Skinny Dipping gone Wrong
Eric and Chrissy
Story will be a continuation of how my wife and I got involved in the cuckold lifestyle. Story is 99% true or the best of my memory.
(If you don't like cuckolding, and sph you won't like this story)
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I (Eric) started working at a local grocery store when I was young. I had limited experience with girls but was an overall decent looking guy that played sports and worked out. I started as a bagger and in about six months had the ability to move to a stocking position. Our store had a specific customer service desk that handled rain checks, cashed checks, etc. That is where I noticed Chrissy.
Chrissy was your girl next door, imagine Hillary Duff. She had an amazing round ass that I couldn't stop looking at, whenever I had an opportunity. We started talking to each other on breaks and normal work small talk conversations. I asked her out a few times and she turned me down citing age difference.
Chrissy and I,shared mutual work friends and occasionally got together at an older co-workers house on Friday or Saturday evenings to hang out. I was obviously attracted to Chrissy and most everyone knew. A co-worker named Josh, who was a few years older than Chrissy, also was attracted to her. He would hit on her and I think she reciprocated his advances more than mine, and openly. I was extremely jealous and thought about giving up. A few co-workers (female) would smirk when they saw me watching her interact with Josh.
I think she gave me several reasons to give up and walk away, but I kept flirting and asking her out. Perseverance paid off and we started seeing each other more often. She invited me to her house to meet her parents and vice versa.
We soon became a couple, and were seeing each other quite often (work and outside of work). I mostly went to her house when we hung out, her family had a nice pool with a wrap-around deck and were supportive of our relationship.
Chrissy was a flirt by nature, and I could tell she liked the male attention. The first time we fondled or sexually touched each other was in my bedroom. We were laying on my bed kissing and touching, she reached down to grab and feel my dick. I was wearing basketball shorts and was hard as a rock. She stroked through my shorts, and started to put her hand inside. When she reached my waist line and her fingers were below, I could tell she was puzzled that she still couldn't feel my dick. She had to reach farther down to grab it and start stroking it, but the look on her face and breath she made, exuded disappointment. I knew I was small, compared to guys in the locker room. The other guys were bigger than me, as I'm barely an inch soft and 4.5" hard.
Chrissy went with the flow, as I think our time spent connecting and talking, we were able to develop feelings that allowed her to overlook the "small" issue.
We continued dating and we became fixtures with each other's families. I thought they all liked me, as I spent a lot of time at her house.
I had been accepted to a University that was approximately 4 hours from our hometown and was excited to go, but also disappointed that Chrissy and I would be separated. We had a few months before I would leave.
Her parents went on a vacation for a couple weeks and it was just Chrissy and her younger brother at home. Her younger brother was a computer and gaming guy that barely left his room, so one night we decided to go skinny dipping in the pool. Her parents asked a family friend (Brian) to stop by and check on things.
Brian came by that night and walked on the deck while we were in the pool (naked), our suits were on the deck. He startled us but he soon realized we were naked as he stood on the deck, the lighting didn't hide much. He started off serious but asked "how's the water?" and said he was actually hoping to get a swim in as well, but would leave us to our fun.
I needed to go to the bathroom and started to get out as he was leaving. I had just reached the top of the ladder, when Brian came back out to say something and we made eye contact with both my hands on the side of the ladder and he saw everything (acorn on a sac). He laughed and said "the water must be freezing, you better go get warm before your body swallows it!"
Brian was in his 30's and quite a bit bigger than me and I didn't say much. Chrissy smirked and asked "what do you want?", he asked "could I swing by tomorrow for a swim?" Chrissy surprisingly said "just swim tonight!" He said "I'm going to the truck to grab my trunks", but Chrissy chuckled and said "No need now, since you've seen everything!"
Brian didn't waste time removing his clothes, but when he removed his boxers (all eyes on him), his soft cock was huge. Chrissy's mouth hung open and she couldn't help but say "Jesus", in which he actually kind of flopped it up with his hand and said "what?"
He then jumped in the water and said "the water's nice, you don't have an excuse man!"
While staring at me and then back to him, Chrissy chuckled and said " No wonder you've had so many girlfriends over the years!" He laughed and quickly grabbed her to dunk her. They started rough housing in the pool where he was behind her and had his arms wrapped around hers where her ass was pressed up against his cock. They looked up at me (on deck) after I had returned from the bathroom, but had been watching them and I was hard. He said "it looks like you like watching!"
Chrissy laughed and said "wow, us wrestling around naked turns you on?" I responded, "I'm not sure why I'm hard?"
Brian squeezed Chrissy hard from behind and Chrissy squealed. She said "The air makes him hard, while my ASS against your COCK seems to make you HARD!"
Brian responded, "As it would any REAL MAN!"
Chrissy squealed "Damn, you're hard as a Rock and HUGE!"
Brian asked me "You going to get back in or stand there watching us with your little hard on?"
Chrissy said "I think he's intimidated, and doesn't know what to do! Are you going to watch?"
All I could do was nod my head ...
Then he kissed her and she didn't resist, she was stroking his cock under the water. I didn't say anything but just watched and I was hard. They kissed while she stroked him and he was fingering her. Brian turned Chrissy around to face me and he entered her from behind. He started slow as she was moaning "Oh GOD, you're so big, GOD, I don't know if I can take you, mmhhh GOD!"
She asked "Oh Fuck, are you all the way in?!?"
Brian chuckled and responded "Nnoo I, I'm just passed the head."
I thought she was going to scream,Chrissy's face in a mixture of pain and pleasure as he pushed a little deeper.
Chrissy screamed "Oh my Goddd!, You're so big, you feel so FUCKING good!"
Brian asked, "You like my BIG COCK?, am I better than him? I'm only halfway in and you're cumming all over my cock"
Chrissy gasps, "I'M CUMMING, GOD, I'M CUMMING!"
Brian, pulled her back to him pushing deeper and she turned her head around to kiss him, while he began to pull out further and push in deeper.
She turned around to look at me, I was jerking my cock and about to cum.
Chrissy asked me, "you like watching him fuck me baby? You like seeing me take his massive cock?"
I shook my head "yes"
I then realized that Brian was fucking her without a condom. We had only always used a condom even though she was also on BC.
I spoke up and asked "What about a condom?"
Chrissy answered " I don't care, I don't care, I just want his cock, I want him to cum in me, I want to feel it!"
Brian said, "YEAH, I'M GOING TO FILL YOU UP WITH ALL MY CUM! You never answered me ... YOU LIKE MY BIG COCK, DO I FUCK BETTER THAN HIM?"
Chrissy responded between moans and heavy breathing, "GOD, YES I LOVE YOUR COCK, GOD YOU FUCK ME SO MUCH BETTER THAN HIM!"
I couldn't contain it, I started spurting cum on the deck as they both watched.
They slightly laughed, in addition to Chrissy's moaning of pleasure.
Brian looked at me and said, "You've got a little baby dick and you cum little baby droplets by watching! How did you end up with this hot ass?"
Chrissy was moaning and said, "OH GOD BRIAN, KEEP FUCKING ME, DON'T STOP! I WANT YOUR COCK EVERYDAY, I CAN'T BELIEVE YOU'RE FUCKING ME!"
Brian asked "what about him?", while looking at me with a smirk.
Chrissy, with her eyes closed, responded, "I'M NOT SURE, RIGHT NOW I WANT YOU AND WANT THIS ALL THE TIME!"