My Dare Biography (non-fiction)

[jess_i_kka]

Sorry guys, like I’ve said I’m a college student and I am up to my ass in school work. I started this as a chronology of my life and realized that I’m not nearly the writer that my brother is and some aspects of my “dare life” is really boring and very similar to everyone else’s who post on getdare. So I’m just going to hit the highlights and things that may be different.

One thing that may be different from other people here is that I’ve done most of my dares with my brother. In most of the limits I’ve read people put family on the off limit list. While I’ve never done anything my parents could find out about at least one member of my family is aware.

So we both entered puberty and high school. Our parents sent us to different high schools because they wanted us to separate. I went to an all girls Catholic school and my brother went to an all boys Catholic school. This was interesting. Somehow in ninth grade we stumbled on diaper dares. On a sleepover, I accidentally discovered that the younger sister of a friend who was about 11 years old wore something called “goodnites” to bed. It gave me a great idea. It was around baseball playoff season and Jack and I were betting on the games. Jack liked the St. Louis Cardinals and I liked the Boston Red Sox. So we had a bet that whoever’s team lost the championship would have to do anything the other person asked. I suggested that the loser had to wear “goodnites” not only to bed but all day and that they weren’t allowed to use the bathroom to pee for 3 school days. Jack accepted and lost.

I can remember going to the store to buy the largest boy goodnites we could find. The next day he had to put on the goodnite and I only let him take one spare to change. He hated it but he did this dare for the whole three days. This was our first extreme dare. Needless to say he reciprocated and very soon I was wearing goodnites to school on a dare. I know a lot of people do diaper dares here but no one really talks about it. I found this dare particularly interesting and fun. Firstly it was really weird the first time I peed in the diaper. I had held it as long as I could but you know that feeling, I HAD to go. So I ran to the bathroom and did it in there because I knew the other girls would see the look on my face as I was going. That was alright until I got home. That first day after school Jack had arranged that we go to the local Walmart with some friends. He “graciously” bought me the largest coke that they sold (I think it was 32 oz which is like a liter for our euro friends). Walking home I had to pee so badly that I just let go. I clearly couldn’t squat down like I had done previously in the day in the toilet. Jack saw the look on my face as I was peeing while the whole group was walking to our neighborhood. He nearly fell on the floor laughing and nobody knew what he thought was so funny.

[jess_i_kka]

I don’t really remember what our first “real” nudity dare developed. By real I mean after we had pretty much fully developed. It was the last summer we went to the house in the mountains (we had convinced our parents that it was too boring there because we couldn’t get internet or cell phone signals or anything so they agreed we could stay home with our friends over the summer school holiday) which would mean that it was the summer after 10th grade. Because we were staying home that summer, they put a swimming pool in the backyard. In addition to the pool, there was a small cabana where we could change without bringing our wet bathing suits into the house (our parents are anal about keeping the house clean, etc.). It was one of those hot summer days when the thunderstorms come every afternoon. We were swimming with some friends and it started to rain. Our friends went home and Jack and I decided to stay in the cabana and play cards. Now I have to give some background here. We live in a place where the houses are fairly close together so our neighbors can see into our backyard even though we have a fence all around it. To our left lives our friend Bryan who is a year older than us. But we know each other like forever. He is Jack’s best friend but I don’t really like him that much.

So we got the cards and Jack asks what are the stakes going to be meaning what’s the bet. I suggested something “chore” related like the loser changes the sheets on the other person’s bed or something like that. Jack thought that was lame and suggested that the loser needed to run around the deck in the rain without their swimsuit on. I was like wtf we’d get busted by our mother. Jack went into the house and learned that mom was going to the store for something or other. I didn’t want to do it protesting that the perv Bryan was probably going to be looking down from his bedroom window, etc. and so forth. LOL. Jack called me a chicken and I hate that (because I can do anything he can do) so I agreed. Needless to say I lost the game of Euchre we were playing and I had to run around the pool deck. By this time I was a bit more modest around my brother. We still shared the bathroom and we would occasionally still shower when the other person was in the room washing up or peeing or something but I didn’t walk around without at least a towel wrapped around my body and neither did he. (needless to say we stopped showering together around the age of 13 or so). So I made Jack turn around and I got out of my bikini and wrapped a large pool towel around me. Standing in the door, on the count of three I dropped the towel and ran as fast as I could around the deck. Jack was holding the towel for me when I returned to the door of the cabana and I quickly wrapped it around myself. Later we learned to my relief that Bryan hadn’t seen me. Since Jack and I are all about retribution, lol, the next dare that I won I made Jack get undressed.

So I was planning an all-girls sleepover like a week after I did my first real nude dare. Jack knew that he wasn’t invited to come down to the basement when my girlfriends were there. So I arranged it with Jack that after the party had begun he would call me on my phone. I had someone else answer it and my friend Tiffany answered it. I had arranged that he would say he had forgotten something and that he wanted me to bring it up to him since he wasn’t allowed downstairs. I told Tiff to tell him I was too busy and he should just come down and get it himself. So before the girls came I planted a pair of Jack’s boxers under the cushion of the sofa. Jack had to come downstairs in his robe, take it off at the top of the stairs and come down wearing nothing, walk over to the sofa, ask whoever was sitting there to move, reach in, get the boxers, and put them on, turn around and walk back upstairs all without saying a word. The plan went off perfectly. We could hear the door at the top of the stairs open, Jack walked down naked and silent, there was a lot of shrieking and laughing, Jack walked up to my friend Meghan (her eyes were level with his dick, hahaha), asked her to move, he reached in and retrieved and put on his shorts. Since I knew what was going to happen I was standing at the far end of the room watching it all. The complication for Jack was that by the time he got down to the bottom of the stairs he had a fully erect boner. He said he couldn’t control it but I’ve thought it was the thought of 8 girls being down there. It was the second time I saw my brother have a hardon the first being when we were like 13 years old. It was also the first time I had really seen what a mature dick looked like hard. Since it was summer after 10th grade we must have been like 16 years old.

[jess_i_kka]

Something happened that summer between me and Jack. We got comfortable being around each other naked again and started skinny-dipping in our pool after our parents would go to bed and all the lights were off. I think this was when I discovered that I’m more of an exhibitionist than Jack. It would bother him when he would get hard when only I was there. It didn’t bother me at all. (Am I weird?).

The next time our extreme dares increased in intensity happened right after Christmas during the time we were in the 11th grade. I’ve already mentioned Jack’s friend Bryan from next door. Well I had to stay after school because I was participating on my school’s track team and we had practices after school. I got home and after changing out of my uniform (did I mention the uniform? This was an absolutely ugly white shirt and skorts with opaque blue tights) I walked through the bathroom to see what Jack was up to. I found Jack and Bryan sitting on the floor looking at some books with pictures of naked women in them. They tried to cover it up but I started to call them perverts and generally making fun of them. I said I wanted to see what they were looking at and Bryan got all defensive saying that they were only photography books (I didn’t mention that Bryan is an awesome photographer). So I convinced that that since they were only photography books I should be able to look at them. They were actually pretty kewl with mostly naked female models and a few male models. I made the mistake of calling this porno and both Bryan and Jack jumped all over me saying that its art and not porn and I was like what’s the difference and Jack took out a Penthouse magazine he had hidden in his closet (which pissed me off because I didn’t think we had secrets from each other but that is another story). They showed me that it was only porn if you could see up the girl’s vagina and clitoris and all. So I was like yeah, so what.

Anyway, Bryan was complaining that he wished that he could have some nude photographs for the portfolio that he was submitting to colleges in a few weeks and that the photography classes at his school (he went to the same all boys school as my brother) didn’t allow nudes because it was a Catholic school. Jack said something like Jess, why don’t you pose for him. I answered yeah right! When hell freezes over and suggested that males could pose nude so why didn’t Jack pose. That got a negative reaction from both the boys. So I asked him if the art colleges he was applying to required nudes and he said no but they like a well rounded portfolio and he would stand a better chance to get in if he had them. I grabbed the books and ran back to my own room telling the boys I was going to give the books to my mother. LOL The boys chased me but Bryan knew he was NEVER allowed in my room so he stopped at the door of the bathroom because I never really liked Bryan anyway so Jack knocked me on the bed and took the books back. What good fun we had back in the day.

So we turned 17 years old on January 16th and my probationary license converted to a full license so I was able to drive. Our parents didn’t really want us driving so we had to share the two cars with our parents. But it was so unfair that I couldn’t drive even though the state said I could. So one day after school one of my friends who had a car but had cheerleader practice that day said I could drive around in her car and pick her up after practice. As luck would have it, Jack and his friends who were hanging out trying to scam on the girls at my school because they were a bunch of horny dogs saw me driving out of the parking lot. Jack got a picture of me driving on his phone. When I went home Jack was waiting and said he was going to blackmail me with this picture because we were not supposed to drive other peoples cars and if I didn’t pay he’d show the picture to our father. I was angry and hurt because Jack never tried anything like this before and I told him to go fuck himself went back to my room and locked my doors. I knew that if our father found out he’d not let me drive even his car for a month or whatever. So when I calmed down I went to Jack’s room and I asked how much he wanted. He grinned and said it wasn’t how much, it was what he wanted. He said that he wanted to help his friend Bryan and that I had to pose nude for his college application portfolio. I was like NO! Doing naked dares in front of him was fun even if there was a risk of getting caught. But posing naked in front of his creepy friend was another thing.

He said if I didn’t do it he would show the picture to our father and, well I have to admit it, I started to cry. Yes girls, Jess cries. I told him that I was hurt that he would try to blackmail me and that he knew how much trouble I would get into and all. He also has a soft side and he put his arm around me and gave me a big hug. He reasoned (jack is very good at reasoning) that this is the sort of game we’ve played for years and that he would have expected me to do the same (and he was right, I really would have done the same). He said he really wanted to help Bryan and that the requirement was firm. I was still protesting that I didn’t want to do this in front of and he told me that Bryan had told him that he watched us skinny dip in the pool all summer so it wouldn’t really matter. I said that that was different than being alone in a room with him taking pictures and Jack said he would be there too. I had no choice to agree. But then Jack put on an additional requirement. Jack told me Bryan couldn’t know it was a dare and that I had to call him to tell him I’d do it on my own idea.

So after dinner we went next door to Bryans room. As I was instructed (get a hint of my first sub role here?) In the course of the convo I asked Bryan if a girl was to agree to pose for him nude, what would it be like. He thought a minute and said that it would have to be during the day when his parents were working and his younger brother was in school. That he could cut classes that day. He said he would make a “classic” backdrop in his basement studio. I asked him what that meant and he said he’d hang some sheets to make it look all soft and cloudy. He said he’d move a small sofa there because he’d want to get the classical poses. I asked him what the classical poses were and he said lying face down, lying face up in something called the Odalisque pose, sitting in a chair, and standing. I asked him to show me examples of those poses in his photography books and he did. But he was getting suspicious and asked me if I knew someone who would do it he could pay like $50 for it. I said I didn’t know anyone but would he want me to do it if I volunteered. He was dumbfounded. He as saying no way, I don’t believe it and all. I said “way” and Jack, who acted surprised said but I have to be there because I need to protect my sister. I told him that I had conditions (which made Jack made a face when I said that) and those conditions were that he had to promise not to show those pictures to anyone around his school or town or to his family or anyone. The second condition was that I wasn’t doing porn. It was to be strictly art.

We set up the day later that week. Jack and I were pretty good at forging our parents signature so on Friday Jack and I appeared to go to school as normal. Our mother left after us because she taught in the local elementary school. After we knew she was gone we went home and I pretended to be mom and Jack pretended to be dad and we called each others school saying we were each sick that day. We snuck out the back door and went to Bryan’s house when he called to say his parents were gone to work. He was also “sick” that day. He and Jack immediately went to the basement to set things up. I stayed in the kitchen thinking what the hell am I doing. In a few minutes they were back and I was having a bowl of Fruit Loops which are my favorite cereal. Bryan said he was ready and we should hurry in case something with the parents went wrong. I asked him how many pictures he had to take and he said he was using the digital and not the film camera so he would like to take 20 or 30 of each pose. I went downstairs and it looked like what I imagined a professional studio would look like. There were two flood lights clipped to the ceiling lighting an area covered with dark brown sheets from the floor and up the wall to the ceiling. There was this small sofa also covered with a brown sheet. I commented that I would have expected white but he said he wanted to contrast my white skin because I have very pail and almost pink skin and red hair. There was a kitchen stool (u know the kind without a back) that was also covered in a sheet. Bryan was nice and asked me if I was ready to start and I bit my lip and said I suppose so. He then suggested we run through the poses with my clothes on so we did. When we finished which took about 20 minutes he suggested that I get undressed so we could start. I was like NO, I don’t think so. I’m not stripping naked in front of you guys like this was some sort of locker room. I told him I would undress in the bathroom on the first floor and he said what if one of his parents came home unexpectedly they would find my clothes there. That seemed to make sense to me at the time so I said ok.

I made the boys turn around and I got out of my school uniform. It seems strange now but I actually folded my clothes in a way that I could hide my bra and undies in my clothes because I didn’t want Bryan to see them. I went over to the sofa and lied down with my face in the cushions. I pulled the sheet covering the back over my butt and told them that I was ready and they could turn around. Bryan got angry that I messed up the sheets (artists are weird) but Jack volunteered to fix it and uncovered my bare butt at the same time. Bryan was very professional and didn’t make any comments. Jack wasn’t so nice. He made a comment about the size of my butt and the whiteness of my skin (he has darker skin and brown hair). Bryan took a bunch of pictures both with the camera on the tripod and holding it when he wanted to get a different angle. At first I was just laying but then he asked me to turn my head toward the camera. . I instinctually smiled and looked at the camera and he didn’t like that. He wanted me to focus in other places like the camera was not there and not smile. This was not too bad except for when he wanted me to move my arms from my sides and put them over my head. I was using them to hide my boobs.

The second pose was to lay on my back sort of sitting up with my legs straight out on the sofa. This was hard. I turned in a way that he couldn’t see my front with my legs crossed tightly and my arms over my boobs. Jack was crude having a great time and said show us some boob Jess. Bryan looked annoyed but said to keep my legs crossed but tilt away from the back of the sofa and put one arm on the sofa back and one by my side. This was weird but I did it anyway. After about 10 flashes I was actually getting used to be nude (remember the exhibitionist thing?). Bryan asked me to uncross my legs and be more relaxed. This was easier than I would have thought. I uncrossed my legs and the right leg slipped off the sofa and so my foot was on the floor. Before I could fix it Bryan said he liked that pose so leave it there. I realized that I was showing the full amount of my red pubic hair which made me blush (I blush when I’m embarrassed). Jack made a comment about this but Bryan said he was going to use only black and white so it didn’t matter.

When Bryan was ready for the next pose, I said I wanted Jack to leave because of all the rude comments he was making. I was actually getting into the modeling thing which shouldn’t have surprised me since I like having my picture taken I already had an inkling that I like being naked. Bryan agreed so we made Jack go upstairs for the remainder of the shoot. I went from the lying down poses to the standing poses. I had to hold various poses from standing stiffly with my feet together to more relaxed poses with one foot in front of the other like I was walking. Bryan shot pictures mostly holding his camera and having me turn around a lot. For the final set of pictures I sat on the sheet covered stool. For most of these I was able to keep my hands in my lap except one where Bryan wanted me to relax my legs. He took a few dozen shots like this and tried to shoot me from the back but couldn’t because he kept getting the basement in the background. Finally he had me turn on the stool with my back to him. Finally he said Jess I think we’re done. I was relieved. But I thought I wanted to get back at Jack. I asked Bryan if he could do a few more shots just for me and not for his portfolio. I had him promise that nobody other than us would see the pictures and I went over to the sofa, sat down and told Bryan to start taking picture and not say a word. He started shooting and the flash went off. I started to move. I layed back on the sofa, stretched my legs, opened and closed them scissor-like, then I surprised myself and Bryan alike and put my feet on the sofa giving him a full shot of my privates. He stumbled and I could actually see the outline of his hard penis in this jeans. I told him I wanted him to take a few close up shots. He did it. I quickly closed my legs and I had a further idea. I told him to keep shooting. I stood up, walked over to the pile of my clothes and started to get dressed. He stumbled again but I told him to keep shooting. He took a complete set of pictures of me getting dressed from pulling on my panties and hooking my bra to buttoning my school uniform blouse.

Bryan left right away and ran upstairs to the bathroom. This was the first time I am sure that 1) I directly gave a boy an erection and 2) that he went to the bathroom to masterbate to what he just saw. I found a perverse sense of pleasure in that because as then I still don’t really like him. He did keep his promise and never showed those final pictures to anyone but I have a complete copy on a flash drive and I’m sure so does he. He did share the art pictures with me and Jack as well. I still don’t like the way my butt looks. I think its out of proportion to my body since I am rather small on top. Bryan, by the way, got into one of the top photography schools in the US called the Parson’s School of Design.

[Komodo Jones]

I feel your sympathy as a college student. Those darn professors are sadists, but I am liking these keep them coming if you have more.

[Bloxo]

If this was published I am sure it would be a best seller, it is wonderfully written, it really did leave me gripped at every stage and I think that it is a wonderful story to share with us all. You have a very strong writting talent at your disposal there. Keep up the good work!

[jess_i_kka]

I had been pretty oblivious to the whole boy thing throughout high school until 11th grade. As I mentioned I went to an all girls school. In had my first real boyfriend that spring. One of my brother’s friends invited me to the junior prom at their school. This was fun because I my brother was there an all his friends whom I knew. I liked Jim and we started hanging out.

I had bought a new bikini and asked Jack to tell me if he thought it looked good. I tried it on in the bathroom and went into his room. Jack laughed when he saw me because I was ghost white. Then he looked down at the bottoms and said that it looked bumpy down there. What he was referring to was the bulge caused by a growth spurt in pubic hair since the last summer. He said that I should shave it off. I was like NO WAY. I had never needed to do it until then but I had friends who did and complained that it itched like hell as it was growing in. I went back into the bathroom and trimmed it down and showed Jack again but he said that it was still visible. I was ready to bring back a perfectly nice bikini when I dared Jack to a contest. I said I could take shaving mine but there was no way he could stand shaving his. (Now we had gotten over the shyness of early teen years and while we didn’t exactly parade around naked if one of us was in the shower or whatever we didn’t exactly care if the other saw anything.) So he took up the challenge. We went into the bathroom and I got a new razor that I used for my armpits and legs and using Jack’s shaving cream, shaved my pubic hair. I handed Jack the razor and said it was his turn. He lowered his pants and lathered up. I laughed at how apprehensive he was to have a razor so close to his willy. (Boys are so much more complex than girls.) Well for the next few weeks we were both a sight. I would catch him rubbing his pubic area as the hair grew in. I took care of that problem by just shaving every 5 days or so. I think I got the better of that dare.

Having a shaved pubic area meant that when Jim and I messed around there was much more stimulation on my clitoris. I had been masturbating since I was much younger but Jim and I would get hot and heavy and ultimately got to second base but a combination of my parents rules and my not wanting to get pregnant kept it that way. (By second base I mean we didn’t do anything under our clothes just over them.) Needless to say I was frustrated and started masturbating much more. I would estimate that I was probably doing it 2 times a day on average and more on the weekends. I was fairly naïve for a 17 year old mostly because our parents put filters on all the computers in the house. So even if I wanted to look at porn the filter would block it. Jack got around that by going to friends houses but I didn’t feel comfortable with that.

Well with all that masturbating I found myself getting sloppy. I almost got caught by my mother when I didn’t realize I left my room door unlocked and didn’t hear her come in from work. I only realized she was home when she hit the top step which always squeaked. I dove under the covers and told her I was sick and had the chills which she believed. One Saturday before school ended that year mom and dad were out playing golf (which they did a lot) and Jack was at a lacrosse game at his high school. I got off the phone with Jim and was feeling horny. I put my techno trance music up loud and slipped off my pajama bottoms and started going at it. Now one thing is that I have these really sensitive nipples and like to rub them when I’m doing IT. I know some girls don’t but I do. So I was wearing a tank top and no bra so after rubbing myself down there for a while I slipped down the straps of the tank top and were rubbing my nipples with one hand and my privates with the other. The music was really loud and I would actually get into a zen-like trance when I was doing it. I would typically get 3 or 4 orgasms at a time and this time was no exception. When I was finally finished I opened my eyes and looked up to see Jack standing in the doorway from the bathroom to my room. I had forgotten to close it and I didn’t hear Jack come in. When I realized I was there I pulled a sheet over me and screamed at him to get out. Instead he came into the room and I could see that he was obviously aroused. He sat on the bed and kept saying that that was the most incredible thing he ever saw. I told him I thought he was a perv and that I was his sister and he shouldn’t be having the thoughts he was having. He denied having any sexual feeling toward me but said what boy wouldn’t be aroused by the sight of any girl masturbating and I kind of bought that reasoning. (For the dirty minded among you, Jack and I have never messed around like that!!!) I told Jack to leave and he did and I got dressed. I went into his room and said that he owed me something for what he did and saw. He said what did I have in mind. I first made him promise that he would never fantasize with me in the picture because that would be sick. He agreed. Then I had an idea. Jim and I hadn’t done anything under our clothes but I was curious. I clearly knew what a penis looked like but I didn’t really understand how it worked. I told Jack that in retribution, I wanted to watch him jerk off. Now I know some of you are saying “ewww,” how many girls out there would either like the opportunity to see how is works before you ever had to touch one?

So Jack thought that was fair (we are a strange couple, aren’t we?) but said our parents were probably coming home soon. That night however our parents were going out with friends and Jack and I had an 11 pm curfew. When we got home I asked Jack if Dad said what time they’d be home and he said Dad said they’d be late, probably like 1 am. I told Jack that it was payback time. He sighed and agreed and said how do I want him to do it. I told him I had no idea but that he should just do what he normally does. Now I was sitting on the edge of the bed and he said it was too weird with me sitting right there on the bed. I agreed and went and sat on the window seat that was about 5 feet away. Jack went to the bathroom and came out in a tee shirt and boxers. He protested that this was going to be weird and he got on the bed and tried to do it. It was so funny because it just wouldn’t work. No matter how much Jack touched it and pulled at it it remained soft. Finally he said that I was inhibiting him. I suggested that he get a magazine that I knew he had hidden in his closet. He got up and got a Playboy magazine and opened it to the porno pictures. He propped up the book on a pillow and started pulling his dick. This time it responded immediately. I was surprised how big it grew almost doubling its length. I was also surprised at how rough he could be with it because I had always thought these were sensitive areas for a boy. I tried to ask him about it and he yelled that he had to concentrate so I should shut up. LOL After about 3-4 minutes Jack’s willy ejaculated with all this stuff shooting all over the place. He said something like oh shit I forgot to put a towel down as the white semen went all over the place. He pulled his boxers back on and went into the bathroom to get a towel to clean up. I was surprised to see that he remained hard for like 10 minutes after his orgasm. I asked him if I could ask him questions and he said sure. I wanted to know if boys like it that rough and he said that it wasn’t that rough but the sensitive parts are the balls not the dick. He also said that boys like it fast. I asked him if he knew what a blow job was and he explained it to me. I was surprised to hear that a girl could stop before a boy ejaculated and the boy wouldn’t then do it in a girl’s mouth which at the time I found disgusting. That was our next extreme dare, so to speak. I was greatful for the education because the next weekend I gave my first hand job to my boyfriend Jim.

[GoogleMaster]

Fantastic! Thank you. I am very impressed with the quality and subject you are writing about. I can't wait for more. I will follow this thread closely!

Jim was clearly a lucky guy. I think that sort of experiance, while unusual and unique, would have benifited many of my partners. I welcome anyone to be open about the details of sex and masterbation. Ask questions, answer truthfully if asked and feel free to share great stories like Jess_i_kka has done.

Well done!

Thanks!

[HSsportsstar 1]

i really like this story, i hope you continue to write it

[jess_i_kka]

I’m not going to go into the details about my relationship life because this is a dare biography and not my sordid life. Suffice it to say that Jim and I decided we should become more intimate over that summer. The summer after 11th grade was different for us since both Jack and I got trivial summer jobs. Jack worked at a pool club as a lifeguard and I worked in a clothing store in a mall. We naturally didn’t have as much time to hang around thinking up dares.

We did discover one of those newspapers that advertise people trying to sell their old junk called the Pennysaver. We would challenge each other to call the seller and act all seriously and then ask some completely inane question or make an appointment to see it never showing up. Jack discovered craigslist after school started that year. We were seniors and he wanted to buy a used scooter with his summer earnings and was able to find some for sale in our area. One day I was in Jack’s room and he had craigslist open on his computer. I had (and for that matter still don’t have) no interest in cars so I started looking at what else this site had to offer. I noticed a myriad of things for sale etc. I also discovered the “personals” section. You know that section. It is where hard up people post pictures in the hope of finding someone to date. I went to the W seeking M (which means women seeking men section and found a large number of lonely hard up older women looking for men. I had an idea. We were already doing stupid dares calling people etc.

So when Jack got back to his room, I proposed a dare to Jack. I said to him I’d bet I could find a dare based on craigslist that he wouldn’t do. He, of course said there was nothing I could come up with that he wouldn’t do. So he agreed to the bet. The bet was that if he didn’t do whatever I came up with, he’d have to do my calculus homework for a month (because although I’m majoring in some sort of bio engineering or whatever I hate calculus). I opened the personals section and I said that I was going arrange for him to meet one of these hard up old women for a date and he had to go on the date. Thinking that they wouldn’t answer a 17 year old high school senior, I replied to 5 of these women ranging in age from 28 years old to 34 years old. I sent them a picture of Jack and pretended I was he. A couple answered but stopped communicating when I told them that I (meaning Jack) was 17 years old and in high school. One who answered was a 32 year old divorced woman with a 2 year old child. I told her that she looked hot (which she didn’t because she was overweight) and that I always liked older women, blah blah blah.
She didn’t seem to care that Jack was only 17 and finally asked if they could talk on the phone. I couldn’t pretend to be Jack any more so I arranged for her to call Jack’s phone when I was going to be there. I listened in on the convo and told Jack what to say in response to her questions. She was ultimately interested and they arranged to have a dinner the next Saturday. I drove Jack to the restaurant and made sure that he went in and looked through the window to see if he actually did meet her. I saw that she actually was the person who had their picture on craigslist. I left and called Jack and told him that I would pick him up when he was done. Well he never did call me. He claims that he went home with the woman and actually had sex with her. I wasn’t there but Jack got home at 11:55 pm which was 5 minutes sooner than our curfew that year. He had a smile on his face and he went into his room and went to sleep. The next day he said that his turn was next and that he would formulate the next dare. It was near the Thanksgiving holiday and then we got into the Christmas season so he forgot about it completely, or so I thought. He got back at me the following Valentines Day 2008.

[jess_i_kka]

We celebrated our 18th birthdays in January of that year. Our parents made a big deal about it and had a rather large party. That was also the year we were busy with college applications and campus visits and the such. Jack and I decided that we wanted to find a school where we could both be happy. This was not easy because Jack wants to be a writer and I’m more into science. We settled on a short list and we both filed our applications. We had finished our applications in early February and then relaxed a bit. Jim and I had broken up before Christmas. The creep had cheated on me and I found out about it from a girlfriend who saw him and a hussy making out in his car.

I didn’t realize that Jack had been planning his “get back” dare in retribution for the “blind date” with the older woman. Valentine’s Day in the United States is a horrible holiday if you are a single girl. All your girlfriends are getting cards and gifts and talking about the romantic dinners that their boyfriends are taking them on. I was sitting home and Jack, who had a girlfriend, got home from his date. He came into my room to bring me a piece of cake that he brought home from the restaurant (he really DOES take care of me) and to console me. As I was eating away my sorrow Jack brought up the fact that I owed him a dare. He reminded me that this would be a dare he came up with and that it would involve the personals section of craigslist. I dreaded that I would have to probably go out on a date with some old guy that Jack picked out for me and that knowing his deviousness he would pick the fattest, oldest, ugliest guy posted.

A few days went by and Jack was very secretive. He would turn off his computer screen each time I walked into his room. That next Sunday night as I was getting ready for bed Jack came into my room with his notebook and said that he had some options for me. Jack opened his email and opened three emails he had received. What Jack had been doing for the previous few days was answering some personal ads from craigslist. I had assumed that he would have been in the section Man seeking Woman, the opposite I had done for his dare. What I couldn’t imagine is that he had responded to ads in the section MW seeking W! Please allow me to interpret: Man and Woman seeking Woman! What Jack was responding to was ads for THREESOMES!!! Now I need to digress here for a moment. I had been intimate with my boyfriend Jim. Jack knew I was sexually active because 1) we used to do it in my room when our parents were out and he would yell at me to be quiet when he was home because he didn’t need to hear that through the bathroom that separated our rooms and 2) I tell Jack everything. Jack also knew something else that no one (not even my ex-bf) knew. Jack knew that I had been curious about being with a girl. To be really honest, sex with my first boyfriend sucked. The “first time” was really ugly and the other times it was like over before it began. Jim also didn’t like DATY so that even though I was having sex HE got all the pleasure and I didn’t get any unless I masturbated (which we did together a few times).

So Jack let me read the responses. He told me that he had responded and sent my picture to 8 ads and that three people responded. All of them enclosed pictures. One enclosed close up pictures of their genitals which I found to be disgusting. One couple was this really fat couple. The third was a couple who said he was 41 and she was 35. Now my mom was 43 at the time and my dad was 44. At first I said to Jack that no way was I going to do this. He told me that he wouldn't force me but since I said I was "curious" why not play along for a while. I ultimately agreed. We (meaning me and Jack together) traded a few emails with this couple. They wanted to know stuff like how old I was and stuff. Then they suggested we talk on the phone. We agreed and we talked. I was so scared that Jack and I put it on speaker and he told me what to respond. I told them that I was 18 and curious and that I wasn't that experienced and that sex with my boyfriend wasn't that good. They asked what I liked to do and if I ever had any experience with a girl. I had to answer no but that didn't seem to matter to them. I also told them that I wouldn't do unsafe sex and that I really still wasn't sure I wanted to do it. They said they were into light bondage and I said that I wouldn't do that and they said fine they would respect my limits. After 3 phone calls (they actually sounded nice and the guy did not sound like my father at all) they suggested that we meet at a Paninis (for my non-US readers that is a restaurant chain in the US) near their house and that if we "hit it off" I could go with them to their house. I agreed with Jack's urging. I said what if they are weirdos or something and Jack said that we'll get their address and he'd be nearby if I needed help and that he would be in the restaurant to help me assess if this was "safe." The the next friday, must have been the first friday that March, I put on some mature looking clothes (I wore a woolen skirt and a sweater top) and Jack drove me to the Paninis. He dropped me off 10 minutes early and parked the car so that he could come in like we weren't together. I got some coffee and sat down. Jack sat at a table next to where I was sitting with a sandwich and a newspaper so he could pretend not to be listening. A few minutes later a couple I recognized from their pictures came in They greeted me and went to the counter to get some sandwiches. They returned to the table and we had some small talk about me not being hungry etc. Then the guy, I'll call him Tom because we agreed not to talk about his, asked to see my ID because I looked so young. I showed it to him and wasn't insulted or anything because I understood that he wanted to protect themselves from any minor issues. They ate and we talked about all sorts of things like what did they do (he is a lawyer she is a nurse) and what I liked to do etc. He was fairly short at like 5'8" with an athletic build. Jane, the woman, was smaller than me at like 5'1" and wasn't exactly thin but not fat either. They told me that they had one child who was 1 year old who was at his grandmothers. Jane complained about still having "baby fat" from having the baby etc.. They seemed decent enough and after about an hour and 2 large coffee they asked if I wanted to go back to their house. I said I needed their address to tell my "friend" where I'd be and they understand. I excused myself and went to the bathroom. Jack followed quickly. I asked him what he thought and he said that they seemed okay but it was up to me. I asked him where he'd be and he said he'd park the car near their house and if I needed him I should just press the speed dial on my phone and he'd be there in a minute. So with a lot of nervousness I returned and said I was ready to go back with them. They said they were so glad and we left the restaurant and walked to their car. Their car was very cool. It was some sort of BMW in black with tan leather upholstery. We drove for only like 10 minutes and arrived at a very nice suburban looking street that looked a lot like the street I lived on but about 30 minutes away. Their house was also a standard US suburban house a lot like ours. There was baby stuff around so I knew they weren't lying about that. I told them I needed to use the bathroom and they told showed me where it was. I didn't really have to use it but I wanted to make sure Jack was nearby. He told me he was parked across the street and anytime I wanted to leave I should just run out the door because I already fulfilled the terms of the dare. I said no that I wanted to see where this was going to go.

I came out of the powder room and Tom was mixing vodkas for him and Jane. He asked me if I wanted one. I said no but then he said that I said I liked wine coolers and offered me one. I accepted and we went to the family room were there was a large sofa and a tv and such. Jane turned on the TV and put on MTV or something. I sat nervously on a chair across from the sofa and Tom and Jane sat on the sofa. We were watching the TV and talking. Before I could finish my smirnoff Tom brought me another one. I wasn't too used to drinking so I was getting light headed. I was into the videos and hardly talking at all when Jane asked if I wanted a "tour" of the house. She showed me all the room and was very proud of how they were decorated. She clearly forgot that I was 18 and not terribly interesting in interior decorating. We went upstairs and she showed me the master bedroom and bath. They had an enormous king sized bed. Jane said she needed to use the bathroom so I went back downstairs. Tom brought me another smirnoff and i drank it very slowly. A few minutes later Jane came downstairs wearing a short silky nightgown. She was slightly pudgy but not that bad for an older woman who had a baby. I noticed that although she didn't have large boobs that they hung down. She sat back down on the sofa next to Tom and they started to get romantic kissing and cuddling. Jane told Tom to go get the gift for me. I was surprised. They handed me a box that was obviously from Victoria's Secret. I went to open it and Jane said, why don't I go upstairs, take a shower and put it on. I was surprised but I figured WTF so I went upstairs to the master bath to this luxurious shower with all these water spouts. I locked the door and called Jack to make sure he was still there. He told me not to worry and asked if I was alright. He suggested I don't drink anymore. I got undressed and took a quick shower but didn't get my hair wet bc I didn't want to dry it. I got out and wrapped myself in a towel and opened the box. Inside was this black lace baby doll nightgown with back lace panties and a lacy robe. I put it on and my nearly pure white skin made the black nearly transparent. I looked in the mirror and could see that even though I was wearing the short robe that you could see skin through 3 layers of fabric. Too embarrassed to go downstairs like that I found a large bath towel and wrapped myself in it. I went downstairs and they asked if I didn't like the gift. I said I liked it fine but it was too sheer for my taste and was more comfortable wrapped in the towel. Tom and Jane were already doing some heavy making out which at the time looked weird for two old people like them. When I cam downstairs and went to sit on the chair they said I should sit on the sofa. I sat next to Tom who was busy kissing and feeling up his wife. He turns to me and plants a large kiss on my lips. I didn't really know how to respond so at first I didn't open my mouth. Jane got on her knees on the sofa and said something like don't be afraid that he was a good kisser. He kissed me again and forced his tongue between my lips. When our tongues touched it wss very weird but I opened my mouth and we engaged in what was my longest french kiss to date. He put his hands on my shoulders and pushed me against the back of the sofa kissing me hard. Compared to Jim, Tom was a great kisser. Jane got up and sat on the other side of me and started kissing my cheek. I turned my head and our lips met. It was so weird because the kiss was so gentle. I don't know how it happened or how long we were kissing for but Jane undid the towel tied around me. I moved my hands up to cover my breasts but Tom took them and kissed me from the other side. They got up and suggested we go up to the bedroom. My head was spinning from a combination of the wine cooler and the events of what was happening to me. We went upstairs and they positioned me in the center with each of them at either side of me. Jane and Tom had clearly done this before because they seemed to know their roles. Jane was straddled across me kissing me with her hands over the fabric of the baby doll. She worked her way down kissing the fabric as she went down to the lace panties. Without saying a word she worked them off my butt and started to do oral on me. It was good but I didn't have an orgasm or anything. Tom, now stripped down to his boxers was behind Jane doing something with her butt. All I could see was his head bobbing up and down.

Tom removed Jane's nighty and she removed his boxers. He was much bigger then Jim was. He also wasn't circumcised which looked weird to me since all the penises i'd seen were. LOL. She gave him a blow job and he got very hard. They got on either side of me and removed my robe. I wanted to protest but I didn't want to at the same time. I had 4 hands all over my body. Tom took charge and lifted up the sheer baby dolls and took it over my head. Soon I had two mouths all over my body. Jane was back at my privates and Tom was kissing my boobs. I have really sensitive nipples and this was driving me wild. I did have an orgasm this time. Well actually more than one. Actually I don't know how many. I lost track because Tom got up and kneeled over me to have me suck him. They moved me over and Jane layed down and I took her place. Tom "ate" me from the back was the weirdest feeling because he was doing stuff with his fingers and my butt. They had a bottle of this stuff called Glide and I had my first finger in my ass which was very weird. After a while Jane said she wanted to get it more exciting so she got up and got some silk cords which Tom used to tie her hands to the center of the headboard and her feet to the bottom of the bed in a spread eagle fashion. He got a vibrator out we used it on Jane. He asked me if I wanted to try it. At first I said know but then watching her like that I got excited so I said yes. He untied her and I layed in the middle of the bed. He tied my hands together in the middle of the headboard. Instead of tying my feet to the bottom of the bed, he tied them to the edges of the headboard. Jane and Tom ate me and then Tom put on a condom and, well, yes. we did it. They untied me and we tied up Tom and Jane and I ravished him until he was hard again and Jane got on him and did it cowgirl style. We messed around a lot more and after about 3 hours I said I had to go home. They offered to drive me back to Paninis because they thought I left my car there. I told them no bc my "friend" was waiting for me. I got dressed and was going to leave the "gift" there but they said I should take it. I called Jack and took the baby doll (I still have it although I haven't worn it because it is too sheer) and went home. Jack wanted me to tell him what happened but I never did. I guess he'll read about it here.

I have a warning for people though. I did this and realized how stupid I was and how lucky I was that nothing bad happened. I WOULD NOT RECOMMEND THAT ANYONE EVER DO THIS AND I WILL NEVER DO THIS AGAIN. There are just too many creeps out there.

[Komodo Jones]

Even though, you said nobody should do this, this has been the hottest dare of yours yet. Even though I'm a guy I wish I could have an experience like that.

[Bloxo]

Wow again breathtaking writing, tom was a lucky man lol!

[GoogleMaster]

I have had the opportunity to be Tom, in this story. In fact my experiance happend very much like this. Thank you Craigslist. Here is what I would caution.

Get to know the other people.

Tell someone where you are and when you will be back.

State your limits early and NEVER cross them.

Don't drink. One glass as an icebreaker, maybe, but you don't need it and it is way fun even without it.

All that being said, it is A LOT of fun. For everyone. As long as everyone is a willing and happy participant. Talk a lot. Ask questions. Be adventuerious in your fantasies, but cautious in your actions.

Thanks Jess_i_kka for telling that story. I hope your brave dare will inspire others who are shy and nervious yet curious like you were. That is exactly what I think a good game of TorD should do.

Keep up the great thread!

[jess_i_kka]

Originally Posted by Komodo Jones

Even though, you said nobody should do this, this has been the hottest dare of yours yet. Even though I'm a guy I wish I could have an experience like that.

This was a stupid dare because these people could have murdered me or abducted me or something. It was hot, but stupid.

[doomed_soul89]

Originally Posted by jess_i_kka

This was a stupid dare because these people could have murdered me or abducted me or something. It was hot, but stupid.

lol rapist and murderers don't use personal ads, one look at your computer and the cops can track them, they just grab you off the street