my now softening cock, and let Stacey shoot into me. She stood legs apart tugging at her cock as spurt after spurt shot into my mouth. I tried to keep my mouth open, but ended up having to swallow what I could as the last remnants of her ejaculation landed on my face and down my shirt front. Both of us continued to stroke ourselves until we were totally spent. I then took her soft cock in my hand, which felt very good indeed, and pulled the skin back and forth over her helmet.

"That was nice, sorry I couldn't hold on much longer. Watching you cum was too much for me. Hope you didn't mind me cumming in your mouth?"

"I guess I didn't have much choice," I replied getting to my feet. "Sorry about your carpet."

"Don't worry about that, it's not the first time," she laughed.

We both sank back into the sofa and cuddled up for a little while, feeling pretty tired after the frenzied activity.

After a while I suggested it would be a good idea if I went home, but Stacey pointed out I would not get the last train out of town now so would be best if I stayed over. She offered me the spare room, but said she would be happy for to share her bed. Guessing there was a bit more than sharing the bed on offer I accepted. We made our way to her bedroom and stripped the rest of our clothes off before getting under the covers. Stacey wrapped her arms around me and started to kiss me again.

"Er, you do know I've just had a mouthful of your cum?" I said.

"And you think I've never tasted my own cum?" she replied mischievously. I didn't doubt that for one minute.

It wasn't long before we were both hard again and stroking each other.

"Would you like to go a bit further this time?" Stacey asked me with a wicked smile on her face.

"How do you mean?" I answered.

She broke away and opened a drawer in her bedside cabinet. She took out a condom and a bottle of lube. I knew exactly where this was going and once again felt another hardening shudder in my penis.

"Don't worry, I'll go easy with you," she said, "but let's have a little more fun first.

Stacey lay me down on my back and then straddled me in the sixty nine position so we could both suck on each other. She still tasted as good as the first time. I licked the fresh pre cum from her as she sucked the full length of my shaft. I could tell she'd had plenty of practice. She was playing with my balls at the same time, and then pushing me up a bit, she slipped her hand underneath me and start to probe at my anus with her fingers. She was having difficulty getting inside me, so grabbed the lube and within seconds had slipped a finger straight up my passage. Fuck that felt so good. I stopped sucking her and shifted my position so she could get right inside me. Stacey pushed another finger inside and started to finger and fuck my hole good and hard. That was enough for me, I couldn't hold on and for the second time that night a jet of cum left my cock and went straight into her mouth and down her throat. She continued fingering me and wanking my cock until she had squeezed every last bit of cream out of me and swallowed the lot as I groaned in pleasure. She certainly knew how not to waste it. She continued sucking me as I softened up until I could take no more.

"Mmmm, you taste so good honey," she purred lying back on the bed, "My turn now."

Having already seen the condom, I was prepared for what was to happen next. I went to get onto all fours so she could penetrate me from behind, but she beckoned me to stay on my back.

"If this is your first time I want to see your face," she grinned.

It was most definitely my first time and after getting me positioned to her liking, she took the condom out of its packet and slipped it onto her cock. A good dose of lube later and her helmet was pushing at my, rather tense, anal opening.

"Relax babe, it won't hurt I promise," she urged.

Stacey was true to her word and very gently and carefully got the whole of her penis inside of me. She kept it very still until she was sure I was happy with things.

"Okay?" she asked.

"Uh huh," was all I could manage in reply.

She leant down and gave me a long kiss before slowly beginning long thrusts of her cock into my arsehole. I felt stretched as the length of her penis filled me right up. I have to admit it was extremely pleasurable and I found that my flaccid cock was starting to get hard again very quickly. Stacey had noticed.

"Wank it for me, let's cum together," she commanded.

I duly obliged.

"Mmm, you're fucking loving have your first cock aren't you?" she moaned.

A stifled "Yes," was all I could manage in reply.

I felt in heaven with this beautiful woman fucking my arse and I could tell she was ready to cum as her thrusts got harder, deeper and faster inside me. I could feel my own build up happening again, three times in one night, that hadn't happened for as long as I could remember...if ever. Stacey, if it was possible, managed to push even deeper inside.

"Cum now," she screamed and as she pulled straight out of me and tore off the condom I ejaculated at the same time she sprayed her own jizz all over my hand and cock. We both wanked ourselves into a frenzy yet again, cum going everywhere, mainly on me. All of it got mixed together in one big mess as Stacey lay down on top of me and thrust her tongue into my mouth, mainly I think so I could get a taste of my own cum from earlier. We lay like that for a while until we both came down from our high. Stacey had an en suite bathroom so we made our way into the shower and cleaned each other before finally hitting her bed out of exhaustion and sleeping the rest of the night away. I had dreams that night like I'd never had before, mainly in anticipation of what would happen after this most amazing night.

litty700
litty700
145 Followers
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13 Comments
algolfcrazyalgolfcrazyover 1 year ago

Wow.Loved this story

SiamKittSiamKittabout 2 years ago

Not a long, drawn-out story, just a simple tale of sheer pleasure...A guy willing to carry on despite the shock of a cock, and the trans keen to have him despite the wedding ring he has... Happy ending, but needs a follow up for sure.....

ShortyMacShortyMacabout 2 years ago

What a great story. Wish I could meet a hot T-girl like her. It’s been too long sence I have been with a hot T-girl.

Rapier875Rapier875over 2 years ago

That was good.

Needs a follow up chapter though......please ?

Rapier

AnonymousAnonymousalmost 4 years ago
Lucky bastard

You are so lucky, wish I could experience that.

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