My first oldie was a teacher from school. Miss Shaw was her name, Helen Shaw. She was fifty when I fucked her and still a miss. I was twenty three and we'd met in a pub one night. She was with a party of women and I was waiting for my mates. We chatted while I waited for my friends, leaving shortly after they arrived, but not before getting her address and an invitation to visit the next day, which was Saturday. She'd put on a few pounds over the years since I'd left school, but she still looked hot. I spent all day Saturday fucking her and man she was good, even doing anal when here in the UK it was still illegal. We fucked for about three months until she left town to take up another appointment. I was sorry to see her go.
Since then I've only ever had older women, at first through contact ads which I thought was always a good choice because the women who advertise in these are, I've found out to my pleasure, on the desperate side and willing to do almost anything and some will do, literally anything.
The first ad I answered was from a forty year old called Zelma. Her ad read, "Zelma, 40, good looking, good figure, no ties. I am looking for a male for sex. Will do ANYTHING ASKED. I can accommodate."
Included in the ad was a photo and she was right, she was good looking. There was an e-mail address on the photo, so I replied, describing myself. Thirty minutes later I had a reply and I couldn't believe my luck when I read she lived only an hours drive from my home.
Two hours later she was answering her doorbell, dressed in only a black basque, black stockings and heeled shoes, exactly as I'd told her how I liked to see women dress. She was right when said that she was willing to do anything, even taking a large dildo up her arse as I fucked her pussy, not that her pussy was exactly tight as I was able to get my hand and lower arm in her cavernous cunt. The woman was a true slut. We fucked for a couple of hours and when I left to go home spunk covered her face and was leaking from her pussy and arse. I had her again a couple of times after that, once with two friends where we spent nearly a day fucking her with no respite, one after the other or all three of us together, with her begging for more. We left her as I usually had, covered in spunk.
My first non ad fuck was with, I am not ashamed to say was my brother's girlfriend's mother, Gina, a decent looking fifty five year old, with medium sized tits, good figure and firm shapely legs. Her husband had left her a couple of years ago for another woman and she'd been on her own ever since.
It started after a BBQ held by my parents. It was mainly a family affair, but there were a few family friends present and Gina as always was invited. The weather was excellent, clear blue skies and temperatures of over 70 degrees Fahrenheit. Most of the men were in shorts with the women in skirts or shorts. Gina arrived with Gary, my brother and Sandra, his girlfriend, about ten minutes after we'd started and looked good in a loose fitting summer dress that was held up by two straps around her neck, tied at the back and it was obvious she was bra less while on her feet she had heeled shoes, as she always did. “Very nice” I kept thinking to myself, wondering what my chances would be of getting her out of that dress and into bed.
"What would you like to eat or drink"? I asked her when I saw her looking round as if lost.
"Hello Phil. I don't know, a burger I suppose", she answered.
"And to drink"? I asked.
"A dry white wine if it's possible", she answered.
"Be straight back, don't move", I said as I left to get her order.
"One burger and one dry white wine for madam", I said on my return.
Well you have to make them feel special if you want to fuck them, don't you, especially if she's a family friend. We chatted for a while about nothing important and as we did I was checking her out. I knew she'd no bra on because of her dress and from the front it showed because you could just see her nipples through the flimsy material. I also wondered if she was wearing anything below and what they would be.
As I pondered I could feel my cock twitch so I made my excuses and left her to circulate. She had stood close to me while we chatted and her perfume, though not strong smelled expensive. I kept looking in her direction for most of the afternoon, wondering what it would be like to get her in bed. As the afternoon wore on people were becoming more intoxicated; me excepted. I was the designated driver and as such was driving everyone home, so I was on soft drinks. I was at one point staring into space when someone touched my shoulder from behind, making me jump back to reality. It was Gina.
"Sorry about that", she said, smiling, "but I don't suppose you could get me a white wine, please".
"Certainly Gina, for you anything", I answered.
"And another burger"? She asked.
"If I have to cook it myself", I answered, laughing.
"You are an angel", she said when I returned with her wine and burger.
"My pleasure", I said.
We chatted again, this time about Gary and Sandra and how they were doing together, when she asked me why I hadn't got a girlfriend of my own.
"I prefer older women. Women of your age and upwards", I answered.
"Single one's I presume", she said.
"Not necessarily", I answered.
"You mean you go out with married women as well", she said, a shocked look on her face.
"Not so much go out with, more go with", I answered.
"You mean you just...."
"Go to bed with them, yes", I said, interrupting her.
"But why older women, why not women of your own age group"? She asked.
"I prefer older ones, they're more mature, willing to experiment and they don't go round telling all their friends", I answered.
"I see", she said.
"I hope I haven't upset you", I said, my heart sinking.
Had I blown my chance?
"No, don't be silly", she laughed. "Now I realise why you've been so attentive with me. Am I on your list of prospective conquests"?
"Only if you want to be", I answered.
"I'm both intrigued and flattered", she said. "Let me tell you later".
With that she walked away.
"Gina", I called after her, "don't mention this to mum and dad will you".
"Don't be silly. I don't think they'd approve", she said, winking.
Was I in, was she going to be mine? I hoped so.
The evening wore on and those who lived locally stayed, but those who needed lifts home now wanted a ride home and I hoped Gina wasn't going to be amongst the first. I made three trips in my car and it was nearing midnight when I returned home to find there was only Gary, Sandra and Gina left. Gina made sure the two love birds were dropped off first at the flat they shared together.
"Now then Casanova, we're on our own", she said when she'd seen that Gary and Sandra had closed the door to the block of flats they lived in.
She leaned over and kissed me, her hands holding my face. My own hands went around her neck and began stroking her shoulders. She's some kisser and my cock was soon straining to grow in my shorts.
"We'd better go before I shoot my load in my shorts", I said as I fidgeted in my seat, trying to get comfortable.
"Before we go, I want to show you something"; she said as she lifted herself from her seat and pulled up her dress, revealing her lack of underwear and her shaven pussy".
"Why you little minx", I said, stretching out an arm to touch it.
"Not now big boy, later. Drive me home", she said, leaving her dress pulled up, but just low enough to cover her decency should anyone happen to glance in.
"When did you take them off"? I asked.
"I didn't put any on", she answered.
"You mean you've been naked beneath that dress all afternoon and evening", I said, shifting in my seat to accommodate my growing cock.
"Yes", was all she said.
My mind was full of pictures of her pussy under that dress as I drove us the two miles to her home. Boy was I glad when we arrived. I stopped the car, got out and helped her out before locking it, then followed her up the path and into the house. The hall light was already on and I presumed she'd left it on a timer or something. I closed the self locking door and walked the few steps to where she was stood, put my arms around her and kissed her once again. She responded and her tongue was soon probing my mouth, caressing the inside of my mouth and playing with my tongue.
Then she broke off.
"Come on Phil. Time for bed", she said, taking my hand and leading upstairs and into her bedroom.
She switched on a bedside light and stood before me.
"Take them off. You've seen mine now it's time now for me to see yours".
I removed my trainers and tee shirt, leaving my shorts until last.
"I'll let you remove the shorts", I said, placing my hands on my hips.
Without a word she knelt in front of me, hooked her fingers in the waistband of my shorts and pulled them down, revealing no underwear, only my hardening cock.
"My turn to surprise", I said.
She didn't answer as she'd already engulfed my cock in her mouth, her head going back and forth as she sucked me, her tongue playing with the tip every time it entered her mouth. Her mouth was filling with saliva, coating my cock and dribbling from the corners of her mouth. As she sucked I could feel myself building to orgasm and tried to take my cock from her mouth but she wouldn't let me and just carried on sucking until eventually I came.
As I did I let out a low groan and held her head still as I jetted spurt after spurt of cum into her mouth. When I looked down after I'd finished, come was dribbling from the corners of her mouth. She motioned me to lie on the bed, laid over me and lowered her head to mine; I opened my mouth and closed my eyes, but opened them quickly when I felt something liquid entering my mouth. She was emptying my own cum into my mouth; I tried to move my head but she held it fast.
"Swallow it", she said gently, "swallow it baby, for me, then I'm yours".
I swallowed and was surprised to find I didn't gag on the taste. It tasted leaden and salty but not overly so. She kissed me, transferring what was left in her mouth.
"I'm yours now, you can do to me what you want and all I ask is that you be gentle and patient because it's a long time since I've been with a man", she said.
"I will", I said, "now stand up and let's see what's hiding beneath this dress.
She unfastened the bow holding the neck band together and the dress slid to the floor, leaving her standing before me, naked bar her shoes, her hands resting on her hips.
"You look wonderful and that pussy looks good enough to eat”.
She was about to remove her shoes but I told her to leave them on and to lie on the bed. I parted her legs by running my fingers up the insides of each one, making her squirm and moan with pleasure. My fingers were replaced by my lips as I reached her pussy and one light touch of my fingertips on her pussy lips was all it took to take her over the edge. I could feel her shaking as she came, a long low moan of pleasure coming from her mouth as her head rolled from side to side.
"Oh Phil that was wonderful", she breathlessly when she came down from her high.
I didn't answer because my face was buried in her groin, my teeth gently biting her labia and clit. I hadn't been down there long when with a cry of "oh God I'm cooommmiiiinnnng", she arched her back as she orgasmed again and had three more before I lifted my cunt juice covered face from her pussy. She pulled me up the bed and kissed me before running her tongue over every inch of my face, licking her juice from me.
"You taste good down there", I said before sliding down her body again.
