Giving in to My Fantasies

A few weeks went by once more, and we continued our new adventurous sex life. Emily continued to explore my prostate whenever we had sex and of course I got the benefit of all the amazing orgasms that came with it. Emily seemed to be really settling into the dominatrix role that she'd created for herself when she was playing with my ass, but I couldn't help but wonder if we were ever going to take it to the next stage. Towards the end of July, we both had some time off, so Emily had booked us a night away in the city. Staying in a posh five-star hotel for the night, we decided to go out drinking on the evening before a day of being tourists before coming home. When we arrived at the hotel, we checked in before throwing our bags onto the bed and got ourselves into a make out session. As I tried to start exploring her body, she kept slapping my hand away.

'Not yet,' she teased me. 'What's the rush? We have all night.'

She got up off the bed and started rummaging around in her bag that was on the floor. 'You need to wait till tonight because I have something I want to show you.' Emily carried on searching through her bag before turning whilst she was holding two different smaller bags.

'So,' it felt like she was about to go into a full speech as she stood holding these bags. 'Over these last few weeks and months, I've kind of enjoyed experiencing this exploration with you. I'm not going to lie, I was freaked out at first but then I listened to the podcast and joined Reddit and spoke to other wives whose husbands were also really into pegging, and I have to say, it helped put me at ease.'

My heart was racing as I sat on the bed, waiting to see what was in the bag. I had a pretty good idea, but I didn't want to get my hopes up.

'With that in mind, I've been busy online, and I've bought us a couple of things to try out. Would you like to see them?' I nodded excitedly. 'Good, but before I show you, you have to agree to everything that I say tonight for things to run smoothly.' Again, I nodded to say that I agree.

She put one bag onto the bed and opened the other before pouring the contents onto the bed in front of me. The first item was clearly a douche. I had a feeling that she might need to me to use one of these, I was more shocked that she hadn't asked me in the past. Emily then went into the other bag and picked out the first item which was a silver butt plug with a jewel on the flared tip, I'd seen plenty of these online and the butt plug was followed by a couple of bottles of lube. Then finally, the moment I'd been waiting for, the last item out of the bag was a harness and a strap on.

'Fucking hell babe,' I was shocked. 'Did they not have anything smaller?' The dildo for the harness must have been at least 8 inches and looked thick.

Emily just laughed. 'When I did my research, it said with a lot of patience and the right foreplay, you should be able to take this easily.'

I was still struggling to pick my jaw up off the floor.

'The rules for tonight,' Emily continued. 'You will need to douche before we go out this evening. You will have the plug in while was out so your cute little asshole is being stretched all night. When we get back, you will have to have a quick douche again in case I peg you and finally, if we do start pegging, I'm going to need you to wear this.'

On her finger, she was twirling a jockstrap. 'When you're wearing this, you'll be less tempted to play with your cock when I'm fucking you.' My cock twitched when she mentioned fucking me. 'Are you okay with all those rules?' I nodded again. 'Well, you better get in the bathroom and get sorted, we leave in about 30 minutes.'

I scooped up the douche off the bed and headed into the bathroom. I'm not going to bore you with the details of what happens when you douche, I'm sure you already know. But I spent a considerable amount of time in the bathroom getting myself cleaned, before re-entering the bedroom in my towel. Emily was sat at the vanity table finishing her makeup with her outfit already on. She was wearing her blue skinny jeans, high heels and a low-cut white bodysuit with no bra on which mean her nipples were practically piercing through the material. My outfit had been laid out on the bed ready for me as well which included my skinny jeans, and a light blue button-down shirt.

Emily turned to face me when she'd finished her make up. 'You all nice and clean?'

'As clean as I'll ever be, I feel like a different man.'

Emily laughed, 'well then, drop the towel and get on all fours.'

I did as I was told, feeling vulnerable and exposed for the first time in my life with my ass sticking up in the air. Emily then made her way around the bed, and I felt a cold sensation around my hole before her finger popped in past my sphincter causing me to let out a low groan of pleasure. She explored my insides with her finger for a few minutes before I felt a considerable increase in pleasure as my ass stretched to accommodate the butt plug.

'Fuccckkkkk,' I moaned as the butt plug entered me. 'There's no way anything bigger is getting in there.' I had my head buried into the sheets until Emily finished what she was doing.

When the butt plug was in, I jumped up off the bed to get ready. Every movement caused the butt plug to adjust slightly inside me which in turn put pressure on my prostate. Very quickly my dick became erect, and it then became a struggle to get my boxers and jeans on. By the time I was dressed you could clearly see the outline of my cock through my jeans which Emily thought was hilarious. I tried to pull my shirt down as much as I could and hoped my jacket would cover it. We headed out for drinks and food, and whilst we were in the lift, Emily showed me a smaller bottle of lube that she had in her purse. 'You're probably going to need it later, so it doesn't get to dry down there,' she told me. Luckily there was no one else in the lift. Even if there was, I don't think I would've cared. I was too turned on to pay attention to anybody but Emily and butt plug that was keeping me aroused.

We made it to the restaurant, I felt like I'd been walking differently all the way there. With every movement, the plug would move around inside me. At some points, I felt like it was going to pop out. I managed to make it through the meal without moving around too much and even forgot about the butt plug being there a lot of the time. After food, we headed into the bars around the city and had a few drinks. We were both mindful that we didn't want to drink too much because of what we had planned when we got back to the room and being drunk was not going to help anybody in that situation.

Towards the end of the night, I started to shift uncomfortably, the lube had started to dry out a little and the plug was now moving comfortably inside me, and it needed to come out soon. Emily seemed to notice that I was now struggling.

'You okay babe?' She asked me.

'Erm, things are starting to get a little uncomfortable down there,' I said quietly pointing towards my crotch.

'We'll be leaving soon, but why don't you go and top on the lube so the walk to the hotel isn't a painful one.' Emily was making no attempt to keep her voice down.

She then reached into her little bag, grabbed the little bottle of lube and slid it across the table to me. I tried to quickly grab onto it and hide it, but she grabbed my hand first.

'Two things before you go', she said. 'Make sure that plug goes back in, I'll be checking when we get to the hotel and no wanking!' She gave me a stern look and sent me on my way.

I headed to the bathroom with the lube in my back pocket and found the first available cubicle. Once inside I lowered my jeans, and noticed a considerable damp patch on the front of my jeans which must've been pre cum. I lowered my boxers and squirted some lube on my hand before gently removing the plug. I relubed the plug, gently fingered myself to get some lube inside my ass and put the plug back where it belonged and once again, it was starting to feel good. I put my boxers and jeans back on and headed back to Emily. I handed her back the lube and planted a kiss on her cheek. Her hand brushed my dick which was hard once again after playing with the plug.

'You really like that plug, don't you? You ready to head back to the hotel?' That was the question I'd been waiting for all night. We quickly got our stuff together and headed back to the hotel. Walking as quickly as I could, I couldn't wait to see what was to come and it was still only early. It was only around 10pm. Once back into the hotel room, I was quickly ushered back into the bathroom for a quick clean up. I removed the plug and had a quick douche before returning to the bed. My cock was standing rock hard in front of me, excited just at the thought of being pegged for the first time.

As I got back to the bed, Emily headed into the bathroom. She'd prepared the bed with a towel and left the big bottle of lube on the bedside table. I waited and waited, it felt like Emily was taking forever. I was slowly stroking my cock whilst playing with my hole. Then I heard the shower start, fuck I was getting impatient. I grabbed the lube from the side of the bed and spread some onto two of my fingers. My fingers slipped easily into my hole after the plug, and I let out a long moan.

I took the focus away from my cock and played with my ass. I fingered my asshole and found my prostate quite quickly but only gently applied pressure. My cock was no longer hard, but I felt amazing. The pressure almost made me feel like I wanted to pee and when I looked down it seemed that my cock was now leaking pre cum. I kept trying different positions and settled on doggy style with my hand between my legs. At some points it felt like I could get deeper in this position, and whilst trying my best not to, I couldn't help but moan.

Then the door to the bathroom opened. 'Fuck babe, couldn't you wait?' Emily was laughing as she approached the bed. She'd gotten herself all dressed up in some new lingerie. A matching purple lace bra, thong and suspender belt with black stockings attached. She climbed onto the bed, and I shifted so I was laying on my back and we started to kiss. As we broke the kiss, she bit the bottom of my lip and said, 'it's good that you've already got yourself ready for me.'

She sat on top of me so that my cock was rubbing against her pussy in the panties. Immediately it came back to life as she started to slowly grind backwards and forwards on me while we kissed. Emily then moved to my neck and started to kiss me whilst her hands roamed over my chest and body. She then kissed her way down my stomach until she reached my cock. She spent the next few minutes teasing me, kissing all around my cock and balls but never actually touching them. It was so frustrating, but I loved it at the same time.

Emily took the head of my cock into her mouth as I let out a long moan. She slowly bobbed up and down on my cock as I laid back and enjoyed the moment. Blowjobs were arguably my favourite part of sex. Feeling yourself explode into your partners mouth was an amazing feeling. Emily then began to explore my body with her spare hand. She began to apply pressure to my taint, stimulating my prostate from outside of my ass. I began to squirm on the bed feeling like I could cum at any moment, but Emily soon put a stop to that when she let my cock fall from her mouth. She then licked from the base of my cock all the way to the tip whilst my cock twitched in front of her face.

Her panties were now pulled to the side as she positioned her pussy just above my cock. She let the head of my cock rub against the lips of her pussy, and I could already feel just how wet she was. Emily then lowered herself onto my cock. Her warm pussy surrounding my cock as Emily started to gently ride me.

'Fuck babe,' I moaned. 'You won't be able to do this for long, I already feel like I'm going to explode.'

Emily just laughed, 'you think that even if you cum now that you're not getting fucked tonight? Think again Mister, you're getting fucked so I suggest you try not to cum.'

Our fucking soon got into a good rhythm, and I was trying my best to focus on anything apart from what was going on. I was staring at the ceiling counting the different patterns on the paintworks but the only way I was going to be able to hold on was if I took a break. I flipped Emily onto her back and pulled my cock out before going to work on her pussy using my tongue. I lapped away at her clit and quickly inserted two fingers into her dripping wet pussy. Very quickly Emily started to writhe around the bed whilst I found it difficult to keep up my oral assault. Before long I had Emily cumming all over my mouth and fingers as she couldn't hold back any longer and I kept going until it became too sensitive for her.

I then kissed my way up her body, eventually bringing us face to face as we began to make out again. My cock now rubbing against her extremely wet pussy and without even trying, it slipped inside causing us both to moan. What happened for the next ten minutes was arguably the most passionate love making we've ever had. Slowly I rocked backwards and forwards as we kissed. Both of us moaning in between as her pussy contracted around my cock bringing me very close to orgasm. We continued to fuck like this until I brought Emily to her second orgasm. It built slowly but when it arrived her full body started to shake, and I eventually pulled my cock out and laid next to her and we cuddled whilst she recovered.

Once we'd had some downtime, Emily had been playing with my cock throughout, so it remained hard. She got up from the bed and went into the bathroom before returning a couple of minutes later. Only this time when she returned, between her legs was an 8" dildo.

'Bring that ass to the end of the bed,' she commanded. I was already moving before she stopped speaking.

Hanging over the end of the bed, I had my legs spread and my virgin asshole exposed to my girlfriend who was about to fuck me. First though, she gave my ass a good slap.

'Ooooo babe, I didn't realise how much jiggle your booty had.' She laughed and then spanked me again causing me to yelp.

Next, I felt her hands exploring my hole as she gently rubbed around the outside sending the pleasure levels through the roof as I waited in anticipation. I then felt the cold sensation of lube being applied before she inserted one of her fingers causing me to bury my head in the duvet and moan.

'Oh yeah, my little slut loves his ass being played with doesn't he,' she taunted me.

All I could do was moan in response as her finger continued to explore my insides before she hit my prostate.

'Ohh fuckkkk,' I moaned.

'You like that?' Is this what you wanted.

'Yes baby,' I whimpered in response.

'What do you want me to do next then?'

'Fuck me.'

'You want me to what? I need you to be clearer.'

'I want you to FUCK ME.' I pretty much shouted.

'I'm still not getting it.'

'Please take your dick and fuck me with, please.' I was now pleading with her as she rubbed my prostate.

'Oh well if that's what you wanted, why didn't you say?'

Her finger was slowly removed from my ass before I felt the pressure of something much bigger. I tried to push out to try and make the entry easier and then I felt the head of her dildo push past my sphincter with a pop as she slowly eased herself inside me. The invasion of the dildo instinctively made me want to move forward but Emily had a reassuring hand on the base of my back as she continued to move forward.

I thought Emily getting into the rhythm of fucking with a penis would be a slow burner, but she seemed like a seasoned pro. Once she'd bottomed out, she slowly began to withdraw herself before slowly pushing herself back in. I looked down between my legs and despite the intense pleasure of the cock rubbing my prostate, my cock was as floppy as it'd ever been. My hole seemed to loosen up with every thrust and before long we had a steady movement going. The pace got quicker as time went on and before long the sounds of moans and Emily's thighs slapping against my ass filled the room.

'Oh, fuck baby.... oh fuck,' I moaned.

'Yeah, you like that? Does my hubby like being fucked in the ass?'

'It feels so fucking good.' I had my head buried in the bed before Emily slapped my ass.

'No, no. Arch that back like a good little slut.' She grabbed me by the shoulders and pulled me towards her so she could really pound my asshole now. This went on for a couple of minutes before my legs couldn't take it anymore and I collapsed onto the bed. I didn't realise how exhausting being fucked could be. As I fell forward onto the bed, Emily's cock slipped out of my ass, and I thought I was going to get some respite.

How wrong I was, whilst I was face down in the bed, I felt Emily's weight on my lower body and her cock was quickly back inside my ass and she resumed her pounding. My cock was trapped beneath my body and the duvet which was now stimulating me with every thrust. It almost felt like I wanted to pee, but I didn't want to release in case I made a mess of the hotel room bed. Emily had now laid her full body on top and me and was slowly moving backwards and forwards with a gentle rhythm. It was almost like we'd gone from a full on fucking to love making.

'Maybe next time we need to try a double ended dildo babe, that way we can both cum together. I bet you'd like to cum while my dick is in your ass, wouldn't you?' She gave my ass a playful slap.

'Yeah.....,' came my muffled response.

'Sorry I can't hear you babe, what did you say?'

I turned my head slightly, so it was off the bed, 'yes, I'd like to cum while your dick is in my ass.'

Emily pulled out of my ass again and I felt her weight lift from my body. 'Come on,' she gives me a slap. 'Stand up.'

I got to my feet and my legs felt a little jelly like as she took me by the hand and towards the hotel room window which went from floor to ceiling.

'What you doing?' I felt a little panicked, we were only on floor 6 so there was a good chance anyone walking past could've seen us.

She pushed me towards the window and bent me forwards slightly before I felt her cock push against my hole once more. I put my hands up onto the glass to stop myself falling forwards. With my head looking down, I could see plenty of people walking past. And in the reflection of the glass, I could see my soft cock flopping between my legs. Emily quickly got into her rhythm and was pounding me again. Looking down, it almost looked like I could see people looking up towards our hotel window, but I couldn't be sure. I mean all they would be able to see would be a guy getting fucked but they wouldn't know that it was by a beautiful woman with a fake penis.

I was seriously impressed by Emily's stamina. She just kept going and going and wouldn't stop. I couldn't resist anymore and reached for my cock and started rubbing it, trying to get it hard which didn't take long. I could quickly feel an orgasm building but that was stopped when Emily slapped my hand away from my cock and moved my hand back onto the window. My prostate was taking a serious bashing and with every thrust, my legs felt more like jelly.

Fuck.... fuck.... babe, I don't think I can stay stood up much longer, fuck.' I moaned.

'Awwww is my baby ready to cum? Do you want me to put you on your back and make you cum?'

'Yes, please baby. Please make me cum.'

'Since you asked so nicely, come on.'

We moved back to the bed, and she laid me down on my back and pulled my ass to the edge of the bed. After reapplying some lube, she spread my legs and had her cock back in my ass again.

'Fuck babe, I love watching you take that dick in your ass.' She said, 'thank you for asking me to do this, I think we'll be doing this more than you fucking me going forward.'