Hello,
About ten years ago, I had my first cuckold experience. I had just graduated college and was working part time at a boutique 'feminist' adult store. I was the only male employee and spent most of the day doing inventory and stocking shelves. Jenny was a few years older than me and worked at the cash register. The store was small and didn't get a lot of foot traffic so Jenny and I spent a lot of time alone there together. It was strange trying to flirt with Jenny amidst walls of dildos and lingerie but she was friendly with me. She liked to tease me whenever I was awkward with her. She'd see me blushing while putting thongs on a rack and jokingly ask me if I had ever even seen a thong before. I eventually worked up the courage to ask her out. I was so scared and had already mentally prepared to quit if she said no. To my surprise though, she said yes.
Jenny was incredible. As you might expect working at an adult store, she had lots of kinky outfits and toys in her personal collection. The first time we had sex, she dressed up like a slutty school girl and roleplayed that she was in detention and needed punishment. I nearly blew my load in my pants when she asked me to spank her while bending over my lap. Needless to say, the sex was amazing and Jenny was 99% responsible for that. I was always on the verge of cumming after just minutes with her. I started to pull out and go down on her just to avoid prematurely cumming. Jenny loved my tongue and would orgasm several times before jumping back on my cock and making me erupt.
When we were alone at work, Jenny would tease me by pretending to jerk off a dildo or holding sexy lingerie against her body. One day when I was sitting behind the cash register, she slipped off her panties under her skirt and let them fall to the floor. Seconds later, a couple customers walked in and Jenny walked out to help them. I quickly picked up her panties so the customers wouldn't see them and I put them in my pocket. More customers walked in several minutes later and Jenny ended up spending over half an hour helping people while full commando. Once all the customers left, Jenny came back behind the register and lifted up her skirt. She said she was dripping wet while laughing. I immediately leaned forward to take her pussy in my mouth. I licked her for a couple minutes until she orgasmed violently while holding the back of my head.
That kinky experience at work wasn't the last. A few days later, she wore a remote control vibrator for an hour and gave me the controller. I set it off while Jenny was with a customer but the customer didn't notice. Jenny loved it and it made her incredibly horny. After the customer left, I set off the vibrator on its highest intensity while Jenny fell to her knees and orgasmed uncontrallably in the middle of the store. Eventually Jenny challenged me to participate more directly in our kinky games. The store didn't have many male focused merchandise though. One day, a customer returned an unopened package with large size pink lingerie. Jenny marked it as damaged and brought it back to the inventory room. She opened the package and handed me a lacy pink thong with a bow on the back. She then dared me to wear them for the rest of the day. I resisted initially until she hinted that she'd let me fuck her in the ass if I did it. Reluctantly, I dropped my pantes and underwear and slipped the thong up my legs. I felt humiliated. It didn't help that I got an erection anytime I got naked in front of Jenny. She laughed and joked that I must like it. I pulled my pants back up and Jenny kissed me before heading back to the register.
After a couple hours, I got used to the thong and almost forgot that I was wearing it. Near the end of the day, a group of college girls came in looking for some sorority party games. Jenny asked me to help by getting a box off the high shelf that they couldn't reach. When I reached up, my shirt rode up above my pants and the pink bow on the back of the thong was momentarily exposed to all of them. They giggled and I immediately felt humiliated. Face down, I handed them the box and then walked quickly back to the inventory room. Jenny sold them the game and then closed the store. She walked back to the inventory room with a big grin. I was about to complain but I noticed she was holding a bottle of lube. She pulled my pants off and slipped my cock out of the edge of the thong. She sucked me for a minute before standing up, taking off her pants, and lubing her asshole. She then straddled me in a chair and guided my cock into her ass. She started to bounce up and down while rubbing her pussy with her hand. It felt incredible but I only lasted seconds before shooting my load. Jenny got off and was a bit displeased that she hadn't been able to cum so quickly. I got on my knees in front of her and licked her pusssy while my cum dripped out of her ass.
A week later, we got some new bdsm themed merchandise in the store. There were handcuffs, collars, and paddles... and there were male chastity devices. Jenny bought one and asked me to wear it for the day. I hesitated but she persisted and promised to go commando all day if I did it. I eventually conceded and tried to put the device on. I had an erection at first with Jenny watching but she left and I was eventually able to get it on. Jenny came back to see. It was a clear plastic cage and my cock strained in the confinement. She took a small key, locked it shut, and then jiggled my cock in the cage while laughing. True to her word though, she then lifted up her skirt and showed me that she had taken her panties off. She kissed me and went back to the register.
When I came out to put merchandise on the shelves, Jenny took every opportunity to tease me and try to get me hard. She flashed her ass several times and also simulated sucking on a big dildo. There weren't very many customers so Jenny was able to keep me on edge for nearly the entire day. When she finally closed the store, she came back to the inventory room and unlocked me. My cock stood straight up instantly. Jenny said she had fun and I agreed it had been an exciting day as well. She bent over a table and I fucked her doggystyle. I pulled out before cumming and got on my knees to lick her pussy. She moaned while I licked her and orgasmed quickly. I was jerking my cock and came as well under the table. Jenny was confused and expected me to put my cock back in her but I then showed her the cumshot on the floor.
After that experience, Jenny made me wear the cock cage every day to work. I got a bit used to it over time and Jenny's theatrics definitely helped keep my spirits up. The clientele at the store changed a bit as we brought in more bdsm gear. There were a lot more men who were obviously more than happy to be helped by a girl like Jenny. She even let one guy try some fuzzy pink handcuffs on her to show how they worked. I watched from the other end of the store with my cock nearly breaking through the cage in my pants. The customer graciously unlocked her after a few seconds and bought the handcuffs immediately after. Jenny saw that I was jealous and made sure to interact with the customers even more as a way to tease me. One guy came in trying to find a dildo for his wife and Jenny told him in detail about the dildos that she preferred and eventually sold him a 8 inch dildo while joking that it was bigger than her boyfriend.
At the end of each day, Jenny was still very horny but we had less and less actual sex. Instead, Jenny would unlock me and have me go down on her while I jerked myself. I also came quickly on the ground but would continue to lick Jenny for several minutes until she orgasmed multiple times. She'd tease me verbally too while I went down on her. She'd say things like a hot guy came into the store and was flirting with her while I was in the inventory room. She noticed I got excited whenever she mentioned other guys so she pressed that theme often.
A week later, the store was about to close and there was just one customer left inside. He was looking for some lingerie for his girlfriend but didn't know the exact size to get. Jenny asked if his girlfriend was similar in size to her and he said yes. She then proposed that she could try some on and so he could judge the fit. The guy immediately agreed and Jenny locked the front door so no one else could come in. She took the set of lingerie the guy was holding and went into the dressing room. The guy sat eagerly outside while I watched from behind the register. A minute later, Jenny emerged wearing a lacy black bra and thong. She looked incredible and the guy looked her up and down while she spun around. He said he loved it and would get it. Jenny then walked over to the rack and got him a fresh pair in the same size. Standing in front of him in just the lingerie, she asked if he needed anything else. He looked around, said he wasn't sure, and asked Jenny if she had any recommendations. She walked him over to the bdsm section and showed him the handcuffs on the table. Jenny said that most girls love getting handcuffed and asked him if he'd ever used them before. The man said no and Jenny said he could try them on her. She turned around and put her hands behind her back. He then handcuffed them together and she turned back around towards him sticking her chest out. He said he liked them and would get them as well. Jenny walked with the guy to the cash register, still handcuffed and wearing lingerie. He unlocked her so she could take his credit card and she put his items in the bag. She then unlocked the front door so he could leave with a big smile on his face.
When Jenny walked back to me, she said I had to buy the lingerie she was wearing cause it was already soaking wet. I quickly hoping Jenny would fuck me after all that excitement. Her normal clothes were still in the dressing room and we headed there together. Inside the dressing room, Jenny told me to strip and l did quickly. Jenny did a sexy dance while she teasingly played with my cage and asked if I wanted her to take it off. I said yes but she asked what I'd do for her if she released me. I said anything. She giggled and left momentarily to get another pair of handcuffs from the table. She cuffed my hands behind my back and around the bench post in the back of the dressing room. She then unlocked my cage but I was unable to jerk my cock with my hands locked behind my back. Jenny continued to dance seductively in the lingerie until there was an unexpected knock at the front door. Jenny peaked out and saw that it was the same customer who had just bought the lingerie and handcuffs. She unlocked the door and asked him if he needed anything else. The guy was trying to see if she'd go on a date with him. Jenny declined his advances at first by telling the guy that he already had a girlfriend. He admitted he did but said it was an open relationship while trying every conceivable way to seduce Jenny. She reciprocated his flirtations but said she could be standing in the doorway just wearing lingerie. She told him to go around and she let him in the back door. He agreed and she locked the front door once again.
Before heading back, Jenny returned to me in the dressing room. I was still completely naked, handcuffed to the wall, and my cock was sticking straight up. With a grin, Jenny reminded me that I had just told her she could do 'anything'. I didn't even know what to say. I just stood there flabbergasted. Jenny told me to be completely quiet or else. She closed the dressing room door and also dimmed the lights in the store. I then heard her walk to the back and open the door. The guy walked in and they stood together in the back section of the store. The guy was telling Jenny that she was incredibly sexy and he had to have her. Jenny was playfully coy and asked what he wanted to do with her. He said he wanted to fuck her. Jenny said she wasn't a slut and didn't just fuck anybody. The guy replied by telling Jenny that she looks like a slut.
We were both caught off guard. The guy then told Jenny to get on her knees and she did. I then heard him unzip his pants. He asked Jenny if she wanted to suck his dick. Jenny said yes and I heard her start to give him a blowjob. The guy moaned and called her a slut again. She sucked him for several minutes while I listened intently. My cock was still rock hard and pulsating. The guy told Jenny that she was a good cock sucker and she moaned audibly. I guessed she was rubbing herself while sucking him. Eventually he pulled his dick out of her mouth and started jerking his cock in front of her face. Without prompting, Jenny started begging him to cum on her face and in her mouth. She pleaded that she needed his cum and admitted again that she was a slut. Hearing her yell all these dirty things to this complete stranger, my cock was twitching and I honest to god ejaculated on myself without being able to touch my dick at all. I hadn't cum in over a week and the combination of being free of the cock cage and hearing Jenny go wild set me over the edge.
Seconds later, the guy told Jenny he was about to cum. He told her to open her mouth and I then heard him moan loudly while shooting his load. Jenny moaned as well and I'm sure she was orgasming at the exact same moment. After he subsided, he pulled his pants up and called Jenny a slut one more time before exiting out the back door. Jenny walked over to the dressing room and opened the door. Her face was covered in cum as was the floor in front of me. She unlocked the handcuffs and we both cleaned up and left the store without much discussion of what had just happened.
Jenny was a bit in shock of how far she had gone the next day but soon gained her composure. She asked if I had enjoyed everything and I said it was the most excited I had been in my entire life. Jenny said she was thrilled as well. She asked what she should do if that guy ever came back to the store. I said we'd just have to react to whatever happened but she had my permission to do anything she wanted with him. The next couple weeks at work, Jenny dressed more provocatively hoping the guy might return each day. She showed off more cleavage and went panty-less with short skirts several days in a row. Each day he didn't come though, Jenny got frustrated and would rub herself behind the cash register whenever the store was empty. I remained locked in the cock cage. To make it more comfortable and be able to wear it for longer durations, Jenny helped me shave my pubes. It made a huge difference and I could now wear it overnight and for multiple days in a row.
Her more revealing outfits were noticed by the other customers which were increasingly male these days. Many of them flirted with her and Jenny was accepting of their advances. She didn't do anything crazy like she had done with that one guy but she did enjoy the attention in general and reciprocated their flirtations openly in front of me. I felt both thrilled and ashamed each time I saw it. Jenny knowing that I enjoyed the humiliation didn't help either. There was a heavyset woman who came into the store one day, saw the cock cages, and asked Jenny about them. Eventually Jenny mentioned to the woman that she had her boyfriend wearing a cock cage. The woman laughed and jokingly said she'd love to see that.
I was in the back room but could hear their conversation. Jenny told the woman that I worked nearby and she could just text me to come over if she really wanted to see it. The woman laughed again and took her up on the offer. Jenny then texted me and told me to exit out the back and walk in the front door a few minutes later. I did so and already felt completely embarrassed walking through the door. Jenny introduced me to the woman and explained that she was interested in seeing a cock cage in use. We were the only people in the store and Jenny instructed me to drop my pants in front of both of them. I did so and the woman erupted in laughter. She pointed at my dick and said it looked so small in the cage. She told Jenny that she understood why she had it locked up. She even called it cute while Jenny laughed along. The woman asked if my dick got bigger outside of the cage but Jenny replied by saying 'not much' with a grin on her face. I had my pants down for over a minute as both girls inspected the cage. The woman eventually thanked me and said I could pull my pants back up. Jenny said 'thanks hunny' and I walked out of the store in complete shame. I waited until the woman left the store before returning. Jenny said sorry but laughed at the same time while saying the opportunity was too good to give up.
A week later, I was at the cash register for a brief moment while Jenny was having her lunch break. To my surprise, the guy who she played with several weeks earlier came in. He walked straight up to the cash register and asked if Jenny was there. I said she was on a break but would be back later. The man said he had a message for her. I felt so submissive standing in front of him, knowing what he had done with Jenny. He wasn't particularly handsome or fit but he was very confident and dominant in his demeanor. After an awkward silence, I got a pen and paper and said he could write her a message and I would hand it to her when she got back. The guy agreed. He wrote a brief message and folded up the paper before handing it back to me.
He then left and Jenny returned about 15min later. I showed her the note and she opened it quickly and read it out loud. It said "Slut. I'm gonna come back tonight at 9pm. I expect you to close the store early and unlock the back door. I will then come in. I expect you to be waiting patiently on your knees for me." Jenny nearly orgasmed just reading the note. She looked at me and I knew she had already decided to go through with it. I said I'd hide in the dressing room again just to make sure she was safe.
There weren't many customers for the rest of the day and the hours flew by. Both Jenny and I grew increasingly anxious as 9pm approached. Jenny perused the store and tried to find the best outfit and accessories to wear for him. She immediately selected a collar that said 'slut' on it. It was perfect, she said, and It came with a leash as well. She looked through all the kinky attire in the store too but didn't find anything to her liking. She eventually decided to be completely naked when he arrived, aside from the collar. Around 8:45 Jenny locked the front door and dimmed the lights of the store. I found a corner in the dressing room where I could peak through the crack but not be seen otherwise. Jenny kept me locked in my cage and said she didn't want me cumming this time without her. Jenny then started to get herself ready, first by stripping off all her clothes, and then by attaching her leash and collar. It was just minutes until 9pm and Jenny kneeled down in front of the back door.
We waited for several minutes but it felt like an eternity. Eventually we heard footsteps, the back door swung open, and the guy walked in. He walked directly in front of Jenny and picked up her leash. He looked pleased that she wore a collar and laughed when he saw it said 'slut' across it. The guy asked if his slut was ready and Jenny replied with "yes sir". He then pulled Jenny by the leash and led her crawling on her hands and knees to the center of the room. He then picked her up and placed her standing straight up with her legs shoulder width apart and her hands up behind her head. With Jenny standing there completely exposed and vulnerable, he proceeded to fondle her entire body, pinch her nipples, finger her pussy, and grope her ass. Jenny moaned with every touch. He then stepped back and started to remove his pants. Jenny instinctively fell back to her knees and he guided his cock into her mouth. She eagerly sucked it and he guided her pace using the leash. Eventually he pulled his cock out of her mouth and slapped it on her face a few times before picking her back up again.
He pulled out a condom and put it on his cock. Then he bent Jenny over a nearby table before inserting his cock into her pussy. Jenny moaned loudly. He put one hand on her hip and used the leash in his other hand to pull her towards him with each thrust. His pace increased and he started asking Jenny humiliating questions. 'Are you a slut?', 'You like my cock?', 'You want my cum?'. In between her moans, Jenny screamed yes to all his questions.
I guessed that she came three separate times as he continued to pound her pussy from behind. He eventually pulled out and laid down on the ground. Jenny mounted him cowgirl style and started bouncing up and down on his cock. He reached up and pinched both her nipples before grabbing her leash again and pulling her body down against his. Jenny put her lips on his and they started making out as she continued to ride his cock. It's weird to say given everything they were doing but somehow that kiss was the worst part for me. The guy was close to cumming and told Jenny to get off of him. He stood up, ripped off the condom, and Jenny immediately took his cock back into her mouth. Seconds later, he moaned loudly and filled Jenny's mouth with his cum. She moaned as well and swallowed every drop. She continued to suck him more slowly for another minute after he came until he pulled out and called her a good slut.
The guy got dressed and left quickly thereafter. Jenny remained naked on her knees, completely exhausted from the entire experience. I emerged from the dressing room and asked Jenny if she was ok. She responded by saying she was more than ok. Since then, the guy fucked Jenny several more times, sometimes at the store and sometimes at a nearby hotel room. Eventually the store when out of business and Jenny and I broke up a year or so later. The entire experience got me hooked on being a cuckold for life.
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