My Cuckolding Journey
A Fictional Story by Sass4bass.
My apartment mate’s name was Will. He greeted me with a firm handshake and a confident grin. He was tall and broad-shouldered, with a strong jawline. Unlike me, he was the kind of guy who walked into a room, and everyone noticed. He worked in Sales and had the right confidence for it.
“Welcome, man. Your room’s down the hall,” he said as he slapped my back hard enough to make me stumble a little.
That first week I kept to myself, unpacking and trying to settle in. Then Kayla showed up.
She was unbelievably sexy. She had perky tits and a big round ass to go with a pretty face and sparkling eyes. She dressed to show off her body in tops that were too deep or too short, skirts which ended mid-thigh or even lower, and shorts that showed her under-butt.
She was flirty and sexual. She was Will’s casual fuck buddy and didn’t mind being called like that.
She moved with confidence, and every time she would come over, my heart would beat faster. She was everything I was not: sexy, bold, and free.
The first time I saw her, she was wearing a tiny tank top and tight shorts. Her nipples were faintly visible through her top. She smiled at me and came forward to introduce herself.
“I am Kayla, Will’s fuck buddy.”
I could only nod and look away as my face turned red. I mumbled something and left the room fast. I could hear her laughter as I walked away.
Despite the embarrassment of the first meeting, I started looking forward to her visits. I would sit in the kitchen or living room just to see her. I felt weak and small next to her, but I could not stop thinking about her or staring at her when she was around. She made me hard.
One night, I was in my room when I first heard her being fucked by Will.
“Mmm… Will… yes… fuck me.”
She moaned louder and louder.
“You feel so good… so deep.”
I listened to every sound and took out my small dick, which was rock hard. I stroked myself while imagining her body moving under Will. They kept going for a long time. Kayla came with a loud noise. I cummed as well.
Two nights later, I saw them on the couch. Kayla was sitting on Will’s lap and facing him. Her skirt was pulled up and showed her bare ass. They were kissing, and Will’s hands were squeezing her tits over her top. Kayla moaned softly into his mouth and rocked her hips against him.
She looked so hot. I felt a mix of jealousy and strong desire. They did not notice me at first. When they did, Will just grinned. Kayla looked over her shoulder and gave me a little smile before going back to kissing him. She didn’t bother to cover her bare ass.
The next night I would hear them again. This time the sounds were even louder.
“Yes, right there!”
“Don’t stop!”
The headboard banged against the wall. I pressed my ear to the wall and jerked off twice that night.
The next morning when I was making coffee, Kayla walked into the kitchen. She wore only one of Will’s shirts, which was half-open. I could see the curve of her big tits and her hard nipples.
“Did you sleep okay?” She asked.
She stepped close to pour coffee. Her arm brushed mine.
I mumbled, “Yeah…it was fine.”
She gave me a naughty look.
“Sorry if we were loud again.”
Will walked in as we were talking. He was shirtless and confident. He kissed Kayla on the lips and continued kissing. I was just a few inches away. He put his hands inside her shirt and groped her. I stepped back, trying to control my hard-on.
Kayla’s eyes flicked down to my loose shorts for a second. The small shape of my dick was slightly visible. She noticed but did not laugh.
Kayla and Will whispered something in each other’s ears and laughed.
“You are a virgin, right?” Kayla asked, looking at me.
I was surprised by her question, but after a pause I gave her an embarrassed nod.
“That’s nothing to be ashamed of,” she said.
She gave me a flirty wink.
“Some girls like that type.”
Will gave her a confused look.
“He’ll get used to it,” he said.
Kayla leaned in a little closer to me.
“We’ll try to keep it down next time,” she said.
But her eyes sparkled like she did not really mean it.
As they went back to Will’s room, Kayla gave me one last warm smile. My heart was pounding. I was falling hard for her.
—
After talking to Kayla, I learned that she worked at the same startup as me. It was a small, fast-moving company with around twenty people.
Ryan was the founder of the startup, and he was very good-looking and rich. Most of the team were his friends. Kayla was in Digital Marketing, and I was the new Data Analyst.
I quickly realized that Kayla was not just sexy but also ambitious and smart. She was well regarded for her work. A bonus was that she dressed sexy for work and had no qualms in showing off her cleavage and thighs.
She had a big crush on Ryan. I saw it every time they talked. She had also expressed that to me multiple times, calling him dishy and a panty dropper.
One morning, I watched from my desk as Kayla leaned over Ryan’s desk to show him something. Her tits were pressed against his arm. She laughed at everything he said and touched his shoulder.
“Ryan, you are so smart,” she said in a flirty voice.
Ryan grinned and put his hand on her lower back. The sight made me want her even more. She looked so confident and hot flirting with him.
At work, Kayla didn’t acknowledge me much. I had a reputation as a shy data guy who was clumsy and awkward.
One afternoon, Ryan asked me to pick up lunch for the whole team since I was the newest. I took the big order carefully, but I got two items wrong. When I brought the bags back, the team opened them and started complaining.
“This is not what I ordered,” one girl said.
“Dude, it’s not rocket science,” another guy said.
Ryan shook his head with a smirk.
“Come on, new guy. Pay attention next time.”
Kayla joined in, smiling playfully.
“You are like our cute little intern.”
The whole team laughed. I stood there, red-faced, and felt small and useless.
During a team meeting the next day, Ryan asked me to present a simple data report. I got nervous and mixed up a couple of numbers. The team was amused.
One guy said loudly.
“Are you still figuring out basic Excel?”
A couple of girls, including Kayla, giggled.
“Don’t laugh, guys! He is our sweet little data boy,” Kayla said.
Everyone laughed again. I wanted to disappear under the table.
Another day, I spilled coffee near the meeting room. It went all over the floor and some papers.
One girl said with a look of disgust, “You can’t even carry coffee without making a mess.”
At that moment, Kayla walked by with Ryan. Both looked at the spill and joined in with a light laugh.
“We might need to get you a bib or something,” Kayla said.
More laughter followed. I felt completely humiliated but continued to clean up.
After work that Friday, Kayla spoke to me in the parking lot.
“Sorry about the teasing today.”
I was surprised by her apology. She continued.
“I have to play along to fit in and get noticed.”
“But I feel bad. You are actually really sweet.”
I just nodded and looked down. She was looking extremely sexy in her low-cut top and mini skirt.
She stepped closer to me, and I felt unsure about how to react.
“Come here,” she said.
She grabbed me by my t-shirt and pulled me in. I felt my heart beating faster. She kissed me lightly on the lips. Her lips were soft and warm. Her big tits pressed gently against me. I kissed her back.
When she pulled away, she smiled.
“I am sorry if that was bad. It was my first kiss,” I said nervously.
“First kiss?” She asked while laughing softly.
We went back to the apartment. Will wasn’t home. Kayla joined me in my room and sat on the bed. She asked me to sit on the bed next to her. She came closer and pulled me towards her by my belt. I didn’t realize she was so strong.
She continued to tug at my belt, looking down at my crotch. I started to sweat. She laughed and asked me to stand up. She then pulled my pants down. My small dick was already rock hard. It felt like she was trying not to laugh.
The second she reached out to touch it gently with her fingers, I came instantly. My tiny cock spurted weakly on the floor. I felt so ashamed.
“I..I am so sorry,” I mumbled, looking down.
Kayla let out a soft laugh. She was more surprised than mean.
“Oh wow, that was quick.”
I could not look into her eyes.
“Really. It’s actually kind of flattering.”
She smiled and kissed my cheek.
“Don’t be embarrassed.”
I nodded as I stood there with my pants down.
She looked at me with a smile again.
“Do you want to go out for dinner?”
I was surprised she still wanted to spend time with me. I immediately said yes.
Kayla went to Will’s room to change. She changed into a black slip dress that fell mid-thigh and had a small slit on both sides. The dress showed a lot of cleavage, and her nipples were outlined.
At the restaurant, Kayla made me feel special. She was listening to me. I voiced my frustration with the job and how the way everyone at work treats me.
Then her phone rang.
“Hey, yeah, I am out right now. But I can step out for a bit.”
She looked at me.
“It’s Will. I will be right back.”
I nodded.
She was gone for about thirty minutes. When she returned, she looked a bit different. Her hair was out of place, and her makeup was a bit smudged. She immediately apologized. I signaled that it’s not a big deal.
“I will have to go for an assignment for six months urgently, so he wanted to say goodbye.”
I was not sure how to feel about that. I was afraid I might not see her as much. She understood my feelings.
“Don’t worry. I will still hang out at your apartment.”
I smiled.
“You are very sweet,” she said.
She leaned in to kiss me. Her mouth tasted different from when we kissed earlier in the day, but it was still sweet. I didn’t know what it was, but I liked it. I kissed her deeper.
When we were done, I could see people looking at us. I felt so proud to be with such a hot woman and kiss her on the mouth.
After dinner, we went back to the apartment. Kayla held my hand and took me into my room. She then pushed me onto the bed and switched off the lights. As my eyes adjusted to the darkness, I realized she was climbing on top of me.
“Lick me,” she whispered as she sat on my face.
I started licking her wet pussy. She tasted so delicious. I had never tasted anything like that. The excitement was too much for me. I came and made a mess in my underwear. I felt so ashamed and hoped she would not notice.
But she had noticed! She let out a harder laugh this time.
“Did you just cum again?”
She gently patted my head.
“It’s cute, really.”
She held my head in place as I kept licking. Her thighs shook as she came on my tongue.
She then got up and mentioned she needed to leave. She gently kissed my cheeks before leaving.
By the end of the night, I felt incredibly grateful to Kayla. She had given me my first kiss and let me lick her. Even though I came twice prematurely, I felt a lot closer to her.
My feelings for her were getting stronger every day. I knew I was falling deeper, even with all the teasing at work and her hots for Ryan.
—
With Will gone on an assignment abroad, my fears that Kayla would no longer hang out at my place were quickly dispelled. In fact, she started relying on me more. On weekdays, we would talk about work and vent out. When she was working late at night, I would rub her foot and make her favorite tea.
One night after she had a bad day, she cried on my shoulder while I held her. I told her she was smart and beautiful.
“You are always here for me.”
She continued to sob.
“No one else listens as you do.”
A few days later, she had a tough deadline. I stayed up late with her and helped her as much as I could.
After she completed the work, she hugged me tightly and said, “I don’t know how I would manage without you right now.”
These moments made my feelings for her grow even stronger.
One Friday evening, I cooked her dinner and served her favorite wine. We were sitting on the couch and talking. She was talking about a work-related issue while I was giving her a foot rub.
“You are such a good listener,” she said out of nowhere.
I blushed and said thank you.
“You are different. Most guys just pretend to listen to get inside my pants.”
I nodded.
“I love you.”
I could not believe her words. I looked at her with surprise. She laughed a little and repeated that she loved me.
I told her I loved her too. She came closer to me, and we kissed. She took my hand and placed it on her tits. She was wearing a thin, sheer nightie. I started to massage her tits. She got on top of me as we continued to kiss. She then took off her nightie and took off her thong. I was mesmerized. She was smooth.
She put her head on the armrest on the other side of the couch and lay down on her back. I knew what I had to do. I eagerly licked her pussy. She tasted so different from last time I licked her. I immediately figured out I was cleaning Will’s cum out of her pussy. Instead of being upset, I got more excited and cummed in my shorts.
Kayla felt my body shake and let out a laugh.
“Already?”
She stroked my hair gently as I kept licking until she came.
Within the next few weeks, I suggested that she move in with me, as she was practically staying with me. She agreed immediately. I could not believe my luck in landing such a hot girl. It was my first time having a girlfriend, and I was absolutely delighted.
One night as she was working on her laptop, I suggested we could make it official on our respective social media accounts. She ignored me, but when I pressed it a few times, she gave me a stern look.
“No. We need to keep this completely secret.”
I was lost for words.
“It will look bad for my career if people know I’m dating the quiet new data guy.”
“You know what your reputation is.”
I felt hurt while she was quite cool about it. She went back to her laptop to finish the office assignment.
I gathered courage to speak.
“So…so I am embarrassing to you?”
She stopped working and closed the laptop lid.
“You don’t understand how competitive this place is. That’s why everyone makes fun of you.”
I kept quiet. She went inside the bedroom. I stayed on the couch and slept there.
We didn’t speak much over the next few days. At the office, she was mean as usual. She openly flirted with Ryan right in front of me. She would sit on his desk, cross her legs in short skirts, laugh loudly, and let him put his hand on her waist.
During team stand-up, when I made a small mistake, she reacted sharply.
“Can you try not to slow everyone down?”
The team laughed. I felt humiliated, but I told myself that she is so beautiful and confident. Maybe she’s right. Maybe I am holding her back.
I tried to stay strong, but was unable to resist her beauty and charm. One evening, as she was sitting on the couch in her barely-there top and shorts, I came up to her.
“Okay, we’ll keep it a secret,” I said quietly.
Kayla’s face softened immediately. She pulled me into a hug and kissed me.
“Thank you, baby. I love you so much.”
I mumbled Love you too.
“This is just for Ryan, okay? I need to stay close to him for my career.”
I took her foot in my hand and started to give her a foot massage. She smiled at me.
“I love you, and I need your support.”
She stroked my cheek lovingly with her foot.
“This doesn’t change how I feel about you.”
Her words made me feel warm and loved again. We had sex that night, which involved me licking her until we both came.
A few weeks later, on Sunday, we went on a date to watch a movie. Kayla looked stunning in a halter top and a micro mini skirt. Her boobs were barely held together in the top, and she was not wearing a bra. I felt so proud walking through the mall, holding her hands, as all eyes were on her.
Halfway through the movie, she got a call. It was Ryan. She jumped out of the seat and went outside to take the call. She came back inside and told me we needed to leave immediately, as Ryan needed her in the office. She told me to come along.
When we reached the empty office, Ryan was waiting. He looked surprised to see me walk in behind Kayla.
“Why did you bring him?” Ryan asked, staring at her chest.
Kayla laughed lightly.
“Oh, he is just my ride.”
“He offered to drive me and help out if we needed anything. You know, like an assistant.”
She glanced at me with a small smirk.
“You don’t mind, right?”
Ryan chuckled and nodded.
“Alright, whatever works.”
He immediately turned his attention back to Kayla and placed his hand on her lower back.
I stood there awkwardly as they worked at the conference table. Kayla asked me to get coffee and water for them, which I duly did.
Ryan was very flirty with my girlfriend. He kept touching her arm, leaning close to her and whispering things that made her giggle. I saw him staring at her tits multiple times. At one point, he brushed a strand of hair from her face. Kayla was loving the attention.
She touched his chest and said, “Ryan, you always know exactly what I need.”
They were acting like I was not even in the room. I was jealous, but I could not stop watching how sexy my girlfriend looked.
After some time, Ryan looked at me with frustration.
“Hey, why don’t you go pick up some dinner for us? There’s a good Chinese place nearby.”
Kayla smiled at me sweetly but with a hint of mockery.
“Yes, be a good boy and bring us food.”
I left quickly and took the money Ryan gave me.
When I returned twenty minutes later with the food bags, the meeting room door was slightly open. I heard loud moaning before I even reached it.
My heart sank, but I peeked inside. Kayla was bent over the conference table. Her skirt was pulled above her waist, and her panties were on the floor. Ryan was behind her and thrusting hard into her.
“Fuck, Ryan… yes!” Kayla moaned loudly.
“You… you are so… big!”
“Deeper… just like that!”
Ryan gripped her hips and pounded her harder.
“You feel so fucking good, Kayla.”
“Such a naughty girl.”
This was the first time I was actually seeing her get fucked. My heart was pounding. I felt a sharp pain of betrayal and deep humiliation, but at the same time I was mesmerized. Her body looked so perfect as her tits bounced wildly and her face twisted in pure pleasure.
She was moaning in ways I can never imagine making her moan. My small dick was rock hard in my pants even as I felt my eyes tearing up. I thought I loved her so much, but I could never give her this.
I quietly stepped back and waited in the hallway until the moans stopped. A few minutes later, they came out and headed to the washroom. She asked me to go inside the conference room and wait for them.
We ate dinner awkwardly and pretended nothing had happened.
When we finally left, I thought she would bring it up in the car, but she didn’t. I finally confronted her later in the night. She was scrolling through her phone when I spoke to her.
“I saw you with Ryan.”
She didn’t look up from her phone and just asked casually, “So?”
I fumbled for words as she continued scrolling on her phone.
“How… how can you fuck him?”
She put her phone down and looked at me with amusement.
“Yes, I fucked him. Was I not supposed to do that?”
I looked at her, astounded. She continued in an assertive tone.
“As per him, I am single. He finds me attractive. I find him attractive. Two mutually consenting adults should be able to fuck each other.”
I could not believe she was not apologetic. She continued in the same tone.
“He’s good for my career, and he actually satisfies me, unlike you.”
Her words were sharp and hit me hard. I stood there without uttering a word.
“I thought we spoke about this already. If you can’t handle this, then we need to rethink our relationship.”
She went inside the bedroom to sleep. I decided to sleep on the sofa. She didn’t care.
She continued to ignore me at home. At work, she continued to flirt with Ryan and cruelly tease me.
Inside, I struggled. I thought, “Why does she treat me like this?” But she is so sexy when she is confident. Maybe I am not enough for her. Maybe this is what I deserve for loving someone like her. I kept rationalizing her behavior because her beauty and raw sexuality had me completely mesmerized.
A few days later, on a Friday night, we had a pizza-and-beer party at the office. Kayla had dressed sexily in a tight white shirt, a brown leather miniskirt, and knee-high boots. She was with Ryan, who was holding her by the waist. His hands would occasionally slide lower.
After a while, Ryan announced that Kayla had been promoted. The room cheered. I clapped too. I was genuinely happy for her.
Later in the night, they both slipped out of the main party area into Ryan’s room. They didn’t even bother closing the door fully. Very soon, loud moans followed.
“Yes, Ryan… fuck me harder!”
Several people, including me, could hear everything. I felt stupid for fighting with such a hot girl.
In the car on the way home, I finally broke down.
“Kayla, I am sorry.”
She kept quiet.
“I’m sorry for fighting. I don’t want to lose you.”
She looked at me with her drunk eyes. She was still angry.
“Then stop making it difficult.”
I promised I would try harder. I congratulated her on her promotion. She didn’t say anything.
When we got home, she straight away took me inside the bedroom. She sat on the edge of the bed and lifted her skirt. She was not wearing panties. Her pussy looked inviting despite being fucked by Ryan. I was kneeling in front of her.
“Please, Kayla,” I whispered as my voice shook.
“Let me lick you.”
She gave me a look and asked, “Will you fight again with me?”
I pleaded again, “No, I won’t. I am extremely sorry. Let me lick you, please.”
She was enjoying it. She knew I was desperately missing her taste. She lifted her legs a little.
“I have just been fucked by Ryan.”
“I know. I heard it,” I said. My eyes were fixated on her pussy.
“He was not wearing a condom. Are you still ok to clean me?” She asked.
I nodded my head to indicate yes. She laughed.
“This is so pathetic and sweet.”
I leaned in and started licking. Her pussy had a strong, salty taste of Ryan’s cum, which was mixed with her sweet juices. I licked deeper and cleaned every drop. She moaned softly and grinded against my face.
“I do love you. I really do.”
She gently stroked my hair. As I was licking her, she finally started to talk to me.
“You are sweet. You support me, and you make me feel cared for.”
“But you are not enough for me.”
I continued licking her harder.
“Ryan’s cock is so much bigger and thicker.”
She was still gently stroking my hair.
“He fucks me so hard and makes me cum in ways your little dick just can’t.”
Her words were too much for me. The mix of her mean and loving tone made me cum. Kayla noticed it right away and laughed a little. She held me by my hair and lifted my head. She looked directly into my eyes.
“See? Even hearing about Ryan’s cock makes you cum instantly.”
She stroked my cheek with her feet.
“That is exactly what I mean, baby. You’re perfect for loving and supporting me, but I need real sex too. Do you understand now?”
I nodded. She guided my face back to her pussy. She pulled me up after she came on my tongue.
“I love you, but you need to remember your place.”
“I love you too. And I will be more careful,” I said.
As we cuddled and slept together, I couldn’t help but think that my love for her was growing only deeper.
Things had gotten even more serious between Kayla and Ryan. As per Kayla, both of them were in a relationship.
She also started posting pictures with Ryan on social media. She would post pics of her sitting on his lap at office parties, holding hands at fancy events, or kissing on the lips on dates. I was conflicted about how to feel about these posts. I would get hard at how good they both looked together, but at the same time I was afraid she would dump me for Ryan. This made me try very hard to keep Kayla happy and to do whatever she asked of me.
One Saturday evening, she had a date night with Ryan. She asked me to help her get ready and choose her clothes.
“I want you to feel you are part of this as well,” she said.
I was grateful she still wanted me part of this. This made me feel loved and special. I chose a black lace bra and a matching thong for her. Her big round tits looked incredible in that bra, and the thong disappeared between her cheeks.
She was being loving but also cruel in a way only she could manage.
“Ryan is taking me to this expensive rooftop restaurant.”
I was searching through her wardrobe for a perfect dress for her.
“I want to look fuckable for him.”
I showed her a red tube dress which is very tight and short.
“You always look amazing in anything you wear,” I said.
She smiled and nodded, indicating she liked the dress. I helped her to get into the dress. As I zipped it from behind, she pushed her ass back against me. The dress was extremely short, and it exposed the bottom of her ass. She looked stunning.
“You’re so good at this,” she said as she turned to kiss my cheek.
“Ryan would never do this for me.”
Then she laughed softly.
“But he doesn’t need to. He just needs to rip this dress off later.”
My face burned with humiliation, but I was so horny.
She noticed the small bulge in my pants and gently patted it.
“Aww, already excited? You are so cute.”
I didn’t say anything.
I drove her to the restaurant across town. The whole ride, Kayla spoke about Ryan and how excited she was for the date.
“He is so charming, you know?”
“The way he talks, the way he touches me, and the way he fucks me.”
She was saying all this very casually while resting her hand on my thigh.
“Ryan is so thick and long. It hits spots you never could.”
“Don’t be jealous, okay?”
“No, I am not. I want you to be happy,” I said.
Throughout the ride, I was torn between heartbreak and arousal. When we reached the restaurant, she checked the time.
“I’ll be back in about two hours.”
She kissed my cheeks and whispered, “No touching yourself while I am gone.”
I waited and ordered food to eat in the car.
It was close to three hours, but she was still not back.
Finally, I saw her walking out of the restaurant with Ryan. They were laughing and holding hands. Instead of coming to my car, she followed him to his luxury SUV.
Another hour passed. When she finally came back to my car, she smelled like sex and his cologne. We both got into a passionate kiss the moment she sat down.
On the drive home, she was very happy.
“Oh my God, tonight was incredible.”
“Ryan is such a great conversationalist. He makes me feel so smart and sexy.”
“And the sex in his car afterward.”
“He bent me over the backseat and fucked me so hard.”
“His cock is just on another level. I came three times.”
She looked at me and touched my cheek lovingly.
“You could never fuck me like that, baby.”
“But that’s okay. You’re sweet in your own way.”
Even while she put me down, I wanted her desperately. When we got home, I dropped to my knees in front of her.
“Please, Kayla… let me eat you.”
She was amused, but there was still an affectionate look in her eyes.
“You are such a pathetic little thing, but I love how eager you are.”
She sat on the couch and removed her dress. She was not wearing her bra and thong.
I buried my face between her thighs and started licking greedily. While I licked, I came in my pants.
Kayla felt me shaking and laughed.
“You are honestly hopeless.”
She held my head in place and made me keep licking until she came on my tongue.
Over the next two weeks, Kayla started spending three to four nights a week at Ryan’s apartment. Every time she packed her bag, I felt sad. One night I finally worked up the courage to say something.
“I don’t like you staying over there so much.”
“I miss you.”
She was doing her makeup and barely glanced at me. She motioned for me to help her put on a sheer mini dress with a scoop neckline. She looked super sexy. As I was helping her with her heels, she got a message that Ryan was waiting for her downstairs. She kissed me on the cheeks and left hurriedly.
Then one evening, she came home excited and hugged me tight.
“I convinced Ryan to come stay here a few nights every week.”
She kissed my cheek.
“Isn’t that great?”
I tried to match her excitement while thinking about how it would work to have my girlfriend’s lover at our place. She probably figured out what I was thinking.
“But he doesn’t know we’re together.”
“You need to move your stuff into Will’s room and pretend you are just my roommate. Okay?”
She looked at me expectantly.
“Ok. Thank you for including me,” I said quietly.
“You are such a good boy,” she said as she stroked my hair. Then her tone turned teasing.
“Just remember that you are my harmless roommate who does all the chores.”
She then held my chin and came closer to me.
“Don’t embarrass me.”
I promised not to embarrass her.
On the first night Ryan came over, Kayla took my help to get dressed like she was trying to get fucked immediately. She wore a tiny nightie-type dress that reached the middle of her ass. She ditched her bra and looked incredibly sexy.
When Ryan arrived, he looked confident and relaxed. Kayla greeted him at the door with a long, deep kiss on his lips. He felt my girlfriend’s body freely with his hands while I watched helplessly.
When he saw me, he smirked with mild amusement.
“So he is your roommate?” he asked Kayla.
“Yeah, he is totally harmless.”
Ryan was not even looking. He was checking out Kayla. I could not blame him. Kayla continued speaking.
“He does all the cleaning and cooking. He’s like a little helper around the house.”
She looked at me with a teasing smile.
“Right?”
“Yes,” I mumbled.
“I will make dinner for you guys.”
I quickly disappeared into the kitchen.
Kayla led Ryan by his hands to the bedroom. The bedroom that I shared with her until this morning. Very soon, I could hear her calling out Ryan’s name as he fucked her.
Once done, they came out and sat on the couch in front of the TV.
I served them dinner and wine and quietly disappeared into Will’s room. I closed the door and had my dinner.
The entire night, I could hear them. They didn’t even try to be quiet. I lay in bed and jerked off my small dick to the sounds of my girlfriend fucking another guy. I felt pathetic but couldn’t stop.
In the morning, Ryan left early. Kayla messaged me to come to our bedroom.
I walked in. She was lying completely naked on the bed. Her pussy was visibly swollen. It was not surprising, as I had heard her having sex just a few minutes back.
She motioned for me to come near her. She gave me a deep kiss and pushed warm liquid inside my mouth. I took it all in as we both kissed for a long time.
She then paused kissing me and stroked my hair affectionately.
“Ryan came in my mouth.”
I knew I was swallowing Ryan’s cum, but it didn’t make me pull away from her. It felt nice to be near her after hearing her all night with another man. She continued speaking.
“I swallowed most of it, but I wanted to keep some for you. You like that, don’t you?
I nodded. She then pushed my head, indicating she wanted me to clean her pussy.
As I started licking her, she began talking about last night.
“Ryan was so rough last night.”
“When you were eating your dinner inside, he bent me over the couch and fucked me so deep.”
“He made me ride him in our bed so many times.”
“I have lost count of how many times he cummed inside me.”
The more she talked, the more turned on I became. My small dick was throbbing painfully in my pants. I was trying to control myself as I didn’t want her to mock me more. But I could not control it!
Kayla noticed immediately and let out a cruel laugh.
“Oh my god! Did you just cum in your shorts again?”
She gently patted my head.
“You’re so easy and predictable.”
She pushed my face deeper into her pussy.
“Be a good boy and lick every drop.”
Even as she made fun of me, there was a hint of affection in her voice. I licked her until she came on my tongue. She then asked me to hug her as we drifted off to sleep.
A few days later, Ryan invited Kayla on a weekend trip to a holiday home with a group of friends and their girlfriends. When she told me, my stomach dropped.
“You are going for two nights?” I asked softly.
Kayla smiled and kissed me on the cheeks.
“Aww, baby! But I’ll miss you,” she said.
She kissed my forehead lovingly.
“I need to look hot for Ryan.”
“Can you be a good boy and pack my suitcase? Pick my sluttiest dresses, lingerie, and bikinis.”
I nodded and got to the task. It was not difficult, as her wardrobe was full of slutty things to wear.
As Kayla looked at what I got for her, she smirked.
“Of course you like the red bikini. It barely covers my nipples.”
“This skirt does not even cover my ass. Should I wear it with no panties?”
I nodded with my eyes down.
She laughed.
“You are so pathetic.”
“You are helping me pack slutty clothes, so my boss can fuck me all weekend.”
She continued laughing as she saw some of my other picks.
“Does this turn you on?”
“A little,” I admitted.
“Good boy.”
She kissed my cheek affectionately.
“I love how honest you are even if it’s embarrassing.”
She continued.
“You have been such a good boy. I think you deserve a small gift.”
I was happy to hear that.
She opened her bedside drawer and took out a small pink chastity cage. She held it against her face and showed it to me.
“Isn’t it nice?”
“Small and cute just like you.”
I hesitated to say anything and kept on staring at the tiny pink device. I finally spoke in a low voice.
“But why?”
She gave me a firm but affectionate look and asked me to sit next to her.
“It is pathetic enough that ever since we have been together, you have cummed so many times without me barely touching you.”
She stroked my hair lovingly.
“You have cummed while eating Ryan’s cum out of my pussy.”
“I am sure you jerked off all night when he fucked me on this bed.”
My face dropped. She pulled me closer and kissed me on the cheeks.
“This is good for you.”
“It will make you more focused on me and less distracted by that useless little thing between your legs”
I was still not convinced, but didn’t speak up for fear of upsetting her.
“Now stop complaining and take off your pants.”
I obeyed reluctantly and pulled down my pants. My small dick was already half-hard. Kayla laughed and locked me in the pink cage.
“So cute and tiny.”
She then put the key on her necklace and let it dangle between her breasts.
“You are always close to my heart.”
She kissed me again on the cheeks, and I went back to finish the packing.
In the morning, when I woke up, Kayla was ready for Ryan to pick her up. She looked super hot in a pleated mini skirt and a tight top. When she heard Ryan’s sports car pull up, she jumped in excitement. Her tits bounced freely without a bra while her mini skirt rode high enough to reveal she was going commando.
She kissed me lightly on the cheeks.
“Send me a photo of your locked cock every few hours. I want proof you are being a good boy.”
I nodded and said bye. From the window, I saw Ryan groping her ass and kissing her on the mouth. I felt a sharp pain in my balls as the cage stopped my erection.
For the entire weekend, she didn’t message me even once. I sent her photos of my locked dick every few hours, but she didn’t reply.
She posted constantly on social media, showing that she was having a good time.
One photo showed her straddling Ryan on a pool lounge chair in a tiny red bikini. It looked like her tits were about to spill out.
Another post was a close-up mirror selfie in the bathroom wearing a sheer black dress with no bra. Her nipples were clearly visible.
She also posted a video of her dancing and grinding against Ryan beside the pool.
My favorite photo of her was Kayla in his shirt on the balcony and looking freshly fucked.
I liked every single post as I stroked my balls and felt my cage painfully tight.
When she returned on Sunday night, she looked tired. She gave me a half-hearted hug and didn’t even kiss me.
I asked her how her trip was. She didn’t give me any details and just mentioned it was fine.
“Can you prepare a bath for me and get me a glass of wine?”
I nodded, wondering why she was so down.
When she took off her clothes to step into the bath, I could not help but notice quite a few hickeys on her neck and tits. Her ass had hand imprints. I thought I should join her in the bath, but she stopped me as I started to take off my clothes.
“Can you go and unpack my bag?”
She sipped her wine and continued.
“Some of the stuff in there is quite expensive and delicate and needs to be hand washed.”
I felt dejected. We had hardly spoken over the last few days, and now she was ignoring me. I was extremely horny too.
When she was done with the bath, she went inside the bedroom without telling me. I came after finishing the laundry to find her on the bed in a deep sleep, totally naked. I hugged her tight from behind and dozed off.
***
What happened on the weekend trip (Unknown to me):
Kayla was having a lot of fun playing Truth or Dare. Her brazenness had won her many admirers, especially men. In addition, her filter was off due to excessive alcohol. That’s why she didn’t think twice when she was dared to show the last message on her phone.
It was one of my pink chastity photos, with the caption “Locked and waiting for you”.
The group was silent in shock before erupting in laughter. She was lapping up all the attention and ended up telling them everything. She told them that I was her secret boyfriend, that I was locked in a tiny pink chastity cage, that I packed her slutty clothes for the trip, and that I cleaned her pussy after Ryan fucked her.
The laughter continued.
“So the quiet little guy from data is actually your boyfriend?”
“I always thought he was a bit pathetic, but this is unbelievable.”
“We should start messing with him at work.”
“Nothing too obvious, just some light teasing.”
Kayla was laughing along and enjoying the thrill.
“Don’t tell him we know. Just play along and join in the fun.”
She hesitated for a moment but finally nodded.
“Ok, I will play along. But don’t be too mean to him.”
Later in the night, after Ryan had dumped another of his load inside her pussy, he brought up the topic again.
“I love how wild and adventurous you are, but I find this situation with your cuck boyfriend weird.”
Kayla nodded. Ryan continued.
“Why don’t you dump him and move in with me?”
Kayla hesitated, not sure how to respond. Ryan spoke again.
“It’s ok. You don’t have to do anything now.”
“Let us have fun with him over the next few weeks. You can decide till then.”
Kayla felt conflicted. She loved the excitement and attention, but a small part of her felt bad for how much she was humiliating the sweet guy waiting for her at home.
—
After the weekend trip, the office became much more uncomfortable. As everyone knew, Ryan and Kayla were officially a couple, which meant they flirted openly in front of everyone. On top of that, I noticed subtle digs at me from everyone in the office.
One morning, after spending the weekend at Ryan’s place, Kayla came to the office with him. Ryan’s hand was resting casually on her lower back. She was wearing a tight red blouse that showed a generous amount of cleavage. She stopped at my desk.
“Did you finish those reports I asked you to do over the weekend?”
I nodded quickly.
“Yes, I sent them to you.”
Ryan smirked.
“You are always so dependable.”
Kayla leaned over my desk.
“He really is. He is very useful to have around.”
She glanced at Ryan with a flirty smile.
“Unlike some people who focus on the bigger picture.”
I smiled awkwardly and mumbled, “Glad I could help.”
Later in the week, I was giving my data update. But I got a bit nervous and stumbled over my words.
One guy grinned.
“Relax, buddy. No need to get flustered.”
Someone else said.
“Some people just are not natural speakers.”
A few people chuckled, including Kayla and Ryan. Another girl chimed in a mocking tone.
“Be nice.”
“He tries his best. Not everyone can be confident.”
I forced an awkward smile and mumbled, “Sorry about that.”
Another day, I was making coffee when Kayla and Ryan walked in. Ryan’s hand was on her waist.
Kayla looked at me.
“Can you make two coffees for us?”
As I prepared the coffee, a girl walked in and commented with a smirk, “He is always so helpful.”
Ryan chuckled.
“He is a reliable guy.”
Kayla took her coffee and patted my shoulder condescendingly.
“He knows how to stay useful.”
I handed them the cups with an awkward smile, mumbling, “Here you go.”
Inside, I felt confused and increasingly small. I did not understand why the teasing had gotten so much more frequent and personal, but I was slowly accepting it as my new normal. A twisted part of me even felt aroused by how openly Kayla flirted with Ryan in front of me.
***
The buzz around the office had been growing all week. Ryan was throwing an exclusive Halloween party at his apartment for couples only with a strict “couple costume” theme. Kayla was incredibly excited and spent almost every evening planning and texting with Ryan about their outfits. I felt completely left out.
One night after she finished a video call with Ryan, laughing and discussing costume ideas, I finally spoke up.
“Kayla, can I come too?”
She turned to me with a teasing smile.
“Aww, baby. It’s couples only.”
She patted my head lovingly as she came closer to me.
“Ryan was very clear. It would be kind of sad if you came alone.”
Her words stung.
I looked down and mumbled, “I just wanted to be there with you.”
Kayla sighed and kissed me on the cheeks.
“Fine, I will talk to Ryan. But you will have to behave and not embarrass me.”
I nodded.
Two days later, she told me I could come.
“You are lucky I convinced him,” she said.
I was so happy. I hugged her tight and thanked her.
“Ryan and I are dressing up as Doctor and Sexy Nurse.”
“You will go as the Patient. I already ordered your costume.”
I thanked her again for ordering the costume.
On the day of the party, when I saw Kayla in her costume, my mouth fell open. Her “Sexy Nurse” costume was extremely slutty. She was not wearing any top, and her tits had just red color pasties in the shape of plus signs. Below, she wore a white, semi-sheer G-string. She completed her outfit with red heels and fishnet stockings. She looked breathtaking and completely shameless.
On the contrary, I felt very self-conscious in the patient costume she picked up for me. It was a thin, pink hospital gown that tied at the back and was completely open from my neck to the bottom. I stood in front of the mirror, tugging at the gown. If someone looked closely, they could make out my pink cage below the gown.
“Kayla, this is really embarrassing.”
I was trying to cover my bare ass to no avail.
“Everyone’s going to see my ass.”
She laughed and slapped my bare ass cheek.
“That’s the point, silly.”
Her slap stung, and I was rubbing my ass.
“Now stop complaining and be grateful you are even coming.”
“You know how difficult it was to convince Ryan.”
She winked at me and laughed.
“I can give you one of my panties.”
I looked at her with horror. She laughed and came near me.
“Do you think your ugly underwear will look good with this?”
Even before I could reply, she spoke firmly.
“You are making me late. If you want, you can stay at home and stroke your tiny balls.”
I spoke in a low tone, “Ok, I will wear your panties.”
She got bright pink lace panties. My face burnt with shame as I wore them. She was happy with the outcome, though.
We arrived at Ryan’s apartment. The place was incredible, and I felt even smaller standing there.
Ryan greeted us at the door, dressed as a sexy Doctor in a tight white coat with his chest exposed. He immediately pulled Kayla into a deep kiss and groped her ass in front of me.
Ryan barely looked at me, but that did not stop him from commenting.
“Nice gown. Pink really suits you.”
Kayla giggled and pressed herself against him while touching his bare chest.
“Doesn’t he look adorable? I told him he had to match the theme.”
Many office colleagues were already there, and they kept laughing at my outfit.
“Oh my god! That gown is so revealing.”
“Turn around, let us see the back!”
I awkwardly turned to show my pink panties.
“You really committed to the bit.”
I smiled awkwardly and mumbled, “Yeah, it was Kayla’s idea.”
I looked around trying to find Kayla. She was making out with Ryan in a corner of the room.
For the rest of the night, I became the default helper. I fetched drinks, took photos for people, adjusted the snacks, and cleaned up small messes. Every time someone needed something, they called me by my new nickname: Panty Patient. It was humiliating, but I was glad to be near Kayla.
Later in the night, the group started playing Truth or Dare in the living room. I tried to stay quiet in the corner, but they dragged me in.
I sat alone on a chair, unlike others who were cozied up with their partners. Kayla was lounging between Ryan’s legs on the big couch. He had his big arms wrapped around her and was casually playing with her tits.
The first dare for me was to pitch my superpowers as the superhero Panty Patient. I hesitated. Kayla shot me a commanding look that made me stand up from my chair.
I stood up in front of everyone and used a high-pitched, whiny voice.
“My superpower is that whenever danger appears, my gown automatically flies open. My pink lace panties become a glowing beacon that distracts all by making them laugh so hard at my bare ass that they forget to attack.”
The room exploded with howling laughter. Kayla mouthed “good boy” to me as I sat down. I felt a pathetic spark of pride mixed with the burning shame inside me.
The next dare for me was to act like a dog. I dropped to all fours, barked loudly, and crawled across the room to fetch a can of beer with my mouth. I brought it back to the girl who had given me the dare. I dropped the can at her feet and barked, “Thank you,” while wiggling my ass hard.
The whole group was losing it, with people rolling on the floor laughing, including Ryan and Kayla.
Ryan gave me the next dare.
“Give yourself a big wedgie and go around the room asking everyone to rate it in your little superhero voice.”
My heart pounded. I was not sure, but it was from Ryan. Kayla was watching me. I grabbed the waistband of my pink lace panties and yanked them up hard. The fabric dug deep between my cheeks as I walked around the circle.
“This wedgie is splitting my superpowers in half!” I squeaked.
The room roared. Most people rated it a 2 or 3 and laughed at how ridiculous I looked. When I reached Ryan and Kayla, they were cracking up.
Ryan smirked down at me.
“You want a real rating? Like a 5?”
I nodded with my face burning. He whispered something in Kayla’s ear. She giggled and playfully slapped his bare chest. They both stood up. A few people pulled out their phones. I was not sure what was going on.
In one swift motion, Kayla and Ryan each grabbed a side of my panties’ waistband. They yanked upward with enormous force and hooked over my head in a perfect atomic wedgie. The pull was so strong it lifted me onto my toes. Eventually the band snapped, and I fell on the ground. It exposed my cage and bare ass to everyone in the room.
The room erupted in loud laughter and cheers. Kayla and Ryan high-fived and kissed on the lips. Kayla glanced over at me mid-kiss with a look of disgust.
“Now it’s a solid 5,” she called out, laughing.
I mumbled a weak thank-you and sat back down on the couch.
While I was getting destroyed with one humiliating task after another, Kayla was getting hot, sexual dares. She was happily doing them with multiple guys, not just Ryan. I could tell it was starting to bother Ryan.
After a while, Ryan stood up and took Kayla’s hand.
“Alright everyone, we are heading upstairs,” he announced loudly.
“The doctor needs to give his favorite nurse a very thorough examination.”
Kayla giggled and kissed him sloppily.
She looked back at me and said, “Can you be a doll and clean up? After that you can sleep on the sofa.”
I nodded. The party was almost empty now, and few remaining guests left after Ryan went upstairs with Kayla.
It took me a while to clean up. After that, I spent the rest of the night alone on the large sofa in the living room. I could hear faint sounds of Kayla getting fucked by Ryan echoing from upstairs. I felt humiliated but content in my submission.
I barely slept. The sofa was uncomfortable, and I kept waking up to Kayla moaning upstairs.
In the morning, my phone buzzed with a text from Kayla.
“Baby, can you get us coffee and breakfast? Two large lattes. Avo toast for me and the protein bowl for Ryan. Don’t take too long!”
I quickly changed and went to the nearby cafe.
When I returned with the food and coffees, I went upstairs to the master bedroom. The door was slightly open. I could hear them clearly.
“Fuck, Ryan, yes, right there!”
“Your cock feels so good”
“That’s it, you little slut. Take it.”
I stood outside the door holding the bags and coffees. My pink cage strained painfully. After almost 30 minutes, Ryan came out of the bedroom wearing only boxer briefs. He barely glanced at me.
“Breakfast?” he asked casually.
I handed him the bag and one coffee.
Ryan took them without a thank you and went downstairs.
I took a deep breath and entered the bedroom. The room smelled strongly of sex. Kayla was lying on the bed completely naked and looked wrecked.
She smiled when she saw me.
“There’s my little boyfriend. Come here and kiss me.”
I leaned down and kissed her. She tasted delicious, as always. Then she gently pushed my head downward.
“You did so well last night. I am really proud of you.”
“As a reward, you can clean me up. Ryan just filled me again.”
I got between her legs and started licking. Kayla stroked my hair and talked down to me.
“Mmm, good boy.”
“You have no idea how good Ryan’s cock feels. He fucked me so much better than you ever could.”
She moaned softly between her words.
“You’re so pathetic. Last night everyone made fun of you, and you didn’t say a word.”
“Ryan was groping me in front of you, and you didn’t have the balls to stop him.”
She was enjoying this and moaning a bit louder as I continued to lick her deeper.
“Now you are fetching breakfast while your girlfriend gets properly fucked.”
“And eagerly cleaning another man’s cum.”
The humiliation was too much for me. I cummed inside my underwear. Even the cage could not stop my premature cumming. Kayla felt my body shake and burst out laughing.
“Oh my god, did you cum in your cage just from licking Ryan’s load out of me?”
“You really are hopeless.”
She patted my head like a pet.
“I love how broken you are for me.”
After she came on my tongue, she sat up and started eating her avocado toast. She was still naked.
“You can go home now,” she said between bites.
“I am going to spend the rest of the long weekend here with Ryan.”
I nodded.
“I love you, Kayla.”
She smiled and gave me a quick kiss on the forehead.
“Now be a good boy and drive safely.”
On the drive back, tears welled up in my eyes as I replayed the entire humiliating weekend. The costume, the dares, listening to them fuck, cleaning her up, and being sent away. But even through the pain, I tried to rationalize it. She still kisses me. She still lets me taste her. She needs me in her own way, and I love her. I will do anything for her.
By the time I reached the apartment, the tears had dried. I was still determined to be hers completely.
The long weekend without Kayla felt endless. She stayed at Ryan’s place and posted nonstop on social media. I spent hours staring at her posts. I furiously stroked my aching balls and missed her desperately.
On Tuesday morning, I was getting ready for work when the front door opened. Kayla walked in with Ryan behind her. She looked incredibly sexy in a tight black crop top, a tiny tennis skirt, and thigh-high boots.
“We need to talk,” she said with a sadness on her face.
My heart sank. I stood there awkwardly. She took a deep breath.
“I am moving in with Ryan permanently.”
She paused before speaking up again.
“This thing between us is not working anymore.”
Tears immediately welled up in my eyes. My voice cracked as I spoke.
“Please, Kayla, don’t do this,” I said as tears slipped down my cheeks.
“I love you. I will do anything you say.”
“I can stay in the other room. I’ll keep supporting you however you want.”
I wiped my eyes and tried to hold myself together, but more tears kept falling.
“Don’t leave me, please.”
Kayla looked a little uncomfortable but stayed firm.
“Ryan already knows everything. The whole office knows since the trip. I am tired of hiding this arrangement.”
“Ryan does not want this arrangement anymore. He wants me fully.”
Ryan nodded and spoke.
“You are a good guy, but this is weird.”
“We are also letting you go from the company. HR will contact you with a decent severance package.”
More tears rolled down my face as I stood there silently. I was heartbroken and stunned.
Kayla sighed and gently touched my arm.
“You were sweet. But I need more.”
She went closer to Ryan and kissed him on the lips.
“I need Ryan.”
She then gathered her things as Ryan helped her out. I stood there quietly crying.
Before walking out, Kayla looked back at me one last time.
“Take care of yourself, okay?”
I didn’t respond. They left and closed the door behind them.
I sat down on the couch as tears continued to fall. The woman I loved had just walked out of my life. Everyone at work knew what a pathetic cuck I was. And now I don’t even have a job.
Even through the pain, a broken part of me still said I loved her.
The End.
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