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Rachel takes it further

Tags: strap on, anal
Rachel introduces her boss to the delights of anal sex

Ah, Las Vegas . We’d landed on time, and after going through immigration, had arrived at our hotel. I’d never been to America before and I was taken aback at the sheer size of some of the hotels and the sight of escalators in the street. The weather was lovely and warm, the sun shining and Dickie was a nervous wreck. He’d spent hours trying to dissuade me from coming, but to no avail. I had him over a barrel, and after how he’d treated me for so long there was no way I was going to let go. Already I was scheming how to ensnare him deeper. Like most men he was always vulnerable to a honey trap, all it needed was the right bait…

The taxi soon whisked us from McCarran Airport to the Mirage hotel. I’d booked our rooms over the web, one luxury suite and one standard room. The luxury suite was for me. As Dick checked us in a porter took my bags up to the room and showed me around. It was wonderful, with a Jacuzzi and more or less everything you could wish for. I sort of hoped that his room would be a bit grotty, but really I knew it would be of a good standard, but mine – oh man mine! I undressed and took a shower, more from habit than anything, then got out of the shower into the Jacuzzi. As the bubbles played around my body I got to thinking. I looked at the hotel guide, there was so much to see and do without leaving the hotel. I wondered if 5 days was going to be enough time!

Drying myself off I rang Dick. “Hi, room ok?”

“Yes, it’s fine”, he answered duly

“Now Dickie, you sound a bit sulky – lets have none of that. We’re here now, so let’s have a great time, there’s lots to do. I’ve been looking in the hotel guide. They do adult movies would you like to watch one of those?”


“I bet you would, Dickie, I bet you’d like to watch one and wank yourself silly while you do”.

“Look Rachel…”

“It’s ok Dickie, your little secret is safe with me – at least as long as you play along with me. I’ve been checking out my clothing, I could really do with some new stuff you know something more – sexy I guess, so I’m going to go shopping, wanna come – shopping that is?”

“Rachel, you know I can’t. I have meetings to go to…”

“Ok Dick, you go to your meetings while I sort out something nice to wear for when you take me to dinner. We are going to dinner later aren’t we Dickie?”

“Yes, anything you say Rachel”

“Good. Well I’d better be off then. I’ve got the company credit card, so I won’t need any money off you. See you later”

There was a muffled noise from the phone as I replaced the receiver. I grinned. I wasn’t really going to use the card, but a little fear would help the situation along.

I took the lift to the lobby, then spent the next 45 minutes trying to find my way out of the casino. I wasn’t really tempted, gambling doesn’t do anything for me, maybe I’m just too cautious, but I work too hard for my money to lose it on the turn of a card. Eventually I found my way out on to the strip, found a mall and started looking at the selection of clothes. They were nearly all designer names and considerably more than I could afford. Sighing a little I turned down a side street and looked along there for a bit. I must have struck lucky because there just down the road was a dress shop. I looked in the window, trying to work out the type of thing they sold and whether I would like it, but the glare of the sun defeated me so I went inside. The clothes were wonderful, but all of a “sexy” nature. Beautiful sequined dresses, with net bodices that were so see through, short, tight skirts, and lingerie that had to be seen to be believed!

I wandered around, feeling the soft material, wondering how I would look in some of the more outrageous costumes. One of them looked wonderful on the model. It had a soft filmy skirt, with a tight plunging neckline. I didn’t see how you could possibly wear a bra with it, and sighed softly for the figure to fill it.

‘Hi’ a voice said, ‘can I help?’

I looked up to see a smiling assistant. She looked young and fresh, pretty in a nondescript way. I thought the smile looked a bit   professional.

‘Not really’, I said, ‘I’m only browsing’

‘Ok, but if you need anything just let me know, and don’t forget to have a look in our other room too’.

‘Other room?’

‘Yes, for more’, she hesitated, ‘for more – personal needs’

‘Really? I may just have a look in there now’,

My mind was on Dickie, and how I could control him even more. The girl stepped aside and I passed her and walked toward a door I hadn’t seen before. There was a disclaimer stuck to it saying no one under 18 was allowed in. I pushed it open and went inside. It was dark, at least dimly lit, but as my eyes became accustomed to it I could see various mannequins draped in what could only be called fuck me lingerie, and row after row of sex toys. There were vibrators, dildos, strap on penises, and every conceivable variation on the theme. The girl followed me in.

I gazed around, almost unable to believe my eyes. ‘People buy this stuff?’

‘Hey, don’t knock it till you’ve tried it, we sell lots of this “stuff”, come on, let me show you around’

Together we moved further into the room, ‘Right’ said the girl, ‘My name’s Sandy , we’re now going into the ladies section, you’ll find everything you could possibly want in here for yourself. We sell wonderful lingerie, toys, oils and lubricants. We want you to be completely satisfied with your purchases, so I’ll be here to advise if you wish’, I noticed how she had emphasised the word satisfied and smiled inwardly. Already I could feel a slight arousal at the thought of using some of the toys in here, ‘also’, she continued, ‘we have a gentlemans section, for if you want to spoil your man, again, just let me know if you want advice. I’ll leave you now to browse’

I browsed, man did I browse! I looked along a row of vibrators, some of which looked positively menacing, some with knobbles running down their length, some black, some pink and every colour in between. I looked at the lingerie, peephole bras, split crutch panties transparent negligees and wondered…

Turning back to the toy counter I looked at the strap on toys. A plan was forming in my head. The girl came back ‘You interested?’

‘Er yes – a little’

‘Well, these are really for lesbian use, do you want it for a girl or a man?’

‘A man’

‘Well you need the smaller girth ones – no sense in killing the poor guy’, she grinned.

I smiled in return, ‘Oh no, suffer a little maybe, but that’s all’

She reached up to a shelf and pulled down a smaller pack, ‘You’ll like this, it’s specially made for your purpose, and it has a small clit stim, so while your fucking him you’ll enjoy the ride just as much.

I looked at the obscene phallus and tried to visualise myself wearing it. I couldn’t.

‘You want to try it on?’

I was chickening our rapidly, ‘No, no thanks, maybe I made a mistake – I must go’

‘It’s ok, you’re nervous, most girls are the first time, let me show you how it fits…’.

‘No, oh no – I couldn’t…

‘…On a model, silly’, she smiled again ‘it’s really pretty easy, watch.

She took the strap on out of the packet while I watched with reluctant fascination, she slid the harness around the thighs of the model, attaching the crutch strap to the girdle at the back. ‘This is the best bit’, she said grabbing the phallus and yanking it up and down in an energetic manner that would probably have most men in tears, ‘the harder you fuck, the more the clit stim works. You’re gonna have a ball with this – sold, yeh?’


‘Right, don’t forget to lube him up or you’ll not be too popular, we use this, my boyfriend swears by it’, she handed me a small bottle, ‘it’s really good and a little goes a long way, if you get my drift’, she smiled

I was embarrassed, excited, turned on by the thought of using this on Dickie, but most of all anxious to get out into sunlight again. I paid and left, wondering if I had bitten off more than I could chew this time. I passed the rest of the day sight seeing and had a great time. When I got back to the hotel it was just turning 6pm , so I knew Dick would be finishing his meeting at any time. I rang his room and left a message, ‘Dinner for two, my room – 8.30, don’t be late. My treat’. He’d wonder what had hit him. I never buy him dinner. Now I set myself to preparing for him. I lay in the Jacuzzi for a little while, just enjoying the jets and thinking I would have to get one of these. Then I got out, dried myself and finally plucked up the courage to look at the strap on. I was a little daunted when I got it out of the packet. Various straps and loops of leather seemed to hang from it, but I eventually figured out which were the leg holes and stepped into it. I drew it up to my hips and reached between my legs for the strap to connect up the harness and pulled it up between my ass cheeks. As I slid in the catch I felt it pull up between my legs as the clit stim came into contact. She was right, this was going to be something else…

Now all I had to do was keep it under cover until the time was right. I pulled on my dressing gown and waited for room service to bring in the meal. I’d ordered it for 8.20, so I had time to preview which film I was going to use. I selected the “adult” section from the T.V. and chose one with lots of anal content. In spite of myself I was becoming more and more aroused at the thought of what Dickie was coming into. I could feel my pussy lips moistening around the harness. I tentatively looked down and saw the hard cock looking back at me. I wondered what it must feel like to have one of those things, to feel it harden and to stroke it, to make it come just like Dickie did.

At exactly 8.20 there was a knock on the door, the waiter brought in the food and set it out on the table, now I was only waiting for Dickie. He arrived as I was tipping the waiter, and looked astonished as I was dressed only in my gown. The waiter grinned and closed the door, he knew what was going on.

‘Come in Dickie, sit down. Had a good day?


‘Well, come and relax, I thought we’d have a nice meal then watch a bit of TV, you might unwind a little don’t you think? Come and sit next to me, are you hungry? Could you eat a steak?

‘I can always eat a steak, medium rare’.

‘I know, I remembered, enjoy this then.’ I lifted the cover on his plate and watched him tuck into his meal I made sure his thigh always stayed in contact with mine as he leaned forward and back while eating.

‘Your not eating Rachel’

‘No, I just wanted to make amends for being so beastly to you’.

‘Aw hey, don’t worry too much, I’ll cover these expenses and I’ll find a way to cover you coming out here with me too – don’t worry’. He wiped his lips on the napkin, ‘that was delicious’

‘Good, sit down while I turn on the TV and get you a drink’

Three large whiskeys later I turned on the film. I sat close to him waiting to see his reaction. It started quietly enough, but soon the girl was fishing the guys trousers and brought out his cock to show the camera. I had let my hand drop to Dickies thigh and was working my fingers round and round in circles slowly ascending his leg. He shifted uncomfortably

‘God, Rachel this is just porn’

‘I know, is it doing its job on you?’ I said shifting my hand over his hardening cock, ‘I do believe it is’ I continued to stroke him through his trousers feeling him getting harder and harder. Before long his hips started thrusting up to meet my questing fingers ‘Nice?’ I murmured. He took a minute to reply his eyes were fixed on the screen. By now the couple had been fucking for a while, his cock sliding in and out like a piston, ‘Oh God yes’ he breathed.

‘Let me undo you a little, in fact would you like to undress, I want to see you naked, hard.’ I undid his shirt buttons sliding my hands over his body as I did. His trousers slid down and he stepped out of them. I knelt before him and slid down his jockeys. His cock sprang free, hard and proud, slapping against his stomach. I caught it gently in my hands and started slowly wanking him. I rubbed him against my cheek feeling the precum oozing from the tip of his shaft, ‘Oh Rach…’.

‘Shsss, watch the film and let me do all the work’ I whispered as I licked along his shaft.

By now the man was fucking the girls arse. I watched fascinated as he slowly slid in to her more and more aware of the strap on. God, I was getting so turned on myself. My pussy was soaking wet and I had to use all my self control not to stroke it. I wanted to be touched, dammit, I wanted to be fucked. This was all going wrong

“Would you like that?” I murmured as a stroked along his shaft.

“Yes, I’d love it”

“Touch me”, I whispered, “touch me wherever you want to”

He looked at me “Rachel!” His hand slowly slid into the top of my gown and came to rest on my breast.    His eyes never left the TV but his hand slowly groped around finding the nipple and flicking over it with his thumb. I took my hand away from his cock and heard him sigh, “no, no don’t stop”, I reached behind me and poured a small amount of lube onto my hand. “I’m only stopping to make it better” I whispered as my hand slid slowly over the head of his penis, “There, I’m back again, lay back and relax”.

I kept on stroking him, feeling my way. I wanted him hot and hard, and he was certainly that, but I didn’t want him to come yet. I let my hand trace down a little caressing around his balls, then lower still until I was just resting between his arse cheeks. My finger was still covered in lube and I circled around his arsehole slowly, gradually increasing the pressure. I waited for him to push back at my finger as it slowly widened his arse. There! There it was. He shifted against me pushing against me. “You want it inside there?, you want me to push it in?” I whispered to him.

“Yes, Oh God yes”

I gradually increased the pressure, feeling my way gently and slowly passed the sphincter muscle, stopping as he groaned then sliding a bit further until my finger was fully home. “Feel good?”

He didn’t answer, at least he didn’t speak, but he moved against my finger as I licked slowly around his balls. Now came the moment.

“Dickie, feel me, feel my cunt see how wet I am”

“Oh God Rachel…Hellfire!! What’s this!!”

“This is what is going to fuck your ass Dickie, feel it, feel how it’s hard, nearly as hard as you. It’s going to slide deep into you and you’re going to love it. But first you need to lube it up, come on Dick rub the oil in and stroke me, just like you stroke yourself ”.

Dicks face crumpled, and for a moment I felt sorry for him, but then I remembered how much misery he had caused me and I hardened my voice.


‘C’mon, rub it, here’s the lube’ I handed him the small bottle, ‘rub it in.’

I waited, not sure of what I would do if he refused, but I was so turned on myself, I’d have to do something.

He took the bottle.

‘That’s right, now take off my robe”

He undid the belt and slid it from my shoulders. I heard his breath catch as my breasts were revealed. I knew the nipples would be hard they stand out and I have to admit I love them being sucked and teased. Dickie did just that. He licked his way around one, then slipped across to the other. His hand came into play as he caressed my right nipple, while sucking on my left. I was in heaven! He pushed me back on the bed and his hand left my nipple and slid downwards. I had to stop him now, or I’d lose control all together.

‘No’ I pushed him away, ‘NO’ He stopped, but looked at me like a puppy that had had it’s bone taken away.

‘Now’, I said, ‘lube up this cock, you’re going to love this’

Slowly, tentatively he reached out and took the bottle from my hand. I watched as he poured a little onto his hand.

‘You may need more than that, Dickie’

He took no notice, but wrapped his hand around my false cock and stroked along it’s length. The slit stim moved against me as he did so and I gasped. Oh man, it felt so good. He kept on stroking the cock and every time   he moved along it’s length the clit stim moved along mine. This was getting out of hand, in a moment he was going to make me come.


‘Why, you’re enjoying it aren’t you?’

‘Just stop – NOW’

Looking a little crestfallen he did so and waited.

‘Now, turn away from me and kneel down.’

‘Aw c’mon Rach…’

‘Do it.’

I held my breath.

Slowly he turned and taking a deep breath he kneeled facing away from me.

‘Good boy. Now open you legs nice and wide and get that ass up in the air. I want to see you.

He did as I told him to.

‘That’s good, we’re getting the hang of this now aren’t we. You are just here for my pleasure, and my pleasure is to dominate you – now hold your ass cheeks wide apart.’

Slowly his hands appeared around his back and pulled on his ass cheeks. He stretched himself wide open. His asshole looked tight, but glistened with the lube we’d been playing with. I took some more from the jar and gave it a good fingering, getting the slippery lube deep inside him. He groaned

It was time.

I positioned myself behind him and allowed the strap on to slide up and down his crack. Each time it slid over his asshole I pushed a little, until it just slid in. I heard him gasp, then felt him pull away slightly. ‘No’, I said, you stay right there’

I pushed forward a little, he was still. ‘That’s good, just stay still.’ I reached around to feel his cock. He was hard as iron and drooling precum. I continued pressing slowly deeper inside him.

“Ah, it’s hurting.”

I stopped and just let him adjust to the newness of his ass being fucked. I didn’t move, just waited, and sure enough I felt him push back against me in a moment. As a reward I stroked his cock a little. I heard his sharp intake of breath as I did so and smiled.

“Good boy, you can take it can’t you.”

I withdrew just a little and let the clit stim slide over me, mmmm it felt delicious. Dickie had realised what was going on by now and started to join in.

“You like that don’t you?” he whispered to me, “slide it back in and feel it over your clit.”

I was losing control again and tried to regain some semblance of it by pulling out altogether. I heard Dickie sigh. “You need more lube?”, I asked

“Yes –   yes please, then come back to me, please come back to me,” he groaned.

I took the bottle and let the lube dribble over my fingers again, then slid two deep inside his ass. He bucked back against me as though he were going to come right then.

“Whoa there, steady down.”

I worked my fingers around probing deeper and deeper inside until I felt the bump of his prostate. Again I heard him gasp. I curled my fingers around in a beckoning motion and stroked over it. He nearly went into orbit, gasping and pushing back against them. I reached around with my free hand to touch his cock and found it literally drooling with prcum. I rubbed it slowly down his length working it from top to bottom and then slowly back again all the time caressing his prostate.

“Oh God, stop, please stop, you’re going to make me come”

“Not yet, Dickie, not yet”.

I withdrew my fingers and slid back into him with the strap on. This time it was much easier. It just disappeared into his arse right up to the hilt. I heard him gasp, and once more my clit was caressed by it. I thrust into him again, then drew back until I was almost out of him. He moved with me, trying desperately to keep it buried deep in his arse. Our dance of lust continued and with each thrust and withdrawal my clit became more and more engorged. I could feel my juices between my thighs, and I knew that I was going to come like never before…

Dickie was gasping now, grinding me deeper and deeper into him. I felt him slow, then stop and I knew it was now. I whispered in his ear, “Stroke it Dickie, make it come for me.”

He groaned, a deep almost mournful sound as his hand slid along his cock. I gave a final push   and he was gone. He jerked back and shot his load. I could feel him squirting even through the strap-on. On and on he went, stroking and shooting until he had nothing left. He became still and quiet. I slowly withdrew from him. I heard a soft “plop” as the dildo came free.

“Dickie”, I whispered, “I haven’t come – lick me, lick me until I come as hard as you did”

I lay back and let my legs open wide. I could feel the juices dribbling out of me. Dick turned and almost fell onto me. He pushed the strap on to one side. His tongue probed and licked, poked and slid deep inside me as I gasped with pleasure. ‘My clit’, I gasped, ‘lick my clit.’

Now it was Dickies time to play. ‘Beg for it, plead for it’, he said as he slid a finger deep into me.

“Oh please, please, lick me, do it now, please.”

He smiled and then   bent to his task. I was so close that I knew it wouldn’t take long. I felt his tongue snake around my clit, teasing and caressing it, “Yes”, I breathed, “Yes, do it harder.”

His tongue kept fluttering around my clit when all I really wanted was some real pressure on me. Eventually, I grabbed his head and hauled him down – hard. At the same time I bucked up against his tongue and ground myself against it. That did it. I felt my orgasm start like a tidal wave of pleasure, it ripped through me driving me onto his tongue harder and harder. I sobbed and gasped my way through it, until my clit became sensitised and I had nothing left to give.

Dickie drew away, his lips covered in my juices. I looked up at him, then reached out and pulled him down to me. We kissed. I loved it. I could taste myself on him and I knew he was mine, hooked with no escape.

Now maybe I could really get to work…

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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