Hello,
Hey. Long time reader of the site. Wanted to describe the unique ways in which my girlfriend has cuckolded me recently.
So Lauren and I have been living together for almost four years. She is incredibly beautiful and also incredibly small. She is barely 5ft tall and weighs about 100lbs. Her personality, however, overshadows her short stature. She is incredibly outgoing and the life of the party wherever she goes. I'm a bit more introverted by comparison but we balance each other out and have a great relationship.
From the beginning of our relationship, I knew that Lauren had a thing for older men... specifically older bear type men with large stature. Her friends knew too and it was kind of a running joke inside their group. They'd be out for lunch and some old guy would walk by and then they'd all look at Lauren and giggle. It was just a funny quirk to Lauren's personality, especially given the dichotomy of her size and their size. It never really amounted to anything early in our relationship. There were maybe a couple times where she was a bit flirtatious with an older guy at a store but that was about it. She was generally flirtatious with everyone to be honest so it was hard to pick out anything unusual in her behavior with older men.
During the past year while we were holed up together in our apartment, I confessed my cuckolding fetish to Lauren. I described how she was so beautiful and it would be incredible to see some guy with ripped abs and a huge cock have sex with her. Lauren was quite open and adventurous sexually so my fantasy didn't freak her out. She watched some videos and read a few articles about cuckolding to get more acquainted with the idea. Overall, she was intrigued and open to trying it. She started by teasing me a bit during sex and taking a more dominant demeanor in general. We had one particularly exhilarating session when she sat on my face and described some kinky experiences she had in college while I licked her pussy and jerked off. She could see that I was really turned on by the experience and that turned her on as well. We both came simultaneously and she continued to grind her pussy into my mouth for another few minutes until she came again.
A week later, Lauren told me she'd do it but she wanted to do it her way. She said she was going to pick whatever guy she wanted and I had to live with it. She even made me pinky promise that she could fuck anyone she wanted, however she wanted, for however long she wanted, and I couldn't make any objections. I eagerly agreed though I guess I didn't comprehend the potential mess I was getting myself into at the time.
Despite my initial desire to see Lauren with a porn star type guy with an athletic physique and giant dick, it was clear she wanted something different. She was looking for more of a Ron Jeremy than a James Deen I guess. And Lauren was intent to be thorough in her search. Whenever we went out somewhere, she was on a mission to talk to as many old men as possible. Some of the men were confused by her attention but the vast majority were obviously excited to be interacting with such a beautiful young girl. On multiple occasions, I just stood awkwardly to the side holding Lauren's purse while she chatted up some random guy. She got more creative over time and started contriving more ways to force interactions. One of her favorite tricks was to ask a guy to get something off a high shelf and then thanking them profusely for their help. Another mainstay was acting like we were arguing about her outfit being inappropriate and then going to a stranger to ask their opinion. She'd say "My boyfriend thinks my skirt is too short but I like it. What do you think?" This always elicited a positive response and gave Lauren the opportunity to then say "Wow, I guess you should be my boyfriend then" or something along those lines.
These games went on for several weeks and Lauren seemed quite comfortable keeping me on edge at every moment. At home, she didn't let me have sex with her anymore. I could lick her pussy and I could jerk off but that was it. She started complaining that she was horny after meeting a new guy and would ask me to drive her home immediately. Once we got home, she'd then make me lick her pussy until she came. And after she came, she'd give me permission to jerk off but would act bored or impatient while I did it. After a few sessions, I was cumming in less than thirty seconds after getting her permission.
At this point in time, our apartment lease was about to expire and Lauren and I were searching for a new place to live. We spent most weekends visiting different apartment complexes in our area. This experience was frustrating because most places had nothing available or were incredibly expensive. We decided to open up our search to include other types of rentals that might be more in our price range. We visited a couple potential options where people were renting out in law units or converted garages behind their homes. They seemed like good options but still a bit on the expensive side. We kept searching until we eventually saw an ad for a guy renting out a room in his home. His name was Tom. He was newly divorced and looking to rent out a guest room in his house. I was a bit skeptical of the setup but Lauren said we should at least check it out since we couldn't afford anything else.
We arrived at Tom's house on a Saturday morning. We knocked on the door and Tom let us in. Standing in front of Tom, I was instantly worried. He looked like he had been an NFL linebacker but 30 years ago. I guessed he was maybe 60 years old, 6'4'', and 300lbs. He had a big belly but also looked strong in his arms and legs. Lauren was unsurprisingly elated to meet Tom and turned on the charm immediately. Tom showed us around the house which was quite small. There were two bedrooms, one bathroom, a living room, and a kitchen. The entire tour was only 5 minutes long. I thought the place was just ok but Lauren was full of excitement. She complimented the accommodations and Tom at every opportunity. Tom noticed her flirty demeanor and reciprocated by saying he'd be so lucky to have a beautiful girl like Lauren living under his roof. Before I could even ask a question, Lauren was shaking Tom's hand and agreeing to become his new tenant. Tom said we could move in immediately if we wanted. Lauren said it was a good idea and said I should head back to the apartment and pack things up while she stayed and planned out how to organize our new bedroom. There was already a bed and some other furniture that she wanted to move around and try out different configurations. I reluctantly went home and left Lauren alone with Tom.
We honestly didn't own a lot of stuff. We had already boxed up most of our items and I was able to load up everything except our clothes into my car in just a couple hours. When I got back to Tom's house, Lauren and Tom were both sweaty and in the living room drinking water. They had been moving furniture around in the bedroom and we're now taking a break to relax. Lauren said I should move our stuff into the room and she'd help after finishing her water. I went to the car to pick up some boxes and was surprised to see that Lauren had accidentally spilled her water onto herself in the twenty seconds I was gone. She acted embarrassed and apologized to Tom. She said she should change but I explained that I wasn't able to fit our clothes in the car and would need to make another trip to bring them over.
Tom said it wasn't a worry and she could just throw her clothes into the dryer for a bit. The dryer was in the bathroom and Tom showed her how to use it. I continued moving boxes from my car into the house and saw brief glimpses of Lauren interacting with Tom every couple minutes in the bathroom. By my third trip, Lauren had removed her shirt and thrown it into the dryer. She was now standing next to Tom in just her bra and some short shorts. As I walked back to go to the car, I heard Lauren say "I hope this is ok, Tom. I just feel very comfortable already in this space and I guess we'll be seeing a lot of each other eventually." Tom confirmed quickly that it was ok as I walked out the door. When I came back, Lauren's shorts were off too and she was asking Tom if he saw any water on her bra or panties. I'm sure Lauren would have stripped completely naked at that moment but Tom said that everything else looked dry. He put the dryer on and they walked out of the bathroom. I had just finished moving the last box and Lauren was complaining that she was a bit cold now. She asked Tom if he had a shirt she could borrow and he said of course. He brought out a t-shirt and she threw it over her head. It looked like a dress on her. It went past her knees on the bottom and hung off her shoulder on the top.
After that, Lauren and I got our bedroom organized and eventually headed to bed. We still had to get our clothes from the apartment but we were both exhausted and decided to do it the following day. Lauren was still wearing Tom's shirt but she had taken off her bra and panties and was now completely naked inside of it. We didn't know if Tom could hear us in the room. Lauren put her finger to her lips to tell to be quiet. She got a piece of paper from a box and wrote "I'm gonna fuck Tom tomorrow. Lick my pussy right now and then we'll go to bed. Don't touch your cock". I got on my knees in front of the bed. Lauren put one leg up, pulled up Tom's shirt, grabbed the back of my head, and pulled my mouth against her pussy. She grinded her pussy into my mouth for a few minutes before cumming. She had her hand covering her mouth the entire time trying to muffle her moans. We then got into bed and fell to sleep.
The next day, Lauren was out of bed before I woke up. When I eventually got up and walked into the living room, Lauren and Tom were there together drinking coffee and watching the morning news. Lauren was still wearing Tom's shirt with nothing underneath. They both greeted me and Lauren handed me a cup of coffee. I sat there and had a few sips before Lauren said I should probably take off and get our clothes from the apartment. I had barely woken up but realized that Lauren was trying to get me out of there as quickly as possible. I got the hint. I grabbed my keys and said goodbye to both Lauren and Tom. I told Lauren that I'd text her when I'm on my way back. I left and heard Lauren telling Tom that she should give him back his shirt as I closed the door. I was simultaneously heartbroken and incredibly turned on.
I worked quickly at the apartment. In addition to collecting our clothes, I had to clean up a bit and turn in our key to the front office. It only took about an hour and I texted Lauren that I was on my way back but she had no response. When I got to Tom's house, I opened the front door and immediately saw Lauren and Tom completely naked. Tom was sitting on the couch and Lauren was on top straddling him. His cock was in her pussy, her arms were around his shoulders, and they were kissing as I opened the door. Tom was a bit startled to see me but Lauren acted cool. She turned to me still bouncing slowly on his cock and explained that she was just thanking Tom for all his generosity. She told me I should move the rest of our things into our room and then turned back to Tom and continued to kiss him. I did as told and made several trips in and out with bags of clothes in my arms. Each time I walked through the living room, Lauren and Tom paid no attention to me. I moved the last bag into our room and then just sat there on the near the door waiting for Lauren and Tom to finish. As I waited, I heard Lauren orgasm and then tell Tom that she wanted him to cum inside her. A couple minutes later, Tom started to cum and Lauren came again at the time. Tom thanked Lauren but Lauren said "No, thank you Tom". She then hopped off him and walked into our bedroom.
I stayed sitting on the floor of the bedroom as Lauren entered. WIthout even a word, she pushed me to lay down on the ground and then straddled my face. She started to masturbate inches in front of my face as Tom's cum leaked out of her pussy and onto my mouth. I had my mouth closed at first but then accepted my fate and opened it to taste Tom's cum. Lauren then dropped her pussy onto my mouth and made me lick her pussy until she came once again. She got up and told me I could masturbate. I took off my shorts and furiously started jerking my cock. She started counting down from ten and I came all over myself before she got to three.
We took turns taking showers and cleaning off and then put our clothes away in the bedroom. We eventually went back out into the living room where Tom was. Lauren acted like nothing usual had happened though I had trouble maintaining any eye contact with Tom after what had happened. We got a pizza delivered and ate it together while watching TV. Later that night, we went back to our bedroom and got ready for bed. I was exhausted but Lauren seemed restless. We heard Tom turn the shower turn on so we knew we could finally talk openly. Lauren turned to me and asked if I was a happy cuckold. I told her it was better than I ever imagined. She smiled and said good. The shower turned off and we heard Tom walk into his bedroom. Lauren then hopped out of the bed and told me she'd see me tomorrow. She walked out of our bedroom and I heard her knock on Tom's room. Tom opened his door and asked Lauren if anything was wrong. She said it was cold in our room and asked if she could sleep with him for the night. Tom said of course and I heard them kiss before Lauren entered his room and Tom closed the door.
BF - thirtyninesixtythree@gmail.com
