Truth or Dare= First time Anal Sex_(0) by SrCIt64

A literotic sexstories: Truth or Dare= First time Anal Sex_(0) by SrCIt64 ,

Playing truth or dare can cause all kinds of Sexual Adventures

Being 14 years old and an 8th grader in middle school, you didn’t have dates you had girlfriends that you walked to each class in school and stole a kiss when you dropped them off at their class. My girlfriend was the same age as I was and being an only child her sexual experience was mainly what she had picked up from her friends at school. Being from a divorced family and raised by my mother, my sexual experience was learned from watching porno’s and trial and error.

Imagine my surprise when one day my phone rang and it was my girlfriend on the other end, She was home alone and bored and decided to call me to see if I wanted to come hang out with her as both of her parents worked during the day and she was the only one home, I said ok and I hitch hiked the two miles to her house to spend the day with her. Now I am from Michigan and during the summer it is very hot so on most occasions you will find me in only a tank top and a pair of shorts, no under ware because they cause your balls to sweat and cause chafing. When I arrived at my girlfriends house she met me at the door and I noticed she was wearing a cotton blouse, NO bra and also shorts and not much else, She had a nice pair of 32C tits that were visible through her blouse and I tried my best not to stare as she invited me in. We retreated to her bedroom which was in the basement and sat down on her bed and started watching some television. I told her that I thought she looked very attractive and very sexy in the clothes she had chose to wear, she blushed but thanked me and then asked If I was up for a game? Being curious I said sure, what do we play and she replied Truth Or Dare. I said Ok but I go first, she said fine and I said truth or dare? She said truth, so I asked why did you really ask me over here today? She responded by telling me that her girlfriends were talking about their boyfriends and how they had been experimenting and playing around with each other and so as not to be a prude she invited me over to answer questions she had and maybe show her a few things. Now I am no sex expert like I said most of my experience came from porno and trial and error but I would answer her questions as best I could. First she asked me if I had ever seen a women naked, now being from a family with 3 sisters, I did on occasion sneek a peek at my sisters when they stepped out of the shower so yes I had seen a naked women before, Then I asked her if she had ever seen a naked man, to which she replied no but that she wanted to. She asked he how big I was and I told her I didn’t know because I never measured myself. She was curious so she asked If I would measure myself for her and proceeded to hand me a ruler, I stood up and removed my tank top and my shorts and there I was completely naked standing in front of her, She let out a little gasp at seeing a man’s cock for the first time but managed to keep herself composed, I held the ruler to my cock just under my ball sack and I measured a little over 4 inches soft, she said that her girlfriends said their boyfriends were at least 6 inches long. I told her that I could make mine bigger but she would have to help me, she asked how and I said well” someone in this room is overdressed and it wasen’t me, with that she stood up and removed her blouse and shorts and panties and she was just as naked as I was. Now being 14 she looked stunning with her 32C titties and her virgin pussy with her blonde hair covering definitly started a feeling in my cock because it started to harden and she was amased at how much bigger I had gotten. We measured again and this time I was almost 6 inches long and standing very erect, She asked me if it hurt like that and I said no it felt very good, She asked me how i got it to go back down and I explained to her that there was only 3 ways to get it down, One was to do nothing and think of something other than sex and it would eventually go down, the second was to Stroke it or stick it in a womens pussy until I came and It went soft again, or the third was to fuck someone in the ass cumming and getting it to go down that way.. She asked me about stroking it, and I asked her if she ever got herself off by rubbing her pussy and stroking her clit? She said no so I said I wanted to try something and asked if she trusted me, she said yes and I assured her that I would not fuck her because she was still a virgin and I wouldn’t take that from her unless she was absolutely sure that was what she wanted but I would help her get off, and with that i laid her on the bed and I started rubbing her titties getting the nipples nice and hard, kissed her gently parting her lips and touching her tongue to mine, and with my other hand I moved down and parted her legs and started rubbing and fingering her pussy taking caution not to probe to deep so as not to break her womenhood. She started moaning and squirming a little at the sensation she was feeling and I asked her if that hurt or felt good? She said it felt good and not to stop, I said ok but don’t freak out as I am going to do something to make you feel even better, and with that I moved my lips over her tits and sucked on each one of them and then I licked a trail down her stomach and kissed her virginal mound just above her pussy and slowly started licking at her clit and her pussy lips which by now were very wet with her juices, That was all she could stand and the next thing I felt was her hips bucking up and she came all over my face soaking me with her pussy juices and me lapping at her trying to get as much as I could into my mouth, god she tasted good, I raised up just as she started cumming down and her breathing got back to normal, She noticed that I was still very hard and decided that she had to do something to return the favor , I showed her how to wrap her hand around my hard cock and how to slowly stroke it up and down and I told her if she continued to do that , Then I was going to cum and she would get her first look at a man shooting cum all over the place, she said she wanted to see it, and didn’t stop pumping my cock, I started feeling like I was going to cum and I told her so, she said go for it and right then I shot my load all over her hand and she just kept pumping me until there was no more cum for me to let loose. She released her grip and we just laid there trying to compose ourselves until our breathing got back to normal. Then she did something I didn’t expect she looked me straight in the eyes and said she wanted to feel me inside here. I told her that in order for that to happen I would have to fuck her and that would mean taking her virginity and I thought she should save that for marriage. She was very excited and said well what about the second way, how does that feel? I explained to her that it was almost the same as fucking her pussy but her ass was tighter and she would have to be able to relax to take it and enjoy it. She said she wanted to try and started stroking my cock again to get it nice and hard, Now spit is a terrible lubricant so I asked her if she had any vaseline and when she said yes I told her to get it and come back to the bed and I would show her how to take a mans erection in her ass. She went to the bathroom and returned with a jar of vaseline, I had her lay on her stomach and I lubricated one of my fingers and slowly moved it to the entrance of her ass, I told her to relax and slowly inserted my finger in her ass and moved it around lubricating as much of her inside as I could, then I lubed my finger again and this time I stuck two fingers in her ass to get the feeling of how big I was and what it was going to feel like being in there. At first she tensed up at feeling my finger probing her asshole but started to relax as the second finger went in and I could tell she was starting to enjoy it.. I asked her if she was ready and she said she was, so I placed her on the bed on her hands and knees and i stood behind her with my cock at the entrance to her asshole. She had a dresser next to her bed with a mirror on it and I told her to look in the mirror and to watch what I was doing and with that, I started to enter her very slowly so as not to hurt her and to allow her to get used to the size of my cock going where no cock had gone before, She took a deep breath as she watched my cock disappear between her ass cheeks and soon I had all 6 inches buried deep in her ass. I held it there so that she could get used to the feel and soon she was telling me to move back and forth and to fuck her ass just as I would if I was in her pussy. I started stroking and soon I was at the point where I was about to cum, I told her so and she said she wanted to feel my cum in her ass and that is exactly what I gave her, I started cumming and filled her up and some was leaking out her asshole but I just kept pumping giving her all I had, It must have been good because she let out a loud moaning and was stroking herself while I was fucking her, she came again and I pulled out of her and turned her over and spread her legs and buried my face in her pussy and sucked as much of her pussy juice out of her that I could , god she tasted good.

I stood up to clean myself off and she saw that I had cum on my cock and the next thing she did was to put her mouth on my cock and she licked and sucked me clean tasting cum for the very first time. When we finished we both showered and I went home feeling very spent and very satisfied at teaching her something she could tell her friends about the next time they talked about haveing sex with their boyfriends.

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