We were Sharing Shirley

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.

I glanced over to her briefly. She didn't look up, but carried on typing away to her friends. I didn't know what to do. Should I reply, or ignore her - difficult now she clearly had my number.

I chose to ignore her for now, but I knew I couldn't for long. About 15 minutes later my phone went again. "Well. why didn't you txt me?" was her message this time.

Once again I chose to ignore it, but it was Andy's turn to buy a drink, and Matt went up to the bar with him, leaving me alone with her to question me.

"You gonna keep ignoring me? Shouldn't keep a girl waiting you know" she whispered across the table.

"How did you get my number?" I demanded.

"I got it from Andy's phone when he wasn't looking. The idiot left it lying around"

"So why not just message me first then if you wanted to speak to me?" I enquired.

"More fun this way" she replied with a wink, before quickly returning to messaging her friends as she spotted the other guys coming back.

I was intrigued to know what she meant by that comment. As the evening ended and I walked home I knew I shouldn't message her, but I couldn't help myself. I typed out the message "what did you mean it's more fun this way" and clicked send.

I didn't expect a reply that quickly, expecting that she was probably busy taking a pounding from Andy before he went home himself, but to my surprise I got a message back within a couple of minutes.

"I saw you checking out my tits last night, so I thought I'd check out your cock. Felt like you wanted to fuck me ;-)" Was the message that came through. It was true, I had been looking at her boobs, and it was also true that when her foot had found my crotch it had made me hard.

Without giving a thought to who it was I was communicating with, I started typing another response. "What if I do? How big are they? You've felt my cock but I haven't felt your tits yet."

I instantly regretted sending it, worrying that I may have overstepped the mark. I soon found out I hadn't. "If you want it come and get it ;-) xox"

"What about Andy?" I sent in reply.

"He's not here. But if you aren't man enough...." This girl really knew what she wanted and how to get it. She had got me hooked and she knew it.

Before I could think how crazy this all was I was replying again. "I'm man enough, but could you handle it?"

"I can handle anything. Come and get it if you want me to fuck your brains out" she demanded.

"Even if I want to I can't 'cos I've been drinking" I replied. It was true, I had been drinking, so was in no position to drive over anyway, but as I lay in bed that night thinking about the messages with the realisation that it was my mates girlfriend who I'd been messaging I didn't think I could have done it anyway.

I eventually drifted off to sleep, receiving no further messages that night. In fact it was a couple of days before I heard from her again, when my day at work was interrupted by a text message. "I was right then, you're not man enough. I knew you wouldn't come"

Stupidly, I responded. "I couldn't 'cos I'd been drinking. I bet you're all talk anyway!"

"Find out if I'm all talk. Pick me up later, if you dare" she challenged.

"I wanna feel those tits. How big are they?"

"You can if you pick me up later. Why do you want to know anyway?"

"You've felt my cock for size, so it's only fair I know how big yours are"

"32DD" she replied

After no messages for about an hour she followed up with a location to pick her up from at 7. I knew roughly where she lived, but I wasn't as familiar with that side of town as the side of town I lived on. However, I knew that location wasn't particularly close to where she lived, so I suspected she may just be using me as a taxi service while Andy wasn't around.

As 7pm approached, she messaged me again, informing me that she wasn't wearing a bra. I guessed that was probably her way of making sure I'd turn up, and to be honest I was having second thoughts about the whole thing, but curiosity got the better of me, and I duly drove over to where she had told me to pick her up from, outside some shops which lined one side of the road while medium sized semi-detached houses lined the other.

On arrival there was no sign of her. I looked towards the shops, assuming this would be where she would come from, and messaged her to inform her I was there. A couple of minutes later I saw her emerge from a house about 50metres down the street on the opposite side which I later discovered was her friend's house, crossing the road and walking swiftly towards my car. She opened the door and slid into the passenger seat. She was wearing tight jeans and a tight fitting t-shirt which showed off her large firm breasts. It quickly became obvious that her message about not wearing a bra was true, and I could clearly see the shape of her nipples through the thin material.

She leaned over and kissed me quickly on the lips, before asking "where are you going to take me then?"

Quite frankly I didn't have a clue where to take her. I had convinced myself that this wouldn't happen, and that it shouldn't happen, to a point where I hadn't even considered what to do if and when it did happen.

She continued to inform me that she didn't mind where we went as long as we didn't go to a spot she had been a couple of times with Andy, and we couldn't go back to her place as it would be too awkward to explain to them why she had come home with a guy that wasn't her boyfriend. Although I had previously thought she was all talk, she seemed to be making it clear that she wanted to have sex.

I started to drive, initially not sure where I was going, trying to think where to go, before I suddenly remembered a quiet country road that passed through some woods. I knew there was a car park there, but that risked being spotted. I was certain there must be somewhere else around there that I could pull off the road.

As I drove we talked. It was the first proper conversation I'd actually had with her. She told me she wasn't seeing Andy that night as he was out with his brother, which I suppose is how she knew I would be free too. I suppose I was something to do rather than be bored at home.

"So why me" I asked her.

She looked at me and smiled. "Why not?" she replied, as she reached over to my crotch and teased my rapidly hardening cock through my jeans. "besides, it doesn't look like you're complaining, big boy" she continued, giving my balls a squeeze.

"Someone seems keen" she laughed as she noticed I'd put my foot down a little more on the accelerator. It was a struggle to concentrate on the road ahead, but eventually we reached the woods.

I continued past the car park on the right hand side and as I slowed down I spotted a track into the woods on the left hand side. Instinctively I turned onto it, my headlights lighting up the tall trees as we followed the dirt track a short way into the forest before it opened out into a small clearing just large enough to turn the car around. I pulled up the car here and turned the lights and engine off. The fading light of the setting sun provided what little light came through the trees, and all was silent except the gentle rustle of leaves in the breeze.

There was an awkward silence as we both sat there looking at each other, until she commanded "kiss me!"

I leant across and kissed her softly at first, then put my right hand behind her head to pull her in for a more passionate kiss. I felt her tongue with mine as I kissed her passionately, and felt her tongue probing my mouth in return. I raised my left hand to her right breast and squeezed it firmly through the fabric of her tight t-shirt, before finding the nipple with my thumb. She moaned softly as my thumb circled her nipple, occasionally brushing over it to tease her a little.

I pulled away from kissing her, and began to lift up her top. She raised her hands, inviting me to remove it completely, which I duly did, tossing it into the passenger footwell of the car as I exposed her large firm breasts. I returned my hand I gazed at them momentarily, before placing my right hand over her left breast, squeezing it firmly. I went to kiss her once more, but she stopped me, instead guiding my head towards her right breast. I kissed and licked around her nipple before gently sucking it into my mouth. She gasped as I bit gently on it before sucking some more, gently flicking my tongue over it as I did so to tease her.

She held my head firmly in place, which I took as a sign that she liked what I was doing, and an opportunity to take things a step further. I removed my hand from her breast, sliding slowly over her stomach towards the waist of her jeans. I paused for a few seconds, then slowly slid a thumb inside her waist band and unfastened the button. Noting no resistance I continued to lower the zipper and slid my hand inside her jeans and her underwear. I could immediately feel that she wasn't completely shaved, although it did feel neatly trimmed, and her panties were soaked through. Her legs parted slightly as I felt for the entrance to her pussy, allowing my fingers to quickly locate their target. I heard a gasp once more as I inserted two fingers into her wetness, and found her clitoris with my thumb. I plunged my fingers deep into her, then began to work them rapidly in and out of her, causing her to emit a loud moan, encouraging me to continue.

Her pussy felt tight around my fingers, but I continued to work in and out of her, gradually increasing the speed. I kissed her again on the lips, a long lustful kiss, and at that moment added a third finger to my assault on her pussy. She let out another loud moan as I did, which drove me to keep going faster and fast, my thumb still teasing her clit as I did. I could feel her hips start to buck against my hand, and she broke off our kiss as her orgasm started to hit and her body shook with the waves of pleasure she was feeling.

"You bastard!" she shouted at me.

"What?" I asked, puzzled.

"I thought you'd chicken out or be really shit, but if you can do that to me so quickly with your fingers I've got to see what you can do with your cock. Get in the back where there's more room!"

I squeezed through the gap between the seats into the back of the car onto the back seat, stretching out across the seat. Shirley followed close behind, swinging her leg over my legs to straddle me. She leant forward to kiss me once more before reaching down to my belt. She maintained eye contact as she fumbled at my belt, biting her lip as she started to undo the clasp and open it, before turning her attention to the button at the top of my jeans and the zip fly. I raised my bum off the seat a little to assist as she started tugging at my loosened jeans to try to pull them down.