The Bet Ch. 02

Story Info
Girlfriend wins bet, dominates her boyfriend.
1.4k words
4.25
94.9k
15

Part 2 of the 4 part series

Updated 10/30/2022
Created 04/23/2009
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ssnatch
ssnatch
271 Followers

"Good evening ladies and gentleman. Flight 2134 to New York City is now boarding through gate number 23," announced the gate agent over the PA system. We boarded the plane, and found our way to our seats. Sarah took the window seat, and I took the aisle. As the stewardesses got everyone seated and bags stowed, I began to relax. I could still feel the plug in my ass, but at least now, I could just sit in my seat for the next couple hours while we flew to the city. I closed my eyes, and felt the plane begin to move as it pulled away from the gate.

I awoke, surprised that I had fallen asleep. We were in the air, and I could see that drink service had begun. Sarah noticed I was awake, and she reached down to pull out her purse from beneath the seat in front of her. She fished out some cash, handing it to me. She leaned over to me.

"Red wine, pantyboy," she whispered into my ear, then flicked her tongue across my ear lobe. "And get yourself a jack and coke. You'll need it."

I didn't really know what she meant, but given how the evening had started, my mind started racing. When the stewardess stopped next to us, I had already pulled down my tray-table. I wasn't so much preparing for the drink as I was trying to hide the tent in my slacks. As soon as I had purchased our drinks, Sarah leaned over again.

"Drink up, I've got something for you," she said with a lilt to her voice that told me that she had more plans for me. I took a deep drink, and put the jack and coke down. Sarah reached with one hand to my drink, and with the other swapped it out. My eyes followed my drink. It was at that instant that I realized my mistake. I looked back at my tray table to discover another butt plug standing up next to a small lube bottle. I reached as quickly as I could and grabbed them both, pulling them down into my lap, trying to hide them. I could feel my face turning a bright red as I hoped that the people seated across the aisle to us were not paying any attention to us. I turned to Sarah, and gave her my best what-are-you-thinking look. She smirked, leaned in and kissed me, then slid her lips along my cheek to my ear.

"Time for you to trade up. If you are going to be able to handle what I have planned, you need to prepare," she growled into my ear. "Go to the lavatory and put that in your sweet ass for me pantyboy. You won't need the other anymore, just toss it."

So much for a relaxing flight. I got up carefully, trying to keep the plug hidden in my hands as best I could. This one was clearly larger than the last. Not really longer, but definitely thicker. I could feel its girth in my hand, and guessed it had to be close to 1 1/2 inches in diameter at its widest point. I walked down the aisle, and only then looked up and noticed that the "Lavatory Occupied" sign was lit up. I stood outside the door of the lavatory, facing away from the passenger cabin, holding the butt plug in my hands. It felt like an eternity, but it was probably just a minute or two when the door opened, and I could slip into the lavatory.

I slid my slacks down to my ankles, and looked down at my cock covered panties. Or more like partially covered cock. Seeing the hot pink panties just made me even more excited, and I could feel my cock swelling to its fullest. I ran my hand over my balls, feeling the smooth satin. I hooked my thumbs into the waistband, and slid the panties down to my ankles. Fortunately, the cramped lavatory has hand holds, as I needed to grab onto one so that I could bend down and slip one foot out of its shoe and out of the slacks and panties. I raised my foot up onto the small counter, and leaned forward, trying to spread my legs as wide as I could. I reached down between my legs, and got ahold of the base of the butt plug. I gently pulled on it, and immediately felt pressure against my anus. It wasn't coming out.

I pulled a little harder, and felt even more pressure on my anus. I felt a bit of panic, but told myself I had to relax. I closed my eyes, took a deep breath, and tried to relax. I reached down again, pulled on the plug harder still. I felt the plug moving. The pressure was intense and I could feel my sphincter stretching, and just as I thought it was going to hurt, I felt the pressure release, and the plug came free. I breathed a deep sigh of relief. I took the new plug, applied some lube, and added a bit more to my anus, then took a deep breath, and started to push the plug into my anus. At first, it felt good going in, and it slid in easier than I had expected. As it got deeper into me, it got wider, and I could feel myself stretching again. I backed off, and then took another deep breath and as I exhaled, I pushed again. Again, it was unable to push the plug all the way in, and so I pushed again, and again. Before I realized it, I was fucking myself with the plug, pushing just a tiny bit harder with each inward thrust. My cock was full erect, and I looked down to see a drop of pre-cum glistening at the tip. With my free hand, I wiped the drop onto my finger, and licked it, tasting it. It was sweet and slick to the taste.

At this point, I wanted to take my cock and stroke myself, but I knew that Sarah would not approve, and I didn't want to find out what punishments she had up her sleeve. Instead, I refocused on inserting the plug, and with one more hard thrust, I was able to push the widest part of the plug past my sphincter, and it popped into place. I pushed it a bit deeper still, reveling in the fullness it created. This plug was definitely larger than the last.

I cleaned up, washing the lube from my hands, and carefully wiping away excess lube from the plug to avoid soaking my panties (and as a result my slacks), pulled my panties back on, and tried to calm myself so that I could fit my cock back into the panties. I fumbled a bit, getting myself redressed in the tight space, but after checking myself over as best I could, I took the first plug, and threw it into the refuse bin. I wondered if the people who cleaned the plane would notice it. I smiled at the thought of someone dumping the trash and seeing it, wondering what was going on during this flight.

As I made my way back to my seat, I again had to focus on trying to walk normally as the new larger plug made movement a little awkward, and with each step, I could feel pressure against my inside like I'd never felt. Each step sent waves of pleasure from my inner core out through my body. The feeling of fullness was both overwhelming and blissful. I locked eyes with Sarah, and I could tell she was amused watching me walk down the aisle. Fortunately, most passengers never look up from their books or computers, or had their eyes closed and iPods on.

I took my seat, and turned to Sarah. "Mission accomplished, Mistress," I reported.

"Mmmm...good pantyboy. How does it feel?"

I took a quick peek to the seat behind me and saw that both passengers had on earphones. I already knew the ones in front of us were dozing. "Mistress, I feel stuffed full. Its like nothing I've ever felt. When I move, I can feel a pressure inside me. I don't know how to describe it, but it feels good–totally wrong, or um...taboo? But definitely it feels good."

"See pantyboy? Mistress is taking care of you isn't she? I think you'll only need one more training plug tonight before the real festivities begin," she said in a sultry voice.

"Yes Mistress," I answered.

ssnatch
ssnatch
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6 Comments
GoodhueGoodhueover 8 years ago
Enough!

- Maybe he goes along with the panties and the first butt plug,but when she gives him the larger one telling him he'll need it for what she has planned,he needs to bail! He's gotta be thinking now that she's planning to strap-on him herself,or plans to watch him take it up the ass from another man.Fuck that shit!

AnonymousAnonymousalmost 15 years ago
Your gay friend is full of crap

Good story.

A man enjoying anal stimulation is no more a sign of being gay than a woman enjoying cunnilingus is of being lesbian.

AnonymousAnonymousalmost 15 years ago
Keep it coming!

Well written with a good pace. I hope the main event is as well written and worth the wait.

AnonymousAnonymousalmost 15 years ago
great

love the slow build up make him a smoothie

AnonymousAnonymousalmost 15 years ago
So when does he come out of the closet?

If this were gay male, then I would say this is hot; but seeing that it is about loving wives I'm confused. A gay friend of mine says that there are no bi-sexual men. Just homosexuals struggling with their identity. Change his name from panty boy to cocklover.

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READ MORE OF THIS SERIES

The Bet Previous Part
The Bet Series Info

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