Chance Encouters

I had a great experience recently that was not only unexpected but unforgettable.

While seeing a friend off at the international terminal, I saw a young woman who looked very familiar. I introduced myself, and we were not only from the same small town, but I had attended the same school as her mum and dad, and I'd met her several times when she was much younger. I moved closer to the city for convenience when I went to university.

Jessie explained that she had just farewelled her parents; they'd gone on an overseas holiday and were not due back for three weeks. Jessie wasn't keen to drive back home in the dark, so I invited her to join me for a coffee at one of the airport's many cafés and catch up on what her mum and dad were up to and what was happening in my old high school.

I soon found out that Jessie preferred the name Jess. She confirmed her age as eighteen, which made her twenty years younger than me. Jess was surprisingly easy to talk to, and as our conversation continued, I suggested she might want to stay the night at my flat and drive home the next day. Jess followed my car back to my place.

As we entered the flat, I suggested TV dinners instead of going out again to a restaurant. Jess agreed, so I popped two of them into the oven, switched the AC on and opened a bottle of chardonnay. By the time dinner was ready, we were halfway through the bottle of wine; the conversation was great and moved easily from one subject to another.

I opened a second bottle of wine during the meal and transferred to the lounge after we finished. Jess explained that she'd been encouraged to drink sensibly by her parents since her thirteenth birthday. I didn't think her parents would consider two bottles as sensible drinking, but they were on holiday, so out of sight, out of mind.

I'd always thought Jess was a pretty girl, but now I was in no doubt that she was a beautiful young woman. When I explained this, she seemed pleased and admitted that she'd always had a crush on me too.

I said, "Oh, thank you, Jess," and slid my arm around her shoulders. Drawing her in closer, I kissed her gently on the lips. She surprised me by returning the kiss with interest. The drink was affecting her far more than I had secretly hoped for.

We cuddled and listened to music for a while; then, I stretched my arms above my head, announcing I was ready for bed. I showed Jess her bedroom and handed her one of my spare pyjama tops. As she changed in the bathroom, I called out that there was a spare toothbrush and paste in the wall cupboard.

I went to my bedroom and undressed. I didn't know what to make of the returned kiss, so with a little anticipation, I put on a pyjama top and got into bed. A short time later, there was a quiet knock on my door. Jess came in, looking far more worldly-wise than eighteen. Her pyjama top reached far enough to cover her panties. She sat on the bed beside me, a little embarrassed and slightly nervous. She told me she had never been in bed with a man before and asked me to promise I would not hurt her as she was still a virgin.

I told her I would not do anything she didn't want me to. I put my arms around her, helped her into bed and kissed her lips and neck while reminding her how gorgeous she was and how fantastic it was being in bed with her.

I knew I would have to take things very slowly if I wanted her to surrender her virginity. Whenever I said how beautiful she was, she snuggled closer and answered softly with a nervous moan or a sigh. After a while, I slid my hand from her shoulder and moved slowly toward her buttocks, then around her flat, smooth stomach and up toward her breasts.

I felt Jess tense as my hands discovered new nooks and crannies that required investigation. Brushing her nipples hardened and enlarged them; each time I did this, her body would rise to meet my hand. She took deep breaths, held them and slowly exhaled.

I considered it the right time to proceed slowly down the outside of her thigh. After repeating this several times, I brought my hand to the inside of her thigh. She shrunk back a little as my fingers brushed across the crotch area of her panties. I didn't linger there, just gently touched and moved on.

When Jess had relaxed enough, I drew my fingers across the material that covered her vagina. Her body twitched as I moved up and down the sensitive area between her anus and vagina. The silk panties became wet and slippery as I quickened the action. Jess gasped when my fingers touched her clitoris. I soothed her by asking if she wanted me to stop. She begged me to continue and asked me to be gentle.

I could feel her clitoris stiffen as I took it between my fingertips and slid the hood back and forth. Jess was very excited, and her kisses became more passionate and urgent. I used the excitement to take the initiative and pull the panties to one side.

As I gently squeezed her warm wet clitoris, I felt it swell and become firm between my fingers. Like a kitten seeking attention, Jess moaned softly and pushed her feet into the mattress. Her body rose and began to sway to her own secret rhythm. When I pulled the hood of her clitoris back, it remained exposed.

The room was warm enough that we did not require the duvet. I pushed it from the side of the bed and then slowly removed Jess's panties. The pyjama top was already up far enough to expose her breasts. I quickly pulled it over her head and threw it onto the same pile as the duvet.

I encouraged Jess to put her hands behind her head and relax, then moved down the bed into a prone position with my face inches from her vagina. Using my thumbs to spread her pussy lips wide, I pressed my tongue onto the exposed nub of her clitoris. The reaction was like lighting the blue touch-paper on a firework. Her body started to jerk upwards as if she was already being fucked.

I placed my middle finger at the entrance to her vagina and applied slight pressure without letting it enter. As she spasmed, I pushed a bit harder, and my finger went in 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. She relaxed somewhat until I slowly rotated my finger around the tight rim of her wet vaginal passage. When she was ready, I slipped my finger to the second knuckle, and her interior muscles went frantic, tightening and relaxing as though she were having a seizure.

Soon, I could slip another finger into her and spread her pussy lips apart. Her hips rose and fell with each excited spasm. She reached for my penis with one hand, but I didn't let her get to it. My cock is not as big as the ones I've seen on xHamster, but I thought the size might frighten her. I kept repeating how well she was doing and shifted our positions slightly so that I could reach her untouched areas.

As she became more 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 slippery pussy lips until I was sure that she was wet enough for penetration. She suddenly became nervous and made me promise not to hurt her.

"I'm still a virgin," she whispered, "but I've been on the pill for over a year now as a safeguard." I sighed when I heard this--no need to halt proceedings to fit a condom.

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. I pushed slowly and felt my cock slide past her tight opening. Jess gasped. I did not move again until she had relaxed a little. Her muscles were going wild, so I took the opportunity to apply more pressure. My cock slid another inch into virgin territory.

Every time I tried to push further, she panicked. I had to be content with easing back a little before any further attempts. I let my rock-hard cock rest inside her and set up a rhythmic throbbing--this had an incredible effect on her. Had she known I still had over four inches to go, her reaction may have been different.

To ease the tension, I told her to get on top. "You will have more control that way, Jess." She agreed.

I suggested we roll over still joined, so it would not hurt to re-enter her. I could not resist cheating a little. I pretended it was tough to keep my balance and made two strong thrusts as we changed position. On the second thrust, I was home. She was too occupied with not falling off the bed and didn't notice how far my penis had disappeared inside her.

I complimented her on how clever she was now that every inch of my cock was inside her. I slowly moved my hips, and my cock slid in and out of her on a cushion of juices. Jess responded beautifully. I increased my speed until we were both almost leaving the bed. Our bodies slapped together feverishly. Jess began a low moan, becoming more guttural as her first orgasm crashed, wave after wave. Her reaction made me push deeper as I had my own orgasm.

Our lovemaking had made us both tired. When I slowly withdrew, Jess altered her position in the bed and curled up against the curve of my 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 moved my hands from cupping her breasts to her warm pussy. Jess must have been pretending to be asleep because she responded by rotating her pelvis. This ex-virgin was now rapidly fucking my fingers. I didn't take long to enter her from behind. After we had simultaneous orgasms, I told her we could stay in this position until morning as she wouldn't get tired by my weight, and we could initiate more lovemaking whenever we wanted.

We were still together mid-morning when Jess said she needed to make a move.

"Make all the moves you want!" I joked.

"No, seriously, I have to feed the cat. I've had a great time, but this is my last day of high school; I'd better attend, even if it was for only a few hours."

I told her I looked forward to seeing her again and reminded her that I would do my best to please her, anywhere, any time.

Bring back any memories to anyone?