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Steph


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Hello,

I have a strange story. Not sure if it's exactly cuckolding but let me know what you think.

I'm a white guy in my mid twenties, very skinny, and a bit nerdy. Just before covid hit, I moved into a crappy apartment complex. It was honestly the only thing I could afford. There are 32 units in the complex and it is owned and operated by this lady named Steph. She is in her early 40s I think and weighs maybe 200lbs. She doesn't look fat but she definitely has a curvy milf type look. After meeting her and getting a tour of the apartment, my initial takeaway was that she was a complete bitch. I didn't expect to interact with her much besides paying my rent each month.

A few weeks later, I saw Steph struggling to carry some boxes to her apartment. I offered to help and she accepted. She gave me the heaviest box and led me to her apartment that was at the far end of the complex. When we got to her door, she opened it and asked me to put the box down on her coffee table.

I did so and she thanked me for the help. I looked around and saw that her apartment was kind of a mess. There were clothes thrown everywhere including her underwear. She caught me staring and asked if I was some kind of pervert or something. I said no and apologized for intruding. I was trying to shuffle my way out her door when she started to explain that she hurt her back recently and hadn't been able to keep things clean like she usually does.

I told her it wasn't a problem and just tried to be nice by saying I could help out if she ever needed anything. She took my offer seriously though and immediately asked if I could help her clean up a bit. I reluctantly agreed and asked what she wanted. She sat down on the couch and directed me to pick up her clothes from around the living room and bring them to her so she could fold them.

I started by grabbing her shirts and jeans but eventually there were just undergarments left. I paused briefly but Steph told me to keep going. I picked up a large bra and handed it to her. She didn't react at all so I continued. Next I picked up a small pile of lacy panties and thongs. I laid them down awkwardly in front of her and then finished up by grabbing a couple more bras and a small robe. Steph didn't react to me and continued folding her clothes as if nothing was amiss. Again I started to shuffle towards the door and asked Steph if she needed anything else. She said that was it for now and thanked me for my help. I quickly exited and headed straight to my apartment.

A week later, Steph came to my apartment to pick up rent. I gave her the check and she thanked me again for my help earlier. I foolishly said I could help anytime and she again took me up on my half hearted offer. Steph complained that her back was still hurting and she needed some help later that night. She got a muscle pain relief cream from the pharmacy and needed help putting it on her back. She added that it was a bit inappropriate to ask me as a tenant and said I didn't have to do it if I didn't want to. After thinking it over, I told Steph it wasn't a problem and agreed to meet her at her apartment later that night. I just thought it would be worse for me long term to upset her as my landlord so I decided to bite my lip and go through with it.

Around 8pm, I arrived at Steph's apartment. She greeted me wearing a robe and let me in. She led me into her bathroom and handed me the cream. I asked her what I should do and she told me to just rub it around on her back. She loosened her robe and she was wearing just a bra and panties underneath.I squirted out some cream into my hand and began rubbing it on Steph's back while she watched me through the mirror. I got most of her upper back but the back of her bra was covering some areas. She said I could undo it, explaining that it hurt her to unsnap it herself.

I tried to unsnap it but I embarrassingly failed several times in a row. Steph laughed and asked if I had ever even been with a girl before. I said yes but added that her bra was more tricky than I'm used to. I eventually got it off and continued rubbing the cream over her back as Steph held the bra over her boobs with her hands. I tried my best to stay focused on the task but I'd be lying to say I wasn't a bit aroused rubbing cream on the back of this half naked lady. I maybe lingered too long and Steph chided me saying I hope you're not enjoying this too much. I apologized and said I think I got her whole back covered. Steph thanked me and then told me to leave. As I walked to her door, I was embarrassed to realize I had a slight boner and did my best to make sure Steph didn't see.

Another week later, I ran into Steph in the hallway and she thanked me for rubbing her back the other day. I said no problem. She explained that she went to the doctor but the doctor told her that nothing was physically wrong. She said the doctor recommended just resting and getting some massages if she could. I was about to leave when Steph asked if I'd be willing to massage her back a bit. I really was afraid to go through with it but worried that it would be worse somehow if I said no at this point. I told Steph I'd try but mentioned that I'm not a professional masseuse by any extent. Steph told me it was ok and told me to come over later that night.

When I arrived at her apartment door, she was wearing the same robe again. I asked her where she wanted to get massaged and she said on her bed. She led me to her bedroom where there were a couple towels already on the bed. She told me to turn around and she removed her robe, laid face down on the bed, and put a towel over her butt. She then told me I could look now and I turned back around. On the bedside table, there was lotion. I picked it up and squirted it into my hands. I started to rub Steph's back as she gave me instructions on different areas to focus on. I started high on her shoulders and eventually worked down to her lower back. I had a rock hard boner the entire time but luckily Steph was face down and couldn't notice.

I thought I might be done but Steph told me to keep going and get her legs as well. I moved down below the towel and started massaging her calves before working my way up to her thighs. I stayed respectfully far away from her butt and crotch. After working on her legs for several minutes, Steph spread her legs slightly to give me better access to the inside of her thighs. I didn't know what to do but Steph told me to keep going but cautioned me to not get any lotion on her panties. I kept moving my hands up, extending them slightly underneath the towel. I could feel the warmth around her crotch and was incredibly turned on.

I thought I had gone far enough and stopped massaging. Steph thanked me and asked me to get her robe. I picked it up, handed it to her, and then turned around so she could put it on. When she told me she was decent, I turned back around but she noticed the slight bulge in my pants. She yelled that I must be enjoying this and I immediately apologized. I tried to explain that it was just natural but she told me to leave. I headed back to my apartment in complete shame. Strangely though, when I saw Steph a few days later, she didn't mention it at all. In fact, she thanked me for the massage and said it helped her back feel a lot better. I didn't know how to respond and just told her she was welcome. She surprised me by asking if I could massage her back again since it helped so much the first time. I asked her if she was sure and she said yes. Reluctantly, I agreed to meet her again that night and give her another massage.

When I met her that night, she led me to her bed, same as before. She took off her robe, laid face down on the bed, and put the towel over her butt. I then grabbed the lotion and started massaging her back. I did the same moves working from her shoulders to her lower back and then from her calves up to her thighs. As I was extending my hand under her towel next to her hip, I realized that she wasn't wearing any panties and was completely naked this time. That fact alone made me incredibly aroused but I wasn't sure how to respond to that decision. I continued to work my way higher and higher up her thighs and Steph reciprocated by spreading her legs more to give me better access.

I knew I must be just inches from her pussy and stopped my advances fearing her reprisal. She cajoled me to keep going though. I apologized and told Steph that I didn't want to go too far and make her uncomfortable. She chided me to just remove the towel if I wasn't familiar with where a woman's private parts were. I slowly pulled the towel off her butt and she was completely naked lying on the bed in front of me. I continued to massage her thighs and worked up the bottom of her butt. As I massaged her butt, Steph said that felt good and I continued to rub her cheeks more deeply. As I did, I separated her butt cheeks and got intermittent views of her pussy and asshole. I was nearly bursting out of my pants.

I didn't know how to end the massage and I worked my way back up Steph's back to her shoulders before stopping. She thanked me and asked for her robe which I handed to her. I turned around as she put it on and tried to exit the bedroom so she didn't see my erection. Steph told me to stop and turn around as I stood in her bedroom doorway. I did so and my bulge was on full display. Steph just laughed and said she couldn't believe it. She asked if I needed stress relief too but I said no. I tried to apologize but didn't want to hear it. She went to her clothes hamper and picked out a pair of her panties. She handed them to me and asked if that is what I wanted after all. I didn't know how to respond. She told me to show her and I slowly unzipped my pants. When my dick spilled out, Steph laughed and said oh my god it's so small.

I was so humiliated. Steph mused that my small size explained why I didn't know how to remove a bra earlier. I just stood there until Steph told me to relieve myself. I started to stroke my dick with my right hand while holding her panties with my right. An embarrassingly short time later, I started to cum and shot my load onto her panties. Steph watched and told me I was gross. She said I needed to wash her panties and bring them back to her the next day. I pulled my pants back up and left her apartment quickly.

When I came back the following night, I had Steph's panties in my pocket. She let me in and was wearing her robe again. I tried to hand her the panties but she refused to take them. She said she didn't want them now that I had ejaculated in them. Instead, she led me into the bedroom, took off her robe, and laid face down on her bed. She didn't bother with a towel this time. I picked up the lotion and started to massage her. As I got down to her legs, she spread them out and her full asshole and pussy were on display. I was fully erect in my pants. I worked up from her calves, to her thighs, and eventually to her butt. She made no objections to where I touched so I started to push the boundaries. I got closer and closer to her asshole without any reaction from her. I then slid back down to her thighs and paid special attention to her inner thighs. Inch by inch, I made my way closer to her pussy.

I eventually got all the way up to the crease between her thighs and crotch and she still had no reaction. With a bit of a gulp, I pressed further and grazed her pussy with the side of my hand. She was completely unperturbed. I brushed past it again and she adjusted her posture to spread her legs even further. I took that as a sign and began to massage all the way up her inner thigh and rub fully across her pussy with each stroke. I continued that move for several minutes without any word from her. I then pushed further and got a finer partially into her pussy. She was soaking wet and pushed her body back so my finger went even deeper. I started to finger her with one hand while massaging her thigh and butt with my other. I started with just one finger and then pressed a second one in. After another couple minutes, I was basically finger banging her and I could tell she was close to an orgasm. I felt her pussy contract and she let out a soft moan.

I pulled my fingers out of her pussy and she turned over on the bed. Her boobs and pussy were on full display to me. She told me to keep massaging and I grabbed some more lotion. I started by spreading it on her chest and boobs, massaging them together and slightly pinching the nipples. I then worked on the front of her thighs which she spread again for me. I was about to finger her again but her pussy looked to invititing. Instead, I leaned forward and kissed the top inside of her thigh. Again she had no reaction so I continued kissing up her leg until my mouth was directly on her pussy.

I stuck out my tongue and started licking her clit and she moaned. I licked her for a minute before she placed her hands on the back of my head and pulled my mouth forcefully against her vagina. It was so hot and I kept licking as best I could. Eventually Steph was humping my face more than I was licking her but I loved it. Just as she was about to cum, she squeezed her thighs together around my head and let out a loud moan. After her orgasm, I continued to lick her for another minute before she pushed me off.

I sat up on the bed as I kneeled off the side. My cock was still rock hard and Steph looked at it. She asked what I wanted and I asked if I could jerk myself again. She said she didn't want to see my tiny dick again and told me to leave. As I walked back to my apartment, I realized her panties were still in my pocket. When I got inside, I took off my pants and started jerking my cock with the panties in my hand. The material felt soft and silky and I was so horny. I came quickly and once again covered her panties in my cum.

Over the next couple months, I continued to go over to Steph's apartment two or three times a week. Eventually her back was better and she didn't need the pretense of massages anymore. Instead, I would typically just go down on her and lick her pussy until she came. We didn't talk about it directly and it just happened as if it was a scheduled meeting between us. Sometimes she would sit on my face and really grind her pussy into my mouth. Other times she would sit on her couch and watch TV while I licked her. She never reciprocated though and I always scurried back to my apartment afterwards to masturbate.

One day, I saw another man enter Steph's apartment. I spied outside from the courtyard and he was in her apartment for nearly an hour. When he left, Steph kissed him at the door and he left the apartment complex. He was probably around the same age as Steph but much taller and muscular than me. I guessed they were dating or maybe just hooking up. A few minutes later, I knocked on Steph's door and tried to act like nothing happened. She let me in and told me to lay down on the ground. She then squatted over me and sat on my face. I started to lick her and nothing seemed different at first.

Eventually though I started to notice a different taste than I was used to. It dawned on me quickly that I was licking a mix of Steph's juices and that guy's cum. He had just fucked her and given her a creampie. I stopped licking her and Steph asked me what was wrong. I mentioned that I noticed another guy leave just before I arrived. Steph laughed and said she had been seeing that guy for several weeks already. I asked if they had sex and she said yes. Meekly, I said that I thought I could taste him a bit. Steph laughed again and explained that it wasn't the first time I've tasted him.

I was horrified and embarrassed but Steph told me to keep going. She grabbed my hair and pinned my mouth against her vagina while thrusting it back and forth. I started licking her again and the taste was now unmistakeable. I was licking his cum straight out of her pussy. Steph orgasmed a couple minutes later and stopped humping my head. Still sitting on my chest, I looked up at her in total humiliation. Steph called me a fag and said she knew I liked it. I didn't know how to respond. She kept teasing me and eventually asked if I wanted to get the taste of my mouth.

I nodded and she got back up on her knees and positioned her pussy in front of my face again. She told me to close my eyes and opened my mouth as she grabbed my hair again. Then to my complete surprise, she squirted a short stream of piss into my mouth and across my face. I gagged and she got off of me laughing once again. I immediately left her apartment completely angry and heated but got horny again by the time I entered my apartment and shamefully mastubated with her piss still covering my face.

Since then, I meet Steph less often but she is crueler than ever whenever I do. I have eaten several more creampies from her and from different men as well. I still masturbate afterwards each time despite the humiliation I endure from her.

K - keykay785@gmail.com




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