A Night She Won't Forget

David was a good 6ft 3 with the most piercing light Green eyes and had a dark olive complexion with what I could only describe as one of the most beautiful bodies I had ever seen. He wasn't overly muscular but everything was just so ripped and developed. I felt my eyes run down his body over what could only be described as a washboard 8 pack and then the most insane V leading down to god knows what was below the shorts. I felt myself blush and a warm sensation wash over me but couldn't bring myself to take my eyes off of him.

As David slipped in besides me he said, you looking hot the GYM is clearly paying off, I felt my nipples stiffen and had to sink lower in the water so that I didn't give myself away, I was very thankful for my underwear about now. We chatted and sipped champagne which was going straight to my head and then Jen's husband suggested a game of truth or dare, this cant be good I thought but had no choice but to play along. The first few rounds were tame with silly questions and dares, but I could feel that the game was about to ramp up quickly. Jens Husband dared her to get us a round of shooters from the bar, but she had to be naked, without hesitation she stood up stripped down and walked off towards the bar.

I wasn't sure where to look but knew in the back of my mind that things would only get worse from here. She had an amazing body and loved the fact that we were all watching her walk to and from the bar, she was so confident in herself and even did a little twirl for us before getting back in.

Jen paid her husband back pretty soon by daring him to remove his shorts, things were getting crazy real quick. Her husband had a nice body for someone of his age and also seemed to be absolutely not shy at all. He stood on the side of the Jacuzzi in full view and removed his shorts. I didn't want to look but couldn't help myself, he had a nice penis, average length and thickness and was neatly groomed. They seemed to be going easy on me, so I was very happy and comfortable at this stage, besides the fact that two of the 4 were now totally naked.

I was avoiding dares like the plague as I was so not removing my clothes in front of these people, but my plan was soon derailed. As Jen chose a dare again David looked us both square in the eyes and he dared Jen to remove my clothes, I almost choked on my champagne as he said this, and she just laughed and said very sneaky David. I was literally shaking, but Jen calmed me down by saying I didn't have to get out she would remove my clothing while I was in the water. Before I could object, she slipped in behind me and positioned me between her legs, I felt her hands move towards my bra strap and in a flash she had it off. I was so thankful for the bubbles about now but still sank a little lower down in the water.

Slowly she let her hands run down my body and hooked her fingers into my panties, she whispered into my ear and said lift your bum and in a flash they were off. Jen didn't move from her current position and stayed behind me, I could feel her nipples gently scaping against my back as she pulled me back to rest on her. Strangely enough I just let myself flop back against her and enjoyed the sensation of her skin against mine. I was so glad I was lying so low down in the water as I knew my nipples were now totally erect and I could already feel I was slightly wet so squeezed my legs together hoping it would soon pass.

My turn again and once again I chose truth, I so wasn't running naked to the bar, Jens husband thought for a minute and then looked at me and asked "do you want to see David naked"? Shit I wasn't expecting that question and I already knew the answer to the question but nervously and as calmly as I could said no.

Before I could say another word Jen slipped her hand under the water and slowly ran her finger up from the bottom of my pussy to my now slightly swollen clit. I was in absolute shock, but I didn't even consider stopping her, instead I instinctively opened my legs just a little wider as she did it, with that she whispered in my ear and said after what I've just felt I think you are lying, maybe you had better answer that question again and this time truthfully. In my croakiest and very alcohol infused voice I slowly whispered yes trying to avoid Davids eyes.

As the boys were topping up out glasses Jen was slowly massaging my shoulders and as she did, she leaned in and whispered in my ear "Good choice, trust me you want to see it you will definitely not be disappointed" she then kissed my ear and gently flicked her tongue inside which you know drives me crazy and once again I could feel that I was so wet. As she stopped, she whispered choose to dare next time just trust me. As the game started up again it went round the room and soon it was back to me again, Truth or dare they asked, I nervously thought about my answer but with Jens message still very fresh in my mind I blurted out dare!

I could see Jen and her husband looking at one another and then she winked at him and turned to me and said Olivia we dare you to first kiss and then remove Davids pants, after all he is the only one left with clothes on. Say WHAT I blurted out, giving Jen and evil eye and pinched her at the same time. What if David doesn't want his pants removed I asked and he looked at me and said hey it's a game and I have to comply but only if you're comfortable with it. With that Jen gave me a push in his direction, as I slowly swam up to him, I realized just how much he dwarfed me.

I was just going to give him a gentle kiss on the lips and that was all. As I got closer, I could feel my whole body shaking with a combination of fear and what was probably excitement. I sat on his knees and gently leaned in for my peck, as our lips touched it felt like a bolt of electricity shoot through my whole body. He put his huge hands on my hips and they almost wrapped around my whole waist, as he did that, I opened my mouth and slowly slipped my tongue into his and met his tongue half way. He kissed rather roughly but at that very moment I knew in my heart that whatever he wanted from me tonight I would not be able to hold back any longer.

The kiss seemed to go on for minutes and I didn't want it to end until I heard Jen in the background shout "the pants Olivia" We finally had to stop but I could have gone on forever, I knew what had to be done and felt my whole face flush and turn Red but I knew that now I so badly wanted to remove his pants and see what could potentially be awaiting me for the night.

David stood up in the Jacuzzi and with slow fumbling hands I undid his draw string and pulled his shorts down. To my surprise he still had a pair of undies on, as I was still in the water my face was about crotch height. Immediately I could see what Jen meant, his undies were struggling to contain whatever was in there and I was so excited and at the same time nervous to see what his penis looked like.

With nervous excitement and shaking hands I gently ran my hands down his ripped stomach and hooked my fingers into the waistband of his jockies, are you ready shouted Jen with drunken laughter, you have no idea said a voice in my head. Slowly I peeled them off and with every inch the undies came down I could feel my eyes grow wider and my jaw drop a little more. Once I had removed them fully, I just looked up at him with what must have been a look of shock, awe and perhaps a little bit of fear.

He was circumcised, well-groomed and as he wasn't yet hard, I don't know how big it would get but the girth and the size of his head was like nothing I had ever seen before. (this was no penis it was simply a cock) I heard Jen say from behind me what do you think and wait until he is erect. I looked into Davids eyes and whispered its sooooo huge. Almost disappointingly he chose to sit back down in the Jacuzzi, by this time Jen had moved over and was now sitting on her husbands lap which left me to stay next to David

As we watched them make out David pulled me towards him and let sit me on his lap and lie back against his chest. Slowly his huge hands started to caress my body as I lay there watching Jen and her husband make out. I could feel myself slipping away into sensual overload and knew that whatever David wanted I would do at this point no question asked. His hands slowly circled my breasts pulling on my nipples and then back to squeezing my whole breast again.

As I felt his hand move down to just where I knew I wanted it to go I felt myself spread my legs a little so that he could have as much access as he wanted. I felt his one large finger push its way over my ever-swelling clit and further down to my opening. Despite being in water I knew I was soaking wet, he kept circling my opening and then moving further back to gently rub his finger over the nerve endings at the back and then back to my clit again over and over again. Every time I tried to push myself down onto his finger but he held me tightly and made sure to control the pace of everything. Watching Jen and her husband make out right in front of me while David was slowly circling my clit and massaging my pussy was driving me insane.

I could feel that I was close, he moved his fingers faster and harder across my clit and the opening and all of a sudden I could feel the waves of my first climax start to shake my body, as it was happening I felt him slide his huge finger deep into me and push against my G Spot which only intensified my orgasm. I moaned loudly and realized this was going to be a long night. As I opened my eyes I was staring straight into Jens eyes who winked at me and mouthed see I told you. Knowing that I had just been watched cumming by total strangers was an absolute turn on for me.

At this point Jen and her husband climbed out of the jacuzzi and said that they were going to retire for the night. I could see her hubby was fully erect as he followed her out and remembered thinking I wonder how big David will get.............I was soon to find out!!

As they were walking towards the bar, Jen turned and said to me I will leave something on the bar counter for you, trust me you will need it later.

And that Mr is as far as I am willing to share about now, what do you think, I nervously asked wondering if maybe I had gone too far or perhaps still thinking I should have left some detail out or told you it wasn't that great? Would you like more detail if so, it will need another challenge as I replenished our wine glasses.

STEVE -- I think my eyes gave me away, I was I must admit shocked, part of me had never believed that you would go through with this challenge or night. I had always wanted it to happen, had always wished that it would be a great experience for you but now I was slightly nervous and having some self-doubt as it seemed as if you had hit the jackpot so far. I know you still had a fair amount to share and I was ever so eager to hear but my nerves were jingling, and I found myself sweating and wondering would I still stack up.

My excitement level was clear for you to see, I was as hard as a rock and even leaking a little after what you had just shared. You laughed and said mmm no pill or injections necessary I do like what I see maybe I should do this more often? my heart skipped a beat at the thought of that. You leaned in and whispered to me do you still want to kiss me? I simply nodded and kissed you so hard that your breath was almost taken away. I felt you hand reach down and grab my now aching member and gently stroke it up and down, mmm so hard and so ready I see. Would you like to hear more you asked and before I could even stop myself, I blurted out the fastest yes ever.

Well then Mr. you want something then you will have to give something and it was about now that I realized that whatever you wanted, I would let you have, I desperately needed to hear more.

So we started with a little pain, went to a lot of embarrassment, now don't you think it's time for some more pain you asked? still stoking me down below. The sensation of your soft hand stroking me and the thought of the information I still wanted was all I needed to say yes. How many do you think the next part is worth you asked with an almost a mocking smile, 4 I answered and with that you threw you head back and laughed, No you said I am sure it's worth double that and all at one go.

I felt a slight pang of fear as I had never taken more than 4 with the stick at once and it was no longer even the weapon that I feared the most now, but my curiosity had gotten the better of me and I had no choice but to agree. I tell you what you said I will give you a 1-minute break between the first 4 and the second 4 just to wipe your tears away you said mockingly. Are you ready you asked not for the first time today?

Come with me as you walked me over to the lowest of the curtain rods, raise your arms and spread them as wide as possible which I did. Slowly and very methodically you tied each wrist to the rod making sure that my hands couldn't move at all. Then you bound and attached both my ankles to the sides of the security gate which made it basically impossible to move at all. With that you stood in front of me and simply said open your mouth, which I did. You slipped off your panties scrunched them up and forced them into the back of my mouth and then pulled a buff down over my head making sure I couldn't see or make a sound at all.

As I stood here motionless the sweet scent of your panties filled my nostrils and I felt myself getting erect again. I heard you walk away and get what at this stage I could only imagine was your tools that you would be using for this. All of a sudden, I felt a strange burning sensation on my nipple and realized you had attached something to one of them and then you did the same to the other. You leaned into my ear and whispered I still have one more clamp wherever do you think I should use it as you ran your hand over my chest and stomach. I could not speak, couldn't move but was pretty sure I knew what was about to come. Suddenly, I felt a sudden blast of pain as you attached something to my scotum, the pain was intense and I heard you chuckle a little.

Right, I think we are about ready to start don't you. I was totally vulnerable and already in pain at this point and I knew what would come would only intensify the feeling. I heard you behind me and braced for what was to come, even if I wanted to tap out, I could no longer even speak.

I felt the air as the first blow struck me squarely on the bum, I couldn't even let out a sound but felt myself exhale deeply and an awful burning sensation spread across my ass. Before I could even steel myself the second one came down and then the 3rd, I wanted to shout out and jump around but all I could do was simply stand and take what was coming to me. I knew from the sound that you had changed weapons and I felt my nerves ramp up even more, the 4th with your new routang landed squarely on the bottom two folds of my bum and it felt as if my eyes were going to pop out of my head.

I could believe we were only halfway, I had sweat running down the sides of my body and each time you hit me whatever was attached to my scrotum pulled down even harder. 30 seconds you said out loud, would you like to quit you said mockingly. Had the first half of your story not been so good, for the first time I thought I may. Mmm already so many red welts I heard you say, but nothing Blue and no bleeding, I think I must stop holding back and really hit hard now. Those words caused me to bite down on your panties, I tried to wiggle to provide some relief, but I couldn't move at all.

Halfway I keep telling myself over and over again, everyone from now is a countdown to the end. Times up you said, I heard something being taken out of the bucket of water and knew immediately what was coming. As I bit down, I felt the next blow right at the top of my cheeks, you were spreading the pain out now and looking for the most sensitive areas. As the next one struck me, I felt myself pull down so hard on my arm restraints I thought the rod would come out of the wall. Wow look at those welts you said, what will just finish them off so nicely is the last two with the stick right on top of each one.

More sweat and definitely a lot of fear now but it was only two more to go, all of a sudden, I knew how prisoners felt that were sentenced to caning. The next one landed squarely on the first welt and I could have sworn I felt my skin open a little, one more I told myself you can do it. The last one made an echo that I thought would be heard outside, I screamed internally and felt my legs almost give way but managed to stabalise myself quickly. I hoped there were no tears in my eyes as you took the buff off of my head, I think I will have these back you said as you removed your panties from my mouth and whatever you had attached to my nipples and scrotum. I was literally dripping in sweat at this stage.

Slowly you undid all my bindings, I felt a little weak as I walked gingerly over to the mirror to see what the state of my ass was. Holy shit was all that I could say, it had red raised welts from top to bottom but no Blue marks and absolutely no blood which left me feeling slightly better even though I was walking very strangely. I put a cushion down as I sat gingerly on the couch and sipped my wine, you seemed totally unremorseful at this stage and I remembered thinking please let this be it!!

OLIVIA -- I couldn't believe how my story had affected you, I had never seen or felt you that hard before. You had kissed me so roughly and hard that I thought you would take my breath away, I absolutely loved it. I could tell that you were nervous about what I was telling you but also knew you wanted to hear everything so wasn't going to hold anything back.

I felt bad, but also surprisingly turned on after the beating I gave you now. I knew that it was bad and could see you were doing your best to man up, but I was intent on breaking you today come hell or high water. I don't like it when you are in pain but also love causing you pain if that makes any sense. Your bum was seriously swollen but I could not believe that you still hadn't bled a little and weren't Blue at all and I quietly promised myself that by the end of the day that would all change. I wanted you to remember today for a long time just as I would remember Sat and Sun for a long time and I still had one very nasty surprise for you that would totally come out of left field and you would have no clue. My Art easel type contraction was still waiting and once you were strapped to that it could tilt in many directions.

I poured us another glass of wine as you smoked, I loved the sight of seeing your bum all swollen and reveled in the fact that I had caused this. I did feel a little sorry for you and told you to come and lie on the couch so I could at least make it up to you a little. I kissed and bit down on your lip and then slowly slipped my tongue in your ear, I heard you moan a little and immediately felt your start to get aroused again. I dragged my nails across your scrotum and up to the head of your penis slowly rubbing what was now gently leaking out with my thumb. I slipped it into my mouth and tasted you while watching your expression.

Then I took all of you in my mouth right down to the very bottom, I could feel your stomach against my nose, I slowly twirled my tongue around your shaft as I gently sucked you from shallow to deep again, I heard you moan a little and picked up my pace and intensity some more as I pinched and twisted your one nipple a little. I have always loved the feel of you in my mouth, you have always tasted so good and it is a manageable size if that makes any sense. But you weren't going to finish just yet and I stopped what I was doing and simply said I suppose you have earned the right to hear more about my night now haven't you?