Peter’s Dilemma

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Note: This is the second part of this series, it goes further down the cuckolding path from “Peter Meets Sarah”. I would suggest starting at the beginning, each part of the series will continue down this path.

Sarah was just lying there and I couldn’t bring myself to wake her up. It was an argument or breakup for another day.

I went back to bed, heartbroken and holding back tears. But there was something else too.

My body seemed to be betraying me.

As I tried to fall back asleep my mind kept flashing to what I had just seen and my body was reacting to the image, not the thought of what it was.

Or so I told myself.

I couldn’t believe how hard I was as I drifted off to sleep, but sleep wasn’t much of a relief as I just kept seeing the image of Jason’s massive cock thrusting into Sarah.

In my heart I knew I wasn’t even a third the size of Jason which made the grief feel worse somehow. Like it was earned.

And that feeling of pain was understandable, what confused me was how hard I was, even as I slept.

I felt relief as I dreamt the images of Jason’s final thrusts and seeing the cum begin dripping down Sarah’s thighs.

The next morning Sarah was whispering into my ear as I woke up.

I didn’t understand at first, she was saying. “It’s okay Peter, I’m sure it happens to some guys.”

Was she about to admit what had happened the night before?

As I woke up a little more and felt it, the wet load in my boxers was almost as embarrassing as what I had seen.

I couldn’t even remember the last time I had a wet dream, not to mention was this my body’s response to seeing Jason take my girlfriend?

I could barely stammer out a response before Sarah followed up with a giggle and saying, “If I had known how turned on my teasing made you I would have rewarded you last night. Now you just have this little silly mess to clean up.”

My mind was racing a bit, I couldn’t help but compare myself to Jason and how he just took Sarah and came inside her. While my small dick could only muster a wet dream as I thought about him.

Wait had I just called my own dick small? Was Sarah getting at that when she said “little silly mess”.

“I think I was just a little drunk last night and” I finally started to say.

But Sarah cut me off saying, “It’s okay, next time I tease, I’ll just make sure you’re rewarded too.” As she hopped out of bed.

I didn’t know what to do, I needed to talk to Sarah about what I saw but something was holding me back.

Would she call out the fact that I had a wet dream that night?

I could hear them giggling in the kitchen but I was too sad and confused to go out there and face them. I wonder if Sarah told him that I had a wet dream.


I didn’t get the nerve to confront Sarah, and a couple more days went by before I could. Thankfully Jason had to go out of town for a long weekend so he wasn’t around as I figured out what to do.

I didn’t bring up anything to Sarah, at that point I was too embarrassed. I figured, or maybe hoped, it was just a one time thing.

With Jason gone it felt like things were back to normal, Sarah and I had a great time.

With the place to ourselves one night we started to get frisky, she had been flirty with me all day and when we got home was all over me.

Pulling me into the bedroom she stripped down naked, her pink puffy nipples turning hard as my fingers explored her sex.

It was our first time since I had seen her and Jason together and the image of his cock in her kept flashing in my head.

When I slid inside her, I couldn’t help but notice how little I filled up Sarah’s pussy compared to him, not to mention the noises she made were not the same.

Sarah flipped over onto her stomach, arching her ass up, leaned up on all fours and harshly said, “Fuck me from behind!”

It was more of an order than the normal sexy voice she had in bed with me.

Her ass looked so nice bouncing there as she waited for me. I complied as I just wanted to prove myself, I slid my small dick into her perfect pussy and began to thrust as best as I could.

I was feeling better as I began to feel Sarah get into it too, she dropped down to leaning on her shoulders as she did her C-cup breasts bounced perfectly as they came to rest on the bed.

I couldn’t see her face but it seemed like she was enjoying it and I felt her bring one hand to her clit to start rubbing.

Her other hand grabbed mine and I felt a glimmer of hope that I was winning her back.

That faded quickly though as she brought my hand to her chest and she yelled, “Squeeze my tits.” I began to realize this was the position Jason had her in, just as I felt something join my dick in her pussy.

My heart sank, her hand had left mine on her bouncing tits and had dropped down to her pussy. She put her fingers in her pussy with my dick!

I’ve never felt so small as she got more wet then I had ever felt.

She began to finger herself with three of her fingers merter escort and my little dick. Her moaning changed, “Yes just like that, yes J…” but the rest trailed off as she pushed her head into the pillows on the bed and I felt her orgasm shiver through her body.

As soon as Sarah came she pulled me out of her and rolled over to her side of the bed, leaning up she gave me a kiss on the cheek while saying good night.

Moments later she was drifting off to sleep, without even a thought of how I didn’t cum.

I was still kneeling on the bed with my limp dick somewhat hard but also feeling a deep sorrow as the thought of helping my girlfriend basically masturbate to another man went through my brain.

What was worse was as I laid down I felt how wet the spot below Sarah’s pussy was on the bed. I tried to shift but I couldn’t get out of the spot.

It was like Jason’s dick was laughing at me with how wet the thought of him made Sarah.

It took me a while to fall asleep, and the dreams of Jason and Sarah came back only this time I was out on the couch below them like Britney had been.

I saw her big ass jiggle with each thrust from the cock of a real man, it wasn’t even a comparison to mine.

I could feel her juices drip down on to me just like the wet spot on the bed.

I heard her tell him to cum inside her and saw him grab her perky tits as the slapped together with each of his thrusts.

Thankfully I woke up but it was as I rolled back into the wet spot on the bed.

This was ridiculous, I… then I realized I wasn’t feeling the wet spot from Sarah.

“Oh did you have another wet dream Peter” Sarah said, as she saw me feeling around at the cum in my boxers. She continued while tracing the outline of me dick with her pinky finger.

“If I had known you wanted to finish I would have helped the little guy out. It just seemed like you didn’t have it in you.”

Finishing with a wink like it was all a joke to her. She climbed out of bed and went to the bathroom as I changed out of my boxers, mind racing.

I was devastated, yet also so confused.

Had I just cum twice to the thought of a real man fucking my girlfriend? Wait why did I keep calling him a real man, am I considering myself less of a man?

My mind was racing and beginning to panic.

I decided I would need to confront Sarah before Jason came home the next night as I couldn’t handle this anymore.

That morning I kept trying to work up the courage to talk to Sarah but she was in such a good mood, my animosity for her all seemed to melt away.

I thought maybe this was just something we could work through, I mean after all it was really my fault for not stepping up and stopping it earlier.

We had a great day together and every time I looked at Sarah I got excited, she was just so beautiful.

That day she was wearing a very thin pair of biker shorts, ones that when she bent over I could see her g-string line through the sheen.

Her ass seemed just stuffed into them and I swear she kept finding reasons to bend over in front of me, and I liked feeling that attention again.

She had a crop top sweatshirt that showed off her great abs. She also wasn’t wearing a bra so whenever she bent over the bottom curve of her C-cup breasts slipped out, just enough to know she didn’t have anything on below the sweatshirt.

It was making me crazy horny and excited to get into bed that night after seeing her bounce around all day.

I knew I could make it up to her after not pleasing her last time.

I knew I could improve.

I got into bed first and was watching as Sarah moved around the room, bending over to untie and take off her shoes when she easily could have just sat down to do it.

Seeing her ass sticking up and her boobs popping out a bit already was getting me pretty hard.

Sarah turned back and saw me staring, she had a glimmer in her eye and I thought I was about to get lucky.

As she walked towards the bed she let out a big yawn and stretched her arms up showing her gorgeous abs and just a peak at her tits again.

I was basically gawking at her at this point, she knew what the teasing did to me.

Next she turned back around and took off her biker shorts and her ass came jiggling out, I could barely contain myself.

Sarah let out a little giggle as she looked towards me and said, “It looks like someone has liked seeing me tease them all day.”

She brought her pinky finger up and down my shaft over my boxers, “Hey little guy!”

I loved seeing her like this but didn’t love the new way she was referencing my dick.

At least she was all mine tonight.

“I had noticed you weren’t quite yourself lately,” Sarah said in a sexy voice while still running her pinky finger up and down my little dick.

Leaning over in just her light gray g-string and crop top sweatshirt, I felt so turned on and now she was even addressing my concerns!

To think I had thought about nişantaşı escort breaking up with her, I knew we could work it out.

She continued in her sexy voice, “So I thought I would tease you throughout the day and show off for you like you enjoy so much.”

She pulled off my boxers and began to climb back onto the bed. My body was already tense with excitement.

Knowing I was about to get so lucky, I couldn’t stop staring at her lips and she spoke so sweetly to me.

They weren’t overly large but stuck out just enough anyone who spoke to her knew how great she could suck a cock.

As she ran her tongue across them I had to shake my head just to make out what she was saying.

“…. and if you last long then I’ll reward you in the morning with your favorite way to wake up.” She ran her tongue across her lips again and I almost blew my load right there.

As I went to pull Sarah on top of me we heard the front door slam shut and Jason yell, “Honey, I’m home!”

Sarah let out a giggle responded, “Be right out sweetie” and pulled away from me saying, “Oh that Jason, isn’t he so funny. I know you’ve missed having him here to see me tease him.”

She gave me a wink, patting my little erection as she leaned in close. I could feel her perky breasts rest on my shoulder.

Then she whispered, “time to see just how much of a tease I can be, I can tell somebody likes that.”

She pinched my dick hard between her fingers, “Isn’t that right little guy!”

I wanted to let out a yelp but a little bit of pre-cum drizzled out and all I managed was a moan.

She laughed, “I knew that would turn you on. You’ve been missing him so much. Those dreams of yours have been a sign!” She patted my little erection with a concerned look.

Then said with a wink, “I’ll go let him know just how much.”

Before I could say anything she hopped out of bed and walked out the door.

I just watched as her ass bounced back and forth, her g-string barely visible between her plump round cheeks.

My last thought as she left the room was that I should have spoken up, but it almost didn’t seem my place. Should I go out there?

I heard a giggle which snapped me out of my head and Jason’s deep voice say, “Twice huh? Jeez, if I…” his voice trailed off. I decided not to risk the embarrassment and to just wait until Sarah came back into the room.

What I thought was going to be a great day was ending in such a gut wrenching way. Time seemed to move so slow.

After 20 minutes and not hearing anyone say anything for a while, I decided I should peak my head out. Better to catch them just after something had happened, that way I wouldn’t have to face the same embarrassment.

Just as I was about to get up I heard what sounded like a hand slapping the counter. Followed by Sarah’s muffled voice, but I couldn’t make out what it was.

My mind flashed back to the other night and seeing Jason’s massive cock pumping into Sarah’s tight slit and I started to panic.

And then Sarah slowly opened the door to my bedroom, her hair was tousled but she still had her crop top sweatshirt on. Her sleek abs looked to have a little glimmer of sweat and tone as if from a workout.

Her g-string was all that covered her lower half and the light gray fabric was almost completely darkened by wetness.

I was too shocked and embarrassed to say anything, all I could do was roll away from the door and act asleep.

Yet as I did, I noticed how stiff my little dick was. What is this reaction? Again aroused by my roommate fucking my girlfriend? I was so confused.

Sarah climbed into bed with a giggle seeing my hard on. She pulled herself in behind me, pressing her tits up against my back. I could feel the wet fabric of her g-string against my butt.

She whispered as she reached around and began to bring her pinky finger up and down my dick, “See, I knew you would like this game. You should have come out to see me teasing Jason like you wanted.”

As she reached the top of my cock she gave it a pinch and nibbled on my ear.

I wanted to tell her how I didn’t like her doing these things but they clearly turned me on so much.

She then instructed me to get out my phone, my mind raced- had she taken pictures and sent them to me?

But instead she had me open to a stopwatch and start the timer as she began to tell me how she teased Jason.

“I knew he was just back from his trip and I offered to get him a beer, he accepted but asked for one of the ones from the bottom of the fridge.”

I thought back to all the times that day Sarah had bent over and her sweatshirt had come up to show off her great tits.

“So I reached down for the one he asked for and I even acted like I couldn’t find them at first. You would have loved it! He was just staring at me and I could even see the outline of his shaft shaft to creep up in his pants as he sat on the bar stool.” She had started running her pinky finger up the underside of my ortaköy escort prick.

“Then as even more of a tease I was about to hand him the beer but instead I turned back around and said I needed to get him a glass to be a proper server. As I spun I could tell his eyes went straight to my ass and I reached up showing how bouncy it is while on my tippy toes for a glass from the shelf.”

As she said, “tippy” she pinched the tip of my cock hard.

I let out a moan, why was I so turned on by this? But it felt good to think about her showing off like I had seen her do all day.

“As I brought him the drink, I told him about… well your little problem.” My face turned bright red, I couldn’t believe she had told Jason about my wet dreams. But just as my mind started racing Sarah began to stroke my cock with her pinky and thumb. I was still so hard and turned on by her.

Sarah continued, “Jason was so funny, he said I needed a real man in here to show you how it’s done.”

She pinched the tip of my little dick harder than she had before.

I could still feel her breasts pushed up on my back as she reached from behind me with her fingers working my hard cock, I let out a moan.

I was getting so turned on but I didn’t know why. I could feel the precum leaking out when she pinched me.

“I know you so well Peter, I knew you’d find this so hot, that’s why I kept going – for you.”

This was for me? But what did she mean kept going? I wanted to argue but I was so close to cumming.

Sarah continued to whisper in my ear, and with every up stroke of her two fingers she pinched the little tip of my little cock.

“So I pointed to the bulge in his pants and asked if that was how he’d show how it’s done.”

My mind was in pain but my body was on edge as she continued, “I could see the outline of his shaft so clearly and finally I told him how he could show you.”

She then pinched my little prick and pulled it up so hard as if to stretch to match the size to that of Jason.

“He stood up in agreement and his pants stretched out so far – I wish you had been there to see! Jason unzipped his pants and pulled out the largest cock I’ve ever seen.”

For the first time that night she used her whole hand, squeezing my dick on the down stroke and I couldn’t take it.

I started cumming on the spot, bursting out all over my sheets.

Sarah leaned closer into my ear, “that’s a good little boy, I knew having a big dick around to show you the way would get you back to normal.”

She had returned to just using her pinky and thumb to stroke me but it didn’t matter, all I had was oozing out as I let out a pitiful moan.

I didn’t know what to do anymore, this clearly turned me on but my roommate had stolen my girlfriend away from me basically turned me into some small dicked creature in her own eyes.

And she had been so open about the infidelity, it’s like she didn’t care.

“What’s the time at?” Sarah said much more sternly, it was definitely an order and I read the time to her, I had lasted only for 1 minute and 13 seconds.

I told myself it was the build up of the whole day, all the teasing she had done.

But I knew that wasn’t true.

I was still so hard and Sarah continued to stroke my little dick with her two fingers, only now would pull hard on every third up stroke and squeeze tightly with her whole hand on the way down but then return back to her two fingers on the next stroke.

“I figured you wouldn’t last long with how much my teasing turns you on, but less than two minutes?”

She took her hand off my prick and grabbed my face, drips of my own cum slapped against my cheek as she turned my head towards her and kissed me deeply.

It was just then that I realized we hadn’t kissed since she came back in the room.

She had something new on her breathe but I couldn’t place it, perhaps she had a beer with Jason.

Her hand returned to my sad, hard cock and repeatedly the tortuous yanking from before even though there was nothing left to come out.

I felt her hot breathe return to my ear as she delivered a final blow to my spirit, “It took both hands just to give Jason’s huge cock a proper tug. I couldn’t believe how it felt in my hand, the strength of it alone made me get dripping wet.”

She pressed her panties into my backside and reminded me of how wet they were then she walked in the room. She let out a deep moan as she twisted my dick on the next tug up and bit her lip.

“I knew that’s what a real man felt like as I worked his cock back and forth. I didn’t even remember to have him start a timer until probably 5 minutes of working it with both of my hands.”

There was nothing left in me, no spirit of the man I was, no cum in my pathetic balls.

“As I compared it to my forearm I told him to start keeping time so I could see how long a real man lasts.” My heart dropped again, tears welled in my eyes, she jerked off my roommate and was bragging about it to me now.

I had already cum but she kept playing with my little dick, still pinching it as if to say with each pinch that Jason was a real man and I was a pathetic boy.

“I don’t think you’ve ever made me as wet as I was while jerking him off. You could have slid into my soaking pussy so easily, though Jason would probably have been too big.”

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