Hello,
My girlfriend Jess and I are in our late twenties. We've been dating for four years and living together for two years now. From the moment we started living together, I told Jess about my cuckolding fetish and my desire for her to have relations with other men. She wasn't scared by the idea but she also wasn't overly enthused by it either. Though very sexy and kinky, Jess is wary of meeting strangers at bars or online and abhors anything resembling a one night stand.
She said if she did try something, she'd want it to be with someone we already knew and felt comfortable with. But at the same time, she wanted to keep things discreet and didn't know who she could pick (friends, coworkers, etc) without everyone else finding out. We agreed to keep an eye out for opportunities but it felt for a long time like it was a dead end.
One other particularity was that Jess had slightly unusual interests in men. She lost her virginity when she was 20 to a guy who was 45. Ever since then (and perhaps before too), she's been really attracted to older men. And not just a little bit older... like a guy in his 50s or 60s would be her prime target today.
She can't really explain the attraction but also doesn't deny it. We joke about it occasionally even. I'm the only guy she's been with who is around her own age so Jess tells me that I'm the outlier more than the older guys are. Anyways, as we were hypothesizing about potential candidates for her to meet, the list of older men we knew was basically non-existent.
That all changed though the day we moved into a new duplex apartment. The place was pretty old but we could afford it and thankfully. We got a tour from the owner who was also the resident on the other side of the duplex. His name was Tim. He was in his early 50s and appeared very fit for his age. He was exactly the type of guy that Jess would like. Tim also took notice of Jess and was trying his best to play up the amenities of the apartment. As he led us through the different rooms, Jess was very complimentary and seemed excited by the place. Finally, Tim led us to the backyard that was shared by both apartments. It wasn't very big but it had some grass and an above ground hot tub.
At the end of the tour, Jess and I accepted the apartment and signed the paperwork. We shook Tim's hand and left together. On the drive back, I asked Jess if she fancied Tim. She admitted she did and asked if we could finally try out my cuckold fantasy. I agreed but asked how we would make it work. Jess explained that we should just let it happen naturally. Our lease was for a full year so we had plenty of time.
We moved together the following. Tim helped us carry our boxes inside and then brought over a few beers to celebrate our move in. We drank them in the backyard since it was warm inside the apartment and our stuff was everywhere. All three of us were sweaty from carrying everything inside. Jess looked great in a crop top and short shorts and I could notice Tim discreetly checking her out. After we finished our drinks, Jess hugged Tim and thanked him for all his help. Tim was surprised but quickly accepted and put his arm around Jess while looking down at her. Jess and I then went into our new apartment and started unpacking our things while Tim went back to his.
Later that night, Tim used the hot tub in the backyard. Jess and I peeked discreetly through the window to watch him. He looked great with his shirt off and he soon put his head back and closed his eyes to relax. Jess put her hand into her pants and started to rub herself while watching Tim. Eventually he opened his eyes and we cowered from the window to not get caught. We got into bed and I went down on Jess. She was already soaking wet and I masturbated while licking her. A couple minutes later, both of us came simultaneously.
The next few weeks were a blur. We interacted with Tim multiple times with Jess taking every opportunity to make physical contact with him when she could. Tim became increasingly flirateous with Jess too and started calling her cutie as a nickname. Finally one weekend, Jess decided she wanted to sun tan in the backyard. In order to make sure Tim noticed, she knocked on his back door and asked if it was ok for her to do that first. Time surprisingly told her of course. Jess got dressed in a skimpy two piece bikini that I bought her a year ago. The top had a tie in the back so it could be undone easily when she was laying down. And the bottom was a thong style that showed off her butt.
She put down a towel in the grass and laid down in the grass in front of Tim's window. She started face up and then turned over, untied the back of her top, and then laid face down topless on the ground. I'm sure Tim was at this window watching every second. I was doing the same at ours. When she was finished, Jess stood up and flashed the side of her boobs for a couple seconds before she got her top tied back on. She then walked over to the hot tub and stuck her hand in. At this moment, Tim walked out his back door and told Jess that she could use the hot tub whenever she liked. Jess said she was too hot now but she'd try it later tonight. She asked Tim if he'd join her and he obliged.
Later that night, I set up at the window again to watch Jess outside. Tim went into the hot tub first with a couple beers and waited for Jess. I told Jess he was waiting for her and she scrambled quickly outside fully clothed. She apologized to Tim for keeping him waiting but he said it wasn't a problem. She said that her bikini from earlier that day got a stain on it and she asked him if he was if she just got in the hot tub in her underwear. Tim said yes quickly and Jess proceed to strip off her clothes just outside of the hot tub. I know he already saw her wearing less earlier in the day but it somehow felt more exciting seeing her actively strip off her clothes in front of him. Tim asked if I'd be joining too but Jess said I was feeling well and was already asleep.
Eventually Jess was just wearing panties and a bralette and she hopped into the hot tub. Tim handed her a beer and they both said cheers. They exchanged small talk for several minutes before the bubbles turned off. Jess then hopped out of the tub to hit the button to turn them back on. She looked so hot in wet semi-see through underwear. Tim got a great look as she climbed back into the tub. She sat down closer to him as they continued to talk. Jess was very flirtatious and laughing at everything he said. They eventually both got out and Jess lamented that she forgot a towel. Tim gave her his which she used to quickly dry off. She then handed it back to him and he dried himself off as well. Jess gave Tim a hug while still just wearing her underwear. He held her for several seconds before they separated. Jess then picked up her clothes from the ground and came back into the apartment.
When she got into the bedroom, Jess said that she felt his cock. Or rather, she said she could feel his semi-erect cock when she hugged him. She took this as evidence that her seduction was working. She stripped off her wet underwear and laid naked on the bed. I stripped to and laid down next to her. We both kissed and then proceeded to masturbate laying side by side.
After their hot tub experience, there was less pretense between Tim and Jess. They openly flirted and hugged all the time. She even went over to his apartment for a half hour to have a beer one day before I came home. Jess had masturbated so many times thinking about Tim though that she was eager to finally make something happen. She walked over to his back door and set another date to use the hot tub with Tim. She told him I'd be gone from the apartment seeing some friends that evening and she wanted some company. I hadn't left though and instead had to stay quiet in the bedroom all day so Tim didn't know I was there.
Come sundown, Tim got into the hot tub first with a couple of beers. Jess came out a minute later wearing her bikini this time. She hopped in next to him and he handed her the drink. After some small talk, Jess turned around and asked Tim to massage her shoulders. As he did, she untied her top to give him full access to her back. She threw her top over the side of the tub and was now topless. After a couple minutes, Tim ended the massage and Jess faced him, revealing her boobs just a couple feet away from him. She asked him if it was ok if she stayed topless and he said yes unsurprisingly.
They chatted a bit more as Jess inched towards him. Eventually they were side by side and then quickly Jess was sitting on his lap and his arms were around her. They stared at each other and then Jess kissed Tim on the lips. He returned her kiss and they made out for a few minutes. Tim then sat up on the side of the tub and Jess pulled his trunks down.
Without any delay, she took his cock into her mouth and sucked him. He put his hand on her headed and guided her pace as I watched the back of her head bob up and down. Then Jess got up, got out of the tub, and peeled her bottoms off. They were both now completed naked. Tim got out as well and led her by hand to his apartment. I then listened through the wall for the next hour as they fucked in his bed.
Since that night, Jess and Tim have sex once or twice a week. It's always with the pretense that I'm gone or sick or busy with work, etc. Jess loves it and I love hearing every second of it.
Nesp - 543nesp345@gmail.com
