Pegging With Friends

This story follows the characters from my previous story, 'Giving in to My Fantasies' and will also include the addition of some new characters.

'Oh yeah, fuck my ass,' the moan echoed around our bedroom. It wasn't a statement that was a massive part of our marriage in the early years, but it was now. And no, it wasn't my wife Emily moaning... it was me, Jamie.

I was on my back, in our marital bed, moaning as my wife stroked my cock. I'd sat down with my wife and discussed deepest fantasy. And that was that I wanted her to peg me. She was reluctant at first, even concerned about my fetish but soon she was doing her own research and surprised me one night by agreeing to try it out. And since that point, we hadn't looked back. Pegging had become a regular occurrence in our sex lives. Emily loved it and I loved it even more. It wasn't very often anymore that I finished sex by cumming inside Emily. It now tended to start out with regular foreplay, followed by regular sex and then once Emily had cum multiple times, she would whip out her plastic dildo and fuck me with it. We discussed bringing a squirting dildo into the bedroom, to give me the chance to experience being creampied but we hadn't got round to that yet.

'Are you going to cum for me?' Emily teased as she stroked my cock slowly.

'Fuck, keep fucking me like that, and I'm gonna blow my load soon,' I moaned at her. She kept fucking me, driving the plastic cock deep inside of me before sliding out and slamming it back in deep again. 'Oh fuck, oh fuck.'

'Cum for me baby, cum for Mommy,' she quickened the pace of her strokes on my cock and the thrusts of her strap on.

'Fuck, I'm gonna cum, I'm gonna cum,' I groaned. 'I'm cumming.' Cum started to shoot from the tip of my cock, covering Emily's hand and my torso. Emily stroked my cock until no more was coming out, then she licked the cum from her hand, bent over and cleaned my torso before kissing me on the lips, making me taste my own cum at the same time.

So, I guess you could say with words like Mummy and Daddy being thrown around in the bedroom and me enjoying the taste of my own cum that maybe a few more fetishes and kinks had been explored since we started pegging. It was like I'd flicked a switch with Emily, she was so open to trying new things and had often come to me with ideas that we could be doing. She even agreed to try having anal sex one night, which I always thought would be a no go with her, and she loved it. The latest thing we'd decided to work on was my underwear drawer. Emily was going through a phase where she was buying me briefs, thongs, and jockstraps, initially just for sex but now she was wanting me to wear them all the time. Jockstraps were a no when I was going to work, I just didn't see how that was practical. But I did find thongs comfortable, and they had tended to become my underwear of choice daily. Was I worried about seeing them at work? Of course I was, but the thought of only me and Emily knowing what I was wearing and why I was wearing it was a complete turn on for me.

As usual, when we'd had sex, we would both get cleaned up, get into bed, and spend some time cuddling and talking. We saw it as an important part to our after-sex activities. We would often talk about things we liked and disliked, as well as some things we'd like to try next time. Plus, cuddling with an insanely beautiful woman, who was naked most of the time was something that got the blood running to my cock again.

'Babe,' Emily said, as I was laid in between her legs, resting my head on her stomach whilst she stroked my hair. 'Don't be mad with me...'

I lifted my head and looked at her before she could go any further, 'what have you done?'

'Please don't me mad,' she started, 'but I was talking to a girl at work, called Skye.' I knew of Skye, her and Emily had been working together for several years and as far as I could tell were quite close. 'Well,' she continued, 'Skye was telling me about some of the things she'd like to try sexually and one of those was pegging.'

'I hope you haven't been offering my ass out,' I said laughing.

'Not exactly,' Emily smiled. 'I may have told her that it's something we've been doing for a while.'

Emily paused, I think she was expecting some sort of explosion of anger from me, but I just said, 'okay, does she have a partner?'

'Wait, you're not mad?' Emily seemed shocked.

'Why would I be?' I reassured her. 'We've always said we're not going to hide anything but also not tell the whole world like we're showing off.'

'You're amazing,' Emily said and leaned down and kissed me on the head. 'Yes, she does have a partner, she's married in fact. To a guy called Sunny.'

'And I'm assuming from the conversation you had, she hasn't told him about this?' I enquired.

'I don't think so,' Emily said. 'I said we could go for drinks tomorrow afternoon seen as though it's the weekend. And I figured you'd be out till after the football is finished anyway. I just wanted to make sure you're okay with me discussing our sex life with Skye?'

'Of course, babe,' I reassured her. 'You know I completely trust you anyway. You can tell her whatever you like, just keep me in the loop. It would be exciting to know another couple who were into pegging.'

Tomorrow came around and I left the house in the early afternoon to head to football and out for something to eat after the game had finished. I left Emily getting ready to go and meet Skye and she was in the bedroom at her makeup table in nothing but a green lace thong. It was incredibly difficult to walk away without fucking her there and then. But it gave me something to think about while I was out this afternoon. To be honest, the afternoon felt like it dragged on forever. Emily had messaged me over an hour ago to say she was home, and now that's where I wanted to be. Thankfully after we'd eaten our food, most of my friends didn't want to stay out any longer and wanted to get home. That suited me fine, and I used the excuse of getting a taxi with one of them to save me walking home.

As I walked in the front door of the house, I could hear some clattering in the kitchen, so I followed the noise to find Emily putting dishes away. She was bent over putting things into the bottom cupboard, wearing a strapless white top & low-rise denim jeans. And the jeans did nothing to hide her underwear. I could see the thong peeking out by a few inches over the top of the jeans. Fuck, it turned me on to see a whale-tail like that.

'Hey babe,' she said when she heard me coming into the kitchen. She stood up, turned to face me and I kissed her.

'Bedroom, now, let's go,' I said. Emily turned and headed for the stairs, and I slapped her ass as she walked away from me.

We both ran up the stairs, eager to rip each other's clothes off. As soon as we were in the bedroom we started kissing again, swapping tongues, and roaming our hands over each other. We eventually fell onto the bed, me landing on top of Emily as she started to pull and tug at my t-shirt before I removed it and threw it across the bedroom. I turned her head to the side and started kissing her neck. She reached down and started to rub my crotch through my jeans, and I reacted by pulling the front of her top down, so I had free access to her tits. I moved myself down her body and took each nipple into my mouth. I gently sucked and teased each one until Emily was squirming beneath me.

'Oh fuck,' she moaned, grabbing at my hair. 'Please can I suck your cock?'

That was one thing that didn't need to be asked twice. I stood, shuffled myself out of my jeans and thong before climbing back on the bed and placing myself next to Emily's head. She turned her head and immediately took my cock into her mouth, making me groan. I was able to reach down and get my hand down the front of her jeans, finding her wet panties first, and then moving them to the side and getting access to her pussy. My finger slipped into her pussy with ease, and she started moaning around my cock. We needed to get her out of her jeans before she made a mess of them. So, we stopped pleasuring each other whilst I stood by the bed again and pulled her jeans off, quickly followed by the thong she was wearing.

I think Emily was expecting me to climb back onto the bed so she could continue sucking my cock, but it caught her by surprise when I immediately got down between her legs and started to lick her clit.

'Fuck, you bastard,' she groaned as she ran her hand through my hair. I slipped two fingers back into her pussy and went for a full-on assault. 'You're going to make me cum.'

I couldn't respond even if I tried. Emily was now pushing the back of my head, forcing me into her pussy with no room to breathe. I lapped away at her clit with what little breath I had left whilst my fingers worked her g-spot.

'I'm cumming,' she screamed, and her legs started to shake, and she tried to close them, wrapping them tightly around my head. I slowed down whilst she went through her orgasm. Her juices now coated my fingers and tongue, and she tasted incredible. As her orgasm subsided and I could see her chest rising and falling quickly as she tried to catch her breath. I moved my attention to her stomach and legs, and placed gentle kisses all around her body, eventually making my way back to the insides of her groins which really made her squirm.

'You ready to go again?' I asked, looking up at her with a cheeky grin on my face.

'What do you mean?!' She managed to ask in between breaths. I didn't answer her question, I just slowly started to run my fingers up and down the sides of her pussy before teasing her clit and sliding them down towards her entrance. 'Oh fuck, you bastard,' she moaned as my two fingers slipped back inside her.

I laughed at her, as she threw her head back and reached her arms out to grab onto the bed sheets. Her breathing was soon rapid once again, as I lowered my head and gently licked her sensitive clit. I took my time with her this time, slowly running my tongue around her pussy, bringing her slowly towards another orgasm in quick succession. She was whimpering underneath my touch; she'd managed to let go of the bed sheets and was now playing with her nipples. She twisted them gently and it seemed like she was matching my tempo when she played with them.

'Please fuck me baby?' She begged.

I lifted my head away from her pussy, just long enough to tell her, 'when you cum again babe, then you can have my cock.' I put my tongue back on her pussy and drove her crazy. My cock was throbbing, I really wanted to cum, and part of me worried that it wouldn't take me long to cum once I started fucking her.

After a couple of minutes of teasing her slowly, I started to increase the tempo, and worked her clit a bit more now it was a little less sensitive. Emily was soon writhing on the bed, legs flying all over the place. They even crashed into me, but it didn't distract me enough to stop. 'I'm gonna cum, fuck, I'm gonna cum,' she started to moan. Then her juices coated my fingers again. I lapped away at her pussy until I'd cleaned up any excess juices whilst Emily laid there, trying to recover. I climbed onto the bed next to her, my fingers still glistening with her cum. Emily looked at me, then took me by the wrist and started to clean her own juices from my hand.

'You're so fucking naughty,' I groaned. She stared at me while she sucked on my fingers, and I almost came just from that. And then she took hold of my cock and stroked it slowly.

'I better get this thing nice and wet,' she said before kissing the head of my cock. 'Not that it needs to be.' Emily took the head of my cock into her mouth and gently sucked on it while running her hands up and down my shaft.

'God that feels so good,' I groaned as I put my hand on her head. 'We can't do this for long though, otherwise you won't get fucked.'

She continued to tease the tip of my cock, but that made it worse for me. The slow tease was what I loved most, especially when she was swirling that tongue around the top of my cock. Eventually I had to pull my cock away from her mouth before I went too close to the edge of an orgasm. Emily smiled at me and started to get up onto her knees on the bed. She kissed me strongly, putting her tongue into my mouth and gently pushing me until I was on my back, cock standing straight up into the air.

'I'll control the pace from here babe,' she said with a devilish smile. She climbed on top of me and positioned my cock at the entrance to her pussy. Without any resistance, her wet pussy accepted me inside as she buried me balls deep inside her. She started to rock backwards and forwards, and I could feel it all as her pussy tightened around me. I reached for her pussy with one hand and started to rub her clit, 'oh yeah, rub my clit,' she started moaning as soon as I started playing with her. I knew if Emily was going to cum again, it had to be quick before I blew my own load early.

Emily was bouncing on my cock like it was the last thing she was ever going to do. With every bounce it was like we were racing each other, trying to see who could make the other cum first. 'Fuck,' I groaned, 'you can't keep doing that, you'll make me cum,' I admitted defeat first as Emily held a finger to my lips and slowed down her bouncing and instead started to grind herself on my cock.

'You can't cum yet big boy,' she teased me. 'Your cock isn't where I'd like it to be when you cum.' My eyes lit up, and I was either going to be slightly disappointed or the happiest man on earth. I went to talk but again she shushed me by keeping her finger to my lips.

Emily smiled at me, 'I'm going to climb off this big cock of yours, and then I want you to fuck me in the ass.' I nearly cum as she said the words. She climbed off my cock and laid down on the bed while I ran off, cock bouncing in front of me, to get the lube. I got back into the bedroom and Emily was slowly teasing her pussy.

I pulled her to the end of the bed and placed one of our pillows underneath the bottom of her back, so her ass was slightly risen. I dripped a generous amount of lube onto my fingers and slowly started massaging it around her ass before sliding one finger inside her. Emily let out a long moan as her hand focused its attention on her clit. I let her get used to the feeling of one finger, before adding in another finger. I made sure I used more than enough lube before I lathered my cock and lined it up with the entrance to her ass.

I pushed in slowly as her asshole stretched around my cock, 'oh fuck, you're so big,' she moaned. And slowly but surely, she took more and more of my cock until I was fully inside her. We always started anal sex off slowly, so I would spend the next few minutes slowly withdrawing my cock before putting it back in again. Emily was still working away on her clit, her other hand stretched out wide, holding onto the bed sheets and her head back, moaning every time I pushed inside her.

After a few minutes I started to increase the pace of my thrusts, Emily had stopped rubbing her clit and now had two fingers deep inside her pussy. The sounds her pussy were making was turning me on, and her juices were dripping out the bottom of her pussy and down towards my cock.

'Oh fuck, shit, I'm gonna cum,' she started to warn me. I fucked her quicker again until her body started to shake and move. 'I'm fucking cumming,' she announced. I stopped fucking her in case she moved around too much, but I tried to hold her in place. Once she got through her orgasm, she looked me deep in my eyes and said, 'cum inside me baby.'

I started to fuck her ass, hard and fast. And Emily could take it in her asshole like a champ. Well, we both could really. It wasn't long before I could feel my own orgasm starting to rise in my balls. 'I'm cumming,' I shouted as I buried myself balls deep inside her and held myself there as I unloaded in her ass. Fuck it felt incredible. I didn't move my cock until I knew my cock had finally stopped leaking cum into Emily's ass before we both quickly got into the bathroom, hoping we'd leave no mess behind, and showered together.

Once we were out of the shower, we sat snuggling on the sofa with a drink before I asked, 'how did things go with Skye?' Now it's worth noting before I tell you about Emily's response, that in the past we had discussed the possibility of swinging and voyeurism. One night when Emily had me overly horny, I admitted to wanting to watch her get fucked. But our conversation went no further than that and neither of us have really mentioned it since.

'It went really well,' Emily beamed with a smile. 'Skye brought up pegging after we'd had a couple of drinks. She said she brought it up at home with Sunny and he was open to the idea. Apparently, it was something he'd always wanted to try as well but didn't bring it up in case Skye thought he was weird. And let's be honest, we've all been there with one fetish or another. But being honest with your partner is the best thing for it, you just never know, you both might end up liking the same things.

'That's amazing,' I said. 'So, are they going to give it a go?'

'Well,' Emily said slowly, 'this is where things get interesting.'

'Go on?' I said, not sure where this was heading or what Emily might have agreed to.

'Skye had obviously had a few drinks, and came up with an idea of them watching us do it first,' she stopped and looked at me. 'I didn't agree to anything, I just said I would have a chat with you first.'

'What do you mean? Like a video recording?' I didn't know what to think.

'No, she means in person,' Emily said quickly.

I think it's safe to say that I was stunned into silence. 'I don't know, would this be heading into a swingers territory for us?'

'It only has to be what we want it to be,' Emily said. She seemed pretty sure of what she wanted to do. 'It's something I've always wanted to do, but I suppose that's the exhibitionist in me.'

'I don't know,' I said. 'What if I freeze on the night and can't perform.'

Emily let out a little laugh, 'have you seen Skye? I don't think you'll have a problem with two hot women in the room.' Emily had shown me Skye in the past, but right now I couldn't remember, and Emily was already scrolling through her phone, trying to find Skye's Instagram page.

She eventually found it and turned her phone up towards me which was now displaying a selfie of Skye. 'Fuck,' I mumbled. I remembered her being attractive, but fuck she was hot. She had long dark brown hair with blonde highlights and a cute nose ring. Emily flicked to the next photo which was Skye with her husband Sunny, and he was an attractive guy. Dark hair, beard, he looked good. But he was one lucky fucker going home to Skye every night.

'So, what are you thinking?' Emily wanted an answer, and partially I wanted to do this for her. She'd stepped into the world of pegging for me, so now it was my turn to do something for her. And plus, I found Skye seriously hot if I hadn't already mentioned it.

'Let's do it,' I announced. And I saw Emily's face light up immediately.

'Really?' She sat up in shock.

'Yeah, why not?' I think it'll be fucking hot.

'Oh my god, you're the best,' she said and jumped on top of me and kissed me. She showered my face with kisses. 'I'll give Skye the good news and make the plans.'

We didn't speak about it again over the next few days. I didn't ask about it and I assumed the next time Emily told me anything about it would be because she'd made the plans, and we now had a date for our live sex show. But it was a couple of weeks before it was mentioned again, but in between that, me and Emily continued our amazing sex life. We fucked each other numerous times and she teased me every time she pegged me now, asking me how much I'd enjoy having Skye in the room, watching me get fucked. And that kind of teasing worked every time because the thought of Skye watching me get fucked made me cum very quickly. Emily only had to mention her name and my cock would twitch.