I am Glad I Won the Bet

Anal

A few years ago, my husband Terry and I had a bet on the results of the Oscars. Once we had made our choice we couldn’t agree on the amount of the bet. We have always shared our accounts, so it felt like who ever won would only be getting their own money so not much point.

So, at Terry’s suggestion which ever one of us lost would have to be the other one’s total slave for the two weeks of our main summer holiday in the south of France. I agreed to this but much to his surprise I won.

When I asked him what he would have done if I had lost he told me that he would have made me wear very short skirts, skimpy T shirts, without any underwear, for the whole of the holiday.

After we had been there a few days, and I was nice and tanned, he would have made me go into a local bar, which we know is frequented by English, Australian and New Zealand sailors from the tall ships that are usually racing there at that time of year, and I would have to have sex with the first man or men who picked me up.

Before going on the holiday, I decided to get my own back on him and without his knowledge purchased a load of items from an on-line sex shop.

On arrival at our holiday villa my orders to him were that he had to be naked in the villa the whole time, wear a slave collar, a cock cage, a heavy ball stretcher and look after me hand and foot, which he did. I also made him lick me out whenever I wanted to, but he could not touch himself or cum because of the cock cage. I told him that if he was a good slave, I might let him make love to me at the end of the holiday.

On the 4th night I told him we were going to have some fun that night and he was to take a shower and completely shave himself, which he did.

When he came out, I gave him some wrist and ankle straps and told him to fasten them on. These straps had small metal rings fitted to the straps. I used small padlocks fitted to the buckles of the straps to make sure he couldn’t unfasten them. I then gave him another large ball stretcher weight and told him to add it to the one he had on, which he did, and it dragged his sac much further down. I then put back on his cock cage, so he couldn’t masturbate and a leather male chastity belt, which I had cut a hole in the front pouch so his cock and balls could hang through.

The belt was fitted with a huge butt plug which was 4″ across and 7″ long and I pulled it up tight and locked it in place which firmly plugged him.

I then made him kneel and padlocked his wrists and ankles together behind his back. I then added a large ball gag which I fastened behind his head and locked it with a small padlock.

All his restraints were padlocked shut so none could be removed. He was completely restrained and unable to move. I showed him the keys and placed them on top of a tall cupboard, so he knew he was trapped until I released him.

I think he thought it was going to be his night as he was very aroused with an attempted erection which was painfully constrained by the small penis cage (smallest I could buy, which was only 2″ long).

He has a very small penis only 2 inches long when flaccid and only grows to just 4 inches when erect. However, he does have a great tongue which he uses on my pussy to great effect.

After he was secured, I took a slow bath, clean shaved my pussy and oiled my skin and went into the bedroom and choose my shortest little leather mini skirt (just over 17″ long), a skinny rib top and a nice pair of 4″ high heeled sandals. I decided not to put on any underwear and went back out into the main room where Terry was tied up. He looked extremely excited but became quite crestfallen when I told him I was going out to the bar on my own and I was going to choose who I had sex with and he would remain here whilst I had fun, and if I was feeling generous I might let him lick me clean when I came home later that night, if I came home.

I found the freedom of dressing like a slut wonderful and drove into town and headed for the bar. It was full of testosterone fuelled men, as usual.

I made my way to the bar and ordered a drink. Just sitting on the high stool at the bar was definitely giving guys a flash of my assets and after a few minutes 3 men came over to talk to me and they asked me if I was meeting anyone.

I told them that I was on my own as my husband had just had to fly back to UK for work and wouldn’t be back until Saturday.

We slid down a few more drinks and I was quite happy when they asked if I would like to see their boat. They were a sales team in town as part of their company’s sales drive and instead of staying in a hotel they had been lent one of the company’s large boats moored in the harbour.

I joined them on board, and we quickly moved to one of the master bedrooms where they helped me undress, which didn’t take very long, and they all stripped off and I was rewarded with the sight of three lovely fat cocks. The largest must have been 9 inches long and nice and fat, the other two slightly escort izmir smaller but still much bigger than my husband’s 4 inches.

I knelt down and started sucking Brian’s cock and felt him grow stiff in my mouth. I reached out and stroked the other two cocks, Peter’s and John’s to keep them nice and hard. After a few moments, Brian picked me up and took me over to the bed and pushed me on my back and lifted my legs and rested them on his shoulders. I couldn’t believe how good it felt as he slipped his cock head into my sopping wet cunt. I felt really stretched.

He slowly pushed all the way in, and I heard myself groaning, as it stretched me in ways I had never experienced. After letting me adjust to his size he began to fuck me with slow and steady strokes, almost pulling all the way out before driving back in. He screwed me for what seemed like hours as I had a series of gut-wrenching orgasms. I am normally a one orgasm woman, but I seemed to be having a series of them each one bigger and more intense than the last. When he finally shot, what felt like a gallon of cum inside me I had the most shattering orgasm of my life.

After he rolled off I lay there with my legs wide and cum streaming out of my fanny and without a moment’s hesitation John got between my legs and pushed his cock all the way in with a single thrust. He then pounded me to even more orgasms before he flooded me with his load.

He was followed by Peter who pushed the cum back inside me as it started to leak out. He was so worked up from watching the other two that he came quite quickly adding another load to my already full snatch. When he pulled out, I just lay there limp with exhaustion having just had more orgasms in an hour than I had managed in the last 5 years.

Brian led me to the shower, so I could clean up and he gave me a robe to wear. We all moved to the lounge area and had a few more drinks before heading back into the bedroom.

This second session was much slower pace and started with Brian lying on the bed with me kneeling over him and slowly impaling myself on his huge cock, When I had worked the full length in, John pushed me forward, so I was able to suck on Peter’s cock as John proceeded to work his cock into my anus. Brian and John got into a rhythm with one pulling out as the other pushed in. It was fantastic I felt so full, and I had sensations I had never felt before. I had let Terry finger my anus when he licks me to orgasm and he has used a small dildo in my arse a few times, but I have never let him have anal sex, so this was a double first, in every sense.

It wasn’t long before Peter fired a load down my throat and both my anus and fanny were filled with loads. As it was after midnight and I was worn out I told the three that I had to be getting back despite their pleas to stay overnight. However, I did agree to meet them the next evening for drinks and a party on their boat. They said they had some clients coming who they wanted to entertain so it was going to be a bigger party than just the three of them.

I turned down the offer of a shower as I wanted to take my last two loads back to torment Terry with and let him lick me clean, so I drove very carefully back to the house where Terry was still restrained. I then told him in detail exactly what I had done and that for the next few nights he would be restrained again whilst I was out meeting with the guys. I pulled him into a kneeling position removed the ball gag and lifted my skirt and made him lick my arse and fanny clean, which brought me to another climax. I took the keys and threw them on the floor and told him to release his hands, but he was to keep the cock cage, chastity belt, but plug and the ball stretchers on, he was not allowed to touch himself and had to sleep in the small spare bedroom. I took a quick shower and headed for bed to a very satisfied but slightly sore sleep.

The next evening was fantastic. I must have spent all day asleep on the beach on my own recovering from the previous evening. That evening I remembered to take some KY jelly to ensure I didn’t get too sore as I was hoping for loads of action. I made Terry get me ready to go out by washing and shaving my fanny then oiling my skin. After that I put Terry back in his full restraints similar to the previous evening and I set off to join the guys on their boat at 8 o’clock.

The party was in full swing by the time I arrived, and it was obvious it had been going on for some time. I downed a few quick drinks and then found myself being taken to the master cabin by Brian who repeated the majestic shag of the previous evening. He was quickly followed by Peter and John who DP me, which was wonderful. They kept going for twenty minutes or so and I again experienced multiple orgasms.

When they finished, I just flopped on the bed too exhausted to move. Before I realised what was happening another man had entered the cabin and stripped off and climbed between my legs and started to fuck me. He was well built and izmir escort bayan had great stamina and pounded away for ages. He never said anything just fucked me and it felt so wicked and exciting that I was sent over the top again and again. When he was about to come, he pulled out and guided his cock into my mouth and pumped his load down my throat, which I swallowed. As soon as I had sucked him clean, he got up, dressed and left and was immediately replaced by another man who came in with a woman.

This felt a little strange as I had never had sex in front of another woman before. It was even odder as she undressed him and then she pushed my legs apart and guided his cock into my wet love hole. It squelched as he pushed into me. He was as large as Brian if slightly thicker and it felt good, and I was soon moaning to yet more climaxes. As he was thrusting his cock into me the woman came around and turned my head and started to kiss me, another first for me but to my surprise I started to respond.

After a few minutes, she lifted her dress and I saw she had no underwear on, and she planted her sopping fanny onto my mouth, and I instinctively started to lick her clit. I have never done anything like this before and found it a huge turn on and it enhanced what was going on at the other end and I kept having to break away as another orgasm rippled through me. Eventually she came and soaked my face in her juices. She lent down and licked it from my face and then stood back as her partner grunted and emptied himself in me. Again, I licked him clean, and he dressed, and they both left.

I was left alone for a little while before a succession of men came in and used my body, some singly and some in pairs. A run of 4 men came in and rolled me over onto my face and fucked my arse, filling it full of cum.

By midnight I had been fucked more than I had in my previous twenty years, and I had cum pouring out of my arse and fanny. Brian came in and asked if I wanted to stay but I so wanted to go back to the house and let Terry see what had happened and hopefully get as much of the cum in me back as I could manage.

Brian told me they were away cruising with clients all the next day, but would I come along to their final night’s party on the Friday and plan to stay the night. I immediately agreed.

I got my little black dress and pulled in on over my sticky body and with cum dripping down my legs made my way back to the car and drove home. I again made Terry lick me out and then left him to sleep in the spare bedroom with his chastity belt, butt plug, cock cage and ball stretchers on. I soaked in a bath for 30 minutes and then fell into bed and slept.

The next day I was so sore I could hardly walk and sitting down hurt, so I was rather glad I wasn’t getting any action that night.

The Friday was the last evening that Brian, John and Pete were there as they had to fly out on the Saturday morning. They were throwing a big party for all their customers, friends and crews from the sailing boats their company sponsored. I restrained Terry after getting him to help me get ready to go out. I had decided on a tiny denim mini skirt a black T shirt and sandals, as usual I had nothing on underneath but had put a spare top, some KY jelly and some Emla cream in my bag. Terry told me I looked so sexy, and he wished he could be there to see me used as a whore slut as it had been a dream of his for years. I left him tied up as usual and drove into town and parked and walked to the boat which was at the end of the harbour.

The party was going full blast and there must have been 40 or so people there, mostly men although there although I saw two or three other women. I also spotted the girl with her partner who had used me on the Wednesday evening so was hoping for a repeat.

I was met by Brian and a martini was thrust into my hand which I quickly downed, and I was given another one as Brian escorted me to the master cabin. The bed had been stripped down and was covered in just a sheet with four large pillows. I was obviously going to be busy that evening. Brian undressed me and turned me round and got me to kneel on the bed, he then squirted some of the KY jelly into my arse and then slid his dick in, in one steady push. He stopped for a few seconds as I adjusted to his size and then he began to fuck me hard. I was so aroused that I had my first orgasm within a few minutes. He kept banging away at me and I was in squelching 7th heaven when I realised there was another cock being pushed into my mouth.

I open my eyes and saw a huge black cock, even bigger than Brian’s sticking out towards my mouth. I open my mouth as Brian’s thrusts pushed me forward onto this monster cock. I could only just fit the head into my mouth but sucked as hard as I could. Brian continued to pump into me and finally emptied his load into my rectum. He pulled out and came around to the front and the black guy who I subsequently found out was called Mike moved round to my rear. izmir escortlar I started to clean Brian’s cock as Mike started to slide his huge cock into my arse. As Brian had already stretched it and it was greased with KY jelly and a full load of cum he was able to get most of his cock in straight away. I did ask him to go slowly as it was hurting a bit. He did and told me to relax that it wouldn’t hurt. I tried to relax but the sensations were causing my rectal muscles to spasm which kept bringing me to one orgasm after another. Eventually after a few minutes he had worked all of it into me and was starting to slide in and out, it was amazing, impossible to describe but feelings like electric shocks coursing through my body, tingles in my clit which I reached back to rub and enhance the sensations. My orgasms were almost continuous, and I thought I might just pass out it was so wonderful.

Brian had left by this time and had been replaced by someone else, I have no idea who it was it was just another cock to suck which I did and was rewarded with a massive load down my throat, which I swallowed. As soon as he had been licked clean, he was replaced by another cock to suck. All this time Mike was sawing back and forth in my arse. I felt him tense, and he pumped a huge load into my arse, I actually felt it splash on my walls, it was sensational, and I had another huge climax. It was so intense I almost sucked the end off the cock in my mouth. Before the guy in my mouth could come, he pulled out of my mouth and moved behind me and slid easily into my much-stretched arse and started pounding away. I was very hard to keep track of time as what was obviously only a few minutes felt like hours. As he pounded away, I became aware that the couple had come into the cabin, which almost acted as a signal for the man fucking me to cum into me. He came around to my head and I sucked him clean, and he dressed and left.

As before the girl undressed the guy and pushed me down onto my stomach and I felt her pull open my arse cheeks and her partner slid his cock easily into my already well used, well lubricated and very stretched arse. She came around and I saw she was already naked, and she sat on the bed with her legs either side of my head and edged forward until her fanny was right against my mouth. She grabbed my hair and pulled my face into her wet snatch. I licked and sucked with enthusiasm as her partner ploughed my furrow with long steady strokes. I loved the flavour and the heat emanating from her core. I concentrated on her clit, trying to bring her to an orgasm and I was rewarded when she had a huge climax and she squirted copious amounts of her juice all over my face. I am not a squirter, but this girl was and in trumps and I think she could have filled a pint mug with it. It sprayed all over my face and hair and I was dripping with it. She then knelt and started kissing me and licking her love juices from my face and neck.

After she finished she got up and I could feel her hands stroking my buttocks around her partner’s cock, she then reached under my legs and pulled my arse higher in the air. This allowed her to slide her head underneath me and start to lick my fanny as her partner was hammering away at my back door. The combination of the two of them drove me to an orgasm of such proportions I did black out for a few seconds.

When I came around her partner was just dumping his load inside me. As he pulled out, she moved her mouth and started to suck on my puckered portal and suck the cum right out of me, at the same time she pressed my stomach to make me eject the deposit. Her partner came around to my head and I licked him clean. I was so shattered by this session with the two of them that I asked her to tell Brian that I need a short rest before taking on anyone else. She said she would tell him.

I think I must have dozed off as the next thing I knew there were 4 men in the room and I was being lifted like a rag doll and put astride one man, who was on his back on the bed next to me, and impaled on his cock, I was pushed forward, and I felt another cock slide into my arse and then two cocks were offered to my face. I alternated sucking the two cocks as the other two men worked magic on my holes. I don’t know if there is a record for the number of orgasms that one can have in a 24-hour period, but if there is, I broke it in three hours.

The two continued to pound away at my holes and I was rewarded for my sucking efforts as first one then the other sprayed all over my face and hair. I used my hand to wipe as much of the cum as I could and then licked my fingers clean. The guy in my butt shot his load and pulled out and the guy I was straddling rolled me over onto my back, lifted my legs over his shoulders and pounded away until he came. They all said thank you and that it had been the best fuck they had ever had. They dressed and left.

I laid on the bed, covered in cum and sweat feeling elated and exhausted. I didn’t have much of a rest as another couple of men entered the cabin; they were the first in a queue of men that kept coming, literally for the next couple of hours. I must have passed out from the shear exhaustion of almost constant orgasms and use by dozens of men.