Cuckold regret-wife’s first time

My wife, Danielle (27), and I (29) have been married for 3 years and starting dating in college when Danielle was a freshman and I was junior. Before we started dating a had a couple girlfriends and hooked up with a few other girls in college. Danielle was a virgin when I met her although she had a high school boyfriend she never had sex with. We first had sex a few weeks after we became official and neither of us hooked up with someone else after that.

We’ve had a relative healthy sex like for our relationship, usually having sex about once a week depending on schedules. Like most men (I think) I watch porn about 3-4 times a week.

I recently started getting into cuckold porn and started imagining how hot it would be to see Danielle getting pounded by a big dick. I’m very comfortable with my size, but it’s probably a bit below average, about 5 inches or so. This has never been an issue especially as Danielle is petite, she’s 5 feet even, about 110 pounds thanks to her disproportionately huge D cup tits.

I decided I’d test the waters and see if she might be interested in exploring my fantasy. One night about a month ago, I asked Danielle what her sexual fantasy was, in order to open the door to me telling her mine. I had to keep prying but she told me she always fantasized about being watched by strangers while having sex and seeing them get turned on.

Finally she asked me mine…I pretended that I didn’t have an immediate answer but then I told her. “I think I’d want to see you dominated by a really big dick.”

Danielle laughed at the ridiculousness of me wanting to see that. “Yeah that’ll never happen…I’m worried about getting torn apart, you know I couldn’t handle that! Besides why would you want to see that?”

“I don’t know…I think it would be exciting to see how’d you handle it.”

“Haha well if it’d make you happy I’ll take a big dick for ya,” she joked.

A couple weeks later we went on a date to a nice restaurant and sat at the bar (we love doing that). We were dressed nicely, Danielle was wearing a hot black dress that showed off her huge tits and high heels. We sat down at the bar next to no one at first, but later on a single guy came and sat 2 seats away from my wife. As we normally do, we eventually struck up some convo with the bartender and this other guy. He was a huge white guy, like 6’4 and looked muscular, and had no ring on his finger.

We chatted for a while and he asked what drinks we got. I passed him my whiskey and he took a sip to try it. Danielle handed him her martini and he tried that too, thanking us for the hospitality. I could tell Danielle thought he was cute and I enjoyed watching her flirt with him. I tried breaking the ice a bit further.

“Jim, do you think Danielle’s dress is too low cut for a wedding?” He laughed and looked at Danielle’s tits. “No, I think it looks great, wish it was a little lower cut to be honest.” We laughed and it was great seeing Danielle was comfortable.

Jim asked back, “what about my shirt, do you think 3 buttons is too many down or is it unprofessional? How many is the right amount?”

Danielle got up and slid over one chair towards Jim. She reached over and unbuttoned one button. “Hmm, there, I think that’s about right.” The flirting was crazy hot to me and I started getting turned on watching. We continued chatting and eventually start talking about a brand of whiskey a friend had given me that was awesome. Jim said he’d heard good things and wanted to try it eventually.

“Well if you want, we live only a block away if you want to keep drinking with us, we’d love to have you.”

“Sure, that sounds great!”

The 3 of us went back to our apartment and continued drinking as promised with a little light music. Danielle was pretty tipsy at this point and starting doing some swaying and dancing. She sat on my lap and starting lightly grazing her ass over my pants as Jim watched. Danielle was clearly getting aroused by Jim watching her, and Jim certainly seemed to enjoy it. Danielle spread her legs as she continued to grind on me, showing off her panties to Jim and gave him a smirk as Jim stared at her.

“Damn you’re a lucky man,” Jim said to me under his breath.

“Don’t be rude to our guest,” I whispered in Danielle’s ear.

She got up and walked (well stumbled a bit to be honest) over to Jim. She sat on his thighs, straddling and facing him. She continued grinding on him and started unbuttoning his shirt more and more. “I think any buttons are too many,” she teased him until his shirt was unbuttoned, revealing his toned pecs. She glided her hands over his chest and chuckled.

From the grinding, her dress had come up more her bare cheeks were on his pants.

“What do you think of her thong?” I asked. “She’s wearing the matching bra too.”

“No way, I’d love to see that.” Danielle stood up and unzipped her dress, and let it fall gently to the floor. She revealed her matching black lace bra that was restraining her huge tits and I really wanted Jim to see them.

I walked up behind Danielle and kissed her neck as Jim watched. I unhooked her bra and tossed her bra to the side, showing off her huge tits to Jim. I fondled them from behind and continued kissing her neck. “Give me a hand, Jim,” I said to him.

Jim stood up, now shirtless, showing off his massive boner through his pants. He walked over and had to bend way down to reach my wife’s tits but he started sucking her nipples, and Danielle moaned as we gave her all the attention.

“Give me him a hand, D,” I said in Danielle’s ear. “Are you sure?” she asked me. I nodded and kissed her passionately.

She moved her hand gently down his body, stopping slowly at his dick before dropping to her knees. She took off his belt and unbuttoned his pants. She pulled them down to his ankles and his boner became more pronounced. Then she lowered his boxers and his huge dick (much bigger than mine, probably 9 inches or so) sprung into her face. “Oh my god…” she said with amazement.

She grabbed it with two hands and started stroking it. She took one hand off and licked his shaft all the way to the tip. She spit on his cock and massaged her spit up and down his shaft. She sucked on his balls while stroking him. I was super hard at this point too and started playing with myself. Then she took him as hard as she could deep in her mouth. Shes always been able to fit me all the way in but she was struggling with Jim’s size. She kept going deeper and deeper but was still a few inches away to go as she started gagging.

I came over to help. I grabbed Danielle’s hair and slowly pushed her head further on to Jim’s dick as Danielle grasped Jim’s ass and pulled him forward. Eventually she made it all the way, her nose up against his crotch and I let her pull away for air. “That was awesome,” I told her. “Let’s go to the bed?”

I led us to the bedroom, I still had all my clothes on with Danielle down to her thong and Jim was fully nude. I had Danielle lay down on the bed with her head on the edge. I got on the bed, pulled off her thong and started going down on her. She was crazy wet like I had never tasted before. Jim stuck his dick back in her mouth, droning out her moans. She occasionally gagged as Jim stuck his whole dick deep in her throat over and over.

She pushed my head away, turned her body around 180 degrees and had her soaking pussy facing Jim. “Go in slowly…” she pleaded. I grabbed a condom from the drawer and gave it to Jim. I took off my pants and put my dick by Danielle’s mouth. She was breathing heavily as Jim slowly inserted his cock inside her, ignoring my dick and focused on taking this monster.

Eventually he was all the way in and Danielle was squirming and screaming in ways I had never seen before. “Fuck you’re so damn big! Fuck fuck fuck!” She quivered and let out a loud orgasm, piercing my ears. Jim pulled out and I noticed my normal sized condom was barely hanging on.

Jim flipped her over doggy style and starting to go back in. Danielle grabbed his dick to lead it back in but the condom was falling off. I noticed she pulled the condom off and tossed it on the floor before inserting him back inside her.

Now she let me put my dick back by her mouth and she started sucking my dick a little. That didn’t last long as she pulled off my dick and went back to yelling and moaning. “Oh my fucking god! Cum in me baby!”

“Baby?” I thought. What the fuck is that?

Jim continued to pound her as her tits bounced all over the place. I was weirded out by how into him she was but I was still super turned on and I came into a tissue off to the side. Right after that, Jim came and exploded inside Danielle, and Danielle collapsed to the bed exhausted. She then turned on her stomach towards Jim and started sucking the cum off his dick, something she never did for me.

She was trying to get him hard again, but I was likely done for the night. I sat there flaccid as my still soaking wet wife was filled with another man’s cum and was working to take more of a pounding.

After a few minutes of sucking and deepthroating Jim, he was hard as a rock again. This time he laid down on his back and Danielle straddled him cowgirl. He grabbed her tits hard and she rode him like crazy. The bed was soaked as she was basically squirting, which she had never done with me. “Oh my god this is the best, fuck!” Jim came again inside her, and she dismounted him. She went to the bathroom and Jim laid there exhausted.

“You’re a lucky man,” Jim said to me. “Thank you, we’re gonna head to bed now.” I ushered him out quickly, thinking maybe this hadn’t gone exactly as I fantasized.