Something Extra...

Story Info
A businessman gets a surprise from a hooker he picks up.
2.1k words
4.21
65.9k
47
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Pussrider
Pussrider
390 Followers

I'm a middle-aged businessman who sometimes has to visit London on business from my home in the north of England. I'm happily married with two teenage daughters and I normally behave myself when I'm away, but there was this one night at a hotel at Heathrow Airport...

I was sitting in the bar sipping a scotch, and there was a hen night going on, all these scantily clad young girls running around, bare legs, skirts up to their bums. Some of them were gorgeous, but not much older than my girls, and I felt like a dirty old man as I sat there ogling them. If I'd been in central London I'd probably have gone out and searched out a hooker to relieve my twitching cock for me, but Heathrow's in the middle of nowhere and doesn't offer the same opportunities.

I was just about to head off to my room, to put myself out of my misery, when I realised that I was maybe wrong about the lack of opportunity. I noticed a Latin woman sitting across the bar -- she couldn't have been there long otherwise I'd certainly have noticed her before. She was gazing over at me with an amused smile on her face, and I realised with embarrassment that she'd probably been watching me staring at the young girls. When she realised she'd caught my eye, her smile broadened and with a slight flick of her head she invited me to join her.

I knew from the moment I set eyes on her that she was a working girl: her look screamed it, though in a classy way, not a tarty one. As I strolled over I glanced her up and down. I guessed she was probably in her early thirties; she had lots of jet black hair, falling in loose curls to her shoulders; a pale complexion, with thin, plucked eyebrows, big dark eyes with long lashes, high cheekbones, a slightly overlong nose, big, pouting lips and a dimpled chin -- I would have described her as striking or attractive rather than pretty. Her dress, which reached to just above her knees, was black flecked with silver, low cut enough to reveal a decent cleavage, and sleeveless -- she had broad shoulders and her arms were very pale, and well defined with noticeable biceps, suggesting she worked out regularly. Her long, shapely legs were clad in sheer black stockings and the look was finished off with shiny leather shoes with perhaps a 4-inch heel.

I sat beside her on a plush velveteen bench and introduced myself (just my first name, naturally), and she replied, "Hello baby, I'm Francesca". She had a sexy throaty voice with what I guessed was an Italian accent. I waved a waiter over and ordered another round of drinks -- she was on white wine spritzers -- then she launched straight into her pitch. "I've seen you looking at those silly little girls. I think a man like you would feel better with a more mature lady...one with lots of experience, and something a little extra for you."

In hindsight, I admit I was naïve -- the deep, sultry voice, that reference to something extra -- but at that point my brain had left my head and was rapidly making its way south! I slipped my arm around her waist and she scooched along to press her hip to mine, her arm in return circling my shoulders. I leaned my head close and murmured, "And how much will it cost me to feel better?"

Francesca responded by emitting a low throaty chuckle and dropping her free hand into my lap, her long slim fingers pressing gently against my fast-stiffening cock. Her lips brushing my ear, she whispered, "I like a man who gets right into it. You wanna get right into it with me darling? Well, a nice massage and however else we decide to enjoy ourselves is one-fifty".

I told her I only had £100 in my wallet. I knew that because I'd restocked it from one of the hotel's cash dispensers just before entering the bar. I expected her to ask me to toddle off back to one of the machines to get the rest of her fee but, to my surprise, after a moment of hesitation, she smiled and said, "Okay" -- presumably a case of a bird in the hand. Then she took me by the hand and drew me to my feet. As we moved from behind the table the waiter arrived with our drinks, and we agreed to take them up to my room. In the lift Francesca continued to hold my hand, our fingers interlocked, her thumb tracing patterns in my palm, sending shivers up my arm. She would have been as tall as me, five-feet-eleven, barefoot; in her high heels she seemed to tower over me.

Once inside my room Francesca took my whisky from my hand and placed it alongside hers on a side table. Then she leaned into me and pushed me against the door, her whole body pressed against mine, her tongue mashing deep into my mouth. Taken by surprise, I reached my arms around her and took two handfuls of her dress. Without breaking the kiss Francesca shrugged her shoulders and the dress slipped down to her waist, revealing her large boobs. They were enhanced, which isn't my favourite, but that had gorgeous big nipples and I squeezed my hands between us, kneading her tits and tweaking the nips between my fingers. At the same time Francesca had been unbuttoning my dress shirt, and her fingernails traced across my hairy chest, she in turn tweaking my nipples. Then her hands dropped to my waist and I felt her unbuckle my belt.

I assumed we would move to the bed at that point but Francesca simply broke the kiss and slipped down my body, her lips trailing across my chest and belly. In a single movement she dragged my trousers and pants down to my ankles then her mouth closed over my rampant cock. Gasping with pleasure I wrapped my fingers in her luxuriant hair. With a moan of arousal she reached her arms around me and clutched a buttock in each hand. I knew I couldn't last long, and in seconds I gasped "I'm cumming". Far from pulling away it seemed Francesca sucked and licked at me all the harder, and as I shot my load into her throat she jerked two fingers hard up my arse. The effect was electric: I groaned and thrust at her face, ejaculating even harder.

As I finished I slumped back against the door, eyes closed, gasping for breath. I felt Francesca rise, and a moment later her arms circled my neck. She kissed me again, smearing my jizz across my tongue. Then, with a chuckle, she whispered, "Okay sweetie, now you're relaxed we move to the massage. Take your clothes off and lie on the bed while I get ready." With that she took a sip of her spritzer then strolled into the bathroom. Her dress had slipped off entirely and my eyes alighted on her jiggling bum, clad in only the narrowest of thing panties. I drained my whisky and, on slightly shaky legs, hobbled by my trousers, I shuffled over to the bed and undressed, then lay on my belly in eager anticipation.

A minute or so later Francesca returned and, lightly running her fingertips across my shoulders, she murmured, "Okay darling, you ready?" Moments later she straddled the small of my back. I was momentarily aware that something didn't feel quite right, but then she began massaging my neck and shoulders. Her hands were soft but she applied firm pressure, and I could feel my skin and muscles beginning to warm as she kneaded them.

After a few minutes Francesca moved further down my body, and that was when I began to realise the misunderstanding under which I was labouring. Something long, hard and warm was nestling between my buttocks. Either this lady was wearing a strap-on dildo or...then she began to stroke my back not only with her hands but also with her nipples and her tongue. I moaned with pleasure and momentarily forgot what I had just been thinking. Next she knelt between my legs and began to knead my buttocks. After a couple of minutes she changed her approach: one hand cupped my balls, two fingers stretching up to caress my shaft, while the other hand passed deep between my buttocks in a series of sweeps, creating surprisingly erotic sensations. She briefly massaged my legs and heels then slapped me lightly on the bum and giggled, "Okay baby, time to turn over."

I rolled onto my back, in a moment Francesca straddled my chest...and suddenly my misunderstanding was staring m in the face. As Francesca grinned down at me a big, meaty, hairless cock rose up before my eyes, 'her' balls resting on my throat. My shock must have been clear on my face, but she shuffle forwards and used a hand to angle the tip of her dick to my lips, then whispered, "Come on honey, suck me then fuck me."

I'd never thought in my life about having sex with a man before, and now I was laying there stiff hot cock pushing between my lips and pressing up against my teeth. Francesca reached behind her and tickled her finger tips up my cock -- that made me gasp and, snatching her opportunity, she twitched her his forwards and thrust her dick into my mouth. Almost instinctively my lips closed around it and my tongue traced its length. Francesca sighed appreciatively and started to see-saw back and forth, fucking my mouth. In spite of the reservations I'd felt, within a few seconds I started to get a feel for it and I began sucking her dick in earnest, my tongue massaging it and swirling around it. The feeling in my mouth, apart from its rubbery tip, was of a steel bar clad in heated velvet. As she fucked me I could feel Francesca's balls gently slapping against my chin. I gripped one of her buttocks between each of my hands and kneaded them, my fingers slipping into the crevice of her arse.

After maybe two minutes she pulled out and shuffled her bum down to my midriff, then finished herself off with her hand, shooting her load onto my chest. Amazingly, until that moment I hadn't even considered the possibility that she might cum in my mouth. I lay back on the bed, panting, while Francesca massaged her sticky juices into my chest hair. Rather surprisingly, sucking another cock had had a remarkable effect on my own, which was ramrod stiff. Francesca produced a condom from somewhere and applied it to me, then stood above me on the bed and swivelled, dropping back down with her back to me. I assumed she'd let me fuck her doggy style, but she surprised me again. Kneeling either side of my hips she manoeuvred my cock to the edge of her hole then sank down on me, riding me reverse cowgirl style. She bucked up and down, driving me deep into her, her head swinging wildly, gasping loudly with each thrust. I held on as long as I could but after no more than a minute I exploded into the condom, my hips rising to meet Francesca as she descended onto me. She made two or three more thrusts then lifted herself off me and collapsed onto the bed alongside me, her chest heaving as she gulped down breaths.

We lay kissing and cuddling for a few minutes, our tongues unselfconsciously wrestling together and our prices happily rubbing together, then I lay back and watched Francesca as she dressed. Just before she left she kissed me on the nose and, with a smile, whispered "Next time darling, I get to fuck you."

I slept deeply that night. The following morning I did feel a little embarrassed, and I told myself it was an aberration that would never happen again. Three weeks later, back in my home town, I made a date with a local T-girl, a very pretty petite lady, maybe 23 or 24, with a cute Scots accent and strawberry blonde hair. We 69'd -- her cock felt tiny in my mouth compared to Francesca's -- and I fucked her while she lay on her back, her hands holding up her thighs, her dick and balls bobbing between us. I'm sure back in London next week, and I've booked a five-hour dinner date with Francesca. My cock twitches in anticipation every time I recall what she said would happen next time we met.

Pussrider
Pussrider
390 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
9 Comments
AnonymousAnonymousover 2 years ago

Thanks for the tag. Saved me from reading this crap.

AnonymousAnonymousover 6 years ago
Part two?

I'd love to see a story about the 5 hour second date.

AnonymousAnonymousabout 7 years ago
Yes, is anyone there that wants to talk about it?

I do

AnonymousAnonymousalmost 8 years ago
Hot baby

Love the way you slipped your cock in my mouth, baby! Wish you'd facefucked me with mouthfull of cum!

AnonymousAnonymousover 8 years ago
Great style

Love the way she tricked me to open my mouth! Love to feel her juicy cock coming in my mouth!

Show More
Share this Story

Similar Stories

Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
Shemale Bar Straight guy goes into a shemale bar and is forever changed.in Transgender & Crossdressers
Shemale Sister-in-Law Man gets massage from sister-in-law with shocking results.in Transgender & Crossdressers
A Surprising Landlady A new tenant gets an unexpected but welcome surprise.in Transgender & Crossdressers
The Happiest of Endings A massage with a big, hard surprise.in Transgender & Crossdressers
More Stories