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Welcome to Portland and to our cuckold personals and classified ads. This city is known for its parks, bridges and bicycle paths, as well as for its eco-friendliness and coffee houses. It also has lots of married wives and girlfriends, who fantasize about being with other men sexually.
My GF thinking about my Dad!
The Start - A couple of years ago I took my girlfriend on a family vacation with me across the country to Arkansas. Whenever we travel we get very high sex-drives, so we get a hotel on the other side of town from my family so that we can have space for one another. We also like to go on excursions as a couple, without the rest of the group if we can. All of us are from Portland but like seeing new states.
So we planned a couples trip to the lake, there's not much to do in Hot Springs. She had brought this white one piece bikini, that was thonged in the back, and had very deep cleavage in the front. It offered absolutely zero support for her breasts, which are 36-D and slightly jiggly. Even when we were getting ready around the apartment, one of her breasts popped out multiple times. She has what some people call pepperoni nipples, very very large areola that are hard to miss when they fall out.
Anyways to make the story shorter, we went to the lake and when she got in the water we noticed just how sheer that bathing suit got when wet. Literally able to distinguish her areola from her nipple, and not the type of thing that you can ignore or pretend not to see. You could literally see her entire areola and nipples through it.
This was all well and good until I heard my family calling me from the dock. There is not much to do in this part of Arkansas and as it turns out, they decided to rent a boat on the same day my girlfriend and I went on our beach trip.
See the last story occuring in Louisville.
Together - Luckily at this point we have not been in the water for about 20 minutes, and my girlfriend's top had dried off to the point that it was not sheer anymore. But her cleavage and side-boob was still very inappropriate. It is the type of bathing suit where you can tell exactly how the breasts rest/ hang.
To make the long story short, we ended up getting on the boat with my family. She was constantly having to adjust her top to keep her breasts in. On top of this, her ass was jiggling when she walked.
My family had also rented one of those large round inner-tube rafts that the boat can tow behind it. The type where 4 seats are in a circle facing one-another. After some convincing, my girlfriend got on the raft with me. But then my Dad told my brother to drive the boat, because he wanted to go on the raft with us (he hadn't gotten a turn yet).
It continues - We were already sitting in the raft and my Dad climbed in. My girlfriend's big areolas were both perfectly visible because her top got wet on the swim over to the raft. Her nipples were hard. Like I said it is not the type of areola you can ignore, very big and firm. At this point I felt very strange because my girlfriend's titties are virtually exposed to my Dad in her sheer top.
My brother towed the raft pretty fast, taking sharp turns to try and spill us off. Within literally 30 seconds, both of my girlfriend's tits flew out and were jiggling all over. You can imagine, two big 36-D breasts bouncing around naked, as the raft is dragged over waves at like 20MPH.
She had to hold onto the seat handles so as not to fall off, and so her boobs were just flopping all over for at least 10 long seconds before she screamed and tried to put them back in. It felt like forever that her tits were completely out, because of the intensity and sheer inappropriateness of the moment.
I saw my dad legit staring the entire time at my girlfriend's naked wet tits flopping around gratuitously. It wasn't just like a simple nip-slip of one breast - it was both of her boobs bouncing all over the place and jiggling pornographically.
The Finish - When we got home that night, her and I finally talked about it after a few drinks. She said how awkward it was, and asked if I, "think he saw." She apologized, and I was like like, "No no no it's not your fault, trust me, it's OK."
Something about the way I said it was OK must have came across as eager, because she got wide-eyed with disbelief and said, in a humorously incredulous way, "NOOOOOO WAY. Really?" She knew even before I did, that it appealed to my cuckold fetish.
That night she stroked me while asking me stuff like, "How does it feel to know that your Dad has seen your girlfriend's titties?" and "Do you think he jacked off to it yet?" Eventually she talked about sucking his dick and getting his load on her boobs. She finished me with a tit fuck and I came onto them.
Basically over the next 3 days of our vacation, she showed as much of her breasts as she could to my dad accidentally, and he looked hard. She then made me cum to the fantasy of her and my dad at night. For example, she wore that same bikini for him in the day and then that night in the shower and I jacked off as she refreshed my memory on what he saw. She also pulled up amateur blowjob videos and stroked me to them saying to imagine it was a video of her and him. She was soaking. We never spoke of it again after the vacation ended. I think she is embarrassed about how far she took it.
So now I have this mind bending memory of a vacation where my dad saw my girlfriend's naked, wet, big boobs. And where she made me a cuckold to the fact that it happened. It is crazy to think that my girlfriend wants my dad to bust a load on her boobs. It is what I think about almost every time I jack off onto her chest now.
Portland has a lot to offer. There are plenty of spouses and girlfriends who like the idea of playing into their man's cuckold fetish.
Happy Cucking!
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