His Sister-In-Law Is Not Naivebyembarassed©
The holidays were approaching and my wife asked if her sister could come over for dinner. It had been over a month since she had visited. Sara was my wife's younger sister who had just recently graduated college and moved to our neighborhood. She was a great girl who was always helping out. Unfortunately she began to think our home was her home and she began to get on my nerves! But it had been a while so I said of course.
A week later we were all having dinner, as we sat around the supper table and caught up, I found myself staring at Sara's very cute body. She was just 5'3" and couldn't have weighed more than 110 lbs. I have never been attracted to her in the past and perhaps it was just the second bottle of wine speaking, but in either case she looked hot tonight. We all continued to chat and drink and drink some more. We went into the living room and listened to music and continued having a great evening. I think the wine was going to my head because I found myself stealing glimpses of Sara more frequently, her butt was firm and when she bent over I was able to see just the top of her G-string panties. At 10:30 just about when Sara should be headed out the door, my wife told me that I needed to be punished for starring at Sara tonight. I laughed nervously, my wife had never mentioned punishment ever before in the nine years we had been happily married? Not to mention feeling like a fool in front of Sara. I was surprised and quickly offered what must have sounded like a very weak excuse. I wasn't looking at your sister's butt. Sara jumped in and said that she had seen me looking at her behind and that she would be able to help with any punishment that was due. I laughed again, Sara is a pretty naive girl, I really didn't think she was up for doling out any punishment. What was she doing? Punishment what are they talking about! Sara again said, don't worry I can do it in 45 minutes on the nose, she looked at my wife who nodded in approval.
Sara said she would punish me but only if I understood this was just going to be a 45 minute punishment, and there was to be no backing out. I looked at my wife and she just nodded. I have to admit this was very odd, never ever has anything like this ever happened. I just lead a normal life, happily married, with no punishment of any kind in the past. Sara jumped up and said she would be right back, she quickly left the room. I clearly had no idea what I had gotten myself in to. Punishment? What was going to happen? I began to think maybe this was actually going to be fun. Maybe a few swats on the backside, or maybe just Sara and my wife had planned a threesome!
She returned with a duffle bag, and pulled out a timer, she set it for 45 minutes and pressed start, it beeped. Cool I thought the timer has already begun how bad can it be? She is such a cute girl, and when she walked over to me I thought this might actually be really fun...who knows maybe tonight is when I will get to see Sara naked! She asked me to stand up and come over to the chair. I did as I was told. As I walked across the room I noticed my wife had a really funny smirk on her face, she must have known of what was to come...? Sara asked me to bend over the chair, it was a very high back chair so I was leaning over just slightly. She pulled a long scarf from the bag and began to tie my hands in front of me, she almost looked like she knew what she was doing? She tied the scarf around my hands and finally over the back and onto the legs of the chair, and a few minutes later she announced she had finished.
I was standing there bound to a chair with my wife and sister-in-law in my living room, how weird. The scarf was not extremely tight, but I definitely knew I was not supposed to be able to get free without some help. Sara and my wife giggled and left the room, Sara said some coffee might be nice. This was strange, the timer read 39 minutes, how much could they accomplish especially if they were walking away? .......just then Sara announced she had forgot something, she walked back into the room walked up behind me and whispered in my ear "now the fun begins." She reached around the front of my pants unbuttoned them, quickly slid her fingers in the waistband of my pants and underwear and slid them down to my ankles! I was nude! And Sara was looking at my ass. I was so embarrassed I almost died, I felt the cool air rush over my skin, my balls retreated with the cold and I realized this was going to be very scary. Sara touched my back with her warm hands and ran her fingers down to my bottom, she laughed very quietly and said your wife doesn't even know I've seen you naked yet, she paused and said how does it feel to be nude in front of me? I Was mortified. I'll be back in just a few, And then she left the room. I heard them making coffee, and still could not believe I was naked! Sara had seen my bum, and probably more!
What was my wife going to say? Did she know I was going to be naked when she entered the room? Did she know that Sara had planned to see me nude? I suppose I could have untied myself but was this part of the plan, would I have gotten in more trouble? Perhaps Sara had gone too far, maybe my wife would be angry I don't know? Well it didn't matter now because it was too late They both just stepped back into the room! My wife gasped at first but then just stood there quietly. Sara jumped in and said come on time to let the punishment begin. I was so embarrassed. My face must have been red as a beet. Sara walked over to me and swatted my ass, it stung a bit but it was really just the feeling of another woman touching my bare skin that felt weird. She reached into the canvas duffel bag and puled out a tube, it looked like a toothbrush holder. She then walked behind me and I heard a beep. It was not the timer, that was sitting in front of me counting down...and not fast enough. My wife giggled and said I can't believe it, Sara then said it was time to take my temperature!! Oh she must be kidding...my temperature this is nuts. Sara then leaned in and told me that this was probably going to cause me to get hard! I almost fainted.. She slowly separated my ass cheeks, but I was so focused on what she had just said about getting hard. She must have known what she was doing because the more I tried not to get hard the harder I was getting. She took her finger and slowly massaged my anus, my dick grew harder, she must of had some Vaseline on her finger because before I knew it she was penetrating my ass. She wiggled her tiny finger slowly in and out and she whispered in my I ear I told you your were going to get hard. She was right!! after just a few teasing strokes I was at full attention, my cock was on display and Sara must have been happy as can be! What was my wife thinking, was she pleased or pissed or was she enjoying this? Sara then took the thermometer and slid it ever so gently in my ass and pressed the start button.... I was dying, I looked at the timer we still had 21 minutes to go, was it going to get worse?...if I only knew.
Sara then asked my wife to come a little closer and watch what was coming up next. Sara reached around to my very hard penis and stroked it just a little, I gasped, Sara's hand was touching my cock, it felt good..was she going to make me cum? Yes Sara I blurted out...Sara laughed and said not yet, and she quickly stopped! My wife was watching intently. And just then I heard a beep....98.6 my wife said, good said Sara, and she quickly pulled out the thermometer.
Sara announced it was time to warm up my bottom. Now I have never been spanked, and especially not in front of my sister-in-law, And never in front of any one with a raging hard on! Sara told my wife that spanking is a great motivator, and that the reason it works so well is because it makes the victim very embarrassed. She was right I was embarrassed, and it seemed like this may be just the beginning. Sara began swatting my ass softly as a warmup. But after just a few minutes she increased the frequency and intensity. It really began to hurt. After every spank I went up on my toes just a little to try and ease the pain. Then she reached in her devilish bag and grabbed a hairbrush. You have got to be kidding I said, she laughed and said oh no, this is going to be fun. Wap ouch I yelled, my wife just stared at my backside, and then came another....ouch that really hurts I said, Sara replied good. She continued to alternate with spanks to each cheek. My ass was on fire. I looked at the timer 14 minutes? Will I make it?
Sara announced that it was time for my wife to help and instructed her to get the camera! This was bull I thought but before I could say anything else the flash had already gone off...twice. My wife was laughing and here I was tied over a chair with a very red ass and a woody! Sara began messaging my bum and every so often she would slide her petite finger just ever so slightly into my ass. Every time she did it I got just a little harder, I was about to explode. I didn't really want to cum in front of her though this was just too embarrassing. I looked at the timer just 6 minutes until it was over...thank goodness.
My wife chimed in and said what about the drawing you mentioned, and Sara quickly said that now was as good of time as any. She reached into her bag and pulled out a small purse she opened it and began reading from many slips of paper. .. The first one said just one word....Enema..... the second.....Mini-Vibrator in ass, they continued for about two minutes reading the most embarrassing things I have ever heard!. And then she said ok time to pick.....My wife reached in and pulled out my fate? Sara unfolded the piece of paper and said this was a good one. She handed it back to my wife who looked very happy, she looked at me and said honey your going to get a chance to show off for Sara. I instantly filled with dread, and humiliation. Sara looked at the timer and It read exactly two minutes and 30 seconds, she quickly untied me and told me it was time to show off. There I was standing there with my underwear at my ankles and a raging hard on in front of my sister-in-law and wife. I began to protest, but Sara reminded my wife that is why we snapped a few photos. I was pretty sure they wouldn't really show them to anyone, but what if I was wrong. Sara told me if I didn't cum by the time the timer reached zero she would email those pictures to all of her friends, I looked at my wife for support but she just sat on the couch and smiled. Was I really going to masturbate in front of her? Oh my God. 90 seconds she yelled.....
I reached down and held my cock and began to stroke, I closed my eyes and pictured Sara's little ass naked and me spanking her, I pictured her bent over my lap, and her pink lips becoming moist. I began to stoke faster and faster when they interrupted my fantasy and told me to open my eyes and look at them. The reality was surely setting in. I saw them smirk and giggle at me. Sara appeared to be commenting on my penis, I stroked and stroked she said I only had 20 seconds left, Oh God hear it comes, and then I shot my load, it shot across the room, but not quite far enough, I wanted to hit Sara in the face. Of course it didn't, but that would have been justice.
They both Clapped and smiled. Sara jumped up and said it was time to go. I'll see you both next week for dinner, and then she grabbed her canvas duffel and walked out the door.