You Lose. Now... Ch. 01byglendale22©
"You lose. Now take off all of your clothes."
Although I had heard this command several times, I never got used to the uneasy feeling it caused. At first, the consequences were actually kind of fun, but what began with my tendency to bet on my old college team eventually led to more and more embarrassing situations.
It started when I was dating Karen, the woman who would become my wife. Both of us had limited experience with relationships, and although I think we both soon knew that we were headed toward real sex in our relationship after a short while, we had not gone that far with each other when the betting games started.
I always backed our school's football and basketball teams, whereas Karen took a more analytical approach to games. However, her ability to pick winners was not giving her any rewards at first. "What's the purpose in saying who's going to win if I don't get anything for being right?" she finally asked.
"Okay, why not have the loser buy the pizza next time we order carry-out?"
"We already take turns paying for dinners, and if there wasn't a bet, we'd still get pizza. The stakes have to be something different and something we wouldn't be doing otherwise."
"How about the loser does what the winner commands for a day? If I won, I could tell you to clean my apartment or do my laundry."
We were standing in my kitchen at the time, and she swatted me on the seat of my pants then. "Not fair, pal. Cleaning your place would be real work. If I won and had you clean my place, you wouldn't really be paying much."
Realizing that she had seen through me on that one, I tried to distract her and exaggerated my hurt from the slap she had given me, whining and rubbing my backside as if I was in serious pain.
"That was nothing, pal. If I wanted to make you hurt, you'd know it."
So she'd seen through me again, but I wasn't giving up so easily. "You sure you're strong enough?"
"Well, maybe not to wrestle you down, but if you're not fighting back, I can make your butt sting."
"Yeah, really. Want to make a bet? That could be the payment. The loser submits to a real spanking. And since I'll win, you'll find out how hard I can hit."
This conversation had taken a strange turn, but I wasn't going to back down. Besides, the prospect of winning and having Karen's bottom at my mercy was too much of a temptation. "Okay, you're on."
It was in the middle of basketball season, so a game was coming up the next night. As was my habit, I wanted to bet on our team. After Karen consulted the paper for a few minutes, she agreed to take the other side. And the next night we watched our team lead the whole game and then blow it in the last minute.
Turning off the TV, I asked, "So what do I do now? Stand before you facing away, or should I lie over your knee?"
"It's not that simple, pal. The stakes were a real spanking. You lose, so take off your clothes."
"Say what? I don't recall hearing those terms of our wager."
"The terms were 'a real spanking,' and maybe you don't know what a real spanking is. Not that I've had much experience with it either, but my roommate Sheila has told stories of how she and some of her kinky friends play punishment games, and it is always on the bare bottom."
"Taking off all your clothes isn't necessary for that," I said, although I didn't want a bare bottom spanking either.
"No, but when she told of turning it into something even more fun with her boyfriend, she said being nude for the spanking increased the pleasure by increasing the embarrassment. In her words, that was a real spanking. We could call her if you don't believe me."
"We can leave her out of it," I replied. I didn't doubt the story, and I certainly didn't want to let anyone else know of my predicament. "Are you telling me that if I won you would be voluntarily stripping for me to get spanked?"
"That's what I'm telling you, pal."
Of course, we both knew there was no way to confirm that claim. Thinking about the possibility, though, made me see my loss in another light. Maybe I was losing tonight, but I couldn't lose forever. Paying off this bet could be sort of a down payment on getting to see Karen's body after another bet.
"Okay, so tell me what else is involved in a real spanking."
"You take off all of your clothes and assume a position that I dictate. I think I'll have you bend over and lean on a chair. Then you get ten spanks on the bottom. After that, you stand where I tell you with your hands on your head to display your red bottom. And I promise you, it will be red. You can get dressed after I have to go back to my room. Ready to start?"
I can't say I was ready, but I began to undress. Karen set a kitchen chair in the middle of the room and sat on the couch to watch. Taking my shoes and socks off was simple, as was pulling off my shirt. Unbuckling my jeans and lowering them was more difficult. I was in reasonably good shape and always thought of myself as at least average in looks. Still, this was a test. Karen was smiling slightly, perhaps wondering if I would really strip all the way.
After I set my jeans aside, she looked at me in my briefs, saying nothing. I turned to the chair, paused a moment, and pushed my underwear down and stepped out of them. With my back to her, I leaned over and placed my hands on the seat of the chair, trying to keep my legs together all the time.
She remained on the couch for a minute, enjoying her first sight of me in the nude. When she finally got up, she approached me from behind. I didn't know how much she could see of my penis, and she wasn't obvious about trying to look at it. First, she reached down to pick up my briefs and toss them aside, as if to emphasize my lack of clothing.
Then the first slap came, suddenly and pretty hard. I grunted a little and braced myself for nine more. She alternated her blows, some on one side of my bottom, some on the other, and some right across the middle.
Karen also paused between spanks, casually walking around me and the chair before suddenly striking my bottom again. Bent over as I was, I couldn't look at her closely as she moved around, so I couldn't see whether she was looking between my legs, and I couldn't anticipate her next blow.
Finally she had spanked me ten times, and I was told to stand up. I became very aware of how my penis had grown during the spanking. From behind, she reminded me to put my hands on my head, and then she passed me as she moved to put the chair back in the kitchen.
Coming back into the room, she saw me facing her, and there was no doubt in my mind then about how much of me she could see. I saw her looking me over. Looking at my erection, that is. It was the first time a girl had seen me fully nude. All my other sexual experiences involved getting my clothes out of the way, but never completely off.
As if to pretend to ignore me, though, she turned the TV back on and sat on the couch. I remained in place, wondering why she chose to sit behind me. Then I realized that she was admiring the deep color she had added to my bottom. However, she sat on the couch only at first. After several minutes, she moved to another chair from which she could stare at me from the side, and later yet, she sat in a chair I was facing directly.
Neither of us said anything until an hour had passed when she was getting ready to leave. "Turn around slowly," she commanded. After watching my display, she came over to say goodnight, careful not to touch my penis. It was still partially erect, and as she kissed me goodnight, she said, "I'm glad to see you enjoyed it too." Going out the door, she was quite obvious in the way she took a last look at my nude body.
I went into the bathroom to check out my bottom in the mirror, and it was as red as she promised. Even so, it did not really hurt that much, and by morning, the color had faded almost completely.
A week later, we had another opportunity for a bet, but my luck had not changed. That spanking began the same way with me taking off my clothes, although Karen told me to stop when I had stripped down to my briefs.
"Leave those on and go ahead and bend over the chair like last time."
As I assumed the position, I wondered if I was going to be spared the embarrassment of being fully nude. No such luck. She gave me a couple of lighter slaps, telling me, "These are just warm-up spanks, not part of the ten you get."
I made no complaint, and when she told me to get ready for the ten spanks, I braced myself. No spank came, however. Instead, she took my pants by the waistband and pulled them down slowly, tossing them aside again. Taking her time, she let her hand caress my bottom.
"Put your feet wider apart," she commanded, and when I did as told, she let her hands slide between my thighs and fondle my balls gently. When she let go, the first spank suddenly came. Again, there were pauses between blows, but this time, rather than simply walking around me, she also let her hands move over my backside.
Once all ten spanks had been delivered, she told me to stand as before. Rather than taking a seat to look at me, she remained beside me, feeling my bottom. "It's very red, pal, and it feels nice and warm too." Then she suddenly reached for my penis. Her grasp made it even harder, and she said, "This is nice and warm too. If you like these spankings so much, you should try to lose all the time."
I didn't know what to say. She was right, though, because I was certainly liking it at the moment. With her fondling and stroking me that way, I couldn't hold back for long, groaning and then getting semen all over her hands.
"Well, having a good time, pal? Looked like fun to me."
The rest of the evening went more or less like the previous occasion until she kissed me goodnight. This time, she held my penis as she kissed me, and then she gave it a quick kiss also. "I like watching you strip naked, and I like spanking your bottom, and I really like playing with this," she said, giving my penis a playful squeeze.
As before, I was not in any real pain, and the red in my cheeks went away by morning. I was beginning to understand that the actual penalty in losing these bets was in the sense of vulnerability and embarrassment from being the one nude. The spanking was just added to emphasize these feelings.
After that second time, I went to pick Karen up one evening at her dorm suite, and Sheila was there too. She looked at me kind of oddly and finally asked, "How do you like losing the bets."
I didn't know what to say at first, wondering how much she knew, but she went on, "From what I hear, you like it a lot. And I wish I could be there sometime to see you bent over and paying your penalty." I probably blushed to learn that Karen had let her know what we had been doing, right down to the details of my position for getting spanked. It made me wonder how much else Karen had described to her, and figuring she had given her all the details, I felt like she had in fact seen me already.
That evening, I asked Karen how much she told Sheila. Turns out she had described everything to her. When I asked why she let Sheila know so much, Karen told me it was sort of a payback. Some weeks before, Sheila and a guy she was dating used spanking each other as foreplay, and Karen could watch some of it when Sheila made the guy strip first in their living room. Before Sheila escorted him to her bedroom, she took him across her knee and spanked him while asking Karen to tell him what she could see. And even once in the bedroom, Sheila left the door open.
Anyway, maybe Karen was trying to make it up to me after she saw how her roommate had embarrassed me, or maybe she was beginning to take pity on me, or maybe she wanted to get us moving more quickly to the day when we really slept together. Either way, I think she gave me a break when a few nights later she agreed to bet on an opponent that our school's team could beat easily.
As soon as the game was over, she got the chair out of the kitchen and then asked, "You want me to take my clothes off myself, or do you want to take them off for me?"
Not a bad pair of choices, but I replied, "I'll watch this time."
Whether she wanted this to happen or not, actually undressing for me was causing her enough embarrassment to make her movements a little tentative. She didn't know exactly where to start after she kicked her shoes off.
"How do you want me to do this?"
"Why not take the shirt and jeans off first? Then your bra before your panties. And be sure to face me the whole time unless I tell you otherwise."
As ordered, she stripped to her underwear, and I stopped her. Her figure was athletically fit from running track in high school, and between her breasts, I could see rippling of her skin over her breastbone. I did not care about their size, though, because Karen's body was what I wanted. "Let me see you turn around slowly like that."
Then I told her to continue, and when she unfastened her bra and dropped it, I could see her thin, practically flat chest. Her wine-dark nipples were hard and poked out like thick erasers. Seeing my smile, she continued to strip, taking off her panties to reveal another striking feature, a shaved vagina.
I must have been staring rather intently, because she said, "I keep it that way to make up for my breasts."
My eyes saw nothing I didn't like, but I simply said, "No complaining. Get yourself ready for a real spanking." I almost couldn't move, though, enthralled by the sight of her lithe body bent over the chair like that. At 5'8", she was just an inch shorter than me, but without her clothes, her legs looked so long and sexy. Before getting up, I realized as I stared at her that I'd never seen a girl's nude body so openly until then. Before, the space was always cramped, like in a car, and the light was always dim at best. With Karen, though, not only was she out in the open and well lit, she was on display for as long as I wanted to stretch out the moment.
Like her, therefore, I took my time, and I took advantage right away, running my hands over her bottom, her back, around to her nipples, and between her legs. She was very wet.
"We haven't really started, and I see you're already enjoying this."
She giggled a bit, and I made her stop with a resounding slap across her slender bottom. Then she took her spanking more seriously, although we both enjoyed the whole experience. When she had to spend time displaying her red bottom, I often told her to turn around for me, unable to decide which view of her body excited me most. And rather than kiss her goodnight, I invited her to stay, and we were both naked the rest of the night.