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

I reached out to touch the slender pink rubber, that was flexible. It was really odd looking, like Sheri grew a pink tail.

"It's a lovense, it's like a butt plug pressed again my g-spot, and it vibrates at random times." She giggled.

"Your're such a....." I laugh but stop talking, because I hate saying the word, and Sheri knows it.

"Say it, you know how hot it makes me." She told me.

"You're such a lil' slut." I said, bringing a big smile to her face.

"I'm your little slut, and proud of it!" she said as she gave me a kiss.

"We better get goin', I'm sure Christie wouldn't mind, if you borrow a pair of panties." I told her.

"That's one option." she said giving me a little wink.

Sheri stood up, and went into the bathroom, and I checked to see if any semen was on my pants. Thankfully the talented vet made sure she swallowed every drop.

Sheri came out of the bathroom, tossing me her keys, and I hand her my vape pen. That meant two things: She's getting high, which makes her horny, and I get to take my dream car for another test drive.

"That was supposed to be a thank you for this mornin', but since I had an orgasm I still owe you one." She laughed.

I help put the light weight coat over her shoulders, and spin her around so I can look at her.

"I ever tell you how amazin' you are?" I asked.

"You may have mentioned a few times." She laughed, before we headed for the car.

"So how often do use that butt plug thing?" I asked out of curiosity.

"A couple times. A few months ago, I woke up so horny, and since my uncle was outta town, I decided to wear it all day." She admitted.

"Slut." I laughed.

"It didn't go off for the longest time, but when it did, it was for 45 minutes straight, I was a mess all day." She laughed.

"How many times did you cum?"

"It was in my ass for ten hours, I had eight orgasms, after the fifth I passed out, until the vibrations woke me up, as soon as I touched myself I came again." She said.

"Damn, I would've loved to see that." I said as I imagine how hot that must've been. I also made a note to myself, that I'm going to make her shatter that record in the near future.

"You may tonight, it's still in my ass!" She laughed.

"Don't cum at Mario's." I said.

"That was the first time that it's ever happened hands free, whatever you did to me on that first night, you woke somethin' in me." Sheri smiled.

The night we had sex for the first time, Sheri told me she couldn't have an orgasm, without one of us stimulating her penis. I took that as a personal challenge to prove her wrong. I wouldn't let her stroke her penis, no matter how much she begged. It took awhile but I rose to the challenge, and made her cum just by fucking her ass. Afterwards when I was holding her, Sheri told me that it was the first time, she truly felt like a girl when she was having sex.

Sheri sat there looking out the window. I can tell she was thinking, because she kept smiling to herself.

"Wanna play a game tonight?" She asked me, as I pulled up to the curb in front of Mario's.

I see the lust in her eyes. I don't know what she's up to, but I know I'll love it.

"Of course." I said as I got out of the car, at the valet stand.

"Since you love watchin' me cum so much, tonight you're in charge of my body, you tell me when or IF I can cum." Sheri said loud enough for the valet to hear.

I hand him the keys, but he keeps looking at Sheri, like he couldn't believe what he just heard. So I thought I'd help him understand what she was saying.

"So if I tell to pull up your dress, and jerk off right now, you'd do it?" I asked as I walk over to her.

"Hell yes, I'm your lil' slut!" she said as she slowly lifted the front of her dress, stopping just short of her penis.

I look at the valet, and he's in a trance. I stop Sheri just in time, so she won't get arrested for indecent exposure. She took me by the arm, as we walk to rhe doors.

"You would've done it, wouldn't you?"

"In a heartbeat. Like I said earlier, you've awoken somethin' in me." Sheri smiled at me.

I know exactly what she means. I'm doing things I never would've thought of doing a week ago. Sheri's brought out a level of passion in me, that I didn't know existed.

"Welcome to Mario's, name please?" The maitre D' said in an Italian accent.

"Santiago." Sheri said.

"Right this way." He said as we follow him.

When we were walking to our table, I can't help but to think of my grandparents, and wish they could've met Sheri. They wouldn't have any issues with her being a trans, they loved Christie even after she came out of the closet. For being from the Boomer generation they were pretty liberal, after all they were hippies in the 60's.

"I'm sure she's hooker, he's gonna blow MY money in a year." I heard a familiar voice say, snapping me out of reminiscing about my grandparents.

"It's ok babe, he's probably drunk." Sheri said quietly, as she held my hand tight.

I can guarntee he is. I would love to ignore this asshole, but unlike Sheri I recognize the voice, it's been haunting me since the day I was born. Two weeks ago I would've fled the restaurant, but I'm done running. I have a new inner strength, to go against the ultimate bullies.

"Dad...." I said, looking him in the eyes, before seeing my mother sitting there, looking like her usual bitchy self, "mom."

I seen the couple with them, it was Will, and his wife Barb. He used to work for my grandfather, who said he was great at his job, but he called Will 'the worlds biggest ass kisser'. I really like Will, he was always nice to me when I was a little kid, and called to congratulate me after I played in my first NHL game.

My lawyer Henry told me a few months ago, that they were going into business together. Henry gave me regular updates on my parents, I wanted to know what they were up to.

"Hi, I'm Sheri, it's..." The always sweet Sheri said, before the bitch cut her off.

"The whore has a name, must've paid for the night." My mother said loud enough for everyone to hear.

Will, and his wife didn't crack a smile, my father thought it was hilarious. To her credit, and strength, Sheri didn't back down.

"You will regret that comment." She ominously to my mom.

I was livid, all I wanted to do was strangle both of them.

"I'm not some little boy anymore, that you can scare." I said to my parents.

"How're you Jay?" A very nervous Will asked.

"I'm good, this is my girlfriend...." I said.

"A whore by any name, is still a whore!" My belligerent father interrupted.

Other tables began to take notice, and were looking our way. I didn't really care, I have nothing to hide, unlike my parents.

"Wow, you wanna keep goin'? cause I can FUCKIN' DESTROY YOU!" I said to my dad.

Sheri held my arm tight, trying to pull me back. She must've been afraid of what I might do to them.

"You conned you're grandfather, with your filthy lies." My mom said angrily.

"Are you serious? Bitch I have the scars, do you wanna see what mommy dearest did to me when I was five, and spilled a glass of milk?" I asked their dinner guests.

Even though I was full of rage, I still had full control of my emotions. It felt like the weight of the world, was being lifted off my shoulders.

"You're full of...." My father tried to say, but I was done with their bullshit.

"Listen you kiddie fucker, do you think grandpa wouldn't leave me ALL the evidence?" I asked cutting him off. As for the 'kiddie fucker' comment, I think that's self explanatory.

For the first time in my life, I seen that my father was scared. it was time to dig the knife in.

"That's right, he always said it was up to ME, when I wanted to burn your life down, so remember that lack of compassion you showed me? Well I can return that life lesson ten fold, 'cause I'm young, rich, and most importantly....." I said, "I DON'T GIVE A FUCK!"

I don't like saying I was 'rich' out loud, but at this point I'm just pissed off, and letting everything fly out of my mouth. I've had 25 years of pent up rage at them, and I was going to say whatever I wanted.

"Excuse me sir, in case his threat didn't work, I have one too." Sheri said to him.

Sheri looked at me, and gave me a little smile, like she was about to blow their minds.

"Judging by your level of arrogance, you have a little money, do you happen to know the name Ricardo Santiago?" She asked.

I never heard the name before, but seeing the reactions around the table, I was in the minority. My father's jaw opened slightly, and Will looked like he was about to pass out.

"That priceless look on your face says you do, I just call him daddy!"

She said showing them a picture on her phone.

"I...." My father tried to say, but Sheri wasn't done with them.

"What'd you think he'd do, if he heard what you called his little girl?" Sheri asked looking straight at him.

Sheri either held my hand or arm the entire time. She not only gave me the confidence to stand up to my tormentors, but she letting them know that we're a team. If you mess with either of us, you'll have to deal with both of us.

"You're lyin', they didn't have a girl, only a...." My mom said.

"Ohhhh, I dare you, to finish that sentence." Sheri said in a threatening tone.

My mother glared at Sheri, before looking at me in disgust, I can tell she felt defeated. I don't know who Sheri's dad is, but he raised one tough girl.

"Will if you ever wanna know the truth about your business partner, give Henry a call, I'll have him tell you the truth." I said to him, who was on the verge of a panic attack.

Will didn't know what to say. I'm sure he was confused, at what just happened. My father didn't say a word either, he threw his linen napkin on the table, and stormed off in a huff.

"Have a nice dinner mom, it might be a while 'til you can show your face in public again." I said.

I really wanted to call the local news, to give them all the nasty details about my parents. They never gave two shits about me, so why would I give a fuck about them? Like I've said, I'm not a forgiving person.

Sheri, and I follow the shell shocked Maitre D' to our table. He pulled out Sheri's chair, and got the Hell away from us. I'm sure I came across like a lunatic.

"Get ready for some serious ass kissing." I laugh quietly when I see Will approaching us.

"Jay, your father's drunk, he didn't mean....." He said in a panic.

"That's bullshit Will, you don't know them like I do, call Henry on Momday." I said.

"I'd like to pay for you, and Ms. Santiago's dinner." He said.

"Call me Sheri, and you don't have to do that." She said politely.

"Please, I insist, I'm a great admirer of your dad, I need to do this on behalf of Jack...." He pleaded.

"No, I'll never accept a thing...." I cut him off.

"I'll let you pay for our dinner." Sheri said as she reached over to hold my hand.

"Thanks Ms. Santi....thank you Sheri." He said, when he saw the way she was looking at him.

"Haven't you wondered why I lived with my grandparents?" I questioned Will.

I was interested to see if my grandpa ever told him or anyone. To my knowledge, the only people who he told were obviously the lawyers, and investigators he hired. Then again, how would he be able to explain how his only son, and wife abused his grandson so bad, that he had to be removed from their custody. That wouldn't be an easy conversation, it had to be difficult to carry around that kind of shame, even though he had no reason to feel that way. It also explains why he drank so much. I still idolize him though, he'll always be my hero.

"Your grandpa never said, Jack said there was behavioral problems." He said softly.

"Not on my part. I'll say this, there was enough evidence on BOTH of 'em, to send their asses to prison for a long time." I told him.

"I'm sorry Jay." He said, and I can tell he meant it.

Maybe Will didn't know after all, but I hope he makes the right decision, and gets away from them. As much as I want to burn everything connected to my parents, I don't want innocent people becoming collateral damage.

"Thanks, take care Will." I told him, wanting to end this.

"You too...." he said as we shake hands, before turning to Sheri, "considering the circumstances, it was a pleasure meetin' you, Jay's grandparents would've really liked you."

"That's sweet of you to say, they sound like were incredible people, who raised a wonderful man." Sheri said.

I've told Sheri how much my grandparents meant to me. Without them, I don't know what kind of person I would be or if I'd still be alive. That's a messed up thought to have in my head, but it's true.

Will went over to talk to the manager as a server came over, to take our drink orders. Now that we were finally alone, I can try to explain the insanity of my parents.

"Now you know why I smoke so much weed." I joked, trying to lighten the mood.

"It's amazin' that's ALL you do." She laughed.

That has crossed my mind a few times in my life. Considering what I went through, it's a miracle I'm not a junkie, alcoholic or a serial killer. My grandparents, and Christie deserve full credit on that, they showed me love when I had no idea what the word meant. Sure I have many deep rooted issues, from my lack of mercy I have for some people, to the rage that flows through my veins. Overall though, I like to think I'm a decent person.

"So how rich are you?" Sheri asked, and cracked up laughing.

"You caught that, uh?" I smile, and shake my head.

"I'm young, rich, and don't give a fuck!" She said imitating my voice.

"I sounded like a douche." I said, but couldn't help but to laugh.

"No you didn't, you were pissed off...." she said, when the waitress came with our drinks, "you're a sexy little thing."

I look at the waitress, and seen that Sheri was right. Her name tag read Rachel, she's maybe 20 years old, dark skin like Sheri, so I assume she's Hispanic. She was five foot, three inches, maybe 129 lbs, large d-cup tits, long brown hair that she wore in a pony tail. Rachel's in terrific shape, with an ass to match. If I was single, there's no doubt in my mind, that I would try to pick her up.

"Thanks sweetie, so are you." Rachel said to her.

"We have a friend, who'd just eat you up." Sheri told her.

I thought the same thing, Christie isn't into relationships, she has a rotation of girls she plays with. That being said, she would love having Rachel in her bed.

"Yeah she would." I agreed.

Rachel looked around to make sure no one can hear. She leaned down to talk to Sheri.

"If she's anythin' like you, I'm very interested." Rachel said in a sexy voice, that made my dick move in my pants.

"Judge for yourself, I took this of us last night." Sheri said, showing her a picture.

Right away I knew what Sheri was showing her. Christie came into my room to tell us goodnight, but Sheri wanted to take a selfie of us. The three of us were in bed with no shirts on, both girls tits on full display. If the sheet didn't cover our lower body's, she would've seen our dicks.

"She's hot, are the three of you in a relationship or something?" She asked.

"We're together, Christie's our best friend." Sheri said.

"That's so cool, that the three of you live together." Rachel said.

I almost spit my Pepsi out. Rachel helped me out without even knowing it. Before Sheri could say anything, I took it as an opportunity.

"That's the other thing I wanted to ask you, will you move in with me....well us?" I asked.

"Oh my God, I'm so sorry...." Rachel tried to apologize.

"It's ok, you did me a favor." I told her.

"You really want that?" Sheri asked with a tear in her eye.

"Hell yes...." I said as I hold her hand, when suddenly she squeezed it tight, as her eyes went wide.

"Oh shit!" Sheri said trying to maintain her composure.

I've seen this look before, it's just like back at the house when she came over, her ass must be vibrating. I start to laugh quietly, as I watch my girlfriend getting pleasured in the middle of a restaurant.

"You have an egg in you, don't you?" Rachel asked, and couldn't hide her amusement.

Sheri couldn't answer her, she just nodded her head over, and over again.

"I can help you to the bathroom." Rachel offered.

"Can't" Sheri said as she motioned for Rachel to look at her lap.

I looked over too, to see Sheri's dress beginning to tent from her hardening seven inch penis. There was no way, she was going to hide what was happening. She had no choice, but to wait until the vibrations came to an end.

"Wow, you're breathtaking." Rachel said.

"That she is, and she better not cum." i said looking into Sheri's eyes.

Sheri got a big smile on her face. She was loving this, as much as I was. Rachel seemed like she was getting turned on as well.

"If you do, your man won't be stickin', his....big...hard....dick...in....your....pussy!" Rachel whispered in Sheri's ear.

Damn, she's good at this. If Christie, and Rachel don't work out, she can hang out with us anytime she wants.

"What time you get off?" I asked Rachel, as we watch Sheri fighting her approaching orgasm.

"Right now, if you stick your cock in me." Rachel joked.

"I like her, can we keep her?" Sheri laughed, as she closed her eyes.

"You're my last table, can you not let her cum until I get out? I wanna watch." She asked.

This girl fits perfect with us, she loves teasing Sheri already, and we just met her.

"She gave me full control of her body, meet us at Club Eden." I said.

"I'll be there, is your friend as special as her?" Rachel asked as she ran a finger along Sheri's bare arm, causing goosebumps to prickle her skin.

"No, she doesn't have a LITTLE penis down there." I said.

It annoys Sheri when people assume she has a small penis, because she's only five foot, four inches, with small feet. Christie, and I are always busting her balls over it.

We watch as Sheri's breathing started to come back to normal, her body began to relax. She took a couple breathes, getting her composure back.

"That could've been bad, don't listen to him, it's not that little." Sheri said to Rachel.

"I can see that," Rachel laughed.

"You'd think he'd know that, as many times as I fucked his ass." Sheri said.

Rachel looked me over, then to Sheri like she was studying us.

"There's no way, he's to much of an alpha, and you're too girlie to ever be a top." Rachel smiled.

That's probably the biggest compliment you can give Sheri. She wants to be seen as a girl, who happens to gave a very large appendage, that she loves to play with.

"Damn, you tell fortunes too?" Sheri laughed.

"No, some things are obvious, and you never gave him an answer." Rachel said.

"He already knows, of course I'll move in with the fool." Sheri told her.

That's all I needed to hear. Despite all the drama with my parents, this is the happiest moment of my life.

Rachel gave us a genuine smile, before she returned to work. We both watch her ass as she walks away, we just met her but she's the type of person I'd hang out with.

I took out my phone to show Sheri pictures of the new house.

"This is OUR new house." I said, and hand her my phone.

"Love the sound of that. WOW, this is really nice." She said of the much bigger home.

I went on to explain to her, how my grandpa screwed my father over one last time from the grave. Upon his death, the company that he owned, and my dad was the Vice President at, was to be sold off, with the money going to different charities. I also told her, how he left me his estate, and how parents tried to sue me over the inheritance.

I know it doesn't make sense, that my grandpa still employed my father at his company, after what my parents did to me. He did that for one simple reason, he didn't want to cause a scandal in the business. So while they remained cordial for work, all personal ties were cut.