First Time with a Hooker

As I nervously knocked the front door I glanced around again. It was dark, raining slightly and the street was empty, but even if someone had been passing or were to see me leave I was pretty sure that I wouldn't be recognised. I'd driven halfway across the city to an area where I didn't know anyone, and now I was outside the address I'd found online.

The door was opened from the inside and in front of me in the dim hallway stood a woman in a short red dress, bare legs and slippers.

"Yes, love?"

"Hi, um... are you still open?"

"We are. Come in."

She turned and I walked after her, closing the door behind me. She climbed a set of stairs and as I followed her up, I could see a set of black panties underneath her dress which she made no effort to hide. Her ass was shapely, and it excited me a little as I watched her go up.

At the top was a well-lit large landing, much neater and tidier than I'd expected - actually, what had I expected? - with a couple of chairs and a mural of the Playboy logo. There were also 4 or 5 closed doors leading to other rooms, my guide opened the furthest one and invited me in. On the other side was a large bedroom with a double bed, a small sink and a long mirror that ran along one wall. She pointed at the bed and said in a gentle tone: "Sit down, love".

Now I could get a good look at her for the first time. She was about average height, maybe mid-30s with bobbed light brown hair and lightly tanned skin. She wasn't thin like a model but had a good figure, which I could see clearly as her dress was maybe a size too small, and her bra and straps were visible underneath. She was certainly attractive, and when she spoke she smiled and sounded friendly:

"So you've already had a good look at me. I'm Heidi, I'm here for the next two hours and so are the other two girls here today. I'll send them in to say hello."

Heidi left the room and I was alone, giving me time to gather my thoughts. I was still nervous, but this had gone more smoothly than I'd thought it might, and the house felt safe. I didn't have time to think much more because another woman had entered.

"Hi, I'm Joanne, how are you today?"

Joanne was a taller black woman with dark ebony skin, maybe early 40s, with frizzy shoulder length hair and green eyes. She wore only a matching set of elegant cream underwear, and as I looked at her she giggled with a girlish voice, put her hand on her hip and gave me a couple of quick twirls so I could see all of her. She was slim, leggy, but with a larger than expected bust, and immediately I knew I had a difficult choice to make. Heidi had been sexy and interested me, but now there was competition.

"Anything you want to ask me, love?"

"Um, not that I can think of. You're very pretty."

"Thank you! Well if you think of anything after I've gone just ask for me!"

Again there was only a short gap after she'd gone before the last girl walked in. Sam was younger than the other two and equally friendly during our brief chat but I simply didn't fancy her. I was learning quickly that in these situations you need to make snap decisions with your gut, and was still weighing up the merits of the other two ladies when she asked a question:

"So I'm the last girl, darling - which of us would you like to spend some time with?"

"I think I'd like to see Joanne please."

"Of course. One minute."

Pretty quickly the door opened again and Joanne came back in, smiling a little. I just sat and smiled back, not really knowing what to do next so she spoke first:

"Thanks for choosing me, love. What's your name?"

"Hi again, I'm Daniel."

"Nice to meet you Daniel, and you know I'm Joanne. You'll learn a lot more about me soon. Have you been here before?"

"No, it's my first time."

"OK, no problem. Well I'm all yours - what would you like? 30 minutes or an hour?"

"Umm... Can I have an hour?"

"No problem. That'll be £60 if that's OK? Do you want anything extra?"

The last question was delivered with a wink. For the first time since I entered the room I felt nervous again, because this was new to me and I was only partially certain of what she meant. I stuttered slightly:

"Um, what's on offer?"

"You can have oral with for an extra 20, or without for 30."

"Oh wow, OK... I've got another 30, please"

Joanne laughed a little as I fumbled with my wallet and handed over the agreed cash, then she took the notes to the door: "Get yourself undressed love, I'll be back in just a minute."

I'd imagined this moment for months but now it was about to happen I almost froze; if the women I'd met hadn't been so friendly I might have found some excuse to bail out. As it was, I slowly removed my clothes and hung them on a hook I'd spotted on the back of the door. When I got down to my boxer shorts though I hesitated. Everything? I kept them on and sat on the bed, a few seconds before Joanne entered the room again. She locked the door behind her then stood above me, still in her cream underwear, and still looking as attractive to me as she had on first sighting. I'd chosen well. She giggled again:

"You kept something on - are you a little shy?"

"Umm... Yeah a little."

"You really don't need to be, you won't want to keep them on. What would you like us to do first?"

"Umm... what do you usually do first?"

She squatted and looked into my face then spoke softly:

"I'm not going to bite you darling."

"Sorry, it's just... I'm a tiny bit scared... This is a first time for me, I've not been with someone like you before."

She smiled: "My colour, darling? We're the same you know. Same breasts... same ass... same pussy." The last word was whispered and stretched out.

"God, no! I didn't mean that! I meant, I've never paid..." My voice trailed off, I could feel myself messing this up. But she still sounded calm when she replied, and it relaxed me as we talked:

"Ah, OK. What brings you here this evening?"

"I've not had sex in a long time. And I miss it."

"How long, Daniel?"

"It's about five years."

"Why so? No girlfriend? Are you married?"

"Yes. But we've had a kid and the two of them are amazing... but now we're both tired so much, and it's been so long I don't know how to ask any more."

This wasn't turning out at all as I'd thought it might, but Joanne smiled slightly again and once more it relaxed me. At least all the cards were on the table now. She spoke again:

"It's more common than you might think, although I don't think all men are as honest about it as you are. That's OK, we don't share secrets like that outside of this place. Now let me help you out."

She reached for my boxer shorts and slid them down my legs so I was exposed in front of her. Then she asked me to lay face down on the bed. A few seconds after I did I could feel her fingers gently start to massage me; first my back, then down my arms, then she knelt between my feet and began to work her way up my legs. It didn't feel like she was a professional masseuse, but while she worked she spoke quietly, telling me to relax and enjoy the sensations.

When she reached my thighs the touches became softer, almost ticklish, and I could feel the graze of a fingernail. Growing confident at last I parted my legs a little wider as she began to caress my buttocks, then a lone finger gently ran over my anus. I gasped.

"You like that darling? Let's do a little more, I don't think you're relaxed enough yet. We've got plenty of time."

They were coming faster now, teasing little strokes all around my most sensitive areas, and I could feel my cock growing hard under me - how long until she touched that too? I raised myself a little so that it didn't become uncomfortable, and then a hand reached under and softly stroked my balls which caused me to gasp again. Still the massage continued, and then I felt Joanne shift her weight so that she was leaning over me and her warm breath was whispering in my ear: "Turn over Daniel, time for something extra."

I was less shy now. After I rolled over she again knelt between my feet and caught my eyes. She reached a hand out and placed it lightly on my erection. With the other hand Joanne reached behind her back and soon her top was removed and she tossed it onto the floor. I stared unashamedly at her full breasts with large black nipples. When she spoke again her voice was harder:

"Do you want me to suck you?"

"Mmm, please."

"Do you want to play with my tits? Do you want to play with my tits while I suck your cock?"

"Oh god, yes."

"OK, so I'm going to suck your cock. And then I want it in my cunt."

She lowered her head, I felt her lips pass over the tip, and then her tongue was swirling around my helmet, lapping at the pre-cum that was already there. The instant pleasure spread through my body and my already hard cock grew harder still. As she continued to lick and suck, I reached down with both hands and found her breasts, running the palms of my hands over their surface and using my fingers to stroke and tweak her nipples. By now I'd started to moan and soon she did the same. She drew back and looked up.

"You like that, baby?"

"You know I do. Don't stop."

Her head went down again but this time she kissed the top of my cock then began to work her way down its length, kissing and sometimes using the tip of her tongue to deliver little licks, then she would then gently blow on the parts she'd touched. When she reached my balls she used her tongue to explore them, moving from one to the other and I moaned again. Then she removed my hands from her and moved lower still until I could feel her kissing, licking and blowing just above my asshole. I'd fantasised about this but no-one had ever indulged me with such treatment. I squirmed with pleasure and arousal. My moans no longer formed any words.

Without speaking, I felt Joanne start to work her way back up my shaft until she'd reached the top. Briefly she looked up to catch my eye, then drooled saliva over the tip and began sucking me again, harder this time and more frantically. Wow! I put my hands into her hair and began pushing her head in rhythm with my hips as they moved up and down, fucking her mouth. My shyness had gone. I wanted to fuck her.

I released her head and she knelt above my chest. Without waiting for permission I put two fingers against her pants between her legs and began to explore and press.

"You want me to take these off Daniel?"

I nodded and she climbed off the bed and took them down while I watched, hungrily looking at her neatly trimmed pubic hair. When she was naked she reached into a bedside table, took out a condom and rolled it easily down my cock.

"Where would you like me? How do you like to fuck your women?"

"Lie back for me. I want to go on top."

She tilted her head back, spread her legs and I stopped for a second to take in the sight. Her naughty eyes, her slender figure, her breasts, her thighs coated with a hint of sweat, and they were all for me.

With the foreplay complete, I didn't wait for long. My cock slipped easily into her, and as I began moving I caught a glimpse of us framed in the mirror on the wall. For a few seconds I enjoyed the view of our bodies as I thrusted inside her, then turned back to Joanne whose hands were on my ass and exploring, some fingers stroking the crack. I arched my back and buried my head in her breasts, kissing and then sucking and tasting each nipple in turn. I wanted to explore all of her. I'd waited so long to do this.

She began to moan again slightly and I increased the pace, her hips moving with mine. The bed creaked slightly. Sensing the acceleration she began to speak, softly again now, though the words were harsh.

"Fuck me. Fuck me Daniel. That's it baby, fuck me hard. Fuck my cunt. It's all yours baby, fuck my pussy. Let me feel that big hard cock inside me. Mmm, that's it, fuck me. Cum for me baby, let it go inside me, I need to feel that. Oh, fuck me. Fill me up."

I knew I was close. Her hands moved closer to my asshole again, and now she wrapped her feet around my ankles, pulling me in closer. As I began to come I groaned, but still she moved her hips with mine as my cock released its load. For a few seconds more I continued to push and then, my legs suddenly weak, I lay on top of her, my cock still inside. After a short while Joanne giggled.

"How was that baby? I think you really did need that!"

"That was... amazing. Wow. Wow wow. Thank you."

"No problem, darling. Happy to help."

"Mmm, thank you."

As I was getting dressed to leave I found my wallet and tipped her some extra. For once it was me that spoke first.

"For you - that was incredible."

"Thank you Daniel, that's sweet. Will you be visiting again? The other girls will look after you too."

"I'm sure they would. But I'd love to see you again."

"I'm here on Mondays, sweetheart. Just ask for me. Maybe next time we could get up to a little more."

"Really? There's more?"

Joanne raised a finger to her lips.

"There can be now I know you. Special offers for regulars. But don't leave it five years!"

"No, I won't wait another five years."