Truth or dare with Heather part 1

I'm breaking this up into a few posts because of how long of a story it is.

Ok so we started out both with a few truth questions. I asked if she was a virgin, - no (but she had only been with one guy, the one she lived with for 3 1/2 years) , she said she knows i'm not because Samantha told her about me, so she asked how many girls i'd been with. I totally lied and told her 5 or 6, no way was I going to tell her that honestly its so many I dont know the number... with how conservative she was being she would likely have freaked out if I disclosed that to her. She had never been part of a 3 some and probably never will, I told her i'd tried it once with two girls and she thought that was disgusting.

What else did I find out about her? She broke up with her ex because he was cheating on her, she caught him in their bed with a much older woman, turns out he'd been cheating on her for over a year with several people and she had no clue. I found out that she didnt really like giving BJs because of a bad gag reflex, her favorite position was being on top, doggy style was a close second. It turned into more of a confessional than a truth or dare after a while because we just started sharing things. She said that her ex had only done oral on a her a few times but she really enjoyed it. She has never masterbated, but since leaving him she has been really horny a few nights and wanted to, but never did. She is completely against porn and would never consider watching it, she said "those girls are someones daughter and as a future mother that disgusts me", interesting way to look at it, but whatever. I also found out that her boobs were indeed fake, her ex bought them for her after a year together because he was tired of her A cup. She never realized how much big boobs could do to your confidence. I inquired if her strawberry blonde hair matched the carpet but she told me that was too much information for right now. So then I asked if she dyes her hair, but she knew that was a trap question so she declined to answer it.

I tried to find out how much she knew about Samantha and my bed life, but she says all that Samantha told her was that I was really good in bed, give excellent head and have "the largest dick she's ever laid eyes on". I asked if she wanted to be the judge of that, she gave me the dirty look and told me nope, she'll let me know when (if) she ever wants to see it, but not now"

After probably 45 minutes or so of talking about our sex lives and other stuff, I reminded her this was truth or dare and I was going to extend a dare, she said thats fine, just remember the rule. So I dared her to give me a lap dance, she said she would but no touching. So she gave me a nice little lap dance. She then dared me to call one of the girls i've slept with (cant be Samantha) and ask them to rate how good I am in bed from 1-10. I was like no, that is stupid. She told me that the more I complied with her dares, the more daring she would be. I almost felt like a puppet, she was totally in control. She knew she had the prize that I wanted, and it was right between her legs, and she could make me do whatever I want to get it. So I jog my mind to figure out who I should call and figure out how the hell I can bring this into conversation. I decide to give Chelsea a call, she's one of my 'friends with benefits', we only got it on once, link to post, back in August of 2005 but I hadn't really heard much from her after that. I had heard through a few friends that she was engaged, so I never tried to call or text her.

So Heather asks who I'm going to call, I tell her Chelsea, she asks how many times we'd slept together, told her once. So she told me I had to ask her on a scale of 1 (bad) to 10 (great), how I was in bed. Then I had to ask her if she thinks my penis is smaller than average, average, or larger than average. I was like no way, one question will be embarassing enough, but to ask about my penis size? Heather said just remember, she'll do more daring things if I comply. So the puppet master won, Chelsea answers the phone, she initially didn't recognize my voice, I told her who I was and she was like "oh hey whats up", told her not much, just was callin to see how things were. She then says "well they're great, wow, i havent heard from you for awhile, if you're calling for, uh, you know, i'm married, got married 4 months ago", i told her congratulations. Told her thats not why I was calling. Without any other way than just throwing the question at her, I asked her to rate me in bed from 1-10. She was like "why does it matter, thats a weird question", I asked her just to answer. She was like well that was almost a year ago or more and just for one night because she was horny. She informed me that she doesnt remember me being a bad lay, if thats what i'm after. Heather was listening in (speaker phone) and mouthed to me that I must get a number for the rating. So I asked Chelsea to just give me a number, she said well i guess a 7, because if it was more than that then i would have called you again for more and laughed. Then she says just kidding, but a 7 works for her if it works for me. Then I said Ok one more question and asked about my penis size. She said well I was the biggest she'd seen up until her husband, so larger than average. She then asked if there was anything else, told her nope, thanks and wished her well in her marriage. Heather grinned and told me she was impressed I would actually make that call.

Not knowing how far I could dare her to go, I decided I’d start to test things out. I told her I wanted her to call her ex and ask him what he thought she was best at in bed. She refused, she said it was an ugly break up and she’s changed her cell # so he wouldn’t keep harassing her. I told her to block her number, but she wouldn’t call him. So then I told her I wanted to see her tits. She hesitated then told me no, she didn’t want to take her shirt off for me, but I could feel them through her shirt. Whatever, I had hoped all our talking earlier had made her horny. So I felt her up, played with her nipples for a second then she pushed my hands away and informed me it was her turn. She then dared me to strip down to my boxers and run go next door and ask to borrow a cup of sugar. She says next door lives an old lady who would freak out if some guy in his boxers came over. After informing her that if I did this, she’d better do good stuff, she finally had me once again, puppeted into doing it. I stripped down to my boxers, went next door and asked to borrow a cup of sugar. Heather told me if the lady asked, just tell her I was a friend of Heathers. So I went next door and knocked, the old lady was taken back by my appearance, I asked her for a cup of sugar, she asked who I was, that she hadn’t seen me before, so I told her I was a friend of Heather. She didn’t invite me in, she went inside, got a baggie of sugar and brought it to me, then asked me to put some clothes on before I come over again.

I go back to Heathers and she’s busting up laughing, she couldn’t believe I had done it. By this point I was wondering if this was just going to be her trying to embarrass me, maybe her and Samantha were in on this. I could tell she was having fun, but I wanted her to do some cool stuff in return. Things took a good turn as I went to put my pants back on, she informed me that she had not told me to put them back on, simply to go get a cup of sugar and then come back. So there I was in my boxers while she had on her sweats and tank top. I dared her to reach her hand down my shorts and feel my cock, she agreed to do it, but only for a quick touch. She reached down, touched it and pulled her hand out, didn’t even really get a feel of it other than a quick touch.

Next she dared me to use her camera phone and take a picture of my cock and send it to Samantha (from her phone) so that Samantha would know I was over there and get curious. I asked if they had this planned out, she insisted they hadn’t planned out anything, I didn’t fully believe it, but continued to go along with her game. I tried to get her to take the picture, but she wouldn’t, and she made me go to the other room. I told her I’d do it if she would look at the picture. She agreed. So I took a picture of my cock, (mind you I’m not hard at this point), I show her and she makes a small dick comment, I informed her it was not hard and I’d be happy to let her heat things up and see how big it gets, she declined. She sends Samantha a picture with the caption “hey Sam, hows it going? Do you recognize this piece of meat?” and sends it. I couldn’t believe where things had turned. I asked her what she thought of the picture, she just smiled and said, 'looks appetizing'

I dared her to strip down to her underwear. After a few seconds of thinking, she agreed that I’d done enough to show that I would obey her and surprisingly, she agreed. She went into her room and came out in a bright pink lacy bra with boy short panties, it was very flattering! The bra was very tight and her tits overflowed.

Now I definitely wasn’t ready for her next dare… she said “lets get in the shower together in our underwear and let me shave your chest”, I have a pretty hairy chest, I used to shave it in high school and for a few years after that, but lately I’ve found that girls don’t mind my hairy chest so I’ve let it grow. But the thought of getting in a shower with her was very intriguing. I told her I didn’t know if I could trust her with a razor, she laughed as she stood up and pulled me up and walked me to the bathroom. She got out a new razor from the cabinet and climbed into the shower… she looked and me and said “well?”, I told her that with as long as my chest hair was, we needed to trim it first to get it shorter or the razor would yank the hell out of it, so she grabbed me some scissors and told me to hurry up and trim it. After trimming it up a bit, I climbed in, unable to believe what was going on, she turned on the water and without even a second thought, pulled out the shaving cream, lathered up my chest and started shaving it. After a few minutes it was smooth as could be. She was looking very hot now as she was wet from the shower. I pulled her close and went to kiss her but she backed away and told me to slow down. I was like SLOW DOWN? You just freaking shaved my chest!