If you haven’t already go back and read Emily’s first threesome, Emily’s one night stand and Emily’s other threesome. This is part 4. Please also forgive any inaccuracies, this happened a little while ago and I had, had a couple to drink. 

Emily had enjoyed herself with 3 guys (and a girl) by this point. But most of that fun had been had without me present. And we both wanted that to change for the next time. You see, by this point the fantasy of me watching her with another man was becoming a big part of our sex life. We spoke about it frequently and role played scenarios. Emily loved the idea of being watched almost as much as I loved the idea of watching her. So it wasn’t a case of if I watched her have sex with another man, but when.

Because I wanted to be involved, well at least watch, for the next night of fun we had to find a guy comfortable with my presence. Not an easy task. Friends were still a no go at this point, we hadn’t told anyone yet, apart from Beth. We were a bit lost. So like any problems we face, we googled it. Fortunately, there are so many sites that cater to our fantasy, it was just a case of finding one that looked legit. We found one of the industry leading sites, you had to pay to post an advert, but that was for the best. We got a surprising about of responses, most terrible to be honest but a few ok. At first we short listed the couple of men that had a nice photo and good chat, and talked to them via the platforms messaging system. One stood out pretty quickly, he was Henry. 

Henry was about five years older then me. Was recently single but had lived ‘the lifestyle’ with his previous girlfriend. Or to put it bluntly, he used to be swinger. He was crazy tall, about 6’ 5” with red hair. He didn’t have huge muscles but a lean figure, kinda of like someone who does lots of cycling. Which he did. But most importantly for us, he was hilarious. I mean I was kinda nervous about the whole thing, that fact I was searching the internet to find a guy to have sex with my girlfriend. But he made the whole thing seem normal and turned it all into a joke. In a good way. (He also didn’t ask or send any nudes, which was rare). We added him to a Whattsapp group with the three of us in it and carried on chatting for a good week or so.

Jump forward and it was Saturday night two weeks later. This was two, three months after Emily’s threesome with Beth. Emily was busy getting ready for us all the meet up with Jack at a bar about 10 minutes from ours. We wanted to meet local but in a neutral setting first to make sure we liked him in real life. We had FaceTimed by this point so knew he wasn’t a catfish, but still. I was sitting around waiting for Emily to finish showering. She was taking ages because she wanted to shave and moisturise her body. When she was finished, she pulled on my favourite set of lace lingerie. She hadn’t told me she wanted to wear it, but I wasn’t complaining. It was a full matching black set, complete with stockings and suspender belt. The bra was almost completely see through and I remember seeing her small pink nipples already standing firm. The bottoms, a tiny thong, were just as transparent. You could just see the faint line of her shaven pussy through the thin lace. She looked outstanding. On top she wore a mustard yellow, floral, summer dress. Tight at the top, pushing her small breasts together and creating and jaw dropping cleavage. It then flowed out loser below the waist and was longer then she normally liked, to cover the top of the stocking. She matched it, as always with stunning makeup, including my favourite red lipstick and curled hair. Finally, the last touch were her high wedges. She looks beautiful and wholesome on top, but was naughty underneath …. And on a site note, if you haven’t seen your girl getting ready to have sex with another man, I am not sure you will understand the emotions and excitement that was I was feeling. It was electric. 

I remember Henry texting us that night to ask if it was still on and asking how he would recognise us. He had seen a few photos, but it’s different in real life. Emily asked if she could send a picture of her outfit so he would know what to look out for. I was expecting for her to snap one on her phone but instead she found one from her archive and asked me if it was ok to send. It was a shock, but I got the joke. In the picture, taken in the mirror a few months beforehand, she was naked apart from the wedges she was going to wear that night. You could see every inch of her slim body apart from her face which was covered by the phone. I agreed and lucky Henry got the photo. He saw the funny side, but I think most importantly, it helped brake the ice for the evening to come. 

When Emily was ready she grabbed her handbag and made sure she had everything while I gave our bedroom a finally tidy. Even removing the half worn cloths from the chair in the corner and placing it next to bed ready. I guess making a stage of our bed. Then we were on our way to meet Henry. It must have been around 9ish and town was buzzing. We grabbed our table ordered some strong cocktails and waited. The bar was dimly lit and felt private which was what we wanted. Henry arrived before our drinks. He recognised us no problem and was a classic extravert, coming alive when he saw us. Within minutes we were taking like old friends and knocking back drinks. Emily sat next to Henry, opposite me. I still remember them getting closer and closer to each other with every sip. Until they were basically arm in arm, their faces just inches apart. Slowly they both leaned in until their lips touched and they shared a short but enjoyable kiss. Suddenly the decision was made to go back to ours and after only an hour or so of arriving we were getting ready the go. I remember I got up first and saw that the way Emily was sitting had let her dress ride up. She had given Henry, and a probably a few other people in the bar, full view of her stocking tops.

The walk back was short but a whirlwind. Emily and Henry were waking hand in hand, making me look like the third wheel. They only stopped once, to kiss. I still remember their lips touching as they held each other. I love watching Emily kiss other men and I couldn’t get enough. Finally we got back to ours. Emily said she was running to the bathroom so I took Henry to grab some champagne (we had been given a bottle a couple weeks before), some glasses and then led him to the bedroom. I opened and poured as he pulled his T-shirt off and slipped down his jeans so he was just wearing some white CK boxers, with a noticeable bludge.

We were chatting about something silly when Emily walked back into the room. She had ditched the dress. Her sexy body just covered by the lingerie. It seemed like we were all out of breath. She walked in, enjoying our eyes on her, right into Henry’s arms. They kissed passionately. A moment later I remember Emily looking back at me and giggling. That night was for me, but she was going to bloody enjoy it as well. They started kissing again, now exploring each other’s bodies. He pulled at her bum and she rubbed the lump in his boxers, firstly on the outside then sliding her hand inside. She told him to get onto the bed, which he did. She gave me a big kiss, told me she loved me then followed him. The show was about to begin.

Henry told me I could get naked or play with myself or whatever, which I guess was nice of him. But for the time being I just pulled the chair right up to bed, around the middle, so I was only inches away from them. They were kneeling on the bed facing each other. They started by kissing and touching each other through their underwear, Emily’s bra somehow removed moments before to expose her small perky breasts. Emily then pulled Henry’s cock free from his boxers, rubbing her hand up and down the shaft. He wasn’t huge, maybe average or the same as me but Emily later told me it was just about perfect for her. Apparently bigger guys could be fun but often hurt after a while, but I digress. By now Henry had pulled her thong to the side and after playing with her for a bit, slipped a finger or maybe two inside her. Then, just as Emily started to moan and squirm from his fingers, he stopped and awkwardly pulled his boxers off leaving him naked. Emily followed suite, sliding the tiny thong down her slender legs and throwing it at me. I presume she had worn it over the suspendier belt for easy access. Henry and I then spent some time enjoying the view of her naked body, only slightly covered by suspender belt and stockings. 

Next, Henry laid on the bed, his head on my pillow and his erect cock next to were I was sitting. Emily wasted no time and started to tease and play with the shaft and balls using her hand. She was on her hands and knees, her ass kind of towards Henry, allowing him to group and play with her from behind. It wasn’t long until she was done teasing. I remember her deliberately looking me in the eyes and flicking her hair behind her ears to make sure it didn’t obstruct my view. Then lowing her month to his cock. She kissed the head at first then allowed her lips to part as she took it down her throat. She never stopped locking eyes with me as she stated to suck him faster and faster. I watched as his cock slide in and out of her mouth. Henry eventually broke the spell by telling her to get into the 69 potion. I sat there as she lifted herself up, and straddled his face. Then lowered herself. She enjoyed the feeling of his tongue for a moment before setting back to work. No eye contact now, she was too busy sucking his dick and having her pussy licked.

The forplay seemed to go on for ages before they both finally came up for air. I finally handed out the glasses of champagne. Emily said to cheers, clinked glasses and basically downed the large glasses eggar to carry on. And soon they were back to kissing and playing with each other in the bed, right next to me sitting on the chair. When finally, the main even started. Emily was on her back, legs wide apart. Henry kneeling between them, holding his hard cock at the entrance of her pussy. He rubbed the head on her, teasing her. I was so close I could see as he nestled it between the lips of her pussy, then saw every detail as he pushed it inside her. Slowly, all the way in. I looked up to see how Emily was enjoying it. She was looking back at me and we locked eyes again as Henry started to fuck her. She moved with each trust and moaned his name, telling how good it felt inside her.

Before long Henry had leaned down so their bodies were close and their lips connected in the most passionate kiss. She’d broken eye contact with me by now but was still telling me how good Henry’s cock felt inside her pussy. After watching him between her legs for a while he switched things up and told her to get on her hands and knees. She followed his command and a second later was facing me, her ass towards Henry. One hand on the bed the other on my knee. He was back inside a moment later and I felt each trust as her grip on my knee tightened. The eye contact was back and she had doubled down on the commentary, telling me im graphic detail how good it felt. When finally, I remember Henry telling me ‘I need a break your girlfriends pussy feels too good’. 

I poured another round while Emily gently licked Henry’s cock clean. Then we sat there, me clothed on my chair, them naked and hugged on the bed. We chatted for a bit, while they intimately kissed and touched each other. When Henry asked me what I wanted to see. It was time for requests. I asked for reverse cowgirl, which I had been desperate to see. They jumped to it almost right away. Henry laid on the bed again and Emily straddled him. She held the shaft, then looking at me, she pushed the head into her soaking pussy and lowered slowly to the base. She took her time as I saw as every inch slid inside her. After enjoying the feeling of him filling her up again, she started to ride him, taking his cock from top to bottom, over and over. Emily loves being watched and she was putting on a show, moaning and taking dirty. Telling me how much she wanted Henry and loved his cock. I was so close I could see and hear every detail. The sight of her drenched pussy stretched by his vainly shaft. The sound of skin slapping and slipping. It was too much to take and I finally gave in, sitting back on my chair, opening my jeans, playing with myself. Much to Emily’s enjoyment. 

When Emily’s legs were finally too tired to continue, she slumped on the bed and lay next to Henry. I poured the last of the champagne as they continued to touch each other. Emily’s hand firmly on Henry’s cock and his hand between her legs. We chatted, discussing favourite positions and what they liked about each other’s bodies. There was a lot. When Henry asked me what I wanted to see next. Emily jumped in saying she wanted to be licked. Henry was happy to help. She sat up against the headboard, champagne still in hand, and opened her legs to him. Henry was quick to start licking and fingering her, making her moan in seconds. Emily gave him words of encouragement and even pulled a few drops of her drink down her pussy for him to lap up as he pleasured her. I was still sitting there, touching myself. Henry went on licking for ages and finally Emily had to put her drink down as she moaned his name and her hips started twitching. She was cumming. As I said, Emily loved and audience and I can only imagine how much she got off on me watching her being pleasured by another man. 

After a brief pause to recover they were back at it. The show had been forgotten about now, they were just fucking each other like I wasn’t in a he room. Mainly switching between missionary and cowgirl. It was amazing to watch her from behind as she rode him on top. His cock disappearing into her, just below her squat toaned bum. Or when she was on her back, him between her thighs. Her legs stretched wide and feet bouncing in the air with each trust as he pounded, groped and kissed her. 

Finally it was time. Henry said he was close and needed to cum, where did I want it? Emily answered for me and told him she wanted it all over face. I loved cumming on her face and she knew that’s what I wanted. A second later Emily was on the floor on her knees, so close to me we were just touching. Still naked apart from the stockings and belt. Henry stood over her. For a while Emily worked his cock and balls with her mouth and hand before he announced he was close again. With one hand he held onto her long brown hair, keeping her steady. Then with the other hand he pumped his own dick until it exploded. Emily kept her eyes open looking up at him as the first jet or two hit her lips and left cheek. The next small shot of cum hit her more or less in the eye and she struggled to keep it open as it gummed up her eyelashes. Finally, he wiped the head of his cock down her right cheek, depositing the last few drops of cum on her face. She was covered.

Henry excused himself to clean up in the bathroom, leaving us. Emily basically pounced me. Straddling me while I still sat in the chair. I had been playing with myself so she removed my hand to sit on me. A moment later I was deep in her noticeably used pussy as she grinded me. I still remember her saying, her face still dripping in Henry‘s cum, ‘I love fucking other men in front of you’. She then kissed me, not exactly what I wanted but I was too turned on to care. Needless to say a moment later I was filling her soaking pussy with my cum.

When Henry returned we had cleaning up as well. Emily didn’t bother to get dressed just throw on a silkish looking dressing gown, left undone. We told Henry to stay but he said he should go. Only asking us for another session soon. We booked one in there and then and Emily saw him out. Kissing him out the door, her naked body still exposed in the undone dressing gown. 

Emily demanded I make her cum again almost straight after he left, and I soon found myself licking her used pussy, before falling into a deep happy sleep. The following day we were both in ecstasy and made love several times, talking through the experience. It always surprises me how close we are after she sleeps with other men. We met Henry a good few times over the following months. They tired almost everything together, I am not sure there is a position I could think of that they didn’t do. Normally right in front of me like that night, but once or twice without me when I inevitability had to travel with work. Still, like most things, it gradually fizzled out.

Not that, that was the end of our fun. Though the next time we took it to another level as Emily requested an open pass for a friend and colleague, Steve.

I’ll write it up when I get a moment!