So Many First Times

I recall the first time as a boy I discovered that there was something under my foreskin and that the soft shrivelled foreskin was not in fact the tip of my penis. At shower time one day my father called me into the shower to show me how to wash under the foreskin. He demonstrated for me by pulling his foreskin back to reveal the head of his penis, but when I tried to do the same mine was too tight to roll back and hurt when I tried, so I gave up.

It was some time before I thought about my penis again, and was quite surprised to find it had a use other than urination. I did not learn about masturbation from other boys, but was somehow instinctively drawn to touch myself and was surprised to find it expanding and that my father was right, the foreskin does pull back. My first ejaculation was a massive surprise. I knew that stroking my dick made me feel good and found it somehow compulsive, but when I came and jizz exploded everywhere, I faced my first clean-up panic attack. Probably as a result I have never been caught in the act, so there is still the chance of a first time for that.

At that stage I still had no idea that vaginas existed. My first wet dream involved an image of an ambiguous figure in a white shirt, who I approached from behind, to realise that the person had no pants on, and as I caught sight of the figure's buttocks I came in my sleep. This has often made me wonder about my sexuality but was probably simple ignorance of anatomy.

This ignorance and my schooling at an all boys school meant that I was over 21 before I experienced kissing and cuddling girls. Painfully shy, it was only through the initiative and persistence of my first girlfriend that I finally took her in my arms and experienced my first kiss that, once started, I never wanted to let go. How easy to lose track of time between lectures at university while lying together kissing and cuddling in the safety of public spaces that inhibited a deeper exploration of female anatomy. The first time I came in my pants after a long session of kissing and cuddling with entwined legs was painfully embarrassing, as I had to run to the bathroom and clean myself up before the stain could spread through my jeans, not to mention facing the girl afterwards.

I then graduated to make out sessions in her room in college, the first hand up her shirt and fondle of a breast, the first hand down her pants to caress her pubes and, to her embarrassment and amusement, my first close visual inspection of her pussy, and the first time I made her come from fingering her pussy. This was all pretty innocent, as we had not yet fucked, and I had not even had my fingers inside her cunt. She gave me so many hand jobs I cannot recall the first, but it was an anti-climax after I came in my pants that first time.

I did meet her parents, and first went down on her in the bedroom she shared with her sisters. The house was empty at the time but they could have returned at any moment, and it was slow going. She was lying on the bed with her legs over the edge, I was kneeling between her legs with my mouth on her snatch, my arms reaching out to fondle her breasts, and my tongue was getting tired. Then I tasted the sweet let-down of pussy juice and felt her hips start to respond and she came suddenly with a moan.

My first attempt to fuck a girl was not a success. After a long make-out session I pressed my hardon against her pubes, and she said 'What are you doing?'. I didn't answer as I thought it was pretty obvious, just kept pushing, but even with her willing participation it was clear her virginal hole was not big enough. So it took a couple of attempts to get in, and I can't recall my first true fuck. I do recall we practised coitus interruptus, so I became good at pulling out at the last minute and coming on her belly. I spilt a lot of cum on her belly during that relationship.

My first '69' was with another girl. She was on top, and I had my face buried in her ass, tongue in her pussy. She tasted fabulous, and I was feeling so good from licking her I hardly could feel her sucking my cock. As my whole body swept towards the point of no return it crossed my mind to tell her I was about to cum, but I didn't want to stop licking her pussy and we both came together. She swallowed my cum, but as I've since learned it might have been better to give her a heads up.

My first hand job from a guy was very memorable. We were both nervous as hell, his cock was huge compared to mine and felt wonderful to stroke. Mine was incredibly hard and I came as soon as he touched me, shooting jizz about 3 feet in the air. The first time another guy went down on me I surprised myself by first letting him take me by the hand. He led me to a quiet corner and lay me down, then pulled my limp dick out of my pants, gave it a coupe of short strokes till it was firm enough to slip a condom over, and he started sucking it till it was hard and bursting to cum. I told him it felt good, very good, then I came. Then he walked away with a laugh, leaving me with a cum-filled condom on my dick to clean up.

I recall the first time a girl fucked me 'reverse cowgirl' and another time a guy climbed on my cock 'reverse cowboy'. I came loudly with the guy, surprised how good his ass felt, but I couldn't see much as he rode up and down my cock. The first time a girl rode me this way I was amazed at the sight of her pussy lips gripping my cock and how my cock glistened with her pussy juice. It was as much that wonderful sight of her actively fucking me as well as the intense feel of my cock pressing against the back of her cunt that made me explode inside her. And then seeing my cum dripping out as she raised herself off my cock.

My first experience with a lesbian occurred after trying to explain to heterosexual girls that I wanted them to dry hump me naked with me receiving in the missionary position. Hard to explain until one girl said to me, 'I have a girlfriend and I know exactly what you mean'.

Lying back with my legs apart, arms and legs wrapped around her as she lies on top humping me with her hips, her pubes against mine, I'm not thinking about my cock. It is hard to describe how the feeling of a whole-body orgasm creeps up and suddenly I cum, shooting my load between her sweating belly and my own.

It was quite a long time before I first experienced deep fingering a girl's cunt, the amazing feeling as it expands inside and responds to fingering the g-spot, and the contractions when she cums. I've never felt that with my penis, and seem to have more acute sensations in my fingers that makes the two-finger-fuck so wonderful. And when a girl kisses with a deep open warm wet mouth, I usually find her cunt is ready in the same way. So when a girl told me after our first time smoking a substance that it had no effect on her, but she kissed open mouthed so passionately, I knew her cunt would be the same, and it was.