How I Met Sheri Pt. 02: The Beginning Of Something Special

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This is a continuation of ‘How I met Sheri’. Its the adventures leading up to us getting engaged.

My name’s James O’Shay, but everyone call me Jay. I’m 25 years old six foot, and 190 lbs, with a typical hockey body, tree trunk for legs, big ass, and a lean upper body, I’ve played since I was 11 years old. I was good enough to play in Juniors, and to get drafted into the NHL, where I played in nine games. I never talk about that time in my life, because I’m embarrassed by it. I still play in a competitive adult league, so I’m in very good shape.

This story takes place about a week after my best friend Christie, set me up with Sheri. The moment I spoke or I should say stuttered to her, I knew she was the one. We’re now engaged, so I guess we were right. This is also, when we met the third in our throuple….but I’m getting ahead of myself.


“We still on for lunch?” Sheri asked me as she was getting ready for work.

“Yes ma’am, we’ll talk to Doug, then grab somethin’ to eat.” I said.

Doug’s our boss at the dog shelter we work at, Sheri’s one of the vets, while I’m just a lowly volunteer. Sheri wanted to tell him, that we’re in a relationship. Nowadays with all the sexual harassment, and Me Too movement going on, we wanted to be honest with him. If he has a problem with it, I’ll be happy to quit, and find another place to volunteer at. It wouldn’t be a big loss for them, I only volunteer 20 hours a week.

“And tonight you’ll meet my uncle.” She smiled.

Sheri must’ve read my face, that I was actually nervous about meeting him.

“Are you scared?” She asked, I can tell she was holding in her laugh.

“A little, I’m better with moms, and grandmas.” I said honestly.

Which is true, I feel more comfortable with women than I do with guys. My best friend’s a girl, and so are most of the people I hang out with. It was like that when I was young too. With guys there’s so much testosterone, and bragging about their sexual conquest. I’m just not that type of guy, who brags about my sex life or anything really.

“Of course you are, bat those baby blues, and you have them eatin’ outta your hand.” She said.

“You don’t do the same?” I laughed.

“Not really, I also use my tits, and ass.” She said.

“Maybe I’ll shake my ass at him.” I joked.

“You don’t wanna do that, he’ll try to fuck you!” Sheri laughed as I walked her to the door.

I had no doubt about that. From what I heard about her uncle, he’s a flamboyant gay guy, and a well known pervert. Not that it bothered me, I could care less who he or anyone else fucks.

“He’ll love you, just trust me.” She said as she gives me a kiss goodbye, and tells me she loves me.

I told her I loved her too. I watch as she pulls out of the driveway, and drives down the street. Its kind of cool on the late June morning, but we live in Buffalo, NY, so at least it’s not snowing.

I didn’t have to be at the shelter for a few hours, so I spent the time packing for our move next month. Before I met Sheri, I bought a new home for me, and Christie. We’re going from a small, two bedroom, one bath house, to a very large home with seven bedrooms, and eight bathrooms. I’m able to afford it, because of the $275 million trust fund my grandpa left me.

I’m actually more worried telling Sheri about my inheritance, than I am about meeting her uncle.

Since the reading of the will, when I was 18 years old, and learned about the large trust fund. I always wondered if people would like me for me, and not because of my bank account. My lawyers, and financial advisors warned me, that people will try to take advantage of me. The only person I’ve told is Christie.

Sheri’s the vet at the shelter, who donates her salary, and drives a Mercedes S-class (my deam car that I plan on buying soon), so she definitely has her own money. Neither of us have talked about our finances, which is fine with me. I want to be honest with her, I’ve already told her about the abuse I went through at the hands of my parents, and how my grandparents saved my life from them.

Before I knew it, it was time to get ready for work. I jumped in the shower, and put on Nike shorts, and a shirt. I don’t care what anybody thinks, about the way I dress. I’m going to be doing chores for the next four hours, so I’m going to be dressed comfortably.

I parked next to Sheri’s car, and took out my vape pen to get high. I’ll be walking dogs, picking up shit, cleaning the kennels, and throwing out garbage, I think I’ll be able to do that stoned. Besides, if I don’t smoke beforehand the social anxiety will kick in, and I don’t want that.

I cruised through the chores, and was really enjoying myself. I’m a big neat freak, so I don’t mind doing this type of work. Whenever I seen Sheri, we shared little smiles or we’d slyly touch each others hands when we passed in the hallways. I got butterflies in my stomach, every time time I saw her beautiful smile.

The people at the shelter were all really friendly. yalova escort Many of them would come over to talk to me asking if I had any questions, and inviting out for happy hour with them. I politely declined, but I didn’t tell them I had a hot date planned with their colleague.

I waited for Sheri in the same hallway that I first met her, and stuttered like a fool. She came walking through the door smiling, even in scrubs, and little make-up on, she’s still breathtaking.

“Hello.” She said.

“Hey there.”

“No stuttering? Looks like the magic’s gone.” She laughed.

“I don’t see that ever leaving.” I said as she grazed my hand with her finger tips.

“I’ve had to change my panties twice already, you’re makin’ me so wet.” She said quietly.


“I’ll show you at lunch, and I’m not the only one.” She said looking around making sure we’re alone.

“Do I wanna know?”

“Babe, there isn’t a girl in this building, who isn’t lusting after you.” Sheri smiled.

I feel my body tempature rising as the blood rushes to my face, which I’m sure is turning all kinds of pink.

“You’re enjoying this aren’t you?” I asked shaking my head at her.

“Which part? watchin’ you blush or knowing that even though every girl in here wants your big cock, I know it’ll be in my ass tonight.” She seductively said.

“Is he here?” I asked desperately wanting to change the subject.

“You crack me up, yeah he’s here, I told him I wanted to talk to him, but I didn’t know how to bring you up.” She said.

“So YOU were scared?” I tease her.

“Asshole.” She said quietly, as she knocked on the door.

“Come on in Sheri…..Oh Mr. O’Shay, please have a seat.” Doug said when he saw us together, and hurried around his desk to greet me.

I look over at Sheri, as she had an expression of ‘what the fuck was that about’ on her face. I ignored her for now, I’ll explain everything to her tonight.

“Hey Doug, nice seein’ you again, we’d like to talk to you.” I said shaking his hand.

Doug’s a good guy. I would guess in his mid-50’s, a little taller than Sheri so maybe five feet, six inches. He has that midlife round belly. He told me last time I saw him, that his wife has been nagging him to start excercising.

“Sure Mr. O’Shay….” He began to say.

“Please, it’s Jay.”

“Right of course, so what can I do for you?” He asked beginning to relax a little.

Sheri seemed a little timid, so I took the lead. I thought about telling him the truth about us: My roommate caught me jerking off to trans porn, and introduced me to Sheri, who has a huge penis. We hit it off, and we’ve been fucking like rabbits ever since. Oh, and this morning I woke her up, by giving her a blow job, and she shot her semen down my throat. Then I thought better of it, and gave him the PG-13 version.

“Well, we were set up last week by a mutual friend, and we really hit it off.” I told him.

I looked over at Sheri, and gave her a little smile. She seemed so nervous, it was both cute, and heartbreaking.

“I’m sorry Doug, I know I haven’t been here very long, I don’t wanna get a reputation for….” Sheri started talking rapidly.

“No, no, no it’s ok, we think the world of you.” Doug interrupted her.

I reach over to hold her hand, trying to calm her down. Sheri put her hand on mine, as she took a deep breath.

“Thank you for that, like Jay was sayin’ we hit it off, and we wanted to be transparent with you.” She said getting her confidence back again.

“If there’s any problems, it’s ok just tell us.” I tell him.

I wanted to tell Doug, that he can still keep the donation even if he does fire me. In fact I’d probably make another donation, just beacuse of his integrity.

“All I ask, is keep professional….” he told us, before he started laughing, and asked Sheri, “did he stutter again?”

The three of us started laughing, he must’ve remembered when I was here last week when I saw Sheri in the hallway. She said ‘hello’ to me, and when I tried to speak I stuttered ‘h-h-h-hi’. It wasn’t the smoothest pickup line, but it worked.

“Oh yeah a few times, that’s what made me fall in love with him.” She smiled.

“Love? I thought you just met.” He said in shock.

“We did, the moment I saw her, I knew she was the one.” I said truthfully.

“That’s exactly what I said when I met my wife. When you know, you know.” He said excitedly.

“Yes you do, I appreciate you hearin’ us out.” I said as I stood up, and shook his hand.

“No problem, why don’t you go introduce him to Bella.” Doug said Sheri.

“I think I will.” She said as we left the office.

“Who’s Bella?”

“My girlfriend….” She laughed, before adding, “Thanks for calming me down.”

“It was kinda funny, watchin’ you get all flustered.” I laughed.

“It went pretty well though, right?” She wondered.

“It did, I’ve talked to him a few times, he seems like a good guy.”

“He edirne escort really is, but I gotta know, why’d he call you ‘Mr. O’Shay’ twice?” She asked looking at me.

I can tell she wanted an answer, but this wasn’t the time nor the place for that conversation.

“I promise I’ll tell you tonight, but it’s nothing bad.” I said, as she led us to the kennels.

“You better…..” she said winking at me, as a pitbul jumped in excitement at seeing Sheri, “down!”

The dog listened, and sat next to Sheri looking up at her. Bella is a black, and white pitbul with grey eyes. Sheri told me the story: About a month ago Bella was brought into the shelter, badly beaten, and malnourished. Right away I related to Bella, she reminded me of myself.

“I’m not supposed to tell anyone yet, but I’m givin’ her a forever home.” She smiled as she petted Bella.

“That’s amazing!” I said, seeing how happy they both were.

We played with Bella for a few minutes, before we went to lunch. We talked about anything, and everything. With us there was no such thing as uncomfortable silences. Sheri did show me her panties she had on this morning that were in a ziplock bag, along with another pair.

“I made reservations at Mario’s, someone told me it’s your favorite restaurant.” She said.

That it was, Christie had to tell her. My grandparents used to take me, and Christie there every Friday night for dinner. The owner insisted on hosting dinner for everyone after my grandpa’s funeral. Even though I didn’t have any money at the time, I tried to give him some money, but he wouldn’t take a penny from me.

I haven’t been back to Mario’s since that night, for a couple reasons. The obvious was, it brought back to many memories of my grandparents. The other was I couldn’t afford it, until now.

“That place is expensive….” I protest.

“Don’t worry about it, like you said earlier ‘I’ll explain everything at dinner’ so we’ll have plenty to talk about.” she laughed.

“We sure do, I’ll see you at 6:00?” I asked as we walk to our cars.

“It’s a date, still love me?” She asked, giving me a little peck on the lips.

“I’ll have to think about it.” I joked.

“Smart ass.” She laughed as we said our goodbyes.

I went home to get high. I put on some Eminem, and began packing again. With a lot of people when they smoke weed they get tired, and take a nap. The sativa strain gives me energy, I’ll spend hours cleaning the house. I think that’s another reason Christie introduced me to pot, she hates to clean.

“You guys comin’ to the club tonight?” Christie asked me.

“After dinner, is her uncle as scary as I imagine?” I asked.

“WOW, I haven’t seen you scared in a long time.” she cracked up laughing at me.

Christie’s right about that, there’s only two people I’m truly scared of, and they’re related to me by blood. I have no idea why I’m so nervous about meeting Sheri’s uncle, I just want it to go well.

“I just don’t wanna fuck this up.” I admit to my only friend.

“You won’t, he’ll see how crazy you two are for each other.” She tried to reassure me.

“Hope you’re right.”

“Always am, you’ll really like him he’s, funny, perverted, and has nonfilter.” She said.

“So he’s like you?” I laughed.

“Pretty much, except he like likes cock. If there’s any doubt, just whip your dick out, and make him scream like you make Sheri scream.” She laughed.

“Let’s call that plan B.” I joked.

“Seriously though, what do you do to that girl? I’ve had some screamers, but nothin’ like her!” She said. Her favorite past time’s to see me getting embarrased.

“I’m takin’ a shower.” I laugh at her.

That’s what I love about Christie, she can bust balls better than most of the hockey players, I’ve played with.

After the shower, I went to look for something to wear to dinner. I knew sweats wouldn’t be allowed at Mario’s, so that left me with two choices; jeans or a suit. I put the jeans back, and grabbed the suit. The last time I wore a suit, was the last game of my playing career. As most people know, hockey players, even when they’re 10 years old, wear suits to all games. I’m not sure how the tradition started, but I respect it.

“Do I look presentable?” I asked Christie.

“You look hot as Hell, she got the reservations?” She asked.

“I told her, it’s too expensive.” I said.

“You gonna tell her about the trust fund?” She asked.

“Yeah, and if it’s ok with you, I’m gonna ask her to move in with us.” I said.

Christie got so excited she ran, and jumped in my arms, wrapping her legs around my waist. I wasn’t worried she’d object about Sheri moving in, she loves her as much as I do.

“Of course it is, I’m gonna be livin’ with my best friends.” She said.

We’ve always promised to live with each other, even if one of us got married. At first I thought it was because Christie was worried what would happen to me if I lived alone. Over the years though, I’ve erzurum escort come to realize how much we like being around each other.

“Don’t say anything.” I said when I heard Sheri’s car pull into the driveway.

“I’m hurt you’d even say that.” She laughed.

The doorbell rang, and when I opened the door, my jaw hit the floor. Sheri looked stunning. She had her wavy black hair down, falling halfway down her back, she had simple diamond studs in her ears. Unlike at work, she wore bright red lipstick, and whatever she did to her eyes, they were sparkling.

Sheri stepped inside, and took off her coat. She was wearing a black mini dress, that went a quarter of the way down her thighs. The dress was being held up by spaghetti straps, it was obvious she didn’t have a bra on, as her nipples tried to break through the fabric. My eyes traveled down further, and I see she’s wearing five inch heels, which made her shiny, smooth, tanned legs look even sexier. I felt my cock twitch in my pants.

Sheri looks very similar to actress Roselyn Sanchez. She’s five feet, four inches, weighing 125 lbs, with c-cup tits, and a perfect ass. It’s her delicate facial features, that make her so gorgeous.

“Fuck me!” I said looking her up, and down, she took my breath away.

“Right back at you, you’re hot as fuck, and you WILL be fuckin’ me tonight.” she said seductively.

“Why wait? I can stay, make some popcorn, and watch the show.” Christie laughed as she grabbed her car keys.

“Where you off to?” Sheri asked as they hugged each other.

“My parents for dinner, but I’ll meet you at the club.” Christie said, as Sheri came over to stand in front of me, staring into my eyes.

I lightly use my finger, and circle her nipple through the fabric, I watch as it gets harder. so I slowly repeat my actions, on her other nipple.

“Did Jay tell you how he woke me up?” She asked Christie, as she slowly backed me into the recliner.

“Not a word.” Christie said.

“I thought I was havin’ the most erotic dream, I couldn’t believe how real it felt, my….” Sheri said as my legs hit the recliner, forcing me to sit down, “alarm woke me up, and I saw my hard penis in your brother’s mouth. I never came so hard in my life.”

“You fuckin’ perv!” Christie joked.

“It looked cold, so I wanted to warm her up.” I said in my defense.

“Be gentle with him, he’s a little twisted in the head.” Christie told Sheri.

“And I fuckin’ love it, you can leave or stay, and watch me suck his dick.” Sheri said, getting down on her knees, and unzipped my pants.

Sheri fished out my already hard cock from my pants. She kissed the head, like she has done from the first night we were together. Right away she started sucking on the crown, causing me to moan out loud.

“I’d love to stay, but I’m late already, have fun you freaks!” Christie laughed, turning away from what was happening with her best friends.

“Won’t we be late?” I asked Sheri.

“Not at all, but I’ll stop if you want me too.” She said as her tongue circled the head of my dick.

“Don’t stop….” I said quickly, when I noticed the tiny diamond stud in her nostril, “you got your nose pierced today?”

“I’ve had since I was 17, you just noticed?” She asked while she stroked me.

“Yeah, I can’t stop lookin’ at your eyes.” I said honestly.

Sheri smiled, and stared into my eyes, as her mouth slowly takes me into her mouth. Inch by inch until I was deep in her throat, never breaking eye contact with me.

I’ve never been hypnotized by anyone’s eyes, like I am with Sheri’s when she looks at me. Besides having the most beautiful brown eyes, with little green specks in them, but I also see the love she has for me.

Keeping our eyes locked on each other, Sheri’s head bobbed up, and down on my cock. It felt so good, I knew I wasn’t going to last very long. Sheri took me out of her mouth, holding my dick in her hands, as she closed her eyes, and moaned softly.

Sheri stroked me with one hand, while the other lifted up her dress, exposing her tiny black panties.

“I’m gettin’ wet, I don’t wanna ruin my dress.” She explained.

She looked at me, and jerked me faster, before deep throating me. Sheri’s moaning as much as I am. Her breathing is becoming rapid, I see her hands, so I know she’s not playing with herself. Whatever she’s doing, it’s getting me close to cumming.

“Oh shit…..just like that…oh DAMN….OH FUCK BABY…FUCK I’M CUMMIN’!” I said as she jerked me in her mouth.

I don’t know how much I came, but it felt like it was never ending. Just as I finished, Sheri threw herself on the ground, as she lifted up her dress to her tits.

“HOLY SHIT….JAY…I’M….” She moaned as she slithered on her back, the black panties barely able to cover her throbbing penis, “I’M FUCKIN’ CUMMIN!”

We both watch as her penis flexed over, and over in her panties. It kept spasming as the white semen started to leak out. It was just sexy to witness her having an orgasm, without touching herself. I’m not really sure what just happened.

“HOLY FUCK….that was a first, there goes another pair!” Sheri laughed as she calmed down from her shaking, and carefully taking off her panties.

“What the Hell just happened…..?” I asked, when I seen something sticking out of her butt, “what’s this?”

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