Penny’s online naughtiness develops into a real-life experience of bondage, discipline, power-play, pain, and pleasure

My online friend, Jack, is the only person who knows the real me. To the rest of the world, I am a good wife, a great mom, and a respected business woman. And everyone always thinks of me as innocent. They don't seem to notice that mischievous twinkle in my eyes. But Jack knows the real Penny. The Penny who wants to be a submissive slut.

My husband does not understand my needs. How can he? He's a good, moral man. He loves me tenderly. He caresses me gently. And I adore his sweet, sensual touch. But sometimes, many times, I secretly crave some not-so-soft touches.

I am a faithful wife. I cannot bear the thought of betraying my husband or destroying my family. So I go online at night, when my husband is not home. And I watch dirty movies while I pleasure myself... repeatedly. Or I have filthy chats with my online friend in which I share all my secrets and fantasies. Sometimes, we even talk on the phone, while my vibrator brings me to heavenly orgasm.

But the fire still burns within me. These chats and movies are not quenching my thirst as I hoped they would. Instead they simply add fuel to my fire.

And I want more.

"Penny, are you ready to take this to the next step?" Jack asked me.

"I...think so." I replied, a bit tentatively.

"Well, as you know, I'll be in New York tomorrow. So, if you are certain that you are ready, then come meet me in my hotel at 2:00 PM. Room 412."

"I'll see if I'm available." That's what I said, but what I really meant was that I'd see if I have the guts to finally live out some of my fantasies. And betray my husband.

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I went into the elevator and took it up to the fourth floor. I hesitated as I walked slowly toward room 412. I knocked ever so gently on the door ‘tap, tap.’ There was a part of me that was feeling nervous and a bit shy, and kind of hoping that he may not hear me.

"Hi Penny! Come sit down."

I walked into the hotel suite, and sat on the couch while Jack sat on the chair next to me. We looked into each other's eyes. Jack held my hands in his. I smiled at him, excited to finally touch and be touched by the man I have fantasized about for several months.

"Wait right here, Penny. I have a gift for you."

Jack left the sitting room and a returned a few moments later with something in his hand.

"Do you know what this is, Penny?"

"Umm...yeah, I guess so."

"Lift up your hair." I put my hands behind my head and into my long brown hair, raising it off my neck and shoulders.

Jack came up behind me and fastened a black, leather collar around my neck.

"Now I own you."

Ooh, how I've longed to hear those words. I suddenly felt more alive than I had ever felt before. My heart was beating loudly within the walls of my chest. And I could feel my blood pumping through my veins.

"Penny, I must go to my meeting now. But I do plan on spending the entire day with you tomorrow. Meet me here at 9:30 AM sharp. Make sure you bring your collar. I also want you to wear something very sexy under your clothes tomorrow, so that I can have fun unwrapping my new toy. Oh and bring those sexy pink panties of yours that you showed me in the first picture you ever sent me."

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When you're married eight years and have 3 kids, sometimes you just don't feel sexy. I have a beautiful, tight figure, but my husband barely even notices me anymore. I felt a rush at the thought of dressing sexy for a man who will appreciate it. And I wanted to look my absolute best.

I put on a black satin overbust corset that proudly displayed my cleavage and sexily laced up my back. I put the tips of my toes into my sheer black stockings and slowly inched them up my legs, attaching them to the garters hanging from the corset. I slipped on a tiny black lace thong which fit snugly against my firm bottom and bald pussy. And I adorned my petite feet with tall shiny black heels. Finally, I picked out a dress to wear -- a form-fitting leopard print dress, that showed off my every curve.

With my collar and pink panties in my purse, I was ready to go meet Jack for our day of living out our fantasies. I hoped that I would enjoy the real-life play as much as I enjoyed my pretend play with him.

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Dolling myself up took some time, so I was running a bit late, but I managed to get to the hotel at 10:00 AM. Jack was already waiting for me outside. He looked a bit ticked at me for being late, but more so, he appeared excited to see me.

Jack walked toward me, took my chin between his thumb and forefinger and brought my face to his. He gave me a long, passionate kiss on my moist lips, as his hands worked their way down my back, only stopping when he reached my bottom. He gave my cheeks a hard squeeze and whispered into my ear, "Making me wait half an hour for you was a big mistake, young lady. You'll pay for that later."

Hearing those words caused a tingle within me that I had never felt before. I was aroused at the thought that I might be punished today. The juices of my pussy were trickling into my skimpy panties. And my nipples were hardening beneath my corset. My body was aching with desire and I pressed myself against him as I moaned softly, quietly letting him know what was happening within me.

"Penny, I thought we might do some shopping before we get started. Let's go." Jack put his arm around my tiny waist as we walked through the crowded streets of Manhattan. There was a part of me that was worried about being seen by a friend or family member. But there was a bigger part of me that simply did not care. At this moment, all I wanted, was to belong to him.

What kind of shopping did Jack have in mind? I wondered. Perhaps he wanted to buy me something sexy to wear for him.

Jack stopped in front of a shop called The Sex Toy Emporium. Hmmm...toys? That could be fun.

We walked inside together, looking like a couple instead of two people who were married to two other people. I felt a bit shy and nervous as I had never been inside one of these unsavory places before.

First, we explored the first floor which had all sorts of vibrators. I had fun examining each one with my fingers and imagining how it would feel to be pressed up against or pushing inside my dripping pussy. There were also many butt plugs, some were made of a squishy material and others were made of glass. Those looked a bit frightening to me.

"So, what do you want to get, Jack?"

"What I'm looking for is upstairs. Come up with me. I need your help for this."

We walked up the stairs together. There were so many toys on the first floor. What could he possibly need that wasn't here? I couldn't imagine what Jack was looking for.

As we reached the top step, my brown eyes opened widely, taking in everything I was seeing. There was a room filled with rows upon rows of masks, collars, gags, whips, floggers and paddles. There were two cute girls looking at the masks, trying them on and giggling. I gave one of them a nervous smile as I followed behind Jack.

"I was thinking about investing in a nice leather paddle, but I need your help picking one out."

"Ummm, I don't really know much about paddles. In fact, this is the first time I've ever seen one." I replied.

Before I could finish my thought, Jack reached for one of the paddles and gave me a whack on my backside.

"Cut that out!" I was a bit embarrassed. The two girls were watching us closely. But they seemed to be enjoying the show.

Jack put the paddle back and grabbed another. This one was a heavy black leather paddle, shaped like a long rectangle. Jack held the handle of the paddle, and before I could get my ass out of the way, he landed another smack on my bottom. This one caused me to leap forward a bit and let out an "Owwww!"

"Thank you for your help, Penny. I'll be getting this one. There's one more purchase I need to make, but it's upstairs."

"There's another floor?" What else could this place possibly have? I followed Jack upstairs yet again. This time I only felt confused. There was all sorts of medical-looking equipment on this floor. Jack grabbed something that looked like a metal syringe. I wasn't sure what it was, but I was definitely nervous.

We went downstairs and Jack paid for his purchases. We left the store together. A car drove by and stopped in front of us. It was the two girls from the store. "Have fun guys!!!" They shouted as they drove off.

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Back in the hotel room, Jack took a seat on the couch and pulled me into a sitting position on his lap. He kissed my lips with his, and pushed his tongue between my parting lips, exploring the insides of my mouth.

"Did you bring your collar?"

"Uh huh." I opened my purse and handed the collar to him. I moved my hair to the side as Jack placed the collar around my neck for the second time.

"From this moment on, you are to only address me as Sir. Understood?"

"Yes." I answered.

"Yes, what?"

"Oh. Yes, Sir."

"Good girl." Jack said as he lifted my dress over my head and tossed it aside. Jack stared at me for a moment, just admiring my body. He ran his fingers over the top of my bulging cleavage.

"Stand up and turn around."

I did so without a word. And Jack inspected me from behind. He untied the laces of my corset and then tightened them, cinching my waist even more.

"You look amazing, Penny."

"Thank you, Sir."

"We're going to have a safe word, just in case you feel like anything is getting too out of hand. If you feel that way, you need to say, ‘red light’. Okay?"

"Okay, Sir." Safe word? Why do we need one? Is he going to actually hurt me?

"Now I want you to walk to the door and then walk back to me. Shake your hips a bit. Be sexy."

I started walking to the door, swaying my hips from side to side. I felt a bit embarrassed being on obvious display like this. I walked back toward Jack, our eyes locking, and a mischievous smile forming on my lips.

"Get on your knees."

I got on my knees before him, my body between his open legs. Jack took a length of rope and tied it through the ring in the front of the collar, creating a leash.

"Now crawl to the door and back to me."

I turned around and crawled away from Jack, my ass wiggling back and forth. When I turned around to crawl back toward him, I saw his new purchase in his hand. Jack stood up and grabbed my leash.

"Keep crawling."

I crawled around while he led me by the leash. I definitely felt silly at this point. But I was also quite aroused. I secretly felt ashamed and freakish that I was turned on by this.

"Whack!" Jack smacked my ass with the leather paddle.

"Ow!" I stopped and looked up at him with big pleading eyes.

"Keep crawling." Jack said as he landed another crack on my bottom.

"Ow!" I shouted again, but this time I kept crawling. Jack laid a few more smacks on my aching backside as I crawled around his hotel room.

"Now I want you to climb onto the ottoman and get on all fours."

"Yes, Sir."

Jack stood in front of me holding the paddle in his right hand and a flogger in his left hand. The flogger had dangling strands of leather and fur. "It's time for me to punish you for your tardiness. Choose one and you're going to get ten spanks with it."

I already knew the harsh sting of the leather paddle. I pointed to the flogger, uncertain as to whether or not I was making the right choice.

Jack walked around me. I could not see what was happening, but I heard a loud, "SWOOSH!" as the flogger came down hard on my sensitive skin. It definitely stung, but the paddle was so much worse. My bottom was struck four more times; the pain increasing with each one. Then two on the back of my right thigh. Ooh, the skin there is so sensitive! Two more on the back of my left thigh. “Yeow!” And a final harder blow once again over my burning derriere. "AAAAH!"

"Stand up, Penny; you're doing great."

I stood up and rubbed my stinging cheeks . Judging from their warmness, I was certain that they were already quite pink. Jack took my place on the ottoman in a sitting position. And I was standing next to him.

"Last week I asked to you to remind me about the first chat we ever had. But instead of reminded me, you teased me for being so forgetful. And that was hurtful."

"C'mon, I was just goofing around." I really was just kidding around. At the time I thought it was funny, but suddenly it seemed like a very big mistake.

"Well, you mocked me. And that was very childish of you. Don't you think? So now you're going to be punished like a bad little girl." And before I could protest any further, Jack took me by my arm and pulled me across his lap. He held me tightly over his knees as he spanked my bottom with his bare hands. I was definitely feeling some heat on my cheeks at this point, but I loved the sensation of being across his lap. And being disciplined like a naughty child.

The spanking stopped briefly as Jack grabbed the waistband of my little black thong and slid it down my thighs all the way to my knees. I felt a bit humiliated. But I liked it. Jack continued with my spanking. With each slap, I could feel his cock growing stiffer beneath me. The spanks were getting harder, faster and more intense. My legs were kicking so furiously that my panties went flying across the room. My entire body was tensed up and squirmy as I tried my best to get out of harm's way. I finally managed to roll myself off his lap and onto the floor. I pressed my bottom against the carpeted floor, protecting myself from any more swats.

"You have three seconds to get back over my lap."

"No. I can't do it anymore. I can't!" I cried as I shook my head from side to side.

"Or you get the paddle again. One...Two..."

I wore a pout as I crawled back over Jack's knees. My already marked up behind on display once again.

"Look how nicely you climb back over my lap. Even though you know what I'm going to do to you." This time Jack locked my legs in place between his own legs. I could hardly move at all. And with that my spanking continued. His merciless right hand came down hard, taking turns with each cheek. I felt so foolish as tears ran down my face. I truly felt like a punished little girl.

But just when I felt like I couldn't take any more of this harshness, Jack's fingers creeped over my ass and found the warmth of my pussy. He gently ran two fingers around my labia and said, "I don't even have to go inside to see how wet you are." He took his soaked fingers and pushed them into my mouth. I hungrily licked and sucked my pussy juices off his digits, enjoying my own sweet taste. My eyes opened wide in amazement at the reaction Jack was able to elicit from my body. I was filled with arousal and excitement as I was getting to know my newly-discovered submissive self.

"My body belongs to you. Do with me as you please."

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When you're having a good time, you can forget to do simple things...

like eat. Our limited time together was going by quickly and we hardly even noticed our hunger. But when our stomachs started growling, Jack wisely suggested that we find something to eat.

There was an old-fashioned Italian restaurant a few short blocks away. The decor was charming with its muted lighting and striking antique fixtures. And the food was delightful. The only thing that could have been better was the softness of the seats. They definitely needed more cushioning. I sat gingerly on the hard wooden chairs, shifting my weight from side to side as my bottom ached beneath me.

"I am very much looking forward to pushing you even further." Jack declared.

"Further?" I questioned as my fork fiddled with the last remaining ravioli on my plate.

"Well, yes. All I really did so far was spank you a bit. I can be more creative than just walloping you." Jack asserted as he stuffed the final forkful of his gnocchi into his mouth.

"I trust you, Jack. So I'm just going to hand myself over to you, and you do with me as you wish. Okay, Sirrrrr." I emphasized the 'sir' in a slightly sarcastic tone.

"I'm not kidding, Penny. You are really going to learn some things about your limits."

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Jack took me out onto the balcony of his suite.

"Do you think anyone can see us here?" I asked.

"Who cares?" He replied as he lifted my dress up and over my head. Jack planted some soft kisses on the top of my cleavage as he began to unhook the front of my corset, exposing my perky breasts and erect nipples. He got onto his knees and pulled my lace panties down a bit, kissing my smooth bare skin.

"Did you do this for me?" He questioned as he ran his index finger up and down my freshly shaved pussy.

"Yes, Sir. I thought you might like it." I responded.

"Well, you were right." He gave me a few kisses on my bald lips, while my legs quivered against his face.

"No, no, no. Not yet. You don't cum without my permission."

I felt slightly disappointed, but I liked that Jack was controlling my pleasure. I stood on the balcony completely naked while Jack fondled and caressed every inch of my body.

"Go sit on the couch. And open your legs wide." Jack ordered.

I walked back into the room and sat in the middle of the couch with my legs stretched open to each side. Jack walked toward me with four long pieces of rope in his hands. He tied a knot around my right ankle, slipped the rope through it and went around 3 times creating a cuff. He took the other end of the rope and tied it to the leg of the couch, so that my right leg was completely open and immobile. He then did the same to my left ankle. Smiling at me, Jack took the remaining two lengths of rope and tied them around each wrist in a similar fashion. With my arms extended out, he tied the opposite ends of the rope to the back legs of the couch. At this point, my body was stretched open and I could hardly move at all.

Jack licked his fingers and rubbed them over my exposed genitalia. He gently pinched my clit between his fingers and pulled on it a bit, forcing a soft moan from my lips. Then he took a clear plastic cylinder and placed it right over my clit, attached a pump to other side and started pumping on it.

"Aaaaah!" What an intense feeling! My meat was being sucked up the tube. I watched as my clit grew longer and thicker, slowly filling up the cylinder. When the pressure reached its max, Jack released the pump, leaving the cylinder attached to my swelling love pearl.

Jack went back to his case and took out a powerful plug-in vibrator. He turned it on the low setting and pressed it against my wet opening.

"Mmmmm." The vibrations felt so good.

"No cumming." He reminded me in a stern voice as he continued moving the vibrator around my lips and on my covered clit.

Jack released the suction of the cylinder and took it off me. I looked at and admired my now puffy and engorged clitoris. He lifted up the vibrator and was about to put it on my swollen flesh....

"No, that's gonna kill! It's too sensitive now. Seriously!"

"Shhh." Jack put his finger over my lips to quiet me. He took out some metal nipple clamps with a connecting chain. And clamped my right nipple and then my left. I squealed from the sudden sharp pain. Jack took the chain that was hanging between the clamps and put it into my mouth. Then he did exactly what I was dreading. He put the vibrator directly on the swollen head of my clit.

"AAAAAAH!!!!!!!!!" I screamed as I spit the chain out of my mouth. I tried to scooch my bottom a bit, in a worthless attempt to get my sensitive button out of the way. But I could really only move an inch or two. The ropes were holding me tightly in place.

"I don't like it. Stop! Please stop." I really felt like I couldn't take it anymore. My cheeks were still stinging from earlier in the day. And now, my tender clit was burning. My nipples were sore and aching too. And my feet were getting numb from the ropes. I knew I could utter the safe word and all this would be over, but I was afraid that I would feel like a failure. Or ruin the game.

"This isn't about what YOU like or don't like, Penny."

"Please, I really really hate this!" I said in a whimper, my tears starting to trickle down my cheeks.

"Then why is your pussy betraying you?" Jack asked as he turned off the vibrator and pushed his fingers into my dripping cunt.

Jack untied me and took me onto his lap. I leaned against him, sobbing as he stroked my hair.

------------

"Did you remember to bring your pink panties?"

"Yes, Sir." I responded as I reached for my purse and pulled them out.

"Well, put them on."

I bought those panties not too long ago, when I first began exploring some of my fantasies. I remember seeing them in the lingerie shop and thinking 'those would be perfect for spanking!' The feminine pink lace. And the cheeky view in the back. I slipped my legs into my lacy pink panties and pulled them up.

"I want you over my knees again."

This time there was no protesting. I simply walked over and laid myself over Jack's lap, like a very good submissive girl. The tips of my toes were touching the floor behind me while the palms of my hands were touching the floor in front of me. And my long brown hair was draping over my face.

My skin was still somewhat pink and tender from my earlier spanking and paddling, so Jack went a bit easier on me this time. Just a bit. He lifted his right hand and came down hard on my exposed skin, spanking each cheek, alternating with a rhythm. He wedged my panties together in order to reveal more of my flesh and continued.

No complaining. No whining. No whimpering. I was toughening up.

"Get up, Penny. You have to see this." Jack led me to the full length mirror.

"Look, your ass is the same color as your panties!" My pink cheeks were in fact just as pink as my lacy panties.

"Wow! Nicely done, Sir." It really was a nice view.

"I know about all those spanking videos you watch at home every night. Is this what the girl's ass looks like at the end of the clip?" Jack whispered in my ear. I nodded my head.

--------

Jack went back to his case and pulled out a satin blindfold and that metal syringe which he purchased earlier in the day. I must admit that I was a bit scared at this point. But I trusted him. Jack blindfolded me and led me over to the ottoman. "I want you on all fours with your ass up high." I got on my hands and knees and raised my bottom. Jack pulled down my pink panties and left them around my knees. I felt his lubed up finger circling my asshole and then penetrating me, and that felt really nice. But then I felt the cold metal tip of the syringe entering my most private area. I started to wonder what was being done to me, but then I felt a sudden rush of warm water flooding my insides. It was an enema syringe! I stayed very still as Jack filled me up with the water. When the syringe was empty, Jack walked away, but I could hear him refilling it. He came back and emptied the second syringe-full of water into me. I could feel my belly getting quite full and I was having a few cramps from all the water. Jack put one hand underneath me to rub my belly, and with this other hand, he was filling me up with a third dose of water. My petite body couldn't handle any more; some of the water started to drip onto my thighs and panties.

"Hold it." Jack ordered me.

I squeezed my cheeks together, trying to hold in all the fluid. After Jack saw that I was managing to keep everything in, he turned on the vibrator and started rubbing it against my pussy. I was moaning from the pleasurable sensations, but too afraid to "let go" because I was scared of the mess I might make.

The cramping was getting worse. "Ow! Please let me go to the toilet. Please, Sir. I can't hold it much longer."

"Off the ottoman and get on your knees on the floor." Jack suggested, thinking a change in position might help me keep everything in a bit longer.

I got onto my knees, panties still around them, clenching my cheeks together and holding all the water in. My insides were aching. Suddenly, I felt warm flesh pressing up against my lips. I opened my mouth, eager to accept this new visitor.

"You may go to the toilet right after you make me cum."

I licked up the right side of Jack's swollen cock, and then the left, getting him wet with my saliva. I twirled my tongue around the head and then flicked my tongue right under his cock head. I opened my mouth wide and moved my head up and down along the length of his shaft, while at the same time moving my tongue back and forth. My right hand began gently massaging his balls. I had to work quickly. I had to get this water out of me! I licked my left hand and wrapped it around his member, moving up and down, jerking him, while I bobbed my head in perfect rhythm. I pressed my lips to increase the pressure a bit. I could feel him getting more swollen in my mouth. I tightened my grip and started going a bit faster. And finally, I could feel my prize was about to come. The swollen meat inside my mouth was twitching as a stream of cum started squirting out. Jack pulled himself out of my mouth quickly and splattered his heavy load all over my face, mouth and hair. I could feel the warm liquid dripping down my chin and onto my naked breasts.

I quickly jumped to my toes, my panties sliding to my ankles. "May I go now? PLEASE!"

Jack removed my blindfold and put his arm around me. "Look at the clock. It's 7:32. You may go at 7:35."

We watched the clock together. Time moved very slowly. I was hopping from one leg to the other, trying to distract myself from the uncomfortable feeling. And trying to keep everything inside.

"7:35!" Jack announced.

I kicked my panties aside and skipped to the bathroom in an obvious hurry. I locked the door behind me, and admired my cum-covered reflection in the mirror quickly before sitting down and expelling what felt like gallons of water. It took me about twenty minutes to empty out and clean myself up. I wondered what Jack might be doing during this time. I was soon to find out.

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I came out of the bathroom in a much more relaxed mood. Jack was standing by the kitchenette holding a glass of water. There was something white sitting inside the glass. I noticed a knife and a vegetable peeler on the counter. I was very confused.

"Penny, do you know what figging is?"

"No."

"I carved some ginger into the shape of a butt plug. I'm going to put it in your ass and it might burn a bit. I haven't done this before, so if it really hurts, you just need to tell me. Okay? Are you willing to give it a try?”

"Yes, Sir." I was a bit nervous, but also curious to try. And I liked the idea of him sticking things in my ass.

Jack sat on the couch and led me across his lap. He licked his finger and brought his saliva down to lubricate my tight little hole. He grabbed the ginger plug and slowly worked it into my asshole while I squirmed over his naked lap.

"How are you doing, Penny?"

"It's fine." I was trying to be brave. It was stinging a bit, but I tried my best to relax and then it wasn't too bad. Just very warm.

"It looks like you really like it, Penny. Your pussy lips just opened up like a flower. And you have a stream of juice dripping out. My leg is getting all wet from you."

I could feel my face blushing.

Jack reached for the vibrator and started rubbing it up and down my lips. I rolled over and opened my legs giving him better access. He started moving the vibrator around in circles, working from the outside in. I started to feel small ripples of pleasure taking over my body, causing pleasurable muscle spasms in my lower region. "Ouch!" Every involuntary tightening of my anus would cause the ginger to get hotter and hotter. I loved it and I hated it. The pleasure was getting more and more intense. I could feel my orgasm approaching. I rocked my hips back and forth against the vibrator. Jack pressed it hard and deep against my skin.

"I'm about to cum... about to cum...." I said in a breathy voice.

"Ask me for permission."

"Please! May I cum? Please! Please! I'm gonna cum. Please." I cried out, tears forming in my eyes. I was panting and sweating.

"I'm going to count to ten and then you may cum. One...two...three...four..."

"Seriously, I'm cumming. I can't hold it." I begged.

"Five, six, seven, eight..." Jack counted a bit quicker, realizing I was on the edge.

"Nine........ten."

"Aaaaahhhhhhhhh!" I screamed as I reached the peak of my orgasm. I felt warm waves of energy taking over every inch of my body. My heart rate was increasing and my breath was getting heavier. I lowered my hips, getting myself away from the vibrator. My clit had become too sensitive to be touched.

Still in a daze, I heard my cell phone ringing and I ran to get it.

"Penny, the barbecue started an hour ago. Is everything okay?" My husband questioned me.

"I... got tied up with some projects at work. I'll be home soon." Wow! I had totally lost track of time.

I got dressed quickly, grabbed my purse and ran for the door. Jack gave me a big hug and we looked into each other's eyes. Each of us feeling conflicting emotions of happiness that we had finally met and lived out some of our fantasies, and sadness that I was leaving and we didn't know when we would see each other again.

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I arrived home close to 9:30 at night. The barbecue was long over. I kissed my husband on the lips, feeling somewhat guilty for my betrayal. We went upstairs to our bedroom. I did not want to undress in front of him because I knew there would be some marks on my bottom that I would need to hide for a few days. I lied on my stomach on my bed, checking my email on my laptop. My husband walked over to me and playfully gave me a slap on my butt.

"Ow!" I screamed out.

My husband scrunched his eyebrows together and asked, "Umm...Penny, why did that hurt?"