(All in this story over 18yrs of age)
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Senior year in high school i dated this girl from a nearby school. Her name was Jenn. Jenn's most noticeable and attention drawing attribute was her big 34DD tits which sat on a smaller figured short body. We would talk on the phone after school and she would complain about this jerk guy that went to her school named Terry that would call her "Titties" and never by her name. Terry would frequently say "whats up Titties, you going to show them to me after school today?". She would just flip him off or roll her eyes at him and ignore him since he said this frequently. He even on occasions when I was picking her up after school or was with Jenn at after school events would arrogantly say "See ya later Titties" right in front of me, which used to infuriate me but Jenn would beg me to let it go as she explained "thats just how Terry is and he is harmless". She said after a few years of being called "Titties" she had kind of gotten used to it. One day after after school when I was picking Jenn up in the school parking lot I saw Jenn walking out with many others when Terry ran up to her and said something I could not make out from my distance away. Jenn smiled back at Terry and then gave him a full frontal hug which seemed to linger longer than I liked and Terry even wiggled just a little and picked Jenn up as his chest pressed against my girlfriends big tits. I had mixed emotions in which I was pissed this asshole was getting a hug from my girlfriend but also felt a little turned on. When she got to the vehicle I asked "what the hell was that hug with Terry about"? Jenn was surprised as she said "oh you saw that". Jenn said he came up and said his usual "Hey Titties, are you going to show them too me" in which she said "in your dreams Terry". His reply was can I at least get a hug to cheer me up in which she said fine. She told me not to be mad as she took my hand and put it on one of her big tits and said don't worry baby these are all yours so I didnt say much more about it but I did notice Terry got hugs pretty frequently after school. I didn't push the issue since I got to get naked hugs from Jenn so I considered myself the winner in the situation.
After senior year we had a short break up over me going to strip club with my buddies and she was pissed about it. She told me the weekend after the breakup she went to bon fire party one night behind some old classmates house. She was drinking a beer and from behind her she heard Terry's voice "whats up Titties! when you gonna show me those?". Jenn thought about how pissed she was at me looking at other girls tits at the strip club and thought about how pissed it would make me if she showed my favorite attribute of hers to another guy. She rolled her eyes for the one thousandth time and turned and asked him…"if i show you will please shut the hell up about it and quit asking me?". Terry quickly agreed and she said "ok but not out here where everyone else can see." So they went into the house and found and empty bedroom. She told him to sit on the bed while she stood a few feet away. She told him "just looking and nothing else ok!". She grabbed the bottom of her shirt and rolled it up to right under the cups of her bra…paused for a minute to see Terry grin with excitement. She gripped the bottom of her bra and snatched it up and let those big titties fall out into view which gave them a nice bounce! Terry immediately said "oh fuck yeah Titty Girl those are amazing! I knew you would show me eventually! " and started rubbing his boner though his basketball shorts. She said after a few seconds he blantantly whipped out his huge cock and started jerking it in front of her. I asked her later about the adjective "huge" she used and she pointed out to me later his cock was the biggest she had seen and seeing him jerk that big thick cock to her was turn on so she gave her tits a few little side to side shimmies and started rubbing on them to give him a good show. He told her "Come here, you have got to let me touch them one time". She thought about how she was pissed with me over our breakup and so she moved closer to him. She was nervous of where this was headed but still said ok. She stood with her tits right in front of his face, him still sitting on the bed, and as one one of his hands went to squeezing and rubbing her tits as the other kept pumping at his cock. I did not take long for his mouth to make his way to her nipples. She said this was seriously turning her on and she could feel her panties getting wet but she really wanted to get back together with me so she ignored her instinct to take it further. She said it didnt take too long of letting him play and suck on her tits while jerking before he started to cum. I asked her where he came and she told me a vague answer with hesitation "mostly on his shorts and the floor" (this leading me to wonder with my perverted mind, where else did he cum). She said after he cum she put up her tits and went back to the party in which a few people snarkily asked with a grin, "where have you two been off to together?" She ignored them and went back to drinking feeling a little dirty for letting this cocky jackass get off to her tits, knowing he would probably tell all of his buddies about it and she worried it might get back to me.
We got back together the next week and a few years later on she told me the story(only after I confessed a cuckold kind of interest in her teasing or maybe showing off some more cleavage to make other guys stare and she made me promise not to be upset in any way if she told me something from her past. Boy was I surprised and turned on when i found out what my sweet innocent Jenn had done) . Every time we saw Terry after that he called her by name and would say "hey Jenn" but he always gave me and her this cocky jackass grin (in which i never knew what it was all about for years until she told me this) i guess because he got to jerk to my girlfriend's big titties. Jenn and I had some great kinky talks and about this after her confession followed by hot sex for a few years. Jenn and I are no longer together but thinking about this TRUE story of my first cuckold experience still makes me hard to this day!
