My boyfriend had never been good with money so it was not the biggest surprise when he said he was in big trouble over a gambling debt. He said if he was unable to come up with a large sum of money within a week he knew he would be lucky to get away with only a severe beating. I asked him how them beating him would solve anything. He said that it would serve as a warning to others but the full debt would still be due.
There was no way I could raise the sort of money he was talking about in a week, or for that matter in a month. I told him what I could get my hands on quickly and said I would help if I could. Thinking I might at least be able to buy him some time he suggested that I put the offer directly to them, as they no longer trusted his word. I agreed thinking that a calm head might help the situation. They agreed to meet a couple of days later. By then I was getting cold feet and more annoyed with him but did not feel I could back out.
We agreed to meet at a nice big house out of town. When we arrived I was regretting my decision as we walked up the wide drive to the front door. I don't know what I had expected but we were led into a very normal, if big, lounge. The décor was very masculine in style but good quality. The very attractive woman who led us in took me by the arm as my boyfriend was taking his coat off. She whispered into my ear that she strongly advised that I did not argue or try and negotiate with her colleagues. She made the whisper sound very menacing indeed. She was gone from the room long before I could ask anything.
The two men that entered the room were very smartly dressed in expensive suits but did not look like they would be at home around a boardroom table. They indicated that Pete and I should sit on the small sofa as they settled into the two chairs opposite. They introduced themselves to me but their names didn't register in my frightened brain. One of them laid out the details of what was owed and said that things were now at a very serious stage. They were prepared to listen to what I had to offer but said they were not authorized to make any agreement that didn't recover the whole debt by the end of the week.
I had thought I had got my proposal well worked out but this did pull the rug from under me somewhat. I started as confidently as I could to tell them what we could manage to repay and when. In fairness they heard me out politely before the taller one said.
"I don't think you quite understand the situation here my dear. A proposal like this might have been acceptable two months ago but things have moved on. The two of us are mere collectors of the debts. At the end of this week if we do not pay the money to our employer, who you owe the money to, our lives will not be worth living. We will pay over the full sum as we have seen what happens when people don't. We are not in the habit of paying across what we have not been able to collect. We would be paying across our money to save your boyfriends skin. You have some nice jewelry on - maybe you could sell or pawn that."
He then addressed Pete directly and said that if I was not prepared to part with my jewelry, to save his skin, then perhaps he could persuade me to make up the shortfall in other ways. My boyfriend's response was more a lack of response. He looked down at his hands and remained silent for a few seconds before turning to me with a nervous look on his face. I could have killed him right there and was very close to just walking out of the house.
Fortunately I was sensible or scared enough not to say what I was thinking. I looked at the two men sitting opposite me in an attempt to check whether they were serious. Nothing in their demeanor suggested they were joking but they seemed to be looking for a response from my boyfriend not me. My response was to this insult rather than the proposal.
"What the fuck are you doing looking to him for permission? Unless I was born yesterday I think you were proposing that sexual favors from me would be a possible way of moving things forward. Don't insult me by suggesting that his permission is what you would need for that. He has got himself in this mess it appears that only I can get him out of it. If you have a suggestion to put to me at least have the balls to put it to me."
"You certainly appear to have some balls. That is nice to see but I suggest you don't talk to us like that again unless you want to see us remove one of your boyfriend's fingers. At least we have some progress here. It sounds to me as if you might be not only understanding the position you are in but also considering ways that you could help."
In that instant I realized that I had in fact suggested that I would consider offering sexual favors in exchange for paying part of the debt off. My head was spinning this would be nothing short of prostitution, had I really sunk this low? I was desperate to find a way to change the dynamics of this situation. I needed time but was not being given it as all eyes were on me.
To buy the time I asked where the bathroom was. I sat on the throne and tried to see things from every angle. If I didn't do as they were asking not only would my Pete be in deep trouble but also our relationship would be over. I had no real choice but would it be as bad as prostitution? Of course I didn't want what the men were demanding of me. I was no blushing virgin but I had always chosen when to have sex and had always been in control. I was angry with my boyfriend for putting me in this position. Working through this in double quick time it suddenly struck me that I was incredibly aroused. Could I possibly be excited by the prospect of what the two men might do to me? What might they do to me? Something a friend of mine had said once flashed through my mind. She said her favorite fantasy was being forced to have sex, being raped. For the first time I did understand this just a bit.
I realized that I had taken in almost nothing about these two men who were asking to fuck me. They didn't have two heads or at least not on their shoulders but I couldn't even remember what they looked like. I made the decision if I was going to be forced into having sex I was going to see whether I could get something out of it myself. I was not going to appear compliant in any way, as I was sure that my humiliation was as important to the two men as the sex.
"I have considered my position very carefully and if we can agree some very clear ground rules I would consider the possibility of coming to an understanding."
I didn't look at my Pete but studied the two men opposite me to see their reaction. The shorter one who seemed to be in charge gave me a knowing smile that disarmed me slightly.
"I would like to remind you that you are not in any position to set any rules or make any demands. We are however very reasonable men. We would promise not to injure you or do you any long-term harm as long as you do exactly as we tell you to. If you manage to entertain us with enthusiasm we may agree to extend the deadlines by a couple of weeks. We are very keen to show your boyfriend that we may just be able to satisfy that beautiful body of yours while we take our pleasure."
I was not going to let my boyfriend just sit back and watch the men fuck me. I wanted to humiliate embarrass and punish him as I was still furious with him.
The closest to actually agreeing the deal I could manage was a resigned nod of my head. I needed to say something to my boyfriend to make him feel bad.
"If I am going to do this for you, you have got to promise me you will not place a single bet for the next year. If you don't I walk out of this house right now."
His apology was convincing along with his promise about the gambling.
"I think it is time for you to take all your clothes off. We have both been dying to see whether you are even better naked and helpless than you are with your clothes on trying to set the rules. This will be the only order we give you that you can take your time with. When you are topless you can serve as drinks so we can sit back and enjoy the show."
I had not expected this. I had thought they would rip my clothes off and fuck me hard. I now realized that they were going to take their time with things and really make me work to entertain them. I wasn't sure how to handle this as arguing about this would be futile. I would save my protest for when things got more physical. If they wanted a striptease I would do my best and try and embarrass my boyfriend as much as possible. I tried taking my blouse off as provocatively as possible. Undoing my bra behind my back I held the cups in place and approached the two men offering them one each to remove from my boobs.
They played along dragging each cup down over my alarmingly erect nipples. It was done so that Pete could see my hard nipples very clearly. I managed to get both men each sucking one of my bright red nipples at the same time. My god they fed on them as if starving and my resolve to tease them evaporated into arousal. For some reason I had not expected to get aroused certainly not as easily and quickly as this. I had thought I still had an element of control but this was going to make it difficult.
I felt let down when they took their mouths off my nipples and told me the drinks they wanted me to pour from the cabinet. They said I could help myself if I wanted. There was no mention of my boyfriend. As I presented their drinks to them they sat back and I knew it was time to remove the rest of my clothes. Remembering what I had been told I managed to take 30 seconds or so to remove my skirt giving all three men a good view as I did so. As I wriggled out of it I could feel that my pussy lips were sliding across each other under my panties. It was hard to admit to myself that I was getting very turned on.
Hands on my hips I turned me round so that I was facing my boyfriend. Fingers of one hand then came round my body and found my bellybutton and started to finger it as you might a pussy. I don't remember anyone doing this to me, or if so whether it had been erotic. This was. The hand soon started an agonizingly slow descent to the waistband of my panties. I was surprised and shocked at myself when I lifted myself as high as possible in an attempt to get the hand down inside my panties. I was sure that the display was to tease and torment my boyfriend but it was teasing me.
"I am so pleased you didn't tell us that your girlfriend is so highly sexually charged. It is so nice to start to reveal it as we go. You're really very hot my dear. Would you like my fingers to go far down?"
"I think your fingers should go on down so that my ******* of a boyfriend can see what a real man can do to my body."
I didn't want to admit that I was desperate to have my clearly damp pussy played with. It also played into the role that we were all trying to humiliate Pete. He looked as if we were doing a good job.
When the first finger found my clit my legs briefly nearly collapsed. I knew I was excited but that first touch and the fact that my pussy was nearly dripping disturbed me. It disturbed me because I knew if I had the choice of walking out of there right then or being bent over and fucked by both of them in turn it would not have been an easy answer. I like to be fingered as much as the next girl but there was a danger that if it lasted much longer I would embarrass myself by coming uncontrollably. Fortunately the two men could not read my mind or if they could they did not want me to cum so soon.
I was invited to kneel in front of the bigger of the two men. By the time I was in position his cock was sticking through his flies. I had never given a man head while he still had his trousers on. It was not an appealing prospect. As I had little option I lent forward and took him into my mouth. No sooner than I began I was aware that I was going to be entered from behind. My panties were not removed but simply pulled aside. For some reason this felt beautifully dirty. I am not sure whether I was not as lubricated as I thought but he felt huge as he stretched my pussy more than I could ever remember since losing my virginity. I didn't want to enjoy him fucking me as much as I was. Even as the lubrication increased he was still filling me up and stretching me to my limits.
I did not want to prolong giving the head but was very confused how I felt about the cock in my pussy. The part of me that wanted the whole ordeal over quickly was losing the battle against the pleasure that made me want it to last at least until my orgasm. To say I was confused was an understatement. Sex had always been simple. I made a connection with somebody emotionally and then enjoyed the physical sexual connection. I didn't want any emotion connection with either of the men but the physical connection of the cock fucking me was wonderful.
"If I am not very much mistaken your girlfriend is rather enjoying my cock. Look if I hold still she starts to fuck me."
The bastard was right. I had hardly noticed that when he slowed his thrusting down I found my hips pushing back to increase the penetration. His full deep thrusting did start again having proved his point. It felt like he was rearranging my insides he was so deep. I was soon enjoying the fuck as I had been before he had embarrassed me. He then gripped my hips and held himself buried as deep as possible. He then very slowly withdrew. It went on and on withdrawing until finally I felt the head of his cock allow my stretched pussy to try and close. I was deeply frustrated with this but furious with myself for allowing a wail to fully reflect this frustration. This was not what I expected to happen when being raped. His reply to my reaction was to laugh as he buried himself in me again and fucked me hard and fast. Unfortunately I had stopped concentrating on the cock in my mouth. While I do not like the taste of cum I had planned to make him cum in my mouth so that he would not be able to fuck me. This plan failed as my devastating orgasm triggered the cock in my pussy to be milked by the spasms that racked my body. I had also planned to hide my orgasm but this plan also failed spectacularly.
The men changed places and I was stunned at the size of the flaccid cock in front of me. It was bigger flaccid then any cock I had seen (other than in porn) erect. The cock behind penetrated me as if it was not touching the sides. For some reason I cannot understand I immediately set about arousing the monster in front of me. I could not remember ever going down on a cock that had already fucked me. It was covered in our combined juices but still I took it in my mouth as well as using my hands on it and his large balls. I say I took his cock into my mouth in fact I only managed the head and an inch or two of the monster. My jaw was so stretched I spend more of the time licking it like a lollipop.
Although the cock in front of me did get much firmer it did not grow as much as for some reason I had hoped. I was delighted when with almost no fuss the prick behind me exploded into me. I had not been sure whether more would be demanded of me but was very happy when the two men made it clear that they had finished with me sexually. The shorter man, with the huge cock, said that my boyfriend owed me a huge debt, as they were so pleased with my performance that they would give him a three-week extension to pay his debt. His final comment as he saw us out was to me.
"I hope for your sake he can find the money in time because if he doesn't your pretty bottom will be stretched like no bottom should ever be stretched."
Over the next few days I was disgusted with myself as my fantasies were filled with memories of being fucked by the two men. The fantasies however were not accurate memories of the evening as they always ended with my anus being stretched by his huge cock. My orgasms were the best masturbatory climaxes I had ever experienced. I was certain my boyfriend was never going to find the money required in three weeks. I was not going to find the money for him but whether I considered going with him to meet them was a much more difficult decision.
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