The Piglet in the Trap

Story Info
Transgirl is taken to dinner by her Dad's best friend.
11.3k words
4.26
18.3k
20
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Author's note: This is based off a fantasy I had about my own, real life Mr. Richards, my boss! Who I don't like. It's written from a more casual perspective than I normally write. I hope you enjoy!

It was awkward from the start. This man had known me since I was three, making that nineteen years, and it's not as if we had spoken one-on-one in that time. He was my Dad's business partner at first, and then his best friend. And then a few years ago he moved to Vancouver for some kind of business (I don't know... blockchain? VPNs? I think they do VPNs in Norway though, so I admit: I don't know what he does. Something with computers.) and so they turned their friendship into that kind of thing old men have where they call each other at the end of ballgames. When my Dad tags me on facebook posts (UGH) his best friend would always comment at me there. He wouldn't @ me, though, he would just like... type my name. But every other relation still using that place would comment too, it wasn't like a weird thing. In fact all his comments were the same bland "lovely girl," "she's all grown up" stuff old people always said. Or most of them anyway, the rest could go to hell.

But that half-assed form of communication for a "relationship" that had lasted almost my whole life was the problem!! What the hell do I call Greg to his face? When I was little it was Mr. Richards (he'd say "sport!") and when I was a teen it was just mumbling or fake talking and then I was out the door and in the family car and I was gone. And of course I didn't ever reply on facebook (lol). But when I moved to Vancouver last year for uni, and Dad insisted that Greg take me out for a good dinner one night, I was put into this awful spot: what the hell do I call Greg to his face!!!

I didn't even think about it until I was picking out my shoes. I had a pair of strappy black heels with a red undertone dangling off two fingers and it hit me. "Fuck."

I was not going to call him Mr. Richards. I was an adult, making my way on my own, an excellent history student and, as I recently discovered, very good at drinking. Or at least I was an enthusiast!! I wasn't a child and he wasn't a prof or a cop or whatever! So I guess he would have to deal with "Gary". Looking at myself in the thin Walmart mirror I had propped up against the closet by the door I tried it out. "Thanks for dinner Mr. G--"

I shook my head. My cute violet-tipped slut strands slapped softly against my cheeks.

"Thanks again for dinner, Gary, my Dad is such a worry-er, as you know." I cocked my head in a sophisticated gesture. "He must calm down Gary dear."

I reached my hand out towards the mirror, all while still bent over with my dangling shoes, as if I was gently resting my fingertips on his forearm. "Do reassure him that his daughter is alright, won't you?" I cocked my head in the opposite sophisticated direction and my breasts swung and wiggled back. "Perhaps the next time the Cubs lose?"

Or the Nicks or whomever. I wasn't studying baseball history.

I wondered if he would blush the first time I called him Gary. I laughed at that thought. I was going to blow this old guy's mind tonight, ha ha ha!

He was taking me to The Boar in Steel, which was like sixty dollars a plate from what I could see. I googled it to see what to expect and all I got was a "local expert" picture of a thick wooden door with a long bronze handle, the plain logo carved (by hand??) into a sign, the basic information of hours and old prices, and a bunch of positive reviews from short-haired white dudes whose profile pics were usually them and their wife smiling on a boat, or at a vineyard, or on a golf cart. It was kind of cute. But I bet I was younger than any of their kids. And there were dozens of them! And here's the part you'll flip at: Gary Richards was one of them!!!

His profile picture was actually pretty good. He had someone else take it for him (or so I assumed, since I don't think you know how to work the timer setting on the front camera if you're over 40) and so you got a good shot of him, at his big oak desk, from the waist up. A huge window showed off the city behind him, big tall buildings reaching up like disastrously huge columns, lined along unevenly across Greg's straight broad shoulders. His crisp white sleeves were rolled up in a master's roll and they sat patiently before the crooks of his elbows, showing off two huge hands and arms covered in salt-and-pepper hair that made him look like a well trimmed wolf. His smile wasn't too big and it wasn't even a little bit self conscious. Straight jaw to match those shoulders, too. Old straight confidence man Greg Richards selling bitcoin through VPNs through the Apple store.

Anyway, his review read: The boys at the Boar in Steel always know how to treat a regular. As dining goes, it's the cadillac of Vancouver's night-life dining. Discretion, exemplary service, the best food from here to the east coast in either direction, and the perfect lighting for a beautiful night. Thanks again, boys!

It was five stars. "You'd give 'em six if you could, wouldn't you, Mr. Richards?"

I fought Dad so hard to get out of this, but I hadn't eaten anything but tomato soup for... quite a while. My last splurge on food had been a philly cheesesteak I bought at 1:57 AM (they closed at two but if you and your friend have loose shirts, pierced nipples, a good smile and a set of working arms they don't mind at all) (they didn't seem to, anyway). I had three bites of it and dropped it in a field, then I had two more bites and dropped it in a puddle.

So Greg's offer was actually coming at a pretty good time. I could kill an hour and a half talking about, I don't know, Heraclius or something, the friends I was fucking but wouldn't mention fucking, and the "clubs" I wasn't in but could fake being in, and then say I had a test and I should turn in. If it was early enough I could ppppp-probably get a boy from Tinder here before it was bed time for little old Elly.

But anyway, The Boar in Steel seemed like a good opportunity to dress up. Tonight, every white-haired head from those profile pics was going to be turning from their tablet camera to my ass (lol). I had my black hair totally degreased from the night before and pulled up into little buns (except for my slut strands which I would never abandon), my hangover was mostly gone, my face was beat like an angel getting curbstomped in heaven onto an especially sexy marshmallow, and This. Dress. Greg might die when he saw my dress. If I had put on a freshman fifteen it was ten across my tits and five in my ass. Actually, I thought, pausing, I guess he might die when he sees my tits!

Giggling, I thought of the old guy seeing me for the first time, seeing the tits I'd grown in the years in between. The mindfuck was going to be fun, lol. "Can I look? Can I comment? Don't be weird, this is your buddy's girl!" But I can't help that my body describes sex just by its shape! I could enjoy it, even highlight it, but just me without anything sitting in a corner would drive a guy wild. And tonight I had This Dress, which my friend Becky had rudely named my Hot Plum Dress.

It's not plum! At all! It is kind of a... well, like, I would say it's more of a violet? But not like totally violet. It's a deep purple, really. Well, anyway, it should look like an old couch but on me it looks like you want to buy me a new car just so I'll drive it over you.

My fancy (slightly slutty) dress was sitting fresh out of the dryer on my bedspread. I was still standing bent in half in front of my nine dollar mirror. Hair, perfect. Face, outstanding. My throat was so... it was like a lily quietly opening up in a burst of morning sunlight. "You would choke me just to get your hands around it." I was actually very pleased with how my skin was for how little sleep I was getting lately. My complexion, all over, was smooth as marble, as if a statue had a racing heartbeat.

I had fat tits, I'll say it. They swelled and fell from my neck like an oil painter had been training to paint one-handed, and then they perked back up to let you know I was real, and ready, and not even half unspoiled by life and experience. Don't these breasts make you want to spoil me, baby? But then my creamy little tummy (it's an innie, fyi) caught your eye and kept you just so interested in where I would go next. A little dark black fuzz gave you a hint. Wasn't my pubic triangle a garden just for you?

I was biting my lip. Down, girl, I thought.

Did I have time for just a quick little bit of fun before I had to get dressed?

My fingers found my soft little clit and gave it a playful tug. I always started like that, I don't know why. I pinch myself when I'm putting on a shirt, too. It just keeps me focused I guess, lol. I split my fingers and ran the warmth of my palm down my soft length, pushing myself through the V between my middle and ring fingers. I pulled my black shoes up by my shoulder, they looked amazing hanging next to my breasts. Their silver buckles flashed and it made my hot pink nipples hard. Or maybe it was the long magenta french tip making a truly evil discovery beneath my foreskin as it bullied the underside of the head of my cock. To be honest, it might have been the sight of my dick getting hard between my nails in that cheap flimsy mirror. "Fuck."

I had a vibrating dildo from my morning "hangover cure" right above my dress, on my pillow. I could get it, just scratch a tiny itch, calm down before my "date".

I giggled. "Just the basics though, right bitch? Right."

I skipped back to my bedroom, shoes in hand. And just as I got there my phone started buzzing.

The screen read Unknown Number but I knew the number from my Dad's messages. Greg. Uggggghh why couldn't you just text Greg??

Still absent-mindedly swirling the tip my clit with my hard purple nails I put on my chipper voice and answered. "Hi, Greg?"

He chuckled. Expecting Mr. Richards, weren'tcha Greggy-kins?

"Hello Eleanor. My god, you sound like a real grown up these days!"

I narrowed my eyes out of reflex and my fingers stopped, and then got meaner. Wow, almost like time marches on, huh, Greggers? Your grey hairs didn't clue you off?? I laughed in my chipper voice. "You sound just like I remember! Sorry I didn't text you to set up everything. Dad, uh, well you know--"

Greg laughed again and it sounded like it was echoing in a stone hall but it was just his chest. It rumbled the phone in my hand. I thought of the stretch of white hair over his arms, it had to be everywhere, right? A whole body of white fur bent gently beneath just a few buttons. Now why the hell are you thinking of that?

I shook my head.

"Yeah, I know what Jason is like," he said. "It's alright, Eleanor. I hate to cut to the chase but I'd much rather talk to you in person! I'm parked in front of your building."

"Oh fantastic!" Fuck. "That's great, oh my god."

I wanted to whine but this wasn't some little skater boy who thought acquiescing would get him laid. And my hungry tummy was starting to get as argumentative as my dick.

"I'll be right down!"

Things didn't stop being awkward once we were face to face. I was annoyed when I realized that the first time he would be seeing me would be in the parking lot, but it was even worse than that: he was waiting in the lobby. I didn't even see him! I was barreling out of the elevator with my face in my phone getting ready to take my first triumphant strides through the double glass doors when he piped up from one of the chairs in front of the rental office. Stupidly, clumsily, I stopped in my tracks. My expression must have made me look like a real idiot because, initially, I didn't understand what was happening. I thought that I had accidentally called him? But then I saw him in my periphery, walking up in no hurry but also very, very fast. He was at least 6'5 and his legs took him wherever he wanted pretty fast. I had to shake my head. Then I gaped like a fish before catching myself.

Phone away. Smile. Boob check. Shit, I thought, and hoped he hadn't seen me plump myself. "G-Greg! Oh my god! I thought you, er--"

He laughed. "A kindly little granny let me in."

So much for my grand re-entry into Greg's life with the evening sun going down behind me, my silhouette sparkling in the glass, a gentle wind rustling my hair as I struck a pose that showed more leg, more hip, and more neck than I really had. Bottomless throat though. I thought. Like, bitch, of course.

Greg's massive chest was right in front of me and he kind of... well, it's hard to describe. But he was just sort of there and he didn't extend a hand to shake and he wasn't there long enough for it to be awkward but, well... I guess I defaulted to how I used to greet him and I gave him a big hug. I felt even dumber! I don't think I'd hugged anyone since I said goodbye to my best friend on the last day of high school.

When was the last time I had hugged Greg? Had I ever? Maybe during an awful little league game I won? My parents and Greg had always been pretty close, it was actually so weird that I felt like he was a stranger. Parents' friends are like that. But I guess I was curious to see how he would react to my ample chest pressing into his.

He seemed happy. His left arm covered my whole back with room to grab my bare shoulder and still have his elbow poking out the other side. He gave me one squeeze and let go.

"Ah, it's good to see you Eleanor. Can I call you Elly?"

UGH, no.

"Of course!" I laughed.

He tilted his head down at me. His eyes were jet blue metal. Maybe he was a white wolf. "Well, on the other hand, maybe you're a little old for that, young lady. Eleanor suits you perfectly. Great name." He palmed my shoulder again. "Not that I'm calling you old, of course. Less wrinkles than a stain glass window."

He perked my chin with the knuckle of his thumb and winked. And I fucking blushed. It was stupid! That was really dumb, Greg!

Even a damn fool skater boy wouldn't have been dumb enough to do that. With his long dirty fingers.

And his clothes! He was dressed like a dad on a weekend. He was wearing a similar white shirt like in his profile picture but this one had a logo over his breast pocket. It was... I wanna say... for golf? It was basically a polo. He had a dark pair of jeans and the only surprise was a well polished pair of brown monk strap shoes. I was beginning to regret my choices. When I walked in with him dressed like that? I was gonna look like... well I don't know what people would think I looked like.

I felt a thrill flutter between my hips imagining some jealous old rich woman muttering "Whore" under her breath. I would look like a whore hauled into the boat and ready for the paddle.

Ew, gross!! This guy saw you do little league Elly get a GRIP

Greg drove a truck that felt more like an armored vehicle. It was icy cold inside from the AC which was one button on a panel four-feet across and all of it was buttons or touch screens. I actually struggled a lot just to get inside it, the floor of my seat was, like, higher than my knee. Of course he stepped in like this was normal, a normal sized truck that everybody was used to. But I had to pull and amble and pick my heels up from the pavement to his clean carpet and hoist my hips up and keep my face from dragging over the seat and knocking into my purse, which had to go up first!! Like I was jumping on a train!! Another dummy moment from Elly. My Hot Plum Dress didn't help. Thank god he hadn't tried to help me up because all the commotion sent the slit way up my thigh and practically popped my ass out into the hot summer air of the parking lot. Bad enough I could feel my tits pushing into each other and threatening to make my cleavage burst out my top.

When I finally got the back of my dress smoothed out and I took a little breath and buckled my massive seat belt (feeling truly like we could drive over an explosion and I would be fine) he was adjusting some setting on something as if nothing in the world could bother him. Like he hadn't noticed! Like hell he hadn't.

He asked if I minded that he turned on "The Game" and I said I didn't. We mostly we spoke over it and talked about my Dad. He asked about Mom and I told him she had turned the garage into a yoga studio for her neighborhood posse. He laughed so hard at that.

"How's Jason feel to have his garage hijacked?"

"Oh Mom does not let him in there anymore he can't even park his car in there. She told me he keeps making excuses to come in when she's leading a class!!"

"That dog," he said and chuckled. "I always told him he was lucky man to land Miranda as his wife. I guess even lottery winners get a little greedy."

"I think he has a crush on our neighbor Tina. Do you know Tina?"

He nodded. "Indeed I do! She was around for all the adult functions you kids snuck off for. Beautiful woman, Tina. Like a showroom caddy. But your mother? Hoo boy, now there's a model they couldn't even make any more."

My jaw must have dropped. I knew I was smiling but it must have swung open too because he put up one big paw and tried to back pedal.

"Sorry, Eleanor, I shouldn't talk that way about your mom. I'm just saying that he was a lucky man long before Miranda bought a pair of of yoga pants. Lolos, you know."

"Lulus??"

He chuckled. "Those must be the ones."

He scratched his chin. "Those still popular? Do you get Lolos?"

"They, uh... let's say they don't fit me."

He nodded thoughtfully.

He drove so smoothly his truck could have been on rails. I was shrunken into the middle of his passenger seat feeling like a teddy bear more than an adult woman in an appropriately-sized carriage. I had my legs crossed business style to keep warm and my arms were very casually wrapped over my chest. I desperately wanted him to turn the AC to heat but I didn't want to draw attention to the hard pink points hiding just beneath my wrists.

Why didn't I bring a jacket! And the answer was, because I was only going to be gone like an hour. He probably had plans after too. He was a little too smart and self aware to think his buddy's girl, half his age, wanted to hear him talk about business all night. Or baseball. Or whatever! It was genuinely very nice of Greg to take said daughter out, though. As we got closer to food I started to feel more and more sentimental about seeing him again, after all these years.

When he parked and shut off his engine (which hummed-down like a fucking rocket) he held up a single tree trunk finger and said, "Wait just a minute."

I think I mumbled "Oh, okay," and watched him step out of his door, swing his keys around the same finger before they disappeared into his slacks, and walk around to my door. He opened it and extended the big paw from earlier. "Here, darlin', let me give you a hand."

"Sorry Greg. It's just so tall!" I giggled.

I took my purse and his hand and awkwardly tried to maneuver myself without flashing him but I guess I took too long getting my angles right because in short order he let go of my daintily bent fingers and grasped me with both hands around my rib cage. His thumbs basically met in the middle. Without a deep breath or word of warning he picked me up from my seat and landed me gently on the asphalt like it was as easy as transporting a kitten from the couch to her carrier.

It wasn't because of Greg, but I really wished he had arrived later. I hadn't gotten the time to properly get off and my sex drive was way too high for my own good. It was so embarrassing but I could feel from the little throb in my cock that I would start to drip soon if I didn't get my head straight. It was already feeling a little crowded between my thighs. Imagine how it will feel with two cocks between your legs! I desperately needed a tinder boy between them later, that I knew. I just thanked God that for now I was wearing panties. Fuck, I thought, I should have worn a bra. Greg must have gotten an eyeful when I was in flight.