Rather than submit a simple story, I thought I’d invite SOL readers to take part in a little game. Does anybody remember a TV show which was on many years ago called “Call my Bluff”? Probably not very many of you.
The show consisted of two teams of three. Each member from one of the teams would tell a little story, one of which was true and the other two were bluffs. Then the other team then had to guess which of the three stories was true.
I thought I’d try something similar here. Below are three short stories describing sexual experiences I had as a young man which all involve a much older woman. However, only one of the three is true and the other two are bluffs. Which one do you think is true?
Please post your guess in the comments section by typing the name of the character from the story you think is true.
If I ever get up to 50 replies I’ll reveal which one is real and then post again describing my further experiences with the female in question.
Of course I would also appreciate any feedback, positive or negative.
So onto the stories...
Story one – School Days
I don’t think I’d be too far off the mark in saying that sometime during their school days every red-blooded boy had a crush on one of their teachers.
I was certainly no exception as by the time I’d reached the ripe old age of 18 I’d been lusting after my English teacher for the last four years. Her name was Gaye and to me, she was drop-dead gorgeous. I guess she was in her early 30s, around 5 feet 8 tall, with straight brown hair a few inches longer than shoulder length. She had a very pretty face with dark brown eyes and classic high cheekbones but what turned me on more than anything was her wonderful hour-glass figure with large firm breasts, a flat stomach, and a nice curvy ass. She usually wore a black knee length skirt, black stockings, and either a blue round-necked woollen sweater or a cherry red V-necked one, both of which were very tight fitting. I spent many a happy hour in her class ogling her wonderful body and imagining what it would be like to have her long legs wrapped around me as I screwed my beautiful teacher. I also lost count of the number of times I got told off for not concentrating!
Although it was now over 30 years ago I can remember what happened like it was yesterday. It was during the lunch break on a lovely sunny early summer’s day and a group of us were playing football. We were very lucky in that the school was set in the grounds of an old country house and along with the sports pitches there were large grass areas and also some woodland with a stream running through it.
The teachers took it in turns to monitor the buildings and grounds to make sure everyone and everything was okay and today it was Gaye’s turn. I noticed the object of my desires walking towards us in her red V-neck sweater and wondered whether we were about to be told off for something but she walked straight past us and continued down the path eventually disappearing into the woods. Now usually nobody was allowed there during the lunch break so I wondered what was going on.
My curiosity got the better of me and I left the others to the football and followed her into the woods. The path split left and right and despite scanning the area I couldn’t see any sign of which way she went. In the end I chose left but after 100 yards I reached the stream and there was still no sign of her so I retraced my steps and started walking down the other path. After a couple of hundred yards there was still no sign of her and I was just about to give up when out of the corner of my eye I caught a glimpse of her red sweater.
I slowly edged closer so I could see what she was doing making sure I remained well hidden behind the trees. Suddenly I froze and my jaw dropped as I got a clear view of what was happening. She was with one of the groundsmen, I’ve no idea what his name was, and they seemed to be in a passionate embrace. Her hands were around his neck and they were French kissing deeply. Meanwhile, his groin was grinding into her lower body, pulled tight against him by his hands on her ass.
“My God, the lucky bastard!” I thought to myself as his hands left her ass to roam all over her magnificent body.
He backed her against a tree, then still with their mouths locked together his hands disappeared under her skirt and her panties were pulled down to her ankles.
“Wow, he’s going to fuck her, I’m going to see him fuck her!”
He unzipped his jeans and lifted her skirt up around her waist. I was too far away to see everything in fine detail but by the way his hips were moving it was obvious his cock was thrusting up and down in my lovely teacher’s cunt. She bent her legs a little presumably to allow him deeper access and he responded by pumping into her faster and faster. She broke their kiss and I heard her moan with pleasure and urge him to fuck her harder but unfortunately for Gaye (and me) he came all too quickly and pulled out of her.
I thought that was going to be the end of the show and was just about to disappear back up the path when she dropped to her knees and took his cock into her mouth. I crept a little nearer to the couple making sure all the time that I was hidden by the trees. By now I was close enough to see her cheeks hollow out as she sucked him lustily and it wasn’t long before his prick started to get hard again.
He pulled her to her feet and turned her around so she was facing away from him. He moved up close behind her and groped her breasts for a few seconds before lifting her skirt up again. He pressed forward feeding his cock inch by inch into her cunt, I was about to see my gorgeous teacher get fucked for the second time in a few minutes.
My own cock was rock hard inside my pants and I had to get some relief. I pulled it out and started wanking off as he began to piston into her. I don’t know whether it was because screwing her in this position was easier but it certainly looked to me that this time he was fucking her harder and deeper than earlier. Indeed one of her hands was covering her mouth to stop her moans of pleasure being heard by anyone else. I was so excited at the show I was watching that it didn’t take me long to blow my load as he continued to ram his cock deep inside the woman of my dreams. I saw her body shake as she was finally brought to orgasm and very shortly afterwards he gave one big thrust and held his cock still as he shot his cum deep inside her.
The whole thing probably only took about five minutes but even after all these years it’s just about the most erotic thing I have ever seen. I have only two regrets. Firstly that it happened before the days of digital cameras and smartphones so I never had the opportunity to record it. And secondly that instead of quickly disappearing back through the woods I wish I’d had the courage to walk up to Gaye and try to get her to let me fuck her as well. Instead of that I had to settle for imagining what might have been.
Story two – Work
This is another story which happened many years ago but just like the previous one, I can remember what happened as clear as anything.
My first job straight after leaving college was working in an office which was open 24/7 mainly dealing with telephone calls and we operated a dual shift system of days and nights. The days were pretty busy with the phones going non-stop and a lot of people around but the nights were a doddle. We went down to single manning and hardly got any calls from mid-evening onwards. Sometimes the only person you would see would be the office cleaner, Jean.
She had started working for us about a month ago and although most people would say she was just average looking, as a sex-starved 22-year-old I found her quite attractive. She was in her early 40s, around 5 feet 4 tall and although by no means fat was definitely carrying an extra pound or two. She always wore a knee-length tunic, zipped down the front, to protect her normal day clothes and even though it was quite baggy you can still see she had nice big breasts and a plump ass.
Two weeks ago rumours started flying around that one of the guys had fucked her on the night shift. At first I didn’t believe it, but then last week somebody else said he’d also had her and what an easy lay she was. Well, that was it, if those two could get in her panties I thought I might as well try to as well.
Last night she came in at the normal time and I started following her around, engaging in small talk with her, and trying to pluck up enough courage to make a move. On a couple of occasions, she was facing away from me and I thought about moving up behind her, grabbing her hips, and pressing my groin into her ass but both times my courage failed me. Before long that was it, she had finished her work for the evening and my chance had gone. I thought to myself what a wimp I was.
After my shift finished I went home and had a couple of hours sleep, then got up and spent the rest of the afternoon reading porn stories. By the time I had to go back to work I promised myself that tonight it would be my turn to screw our mature cleaner.
Just like the previous night I followed her around chatting with her. My chance came when she bent forward to empty a waste bin presenting her plump ass to me. I was only a few feet away and all I had to do was to step forward and press myself against her but it was like my feet were stuck in concrete, I couldn’t move. I had bottled it again.
I retreated back to the restroom and flopped down in the armchair thinking what an idiot I was. Here was this curvy older woman, apparently ready and willing to be fucked, and I was too shy to make a move. A couple of minutes later my thoughts were interrupted when Jean came in and started tidying up ready to go home.
To this day I have no idea what finally gave me the courage but as she walked past I grabbed her wrist and pulled her down onto my lap. I put one hand on her waist and with the other slowly pulled her head down towards mine. For a few seconds I wondered whether she was going to scream or slap me but nothing happened. She stared straight into my eyes and I saw her smile as her lips parted. Suddenly she pushed forward and I felt her tongue invade my mouth as she ran her fingers through my hair. My tongue met hers and then I felt her sucking it into her mouth.
I couldn’t believe it. The rumours about her were true and I was about to fuck my first real woman.
I moved my hand from her waist and unzipped her tunic, slipped my hand inside and grabbed a full round breast, it felt so good. Although I would have been quite happy to spend the next couple of hours kissing her and exploring her body she had other ideas.
“We haven’t much time. If you want to fuck me, fuck me now.” she said standing up and pulling me up with her.
She lifted her tunic and skirt up around her waist and then leaned face down over the table. I quickly freed my cock and pulled her panties down as I moved up behind her and edged forward, allowing me to enter her wet cunt. Holding onto her hips I pushed more and more of my meat inside her until I was buried balls deep in the mature woman. I then began to slide my cock gently in and out, but apparently I was a little too gentle for her.
“Come on love, I’m not a china doll. Give it to me. Fuck me properly!”
It was all my dreams come true, an older woman begging me to fuck her hard, and encouraged by her demands I began to pump into Jean faster and faster. My hands left her hips and moved forward to fondle her breasts, kneading them roughly, then I grabbed a handful of hair pulling her to a more upright position.
“That’s more like it baby, shove that gorgeous prick into me!”
I’d love to say that I continued working her over for the next half hour, giving her the fuck of her life, but unfortunately I was so excited I shot my load up her after just another couple of thrusts. I don’t think I was anywhere near bringing her to orgasm. We quickly cleaned ourselves up and straightened our clothing.
“Never mind, maybe next time?” she said winking at me as she walked out the door.
So there it was, just a quickie, but it always stayed in my memory as the first time I’d had a mature woman. Our fucking sessions continued on subsequent night shifts, and yes I did learn to last long enough to give her plenty of orgasms! All good things must come to an end however and a few months later a new cleaner started work. I never did find what happened to Jean but I’ll never forget her.
Story three - Party.
This is another story of one of my earliest sexual encounters. Just like the other two it happened nearly 30 years ago when I was in my early twenties but I still have a very clear recollection of events.