Winning Cupcakes Chapter 4

“So I just go on this date, we’re all hunky dory, we move on,” I said at the dinner table the next day.  I was digging into some really good food, which calorically speaking probably twice exceeded what I needed in a day, even with my limited serving.  I could tell Julie and Debbie were not as relaxed about the current situation.

“We just think you should be careful,” Julie said, her thin arms clearly trying to limit her intake even more than mine.

“You didn’t have to agree to this, Tom,” said Debbie, stuffing even more food than usual into her mouth.  “You have nothing to prove.  We’re just associates.  Everyone knows it, and when we win the bake off, that should prove it.”

“I don’t think it’s just Tammy that thinks that, Debbie,” I said.  “When we were at the grocery store, people were constantly talking and pointing.  We were a pretty big discussion topic, one lady even approached us to ask.”

“Mom, is that true?” asked Julie.  Debbie’s face went completely red.  “Anyways, Tom, I assume there’s an ulterior motive going on.  Maybe Tammy wants to get you without Debbie around to spill the beans on her recipe for cupcakes.”

“You think so?” I asked.

“I wouldn’t put it past her,” she said.  “They have been rivals for as long as I can remember.  Mom always beats her at the bake offs.”

“Hmm…” I said.  “I’ll keep that in mind.”

Julie nodded.  “And try not to get crushed-” she started, but she was interrupted by the doorbell ringing.  They all looked at each other, not sure what to make of it, but knowing full well who it was.  Julie got up and opened the door, and the slim but tall figure of Tammy stood in the doorway.

“Evening, all,” she said, looking around.  Her eyes met mine, still sitting at the table.  “Tommy boy, are you prepared for your date tonight?”

I had indeed dressed nice for our date.  “Yes ma’am.”

“Good,” she said with a smirk.  “Geraldine, come in and give your date a kiss, he is looking extra cute for you tonight!”

On cue, Debbie walked in, a little bit shorter than the doorway but perhaps wider.  She wore a yellow polka dot dress that was extremely low cut, showing off an amount of cleavage I would have never assumed possible just a few days ago.  Her dark hair was in curls, and she was wearing more lipstick than before.  It was clear she wasn’t the prettiest girl in the world, nor was she able to apply makeup effectively, but the effort was clear on her part.  The dress did little to cover her legs, which were insanely thick.  She brushed past Debbie and stood behind me, saying nothing but watching me intently.  Just to look down at me, she bent forward, putting her lengthy and weighty breasts on full display.

“Why don’t you give her a kiss, Tommy,” Tammy said.

“Of course,” I replied.  I turned back towards her, trying not to look at the immense breasts in front of me and into Geraldine’s face.  I closed my eyes and moved into her mouth, feeling the tension coming from Debbie and Julie as my lips met hers.  As soon as they locked, she took over and stuck her tongue in my mouth.  I had never been kissed like this in my life; this massive girl had totally dominated me with just her mouth and tongue.  I opened my free eye to see Tammy smiling maniacally, and conversely saw Debbie and Julie looking away.  More and more, I was realizing that this date may have been a mistake.

Eventually, in what in all actuality was probably ten seconds but felt like minutes, she would stop kissing me and let me go with a popping sound.  I tried to wipe off some of her lipstick, but it was clear my face would likely need some retouching.

“I’m going to be your chauffeur for the night, Tommy boy!” exclaimed Tammy with her most insincere voice.  “We are going to see a new movie, The Alligator From Hell.  Don’t worry if it’s too scary, Geraldine will be there to keep you safe.”

With that, Geraldine hoisted me in the air by my armpits and slung me over her shoulder like I weighed nothing.  Her thick arms were already wider than my whole body, and while I felt safe on her shoulder, I couldn’t help but look down and see just how tall she was.  Tammy opened the door and Geraldine exited with me in tow.  I waved goodbye to Debbie and Julie, who both had concerned looks on their faces.

“Have a good night!” Debbie called out.

“He will…” Tammy answered for me before shutting the door.

Outside was the car.  Just a sedan.  Interesting.  Geraldine opened the back passenger’s seat door and placed me in.  She then buckled me in with her burly hands, like I was a helpless baby.  As she was doing it, she was bent forward, her massive cleavage inches from my face.  I would be lying if I said I wasn’t thinking at all about how huge her breasts were, and how much bigger than my head each of them were.  My eyes must have been on them a little too long, and her eyes caught mine.  I smiled at her, a little embarrassed.  She gave me a big smile, gave me a kiss on the forehead, and closed the door.

As she made her way to the other side, I looked out the window.  I could see Debbie looking at me through her window, and I gave her a thumbs up to let her know I was okay.  Her generally nervous expression didn’t change, and I couldn’t tell why.  Suddenly, I felt the car take a huge dip, and before I could react, A massive amount of Geraldine smashed into me, flattening me against the window.  Indeed, this car was way too small to transport a girl like her, and she took up basically the entire back seat.  I didn’t even have enough room to turn my head.  Debbie bit her lip as Tammy got in the car.

“Are we all set back there?” she asked.

“Mmmhmm…” was all I was able to muster.

The car lurched forward and we turned a corner, Debbie disappearing.  I was suddenly alone.  Well, with the enemy, and her gigantic fat daughter, but alone.  I wasn’t sure what to expect, but if Tammy was involved, it couldn’t be good.

When we got to the movies, Tammy parked the car and opened the door for me first.  I fumbled around for the seat belt, which was stuck against a mound of flesh, but I managed to click the button and I came loose, almost falling out of the car.  Being the gentleman I am, I made my way to the other side of the car and opened the door for Geraldine.  It was like a mountain being squeezed out of a tube.  The car instantly rose 6 inches, if not more.  She towered over me, and I can only imagine what onlookers thought as she grabbed my hand with her big hand and began walking to the theater.

Tammy bought us tickets, and I was surprised that she only bought 3 seats.  It was one of those theaters where you had to specify which seats you were buying.  I mean, I didn’t want to be rude, but Geraldine comfortably took up 2 seats on her own, if not more.  Of course, I didn’t say anything and we proceeded to the theater.  As we were walking, I was wondering why Tammy was following us around.  Her presence made it so bizarre; the date might actually be okay if she wasn’t hovering over us every second.  Then maybe Geraldine would actually say something.

When we got the seats, Geraldine moved one of the arm rests down and sat in two seats, and Tammy sat in the third.  I looked around for where to park, and Geraldine held out her hands, implying she was going to hold me.  More feeling like a baby.  I sighed and walked in front of her, then turned around.  She lifted me up and put me on her lap.  She held onto my waist with her hands.

“So… we have a few minutes before the preview starts,” said Tammy.  “I noticed you and Debbie were out shopping the other day.”

“Yep,” I said.

“That sounds so fun!  What were you two shopping for?”

“Oh… just some things,” I said, not wanting to play into her hands.  I knew she was trying to figure out her recipe, and I wasn’t foolish enough to fall for her trap.  She stroked her chin for a second.

“Geraldine, you don’t want him to fall off your lap during the movie do you?” she asked.  Geraldine shook her head with a big smile.  “Good girl.  You need to hold him really tight, for the WHOLE movie.  Okay?”  Tammy’s eyes went from Geraldine to mine, staring daringly at me, as if to say “Game On.”

Geraldine’s large arms pulled me in, squeezing my ribs and shoving my head between her huge breasts.  I could feel her breast flesh on either cheek, and they were so big and heavy and being mashed between her arms that they were now blocking the movie screen from view.  I was completely trapped.  Two hands parted her tits and Tammy’s face appeared in front of me, that sly smile on her face never wavering.

“I’m going to get some popcorn, do you want anything, Tommy boy?”

“...no thank you…” I said.

With one final smirk, she let go, and Geraldine’s breasts covered my view again.  I was losing track of time while most of my vision was obstructed, but I could tell the movie was in full bloom.  It was during a fairly quiet moment that I realized something:  I was comfortable.  Too comfortable.  I was sandwiched in between the biggest breasts I had ever seen in my life, and I felt… good.  And much to my horror, I was hard.  My cock was suddenly pitching a tent in my pants.  But there was nothing I could do about it.  My arms were restrained by Geraldine’s huge arms.  I tried shifting my legs a little bit, but there was nothing I could do about it.  Unfortunately, I must have drawn attention to it, because I felt two of Geraldine’s fat fingers touching it.  She was now restraining me with one of her huge arms, and with the other she was now massaging my cock.

She then turned me around with her hands so my face was now buried in her cleavage.  With one hand she pulled my face out of her breasts, and she pulled me in for a kiss, much like she had done before, but this time with even more passion.  And it didn’t stop.  We made out for the rest of the movie, which I had barely even seen to begin with.

“Looks like you two are coming along swimmingly!” I heard Tammy say.