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This is a question Cougars and Sugar Daddies

Tell us your stories of age gap shags. No paedo gags please.

Inspired by The Resident Loon

(, Thu 4 Dec 2008, 13:55)
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The story of my first-time
would have made a good story for last week's QOTW, but as it's relevant, I though I'd post it here.

It was just another typical Monday night in the middle of the summer and I had gone out with my work-colleagues drinking. Gradually, we were petering out, and there were only two of us left - me and my friend "Chris" (not his real name). Usually when in large groups, I tend to get sidelined, but there were only two of us left, so the conversation at my end was starting to flow smoothly. It was one of those pubs with an atmosphere that was good for just sitting down and having a chat.

It was then that she appeared. She recognised my friend and started chatting. Quickly, he introduced her to me. In true "introductions went well, fuck the rest" style, I instantly forgot her name (but we'll refer to it as "Cassandra" (not her real name of course)). She looked about 40, had dark red hair - quite possibly dyed, but it looked like a good dye-job. She spoke in a deep and husky voice (but then again, so did most of the women from around those parts). Once she joined us, the focus of the conversation changed, but I still felt I was doing my part conversationally. No longer were we talking about geek-stuff, but she told me she was doing Karate. Being a fellow martial artist, it gave us something to talk about.

The evening flowed smoothly and drunkenly, and pretty soon, it was chucking out time. She invited both of us back to her place. I was wondering whether or not I could still make it to the kebab-shop before it closed, but decided instead to follow my new friend and see where the night would lead. On the way back, she said "The night is young". I'd heard of that phrase before. "Could it be what I think it means?" "Naaah!" She did however mention she had a boyfriend, but he was away this night. "Who knows..."

Back at her place (which was pretty close to the office), we cracked open some more cans of beer. By now, I was at that stage of drunken-ness where I tend to drift off into my own world. Cassandra had decided to go to the toilet for a bit, leaving me and Chris alone.

"You want to shag her, don't you!". He said.

Having just been in my alcoholic haze, this seemed to come out a bit out of the blue. Not sure how to respond, I just remained silent. This way, I was able to do absolutely nothing, but give both answers to the question at once. Before any elaboration could take place, she returned.

In my drunken haze, I noticed she was doing something with her clothes. I wasn't sure if she was taking them off or putting them on, I really hadn't been paying that much attention. I kept watching. The decreasing mass of clothing implied that she was taking them off.

Pretty soon, she was down to her underwear. " Could she possibly?" I asked myself. The question was soon answered with a resounding "Yes" as her tits came out. They looked somewhat deflated, but I was convinced she had a nice personality, so that didn't seem to matter. As if that wasn't enough, off came her knickers. She was definitely a redhead, and had made a pretty good job at dyeing her hair.

So there I was, me, some guy from the office, and a naked lady. "Now what?" I wondered to myself. "Where could things possibly go from here?"

That question was soon answered. Chris sensed my state of shyness/confusion from my silence and told Cassandra that I was a bit shy and had decided to let me go first. Not sure what I wanted to do next, I was frozen with fear, although I was by far more bemused than either scared or looking forward to having a go. And so, Cassandra agreed to have a go on me first. She was going to do both of us (but thankfully not at the same time, now that really would have made me scared). I was in my mid/late 20s, and Chris was in his early 30s. Cassandra was cheating on her boyfriend, and Chris was cheating on his girlfriend. Me on the other hand - single as a single thing. Cassandra perched herself on my leg, and Chris left the room, leaving just myself and a somewhat older naked lady sitting on my leg.

"Is this your first time?" she said.

"Was it really that obvious?" I thought to myself.

"Yes", I responded without any hesitation.

Being shy, I always considered it to be a great effort to try and initiate a relationship. For anything less than a full-blown relationship, it just did not seem worth the effort on my part to overcome my shyness. Women who in my mind were "that special someone" were few and far between. It's not that I was saving myself up - I was just rubbish at getting things going.

I had recently given Internet Dating a try. My first attempt the previous summer involved me meeting a lady called "Eleanor" (not her real name of course) who I instantly fell in love with (when I met her in the real-world). Unfortunately, she had to go off to the States for a few months, and it took ages before we met again, by which time, she was seeing someone else, which totally gutted me. I had recently started my second attempt at Internet Dating. So far, I had not managed another real-world meeting (although things were looking promising with an American lass called Lisa (name - not real) but she hadn't responded to my mail for a while). Even so, I was still feeling burned from my experience with Eleanor. I didn't really care that much about saving it up for a special someone.

As for Cassandra, she had come off my leg and was now sprawled over the sofa on her back gesturing for me to come over. One thing she did have going for her was her "No Bullshit" approach. She wasn't just giving hints, she was going for it! Now, I've always been crap at recognising when a woman wants it. This seemed pretty obvious, but even in the back of my mind, there was something asking me if I was sure I thought she was and to not do anything that might embarrass myself. Now, I did just tell you I was rubbish, didn't I?

So since that fateful day my pituitary gland went 'ping', I had been coming up with grand schemes to overcome my shyness and get laid. But here, I had done absolutely nothing and had an opportunity right in front of me.

It was now fight or flight. I chose fight. So I moved over to the sofa and started to take my clothes off despite still being shy and nervous. So anyway, I was moving my crotch towards hers, when suddenly, I realised I had forgotten something. In my mixture of nervousness and "this is it!", I all of a sudden remembered that I had forgotten to take off my underpants. I had to interrupt myself to remove said undies.

"Christ! I'm such a complete spacker!" I thought to myself, but really, I was too drunk to find it an embarrassment.

When I finally took off my undies, my nervousness was clearly making itself shown. I couldn't get it up! "Improvisation time" I thought - "think on my feet". So using my hands, I started stroking her lady-bits. Having watched many *ahem* 'educational' videos, I seemed to know what I was doing, but it seemed to come out like I was trying to do everything at once - quickly alternating between her upstairs and downstairs. Somehow, I think I managed to do something right, as she did seem to be enjoying it a bit. In the meantime, she grabbed hold of my still flaccid willy, but that was having no effect.

Things were made more nervous by hearing a knock at the door. Presumably, it was Chris becoming impatient at waiting for his turn (as it turned out, Chris was dyeing to get home in case his girlfriend was wondering where he had got to).

So there I was about to pop my cherry with a woman who'se name I had forgotten, was clearly many years older than myself who was cheating on her boyfriend, and I couldn't get it up. To make things worse, I was under pressure to finish quickly so my friend could have ago before his girlfriend got suspicious. Not good! Not good!

I just decided to give up and finish off quickly. Perhaps having a wank that morning wasn't such a good idea - nor was getting wankered down the pub. I had finished without even getting a hardon - let alone cumming. "Don't take it personally" I said. "Not bad for a virgin" she whispered. As I was starting to put my clothes on, she suggested I stay around. By then, Chris had gotten fed up of waiting and burst into the room. By now, my denim shorts were back on and I was adjusting the belt, but my top was still off. Had he come in a few seconds earlier ... the thought was just unbearable.

I put the rest of my clothes on, and moved out the room. At first, I stayed near the living-room door. Not really sure if I wanted to leave or stay around, I just stayed. I was feeling disorientated from having just had my first 'go' on someone and that someone being someone who I don't think I really wanted to have a go on. There was hardly any noise coming from the living room, but at one stage, I did hear Chris giggle for no reason at all. Gradually, I moved my way up the staircase. Chris soon left. As I had by now climbed up the stairs, Chris did not see me and assumed I had gone, so he just left. Cassandra soon came up the stairs to find me still there. Through the process of my beer-scooter, I ended up in her bed.

Now, this was more like it. Unlike the sofa, it felt more cosy in here. But even so, I still couldn't get it up! I was still somewhat confused. "How long have you known Chris?" I said for want of anything better to say. In bed, we were able to get closer together, and I was able to feel more of her. Her skin felt slightly rubbery, and smelled of tobacco. But even so, the atmosphere felt more relaxed, and I could take my time. I was gently caressing her back, gradually letting my stroking hands drift down to her inner thighs. One of them came up to play with her norks. This hand was assisted by my mouth which was longing to join in the fun. This was having an effect on her. Her pelvis was gyrating and she was clearly enjoying it. But I still couldn't get my todger up! Damnit! I still had fingers, so I decided to use them.

Nestled under her pubes was her slit. My fingers were going to work moving apart the flaps, folds, lips and labia that lay therein, all the while, making sure I gave everything a good stroke. Unfortunately, my fingers could not find the clitoris. She did however have a spot she liked having caressed and even grabbed my fingers to re-position them, but even so, it didn't seem very clit-like to me. I had seen many *ahem* pictures where it was obvious where the clitoris was. Why couldn't I have picked a woman with a beginner's clitoris? Soon, my Marco-Polo like fingers went off in search of the Polo-mint hole. That was much easier to find. In they went. First one, and then two. It was obvious this one preferred penetration to stimulation. And it was so. I kept pumping them in and out, and she kept responding with her hips. This went on until all of a sudden, she started shaking. This must be it, she must have come. Her mouth made no noise at all. Either she was more of a shaker than a screamer, or she had trained herself to keep quiet. The shaking took a while to subside. I slowed down my pace but was still moving inside her. It was clear she was having a better time than me. I was still pretty nervous and still couldn't get it up, but I was still enjoying myself through giving her pleasure. I thought if I had another go at mounting her, it might just work. It didn't. I was suspending my crotch over hers but there was no life between my legs. I was persistent but not getting anywhere. Pretty soon, she said "I'm drying up". This was a cue to have a rest. As she relaxed, she farted loudly and clearly. Obviously, she was a lot more relaxed than I was. In fact, I was still wondering if Chris would pop in at any minute.

And so, the legendary pillow-talk began. In her post orgasmic bliss, she described a vision she kept having of seeing some boats in a harbour in a sunny climate. She also told me that she had lived in the West-Yorkshire mill town all her life and never left the UK, but had been to Belfast (for some reason, just about everyone who I've spoken to who has never left the UK has been to Belfast). And so, it came to discussing our ages. "How old are you?" she asked. "27" was the reply. "Please, for the love of God, let her be this side of 40!" I prayed to myself. "46" was her response. Ouch! "Does that bother you?" she said. "No." was my response. This of course was a bare-faced lie. I had learned yet another thing about myself that night - that I was capable of telling a bare-faced lie to someone even in such an intimate situation. Double-Ouch!! Back in my teenaged years, I wondered if the age difference was too great if the girl of my affections's age was closer to that of my sister than me. Now, I was with someone who's age was closer to my mother than me. Triple-Ouch!!! I've always liked learning things about myself, but I was not liking what I was learning about myself that night.

Cassandra told me that it had been a fantasy of hers to deflower someone. It was the first time she'd been with a virgin. She also told me she thought I looked younger than 27. Did she want an even younger man? The feeling was certainly not mutual. She told me that she thought her body had fared well despite her age. Now that she had pointed this out, I did notice some grain of truth, but I somehow thought it was a bit egotistical of her to mention it. She also told me that her first time was when she was 15, and that she was a bit of a tomboy back in the day (can't quite remember how the two things fitted together).

She pressed her back to my front, and entangled her legs between mine. My lowest leg was on the bed, and her lowest thigh was sandwiched between my two thighs. I had quite heavy upper legs, and was wondering if I'd cut off her circulation. This caused me to keep my upper leg lifted - not lifted above, but just not applying pressure. This was making me less relaxed and I did not fall asleep. Soon, I was getting bored. Just how long could I prevent my leg from putting it's full weight on hers? Eventually, my boredom must have had an effect, as she started moving again. But it was really just the beginnings of a trip to the toilet. Despite my company, she still felt comfortable. She went straight to the toilet without even bothering to close the toilet door, and came straight back as soon as she had finished. Clearly, her Yang was very strong!

When she came back, I decided to have another go. Still not being able to get it up, she decided to change positions. She went up on her hands and knees. "Entry will be easier like this" she said. I got up on my knees and moved towards her sticking out behind. Still couldn't get it up, let alone get it in. Things were made worse by her moving her hips around. "Stop moving around, damnit!" I thought to myself. The nervousness was making me shake. She could sense my shaking. She knew I was feeling too nervous, so told me it was best to rest a bit. Clearly, she knew what she was doing!

Thinking of my flaccid member, I said to her "Don't take this personally". Trying to re-assure me, she said "It's all in the mind". "Hey, that's my line!" I thought to myself. Ever since I had seen Yellow Submarine, I liked to use that line a lot myself (or at least I liked to imagine I'd use it). "Not bad for a virgin" she said again. She knew very clearly what she was doing, and knew just what to say, so I left it at that and tried to go to sleep. Once again, she farted without shame.

The 'break' did not last very long. I decided to have another go at it. This time, she positioned herself between my legs. She tried several things to get me going. One of which involved doing something to my pee-hole. That hurt more than it did anything else. She also tried draping her norks across my cock. They were pretty deflated, so when she was face-down, they stuck out, but when lying on her back, they seemed to vanish into almost nothing. Finally, she kissed my willy. "Was she going to go down on me?" I thought? The answer appeared to be no, but this did put thoughts of my own into my mind. I had been wondering whether or not I should go down on her. "Why not" I thought to myself, so I did.

I had never before paid any consideration to the effect pubic hair would have on cunnilingus. Now, I did. She by no means had anything that even closely resembled a 'Judith' - her ginger hairs were too thinly distributed for that, but they were as long as pubes could get. They didn't bother me in any way, but I certainly felt their presence. She was responding well. I decided to do the trick with my fingers, and pretty soon, she was shaking again.

And so, it was time for some more pillow-talk. Cassandra lay herself in front of me again. This time, I had my arm over her and was gently flicking my finger over her nipple as she talked. At first, it was the boats in a sunny climate thing again. She told me that one of her regrets in life was getting married too young. That did not last, and ended up having a daughter with someone else. She was telling me about how she had an evil aunt who died when she was about 3. The aunt still appeared as a ghost to her, and in fact, I think she even said she could still see the ghost occasionally. She also had a daughter aged 16-18 ish. When the daughter was aged 3, she seemed to go through a phase of drawing devils. In more recent times, the daughter stole Cassandra's wedding-ring to buy drugs, but despite this, they were both on texting-eachother terms. Cassandra also mentioned she was taking painkillers. They were prescribed for a condition she was having, but I could but not help wonder whether or not she used them as a means of escapism. To make things more interesting, she told me that her boyfriend could come back at any time. Fortunately, he did not.

We got back into the leg-entanglement position. I asked if my leg was too heavy, and she said no. This was my cue to totally relax my upper-leg but even so, I still did not get to sleep. In fact, I did not get any sleep at all that night. Amongst the things that were going through my mind was that I had heard rumours that the company I was working for was in unhealthy financial shape. Now, if things blow up with Cassandra and my company goes bust or makes me redundant, I'd have an eject-mechanism. However, I also thought about things in a different way. At the time, I was getting involved in the Anti-Globalisation movement. I thought that if ever thought I was about to be arrested, I could use Cassandra's house as a hiding-place (although it was a bit too close to the office for comfort). In the meantime, I had just started corresponding with another woman from the Internet Dating site I was on and was wondering if she had responded to my message.

By now, it was morning. At last, I was beginning to feel the first stirrings of life in my cock. I let her know that I was interested again, but alas, I softened again. I tried to get it in again. She told me that she was dry. Usually, she used some lube when in such situations, but she seemed to have run out. Improvising, she decided to just use water instead. From my 'research', I realised that the best position seemed to be with her on top. This may have just been because I was much bigger than she was, and I could take her weight much better than she could take mine. For a brief moment, it appeared to go in, but as usual, she was moving around too much so it popped out. Damnit!

Realising I was having more fun trying to please her than being pleased, I decided to go down on her again. The room was flooded with daylight, so I could finally see where everything was and what I was doing. I had figured most of it out by now, but it was nice to see things. This time, she grabbed the back of my head and pushed me towards her. As usual, she shook in silence.

We ended up in a snog. Not wanting to get too close to her, this made me feel very uncomfortable.

"don't take it personally" I kept saying. "It's all in the mind" she said.

"How was I?" she said. To be honest, I just wanted to say "You moved around too much", but didn't. I didn't really feel like asking her, but even so, she once again repeated her mantra "Not bad for a Virgin". Hooray for my *ahem* 'educational' videos. I also realised that our physical closeness gave her a chance to sense my legendary keen-ness in a way that can only be sensed when intimate. Once again, she verbally reminded me of how well her body had fared despite her age. It was too late for me to go to sleep. I needed to be at the office in two hours.

About an hour later, we started talking. "I think we should just be friends" she said. This was exactly what was going through my mind. We just weren't meant for eachother, but we got on well. In retrospect, what she said was what many of my attempts to start a relationship had lead to the other person saying. It was basically the same thing, but this time round, I felt relieved, rather than heartbroken. She asked me not to mention any of this to her boyfriend. As if I would! We decided to meet eachother that evening for some drinks, and possibly even a 'round two' if her boyfriend was not going to be back.

It was too late for me to go back to my flat and shower, so instead, I made do with a bath at her place. She gave me some tea and we watched a bit of breakfast-television together (I usually don't watch TV before work). I soon left her place, but instead of going straight to the office, I went to get some bananas, as I had not eaten anything yet. In my bag of things, I had some deodorant which I had purchased yesterday. As Cassandra lived with her boyfriend, I thought I'd better not leave any traces of an alien-deodorant, so I applied it outside the house (also, the less I smelled of her and her place, the better).

When I arrived at work, I was once again in familiar surroundings. As I was signing in, the receptionist noticed my bananas and worse-for-the-ware posture. She jokingly asked if I had evolved back into an ape. All I could do was grunt. I was imagining Chris coming along and saying "Leave the poor guy alone, he's just lost his virginity!". I arrived at my desk. I soon got an e-mail from Chris that said "I think we'd better keep quiet about last night". No shit dude!

Having been awake all night was clearly having an effect. During the day, my boss asked if I was feeling alright. I did not want to mention my sleep deprivation - especially not why I was sleep-deprived, so I just blamed it on a hangover. My boss had been known to go out on our midweek pub-trips and get shitfaced himself, so at least he'd be sympathetic to a hangover. In reality, I wasn't hungover, but felt more like I was still drunk from the night before.

When the day ended, I went to the pub we agreed on meeting in. I was to meet the woman I had at that time been more intimate with than anyone else before, yet I made zero effort. I did not even bother to change my clothes (although to be fair, I could not be arsed to go back to my flat). At first, I was all by myself, but after 3/4 of my first pint, she turned up.

The evening was mostly her doing a monologue of her life-story, some local history and a few odd bits and pieces (she seemed to think the carpet-industry in London was run by the Mafia), and me drifting off into an alcoholic haze. Towards the end of the evening, I inadvertently discovered one of life's secrets. After last-orders, she told me that she thought I was a good listener. I protested that I was in fact not paying attention half the time, but she was having none of it. She kept insisting I was a good listener. We did not go back to hers for a 'round two', but at least I made it to the kebab-shop before it closed. I finally got back to my flat, where I ate my kebab and had a wank - thankfully, the experience hadn't traumatised me in any way, and I was still capable of getting it up.

The rest of the week felt somewhat unreal. It was more a feeling of excitement than of bliss. While we were clearly not meant to be together, my life had all of a sudden gained a lot of spice. I was looking at things in a positive - if slightly unholy manner. Would this experience mean that I was at last immune to having my life taken over by having an intense crush on someone? In fact, I was mostly curious about how things would turn out.

As it turned out, things felt like they were back to normal the following Monday. I did have a few more encounters with Cassandra, and on one occasion, she even introduced me to her boyfriend, but a few months later, I moved somewhere far, far away and did not have another encounter again. It wasn't long before I realised just how little the experience had changed me. Basically, I had mostly confirmed a few things that I had suspected for a long time. I realised a bit about the darker side of my character - I can lie even in intimate moments (although this may have just been me being polite), can take part in someone's cheating on their partner (although to be fair, it was her decision to make, not mine, and she clearly made her own mind up). One good outcome from all this was my closer friendship with Chris (as well as being closer friends, we were now Custard Cousins). Also, pr0n is good for you - it's educational.

I did not tell my other friends about this. In fact, things seemed just like they were. A few months later, I realised that yes, I was still capable of having intense crushes (though thankfully, not on Cassandra, but with someone else I later met through Internet Dating).

They say that losing your virginity is a life-changing experience. Is it bollocks! However, looking back, I can honestly say I have no regrets about the incident.

Apologies for length.
(, Thu 11 Dec 2008, 5:05, 11 replies)
apologies for length?
Length is an understatement. I needed a tea break half way through ;)

And yes, it is all in the mind.
(, Thu 11 Dec 2008, 6:54, closed)
might read this later if I have a free weekend ;)
(, Thu 11 Dec 2008, 9:21, closed)
I'm not reading all that......
.... Summarise it in one word
(, Thu 11 Dec 2008, 9:45, closed)
Not quite one word
"I went out with a friend from work, got drunk, and had a rather unsatisfactory drunken encounter with an older friend of his, which ended in brief intercourse. It was OK, but not great."

(, Thu 11 Dec 2008, 12:26, closed)
Don't listen to them, spakka
That was an epic tale, nicely written. Gets a big click from me. And not just because I was also in my mid-twenties before the v-plates came off!
(, Thu 11 Dec 2008, 9:50, closed)
Bugger off...
I'm not reading that. What the hell do you do that gives you enough time in the world to put that together in one sitting? o.0

Moving on...
(, Thu 11 Dec 2008, 11:00, closed)
shit me
that's long.
I'll let you know what I thought when I've read it (let's hope it isn't closed by then)

\edit - err... long. Yes. With rude bits.
(, Thu 11 Dec 2008, 11:06, closed)
I was hesitant
to read this at first.

I'm so glad I took the 10 minutes to do it after all.

*Click* and kudos for being willing to reveal your story.
(, Thu 11 Dec 2008, 11:06, closed)

I'm one of these surrepticiously read at work types and therefore have an internet browser squished into the bottom of the screen so it looks like I'm doing work...

I read the first few lines and was hooked, little did I know of the LENGTH.

However you get a big click for an awesome story. Seriously I've read published books that I've enjoyed less. Kind of read like Martin Amis 'Money' but set in the lead roles early twenties!
(, Thu 11 Dec 2008, 11:41, closed)
I went straight to the end
to see if there was a shit pun.

It seems there isn't, so I've booked next week off work in order to read it.

Message ends.
(, Thu 11 Dec 2008, 11:43, closed)
I went to the end too!
TO check for punnage, but then read through it anyway and really enjoyed the story!

(, Thu 11 Dec 2008, 11:57, closed)

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