My mother was in her second marriage with a man I didn't like because he was a jerk to us kids and even to his own. 3 of us belong to my mother from previous marriage and 10 belonged to him from his previous marriage. His son was married to a woman who had a girl from a previous relationship many years back which didn't work out. Her name was Cindy and we've gotten close perhaps some would say too close as she was my first in any sexual experience. With the family sisutation I explained I don't know if she'd be concidered as my cousin or not but we thought of eachother as cousin's anyway.
I lived in a house that had a deck attached to it, whenever she'd come over with her parents, she and I would hang out under the porch playing such games as truth or dare and more often took the dares which lead us to flashing eachother our body parts, kissing and even touching eachother but nothing more ever happened.
(me) truth or dare?
(me) I dare you to lift up your shirt
Cindy blushed at first but didn't hold back as she lifted up her shirt showing me her small boobs with hudge nipples and now it's her town.
(Cindy) truth or dare?
Cindy protested saying that's not fair so I took a dare.
(Cindy) I dare you to lift up your shirt
I did then it went even further
(Cindy) I dare you to show me your penis
Being shy I hestitated but then showed her which at the time was hard and so it was my turn.She took the dare again.
(me) I dare you to show me your vagina and ass
Oh my did she ever.
It went on like that for us for a couple of years before we got bolder at the age thrt-teen when I lived in a new house that had the oldstyle basement with the cellor door outside as we went in. She was talking about looking at her dad's porn mags which showed a man in a woman's ass and she told me she wants to try that. Not having any sexual experience I didn't think that was possible but I found out that day it is and been hooked on anal sex every since.
The basement had stone brik walls with a dirt floor and we were sitting on a blanket facing eachother. I reached for her boobs carressing them as she reached for my cock stroking it and we kissed on the lips open mouth with our tongues exploring eachother. Shen then unbuttoned and unzipped my pants pulling my hard cock out and she touched the head with your tongue. Never experiencing anything like this I jumped and she looked up at me saying "relax." Guessing from her skills, I figured she had done this before because it felt damn good for a blowjob and I couldn't help what happened next as I shot my load into her mouth. Thinking it was over but not by a long shot as she clamped her lips down my cock firmer and swallowed my cum to the very last drop. Wanting to return the favor I asked her to lay back which she did legs spread, I layed on my stomach and imediately started using my tongue on and in her pussy, of course I wasn't doing it right at first but she was patient with me letting me know when I was touching the right spot as she came hard with her hand over her mouth trying to muffle her screams. Then outside her parents were calling for her, we both smiled at eachother , got dressed quickly and I seen her off with her parents.
The next time she came over with her parents, we immediately went to the basement kissing and touching eachother again. We both admitted to eachother that we missed eachother and been looking forward to our time alone again. She then got a smile on her face, I asked her why and she said "you remember shooting stuff in my mouth and I swallowed it?" Of course I remember, how does a teen boy forget something like that? She proceeded to say "I want that to happen again but in my....ass." Of course I was puzzled not knowing how my cock would fit in such a tiny hole but must admit the thought did turn me on as I felt my cock hardening.
I spreaded out the blanket as she was pulling her shorts down along with her panties, then got in doggy position and looked back watching me pull my shorts down as my cock sprung out in the open. Smiling at the site she said "I want to feel it in my ass, please." Not sure what to do, I asked how the couple did it in the mag and she instructed me on what she had seen. So, I'm on my knees behind her admiring her ass while bringing my cock closer to her asshole and we both gasped as the head of my cock disappeared into your asshole and since we had no lube, I took my time when she asked me too until I was finally balls deep as we both are panting heavy and she tells to go slow at first which I did. Both of us panting even harder as it was feeling good for both of us I was by now fucking her ass faster. Cindy moaned but in pain, instead with pleasure and talked dirty to me which she didn't need to as her ass was feeling good taking my cock but her dirty talk did add to the good feeling we were experiencing. I grabbed her hips pounding my cock in/out, in/out of her asshole and she was matching my every thrust with her moans, my heavy breathing and sounds of our bodies slapping loud enough for us to hear.All this became too much for me as I stopped moving as so did she while enjoyed the feeling of my cum filling her ass up. By then she was laying on her stomach, I was resting on her back with my cock in her ass pumping load after load of cum deep in her ass and we managed to kiss with my cock still in her ass.
After getting dressed, we heard her parents calling for her as we snuck on last tongue filled kiss and as we made our way outside, both her parents and mine were standing there with a look that told us we were busted and of course we tried to deny anything they were accussing us of. It's been a long time of her parents not bringing her over which was driving me crazy, I wanted in Cindy's ass again as she later told me she wanted it again much as I do but that's a different story.
If you want to read our second encounter, give me your feedback on this story that acctually happened.