A First Time for Everything

A few months ago I had a great experience that was not only unexpected but unforgettable.

I had been seeing a friend off from the International Airport. By chance I met a young woman who had just farewelled her parents on an overseas holiday.

She lived with her parents in a small country town on the West Coast and I had known her mum and dad before I moved to the city. The daughter, I’ll call Jessie, was still in high school, and was now a gorgeous young woman of eighteen; some twenty years younger than me. While we were having a coffee in one of the airport café’s she mentioned that she wasn’t all that keen on driving the long way back home in the dark, especially as she would then be there by herself.

I suggested that she stay at my flat and then continue the drive home the next day. When she agreed I told her to follow my car back to my place.

When we arrived I put a couple of TV dinners in the oven to heat and opened a bottle of cold chardonnay. By the time dinner was ready we were almost through the first bottle of wine; the conversation was moving well, going from one subject to another with ease.

The meal, accompanied by another bottle of wine, followed. When we’d finished the meal we sat in the lounge, talking and savouring the wine. Jessie said she loved wine and had been encouraged to drink sensibly by her parents from the age of thirteen. I don’t think her parents would think that two bottles was sensible, but they were on holiday anyway.

While we talked, I told her that I’d always thought that she was very pretty and now thought she was a beautiful young woman. This seemed to please her and she told me that she’d always had a crush on me too. I put my arm around her, kissing her gently; she surprised me by returning the kiss very passionately. I imagined the drink was having an effect on her.

After talking and listening to music for about another hour I said that I was ready for bed. I showed Jessie her bedroom and went and got her a pyjama top. She went to the bathroom to change and I went to my bedroom and undressed. I didn’t know what to make of the returned kiss, so with a little anticipation I too only put on a pyjama top and got into bed.

A short time later there was a quiet knock on the door and she came in, looking anything but seventeen. Her pyjama top just reached far enough to cover her pussy. After getting into bed beside me she was quite embarrassed and nervous, she told me she had never been in bed with a man before. She asked me to promise that I would not do anything to her as she was still a virgin.

I told her that I would not do anything to her unless she wanted me to. I put my arms around her and kissed her a few times, saying how gorgeous she was and how fantastic it was being in bed with her. I knew I would have to take things very slowly and keep talking quietly – if I hoped to have her surrender to me. Every time I said how beautiful she was she snuggled up a bit closer and answered softly with a moan or a sigh. After a while I slowly slid my hand over her smooth body, held her breast and felt the nipples starting to firm up.

By just brushing my fingers over her nipples they were soon hard and enlarged. Each time I did this her body would rise up to meet my hand and she would start to take deep breaths and hold them before slowly exhaling. I considered the time was right to proceed slowly and gently down the outside of her thigh. After doing this a few times I brought my hand upwards on the inside of her thigh; she shrunk back a bit as my fingers pressed up to briefly touch her pussy lips. I didn’t linger there the first few times.

When I thought she had relaxed enough I slid my hand down further and gently drew my fingers up and down the sensitive area between her anus and her vagina, her body twitched every time I did it. She soon started to get quite wet and slippery and as I quickened the action it made her gasp. Then as I drew my hand upwards again my fingers moved slowly up to the closed lips of her pussy, until I located her clitoris. This almost made her jump off the bed, so I soothed her by asking if she wanted me to stop. I knew that she was too worked up to want that… She begged me to be gentle.

Just at the top of her pussy lips I could feel the firm shaft of her clitoris. I took it between my fingertips and slid the hood that covered it backwards and forwards. She began to get very excited and her kisses became even more passionate and urgent. Then I slid the hood gently back so that her shaft was exposed for a moment. All I did was gently hold her clitoris through the hood for about a couple of minutes, I could feel it swelling and firming between my fingers. All the time she was moaning softly and her body began a gentle swaying motion. When I let the hood go the bared clit remained exposed.

I gently spread her pussy lips wide… and this had a terrific effect on her. Her body started to jerk upwards as if she was already being fucked. I next placed my finger at the entrance to her vagina and applied slight pressure, but without letting it enter. Soon I pushed a bit harder and my finger went into her up to the first knuckle. It was still very tight and she pulled back slightly. I kept my finger quite still until she got used to it, then she relaxed slightly. I was soon able to slowly rotate my finger gently around the tight rim of her entrance. When I thought she was ready I slipped my finger in up to the second knuckle. Her pussy was really wet and oozing by this stage and her interior muscles were going frantic, tightening and relaxing.

Before long I was able to slip another finger into her and gently spread her apart as her hips rose and fell. She was now reaching for my penis with one hand, but I would not let her get to it as I thought the size might frighten her. I kept on telling her how marvellous she was, and shifted our positions slightly so that I could reach other untouched areas.

She now seemed quite brave and confident; I knew it was time to attempt to enter her. I took my penis in my hand and started to rub it around her cunt lips until I was sure that she was slippery enough for me to penetrate. She got a bit nervous at this stage and made me promise not to hurt her. She said that although she was still a virgin she had been on the pill for over a year as a safeguard; I gave a sigh when I heard this… no need to halt proceedings for a condom fitting performance.

I told her to spread her legs wide, then pulled my foreskin forward right over my penis, placing it at the entrance to her vagina. Finally I pushed slowly but firmly and felt my cock slide past her entrance. This made her gasp, and I attempted no further until she had relaxed a little. All her cunt muscles were going wild at this stage so I put a bit more pressure on and felt my cock slide another inch or so inside.

Every time I went to push a little further she got a bit panicky, so I had to be content with easing back a little before any further attempts. Without trying to get further I just let my cock rest inside her and set up a throbbing action. This had an incredible effect on her, and although I teased her with this a while, I still had about four inches still to go.

At this point I suggested that she get on top so she would have total control of how much she wanted to take. She agreed – by now she wanted everything inside her. I said that we should roll over still joined together. I cheated a bit on her, as I pretended it was very hard to keep my balance, and made strong thrusts as we changed position – on the second thrust I was home. She had been too occupied with not falling off the bed and didn’t notice too much.

I told her that she now had every inch of my cock inside her cunt and how clever she was. For a while I began to move in and out of her, with Jessie responding beautifully. Then I increased the speed until we were both almost leaving the bed. Our bodies slapped together feverishly. Jessie began a low moan that got more guttural as she had her first orgasm. Naturally, this finished me and I pushed deep into her as I came far, far inside.

It had been a long session and we were both fairly weary, so I slowly withdrew from her. She rolled back on the bed and I curled up against her curved back. That could have been the end of the night - but not so. Less than an hour later I was starting to get urges again with such a gorgeous woman next to me. I slowly moved my hands from her breasts down to her warm pussy and although she pretended to be asleep she responded by moving her pelvis. Soon she was rapidly fucking my fingers. I didn’t take long to enter her from behind as we lay beside each other. I told her we could stay like that until morning as she wouldn’t get tired by my weight… and we could both do anything we wanted.

We were still together mid-morning, when she said she really needed to make a move. I said: “Make all the moves you want – I love it!” I told her there was another way we could make it before she left. I asked her to get on her hands and knees and I would show her how. When she got into position it was fairly easy to enter her as she was still stretched and juicy. I asked her to lower her head onto the bed and keep her arse as high as she could. This enabled me to get right in up to the balls. After a few hard thrusts she said she was getting closer to coming and that she would like to finish off having me lying on her back – and that’s how we finished a glorious long session, with her legs spread as wide as she could get them and pulled up alongside her body as far as possible.

We both came at about the same time and lay there exhausted. I told her that I would look forward to any return she might consider and that she must know that nothing would ever equal the fantastic time we had when she lost her virginity… but I would do my best to please her, anywhere, any time.

Bring back any memories?