First Time

I was a pretty naïve 17 year old. I had kissed a couple of female friends, possibly grabbed a boob through clothes but otherwise was very limited in my experiences. I started dating Lisa, a pleasant, homely sort of girl in the year above me at School. She was everything I wasn’t – smiley, outgoing, friendly and very popular. We had been friends for a while and unbeknownst to me, she had always had a thing for me.

On one of our regular nights out with the 2 classes in our 6th Form College, drunken dancing led to drunken flirting which led to drunken kissing. From then on, we were an item.

Friday nights were always over at her house, her Mum and older brother were usually around, so other that watching TV and the occasional can of beer, things never got any racier than that.

After about 4 or 5 weeks of dating, her Mum announced she had a weekend away with some friends and Lisa and her brother were to see to themselves (aged 17 and 21 they were more than capable). Lisa’s brother took that as license to stay at his girlfriend’s house, leaving Lisa and I alone as she saw her Mother off for the weekend.

“No funny business,” her Mother said, eying me suspiciously as my face immediately went to the default ‘butter wouldn’t melt’ expression I had perfected over the years. Having Catholic parents, there was no chance of me being allowed to stay out overnight, but at least we hade the house, and more importantly, the sofa to ourselves that night.

So, the evening progressed, we watched TV, ate a takeout pizza and made out at regular intervals. After a while, the TV and the pizza became less interesting as we slipped into a long make out session on the sofa. Feeling brave, I moved my hand off her head, down her arm and gently caressed her small breast over her top. Getting neither protest nor encouragement, I moved my hand down to her waist, under her shirt and back up to her breast, this time feeling the nipple through the thing material of her bra. I massaged her breast as we kissed, feeling the small nipple grown hard between my fingers as my cock started to thicken.

Lisa parted our bodies, moving my hand away as she sat up. I sensed this was the end of our session, but to my surprise, she pulled her shirt over her head revealing her cotton white bra and pale torso, before pulling me back in to resume our making out. By now, my full focus was on her breasts through her bra, and trying to build up the courage to remove it (not that I knew how in those days LOL).

Being the inexperienced 17 year old that I was, I fiddled with the clasp at the back to no avail, then concentrated on getting my finger inside the cup, with limited success. Sensing my frustration/ineptitude, Lisa pulled at the shoulder strap of her bra, releasing the cup and revealing the most amazing sight of her small white breast and erect pink nipple. My mouth went straight to her breast as I sucked her nipple, whilst massaging her other (still covered) breast. Again, Lisa parted our bodies, reached behind her to unhook her bra, leaving her completely topless in front of my for the first time.

I was in heaven, playing with, kissing, sucking and looking at her (what I’d guess were B cup) breasts. She removed my t-shirt and the feeling of her naked breasts against my chest was the sexiest thing I’d ever encountered. We continued our make out session, but this time slipping on to the floor as Lisa started to explore my own body, running her hands over my chest and kissing my nipples.

Unsurprisingly my cock was rock hard, and pressing against the waistband of my jeans. As Lisa caressed my body whilst I kissed her and played with her boobs I took a massive gamble….. gently caressing her upper arm, then her wrist, I took her hand off my stomach and placed on the bulge in my jeans.

 Lisa responded by rubbing my bulge, then lightly gripping my cock through my jeans. The feeling was unbelievable and something I had never experienced. Here was the first person ever to touch my cock (albeit through thick jeans) and it felt as though she liked what she felt.

We continued making out for ages, her rubbing my cock, or sometimes just leaving her hand there as we kissed. It was almost as if she wasn’t sure what the next move was, or whether she was allowed to take things further. I helped the situation – being the skinny teen that was at the time, I was able to pull my jeans down without undoing my belt or the buttons – I pulled them down just enough so that the head of my cock appeared out from the waist band and immediately placed her hand upon it. The sensation of another person’s hand touching my cock was amazing as what felt like ever drop of blood in my body rushed to my cock.

Taking my encouragement, Lisa pulled my jeans down further until my entire cock was exposed. She took a few seconds to take in the view and assess my size and shape. She resumed kissing me as she wrapped her hand around my cock and started to jerk me. This was the moment, my first hand job and my first orgasm at the hands of another. Unsurprisingly, given the build up and my immature nature, it wasn’t long before I felt my legs starting to shake with pleasure and my balls tighten. I exploded with 2 or 3 huge ropes of cum, far more than I’d ever produced before as I spurted up in the air and landed on my chest, her arms and chest.

I slumped back on the carpet, my head swimming in extasy as Lisa grabbed her shirt to clean me up. Feeling her hands on my rapidly softening and highly sensitive cock had me in dreamland. She cleaned me up, we went back to watching TV and she repeated the hand job later on that night…

My first hand job, led to my first blow job and a few days later she taught me how to bring her to orgasm with my fingers and then my tongue. Things ended a few months later, my immaturity got the better of us and whilst I think of her fondly, I will always be grateful for those first experiences and everything she taught me.