Little did I know that New Years Eve would end so well...
It was the Christmas Holidays in my first year at Uni. As a fresh faced, and somewhat naive 18 year old I hadn't seen much "action" at Uni and returned to my friends and family for a couple of weeks. I had at the time, a decent circle of close friends, mainly girls, whom I'd grown up with through primary and secondary school. There had been the odd drunken kiss here and there but nothing more than that.
My oldest, and probably best friend was a girl named Caitlin - tall, slim girl with dark hair and piercing Irish eyes that always sparkled when she laughed. I'd never had "a thing" for Caitlin - we had been friends since the age of 6 and I guess, growing up together became more like buddies than anything else.
Christmas came and went (as did I, back in the old routine of solo masturbation in my old room at my parents' house) and New Year's Eve rolled around and Caitlin's family were holding their usual New Years party - loads of family and friends filling their big house with sings, chat and laughter. As the "youngsters" Caitlin, myself and about six others holed up in her attic room drinking, messing about and generally catching up after a term away. Midnight came and went, people started to drift away leaving Caitlin's parents, a few family members and we youngsters upstairs.
After getting the "ok" for us to sleep over (two guys, five or six girls) we set about gathering cushions, pillows, blankets etc for the mass sleepover that was about to happen. Most of us grabbed a corner, or some floor space of Caitlin's bedroom. Caitlin graciously gave up her bed to two of the girls who seemed a bit worse for wear and settled down next to me on the floor in the centre of the room. Caitlin was now appearing a bit giddy and starting to get silly with me.... "Get your belt off, you can't sleep in your belt. Why would anyone try and sleep in their belt?" She asked no one in particular I acquiesced and let her remove the belt from my jeans before settling down under my blanket.
The lights went off as everyone started to drift off into various states of drunken stupor. I started to drift into a light sleep, feeling the effects of too many beers swirling around my head when I felt a tug on my jeans. "You can't sleep in your jeans. It's too uncomfortable. Take them off" whispered Caitlin. "What you talking about? I'm fine" I protested half heartedly. "Get them off!" She insisted and expertly opened my button fly and dragged my jeans off by my feet "Shhh. What's all the noise?" Protested one of the girls "Nothing" I murmured. "Go to sleep"
Again, I started to drift off until I felt a hand moving under my blanket. "Caitlin?" I whispered. No reply. The hand found my chest and moved downwards over my stomach until it paused at the waistband of my boxers. "What you doing?" I whispered, trying to disguise my excitement and nervousness. Again, no reply. This time the hand, which I now knew was Caitlin's, gently caressed my semi-hard cock through the fabric of my underwear. Instantly I grew rock hard and could feel my legs quivering at what was happening. "Take your pants off" said Caitlin. "You can't sleep in your pants" I did as instructed, letting my erection spring out under the covers. Caitlin wrapped her hand around my cock and started stroking me slowly. "Too hot under here" said Caitlin and threw the covers off me exposing my cock to all and sundry in the room.
Thankfully it was dark, and by the sounds of the various breathing patterns, everyone was asleep. As she continued to stroke me, I shuffled towards her, turned my head and met her lips. It felt incredible and quite strange to be kissing my best friend like this. I reached down and found her breasts underneath her top - I cupped her beautiful B cups in my hand, craning my neck down to suck her nipples. This was all new territory for me having had one girlfriend who used to jerk me off, but no more... I felt my orgasm rise as she continued to stroke me. I released her nipple, and lay back on my pillow as my cock erupted with several ropes of cum.
She wasn't finished there.....after cleaning me up with my blanket, she took my hand and moved it down over her stomach, through her pubic hair until we reached her wet lips and wonderful mound. She guided my fingers into her lips, and up to her clit teaching me the motions and rhythm to bring her to orgasm. I felt her writhe and stifle a moan as I continued to rub until she jackknifed and came to a (clearly) very much needed orgasm. "That was amazing" I stammered. "Mmmm....now go to sleep" she whispered and turned on her side.
I lay on my back, drinking in the feeling of amazing pleasure and my first experience of a female orgasm. I turned to one side and my eyes met those of one of our friends who was lying in bed, eyes wide open with a huge grin on her face.... Needless to say, the story of my experience was passed around the group the next day and became stuff of folklore in the ensuing years.... I went on to have a few more experiences with Caitlin, and also with the friend who watched us.....