Looking back as a guy in his 40's, there aren't many sexual "conquests" that I regret over the years. Not that there have been huge numbers of different partners to remember, but before meeting the woman I eventually married I did have a few other relationships, and the odd one night stand or two, with each occasion being an experience from which I learnt a little more about how to please a woman, as well as the obvious pleasure experienced at the time. I remember each of these previous lovers with happiness and satisfaction, except for one.
I was 19, and had two best mates that I saw several evenings a week. Andy was a year older than me, and someone I had only met since leaving school because he was the son of someone my dad worked with, and a friend of Matt. Matt was still 18, and someone I had known for a few years, although I had only got to know him well since leaving school, both of us having in common the fact that the majority of our close friends from school had moved away to various universities while we remained at home living with parents and entering the world of work. Unlike Andy and I, Matt didn't drive at the time, so either Andy or I would usually pick him up.
The three of us quickly became very good friends, sharing many common interests such as football, music, and trying to chat up Becci, the girl with big boobs who worked in the local corner shop - sadly none of us succeeded with her, although I remain in contact with her to this day having struck up a good friendship with her over the years.
One evening Matt told us about a girl from the other side of town who he had met in an internet chatroom, and had been talking to a lot online. The town we lived in was a medium sized town, with two high schools. Matt, Andy and I had all attended the same high school, whereas Shirley, as that was the name of the girl he had met, had attended the other. She was also 18, worked at a ladies clothing store in the town, and attended a local university so that she could remain living at home with her parents.
A week later things had progressed from chatting online and emailing to exchanging mobile numbers, and Matt showed us some of the messages she had sent to him, which quite explicitly described what she wanted to do to a guy before she would "fuck his brains out." She certainly seemed to be a girl who knew what she wanted, and looking back alarm bells should probably have started sounding, but when you're a young red blooded male you only think with a certain part of your anatomy, and that was true of the three of us mates on reading that.
Matt arranged to meet with Shirley at a cafe in the town. Both Andy and I wondered how he would handle her if she was as wild as her messages suggested. Neither of us had known him to have a girlfriend before, and suspected he may still be a virgin, so either he was going to learn a lot of new things very quickly or she was going to be very disappointed. Nevertheless the meeting took place, and he reported that it had gone well and they had arranged to meet again.
After a couple of meetings with her, he brought her with him one evening when he met up with Andy while I was away for work. Matt had told us he hadn't slept with Shirley at that point, but that he thought things were going well and he would progress to that stage soon. So I was surprised to find on my return that Matt and Shirley were no longer a couple (if they could ever have been described as such), having agreed to be friends. Meanwhile, Shirley had apparently taken a liking to Andy, and the two of them had seen each other again since that first meeting, with Andy having parked up in a quiet country lane when taking Shirley home and got to know her a lot better. Indeed, Andy took Shirley to that same quiet spot several times over the coming weeks as she put the smile back on his face following his split from his previous girlfriend.
Having seen the messages he had previously sent to Matt, and heard about her appetite for sex from Andy, I was somewhat surprised when I eventually met her to find her to be a shy, quiet girl, sitting nervously by Andy's side, reluctant to join in the conversation. My first impressions of her were very different to the image I had from reading the explicit messages she had sent to Matt, and to be honest I wondered what all the fuss was about. She was quite short, curly brown hair tied in a ponytail, and nothing spectacular to look at. No make-up and slightly scruffy clothes suggesting she didn't care too much about her appearance. However, despite that it looked like she had a decent figure, with her large boobs straining against her top and the outline of her nipples showing that she wasn't wearing a bra, and the tightness of her jean showing off her perfect round ass.
I was sat immediately opposite Shirley, and as the evening went on I was certain I could feel her leg brush against mine. I withdrew my leg, assuming that I must have had it stretched out too far and she had caught it by accident, but then I felt her leg touch mine again and hold there. I caught her look me in the eye as her foot moved slowly up the inside of my leg, and a little smile as she knew she had caught my attention. I tried to ignore it, continuing the conversation with the other guys, and she withdrew her leg, getting up to go to the ladies. I wasn't sure what to do - should I say something to Andy, but risk the backlash when she inevitably denied it or claimed it was an accident and I had made more of it than I should, or just keep quiet. I opted for keeping quiet about it for now rather than ruin the evening.
On her return, Andy got up to get some drinks, and Matt went off to use the toilet, leaving Shirley and I alone at the table for a moment. There was an awkward silence for a moment. I didn't really know what to say to her. Should I challenge her on what she was doing, or just ignore it for now? I opted to ignore it.
"You seem nervous" I observed.
"So do you" she replied with a hint of a smile. "Have I made you nervous? she continued.
"No, why would I be nervous?" I enquired
"I think you know why" she replied, biting her lip as her leg once again made contact with mine. Her foot felt different this time as it slowly moved up the inside of my leg. This time she didn't stop, continuing over my inner thigh towards my crotch.
I gasped in shock as her bare foot made contact with my crotch, rubbing briefly against my cock before withdrawing as she saw Andy returning. Now I knew what felt different - she had removed her shoe to tease me and feel what I had. 'This girl may appear shy, but she definitely knows what she's doing and wants the attention' I thought to myself. Deep down I knew I should take Andy to one side and tell him what she had done, but I feared he wouldn't believe me, and therefore opted to keep silent about it. I also knew that by saying nothing there was a chance she would go further, and I would be able to reveal what she was trying to do without causing any tension between myself and Andy. However, I am ashamed to say that a part of me also enjoyed the attention, and wondered just how far things might go.
I tried to put those thoughts to the back of my mind as the evening continued, and indeed the rest of the evening passed without further incident. As we all said our goodbyes outside, I felt Shirley slip something into my hand, glaring at me as she did so which I took as an instruction not to say anything. I closed my fist to conceal what I realised was a slip of paper, and thrust it into my pocket before saying a final goodnight and heading home.
As I walked I pulled the slip of paper from my pocket and opened it up. Scribbled on it was a mobile phone number, and the words "txt me in the morning xox"
Immediately I knew I shouldn't message her. It could be a trap, and it would certainly be trouble. However, it couldn't do any harm to save her number just in case I needed to contact Andy sometime when he was with her - I know, who was I kidding, but I convinced myself that was the reason for doing it.
I thought about her note briefly the next morning at work, and while I considered sending her a message to find out what she wanted, I stuck to my original thought that it wouldn't be a good thing to do, and sent her nothing. The day passed uneventfully, and I forgot all about the note given to me the night before.
That evening I had arranged to meet up with Matt and Andy again. It was a warm summer's evening, so a pub with an outdoor drinking area was the venue of choice. I arrived early, closely followed by Matt, with us both having finished our first beer before Andy arrived with Shirley.
"Sorry I'm a bit late lads" he apologised. "The Missus asked if she could come too as she had nothing else planned tonight. You don't mind do you?"
"No, that's fine" we both replied in unison, although after the previous evening I wasn't so sure about her presence. As had been the case the previous evening, Shirley was fairly quiet, sat next to Andy again, but opposite Matt this time rather than me. As we chatted, she was typing away on her mobile, responding to messages from some of her girl mates, to the point where we almost forgot she was there other than topping up her drink when one of us went to the bar. Then suddenly I felt my own mobile vibrate in my pocket. I pulled it out and saw it was from her.
It read "You didn't txt me this morning :-( " Being the days before proper emojis were developed for use in phone messages, :-( was the symbol for a sad face.