Cheryl and Mike

This fantasy occurred to me as my GF Cheryl and I were lying in bed one morning, and I was fingering her pussy, trying to make her come. She was still sleepy and though she kept getting close again and again, we had trouble getting her over the top. Eventually we did, and her orgasm lasted nearly a minute. In the meantime (almost an hour) I alternated between focusing intently on the job at hand and imagining this scenario. Sex between Cheryl and my friend Mike is a recurring fantasy of mine, as he has a big cock and a reputation for knowing how to use it, and for sweet talking hot girls into letting him try it out on them. (Also I’ve always fantasized about my girls cuckolding me, although I don’t think I could ever actually go through with it. Kinda the same as my occasional bisexual fantasies.) I know his dick is big because I once walked outside to (my and my ex’s) hot tub area during a Saturday night house party, and Mike was standing in the hot tub with our friend Jennifer kneeling in front of him, his entire shlong down her throat. When she saw me, she pulled back and all 10+ inches of it slowly sluuuuuurped out of her mouth. I hope he didn’t think I was gay just because I was staring at it with my mouth open.

I think (though I’m not 100%) Mike fucked my promiscuous ex wife Misty a few times while he was renting a room from us and didn’t have a job. Misty worked evenings at a local restaurant and I worked days, so the two of them were alone at the house most days, ample opportunity for him to talk her into taking his bone into her slutty pussy. I’ve fantasized about that possibility dozens of times. Anyway, I digress.

Mike and my Cheryl have always had a flirty relationship. When Cheryl and I were first seeing each other we were keeping it on the DL, as she was recently divorced and I was sorta friends with her ex. Mike was hitting on Cheryl at the time (via text) even though I had told him we had hooked up a couple times. She resisted him, but has admitted to me she likes him and thinks he’s cute, and is intrigued by his big member. My latest fantasy…

Mike came to town one weekend just to get away, and the three of us went out to a local watering hole Cheryl and I like. Mike and I were shooting pool and Cheryl was running the juke box. We all started catching a buzz and having fun. Mike was making occasional friendly comments about how pretty my girlfriend was, and soon started making innuendos, after seeing how well his compliments were being received by my smiling and laughing girlfriend.

The conversation suddenly pivoted to female orgasms. Cheryl told a funny story about a friend’s troubles in this area (“the wind has to be blowing from the west, that one John Legend song has to be playing, she has to be debt-free…”), and also mentioned it wasn’t until our fourth or fifth time together that Cheryl was finally able to relax enough to let go and come.

Mike interjected, “I’ve made every chick I’ve ever been with come the first time. Almost always more than once.”

I instantly pictured it in my mind. Him fingering Cheryl, or licking her pussy. Her moaning. Coming. I started to get hard.

“No fucking way,” replied Cheryl. “I know women who have never orgasmed in their life, let alone the first time with a new guy.”

Smirking, Mike replied, “That’s because they’ve never been with me.” He laughed, staring into her eyes. She was staring back, and it looked like she was thinking. Imagining the same thing I was.

There was a short but significant pause, during which I imagined we were all thinking about the same thing. I got harder. I snuck a glance over towards Mike down and at his crotch. I couldn’t be sure but it looked like he might be sporting a semi himself. Finally Cheryl shook her head and spoke up. “There’s no way you could make me come the first time, that’s for sure.” She laughed nervously as if trying to pass the idea off as ludicrous, but there was something that made me wonder…

We had talked about it in bed, role playing, her breathing into my ear that she could do with a real man with a big cock to satisfy her. Someone like Mike, someone we knew and trusted to be clean so he could fuck her bareback, so they could really make each other feel good. Think of how much Mike would like to shoot his come into her hot, tight, wet pussy, she told me. How much it would mean to him. Didn’t I want them both to feel good, she asked? My good friend and my sweet girlfriend? I always had to admit I did. We didn’t talk about these kinds of fantasies much, as it always ended with me coming way too soon.

Which is why my hardening, pre-come leaking cock twitched when Mike asked, “Wanna bet?” His million dollar panty-dropping smile was now on full display.

Cheryl was silent for several seconds, contemplating. “Bet what,” she finally replied, so softly we could hardly hear her.

Now it was Mike’s turn to be quiet. He turned and stared at me. I thought I saw a glimpse… if he had fucked Misty, she would have told him about my cuckold fantasies. He may have decided it was okay to do but didn’t want me to know so things weren’t weird between us. He at least could see that right now I was waiting almost eagerly to hear what he had to offer. We both turned and looked at Cheryl, who was staring at Mike, slightly smiling.

“We’ll get to that,” Mike began. “First, what are the ground rules?”

Cheryl answered almost immediately. I could hardly believe what was happening. “You can only use your fingers. You keep yours clothes on and I’m under a blanket. No peeking.”

“Can I kiss you?” Mike also answered quickly, trying to keep up the momentum.

“Of course!” Cheryl replied, smiling.

Mike sighed and shook his head. “I don’t think I can do it. It would be super awkward if we weren’t both naked.” He shook his head again and laughed. “Yeah, we better not.”

A lot of time went by in a sort of tense silence. I was about to get up and go into the bathroom and quickly masturbate. Cheryl had been staring at Mike for what seemed like 5 minutes when she finally spoke, sounding like her mind had been made up. “OK. All three of us naked. I want Brian to watch, to make sure you don’t cheat.” I’m Brian, by the way.

“Sounds hot,” Mike said. “What else?”

Cheryl said, “I get to decide when it’s over.”

“Ok, sure. Not that this will happen, but what do you get if you don’t come?” He was leaning in towards her from across the table. They were staring at each other and smiling.

“You take me and Brian out to your favorite place the next time we come to Denver.”

“Sold!” Mike answered enthusiastically.

“What do you get if you win?” Cheryl asked. Her cheeks were noticeably flushed.

The smile faded from Mike’s face. He leaned in close and stared right into Cheryl’s eyes. “Well, beautiful… After I make you come — and I will —” He turned and looked and me as he said that last bit, smiling again. “Well, how do I put this. We’re gonna have sex, Cher.” Cheryl gasped slightly. Mike let it hang in the air for a few moments before continuing. “I’m going to fuck you in your and Brian’s bed. I’m going to make you come again with my big dick and you’re going to look Brian in the eye when you do,” he said, smiling all the while.

Cheryl just stared at him with her mouth slightly open. “Jesus, Mike,” I protested. “Sounds like you’ve been thinking about that for a while, buddy!” I was aroused, but also offended at how brazen he was being.

“I have been. I think about her sometimes when I jack off,” he said, looking directly into Cheryl’s eyes. “Chill, Brian. Misty told me you get off on your girl fooling around with other guys. We both know you’re into this”.

“She told you that? When?”

Mike shrugged, not saying what I now knew. I know Misty wouldn’t have told him that if she wasn’t trying to convince him to fuck her.

“Well? You want to see me try to make her come, right?”

I looked down. “Yeah.”

“Those are my terms, take it or leave it.”

Cheryl and I looked at each other. I gulped and nodded slightly, giving my girlfriend permission to go to 3rd base with my lothario friend. Maybe all the way. What was I thinking?

Cheryl said, “Hang on, Brian. That nod isn’t gonna cut it. You need to say it. I’m not going to have this be an issue later, like I was doing something you didn’t want.”

I gulped. I could feel Mike staring at me, almost gloating. My face turned red. I gulped again and croaked out, “I want to see him try.”

Cheryl slapped the table. “Check please!” She smiled, looking back and forth between the two of us. Mike grinned from ear to ear, and I laughed nervously. Was this really going to happen? Did I really want it to?

20 minutes later we were pulling into our driveway. I noticed they hadn’t wasted any time paying the check (Mike threw down $100 on a $70 tab as we walked out) or getting us all back to our place (Cheryl sped through two yellow lights that turned red on us). I unlocked the front door and walked inside (I noticed them holding hands behind me when I turned), and just like that Mike and Cheryl were making out on our bed, and I was sitting in a chair next to it, trying not to be the first one to pull out my dick. Mike was rubbing Cheryl’s crotch over her dress as they kissed. She was moaning and squirming a little. His enormous phallus was semi-erect and putting some strain on the seams in the crotch of his Levi’s. I was painfully hard.

She stopped and looked at me. “Are you okay, honey? Are you sure this is ok?”

“Yes baby. You’re so fucking sexy right now. I want to watch Mike try to make you feel good!”

She smiled and said, “Oh, good,” turning back to him. They resumed exploring each other’s mouths and tongues, and Mike’s hand started to make its way up her dress and inside her panties. She stopped him, smiling. “Take your clothes off, Mikey. Honey, will you help me?”

She sat up and we worked her dress up and over her head while Mike took off his shirt. She laid back and lifted her hips, and I slid her panties down and off her legs. She undid her bra and watched Mike slipping his pants and underwear off. His huge, veiny cock was already hard, and it stuck out menacingly as he climbed back onto the bed.

“I guess the rumors are true, huh?” Cheryl said, staring down at it. “You’re a big boy, Mikey.”

Mike smiled proudly. “Yep,” he stated, simply. He squeezed and made it bounce. It was a lot bigger than mine, in every way. The shaft had a slight downward curve, like mine, but the similarities ended there. In comparison, his looked like a man’s, mine looked like a boy’s. Cheryl just kept staring at it, blushing. I quickly got undressed and sat back down, lightly stroking myself, on the verge of coming.

Mike laid down on his side next to my girlfriend (who was on her back, her amazing tits on full display) and they started kissing again. He stroked his fingers through Cheryl’s trimmed pubes and explored the area for a minute before sliding his finger up her already very wet slit. She moaned into his mouth, and reached down and grasped his cock. Her hand looked tiny as she stroked it up and down. He whispered, “Yeah, Cher. That feels good.”

Within a minute or so she stopped stroking him so she could concentrate. She reached over to hold my hand (the one that wasn’t lightly stroking my cock), but apparently that was too distracting, so she put her hand behind Mike’s neck and pulled his face close to hers. Usually, when I’m trying to make her come she closes her eyes, but they were open now, looking right at Mike as he diddled her clit.

She was breathing kinda hard now and started giving him instructions: more up and down, softer, alternate between that and circles… RIGHT THERE, do NOT stop doing that. After only a few minutes she was moaning sweetly and sighing a lot. I could tell she was getting close. Oh fuck, I thought, he might actually do it. My dick twitched and I pulled my hand away just in time. I felt like I might cum anyway.

But he lost her. Some thought probably distracted her, and the moment was gone. Haha, motherfucker, I thought. Cheryl’s too self conscious. You’ve met your match. Mike 999, non-orgasming women 1.

Not that they were done trying. Time and time again, they would start over, kissing, him fingering her, her giving him instructions, getting close but not quite there…

After about 30 minutes, Mike must have tried something different. She gasped and told him, “Oh Mikey, right there. Remember that. Remember what you’re doing so you can show Brian.” She began moaning and whimpering, her legs twitching slightly. I think we all realized at the same time that it was really going to happen. Clearly we all wanted it to happen. Cheryl wanted to come, Mike wanted to make her come so he could fuck her, and I wanted her to come AND for them to fuck AND for them both to really like it AND for him to be better than me…

Mike’s cock stuck up between them in all its glory. Cheryl got closer to coming than she had yet; she was clinging to him, burying her face in his neck and whimpering. His massive cock throbbed and got even harder as he realized he would be inside her within minutes. I stared at his cock and listened to the sounds of her impending orgasm, and my cock responded in kind. I really wanted him to fuck my girlfriend. I wanted her to come. I wanted her to make him come. I wanted her to WANT to make him come.

“Oh god, Mike. I’m going to come all over your hand!” she exclaimed, and her body tensed. She moaned out, “AHH! AHH! AHH!” for a solid 30 seconds as waves of orgasm washed over her. Her pussy squirted a little on the mattress. I came hard, my semen spurting onto the side of the bed and pooling on the hardwood floor.

“Hey man, watch out,” Mike said. “You better not get any of that on me.” As Cheryl was descending back to earth, Mike took her wrist and had her start stroking his cock again, which was so engorged it was almost purple. It was clear to me what was on his mind, though Cheryl still seemed at little dazed after her powerful orgasm.

She finally became aware again of the monster in her hand. She stared into Mike’s eyes and slowly stroked him all the way up and down. She softly kissed his slightly open mouth — it was his turn to moan. She paused and turned to me, still slowly jacking him. “Honey, get Mike a condom, please. Fair’s fair,” she said, turning back to him and smiling. My cock was already fully hard again.

Mike said, firmly, “No. No condoms. I’m allergic to latex. Besides, Brian’s tiny condoms aren’t going to fit me. And sweetie, remember you told me you have an IUD.”

When had she told him that? My cock softened slightly.

She looked at me and cringed slightly. “Sorry, honey. I don’t know why I told him that.”

“Yes she does. You’ve been thinking about my cock, haven’t you? For a long time. Ever since Melody (his ex GF) told you about it, and how good it made her feel. You’ve made yourself come thinking about it.”

Cheryl looked at him for a moment, then turned to me and nodded slightly. “Sorry, honey,” she said again.

Mike moved on top of her, ending the conversation. Despite my feelings of having been something like betrayed, my cock swelled again. In fact, my hurt feelings quickly morphed into cuckold arousal. He pushed her legs apart with his knees and held himself up with his left hand, as his other hand guided the tip of his rigid phallus towards Cheryl’s puffy, swollen, dripping wet vulva. She pulled her knees apart slightly with her hands and her pussy flowered open, ready to receive him. I thought, why doesn’t she stop him? She always makes me wear a condom. Then I thought, I should stop him. Then I thought, I don’t want to stop him.

I expected they would fuck, fast and hard. I thought Mike would take her, roughly, dominating her and satisfying himself. I was wrong. He put his arms under her knees, spreading her wide, put the tip of his horse cock between her puffy labia and began to push it inside. It took them almost three minutes to get it all the way in, for him to press his pelvis down firmly against hers, for her vaginal walls to stretch to accommodate his girth, despite the notable amount of self lubrication her pussy had done… She sighed and moaned and gave him instructions — “ooh go slow, wait, be gentle… ah yes, that feels good, more” — pushing her crotch up to meet him and rotating her hips, determined, until he was all the way in, several inches past the deepest I had ever been, the head of it violating her cervix, the shaft dilating her opening so much she probably wouldn’t feel anything at all if Mike and I traded places… and they proceeded to make slow, passionate love, kissing and moaning, for almost 25 minutes. Almost all the way out, and ALL the way back in. Slowly, then faster, then urgent, then back down again. I stroked my hard dick and lost count of how many times I came, getting aroused again immediately after the last spasm of my previous orgasm.

Mike was a man of his word. Cheryl came again, just from his penetration. Three times in all before he finally tensed up, his cock swelling and hardening to it’s maximum, his breathing becoming ragged. Cheryl’s pussy was squirting, splashing against his lower abdomen when she whispered “come in my pussy, honey” sweetly into his ear. Honey? That’s what she called me. I lurched, a feeble dribble of semen coating my knuckles as I came again for the umpteenth time. Mike finally thrust one final time, grunting loudly — UHHHHH!—pushing his entire monster cock into my girlfriend’s vagina and holding it there, shooting pulse after pulse of his potent sperm deep into her eager womb. He grunted — UH! UH! UH! — for a good 10 seconds, his face in Cheryl’s neck. Copious amounts of thick come started leaking out of her around his massive, throbbing shaft. I knew from experience her pussy was squeezing him tightly, but I never get to fuck her without a condom. I could only imagine how her wet soft vagina felt, squeezing the last of his come out as he softened inside her.

He rolled off and she motioned for him to move over a little so she could, too, patting the mattress for me to get in next to her. I climbed in bed and hugged her. We kissed softly and she just kept smiling, her eyes half open. “Thank you, honey! That was amazing.”

Mike said, “Yeah, thanks honey. Your girlfriend really knows how to take a dick! Just kidding, buddy. Thank you. I thought it was fucking hot. Looks like you did too, huh?” I looked down where he was looking, and saw my own semen drying all over my thighs. “I’m going to leave you two lovebirds alone.” He got up and headed towards the spare bedroom, his (still huge) flaccid cock trailing a sticky string of his come, the shaft still shiny from her.

“Wait, let me get it set up for you. It needs fresh sheets,” Cheryl said, getting up to put on her robe and follow him. I could hear them talking as they made the bed, almost whispering. I couldn’t make it out.

She came back into the room after a few minutes, but she didn’t get in bed as I expected. She sat on the edge next to me.

“Thank you so much for being such a great boyfriend. I love you so much!! Would it be okay if I slept with Mike in the guest room? I know you have to get up early for work, and we’re both still kinda horny. Would that be okay, baby?”

“Uh, sure, I guess, if that’s what you two want.”

“I know I do! Did you see the size of that thing? You know I’ve only come once before from penetration, right? He made me come three times!” She giggled and squeezed my hand. “Thanks honey. We’ll try to be quiet.”

She kissed me, got up and walked over to her dresser, opening the top left drawer and pulling out the teddy I got her for Valentine’s Day last year. Letting her robe fall to the floor, she put the lingerie on. Cheryl turned away from me and arched her back, sticking out her cute behind.