Fifteen Years of Memories Part 3 – Asking and Watching Greg Fuck Nicole [cuckold][watching]

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Greg was certainly expecting a phone call from me regarding the night we shared Nicole, but I don’t think he was really expecting it to go the way it did.

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We arranged to meet at a local sports bar for a couple drinks and talk things over.

He apologized over and over again for the night and how he felt he monopolized the time with Nicole. I accepted his apology. Even though I think things turned out the way I wanted, even if we didn't know it at the time, there was no way of knowing that beforehand so things could have been a problem for the three of us. 

There’s no easy way to tell another guy that you’d like him to fuck your girlfriend again, but my longtime friendship with Greg helped. We’ve seen each other's best and worst over the years and I knew I could trust him with this even if he wasn’t up to doing it again.

I told him that Nicole and I were talking and that we might be interested in a repeat if he was up for it. He was surprised but listened to what we had in mind and agreed to try again as long as he heard it from Nicole too.

The three of us talked together and we made plans for him to come over the next Friday night and we’d see how things went. No promises and no expectations were understood by all of us.

Over the week I think I was more nervous than excited and Nicole was the exact opposite, she seemed really excited at the idea of us trying it again with everyone being on the same page. She thought it was cute how tense and nervous I was and did her best to calm and reassure me during the week that everything would be okay and no one would be upset if I decided not to go through with it.

We didn’t cover a lot of ground rules, because I didn’t want her to feel restricted and wanted her to feel like she could completely let loose and enjoy herself, but I did ask Nicole and Greg not to try and make fun of or humiliate me. I was already struggling with my my desire to see her fucked by another man and I was worried that would put me in a bad mental spot for our first real time. I did privately admit to Nicole that I might want to explore other aspects of this lifestyle down the road but I didn’t think I was ready for that. She totally agreed on all fronts and both Nicole and Greg agreed to keep things light and fun.

When Friday finally came I was a nervous wreck and was pacing back and forth waiting for Greg to arrive. Nicole had to force me to sit down and relax.

“Stop it,” she told me. “You’re driving me crazy. There’s nothing to stress about, we’ve been friends with Greg forever. We all have a veto tonight, and there will be no hard feelings between anyone if any of us wants to stop.”

“You’re right,” I sighed. “I just… I want you to be happy.”

“I am happy,” she replied. “Don’t do this because of me, do it because it’s what you want. We’re only going through with it if everyone feels the same way. There’s no pressure tonight. Pressure is a huge turn off for me and I guarantee you if I feel it towards anyone from anyone I’m shutting it all down and sending everyone home.”

“You know this is my house right?” I smiled at Nicole.

“I’ll send you to my apartment,” she laughed. “I like your bed better.”

“You’re right,” I said and sat down beside her. “It’s just another night of us hanging out. We’ve done it hundreds of times before.”

“Exactly. Don’t even worry about bringing it up. I’ll handle everything. I’ll start the ball rolling if the moment feels right and we’ll stop if I get the slightest whiff that you’re not into it, okay?” she told me.

“Okay. Thanks.”

The doorbell rang and I practically jumped out of my seat.

“Oh my god,” Nicole laughed. “Go get us some drinks, I think you need it.”

I went down to the basement to get some beer from the fridge down there while Nicole greeted Greg. I grabbed three then thought better of it and just brought the case up, I was sure I was going to need it. 

I paused at the bottom of the stairs, my mind was racing and I wasn’t entirely sure I could go through with it. I desperately wanted to see her with him again, I’d been fantasizing about it every night since it first happened. It was obvious that Nicole was looking forward to it again too but I could tell she was trying to minimize her excitement around me. She didn’t want me to do it for her, she wanted me to do it for me. Greg was good too, after our talk he didn’t bring it up again and was just acting like nothing was different between us. That’s exactly what I needed from the two of them.

As I approached the top of the stairs, I could see the two of them having a quiet serious conversation. I waited for a moment and tried to listen, but they were talking too softly to hear anything. I saw Nicole smile and give Greg a hug, the only words I could make out were “thank you” before they broke the hug and I came into the room.

I greeted Greg and offered him and Nicole beers from the case I brought up. Greg flipped on the TV and put on the evening baseball game and I was instantly relieved that conversation was just like it always was, complaining about the manager and the team's recent performance. I was instantly put at ease.

The next hour or so was just like any other time, Nicole served us snacks, I made sure we all had drinks and we all just hung out, laughed and had a good time. 

When I left to use the bathroom I think I saw Nicole give Greg some kind of signal, my heart skipped a beat thinking that something might start but I calmed myself down. Nicole and Greg had been playing it slow all night and I knew they wouldn’t rush it. Part of me wondered if that was for my benefit or theirs. They both obviously wanted each other again, but I was the most nervous by far. I’m sure they thought easing me into it was the best way for everyone to get what they want, I was after all the one most likely to call it off. They didn’t need to worry though, whatever happened now, I wasn’t going to stop it. If I did I would probably never get this opportunity again. I wanted to see her get fucked, I wanted to see her cum and when the moment came I was going to make sure they went through with it.

When I got back to the room I could tell that the energy had shifted. There was a growing nervous tension between Nicole and Greg that I hadn’t noticed all night. Maybe I was too caught up in my own nerves to notice it, but it was definitely there now. I thought it was hilarious as I sat down, for the first time tonight I wasn’t the most nervous one.

Nicole started things by making innocent little bets on upcoming plays in the game. The wagers weren’t anything too serious, silly dares and things like that. But it progressed to Nicole offering things like flashing her boobs, or removing an article of clothing. 

I laughed along with them and unsurprisingly Nicole was completely naked within the next 15-20 minutes having “lost” a series of bets. To be honest, I’m not sure any of the bets after the first few made any sense, they just were there to provide a plausible reason for her to shed clothing once she saw I was comfortable with what was happening.

“I don’t have anything left to bet,” Nicole teased once she was naked. 

Greg suggested she’d have to masturbate in front of him if she lost. She agreed and it was the first time I’ve seen her blush in a long time. I don’t think she was expecting that request but said she would do it and a couple minutes later the bet was lost and she was getting into position.

Greg sat on the floor and Nicole scooched close to him and lay down in front of him with her legs bent and positioned on either side of him. He was already getting a nice view of my girlfriend's pussy, but he had an idea to make it better.

Greg grabbed a couple pillows off the sofa and placed them under Nicole’s butt, raising her pelvis. As she raised up, her legs spread more apart, obscenely exposing herself to our friend.

Nicole’s face was beet red, but I could tell she was still into it, there was no hesitation in doing what Greg asked.

“You look perfect. Now, play with yourself,” he commanded.

Nicole briefly looked at me and motioned for me to come closer. When I smiled and approached her she relaxed seeing I was comfortable with this latest escalation.

I sat on the sofa behind and to the side of Greg to get a perfect view of Nicole performing for our friend. Once I was comfortable she closed her eyes and started rubbing her clit, a soft moan leaving her lips as she did.

“That’s good,” Greg smiled at her. “But I want you to open your eyes and look at me while you do it.”

Nicole did as she was asked and stared at Greg as her breaths started getting shorter. The room was silent except for the background noise of the television and Nicole’s increasingly urgent panting. Greg and I stared at her pussy as she played with herself, she was fully aroused now and it was glistening with her juices.

“You look so hot like that,” Greg said to her. “Your pussy is so wet. Cum for us Nic.”

Nicole’s body shook as she let a small orgasm overtake her.

“I think that’s enough,” he told her once her orgasm subsided and helped her down from her awkward position. 

She took a quick glance over and me and I smiled at her, she looked equal parts embarrassed and turned on but smiled back pleased that things seemed to be progressing well.

“You’re so bad making me do that,” she laughed and playfully slapped Greg’s arm. “But I loved every minute of it.”

Greg took her in his arms and pulled her close into an intimate embrace. They held each other like that for a couple minutes before they started kissing and their hands started wandering over each other's body. Nicole shifted her position and angled her body towards me, parting her legs. I instantly saw why. Greg’s hand had found her pussy and I watched as he slipped one, then two fingers inside her.

I watched and listened in silence as Greg finger fucked my girlfriend, her soft moans and the wet slapping sounds filled my ears. Nicole looked at me with glazed eyes.

“Oh Mike, it feels so good,” she told me. “I love you watching me like this. Can you see my pussy like you wanted? Can you see how wet I am?”

Nicole leaned back and spread her legs further apart, hiding absolutely nothing from my view.

“I need your cock Greg, please,” she pleaded after a couple minutes of his hands working their magic.

Greg lifted her off the floor and placed her on the sofa beside me. He pulled her forward so her ass was on the edge of the seat and raised her legs up. Nicole held her legs up with her hands and parted them for Greg as he took his position kneeling in front of her.

Nicole turned her head and looked at me, the look on her face was one of pure lust.

“Are you ready Mike? I need this so bad,” she told me. “I want you to see everything, just like you told me.”

She turned back to Greg who now had his cock pushing against her pussy.

“Fuck me Greg,” she begged.

Nicole was so wet and ready that Greg was able to push all the way in on his first stroke. Nicole threw her head back and let out a loud low moan as he buried his cock inside her.

“Oh god Greg,” she cried. “Your cock is so good.”

I sat there stunned and watched Greg pound in and out of her, her familiar groans and cries were for him tonight, not me.

“Mike, your hand,” she pleaded after a couple minutes. “Please?”

I reached over and put my hand in hers, the same hand of hers that was holding her legs open for Greg. I know she wasn’t intentionally trying to humiliate me, but it felt like it all the same. I felt my face start to redden. She may not have meant it this way, but I was helping hold her legs open so Greg could fuck her easier.

Taking her hand was all she needed to completely let go and think of nothing other than the pure pleasure of the cock driving in and out of her. It was almost like she immediately lost herself in an orgasmic haze. 

I’d never seen her cum so fast and so hard, and from the look on Greg’s face this was new territory for him too.

She cried out both our names as she came over and over again.

Greg briefly pulled out and a disappointed whimper left her lips, “Greg, please. Just a little more.”

Nicole didn’t need to worry, Greg wasn’t finished with her yet. I let go of her hand and he moved off the sofa and onto knees, with her chest resting on the floor and ass in the air. She looked back at me and our eyes locked. Nicole had positioned herself so I could see everything as she offered herself up to him. I felt a lump in my throat as she reached back with her hands and spread her cheeks completely exposing her pussy and asshole for him to continue his assault. Nicole’s grunts once again filled the room as Greg took his place behind her and pounded her doggy style.

“Where do you want my cum?” he asked as he got close to finishing.

“Cum inside me,” she whispered. “I want to feel your cock inside me when you cum.”

Greg couldn’t take much more and with one final push he erupted inside then collapsed on top of her, the two tangled in a sweaty mess of arms and legs.

“Thank you so much Greg, that was amazing,” she told him as he rolled off her. “I’ve never been fucked so good before.”

She kissed him passionately on the lips and I could feel jealousy starting to build inside me.

“Thank you for everything, please stay the night. You can have the sofa or spare room, whatever you’d like. I’m sorry I can’t set it up for you, but you know where the blankets are, right? I need to go. I really need to be alone with Mike right now,” she said.

He nodded and I picked up Nicole off the floor and carried her to our bedroom.

“I love you so much,” she whispered in my ear as I placed her gently on the bed. “Will you make love to me now? I need you to take me, I need to know we didn’t go too far and you’re okay.”

“I’m okay,” I promised her. My mind was swimming and I didn’t know what to say. M\aybe I wouldn’t be okay in the morning, maybe I’d have regrets, but for now I was more than okay with everything.

She reached for my pants and helped me undress for bed.

“You’re so hard,” she said. “Will you make love to me now? Please? Are we okay?”

“Yes, we’re more than okay. Everything is perfect,” I said and crawled between her legs. At that moment I didn’t care that she was full of Greg’s cum I wanted her more than I ever had before. 

A wave of relief washed over Nicole’s face.

“Take me,” she smiled. “As hard as you want, however you want. I’m all yours.”

With that I slammed into Nicole’s pussy and before long she had her final orgasm of the night, one of the biggest ones yet, as my cum mixed with Greg’s inside her.

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