How I Met Sheri Pt. 06: Going on Vacation

My name's James Marshall O'Shay, but everyone calls me Jay. I'm six feet, 185 lbs, with short brown hair, and a well trimmed beard.

I've played hockey since I was ten years old, and I have the typical player physique; lean upper body with an eight pack of abs, thick legs, and a big ass. I was good enough in Juniors to get drafted, and played in nine games in the NHL. Even though I was living a dream, I was absolutely miserable off the ice. I chose to walk away instead of getting some help for my depression.

I was totally lost when I was away from the rink. Here I was a lonely, odd, shy, and in many ways a broken teenager, who was spending all my time with guys much older than me, and who had families. There were a couple players closer to my age, but I didn't know how to socialize with them.

The reason I didn't go to a psychologist, was because I didn't want the stigma of having a mental illness. Nowadays I realize that was an immature way of thinking. Having depression or anxiety is nothing to be ashamed about. That's why I've been thinking about sharing what I've been through with a reporter, who's been wanting to do a story about why I walked away from the NHL.

My parents were abusive, and my grandparents took custody of me when I was ten years old. Little did I know that they were extremely rich, and left me over $275 million when they passed away. (You can read about that in my previous stories).

My girlfriend Sheri Santiago's also 25 years old, and is drop dead gorgeous, with delicate facial features. She has natural dark skin from her Puerto Rican heritage. Standing at five feet, five inches, 123 lbs, with a flawless body, c-cup tits, flat stomach, and a nice ass. But it's her sparkling brown eyes that melt my heart every time I look in them.

Sheri comes from a very wealthy family, her dad is one of the richest, and most powerful men in the country. She's originally from South Florida, but after a nasty break-up with an abusive ex boyfriend, she moved to Buffalo, NY with her uncle Alex.

We both work at a dog shelter. I'm basically the gopher there, but Sheri followed her dream, and became a veterinarian.

My other or I should say OUR girlfriend's Rachel Sanchez. She's a hot 21 year old we met at a restaurant about a week after we started dating. We originally intended to set her up with our friend Christie, but there was a chemistry between myself, Sheri, and Rachel that everyone noticed, and commented on.

At first we'd laugh them off, but as the weeks went by we realized they were right. We were in love with each other.

Like I was saying, Rachel's hot. Her great grandparents came from Cuba, and her mom's Italian (like mine) so she has olive colored skin. Rachel's only five feet, three inches tall, weighing 125 lbs with a pornstar body; big d-cup tits, and an outstanding ass. She can be identical twins with pornstar Autumn Falls. Rachel's going to school with plans on being a lawyer.

Last but not least is my best friend Christie. We were neighbors once I moved in with my grandparents. She has blue eyes like mine, and she's a tiny five feet, one inch, with b-cup breasts, and a little bubble butt. She works as a nurse in the ER.

The four of us live together. Along for the ride is Bella, a three year old Pit bull, who was brought into the shelter badly beaten, and malnourished. Sheri instantly fell in love with her, and adopted Bella when she was healthy.

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"You packed yet?" Marcus asked me from behind, while we watched Rachel's brother Josh playing hockey.

I've played against Marcus from when we were 12 years old. We were always considered the top two players in our age group. We were on rival Junior teams, and for the last three years we've been teammates in an adult league.

Our household, Marcus, his fiancé Eve, and our neighbors Dave, and Melissa decided to go on vacation when Rachel was on her winter break from school. Sheri's dad Ricardo was going to Europe with his new girlfriend, so he offered us his home to stay in.

"With his OCD? He's been packed for a week." Rachel laughed next to me.

"I know the name of a good doctor." Marcus joked. He was referring to Eve who's a trained psychiatrist.

"I'm not paying a doctor to tell me what I already know." I said. There's not a doubt in my mind that I could use some counseling, but I'm still afraid of shrinks.

"It'd be nice to have it diagnosed." He laughed.

"Fuckin' prick." I joked. I know he's only busting my balls.

Up until I started dating Sheri, I only had Christie as a friend. Even though I've known Marcus for years, we never hung out away from the rink. Now I'm going on vacation with many friends.

"Where's mama?" Sheri asked Rachel, who was sitting in the middle of us.

"Where you think?" Rachel laughed. She moved me out of the way, so Sheri can see Marie sitting next to me.

Marie Sanchez is a 50 year old version of Rachel. The only difference is Marie is eight inches taller than her daughter.

"You know he's taken, and you're married, right?" Sheri joked.

The girls are always saying that Marie's flirting with me, but I think she's being friendly. It's not like anything would ever happen, I'm madly in love with her daughter, and Sheri. Yes, we're in a three way relationship, but we're committed to each other, and will never ever swap partners or anything like that.

"We've been talkin' 'bout Josh, are they always this jealous?" Marie asked me.

"A girl can't even talk to me, without them flipping out." I lied.

"You're so full of shit." Sheri said to me.

One of the things I appreciate about the girls is, they don't get jealous when girls talk to me. Just like I don't when guys approach them, we're very secure in our relationship.

"He's gotten better." Rachel told me, while we watch Josh play.

After I seen Josh play for the first time, I've been bringing him out to practice with us. He's a big kid, and we've been coaching him on how to be more physical on the ice.

I'm more like a throwback kind of player, who should've played in the late 90'-2000's. I have high enough skill for today's game, but I'm also extremely physical on the ice, and won't think twice before I put my shoulder under your chin. I personally think today's style is getting to soft.

While we waited for Josh to come out of the locker room, we chatted about the game. He played well, but his team lost. Marie told us how Josh can't stop talking about the practices we've been putting him through.

"You're gettin' better bro." Rachel said to Josh.

"Thanks, what'd you guys think?" Josh asked me, and Marcus.

"Certainly improving, but we still have a lot of work to do." Marcus said.

I think we both respect that Josh wants to get better. There's a lot of kids his age who think they have it all figured out, Josh is mature enough to know that's not the case.

We were honest with Josh when we broke down what we saw. I told Josh when we get back from vacation, he's more than welcome to come over to work-out with me if he wants.

"You girls take care of my boy down there." Marie said to the girls, as we gave her a kiss goodbye.

"OUR man will be fine, and we'll be goin' down on him all week!" Rachel said to her mom.

"A slut just like her mother." Marie laughed.

I was shocked when I first heard how Rachel talked so openly about sex with her parents. The only thing she hasn't told them about was our adventures in public, but I'm sure she will eventually.

"You ready for your exam?" I asked, while I drove us home.

"It should be pretty easy, I have a few errands to run afterwards." Rachel said to me.

I looked in the rearview mirror at Sheri, who had a little smile on her face. A few months ago Rachel, and I went an adult bookstore to get a strap-on for Sheri. When we there, I noticed how well she navigated the aisles, and how she knew where everything was. She admitted to me that she's been going there since her eighteenth birthday.

Rachel told me that she'd take a DVD into the viewing booth to masturbate. It's a part of her ritual after she takes a big test or an exam. She also said she gets real turned on when cocks start to appear through the glory holes.

That's what Rachel kept thinking about as her eighteenth birthday approached. She wanted to live out her fantasy of strangers jerking off to her, while she plays with her pussy in the porn shop.

Rachel said she's never sucked off any of the guys, and I believe her. There's not a doubt in my mind that she would tell us if she did, the girl really has no shame. Well we'll see how she reacts tomorrow, when two dicks that she's very familiar with comes through the wall.

"I can't wait to sleep in tomorrow." Sheri said convincingly.

I have to laugh at Sheri. She's able to keep a poker face no matter what the situation is, and I'm the complete opposite. We hosted a game night a few weeks ago where we played strip poker, and I was the first one naked. Sheri ended up winning, but she was also upset that her clothes were still on. If it was up to Sheri, she'd walk around in public with no clothes on.

When we got home it was after 11:00 so the girls were going to go to bed, I followed them up to the bedroom. I was going to get a couple joints to take to the theater room with me, so I can get high, and watch Netflix.

"Can you set an alarm to wake me up?" Sheri asked me quietly before I left the bedroom.

I understand what Sheri's asking, and why she didn't want Rachel to hear. I nod my head at her, and she gets a big smile on her face, before jumping into my arms to give me a kiss.

I know what's waiting for me when I close my eyes, so I'm never in a hurry to go to sleep. The weed has helped so much, but I doubt anything will stop the nightmares completely.

I finally crawled into bed around 2:30 am, and hoped for a peaceful nights sleep. No such luck though. I wake in a cold sweat before the sun came up. I laid down some towels so Sheri, who sleeps in the middle, doesn't roll onto the wet sheets.

I took a quick shower, before taking Bella for her morning walk. I inhale on the joint I lit, and hope a little wake, and bake will get the latest nightmare out of my head.

Maybe I do need to talk to someone, I think to myself. I can't go through life getting three hours of sleep a night. People can go insane without enough sleep.

I go into the kitchen, and I see Rachel coming toward me with a Pepsi, and a big smile. Even so early in the morning she's happy to see me. She was wearing one of my old t-shits, and I can see her dark nipples through the fabric.

"Mornin' babe." Rachel said, as she stood on her tiptoes to give me a kiss.

"How'd you sleep?" I asked when we sat down at the kitchen island.

"Better than you. You tossed, and turned all night, was it a bad one?" Rachel asked, as she held my hand.

Rachel, and Sheri knows about my nightmares, and try to help me as best as they can. They'll try to wake me up or hold me until I fall back to sleep. Yeah, I know I sound like a pussy, but walk a mile in my shoes, and then you can give me a call.

"Just anxious 'bout flyin'." I joked.

"And I'm the motherfuckin' Queen of England!" She laughed.

"You'll have to settle for bein' one of my Queens instead." I said.

"I'm here if you need to talk." She said seriously.

" I know, thank you." I said, as I lean in to kiss her lips.

I feel like an asshole. All Rachel wants to do is help me out, but I'm not ready yet. By now the girls realize, that's it's not easy for me to share my nightmares. I need to do it on my own timetable.

"Wanna eat before or after?" Rachel asked.

This has been a part of our morning routine since we started living together. We're both early risers so we'd go for a run, workout, and eat breakfast before anyone else wakes up.

In the evenings Sheri, and Christie (if she's not working) join us in the gym, where we'll do yoga. I recently started doing yoga. I might be in good shape, but these girls, and especially Rachel have the bodies to prove it. I see them naked all the time, but I can't wait to see them in bikinis when we hit the beach.

"Go change." I said, as I stood up.

"No need, I'm just gonna do light cardio." Rachel said, as we go down the stairs.

We walk past the greenhouse that I built in our basement. For the past few months I've been growing my own weed, and have created a few hybrid pot plants. Me, and the husband of a woman we work with at the shelter, have also been making weed infused butter, chocolate, and other edibles. We're planning to get into the legal Canibus business.

"This is one thing that keeps me sane." I said, as I point to the greenhouse.

"We know, why you think we encouraged it so much." She smiled to me.

When I told the girls about my idea, I thought they would laugh at me. Instead they did research on YouTube of how to make a greenhouse. They know about the marijuana plants, and are very supportive of the plans for the business.

I took off my sweatshirt when we enter the gym, leaving me only in my sweats. I was stretching while Rachel got on the stairclimber.

"What're you lookin' at?" I asked Rachel, when I busted her staring at me.

"I fuckin' love your body." She told me.

"Whatever." I laughed, as I wave a hand at her.

After I do a set of burpees, push-ups, and sit-ups. I go over to the bar to sit on the stool, and drink a Powerade. Rachel hoped on top of the bar in front on me, and crossed her legs.

"You look dehydrated." She said.

I seen myself in the mirror, I didn't look pale, and my eyes weren't sunken in. I even pinched myself to see if my skin still had the same elasticity. I was recently extremely sick, so I've been on the lookout for any signs of getting sick again.

"Good thing you're studyin' law, and not medicine." I tell her.

"I don't think you're gettin' enough liquids." She said seriously.

Now I know she's lost her mind. I may smoke a lot of weed, but I've never had a drop of alcohol. It's not that I don't drink for religious reasons, it's because I come from a long line of alcoholics, and I wanted to end that cycle.

"I drink more water, and sports drinks than the three of you combined." I laughed.

"True, but it doesn't hurt to have more." She said.

"Do you even know what you're talkin' 'bout?" I asked.

"I'm tryin' to tell you; I know of a 'special' liquid, that works better than any sports drink." Rachel told me.

"And what would that be?" I asked, while trying not to laugh in her face.

Rachel smiled at me, like she was pleased I asked the question.

"It's my pussy juice, it's been a few days since you've had some." Rachel said, as she opened her legs in front of me.

I seen she wasn't wearing any panties as I saw her neatly trimmed bush. I look back up at her face, and seen her bite her bottom lip.

"You're not wearin' panties, it's almost like you planned this." I said, as I touch her soft inner thighs.

"I woke up a lil' horny this mornin', and I had a choice; either play with myself or get you to take care of me." She said.

On the inside I'm jumping for joy that Rachel picked option B, but I want to drag this out for a little bit. So for now, I resist all temptation to bury my face between her legs.

"As a nutritionist, you'd recommend this for my hydration?" I asked. I touched her damp vagina, and showed her my wet fingers.

"Without a doubt, and I taste as sweet as candy." She smiled.

"Now that's a fact!" I said, as I suck on my finger.

I use my hands to spread her legs wider, while I bring my face closer. Instead of licking her, I nibble on the delicate skin of her inner thighs, kiss her bush, and lick the outer lips. I can tell it's driving her crazy, so I kept repeating the process over, and over.

"Please babe." Rachel pleaded, as she squirmed on the bar.

I smile to myself, and take a deep breath so I can smell her arousal. It's an intoxicating smell, that gets my cock hard in my sweats.

"What'd you want?" I asked.

Rachel didn't say anything, she just grabbed the back of my head, and shoved my face into her. I took a long lick from her perineum to the top of her pussy.

"Ahhhh!" Rachel sighed, when I slid two fingers in her.

Rachel took off her shirt, and laid naked on the bar, while I continued to orally please her.

"FUUUUCCKK, you're gonna make me cum so fast!" Rachel said, as she played with her nipples.

If Rachel woke up horny, and I scratch her itch, will she still go to the bookstore? I asked myself. Sheri will be disappointed if Rachel comes home right after her exam. Then again, Rachel still might go through with her ritual, I mean that's why it's called a 'ritual'. I guess I'll take my chances, because right now I want to get her off.

"Yes, yes...YES...I'm so fuckin' close." Rachel panted, as she ground her pussy against my mouth.

I increased my speed with my fingers, and flick her clit with my tongue. Rachel's internal wall constricted around my fingers. I felt the beginning of her orgasm.

Rachel wasn't saying anything, but her body was. She grabbed the back of my head to make sure I didn't pull away, as her body went stiff. She didn't breath for a few seconds, while her body shivered. I tasted her sweet cum on my tongue.

When Rachel came down from her orgasmic high, she slid off the bar, and onto my lap.

"Fuck, I needed that." Rachel smiled, as she kissed me deeply.

My hands roamed her glorious ass, as my cock swelled in my pants. I know she can feel it, because she keeps sliding up, and down on me.

"Oh my princess, we're not done yet." I said, as I pick her up, and carry her to the couch in the gym.

"I was hopin' you'd say that." Rachel said in delight when I laid her down. She reached out to rub my sweaty abs, but I took a step back.

"Touch yourself." I said. Rachel didn't need to be told twice, she was more than happy to touch her wet pussy.

"Show me your cock." Rachel demanded.

I took off my sweats, and left the boxer briefs on. Rachel can see my nine inch thick cock is rock hard for her. I watch as she uses her fingers to spread her pussy lips apart, and rubs her clit.

"You know you want this, so stop playin' games, and come fuck me." She smiled.

I slid my boxer briefs off as as Rachel put one leg over the back of the couch to spread her legs wider. I got between her legs, and smacked my hard cock against her pussy before I slide into her.

"Aaahhh yes, fuck me slowly." She said.

"Yes ma'am." I told her. I pull half way out, before going back in.

I was in no hurry to cum, so we continued going slow for awhile. My dick was just enjoying the soft, and slippery hole. We stared in each other's eyes, when a big smile came across her face. She tried to rub her clit, but I pinned her arms above her head. I wasn't going to let her have another orgasm so quick.

"Oh hell no, not this mornin'. Lay down!" Rachel said. She put her leg in between our bodies, and pushed me away.

"You're awfully bossy this mornin'." I laughed, as I laid down on the rubber matted floor, and watched her straddle me.

"'Cause I lied to you, I didn't wake up a lil' horny, I'm horny as fuck!" She admitted.

As soon as Rachel's ass hit my thighs, she started to grind on me. She put her hands in either side of my head, and rode me faster. I held onto her hips as she bounced up, and down.

"Holy shit!" I said, the sensation I was feeling was incredible.

I smacked her ass a couple times, before I spread her ass cheeks apart. This just encouraged her the buck on my dick harder.

"You like my college pussy?" She asked rhetorically.

"You know I do."

Rachel stopped bouncing so she can give me a passionate kiss, our tongues wrestled with each other. She sat back up to grind some more, while she massaged my sweaty chest, and abs.