The first proper emasculation I’ve ever felt that lead me to where I am today is when my gf, who I’ll call Ashley, wanted to compare my dick size to some of her close guy friend’s while we were at a beach over summer. I was driving, and Ashley was in the back sleeping on the ride. She was in a bikini top with her 32DD boobs spilling out of it, while wearing shorts with her legs across another guy’s lap so she could sleep on the ride. I felt a little jealous about her being on him as he rested his hands on her long legs, as well as noticing them constantly staring at her cleavage, but ignored it as I drove.
Ashley took her shorts off when we arrived to show her thong bikini she had under, her friends and I all know she only wears them which they love and I get insecure about as already one of them, I’ll call him Ryan, goes “I see you been hitting the gym”, making Ashley giggle and say “my butt isn’t as big as I’d like but it’s good for now”.
When we got out to the water since the beach was practically empty we went with pool noodles, preparing to play “shoulder wars” or “chicken fight” as the waves made it more exciting than when we were all kids in a pool. My gf is 5’9 and in shape from working out all the time while I’m 5’6 and very skinny, which means I can’t even balance her on my shoulders. Ryan, who’s 6’1 and is also a gym lover, picks her up and puts her on his without issue. They stay partnered the rest of the time we played, her legs locked around him and his hands all over her thighs, until a big wave knocked them over.
They were under water for at least a minute for some reason, which lead to us all noticing the wave had taken half her bikini off, leaving her boobs exposed if she didn’t immediately cover her nipples with her hand. Ashley asked the other guys to search for her top, then came over. She whispered to me “when we fell, I felt his cock when trying to stand up, i couldn’t let go of it at first” she then went “while playing he was rubbing on my thighs and accidentally grabbed butt a lot he must be really down bad right” I felt myself get turned on at that, then Ashley continued saying “you know I love teasing boys but can you do me a favor and let me try something”, then slid her hand down my shorts without a word, grabbed my dick, then immediately laughed a little as she started giving me the most salt-water filled handjob under my shorts. I asked why she laughed and Ashley said bluntly, “hes way over double yours, I really want to test it just once please I miss guys that big” I grew to my full around 2 inches at that, grabbing her ass while she jacked me off with 3 fingers. When they started to head back we pretended nothing happened then headed back for a towel when they didn’t have her top.
I gave Ashley a towel to cover her chest and they all began to drink the alcohol we had brought, I was driving so I couldn’t but the others got pretty drunk fast due to being lightweights. Ashley calls out, “so I saw all of you horny ass boys had a bulge in your shorts, so who’s the biggest”. Immediately they all began debating and making numbers up, so she got off my lap and says “lll suck off whoever is biggest right here in the car if you prove it” She then dropped the towel, showing her nipples off to everyone to show she’s serious. 4 of the other guys ended up going along with it, all 4 being far bigger than me to the point that Ashley started to laugh again when she pulled mine out “just to make sure you’re smaller.” It was Ryan like she expected, so I watched as her and Ryan went into my car as he grabbed her ass, then saw her head go down below the window and start bobbing up and down.
The other guys have been drinking even more by now, not paying full attention so I just stare at the beach. I went to go check on her after about 10 minutes, arriving to see her gagging on him. He saw me watching and gave a thumbs up, his other hand on her head. I just watched as swallowed, then she looked at me and smiled before kissing me. The ride home was definitely quieter than before, this time Ashley and Ryan were sitting together though and he had his hand on her thigh. I felt hard the whole time, this was so memorable to me as it was the first time I had a sign I was into being a cuck.
FUCK MY WIFE!
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