What Friends Are For!

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True story about how I met and slept with an older woman
5.4k words
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Part 1 of the 2 part series

Updated 09/22/2022
Created 10/24/2001
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At the time of the start of this true story I was thirty years old. I had been taking part in 'free n easy's' for about seven years. Free n easy's are where a keyboard player, or band, invite anyone who wants to sing up to do so.

I had a regular keyboard player that backed me, and we had become good friends. It was while going along to various places that he played, that I ended up at a small pub in the 'Black Country', here in the UK. The area used to be an industrial heartland, but sadly that has all but ended, and it is now known for various Indian restaurants, and friendly pubs, including the legendary 'Crooked House', which is a pub with as good foundations as the Leaning Tower Of Pisa.

Although I have had a few offers of paid work due to my singing, I leave it as a hobby, and prefer to sing as relaxation, rather than adding the extra pressure of it as a job. I went along to the pub with an old singing friend of mine, and was introduced to a face I remembered from the past, as well as a couple of new ones. The face from the past was the daughter of a couple who we had both sang with over the years. I never really took much notice of Melanie, that was her name, although good looking, she was always very quiet, and had never really spoken to me. Along with her was a equally sexy looking blonde. She was introduced to us as Dana and she was very open and cheery. I instantly took an interest in her, despite her being some seventeen years my senior, she did not look it.

I was a little disappointed then, when I was introduced to Dana's boyfriend, Martin, who was the other new face. He was about halfway between our ages, at thirty-eight. He seemed a nice guy, but I noticed he had a very high opinion of himself, and as he was the compare, which is the host of the show who introduces the singers. He spent most of the time in and out of his seat, giving me the chance to chat to both women.

I was one of the last to get called up to sing, and I didn't like the way Martin, Dana's boyfriend, made a crack about me chatting to Dana while he was 'comparing'. I took the mic and sang my songs, but I was still a bit peeved by the time I had finished and sat down.

As I was getting ready to leave later, Dana came over and apologised for what her guy had said to me, I told her it wasn't her fault, but she replied that he could be an asshole at times. We laughed and I wished her good night, she giving me a friendly peck on the cheek I didn't think I would see her again till the next gig at the pub, but I was pleased to find she came, along with Melanie, to our next gig in a small club, also in the 'Black Country'.

I took more notice of Dana's features that night, and I noticed what a great smile and eyes she had. She was very easy to chat to and we got on like old friends. This club was larger than the pub, so I was able to chat with her without Martin always staring at me. She confessed that things were not good between them, as she was convinced he was 'playing away' behind her back. Despite the fact they had discussed marriage, Martin was spotted taking a young girl into a pub near his flat, and someone told someone else, who told Dana. He denied it, but she did not believe him.

It was only a few weeks later that I arrived at the club to find Melanie alone. I asked her where Dana was, and she told me that her and Martin had split, so she was upset, and would not be coming for a while. I told Melanie to tell her I asked about her, and that she should come out and enjoy herself on the next gig, and Id take care of her, besides I missed her smily face.

I was pleased to see that Dana came to the next gig with Melanie, and we chatted well, without the problem of her boyfriend, now her ex, looking over our shoulders. I finally plucked up the courage to tell her how pretty I thought she was, and she seemed thrilled that I told her. The next few weeks flew by, as we got to know each other better, often we both ignored our companions, Dana not paying much attention to Melanie, and me not paying much to my friend, who did not actually always come with me, as I had recently moved into a flat a good way from him, and it was awkward to pick him up now, as it meant me doing a round trip of thirty-odd miles, instead of just the twelve miles if I came direct from my flat.

It was after one such night when we where getting on great that as I walked Dana to her car, she kissed me on the lips for the first time. I told her it was a nice kiss, to which she replied that she had not kissed me yet. She laughed as she got into her car and drove off. I was to find out what she meant over the next few visits, as each time she kissed me goodbye, her kisses got more passionate, until she finally pushed her tongue into my mouth and french-kissed me deeply. "Now I've kissed you!" she smiled, as I got my breath back.

We were sitting next to each other the next time I went to the club, and Dana asked me if I would do her a favour. She wanted me to flirt with, and snog her, in the club, to wind up her ex. I wasn't sure at first, but she convinced me by saying she'd make sure I enjoyed it.

All night we were sitting there, my arm round her shoulders, her softly kissing my cheek, and whispering in my ear every time Martin looked over. He did not seem particularly bothered, but she was convinced he was not as cool inside as he looked from the outside. This went on for a couple of weeks, and I eventually told her I thought he had gotten the idea. She looked at me disappointedly, and asked if I wanted her to stop. I told her I did not, but I did not think we had to limit it to just this club.

It was as we were kissing goodbye that she asked me to pick her up on the Sunday night, as it was a good idea for us to share fuel, as we did not live too far apart, and Melanie was not coming that night, so we could have an even better time, as Melanie always looked a little embarrassed as we sat there snogging next to her.

We had a great night, just Dana and I. We spent the evening tirelessly flirting, although I thought I had blown it when she asked me to dance. I just said no at first, and that I was not a very good dancer, but she would not take no for an answer. Dana looked me in the eyes and asked me what was wrong. I confessed that almost every time I danced with a sexy woman, I got hard. Dana burst out laughing, and told me that she would be offended if I did not get stiff dancing against her to a slow, smoochy number.

She pulled me onto the dance floor, and I did indeed get an erection, but instead of backing away, Dana pushed herself harder against me as we danced. We had a few dances, and I half the night with an erection. After we had been sitting for a while, relaxing, I noticed Dana was looking at me more, and occasionally letting her hand drift into my lap, saying sorry, but it was not a very good 'accident'. especially after the umpteenth time, and her obvious squeeze as she removed her hand was doing wonders for my state of erection.

I was driving Dana home when she dropped an idea out of the blue. It was my birthday on the Tuesday coming, and she asked if I had any plans. I did not, so she asked if I would like her to bring a movie over to my flat, rather than me being alone, she thought I might enjoy the company. I gladly accepted.

Before that night, the words in the birthday card she had sent me did not really register in my brain. The printed message on the front of her birthday card read, 'When people say to you, do you want a shag, some think of a carpet, some of a pipe tobacco, and others say its a bird. But you'd just say Yes Please!!'. The words inside were also to read true, she had written, ' May this birthday be the most memorable you've ever had'. I did not really put much thought into the words as I read them, but I liked her sense of humour, the card was funny, and so was she.

Tuesday arrived, and finishing work, I rushed home to shower and eat. I was expecting Dana at around eight-thirty, and I only had an hour to get ready. The phone suddenly rang, and it was Dana, she told me she would be able to get over early, if that was okay with me, I told her I had just got in, and had to shower, she laughingly told me she did not mind if I was still dripping wet when she arrived, and she said she would be over in twenty minutes. I took that as a joke, but it gave me an instant erection, and I had to rub it away as I showered.

My mobile rang just as I put my tracksuit bottoms and a t-shirt on, and it was Dana, she was outside, but was not sure which flat I lived in. I went down to let her in, welcoming her with a kiss on the lips, but not a full snog.

The coffee made and drunk, we settled down to watch the film she had brought with her. It was 'The Truman Show', and I was looking forward to it as I had heard it was funny. Dana sat beside me on my couch, and about fifteen minutes into the film she asked if she could snuggle up to me as she would be more comfortable. I let her put her feet up over one end of my sofa, and she lay her head on my chest, with my arm across her belly. As she snuggled more against me, I ran my fingers slowly, and softly, through her long blonde hair. She did not seem to mind, so I continued to caress it.

My arm moved further across her as she shifted position, and I soon found my fingers brushing the underneath of her right boob. She did not try to move my arm away, or make any comment so I left it there for a while. As she continued to shift her position, I asked her if she was okay, and she said fine, but asked was I okay with her weight on me, and I replied I was fine too. As she rested her head back onto my chest, her position now left my fingers on her boob, and I slowly moved my hand across it in slow circular movements, waiting for her to either say something, or move my hand away, but she never once made any attempt to stop me touching her boob.

God was I being naive or what? It just never occurred to me she may have come over with anything else on her. mind other than to watch the movie, and keep me company on my birthday. The fact that she was much older did not put me off her, but I thought that all the flirting she had done with me was for the benefit of her ex, and that was why she had done it in the club and pub we visited.

I decided I had nothing to loose, and caressed her more firmly, moving my fingers all around the bulge of her boob, and squeezing the flesh, as well as the nipple which was now pressing against her top through her bra. She shifted again, making me pause, but she touched my hand with hers, squeezing it, giving me her go ahead to continue. I asked her again if she was comfortable, and she turned her head to face mine, telling me she was now, and she turned her head again to rest onto my chest, as I continued to grope at her boob through her top. I decided to work my hand up towards the open neckline of her blouse, and I pushed my hand into the gap, caressing the flesh that was at the top of her boob, and moving across to touch the other one too.

Dana grabbed my hand, and pulling away the material of her bra, pushed my hand down, and under it, asking if that was what I was trying to do. I just leant forward and planted a kiss on her hair. She grabbed my arm and ran her fingers up it as I continued to kneed her tit flesh. I worked my hand further into the bra, and found her nipple, I squeezed it between two of my fingers, and she tightened her grip on my arm, I did it again, and she too again tightened her grip. I was trying to both grope her boob, and tweak her nipple, but it was awkward with her bra still on.

Suddenly Dana pulled her arm away and grabbed at her leg. I asked her if she was okay, and she said she had cramp in her leg, I offered to let her sit up, pulling my hand out of her bra, but she said she'd be okay in a minute. She rubbed the back of her calf as I rested my arm across her chest, and then I offered to help her.

Stretching my arm as far as I could, I managed to reach her calf, and ran my hand firmly down her leg, unconsciously making the strokes longer, as I got into it. I suddenly realised her legs were falling open, the more I made my strokes end near the warmth between her thighs, and I purposefully did not stop as I came to the top of her thigh on several occasions. After about ten minutes, she relaxed again, and I asked if she wanted me to keep rubbing her thigh, she answered that I could if I wanted, but the cramp had subsided now. I took the step of continuing, and made more effort to prolong the time my fingers spent grazing her crotch, until I just left it there, resting, and slowly rubbing her red hot pussy through her stretch pants.

Dana again grabbed my arm, and motioned for me to rub her harder, by putting her other hand on the back of mine, and circling over her pussy, before leaving my hand to do it on its own. Everything seemed a blur to me by now, and I did not protest as she took my hand away, pulled her pants away from her body, and thrust my hand into the source of the heat that had been making my hand sweat. I found her pubic hair, and ran my fingers slowly through it, searching for her pussy, she opened her legs more, and forced my hand down, till I found my finger run over a little bump, forcing her to jump. She laughed, and said she hoped Id found what I was looking for, again, then left my fingers to slowly rub her clitty.

I worked my fingers over her clit, and then down into her pussy. collecting a little of her wetness, so I could use this to lube my finger, and give her a smooth rub. It only took a few minutes of this before she started to pant, and grabbing my arm, digging her nails in, she begged me to rub her faster. As I complied with her request, she bucked on top of me, and her thighs clamped down around my wrist. As Dana came down from her orgasm, she thanked me, saying she'd needed it so much. I was only too glad to help, and I told her so, anytime. She laughed again, and said we had all night. Believe it or not, we turned our attentions back to the film, and within a few minutes her breathing had returned to normal.

I slowly moved my hand back across her boobs some ten minutes or so later, and she this time took my arm and plunged it straight down her top, pulling it open, allowing my hand get a better grip on her boob. While I continued to grope one boob, she pulled her top open completely, and then tugged her bra down, giving a full look at both of her boobs. For a woman of 47, she had a lovely pair of boobs, quite firm, and not what I expected to find on a woman of her age, they were still a proud asset, topped by quite large, and pinkish nipples. I continued my investigations, and found that the harder I squeezed her nipples, the more she writhed on me, and gave an audible moan too.

Neither of us had any interest in Jim Carrey now, and I just continued to grope Dana's boobs, as she held my arm, and directed it to squeeze and pull harder on them. Dana had obviously had enough by now, and she decided to take the lead. Dropping off my lap, she turned towards me, and pulling at my tracksuit bottoms, got them off, with little of my help. She tugged at my pants too, and then bent over me to take my dick straight into her mouth. Having took me right in, she moved her mouth off it, then ran her tongue around my helmet, grinning at me like the cat who had gotten the cream, and if she kept this up, she pretty soon would be. I despite having had a couple of relationships, and previous sexual relations, I had never received a half-decent blow job, and this was getting to be much more than half-decent.

As Dana sucked on my dick, she used her hands to remove her clothing, leaving her in front of me naked. I pulled her bum around towards me, and shifting her position, she allowed me to reach her ass and pussy. I pushed a finger along her wet pussy lips, still not getting a clear view of them, but enough to know where my fingers were. I slid a finger, knuckle deep into her pussy, causing her to bear down harder on my dick, as she continued to suck like her life depended on it. I risked a second finger, and she just moaned, or tried to, it was difficult with her mouth full. I later found out that her ex was not well blessed, and that this was the first decent sized dick she had had for at least a year. She kept telling me how nice it was, between mouthfuls of sucking, and also told me to finger her harder.

Dana stopped her attack on my dick, and sensing my disappointment, she just kissed me full on the lips, pushing me down onto the floor as she forced her tongue into my mouth. She asked me if I had had time to eat before she had came, I told her no, Id only had time to shower. She grinned at me, and turned round, telling me she had something I might like to eat. I was presented with my first good view of her pussy, as she lowered it over my mouth, getting into a sixty-nine, as she went back to sucking my dick.

Her pussy had large outer lips, and I gladly ran my tongue over them, before taking one into my mouth, tasting her for the first time, and loving it. The more I sucked on her lips, the harder she sucked on my dick, raking her teeth down it as she came up, then pulling my foreskin back down hard, as she coated it with her spit, and then took me back into her throat. Her throat and mouth were not quite big enough to take all my dick, but she was having a good go at it. (And before you all think I'm trying to say I'm hung like a horse, I'm not, It is just that her mouth was small, and she could not take my seven inches all in, it is quite thick though!!...lol..)

I managed to get my tongue into the wetness, and ran it along her slit, pulling open her lips with my fingers as I stuck my tongue into her pussy. I dipped my tongue as far into her folds as I could from this angle, and got a good amount of her juices onto my face for my trouble. The more I tongued her, the wetter it got, and I was lapping up the slick as it ran out of her delicious pussy. I managed to put two fingers into her, and ran my tongue over her clitty as I reamed my fingers in and out slowly.

I had to stop for a minute though, as I was going to come. I told Dana, and instead of stopping, she sucked away harder at my dick, causing me to erupt into her slurping mouth, she swallowed it all, before licking my dick clean, and managed to get me hard again, due to her wonderful technique.

Dana shifted off my face, and turned to mount me. She asked if I was ready to slide my dick into her pussy, and I just dumbly nodded. Dana positioned my now shiny dick at her pussy lips, and pulling them open, slowly slid onto me. I could not believe how tight she was, I knew that not only was she forty-seven, but that she had had three children. It was like fucking a virgin, and it was heaven. Her well muscled pussy squeezing my dick as it pushed in and out of her boiling pussy. Her boobs swinging in my face as she lowered herself so she was almost lain on top of me. I took the opportunity of one of their 'swing-bys', to attach my mouth to one of them, and sucked on the nipple, trying to gently bite, but it kept jumping out of my mouth as she pounded on top of me.

I decided to concentrate on my dick, and tried to match her thrusts with some of my own as she bucked away. It was amazing to me that she seemed to come so quickly, then keep going after a few seconds, then come again soon after, and keep going like that. She had to rest for a few seconds while each orgasm took her, but she just continued to bounce away again as soon as she could. I could feel her pussy pulsing as she came each time, but the few seconds she stopped for, enabled me to hold off on coming myself till she had come at least a dozen times. It was a big orgasm that took me over the edge, and I felt her pussy almost trying to pull my dick off as she went almost cross-eyed on top off me. It was as she relaxed her pussy muscles that I finally unloaded into her, and this made her have another little orgasm herself, as she dropped down onto my chest.

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