Meeting a school friend (After the dare)

Dareman

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Part 7
This story continues from part 6 of Meeting a school friend.
Jim started by asking me if I remembered Susan who was a girlfriend of his at school? After thinking about it I said that I did remember a girlfriend of his but was not sure of her name. It was Susan he said; and do you remember at the time we were doing dares and what you did to make me do a dare that I did not want to do.
It was then that I remembered what had happened and the thought made my stomach turn over; so I replied that I seemed to remember what happened, but was not sure about the details and added that it was just another dare we did when we were younger.
He said; well it may have been just another dare to you but what you forced me to do made me feel humiliated and dirty. I am sorry it made you feel like that but I am sure it was just another dare and I cannot honestly remember what took place.
He said; well I remember it very well, in fact it was the last dare that we ever did because after that I no longer wanted to do dares with you and our friendship ended. So let me refresh your memory about what happened that day.
We were walking back home form school when you asked me how much I liked Susan and I said that I liked her very much. You then asked me; if I had to choose between doing something I did not want to do or not see Susan again, what would I choose? As I liked Susan so much I said; that I would do anything not to loose her. You then asked me if I would do a dare to keep her, to which I replied that I would.
Then you said; okay I will give you a choice, either you do a dare or Susan will find out about the dares you have been doing and you will loose her, what’s it going to be? I knew Susan would never understand about me doing dares as she was not into that sort of thing so I said that I would do the dare.

So the next day in your bathroom, as your parents were out for the day, you made me do the dare. I remember that you first made me strip down to my briefs and show you between my legs. Then pull them down and show you between my legs again. You then made me show you my hole and made me put a finger inside my hole, I had never done this before and found very humiliating and dirty.
After this you made me get into different positions to show my cock and balls and got me to play with myself while you watched. There were other things you made me do but the worst was when you went and got a carrot out of the fridge and made me push it into my hole, which I remembered hurt quite a lot. I found this so degrading but even worse was when you wanted to see my cock erect so you watched as I stroked my cock to get it hard, after which you made me masturbate myself, making sure that you got a good view of my sperm shooting out the end of my cock when I cum.
The dares we had done before where nowhere like what you made me do, they were as you said just strip and show dares. What you made me show you, and do for you, I had never shown anybody before and it made me feel so humiliated, embarrassed and dirty that I have never forgot it to this day.
He said; so do you remember it now Dave. Yes I do now I replied and I am so sorry but we were young and I must have wanted to see how far you would go for a dare. Well he said; you made me go all the way and got to see a lot more of me then anyone else. So why have you bought this up now Jim as I have just done a dare and surely that means we are even?
Then he said; Do you know it was not until I saw you in the Mall on Friday evening that it all came back to me and realized that I had a chance to get even, and lucky for me that you had to do the dare as now I really have a chance to get even. I said; what do you mean. He replied that the dare I had done was nothing like the one I had made him do and doing this strip dare I had not really shown anything like I had made him show.
It was then that he dropped the bombshell when he said: okay Dave either you do a dare or your wife gets to find out what you have just done, which is it to be? My stomach turned over when I heard him say this and I felt like I was going to be sick so said, Jim what we did was a long time ago and all in the past so lets just forget what happened.
Problem is Dave I cannot forget; so are you going to do what I tell you to do or does your wife get to find out that you stripped yourself naked in front of another guy and let him take pictures, which by the way I have and only show you. Oh my god I thought what have I done, so said; Please Jim I do not want to do this, to which he replied; neither did I at the time, so what is it to be Dave? My stomach by this time was in knots and as there was no way that I could let my wife find out what I had done I just said okay Jim I will do your dare
So I just sat there numb and feeling sick with nerves as Jim said; well as it is late and, like me, you have a free weekend why not come around here at 10am tomorrow and you can start the dare. By the way why not wear those same white briefs as I like them, they are nice thin material, and look like a pair of girls briefs. Jim then saw me to the door and I went home trying my hardest to not be sick. All that night I got very little sleep with thinking what Jim would make me do and if there was any way out, but I knew there was not, he had me where he wanted me and could make me do anything (Continued in part 7)
 

Dareman

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Meeting a school friend (Part 7)

Part 7
Being unable to sleep I got up at 6am, showered, and put on the same white briefs that I had worn the night before, which Jim had told me to wear. While putting them on I noticed how small my cock and balls looked and wished they were bigger. It was bad enough that Jim had seen how small I was but now with pictures of me naked on the internet anyone would be able to see the size of them. After dressing I sat on the couch going over in my mind again how I had got myself into this and wondering what Jim was going to make me do. As he intended to make me pay for what I had made him do I was certain that he would make me do and show more of than I had the night before.
It was 7am when the phone rang and it was Jim on the line. He said; hi Dave just wondered if you were up and if you would like to come over earlier. Jim I said; I am not feeling to good so could I come over tomorrow, sure if you want to but then I would have to let your wife know what you have been doing. So if you are not here by 7.30am it will be too late and knowing I had no choice I said that I was on my way.
Before 7.30am I was again parking my car in the motel parking lot and this time I noticed how run down the place looked, it must have been a cheap motel. There was only one other car parked in the parking lot with Jims.
Jim had the curtains closed and the light on in the motel room and I could see that there was a dining chair with its back to the table facing the closed curtains. What I noticed next was that he had set his camera up on a tripod about six to eight feet away from the chair. He asked me if I wanted a drink and I said no thank you as it was too early for me. Okay he said; Let’s sit down on the couch and I will explain the dare you are going to have to do. Then before I had sat down he said something that made my stomach turn over, he said: before you sit down Dave I want you to strip down to your underwear. Jim I said I thought we would be using the bathroom again, no he said; what do you think I have sat the camera up in here for.
But Jim the curtains have some gaps in them, what if anyone should see me. Look Dave the rooms in this motel can be rented by the hour so anyone who might see you will have seen it all before. With that he sat down on the couch and as he watched I, with shaking hands, stripped down to my briefs. Well done Dave you are wearing those sexy white briefs you wore last night, now sit down next to me.

It felt very uncomfortable sitting next to him on the couch with me just in my white briefs and him fully dressed. I just looked straight ahead and could feel his trouser leg against my bare leg. He then started to tell me that the dare would be a pose and show dare, with pictures, he would tell me what to do and show, and as before the story, along with pictures, was to be but onto the web site.
Is this the first time you have ever sat next to another guy in you underwear Dave, yes I said, so I am the first one then he said, yes I replied. Does it make you feel embarrassed and humiliated? Yes it does I said. Now you know how I felt he said and added that he was going to make me feel far more embarrassed, humiliated and dirty than he had. Please Jim I do not want to do this, could we not just settle this some other way? Like I keep saying Dave you did not give me any choice and I am not going to give you any choice, okay. Yes Jim I said. Then he told me to go and sit on the chair in front of the camera.
I was so nervous while sitting on the chair in front of the camera that I was having trouble trying to stop my legs from shaking. He now picked up a little remote from the couch and I realized it was so that he did not have to keep getting off the couch to take the pictures. He told me to open my legs and he pointed the remote at the camera and the flash went as the picture was taken. Noticing the small gaps in the curtains made me feel uncomfortable but at least I had my briefs on and was sure nobody could see through them.
He told me to turn around and sit with my legs on either side of the chair so as to get a picture of my bottom with my briefs on. With me sitting this way around I could see a mirror hanging on the wall to my left and in the reflection was able to see the curtains behind me. I noticed that I was able to see the small gaps in the curtains and possibly due to the angle of the mirror could see a gap that I had not noticed before. This gap was wider than the rest and to my horror noticed that I was able to see the motel parking lot quite clearly. It dawned on me that if I could see out then possibly anybody outside could see in and even though I could not see anyone at that moment dreaded the thought that someone might see me through that gap in the curtains.
Jim asked me if I had ever given myself a wedgy, to which I replied that I had not. Okay do it he said; so I stood up then taking hold of the waist band of my briefs gave myself a wedgy. This caused my briefs to go between the cheeks of my bottom and to pull my balls up tight, which I found quite uncomfortable and very embarrassing. He then told me to sit down facing the camera with my legs open and took a picture then to sit with my back to the camera for another picture. Once again with my back to the curtains I could see through the reflection in the mirror the wider gap in the curtains, but with relief could not see anyone outside.
It was just as Jim was saying that he wanted a picture of me with my briefs pulled down to get a picture of my bottom that I saw to my horror, through the gap in the curtains, a car pulling into the parking lot. I watched panic stricken as I saw a guy get out of his car and start to walk towards the motel. I was sure that if he got close enough to the window that he would be able to see into the room through the gap in the curtains. It was bad enough sitting on the chair with my briefs pulled up between the cheeks of my bottom but could not bring myself to pull down my briefs as I could see he was getting closer to the window. It was then I panicked and said; please Jim I cannot do this, I am scared that someone might see me through the curtains. Why is somebody there he said; I just replied; please Jim do not make me do this.

Saying this must have made him realize that I had might have seen someone through the gap in the curtains. He told me not to move and then looked through the corner of the curtains. He said; well what do you know there is somebody there so are you going to pull them down. I was so scared that I just said, please Jim I cannot. Okay he said; then I am going to have to make you do it. Make a move and your wife gets to find out what you are doing and to my horror he pulled the curtains open to make the gap in the curtains wider. Now with the gap in the curtains wider I could see more of the motel parking lot and even worse the guy who was now very close to the window.
In fact the guy was so close to the window that he would have had to be blind not to see me through the wider gap in the curtains. Then all of a sudden he stopped walking and stared directly at me, possibly not believing what he could see. I just sat there paralyzed with fear not able to move while he looked at me just praying that he would just go away. But he did not go away instead to my amazement he walked up closer to the window to get a better look. With him now so close to the window I could see that he looked to be in his sixties, medium built and not to well dressed, also I could tell from the look on his face that he could not believe his luck at what he had found me doing. In fact it seemed form the slight smile on his that he could not believe his luck In finding me like this.
This is when I found myself saying in very shaky voice; please I beg you Jim draw the curtains or let me get off the chair as he is looking at me, I cannot be seen like this I am a married man. But Jim also seemed to be getting pleasure from seeing how humiliated and embarrassed I was. Jim then said; I told you Dave you get some strange types around this motel, adding that the guy looked like he wanted to see more. I think you should show him more he said; so pull down your briefs to show him your bottom, then while he is looking at your rear I will take a picture and let’s see what he does.
Please Jim not this I said; he is a total stranger and I am scared of what might happen if I show him anymore than I am showing him at this moment, please I beg you close the curtains. All Jim said was; do it Dave or you know what will happen. So it was with shaking hands that I took hold of the waistband of my briefs and slowly pulled them down to uncover my bottom. I just sat there feeling so humiliated and embarrassed, more than I had ever done before, while he seemed to really enjoy the fact that I had exposed my bottom to him.
Oh my god I thought; if this guy is getting pleasure looking at me he must be gay, bisexual or just a dirty old man. I knew whatever his sexual pleasures were that he would not be satisfied until he had seen more and was sure that Jim, while taking pictures of me, would let him. Jim just wanted to make me feel as humiliated, embarrassed and dirty as he could and he had the hold over me to make me do whatever he wanted, this to me now was more than a dare; it was Jim getting his revenge for what I had made him do. (Continued in part 8)
 

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Dareman

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Meeting a school friend (Part 8)

Part 8
Being made to expose and show my bottom to this total stranger made me feel so humiliated and degraded more than I had ever felt in my whole life. It was only two days ago that I was a happily married family man who had never been naked in front of another guy before. But now since Friday night that had all changed and not only had I stripped myself naked in front of Jim, who was more like a stranger than a friend, but was now sitting in a motel room exposing bottom for a total stranger to look at. I knew that I was being used by Jim to get his own back for what I done to him and I could do nothing to stop it. Not knowing what Jim would make do next was paralyzing me with fear, especially with this other guy now looking at me through the window.
Once again I looked in the mirror, noticing that the guy was still staring at my bottom, and the thought crossed my mind that even though he seemed to be not sure what was going on he certainly looked like he was enjoying seeing me doing what I was doing. Jim then got off the couch, walked towards the door and opened it. With the door open the air coming into the room felt cool on my exposed bottom and I started to feel sick as I heard Jim ask the guy if he would like to come in to watch. As the guy came into the room Jim shut the door and I could feel my face turning red with embarrassment so just lowered my head. This made things worse as with my briefs pulled down I could clearly see my small cock and balls between my legs and they looked so very small.
I just sat there with my back to them with my bottom still exposed listening to what they were saying. They were now both sitting on the couch looking at me when Jim asked the guy what his name was and he said it was Ben and also asked if he liked what he was seeing. Very much Ben said; I am married but bisexual so love to see guys showing themselves and use the internet a lot to look at naked guys. He then asked Jim if he had ever done anything sexual with another guy to which Jim replied that he had got together with a guy a few years ago and they had sucked each others cocks, but no anal. Ben then asked if he had ever fancied fucking a guy’s hole, to which Jim replied that he often thought about it and would like to try it.
How about you Ben, have you ever done anything with another guy. Ben said; that he had sucked a guy off once and also fucked a guy who had done it a few times before, so his hole was not very tight. He then said that he had fantasized about impregnating a tight virgin hole with his sperm. Jim then said; Dave you have never done anything sexual with another guy so you have a virgin hole don’t you, yes I answered in a shaky voice. Ben then said; so has he ever been naked in front of another guy? Not since school have you Dave? I just said no. That’s incredible Ben said; so how did you manage to make him sit on that chair and pull his briefs down to expose his bottom, which I must say looks very sexy. This made me feel like I just wanted to crawl into a hole and disappear.
Then Jim told him about what I had done to him at school and all about what had took place Friday evening also how I now have to do as I am told or my wife and family find out. He also mentioned about taking pictures and putting the story on the web site. Well Ben said; you should make him pay for what he did to you and If I were you I would make him as dirty and slutty as I could. I intend to said Jim, and then to my horror asked Ben if he would like to join in, to which Ben replied that he would love to but only if Jim would let him fulfill his fantasy of impregnating a tight virgin hole with his sperm. Jim said, that’s not a problem, I am sure Dave would love to have you fuck his tight virgin hole, wouldn’t you Dave.

Please Jim I said; not that, I do not want a cock inside of me; it would hurt to much so don’t make me do it; anything but that. Then I said to Jim, that this was going too far and that I had never done anything like this before, just sitting here naked in front of you guys makes me feel so humiliated and dirty.
That’s what it is all about Dave Jim said. Then told Ben that if there was anything he wanted me to show or do then to just tell him, sure will Ben replied this is better than the internet. How about if we get him to show his tight hole to us Jim said and at the same time take pictures, I would love to see it replied Ben.
Okay Dave why don’t you push your ass back towards the edge of the chair and having no choice I did as I was told, Jim took a picture. Ben said that it looked a nice tight hole but could he see more of it, so Jim told me to pull my briefs further down then to move my ass further back and lift myself up a little. I managed to pull my briefs down without moving too much and when they were around my ankles I was able to open my legs more and push my bottom further out. In this position I could tell that I was more open and showing more of my hole. Also in this position I could feel the material of the chair seat against my cock and knew that not only was my hole now exposed but also the back of my balls.
He took a picture. That’s better said Ben; it does look a nice tight hole to fuck and his balls look nice as well but they look quite small. Push your cock between your legs for a picture Dave, then turn around and sit facing us with your legs open so that Ben can see your cock and balls. I put my hand between my legs and pushed my cock back until it went over the edge of the seat; in this position another picture was taken. Being made to sit in this position so that my genitals were exposed for these two guys to look at made me feel so degraded and dirty. But knowing that I was now going to have to sit facing them with my legs apart to show my cock and balls to them was making me feel sick as I was so shy and embarrassed about being so small.
Slowly I stood up with my bottom facing them and as my briefs were now around my ankles I just stepped out of them then turned around and sat down on the chair. With me now facing them I slowly opened my legs and not knowing where to look I just looked to one side at a picture on the wall. Sitting with my legs open exposing my genitals to them was making my face turn red with embarrassment. Out the corner of my eye I could se them both looking between my legs and my face got redder when Ben said; my god Jim he is small, it’s the smallest cock and balls that I have ever seen, his cock is smaller than my wife’s clitty. Jim replied; that’s what I said when I saw them on Friday, I wonder what his wife would say if she could see him now exposing his little cock and balls in front of two guys, Jim then took a picture of my exposed cock and balls. Then he told me to hold my legs up in the air so that he could get a picture of my cock, balls and hole at the same time. Seeing the way they were both looking at my exposed genitals made me realize that they would now be making me do things that I had never in my life done before for their own sexual pleasure. (Continued in part 9)
 

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Dareman

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Meeting a school friend (Part 9)

Part 9
The thought revolted me that they were going to make me do things that I did not want to do just so that they could get sexual pleasure from watching me. Also I realized that it would not end in them just watching me and taking pictures as I was sure they would not be satisfied until they had both used me for their sexual pleasures. This I could not bare to think about but what terrified me the most was that now Ben knew I had a virgin hole that he would not be satisfied until he had used me to fulfill his fantasy of impregnating a tight virgin hole with his sperm. Then I was not sure about Jim and think that he might want to try it for the first time after he had watched Ben fuck me.
Ben must have been getting turned on looking at me as he wanted Jim to get me to feel myself and make my cock hard. So once again to my embarrassment I was made to rub my cock while feeling my balls and hole. I did this while sitting on the chair and even though it was not the first time that I had touched my cock and balls for pleasure, I found it very humiliating to do it while they were watching me, even more so when they told me to put a finger into my hole, which I had never done before.
As is normal for me, due to the size of my cock, I just used two fingers and my thumb of my right hand to stroke my cock and used the fingers of my left hand to touch balls. But as they wanted me to insert a finger into my hole I stopped touching my balls and cock then put a finger of my left hand onto my hole and tried to insert it. But my hole was so tight that I only manage to get the very tip of my finger in and nd was scared to try and push it in any further. Jim then said, can you not get it in further than that? To which I replied that it was tight and that it would not go in. Ben said; put your finger into your mouth and give it a good wetting then try again.
So taking my finger away from my hole I put it into my mouth and made it as wet as I could. While doing this I could smell and taste where my finger had been in my hole, which I did not like. With my finger now quite wet I once again put it onto my hole and started to push it in. It was tight at first so I move my finger around and then felt my hole open up and my finger went in.
With my finger now up my hole I started to rub my cock again and found that even after stroking it for a while it remained quite soft and I was unable to make myself hard like they wanted due to being so embarrassed with them watching me. Jim had just taken two pictures of me stroking myself with my finger in my hole when Ben said that maybe I needed a hand to make me hard but Jim said not yet I want more pictures first. (Continued in part 10)
 

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Dareman

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Meeting a school friend (Part 10)

Part 10
After they had watched me stroke my cock and finger fuck myself for a while and it was certain that I was not going to be able to show them, as they wanted, my cock erect and hard they both decided that I should put on my briefs to cover up, as they put it, my little soft girlie clit. They were both quite annoyed that I had not done as I was told so as I was putting on my briefs Ben said; that as I was unable make my cock hard then I should be made to ware a a cock ring which would make my cock and balls swell and I would become hard.
Jim said; that he thought that was a good idea but he wanted more pictures for the web site first and maybe that would get me aroused. To which Ben replied that it had not so far and with that they made me pose in different positions against a wall so that with Jim sitting on the floor with the camera could take close up pictures looking up between my legs and my bottom.
 

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