I wondered if I learnt my lesson as we drove home. Not only that, I started to calculate how much my stupid adventure with Caitlyn cost. Between her dress and shoes and stuff, my new clothes, the dinner and tip, her cab fare that I gave her money for, and gas; it must have been close to nine bills. Plus the frikkin’ tire needed to be fixed.
I looked over to Caitlyn. She was asleep.
Was there anything positive to come out from this whole misadventure? Her pussy was shaved. But I wouldn’t be seeing any of that tonight. Did she really feel she was being humiliated by being forced to wear that dress? Suddenly I felt guilty. If I was humiliating her, was her behavior tonight to punish me as a response, or was that just the alcohol talking?
There was really only two ways to find out. Get her drunk again, or get her dressed up again but without alcohol. For now though I just needed to have her settle down. After four martinis and two glasses of wine maybe she won’t even remember the evening at all.
I managed to get her into the spare bedroom. It was the first time she slept in it. I slipped her pink shoes off, the necklace and earrings too. She slept in the dress.
*
Caitlyn was still sleeping the next morning when I took off to do some shopping in town. At an adult store I picked up a little white vibrator, really no bigger than a finger. It had a breast cancer awareness pink ribbon logo on it. It was waterproof and designed to buzz the clit. I also picked up two pairs of Velcro cuffs. Also in pink, just to piss her off.
She was in the kitchen wearing sweatpants and a t-shirt eating toast and jam and nursing a big cup of coffee when I got back. It was okay. It was Saturday she had all the time in the world to recover.
“How’s your head?” I asked.
“I’m sorry Doug.”
“No, Cate. It’s my fault. I shouldn’t have forced you into an uncomfortable position.”
“I shouldn’t have drunk so much.”
“You did look very pretty though. Maybe you’ll wear the dress just for me?”
“What? Is that some sort of a kink thing?” she asked.
“Now that you mention it,” I replied, “yes, my cock will respond to feminine and pretty every time.”
I could see the wheels turning in her head.
She lazed around recovering all day. I vacuumed. She did some cleaning too but mainly stayed away from the vacuum cleaner noise. By mid-afternoon she was fine. By five she had a glass of wine.
Dinner was inch thick strip loin steaks on the barbeque. Now that Caitlyn trusted me, I was permitted to attend to them myself. She did baked potatoes in the microwave. They were topped with butter, sour cream and chopped chives. Sautéed garlic mushrooms, peas with butter and a side salad with that Russian dressing that she makes rounded out the meal.
As we ate I laid out exactly want I wanted her to do after dinner. Eagerly her head bounced up and down with every suggestion that I made.
After we cleared up she headed off upstairs. I went to the shop to get a few things.
She was in the pink floral dress again. Her pussy was freshly shaved. Pearl earrings and necklace. Lipstick, eye make-up, pink finger nails the whole bit. Even the shoes and panties.
She was kneeling on the carpet. Her wrists were bound with pink Velcro cuffs, extended horizontally to each side. Ropes connected to D-clips on the cuffs extended tightly to a door handle on one side and the stair banister on the other. She wasn’t going anywhere.
The little white and pink dildo was pressed into her slit, the business end right up against her clit, and the rings on her labia were tied together with dental floss enveloping the whole dildo. Just the bottom end stuck out from her labia with the push button control. The crotch of her panties kept everything snuggly in place.
Her tits hung out of the dress. A small padlock was attached to each nipple ring. She was okay with the weight. Just.
My cock was already hard. I was naked.
“Are you ready?” I asked.
Breathlessly she answered, “Yeah.”
I reached under her dress and found the end of the little vibrator in her crotch. Two presses clicked it into high.
She reacted immediately lunging forward, pulling at the ropes as her body twisted. Her motion made the padlocks swing from her nipples that were pulled down from the weight.
I stepped in front of her, my cock standing at attention.
Her mouth opened up like a baby bird’s ready to be fed.
I stuffed my cock into her mouth.
With a gusto that surprised me Caitlyn sucked on my cock. She rolled her tongue around the head and repeatedly plunged the length deep down her throat each time holding it down for a second or two before pulling back for air. Saliva was dripping on her chin. Her nostrils flared with each breath. Her face, neck and the nape to her shoulders were pink, matching her dress.
Padlocks swung as her head bounced on my cock. I put my hands on the back of her head.
“No! Don’t push my head,” she garbled looking up to me. Spit rolled down her chin.
“Okay,” I said and clasped my hands together behind my back.
Back down my shaft, she impaled herself with my cock deep into her throat. Her eyes bulged and watered. Her face was flushed red as she pulled back trailing spit. Cool air rushed past my cock as she gasped for air. Up and down the length of my cock she went. Gulping it down, almost gagging and then sucked it hard.
I couldn’t believe she was enjoying that.
I saw her belly and thighs quivering below me. Clearly she was.
I was too. My hips started thrusting forward. She wasn’t giving me a blow job by any stretch of the imagination, I was fucking her throat and she was loving it!
My hips swung from side to side pushing my cock head to one cheek, bulging it out, then the next and back again. Then she swallowed my cock again, balls deep and held for a second or two, wet red faced gasping as she pulled back.
“Auuughh” she growled and slightly bit down on my cock. Her whole body shook. The padlocks bounced. “Auugh,” she shook again and jammed my cock back down her throat, holding as her body quivered.
The vibrator must have gotten to her.
My cocked picked up the in – out pace. I couldn’t help myself. She continued to shudder below me. Her head and neck were red, tears ran from her bulging eyes, her runny nose flared in search of air and spit covered her cheeks and chin hanging in threads to her chest. “Mmmnnff,” she trembled, “mmmnff” as my cock slipped in and out of her wet mouth. The pink lipstick was long gone.
The visual was too much.
I knew I was going to cum at any moment. Both my cock and my brain were ready to explode. My knees were shaking. I had trouble keeping my balance. My heart was racing. My breath deep and vocal.
Caitlyn never let up on her orgasm. She just kept on cumming. The sights and sounds of her spasm sent me over the top. I grabbed a hold of her shoulders to steady myself as I came.
Her mouth gurgled with my cum and her own tremors as I emptied myself into her. “Nnaaaghh,” she contracted so hard that she bit down on my cock. It didn’t stop spurting though. She swallowed come as quickly as she could as her body jerked in time with mine.
She pulled her head back, with mouth open and gasped for air. Her body jerked again. The end of my cock flopped on her chin, glistening wet. She sucked it back into her mouth. Her cheeks drew in as she sucked the last of my cum through my hole.
Everything was going grey. I had to sit down.
I was hyperventilating as I heard, “Get the vibrator out. Stop it.”
I reached under Caitlyn’s pink dress. The crotch of her panties were soaked. I wondered if she pissed herself. I pushed the vibrator through her slit until it popped onto the floor still buzzing like an angry bee.
I unhooked one D clamp, then the other. Caitlyn slumped to the carpet.
“Find the keys,” she gasped.
They were on the table, I had to stumble up to get them. I unhooked each padlock and kissed her nipples and gently sucked them better. Caitlyn seemed to enjoy the nipple attention I gave her.
She turned the vibrator off and dropped it to the floor.
We lay on the floor, hugged and kissed each other. Her boobs slipped back into the dress. The pink Velcro wrist cuffs were still on.
“I can’t believe you loved that,” I said as we stared at the ceiling.
“My clit is numb,” she answered.
“You didn’t stop cumming,” I said.
“I can still taste your cum.” With that she rolled over and gave me a deep kiss, shoving her tongue into my throat. “Can you taste it?”
“Yes.”
“Good isn’t?” she smiled at me.
“You are one crazy lady.”
“This crazy lady needs to have a shower and go to bed.”
We cleaned up the ropes and put the things away. I had to clean a few spots off the carpet before we made our way upstairs.
She was standing in the bathroom after her shower, naked and shaved perfectly with toothbrush working away. I asked her from the bedroom, “Did you really enjoy getting tied-up like that?”
“Un-huh,” she mumbled still brushing her teeth.
“Did you want me to do it again some time?”
“Un-huh,” still brushing her teeth.
“What part did you like the best?” I asked.
I heard her spit, rinse and turn off the tap.
“Your cock,” she said smiling as she walked into the bedroom and then added, “and I love that little vibrator, thank you.”
“Maybe I’ll shove it up your ass next time,” I grinned at her.
“Maybe I’ll shove it up yours,” she grinned back.
“Turn the lights off.”
*
I woke up first. As I lay in bed I watched Caitlyn sleeping nestled up next to me. Her tattooed arm stretched across my chest. She was lovely. She looked very comfortable.
She stirred. I kissed her forehead.
“Good morning sweetheart,” I whispered. She hugged me and kissed my shoulder.
After peeing, we dressed to go downstairs in search of coffee.
“Are you staying for Sunday dinner?” I asked hopeful that she would.
“Only if you want me too,” she answered coyly.
“Of course I want you too. I love Sunday dinner with you. I love every dinner with you,” I grinned.
She insisted that she was going to buy stuff for dinner, complaining that I always tried to pay for everything. I talked her into taking the pick-up truck into town rather than her car. At least that way I was covering the fuel costs. Plus it was safer than that little Yaris.
I raked the lawn while she shopped in town. She was gone for hours. By the time she got back, I was raked out.
“I found a nice piece of roast beef,” she said as she packed away the shopping.
“Great,” I said watching her ass as she stuffed the fridge.
“It doesn’t need to go in the oven until,” she glanced at the clock, “about five o’clock. What do you want to do in the meantime?” she grinned.
She wanted to play.
*
Caitlyn and I were both completely naked.
As agreed, I let her tie me up. Pink Velco cuffs were attached to my wrists and ankles. Pink is not exactly my color, but what the hell, I bought them. Serves me right. She had carefully laid a bunch of pillows on the staircase and then, using rope from the shop, attached the D-clamps from the cuffs to the rails and spindles of the staircase.
I was spread eagled and my butt hole was somewhat exposed. I didn’t like that bit. I wasn’t going anywhere.
I had a hard-on thinking about what she was going to do. I had no idea. I just knew I was completely vulnerable. I couldn’t move.
“Heh heh heh!” she winced at me as she secured the final rope. “Payback time, heh, heh heh.”
She disappeared into the kitchen. What was that devious cunt going to do to me?
She came back with a big piece of ginger root. I’d seen her put it in the fridge. I thought she was going to make Chinese with it. She also had a paring knife and the potato peeler.
Naked, with her shaved pussy almost in my face, she started to peel the ginger root.
“Ever heard of figging?” she asked in a nonchalant manner.
“No. What’s that?”
“Heh, heh, you’ll see.” She was giddy.
She carved the ginger letting the peels fall onto my chest. She couldn’t stop giggling. All I could smell was ginger.
“What do you mean by payback time?” I asked, a little unsure.
She paused for a moment, still peeling the ginger. “I want to thank you for the dress, shoes and purse. And for the Italian dinner. I just want to say thank you in a very special way.”
It warmed my heart.
She carved, what I could only describe as a butt plug. She held it in front of my face, popped it into her mouth coating with saliva and then shoved it into my ass.
“Owww! Fuuuck!”
“Heh, heh, heh.”
Except for a finger, I’d never had anything in my ass before. That was way bigger than a finger. It hurt.
“Shit! Don’t do that. It hurts. Take it out!” I was furious.
She gazed at me with a curious smile on her face, but said nothing.
Then I felt it. Oh shit, I felt it!
“Aaaaagghhhhhh! Fuuuuuckkk!”
My asshole was burning. Burning ring of fire times a million. Holy shit!
I started writhing in the restraints. I couldn’t move. A Gila Monster tuber was stuck up my ass spitting out venom.
She was laughing, really enjoying herself. The cruel bitch.
I was sweating, in burning pain. The initial sting from the anal assault was gone, or eclipsed by the unbearable flame in my ass. It was getting worse by the moment. My chest was heaving.
“Fuuuuckkk!” It hurt. It stung. Big time.
“Don’t squeeze your bum hole together, it will only release more ginger juice. You’ve got to control yourself. Relax and the burning will fade away. In the meantime, eat my cunt!” She moved up the stairs and straddled my face.
How could that be sex?
I stuck my tongue out. I had no choice. I licked her. Tears were rolling down my cheeks. I tried to relax my bum, it didn’t seem to want to listen to instructions from my brain.
“Oh yeah! I’ve got your attention now,” she said as she ground her pussy into my face.
My asshole was on fire. She didn’t have my attention. She kept grinding her pussy onto my face. I was cognizant of the fact that she was making happy sounds. I was ablaze. Scorching hot. Consciously I tried to force myself to relax my ass.
Quickly she stood up and ran away. I heard my cell phone ring, once.
“It’s Frank Proulx,” she said reading the call display and pressed the phone to my ear.
“Hello?” I gasped.
(Doug, it’s Frank Proulx, how are you?”)
“I-I-m okay” I stammered. I wasn’t. I was a long, long way from okay. Try to relax I told myself.
(Listen Doug, I’m on my way back from the client’s now. They loved your proposal and especially the light fixtures. Sorry to call you on a Sunday.)
“O-okay,” I squeaked out.
(Your Caitlyn, she’s done a great job. She’s making me look good.)
“Ggrrhhh” Oh fuck. I’m burning! I couldn’t help but pull at the restraints.
(You okay Doug?) She kept the phone pressed next to my face.
“C-caitlyn’s here, do you want to talk to her?”
He paused then said, “Sure.”
Caitlyn put the phone to her ear as she sat down on my face again.
“Frank how are you?” she said in a graceful, yet professional tone.
(…)
“Oh he’s fine, just a little tied up right now.”
(…)
She was crushing my face.
“Great! That’s great,” she said to Frank
I was in melt-down. Chernobyl had nothing on me. She lifted her crotch momentarily to allow me a breath of air.
(…)
“Mmmm, unh-huh,” she said.
(…)
“Yeah.” She let me breathe again.
(…)
“Yeah we can make a mock up.”
I was fucking dying. It wasn’t just my asshole; my entire body was on fire.
(…)
“Just the pendant?”
She kept grinding her pussy onto my face. I needed air. And a fire hose.
(…)
“Cost plus twenty five sounds reasonable. Do we split the twenty five?”
She lifted again. I gasped.
(…)
“We’re good with fifteen.”
(…)
“That’s great, thanks Frank. I’ll have Doug call you tomorrow.” She lifted her pussy off my face. “I’ll just let you say bye to Doug, bye.” she stuck the phone to my face.
I gasped, “Gruumphtt.”
(You okay Doug?)
“I-I was just choking on a piece of ginger.” I stammered.
(Sorry, I didn’t realize that you were eating. You know Caitlyn did very well. The clients are impressed. She’s very talented.)
“F-frank, you have no idea what she’s capable of.” I must have been sweating blood.
(You must be very happy with her.)
“I’m absolutely delighted.” I was silently screaming. “I’ll call you tomorrow.”
(Okay Bye.)
“Bye Frank,” Caitlyn hit the end call button.
“Auuuuughh Fuuuuckk!” I screamed. The fucking lava stick was not letting up in my ass.
Caitlin bounded down the stairs and started doing a happy dance in front of me holding the cell phone in her right hand.
“They liked the proposal,” she sang as she danced.
I was in agony.
“Liked the proposal,” she swayed her hips side to side.
Shoot me, put me out of my misery.
“Liked the proposal,” her elbows were flapping, “liked the proposal.”
“Cate! Help!”
“Liked the proposal.” She stopped dancing. Stood with the stupid mock innocence in her face and asked, “Something wrong Doug? You should be happy. They liked the proposal.”
“It’s fucking killing me, stop it.”
“Ohhh…Dougie…it’s burning a little is it?”
“Please.”
She climbed up the few steps, straddled over top of me and looked down at me. “Doug, I’m going to ask you questions and you’re going to answer them honestly. If I don’t believe your answers, your figging continues for another fifteen minutes plus I’ll add some ginger into your pee hole. Got that? And don’t just give me the answers that you think I want to hear. Be honest.”
I nodded emphatically.
“Did you make me wear a pink dress in public to humiliate me?”
“No,” I squeaked.
“Why did you do it then?”
“I just wanted you to be more lady like, I hate that Goth look,” I gasped out.
“Hmmm.”
“When you say ‘I’ is that Doug my boss speaking or Doug with ginger up his ass, or both?
“Boss Doug doesn’t have a say. Only Ginger Doug does.” My ass was numb. My whole body was shaking.
“Good answer. But what makes you think Ginger Doug has a say in how I look?”
“Ginger Doug is falling for you big time. He only wants you to be happy.”
“And what the hell is wrong with Goth?” she demanded.
“Nothing,” I snorted back, “there’s nothing wrong with Goth…”
“It can be a little high maintenance,” she interjected then continued, “are you suggesting a Goth girl can’t be a lady?”
“No! No!” I yelled, burning away, “You’ve got me wrong! I just don’t like it on you. You’re lovely. Beautiful. You don’t need to paint yourself up and wear funny jewelry. Not for me! I’m falling for the Caitlyn that’s underneath all that Goth stuff. The one that dances when she paints, the one that teaches me how to set the table right.”
“What makes you think I will be happier not in Goth?”
“Right now, I can’t think.” I was in agony.
She smiled. “Last question,” she said.
“If I find myself in a vulnerable situation again, are you going to demand that I go girly again? Be honest.” She had a very serious look on her face.
I had to think this one through. It was impossible to rationally process anything with Dante’s Infernos burning in my ass. I decided to just answer honestly and hope for the best.
“Yes, every time,” I croaked out.
“Why?” she pressed an extra question home.
“Because you are far prettier than what you give yourself credit for. Sexy too.”
She smiled and pulled out the butt plug.
“Ohhh…it’s still burning.”
She untied me from the railings.
“Go have a shower and sort yourself out.” I scampered off.
After a shower where I basically gave myself an enema with the shower hose, I came downstairs with my tail between my legs. I was dressed in sweats and a tee.
She was too. She was making some tea.
“It will be a long, long time before I agree to letting you tie me up again,” I said.