I was still in high school when I got started on my road to family intimacy. It wasn't at all what I was planning on -- I had never even had a sexual thought about my two older brothers, and certainly had never thought about my parents in that way. I was extremely curious about sex and had had a few experiences with boys I had dated; but they were boys, and didn't know what they were doing.
And, to be honest, neither did I. Technically I wasn't a virgin anymore, but somehow pulling my jeans down to have hurried sex in the backseat of my boyfriend's parent's mini-van left me unsatisfied - shocking, right? The second and third times weren't any better; my boyfriend could barely get the condom on and slide inside of me before he was coming. That was the extent of my sexual education. I knew there was more to it, and wanted more. I just had no idea what would be in store for me...
The summer before my senior year of high school our family went on a road trip from California to New Jersey to visit family. It was miserable being stuck in the car for long, boring hours, not to mention it took three weeks off of my summer vacation. Neither of my brothers had to go; they were "too busy earning money for college". It wasn't fair, but I tried to make the best of it, and did have some good times reconnecting with some of my cousins, aunts, and uncles along the way.
As soon as I got home I immediately headed over to my best friend's house. Ana and I had been friends since 6th grade and didn't have any secrets from each other. We were an unlikely pair -- she had beautiful, caramel skin, lustrous black wavy hair, and gorgeous, deep brown eyes that complimented her short, curvy, hourglass body.
I, on the other hand, was tall, had thick, straight, dirty blonde hair that I kept in a bob, pale blue eyes, freckles across my nose, and small, perky breasts. My one redeeming physical attribute was my ass. Years of playing soccer had given me thick, toned legs and a nicely shaped bubble butt. It was my best asset, pun intended.
By the time I got there she was ready to burst with excitement and we quickly went to her room. Once we were alone she told me how her and her brother, Miguel, had messed around. After being completely shocked by the news, I had to admit it got me excited, more than I realized. I had had sort of a crush on Miguel for a couple years, mostly because my parents didn't like him -- he was 3 years older than me, and had long hair, wore a leather jacket, played the guitar, and was always on the verge of dropping out of college. In reality he was a really sweet guy, and was hard to resist.
It took a while to get all the details out of Ana but eventually she told me how it had all happened -- she had been spying on Miguel and his girlfriend having sex, and was fascinated at what she had seen. It had taken her a few days to work up the courage, but eventually she asked Miguel about what she had seen, and that led to them playing show and tell, and more. They had done just about everything, except for "up the butt", as she put it. I was blown away and we talked about it a lot over the next few weeks.
Ana made it worse because every now and then, when they were home alone, Ana and Miguel would mess around or have sex, and then she would call me and give me the gory details. I was really jealous and eager to try messing around, and kept hinting to Ana that I wanted to play too. She eventually caught on and talked to Miguel, and of course he was interested -- what 21-yr old American man wouldn't be interested in a very inexperienced, eager-to-learn 18-yr old woman?
So, one Friday night when I was spending the night at Ana's house, it happened. Their parents were gone so it was just us three. I was nervous but really wanted to try, and Miguel was so sweet and gentle. Ana stayed and watched; at first it was kind of embarrassing to undress in front of her while Miguel was undressing too, but then I remembered all the times that Ana and I had changed in front of each other and I got over it fast.
Miguel let me play with his cock, then I sucked it off and on while stroking it, and then stroked him until he came with a pop and a spurt. I had taken 9th grade health but nothing prepared me for the come shooting out of the end of his cock. For a brief second I thought he was peeing but it was thick, white, stringy come, and it shot all over his chest and legs and up my hand and arm.
We cleaned up and then he got between my legs. As most women can probably attest, the first time someone other than yourself touches you can be quite powerful, and Miguel knew what he was doing. It felt amazing and despite my best efforts I was moaning and crying out. He played around with me until I was really wet, and then ate me out. I didn't last long; I had figured out how to make myself come but this orgasm was so much more powerful. And so much more enjoyable.
At this point Ana wanted some attention so Miguel moved over and began playing with her for a few minutes, before having her sit on his face. It was mind-blowing to be lying there next to them, completely naked, watching my best friend getting eaten out by her brother. I watched his cock grow hard as he enjoyed her wetness, and soon she came loudly.
She laid back and watched as Miguel had me get on top of him so we could 69. I found this to be an odd mix of distraction and pleasure, and had a hard time focusing on sucking him while his tongue was giving me such pleasure. After a few moments he had me turn around and straddle him, his cock ready to slide into me. This was the moment I had been waiting for and I was ready to have him inside me.
He guided his cock into my pussy and had me slowly slide down until he was inside me fully. It was somewhat uncomfortable -- his cock was bigger than my ex-boyfriend's - and there were a few moments of pain, but eventually my hips made contact with his body, which meant all of him was inside. He held me like that and just let my body acclimate to the new sensations that were shooting through my body. It felt good but also like I was going to split in two, like an overly full feeling. We took it slow and he showed me how to ride him, to give us both pleasure. It was a lot of fun and I rode him for a while.
Then he had me stop because he was getting ready to come and wanted to get on top of me. I laid back and spread my legs for him, and he slid inside of me and started to pump me. He was really enjoying watching his cock slide in and out of me and before I knew it he was coming inside of me, his head tilted back, eyes closed, a long low groan escaping from his open mouth.
We took a break and then Ana sucked him hard and took her turn on his cock, riding him while kissing him until she came, and then letting him fuck her from behind until he came inside of her. It was an extremely enjoyable and erotic night and we had another round of sex in the early morning hours, before I went home. I felt so naughty walking back into the house, my panties full of come, having just had Miguel fuck me from behind a few hours before.
Ana and I talked about it non-stop for the next week. We talked about sucking Miguel, the feel of his cock inside us, being eaten, his come... just about every aspect of our sexual escapades with him. And every chance we got we played with him, getting more and more confident in our sexuality and our bodies, and getting more and more eager to try new positions and try new things. It didn't bother either of us to taste each other on Miguel's cock; in fact it was kind of kinky, and eventually we got the point where we were eating each other and kissing and playing with each other in front of Miguel. We both enjoyed it and it blew Miguel's mind to watch us together, especially when I ate his come out of Ana and vice versa.
It was a very fun summer, but like all good things it came to an end. September arrived and we started our senior year in high school. Miguel did not go back to college; his parents refused to pay based on his poor performance in his coursework, and so he chose to rebel and enlisted in the Marines. Two days later he was on a bus to boot camp. He and Ana wrote letters and talked on the phone, and she told me that he was missing both of us and thought of us often.
Around the middle of October Ana told me that Miguel would be home during our winter break, and that he had asked her for a huge favor -- to go off birth control pills, so that he could try to get her pregnant when he was home on leave. He had always joked about wanting to get us both pregnant, but we thought it was just him kidding around.
Apparently he had thought a lot about it and really wanted to try. It had taken several weeks to convince Ana, but she eventually said yes and that she would ask me, too. At first I completely refused, even when Ana stopped taking the pill. She told me how she had mailed all of her birth control pills to Miguel, and the thought of that made my head spin with arousal.