There comes a point in everyone's life when they ask themselves, how did I end up like this? Unsurprisingly, it usually occurs around their middle-aged years, when life has lost its excitement and they find themselves living out the same humdrum routine, with each day blending into the next. For me, the question surfaced not long after my forty-eighth birthday. I’d been married for nearly thirty years, my children had grown up, and me and my husband had become like a couple of friends, house sharing.
The trouble with analysing your life, is you begin to compare yourself, and that's when your problems really begin. You see, no matter who you are, there is always someone who's circumstances are better. It doesn't matter that there are lots more whose circumstances are worse; it's always the better ones that stand out. In my case, the person whose circumstances were better, was my best friend, Jean Barrowman.
Jean was the same age as me. She had been divorced for five years, had two children still living at home and jumped from job to job. So, why was I jealous? Because Jean had a thirtysomething boyfriend and every time we’d meet, jean would insist on describing – in intimate detail – just how great her sex life was. It was torture. I mean, I hadn't had sex in years, and listening to Jean was like being a victim of a famine watching a morbidly obese woman devour a steak. I became obsessed and used to masturbate thinking about her boyfriend. I’d rub myself fantasising about her young man, who I'd never met, sliding his tongue inside me and holding me down as he pounded me with his powerful cock.
In my desperation I joined a dating site, and while my husband was at work, I’d meet with guys. At first, I set my age filter to men who were around my age, but that didn't work. Most where either overweight, balding or worse, both, and not one excited me. So, I set my age filter to thirty-somethings. To be honest, the reason I didn't start with thirty-year-olds, is because I didn't think they'd be interested. I mean, I wasn't ugly, or overweight, but I definitely wasn't in my prime. I had a few wrinkles, a few more pounds, and more than one or two grey hairs, but my figure was still ok, and despite breastfeeding two children, my boobs were holding up well. Still, I was I certain I couldn't compare to the average thirty-year-old, or so I thought.
It turned out I was wrong. There were plenty of younger guys looking for an older woman. After wading thought a flood of messages, I met a lovely young guy named Matt. Matt was everything I could hope for. He was good looking, masculine and sex with him was great. Best of all, Matt didn't care that I was married. I honestly thought things couldn't be better until, Jean convinced me to accompany her on holiday.
Jean had split with her boyfriend and on the spur of the moment, she decided to organise a week long holiday in Magaluf. It was easy to guess what she had in mind. I mean, Magaluf isn't known for its quite nights. It's the kind of place frequented by stag and hen parties, and has a reputation for excessive sex. Despite being happy with my new boyfriend, I agreed to go. It wasn't that I was looking for sex, I just wanted a bit of fun, and after twenty years of holidays where I did nothing but sit by a pool, who could blame me?
Along with Jean, four more of our friends accompanied us. There was Cathy; a fifty-five-year-old nurse, Sandra and Debs; both former school friends, and Angie; a personal trainer who we all knew from the gym. Jean had organised a hotel close to the beach and the nightlife. Her plan was to lie in the sun during the day and then to party all night long. I was well up for it. I mean, I wasn't over the hill quite yet and so why shouldn't I enjoy myself?
The first day went exactly as I expected. We sunbathed until the sun was extinguished by the sea, then went back to our hotel for dinner. After throwing on our party gear, we hit the clubs. We started at the closest, where we gathered around the bar. Jean ordered us some drinks, then after checking out the local talent, we strutted on to the dance floor. I danced with a few guys and even exchanged a couple of kisses, but as soon as someone tried to take it further, I'd make an excuse and return to my friends. At the end of the night, I wandered back to my room, alone, but happy.
In the morning I phoned my husband and Matt, just to let them know I was having a great time, but not that great that I was misbehaving. Not that I intended to misbehave. I was happy with my situation, and was only there for fun.
The second night began in a similar fashion to the first. We entered the nearest club and gathered round the bar. Only, on this night, I noticed a young guy staring at me as we arrived. I was wearing a short red skirt and looked pretty hot, but no hotter than my mates. Still, for some reason the guy seemed to have singled me out. Not that I cared. I mean, don't get me wrong, he was cute, tall and slender, but he looked way to young – at least for me. So, I ignored him. It didn't seem to put him off and he continued to stare.
After about fifteen minutes, the lad approached. I was quite impressed, I mean, there were six of us and we were all way older, so he had some balls, but not enough that he wasn't nervous. Faced with a gang of six older women, he looked like rabbit caught in the headlights of an on-coming car. “Eh how about um a dance?” he faltered, smiling awkwardly. I completely ignored him. I mean, it was like being asked out by my son, or worse, my grandson. If he had ten more years I wouldn't have hesitated, but I wasn't a cradle snatcher. The lad wasn't deterred and repeated, only louder, “How about a dance?”
Everyone was now looking our way. It was majorly embarrassing and left me with little choice but to respond curtly, “No thank you, I'm not interested."
The guy visible sank.
Jean, who had witness the incident, glared at me. “What'd ya do that for?”
“What?” I said, holding up my hands.
“Turn him down so harshly.” Jean looked at the boy with a sympathetic smile. “Look at him; you've crushed him. It's not like he did anything wrong. He just asked you for a dance. You should make it up to him and give him that dance.”
The boy looked at me, his brows raised in hope.
Shaking my head, I exhaled, “Fine,” and took his hand.
He led me to the dance floor, and I have to say, he was quite a dancer. I quickly forgot about his age and the incident, and just enjoyed myself. In fact, I enjoyed myself so much, we had not one, but five dances. At the end of the fifth he leant over and attempted to kiss me. I wasn't interested, so I told him, “I need to go check on my mates, just to make sure everything’s ok.” He nodded and escorted me back across the dance floor.
When we arrived, my friends were nowhere to be seen. I checked my phone; there was nothing. I asked the barman. He said ‘they left about ten minutes earlier’ but he didn't know where they'd gone. I was about to tell the lad I had to go, but before I could, he offered to buy me a drink. I thought, why not? I mean, what else was I going to do? The only alternative was to return to my room.
The lad bought me a G&T and we found a table. We sat down opposite each other and chatted. He told me his name was Alex and that he was from Manchester. I told him I was Jo and from London. We talked for a bit, then from nowhere he blurted, “I have to say, when you walked into the club, I couldn't believe my eyes.”
“Why?” I inquired.
“Because, you're the most beautiful woman I've ever seen!”
I laughed. Mostly out of embarrassment. I was old enough to be his gran and doubted very much that he hadn't seen someone more beautiful. “I bet you say that to all the girls,” I said, giggling.
“If I’d met any as beautiful as you, I would have, but I haven't,” said Alex.
I blushed. Alex was a charmer and I have to admit, I was starting to fancy him although, I suspect the alcohol was more than playing its part. Despite the attraction, I was determined not to go to bed with him which, I guessed was what he was trying to engineer.
Alex stood up and held out his hand. “How about another dance?”
The music had dropped tempo. It wasn't my cup of tea, but it seemed a good way to escape Alex’s advances. I took his hand and followed. When we reached the dance floor, he wrapped his arms around me and pulled me close. Pushing his leg between mine, he slowly gyrated it against me.
As we danced, I feel Alex's leg rub against my crotch. I didn't stop it. I'm not sure why I didn't, but I suspect it had something to do with the damp patch quickly forming in my knickers.
Alex hands dropped to my bum. At this point I was quite wet. He squeezed, testing how far he could go. My lack of resistance must have told him as far as he wanted, as he continued. He stared into my eyes. I stared back into his. He kissed me; his mouth and tongue entwining with mine in an explosion of passion. At the same time Alex’s hand moved to my thigh. As we kissed, I could feel it rise up my skirt. He paused briefly on my waist, before plunging down inside my knickers. I was so turned on; my vagina was a watery inferno. I needed release and wanted Alex to touch me. He didn't disappoint and slid his finger inside my hot, wet hole. I gasped. It was heavenly.
Not wanting a scene on the dance floor, I took Alex back to my room. Once inside, he pushed me against the wall and kissed me. He was young, but dominant, which really turned me on. As we kissed, Alex unbutton my top. He removed it and discarded it to the floor like a piece of trash. Next, he unhooked my bra. Yanking it upwards, he exposed my sizable white tits. Like an animal Alex set upon them, his tongue dancing around my nipples. He bit, he licked and he sucked. The attention felt fantastic and I was soon dripping.
Without pausing, Alex unzipped my skirt. It fell to the floor and my knickers soon followed. Standing before him, my hairy vagina inches from his face, I was like a dog in heat. All Alex had to do was touch me and I was going to orgasm. He got to his feet. I watched eagerly as he took off his shirt and trousers. I desperate to see what lay beneath. I wasn't disappointed. Alex's pants fell to floor and like a mighty flagpole, his cock sprung into the air.
He pushed me on to the bed. Keeling before me, he lifted my legs to exposed my hairy, wet mound. I watched, my heart pounding. I knew what he intended and the anticipation sent shivers down my spine. I gripped the bed and opened my legs wider. Alex slid his tongue inside me. Like a match to gasoline, a fire exploded within.
With each lick, electricity shot through my body. I was close to cumming and as much as I wanted to saviour it, I wasn't going to last. Alex licked up on to my clitoris and thrust a finger inside me. His tongue sucking away on my button and his finger poking away at my soaking wet hole, was too much. Like I'd been struck by lightning, my muscles contracted and I screamed, “Huh, huh, huh, HUHHHHH!” My last scream was so loud it was heard all over the hotel.
"That was amazing," I said, smiling.
Alex smiled back at me. "Glad you enjoyed it."
"Enjoyed it? I more than enjoyed it! Now, let me do something for you." I wanted to give Alex something he would never forget. Pulling him up, I kissed him passionately. He tried to kiss me back, but I had other ideas. I got him to straddle my face, then I took hold of his cock and swallowed it. I sucked on it hungrily, sliding it in and out of my mouth. It was perfect. Not too big, or too small and just the right girth. I ran my tongue around its pretty pink head and up and down its beautiful thick shaft. When I reached the base, I took his balls in my mouth and gently sucked.
I must have played with Alex's cock and balls for ten minutes. I explored every inch of them, sucking and licking till Alex was ready to shoot. With his cock in my mouth, I inserted my finger into his anus. It was clearly an experience he enjoyed, as seconds later he groaned and my throat received explosion of cum. I don't usually swallow, but this time I sucked him dry and swallowed the lot.
Alex lay beside me and we exchanged passionate kissed. In no time his manhood was standing to attention. Ready for round two, he kissed down my neck, biting and nibbling as he went. I was pretty satisfied, but as his tongue ambled over my body, I could feel my juices flow. Alex kissed over my breasts, stopping briefly to suck and lick my nipples, before continuing down to my tummy. It was clear where he was heading and I couldn't wait for him to arrive.
Alex pushed apart my legs and kissed along my inner thighs. I was desperate to be licked and spread my legs wide in anticipation. He kissed my clit and ran his tongue down my pussy lips, but he didn't stop. It appeared my finger had given him ideas, as Alex slid his tongue inside my anus. I groaned. No one had ever licked my ass before and I loved it. As Alex's tongue explored my bum, he thrust a finger inside me. It was pleasure overload. The feeling of his tongue circling my rim and burrowing into my anus, while he finger-fucked me, had me gushing. Like a broken pipe, a tsunami of my juices covered his hand. I began to moan, “Huhhhh, huhhhhh, huhhhhhhh.”
Before I could orgasm Alex stopped. I frowned, unable to hide my disappointment. Alex paid no attention and knelt before me. He pushed back my legs and with one mighty thrust, plunged his cock inside me. In an instant my disappointment turned to ecstasy.
Alex fucked me slow and hard, his stiff, young cock bashing my uterus, and his balls slapping against my bottom. I loved every minute of it. The feeling of my vagina gripping his rock-hard cock as it slid inside me, was indescribable.
He fucked me faster and harder, and the tingles of electricity shooting through my body multiplied. I was so turned on my juices coated hm. As the speed of his thrusts increases, so my excitement grew. Alex thrust extra hard and I felt as though I'd been electrocuted. My body trembled and I screamed, “Aaagghhhh, aaagghhhh, aaagghhhhh!” My orgasm was so powerful, I had convulsion after convulsion.
Rather than stop, Alex fucked me like a sex starved beast. I'd never experienced anything like it. Wave after wave of pleasure shot through my body. It was overwhelming and I cried out constantly. After several minutes of the most unbelievable sex, Alex thrust inside me like a jackhammer. buried deep within my pussy, his cock pulsate away, filling me up with spurt, after spurt of thick, warm cum.
It was without a doubt the best fuck I'd ever experienced and for several minutes I could do nothing more than lay on the bed, quivering. Unbelievably, there was still more to come. Alex fucked me so many times that night, I lost count and it wasn't until deep into the morning that we finally rested.
When I came to, Alex was still sleeping. I leant over to kiss him, but as I looked down at his face, he appeared to be just a boy. I hoped he was at least eighteen as the thought of being arrest gave me chills. It was odd, he had given me the best sex of my life, yet he looked as though he'd yet to go through puberty.
As I struggled with my dilemma, Alex awoke. He smiled at me. I wanted to smile back, but was gripped with fear. He moved to kiss me, but I turned away. Far from putting him off, Alex grabbed me and held in his arms. He looked into my eyes. I couldn't resist. Before I knew what was happening, I was on my back with Alex’s tongue inside me. It was the start of another mind-blowing session of sex that would last all afternoon.
I saw Alex every day of the holiday and we fucked so many times I lost count. My orgasms must have numbered in the hundreds. I was having at least ten a day, sometimes double and on the first day I had more like thirty. I had so much fun, I forgot to phone Matt and my husband, which took some explaining when I got back home. I did eventually learn Alex's age, but I'm not going to say. Instead, I'll leave that up to you to think what you will.