She was 19 at the time and I was 24.
Pennie was my first intimate girlfriend. Whenever we were together, we could not resist deep passionate french kisses and fondling each other through our clothes. Pennie soon moved into an apartment near me and we were soon spending much of our alone time together naked, exploring each others sexual parts, learning how to touch and masturbate each other, maximizing our mutual sexual pleasure. We had agreed to abstain from actual intercourse for a period of time, but had not necessarily agreed to abstain from any sexual pleasure all together. It did not matter because with Pennie, no intercourse did not mean no pleasure. We both became quite skilled in our techniques on each other.
In her apartment, we were rarely dressed. This lasted at least until she took in a female roommate to help her with the living expenses. Our unrestricted mutual masturbation became somewhat limited to times when her roommate was gone or asleep in the bedroom, then we would go at it in the living room, but always under a cover and never totally naked. One day, however, Pennie and I had been out running and I was so very horny watching her in her tight fitting shorts and sports bra. By the time we got back to her apartment, I had an erection that was literally begging for her attention, and she was loving the effect that her hot body was having upon me. Her roommate was home, so I was anticipating continued discomfort in my underwear. The roommate was in the bedroom of their one bedroom apartment studying for an exam the next day.
Pennie and I went to the living room and laid down facing each other on her couch. We began kissing and as we did, I began rubbing her petite breasts through her sports bra. Our kissing became more passionate as I moved my hand underneath her bra. I always loved stroking her wonderful nipples with my fingers and feeling her getting more and more turned on. Pennie began squirming and moaning as we kissed and as I caressed her nipples. This always made her (and me) very horny. I could not resist the urge to feel the soft lips of her pussy with my fingers. I moved my hand lower and began to caress her inner thighs as she moved her legs further apart. All of a sudden, she mouthed her roommate's name, to remind me that it wasn't safe to be going further. My response was to move my fingers upward and I started stroking her pussy through her shorts.
Any concerns that Pennie might have had soon evaporated. As she moaned in pleasure, I moved my hand into her underwear and soon found her very wet and very aroused pussy. I continued kissing her as I masturbated her with my hand still in her underwear. I had learned that the key to making her cum at this point was to concentrate on rubbing her clit with one finger on top of it and one along the side of it. The magic worked again. Her orgasm was very intense, but she suppressed her vocalizations so as not to reveal our activity to her roommate. She slowly relaxed in my arms and smiled as she called me a 'naughty boy'. I did not remove my hand for a time as I really loved feeling the shape and texture of her lovely pussy with my fingers. Momentarily, she pulled my hand out of her underwear and licked my fingers.
Then, without breaking her gaze into my eyes, she reached down and began to stroke my penis through my shorts. I was already rock solid and her touch was awesome, even if there was fabric between her fingers and my penis. Pennie made several unsatisfactory attempts to get her hand down my shorts to stroke my uncircumcised penis with her hand. Then she attempted to put her hand up the leg of my shorts to access my very erect penis. That did not work very well for her either. At that moment, Pennie surprised me by unbuttoning and unzipping my shorts with one hand and tugging them down with the other. There I was laying on her couch with my shorts down to about my knees, with my aching and very hard penis in her hand. Kissing me passionately, she began to masturbate me in the expert technique that she had previously developed. Holding my penis with her right hand, with her thumb around the front side of my penis head, and her other fingers around the underside, she began the glide my foreskin up and down my penis, massaging the rim each time.
Pennie had never seen or played with an uncircumcised penis before mine, but she definitely discovered many ways to maximize my pleasure...and hers. It was all so erotic with me being so aroused, feeling her wonderful warm hand around the head of my penis, and the cool air from the apartment on my foreskin and the head of my penis each time that she pulled the skin back revealing the ultra sensitive head. Pennie knew just when to speed up to get me going and when to slow down to make the pleasure last. The situation was also greatly erotically charged with her roommate awake and in the adjacent room. She could have come in at any time. It was a fantasy of mine that the three of us could be naked together. I would have loved to have had her watch Pennie masturbate me or even to lend a hand to help. At last Pennie sensed that I could not stand to put off my orgasm any longer. As she brought me to an intense orgasm, I shot out my cum all over her hand and stomach and chest. It was one of the most intense orgasms I have ever had. So far as I know her roommate never knew. Pennie and I broke up a year later. To this day, I have never been with anyone as erotic as she. I still masturbate fantasizing about her. If she was agreeable today, I would definitely love to masturbate with her again.