The first part of my continuing masturbatory history.
My name is Tessa, I am 17, have 34B tits, red hair and stand about 5'6'.
It all started when I was twelve. I come from a large family, I have three sisters ((Steph) two years younger, (Beth) my identical twin, and (Sam) two years older) and one brother (James) two years older than me), thus privacy has always been a bit of an issue, though we have always been rather open about our bodies. Cousins (Caitlin and Madeline) of ours had come to town for Christmas, Caitlin was 15 and had a beautiful body, and Madeline was 21 and did not have much to do with the younger kids. I had just hit puberty, already had my first period, and little wisps of red pubic hair, my tits hadn't developed yet. Sam, Beth and I shared the room in which Caitlin would sleep while she stayed with us, Beth and I had a bunk bed, while Sam had a double bed, it was decided that Cait and Sam would share the double bed rather than have Cait sleep on the floor.
The first night Sam and Cait talked long into the night about boys, I learned that Sam had never seen anyone, but Cait had had a string of boyfriends since she was 13. As the night progressed, Cait asked Sam if she masturbated. Sam did not know what masturbate meant, neither did I for that matter, so I listened intently as Cait said.
'You know, masturbation, when you finger your pussy.' Sam replied that she had never tried, Cait asked if she would like to learn how to, Sam said she would. After checking Beth and I to see that we were sleeping, Sam sat facing Cait, they were both nude. From my top bunk I could see Cait's body, but Sam had her back to me. Cait began her instructions, which I followed in my bunk.
'Ok Sam, first take two fingers on your right hand, use those to spread your pussy lips.' Sam and I both followed suit. 'Then take your left hand and gently touch the top, where your lips meet, that lump there is called your clit, it is your friend, now very gently touch it.' We did, I felt I fluttering between my hips as my pussy moistened. 'Now, while holding open your lips and keeping a finger on your clit, slide two fingers into your pussy, just a little bit, I don't think we want to break your hymen just yet.' As my fingers slid into my lubricated pussy I felt them hit something, this must be my hymen, I thought. 'Okay Sam, now we are going to finger your clit until you orgasm. Stroke it softly now, that's it.' I felt like I needed to pee really badly, Sam voiced my worries for me, 'uh Cait, it feels like I'm going to pee, should I stop.' Cait replied, 'No sweety, your about to come, just keep going.'
I moaned softly, but not softly enough to escape Cait's ears, 'Sam, I think Tessa is awake, hey Tessa?' She whispered, 'you awake.' 'Unnhah.' was my groaning reply. Cait sighed, 'Tess, if you are going to finger yourself, at least get down here and let us watch.' I slowly crept down to avoid waking Beth, who was still fast asleep. We sat in a triangle, naked, 'continue,' Cait said, and we did. I moaned and shook as I reached my first orgasm, as did Sam, Cait was fingering herself while watching us get off, she seemed to be enjoying the whole thing more than we did.
The next night we decided to clue Beth in on what she had been missing, Cait sat alone with her on the bedroom floor while Sam and I watched nude from our hiding place in the closet. 'Now girls, we are going to get rid of those pesky hymens, here Sam, you take Beth, I'll work on Tess.' Cait smiled, pulling two hairbrushes from her bag, 'use the handle, gently now.' I hissed as the rubbery plastic entered my pussy, I could feel a popping sensation, it hurt, but felt good at the same time. 'That's just your hymen sweetie.' Cait said soothingly, reaching down, she kissed me, 'you have such a beautiful body, babe, and you are so wet.' Beth's moans announced her second orgasm of the night, as they finished off I approached my own orgasm at the hands of my cousin.
'good,' Cait said with a satisfied glance around the room, 'now all of you can do me.'
She lay back and let us work our probing fingers over her glistening body. Beth and I each grabbed a nipple and gently rubbed and licked it, Cait moaned her approval. While we worked on the upper body, Sam worked on the pussy and asshole. Our efforts were soon rewarded by Cait's glistening, wet orgasm. Cait's sweet brown eyes looked at Sam, 'Sam, lay back and let us do you.' Soon we had all orgasmed and decided to turn in, it was going to be fun two weeks.
Our parents took Stephanie shopping the next day, leaving us kids alone with Madeline, who soon left, to watch us. James put in some B-movie by Troma and we all sat down to watch. It turned out this movie was very sexually explicit, which seemed to make James uneasy, but turned us right on. Cait curled over next to James, staring intently at his pants, which were beginning to form a tent around his crotch. He squirmed a little as she cuddled next to him, it was obvious he was hard as a rock.
'Hey James,' Cait said, 'Want us to jack you off...you can do it to us if you'd like?'
'Uhhh,' James managed to stutter out, 'I'm not sooo sure that would be a good idea...'
'...Well,' Cait said impishly, 'we will be upstairs, naked, if you want us...c'mon girls.' And we followed her out of the room and up the stairway.
We stripped when we reached our room, Cait began to moan and make other fake noises of pleasure. James could soon be heard clomping up the stairs, his pants dropped as he hit the hallway, he walked into the room naked as the day and hard as a rock.
'Okay James, lie down on the bed,' Cait ordered, James complied, 'Now, I am going to jack you off while these girls finger us, got it.' James nodded 'First I am going to play with you foreskin' She rolled it back, revealing shinning pinkish head. As we fondled them, James came closer and closer to orgasm, eventually cumming all over Cait's face, which she licked clean of cum, 'Mmmm, salty, yet sweet.'
James gasped, 'Oh my god, Cait, that was wonderful.'
We cleared some space on the floor, James lay down on his back. I realized how wet I was, and why, 'James, can I find out what your cum tastes like?' I asked innocently as I watched his uncircumised penis slowly erect.
...Over the next few weeks and years I found out much about myself and my friends/family which will be retold in the next instalment.